NO744034L - - Google Patents
Info
- Publication number
- NO744034L NO744034L NO744034A NO744034A NO744034L NO 744034 L NO744034 L NO 744034L NO 744034 A NO744034 A NO 744034A NO 744034 A NO744034 A NO 744034A NO 744034 L NO744034 L NO 744034L
- Authority
- NO
- Norway
- Prior art keywords
- textile
- free radical
- catalyst
- acid
- reactant
- Prior art date
Links
- 239000004753 textile Substances 0.000 claims description 52
- 238000000034 method Methods 0.000 claims description 45
- -1 methylol, hydroxy Chemical group 0.000 claims description 32
- 239000000376 reactant Substances 0.000 claims description 29
- 239000004744 fabric Substances 0.000 claims description 20
- 239000003054 catalyst Substances 0.000 claims description 17
- 239000000178 monomer Substances 0.000 claims description 17
- 150000003254 radicals Chemical class 0.000 claims description 15
- RNFJDJUURJAICM-UHFFFAOYSA-N 2,2,4,4,6,6-hexaphenoxy-1,3,5-triaza-2$l^{5},4$l^{5},6$l^{5}-triphosphacyclohexa-1,3,5-triene Chemical compound N=1P(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP=1(OC=1C=CC=CC=1)OC1=CC=CC=C1 RNFJDJUURJAICM-UHFFFAOYSA-N 0.000 claims description 10
- CNCOEDDPFOAUMB-UHFFFAOYSA-N N-Methylolacrylamide Chemical compound OCNC(=O)C=C CNCOEDDPFOAUMB-UHFFFAOYSA-N 0.000 claims description 10
- 239000003063 flame retardant Substances 0.000 claims description 10
- 238000004519 manufacturing process Methods 0.000 claims description 6
- 238000010526 radical polymerization reaction Methods 0.000 claims description 6
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 5
- 238000006482 condensation reaction Methods 0.000 claims description 5
- 125000000524 functional group Chemical group 0.000 claims description 5
- ZEYUSQVGRCPBPG-UHFFFAOYSA-N 4,5-dihydroxy-1,3-bis(hydroxymethyl)imidazolidin-2-one Chemical compound OCN1C(O)C(O)N(CO)C1=O ZEYUSQVGRCPBPG-UHFFFAOYSA-N 0.000 claims description 4
- RAHZWNYVWXNFOC-UHFFFAOYSA-N Sulphur dioxide Chemical compound O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 claims description 4
- 125000003277 amino group Chemical group 0.000 claims description 4
- 238000009833 condensation Methods 0.000 claims description 4
- 230000005494 condensation Effects 0.000 claims description 4
- JRKICGRDRMAZLK-UHFFFAOYSA-L persulfate group Chemical group S(=O)(=O)([O-])OOS(=O)(=O)[O-] JRKICGRDRMAZLK-UHFFFAOYSA-L 0.000 claims description 4
- 229910052717 sulfur Inorganic materials 0.000 claims description 4
- 239000011593 sulfur Substances 0.000 claims description 4
- 230000002378 acidificating effect Effects 0.000 claims description 3
- 239000012190 activator Substances 0.000 claims description 3
- 125000003545 alkoxy group Chemical group 0.000 claims description 3
- 238000006555 catalytic reaction Methods 0.000 claims description 3
- BHEPBYXIRTUNPN-UHFFFAOYSA-N hydridophosphorus(.) (triplet) Chemical compound [PH] BHEPBYXIRTUNPN-UHFFFAOYSA-N 0.000 claims description 3
- 238000010438 heat treatment Methods 0.000 claims description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 2
- 239000005864 Sulphur Substances 0.000 claims 1
- 230000018044 dehydration Effects 0.000 claims 1
- 238000006297 dehydration reaction Methods 0.000 claims 1
- 239000000835 fiber Substances 0.000 description 29
- 229920000742 Cotton Polymers 0.000 description 14
- OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Natural products OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- 229920000642 polymer Polymers 0.000 description 12
- 238000006243 chemical reaction Methods 0.000 description 8
- 230000002045 lasting effect Effects 0.000 description 8
- 150000001408 amides Chemical class 0.000 description 7
- 238000002360 preparation method Methods 0.000 description 7
- 230000000694 effects Effects 0.000 description 6
- 238000011065 in-situ storage Methods 0.000 description 6
- 150000004819 silanols Chemical class 0.000 description 6
- 238000005406 washing Methods 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 5
- 229920001577 copolymer Polymers 0.000 description 5
- 229910052698 phosphorus Inorganic materials 0.000 description 5
- 239000011574 phosphorus Substances 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- AEMRFAOFKBGASW-UHFFFAOYSA-N Glycolic acid Chemical class OCC(O)=O AEMRFAOFKBGASW-UHFFFAOYSA-N 0.000 description 4
- 229920000877 Melamine resin Polymers 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- 239000003377 acid catalyst Substances 0.000 description 4
- 229920003180 amino resin Polymers 0.000 description 4
- 239000011953 free-radical catalyst Substances 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- OMNKZBIFPJNNIO-UHFFFAOYSA-N n-(2-methyl-4-oxopentan-2-yl)prop-2-enamide Chemical compound CC(=O)CC(C)(C)NC(=O)C=C OMNKZBIFPJNNIO-UHFFFAOYSA-N 0.000 description 4
- 238000012360 testing method Methods 0.000 description 4
- 229920002554 vinyl polymer Polymers 0.000 description 4
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 description 3
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical class OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
- MBHRHUJRKGNOKX-UHFFFAOYSA-N [(4,6-diamino-1,3,5-triazin-2-yl)amino]methanol Chemical class NC1=NC(N)=NC(NCO)=N1 MBHRHUJRKGNOKX-UHFFFAOYSA-N 0.000 description 3
- 238000010521 absorption reaction Methods 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 150000001298 alcohols Chemical class 0.000 description 3
- 150000001412 amines Chemical class 0.000 description 3
- 235000013877 carbamide Nutrition 0.000 description 3
- 229920002678 cellulose Polymers 0.000 description 3
- 239000001913 cellulose Substances 0.000 description 3
- 238000004132 cross linking Methods 0.000 description 3
- 239000003599 detergent Substances 0.000 description 3
- 150000002148 esters Chemical class 0.000 description 3
- 150000002170 ethers Chemical class 0.000 description 3
- FQPSGWSUVKBHSU-UHFFFAOYSA-N methacrylamide Chemical compound CC(=C)C(N)=O FQPSGWSUVKBHSU-UHFFFAOYSA-N 0.000 description 3
- 150000003138 primary alcohols Chemical class 0.000 description 3
- 230000005855 radiation Effects 0.000 description 3
- 239000005871 repellent Substances 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 3
- OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 description 2
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 2
- OMIGHNLMNHATMP-UHFFFAOYSA-N 2-hydroxyethyl prop-2-enoate Chemical compound OCCOC(=O)C=C OMIGHNLMNHATMP-UHFFFAOYSA-N 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical class CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
- 240000000491 Corchorus aestuans Species 0.000 description 2
- 235000011777 Corchorus aestuans Nutrition 0.000 description 2
- 235000010862 Corchorus capsularis Nutrition 0.000 description 2
- WOBHKFSMXKNTIM-UHFFFAOYSA-N Hydroxyethyl methacrylate Chemical compound CC(=C)C(=O)OCCO WOBHKFSMXKNTIM-UHFFFAOYSA-N 0.000 description 2
- TWRXJAOTZQYOKJ-UHFFFAOYSA-L Magnesium chloride Chemical compound [Mg+2].[Cl-].[Cl-] TWRXJAOTZQYOKJ-UHFFFAOYSA-L 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 229920000297 Rayon Polymers 0.000 description 2
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric Acid Chemical class [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 2
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 2
- 238000007171 acid catalysis Methods 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- ROOXNKNUYICQNP-UHFFFAOYSA-N ammonium persulfate Chemical compound [NH4+].[NH4+].[O-]S(=O)(=O)OOS([O-])(=O)=O ROOXNKNUYICQNP-UHFFFAOYSA-N 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- MRVZORUPSXTRHD-UHFFFAOYSA-N bis(hydroxymethyl)phosphorylmethanol Chemical compound OCP(=O)(CO)CO MRVZORUPSXTRHD-UHFFFAOYSA-N 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical class OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 235000014113 dietary fatty acids Nutrition 0.000 description 2
- 229920001971 elastomer Polymers 0.000 description 2
- 239000000194 fatty acid Substances 0.000 description 2
- 229930195729 fatty acid Natural products 0.000 description 2
- 150000004665 fatty acids Chemical class 0.000 description 2
- 229940104869 fluorosilicate Drugs 0.000 description 2
- BTFJIXJJCSYFAL-UHFFFAOYSA-N icosan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCCCO BTFJIXJJCSYFAL-UHFFFAOYSA-N 0.000 description 2
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical class CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
- 150000004668 long chain fatty acids Chemical class 0.000 description 2
- YIXJRHPUWRPCBB-UHFFFAOYSA-N magnesium nitrate Chemical compound [Mg+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O YIXJRHPUWRPCBB-UHFFFAOYSA-N 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- DNTMQTKDNSEIFO-UHFFFAOYSA-N n-(hydroxymethyl)-2-methylprop-2-enamide Chemical compound CC(=C)C(=O)NCO DNTMQTKDNSEIFO-UHFFFAOYSA-N 0.000 description 2
- LYRFLYHAGKPMFH-UHFFFAOYSA-N octadecanamide Chemical compound CCCCCCCCCCCCCCCCCC(N)=O LYRFLYHAGKPMFH-UHFFFAOYSA-N 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- 229920000728 polyester Polymers 0.000 description 2
- 238000006116 polymerization reaction Methods 0.000 description 2
- 229920001296 polysiloxane Polymers 0.000 description 2
- USHAGKDGDHPEEY-UHFFFAOYSA-L potassium persulfate Chemical compound [K+].[K+].[O-]S(=O)(=O)OOS([O-])(=O)=O USHAGKDGDHPEEY-UHFFFAOYSA-L 0.000 description 2
- 125000000075 primary alcohol group Chemical group 0.000 description 2
- 239000002964 rayon Substances 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 238000005507 spraying Methods 0.000 description 2
- 238000009988 textile finishing Methods 0.000 description 2
- 230000037303 wrinkles Effects 0.000 description 2
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 2
- ONDPHDOFVYQSGI-UHFFFAOYSA-N zinc nitrate Chemical compound [Zn+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O ONDPHDOFVYQSGI-UHFFFAOYSA-N 0.000 description 2
- UOCLXMDMGBRAIB-UHFFFAOYSA-N 1,1,1-trichloroethane Chemical compound CC(Cl)(Cl)Cl UOCLXMDMGBRAIB-UHFFFAOYSA-N 0.000 description 1
- IQDKUTQPYBHPJK-UHFFFAOYSA-N 1,3-bis(hydroxymethyl)-1,3-diazinan-2-one Chemical compound OCN1CCCN(CO)C1=O IQDKUTQPYBHPJK-UHFFFAOYSA-N 0.000 description 1
- NQPJDJVGBDHCAD-UHFFFAOYSA-N 1,3-diazinan-2-one Chemical compound OC1=NCCCN1 NQPJDJVGBDHCAD-UHFFFAOYSA-N 0.000 description 1
- RGPFLNIHXDCHKE-UHFFFAOYSA-N 1-(octadecoxymethyl)pyridin-1-ium Chemical class CCCCCCCCCCCCCCCCCCOC[N+]1=CC=CC=C1 RGPFLNIHXDCHKE-UHFFFAOYSA-N 0.000 description 1
- FYZNXVFKBHWTFN-UHFFFAOYSA-N 1-[2-(2-octadecoxyethoxy)ethoxymethylidene]-2h-pyridin-1-ium Chemical class CCCCCCCCCCCCCCCCCCOCCOCCOC=[N+]1CC=CC=C1 FYZNXVFKBHWTFN-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
- MBEVSMZJMIQVBG-UHFFFAOYSA-N 2-(hydroxymethyl)guanidine Chemical class NC(N)=NCO MBEVSMZJMIQVBG-UHFFFAOYSA-N 0.000 description 1
- MTLWTRLYHAQCAM-UHFFFAOYSA-N 2-[(1-cyano-2-methylpropyl)diazenyl]-3-methylbutanenitrile Chemical compound CC(C)C(C#N)N=NC(C#N)C(C)C MTLWTRLYHAQCAM-UHFFFAOYSA-N 0.000 description 1
- RILZRCJGXSFXNE-UHFFFAOYSA-N 2-[4-(trifluoromethoxy)phenyl]ethanol Chemical class OCCC1=CC=C(OC(F)(F)F)C=C1 RILZRCJGXSFXNE-UHFFFAOYSA-N 0.000 description 1
- WFUGQJXVXHBTEM-UHFFFAOYSA-N 2-hydroperoxy-2-(2-hydroperoxybutan-2-ylperoxy)butane Chemical compound CCC(C)(OO)OOC(C)(CC)OO WFUGQJXVXHBTEM-UHFFFAOYSA-N 0.000 description 1
- DLTLLZLEJKRETK-UHFFFAOYSA-N 2-n,2-n,4-n,4-n,6-n-pentamethoxy-6-n-methyl-1,3,5-triazine-2,4,6-triamine Chemical compound CON(C)C1=NC(N(OC)OC)=NC(N(OC)OC)=N1 DLTLLZLEJKRETK-UHFFFAOYSA-N 0.000 description 1
- JTNCEQNHURODLX-UHFFFAOYSA-N 2-phenylethanimidamide Chemical compound NC(=N)CC1=CC=CC=C1 JTNCEQNHURODLX-UHFFFAOYSA-N 0.000 description 1
- FRIBMENBGGCKPD-UHFFFAOYSA-N 3-(2,3-dimethoxyphenyl)prop-2-enal Chemical compound COC1=CC=CC(C=CC=O)=C1OC FRIBMENBGGCKPD-UHFFFAOYSA-N 0.000 description 1
- AUBCOVMWQWFBIJ-UHFFFAOYSA-N 3-[bis[3-(hydroxymethylamino)-3-oxopropyl]amino]-n-(hydroxymethyl)propanamide Chemical compound OCNC(=O)CCN(CCC(=O)NCO)CCC(=O)NCO AUBCOVMWQWFBIJ-UHFFFAOYSA-N 0.000 description 1
- NNTWKXKLHMTGBU-UHFFFAOYSA-N 4,5-dihydroxyimidazolidin-2-one Chemical class OC1NC(=O)NC1O NNTWKXKLHMTGBU-UHFFFAOYSA-N 0.000 description 1
- OXDFBFQNFZGTRO-UHFFFAOYSA-N 4-tert-butylperoxy-4-oxobutanoic acid Chemical compound CC(C)(C)OOC(=O)CCC(O)=O OXDFBFQNFZGTRO-UHFFFAOYSA-N 0.000 description 1
- ZMGMDXCADSRNCX-UHFFFAOYSA-N 5,6-dihydroxy-1,3-diazepan-2-one Chemical compound OC1CNC(=O)NCC1O ZMGMDXCADSRNCX-UHFFFAOYSA-N 0.000 description 1
- PXRKCOCTEMYUEG-UHFFFAOYSA-N 5-aminoisoindole-1,3-dione Chemical class NC1=CC=C2C(=O)NC(=O)C2=C1 PXRKCOCTEMYUEG-UHFFFAOYSA-N 0.000 description 1
- 244000198134 Agave sisalana Species 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
- 239000004160 Ammonium persulphate Substances 0.000 description 1
- 239000004342 Benzoyl peroxide Substances 0.000 description 1
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- 244000025254 Cannabis sativa Species 0.000 description 1
- 235000012766 Cannabis sativa ssp. sativa var. sativa Nutrition 0.000 description 1
- 235000012765 Cannabis sativa ssp. sativa var. spontanea Nutrition 0.000 description 1
- 229920002134 Carboxymethyl cellulose Polymers 0.000 description 1
- 229920003043 Cellulose fiber Polymers 0.000 description 1
- 229920002284 Cellulose triacetate Polymers 0.000 description 1
- XZMCDFZZKTWFGF-UHFFFAOYSA-N Cyanamide Chemical compound NC#N XZMCDFZZKTWFGF-UHFFFAOYSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical class Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- 229920000663 Hydroxyethyl cellulose Polymers 0.000 description 1
- 239000004354 Hydroxyethyl cellulose Substances 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- 239000004640 Melamine resin Substances 0.000 description 1
- 229920000914 Metallic fiber Polymers 0.000 description 1
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 1
- 229920002821 Modacrylic Polymers 0.000 description 1
- VGGLHLAESQEWCR-UHFFFAOYSA-N N-(hydroxymethyl)urea Chemical compound NC(=O)NCO VGGLHLAESQEWCR-UHFFFAOYSA-N 0.000 description 1
- PSEHMGJAZZCJBS-UHFFFAOYSA-N NC(=O)N.COC(OC)C=C Chemical compound NC(=O)N.COC(OC)C=C PSEHMGJAZZCJBS-UHFFFAOYSA-N 0.000 description 1
- 239000004677 Nylon Substances 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- CYTYCFOTNPOANT-UHFFFAOYSA-N Perchloroethylene Chemical group ClC(Cl)=C(Cl)Cl CYTYCFOTNPOANT-UHFFFAOYSA-N 0.000 description 1
- 239000004743 Polypropylene Substances 0.000 description 1
- 239000004159 Potassium persulphate Substances 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-N Sulfurous acid Chemical class OS(O)=O LSNNMFCWUKXFEE-UHFFFAOYSA-N 0.000 description 1
- 229920001807 Urea-formaldehyde Polymers 0.000 description 1
- 229920002978 Vinylon Polymers 0.000 description 1
- USDJGQLNFPZEON-UHFFFAOYSA-N [[4,6-bis(hydroxymethylamino)-1,3,5-triazin-2-yl]amino]methanol Chemical compound OCNC1=NC(NCO)=NC(NCO)=N1 USDJGQLNFPZEON-UHFFFAOYSA-N 0.000 description 1
- YGCOKJWKWLYHTG-UHFFFAOYSA-N [[4,6-bis[bis(hydroxymethyl)amino]-1,3,5-triazin-2-yl]-(hydroxymethyl)amino]methanol Chemical compound OCN(CO)C1=NC(N(CO)CO)=NC(N(CO)CO)=N1 YGCOKJWKWLYHTG-UHFFFAOYSA-N 0.000 description 1
- SYDYRFPJJJPJFE-UHFFFAOYSA-N [[4,6-bis[bis(hydroxymethyl)amino]-1,3,5-triazin-2-yl]amino]methanol Chemical compound OCNC1=NC(N(CO)CO)=NC(N(CO)CO)=N1 SYDYRFPJJJPJFE-UHFFFAOYSA-N 0.000 description 1
- SUPOBRXPULIDDX-UHFFFAOYSA-N [[4-amino-6-(hydroxymethylamino)-1,3,5-triazin-2-yl]amino]methanol Chemical compound NC1=NC(NCO)=NC(NCO)=N1 SUPOBRXPULIDDX-UHFFFAOYSA-N 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 239000000443 aerosol Substances 0.000 description 1
- 125000004422 alkyl sulphonamide group Chemical group 0.000 description 1
- 239000002168 alkylating agent Substances 0.000 description 1
- 229940100198 alkylating agent Drugs 0.000 description 1
- 125000003368 amide group Chemical group 0.000 description 1
- 235000019270 ammonium chloride Nutrition 0.000 description 1
- LFVGISIMTYGQHF-UHFFFAOYSA-N ammonium dihydrogen phosphate Chemical compound [NH4+].OP(O)([O-])=O LFVGISIMTYGQHF-UHFFFAOYSA-N 0.000 description 1
- 229910000387 ammonium dihydrogen phosphate Inorganic materials 0.000 description 1
- 229910001870 ammonium persulfate Inorganic materials 0.000 description 1
- 235000019395 ammonium persulphate Nutrition 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- OGBUMNBNEWYMNJ-UHFFFAOYSA-N batilol Chemical class CCCCCCCCCCCCCCCCCCOCC(O)CO OGBUMNBNEWYMNJ-UHFFFAOYSA-N 0.000 description 1
- 235000019400 benzoyl peroxide Nutrition 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
- AOJDZKCUAATBGE-UHFFFAOYSA-N bromomethane Chemical compound Br[CH2] AOJDZKCUAATBGE-UHFFFAOYSA-N 0.000 description 1
- 235000009120 camo Nutrition 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- 239000001768 carboxy methyl cellulose Substances 0.000 description 1
- 235000010948 carboxy methyl cellulose Nutrition 0.000 description 1
- 239000008112 carboxymethyl-cellulose Substances 0.000 description 1
- 229920002301 cellulose acetate Polymers 0.000 description 1
- 235000005607 chanvre indien Nutrition 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 239000011093 chipboard Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 230000003111 delayed effect Effects 0.000 description 1
- LSXWFXONGKSEMY-UHFFFAOYSA-N di-tert-butyl peroxide Chemical compound CC(C)(C)OOC(C)(C)C LSXWFXONGKSEMY-UHFFFAOYSA-N 0.000 description 1
- QGBSISYHAICWAH-UHFFFAOYSA-N dicyandiamide Chemical compound NC(N)=NC#N QGBSISYHAICWAH-UHFFFAOYSA-N 0.000 description 1
- WVJOGYWFVNTSAU-UHFFFAOYSA-N dimethylol ethylene urea Chemical compound OCN1CCN(CO)C1=O WVJOGYWFVNTSAU-UHFFFAOYSA-N 0.000 description 1
- 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 239000000806 elastomer Substances 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 125000002573 ethenylidene group Chemical group [*]=C=C([H])[H] 0.000 description 1
- LQZZUXJYWNFBMV-UHFFFAOYSA-N ethyl butylhexanol Natural products CCCCCCCCCCCCO LQZZUXJYWNFBMV-UHFFFAOYSA-N 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000006260 foam Substances 0.000 description 1
- IVJISJACKSSFGE-UHFFFAOYSA-N formaldehyde;1,3,5-triazine-2,4,6-triamine Chemical compound O=C.NC1=NC(N)=NC(N)=N1 IVJISJACKSSFGE-UHFFFAOYSA-N 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 239000003365 glass fiber Substances 0.000 description 1
- 239000003292 glue Substances 0.000 description 1
- 125000005456 glyceride group Polymers 0.000 description 1
- 229940015043 glyoxal Drugs 0.000 description 1
- 239000004519 grease Substances 0.000 description 1
- 239000011487 hemp Substances 0.000 description 1
- ALBYIUDWACNRRB-UHFFFAOYSA-N hexanamide Chemical compound CCCCCC(N)=O ALBYIUDWACNRRB-UHFFFAOYSA-N 0.000 description 1
- 235000019447 hydroxyethyl cellulose Nutrition 0.000 description 1
- DAXMOHXHMXTTQF-UHFFFAOYSA-N hydroxymethyl hydrogen carbonate Chemical class OCOC(O)=O DAXMOHXHMXTTQF-UHFFFAOYSA-N 0.000 description 1
- YAMHXTCMCPHKLN-UHFFFAOYSA-N imidazolidin-2-one Chemical compound O=C1NCCN1 YAMHXTCMCPHKLN-UHFFFAOYSA-N 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 239000003999 initiator Substances 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- SXQFCVDSOLSHOQ-UHFFFAOYSA-N lactamide Chemical compound CC(O)C(N)=O SXQFCVDSOLSHOQ-UHFFFAOYSA-N 0.000 description 1
- 229910001629 magnesium chloride Inorganic materials 0.000 description 1
- 235000011147 magnesium chloride Nutrition 0.000 description 1
- JDSHMPZPIAZGSV-UHFFFAOYSA-N melamine Chemical compound NC1=NC(N)=NC(N)=N1 JDSHMPZPIAZGSV-UHFFFAOYSA-N 0.000 description 1
- 150000007974 melamines Chemical class 0.000 description 1
- XMYQHJDBLRZMLW-UHFFFAOYSA-N methanolamine Chemical class NCO XMYQHJDBLRZMLW-UHFFFAOYSA-N 0.000 description 1
- SXVDZIOMWSPFCO-UHFFFAOYSA-N methyl n,n-bis(hydroxymethyl)carbamate Chemical compound COC(=O)N(CO)CO SXVDZIOMWSPFCO-UHFFFAOYSA-N 0.000 description 1
- GRVDJDISBSALJP-UHFFFAOYSA-N methyloxidanyl Chemical compound [O]C GRVDJDISBSALJP-UHFFFAOYSA-N 0.000 description 1
- 235000019837 monoammonium phosphate Nutrition 0.000 description 1
- 239000006012 monoammonium phosphate Substances 0.000 description 1
- NVUBFYYOVIBBBL-UHFFFAOYSA-O n-(pyridin-1-ium-1-ylmethyl)octadecanamide Chemical class CCCCCCCCCCCCCCCCCC(=O)NC[N+]1=CC=CC=C1 NVUBFYYOVIBBBL-UHFFFAOYSA-O 0.000 description 1
- BXWNKGSJHAJOGX-UHFFFAOYSA-N n-hexadecyl alcohol Natural products CCCCCCCCCCCCCCCCO BXWNKGSJHAJOGX-UHFFFAOYSA-N 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 239000004745 nonwoven fabric Substances 0.000 description 1
- 229920001778 nylon Polymers 0.000 description 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000006384 oligomerization reaction Methods 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- QUBQYFYWUJJAAK-UHFFFAOYSA-N oxymethurea Chemical compound OCNC(=O)NCO QUBQYFYWUJJAAK-UHFFFAOYSA-N 0.000 description 1
- 229950005308 oxymethurea Drugs 0.000 description 1
- 125000000913 palmityl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000000123 paper Substances 0.000 description 1
- 230000035515 penetration Effects 0.000 description 1
- 150000002978 peroxides Chemical class 0.000 description 1
- 125000000864 peroxy group Chemical group O(O*)* 0.000 description 1
- 125000005342 perphosphate group Chemical group 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 229920000233 poly(alkylene oxides) Polymers 0.000 description 1
- 229920000058 polyacrylate Polymers 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 238000012643 polycondensation polymerization Methods 0.000 description 1
- 229920000139 polyethylene terephthalate Polymers 0.000 description 1
- 239000005020 polyethylene terephthalate Substances 0.000 description 1
- 239000002685 polymerization catalyst Substances 0.000 description 1
- ODGAOXROABLFNM-UHFFFAOYSA-N polynoxylin Chemical compound O=C.NC(N)=O ODGAOXROABLFNM-UHFFFAOYSA-N 0.000 description 1
- 229920000098 polyolefin Polymers 0.000 description 1
- 229920001155 polypropylene Polymers 0.000 description 1
- 229920002635 polyurethane Polymers 0.000 description 1
- 239000004814 polyurethane Substances 0.000 description 1
- 229920000915 polyvinyl chloride Polymers 0.000 description 1
- 239000004800 polyvinyl chloride Substances 0.000 description 1
- 229910000343 potassium bisulfate Inorganic materials 0.000 description 1
- 235000019394 potassium persulphate Nutrition 0.000 description 1
- 238000003825 pressing Methods 0.000 description 1
- 150000003141 primary amines Chemical class 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920006298 saran Polymers 0.000 description 1
- 150000003335 secondary amines Chemical class 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- WBHQBSYUUJJSRZ-UHFFFAOYSA-M sodium bisulfate Chemical compound [Na+].OS([O-])(=O)=O WBHQBSYUUJJSRZ-UHFFFAOYSA-M 0.000 description 1
- 229910000342 sodium bisulfate Inorganic materials 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L sodium sulphate Substances [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 229940037312 stearamide Drugs 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 229940124530 sulfonamide Drugs 0.000 description 1
- 150000003456 sulfonamides Chemical class 0.000 description 1
- 238000001356 surgical procedure Methods 0.000 description 1
- 230000002195 synergetic effect Effects 0.000 description 1
- 229920002994 synthetic fiber Polymers 0.000 description 1
- 239000012209 synthetic fiber Substances 0.000 description 1
- 239000011975 tartaric acid Chemical class 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- GJBRNHKUVLOCEB-UHFFFAOYSA-N tert-butyl benzenecarboperoxoate Chemical compound CC(C)(C)OOC(=O)C1=CC=CC=C1 GJBRNHKUVLOCEB-UHFFFAOYSA-N 0.000 description 1
- CIHOLLKRGTVIJN-UHFFFAOYSA-N tert‐butyl hydroperoxide Chemical class CC(C)(C)OO CIHOLLKRGTVIJN-UHFFFAOYSA-N 0.000 description 1
- 229950011008 tetrachloroethylene Drugs 0.000 description 1
- ILJSQTXMGCGYMG-UHFFFAOYSA-N triacetic acid Chemical compound CC(=O)CC(=O)CC(O)=O ILJSQTXMGCGYMG-UHFFFAOYSA-N 0.000 description 1
- 150000003672 ureas Chemical class 0.000 description 1
- 150000003673 urethanes Chemical class 0.000 description 1
- 238000009834 vaporization Methods 0.000 description 1
- 230000008016 vaporization Effects 0.000 description 1
- 238000004804 winding Methods 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
- 210000002268 wool Anatomy 0.000 description 1
- 235000005074 zinc chloride Nutrition 0.000 description 1
- 239000011592 zinc chloride Substances 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
- D06M15/00—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment
- D06M15/19—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment with synthetic macromolecular compounds
- D06M15/21—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
- D06M15/263—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds of unsaturated carboxylic acids; Salts or esters thereof
-
- 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
- D06M13/285—Phosphines; Phosphine oxides; Phosphine sulfides; Phosphinic or phosphinous acids or derivatives thereof
-
- 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
-
- 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
- D06M14/00—Graft polymerisation of monomers containing carbon-to-carbon unsaturated bonds on to fibres, threads, yarns, fabrics, or fibrous goods made from such materials
-
- 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
- D06M15/00—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment
- D06M15/19—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment with synthetic macromolecular compounds
- D06M15/21—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
- D06M15/285—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds of unsaturated carboxylic acid amides or imides
-
- 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
- D06M15/00—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment
- D06M15/19—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment with synthetic macromolecular compounds
- D06M15/21—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
- D06M15/285—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds of unsaturated carboxylic acid amides or imides
- D06M15/29—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds of unsaturated carboxylic acid amides or imides containing a N-methylol group or an etherified N-methylol group; containing a N-aminomethylene group; containing a N-sulfidomethylene group
Landscapes
- Engineering & Computer Science (AREA)
- Textile Engineering (AREA)
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
Description
"Fremgangsmåte for frembringelse av"Procedure for producing
en vaskefast finish på tekstiler".a washable finish on textiles".
Foreliggende oppfinnelse gjelder en fremgangsmåte for finish-behandling av tekstiler. Mer spesielt gjelder oppfinnelsen en in situ fremgangsmåte for å gi en varig finish til tekstiler ved å gjennomføre en friradikalpolymerisasjon og en kondensasjon via aminoplastfunksjonalitet på tekstilet, slik at det oppnås varige egenskaper som f.eks. flammehemmende evne, flekkfasthet, fettfasthet, vannfasthet og liknende hos tekstilet. The present invention relates to a method for the finish treatment of textiles. More particularly, the invention relates to an in situ method for giving a lasting finish to textiles by carrying out a free-radical polymerization and a condensation via aminoplast functionality on the textile, so that lasting properties such as e.g. flame retardant ability, stain resistance, grease resistance, water resistance and similar in the textile.
Det er blitt en kraftig økning i aktiviteten på området sikkerhetsbestemmelser for tekstiler, og forbrukerne krever all-sidige anvendelsesmuligheter hos tekstilene. Dette har stilt tekstilindustrien på en alvorlig prøve når det gjelder den aktuelle tekstilfinish-teknologi, og spørsmålet er om den er fullgod. There has been a sharp increase in activity in the area of safety regulations for textiles, and consumers demand all-round application possibilities for textiles. This has put the textile industry to a serious test when it comes to the current textile finish technology, and the question is whether it is fully satisfactory.
Selv om tekstilbehandlingsmetoder er blitt utviklet som er egnet til å gi tekstilene ildfasthet, flekkfasthet, vannfasthet og liknende, er disse behandlingsmetoder vanligvis blitt ansett å være utilstrekkelige fordi de mangler varighet.Etterhvert som bestem-melsesaktiviteten og strengheten når det gjelder standarden øker, oppstår det også et behov for fremgangsmåter som gir forskjellige varige finisher til tekstilene. Selv de aktuelle pålagte brann-sikkerhetsbestemmelser som tekstilindustrien møter, innebærer et klart og aktuelt behov for å anvende slike fremgangsmåter. Although textile treatment methods have been developed which are suitable for giving the textiles fire resistance, stain resistance, water resistance and the like, these treatment methods have generally been considered insufficient because they lack permanence. also a need for processes that give different lasting finishes to the textiles. Even the current imposed fire safety regulations that the textile industry meets, imply a clear and current need to use such methods.
Forskjellige forhåndsfremstilte polymerer som f.eks. polyakrylater, polyvinylklorid og liknende er hittil blitt anvendt i tekstilfinish-fremgangsmåter for å gi tekstilene de ovenfor nevnte egenskaper. Et problem som har vært felles for slike finishfremgangsmåter, er at disse polymerer ikke trenger inn i fibrene, som f.eks. er av bomull, rayon og liknende, og derfor bare dekker overflaten av fibrene. Under disse omstendigheter blir polymeren fjernet ved vasking og/eller slitasje under normal bruk av tekstilene. Også når polymeren er en ganske stiv sådan, påvirkes "grepet" (kvalitet hos tekstilet når det gjelder følelsen ved å kjenne på det med hånden) for tekstilet uheldig. Videre forårsaker polymeren, siden den befinner seg på overflaten av fibrene, sammenklebing av fiber til fiber, noe som hindrer den vanlige frie bevegelse av fibrene, hvorved grepet og noen ganger styrken hos tekstilet ytterligere påvirkes. Various pre-made polymers such as polyacrylates, polyvinyl chloride and the like have hitherto been used in textile finishing processes to give the textiles the above-mentioned properties. A problem which has been common to such finishing methods is that these polymers do not penetrate into the fibres, which e.g. are of cotton, rayon and the like, and therefore only cover the surface of the fibres. Under these circumstances, the polymer is removed by washing and/or wear during normal use of the textiles. Also when the polymer is a fairly stiff one, the "grip" (quality of the textile in terms of the feeling when feeling it with the hand) of the textile is adversely affected. Furthermore, the polymer, since it is on the surface of the fibers, causes fiber to fiber adhesion, which prevents the normal free movement of the fibers, thereby further affecting the grip and sometimes the strength of the textile.
Forskjellige fremgangsmåter er tidligere anvendt for fremstilling av polymerer in situ i fibre fra ikke-polymere reaktanter. Disse er referert av Mark, Wooding og Atlas i "Chemical Various methods have previously been used for the production of polymers in situ in fibers from non-polymeric reactants. These are referenced by Mark, Wooding and Atlas in "Chemical
Aftertreatment of Textiles", Wiley-Interscience, New York (1971). Disse fremgangsmåter faller i to hovedklasser: Aftertreatment of Textiles", Wiley-Interscience, New York (1971). These methods fall into two main classes:
1) Friradikal-, in situ-polymerisasjon.1) Free radical, in situ polymerization.
Ved disse fremgangsmåter polymeriseres en vinylmonomerIn these methods, a vinyl monomer is polymerized
som f.eks. akrylsyre eller dens derivater på og om mulig inne i fibrene ved hjelp av en friradikalkatalysator til en vinylpolymer. Noen ganger følger en poding på tekstilfibrene en slik polymerisasjon, spesielt om det anvendes midler til å danne "podesteder" like for example. acrylic acid or its derivatives on and if possible inside the fibers by means of a free radical catalyst to a vinyl polymer. Sometimes a grafting on the textile fibers follows such polymerization, especially if agents are used to form "grafting sites"
på fibrene. Slike fremgangsmåter har funnet meget liten aktuell anvendelse fordi de er dyre og det er vanskelig å indusere tilstrekkelig mange podesteder på fibrene eller få det til å dannes tilstrekkelig av podepolymerer. on the fibers. Such methods have found very little current application because they are expensive and it is difficult to induce a sufficient number of grafting sites on the fibers or to cause sufficient grafting polymers to form.
2) Aminoplastdannelse.2) Aminoplast formation.
Ved disse fremgangsmåter fås -NH- og -NCH(OR)-holdige forbindelser som f.eks. ureaformaldehyd, urea-glyoksal eller melaminformaldehyd til å danne harpikser, vanligvis av en tverr-bundet type, ved hjelp av sur katalyse som får i stand dannelse av -NCH-N-bindinger og/eller at NCH-grupper festes til fiberen By these methods -NH- and -NCH(OR)-containing compounds such as e.g. urea formaldehyde, urea-glyoxal or melamine formaldehyde to form resins, usually of a cross-linked type, by means of acid catalysis which enables the formation of -NCH-N bonds and/or the attachment of NCH groups to the fiber
(hvor fiberen er reaktiv som i tilfeller hvor fibrene har -0H-(where the fiber is reactive as in cases where the fibers have -0H-
eller -NH-grupper som kan danne -NCH-N- eller -NCH-O-bindinger). or -NH groups which can form -NCH-N or -NCH-O bonds).
Vanligvis anvendes de ovenfor beskrevne fremgangsmåterGenerally, the methods described above are used
som to adskilte fremgangsmåter eller operasjorter. Eksempelvis er det kjent å påføre N-metylolakrylamid på cellulosetekstiler, hvor- as two separate procedures or surgical procedures. For example, it is known to apply N-methylolacrylamide to cellulose textiles, where
ved amidet festes til cellulosen via syrekatalysert aminoplast,when the amide is attached to the cellulose via acid-catalyzed aminoplast,
og deretter, som en adskilt operasjon, å anvende høy-energibestrå-ling for å indusere friradikalpolymerisasjon av dobbeltbindingene. and then, as a separate operation, using high energy irradiation to induce free radical polymerization of the double bonds.
(Se f.eks. W. Walsh, US-PS 3.434.161). Denne fremgangsmåte har(See, e.g., W. Walsh, US-PS 3,434,161). This method has
ikke funnet kommersiell anvendelse, hovedsakelig fordi det er innbefattet spesiell bestrålingsapparatur. not found commercial application, mainly because it involves special irradiation equipment.
Det er også kjent på forhånd å feste en ønsket gruppe,It is also known in advance to attach a desired group,
som f.eks. (CH30)2P(0)CH2CH2CONHCH2OH (som iDT-PS 1.495.383)like for example. (CH3O)2P(0)CH2CH2CONHCH2OH (as iDT-PS 1,495,383)
eller en melaminharpiks (som i GB-PS 779.231) til en vinylmonomer-gruppe ved hjelp av aminoplast (syrekatalysert), og slike mono- or a melamine resin (as in GB-PS 779,231) to a vinyl monomer group using aminoplast (acid catalyzed), and such mono-
merer kunne antagelig deretter påføres i et friradikal-herdetrinn på tekstilet. Men også her er det innbefattet to adskilte fremgangsmåter (operasjoner). more could presumably then be applied in a free-radical hardening step to the textile. But here too, two separate procedures (operations) are included.
Det er også kjent (Kamogawa et al, JA-PS 363.142, rap-portert av Mark et al, se ovenfor, s. 2 60) at N-metylolakrylamid både kan polymeriseres og kondenseres i bomull. Det er imidlertid ikke gjort bruk av dette reaksjonsskjerna for å binde en med-reaktant til tekstilet for å gi tekstilet et stort antall finish-egenskaper. It is also known (Kamogawa et al, JA-PS 363,142, reported by Mark et al, see above, p. 260) that N-methylolacrylamide can be both polymerized and condensed in cotton. However, this reaction core has not been used to bind a co-reactant to the textile to give the textile a large number of finish properties.
Foreliggende oppfinnelse skiller seg fra det som er kjent og beskrevet ovenfor ved at den anvender både friradikal- og syre-katalysert kondensasjonskjemi samtidig, dvs. et enkelt fremgangs-måtetrinn som anvender en katalysator eller kombinasjon av katalysatorer med både friradikal- og syrekatalyse-egenskaper, slik at det dannes nye polymere tekstilfinisher. I de nye tekstilfinishene ansees de polymere nettverk hele tiden å være basert på C-C-bindinger dannet ved friradikalpolymerisasjon så vel som bindinger dannet ved syre-katalysert kondensasjonspolymerisasjon mellom poly-merkjedene og/eller mellom polymerkjeder og fiberen og/eller mellom polymerkjeder og nyttige sidekjeder. Siden oppfinnelsen anvender reaktanter med lave molekylvekter i motsetning til polymeren fra de tidligere kjente fremgangsmåter på området angitt i 1) ovenfor, er det mulig å oppnå god fibergjennomtrengning og varige finisher med godt grep. Siden fremgangsmåten ifølge oppfinnelsen bare krever ett reaksjonstrinn, er den økonomisk fordelaktig sam-menlignet med de tidligere på området anvendte to-trinns- eller fleretrinnsfremgangsmåter. The present invention differs from what is known and described above in that it uses both free-radical and acid-catalyzed condensation chemistry at the same time, i.e. a simple process step that uses a catalyst or combination of catalysts with both free-radical and acid catalysis properties, so that new polymeric textile finishes are formed. In the new textile finishes, the polymeric networks are always considered to be based on C-C bonds formed by free radical polymerization as well as bonds formed by acid-catalyzed condensation polymerization between the polymer chains and/or between polymer chains and the fiber and/or between polymer chains and useful side chains. Since the invention uses reactants with low molecular weights in contrast to the polymer from the previously known methods in the area indicated in 1) above, it is possible to achieve good fiber penetration and lasting finishes with good grip. Since the method according to the invention only requires one reaction step, it is economically advantageous compared to the two-step or multi-step methods previously used in the area.
Det er derfor et formål med foreliggende oppfinnelse å skaffe en fremgangsmåte som gir tekstiler mange forskjellige varige finisher. It is therefore an object of the present invention to provide a method which gives textiles many different lasting finishes.
Det er et annet formål med oppfinnelsen å skaffe en in situ-, ett-trinnsfremgangsmåte for finishbehandling av tekstiler hvor tekstiler ved passende valg av reaktanter kan gis varige finisher av mange slag. It is another object of the invention to provide an in-situ, one-step process for the finishing treatment of textiles where, by suitable choice of reactants, textiles can be given lasting finishes of many kinds.
Disse, så vel som andre formål, oppnås ved foreliggende oppfinnelse som skaffer en fremgangsmåte for frembringelse av vaskefast finish på tekstiler som omfatter å påføre på tekstilene en effektiv mengde av minst en friradikalpolymeriserbar monomer med en funksjonell gruppe som kan gjennomgå en syre-katalysert kon-densas jonsreaksjon med minst en ko-reaktant med reaktive metylol-, hydroksy-, alkoksy- eller aminogrupper istand til å gjennomgå syre-katalysert kondensasjon med en reaktiv metylolgruppe på nevnte friradikalpolymeriserbare monomer, sammen med en friradikalgenererende katalysator og en syre-katalysator eller en enkelt katalysator med både friradikal- og syre-katalysatorkarakter og å underkaste nevnte tekstil for herdebetingelser for samtidig å gjennomføre friradikalpolymerisasjon og syre-katalyserte kondensasjonsreaksjoner. These, as well as other objects, are achieved by the present invention which provides a method for producing a wash-resistant finish on textiles which comprises applying to the textiles an effective amount of at least one free radical polymerizable monomer with a functional group capable of undergoing an acid-catalyzed con- densa's ion reaction with at least one co-reactant with reactive methylol, hydroxy, alkoxy or amino groups capable of undergoing acid-catalyzed condensation with a reactive methylol group on said free radical polymerizable monomer, together with a free radical generating catalyst and an acid catalyst or a single catalyst with both free-radical and acid-catalyst character and subjecting said textile to curing conditions in order to simultaneously carry out free-radical polymerization and acid-catalyzed condensation reactions.
Et løsningsmiddel som f.eks. vann, alkohol, perkloretylen, metylkloroform eller liknende kan anvendes om ønsket, som en bærer for disse reaktanter og katalysatorer. A solvent such as water, alcohol, perchlorethylene, methyl chloroform or the like can be used if desired, as a carrier for these reactants and catalysts.
Egnede friradikalpolymeriserbare monomerer med funksjonelle grupper som er i stand til å reagere under syre-katalyserte aminoplast-dannende betingelser med en ko-reaktant med reagerende metylol-, hydroksy-, alkoksy- eller aminogrupper, omfatter akryl- Suitable free radical polymerizable monomers having functional groups capable of reacting under acid-catalyzed aminoplast-forming conditions with a co-reactant having reactive methylol, hydroxy, alkoxy or amino groups include acrylic-
amid, metakrylamid, N-metylolakrylamid, N-metylolmetakrylamid, N-(alkoksymetyl)akrylamid, diacetonakrylamid, dvs. amide, methacrylamide, N-methylolacrylamide, N-methylol methacrylamide, N-(Alkoxymethyl)acrylamide, diacetoneacrylamide, i.e.
CH2=CHCONHC(CH3)2CH2COCH3, de metylolerte produkter av diacetonakrylamid, og 2-hydroksyetylakrylat og 2-hydroksyetylmetakrylat. CH2=CHCONHC(CH3)2CH2COCH3, the methylolated products of diacetoneacrylamide, and 2-hydroxyethyl acrylate and 2-hydroxyethyl methacrylate.
Den foretrukne monomer er, på grunn av fordelaktig kombinasjon av lav pris, lav flyktighet og høy aktivitet, N-metylolakrylamid.Innen klassen av mSnomerer egnet for anvendelse ved fremgangsmåten ifølge oppfinnelsen, kan to underklasser utskilles: The preferred monomer is, due to the advantageous combination of low price, low volatility and high activity, N-methylolacrylamide. Within the class of monomers suitable for use in the method according to the invention, two subclasses can be distinguished:
a) de som har passende funksjonalitet til å tillate dema) those that have the appropriate functionality to allow them
å reagere under syre-katalyserte betingelser med en -0H-, O-alkyl-eller -NH-gruppe til å danne C-0- eller C-N-bindinger, og en slik funksjonalitet omfattes av uttrykket "reaktive metylolforbindelser", eksemplifisert med forbindelser som har metylolgrupper eller etere eller estere derav (dvs. ved -N(CH2OH)-, -N(CH20-alkoksy)-, -N(CH2~O-acyloksy)- og C(=0)C-CH2OH-grupper, og to react under acid-catalyzed conditions with an -OH-, O-alkyl or -NH group to form C-O or C-N bonds, and such functionality is encompassed by the term "reactive methylol compounds", exemplified by compounds such as have methylol groups or ethers or esters thereof (i.e. by -N(CH2OH)-, -N(CH2O-alkyloxy)-, -N(CH2~O-acyloxy)- and C(=0)C-CH2OH groups, and
b) de som ikke i og for seg er reaktive metylolforbindelser, men som inneholder -0H-, -0-alkyl- eller -NH-grupper som b) those which are not in and of themselves reactive methylol compounds, but which contain -OH-, -O-alkyl- or -NH groups which
kan gjennomgå syre-katalyserte kondensasjonsreaksjoner med re.ak-tive metylolforbindelser. can undergo acid-catalyzed condensation reactions with reactive methylol compounds.
Undergruppe a) eksemplifiseres ved N-metylolakrylamid, N-metylolmetakrylamid, N-(alkoksymetyl)akrylamid, N-(alkoksy-metyl) metakrylamid og metyloleringsproduktene av diacetonakryl- Subgroup a) is exemplified by N-methylol acrylamide, N-methylol methacrylamide, N-(Alkoxymethyl)acrylamide, N-(Alkoxymethyl) methacrylamide and the methylolation products of diacetonacryl-
amid, mens undergruppe b) er eksemplifisert ved akrylamid, metakrylamid, diacetonakrylamid, 2-hydroksyetylakrylat og 2-hydroksyetylmetakrylat. amide, while subgroup b) is exemplified by acrylamide, methacrylamide, diacetonacrylamide, 2-hydroxyethyl acrylate and 2-hydroxyethyl methacrylate.
En effektiv mengde av den friradikalpolymeriserbare monomer vil vanligvis ligge i området fra 2 til 50%, og fortrinnsvis An effective amount of the free radical polymerizable monomer will usually be in the range from 2 to 50%, and preferably
fra 3 til 40%, beregnet på vekten av tekstilstoffet.from 3 to 40%, calculated on the weight of the textile fabric.
Reaktanter som er i stand til å reagere sammen under syre-katalyserte kondensasjonsreaksjonsbetingelser, kan likeledes oppdeles i to underklasser: a) de som har reaktive -0H-, -O-alkyl- eller -NH-grupper som er i stand til syre-katalysert kondensasjonsreaksjon med reaktive metylolgrupper, men som ikke i og for seg er reaktive metylolforbindelser, og b) de som i og for seg er reaktive metylolforbindelser og som kan reagere både med reaktive metylolgrupper hos monomeren Reactants capable of reacting together under acid-catalyzed condensation reaction conditions can likewise be divided into two subclasses: a) those having reactive -OH-, -O-alkyl- or -NH groups capable of acid-catalyzed condensation reaction with reactive methylol groups, but which are not in and of themselves reactive methylol compounds, and b) those which are in and of themselves reactive methylol compounds and which can react both with reactive methylol groups of the monomer
(eller dens polymer) eller som kan reagere med -0H- eller -NH-grupper i monomerenheter som ikke i og for seg har reaktive metylolgrupper. (or its polymer) or which can react with -OH or -NH groups in monomer units that do not have reactive methylol groups per se.
Klasse a) omfatter alkoholer, spesielt primære alkoholer, primære og sekundære aminer og amider med -NH-grupper, aminoalkyl-substituerte polysiloksansilanoler og alkoksysilaner som kan hydro-lysere til silanoler. Class a) includes alcohols, especially primary alcohols, primary and secondary amines and amides with -NH groups, aminoalkyl-substituted polysiloxanesilanols and alkoxysilanes which can hydrolyse to silanols.
Klasse b) omfatter metylolamider, metylolmelaminer, metylolureastoffer, metylolkarbonater, metylolguanidiner, metylol-dicyandiamider, glyoksalurinstoff-addukter og etere og estere av disse, og kvartære alkyleringsmidler av typen R" ^NC^NHCOR' (hvor R' og R" begge kan være alkyl eller R^N kan representere en pyridinring). Class b) includes methylolamides, methylolmelamines, methylolureas, methylolcarbonates, methylolguanidines, methylol dicyandiamides, glyoxalurea adducts and ethers and esters thereof, and quaternary alkylating agents of the type R" ^NC^NHCOR' (where R' and R" can both be alkyl or R^N may represent a pyridine ring).
En effektiv mengde av ko-reaktanten vil vanligvis liggeAn effective amount of the co-reactant will usually lie
i området fra 2 til 50, og mer foretrukket fra 3 til 40%, beregnet på vekten av tekstilstoffet. in the range from 2 to 50, and more preferably from 3 to 40%, calculated on the weight of the textile fabric.
Friradikalkatalysatorer som kan anvendes, innbefatter organiske og uorganiske peroksyforbindelser og azoforbindelser, eksempelvis persulfater, perfosfatsalter, t-butylhydroperoksyder, di-t-butylperoksyd, kumenhydroperoksyd, metyletylketonperoksyd, benzoylperoksyd, t-butylperoksysuksinat, t-butylperbenzoat, azobis-isobutyronitril og azobis-isovaleronitril. Foretrukne katalysatorer er på grunn av vannløselighet og evne til også å ticene som sure katalysatorer, de vannløselige persulfater, som f.eks. ammo-nium-, natrium- og kaliumpersulfat. Free radical catalysts that can be used include organic and inorganic peroxy compounds and azo compounds, for example persulfates, perphosphate salts, t-butyl hydroperoxides, di-t-butyl peroxide, cumene hydroperoxide, methyl ethyl ketone peroxide, benzoyl peroxide, t-butyl peroxysuccinate, t-butyl perbenzoate, azobis-isobutyronitrile and azobis-isovaleronitrile. Preferred catalysts are, due to their water solubility and ability to also act as acid catalysts, the water-soluble persulphates, such as e.g. ammonium, sodium and potassium persulphate.
Sure katalysatorer som kan anvendes, omfatter salt-, svovel-, fluorbor-, eddik-, melke-, glykol-, sitron-, vin- og oksalsyre, sure salter som f.eks. magnesiumklorid, ammoniumklorid, sinkklorid, magnesiumnitrat, -fluorborat eller -fluorsilikat, sink-nitrat, -fluorborat eller -fluorsilikat, aminohydroklorider, natriumbisulfatvikaliumbisulfat, monoammoniumfosf at og liknende. Acid catalysts that can be used include hydrochloric, sulphurous, fluoroboric, acetic, lactic, glycolic, citric, tartaric and oxalic acid, acid salts such as magnesium chloride, ammonium chloride, zinc chloride, magnesium nitrate, -fluoroborate or -fluorosilicate, zinc nitrate, -fluoroborate or -fluorosilicate, aminohydrochlorides, sodium bisulfate, potassium bisulfate, monoammonium phosphate and the like.
Det er imidlertid ansett mest fordelaktig å anvende et persulfatsalt som samtidig danner den sure så vel som friradikal-katalysatoren som kreves ved fremgangsmåten ifølge oppfinnelsen. However, it is considered most advantageous to use a persulphate salt which simultaneously forms the acid as well as the free radical catalyst required by the process according to the invention.
En effektiv mengde katalysator ligger vanligvis i området fra ca. 0,01 til 10 vekt% av reaktantene, og fortrinnsvis mellom 0,05 og 5%. An effective amount of catalyst is usually in the range from approx. 0.01 to 10% by weight of the reactants, and preferably between 0.05 and 5%.
Ko-reaktanter av klasse a) ovenfor omfatter primære alkoholer inneholdende fosfor, som f.eks. pentavalente fosforestere inneholdende primære alkoholgrupper som angitt i søkerens US-søknad nr. som ble innlevert på samme dag som denne søknad, (HOCH2)3PO,(HOCH2)2P(0)CH2[0CH2P(0)(CH20H)CH2]OH, HO-alkylen-P0(0R)2 o.l., aminer, f.eks. NH2CH3~a(CH3)aP0(0-alkyl)2, fosfor-holdige amider, f.eks. NH2C(0)CH2CH2P(0)(0CH3)2, (NH-[alkyl eller H] 1 2p(°)(0-alkyl)2 PO(NH2)3, PO(NH-alkyl)3, [P(0)(CH3)NHCH2CH2NH-]x, [P(0)(CH3)OCH2CH2NH]x, sulfonamider, f.eks. NH2S02NH2, NH2S03H, og NH2S03NH4, og brom-holdige reaktanter som f.eks. HOCH2NHCOOCH2CHBrCH2Br eller H0CH2C(CH2Br)2CH2OH. Foretrukne eksempler på grunn av kommersiell tilgjengelighet er PO(NHCH3)3, NH2S03NH4, og (HOCH2CH2)2NCH2P(°) (°C2H5*2 * Co-reactants of class a) above include primary alcohols containing phosphorus, such as e.g. pentavalent phosphorous esters containing primary alcohol groups as set forth in Applicant's US Application No. which was filed on the same date as this application, (HOCH2)3PO,(HOCH2)2P(0)CH2[0CH2P(0)(CH20H)CH2]OH, HO -alkylene-P0(OR)2 and the like, amines, e.g. NH2CH3~a(CH3)aP0(O-alkyl)2, phosphorus-containing amides, e.g. NH2C(0)CH2CH2P(0)(0CH3)2, (NH-[alkyl or H] 1 2p(°)(0-alkyl)2 PO(NH2)3, PO(NH-alkyl)3, [P(0 )(CH3)NHCH2CH2NH-]x, [P(0)(CH3)OCH2CH2NH]x, sulfonamides, e.g., NH2S02NH2, NH2S03H, and NH2S03NH4, and bromine-containing reactants such as HOCH2NHCOOCH2CHBrCH2Br or H0CH2C(CH2Br) 2CH2OH. Preferred examples due to commercial availability are PO(NHCH3)3, NH2SO3NH4, and (HOCH2CH2)2NCH2P(°) (°C2H5*2 *
De mengder som kreves for å gi flammehemmende egenskaper, er slike som får 0,5 til 5% fosfor eller svovel til å festes til stoffet. The amounts required to provide flame retardant properties are such as to cause 0.5 to 5% phosphorus or sulfur to attach to the fabric.
Ko-reaktanter av klasse b) ovenfor omfatter hydroksy-metylerte eller alkoksymetylerte triazinylaminoalkylfosfonater som f.eks. de fra søkerens US-PS 3.755.323 eller fra Tesoro's US-PS 3.551.422 (1970), metylolerte amidfosfonater som f.eks. HOCH2NHCOCH2CH2P(0)(0CH3)2eller metylolert NH2C0-0-alkylen-P0(0-alkyl)2. Co-reactants of class b) above comprise hydroxy-methylated or alkoxy-methylated triazinylaminoalkylphosphonates such as e.g. those of applicant's US-PS 3,755,323 or of Tesoro's US-PS 3,551,422 (1970), methylolated amide phosphonates such as HOCH2NHCOCH2CH2P(0)(0CH3)2 or methylolated NH2C0-0-alkylene-P0(0-alkyl)2.
Ko-reaktanter av type a) som kan anvendes for å gi vann-frastøtende og myknende egenskaper, omfatter langkjedede ( C§~ C22^ ~ primære alkoholer eller aminer, som f.eks. oktyl-, dodecyl-, heksadecyl- og eikosylalkohol, langkjedede amider som f.eks. kaproamid eller stearamid, fettsyredietanolamider, monoglycerider, polyfluoralkylalkoholer eller -aminer, amider av polyfluorerte fettsyrer, polyfluorerte alkylsulfonamider, eller silanoler eller alkoksysilaner som hydrolyserer til silanoler eller aminoalkyl-substituerte polysiloksaner. Co-reactants of type a) which can be used to provide water-repellent and softening properties, include long-chain (C§~ C22^ ~ primary alcohols or amines, such as, for example, octyl, dodecyl, hexadecyl and eicosyl alcohol, long-chain amides such as caproamide or stearamide, fatty acid diethanolamides, monoglycerides, polyfluoroalkyl alcohols or amines, amides of polyfluorinated fatty acids, polyfluorinated alkylsulfonamides, or silanols or alkoxysilanes which hydrolyze to silanols or aminoalkyl-substituted polysiloxanes.
Ko-reaktanter av type b) som kan anvendes for å gi vann-frastøtende og myknende egenskaper, omfatter N-metylolerte, lang kjedede fettsyreamider, også N-metylolerte, langkjedede alkylurin-stoffer, foretrede metylolmelaminer inneholdende minst én lang kjede, kvartære, ammoniometylerte, langkjedede fettsyreamider som f.eks. N-(stearamidometyl)pyridiniumsalter, kvartære, ammoniometylerte, langkjedede alkoholer som f.eks. N-(oktadecyloksymetyl)-pyridiniumsalter, 3,6-dioksatetrakosyloksymetylenpyridiniumsalter eller stearatoetoksymetylpyridiniumsalter. Disse kvartære salter er vannløselige ekvivalenter til de tilsvarende metylolforbindelser. Co-reactants of type b) which can be used to provide water-repellent and softening properties include N-methylolated, long-chain fatty acid amides, also N-methylolated, long-chain alkylureas, etherified methylolmelamines containing at least one long chain, quaternary, ammoniomethylated , long-chain fatty acid amides such as N-(stearamidomethyl)pyridinium salts, quaternary, ammoniomethylated, long-chain alcohols such as e.g. N-(octadecyloxymethyl)-pyridinium salts, 3,6-dioxatetracosyloxymethylenepyridinium salts or stearate ethoxymethylpyridinium salts. These quaternary salts are water-soluble equivalents of the corresponding methylol compounds.
Anti-flekkegenskaper kan oppnås ved å anvende som ko-reaktanter karboksymetylcellulose, hydroksyetylcellulose, hydroksy-avsluttede poly(alkylenamider), glykolsyre, polyfluoralkylaminer, polyfluoralkanoler eller polyfluoralkanamider. Anti-stain properties can be achieved by using as co-reactants carboxymethyl cellulose, hydroxyethyl cellulose, hydroxy-terminated poly(alkylene amides), glycolic acid, polyfluoroalkylamines, polyfluoroalkanols or polyfluoroalkanamides.
Antistatiske egenskaper kan oppnås ved å anvende som ko-reaktanter hydroksy-avsluttede poly(alkylenoksyd), polyetoksylerte alkylfenoler og polyetoksylerte glycerider. Antistatic properties can be achieved by using as co-reactants hydroxy-terminated poly(alkylene oxide), polyethoxylated alkylphenols and polyethoxylated glycerides.
Tverrbinding, som gir skrukke-fasthet eller varige press-egenskaper, kan oppnås ved å anvende som ko-reaktanter ved fremgangsmåten ifølge oppfinnelsen slike reaktive metylolforbindelser som f.eks. metylolerte urinstoffer, cykliske urinstoffer, uroner, triazoner, melaminer, dicyandiamider og uretaner eller etere eller estere derav. Eksempler er dimetylolurea, dimetyloletylenurea, dimetylolpropylenurea, dimetylolmetyluron, dimetoksymetyletylen-urea, metylolmelamin, dimetylolmelamin, trimetylolmelamin, penta-metylolmelamin, heksametylolmelamin (eller de delvis eller fullstendig foretrede derivater derav som f.eks. pentametoksymetyl-melamin), dimetylolmetylkarbamat, dimetylisobutylkarbamat, tris(N-metylol-2-karbamoyletyl)amin, trimetylolglyoksaldiurein, dimetyloldihydroksyetylenurea og dimetyloldicyandiamid. Cross-linking, which gives wrinkle resistance or lasting pressure properties, can be achieved by using as co-reactants in the method according to the invention such reactive methylol compounds as e.g. methylolated ureas, cyclic ureas, urones, triazones, melamines, dicyandiamides and urethanes or ethers or esters thereof. Examples are dimethylolurea, dimethylolethyleneurea, dimethylolpropyleneurea, dimethylolmethyluron, dimethoxymethylethylene urea, methylolmelamine, dimethylolmelamine, trimethylolmelamine, pentamethylolmelamine, hexamethylolmelamine (or the partially or fully etherified derivatives thereof such as pentamethoxymethylmelamine), dimethylolmethylcarbamate, dimethylisobutylcarbamate, tris( N-methylol-2-carbamoylethyl)amine, trimethylolglyoxaldiurein, dimethyloldihydroxyethyleneurea and dimethyloldicyandiamide.
Når den monomer som kan herdes ved friradikalkatalyse, er en som har reaktive metylolgrupper,, som f. eks.- N-metylolakrylamid eller hydroksymetylert diacetonakrylamid, kan ko-reaktanten være av ovennevnte type eller kan være av typen a) som f.eks. en umetylolert urea, etylenurea, propylenurea eller en annen cyklisk urea, melamin, dicyandiamid, cyanamid, uretan eller laktamid. When the monomer that can be cured by free radical catalysis is one that has reactive methylol groups, such as, for example, N-methylolacrylamide or hydroxymethylated diacetoneacrylamide, the co-reactant can be of the above-mentioned type or can be of the type a) such as, for example an unmethylolated urea, ethyleneurea, propyleneurea or another cyclic urea, melamine, dicyandiamide, cyanamide, urethane or lactamide.
Når de anvendes sammen med fosfor- eller svovelholdige flammehemmende ko-reaktanter, synergiserer disse nitrogenholdige ko-reaktanter den flammehemmende virkning av fosfor eller svovel. When used together with phosphorus or sulfur containing flame retardant co-reactants, these nitrogen containing co-reactants synergize the flame retardant effect of phosphorus or sulfur.
Synergistiske flammehemmende egenskaper oppnås også vedSynergistic flame retardant properties are also achieved by
å anvende silanoler eller alkoksysiloksaner som kan hydrolyseres to use silanols or hydroxysiloxanes which can be hydrolysed
til silanoler som ko-reaktanter som kan gjennomgå syre-katalysert ko-reaksjon med monomerenheter med metylolreagenskarakter. to silanols as co-reactants that can undergo acid-catalyzed co-reaction with monomer units of methylol reagent character.
Spesielt effektive er silanoler eller silikoner med primære alkoholgrupper, amino- eller amidogrupper. Particularly effective are silanols or silicones with primary alcohol groups, amino or amido groups.
Når den ko-reagerende metylolforbindelse har to typer av funksjonelle grupper som avviker i graden av syre-katalysert reak-tivitet, kan fremgangsmåten ifølge oppfinnelsen anvendes som det første trinn i en fremgangsmåte for frembringelse av permanent press. Ved eksempelvis å anvende N-metylolakrylamid og dimetyloldihydroksyetylenurea som monomer og ko-reaktant og anvende tilstrekkelig lav temperatur til å unngå fullstendig reaksjon av de funksjonelle gruppene av dimetyloldihydroksyetylenurea, oppnås en finish som tillater at materialet kan klippes og presses og deretter utsettes for en endelig, kraftigere herding som da gir en permanent press-finish. When the co-reacting methylol compound has two types of functional groups that differ in the degree of acid-catalyzed reactivity, the method according to the invention can be used as the first step in a method for producing permanent pressure. By, for example, using N-methylolacrylamide and dimethyloldihydroxyethyleneurea as monomer and co-reactant and using a sufficiently low temperature to avoid complete reaction of the functional groups of dimethyloldihydroxyethyleneurea, a finish is obtained that allows the material to be cut and pressed and then subjected to a final, stronger hardening which then gives a permanent press finish.
Fremgangsmåten ifølge oppfinnelsen kan gjennomføres vedThe method according to the invention can be carried out by
å anvende reaktantene i enhver av de metoder som er kjent på tekstilfinishbehandlingsområdet, som f.eks. stopping, spraying, aerosolspraying, påføring med en "kyssevalse" eller ved trykking. to use the reactants in any of the methods known in the textile finishing treatment field, such as e.g. stopping, spraying, aerosol spraying, application with a "kissing roller" or by pressing.
Alle typer av tekstiler kan behandles ved hjelp av fremgangsmåten ifølge oppfinnelsen for å gi dem varige finisher. Så-ledes kan det behandles tekstiler oppnådd fra naturfibrer som f.eks. bomull, ull, silke, sisal, jute, hamp og lin, og fra syntetiske fibrer omfattende nylon og andre polyamider, polyolefiner som f.eks. polypropylen, polyestere som f.eks. polyetylentereftalat, cellulosefibrer som f.eks. rayon, celluloseacetat og -triacetat, glassfibrer, akryl- og modakrylfibrer, dvs. fibrer som er basert på akrylonitrilkopolymerer, saranfibrer, dvs. fibrer som er basert på vinylidenkloridkopolymerer, nytrilfibrer, dvs. fibrer som er basert på vinylidendinitrilkopolymerer, gummibaserte fibrer, spandex-fibrer, dvs. fibrer som er basert på segmentert polyuretan, vinyl-fibrer, dvs. fibrer som er basert på vinylalkoholkopolymerer, vinyonfibrer, dvs. fibrer som er basert på vinylkloridkopolymerer, og metalliske fibrer. Tekstiler som er oppnådd fra blandinger av hvilke som helst av de ovennevnte natur- og/eller syntetiske All types of textiles can be treated using the method according to the invention to give them lasting finishes. In this way, textiles obtained from natural fibers such as e.g. cotton, wool, silk, sisal, jute, hemp and linen, and from synthetic fibers including nylon and other polyamides, polyolefins such as polypropylene, polyesters such as polyethylene terephthalate, cellulose fibers such as rayon, cellulose acetate and triacetate, glass fibers, acrylic and modacrylic fibers, i.e. fibers based on acrylonitrile copolymers, saran fibers, i.e. fibers based on vinylidene chloride copolymers, nytril fibers, i.e. fibers based on vinylidene dinitrile copolymers, rubber-based fibers, spandex- fibers, i.e. fibers based on segmented polyurethane, vinyl fibers, i.e. fibers based on vinyl alcohol copolymers, vinylon fibers, i.e. fibers based on vinyl chloride copolymers, and metallic fibers. Textiles obtained from mixtures of any of the above natural and/or synthetic
fibrer, kan også behandles ved hjelp av fremgangsmåten ifølge oppfinnelsen. fibres, can also be treated using the method according to the invention.
Slik det anvendes her, betyr uttrykket "tekstil" eller "tekstiler" vevede eller strikkede stoffer så vel som ikke-vevede stoffer som består av kontinuerlige og/eller diskontinuerlige fibrer som er sammenbundet slik at de danner et stoff ved mekanisk vikling, termisk mellomfiberbinding eller ved anvendelse av lim-eller bindesubstanser. As used herein, the term "textile" or "textiles" means woven or knitted fabrics as well as non-woven fabrics consisting of continuous and/or discontinuous fibers joined together to form a fabric by mechanical winding, thermal inter-fiber bonding or when using glue or binding substances.
Det skal også bemerkes på dette punkt at i tillegg til å anvendes for å gi varige finisher til tekstiler, kan finishfrem-gangsmåten ifølge oppfinnelsen anvendes for å gi varige finisher til forskjellige substrater som f.eks. cellulose i form av papir, tre, finer, sponplater, jute, "batting" og liknende, uretanskum, rebundne uretanbelegg, elastomerer og liknende. It should also be noted at this point that in addition to being used to provide durable finishes to textiles, the finishing method according to the invention can be used to provide durable finishes to various substrates such as e.g. cellulose in the form of paper, wood, veneer, chipboard, jute, "batting" and the like, urethane foam, rebonded urethane coatings, elastomers and the like.
Herding kan gjennomføres ved enhver behandling som star-ter både friradikal- og syre-katalyserte reaksjoner. Vanligvis vil dette foregå ved å anvende varme i området fra 50 til 200°C. Lavere temperaturer kan anvendes, men problemet med for lange herdetider dersom det anvendes en meget reaktiv katalysator, er at stabiliteten for behandlingsløsningene kan bli dårlig. Høyere temperaturer kan forårsake skader på stoffene. Herdetider på fra noen sekunder ved høyere temperaturer til noen få dager ved lavere temperaturer anvendes. Fagmannen vil forstå at den nødvendige tid lett kan bestemmes ved rutineforsøk i ethvert gitt utstyr, hvor tiden varieres oppover inntil det finnes at en adekvat herding er oppnådd, noe som viser seg ved vaskefastheten for finishen. Den aktuelle tid vil være en funksjon av katalysatorvalg og -mengde, stofftype, varmeoverføringsegenskaper for utstyret, nærværet av farvestoffer og andre ingredienser på stoffet eller i finishen, fuktighetsinnhold i stoffet og andre variabler som er velkjente på området. Curing can be carried out by any treatment that starts both free-radical and acid-catalysed reactions. Usually this will take place by applying heat in the range from 50 to 200°C. Lower temperatures can be used, but the problem with too long curing times if a highly reactive catalyst is used is that the stability of the treatment solutions can be poor. Higher temperatures can cause damage to the materials. Curing times of from a few seconds at higher temperatures to a few days at lower temperatures are used. The person skilled in the art will understand that the required time can easily be determined by routine testing in any given equipment, where the time is varied upwards until it is found that adequate curing has been achieved, which is shown by the washing fastness of the finish. The appropriate time will be a function of catalyst selection and amount, fabric type, heat transfer characteristics of the equipment, presence of dyes and other ingredients on the fabric or in the finish, moisture content of the fabric, and other variables well known in the art.
Den samtidige radikal-syrekatalyserte herding kan også frembringes ved anvendelse av en katalysatoraktivator, som f.eks. svoveldioksyd som frembringer en "redoks"-reaksjon med den frie radikal-initiatoren av peroksydtypen og også frembringer en sur reaksjon ved hjelp av svovelsyrling og svovelsyre som dannes på stoffet. The simultaneous radical-acid-catalyzed curing can also be produced by using a catalyst activator, such as e.g. sulfur dioxide which produces a "redox" reaction with the peroxide type free radical initiator and also produces an acidic reaction by means of sulfuric acid and sulfuric acid being formed on the substance.
Når varme er det middel som anvendes, kan den tilføresWhen heat is the agent used, it can be added
ved bestråling (som f.eks. ved varmelamper), konveksjon (som i en ovn), ledning (som ved hjelp av varmevalser) eller ved pådamping eller påføring av annen oppvarmet gass på eller gjennom stoffet.Friradikaldelen av reaksjonen kan fremmes ved samtidig anvendelse by irradiation (such as by heat lamps), convection (such as in an oven), conduction (such as by heating rollers) or by vaporization or application of another heated gas to or through the substance. The free radical part of the reaction can be promoted by simultaneous application
av aktinisk stråling som f.eks. ved ultrafiolett lys, koronautlad-ning, elektronstråling eller gammastråling. of actinic radiation such as by ultraviolet light, corona discharge, electron radiation or gamma radiation.
For ytterligere å illustrere oppfinnelsen gis følgende eksempler- Disse eksempler er bare illustrerende og skal ikke opp-fattes som en begrensning av oppfinnelsen. Om ikke annet er angitt, er alle prosenter og vekter angitt etter vekt. To further illustrate the invention, the following examples are given - These examples are only illustrative and should not be understood as a limitation of the invention. Unless otherwise stated, all percentages and weights are given by weight.
Eksempel 1Example 1
Dette eksempel illustrerer fremstilling av en vannav-støtende og stoffmyknende finish in situ på bomull. This example illustrates the production of a water repellency and fabric softening finish in situ on cotton.
Et preparat lages med følgende sammensetning:A preparation is made with the following composition:
Bomullsduk dynkes til 70%-ig fuktighetsopptak og tørkes ved 60 til 70°C, og oppvarmes så til 150°C i 5 minutter for å gjennomføre herding.'Det resulterende stoff oppviser varige vannavstøtende egenskaper og mykt grep. Cotton fabric is soaked to 70% moisture absorption and dried at 60 to 70°C, then heated to 150°C for 5 minutes to effect curing.'The resulting fabric exhibits durable water-repellent properties and a soft grip.
Eksempel 2Example 2
Dette eksempel illustrerer tilveiebringelse av permanent press-finish i bomullstøy ved en forsinket herding. This example illustrates the provision of a permanent press finish in cotton fabric by a delayed cure.
Et vandig preparat med følgende sammensetning fremstilles: An aqueous preparation with the following composition is prepared:
Et bredt bomullstøy fuktes til 75%-ig fuktighetsopptak og oppvarmes så til 120°C i 2 minutter for å gjennomføre tørking og noe herding, men meget lite tverrbinding (noe som viser seg ved at stoffet er lett å klippe og sy). Stoffet klippes så og syes til klær som presses ved 145 til 150°C. Herdingen fullføres så for å gjennomføre tverrbindingen ved 165 til 170°C i 3 minutter. Den ferdige artikkel beholder sin press og skrukk-fasthet ved vanlig bruk og vask. A broad cotton fabric is moistened to 75% moisture absorption and then heated to 120°C for 2 minutes to effect drying and some curing, but very little cross-linking (which is shown by the fabric being easy to cut and sew). The fabric is then cut and sewn into clothes that are pressed at 145 to 150°C. Curing is then completed to effect crosslinking at 165 to 170°C for 3 minutes. The finished article retains its pressure and wrinkle resistance with normal use and washing.
Eks empel 3Example 3
Dette eksempel illustrerer fremstilling av en flammehemmende finish in situ på bomull. This example illustrates the production of a flame retardant finish in situ on cotton.
Det lages tre finishløsninger som følger:Three finish solutions are made as follows:
Bomull (129 g/m<2>flanell) fuktes til 101-102% fuktighetsopptak, tørkes i 1,5 minutter ved 121°C og herdes i 1 minutt ved 177°C. Etter vasking med vann ble stoffet funnet å passere Federal Vertical Flammability Test DOC FF-3-71 med 7,5-10 cm brennelengde. Cotton (129 g/m<2>flannel) is moistened to 101-102% moisture absorption, dried for 1.5 minutes at 121°C and cured for 1 minute at 177°C. After washing with water, the substance was found to pass the Federal Vertical Flammability Test DOC FF-3-71 with 7.5-10 cm burn length.
Etter ti gangers vasking med vaskemiddel klarte bare tøyet behån-diet med preparatene A og C testen, noe som indikerte nødvendig-heten av friradikal-polymerisasjonskatalysatoren. After ten washings with detergent, only the laundry treated with preparations A and C passed the test, which indicated the necessity of the free radical polymerization catalyst.
Liknende resultater oppnås ved å erstatte N-metylolakrylamid med metylolert diacetonakrylamid (Lubrizol Corp. "HMDAA") og kaliumpersulfat med ammoniumpersulfat. Similar results are obtained by replacing N-methylolacrylamide with methylolated diacetoneacrylamide (Lubrizol Corp. "HMDAA") and potassium persulfate with ammonium persulfate.
Eksempel 4Example 4
Dette eksempel skal ytterligere illustrere fremstilling This example will further illustrate the preparation
av en flammehemmende finish på bomull.of a flame retardant finish on cotton.
Det fremstilles et vandig preparat som følger:An aqueous preparation is prepared as follows:
Bomullstøy fuktes i denne løsning og tørkes ved 121°C i 1,5 minutter og herdes så ved 177°C i 1 minutt. Brennbarheten bestemmes ved den begrensende oksygenindeks (LOI)-metoden (ASTM D-2863). Se også for anvendelse på tekstiler Tesoro og Meiser, Text Res. J. 40 430-436 (1970). • Opprinnelig LOI for behandlet tøy er 30,78%. Cotton fabric is moistened in this solution and dried at 121°C for 1.5 minutes and then cured at 177°C for 1 minute. Flammability is determined by the limiting oxygen index (LOI) method (ASTM D-2863). See also for application to textiles Tesoro and Meiser, Text Res. J. 40 430-436 (1970). • Original LOI for treated cloth is 30.78%.
LOI for ubehandlet tøy er 17,8%. Etter ti gangers vask med vaskemiddel var LOI for det behandlede tøy 27,25%, og dette indikerer LOI for untreated cloth is 17.8%. After ten washes with detergent, the LOI for the treated laundry was 27.25%, and this indicates
at hoveddelen av den flammehemmende finish var i behold.that the main part of the flame-retardant finish was preserved.
Et liknende forsøk ved å anvende et produkt oppnådd ved syre-katalysert, dehydrativ oligomerisasjon av tris(hydroksymetyl)-fosfinoksyd istedenfor tris(hydroksymetyl)fosfinoksyd, viser en enda større grad av holdbarhet, både på bomull og på en bomull-polyesterblanding. A similar experiment using a product obtained by acid-catalyzed, dehydrative oligomerization of tris(hydroxymethyl)phosphine oxide instead of tris(hydroxymethyl)phosphine oxide shows an even greater degree of durability, both on cotton and on a cotton-polyester blend.
Eksempel 5Example 5
Dette eksempel illustrerer ytterligere fremstilling av en flammehindrende finish på bomullsflanell. This example further illustrates the preparation of a flame retardant finish on cotton flannel.
Vandige preparater fremstilles som følger:Aqueous preparations are prepared as follows:
Bomullsflanell (129 g/m 2) fuktes, tørkes og herdes som i de fore-gående eksempler. Begge tøyer oppviser opprinnelige verdier på over 31 og beholder hoveddelen av sin flammehemming etter kraftig vasking med et kommersielt fosfat-bygget vaskemiddel. Cotton flannel (129 g/m 2 ) is moistened, dried and hardened as in the previous examples. Both fabrics show original values above 31 and retain most of their flame retardancy after heavy washing with a commercial phosphate-based detergent.
Claims (12)
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
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US41064373A | 1973-11-12 | 1973-11-12 |
Publications (1)
Publication Number | Publication Date |
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NO744034L true NO744034L (en) | 1975-06-09 |
Family
ID=23625613
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NO744034A NO744034L (en) | 1973-11-12 | 1974-11-08 |
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JP (1) | JPS5337472B2 (en) |
AR (1) | AR203054A1 (en) |
BE (1) | BE822094A (en) |
BR (1) | BR7409452A (en) |
CA (1) | CA1042158A (en) |
CH (2) | CH1478674A4 (en) |
DD (1) | DD116872A5 (en) |
DE (1) | DE2452356A1 (en) |
DK (1) | DK587774A (en) |
FR (1) | FR2323800A1 (en) |
GB (1) | GB1473955A (en) |
IL (1) | IL45903A (en) |
IT (1) | IT1023195B (en) |
NL (1) | NL7414598A (en) |
NO (1) | NO744034L (en) |
SE (1) | SE7414119L (en) |
ZA (1) | ZA747122B (en) |
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JPH0730511B2 (en) * | 1985-05-15 | 1995-04-05 | 日東紡績株式会社 | Flameproofing agent and flameproofing method |
KR101723654B1 (en) * | 2016-04-22 | 2017-04-06 | 오스템임플란트 주식회사 | Method for generating a tooth chart, apparatus and recording medium thereof |
KR101723652B1 (en) * | 2016-04-22 | 2017-04-06 | 오스템임플란트 주식회사 | Method for generating a tooth chart, apparatus and recording medium thereof |
CN111945428B (en) * | 2020-08-26 | 2023-09-08 | 染格材料科技(上海)有限公司 | Preparation method of fluorine-free waterproof agent and product thereof |
KR102590774B1 (en) * | 2020-10-30 | 2023-10-19 | 주식회사 메디트 | Method for optimizing archline and apparatus using thereof |
-
1974
- 1974-10-22 IL IL45903A patent/IL45903A/en unknown
- 1974-11-04 AR AR256384A patent/AR203054A1/en active
- 1974-11-05 FR FR7436750A patent/FR2323800A1/en active Granted
- 1974-11-05 CH CH1478674D patent/CH1478674A4/xx unknown
- 1974-11-05 CH CH1478674A patent/CH582780B5/xx not_active IP Right Cessation
- 1974-11-05 DE DE19742452356 patent/DE2452356A1/en active Pending
- 1974-11-05 CA CA212,974A patent/CA1042158A/en not_active Expired
- 1974-11-06 ZA ZA00747122A patent/ZA747122B/en unknown
- 1974-11-06 GB GB4794374A patent/GB1473955A/en not_active Expired
- 1974-11-08 NO NO744034A patent/NO744034L/no unknown
- 1974-11-08 NL NL7414598A patent/NL7414598A/en not_active Application Discontinuation
- 1974-11-09 JP JP12947874A patent/JPS5337472B2/ja not_active Expired
- 1974-11-11 IT IT53958/74A patent/IT1023195B/en active
- 1974-11-11 BR BR9452/74A patent/BR7409452A/en unknown
- 1974-11-11 SE SE7414119A patent/SE7414119L/xx unknown
- 1974-11-11 DD DD182290A patent/DD116872A5/xx unknown
- 1974-11-12 DK DK587774A patent/DK587774A/da unknown
- 1974-11-12 BE BE7000580A patent/BE822094A/en unknown
Also Published As
Publication number | Publication date |
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CH1478674A4 (en) | 1976-06-15 |
NL7414598A (en) | 1975-05-14 |
ZA747122B (en) | 1975-12-31 |
FR2323800B1 (en) | 1978-07-13 |
SE7414119L (en) | 1975-05-13 |
BR7409452A (en) | 1976-05-25 |
BE822094A (en) | 1975-05-12 |
IL45903A (en) | 1977-03-31 |
JPS5077698A (en) | 1975-06-25 |
GB1473955A (en) | 1977-05-18 |
DK587774A (en) | 1975-07-14 |
CA1042158A (en) | 1978-11-14 |
CH582780B5 (en) | 1976-12-15 |
FR2323800A1 (en) | 1977-04-08 |
DE2452356A1 (en) | 1975-05-15 |
DD116872A5 (en) | 1975-12-12 |
JPS5337472B2 (en) | 1978-10-09 |
IL45903A0 (en) | 1974-12-31 |
IT1023195B (en) | 1978-05-10 |
AR203054A1 (en) | 1975-08-08 |
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