EP0574507B1 - Fibres de polyamide aromatique a capacite elevee de traitement, leur production et leur utilisation - Google Patents
Fibres de polyamide aromatique a capacite elevee de traitement, leur production et leur utilisation Download PDFInfo
- Publication number
- EP0574507B1 EP0574507B1 EP92907819A EP92907819A EP0574507B1 EP 0574507 B1 EP0574507 B1 EP 0574507B1 EP 92907819 A EP92907819 A EP 92907819A EP 92907819 A EP92907819 A EP 92907819A EP 0574507 B1 EP0574507 B1 EP 0574507B1
- Authority
- EP
- European Patent Office
- Prior art keywords
- acid
- weight
- fibers
- alkyl
- surface treatment
- 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 - Lifetime
Links
- 239000004760 aramid Substances 0.000 title claims abstract description 30
- 239000000835 fiber Substances 0.000 title claims description 62
- 229920003235 aromatic polyamide Polymers 0.000 title claims description 20
- 238000004519 manufacturing process Methods 0.000 title description 3
- 238000000034 method Methods 0.000 claims abstract description 24
- 229920006231 aramid fiber Polymers 0.000 claims abstract description 19
- 230000001804 emulsifying effect Effects 0.000 claims abstract description 12
- 239000000314 lubricant Substances 0.000 claims abstract description 11
- 239000011248 coating agent Substances 0.000 claims abstract description 10
- 238000000576 coating method Methods 0.000 claims abstract description 10
- 239000010696 ester oil Substances 0.000 claims abstract description 10
- 239000002216 antistatic agent Substances 0.000 claims abstract description 9
- 150000002191 fatty alcohols Chemical class 0.000 claims abstract description 5
- 235000021122 unsaturated fatty acids Nutrition 0.000 claims abstract description 5
- 150000004670 unsaturated fatty acids Chemical class 0.000 claims abstract description 5
- 150000003973 alkyl amines Chemical class 0.000 claims abstract description 4
- 239000012756 surface treatment agent Substances 0.000 claims description 17
- -1 2-phenylethenyl Chemical group 0.000 claims description 15
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 12
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 claims description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 10
- 239000000654 additive Substances 0.000 claims description 9
- 150000002148 esters Chemical class 0.000 claims description 9
- YWWVWXASSLXJHU-AATRIKPKSA-N (9E)-tetradecenoic acid Chemical compound CCCC\C=C\CCCCCCCC(O)=O YWWVWXASSLXJHU-AATRIKPKSA-N 0.000 claims description 8
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims description 8
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 8
- SECPZKHBENQXJG-FPLPWBNLSA-N palmitoleic acid Chemical compound CCCCCC\C=C/CCCCCCCC(O)=O SECPZKHBENQXJG-FPLPWBNLSA-N 0.000 claims description 8
- JYVLIDXNZAXMDK-UHFFFAOYSA-N pentan-2-ol Chemical compound CCCC(C)O JYVLIDXNZAXMDK-UHFFFAOYSA-N 0.000 claims description 8
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 8
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 claims description 6
- QPRQEDXDYOZYLA-UHFFFAOYSA-N 2-methylbutan-1-ol Chemical compound CCC(C)CO QPRQEDXDYOZYLA-UHFFFAOYSA-N 0.000 claims description 6
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 claims description 6
- 239000005642 Oleic acid Substances 0.000 claims description 6
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 claims description 6
- BTANRVKWQNVYAZ-UHFFFAOYSA-N butan-2-ol Chemical compound CCC(C)O BTANRVKWQNVYAZ-UHFFFAOYSA-N 0.000 claims description 6
- 239000003112 inhibitor Substances 0.000 claims description 6
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 claims description 6
- 125000001624 naphthyl group Chemical group 0.000 claims description 6
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 claims description 6
- 229910019142 PO4 Inorganic materials 0.000 claims description 5
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 claims description 5
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 5
- 235000014113 dietary fatty acids Nutrition 0.000 claims description 5
- 229930195729 fatty acid Natural products 0.000 claims description 5
- 239000000194 fatty acid Substances 0.000 claims description 5
- 150000004665 fatty acids Chemical class 0.000 claims description 5
- 235000021317 phosphate Nutrition 0.000 claims description 5
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 4
- MXLMTQWGSQIYOW-UHFFFAOYSA-N 3-methyl-2-butanol Chemical compound CC(C)C(C)O MXLMTQWGSQIYOW-UHFFFAOYSA-N 0.000 claims description 4
- YWWVWXASSLXJHU-UHFFFAOYSA-N 9E-tetradecenoic acid Natural products CCCCC=CCCCCCCCC(O)=O YWWVWXASSLXJHU-UHFFFAOYSA-N 0.000 claims description 4
- 239000005711 Benzoic acid Substances 0.000 claims description 4
- DPUOLQHDNGRHBS-UHFFFAOYSA-N Brassidinsaeure Natural products CCCCCCCCC=CCCCCCCCCCCCC(O)=O DPUOLQHDNGRHBS-UHFFFAOYSA-N 0.000 claims description 4
- URXZXNYJPAJJOQ-UHFFFAOYSA-N Erucic acid Natural products CCCCCCC=CCCCCCCCCCCCC(O)=O URXZXNYJPAJJOQ-UHFFFAOYSA-N 0.000 claims description 4
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical group C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 claims description 4
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 claims description 4
- RZKSECIXORKHQS-UHFFFAOYSA-N Heptan-3-ol Chemical compound CCCCC(O)CC RZKSECIXORKHQS-UHFFFAOYSA-N 0.000 claims description 4
- 235000021319 Palmitoleic acid Nutrition 0.000 claims description 4
- 239000004952 Polyamide Substances 0.000 claims description 4
- 150000001447 alkali salts Chemical class 0.000 claims description 4
- 229940045714 alkyl sulfonate alkylating agent Drugs 0.000 claims description 4
- 235000010233 benzoic acid Nutrition 0.000 claims description 4
- XZJZNZATFHOMSJ-KTKRTIGZSA-N cis-3-dodecenoic acid Chemical compound CCCCCCCC\C=C/CC(O)=O XZJZNZATFHOMSJ-KTKRTIGZSA-N 0.000 claims description 4
- SECPZKHBENQXJG-UHFFFAOYSA-N cis-palmitoleic acid Natural products CCCCCCC=CCCCCCCCC(O)=O SECPZKHBENQXJG-UHFFFAOYSA-N 0.000 claims description 4
- DPUOLQHDNGRHBS-KTKRTIGZSA-N erucic acid Chemical compound CCCCCCCC\C=C/CCCCCCCCCCCC(O)=O DPUOLQHDNGRHBS-KTKRTIGZSA-N 0.000 claims description 4
- LQJBNNIYVWPHFW-QXMHVHEDSA-N gadoleic acid Chemical compound CCCCCCCCCC\C=C/CCCCCCCC(O)=O LQJBNNIYVWPHFW-QXMHVHEDSA-N 0.000 claims description 4
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 claims description 4
- QQVIHTHCMHWDBS-UHFFFAOYSA-N isophthalic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 claims description 4
- SJWFXCIHNDVPSH-UHFFFAOYSA-N octan-2-ol Chemical compound CCCCCCC(C)O SJWFXCIHNDVPSH-UHFFFAOYSA-N 0.000 claims description 4
- 229920002647 polyamide Polymers 0.000 claims description 4
- CYIDZMCFTVVTJO-UHFFFAOYSA-N pyromellitic acid Chemical compound OC(=O)C1=CC(C(O)=O)=C(C(O)=O)C=C1C(O)=O CYIDZMCFTVVTJO-UHFFFAOYSA-N 0.000 claims description 4
- WBHHMMIMDMUBKC-XLNAKTSKSA-N ricinelaidic acid Chemical compound CCCCCC[C@@H](O)C\C=C\CCCCCCCC(O)=O WBHHMMIMDMUBKC-XLNAKTSKSA-N 0.000 claims description 4
- 229960003656 ricinoleic acid Drugs 0.000 claims description 4
- FEUQNCSVHBHROZ-UHFFFAOYSA-N ricinoleic acid Natural products CCCCCCC(O[Si](C)(C)C)CC=CCCCCCCCC(=O)OC FEUQNCSVHBHROZ-UHFFFAOYSA-N 0.000 claims description 4
- 229920006395 saturated elastomer Polymers 0.000 claims description 4
- 239000003760 tallow Substances 0.000 claims description 4
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 claims description 4
- ARCGXLSVLAOJQL-UHFFFAOYSA-N trimellitic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C(C(O)=O)=C1 ARCGXLSVLAOJQL-UHFFFAOYSA-N 0.000 claims description 4
- PFNHSEQQEPMLNI-UHFFFAOYSA-N 2-methyl-1-pentanol Chemical compound CCCC(C)CO PFNHSEQQEPMLNI-UHFFFAOYSA-N 0.000 claims description 3
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 3
- FKLSONDBCYHMOQ-UHFFFAOYSA-N 9E-dodecenoic acid Natural products CCC=CCCCCCCCC(O)=O FKLSONDBCYHMOQ-UHFFFAOYSA-N 0.000 claims description 3
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical group CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 claims description 3
- 125000003118 aryl group Chemical group 0.000 claims description 3
- 125000004432 carbon atom Chemical group C* 0.000 claims description 3
- 150000001991 dicarboxylic acids Chemical class 0.000 claims description 3
- 238000001035 drying Methods 0.000 claims description 3
- 229910052736 halogen Inorganic materials 0.000 claims description 3
- 150000002367 halogens Chemical class 0.000 claims description 3
- 229910052740 iodine Inorganic materials 0.000 claims description 3
- 239000011630 iodine Substances 0.000 claims description 3
- 229920000847 nonoxynol Polymers 0.000 claims description 3
- 238000007711 solidification Methods 0.000 claims description 3
- 230000008023 solidification Effects 0.000 claims description 3
- CFOQKXQWGLAKSK-KTKRTIGZSA-N (13Z)-docosen-1-ol Chemical compound CCCCCCCC\C=C/CCCCCCCCCCCCO CFOQKXQWGLAKSK-KTKRTIGZSA-N 0.000 claims description 2
- NMRPBPVERJPACX-UHFFFAOYSA-N (3S)-octan-3-ol Natural products CCCCCC(O)CC NMRPBPVERJPACX-UHFFFAOYSA-N 0.000 claims description 2
- OYHQOLUKZRVURQ-NTGFUMLPSA-N (9Z,12Z)-9,10,12,13-tetratritiooctadeca-9,12-dienoic acid Chemical compound C(CCCCCCC\C(=C(/C\C(=C(/CCCCC)\[3H])\[3H])\[3H])\[3H])(=O)O OYHQOLUKZRVURQ-NTGFUMLPSA-N 0.000 claims description 2
- WBYWAXJHAXSJNI-VOTSOKGWSA-M .beta-Phenylacrylic acid Natural products [O-]C(=O)\C=C\C1=CC=CC=C1 WBYWAXJHAXSJNI-VOTSOKGWSA-M 0.000 claims description 2
- 125000004958 1,4-naphthylene group Chemical group 0.000 claims description 2
- 125000001140 1,4-phenylene group Chemical group [H]C1=C([H])C([*:2])=C([H])C([H])=C1[*:1] 0.000 claims description 2
- XUJLWPFSUCHPQL-UHFFFAOYSA-N 11-methyldodecan-1-ol Chemical compound CC(C)CCCCCCCCCCO XUJLWPFSUCHPQL-UHFFFAOYSA-N 0.000 claims description 2
- CFOQKXQWGLAKSK-UHFFFAOYSA-N 13-docosen-1-ol Natural products CCCCCCCCC=CCCCCCCCCCCCCO CFOQKXQWGLAKSK-UHFFFAOYSA-N 0.000 claims description 2
- 125000004959 2,6-naphthylene group Chemical group [H]C1=C([H])C2=C([H])C([*:1])=C([H])C([H])=C2C([H])=C1[*:2] 0.000 claims description 2
- WOFPPJOZXUTRAU-UHFFFAOYSA-N 2-Ethyl-1-hexanol Natural products CCCCC(O)CCC WOFPPJOZXUTRAU-UHFFFAOYSA-N 0.000 claims description 2
- YIWUKEYIRIRTPP-UHFFFAOYSA-N 2-ethylhexan-1-ol Chemical compound CCCCC(CC)CO YIWUKEYIRIRTPP-UHFFFAOYSA-N 0.000 claims description 2
- WETBJXIDTZXCBL-UHFFFAOYSA-N 3,5-dimethylhexan-1-ol Chemical compound CC(C)CC(C)CCO WETBJXIDTZXCBL-UHFFFAOYSA-N 0.000 claims description 2
- WVYWICLMDOOCFB-UHFFFAOYSA-N 4-methyl-2-pentanol Chemical compound CC(C)CC(C)O WVYWICLMDOOCFB-UHFFFAOYSA-N 0.000 claims description 2
- PCWGTDULNUVNBN-UHFFFAOYSA-N 4-methylpentan-1-ol Chemical compound CC(C)CCCO PCWGTDULNUVNBN-UHFFFAOYSA-N 0.000 claims description 2
- WBYWAXJHAXSJNI-SREVYHEPSA-N Cinnamic acid Chemical compound OC(=O)\C=C/C1=CC=CC=C1 WBYWAXJHAXSJNI-SREVYHEPSA-N 0.000 claims description 2
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims description 2
- 239000002253 acid Substances 0.000 claims description 2
- 125000004423 acyloxy group Chemical group 0.000 claims description 2
- 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 claims description 2
- 235000020661 alpha-linolenic acid Nutrition 0.000 claims description 2
- 125000000751 azo group Chemical group [*]N=N[*] 0.000 claims description 2
- 125000005337 azoxy group Chemical group [N+]([O-])(=N*)* 0.000 claims description 2
- 229930016911 cinnamic acid Natural products 0.000 claims description 2
- 235000013985 cinnamic acid Nutrition 0.000 claims description 2
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 2
- 239000001530 fumaric acid Substances 0.000 claims description 2
- 235000011087 fumaric acid Nutrition 0.000 claims description 2
- 125000001072 heteroaryl group Chemical group 0.000 claims description 2
- BXWNKGSJHAJOGX-UHFFFAOYSA-N hexadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCO BXWNKGSJHAJOGX-UHFFFAOYSA-N 0.000 claims description 2
- CFSSWEQYBLCBLH-UHFFFAOYSA-N iso-hexadecyl alcohol Natural products CC(C)CCCCCCCCCCCCCO CFSSWEQYBLCBLH-UHFFFAOYSA-N 0.000 claims description 2
- 229960004488 linolenic acid Drugs 0.000 claims description 2
- KQQKGWQCNNTQJW-UHFFFAOYSA-N linolenic acid Natural products CC=CCCC=CCC=CCCCCCCCC(O)=O KQQKGWQCNNTQJW-UHFFFAOYSA-N 0.000 claims description 2
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 claims description 2
- 239000011976 maleic acid Substances 0.000 claims description 2
- WBYWAXJHAXSJNI-UHFFFAOYSA-N methyl p-hydroxycinnamate Natural products OC(=O)C=CC1=CC=CC=C1 WBYWAXJHAXSJNI-UHFFFAOYSA-N 0.000 claims description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
- 229920002113 octoxynol Polymers 0.000 claims description 2
- ALSTYHKOOCGGFT-MDZDMXLPSA-N oleyl alcohol Chemical compound CCCCCCCC\C=C\CCCCCCCCO ALSTYHKOOCGGFT-MDZDMXLPSA-N 0.000 claims description 2
- 125000001424 substituent group Chemical group 0.000 claims description 2
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 2
- 125000004001 thioalkyl group Chemical group 0.000 claims description 2
- ALYNCZNDIQEVRV-UHFFFAOYSA-N 4-aminobenzoic acid Chemical compound NC1=CC=C(C(O)=O)C=C1 ALYNCZNDIQEVRV-UHFFFAOYSA-N 0.000 claims 2
- PHTQWCKDNZKARW-UHFFFAOYSA-N isoamylol Chemical compound CC(C)CCO PHTQWCKDNZKARW-UHFFFAOYSA-N 0.000 claims 2
- 238000004381 surface treatment Methods 0.000 claims 2
- AJHPGXZOIAYYDW-UHFFFAOYSA-N 3-(2-cyanophenyl)-2-[(2-methylpropan-2-yl)oxycarbonylamino]propanoic acid Chemical compound CC(C)(C)OC(=O)NC(C(O)=O)CC1=CC=CC=C1C#N AJHPGXZOIAYYDW-UHFFFAOYSA-N 0.000 claims 1
- 125000003368 amide group Chemical group 0.000 claims 1
- 229960004050 aminobenzoic acid Drugs 0.000 claims 1
- 125000001117 oleyl 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])=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])[H] 0.000 claims 1
- 229920000889 poly(m-phenylene isophthalamide) Polymers 0.000 claims 1
- 229920003366 poly(p-phenylene terephthalamide) Polymers 0.000 claims 1
- 239000000203 mixture Substances 0.000 description 20
- 238000009472 formulation Methods 0.000 description 13
- 239000004744 fabric Substances 0.000 description 12
- 238000010276 construction Methods 0.000 description 6
- 230000035515 penetration Effects 0.000 description 6
- 206010061592 cardiac fibrillation Diseases 0.000 description 5
- 230000002600 fibrillogenic effect Effects 0.000 description 5
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- 238000005406 washing Methods 0.000 description 5
- 208000016261 weight loss Diseases 0.000 description 5
- 230000004580 weight loss Effects 0.000 description 5
- 238000005299 abrasion Methods 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- 239000002184 metal Substances 0.000 description 4
- 229910052751 metal Inorganic materials 0.000 description 4
- 239000003380 propellant Substances 0.000 description 4
- 238000012360 testing method Methods 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- 238000005260 corrosion Methods 0.000 description 3
- 230000007797 corrosion Effects 0.000 description 3
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical class OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 3
- 238000010304 firing Methods 0.000 description 3
- 239000003921 oil Substances 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 238000009991 scouring Methods 0.000 description 3
- IEORSVTYLWZQJQ-UHFFFAOYSA-N 2-(2-nonylphenoxy)ethanol Chemical compound CCCCCCCCCC1=CC=CC=C1OCCO IEORSVTYLWZQJQ-UHFFFAOYSA-N 0.000 description 2
- YCGKJPVUGMBDDS-UHFFFAOYSA-N 3-(6-azabicyclo[3.1.1]hepta-1(7),2,4-triene-6-carbonyl)benzamide Chemical compound NC(=O)C1=CC=CC(C(=O)N2C=3C=C2C=CC=3)=C1 YCGKJPVUGMBDDS-UHFFFAOYSA-N 0.000 description 2
- WRDNCFQZLUCIRH-UHFFFAOYSA-N 4-(7-azabicyclo[2.2.1]hepta-1,3,5-triene-7-carbonyl)benzamide Chemical compound C1=CC(C(=O)N)=CC=C1C(=O)N1C2=CC=C1C=C2 WRDNCFQZLUCIRH-UHFFFAOYSA-N 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 125000001931 aliphatic group Chemical group 0.000 description 2
- UJMDYLWCYJJYMO-UHFFFAOYSA-N benzene-1,2,3-tricarboxylic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1C(O)=O UJMDYLWCYJJYMO-UHFFFAOYSA-N 0.000 description 2
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- LRHPLDYGYMQRHN-UHFFFAOYSA-N 1-butanol Substances CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 1
- GXJLQJFVFMCVHG-QXMHVHEDSA-N 2-methylpropyl (z)-octadec-9-enoate Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OCC(C)C GXJLQJFVFMCVHG-QXMHVHEDSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 1
- 230000006750 UV protection Effects 0.000 description 1
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- 230000003064 anti-oxidating effect Effects 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
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- 239000003899 bactericide agent Substances 0.000 description 1
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- 125000002843 carboxylic acid group Chemical group 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
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- 238000007598 dipping method Methods 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
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- 238000009533 lab test Methods 0.000 description 1
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- 239000002480 mineral oil Substances 0.000 description 1
- 235000010446 mineral oil Nutrition 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- FCBBRODPXVPZAH-UHFFFAOYSA-N nonan-5-ol Chemical compound CCCCC(O)CCCC FCBBRODPXVPZAH-UHFFFAOYSA-N 0.000 description 1
- 229940055577 oleyl alcohol Drugs 0.000 description 1
- XMLQWXUVTXCDDL-UHFFFAOYSA-N oleyl alcohol Natural products CCCCCCC=CCCCCCCCCCCO XMLQWXUVTXCDDL-UHFFFAOYSA-N 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 230000019612 pigmentation Effects 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 229920001296 polysiloxane Polymers 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 230000002787 reinforcement Effects 0.000 description 1
- 230000003014 reinforcing effect Effects 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- AIMUHNZKNFEZSN-UHFFFAOYSA-M sodium;decane-1-sulfonate Chemical compound [Na+].CCCCCCCCCCS([O-])(=O)=O AIMUHNZKNFEZSN-UHFFFAOYSA-M 0.000 description 1
- 239000008234 soft water Substances 0.000 description 1
- 230000006641 stabilisation Effects 0.000 description 1
- 238000011105 stabilization Methods 0.000 description 1
- 229920001169 thermoplastic Polymers 0.000 description 1
- 229920001187 thermosetting polymer Polymers 0.000 description 1
- 239000004416 thermosoftening plastic 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
- 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
- D06M13/372—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 containing etherified or esterified hydroxy groups ; Polyethers of low molecular weight
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
- D06M13/00—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment
- D06M13/10—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with compounds containing oxygen
- D06M13/165—Ethers
- D06M13/17—Polyoxyalkyleneglycol ethers
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
- D06M13/00—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment
- D06M13/10—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with compounds containing oxygen
- D06M13/224—Esters of carboxylic acids; Esters of carbonic acid
-
- 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
- D06M7/00—Treating fibres, threads, yarns, fabrics, or fibrous goods made of other substances with subsequent freeing of the treated goods from the treating medium, e.g. swelling, e.g. polyolefins
-
- 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
- D06M2200/00—Functionality of the treatment composition and/or properties imparted to the textile material
- D06M2200/40—Reduced friction resistance, lubricant properties; Sizing compositions
Definitions
- the finishes according to the above reference are not suitable for the purposes of the present invention in terms of surface frictional properties, scourability, the protection from depositing due to abrasion, fibrillation and antistatic properties of the resulting treated fibers.
- the present invention accordingly relates to highly processable aramid fibers of high modulus, improved surface frictional properties, improvedscourability, low abrasion polymer depositing, low fibrillation and improved longterm antistatic properties, having a coating of a lubricant, an emulsifying system, an antistatic agent, and other components, derived from a surface treatment agent which consists of
- the aramid fibers of this invention are further characterized by a specific breaking strength of 2.65 to 33.5 cN/dtex (3 to 38 g/den), a specific modulus of 8.83 to 2207 cN/dtex (10 to 2500 g/den), a fiber to metal dynamic friction coefficient on a 1100 dtex aramid yarn of lower than 0.55, preferably below 0.50 at 200 m/min, a fiber to metal boundary friction coefficient on a 1100 dtex aramid yarn of lower than 0.10, preferably below 0.05 at 0.016 cm/s, an amount of deposit due to abrasion of lower than 0.5 mg/kg of yarn, a residual finish level of lower than 15% by weight of the initial finish level after washing.
- the fiber of this invention provides an improved blend of properties in terms of fume emission measured by weight losses, washability of the fiber and cohesiveness of the fiber compared with fibers using other finishes.
- Additives can be used with the aramid and, in fact, it has been found that up to as much as 10 percent by weight of other polymeric material can be blended with the aramid or that copolymers can be used having as much as 10 percent by weight of other diamine substituted for the diamine of the aramid or as much as 10 percent by weight of other diacid chloride substituted for the diacid chloride of the aramid.
- finish levels for both processes, (a) and (b), are in the range of 0.05 to 2% by weight, preferably 0.2 to 1.0% by weight.
Landscapes
- Engineering & Computer Science (AREA)
- Textile Engineering (AREA)
- Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
- Artificial Filaments (AREA)
Abstract
Claims (16)
- Fibres d'aramide présentant un revêtement à base d'un lubrifiant, d'un système émulsifiant, d'un agent antistatique et d'autres composants, dérivant d'un agent de traitement de surface qui consiste en:a) 30 à 70% en poids d'un lubrifiant constitué d'une huile à base d'ester, consistant en un ester, composé de(I) un composant alcool qui est un alcool monovalent saturé, primaire ou secondaire, ramifié, de formule générale
R¹ représente un groupe alkyle en C₁ à C₁₆,
R² représente un atome d'hydrogène, un groupe alkyle en C₁ à C₁₆, si k=1 et
R² représente un groupe alkyle en C₁ à C₁₆, si k=0,h = 0 à 5j = 0 à 4k = 0 ou 1m = 0 à 16et dans laquelle le nombre total d'atomes de carbone est inférieur à 25,
et(II) un composant acide carboxylique qui est un acide gras insaturé de formule générale
R³-(COOH)s ; s= 1 à 6
dans laquelle R³ représente un groupe alkényle en C₄-C₁₉, un groupe alkadiényle en C₄-C₁₉, un groupe alkatriényle en C₄-C₁₉, phényle, naphtyle, 2-phényléthényle, ou qui est un acide dicarboxylique insaturés de formule générale
HOOC-(CH=CH)n-COOH
dans laquelle n = 1 ou 2,
et ledit ester présente un point de solidification inférieur à +5°C, une viscosité cinématique de 100 à 350 mm²/s (à 20°C) et un indice d'iode compris entre 30 et 140,b) 20 à 50% en poids d'un système émulsifiant qui consiste en acides gras éthoxylés insaturés et/ou en alcools gras éthoxylés insaturé et/ou en alkylamines éthoxylées de formule générale
R⁴-X-(EO)p(PO)q-OH
dans laquelle
R⁴ représente un groupe alcényle en C₅-C₂₀, phényle, naphtyle, ou alkylphényle en C₈ ou C₉,
X représente-COO-, -NH- ou -O-,
EO représente une unité oxyde d'éthylène,
PO représente une unité oxyde de propylène,
p = 2 à 15, et
q = 0 à 10,c) 5 à 15% en poids d'un agent antistatique, consistant en sels alcalins d'alkylsulfonates en (C₄-C₁₂), alkyl (C₄-C₁₂) phosphates, ou acides alkyl(C₄-C₂₀)carboxyliques,d) 0,2 à 2% en poids d'un inhibiteur de corrosion, ete) éventuellement des additifs, et de sorte que la quantité dudit revêtement sur lesdites fibres soit de 0,05 à 2% en poids. - Fibres selon la revendication 1, caractérisées en ce que ledit composant alcool (I) de (a) est 2-méthyl-1-propanol, 2-butanol, 2-pentanol, 2-méthyl-1-butanol, 3-méthyl-1-butanol, 3-méthyl-2-butanol, 2-méthyl-1-pentanol, 4-méthyl-1-pentanol, 4-méthyl-2-pentanol, 2-pentanol, 3-heptanol, 2-octanol, 2-éthyl-1-héxanol,3,5-diméthyl-1-héxanol, 5-nonanol, 2-6-diméthyl-4-heptanol, alcool iso-héxadécylique ou alcool iso-tridécylique.
- Fibres selon la revendications 1, caractérisées en ce que ledit composant acide carboxylique (II) de (a) est: acide lauroléique, acide myristoléique, acide palmitoléique, acide oléique, acide gadoléique, acide érucique, acide ricinoléique, acide de suif, acide linoléique, acide linolénique, acide fumarique, acide maléique, acide cinnamique, acide naphtaline carboxylique, acide benzoique, acide téréphtalique, acide isophtalique, acide trimellitique ou acide pyromellitique.
- Fibres selon la revendication 1, caractérisées en ce que ledit système émulsifiant comprend des octylphénoléthoxylates (5 à 15 moles de EO) et/ou des nonylphénoléthoxylates (5 à 15 moles de EO) et/ou de l'acide oléique, ricinoléique, érucique, gadoléique, palmitoléique, myristoléique, ou lauroléique éthoxylé (3 à 15 moles de EO) et/ou des éthoxylates d'alcool élaidylique, alcool érucylique, d'alcool brassidylique, ou d'alcool oléylique (3 à 10 moles de EO) et/ou de l'éthoxylate d'alcool de suif (3 à 10 moles de EO).
- Fibres selon la revendication 1, caractérisées en ce que ledit agent de traitement de surface consiste en
50 à 60% en poids de (a),
25 à 40% en poids de (b),
5 à 10% en poids de (c),
0,3 à 1% en poids de (d) et
éventuellement des additifs (e). - Fibres selon la revendication 1, caractérisées en ce que les unités répétées de l'aramide présentent la formule générale
(-NH-A₁-NH-CO-A₂-CO-)n
dans laquelle
A₁ et A₂ sont identiques ou différents et représentent des cycles hétéroaromatiques et/ou polyaromatiques et/ou aromatiques substitués ou non substitués. - Fibres selon la revendication 6, caractérisées en ce que A₁ et A₂ sont indépendamment l'un de l'autre sélectionnés parmi 1,4-phénylène,1,3-phénylène,1,2-phénylène, 4,4'-biphénylène, 2,6-naphtylène,1,5-naphtylène,1,4-naphtylène, phénoxyphényl-4,4'-diyl, phénoxyphényl-3,4'-diyl, 2,5-pyridylène et 2,6-quinolylène, et qui peuvent être ou ne pas être substitués par un ou plusieurs substituants comprenant atomes d'halogène, groupes alkyle en C₁-C₄, phényle, carboalkoxyle, alkoxyle en C₁-C₄,
acyloxy, nitro, dialkylamino, thioalkyle, carboxy et sulfonyle et dans lesquels le groupe amide peut également être remplacé par un groupe carbonylhydrazide, azoxy ou azo. - Fibres selon la revendication 6, caractérisées en ce que le polyamide aromatique est un copolyamide dans lequel de préférence au moins 80% en moles du total A₁ et A₂ représentent du 1,4-phénylène et du phénoxyphényl-3,4′-diyl qui peuvent être ou ne pas être substitués, et la teneur en phénoxyphényl-3,4'-diylène est de 10 à 40% en moles.
- Fibres selon la revendication 6, caractérisées en ce que les fibres de polyamide consistent en poly-(m-phénylène-isophtalamide).
- Fibres selon la revendication 6, caractérisées en ce que les fibres de polyamide consistent en poly-p-(phénylène-téréphtalamide).
- Fibres selon la revendication 6, caractérisées en ce que lesdites fibres de polyamide contiennent éventuellement des unités dérivées de l'acide 3- ou 4-aminobenzoique.
- Un procédé de préparation de fibres d'aramide présentant un revêtement constitué d'un agent de traitement de surface, comprenant les étapes consistant à appliquer l'agent de traitement de surface sur lesdites fibres dans un système aqueux à une concentration de 1 à 100% en poids, à sécher les fibres à une température comprise entre 150 et 190°C, éventuellement à répéter l'application de l'agent de traitement de surface, caractérisé de plus en ce que l'agent de traitement de surface consiste ena) 30 à 70% en poids d'un lubrifiant constitué d'une huile à base d'ester, consistant en un ester, composé de(I) un composant alcool qui est un alcool monovalent saturé, primaire ou secondaire, ramifié, de formule générale
R¹ représente un groupe alkyle en C₁ à C₁₆,
R² représente un atome d'hydrogène, un groupe alkyle en C₁ à C₁₆, si k=1 et
R² représente un groupe alkyle en C₁ à C₁₆, si k=0,h = 0 à 5j = 0 à 4k = 0 ou 1m = 0 à 16et dans laquelle le nombre total d'atomes de carbone est inférieur à 25,
et(II) un composant acide carboxylique qui est un acide gras insaturé de formule générale
R³-(COOH)s; s= 1 à 6
dans laquelle R³ représente un groupe alkényle en C₄-C₁₉, un groupe alkadiényle en C₄-C₁₉, un groupe alkatriényle en C₄-C₁₉, phényle, naphtyle, 2-phényléthényle, ou
qui est un acide dicarboxylique insaturé de formule générale
HOOC-(CH=CH)n-COOH
dans laquelle n = 1 ou 2,
et ledit ester présente un point de solidification inférieur à +5°C, une viscosité cinématique de 100 à 350 mm²/s (à 20°C) et un indice d'iode compris entre 30 et 140,b) 20 à 50% en poids d'un système émulsifiant qui consiste en acides gras éthoxylés insaturés et/ou en alcools gras éthoxylés insaturés et/ou en alkylamines éthoxylées de formule générale
R⁴-X-(EO)p(PO)q-OH
dans laquelle
R⁴ représente un groupe alcényle en C₅-C₂₀, phényle, naphtyle, ou alkylphényle en C₈ ou C₉,
X représente -COO-, -NH- ou -O-,
EO représente une unité oxyde d'éthylène,
PO représente une unité oxyde de propylène,
p = 2 à 15, et
q = 0 à 10,c) 5 à 15% en poids d'un agent antistatique, consistant en sels alcalins d'alkylsulfonates en (C₄-C₁₂), alkyl (C₄-C₁₂) phosphates, ou acides alkyl(C₄-C₂₀)carboxyliques,d) 0,2 à 2% en poids d'un inhibiteur de corrosion, ete) éventuellement des additifs. - Procédé selon la revendication 12, caractérisé en ce que la concentration de l'agent de traitement de surface dans l'eau est de 30% en poids.
- Procédé selon la revendication 12, caractérisé en ce que la concentration de l'agent de traitement de surface est de 100% en poids, c'est-à-dire que l'agent de traitement de surface est pur.
- Procédé selon la revendication 12, caractérisé en ce que l'agent de traitement de surface est appliqué à des fibres d'aramides qui ne sont jamais séchées.
- Procédé selon la revendication 12, caractérisé en ce que l'agent de traitement de surface est appliqué à des fibres d'aramides déjà séchées.
Applications Claiming Priority (4)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE4106682A DE4106682C2 (de) | 1991-03-02 | 1991-03-02 | Aromatische Hochleistungs-Polyamid-Fasern, ihre Herstellung und Verwendung |
DE4106682 | 1991-03-02 | ||
PCT/US1992/001891 WO1992015747A1 (fr) | 1991-03-02 | 1992-03-02 | Fibres de polyamide aromatique a capacite elevee de traitement, leur production et leur utilisation |
CN92103391A CN1049462C (zh) | 1991-03-02 | 1992-04-03 | 可加工性优良的芳族聚酰胺纤维及其生产和用途 |
Publications (2)
Publication Number | Publication Date |
---|---|
EP0574507A1 EP0574507A1 (fr) | 1993-12-22 |
EP0574507B1 true EP0574507B1 (fr) | 1994-08-10 |
Family
ID=25742744
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
EP92907819A Expired - Lifetime EP0574507B1 (fr) | 1991-03-02 | 1992-03-02 | Fibres de polyamide aromatique a capacite elevee de traitement, leur production et leur utilisation |
Country Status (8)
Country | Link |
---|---|
EP (1) | EP0574507B1 (fr) |
JP (1) | JP3383860B2 (fr) |
CN (1) | CN1049462C (fr) |
AU (1) | AU660455B2 (fr) |
BR (1) | BR9205704A (fr) |
DE (2) | DE4106682C2 (fr) |
ES (1) | ES2057991T3 (fr) |
WO (1) | WO1992015747A1 (fr) |
Families Citing this family (11)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5269952A (en) * | 1992-12-21 | 1993-12-14 | E. I. Du Pont De Nemours And Company | Antistatic finish for dyeable surfactant-containing poly(m-phenylene isophthalamide) fibers |
ES2202148T3 (es) | 1999-07-12 | 2004-04-01 | Societe De Technologie Michelin | Cubierta de neumatico, cuyos flancos pueden comprender una pelicula barnizada. |
US6706931B2 (en) * | 2000-12-21 | 2004-03-16 | Shell Oil Company | Branched primary alcohol compositions and derivatives thereof |
JP4747255B2 (ja) * | 2000-12-27 | 2011-08-17 | Jnc株式会社 | 帯電性を有するトウおよびそれを用いた積層体 |
EP1435407A1 (fr) | 2003-01-02 | 2004-07-07 | Teijin Twaron B.V. | Fil d'aramide ayant un apprêt conducteur |
CN1318684C (zh) * | 2004-07-09 | 2007-05-30 | 竹本油脂(苏州)有限公司 | 兽毛纤维的纺纱用处理剂 |
JP4480176B2 (ja) * | 2006-12-27 | 2010-06-16 | 竹本油脂株式会社 | 合成繊維用処理剤の水性液及び合成繊維の処理方法 |
JP5604141B2 (ja) * | 2010-03-11 | 2014-10-08 | Jx日鉱日石エネルギー株式会社 | 油剤組成物及び極微量油剤供給式切削・研削加工方法 |
JP5260621B2 (ja) * | 2010-12-15 | 2013-08-14 | 花王株式会社 | 繊維用処理剤 |
EP3411351A4 (fr) | 2016-02-03 | 2019-09-04 | Elevance Renewable Sciences, Inc. | Acides gras insaturés alcoxylés et leurs utilisations |
CN109486181A (zh) * | 2018-11-22 | 2019-03-19 | 江苏利德尔新材料科技有限公司 | 一种抗静电高阻燃mc尼龙复合材料的制备方法 |
Family Cites Families (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3177143A (en) * | 1959-05-25 | 1965-04-06 | Exxon Research Engineering Co | Emulsion for the conditioning of raw cotton fibers |
US3287324A (en) * | 1965-05-07 | 1966-11-22 | Du Pont | Poly-meta-phenylene isophthalamides |
US3368917A (en) * | 1967-01-06 | 1968-02-13 | Deering Milliken Res Corp | Coated textile yarn |
CH1858269D (fr) * | 1968-12-18 | |||
US3682694A (en) * | 1970-01-23 | 1972-08-08 | Yasuharu Kato | Oils for heat treatment of thermoplastic fibers |
US4019990A (en) * | 1975-07-23 | 1977-04-26 | Allied Chemical Corporation | Production of polyester tire yarn polyglycol ether spin finish composition |
DE3929376C1 (fr) * | 1989-09-05 | 1991-04-18 | E.I. Du Pont De Nemours And Co., Wilmington, Del., Us |
-
1991
- 1991-03-02 DE DE4106682A patent/DE4106682C2/de not_active Expired - Fee Related
-
1992
- 1992-03-02 EP EP92907819A patent/EP0574507B1/fr not_active Expired - Lifetime
- 1992-03-02 JP JP50744992A patent/JP3383860B2/ja not_active Expired - Fee Related
- 1992-03-02 AU AU14608/92A patent/AU660455B2/en not_active Ceased
- 1992-03-02 BR BR9205704A patent/BR9205704A/pt not_active IP Right Cessation
- 1992-03-02 ES ES92907819T patent/ES2057991T3/es not_active Expired - Lifetime
- 1992-03-02 DE DE69200321T patent/DE69200321T2/de not_active Expired - Fee Related
- 1992-03-02 WO PCT/US1992/001891 patent/WO1992015747A1/fr active IP Right Grant
- 1992-04-03 CN CN92103391A patent/CN1049462C/zh not_active Expired - Fee Related
Also Published As
Publication number | Publication date |
---|---|
ES2057991T3 (es) | 1994-10-16 |
JP3383860B2 (ja) | 2003-03-10 |
BR9205704A (pt) | 1994-08-02 |
CN1076977A (zh) | 1993-10-06 |
DE4106682A1 (de) | 1992-10-08 |
AU1460892A (en) | 1992-10-06 |
DE69200321D1 (de) | 1994-09-15 |
CN1049462C (zh) | 2000-02-16 |
JPH06505312A (ja) | 1994-06-16 |
EP0574507A1 (fr) | 1993-12-22 |
AU660455B2 (en) | 1995-06-29 |
DE4106682C2 (de) | 1995-08-10 |
DE69200321T2 (de) | 1995-02-09 |
WO1992015747A1 (fr) | 1992-09-17 |
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17P | Request for examination filed |
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