NO742230L - - Google Patents
Info
- Publication number
- NO742230L NO742230L NO742230A NO742230A NO742230L NO 742230 L NO742230 L NO 742230L NO 742230 A NO742230 A NO 742230A NO 742230 A NO742230 A NO 742230A NO 742230 L NO742230 L NO 742230L
- Authority
- NO
- Norway
- Prior art keywords
- carbon atoms
- alkyl
- formula
- compound
- fiber material
- Prior art date
Links
- 125000004432 carbon atom Chemical group C* 0.000 claims description 113
- 150000001875 compounds Chemical class 0.000 claims description 94
- -1 methylenedioxybenzene compound Chemical class 0.000 claims description 70
- 125000000217 alkyl group Chemical group 0.000 claims description 46
- 239000002657 fibrous material Substances 0.000 claims description 43
- 238000000034 method Methods 0.000 claims description 41
- 125000001188 haloalkyl group Chemical group 0.000 claims description 35
- 150000002367 halogens Chemical class 0.000 claims description 22
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 22
- 229910052736 halogen Inorganic materials 0.000 claims description 21
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 21
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 20
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 20
- 239000000835 fiber Substances 0.000 claims description 20
- 239000001257 hydrogen Substances 0.000 claims description 20
- 229910052739 hydrogen Inorganic materials 0.000 claims description 20
- 229910052794 bromium Inorganic materials 0.000 claims description 19
- 239000000463 material Substances 0.000 claims description 19
- 229920000728 polyester Polymers 0.000 claims description 18
- 238000004043 dyeing Methods 0.000 claims description 15
- 238000002360 preparation method Methods 0.000 claims description 15
- 238000012546 transfer Methods 0.000 claims description 15
- 239000011230 binding agent Substances 0.000 claims description 13
- 125000002947 alkylene group Chemical group 0.000 claims description 12
- 239000004952 Polyamide Substances 0.000 claims description 11
- 230000000694 effects Effects 0.000 claims description 11
- 229920002647 polyamide Polymers 0.000 claims description 11
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 10
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 9
- 125000004218 chloromethyl group Chemical group [H]C([H])(Cl)* 0.000 claims description 9
- 150000002366 halogen compounds Chemical class 0.000 claims description 9
- 229910052698 phosphorus Inorganic materials 0.000 claims description 9
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 8
- 239000012876 carrier material Substances 0.000 claims description 8
- 239000011574 phosphorus Substances 0.000 claims description 8
- 239000011888 foil Substances 0.000 claims description 7
- 150000002431 hydrogen Chemical class 0.000 claims description 7
- 125000003342 alkenyl group Chemical group 0.000 claims description 6
- 125000003545 alkoxy group Chemical group 0.000 claims description 6
- 229910052782 aluminium Inorganic materials 0.000 claims description 6
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 claims description 6
- 239000003960 organic solvent Substances 0.000 claims description 6
- 125000005041 acyloxyalkyl group Chemical group 0.000 claims description 5
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 5
- 239000003086 colorant Substances 0.000 claims description 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 5
- 239000003791 organic solvent mixture Substances 0.000 claims description 5
- 229920002239 polyacrylonitrile Polymers 0.000 claims description 5
- 239000005711 Benzoic acid Substances 0.000 claims description 4
- WPYMKLBDIGXBTP-UHFFFAOYSA-N Benzoic acid Natural products OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims description 4
- 125000002252 acyl group Chemical group 0.000 claims description 4
- 235000010233 benzoic acid Nutrition 0.000 claims description 4
- PXQLVRUNWNTZOS-UHFFFAOYSA-N sulfanyl Chemical class [SH] PXQLVRUNWNTZOS-UHFFFAOYSA-N 0.000 claims description 4
- 230000000903 blocking effect Effects 0.000 claims description 3
- 238000000605 extraction Methods 0.000 claims description 3
- 125000000262 haloalkenyl group Chemical group 0.000 claims description 3
- 125000005059 halophenyl group Chemical group 0.000 claims description 3
- 125000005191 hydroxyalkylamino group Chemical group 0.000 claims description 3
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 2
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims description 2
- 239000001301 oxygen Substances 0.000 claims description 2
- 229910052760 oxygen Inorganic materials 0.000 claims description 2
- 125000004423 acyloxy group Chemical group 0.000 claims 1
- 150000001990 dicarboxylic acid derivatives Chemical class 0.000 claims 1
- 125000004438 haloalkoxy group Chemical group 0.000 claims 1
- BHEPBYXIRTUNPN-UHFFFAOYSA-N hydridophosphorus(.) (triplet) Chemical compound [PH] BHEPBYXIRTUNPN-UHFFFAOYSA-N 0.000 claims 1
- 239000000975 dye Substances 0.000 description 55
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 28
- 239000004744 fabric Substances 0.000 description 26
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 21
- 239000000203 mixture Substances 0.000 description 18
- BDZBKCUKTQZUTL-UHFFFAOYSA-N triethyl phosphite Chemical compound CCOP(OCC)OCC BDZBKCUKTQZUTL-UHFFFAOYSA-N 0.000 description 18
- 239000000123 paper Substances 0.000 description 15
- 239000011541 reaction mixture Substances 0.000 description 14
- 239000004753 textile Substances 0.000 description 14
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical class OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 13
- 239000000047 product Substances 0.000 description 13
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 12
- 238000006243 chemical reaction Methods 0.000 description 12
- 239000002253 acid Substances 0.000 description 11
- 235000019441 ethanol Nutrition 0.000 description 11
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 11
- 150000003018 phosphorus compounds Chemical class 0.000 description 11
- 239000002904 solvent Substances 0.000 description 10
- 239000002759 woven fabric Substances 0.000 description 10
- 239000003795 chemical substances by application Substances 0.000 description 9
- 238000004040 coloring Methods 0.000 description 9
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 8
- 125000005843 halogen group Chemical group 0.000 description 8
- 238000010438 heat treatment Methods 0.000 description 8
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 7
- 239000002202 Polyethylene glycol Substances 0.000 description 7
- 239000000987 azo dye Substances 0.000 description 7
- 239000000460 chlorine Substances 0.000 description 7
- 229910052801 chlorine Inorganic materials 0.000 description 7
- 229920001223 polyethylene glycol Polymers 0.000 description 7
- KKEYFWRCBNTPAC-UHFFFAOYSA-L terephthalate(2-) Chemical compound [O-]C(=O)C1=CC=C(C([O-])=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-L 0.000 description 7
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
- 229910052751 metal Inorganic materials 0.000 description 6
- 239000002184 metal Substances 0.000 description 6
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
- 239000000126 substance Substances 0.000 description 6
- 125000001931 aliphatic group Chemical group 0.000 description 5
- HRYZWHHZPQKTII-UHFFFAOYSA-N chloroethane Chemical compound CCCl HRYZWHHZPQKTII-UHFFFAOYSA-N 0.000 description 5
- 239000007859 condensation product Substances 0.000 description 5
- 229960003750 ethyl chloride Drugs 0.000 description 5
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 5
- 238000006068 polycondensation reaction Methods 0.000 description 5
- 239000001856 Ethyl cellulose Substances 0.000 description 4
- ZZSNKZQZMQGXPY-UHFFFAOYSA-N Ethyl cellulose Chemical compound CCOCC1OC(OC)C(OCC)C(OCC)C1OC1C(O)C(O)C(OC)C(CO)O1 ZZSNKZQZMQGXPY-UHFFFAOYSA-N 0.000 description 4
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 4
- 235000011054 acetic acid Nutrition 0.000 description 4
- 150000007513 acids Chemical class 0.000 description 4
- BFNBIHQBYMNNAN-UHFFFAOYSA-N ammonium sulfate Chemical compound N.N.OS(O)(=O)=O BFNBIHQBYMNNAN-UHFFFAOYSA-N 0.000 description 4
- 229910052921 ammonium sulfate Inorganic materials 0.000 description 4
- 235000011130 ammonium sulphate Nutrition 0.000 description 4
- RDHPKYGYEGBMSE-UHFFFAOYSA-N bromoethane Chemical compound CCBr RDHPKYGYEGBMSE-UHFFFAOYSA-N 0.000 description 4
- 125000005997 bromomethyl group Chemical group 0.000 description 4
- 125000002091 cationic group Chemical group 0.000 description 4
- 239000011248 coating agent Substances 0.000 description 4
- 238000000576 coating method Methods 0.000 description 4
- 239000006185 dispersion Substances 0.000 description 4
- 238000004821 distillation Methods 0.000 description 4
- 229920001249 ethyl cellulose Polymers 0.000 description 4
- 235000019325 ethyl cellulose Nutrition 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- 239000000155 melt Substances 0.000 description 4
- 238000010992 reflux Methods 0.000 description 4
- 150000003839 salts Chemical class 0.000 description 4
- 229920002994 synthetic fiber Polymers 0.000 description 4
- 239000012209 synthetic fiber Substances 0.000 description 4
- 125000001340 2-chloroethyl group Chemical group [H]C([H])(Cl)C([H])([H])* 0.000 description 3
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 3
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
- 229910021586 Nickel(II) chloride Inorganic materials 0.000 description 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 244000172533 Viola sororia Species 0.000 description 3
- 238000010521 absorption reaction Methods 0.000 description 3
- 239000001166 ammonium sulphate Substances 0.000 description 3
- 125000000129 anionic group Chemical group 0.000 description 3
- PYKYMHQGRFAEBM-UHFFFAOYSA-N anthraquinone Natural products CCC(=O)c1c(O)c2C(=O)C3C(C=CC=C3O)C(=O)c2cc1CC(=O)OC PYKYMHQGRFAEBM-UHFFFAOYSA-N 0.000 description 3
- 150000004056 anthraquinones Chemical class 0.000 description 3
- 125000004429 atom Chemical group 0.000 description 3
- 125000004799 bromophenyl group Chemical group 0.000 description 3
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- 229920002678 cellulose Polymers 0.000 description 3
- 238000013461 design Methods 0.000 description 3
- 235000019253 formic acid Nutrition 0.000 description 3
- 230000007062 hydrolysis Effects 0.000 description 3
- 238000006460 hydrolysis reaction Methods 0.000 description 3
- 238000005470 impregnation Methods 0.000 description 3
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 3
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 3
- QMMRZOWCJAIUJA-UHFFFAOYSA-L nickel dichloride Chemical compound Cl[Ni]Cl QMMRZOWCJAIUJA-UHFFFAOYSA-L 0.000 description 3
- 229920000642 polymer Polymers 0.000 description 3
- 238000002203 pretreatment Methods 0.000 description 3
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 3
- 229920006395 saturated elastomer Polymers 0.000 description 3
- 239000011734 sodium Substances 0.000 description 3
- 229910052708 sodium Inorganic materials 0.000 description 3
- 125000001424 substituent group Chemical group 0.000 description 3
- QQZOPKMRPOGIEB-UHFFFAOYSA-N 2-Oxohexane Chemical compound CCCCC(C)=O QQZOPKMRPOGIEB-UHFFFAOYSA-N 0.000 description 2
- HVBSAKJJOYLTQU-UHFFFAOYSA-N 4-aminobenzenesulfonic acid Chemical compound NC1=CC=C(S(O)(=O)=O)C=C1 HVBSAKJJOYLTQU-UHFFFAOYSA-N 0.000 description 2
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 2
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 241000196324 Embryophyta Species 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- 229920002302 Nylon 6,6 Polymers 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- 239000004372 Polyvinyl alcohol Substances 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 2
- 235000005811 Viola adunca Nutrition 0.000 description 2
- 235000013487 Viola odorata Nutrition 0.000 description 2
- 235000002254 Viola papilionacea Nutrition 0.000 description 2
- 235000010443 alginic acid Nutrition 0.000 description 2
- 229920000615 alginic acid Polymers 0.000 description 2
- 125000005907 alkyl ester group Chemical group 0.000 description 2
- ZRSKSQHEOZFGLJ-UHFFFAOYSA-N ammonium adipate Chemical compound [NH4+].[NH4+].[O-]C(=O)CCCCC([O-])=O ZRSKSQHEOZFGLJ-UHFFFAOYSA-N 0.000 description 2
- 239000001000 anthraquinone dye Substances 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- 239000004305 biphenyl Substances 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 2
- 230000009918 complex formation Effects 0.000 description 2
- MGNCLNQXLYJVJD-UHFFFAOYSA-N cyanuric chloride Chemical compound ClC1=NC(Cl)=NC(Cl)=N1 MGNCLNQXLYJVJD-UHFFFAOYSA-N 0.000 description 2
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 2
- 150000001991 dicarboxylic acids Chemical class 0.000 description 2
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
- 239000002270 dispersing agent Substances 0.000 description 2
- 238000005187 foaming Methods 0.000 description 2
- 229910001385 heavy metal Inorganic materials 0.000 description 2
- 125000004464 hydroxyphenyl group Chemical group 0.000 description 2
- QQVIHTHCMHWDBS-UHFFFAOYSA-N isophthalic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 125000001434 methanylylidene group Chemical group [H]C#[*] 0.000 description 2
- HBADOEPLAWDIOZ-UHFFFAOYSA-N methyl 5-(chloromethyl)-2-hydroxybenzoate Chemical compound COC(=O)C1=CC(CCl)=CC=C1O HBADOEPLAWDIOZ-UHFFFAOYSA-N 0.000 description 2
- 150000002763 monocarboxylic acids Chemical class 0.000 description 2
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 2
- PSZYNBSKGUBXEH-UHFFFAOYSA-N naphthalene-1-sulfonic acid Chemical compound C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1 PSZYNBSKGUBXEH-UHFFFAOYSA-N 0.000 description 2
- 229910052759 nickel Inorganic materials 0.000 description 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N nickel Substances [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
- XNLICIUVMPYHGG-UHFFFAOYSA-N pentan-2-one Chemical compound CCCC(C)=O XNLICIUVMPYHGG-UHFFFAOYSA-N 0.000 description 2
- OJMIONKXNSYLSR-UHFFFAOYSA-N phosphorous acid Chemical compound OP(O)O OJMIONKXNSYLSR-UHFFFAOYSA-N 0.000 description 2
- 229920002451 polyvinyl alcohol Polymers 0.000 description 2
- 238000003825 pressing Methods 0.000 description 2
- 238000007639 printing Methods 0.000 description 2
- 238000012545 processing Methods 0.000 description 2
- 239000001294 propane Substances 0.000 description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 230000005855 radiation Effects 0.000 description 2
- 239000000985 reactive dye Substances 0.000 description 2
- YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical group OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 2
- 238000003860 storage Methods 0.000 description 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- 239000002562 thickening agent Substances 0.000 description 2
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
- 238000010023 transfer printing Methods 0.000 description 2
- 230000007704 transition Effects 0.000 description 2
- CYTQBVOFDCPGCX-UHFFFAOYSA-N trimethyl phosphite Chemical compound COP(OC)OC CYTQBVOFDCPGCX-UHFFFAOYSA-N 0.000 description 2
- 238000005292 vacuum distillation Methods 0.000 description 2
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 2
- 210000002268 wool Anatomy 0.000 description 2
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 2
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 1
- UOCLXMDMGBRAIB-UHFFFAOYSA-N 1,1,1-trichloroethane Chemical compound CC(Cl)(Cl)Cl UOCLXMDMGBRAIB-UHFFFAOYSA-N 0.000 description 1
- RELMFMZEBKVZJC-UHFFFAOYSA-N 1,2,3-trichlorobenzene Chemical compound ClC1=CC=CC(Cl)=C1Cl RELMFMZEBKVZJC-UHFFFAOYSA-N 0.000 description 1
- FTNJQNQLEGKTGD-UHFFFAOYSA-N 1,3-benzodioxole Chemical class C1=CC=C2OCOC2=C1 FTNJQNQLEGKTGD-UHFFFAOYSA-N 0.000 description 1
- ONGBRSYRDRQMBB-UHFFFAOYSA-N 1-(chloromethyl)-3-ethylbenzene Chemical compound CCC1=CC=CC(CCl)=C1 ONGBRSYRDRQMBB-UHFFFAOYSA-N 0.000 description 1
- VGISFWWEOGVMED-UHFFFAOYSA-N 1-(chloromethyl)-3-methoxybenzene Chemical compound COC1=CC=CC(CCl)=C1 VGISFWWEOGVMED-UHFFFAOYSA-N 0.000 description 1
- VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical group CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 description 1
- DDGRAFHHXYIQQR-UHFFFAOYSA-N 1-chloro-3-(chloromethyl)benzene Chemical compound ClCC1=CC=CC(Cl)=C1 DDGRAFHHXYIQQR-UHFFFAOYSA-N 0.000 description 1
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 1
- OEPOKWHJYJXUGD-UHFFFAOYSA-N 2-(3-phenylmethoxyphenyl)-1,3-thiazole-4-carbaldehyde Chemical compound O=CC1=CSC(C=2C=C(OCC=3C=CC=CC=3)C=CC=2)=N1 OEPOKWHJYJXUGD-UHFFFAOYSA-N 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 1
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 1
- CWBAMDVCIHSKNW-UHFFFAOYSA-N 2-iminonaphthalene-1,4-dione Chemical compound C1=CC=C2C(=O)C(=N)CC(=O)C2=C1 CWBAMDVCIHSKNW-UHFFFAOYSA-N 0.000 description 1
- FCYVWWWTHPPJII-UHFFFAOYSA-N 2-methylidenepropanedinitrile Chemical compound N#CC(=C)C#N FCYVWWWTHPPJII-UHFFFAOYSA-N 0.000 description 1
- AGBXYHCHUYARJY-UHFFFAOYSA-N 2-phenylethenesulfonic acid Chemical class OS(=O)(=O)C=CC1=CC=CC=C1 AGBXYHCHUYARJY-UHFFFAOYSA-N 0.000 description 1
- SMTDFMMXJHYDDE-UHFFFAOYSA-N 2-prop-1-enylpyridine Chemical compound CC=CC1=CC=CC=N1 SMTDFMMXJHYDDE-UHFFFAOYSA-N 0.000 description 1
- BCHZICNRHXRCHY-UHFFFAOYSA-N 2h-oxazine Chemical compound N1OC=CC=C1 BCHZICNRHXRCHY-UHFFFAOYSA-N 0.000 description 1
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Classifications
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- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
- D06M23/00—Treatment of fibres, threads, yarns, fabrics or fibrous goods made from such materials, characterised by the process
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- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
- D06M13/00—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment
- D06M13/08—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with halogenated hydrocarbons
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
- D06M13/00—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment
- D06M13/10—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with compounds containing oxygen
- D06M13/137—Acetals, e.g. formals, or ketals
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- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
- D06M13/00—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment
- D06M13/244—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with compounds containing sulfur or phosphorus
- D06M13/282—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with compounds containing sulfur or phosphorus with compounds containing phosphorus
- D06M13/288—Phosphonic or phosphonous acids or derivatives thereof
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- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
- D06M13/00—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment
- D06M13/244—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with compounds containing sulfur or phosphorus
- D06M13/282—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with compounds containing sulfur or phosphorus with compounds containing phosphorus
- D06M13/292—Mono-, di- or triesters of phosphoric or phosphorous acids; Salts thereof
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- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
- D06P1/00—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed
- D06P1/44—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed using insoluble pigments or auxiliary substances, e.g. binders
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Description
Fremgangsmåte til farging av syntetisk, organisk fibermateriale under frembringelse av differensierte effekter. Procedure for dyeing synthetic, organic fiber material while producing differentiated effects.
Den foreliggende oppfinnelse vedrbrer en ny fremgangsmåte til farging av syntetisk fibermateriale under tilveiebringelse av differensierte effekter på tekstilfibre av syntetisk, organisk materiale. The present invention relates to a new method for dyeing synthetic fiber material while providing differentiated effects on textile fibers of synthetic, organic material.
Den nye fremgangsmåten består i at man ved hjelp av en torr, termisk fremgangsmåte forbehandler fibermaterialet på enkelte steder med et nytt preparat som oker fargeopptaket, som minst inneholder en forbindelse som ved atmosfærisk trykk over 80°C, og fortrinnsvis over 130°C overgår på fibermaterialet og deretter farger fibermaterialet. The new method consists in using a dry, thermal method to pre-treat the fiber material in certain places with a new preparation that increases color absorption, which at least contains a compound which, at atmospheric pressure above 80°C, and preferably above 130°C, transforms into the fiber material and then dyes the fiber material.
Denne stedvise forbehandling utfores hensiktsmessig idet man anbringer preparatet på et inert bærestoff, bringer det behandlede sted på bærestoffet i kontakt med fibermaterialet som skal farges, underkaster bærestoffet og fibermaterialet en varmepåvirkning på minst 80°C og.fortrinnsvis på minst 130 C, og skiller fibermaterialet fra bærestoffet. This local pre-treatment is suitably carried out by placing the preparation on an inert support material, bringing the treated area on the support material into contact with the fiber material to be dyed, subjecting the support material and the fiber material to a heat effect of at least 80°C and preferably at least 130 C, and separating the fiber material from the carrier material.
Det bærestoff som er nbdvendig for fremgangsmåten,The carrier material that is necessary for the method,
kan være endelost eller tilpasset de tekstilformer som skal behandles, dvs. det kan være oppdelt i kortere eller lengre stykker. Dette bærestoffet .har som regel ingen affinitet til det anvendte preparat. Det er hensiktmessig et fleksibelt, fortrinnsvis romlig stabilt bånd, en stripe eller en folie, fortrinnsvis med glatt overflate, som er varmebestandig og som kan bestå forskjellige materialer, f.eks. metall, såsom en aluminium- eller stål-folie, kunststoff, papir eller tekstiler som kan være strikket eller vevet eller være filt, som eventuelt kan være belagt med en film av vinylharpiks, etylcellulose, polyuretanharpiks eller polytetrafluoretylen. Der anvendes hensiktsmessig en fleksibel folie av aluminium, glassfiberstoff eller fremfor alt av papir. can be continuous or adapted to the textile forms to be processed, i.e. it can be divided into shorter or longer pieces. This carrier usually has no affinity for the preparation used. It is suitably a flexible, preferably spatially stable tape, a strip or a foil, preferably with a smooth surface, which is heat-resistant and which can consist of different materials, e.g. metal, such as an aluminum or steel foil, plastic, paper or textiles which may be knitted or woven or felt, which may optionally be coated with a film of vinyl resin, ethyl cellulose, polyurethane resin or polytetrafluoroethylene. A flexible foil made of aluminium, fiberglass or, above all, paper is suitably used.
Det tekstilbehandlingsmiddel som ifolge oppfinnelsen ved atmosfærisk trykk over 80°C går over på fibermaterialet, dreier seg om en fibermodifiserende substans som fpå fiberen frembringer en svellevirkning, eventuelt ved nedsetning av glass-punktet, eventuelt ved å forårsake en opplosning av fiberstruk-turen. Disse tekstilbehandlingsmidlene er delvis kjent, og kan fremstilles på i og for seg kjent måte. De tilhorer forskjellige klasser. The textile treatment agent which, according to the invention, transfers to the fiber material at atmospheric pressure above 80°C, is a fiber-modifying substance that produces a swelling effect on the fiber, possibly by lowering the glass point, possibly by causing a dissolution of the fiber structure. These textile treatment agents are partially known, and can be produced in a manner known per se. They belong to different classes.
Særlig forbindelser av folgende fem typer har vist seg å være fordelaktige: In particular, compounds of the following five types have proven to be beneficial:
(a) metylendioksybenzenforbindelser med formelen (a) methylenedioxybenzene compounds of the formula
hvor R? og Rp hver er alkyl med fra 1-6 karbonatomer, alkenyl med fra 2-6 karbonatomer, hydroksyalkyl med fra 1 - 6.karbonatomer, halogenalkyl med fra 1-6 karbonatomer eller eventuelt halogenert dialkylfosfonalkyl med fra 1-4 karbonatomer pr. where R? and Rp each is alkyl with from 1-6 carbon atoms, alkenyl with from 2-6 carbon atoms, hydroxyalkyl with from 1-6 carbon atoms, haloalkyl with from 1-6 carbon atoms or optionally halogenated dialkylphosphonoalkyl with from 1-4 carbon atoms per
alkylgruppe hvor minst en av restene R^ og R^inneholder halogen-eller fosfor; alkyl group where at least one of the residues R^ and R^ contains halogen or phosphorus;
(b) fosforforbindelser med formelen(b) phosphorus compounds with the formula
hvor R^ og R£ hver er alkyl med fra 1-6 karbonatomer, X" er alkylen med fra 1-4 karbonatomer og A" er fenyl, fenyl substituert med hydroksyl, alkoksy med fra 1-4 karbonatomer, alkyl med fra 1-4 karbonatomer, alkoksykarbonyl med fra 1-5 karbonatomer, fenyl eller halogen og hvor n er 1 eller 2; where R^ and R£ are each alkyl with from 1-6 carbon atoms, X" is the alkylene with from 1-4 carbon atoms and A" is phenyl, phenyl substituted with hydroxyl, alkoxy with from 1-4 carbon atoms, alkyl with from 1- 4 carbon atoms, alkoxycarbonyl with from 1-5 carbon atoms, phenyl or halogen and where n is 1 or 2;
(c) fosforforbindelser med formelen(c) phosphorus compounds of the formula
hvor R^' og R£' hver er alkyl eller halogenalkyl hvor med fra 1 - 6 karbonatomer, X,<M>er oksygen eller -NH- og hvor Z er hydrogen, alkyl, hydroksyalkyl, halogenalkyl eller alkenyl med hoyst 6 karbonatomer eller acyloksyalkyl med fra 1-6 karbonatomer i alkylresten og hvor acyl ar resten av en alifatisk monokarbonsyre med hoyst 5 karbonatomerj where R^' and R£' are each alkyl or haloalkyl with from 1 - 6 carbon atoms, X,<M>is oxygen or -NH- and where Z is hydrogen, alkyl, hydroxyalkyl, haloalkyl or alkenyl with at most 6 carbon atoms or acyloxyalkyl with from 1-6 carbon atoms in the alkyl residue and where acyl is the residue of an aliphatic monocarboxylic acid with no more than 5 carbon atoms
(d) halogenforbindelser med formel(d) halogen compounds of formula
hvor RQer halogenalkyl med fra 1-4 karbonatomer, X' er -CO-NY-, -C00-, -0C0- eller -0-, Y er hydrogen eller hydroksyalkyl med fra 1-4 karbonatomer, er halogenalkyl med fra 1-4 karbonatomer -NH2, alkylen-COOH med 3 eller 4 karbonatomer eller -alkylen-0-halogenalkyl hver med fra 1-4 karbonatomer i alkylen- eller halogenalkylresten, og hvor A^ eventuelt kan være hydrogen når X er -CO-NY- og Y er hydrogen og hvor RQ og A^ eventuel* kan være halogenalkyl eller halogenalkenyl med fra 3-6 karbonatomer når where RQ is haloalkyl with from 1-4 carbon atoms, X' is -CO-NY-, -C00-, -OC0- or -0-, Y is hydrogen or hydroxyalkyl with from 1-4 carbon atoms, is haloalkyl with from 1-4 carbon atoms -NH2, alkylene-COOH with 3 or 4 carbon atoms or -alkylene-0-haloalkyl each with from 1-4 carbon atoms in the alkylene or haloalkyl residue, and where A^ may optionally be hydrogen when X is -CO-NY- and Y is hydrogen and where RQ and A^ may optionally* be haloalkyl or haloalkenyl with from 3-6 carbon atoms when
X er -0-, ellerX is -0-, or
(e) halogenforbindelser med formelen (e) halogen compounds of the formula
hvor A"' er halogen, hydroksyl, alkoksykarbonyl med fra 2-5 karbonatomer, halogenalkoksy med fra 1-4 karbonatomer eller halogenfenyl og hvor X1?X2, X^, X^ og X^hver er halogen, alkyl med fra 1-4 karbonatomer, hydroksyl, merkapto eller hydrogen, hvor hoyst én av restene X-^X2, X^, X^og X^er alkyl eller hydroksyl eller merkapto og minst én av restene er halogen og hvor X-^ og A sammen kan være en rest med formelen -C0-0-CCK where A"' is halogen, hydroxyl, alkoxycarbonyl with from 2 to 5 carbon atoms, haloalkyl with from 1 to 4 carbon atoms or halophenyl and where X1?X2, X^, X^ and X^ are each halogen, alkyl with from 1 to 4 carbon atoms, hydroxyl, mercapto or hydrogen, where at most one of the residues X-^X2, X^, X^ and X^ is alkyl or hydroxyl or mercapto and at least one of the residues is halogen and where X-^ and A together can be a residue with the formula -C0-0-CCK
Her er forbindelsene av typen (b), (c), (e) og særlig av typen (d) foretrukne. Here, the compounds of type (b), (c), (e) and especially of type (d) are preferred.
Foretrukne forbindelser av typen (a) tilsvarer formelen Preferred compounds of type (a) correspond to the formula
hvor R-^ er en alkyl- eller alkylenrest med hoyst 6 karbonatomer som eventuelt er substituert med halogen og hvor R2er en halogen-alkylrest med fra 1-6 karbonatomer eller en dialkylfosfonometylgruppe med fra 1-4 karbonatomer pr. alkylrest. Blant forbindelsene av typen (a) er forbindelsene med formelen spesielt foretrukket, hvor R£ er en allylrest eller en mono-eller dibromert alkylrest med fra 2-4 karbonatomer og hvor R2er en klormetylgruppe eller en dialkylfosfonometylgruppe med fra 1-4 karbonatomer pr. alkylrest. Forbindelser av typen (a) av særlig interesse er forbindelser med formelen hvor X^ er brom, X^ er brom eller en rest med formelen eller hvor XX° og X^ tilsammen er en kovalent binding og hvor r2er klormetyl eller en rest med formelen where R-^ is an alkyl or alkylene residue with at most 6 carbon atoms which is optionally substituted with halogen and where R 2 is a halo-alkyl residue with from 1-6 carbon atoms or a dialkylphosphonomethyl group with from 1-4 carbon atoms per alkyl residue. Among the compounds of type (a), the compounds with the formula are particularly preferred, where R£ is an allyl radical or a mono- or dibrominated alkyl radical with from 2-4 carbon atoms and where R2 is a chloromethyl group or a dialkylphosphonomethyl group with from 1-4 carbon atoms per alkyl residue. Compounds of type (a) of particular interest are compounds of the formula where X^ is bromine, X^ is bromine or a residue of the formula or where XX° and X^ together are a covalent bond and where r2 is chloromethyl or a residue of the formula
og hvor Z1?Z2, Z^ og Z2hver er metyl eller etyl. and wherein Z 1 , Z 2 , Z 2 and Z 2 are each methyl or ethyl.
Substituentene i benzenresten i formelen (l) dreierThe substituents in the benzene residue in formula (l) rotate
seg fortrinnsvis om alkyl-, aSiRenyl-, hy dr ok sy alkyl- eller halogenalkylrester med 1-4 karbonatomer. Halogenalkylrestene kan f.eks. ha opptil 4, og fortrinnsvis fra 1-2 halogenatomer som klor eller fremfor alt brom. Eksempler på slike rester er metyl, etyl, propyl, isopropyl, butyl, sek.butyl eller tert.butyl, brommetyl, 2-brometyl, 3-brom-n-propyl, 2,2,3,3-tetrabrom-n-propyl, 2, 2,3-tribrompropyl, 2-klor-2,3-d.ibrompropyl, alkyl, metylol, 2-hydroksyetyl og særlig klormetyl og 2,3-dibrom-n-propyl. are preferably alkyl, aSiRenyl, hydroxy alkyl or haloalkyl residues with 1-4 carbon atoms. The haloalkyl radicals can e.g. have up to 4, and preferably from 1-2 halogen atoms such as chlorine or, above all, bromine. Examples of such residues are methyl, ethyl, propyl, isopropyl, butyl, sec.butyl or tert.butyl, bromomethyl, 2-bromomethyl, 3-bromo-n-propyl, 2,2,3,3-tetrabromo-n-propyl , 2, 2,3-tribromopropyl, 2-chloro-2,3-dibromopropyl, alkyl, methylol, 2-hydroxyethyl and especially chloromethyl and 2,3-dibromo-n-propyl.
Alkylrestene i dialkylfosfonoalkylgruppen henholdsvis Z-^, Z2, Z-j^og Z2representerer de samme alkylrester eller halogenalkylrester som er angitt for R-substituentene på benzenresten. The alkyl residues in the dialkylphosphonoalkyl group respectively Z-1, Z2, Z-12 and Z2 represent the same alkyl residues or haloalkyl residues as indicated for the R-substituents on the benzene residue.
Forbindelser av typen (b) og (c) representeres av fosforforbindelser med formelen Compounds of type (b) and (c) are represented by phosphorus compounds with the formula
hvor Q er en eventuelt ringsubstituert benzosyrealkylestergruppe som kan være bundet over en metylenbro, en hydroksyalkylaminogruppe eller en acyloksyalkyloksygruppe, R-, og R^er uavhengig av hverandre alkyl eller halogenalkyl med fra 1-6 karbonatomer. where Q is an optionally ring-substituted benzoic acid alkyl ester group which can be linked via a methylene bridge, a hydroxyalkylamino group or an acyloxyalkyloxy group, R- and R^ are independently alkyl or haloalkyl with from 1-6 carbon atoms.
Som hydroksyalkylamino- eller acyloksyalkoksygruppeAs a hydroxyalkylamino or acyloxyalkyl group
di formel (2) har Q fortrinnsvis alle fra 2~6 karbonatomer. Acylresten i acyloksyalkoksygruppen er med fordel en eventuelt halogensubstituert alkenoylrest med fra 3-4 karbonatomer og særlig de folgende rester: in formula (2), Q preferably has all from 2~6 carbon atoms. The acyl residue in the acyloxyalkyl group is advantageously an optionally halogen-substituted alkenoyl residue with from 3-4 carbon atoms and in particular the following residues:
og de tilsvarende brom-analoge. and the corresponding bromine analogues.
Som en eventuelt ringsubstituert benzosyrealkylestergruppe er Q fortrinnsvis en salicylsyrealkylestergruppe som fortrinnsvis er bundet direkte på fosforatomet, og hvor alkylester-gruppen fortrinnsvis inneholder fra 1-4 karbonatomer. As an optionally ring-substituted benzoic acid alkyl ester group, Q is preferably a salicylic acid alkyl ester group which is preferably attached directly to the phosphorus atom, and where the alkyl ester group preferably contains from 1 to 4 carbon atoms.
Fosforforbindelser av typen (b) med formelen Phosphorus compounds of type (b) with the formula
hvor R^ og R^ er bromalkylrester hver med fra 1-4 karbonatomer og hvor R^ er en alkylrest med fra 1-4 karbonatomer er av særlig interesse. Forbindelser av typen (b) som egner seg særlig er fosforforbindelser med formelen hvor A^ er fenyl, hydroksyfenyl, alkoksykarbonyl-hydroksyfenyl eller hydroksydifenyl og hvor R£ og n har den angitte betydning. Fordelaktige resultater har fremfor alt fosforforbindelser med formelen hvor RU er metyl eller etyl, n er 1 eller 2 og hvor AjJ er fenyl, 3-metoksykarbonyl-4-hydroksyfenyl eller 3-fenyl-4-hydroksyfenyl. Forbindelser med formelen (2) som fremfor alt er egnet til fremgangsmåten ifblge oppfinnelsen er f.eks. fosforforbindelser som er substituert på fenylkjernen som har formelen hvor R^ og RJJ hver er alkyl med fra 1-6 karbonatomer, X" er alkylen med fra 1-4 karbonatomer og hvor A^ er fenyl sam er substituert med hydroksyl, alkoksy med fra 1-4 karbonatomer, alkyl med fra 1-4 karbonatomer, alkoksykarbonyl med fra 1-5 karbonatomer, fenyl eller halogen og hvor n er 1 eller 2, og fortrinnsvis fosforbindelser som har formelen hvor AV er hydroksyfenyl, alkoksykarbonyl-hydroksyfenyl eller hydroksydifenyl og hvor og n har den angitte betydning, og særlig fosforforbindelser med formelen where R^ and R^ are bromoalkyl residues each with from 1-4 carbon atoms and where R^ is an alkyl residue with from 1-4 carbon atoms are of particular interest. Compounds of the type (b) which are particularly suitable are phosphorus compounds of the formula where A^ is phenyl, hydroxyphenyl, alkoxycarbonyl-hydroxyphenyl or hydroxydiphenyl and where R£ and n have the indicated meaning. Advantageous results have above all phosphorus compounds of the formula where RU is methyl or ethyl, n is 1 or 2 and where AjJ is phenyl, 3-methoxycarbonyl-4-hydroxyphenyl or 3-phenyl-4-hydroxyphenyl. Compounds with the formula (2) which are above all suitable for the method according to the invention are e.g. phosphorus compounds which are substituted on the phenyl nucleus having the formula where R^ and RJJ are each alkyl with from 1-6 carbon atoms, X" is the alkylene with from 1-4 carbon atoms and where A^ is phenyl sam is substituted with hydroxyl, alkoxy with from 1 -4 carbon atoms, alkyl with from 1-4 carbon atoms, alkoxycarbonyl with from 1-5 carbon atoms, phenyl or halogen and where n is 1 or 2, and preferably phos compounds having the formula where AV is hydroxyphenyl, alkoxycarbonyl-hydroxyphenyl or hydroxydiphenyl and where and n has the stated meaning, and in particular phosphorus compounds with the formula
hvor R^ er metyl eller etyl, n er 1 eller 2 og hvor AJI er 3-metoksykarbonyl-4-hydroksyfenyl eller.3-fenyl-4-hydroksyfenyl. where R 1 is methyl or ethyl, n is 1 or 2 and where A 1 is 3-methoxycarbonyl-4-hydroxyphenyl or .3-phenyl-4-hydroxyphenyl.
R^ og RJJ i formelen (2) er fortrinnsvis alkyl med fra 1-4 karbonatomer. F.eks. er R^ og RJJ hver n-heksyl, n-butyl, tert.butyl, isopropyl, n-propyl og særlig etyl eller metyl. R^ and RJJ in formula (2) are preferably alkyl with from 1 to 4 carbon atoms. E.g. R 1 and RJ 1 are each n-hexyl, n-butyl, tert-butyl, isopropyl, n-propyl and especially ethyl or methyl.
A^ er fenyl eller en fenylrest som eventuelt kan være substituert. F.eks. kan A^. være toluyl, fenyl, 4-hydroksyfenyl, 3-metoksykarbonylfenyl, 3-fenyl-4-hydroksy-fenyl, kresyl, klor-eller bromfenyl, eller særlig 3-metoksykarbonyl-4-hydroksy-fenyl. A^ is phenyl or a phenyl residue which may optionally be substituted. E.g. can A^. be toluyl, phenyl, 4-hydroxyphenyl, 3-methoxycarbonylphenyl, 3-phenyl-4-hydroxy-phenyl, cresyl, chloro- or bromophenyl, or especially 3-methoxycarbonyl-4-hydroxy-phenyl.
X" er fortrinnsvis metylen, men også rester som etylen, X" is preferably methylene, but also residues such as ethylene,
n-propylen eller n-butylen kommer i betraktning.n-propylene or n-butylene comes into consideration.
Forbindelsene med formel (2) er kjent og kan fremstilles på i og for seg kjent måte f.eks. ved at angjeldende benzosyre-ester omsettes med en passende fosfitt. Særlig er de forbindelser som er usubstituert på fenylkjernen. kjent, méns de forbindelser som er substituert på fenylkjernen er nye, men kan fremstilles etter i og for seg kjente fremgangsmåter. The compounds with formula (2) are known and can be prepared in a manner known per se, e.g. in that the relevant benzoic acid ester is reacted with a suitable phosphite. In particular, those compounds are unsubstituted on the phenyl nucleus. known, while the compounds which are substituted on the phenyl nucleus are new, but can be prepared according to methods known per se.
Særlig egnede forbindelser av typen (c) er fosforforbindelser med formelen hvor Z-z er hydroksyl, 2,3-clibrom-n-propoksy, 2-hydroksyetylamino eller metakryletoksy. Particularly suitable compounds of the type (c) are phosphorus compounds of the formula where Z-z is hydroxyl, 2,3-clibromo-n-propoxy, 2-hydroxyethylamino or methacrylethoxy.
Restene R^<1>, RJJ<1>°&^3^an være alkyl eller halogen-The residues R^<1>, RJJ<1>°&^3^can be alkyl or halogen-
alkyl (med fra 1-3 halogenatomer) med fra 1-6, og fortrinns-alkyl (with from 1-3 halogen atoms) with from 1-6, and preferably
vis fra 1-4 karbonatomer, som f.eks. n-heksyl, n-pentyl, tert.-butyl, n-butyl, isopropyl, n-propyl, etyl, metyl, klormetyl, brommetyl, 2-brometyl, 2,2-dibrom-n-propyl, 3-brom-n-propyl, 2,2,3-tribrom-n-propyl, 2-klor-2,3-dibrom-n-propyl etc. Halogen er fortrinnsvis kifcjor og særlig brom. Z^ kan videre også være hydroksyl med fra .1 - 6, fortrinnsvis fra 1-4 karbonatomer f.eks. metylol, hydroksyetyl eller 4-hydroksybutyl. Som alkenyl for Z kommer rester med fra 2-6, og særlig fra 2 -^/karbonatomer i betraktning, såsom allyl eller 2,3-butenyl. Acyloksy-alkylrestene i definisjonen av Z dreier seg om rester av :esibe<p>av mono karbonsyrer med dialkanoler som inneholder hydroksylgrupper hvor syredelen skriver seg fra f.eks. akrylsyre, metakrylsyre, vinyl-eddiksyre, smbrsyre, propionsyre eller eddiksyre, mens alkohol-delen i fbrste rekke skriver seg fra glykoler såsom etylen-, propylen- eller butylenglykol. show from 1-4 carbon atoms, such as e.g. n-hexyl, n-pentyl, tert-butyl, n-butyl, isopropyl, n-propyl, ethyl, methyl, chloromethyl, bromomethyl, 2-bromomethyl, 2,2-dibromo-n-propyl, 3-bromo-n -propyl, 2,2,3-tribromo-n-propyl, 2-chloro-2,3-dibromo-n-propyl etc. Halogen is preferably chlorine and especially bromine. Z^ can furthermore also be hydroxyl with from .1 - 6, preferably from 1-4 carbon atoms, e.g. methylol, hydroxyethyl or 4-hydroxybutyl. As alkenyl for Z, residues with from 2-6, and especially from 2 -^/carbon atoms come into consideration, such as allyl or 2,3-butenyl. The acyloxy-alkyl residues in the definition of Z concern residues of :esibe<p>of mono carboxylic acids with dialkanols containing hydroxyl groups where the acid part is written from e.g. acrylic acid, methacrylic acid, vinyl acetic acid, sambaric acid, propionic acid or acetic acid, while the alcohol part is primarily derived from glycols such as ethylene, propylene or butylene glycol.
Forbindelsene med formel (3) er i og for seg kjentThe compounds with formula (3) are known per se
eller kan fremstilles etter i og for seg kjente fremgangsmåter. or can be produced according to methods known per se.
Forbindelser av typen (d) og (e) som.kan anvendesCompounds of type (d) and (e) which can be used
ifblge oppfinnelsen er halogenerte alifatiske eller aralifatiske eterforbindelser med fortrinnsvis fra 4-12 karbonatomer såsom halogenerte, fortrinnsvis bromsubstituerte fenoksyalkaner eller alkylfenoler, eller bromholdige alifatiske mon©-eller dikarbonsyreestere, alkylkarbamater eller dieterforbindelser såvel som eventuelt C—alkylerte, halogenerte, fortrinnsvis bromerte eller klorerte fenoler eller tiofenoler. according to the invention are halogenated aliphatic or araliphatic ether compounds with preferably from 4-12 carbon atoms such as halogenated, preferably bromine-substituted phenoxyalkanes or alkylphenols, or bromine-containing aliphatic mon©- or dicarboxylic acid esters, alkylcarbamates or diether compounds as well as optionally C-alkylated, halogenated, preferably brominated or chlorinated phenols or thiophenols.
Forbindelser av typen (d) som egner seg er videre halogenforbindelser med formelen Compounds of the type (d) which are suitable are further halogen compounds with the formula
hvor R' er halogenalkyl med 2 eller 3 karbonatomer og fra 1-3 halogenatomer, X-j er -CO-NY-^-, -0C0- eller -0-, Y-^er hydrogen eller metylol, Aq' er n-2,3-dibrompropyl, -NH2, -CH=CH-C00H eller alkylen-0-hilogenalkyl hver med 2 eller 3 karbonatomer i where R' is haloalkyl with 2 or 3 carbon atoms and from 1-3 halogen atoms, X-j is -CO-NY-^-, -OCO- or -0-, Y-^ is hydrogen or methylol, Aq' is n-2, 3-dibromopropyl, -NH2, -CH=CH-C00H or alkylene-0-halogenalkyl each with 2 or 3 carbon atoms in
henholdsvis alkyl- og halogenalkylresten og med fra 1-3 halogenatomer og hvor Aq' kan være hydrogen når A-^ er -CO-NY^- og Y-^er hydrogen. respectively the alkyl and haloalkyl residue and with from 1-3 halogen atoms and where Aq' can be hydrogen when A-^ is -CO-NY^- and Y-^ is hydrogen.
Halogenforbindelser av typen (d) dreier seg særlig om forbindelser med formelen Halogen compounds of the type (d) relate in particular to compounds with the formula
hvor R er halogenalkyl med fra 1-4 karbonatomer, X' er -CO-NY-, -C00-, -0C0- eller -0-, Y er hydrogen eller hydroksyalkyl med fra 1-4 karbonatomer, A' er halogenalkyl med fra 1-4 karbonatomer, -NH2, alkylen-COOH med 3 eller 4 karbonatomer eller -alkylen-0-halogenalkyl hver med fra 1-4 karbonatomer i alkylen- og halogenresten, og fremfor alt forbindelser med formelen where R is haloalkyl with from 1-4 carbon atoms, X' is -CO-NY-, -C00-, -0C0- or -0-, Y is hydrogen or hydroxyalkyl with from 1-4 carbon atoms, A' is haloalkyl with from 1-4 carbon atoms, -NH2, alkylene-COOH with 3 or 4 carbon atoms or -alkylene-0-haloalkyl each with from 1-4 carbon atoms in the alkylene and halogen residue, and above all compounds with the formula
hvor R' er halogenalkyl med 2 eller 3 karbonatomer og 1 - 3 halogenatomer, X£ er -CO-NY^, -0C0- eller -0-, Y-^ er hydrogen eller metylol, A£ er n-2,3-dibrompropyl, -NH2, -CH=CH-C00H eller alkylen-O-halogenalkyl hver med 2 eller 3 karbonatomer i henholdsvis alkylen- og halogenalkylresten og med 1-3 halogenatomer . where R' is haloalkyl with 2 or 3 carbon atoms and 1 - 3 halogen atoms, X£ is -CO-NY^, -OCO- or -0-, Y-^ is hydrogen or methylol, A£ is n-2,3- dibromopropyl, -NH2, -CH=CH-C00H or alkylene-O-haloalkyl each with 2 or 3 carbon atoms in the alkylene and haloalkyl residue respectively and with 1-3 halogen atoms.
Foretrukne halogenforbindelser er også de forbindelser med formelen (4) eller (18) hvor henholdsvis Kq og Aq kan være hydrogen når henholdsvis X og X-^er -CO-NY- og -CO-NY^-, og henholdsvis Y og Y-^er hydrogen og slike forbindelser med formelen (4) hvor Rq og Aq' kan være halogenalkyl eller -alkenyl med fra 3-6 karbonatomer når X er -0-. Preferred halogen compounds are also those compounds with the formula (4) or (18) where respectively Kq and Aq can be hydrogen when respectively X and X-^ are -CO-NY- and -CO-NY^-, and respectively Y and Y- ^ is hydrogen and such compounds with the formula (4) where Rq and Aq' can be haloalkyl or -alkenyl with from 3-6 carbon atoms when X is -0-.
Forbindelsene med formelen (4) er i og for seg kjent eller kan fremstilles etter i og for seg kjente fremgangsmåter. The compounds with the formula (4) are known in and of themselves or can be prepared according to methods known in and of themselves.
Som halogenalkylrester i definisjonen av henholdsvisAs haloalkyl radicals in the definition of respectively
Rq og A^ kommer i forste rekke rester med 2 eller 3 karbonatomer og fra 1-3 halogenatomer såsom klor og særlig brom på tale. Mulige halogenalkylrester er f.eks. klormetyl, brommetyl, 2-brometyl, 2-kloretyl, 1,2-dibrometyl, 2,3-dibrom-n-propyl, 3-brom-n-propyl, 2,2,3-tribrom-n-propyl, 2-klor-2,3-dibrom-n-propyl etc, mens klormetyl og fremfor alt 2-kloretyl, 1,2-dibrometyl og særlig 2,3-dibrom-n-propyl er foretrukket, Hydroksyalkyl i definisjonen av Y og er f.eks. 2-hydroksyetyl og særlig mety J lol.' Aof avledes videre av rester av umettede dikarbon-syrer såsom fumar- eller maleinsyre. -Alkylen-O-halogenalkyl drier seg fortrinnsvis om -metylen-O-halogen-n-propyl, mens halogen "blant annet betyr klor eller særlig brom. Når X er -0-, kan hver av Rq og Aq<1>være halogenalkenyl, fortrinnsvis halogenalkyl med 6, fortrinnsvis 5 karbonatomer og 2 halogenatomer, særlig bromatomer. Rq and A^ come primarily from residues with 2 or 3 carbon atoms and from 1-3 halogen atoms such as chlorine and especially bromine in question. Possible haloalkyl residues are e.g. chloromethyl, bromomethyl, 2-bromomethyl, 2-chloroethyl, 1,2-dibromomethyl, 2,3-dibromo-n-propyl, 3-bromo-n-propyl, 2,2,3-tribromo-n-propyl, 2- chloro-2,3-dibromo-n-propyl etc, while chloromethyl and above all 2-chloroethyl, 1,2-dibromomethyl and especially 2,3-dibromo-n-propyl are preferred, Hydroxyalkyl in the definition of Y and is e.g. e.g. 2-hydroxyethyl and especially methyl J lol.' Aof is further derived from residues of unsaturated dicarboxylic acids such as fumaric or maleic acid. -Alkylene-O-haloalkyl is preferably about -methylene-O-halo-n-propyl, while halogen "among other things means chlorine or especially bromine. When X is -0-, each of Rq and Aq<1> can be haloalkenyl , preferably haloalkyl with 6, preferably 5 carbon atoms and 2 halogen atoms, especially bromine atoms.
Forbindelser av typen (e) som er spesielt egnet har formelen Compounds of type (e) which are particularly suitable have the formula
hvor A^' er brom, hydroksyl, alkoksykarbonyl med 2 eller 3 karbonatomer, bromalkoksy med 2 eller 3 karbonatomer og fra 1-3 brom- eller bromfenyl med 1-5 brom og Xg, X^, XQ, X^pg<X>1Q er hver brom, metyl, hydroksyl eller hydrogen, hvor hoyst én av restene Xg, X^, Xq, X^ og X^q erhydroksyl og minst én av restene er brom og hvor Xg og A^ sammen kan være en rest med formelen where A^' is bromine, hydroxyl, alkoxycarbonyl with 2 or 3 carbon atoms, bromoalkoxy with 2 or 3 carbon atoms and from 1-3 bromo- or bromophenyl with 1-5 bromine and Xg, X^, XQ, X^pg<X> 1Q is each bromine, methyl, hydroxyl or hydrogen, where at most one of the residues Xg, X^, Xq, X^ and X^q is hydroxyl and at least one of the residues is bromine and where Xg and A^ together can be a residue with the formula
-C0-0-C0-; og særlig formelen-C0-0-C0-; and especially the formula
hvor X11?X12>xi3<»><x>i4°S X-^hver er hydrogen, metyl eller brom mens minst tre av restene X-^, X^2, X]_3><x>i4°S X-^er brom. where X11?X12>xi3<»><x>i4°S X-^each is hydrogen, methyl or bromine while at least three of the residues X-^, X^2, X]_3><x>i4°S X- ^ is bromine.
Resten A"' er halogen, f.eks. klor og særlig brom; alkoksykarbonylgrupper er f.eks. karboksylgrupper som er forestret med n-butanol, n-propanol, isopropanol, etanol og fremfor alt metanol; halogenalkoksygrupper er som regel fra mono- til tetrahalogenerte alkoksyrester hvor halogen i forste rekke er klor og fremfor alt brom, det dreier seg f.eks. om klormetyl, brommetyl, 2-kloretyl, 2,3-dibrom-n-propyl, 2, 2,3-trajbrom-n-propyl, 2,2,3,3-tetrabrom-n-propyl-2-klor-2,3-dibrom-n-propylj halogenfenyl er i forste rekke fra mono- til pentahalogenerte, dvs. klorerte eller fremfor alt bromerte fenylrester såsom p-bromfenyl, 2,3,5-tribromfenyl eller pentabromfenyl. The residue A"' is halogen, e.g. chlorine and especially bromine; alkoxycarbonyl groups are e.g. carboxyl groups which are esterified with n-butanol, n-propanol, isopropanol, ethanol and above all methanol; to tetrahalogenated carboxylic acid residues where the halogen is primarily chlorine and above all bromine, these are for example chloromethyl, bromomethyl, 2-chloroethyl, 2,3-dibromo-n-propyl, 2, 2,3-tribromo-n -propyl, 2,2,3,3-tetrabromo-n-propyl-2-chloro-2,3-dibromo-n-propylj halophenyl are primarily from mono- to pentahalogenated, i.e. chlorinated or above all brominated phenyl radicals such as p-bromophenyl, 2,3,5-tribromophenyl or pentabromophenyl.
X-restene i formel (5) betyr som halogen i forste rekke klor og særlig brom, som alkyl kommer i feiste rekke rester som n-butyl, n-propyl, isopropyl, etyl og særlig metyl på tale. Fortrinnsvis står minst tre X-rester for halogen. The X-residues in formula (5) mean, as halogen, primarily chlorine and especially bromine, as alkyl, residues such as n-butyl, n-propyl, isopropyl, ethyl and especially methyl are mentioned. Preferably, at least three X residues represent halogen.
Forbindelser med formel (5) er kjent, og blir fremstilt på i og for seg kjent måte. Compounds with formula (5) are known, and are prepared in a manner known per se.
Typiske representanter for forbindelser som er egnetTypical representatives of compounds that are suitable
til fremgangsmåten ifblge oppfinnelsen er de folgende:to the method according to the invention are the following:
Blant disse forbindelsene er forbindelsene med formlene (23.1) og særlig (23.4) foretrukket. Among these compounds, the compounds with the formulas (23.1) and especially (23.4) are preferred.
Av disse er forbindelsene med formlene (24.1), (24.3) og særlig (24.4) foretrukket. Of these, the compounds with the formulas (24.1), (24.3) and especially (24.4) are preferred.
Blant disse er særlig forbindelsene med formlene (25.1), (25.2) og særlig (25.4) foretrukket. Among these, the compounds with the formulas (25.1), (25.2) and especially (25.4) are particularly preferred.
Blant disse er særlig forbindelsene med formlene (26.4), (26.6) csg særlig (26.1) og (26.7) foretrukket. Among these, the compounds with the formulas (26.4), (26.6) csg especially (26.1) and (26.7) are preferred.
Blant disse er forbindelsene med formlene (27.1), (27.2), (27.4), (27.5), (27.7) og særlig (27.6) foretrukket. Among these, the compounds with the formulas (27.1), (27.2), (27.4), (27.5), (27.7) and especially (27.6) are preferred.
Metylendioksyforbindelser som kan Smrendes til fremgangsmåten ifblge oppfinnelsen med formelen (1), hvor R^ er en di-lavere-alkyl-fosfonometylgruppe kan f.eks. fremstilles ved at man omsetter en forbindelse med formelen Methylenedioxy compounds which can be added to the method according to the invention with the formula (1), where R1 is a di-lower-alkyl-phosphonomethyl group can e.g. is produced by reacting a compound with the formula
hvor G-^er en alkenylgruppe med hoyst 6 karbonatomer og hvor G2 where G-^ is an alkenyl group with at most 6 carbon atoms and where G2
er en halogenalkylgruppe med fra 1-6 karbonatomer, fortrinns-is a haloalkyl group with from 1-6 carbon atoms, preferably
vis klormetyl, med en trialkylfosfittforbindelse med fra 1-4 karbonatomer i alkylresten, fortrinnsvis ved temperaturer mellom 100 og 180°C, og eventuelt halogenerer, fortrinnsvis bromerer og/eller hydrerer det tilveiebragte kondensasjonsprodukt. Fremstilling av forbindelser med formel (l) hvor og R?, er halogenalkyl, inntreffer derimot ved halogenering, fortrinnsvis bromer-ing av l-alkenyl-3,4-metylendioksy-6-halogenalkyl-benzenforbindelsen med formel (28).- vis chloromethyl, with a trialkylphosphite compound with from 1-4 carbon atoms in the alkyl residue, preferably at temperatures between 100 and 180°C, and optionally halogenates, preferably brominates and/or hydrates the provided condensation product. Preparation of compounds of formula (1) where and R? is haloalkyl, on the other hand, occurs by halogenation, preferably bromination of the 1-alkenyl-3,4-methylenedioxy-6-haloalkyl-benzene compound of formula (28).-
Fosforforbindelser med formelen (2) som kan anvendes ifolge oppfinnelsen kan f.eks. fremstilles ved at man omsetter en forbindelse med formelen Phosphorus compounds with the formula (2) which can be used according to the invention can e.g. is produced by reacting a compound with the formula
hvor X er alkylen med fra 1-4 karbonatomer, Y er halogen, Z-^ og Z 2 er hver alkoksy med fra 1-4 karbonatomer, alkyl med fra 1 - 4 karbonatomer, alkoksykarbonyl med fra 1-5 karbonatomer, fenyl,. halogen eller en eventuelt acylert hydroksylgruppe med fra 2-5 karbonatomer i acylresten, og hvor m og n er 1 eller 2, med en fosfitt med formelen where X is alkylene with from 1-4 carbon atoms, Y is halogen, Z-^ and Z 2 are each alkoxy with from 1-4 carbon atoms, alkyl with from 1-4 carbon atoms, alkoxycarbonyl with from 1-5 carbon atoms, phenyl,. halogen or an optionally acylated hydroxyl group with from 2-5 carbon atoms in the acyl residue, and where m and n are 1 or 2, with a phosphite of the formula
hvor R-p R2og R^hver er alkyl med fra 1-6 karbonatomer, ved where R-p R2 and R^ are each alkyl with from 1-6 carbon atoms, by
fra 100 - 180°C i en smelte, og anvender et toverdig nikkelhalogenid som katalysator hvis n er 1, og eventuelt deretter hydrolyserer de acylerte hydroksylgrupper i den tilveiebragte fosforforbindelse. from 100 - 180°C in a melt, and use a divalent nickel halide as a catalyst if n is 1, and optionally then hydrolyze the acylated hydroxyl groups in the phosphorus compound provided.
Omsetningen finner fortrinnsvis sted mellom 140 og 190°C, og særlig mellom 170 og 180°C, hvor henholdsvis alkyl-halogenidene R-[_Y, R2Y eller R^Y "blir avspaltet. The reaction preferably takes place between 140 and 190°C, and in particular between 170 and 180°C, where respectively the alkyl halides R-[_Y, R2Y or R^Y are split off.
Det toverdige nikkelhalogenid som anvendes i omsetningen hvis n i formelen (29) er 1, er nikkel (Il)-bromid eller særlig nikkel (II)-klorid,' The divalent nickel halide used in the reaction if n in formula (29) is 1 is nickel (II) bromide or particularly nickel (II) chloride,
Dersom Z-^og/eller Z2i formelen (29) er en acylert hydroksylgruppe, tilveiebringer hreaksjonen acylerte fosforforbindelser . hvis acylerte hydroksylgruppe kan hydrolyseres til en fri hydroksylgruppe. If Z-^ and/or Z2 in the formula (29) is an acylated hydroxyl group, the reaction provides acylated phosphorus compounds. whose acylated hydroxyl group can be hydrolyzed to a free hydroxyl group.
Fortrinnsvis utfores denne hydrolysen i et løsnings-middel eller i en blanding av løsningsmidler hvor den tilveiebragte fosforforbindelse er loselig, under ammoniakalske beting-elser ved kokepunktstemperaturen til det anvendte løsningsmiddel eller losningsmiddelblanding. Preferably, this hydrolysis is carried out in a solvent or in a mixture of solvents in which the phosphorus compound provided is soluble, under ammoniacal conditions at the boiling point temperature of the solvent or solvent mixture used.
Som lbsningsmiddel anvendes f.eks. alkanoler med fra 1-4 karbonatomer, såsom metanol og særlig etanol, og/eller f.eks. alifatisk mettede monoketoner med fra 3-6 karbonatomer, såsom 2-heksanon, metylpropylketon, aceton eller særlig metyletylketon. Særlig egnet er etanol eller blandingen etanol: As a solvent, e.g. alkanols with from 1-4 carbon atoms, such as methanol and especially ethanol, and/or e.g. aliphatically saturated monoketones with from 3-6 carbon atoms, such as 2-hexanone, methyl propyl ketone, acetone or especially methyl ethyl ketone. Ethanol or the ethanol mixture is particularly suitable:
metyletylketon i forholdet 1:1.methyl ethyl ketone in a ratio of 1:1.
Hydrolysen utfores i ammoniakalsk medium hvor hensiktsmessig alifatiske aminer med fra 1-4 karbonatomer, fortrinnsvis di- eller trialkylaminer eller blandinger av disse aminene, særlig dietylamin, anvendes. The hydrolysis is carried out in an ammoniacal medium where suitable aliphatic amines with from 1-4 carbon atoms, preferably di- or trialkylamines or mixtures of these amines, especially diethylamine, are used.
Ved hydrolysen blir de angjeldende alifatiske, mettede During the hydrolysis, they become aliphatic, saturated
monokarbonsyrer med fra 2-5 karbonatomer avspaltet.monocarboxylic acids with from 2-5 carbon atoms split off.
De preparater som anvendes ifblge oppfinnelsen-, kan ved siden av det forbehandlingsmiddel som overfores til fibermaterialet minst inneholde et bindemiddel som er stabilt under 250°C, vann og/eller et organisk løsningsmiddel. The preparations used according to the invention can, in addition to the pre-treatment agent which is transferred to the fiber material, at least contain a binder which is stable below 250°C, water and/or an organic solvent.
Syntetiske, halvsyntetiske og naturlige harpikser såvel som polykondensasjons- og polyaddisjonsprodukter egner seg som bindemidler. Prinsipielt kan alle de bindemidler som anvendes i' lakk- eller trykkfargeindustrien anvendes. Bindemidlet tjener til å holde den forbindelsen som skal overfores fast på det behandlede sted på bærestoffet. Ved overforingstemperaturen åcal det ikke smelte, ikke reagere med seg selv, f .eks. ±>r-nettes, og frigi den forbindelsen som skal overfores. Foretrukne ér slike bindemidler som f.eks. torker raskt i en varm luftstrbm og som danner en fin, fortrinnsvis ikke klebende film på bærestoffet. Som egnede bindemidler som er løselige i vann er alginater, tragant, karubin (som johannisbrodkjernemel), dekstrin, foretret eller forestret planteslim, karboksymetyl-cellulose eller polyakrylamid og som bindemiddel som er lbselig i organiske løsningsmidler celluloseester, såsom nitrocellulose eller celluloseacetat og særlig celluloseeter såsom metyl-, etyl-, propyl-, isopropyl-, benzyl- eller hydroksyetylcellulose, såvel som deres blandinger. Særlig gode resultater gir etylcellulose. Synthetic, semi-synthetic and natural resins as well as polycondensation and polyaddition products are suitable as binders. In principle, all the binders used in the lacquer or printing ink industry can be used. The binder serves to keep the compound to be transferred firmly on the treated site on the support material. At the transition temperature it does not melt, does not react with itself, e.g. ±>r-nets, and release the connection to be transferred. Preferred are binders such as e.g. dries quickly in a hot air stream and which forms a fine, preferably non-sticky film on the carrier material. Suitable binding agents which are soluble in water are alginates, tragacanth, carubin (such as carob seed meal), dextrin, etherified or esterified plant mucilage, carboxymethyl cellulose or polyacrylamide and as binding agents which are soluble in organic solvents cellulose esters, such as nitrocellulose or cellulose acetate and especially cellulose ethers such as methyl, ethyl, propyl, isopropyl, benzyl or hydroxyethyl cellulose, as well as their mixtures. Ethyl cellulose gives particularly good results.
Som organiske løsningsmidler kan anvendes organiske løsningsmidler eller losningmiddelblandinger som er blandbare med vann eller ikke med et kokepunkt ved normaltrykk under 150°C, fortrinnsvis under 120°C. Man anvender fortrinnsvis alifatiske, cykloalifatiske eller aromatiske hydrokarboner såsom toluen, cykloheksan, petroleter; lavere alkanoler såsom metanol, etanol, propanol, isppropanol, estere av alifatiske monokarbonsyrer, såsom eddiksyreetylester eller -propylester; alifatiske ketoner såsom metyletylketon og halogenerte alifatiske' hydrokarboner såsom perkloretylen, trikloretylen, 1,1,1-trikloretan eller 1,1,2-triklor-2,2,1-trifluoretylen. Særlig foretrukne løsningsmidler er lavere alifatiske estere, ketoner eller alkoholer såsom butyl-acetat, aceton, metyletylketon, etanol, isopropanol eller butanol, såvel som deres blandinger, f.eks. en blanding av metyletylketon og etanol i forhol 1:1. Med den sistnevnte fåes spesielt gode resultater. Den ønskede viskositet i trykkpastaene kan deretter tilveiebringes gjennom tilsats av de nevnte bindemidler med et egnet opplosningsmiddel. As organic solvents, organic solvents or solvent mixtures can be used which are miscible with water or not with a boiling point at normal pressure below 150°C, preferably below 120°C. Aliphatic, cycloaliphatic or aromatic hydrocarbons such as toluene, cyclohexane, petroleum ether are preferably used; lower alkanols such as methanol, ethanol, propanol, isopropanol, esters of aliphatic monocarboxylic acids, such as ethyl acetate or -propyl ester; aliphatic ketones such as methyl ethyl ketone and halogenated aliphatic hydrocarbons such as perchlorethylene, trichloroethylene, 1,1,1-trichloroethane or 1,1,2-trichloro-2,2,1-trifluoroethylene. Particularly preferred solvents are lower aliphatic esters, ketones or alcohols such as butyl acetate, acetone, methyl ethyl ketone, ethanol, isopropanol or butanol, as well as their mixtures, e.g. a mixture of methyl ethyl ketone and ethanol in a ratio of 1:1. With the latter, particularly good results are obtained. The desired viscosity in the printing pastes can then be provided through the addition of the aforementioned binders with a suitable solvent.
Vektforholdet mellom de enkelte komponenter til det preparat som skal vanvendes til forbehandlingen, kan være meget forskjellig og ligger f.eks. på de forbindelser som skal overfores til fibermaterialet fra 0,1 - 50 vektprosent, for et eventuelt bindemiddel mellom 0,5 - 30 vektprosent, for vann eller det organiske løsningsmiddel eller losningsmiddelblanding mellom fra 20 - 99,4 vektprosent, "beregnet på grunnlag av preparatets total-vekt. På bærestoffet anbringes fra 1 - 100 g, og fortrinnsvis fra 15 - 40 g/m 2bærestoff av den forbindelse som skal overfores til fibermaterialet. The weight ratio between the individual components of the preparation to be used for pre-treatment can be very different and is, for example, on the compounds to be transferred to the fiber material from 0.1 - 50 percent by weight, for any binding agent between 0.5 - 30 percent by weight, for water or the organic solvent or solvent mixture between from 20 - 99.4 percent by weight, "calculated on the basis of total weight of the preparation From 1 - 100 g, and preferably from 15 - 40 g/m 2 carrier of the compound to be transferred to the fiber material, is placed on the carrier material.
Preparatene ifolge oppfinnelsen fremstilles ved at man opplbser eller findispergerer den forbindelse som ved'atmosfærisk trykk og over 80°C overfores på fibermaterialet i vann- og/ eller et organisk opplosningsmiddel, fortrinnsvis i nærvær av The preparations according to the invention are produced by dissolving or finely dispersing the compound which, at atmospheric pressure and above 80°C, is transferred to the fiber material in water and/or an organic solvent, preferably in the presence of
. et bindemiddel som er stabilt under 250°C.. a binder which is stable below 250°C.
Videre er det også mulig å påfore forbindelser med formel (l) direkte som sådanne, dvs. uten opplosningsmiddel eller bindemiddel på bærestoffet, f.eks. ved påstroing, påhelling eller påsproyting. Furthermore, it is also possible to apply compounds of formula (1) directly as such, i.e. without solvent or binder to the carrier, e.g. by sprinkling, pouring or sprinkling.
Kjemikalieoverfbringen gjennomfores stedvis idet man f.eks. påtrykker kjemikaliene mbnsterformig på en stoffbredde eller man anvender utskårne monstere av hjelpestoffet istedenfor en sammenhengende stoffbredde og anbringer disse på fibermaterialet. Man får disse monstere ved å stanse eller skjære ut passende stykker av bærestoffet. På denne måte kan man samtidig eller i rekkefolge behandle begge sidene av tekstilstoffet på lik eller forskjellig måte. The chemical transfer is carried out locally, e.g. the chemicals are printed in a pattern on a width of fabric or you use cut-out patterns of the auxiliary material instead of a continuous width of fabric and place these on the fiber material. You get these monsters by punching or cutting out suitable pieces from the carrier material. In this way, both sides of the textile can be treated simultaneously or in sequence in the same or different way.
En annen utforing ifolge den foreliggende oppfinnelse for å tilveiebringe sjatterte monstere består i at man delvis blokkerer fibermaterialet for overfbringstrykkingen med et blokkeringmiddel på grunnlag av fiberreaktive, sulfonsyregruppe-holdige halogenaminotriazin-forbindelser såsom kondensasjonspro-duktet av cyanurklorid og p-sulfoanilin eller med stivelse eller en polyvinylalkoholfortykker og deretter bringer det i berbring med det behandlede bærestoff. Another embodiment according to the present invention for providing shaded monsters consists in partially blocking the fiber material for the transfer printing with a blocking agent based on fiber-reactive, sulfonic acid group-containing haloaminotriazine compounds such as the condensation product of cyanuric chloride and p-sulfoaniline or with starch or a polyvinyl alcohol thickens and then brings it into contact with the treated carrier.
Etter at preparatet er påfbrt bærestoffet, blir dette tbrket, f.eks. ved hjelp av en varm luftstrbm eller infrarbd bestråling eller eventuelt under gjenvinning av det anvendte l;®s7ningsmiddel. After the preparation has been applied to the carrier, this is used, e.g. by means of a hot air stream or infrared irradiation or possibly during recovery of the solvent used.
Derved blir den behandlede side av bærestoffet buagtThereby, the treated side of the carrier material is curved
i nær kontakt med den overflate av fibermaterialet som skal farges og sammen underkastes disse en varmebehandling på minst 80°C og fortrinnsvis mellom 150 og 200°C. in close contact with the surface of the fiber material to be dyed and together these are subjected to a heat treatment of at least 80°C and preferably between 150 and 200°C.
Disse temperaturene holdes så lenge, fortrinnsvis fraThese temperatures are maintained for a long time, preferably from
5 - 120 sekunder, at det definisjonsmessige tekstilbehandlingsmiddel overfores til det fibermateriale som skal farges. 5 - 120 seconds, that the definitional textile treatment agent is transferred to the fiber material to be dyed.
Temperatur, og tidsforandringer kan ved den sammeTemperature, and time changes can at the same
, kjemikaliesammensetning gi forskjellige sjatteringer. Det er derfor mulig ved hjelp av temperatur- og overføringstiden å styre overgangen av kjemikaliene til fibermaterialet og derved tilveiebringe differensiert farging av de behandlede steder. , chemical composition give different shades. It is therefore possible by means of the temperature and transfer time to control the transition of the chemicals to the fiber material and thereby provide differentiated coloring of the treated areas.
Varmepåvirkningen kan skje på forskjellige i og forThe heat effect can occur on different i and for
seg kjente måter, f.eks. ved hjelp av en varmeplate eller ved passering gjennom en tunnelformet varmesone, en varmetrommel, fortrinnsvis i nærvær av en oppvarmet eller uoppvarmet trykkbe-lastet valse eller en varm kalander eller også ved hjelp av en oppvarmet plate,(et strykejern eller en varmpresse) eventuelt under vakuum, som er oppvarmet til en passende temperatur ved hjelp av damp, olje eller infrarod bestråling eller som eventuelt befinner seg i et varmekammer. Etter at varmebehandlingen er avsluttet, skilles tekstilstoffet fra bærestoffet. known ways, e.g. by means of a heating plate or by passing through a tunnel-shaped heating zone, a heating drum, preferably in the presence of a heated or unheated pressure-loaded roller or a hot calender or also by means of a heated plate, (an iron or a hot press) possibly under vacuum, which is heated to a suitable temperature by means of steam, oil or infrared radiation or which is possibly located in a heating chamber. After the heat treatment has ended, the textile fabric is separated from the carrier fabric.
Som syntetisk fibermateriale som kan behandles ved fremgangsmåten ifolge oppfinnelsen, kan nevnes celluloseester-fibre såsom cellulose-2<1>/2- og triacetatfibre, syntetiske poly-amidfibre, f.eks. fibre av poly-2-kaprolaktam (fiylon 6), poly-aminoundekansyre (Hylon 7) eller særlig av polyheksametylen-diaminadipat (nylon 6,6); polyuretan- eller polyolefin- f.eks. polypropylenfibre av syremodifiserte polyamider såsom polykondensasjonsprodukter av 4,4'-diamino-2,2'-difenyldisulfonsyre eller 4,4'-diamino-2,2'-difenylalkandisulfonsyrer med polyamiddannende utgangsstoffer, polykondensasjonsprodukter av monoaminokarbon-syrer eller deres amiddannende derivater eller tobasiske karbonsyrer og diaminer med aromatiske dikarboksysulfonsyrer, f.eks. polykondensasjonsprodukter av £. -kaprolaktam eller heksametylen-diammoniumdipat med kalium-3,5-dikarboksybenzensulfonat eller syremodifiserte polyesterfibre såsom polykondensasjonsprodukter av aromatiske polykarbonsyrer, f.eks. isoftalsyre eller særlig tereftalsyre, flerverdige alkoholer, f.eks. 1,2- eller 1,3-di-hydroksy-3-(3-natriumsulfopropoksy)-propan, 2,3-dimetylol-l-(3-natriumsulfopropoksy)-butan, 2,2-bis-(3-natriumsulfopropoksyfenyl)-propan eller særlig etylenglykol; eller 3,5-dikarboksybenzensul- fqnsyre eller sulfonert tereftalsyre, sulfonert 4-metoksybenzen-karbonsyre eller sulfonert difenyl-4,4'— dikarbonsyre. As synthetic fiber material that can be treated by the method according to the invention, mention may be made of cellulose ester fibers such as cellulose 2<1>/2 and triacetate fibers, synthetic polyamide fibers, e.g. fibers of poly-2-caprolactam (nylon 6), polyaminoundecanoic acid (Hylon 7) or especially of polyhexamethylene diamine adipate (nylon 6,6); polyurethane or polyolefin, e.g. polypropylene fibers of acid-modified polyamides such as polycondensation products of 4,4'-diamino-2,2'-diphenyldisulfonic acid or 4,4'-diamino-2,2'-diphenylalkanesulfonic acids with polyamide-forming starting materials, polycondensation products of monoaminocarboxylic acids or their amide-forming derivatives or dibasic carboxylic acids and diamines with aromatic dicarboxysulfonic acids, e.g. polycondensation products of £. -caprolactam or hexamethylene diammonium dipate with potassium 3,5-dicarboxybenzenesulfonate or acid-modified polyester fibers such as polycondensation products of aromatic polycarboxylic acids, e.g. isophthalic acid or especially terephthalic acid, polyhydric alcohols, e.g. 1,2- or 1,3-di-hydroxy-3-(3-sodium sulfopropoxy)-propane, 2,3-dimethylol-1-(3-sodium sulfopropoxy)-butane, 2,2-bis-(3-sodium sulfopropoxyphenyl) -propane or especially ethylene glycol; or 3,5-dicarboxybenzenesulfonic acid or sulfonated terephthalic acid, sulfonated 4-methoxybenzenecarboxylic acid or sulfonated diphenyl-4,4'-dicarboxylic acid.
Det dreier seg imidlertid fortrinnsvis om fibermateriale av polyakrylnitril eller akrylnitrilblandingspolymere, fremfor alt polyheksametylen-diaminadipat. (nylon 6,6) og særlig rette polyesterfibre særlig av polyetylenglykoltereftalat eller poly-(l,4-cykloheksandimetylol)-tereftalat. Dersom det dreier seg om akrylnitrilblandingspolymere, utgjor akrylnitrilandelen hensiktsmessig minst 50% og fortrinnsvis minst 85 vektprosent av blandpolymeren. Som komonomere anvender man vanligvis andre vinylforbindelser f.eks. vinylidenklorid, vinylidencyanid, vinyl-klorid, metakrylat, metylvinylpyridin, N-vinylpyrrolidon, vinyl-acetat, vinylalkohol, akrylamid eller styrensulfonsyrer.: Disse fibermaterialene kan også anvendes i blandings-vev med seg selv eller med andre fibre, f.eks. blandinger av polyakrylnitril/polyester, polyamid/polyester, polyester/viskose og polyester/ull. However, it is preferably fiber material of polyacrylonitrile or acrylonitrile mixture polymers, above all polyhexamethylene diamine adipate. (nylon 6,6) and in particular straight polyester fibers in particular of polyethylene glycol terephthalate or poly-(1,4-cyclohexanedimethylol) terephthalate. If it concerns acrylonitrile mixture polymers, the acrylonitrile proportion suitably constitutes at least 50% and preferably at least 85% by weight of the mixture polymer. Other vinyl compounds are usually used as comonomers, e.g. vinylidene chloride, vinylidene cyanide, vinyl chloride, methacrylate, methylvinylpyridine, N-vinylpyrrolidone, vinyl acetate, vinyl alcohol, acrylamide or styrene sulfonic acids.: These fiber materials can also be used in mixed fabrics with themselves or with other fibers, e.g. mixtures of polyacrylonitrile/polyester, polyamide/polyester, polyester/viscose and polyester/wool.
Fibermaterialet kan foreligge på forskjellige bearbeid-ningstrinn, f.eks. i form av flokk, kamgarn, garn, teksturerte tråder, vevet stoff, strikkevarer, fiberull eller gulvbelegg såsom nålefUttepper, flortepper eller garnhespler. The fiber material can be present at different processing stages, e.g. in the form of flock, worsted yarn, yarn, textured threads, woven fabric, knitwear, fiber wool or floor coverings such as needlepoint rugs, rugs or yarn spools.
De preparater som anvendes ifolge oppfinnelsen, kan-bringes på bærestoffet ved hel eller delvis påsproytning, belegging eller påtrykking. The preparations used according to the invention can be applied to the carrier material by full or partial spraying, coating or pressing.
Bærestoffet kan behandles på begge sider eller eventuelt på baksiden og man kan anvende forskjellige konsentrasjon-er for overforingen på de to sidene. The carrier can be treated on both sides or possibly on the reverse side and different concentrations can be used for the transfer on the two sides.
Fargingen av det fibermateriale som.er forbehandlet ifolge oppfinnelsen kan skje ved i og for seg kjente fargemetoder. Som fargestoffer anvendes organiske fargestoffer som ellers anvendes i tekstilfargerier for farging av syntetiske fibermaterialer og særlig av tekstilfibre i vannbad. Irøhengig av det stoff som skal farges dreier det seg om vannloselige anioniske eller kationiske fargestoffer og særlig om dispersjonsfargestoffer. The dyeing of the fiber material which has been pre-treated according to the invention can be done by dyeing methods known per se. As dyes, organic dyes are used which are otherwise used in textile dyeing plants for dyeing synthetic fiber materials and especially textile fibers in a water bath. Depending on the material to be dyed, these are water-soluble anionic or cationic dyes and especially dispersion dyes.
Anioniske fargestoffer dreier seg f.eks. om alkali-eller ammoniumsaltene av de såkalte sure polyamidfargestoffer eller reaktivfargestoffer i azo- og antrakinonrekken. Som azofargestoffer kommer fortrinnsvis metallfrie mono- og diazofarge- stoffer som inneholder en eller to sulfosyregrupper, tungmetall-holdige, særlig krom-, nikkel- eller koboltholdige monoazo, disazo- og formazonfarvestoffer og fremfor alt metalliske azofargestoffer som er bundet to molekyler azofargestoff på et metallatom i betraktning. Som antrakinonfargestoffer kan særlig nevnes sulfonerte 1-amino- eller l-alkylamino-4-aryl-amino-antrakinon og som reaktivfargestoffer kan særlig nevnes sulfon-gruppeholdige azo- og antrakinonfargestoffer som særlig har en akrylami- eller cc-halogenakrylamidgruppe som fiberæfeåtiv gruppe. Som anioniske fargestoffer anvendes fortrinnsvis 1:2 metallkom-plekser som inneholder et tungmetallatom såsom et kromatom og særlig et koboltatom. Til metallatomet er bundet to kompleks-dannende komponenter og av disse er minst en et fargestoffmole-kyl, men fortrinnsvis er begge fargestoffmolekyler. Egnede fargestoffmolekyler er fremfor alt azofargestoffer som i o,o'-stilling til azobroen hver har en substituent som egner seg kompleksdannelse. Derved kan begge de fargestoffmolekyler som deltar i kompleksdannelsen være elike eller forskjellige fra hverandre og ha en eller flere azobroer. Som komp<he.ksdannende sub-stituenter,kjSmmBiis, fgisfcso amino-, karboksy-, karbometoksy- eller metoksygrupper i betraktning og fremfor alt hydroksylgruppen. Særlig egnet er f.eks. fargestoffer med en av de folgende grupper-inger: o,o'-diamino-azo-, o-oksy-o'-amino-azo-, o-karboksy-o'-oksy-azo-, po-karboksy-o'-amino-azo-, o-karbometoksy-o'-oksy-azo-, o-karbometoksy-o'-amino-azo- og særlig o,o'-dioksy-azogrupperingen. Anionic dyes are e.g. about the alkali or ammonium salts of the so-called acidic polyamide dyes or reactive dyes in the azo and anthraquinone series. Azo dyes are preferably metal-free mono- and diazo dyes that contain one or two sulpho acid groups, heavy metal-containing, especially chromium-, nickel- or cobalt-containing monoazo, disazo and formazon dyes and, above all, metallic azo dyes that have two molecules of azo dye attached to a metal atom considering. As anthraquinone dyes, sulfonated 1-amino- or 1-alkylamino-4-aryl-amino-anthraquinone can be mentioned in particular, and as reactive dyes, azo and anthraquinone dyes containing sulfone groups can be mentioned in particular, which in particular have an acrylami- or cc-haloacrylamide group as a fiber-active group. 1:2 metal complexes containing a heavy metal atom such as a chromium atom and especially a cobalt atom are preferably used as anionic dyes. Two complex-forming components are bound to the metal atom and at least one of these is a dye molecule, but preferably both are dye molecules. Suitable dye molecules are above all azo dyes which in the o,o' position of the azo bridge each have a substituent which is suitable for complex formation. Thereby, both of the dye molecules that participate in the complex formation can be the same or different from each other and have one or more azo bridges. As comp<he.x forming substituents, kjSmmBiis, fgisfcso amino, carboxy, carbomethoxy or methoxy groups in consideration and above all the hydroxyl group. Especially suitable are e.g. dyes with one of the following groups: o,o'-diamino-azo-, o-oxy-o'-amino-azo-, o-carboxy-o'-oxy-azo-, po-carboxy-o' -amino-azo-, o-carbomethoxy-o'-oxy-azo-, o-carbomethoxy-o'-amino-azo- and especially the o,o'-dioxy-azo grouping.
Vannloselige, kationiske fargestoffer er særlig anvende-lige salter og metallhalogenid-, f.eks. sinkkloriddobbeltsalter Water-soluble, cationic dyes are particularly useful salts and metal halides, e.g. zinc chloride double salts
av kjente kationiske fargestoffer f.eks. metin-, azometin- og særlig azofargestoffer som inneholder en indolinium-, triazolium-, tetrazolium-, oksadiåzolim-, oksazolium-, pyridinium-, pyrimidi-nium-, pyrazinium-, tiodiazolium- eller fremfor alt tiazolium-ring. Videre kommer også kationiske fargestoffer i difenylmetan-, trifenylmetan-, oksazin- og tiazinrekken på tale såvel som også fargesalter av arylazo- og antrakinonrekken med en ytre oniumgrup-pe, f.eks. en ytre cyklammoniumgruppe eller alkylammoniumgruppe. of known cationic dyes, e.g. methine, azomethine and especially azo dyes containing an indolinium, triazolium, tetrazolium, oxadiazolium, oxazolium, pyridinium, pyrimidinium, pyrazinium, thiodiazolium or above all thiazolium ring. Furthermore, cationic dyes in the diphenylmethane, triphenylmethane, oxazine and thiazine series are also mentioned, as well as dye salts of the arylazo and anthraquinone series with an outer onium group, e.g. an outer cyclammonium group or alkylammonium group.
Foretrukne dispersjonsfargestoffer dreier seg .særlig om azofargestoffer såvel Som fremfor alt om antrakinon-, videre om akridon-, nitro-, metin-, styryl-, azostyryl-, naftoperinon-, kumarin-, kinoftalon- eller naftokinonimin-fargestoffer. Disse fargestoffer som er meget tungt opploselige i vann danner i finmalt tilstand ved hjelp av dispergeringsmidler meget fine vandige suspensjoner. Preferred dispersion dyes relate in particular to azo dyes as well as above all to anthraquinone, further to acridone, nitro, methine, styryl, azostyryl, naphthoperinone, coumarin, quinophthalone or naphthoquinonimine dyes. These dyes, which are very poorly soluble in water, form very fine aqueous suspensions in the finely ground state with the help of dispersants.
Den mengde av hvert fargestoff som anvendes i fargebadene, kan etter bnsket fargedybde varieres innenfor vide grenser. •Vanligvis dreier det seg om mengder på fra 0,1 - 10 og særlig fra 1-4 vektprosent, beregnet på grunnlag av totalt farge-materiale. The amount of each dye used in the dye baths can be varied within wide limits, depending on the desired color depth. •Usually it concerns amounts of from 0.1 - 10 and especially from 1-4 percent by weight, calculated on the basis of total color material.
Fargingen foregår fortrinnsvis i vannbad ved uttrekkingsmetoden, eventuelt under tilsats av ytterligere hjelpemiddel som alt etter fargestoff og stoff som skal farges kan være dispergeringsmidler, emulgeringsmidler, egaliseringsmidler, midler for hurtig fargeopptak, retarderingsmidler osv. Fargingen kan også finne sted i et lukket system, f.eksfg i sirkulasjonsappara-turer såsom krysspole- eller bomfargeapparaturer, haspelkufer, dyse- eller jbrommelmaskiner, padleapparater eller jigger. Derved kan materialet under hele fargeprosessen oppholde seg i et kon-stant volum i Ibs form eller anbringes på mekaniske innretninger. The dyeing takes place preferably in a water bath by the extraction method, possibly with the addition of additional aids which, depending on the dye and the fabric to be dyed, can be dispersants, emulsifiers, leveling agents, agents for rapid color absorption, retarders, etc. The dyeing can also take place in a closed system, e.g. .exfg in circulation apparatus such as cross coil or boom dye apparatus, reel boxes, nozzle or jbrommel machines, paddle apparatus or jigs. Thereby, the material can remain in a constant volume in the form of Ib during the entire dyeing process or be placed on mechanical devices.
Ved fremstilling av fargebadene anvender man hensiktsmessig vandige fargestoffopplbsninger eller fargestoffdispersjon-er og tilforer disse egnede hjelpestoffer. Dersom det er nbdvendig, kan fargestoffene inneholde mineralsyrer såsom svovel-syre eller fortrinnsvis fosforsyre, organiske syrer, fortrinnsvis lavere alifatiske karbonsyrer såsom maursyre, eddiksyre eller oksalsyre og/eller salter såsom ammoniumacetat, ammoniumsulfat eller natriumacetat. Syrene tjener fremfor alt innstilling av pH-verdiene i badene som anvendes ifolge oppfinnelsen,iiregelen fra 2 6 og fortrinnsvis fra 3 - 5.. In the production of the dye baths, aqueous dye solutions or dye dispersions are suitably used and suitable auxiliaries are added to these. If necessary, the dyes may contain mineral acids such as sulfuric acid or preferably phosphoric acid, organic acids, preferably lower aliphatic carboxylic acids such as formic acid, acetic acid or oxalic acid and/or salts such as ammonium acetate, ammonium sulphate or sodium acetate. The acids above all serve to adjust the pH values in the baths used according to the invention, usually from 2 to 6 and preferably from 3 to 5.
Man plaserer det forbehandlede tekstilmateriale i badet som har en temperatur på fra 50 - 70°C og hever deretter eventuelt temperaturen i badet til temperaturområdet fra 75 - 98°C The pre-treated textile material is placed in the bath, which has a temperature of from 50 - 70°C and then optionally raises the temperature in the bath to the temperature range from 75 - 98°C
for å gjennomfbre fargingen. Bådforholdet dreier seg om 1:4 til 1:100 og fortrinnsvis 1:10 til 1:50. Det fargede materiale vaskes og tbrkes. to carry out the dyeing. The boat ratio is about 1:4 to 1:100 and preferably 1:10 to 1:50. The colored material is washed and dried.
Polyesterfibre kan eventuelt også farges ved den såkalte hbytrykksmetoden i lukkede kar under trykk og ved temperaturer på over 100°C, hensiktsmessig mellom 110° og 140°C. Polyester fibers can optionally also be dyed by the so-called high-pressure method in closed vessels under pressure and at temperatures above 100°C, suitably between 110° and 140°C.
Det syntetiske fibermaterialet kan også farges kontinuer-lig, dvs. ved impregnering med et fargehjelpemiddel som velges etter det stoff som skal farges, såsom et fortykket fargebad som inneholder fargeoverforer og syre, hvoretter der skjer en ut-pressing til det ionskede innhold i impregneringsbadet på fra 60 - 120% av fibervekten og endelig en varmebehandling såsom damping ved temperaturer fra 98 - 105°C med en noytra, mettet damp eller termofiksering mellom 180 og 210°C. The synthetic fiber material can also be dyed continuously, i.e. by impregnation with a dye aid selected according to the fabric to be dyed, such as a thickened dye bath containing dye transfer agent and acid, after which the ionized content in the impregnation bath is extruded onto from 60 - 120% of the fiber weight and finally a heat treatment such as steaming at temperatures from 98 - 105°C with a neutral, saturated steam or thermofixation between 180 and 210°C.
Etter fremgangsmåten ifolge oppfinnelsen får man på de forbehandlede steder på fibermaterialet fargesterke, like, strek-frie farginger som er godt gjennomfargede og som i sammenligning med de ubehandlede steder på fibermaterialet utviser et sterkere fargeopptak i forholdet fra 1,1:1 til 30:1, og i de fleste til-feller fra 1,4:1 til 4:1. De storste forskjeller i opptak av According to the method according to the invention, in the pre-treated areas of the fiber material, strong, uniform, streak-free dyeings are obtained which are well dyed through and which, in comparison with the untreated areas of the fiber material, show a stronger color absorption in the ratio from 1.1:1 to 30:1 , and in most cases from 1.4:1 to 4:1. The biggest differences in uptake of
fargestoff får man ved dispersjonsfargestoffer og forbindelsene med formlene (27.7)" fremfor alt (27.4), (27.5) og (27.6) og særlig (24.1), (24.3) og (24.4), og effekten er særlig god på poly-esterstoffer uten at der samtidig anvendes et middel som oker fargehastigheten. Alt etter den type forbehandling som anvendes, eventuelt en kombinasjon av forbehandling ifolge oppfinnelsen med ubehandlet og/eller eventuelt blokkert fibermateriale, tilveiebringes meget virkningsfulle to- eller flertoneeffekter. Fibermaterialet kan forbehandles gjennom overforingstrykking ifolge oppfinnelsen på et tidlig bearbeidingstrinn og deretter bearbeides til den ferdige artikkel og i denne form farges i den onskede fargetone og den ensfarge design, hvorigjennom kost-bart lagerhold av store mengder farget materiale faller bort. F.eks. kan man behandle garn i form av garnhespler ved hjelp av kjemikalier ifolge oppfinnelsen i den onskede design, deretter stj?±kke, veve eller tufte varen og til slutt farge i lange bad. Man kan derved tilveiebringe lysere og morkere farger på den samme vare. dye is obtained from dispersion dyes and the compounds with the formulas (27.7)" above all (27.4), (27.5) and (27.6) and especially (24.1), (24.3) and (24.4), and the effect is particularly good on polyester fabrics without that at the same time an agent that increases the color speed is used. Depending on the type of pretreatment used, possibly a combination of pretreatment according to the invention with untreated and/or possibly blocked fiber material, very effective two- or multi-tone effects are provided. The fiber material can be pretreated through transfer printing according to the invention on an early processing step and then processed into the finished article and in this form dyed in the desired hue and the single-colour design, whereby expensive storage of large quantities of colored material is eliminated. For example, yarn can be processed in the form of yarn spools by with the help of chemicals according to the invention in the desired design, then stretch, weave or tuft the item and finally color in a long a bathroom. You can thereby provide lighter and darker colors on the same product.
Fremgangsmåten ifolge oppfinnelsen gjor det mulig å fremspille skyformede design på tepper såvel som forskjellig fargestyrke i flortoppen og florbunnen som særlig er av stor betydning ved fremstilling av tepper. Man kan på denne måten få tepper som farges okonomisk selv om den fiberdelen som er festet til teppebunnen ér mindre sterkt farget og hver ny farget del kan ha en ny monstereffekt. Det forbehandlede fibermateriale som foreligger i krystallinsk eller amorf form er etter kvantita-tiv fjerning av-den overforte forbindelse med formelen (l) til og med (5) lagringsdyktig i minst 8 uker. The method according to the invention makes it possible to produce cloud-shaped designs on carpets as well as different color strengths in the pile top and the pile bottom, which are of particular importance in the manufacture of carpets. In this way, you can get carpets that are dyed economically, even if the fiber part that is attached to the carpet base is less strongly colored and each new colored part can have a new monster effect. The pre-treated fiber material which is in crystalline or amorphous form is, after quantitative removal of the above compound with the formula (1) to (5) suitable for storage for at least 8 weeks.
I de etterfølgende fremstillingsbeskrivelser og eksempler betyr prosent vektprosent. In the subsequent manufacturing descriptions and examples, percent means percent by weight.
FremstillingsanvisningerManufacturing instructions
A) Forbindelser med formel ( 23. 1)A) Compounds with formula ( 23. 1)
21 g l-allyl-3,4-metylendioksy-6-klormetylbenzen varmes under opproring til 100°C. Ved denne temperatur tilfores 16,6 g trietylfosfitt i dråpeform og temperaturen stiger ytterligere 2°C. Reaksjonsblandingen varmes deretter opp til 160 - 165°C og den hensettes i en time under omrbring. Blandingen avkjbles og produktet destilleres ved Kp0oimmm1^1~-L50°C. Dette gir 25,6 g av forbindelsen med formel (23.1). 21 g of 1-allyl-3,4-methylenedioxy-6-chloromethylbenzene is heated with stirring to 100°C. At this temperature, 16.6 g of triethyl phosphite are added in drop form and the temperature rises a further 2°C. The reaction mixture is then heated to 160 - 165°C and left for one hour with stirring. The mixture is cooled and the product is distilled at Kp0oimmm1^1~-L50°C. This gives 25.6 g of the compound with formula (23.1).
<C>15<H>21<P>5<P><C>15<H>21<P>5<P>
Analyse:Analysis:
B) Forbindelse med formelen ( 23. 2) B) Connection with the formula ( 23. 2)
47,2 g' l-(2',3l<->dibrompropyl)-3,4-metyiendioksy-6-dietylfosfonometylbenzenforbindelse som er fremstilt ifolge anvisning Q) oppvarmes under omrbring til 100°C og ved denne temperaturen tilsettes trietylfosfitt dråpevis. Blandingen oppvarmes deretter til 170°C og omrbres i ytterligere 48 timer. Etter avkjbling tilveiebringes 49,3 g av et produkt med formelen (23.2). 47.2 g of 1-(2',3l<->dibromopropyl)-3,4-methylenedioxy-6-diethylphosphonomethylbenzene compound which is prepared according to instruction Q) is heated with stirring to 100°C and at this temperature triethylphosphite is added dropwise. The mixture is then heated to 170°C and stirred for a further 48 hours. After cooling, 49.3 g of a product with the formula (23.2) is obtained.
ClgH31Br 08P2ClgH 3 1 Br 0 8 P 2
Analyse:Analysis:
C) Forbindelse med formelen ( 23. 3) C) Connection with the formula ( 23. 3)
31,2 g l-allyl-3,4-metylendioksy-6-dietylfosfonometyl-benzen opplbses i 100 ml metylenklorid og avkjbles til -10°C. Ved denne temperatur tilfores dråpevis og langsomt 16 g brom. Deretter oppvarmes reaksjonsblandingen til værelsetemperatur og losningsmidlet fjernes under redusert trykk. Dette gir 45,2 g av et bromfarget, viskost produkt med formel (23.3). 31.2 g of 1-allyl-3,4-methylenedioxy-6-diethylphosphonomethyl-benzene are dissolved in 100 ml of methylene chloride and cooled to -10°C. At this temperature, 16 g of bromine are added dropwise and slowly. The reaction mixture is then heated to room temperature and the solvent is removed under reduced pressure. This gives 45.2 g of a bromine-coloured, viscous product with formula (23.3).
<C>15<H>21°5<P>Br2<C>15<H>21°5<P>Br2
Analyse: Analysis:
D) Forbindelse med formel ( 25»4) D) Compound with formula ( 25»4)
21 g l-allyl-3,4-metylendioksy-6-klormetylbenzen tilfores til metylenklorid som avkjbles med en blanding og koksalt til -10°C. Ved denne temperatur tildryppes langsomt 16 g brom. Reaksjonsblandingen varmes deretter opp til værelsestemperatur. Etter at losningsmidlet er avdampet får man en brun olje som 21 g of 1-allyl-3,4-methylenedioxy-6-chloromethylbenzene are added to methylene chloride which is cooled with a mixture and sodium chloride to -10°C. At this temperature, 16 g of bromine are slowly added dropwise. The reaction mixture is then warmed to room temperature. After the solvent has evaporated, a brown oil is obtained which
stbrkner ved henstand. Dette gir 29.6 g forbindelse med formel (23.4) som etter omkrystallisering fra cykloheksan smelter ved 69 - 70°C. stbrkener with respite. This gives 29.6 g of compound with formula (23.4) which, after recrystallization from cyclohexane, melts at 69 - 70°C.
CllHll°2Br2C1CllHll°2Br2C1
Analyse:Analysis:
E) Forbindelse med formel ( 24. 2) E) Compound with formula ( 24. 2)
23,1 g 5-brom-2-hydroisy-benzosyre-metylester oppvarmes sammen med 0,5 g nikkel(ll)-klorid til 170°C under omrbring. Ved denne temperatur tildryppes 16,6 g trietylfosfitt. Løsning-en farges forst dypt blåfiolett, hvoretter reaksjonen inntrer under heftig skumming og det dannede etylbromid unnviker. Reaksjonen er avsluttet når ikke mer etylbromid unnslipper. Dette tilveiebringer 15,1 g av forbindelsen med formel (24.2), som destillerer ved K 129 - 131°C. 23.1 g of 5-bromo-2-hydroisobenzoic acid methyl ester are heated together with 0.5 g of nickel(II) chloride to 170°C with stirring. At this temperature, 16.6 g of triethyl phosphite are added dropwise. The solution is first colored a deep blue violet, after which the reaction occurs under vigorous foaming and the ethyl bromide formed escapes. The reaction is finished when no more ethyl bromide escapes. This provides 15.1 g of the compound of formula (24.2), which distills at K 129 - 131°C.
v0, 01 mmv0.01 mm
<C>12<H>17°6<P><C>12<H>17°6<P>
Analyse:Analysis:
F. Forbindelse med formel ( 24. 3) F. Connection with formula ( 24. 3)
20,1 g 5-klormetyl-2-hydroksy-benzosyremetylester oppvarmes som en smelte til 100°C og i lbpet av 50 minutter ved denne temperaturen tilsettes langsomt 16,6 g trietylfosfitt. Ved slut-ten av tilsatsen av trietylfosfitt inntrer en eksoterm reaksjon under utvikling av etylkloriddamp som blir dannet under reaksjonen og unnslipper samtidig som man får en temperaturstigning på ca. 10°C. Dannelsen av etylkloriddamper stopper etter at tilsatsen 20.1 g of 5-chloromethyl-2-hydroxybenzoic acid methyl ester is heated as a melt to 100°C and over the course of 50 minutes at this temperature, 16.6 g of triethyl phosphite is slowly added. At the end of the addition of triethyl phosphite, an exothermic reaction occurs with the development of ethyl chloride vapor which is formed during the reaction and escapes at the same time as a temperature rise of approx. 10°C. The formation of ethyl chloride vapors stops after the addition
av trietylfosfitt opphorer. Reaksjonsblandingen oppvarmes deretter til 140°C og holdes en time ved denne temperaturen, hvor-ved den opprinnelig fargelose reaksjonsblandingen farges svakt gul. Dette gir 25,0 g av forbindelsen med formel (24.3). of triethyl phosphite ophorer. The reaction mixture is then heated to 140°C and held for one hour at this temperature, at which point the initially colorless reaction mixture turns slightly yellow. This gives 25.0 g of the compound with formula (24.3).
<C>13<H>19°6<P><C>13<H>19°6<P>
Analyse:Analysis:
G) Forbindelse med formel ( 24. 4) G) Compound with formula ( 24. 4)
50,15 g 5-klormetyl-2-hydroksy-benzosyremetylester oppvarmes til 100°C som en smelte og tilsettes langsomt 31 g trimetylfosfitt som får temperaturen til å stige til 110°C. Etter at tilsatsen av trimetylfosfitt er avsluttet, oppvarmes reaksjonsblandingen til 160°C og holdes ved denne temperaturen i 1 time. Forbindelsene med formel (24.4) destilleres som rå-produkt ved 0,01 Torr og bare den fraksjonssom avdestilleres ved 147°C som en lett uklar olje med refraksjonsindeks n2o°C -'■>5292 blir oppsamlet. 50.15 g of 5-chloromethyl-2-hydroxy-benzoic acid methyl ester is heated to 100°C as a melt and 31 g of trimethylphosphite is added slowly which causes the temperature to rise to 110°C. After the addition of trimethylphosphite is finished, the reaction mixture is heated to 160°C and held at this temperature for 1 hour. The compounds of formula (24.4) are distilled as crude product at 0.01 Torr and only the fraction which is distilled off at 147°C as a slightly cloudy oil with refractive index n20°C -'■>5292 is collected.
<C>11<H>15°6<P><C>11<H>15°6<P>
Analyse:Analysis:
H) Forbindelse med formel ( 24. 5) H) Compound with formula ( 24. 5)
29,1 g 2-acetyl-5-brom-difenyl oppvarmes sammen med 0,5 g nikkel (II)-klorid til 170°C under omroring. Denne sus-pensjonen tilsettes ved 170°C 16,6 g trietylfosfitt i lopet av 1 time. Reaksjonen inntrer under heftig skumming umiddelbart etter at tilsatsen av trietylfosfitt er begynt, og reaksjonsblandingen farges blåfiolett. Trietylfosfitttilgangen reguleres slik at den etylbromid som dannes under reaksjonen avdestilleres umiddelbart. Etter at tilsatsen av trietylfosfitt er avsluttet, holdes reaksjonsblandingen i 30 minutter på 170°C inntil etylbromid ikke mer avdestilleres. 29.1 g of 2-acetyl-5-bromo-diphenyl are heated together with 0.5 g of nickel (II) chloride to 170°C with stirring. 16.6 g of triethylphosphite are added to this suspension at 170°C over the course of 1 hour. The reaction occurs under vigorous foaming immediately after the addition of triethyl phosphite has begun, and the reaction mixture is colored blue-violet. The triethyl phosphite supply is regulated so that the ethyl bromide formed during the reaction is immediately distilled off. After the addition of triethyl phosphite has ended, the reaction mixture is kept for 30 minutes at 170°C until no more ethyl bromide is distilled off.
Råproduktet renses ved vakuumdestillering. Dette gir 21,8 g 2-acetyl-difenyl-5-fosfonsyre-dietylester, som foreligger som et klart, fargelbst, oljeaktig destillat (Kp 122 - 126°C ved 0,08 Torr). The raw product is purified by vacuum distillation. This gives 21.8 g of 2-acetyl-diphenyl-5-phosphonic acid diethyl ester, which is present as a clear, colorless, oily distillate (Kp 122 - 126°C at 0.08 Torr).
Den tilveiebragte 2-acetyl-difenyl-5-fosfonsyredietyl-ester holdes sammen med 7,7 g dietylamin og 4,5 g etanol i 1 time på tilbakelbpstemperatur. Deretter fjernes biproduktene (trietylamin og eddiksyre) fra den mbrkt brune, oljeaktige reaksjonsblanding ved destillasjon ved 0,05 Torr. Det gule, krystallinske deiillasjonsresiduum omkrystalliseres to ganger fra tetraklorkullstoff. Dette gir 12,1 g av forbindelsen med formel (24.5) som hvite, krystallinske nåler, Smeltepunkt 156°C. The obtained 2-acetyl-diphenyl-5-phosphonic acid diethyl ester is kept together with 7.7 g of diethylamine and 4.5 g of ethanol for 1 hour at reflux temperature. The by-products (triethylamine and acetic acid) are then removed from the dark brown, oily reaction mixture by distillation at 0.05 Torr. The yellow, crystalline distillation residue is recrystallized twice from carbon tetrachloride. This gives 12.1 g of the compound of formula (24.5) as white, crystalline needles, melting point 156°C.
<C>16<H>19°4<P>Analyse: <C>16<H>19°4<P>Analysis:
I) Forbindelse med formel ( 24. 6) I) Connection with formula ( 24. 6)
50,0 g 3-etyl-benzylklorid oppvarmes til 120°C og tilsettes i lbpet av 2 timer 53,7 g trietylfosfitt hvoretter gassformet etylklorid feSrni ble dannet under reaksjonen unnviker. Reaksjonsblandingen oppvarmes etter at tilsatsen av trietylfosfitt er avsluttet til tilbakelbpstemperen på 140°C og holdes på tilbakelbp i 15 timer. Råproduktet renses deretter gjennom vakuumdestilla-sjon. Dette .gir 56,2 g av forbindelsen med formel (24.6) som destillat (Kp 120°C ved 0,1 Torr). 50.0 g of 3-ethyl benzyl chloride is heated to 120°C and 53.7 g of triethyl phosphite is added over the course of 2 hours, after which gaseous ethyl chloride was formed during the reaction and the mixture evaporates. The reaction mixture is heated after the addition of triethyl phosphite has been completed to the reflux temperature of 140°C and kept at reflux for 15 hours. The raw product is then purified through vacuum distillation. This gives 56.2 g of the compound of formula (24.6) as distillate (Kp 120°C at 0.1 Torr).
<C>13<H>21°3<P><C>13<H>21°3<P>
Analyse:Analysis:
J) Forbindelse med formel ( 24. 7) J) Connection with formula ( 24. 7)
54 g 3-metoksy-benzylklorid oppvarmes til 120°C og tilsettes i lbpet av 45 minutter 57,3 g trietylfosfitt hvoretter gassformet etylklorid som er dannet under reaksjonen unnviker. Etter at tilsatsen av trietylfosfitt er avsluttet oppvarmes reaksjonsblandingen til 190°C. Fra reaksjonsblandingen fjernes ■ deretter ved 22°C og 0,1 Torr 5 g ikke-reagert trietylfosfitt. Dette gir 76 g av forbindelsen med formel (24.7) som destillasjonsresiduum, som foreligger som en lys gulaktig væske. 54 g of 3-methoxy-benzyl chloride is heated to 120°C and 57.3 g of triethyl phosphite is added over the course of 45 minutes, after which gaseous ethyl chloride formed during the reaction escapes. After the addition of triethyl phosphite has ended, the reaction mixture is heated to 190°C. 5 g of unreacted triethyl phosphite are then removed from the reaction mixture at 22°C and 0.1 Torr. This gives 76 g of the compound of formula (24.7) as distillation residue, which is present as a light yellowish liquid.
<C>12<H>19°4<P><C>12<H>19°4<P>
Analys e:Analysis e:
K) Forbindelse med formel ( 24. 8) K) Connection with formula ( 24. 8)
97,9 g 3-klor-benzylklorid oppvarmes til 120°C og tilsettes ved denne temperaturen i lbpet av 45 minutter 100,1 g 97.9 g of 3-chloro-benzyl chloride is heated to 120°C and added at this temperature over 45 minutes 100.1 g
trietylfosfitt hvoretter gassformet etylklorid som er dannet under reaksjonen unnviker. Reaksjonsblandingen holdes etter at tilsatsen av trietylfosfitt er avsluttet i 15 timer på tilbakelopstempera-turen som vanligvis stiger fra 130°C til 170°C.' Deretter fjernes ikke-reagert trietylfosfitt fra reaksjonsblandingen ved 25 - 50°C og 0,04 Torr. Dette gir 111 g av forbindelsen med formel (24.8) som destillasjonsresiduum som foreligger som en klar væske. triethyl phosphite after which gaseous ethyl chloride formed during the reaction escapes. The reaction mixture is kept after the addition of triethyl phosphite is completed for 15 hours at the reflux temperature which usually rises from 130°C to 170°C. Unreacted triethylphosphite is then removed from the reaction mixture at 25 - 50°C and 0.04 Torr. This gives 111 g of the compound of formula (24.8) as a distillation residue which is present as a clear liquid.
C11H1603C1 P C11H1603C1 P
Analyse:Analysis:
Eksempel 1 Example 1
400 g av en forbindelse med formel (24.2) bearbeides sammen med 100 g etylcellulose i 1000 g av en blanding av 500 g etylalkohol og 500 g metyletylketon i lopet av 1 time under omroring til en pasta. Denne pastaen tilfores en papirstrimmel ved bestrykning eller påtrykking i monstret form på en slik måte at en mengde på 36 g/m blir igjen. På den behandlede papirbærer legges et vevet stoff av polyetylenglykoltereftalat (250 g/m ) hvoretter bæreren og det vevede stoff bringes i kontakt med hverandre mellom oppvarmede metallplater ved 195°C i 25 sekunder. Deretter skilles det forbehandlede vevede stoff og bæreren fra hverandre. 400 g of a compound of formula (24.2) is processed together with 100 g of ethyl cellulose in 1000 g of a mixture of 500 g of ethyl alcohol and 500 g of methyl ethyl ketone over the course of 1 hour while stirring to form a paste. This paste is applied to a paper strip by coating or pressing in the monster shape in such a way that a quantity of 36 g/m remains. A woven fabric of polyethylene glycol terephthalate (250 g/m 2 ) is placed on the treated paper carrier, after which the carrier and the woven fabric are brought into contact with each other between heated metal plates at 195°C for 25 seconds. The pretreated woven fabric and carrier are then separated.
Det torkede, vevede stoff med monster overfores til et fargebad, som i badforholdet 1:30 inneholder 1 g/l av et kondensasjonsprodukt av naftalinsulfon syre og formaldehyd, The dried, woven fabric with sample is transferred to a dye bath, which in the bath ratio 1:30 contains 1 g/l of a condensation product of naphthalene sulfonic acid and formaldehyde,
1 g/l ammoniumsulfat og 2 g/lav en blanding av1 g/l ammonium sulphate and 2 g/low a mixture of
39 deler triklorbenzen og 18 deler difenyl. Temperaturen heves i lopet av 15 minutter fra 20 - 70°C og man behandler godset som skal farges i 15 minutter ved denne temperaturen. Man tilsetter 0,65% av et fargestoff med formelen 39 parts trichlorobenzene and 18 parts diphenyl. The temperature is raised over the course of 15 minutes from 20 - 70°C and the goods to be dyed are treated for 15 minutes at this temperature. 0.65% of a dye is added with the formula
i badet og innstiller pH-verdien med maursyre til 5,5. Badet in the bath and adjust the pH value with formic acid to 5.5. The bathroom
fornyes etter 30 minutter og oppvarmes til 98°C og holdes på denne temperaturen i 60 minutter. Badet avkjoles deretter til 80°C og det fargede stoff spyles og torkes. Dette gir et godt gjennomfarget rodt monster med lik farge, idet man på de forbehandlede steder av polyesterveven får et opptak på 220% fargestyrke sammenlignet med den farging man får på de ikke forbehandlede deler av polyesterveven. renewed after 30 minutes and heated to 98°C and held at this temperature for 60 minutes. The bath is then cooled to 80°C and the dyed fabric is rinsed and dried. This gives a well-dyed red monster with the same colour, as the pre-treated parts of the polyester fabric have an uptake of 220% color strength compared to the coloring you get on the non-pre-treated parts of the polyester fabric.
Dersom man istedenfor fosfatforbindelsen anvender en av de forbindelser som er angitt i den etterfølgende tabell I, som kan overfores ved atmosfærisk trykk over 80°C og ibvrig går frem som beskrevet, tilveiebringes også godt gjennomfargede rode monstere på polyestervever og på de steder av polyesterveven som er forbehandlet, får man, sammenlignet med de ikke behandlede deler på polyesterveven, den prosentuelle okning i fargestyrke som er angitt i den siste kolonnen i tabell I. If, instead of the phosphate compound, one of the compounds indicated in the following table I is used, which can be transferred at atmospheric pressure above 80°C and otherwise proceeds as described, well-dyed red monsters are also provided on polyester fabrics and on the places of the polyester fabric which is pre-treated, when compared to the untreated parts of the polyester fabric, the percentage increase in color strength given in the last column of Table I is obtained.
Eksempel 2 Example 2
Den papirbærer. som er laget ifolge eksempel 1 i monstret form legges på et teppe hvis flor består av 400 - 1000 g/m poly-etylenglykoltereftalfibere. Bærer og teppe oppvarmes deretter i 25 sekunder til 195°C og skilles fra hverandre. Deretter farges teppet som beskrevet i eksempel 1. Teppefloren viser et tyde-lig monster med inorke og lyse fargede, rode områder, som tilsvarer formen på den pålagte, forbehandlede papirbærer. Den storste forskjell mellom lyse og morke steder utgjor ca. 200% i fargestyrke. The paper carrier. which is made according to example 1 in the monster shape is laid on a carpet whose pile consists of 400 - 1000 g/m polyethylene glycol terephthal fibers. Carrier and blanket are then heated for 25 seconds to 195°C and separated. The carpet is then dyed as described in example 1. The carpet pattern shows a clear monster with black and light colored, red areas, which corresponds to the shape of the applied, pre-treated paper carrier. The biggest difference between light and dark places is approx. 200% in color intensity.
Eksempel 3Example 3
Den papirbærer som er tilberedt ifolge eksempel 1 i monstret form, plaseres på florsiden av et teppe som består av 400 - 1000 g/m polyetylenglykoltereftalatfibre. Bærer og teppe oppvarmes deretter i 25 sekunder til 195°C og skilles fra hverandre. Deretter farges i lange bad som beskrevet i eksempel 1. Dette gir dels morkt rode og dels lyst rode fargede flor-topper, som tilsvarer formen på den pålagte, forbehandlede papirbærer og en lys farget teppebunn. Den storste forskjell mellom lyse og morke steder på flortoppene utgjor 200 %. The paper carrier prepared according to example 1 in the monster form is placed on the fleece side of a carpet consisting of 400 - 1000 g/m polyethylene glycol terephthalate fibers. Carrier and blanket are then heated for 25 seconds to 195°C and separated. Then dye in long baths as described in example 1. This gives partly dark red and partly light red colored flor tops, which correspond to the shape of the applied, pre-treated paper carrier and a light colored carpet base. The biggest difference between light and dark places on the flower tops is 200%.
Eksempel 4Example 4
På en aluminiumfolie fordeles i uregelmessig form 30 g/m metylen-bis-di-brompropyleter med formel (26.1). Den belagte aluminiumsfolie oppvarmes ved hjelp av infrarod bestråling til 200°C. De utviklede damper oppsuges i lopet av 30 sekunder gjennom et teppe med fibre av polyetylenglykoltereftalat og som er oppspent over folien. Aluminiumbærer og teppe oppvarmes derved samtidig til 200°C. Deretter farges teppet som beskrevet i eksempel 1. 30 g/m of methylene-bis-dibromopropyl ether with formula (26.1) is distributed irregularly on an aluminum foil. The coated aluminum foil is heated using infrared radiation to 200°C. The developed vapors are absorbed in the course of 30 seconds through a carpet with fibers of polyethylene glycol terephthalate and which is stretched over the foil. The aluminum carrier and blanket are thereby heated simultaneously to 200°C. The carpet is then dyed as described in example 1.
De steder på teppet som kommer i kontakt med metylen-bis-dibrom-propyleterdampen farges morke rode og de steder som ikke er kommet i beroring med dampen, blir farget lyst rode. Herved oppstår skyformede monstere pg den storste forskjellen i fargestyrke mellom de lyse og morke stedene utgjor 250 %. The places on the carpet that come into contact with the methylene-bis-dibromo-propyl ether vapor are colored dark red and the places that have not come into contact with the vapor are colored bright red. This creates cloud-shaped monsters because the largest difference in color intensity between the light and dark areas is 250%.
Eksempel 5Example 5
400 g l-hydroksy-2-metyl-3,4,576-tetrabrombenzen400 g of 1-hydroxy-2-methyl-3,4,576-tetrabromobenzene
(27.7) bearbeides til en pasta som i eksempel 1 og overfores på en papirbærer i monstret form. Strikket stoff av polyamid,6,6 (27.7) is processed into a paste as in example 1 and transferred onto a paper carrier in monster form. Knitted fabric of polyamide, 6,6
på o 160 g/cm 2 legges på den behandlede bærer7 og bærer og vare holdes i kontakt med hverandre i 25 sekunder ved 195°C ved hjelp av en varmeplate. Deretter skilles strikkevaren og bæreren. Deretter overforer man strikkevaren til et fargebad på 60°C, som of o 160 g/cm 2 is placed on the treated carrier7 and the carrier and product are kept in contact with each other for 25 seconds at 195°C using a hot plate. The knitwear and carrier are then separated. The knitwear is then transferred to a dye bath at 60°C, which
i badforholdet 1:40 inneholderin the bath ratio 1:40 contains
1% av et fargestoff med formelen 1% of a dye with the formula
1:2 koboltkompleks 1:2 cobalt complex
2% ammoniumsulfat2% ammonium sulfate
2% av et egaliseringsmiddel på basis av dodecylbenzen-sulfonat. 2% of an equalizing agent based on dodecylbenzene sulfonate.
Deretter oppvarmes badet i 15 minutter til 98°C og man fargerThe bath is then heated for 15 minutes to 98°C and dyed
i 1 time ved denne temperaturen. Etter at badet er avkjolt spyles og torkes det fargede materialet. Dette tilveiebringer en stripefri lys og mbrk farget bordeaufarging og fargestyrken i det morktfargede på de behandlede steder i sammenligning med den lyse farging- på de ubehandlede steder utgjor 300%. for 1 hour at this temperature. After the bath has cooled, the colored material is rinsed and dried. This provides a streak-free light and mbrk colored burgundy coloring and the color strength in the dark colored in the treated areas compared to the light coloring in the untreated areas amounts to 300%.
Eksempel 6Example 6
400 g dibrompropylkarbamat (26.4) bearbeides som i eksempel 1 til en pasta og påfores en papirbærer i monstret form. Vevet stoff av polyakrylnitril. på 130 g/m legges på bæreren og bæreren og tekstilvaren holdes i kontakt med hverandre i 25 sekunder ved 185°C ved hjelp av varmeplater. Deretter skilles det vevede stoff fra bæreren. 400 g of dibromopropyl carbamate (26.4) is processed as in example 1 into a paste and applied to a paper carrier in monster shape. Woven fabric of polyacrylonitrile. of 130 g/m is placed on the carrier and the carrier and the textile are kept in contact with each other for 25 seconds at 185°C using heating plates. The woven fabric is then separated from the carrier.
Deretter anbringes det vevede stoff i et fargebadThe woven fabric is then placed in a dye bath
på 70°C som i badforholdet 1:40 inneholderat 70°C which in the bath ratio 1:40 contains
1% av et fargestoff med formelen1% of a dye with the formula
2% 80%ig eddiksyre 2% 80% acetic acid
10% glaubersalt og10% Glauber salt and
1 g/l av addisjonsproduktet av 1 mol sterol og 35 mol etylenoksyd. 1 g/l of the addition product of 1 mol of sterol and 35 mol of ethylene oxide.
I lopet av 20 minutter oppvarmes fargebadet fra 70 - 98°C ogIn the course of 20 minutes, the dye bath is heated from 70 - 98°C and
man farger 1 time ved denne temperaturen. Deretter avkjolesyou dye for 1 hour at this temperature. Then cool off
badet i lopet av 15 minutter til 70°C og det fargede materialet spyles og torkes. the bath for 15 minutes at 70°C and the colored material is rinsed and dried.
På de steder som er forbehandlet med dibrompropylkarbamat får man morkt gule farginger og på de fkke forbehandlede steder får man lyst gule farginger hvor fargestyrken mellom de morke og lyse stedene utgjor ca. 100%. In the areas that have been pre-treated with dibromopropylcarbamate, dark yellow colorings are obtained and in the lightly pre-treated areas, light yellow colorings are obtained, where the color intensity between the dark and light areas amounts to approx. 100%
Eksempel 7Example 7
50, 100, 200, 400 og 800 g av en forbindelse med formel (2§.4) bearbeides sammen med 100 g etylcellulose i en blanding av etylalkohol og metyletylketon i forholdet 1:1 til en pasta på tilsammen 1500 g. Disse pastaer overfores i monstret form til et papirbånd slik at man får et pastabelegg på 36 g/m . 50, 100, 200, 400 and 800 g of a compound with formula (2§.4) are processed together with 100 g of ethyl cellulose in a mixture of ethyl alcohol and methyl ethyl ketone in a ratio of 1:1 to a paste of a total of 1500 g. These pastes are transferred in monster shape to a paper strip so that a paste coating of 36 g/m is obtained.
De behandlede papirbærere legges ved siden av hverandre på et strikket stoff på 250 g/m 2 av polyetylenglykolter-eftalfibre og bærer og strikket stoff holdes sammen i 25 sekunder ved 195°C. Deretter skilles bærer og strikket stoff og tekstilvaren farges som beskrevet i eksempel 1. The treated paper carriers are placed next to each other on a knitted fabric of 250 g/m 2 of polyethylene glycol terephthalate fibers and the carrier and knitted fabric are held together for 25 seconds at 195°C. The carrier and knitted fabric are then separated and the textile is dyed as described in example 1.
Dette gir rode farginger som på de steder som er forbehandlet med den storste preparatkonsentrasjon utviser et storre opptak av fargestoff. De mbrkeste farginger utviser en forskjell i fargestyrke på 300% sammenlignet med de lyseste farginger. This gives red dyeings which, in the areas that have been pre-treated with the highest preparation concentration, show a greater uptake of dye. The darkest colors show a difference in color strength of 300% compared to the lightest colors.
Eksempel 8Example 8
Man går i dette eksempel frem som i eksempel 7, men . istedenfor å farge etter uttrekkingsmetoden farges etter Foulardier-fremgangsmåten, idet man impregnerer den forbehandlede' tekstil-vare med et impregneringsbad som inneholder 15 g/l av et fargestoff med formelen In this example, you proceed as in example 7, but . instead of dyeing according to the extraction method, dye according to the Foulardier method, impregnating the pre-treated textile item with an impregnation bath containing 15 g/l of a dye with the formula
og 400 g/l alginatfortykker ved 20 .- 30°C. Varen, utpresses til and 400 g/l alginate thickener at 20 - 30°C. The item, is blackmailed to
et opptak som tilsvarer 100% av torr vekt, torkes ved 80°C i 10 minutter og varmebehandles endelig i 40 sekunder ved 195°C. an uptake corresponding to 100% of dry weight is dried at 80°C for 10 minutes and finally heat treated for 40 seconds at 195°C.
Etter behandling med hydrosulfitt får man like, avtrappede blå farginger, hvor de morkeste fargingene viser en forskjell på 40% i fargestyrke i forhold til de lyseste fargingene. After treatment with hydrosulphite, the same, stepped-off blue colorings are obtained, where the darkest colorings show a difference of 40% in color strength compared to the lightest colorings.
Eksempel 9Example 9
Man går frem som i eksempel 5, men blokkerer i monstret form polyamidstrikkevaren for overforingen av tetrabromkresol-forbindelsen (27.7) med et kondensasjonsprodukt fra cyanurklorid og p-sulfoanilin. Dette gir etter fargingen et monster som er avtrappet i tre trinn, hvor de blokkerte stedene er svakt farget, de ubehandlede stedene normalt farget og de dampede stedene er meget dypt farget. Den storste forskjell i fargestyrke mellom de morkt og svakt bordeaufargede stedene er ca. 300%. One proceeds as in example 5, but blocks in the monster form the polyamide knitwear for the transfer of the tetrabromocresol compound (27.7) with a condensation product from cyanuric chloride and p-sulfoaniline. After staining, this gives a monster that has been stepped down in three steps, where the blocked areas are lightly stained, the untreated areas are normally stained and the steamed areas are very deeply stained. The biggest difference in color strength between the dark and slightly burgundy-coloured areas is approx. 300%.
Eksempel 10Example 10
Ved å gå frem som i eksempel 6, men ved å blokkere i monstret form polyakrylnitrilveven for overforingen av dibrom-propylkarbamatforbindelsen med potetstivelse eller en polyvinylalkoholfortykker, tilveiebringes etter fargingen et monster som er avtrappet i tre trinn, hvor de blokkerte stedene er ufarget, de ubehandlede stedene er normalt farget og de dampede stedene er dypt farget. Den storste forskjell i fargestyrke mellom lyst og dypt gulfargede steder er 300%, beregnet på grunnlag av de ikke behandlede og ikke blokkerte steder. By proceeding as in Example 6, but by blocking in the monster form the polyacrylonitrile tissue for the transfer of the dibromo-propylcarbamate compound with potato starch or a polyvinyl alcohol thickener, a monster is provided after the dyeing which is stepped down in three steps, where the blocked sites are undyed, the untreated the spots are normally colored and the steamed spots are deeply colored. The largest difference in color strength between light and deep yellow areas is 300%, calculated on the basis of the untreated and unblocked areas.
Eksempel 11Example 11
400 g av en forbindelse med formel (24.1) bearbeides til en pasta som beskrevet i eksempel 1. En papirstrimmel som er utstanset i monstret form, slik at de utskårne delene utgjor 50% av totaloverflaten, blir belagt med pastaen med forbindelsen med formel (24.1) slik at belegget er 36 g/m . Et vevet stoff av polyetylenglykoltereftalat (250 g/m ) legges på 400 g of a compound of formula (24.1) is processed into a paste as described in example 1. A paper strip that has been punched in the monster shape, so that the cut-out parts make up 50% of the total surface, is coated with the paste of the compound of formula (24.1 ) so that the coating is 36 g/m . A woven fabric of polyethylene glycol terephthalate (250 g/m ) is laid on
den belagte papirbærer hvoretter bæreren og det vevede stoff ut-settes for en varmepåvirkning ved 185°C i lopet av 25 sekunder mellom to oppvarmede metallplater, hvoretter de skilles fra hverandre. Deretter blir det tbrkede monstrede stoff overfort i et fargébad som i badforholdet 1:30 inneholder 1 g/l av et kondensasjonsprodukt av naftalinsulfon-syre og formaldehyd og the coated paper carrier, after which the carrier and the woven fabric are exposed to a heat effect at 185°C for 25 seconds between two heated metal plates, after which they are separated from each other. Then the broken sampled fabric is transferred to a dye bath which, in a bath ratio of 1:30, contains 1 g/l of a condensation product of naphthalene sulfonic acid and formaldehyde and
1 g/l ammoniumsulfat.1 g/l ammonium sulphate.
Fargebadet oppvarmes i lbpet av 15 minutter fra 20 - 70°C hvoretter stoffet som skal farges behandles i 15 minutter ved denne temperatur. The dye bath is heated for 15 minutes from 20 - 70°C, after which the fabric to be dyed is treated for 15 minutes at this temperature.
Badet tilfores deretter 2% av et fargestoff med formelen The bath is then infused with 2% of a dye with the formula
og pH-verdien innstilles på 5,5 med maursyre. Badet oppvarmes i lbpet av 30 minutter til 95°C og stoffet som skal farges behandles i 60 minutter ved denne temperaturen. Dette tilveiebringer godt gjennomfargede, like, skarpe, rode monstere, og forskjellen i fargestyrke mellom de lyse og de morke stedene, and the pH value is adjusted to 5.5 with formic acid. The bath is heated in 30 minutes to 95°C and the fabric to be dyed is treated for 60 minutes at this temperature. This provides well-colored, even, sharp, red monsters, and the difference in color strength between the light and dark areas,
som tilsvarer det utstansede monsteret i papirstrimmelen, utgjor 200%. which corresponds to the punched monster in the paper strip, adds up to 200%.
Dersom'man istedenfor forbindelsen med formel (24.1) anvender de forbindelser som er oppfort i den etterfølgende tabell II og går frem som beskrevet, får man likeledes godt gjennomfargede rode monstere på polyesterveven, hvor de forbehandlede, morke stedene' i monsteret sammenlignet med de ikke-behandlede, lyse stedene i monsteret, utviser en prosentuell bkning i fargestyrke som er angitt i annen spalte i tabell II. If instead of the compound with formula (24.1) you use the compounds listed in the subsequent table II and proceed as described, you also get well-dyed red monsters on the polyester fabric, where the pre-treated, dark places' in the monster compared to those that are not -treated light spots in the sample show a percentage decrease in color strength which is indicated in the second column of Table II.
Eksempel 12 Example 12
Man går frem som i eksempel 11, men tilsetter badet 1, 5% av et fargestoff med formelen Proceed as in example 11, but add 1.5% of a dye with the formula to the bath
så får man et godt gjennomfarget, likt, skarpt, oransje monster, og den storste forskjell i fargestyrke mellom de morke stedene som er forbehandlet med forbindelsen med formel (24.1) og de lyse, ikke forbehandlede stedene, utgjor 1800%. then you get a well-colored, even, sharp, orange monster, and the biggest difference in color strength between the dark areas that have been pretreated with the compound of formula (24.1) and the light, non-pretreated areas, amounts to 1800%.
Dersom man istedenfor forbindelsen med formel (24.1) anvender de forbindelser som er angitt i tabell III og for-øvrig går frem som beskrevet, tilveiebringes likeledes godt gjennomfarge oransje monstere på polyesterveven, hvor de forbehandlede, morkeste stedene i monsteret sammenlignet nrecd de ikke forbehandlede, lyse stedene i monsteret utviser en forskjell i fargestyrke som er angitt i annen spalte i tabell III. If, instead of the compound with formula (24.1), the compounds indicated in table III are used and otherwise proceed as described, good through-colour orange samples are also provided on the polyester fabric, where the pre-treated, darkest places in the sample are compared to those not pre-treated, the light spots in the monster exhibit a difference in color strength which is indicated in the second column of Table III.
Eksempel 15 Example 15
Dersom man går frem som i eksempel 11, men tilsetter badet 1,6% av et fargestoff med formelen If you proceed as in example 11, but add 1.6% of a dye with the formula to the bath
så tilveiebringes godt gjennomfargede, like, skarpe, skarlagenfargede monstere ; hvor den storste forskjell i fargestyrke mellom de morkeddelene som er forbehandlet med forbindelsen med formelen (24.1) og de lyse, ikke forbehandlede stedene, utgjor 1200%. then well-colored, equal, sharp, scarlet-colored monsters are provided; where the biggest difference in color intensity between the mother parts that have been pre-treated with the compound of the formula (24.1) and the light, non-pre-treated areas, amounts to 1200%.
Dersom man istedenfor forbindålsen (24.1) anvenderIf you use the connecting rod (24.1) instead
de forbindelser som er oppfort i tabell IV, og forbvrig går frem som beskrevet, så får man likeledes godt gjennomfargede, skarlagenfargede monstere på polyesterveven, hvor de forbehandlede, morke stedene i monsteret utviser den prosentuelle bkning i fargestyrke som er angitt i annen spalte i tabell IV sammenlignet med de ikke forbehandlede, lyseste stedene i monsteret. the compounds listed in Table IV, and otherwise proceeding as described, one likewise obtains well-dyed, scarlet-colored samples on the polyester fabric, where the pre-treated, dark areas in the sample show the percentage decrease in color strength indicated in the second column of the table IV compared to the non-pretreated, brightest spots in the sample.
Eksempel 14 Example 14
Dersom man går frem som i eksempel 11, men tilsetter badet 3% av et fargestoff med formelen tilveiebringes et godt gjennomfarget, likt, skarpt, fiolett monster, hvor den storste forskjell i fargestyrke mellom de morke stedene som er forbehandlet med forbindelsen med formel (24.1) og de lyse, 'ikke forbehandlede stedene, utgjor 1100%. If you proceed as in example 11, but add to the bath 3% of a dye with the formula, a well-dyed, even, sharp, violet monster is provided, where the biggest difference in color strength between the dark areas that have been pre-treated with the compound with formula (24.1 ) and the bright, 'not pre-treated places, make up 1100%.
Dersom man istedenfor forbindelsen med formel (24.1.) anvender de forbindelser som er oppfort i den etterfølgende tabell V og forøvrig går frem som beskrevet, tilveiebringes likeledes godt gjennomfargede, fi&lette mønsterce på polyesterveven, hvor de forbehandlede, mørkeste stedene i mønsteret utviser en prosentuell økning i fargestyrken som angitt i annen spalte i tabell V sammenlignet med de ikke forbehandlede, lyse stedene i mønsteret. If instead of the compound with formula (24.1.) one uses the compounds listed in the following table V and otherwise proceeds as described, well-dyed, light patterns are also provided on the polyester fabric, where the pre-treated, darkest places in the pattern show a percentage increase in the color strength as indicated in the second column of Table V compared to the non-pretreated light areas of the pattern.
Eksemp- pl 15 Example 15
Dersom man går frem som angitt i eksempel 12, menIf you proceed as indicated in example 12, however
farger strikket stoff av polyamid 6,6 (160 g/m 2 ), tilveiebringes<1>colors knitted fabric of polyamide 6.6 (160 g/m 2 ), provided<1>
likeledes et godt .gjennomfarget, likt, skarpt og oransje monster hvor den storste forskjell i fargestyrke mellom de morke stedene som er forbehandlet med forbindelsen med formel (24.1) og de lyse, ikke forbehandlede stedene, utgjor 30%.. likewise a well-dyed, even, sharp and orange monster where the biggest difference in color strength between the dark areas that have been pre-treated with the compound of formula (24.1) and the light, non-pre-treated areas is 30%.
Dersom man istedenfor forbindelsen med formel (24.1) anvender de forbindelser som er angitt i den etterfølgende tabell VI og går frem som beskrevet, tilveiebringes likeledes godt gjennomfargede, oransje monstere på polyamidstrikkevaren, hvor de forbehandlede, morke stedene i monsteret utviser en prosentuell økning i fargestyrke som er angitt i annen spalte i tabell VI sammenlignet med de ikke forbehandlede lyseste stedene i monsteret. If, instead of the compound of formula (24.1), the compounds indicated in the subsequent table VI are used and the procedure is as described, well-dyed, orange samples are also provided on the polyamide knitwear, where the pre-treated, dark areas in the sample show a percentage increase in color strength which is indicated in the second column of Table VI compared to the non-pretreated brightest spots in the sample.
Eksempel 16 Example 16
Dersom man går frem som angitt i eksempel 15, men tilsetter badet 1,6% av fargestoffet med formelen (102), s^ tilveiebringes likeledes et godt gjennomfarget, likt, skarpt, skarlagens-farget monster, hvor den storste forskjell i fargestyrke mellom de morke stedene som er forbehandlet med forbindelsen med formel (24.1) og de lyse, ikke forbehandlede stedene utgjor 70%. If one proceeds as indicated in example 15, but adds to the bath 1.6% of the dye with the formula (102), s^ is likewise provided with a well-dyed, uniform, sharp, scarlet-colored monster, where the greatest difference in color strength between the the dark areas pretreated with the compound of formula (24.1) and the light, non-pretreated areas make up 70%.
Dersom man istedenfor forbindelsen med formel (24.1) anvender de forbindelser som er oppfort i den etterfølgende tabell VII, og går frem som beskrevet, tilveiebringes likeledes godt gjennomfargede, skarlagensfargede mønstere på polyamidstrikkevaren hvor de forbehandlede, mørkeste stedene i mønsteret utviser en prosentuell økning i fargestyrke som er angitt i annen spalte i tabell VII, ssammenlignet med de ikke forbehandlede, lyse stedene i mønsteret. If, instead of the compound with formula (24.1), the compounds listed in the following table VII are used, and the procedure is as described, well-dyed, scarlet-colored patterns are also provided on the polyamide knitwear, where the pre-treated, darkest areas of the pattern show a percentage increase in color strength which is indicated in the second column of Table VII, compared to the non-pretreated, light spots in the pattern.
Eksempel 17 Example 17
Dersom man går frem som angitt i eksempel 15, men tilsetter badet 3% av et fargestoff med formelen (10$), tilveiebringes et godt gjennomfarget, likt, skarpt fiolett monster, hvor den storste forskjell i far gestyrke mellom de morke stedene som er forbehandlet med forbindelsen med formel (24.1) og de lyse, ikke forbehandlede stedene, utgjor 60%. If one proceeds as indicated in example 15, but adds to the bath 3% of a dye with the formula ($10), a well-dyed, even, sharp violet monster is provided, where the greatest difference in color strength is between the dark areas that have been pre-treated with the compound of formula (24.1) and the light, non-pretreated areas, make up 60%.
Dersom man istedenfor forbindelsen med formel (24.1) anvender forbindelser som er oppfort i den etterfølgende tabell Vin og iovrig går frem som angitt, tilveiebringes likeledes godt gjennomfargede, fiolette monstere på polyamidstrikkevaren, hvor de forbehandlede, morke stedene utviser en prosentuell okning i fargestyrken som er angitt i annen spalte i tabell VIII, sammenlignet med de ikke forbehandlede, lyseste stedene i monsteret. If, instead of the compound with formula (24.1), compounds listed in the subsequent table Vin are used and otherwise proceed as indicated, well-dyed, violet monsters are also provided on the polyamide knitwear, where the pre-treated, dark areas show a percentage increase in the color intensity which is indicated in the second column of Table VIII, compared to the non-pretreated, brightest spots in the sample.
Claims (21)
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
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CH918773A CH571613B5 (en) | 1973-06-22 | 1973-06-22 | |
CH1092373 | 1973-07-26 |
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NO742230L true NO742230L (en) | 1975-01-20 |
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NO742230A NO742230L (en) | 1973-06-22 | 1974-06-19 |
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BE (1) | BE816697A (en) |
BR (1) | BR7405102A (en) |
CA (1) | CA1033510A (en) |
DE (1) | DE2428246A1 (en) |
DK (1) | DK336974A (en) |
ES (1) | ES427502A1 (en) |
FI (1) | FI187774A (en) |
FR (1) | FR2236997B1 (en) |
GB (1) | GB1470113A (en) |
IL (1) | IL45049A0 (en) |
LU (1) | LU70363A1 (en) |
NL (1) | NL7408410A (en) |
NO (1) | NO742230L (en) |
SE (1) | SE7407373L (en) |
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GB2043073B (en) * | 1979-02-13 | 1983-05-11 | Symphar Sa | Mono-and diphosphonate compounds |
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AT285516B (en) * | 1967-08-14 | 1970-10-27 | Glanzstoff Ag | Process for creating multicolored pattern effects on textiles made from synthetic polyamides |
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1974
- 1974-06-05 SE SE7407373A patent/SE7407373L/ not_active Application Discontinuation
- 1974-06-12 DE DE19742428246 patent/DE2428246A1/en active Pending
- 1974-06-17 IL IL45049A patent/IL45049A0/en unknown
- 1974-06-19 FI FI1877/74A patent/FI187774A/fi unknown
- 1974-06-19 NO NO742230A patent/NO742230L/no unknown
- 1974-06-20 GB GB2744074A patent/GB1470113A/en not_active Expired
- 1974-06-20 CA CA202,946A patent/CA1033510A/en not_active Expired
- 1974-06-20 FR FR7421491A patent/FR2236997B1/fr not_active Expired
- 1974-06-20 LU LU70363A patent/LU70363A1/xx unknown
- 1974-06-21 DK DK336974A patent/DK336974A/da unknown
- 1974-06-21 NL NL7408410A patent/NL7408410A/xx unknown
- 1974-06-21 BE BE145739A patent/BE816697A/en unknown
- 1974-06-21 BR BR5102/74A patent/BR7405102A/en unknown
- 1974-06-21 ES ES427502A patent/ES427502A1/en not_active Expired
- 1974-06-22 JP JP49072174A patent/JPS5035483A/ja active Pending
Also Published As
Publication number | Publication date |
---|---|
FI187774A (en) | 1974-12-23 |
DK336974A (en) | 1975-02-10 |
DE2428246A1 (en) | 1975-01-16 |
LU70363A1 (en) | 1976-05-31 |
BE816697A (en) | 1974-12-23 |
FR2236997A1 (en) | 1975-02-07 |
NL7408410A (en) | 1974-12-24 |
FR2236997B1 (en) | 1977-03-11 |
CA1033510A (en) | 1978-06-27 |
SE7407373L (en) | 1974-12-23 |
IL45049A0 (en) | 1974-09-10 |
JPS5035483A (en) | 1975-04-04 |
GB1470113A (en) | 1977-04-14 |
ES427502A1 (en) | 1976-08-01 |
BR7405102A (en) | 1976-02-17 |
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