EP0225281B1 - Combinaison d'agents auxiliaires et son utilisation comme agent d'ennoblissement - Google Patents
Combinaison d'agents auxiliaires et son utilisation comme agent d'ennoblissement Download PDFInfo
- Publication number
- EP0225281B1 EP0225281B1 EP86810500A EP86810500A EP0225281B1 EP 0225281 B1 EP0225281 B1 EP 0225281B1 EP 86810500 A EP86810500 A EP 86810500A EP 86810500 A EP86810500 A EP 86810500A EP 0225281 B1 EP0225281 B1 EP 0225281B1
- Authority
- EP
- European Patent Office
- Prior art keywords
- carbon atoms
- formula
- combination according
- ammonium salt
- lower alkyl
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- 239000003795 chemical substances by application Substances 0.000 title claims description 5
- 238000009988 textile finishing Methods 0.000 title claims description 3
- 239000012752 auxiliary agent Substances 0.000 title 1
- 150000003863 ammonium salts Chemical class 0.000 claims description 53
- 239000000975 dye Substances 0.000 claims description 42
- 210000002268 wool Anatomy 0.000 claims description 35
- 125000004432 carbon atom Chemical group C* 0.000 claims description 31
- 238000000034 method Methods 0.000 claims description 20
- 125000000217 alkyl group Chemical group 0.000 claims description 18
- 150000001450 anions Chemical class 0.000 claims description 15
- 235000014113 dietary fatty acids Nutrition 0.000 claims description 12
- 239000000194 fatty acid Substances 0.000 claims description 12
- 229930195729 fatty acid Natural products 0.000 claims description 12
- 150000004665 fatty acids Chemical class 0.000 claims description 12
- 229910052757 nitrogen Inorganic materials 0.000 claims description 12
- 239000001301 oxygen Substances 0.000 claims description 12
- 229910052760 oxygen Inorganic materials 0.000 claims description 12
- 239000000463 material Substances 0.000 claims description 11
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 10
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 9
- 150000007524 organic acids Chemical class 0.000 claims description 9
- 150000007522 mineralic acids Chemical class 0.000 claims description 8
- 229920002647 polyamide Polymers 0.000 claims description 8
- 239000004952 Polyamide Substances 0.000 claims description 7
- 125000000129 anionic group Chemical group 0.000 claims description 6
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 5
- ZRALSGWEFCBTJO-UHFFFAOYSA-N Guanidine Chemical compound NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 claims description 4
- 125000003277 amino group Chemical group 0.000 claims description 4
- 150000003242 quaternary ammonium salts Chemical class 0.000 claims description 4
- 125000002947 alkylene group Chemical group 0.000 claims description 3
- 150000001767 cationic compounds Chemical class 0.000 claims description 3
- QGBSISYHAICWAH-UHFFFAOYSA-N dicyandiamide Chemical compound NC(N)=NC#N QGBSISYHAICWAH-UHFFFAOYSA-N 0.000 claims description 3
- 125000005843 halogen group Chemical group 0.000 claims description 3
- 239000004215 Carbon black (E152) Substances 0.000 claims description 2
- XZMCDFZZKTWFGF-UHFFFAOYSA-N Cyanamide Chemical compound NC#N XZMCDFZZKTWFGF-UHFFFAOYSA-N 0.000 claims description 2
- CHJJGSNFBQVOTG-UHFFFAOYSA-N N-methyl-guanidine Natural products CNC(N)=N CHJJGSNFBQVOTG-UHFFFAOYSA-N 0.000 claims description 2
- 238000009833 condensation Methods 0.000 claims description 2
- 230000005494 condensation Effects 0.000 claims description 2
- SWSQBOPZIKWTGO-UHFFFAOYSA-N dimethylaminoamidine Natural products CN(C)C(N)=N SWSQBOPZIKWTGO-UHFFFAOYSA-N 0.000 claims description 2
- 239000000835 fiber Substances 0.000 claims description 2
- 229930195733 hydrocarbon Natural products 0.000 claims description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 2
- ZILVNHNSYBNLSZ-UHFFFAOYSA-N 2-(diaminomethylideneamino)guanidine Chemical compound NC(N)=NNC(N)=N ZILVNHNSYBNLSZ-UHFFFAOYSA-N 0.000 claims 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims 1
- 239000005977 Ethylene Substances 0.000 claims 1
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 claims 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 claims 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 37
- 239000000203 mixture Substances 0.000 description 36
- 239000000243 solution Substances 0.000 description 36
- UKMSUNONTOPOIO-UHFFFAOYSA-N Behenic acid Natural products CCCCCCCCCCCCCCCCCCCCCC(O)=O UKMSUNONTOPOIO-UHFFFAOYSA-N 0.000 description 33
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 31
- -1 aliphatic hydrocarbon radicals Chemical class 0.000 description 30
- 230000033228 biological regulation Effects 0.000 description 30
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 28
- 238000004043 dyeing Methods 0.000 description 27
- 150000001412 amines Chemical class 0.000 description 25
- 239000002253 acid Substances 0.000 description 24
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 21
- 238000006243 chemical reaction Methods 0.000 description 18
- 235000021357 Behenic acid Nutrition 0.000 description 15
- 229940116226 behenic acid Drugs 0.000 description 15
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 14
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 13
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 13
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 11
- 239000004593 Epoxy Substances 0.000 description 11
- 229910052804 chromium Inorganic materials 0.000 description 11
- 150000003839 salts Chemical class 0.000 description 11
- 239000004744 fabric Substances 0.000 description 10
- 238000003756 stirring Methods 0.000 description 10
- 125000000542 sulfonic acid group Chemical group 0.000 description 10
- 239000011651 chromium Substances 0.000 description 9
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 8
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 8
- 239000007795 chemical reaction product Substances 0.000 description 8
- 230000002378 acidificating effect Effects 0.000 description 7
- 150000001875 compounds Chemical class 0.000 description 7
- 238000004382 potting Methods 0.000 description 7
- WKSHSACKVQQYHJ-UHFFFAOYSA-N 2-[3-(dimethylamino)propyl]docosanamide Chemical compound CCCCCCCCCCCCCCCCCCCCC(C(N)=O)CCCN(C)C WKSHSACKVQQYHJ-UHFFFAOYSA-N 0.000 description 6
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 6
- 150000007513 acids Chemical class 0.000 description 6
- 229920000768 polyamine Polymers 0.000 description 6
- 238000001816 cooling Methods 0.000 description 5
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 5
- 239000000434 metal complex dye Substances 0.000 description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 5
- 239000003921 oil Substances 0.000 description 5
- 229920001281 polyalkylene Polymers 0.000 description 5
- 229920000151 polyglycol Polymers 0.000 description 5
- 239000010695 polyglycol Substances 0.000 description 5
- 238000002360 preparation method Methods 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- 239000011541 reaction mixture Substances 0.000 description 5
- 235000013162 Cocos nucifera Nutrition 0.000 description 4
- 244000060011 Cocos nucifera Species 0.000 description 4
- OYHQOLUKZRVURQ-HZJYTTRNSA-N Linoleic acid Chemical compound CCCCC\C=C/C\C=C/CCCCCCCC(O)=O OYHQOLUKZRVURQ-HZJYTTRNSA-N 0.000 description 4
- 125000004429 atom Chemical group 0.000 description 4
- 239000002657 fibrous material Substances 0.000 description 4
- NYGZLYXAPMMJTE-UHFFFAOYSA-M metanil yellow Chemical group [Na+].[O-]S(=O)(=O)C1=CC=CC(N=NC=2C=CC(NC=3C=CC=CC=3)=CC=2)=C1 NYGZLYXAPMMJTE-UHFFFAOYSA-M 0.000 description 4
- 229910052938 sodium sulfate Inorganic materials 0.000 description 4
- 235000011152 sodium sulphate Nutrition 0.000 description 4
- 239000003760 tallow Substances 0.000 description 4
- VILCJCGEZXAXTO-UHFFFAOYSA-N 2,2,2-tetramine Chemical compound NCCNCCNCCN VILCJCGEZXAXTO-UHFFFAOYSA-N 0.000 description 3
- SHKUUQIDMUMQQK-UHFFFAOYSA-N 2-[4-(oxiran-2-ylmethoxy)butoxymethyl]oxirane Chemical compound C1OC1COCCCCOCC1CO1 SHKUUQIDMUMQQK-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- GAWIXWVDTYZWAW-UHFFFAOYSA-N C[CH]O Chemical group C[CH]O GAWIXWVDTYZWAW-UHFFFAOYSA-N 0.000 description 3
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 3
- 239000000654 additive Substances 0.000 description 3
- 150000007933 aliphatic carboxylic acids Chemical class 0.000 description 3
- DTOSIQBPPRVQHS-PDBXOOCHSA-N alpha-linolenic acid Chemical compound CC\C=C/C\C=C/C\C=C/CCCCCCCC(O)=O DTOSIQBPPRVQHS-PDBXOOCHSA-N 0.000 description 3
- 235000020661 alpha-linolenic acid Nutrition 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- 239000000987 azo dye Substances 0.000 description 3
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical group [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 3
- 239000008367 deionised water Substances 0.000 description 3
- 229910021641 deionized water Inorganic materials 0.000 description 3
- SWXVUIWOUIDPGS-UHFFFAOYSA-N diacetone alcohol Natural products CC(=O)CC(C)(C)O SWXVUIWOUIDPGS-UHFFFAOYSA-N 0.000 description 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 229910001385 heavy metal Inorganic materials 0.000 description 3
- 235000020778 linoleic acid Nutrition 0.000 description 3
- OYHQOLUKZRVURQ-IXWMQOLASA-N linoleic acid Natural products CCCCC\C=C/C\C=C\CCCCCCCC(O)=O OYHQOLUKZRVURQ-IXWMQOLASA-N 0.000 description 3
- 229960004488 linolenic acid Drugs 0.000 description 3
- KQQKGWQCNNTQJW-UHFFFAOYSA-N linolenic acid Natural products CC=CCCC=CCC=CCCCCCCCC(O)=O KQQKGWQCNNTQJW-UHFFFAOYSA-N 0.000 description 3
- 150000002763 monocarboxylic acids Chemical class 0.000 description 3
- IPCSVZSSVZVIGE-UHFFFAOYSA-N palmitic acid group Chemical group C(CCCCCCCCCCCCCCC)(=O)O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 description 3
- 150000003254 radicals Chemical class 0.000 description 3
- 239000000985 reactive dye Substances 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 229960001124 trientine Drugs 0.000 description 3
- OBETXYAYXDNJHR-SSDOTTSWSA-M (2r)-2-ethylhexanoate Chemical compound CCCC[C@@H](CC)C([O-])=O OBETXYAYXDNJHR-SSDOTTSWSA-M 0.000 description 2
- ONMOULMPIIOVTQ-UHFFFAOYSA-N 98-47-5 Chemical compound OS(=O)(=O)C1=CC=CC([N+]([O-])=O)=C1 ONMOULMPIIOVTQ-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- ZNSMNVMLTJELDZ-UHFFFAOYSA-N Bis(2-chloroethyl)ether Chemical compound ClCCOCCCl ZNSMNVMLTJELDZ-UHFFFAOYSA-N 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- RPNUMPOLZDHAAY-UHFFFAOYSA-N Diethylenetriamine Chemical compound NCCNCCN RPNUMPOLZDHAAY-UHFFFAOYSA-N 0.000 description 2
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 125000001931 aliphatic group Chemical group 0.000 description 2
- 125000004390 alkyl sulfonyl group Chemical group 0.000 description 2
- BFNBIHQBYMNNAN-UHFFFAOYSA-N ammonium sulfate Chemical compound N.N.OS(O)(=O)=O BFNBIHQBYMNNAN-UHFFFAOYSA-N 0.000 description 2
- 229910052921 ammonium sulfate Inorganic materials 0.000 description 2
- 235000011130 ammonium sulphate Nutrition 0.000 description 2
- YZXBAPSDXZZRGB-DOFZRALJSA-N arachidonic acid Natural products CCCCC\C=C/C\C=C/C\C=C/C\C=C/CCCC(O)=O YZXBAPSDXZZRGB-DOFZRALJSA-N 0.000 description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 2
- 229910017052 cobalt Inorganic materials 0.000 description 2
- 239000010941 cobalt Substances 0.000 description 2
- 238000004040 coloring Methods 0.000 description 2
- 230000009918 complex formation Effects 0.000 description 2
- 239000002270 dispersing agent Substances 0.000 description 2
- 239000000428 dust Substances 0.000 description 2
- 150000002118 epoxides Chemical class 0.000 description 2
- 150000002170 ethers Chemical class 0.000 description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- YWFWDNVOPHGWMX-UHFFFAOYSA-N n,n-dimethyldodecan-1-amine Chemical compound CCCCCCCCCCCCN(C)C YWFWDNVOPHGWMX-UHFFFAOYSA-N 0.000 description 2
- NHLUVTZJQOJKCC-UHFFFAOYSA-N n,n-dimethylhexadecan-1-amine Chemical compound CCCCCCCCCCCCCCCCN(C)C NHLUVTZJQOJKCC-UHFFFAOYSA-N 0.000 description 2
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 2
- 235000005985 organic acids Nutrition 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 239000002798 polar solvent Substances 0.000 description 2
- 239000001632 sodium acetate Substances 0.000 description 2
- 235000017281 sodium acetate Nutrition 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 239000004753 textile Substances 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- 229910052724 xenon Inorganic materials 0.000 description 2
- FHNFHKCVQCLJFQ-UHFFFAOYSA-N xenon atom Chemical compound [Xe] FHNFHKCVQCLJFQ-UHFFFAOYSA-N 0.000 description 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- INZDTEICWPZYJM-UHFFFAOYSA-N 1-(chloromethyl)-4-[4-(chloromethyl)phenyl]benzene Chemical group C1=CC(CCl)=CC=C1C1=CC=C(CCl)C=C1 INZDTEICWPZYJM-UHFFFAOYSA-N 0.000 description 1
- DURPTKYDGMDSBL-UHFFFAOYSA-N 1-butoxybutane Chemical compound CCCCOCCCC DURPTKYDGMDSBL-UHFFFAOYSA-N 0.000 description 1
- SBASXUCJHJRPEV-UHFFFAOYSA-N 2-(2-methoxyethoxy)ethanol Chemical group COCCOCCO SBASXUCJHJRPEV-UHFFFAOYSA-N 0.000 description 1
- ZNVUMROFMGSJRL-UHFFFAOYSA-N 2-(dimethylamino)-2-(2,2-dimethylpropyl)docosanamide Chemical compound CCCCCCCCCCCCCCCCCCCCC(C(N)=O)(N(C)C)CC(C)(C)C ZNVUMROFMGSJRL-UHFFFAOYSA-N 0.000 description 1
- XLNGIEBZLHISNS-UHFFFAOYSA-N 2-(dimethylamino)-2-propyldocosanamide Chemical compound CCCCCCCCCCCCCCCCCCCCC(C(N)=O)(N(C)C)CCC XLNGIEBZLHISNS-UHFFFAOYSA-N 0.000 description 1
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical group COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 1
- HPILSDOMLLYBQF-UHFFFAOYSA-N 2-[1-(oxiran-2-ylmethoxy)butoxymethyl]oxirane Chemical compound C1OC1COC(CCC)OCC1CO1 HPILSDOMLLYBQF-UHFFFAOYSA-N 0.000 description 1
- MBCLLMVHIVXEJG-UHFFFAOYSA-N 2-[2-(diethylamino)ethyl]docosanamide Chemical compound CCCCCCCCCCCCCCCCCCCCC(C(N)=O)CCN(CC)CC MBCLLMVHIVXEJG-UHFFFAOYSA-N 0.000 description 1
- JTRWPQSNDAXIFX-UHFFFAOYSA-N 2-[2-(dimethylamino)ethyl]docosanamide Chemical compound CCCCCCCCCCCCCCCCCCCCC(C(N)=O)CCN(C)C JTRWPQSNDAXIFX-UHFFFAOYSA-N 0.000 description 1
- AKQKVFJCWVGHAB-UHFFFAOYSA-N 2-[3-(dimethylamino)propyl]-2-ethylhexanamide Chemical compound CCCCC(CC)(C(N)=O)CCCN(C)C AKQKVFJCWVGHAB-UHFFFAOYSA-N 0.000 description 1
- CYZLTHZXZYNWKA-UHFFFAOYSA-N 2-[di(propan-2-yl)amino]-2-ethyldocosanamide Chemical compound CCCCCCCCCCCCCCCCCCCCC(CC)(C(N)=O)N(C(C)C)C(C)C CYZLTHZXZYNWKA-UHFFFAOYSA-N 0.000 description 1
- KZMAWJRXKGLWGS-UHFFFAOYSA-N 2-chloro-n-[4-(4-methoxyphenyl)-1,3-thiazol-2-yl]-n-(3-methoxypropyl)acetamide Chemical compound S1C(N(C(=O)CCl)CCCOC)=NC(C=2C=CC(OC)=CC=2)=C1 KZMAWJRXKGLWGS-UHFFFAOYSA-N 0.000 description 1
- 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 1
- FBWSRAOCSJQZJA-UHFFFAOYSA-N 4-iminonaphthalen-1-one Chemical compound C1=CC=C2C(=N)C=CC(=O)C2=C1 FBWSRAOCSJQZJA-UHFFFAOYSA-N 0.000 description 1
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- DPUOLQHDNGRHBS-UHFFFAOYSA-N Brassidinsaeure Natural products CCCCCCCCC=CCCCCCCCCCCCC(O)=O DPUOLQHDNGRHBS-UHFFFAOYSA-N 0.000 description 1
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- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 1
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- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 1
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- CQXMAMUUWHYSIY-UHFFFAOYSA-N Lignoceric acid Natural products CCCCCCCCCCCCCCCCCCCCCCCC(=O)OCCC1=CC=C(O)C=C1 CQXMAMUUWHYSIY-UHFFFAOYSA-N 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- DFPAKSUCGFBDDF-UHFFFAOYSA-N Nicotinamide Chemical group NC(=O)C1=CC=CN=C1 DFPAKSUCGFBDDF-UHFFFAOYSA-N 0.000 description 1
- MUBZPKHOEPUJKR-UHFFFAOYSA-L Oxalate Chemical compound [O-]C(=O)C([O-])=O MUBZPKHOEPUJKR-UHFFFAOYSA-L 0.000 description 1
- 235000021314 Palmitic acid Nutrition 0.000 description 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-N Propionic acid Chemical compound CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 1
- 235000021355 Stearic acid Nutrition 0.000 description 1
- 241001584775 Tunga penetrans Species 0.000 description 1
- 239000001089 [(2R)-oxolan-2-yl]methanol Substances 0.000 description 1
- PDWCVHGVTVOSIE-UHFFFAOYSA-N [nitro(diphenyl)methyl]benzene Chemical compound C=1C=CC=CC=1C(C=1C=CC=CC=1)([N+](=O)[O-])C1=CC=CC=C1 PDWCVHGVTVOSIE-UHFFFAOYSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- LFVVNPBBFUSSHL-UHFFFAOYSA-N alexidine Chemical compound CCCCC(CC)CNC(=N)NC(=N)NCCCCCCNC(=N)NC(=N)NCC(CC)CCCC LFVVNPBBFUSSHL-UHFFFAOYSA-N 0.000 description 1
- 229950010221 alexidine Drugs 0.000 description 1
- 150000001338 aliphatic hydrocarbons Chemical group 0.000 description 1
- 150000001336 alkenes Chemical class 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 150000001346 alkyl aryl ethers Chemical class 0.000 description 1
- OBETXYAYXDNJHR-UHFFFAOYSA-N alpha-ethylcaproic acid Natural products CCCCC(CC)C(O)=O OBETXYAYXDNJHR-UHFFFAOYSA-N 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 229940043376 ammonium acetate Drugs 0.000 description 1
- 235000019257 ammonium acetate Nutrition 0.000 description 1
- 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 1
- 150000004056 anthraquinones Chemical class 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 229940077388 benzenesulfonate Drugs 0.000 description 1
- SRSXLGNVWSONIS-UHFFFAOYSA-M benzenesulfonate Chemical compound [O-]S(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-M 0.000 description 1
- KCXMKQUNVWSEMD-UHFFFAOYSA-N benzyl chloride Chemical compound ClCC1=CC=CC=C1 KCXMKQUNVWSEMD-UHFFFAOYSA-N 0.000 description 1
- 229940073608 benzyl chloride Drugs 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 125000002843 carboxylic acid group Chemical group 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- JOYKCMAPFCSKNO-UHFFFAOYSA-N chloro benzenesulfonate Chemical compound ClOS(=O)(=O)C1=CC=CC=C1 JOYKCMAPFCSKNO-UHFFFAOYSA-N 0.000 description 1
- 150000001844 chromium Chemical class 0.000 description 1
- 150000001845 chromium compounds Chemical class 0.000 description 1
- 238000003776 cleavage reaction Methods 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 150000004696 coordination complex Chemical class 0.000 description 1
- 239000003599 detergent Substances 0.000 description 1
- 150000004985 diamines Chemical class 0.000 description 1
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 1
- GYZLOYUZLJXAJU-UHFFFAOYSA-N diglycidyl ether Chemical compound C1OC1COCC1CO1 GYZLOYUZLJXAJU-UHFFFAOYSA-N 0.000 description 1
- 238000007865 diluting Methods 0.000 description 1
- 238000006471 dimerization reaction Methods 0.000 description 1
- IUNMPGNGSSIWFP-UHFFFAOYSA-N dimethylaminopropylamine Chemical compound CN(C)CCCN IUNMPGNGSSIWFP-UHFFFAOYSA-N 0.000 description 1
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical compound C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- DPUOLQHDNGRHBS-KTKRTIGZSA-N erucic acid Chemical compound CCCCCCCC\C=C/CCCCCCCCCCCC(O)=O DPUOLQHDNGRHBS-KTKRTIGZSA-N 0.000 description 1
- FARYTWBWLZAXNK-WAYWQWQTSA-N ethyl (z)-3-(methylamino)but-2-enoate Chemical compound CCOC(=O)\C=C(\C)NC FARYTWBWLZAXNK-WAYWQWQTSA-N 0.000 description 1
- 239000003925 fat Substances 0.000 description 1
- 235000019197 fats Nutrition 0.000 description 1
- 239000013505 freshwater Substances 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 150000002334 glycols Chemical class 0.000 description 1
- 238000009944 hand knitting Methods 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- VKOBVWXKNCXXDE-UHFFFAOYSA-N icosanoic acid Chemical compound CCCCCCCCCCCCCCCCCCCC(O)=O VKOBVWXKNCXXDE-UHFFFAOYSA-N 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 125000003253 isopropoxy group Chemical group [H]C([H])([H])C([H])(O*)C([H])([H])[H] 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 229940039717 lanolin Drugs 0.000 description 1
- 235000019388 lanolin Nutrition 0.000 description 1
- QDLAGTHXVHQKRE-UHFFFAOYSA-N lichenxanthone Natural products COC1=CC(O)=C2C(=O)C3=C(C)C=C(OC)C=C3OC2=C1 QDLAGTHXVHQKRE-UHFFFAOYSA-N 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- VMGAPWLDMVPYIA-HIDZBRGKSA-N n'-amino-n-iminomethanimidamide Chemical compound N\N=C\N=N VMGAPWLDMVPYIA-HIDZBRGKSA-N 0.000 description 1
- WQEPLUUGTLDZJY-UHFFFAOYSA-N n-Pentadecanoic acid Natural products CCCCCCCCCCCCCCC(O)=O WQEPLUUGTLDZJY-UHFFFAOYSA-N 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 239000004745 nonwoven fabric Substances 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- UKODFQOELJFMII-UHFFFAOYSA-N pentamethyldiethylenetriamine Chemical compound CN(C)CCN(C)CCN(C)C UKODFQOELJFMII-UHFFFAOYSA-N 0.000 description 1
- 125000001918 phosphonic acid ester group Chemical group 0.000 description 1
- ABLZXFCXXLZCGV-UHFFFAOYSA-N phosphonic acid group Chemical group P(O)(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 description 1
- 239000001007 phthalocyanine dye Substances 0.000 description 1
- 229920006122 polyamide resin Polymers 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 230000008092 positive effect Effects 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical class CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 239000011814 protection agent Substances 0.000 description 1
- 150000003856 quaternary ammonium compounds Chemical class 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- BOLDJAUMGUJJKM-LSDHHAIUSA-N renifolin D Natural products CC(=C)[C@@H]1Cc2c(O)c(O)ccc2[C@H]1CC(=O)c3ccc(O)cc3O BOLDJAUMGUJJKM-LSDHHAIUSA-N 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- WBHHMMIMDMUBKC-XLNAKTSKSA-N ricinelaidic acid Chemical compound CCCCCC[C@@H](O)C\C=C\CCCCCCCC(O)=O WBHHMMIMDMUBKC-XLNAKTSKSA-N 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 125000000467 secondary amino group Chemical group [H]N([*:1])[*:2] 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 230000003381 solubilizing effect Effects 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 125000000565 sulfonamide group Chemical group 0.000 description 1
- 125000001174 sulfone group Chemical group 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000001302 tertiary amino group Chemical group 0.000 description 1
- FAGUFWYHJQFNRV-UHFFFAOYSA-N tetraethylenepentamine Chemical compound NCCNCCNCCNCCN FAGUFWYHJQFNRV-UHFFFAOYSA-N 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- BSYVTEYKTMYBMK-UHFFFAOYSA-N tetrahydrofurfuryl alcohol Chemical compound OCC1CCCO1 BSYVTEYKTMYBMK-UHFFFAOYSA-N 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- 235000021122 unsaturated fatty acids Nutrition 0.000 description 1
- 150000004670 unsaturated fatty acids Chemical class 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- DTOSIQBPPRVQHS-UHFFFAOYSA-N α-Linolenic acid Chemical compound CCC=CCC=CCC=CCCCCCCCC(O)=O DTOSIQBPPRVQHS-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- 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
- D06M13/322—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 nitrogen
- D06M13/402—Amides imides, sulfamic acids
- D06M13/405—Acylated polyalkylene polyamines
-
- 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
- D06M13/322—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 nitrogen
- D06M13/325—Amines
- D06M13/332—Di- or polyamines
-
- 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
- D06M13/322—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 nitrogen
- D06M13/46—Compounds containing quaternary nitrogen atoms
- D06M13/467—Compounds containing quaternary nitrogen atoms derived from polyamines
-
- 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
- D06P1/52—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 using compositions containing synthetic macromolecular substances
- D06P1/5264—Macromolecular compounds obtained otherwise than by reactions involving only unsaturated carbon-to-carbon bonds
- D06P1/5278—Polyamides; Polyimides; Polylactames; Polyalkyleneimines
-
- 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
- D06P1/655—Compounds containing ammonium groups
- D06P1/66—Compounds containing ammonium groups containing quaternary ammonium groups
-
- 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
- D06P5/00—Other features in dyeing or printing textiles, or dyeing leather, furs, or solid macromolecular substances in any form
- D06P5/02—After-treatment
- D06P5/04—After-treatment with organic compounds
- D06P5/06—After-treatment with organic compounds containing nitrogen
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S8/00—Bleaching and dyeing; fluid treatment and chemical modification of textiles and fibers
- Y10S8/916—Natural fiber dyeing
- Y10S8/917—Wool or silk
Definitions
- the present invention relates to a new combination of auxiliaries and their use as textile finishing agents, in particular in post-treatment processes for wool dyeings.
- DE-B 1 281 998 discloses diquaternary ammonium salts with preferably two higher molecular weight aliphatic hydrocarbon radicals, which together with nonionic dispersants, such as e.g. Polyglycol ethers of higher fatty acid amides can be used in dyeing nitrogen-containing fibers.
- auxiliary combination of cationic compounds with such diquaternary ammonium salts has been found, which is distinguished from the previously known agents for improving the fastness properties, especially wet and rub fastness properties of wool dyeings, in that it not only improves the fastness properties, but is also capable of to suppress the soiling tendency of the textile material, which, for example caused by dust (dry soiling) or by re-lifting dirt detached from washing or solvent baths in the laundry (wet soiling). Thanks to the additional softening properties, the new combination also gives the textile material a soft, fluffy feel and thus conveys pleasant wearing properties.
- Components (1) and (2) can be present as individual compounds or as mixtures with one another.
- Lower alkyl and lower alkoxy in the definition of the radicals in formula (1) and in the formulas below represent those groups or group components which have 1 to 5, in particular 1 to 3, carbon atoms, such as, for example, Methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, tert-butyl or amyl or methoxy, ethoxy or isopropoxy.
- the aliphatic radicals R 1 and R 2 can be straight-chain or branched. Together with the CO group, they advantageously represent the acid residue of an unsaturated or preferably saturated aliphatic carboxylic acid having 8 to 24 carbon atoms.
- aliphatic carboxylic acids are 2-ethylhexanoic acid, capric, lauric, coconut fatty, myristic and palm kernel fatty acids, Called palmitic, tallow fatty, oil, ricinoleic, linoleic, linolenic, stearic, arachic, arachidonic, behenic, erucic or lignoceric acid.
- Behenic acid is the preferred acid. Mixtures of these acids can also be used, such as those obtained from the cleavage of natural oils or fats.
- Coconut fatty acid, palm kernel fatty acid, palmitic / stearic acid mixtures, tallow fatty acid and especially arachinic / behenic acid mixtures are particularly preferred mixtures.
- R i and R 2 each preferably represent an alkyl radical having 7 to 23 carbon atoms and in particular having 19 to 21 carbon atoms.
- the lower radicals R 3 to R 6 are preferably identical and are in particular methyl, ethyl, isopropyl or hydroxyethyl. Methyl is particularly preferred.
- X 1 and X 2 are preferably -HN-.
- Z 1 and Z 2 represent in particular an alkylene group which contains 2 to 5 carbon atoms and can be straight-chain or branched. These are, for example, the -CH 2 -CH 2 -, -CH 2 CH 2 CH 2 - -CH 2 -CH 2 and especially -CH 2 CH 2 CH 2 - are particularly preferred.
- the aliphatic hydrocarbon chain in the bridge member Q preferably has 3 to 10 carbon atoms. It can be straight or branched.
- Q is preferably an alkylene radical with 3 to 10 carbon atoms which is optionally interrupted in the chain by oxygen and optionally substituted by hydroxyl groups.
- Anions Y e include both anions of inorganic acids, such as, for example, the chloride, bromide, fluoride, iodide or sulfate ion, and also anions of organic acids, for example aromatic or aliphatic sulfonic acids, such as, for example, benzenesulfonate, p-toluenesulfonate, Chlorobenzenesulfonate, methane or ethanesulfonate ion, furthermore the anions of lower carboxylic acids, such as acetate, propionate or oxalate ion.
- inorganic acids such as, for example, the chloride, bromide, fluoride, iodide or sulfate ion
- organic acids for example aromatic or aliphatic sulfonic acids, such as, for example, benzenesulfonate, p-toluenesulfonate, Chlorobenzen
- Y e is primarily the chloride, bromide, sulfate or p-toluenesulfonate ion.
- the diquaternary ammonium salts of the formula (I) are prepared in a manner known per se.
- the preparation can preferably be carried out by adding 1 mol of a compound of the formulas
- a Q-introducing compound having two functional groups such as, for example, epihalohydrin, dihaloalkanes, dihaloalkyl ethers, olefin dioxides, diepoxy compounds, such as a, ro-alkanediol diglycidyl ether or alkanediol alkyl or aryl sulphonates.
- the reaction is preferably carried out in a polar solvent and, if necessary, with the addition of a hydrohalic acid, e.g. Hydrochloric acid or sulfuric acid.
- a hydrohalic acid e.g. Hydrochloric acid or sulfuric acid.
- Suitable polar solvents are water or preferably water-miscible organic solvents.
- water-miscible organic solvents are aliphatic C 1 -C s alcohols, such as methanol, ethanol or the propanols; Alkylene glycols, such as ethylene glycol or propylene glycol; Monoalkyl ethers of glycols, such as, for example, ethylene glycol monomethyl, ethyl or butyl ether and diethylene glycol monomethyl or ethyl ether; Ketones such as acetone and diacetone alcohol; Ethers, such as diisopropyl ether, diphenyl oxide, dioxane, tetrahydrofuran, and also tetrahydrofurfuryl alcohol, acetonitrile, y-butyrolactone, N, N-dimethylformamide. Mixtures of the solvents mentioned can also be used.
- quaternary ammonium salts (A) for component (2) there can be reaction products of aliphatic or araliphatic mono- and / or diamines, which contain tertiary amino groups and a lipophi len rest, can be used with epihalohydrin.
- reaction products of aliphatic or araliphatic mono- and / or diamines which contain tertiary amino groups and a lipophi len rest, can be used with epihalohydrin.
- Such compounds are described, for example, in DE-AS 1 092 878 or DE-PS 1 921 827.
- a suitable polymeric ammonium salt (B) in component (2) is advantageously a water-soluble reaction product of a peralkylated di- or triamine with a dihaloalkane, dihalodimethyldiphenyl, dihaloalkyl ether or preferably an epihalohydrin.
- Such polymeric quaternary ammonium salts are e.g. described in DE-OS 26 57 582 and 28 24 743.
- a particularly preferred polymeric ammonium salt for component (2) is that it is the repeating unit of the formula wherein or and si are 3 to 30 and Y 3 9 has the meaning given.
- condensates containing amino groups which have been prepared by reacting dicyandiamide, cyanamide, guanidine or bisguanidine and polyalkylene amines with at least three primary and / or secondary amino groups, can be used, the condensates can be implemented even further with an epihalohydrin.
- polycondensates (C) and the corresponding starting materials are known from DE-AS 1 595 390 and can be prepared by the process described there.
- suitable nitrogen-containing polycondensates are basic polyamides which are obtained by condensation of polymeric, preferably di- to trimer-unsaturated fatty acids and polyalkylene polyamines having at least 3 amino groups and 4 to 12 carbon atoms, expediently in such a ratio that the resulting polyamide resin has an amine value in the range of 200 has up to 650 mg of potassium hydroxide per gram of polyamide polyamine.
- polyamide polyamines are described for example in GB-PS 1 276 461 or DE-OS 2 000 204.
- the polymerized unsaturated fatty acids required here are preferably di- to trimerized fatty acids which are derived from monocarboxylic acids having 12 to 24, preferably 16 to 22 and in particular 16 to 18 carbon atoms. These monocarboxylic acids have at least one, preferably 2 to 5, ethylenically unsaturated groups. Representatives of this class of acids are e.g.
- Laurolein myristolein, palmitolein, physet oil, oil, elaidin, petroselin, eikosen, cetolein, gadolein, eruca, eläostoarin, parinar, arachidone, clupanodone, nisine and especially linole and linolenic acid.
- These fatty acids can be obtained from natural oils of vegetable or animal origin.
- di- to trimerized fatty acids are obtained in a known manner by dimerization of monocarboxylic acids of the type specified.
- the polymerized fatty acids are technical mixtures which always have a content of trimerized and a small content of monomeric acids.
- the di- to trimerized linoleic or linolenic acid is particularly suitable.
- the technical mixtures of these acids generally contain 75 to 95 percent by weight of dimerized acid, 4 to 25 percent by weight of trimerized acid and a trace to 3 percent by weight of monomeric acid.
- the molar ratio of dimerized to trimerized acid is accordingly about 5: 1 to 36: 1.
- Amines of the formula are suitable as polyalkylene polyamines wherein ni is 1 to 5, preferably 1, 2 or 3, ie diethylene triamine, triethylene tetramine or tetraethylene pentamine, triethylene tetramine being of particular importance.
- a polyalkylene polyaminopolyamide of di- to trimerized linoleic or linolenic acid and triethylene tetramine is preferably used.
- polyamide resins are, for example, those obtained by reacting haiogenohydrins e.g. Products obtained from epichlorohydrin with aminopolyamides and polyalkylene amines and aliphatic dicarboxylic acids of 2 to 10 carbon atoms, e.g. in U.S. Patent 3,311,594.
- Components (1) and (2) are usually preferred in a weight ratio of 2: 1 to 1: 5 used 1: 1 to 1: 2.
- the new combination of auxiliaries is preferably used as an aftertreatment agent for wool dyeings, while at the same time improving the fastness of the dyeings and acting as an inhibitor for the soiling of the goods.
- components (1) and (2) are usually added separately to the aftertreatment solution.
- the combination mentioned can also be used in the form of an aqueous preparation. This preparation can be obtained by simply stirring the components in water, if necessary by heating to 50 to 70 ° C. and diluting with water to a 20 to 40% solution.
- the present invention accordingly also relates to a process for the aftertreatment of wool-containing fiber material dyed with anionic dyes, which is characterized in that this material is treated with an aqueous liquor which comprises the auxiliary combination according to the invention, i.e. Contains components (1) and (2).
- the fiber material can be in a wide variety of processing stages. For example, the following can be considered: flake, sliver, fabric, knitted fabric, nonwovens, yarn or knitwear.
- the anionic dyes are, for example, salts of heavy metal-containing or metal-free mono-, dis- or polyazo dyes including the formazan dyes and the anthraquinone, xanthene, nitro, triphenylmethane, naphthoquinoneimine and phthalocyanine dyes.
- the anionic character of these dyes can be caused by metal complex formation alone and / or preferably by acidic, salt-forming substituents, such as carboxylic acid groups, sulfuric acid and phosphonic acid ester groups, phosphonic acid groups or sulfonic acid groups.
- These dyes can also have so-called reactive groups in the molecule, which form a covalent bond with the material to be colored. Acidic metal-free reactive dyes which preferably have at least two sulfonic acid groups are preferred.
- the 1: 1 or preferably 1: 2 metal complex dyes are also of interest.
- the 1: 1 metal complex dyes preferably have one or two sulfonic acid groups. As metal they contain a heavy metal atom, e.g. Copper, nickel or especially chrome.
- the 1: 2 metal complex dyes contain a heavy metal atom as the central atom, e.g. a cobalt atom or in particular a chromium atom.
- Two complex-forming components are connected to the central atom, at least one of which is a dye molecule, but preferably both are dye molecules.
- the two dye molecules involved in the complex formation can be the same or different from one another.
- the 1: 2 metal complex dyes can e.g.
- the azo dye molecules can have water solubilizing groups, e.g. Acid amide, alkylsulfonyl or the acid groups mentioned above. Preference is given to 1: 2 cobalt or 1: 2 chromium complexes of monoazo dyes which have acid amide groups, alkylsulfonyl groups or a total of a single sulfonic acid group.
- anionic dyes can also be used.
- dye mixtures of at least 2 or 3 anionic dyes can be used to produce level bichromy or trichromatic dyeings.
- Dye mixtures which contain a reactive dye with at least two sulfonic acid groups and a 1: 2 metal complex dye are particularly preferred.
- the mixing ratio can vary from 9: 1 to 1: 9.
- the dyeings can be produced by the exhaust process, padding process or by printing.
- the amount of dyes used depends on the desired depth of color. In general, amounts of 0.1 to 10 percent by weight, in particular 0.5 to 5 percent by weight, based on the fiber material used, have proven successful.
- the aftertreatment of the dyed wool material according to the invention is generally followed Send a color, but preferably carried out from a fresh bath.
- the liquor ratio can be selected within a wide range, for example: 1: 3 to 1: 100, preferably 1:10 to 1:50. It is convenient to work at a temperature of 20 to 98 ° C, preferably 40 to 60 ° C in the exhaust process and 20 to 30 ° C in the padding process. Special devices are not required in the method according to the invention.
- the usual dyeing devices such as open baths, reel runners, jiggers, paddle, nozzle or circulation devices, can be used.
- the treatment liquors contain components (1) and (2) in the exhaust process, preferably each in an amount of 0.2 to 5% by weight, in particular 0.5 to 2% by weight, based on the weight of the wool or, in the case of padding liquors, expediently in each case in an amount of 1 to 50 g / l, preferably 10 to 30 g / l, components (1) and (2) being present in the weight ratio mentioned above.
- the squeezing effect is appropriately 60 to 90% by weight.
- the aftertreatment fiotts can include mineral acids, e.g. Sulfuric acid or phosphoric acid, organic acids, suitably lower aliphatic carboxylic acids, e.g. Formic, acetic or oxalic acid and / or salts such as ammonium acetate, ammonium sulfate or sodium acetate.
- the acids primarily serve to adjust the pH of the liquors, which can be 4 to 8, but preferably 5 to 6.
- the liquors can also contain other common additives, such as Wool protection, dispersing and wetting agents as well as defoamers included.
- the aftertreatment of the wool-containing material is expediently carried out in such a way that the material is then treated with an aqueous liquor which contains components (1) and (2) and, if appropriate, acid, followed by dyeing from a fresh bath.
- the dyed wool-containing materials are preferably added to a liquor which contains components (1) and (2) and acid and has a pH of 4.5 to 6 and a temperature of 40 ° C., and the wool is treated in this Temperature for 15 to 45 minutes, preferably 20 to 30 minutes.
- the wet fastness properties and the rub fastness properties are improved and, surprisingly, a soiling inhibition is also achieved at the same time. Color yield and light fastness are not affected.
- the parts are parts by weight and the percentages are percentages by weight.
- R , residual behenic acid.
- n 10-18.
- the product has a molecular weight of 4500-6300.
- reaction mixture is then stirred for a further 5 hours at 110 ° C. and then the excess dichloroethyl ether is removed at 80 ° C. and 1.33.104 Pa.
- the pH of a 5% aqueous solution is 4.0.
- Example 1 In a dyeing machine, 10 g of chlorinated wool fabric are dyed as follows: One starts at 40 ° C. with a liquor ratio of 1:30, the fabric in the aqueous liquor being constantly moved.
- a fresh bath at 40 ° C. and a liquor ratio of 1:30 is admixed with 0.6% of the ammonium salt of the formula (101) and 0.6% of the polymeric ammonium salt according to instruction F with units of the formula (125). After 10 minutes, the pH is adjusted to 5 with acetic acid and treated for a further 15 minutes. It is then dewatered and dried.
- the three tissues treated in this way are then examined for their stainability.
- the fastnesses of the dyeings are checked for potting, wash 3 and xenon light.
- the soiling behavior test is carried out as follows:
- the dye bath is heated to boil in 45 minutes and boiled for 60 minutes. The bath is then cooled and the goods are rinsed. In a fresh bath (liquor ratio 1:30), the dyeing is aftertreated at 40 ° C. with 1% of the reaction product according to preparation G with units of the formula (126) and 0.6% of the ammonium salt of the formula (101) for 20 minutes. It is then rinsed and dried. 2 Parallel tests or soiling tests are carried out as described in Example 1. The fastness to perspiration, alkaline, the wet heat test and the xenon light fastness were evaluated from the three colors. The results are shown in Table 2.
- ammonium salt of the formula (101) the diquaternary ammonium salts of the formulas (100) or (102) to (112) are used, and instead of the ammonium salt of the formula (126), ammonium salts of the formulas (120) to (123) or polymeric ammonium salts according to Before writing E or F with units of the formula (124) or (125), similarly good results are achieved.
- Example 4 A hand-knitting yarn made of 100 kg of wool is on a strand dyeing machine at a liquor ratio of 1:15 with 5% of a mixture consisting of a 1: 1 chromium complex of the dye of the formula and a 1: 1 chromium complex of the dye of the formula (Mixing ratio 3: 2) colored. The bath is then cooled and the wool is rinsed. In the same apparatus, from a fresh bath also at a liquor ratio of 1:15, the dyeing is aftertreated as follows.
- the mixture is warmed to 85 ° C. in the course of 25 minutes and dyed at this temperature for 60 minutes. Then 3% of the diquaternary diammonium salt of the formula (109) and 3% of the polyammonium salt according to specification G with units of the formula (126) are added to the completely dyed bath. It is treated in the cooling belt, in particular at 40-50 ° C. for 15 minutes, after which the goods are rinsed and dried.
- a strong, level, level black dyeing is obtained which has a potting fastness of 4-5.
- the handle of the sliver is very soft, which has a positive effect on the processability.
- the wool is treated for 15 minutes at 50 ° C. Then it is rinsed and dried.
- the wool shows a full, level, brown shade and a potting fastness of grade 4.
- the feel of the wool is pleasantly soft.
- the wool is treated in a cooling bath, in particular at 40-50 ° C. for 15 minutes, after which the wool is rinsed and dried.
- the wool shows a level, black shade with a potting fastness of 4-5.
- the wool has a soft feel.
Landscapes
- Engineering & Computer Science (AREA)
- Textile Engineering (AREA)
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Coloring (AREA)
- Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
- Macromolecular Compounds Obtained By Forming Nitrogen-Containing Linkages In General (AREA)
Claims (15)
minéral ou organique fort.
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CH4802/85 | 1985-11-08 | ||
CH480285 | 1985-11-08 |
Publications (2)
Publication Number | Publication Date |
---|---|
EP0225281A1 EP0225281A1 (fr) | 1987-06-10 |
EP0225281B1 true EP0225281B1 (fr) | 1989-06-14 |
Family
ID=4282802
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
EP86810500A Expired EP0225281B1 (fr) | 1985-11-08 | 1986-11-03 | Combinaison d'agents auxiliaires et son utilisation comme agent d'ennoblissement |
Country Status (7)
Country | Link |
---|---|
US (1) | US4728337A (fr) |
EP (1) | EP0225281B1 (fr) |
JP (1) | JPS62117887A (fr) |
AU (1) | AU589463B2 (fr) |
CA (1) | CA1278402C (fr) |
DE (1) | DE3663965D1 (fr) |
ZA (1) | ZA868485B (fr) |
Families Citing this family (20)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4728337A (en) * | 1985-11-08 | 1988-03-01 | Ciba-Geigy Corporation | Assistant combination and use thereof as wool textile finishing agent |
DE3672564D1 (de) * | 1985-11-08 | 1990-08-16 | Ciba Geigy Ag | Diquaternaere ammoniumsalze und deren herstellung und verwendung als textilveredelungsmittel. |
GB9202375D0 (en) * | 1992-02-05 | 1992-03-18 | Ici Plc | Process |
IT1254994B (it) * | 1992-06-24 | 1995-10-11 | Giuseppe Raspanti | Composti poliquaternari e loro utilizzo come fissatori di coloranti |
ES2088654T3 (es) * | 1992-10-01 | 1996-08-16 | Ciba Geigy Ag | Procedimiento para teñir materiales de fibra de lana. |
US5395967A (en) * | 1993-06-07 | 1995-03-07 | 3V Inc. | Polyquaternary compounds and the use thereof as dye fixers |
US5643864A (en) * | 1994-08-19 | 1997-07-01 | Rhone-Poulenc, Inc. | Anionic surfactants having multiple hydrophobic and hydrophilic groups |
GB2310659A (en) * | 1996-02-27 | 1997-09-03 | Procter & Gamble | Cationic detergent compounds |
US5830240A (en) * | 1996-10-23 | 1998-11-03 | Solutia Inc. | Fibers and textile materials having enhanced dyeability and finish compositions used thereon |
US5944852A (en) * | 1996-10-23 | 1999-08-31 | Solutia Inc. | Dyeing process |
KR100579717B1 (ko) * | 1998-12-03 | 2006-09-27 | 주식회사 엘지생활건강 | 양이온성 당류계 계면활성제 및 그의 제조 방법 |
JP4443929B2 (ja) * | 2002-01-07 | 2010-03-31 | チバ ホールディング インコーポレーテッド | 染料固着剤を含む微粒子組成物 |
DE102004018051A1 (de) * | 2004-04-08 | 2005-11-10 | Clariant Gmbh | Wasch- und Reinigungsmittel enthaltend Farbfixiermittel und Soil Release Polymere |
JP4709693B2 (ja) * | 2006-06-07 | 2011-06-22 | 株式会社東芝 | 電子機器 |
EP2185678A2 (fr) * | 2007-08-31 | 2010-05-19 | The Procter and Gamble Company | Procédés visant à modifier une perception visuelle et compositions associées |
CN103696245A (zh) * | 2013-12-16 | 2014-04-02 | 常熟市天赢印染有限公司 | 提高织物穿着舒适性的微凝胶整理剂 |
CN105037176A (zh) * | 2015-07-07 | 2015-11-11 | 西北大学 | 含羟基的季铵盐型双子表面活性剂的制备方法及在三次采油中的应用 |
CN113322697A (zh) * | 2021-06-08 | 2021-08-31 | 肇庆纤博新材料科技有限公司 | 一种莱赛尔、莫代尔纤维面料的浸染保护剂 |
CN115197077A (zh) * | 2022-08-15 | 2022-10-18 | 中国日用化学研究院有限公司 | 一种含多季铵头基阳离子低聚表面活性剂及其制备方法 |
CN115975742A (zh) * | 2022-11-18 | 2023-04-18 | 浙江传化日用品有限公司 | 一种抑菌易漂洗的洗涤剂及其制备方法 |
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Publication number | Priority date | Publication date | Assignee | Title |
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US27386A (en) * | 1860-03-06 | Mill-spindle | ||
US3097039A (en) * | 1963-07-09 | Hoas oh | ||
US27333A (en) * | 1860-02-28 | Improvement in tools for forming the necks and orifices of glass bottles | ||
DE582101C (de) * | 1930-10-16 | 1933-08-10 | Chem Ind Basel | Verfahren zur Verbesserung der Echtheitseigenschaften von mit wasserloeslichen Farbstoffen gefaerbten Textilien |
US2891835A (en) * | 1956-10-10 | 1959-06-23 | Ciba Ltd | Diquaternary ammonium compounds used in the cationic dyeing of fibers of polyacrylonitrile |
CH369110A (de) * | 1959-04-10 | 1963-01-31 | Ciba Geigy | Verfahren zum Färben und Bedrucken von stickstoffhaltigen Fasern mit 1 :2-Metallkomplexverbindungen von Azofarbstoffen |
CH375692A (de) * | 1962-07-31 | 1963-11-30 | Geigy Ag J R | Verfahren zur Fertigstellung von Färbungen und Drucken mit Reaktivfarbstoffen auf natürlichen oder synthetischen Polyamidfasern |
US3490859A (en) * | 1967-09-05 | 1970-01-20 | Geigy Ag J R | Process for aftertreatment of colored polyamide fibers |
CH643868A4 (fr) * | 1968-04-30 | 1972-10-31 | ||
CH37469A4 (fr) * | 1969-01-13 | 1971-08-31 | ||
CH1669775A4 (fr) * | 1975-12-23 | 1977-06-30 | ||
US4312813A (en) * | 1980-06-26 | 1982-01-26 | Johnson & Johnson Baby Products Company | Bisquaternary ammonium compound |
CH660940GA3 (fr) * | 1981-01-10 | 1987-06-30 | ||
DE3151594A1 (de) * | 1981-01-10 | 1982-08-26 | Sandoz-Patent-GmbH, 7850 Lörrach | Verfahren zur verbesserung faerberischer eigenschaften von polyamidfaser-textilmaterialien |
US4467486A (en) * | 1982-08-26 | 1984-08-28 | Virginia Adjustable Bed Manufacturing Corp. | Headboard bracket |
JPS60134080A (ja) * | 1983-12-16 | 1985-07-17 | 一方社油脂工業株式会社 | 繊維材料の染色性改良方法、カチオン性の繊維反応性化合物及びその製造方法 |
DE3505018A1 (de) * | 1984-02-24 | 1985-09-05 | Sandoz-Patent-GmbH, 7850 Lörrach | Nachbehandlungsverfahren fuer gefaerbtes textilmaterial |
FR2560240B1 (fr) * | 1984-02-24 | 1987-07-10 | Sandoz Sa | Procede de post-traitement des fibres textiles |
US4661269A (en) * | 1985-03-28 | 1987-04-28 | The Procter & Gamble Company | Liquid fabric softener |
US4728337A (en) * | 1985-11-08 | 1988-03-01 | Ciba-Geigy Corporation | Assistant combination and use thereof as wool textile finishing agent |
AU6195686A (en) * | 1986-08-04 | 1988-02-24 | James G. Fuller | Particulate water dispersible free flowing fabric softener composition and process for making same |
-
1986
- 1986-10-30 US US06/925,027 patent/US4728337A/en not_active Expired - Lifetime
- 1986-11-03 EP EP86810500A patent/EP0225281B1/fr not_active Expired
- 1986-11-03 DE DE8686810500T patent/DE3663965D1/de not_active Expired
- 1986-11-06 CA CA000522298A patent/CA1278402C/fr not_active Expired - Lifetime
- 1986-11-07 AU AU64951/86A patent/AU589463B2/en not_active Ceased
- 1986-11-07 ZA ZA868485A patent/ZA868485B/xx unknown
- 1986-11-08 JP JP61264918A patent/JPS62117887A/ja active Granted
Also Published As
Publication number | Publication date |
---|---|
DE3663965D1 (en) | 1989-07-20 |
JPS62117887A (ja) | 1987-05-29 |
AU589463B2 (en) | 1989-10-12 |
CA1278402C (fr) | 1991-01-02 |
JPH0127189B2 (fr) | 1989-05-26 |
US4728337A (en) | 1988-03-01 |
ZA868485B (en) | 1987-06-24 |
EP0225281A1 (fr) | 1987-06-10 |
AU6495186A (en) | 1987-05-14 |
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