AU660455B2 - Highly processable aromatic polyamide fibers, their production and use - Google Patents
Highly processable aromatic polyamide fibers, their production and use Download PDFInfo
- Publication number
- AU660455B2 AU660455B2 AU14608/92A AU1460892A AU660455B2 AU 660455 B2 AU660455 B2 AU 660455B2 AU 14608/92 A AU14608/92 A AU 14608/92A AU 1460892 A AU1460892 A AU 1460892A AU 660455 B2 AU660455 B2 AU 660455B2
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- Prior art keywords
- acid
- weight
- fibers
- document
- alkyl
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- 239000000835 fiber Substances 0.000 title claims description 68
- 239000004760 aramid Substances 0.000 title claims description 32
- 229920003235 aromatic polyamide Polymers 0.000 title claims description 22
- 238000004519 manufacturing process Methods 0.000 title description 5
- 238000000034 method Methods 0.000 claims description 25
- 229920006231 aramid fiber Polymers 0.000 claims description 19
- 230000008569 process Effects 0.000 claims description 19
- 239000012756 surface treatment agent Substances 0.000 claims description 17
- -1 2-phenylethenyl Chemical group 0.000 claims description 16
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 12
- 230000001804 emulsifying effect Effects 0.000 claims description 12
- 239000000314 lubricant Substances 0.000 claims description 11
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 claims description 10
- 239000010696 ester oil Substances 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
- 239000002216 antistatic agent Substances 0.000 claims description 9
- 239000011248 coating agent Substances 0.000 claims description 9
- 238000000576 coating method Methods 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
- 150000002148 esters 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
- 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
- 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
- JYVLIDXNZAXMDK-UHFFFAOYSA-N pentan-2-ol Chemical compound CCCC(C)O JYVLIDXNZAXMDK-UHFFFAOYSA-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
- 150000002191 fatty alcohols Chemical class 0.000 claims description 5
- 235000021317 phosphate Nutrition 0.000 claims description 5
- 235000021122 unsaturated fatty acids Nutrition 0.000 claims description 5
- 150000004670 unsaturated fatty acids Chemical class 0.000 claims description 5
- 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
- 150000003973 alkyl amines 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
- 229910052799 carbon Inorganic materials 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
- 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
- 125000001140 1,4-phenylene group Chemical group [H]C1=C([H])C([*:2])=C([H])C([H])=C1[*:1] 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
- 150000008052 alkyl sulfonates Chemical class 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
- 229910052739 hydrogen Inorganic materials 0.000 claims description 3
- 229910052740 iodine Inorganic materials 0.000 claims description 3
- 239000011630 iodine Substances 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
- ALSTYHKOOCGGFT-KTKRTIGZSA-N (9Z)-octadecen-1-ol Chemical compound CCCCCCCC\C=C/CCCCCCCCO ALSTYHKOOCGGFT-KTKRTIGZSA-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
- 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
- YIWUKEYIRIRTPP-UHFFFAOYSA-N 2-ethylhexan-1-ol Chemical compound CCCCC(CC)CO YIWUKEYIRIRTPP-UHFFFAOYSA-N 0.000 claims description 2
- PFNHSEQQEPMLNI-UHFFFAOYSA-N 2-methyl-1-pentanol Chemical compound CCCC(C)CO PFNHSEQQEPMLNI-UHFFFAOYSA-N 0.000 claims description 2
- QPRQEDXDYOZYLA-UHFFFAOYSA-N 2-methylbutan-1-ol Chemical compound CCC(C)CO QPRQEDXDYOZYLA-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
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- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
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- 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
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- 229920001296 polysiloxane Polymers 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 125000005551 pyridylene group Chemical group 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
- 229910052717 sulfur Inorganic materials 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
Landscapes
- Engineering & Computer Science (AREA)
- Textile Engineering (AREA)
- Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
- Artificial Filaments (AREA)
Description
OPI DATE 06/10/92 INTE AOJP DATE 12/11/92 (51) International Patent Classification 5 D06M 13/224, 13/17, 13/372 APPLN. ID 14608 92 PCT NUMBER PCT/US92/01891 ON TREATY (PCT) (11) International Publication Number: WO 92/15747 Al (43) International Publication Date: 17 September 1992 (17.09.92) (21) International Application Number: (22) International Filing Date: Priority data: P 4106 682.0 2 March PCT/US92/01891 2 MarcL 992 (02.03.92) 1991 (02.03.91) (71) Applicant: E.I. DU PONT DE NEMOURS AND COM- PANY [US/US]; 1007 Market Street, Wilmington, DE 19898 (US).
(72) Inventor: REBOUILLAT, Serge 14703 Duck Cove Place, Midlothian, VA 23112 (US).
(74) Agent: SHAFER, Robert, E.I. du Pont de Nemours and Company, Legal/Patent Records Center., 1007 Market Street, Wilmington, DE 19898 (US).
(81) Designated States: AT (European patent), AU, BE (European patent), BR, CA, CH (European patent), DE (European patent), DK (European patent), ES (European patent), FR (European patent), GB (European patent), GR (European patent), IT (European patent), JP, KR, LU (European patent), MC (European patent), NL (European patent), SE (European patent).
Published With international search report.
Before the expiration of the time limit for amending the claims and to be republished in the event of the receipt of amendments.
66 0455 (54)Title: HIGHLY PROCESSABLE AROMATIC POLYAMIDE FIBERS, THEIR PRODUCTION AND USE (57) Abstract The invention relates to aramid fibers having a coating of an esteroil lubricant, an emulsifying system consisting of ethoxylated derivatives of unsaturated fatty acids and/or unsaturated fatty alcohols and/or ethoxy-propoxylated alkylamines and an antistatic agent; and to a process for making them.
WO 92/15747 1 PCT/US92/01891
TITLE
HIGHLY PROCESSABLE AROMATIC POLYAMIDE FIBERS. THEIR PRODUCTION AND USE Background of the Invention Field of the Invention The present invention relates to highly processable aromatic polyamide fibers, their production and use.
Description of the Prior Art Research Disclosure, July 1980, No. 195, disclosure 19520, discloses finishes useful for treating industrial fibers,such as polyamide and aramid fibers, which finishes include a lubricant, comprising esters composed of an aliphatic, saturated carboxylic acid and a polyhydric or aliphatic unbranched alcohol. These finishes also contain an emulsifier or emulsifying system, an anti-oxidant to increase the stability of the composition, polysiloxanes as a further thermostable lubricant, 2 o and a sulfonated natural oil as an antistatic agent. Furthermore, these finishes may contain biostats, further emulsifiers, and lubricants.
However, 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.
High strength, high modulus fibers, have been proposed to reinforce elastomeric and plastic materials.
Summary of the Invention Most commercial fibers have a high rigidity, poor surface functional characteristics leading to fibrillation, mainly caused by excessive friction among filaments, and poor surface affinity to most traditional elastomeric, thermoplastic and thermoset matrices which they reinforce.
These drawbacks and defects, which result in a degradation of physical properties such as strength and modulus, have been driving a high demand WO 92/15747 2 PCT/US92/01891 for highly processable fibers which have to be easy to process through knitting or weaving operations and do not lead to machine deposits.
According to this invention, the application of a particular combination of surface treatment agents on the surface of previously dried aramid fibers asing a finishing process already known; or the application of those agents on never-drawn never-dried aramid fibers yields a new surface treated fiber which exhibits excellent processability characteristics in its use as a reinforcing element for rubber applications or as a yar for fabric woven structures. The end use performance of final products, using the fibers, is consequently significantly improved.
The present invention accordingly relates to highly processable aramid fibers of high modulus, improved surface frictional properties, improved scourability, low abrasion polymer iepositing, 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 30 to 70% by weight of an esteroil lubricant, consisting of an ester, composed of an alcohol component which is a branched, primary or secondary, saturated monohydric alcohol of the general formula R1 R 2 I I CH3-(CH2)h-(CH)k-(CH2)j-CH-(CH2)m-OH wherein
R
1 represents C1-C16-alkyl,
R
2 represents H, C 1
-C
16 -alkyl,, if k= 1 and
R
2 represents C1-C16-alkyl, if k= 0, h 0 to k= 0or1 j 0 to 4 m =0 to 16 and wherein the total number of carbon atoms is below 25, and (II) a carboxylic acid component which is an WO 92/15747 3 PCT/US92/01891 unsaturated fatty acid of the general formula
R
3 -(COOH)s; s 1-6 wherein
R
3 represents C 4
-C
1 9-alkenyl, C4-C 1 9-alkadienyl, C 4
-C
19 -alkatrienyl, phenyl, naphthyl, 2-phenylethenyl, or which is an unsaturated dicarboxylic acid of the general formula HOOC-(CH CH)n-COOH wherein n 1 or 2, and said ester has a solidification point of below +5C, preferably below 0°C, a kinematic viscosity of 100 to 35C mm 2 /s (at 200C) and an iodine value between 30 and 140, preferably between 30 and 20 to 50% by weight of an emulsifying system which consists of unsaturated ethoxylated fatty acids and/or'unsaturated ethoxylated fatty alcohols and/or ethoxylated alkylamines of the general formula
R
4 -X-(EO)p(PO)q-OH wherein
R
4 represents C5-C 2 0-alkenyl, phenyl, naphthyl, or C 8 or C9-alkylphenyl, X represents -COO-, -NH- or EO represents an ethylene oxide unit, PO represents a propylene oxide unit,, p =2to q 0 to 5 to 15% by weight of an antistatic agent, consisting of alkali salts of C 4
-C
1 2 alkyl sulfonates, C4-C12-alkyl phosphates or C4-C 2 0 -alkyl carboxylic acids, 0.2 to 2% by weight of a corrosion-inhibitor, and optionally additives, and whereby the amount of said coating on said fibers is 0.05 to 2.0% by weight, preferably 0.2 to 1.0% by weight, of the fiber.
The coating preferably consists of to 60% by weight, most preferably 55 to 60% by weight of the esteroil WO 92/15747 PCT'/US92/01891 to 40% by weight, most preferably 29 to 35% by weight of the emulsifying system 5 to 10% by weight, most preferably 5 to 7% by weight of the antistatic agent 0.3 to 1% by weight, most preferably 0.3 to 0.5% by weight of the corrosion inhibitor and, if desired, optionally additives 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 yar 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 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 1 )sses, washability of the fiber and cohesiveness of the fiber compared with fibers using other finishes.
Within the scope of this invention, by "fibers" are meant continuous filaments as well as a single yarn or cord, staple fibers, fiber tows (for example from stretch breaking processes), yarns or flat textile skeins, staple crimped fibers, pulps, industrial woven, twisted, knitted, braided, spiralled or wrapped textiles from 2 0 aramids with a fiber type structure.
Aramids are such polymers that are partially, preponderantly or exclusively composed of aromatic rings, which are connected through carbamide bridges or optionally, in addition also through other bridging structures. The structure of such aromatic polyamides can be elucidated by the following general formula of repeating units: (-CO-NH-AI-NH-CO-A2-CO-)n wherein A 1 and A 2 are the same or different and signify aromatic and/or polyaromatic and/or heteroaromatic rings, that can also be substituted. Typically Al and A 2 may, independently from each other, be selected from 1,4-phenylene, 3 o 1,3-phenylene, 1,2-phenylene, 4,4'-biphenylene, 2,6-naphthylene, 1,4-naphthylene, phenoxyphenyl-4,4'-diylene, phenoxyphenyl-3,4'-diylene, pyridylene and 2,6-quinolylene which may or may not be substituted by one or more substituents which may comprise halogen, C 1
-C
4 -alkyl, phenyl, carboalkoxyl, CI-C 4 alkoxyl, acyloxy, nitro, dialkylamino, thioalkyl, carboxyl and sulfonyl. The WO 92/15747 PCr/US92/01891 -CONH-group may also be replaced by a carbonyl-hydrazide (-CONHNH-) group, azo-or azoxy-group.
Fibers derived from wholly aromatic polyamides are preferred.
Examples of aramids are poly-m-phenylene-isophthalamide and poly-p-phenyleneterephthalamide.
Especially suitable are poly-m-phenyleneisophthalamide fibers according to US 3,287,324 and poly-p-phenyleneterephthalamide fibers according to US 3,869,429 and DE 22 19 703.
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 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.
Additional suitable aromatic polyamides are of the following structure (-NH-Arl-X-Ar2-NH-CO-Arl-X-Ar 2 -CO-)n in which X represents O, S, SO 2 NR, N 2
CR
2
CO,
R represents H, C 1 -C4-alkyl, and Ar 1 and Ar 2 which may be same or different are selected from 1,2-phenylene, 1,3phenylene and 1,4-phenylene and in which at least one hydrogen atom may be substituted with halogen and/or C 1 -C4-alkyl.
The finish formulation of this invention comprises a lubricant, an emulsifying system, an antistatic agent and a corrosion inhibitor, and if desired, water and/or other additives.
The lubricant is an esteroil which is characterized as stated above.
Examples for the alcohol compound of the ester can be 2-methyl-l-propanol, 2butanol, 2-pentanol, 2-methyl-l-butanol, 3-methyl-3-1-butanol, 3-methyl-2-butanol, 2-methyl-l-pentanol, 4-methyl-l-pentanol, 4-methyl-2-pentanol, 2rpentanol, 3heptanol, 2-octanol, 2-ethyl-l-hexanol, 3,5-dimethyl-l-hexanol, 5-nonanol, 2-6dimethyl-4-heptanol,.iso-hexadecyl alcohol or iso-tridecyl alcohol. Examples for the carboxylic acid component can be lauroleic acid, myristoleic acid, palmitoleic acid, oleic acid, gadoleic acid, erucic acid, ricinoleic acid, tallow acid, linoleic acid, linolenic acid, fumaric acid, maleic acid, cinnamic acid, naphthaline carboxylic acid, benzoic acid, terephthalic acid, isophthalic acid, trimellitic acid or pyromellitic acid.
WO 92/15747 V PCT/US92/01891 The kinematic viscosity of the esteroil preferably is in the range of 200 to 300 mm 2 /s The emulsifying system of this invention is as defined above.
Examples of unsaturated fatty acids are lauroleic acid, myristoleic acid, palmitoleic acid, gadoleic acid, erucic acid or ricinoleic acid, preferably oleic acid (with 3-15 moles ethylene oxide). Examples of unsaturated fatty alcohol are elaidyl alcohol, erucyl alcohol, brassidyl alcohol, preferably oleyl alcohol and/or tallow alcohol (with 3-10 moles of EO). Further examples are C 8 or C9-alkylphenolethoxylates, preferably octylphenol-or nonylphenolethoxylates 5 moles of EO).
The antistatic compounds are alkali salts, preferably sodium salts of alkyl sulfonates lauryl or oleyl sulfonate), alkyl phosphates like C 4
-C
12 -alkyl phosphates (mono/diester mixture) and salts of fatty acids, e.g. oleic acid. The sodium chloride content should be below It is also possible to use alkylsulfates, however, they are not preferred because they hydrolyze easily and therefore loose their antistatic efficiency.
Useful corrosion inhibitors are diethanolamine salts of C 4
-C
12 alkylphosphate-esters (mono/di) or amine salts of fatty acids or benzoic acid.
The formulation may optionally contain water for stabilization reasons even before it is diluted with water in order to obtain the concentration at 2 o which it is applied to the fibers.
Additives can optionally be incorporated in the formulation if specific properties or process conditions are required, for example adhesion, specific crosslinkage, UV-protection, antioxidation, pigmentation or rheological adjustment.
These additives may further comprise fungicides, bacteriocides and biocides.
A formulation for the treatment of aramid fibers can be prepared by mixing all components at an elevated temperature, preferably at a temperature between 30* and 40 0 C, in order to obtain a homogeneous and clear oil. Thus, for example, a mixture consisting of 550 g of isobutyl oleate, 350 g of emulsifying system which consists of 200 g nonylphenol ethoxylate (8 EO) and 150 g of oleic acid 3 o ethoxylate (10 EO), 70 g of sodium decylsulfonate and 5 g of the diethanolamine salt of benzoic acid can be prepared. If necessary, about 25 g of water is added to the mixture to eliminate any turbidity. The addition of water may also be necessary to obtain a stable clear oil. If required, the pH value can be adjusted to be within 6 and 8, preferably 7, using diethanolamine or acetic acid.
WO 92/15747 PCT/US92/01891 The finish formulation of this invention is further characterized by a viscosity of 150 to 500 mm 2 preferably of 150 to 300 mm 2 /s (at 200C), a weightloss of less than 25%, preferably less than 15%, after 2 h at 200°C, a surface tension of a 1% emulsion of less than 35 mN/m, preferably less than 32 mN/m at The invention further relates to a process for the production of a highly processable aromatic polyamide fiber coated on the surface with a surface treatment agent.
Coating of aramid fibers with the surface treatment agent of this invention can take place in various ways and, more specifically, for example, according to the following processes and According to process the application of the surface treatment agent is made on never-dried never-drawn aramid fiber; and according to process the application of the surface treatment agent is done on previously dried aramid fiber, in each case using any known coating device. The finish formulation is used neat or in a diluted aqueous form, which is in a concentration of as low as 1% by weight.
In the preferred route for process the finish formulation is applied in a concentration of about 30% by weight in water (this means 30 parts by weight finish formulation 70 parts by weight water) on a wet aramid fiber. The emulsion treated fiber is then dried during the fiber stretching drying step at a temperature between 150 and 190°C, preferably at around 170°C for few seconds (5-10 s) while the yarn speed is around 630 m/min (workable range 120-1200 m/min).
In the preferred route of process yarns and cords of aramid fibers are passed through a dip of the finish formulation in a dipping unit to coat them and then are dried in an air heated chamber at 80 to 190°C, preferably at 110 to 1300C with a predetermined tension of 6 N for an untwisted 1670 dtex yarn. The most preferred temperature for this step is about 1200C. Depending oh the dip concentration for the finish formualtion, which may be from 1% to 100% by weight in water, the speed is adjusted to be from 15 to 100 m/min. By a finish formulation of 100%, is meant that the finish is neat.
The finish levels for both processes, and are in the range of 0.05 to 2% by weight, preferably 0.2 to 1.0% by weight.
If desired, processes and can be conducted as a multi-step pro cess in which the fiber may be several times immersed in a surface treatment agent and in turn dried. For example, the treatment agent can be applied on the WO 92/15747 PCT/US92/01891 never-dried wet fiber, then the fiber can be dried and thereafter the surface treatment agent can be applied once more or even several times more with or without intermediate drying.
Fibers of this invention can be used in the reinforcement of hoses, belts, ropes and cables including optical cables, rubber goods and composite structures sporting goods, medical supplies, building and acoustic material, transport and protective equipment for civil and military applications Description of Preferred Embodiments Example 1 In this example, aramid fiber in a yam of 1100 dtex and coated by the finish of this invention was compared with commercially-available aramid yarn of the same dtex coated by a standard finish.
The aramid fiber of this invention shows superiority, in terms of friction, especially dynamic friction F/M (200 m/min), deposit measured in mg/kg of yarn, and fibrillation compared to the control aramid fiber (Comparison) which is commercially available.
For antistatic evaluation, a generally good performance starts at -6 kV, consequently the measured value of -2.5 kV for the fiber of this invention is excellent in terms of staticity.
The scourability (wash-off property) is a very important factor since the residual finish level after a washing-step (measured in impacts any subsequent finishing operation. Scourability values mentioned in the Table below were obtained on an industrial scale using fabrics made of the yarn of this invention and compared with a control yarn which was a commercial product of the same denier treated with a standard finish. The values were confirmed in the laboratory by washing the yarns two times with soft water at 50 0 C using 100 inl of water for g of yam.
Friction coefficients were determined according to the following method: A package of yarn is threaded through a tensioning device, between a guide roll and two strain gauges, and onto a take-up roll driven by a variable speed motor. The two strain gauges record T 1 and T 2 input and output tension respectively. The coefficient of friction is computed according to the formula: Ti/T2 exp (a.f) WO 92/15747 PCT/US92/01891 where a is the friction angle and f the friction coefficient (fiber to fiber, fiber to metal or fiber to ceramic, depending on whether a polished chrome or ceramic pin was used). The Rothschild friction meter R-1182 has been used according to the standard procedure known in the art.
The deposit due to abrasion was measured on a "Staff-Tester G 555" (Zweigle, West Germany) with which the weight of the abraded fiber-material arising from fiber to fiber friction was determined.
The fibrillation index was determined on a "G 566" apparatus (Zweigle, West Germany).
Comparison of physical properties Com- This (1100 dtex Fiber) parison Invention 1. Friction Fiber/Fiber (0.016 cm/s) 0.22 0.215 (128 cm/s) 0.28 0.265 Fiber/Metal (0.016 cm/s) 0.12 0.045 (128 cm/s) 0.30 0.265 (200 m/min) 0.70 0.55 2. Deposit (mg/kg) 10 3. Fibrillation index 21 4. Scourability 46% 9% (Residual finish level) Example 2 In this example, a fabric woven from the yam of this invention and a comparison fabric woven from commercially available yarn having a standard finish were tested for ballistic performance.
The fabrics were made of 1111 dtex (1000 denier) yarns.
3 o Usually in the area of high tenacity fiber the weaving operation of ballistic fabrics leads to strength losses usually quantified by extracting the yarn out of the fabric and measuring the tenacity according to the standard procedures known in the art. The following Table shows that the product of this invention yields a significant advantage since, in a heavy fabric construction (typically 12 ends per cm), the strength loss is reduced by half (7 vs. The ballistic performance WO 92/15747 10 PCT/US92/01891 see test procedure) is also improved by 8% at the greige fabric level and 5 to 8% at the finished level (meaning after final fabric treatment).
In the case of light weight fabric, typically 8 ends per cm, the ballistic performance is also increased by 4.5% at the greige fabric level.
Strength Conversion and Ballistic Performance Fabric Grade Strength Strength Percentage Loss, Loss, improvement This Cor- in Ballistic Invention parison Performance
V
5 0 of This Invention vs.
Comparison HEAVY FABRIC of the state of the art: 1. greige 14%-18% 2. ballistic perform.
(greige fabric) 8% 3. ballistic perform.
(finished fabric) 5-8% LIGHT FABRIC of the state of the art 1. greige 0-2% 0-2% 2. ballistic perform.
(greige fabric) Ballistic tests 3 o The ballistic test method for determining V 5 0 was carried out according to the NATO standardization agreement STANAG 2920.
The V 5 0 ballistic limit velocity for a material or armour is defined as that velocity for which the probability of penetration of the chosen projectiles is exactly 0.5, using the Up and Down firing method and calculation described below.
WO 9215747 PCT/US92/01891 WO 92/15747 The Up and Down firing method: The first round shall be loaded with the amount of propellant caculated to give the projectile a velocity equivalent to the estimated V 5 0 ballistic limit of the armour. If the first round fired produces a complete penetration, the second round shall be loaded with a fixed decrement of propellant calculated to produce a velocity about 30 m/s lower than the first. If the first round fired results in a partial penetration, the second round shall be loaded with a fixed increment of propellant cr culated to produce a velocity about 30 m/s higher than the first round.
Upon achieving the first set of penetration reversals, the propellant charge should be adjusted with the fixed amount to yield an increment or decrement of velocity of about 15 m/s. Firing will then continue in accordance with a given procedure *to obtain an estimate of the V 5 0 (BLP) [Ballistic Limit Protection].
V
5 0 calculation: After a number of projectiles have been fired the V 5 0 is calculated as the mean of the velocities recorded for the fair impact the fair impacts consisting of the three highest partial velocities for partial penetration and the three lowest velocities for complete penetration provided that all six velocities fall within a bracket of 40 m/s.
Example 3 In this example, knitting processability evaluation was carried out under the following conditions: ELHA Circular Knitting Machine (Model RRU), test duration 4 hours, machine speed 6 7 0 rpm, knitting speed 1 5 m/min; knitting construction 3 stitches /cm.
WO 92/15747 1 2 PCY/US92/01891 End-Use Performance of Different Yarn Types Yarn Type Comparison 0 T/m Comparison 120 T/m This invention Process and (b) 0 T/m Fibrillation Knit Design Deposit high none none not uniform build-up, deposit not uniform uniform slight deposit low uniform no deposit optimum Coverage Factor As can be seen in the table, above, optimum productivity levels and maximum value in use could be obtained using yars of this invention versus the Comparison yarns. The state of the art product is used twisted. The results clearly show the advantage related to the possibility of avoiding the twisting operation by using yarns of this invention.
Example 4 In this example, fatigue trials on hoses, made using yarn of this invention, were carried out to the Ford specification with pressures of 1-3.5 bar at Hz according to the most severe trapezoid waveform.
With Comparison yar, 50,000 cycles to failure are generally obtained and are sufficient to pass the test. However, a result of 80,000 cycles has been obtained for five hose samples containing yarns of this invention. This shows a significant superiority of the yarns of this invention in terms of fatigue resistance.
WO 92/15747 PCT/US92/01891 Example In this example, the strength efficiency conversion of cords made using yarns of this invention was compared with that of cords made using Comparison yarns.
Compared with commercially available aramid based construction, up .o 30% better strength efficiency conversion was obtained by using yarn of this invention for cord construction. If a cord is made of several yarns, the strength of the cord theoretically should be equal to the strength of each yam, multiplied by the number of yarns, which is never the case in practice. However, the finish of this invention helps to overcome this problem.
In a laboratory test, the strength of a parallel construction made of three commercial 1100 dtex (1000 filaments) aramid yarns with a final twisting of 140 T/m (twists per meter) was determined to be 524 N. This was compared with a parallel cord construction made of three 1100 dtex yarns which were treated with the finish of this invention by weight finish level). The finally obtained strength of a yam with a twist level of 140 T/m was 592 N which corresponds to a increase.
Example 6 In this example, several qualities of yam of this invention were tested and compared with those qualities as exhibited by Comparison yarn.
Test conditions: Weight loss is measured by the percentage of finish material lost after exposing the fibers at 230°C for 8 hours. The finish percentage is determined by solvent extraction before and after the heat exposure.
The percentage of residue after scouring is also determined by solvent extraction of the residual finish remaining on the fiber after washing (scouring) the fiber according to washing procedures known and applied in the industry. The percentage is calculated versus the initial finish level determined prior to the scouring step.
The fiber to metal friction coefficient is measured at 150 m/min using the Rothschild equipment and method as described previously.
WO 92/15747 PCT/US92/01891 Finish weight Finish remaining F/M loss on after friction Fiber heating scouring coefficient
A
This invention 5 8 0.50 ("non-fuming")
B
This invention 11 14 0.47 Comparison 23 45 0.65 All yarns were 1000 denier, 670 filament and were coated in the dried .state using a neat finish formulation at a rate of 750 m/minute to a level of 0.8%.
The finish of A included a 70/30 mixture of benzene tricarboxylic acid and benzene dicarboxylic acid as the carboxylic acid component for the esteroil.
The finish of B included a 70/30 mixture of C-18/C-16 alkenyl monocarboxylic acid component for the esteroil.
The finish of the Comparison was C-12/C-15 mineral oil-based as disclosed in Research Disclosure No. 195, disclosure 19520, July, 1980.
By this example, it is noted that finish formulations of this invention in which a carboxylic acid component for the esteroil is used having more than one carboxylic acid group, that is, where n 2-6, the finish formulation yields considerably less weight loss on heating. Less weight loss on heating means less fuming in use and operation at elevated temperatures.
Claims (15)
1. Aramid fibers having a coating of a lubricant, an emulsifying system, an antistatic agent, and other components, derived from a surface treatment agent which consists of 30 to 70% by weight of an esteroil lubricant, consisting of an ester, composed of an alcohol component which is a branched, primary or secondary, saturated monohydric alcohol of the general formula R 1 R2 I I CH 3 -(CH2)h-(CH)k.(CH2)j-CH-(CH2)m-OH wherein R 1 represents C1-C16-alkyl, R 2 represents H, C1-C 16 -alkyl, if k= 1 and R 2 represents C 1 -C16-alkyl, if k= 0, h 0 to j 0 to 4 k 0 or 1 m =0 to 16 and wherein the total number of carbon atoms is below and (II) a carboxylic acid component which is an unsaturated fatty acid of the general formula R 3 -(COOH)s; s 1-6 wherein R 3 represents C 4 -C 19 -alkenyl, C 4 -C 19 alkadienyl, C 4 -C 19 -alkatrienyl, phenyl, 3 o naphthyl, 2-phenylethenyl, or which is an unsaturated dicarboxylic acid of the general formula HOOC-(CH= CH)n-COOH wherein n 1 or 2, WO 92/15747 1 PCT/US92/01891 and said ester has a solidification point of below a kinematic viscosity of 100 to 350 mm 2 /s (at 200C) and an iodine value between 30 and 140, 20 to 50% by weight of an emulsifying system which consists of unsaturated ethoxylated fatty acids and/or unsaturated ethoxylated fatty alcohols and/or ethoxylated alkylamines of the general formula R 4 -X-(EO)p(PO)q-OH wherein R 4 represents C5-C 2 0 -alkenyl, phenyl, naphthyl, or C 8 or Cg-alkylphenyl, X represents -COO-, -NH- or EO represents an ethylene oxide unit, PO represents a propylene oxide unit, p 2 to 15 and q 0 to 5 to 15% by weight of an antistatic agent, consisting of alkali salts of C 4 -C 12 alkyl sulfonates, C 4 -C 12 -alkyl phosphates or C4-C 2 0 -alkyl carboxylic acids, 0.2 to 2% by weight of a corrosion-inhibitor, and 2 0 optionally additives, and whereby the amount of said coating on said fibers is 0.05 to 2.0% by weight.
2. Fibers according to Claim 1, characterized in that said alcohol component (I) of is 2-methyl-l-propanol, 2-butanol, 2-pentanol, 2-methyl-l-butanol, 3-methyl-l- butanol, 3-methyl-2-butanol, 2-methyl-l-pentanol, 4-methyl-l-pentanol, 4-methyl-2- pentanol, 2-pentanol, 3-heptanol, 2-octanol, 2-ethyl-l-hexanol, hexanol, 5-nonanol, 2-6-dimethyl-4-heptanol, iso-hexadecyl-alcohbl or iso-tridecyl alcohol.
3. Fibers according to Claim 1, characterized in that said carboxylic acid component (II) of is lauroleic acid, myristoleic acid, palmitoleic acid, oleic acid, gadoleic acid, erucic acid, ricinoleic acid, tallow acid, linoleic acid, linolenic acid, fumaric acid, maleic acid, cinnamic acid, naphthaline carboxylic acid, benzoic acid, terephthalic acid, isophthalic acid, trimellitic acid or pyromellitic acid. WO 92/15747 I PCT/US92/01891
4. Fibers according to Claim 1, characterized in that said emulsifying system comprises octylphenol-ethoxylates (5-15 moles of EO) and/or nonylphenoleth- oxylates (5-15 moles of EO) and/or ethoxylated lauroleic acid, myristoleic acid, palmitoleic acid, gadoleic acid, erucic acid, ricinoleic acid, or oleic acid (3-15 moles of EO) and/or ethoxylates of elaidyl alcohol, erucyl alcohol, brassidyl alcohol, or oleyl alcohol (3-10 moles of EO) and/or tallow alcohol ethoxylate (3-10 moles of EO). Fibers according to Claim 1, characterized in that said surface treatment agent consists of to 60% by weight, of to 40% by weight, of to 10% by weight, of c 0.3 to 1% by weight, of and optionally additives
6. Fibers according to Claim 1, characterized in that repeating units of the aramid have the general formula (-NH-A1-NH-CO-A2-CO-)n 2 o wherein A 1 and A 2 are the same or different and represent substituted or unsubstituted aromatic and/or polyaromatic and/or heteroaromatic rings.
7. Fibers according to Claim 6 characterized in that Al and A 2 are, independently from each other, selected from 1,4-phenylene, 1,3-phenylene, 1,2- phenylene, 4,4'-biphenylene, 2,6-naphthylene, 1,5-naphthylene, 1,4-naphthylene, phenoxyphenyl-4,4'-diyl, phenoxyphenyl-3,4'-diyl, 2,5-pyridylene and 2,6-quinolylene and which may or may not be substituted by one or more substituents comprising halogen, C 1 -C 4 -alkyl, phenyl, carboalkoxyl, C 1 -C4-alkoxyl, acyloxy, nitro, 3o dialkylamino, thioalkyl, carboxyl and sulfonyl and in which the amide-group may also be replaced by a carbonylhydrazide-, azo- or azoxy-group.
8. Fibers according to Claim 6, characterized in that the aromatic polyamide is a copolyamide in which preferably at least 80% by mole of the total A 1 and A2 are WO 92/15747 u PCT/US92/01891 1,4-phenylene and phenoxyphenyl-3,4'-diyl which may or may not be substituted, and the content of phenoxyphenyl-3,4'-diylene is 10% to 40% by mcle.
9. Fibers according to Claim 6, characterized in that the polyamide fibers consist of poly-(m-phenylene-isophthalamide). Fibers according to Claims 6, characterized in that the polyamide fibers consist of poly-p-(phenylene-terephthalamide).
11. Fibers according to Claims 6, characterized in that said polyamide fibers contain optionally units which are derived from 3- or 4-aminobenzoic acid.
12. A process for making aramid fibers having a coating of a surface treatment agent, comprising the steps of applying the surface treatment agent to said fiber in an aqueous system of concentration 1 to 100%, by weight, drying the fibers at a temperature between 150 and 190°C, optionally, repeating the application of the surface treatment agent, characterized further in that the surface treatment agent consists of 30 to 70% by weight of an esteroil lubricant, consisting of an ester, composed of an alcohol component which is a branched, primary or secondary, saturated monohydric alcohol of the general formula R 1 R2 I I CH3-(CH2)h-(CH)k-(CH2)j-CH-(CH2)m-OH wherein R 1 represents C 1 -C 16 -alkyl, R 2 represents H, C 1 -C16-alkyl, if k= 1 and R2 represents C 1 -C 16 -alkyl, if k= 0, h j 0to 4 k =0orl m =0to16 WO 92/15747 PCT/US92/01 891 and wherein the total number of carbon atoms is below and (II) a carboxylic acid component which is an unsaturated fatty acid of the general formula R 3 -(COOH)s; s 1-6 wherein R 3 represents C 4 -C 19 -alkenyl, C 4 -C 19 alkadienyl, C4-C 19 -alkatrienyl, phenyl, naphthyl, 2-phenylethenyl, or which is an unsaturated dicarboxylic acid of the general formula HOOC-(CH CH)n-COOH wherein n 1 or 2, and said ester has a solidification point of below 5°C, a kinematic viscosity of 100 to 350 mm 2 /s (at 20 0 C) and an iodine value between 30 and 140, 20 to 50% by weight of an emulsifying system which consists of unsaturated ethoxylated fatty acids and/or unsaturated ethoxylated fatty alcohols and/or ethoxylated alkylamines of the general formula R 4 -X-(EO)p(PO)q-OH wherein R4 represents C 5 -C 2 0 a lkenyl, phenyl, naphthyl, or C 8 or C 9 -alkylphenyl, X represents -COO-, -NH- or EO represeiits an ethylene oxide unit, PO represents a propylene oxide unit, p 2 to 15 and q 0 to 5 to 15% by weight of an antistatic agent, consisting of alkali salts of C4-C12- 3o alkyl sulfonates, C 4 -C 12 -alkyl phosphates or C 4 -C 2 0 -alkyl carboxylic acids, 0.2 to 2% by weight of a corrosion-inhibitor, and optionally additives
13. Process according to Claim 12, characterized in that the concentration of the surface treatment agent in water is 30% by weight. WO 92/15747 20 PCT/US92/01891
14. Process according to Claim 12, characterized in that the concentration of the surface treatment is 100%, by weight, that is, that the surface treatment is neat.
15. Process according to Claim 12, characterized in that the surface treatment agent is applied to never-dried aramid fibers.
16. Process according to Claim 12, characterized in that the surface treatment agent is applied to previously-dried aramid fibers. INTERNATIONAL SEARCH REPORT International Application No PCT/US 92/01891 I. CLASSIFICATION OF SUBJECT MATTER (if several classification symbols apply, indicate all)b According to International Patent Classification (IPC) or to both National Classification and IPC D 06 M 13/224 D 06 M 13/17 D 06 M 13/372 II. FIELDS SEARCHED Minimum Documentation Searched 7 Classification System I Classification Symbols C 10 M D 06 M Documentation Searched other than Minimum Documentation to the Extent that such Documents are Included in the Fields Searched' I. DOCUMENTS CONSIDERED TO BE RELEVANT 9 Category Citation of Document, t with indication, where appropriate, of the relevant passages 12 Relevant to Claim No. 13 A DE,A,1815361 (HOECHST) 2 July 1970, 1 see the whole document A US,A,4019990 (MARSHALL et al.) 26 1 April 1977, see the whole document A US,A,3177143 (LENSE) 6 April 1965, 1 see the whole document A US,A,3368917 (BELCHER et al.) 13 1 February 1968, see the whole document A US,A,3682694 (YASUHARU KATO) 8 1 August 1972, see the whole document Special categories of cited documents :10 T' later document published after the international filing date or priority date and not in conflict with the application but document defining the general state of the art which is not cited to understand the principle or theory underlying the considered to be of particular relevance invention earlier document but published on or after the international document of particular relevance the claimed invention ti.Pe dat' cannot be considered novel or cannot be considered to L' documen' which may throw doubts on priority claim(s) or involve an inventive step which is cited to establish the publication date of another document of particular relevance the claimed invention citation or other special reason (as specified) cannot be considered to involve an inventive step when the document referring to an oral disclosure, use, exhibition or document is combined with one or more othotr such docu- other means ments, such combination being obvious to a person skilled document published prior to the international filing date but in the art. later than the priority da.te claimed document member of the same patent family IV. CERTIFICATION Date of the Actual Completion of the International Search Date of Mailing of this International Search Report
19-06-1992 16f 07. 92 International Searching Authority Signature of Authorized Officer EUROPEAN PATENT OFFICE Mra y Form PCTIlSAIZtO (iond tt_ (JMarnaP [9 Form PCTtISA21(1 4ecd tUetl tjiSaUy t1 ANNEX TO THE INTERNATIONAL SEARCH REPORT ON INTERNATIONAL PATENT APPLICATION NO. US 9201891 SA 58217 This annex lists the patent family members relating to the patent documents cited in the above-mentioned international search report. The members are as contained in the European Patent Office EDP file on 08/07/92 The European Patent Office is in no way liable for these particulars which are merely given for the purpose of information. Patent document Publication Pat2nt family Publication cited in search report date members) date DE-A- 1815361 02-07-70 BE-A- 743360 18-06-70 CH-A- 1858269 FR-A- 2026463 18-09-70 GB-A- 1233330 26-05-71 NL-A- 6918522 22-06-70 .US-A- 4019990 26-04-77 None US-A- 3177143 BE-A- 591186 DE-B- 1168860 DE-A- 1419430 24-10-68 FR-A- 1258042 FR-A- 1258564 GB-A- 878846 GB-A- 920659 NL-A- 251989 NL-A- 251990 US-A- 3010849 US-A- 3061474 US-A- 3368917 None US-A- 3682694 08-08-72 None For more details about this annex see Oicial Journal of te European Patet Office, No. 1282 A' For more details about this annex :see Official Journal of the European Patent Office, No. 12/82
Applications Claiming Priority (4)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE4106682A DE4106682C2 (en) | 1991-03-02 | 1991-03-02 | Aromatic high-performance polyamide fibers, their production and use |
DE4106682 | 1991-03-02 | ||
PCT/US1992/001891 WO1992015747A1 (en) | 1991-03-02 | 1992-03-02 | Highly processable aromatic polyamide fibers, their production and use |
CN92103391A CN1049462C (en) | 1991-03-02 | 1992-04-03 | Highly processable aromatic polyamide fibers, their production and use |
Publications (2)
Publication Number | Publication Date |
---|---|
AU1460892A AU1460892A (en) | 1992-10-06 |
AU660455B2 true AU660455B2 (en) | 1995-06-29 |
Family
ID=25742744
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
AU14608/92A Ceased AU660455B2 (en) | 1991-03-02 | 1992-03-02 | Highly processable aromatic polyamide fibers, their production and use |
Country Status (8)
Country | Link |
---|---|
EP (1) | EP0574507B1 (en) |
JP (1) | JP3383860B2 (en) |
CN (1) | CN1049462C (en) |
AU (1) | AU660455B2 (en) |
BR (1) | BR9205704A (en) |
DE (2) | DE4106682C2 (en) |
ES (1) | ES2057991T3 (en) |
WO (1) | WO1992015747A1 (en) |
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 |
EP1131377B1 (en) * | 1999-07-12 | 2003-07-02 | Société de Technologie Michelin | Tyre casing whereof the sidewalls can comprise a glazed film |
US6706931B2 (en) * | 2000-12-21 | 2004-03-16 | Shell Oil Company | Branched primary alcohol compositions and derivatives thereof |
JP4747255B2 (en) * | 2000-12-27 | 2011-08-17 | Jnc株式会社 | Tow having charging property and laminate using the same |
EP1435407A1 (en) * | 2003-01-02 | 2004-07-07 | Teijin Twaron B.V. | Aramid filament yarn provided with a conductive finish |
CN1318684C (en) * | 2004-07-09 | 2007-05-30 | 竹本油脂(苏州)有限公司 | Treatment agent for spinning of animal hair fiber |
JP4480176B2 (en) * | 2006-12-27 | 2010-06-16 | 竹本油脂株式会社 | Synthetic fiber treatment liquid and synthetic fiber treatment method |
JP5604141B2 (en) * | 2010-03-11 | 2014-10-08 | Jx日鉱日石エネルギー株式会社 | Oil composition and ultra-trace oil supply type cutting / grinding method |
JP5260621B2 (en) * | 2010-12-15 | 2013-08-14 | 花王株式会社 | Fiber treatment agent |
EP3411351A4 (en) * | 2016-02-03 | 2019-09-04 | Elevance Renewable Sciences, Inc. | Alkoxylated unsaturated fatty acids and uses thereof |
CN109486181A (en) * | 2018-11-22 | 2019-03-19 | 江苏利德尔新材料科技有限公司 | A kind of preparation method of antistatic high fire-retardance MC nylon composite materials |
Citations (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3368917A (en) * | 1967-01-06 | 1968-02-13 | Deering Milliken Res Corp | Coated textile yarn |
Family Cites Families (6)
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 |
CH1858269D (en) * | 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 (en) * | 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/en not_active Expired - Fee Related
-
1992
- 1992-03-02 DE DE69200321T patent/DE69200321T2/en not_active Expired - Fee Related
- 1992-03-02 ES ES92907819T patent/ES2057991T3/en not_active Expired - Lifetime
- 1992-03-02 EP EP92907819A patent/EP0574507B1/en not_active Expired - Lifetime
- 1992-03-02 JP JP50744992A patent/JP3383860B2/en not_active Expired - Fee Related
- 1992-03-02 AU AU14608/92A patent/AU660455B2/en not_active Ceased
- 1992-03-02 BR BR9205704A patent/BR9205704A/en not_active IP Right Cessation
- 1992-03-02 WO PCT/US1992/001891 patent/WO1992015747A1/en active IP Right Grant
- 1992-04-03 CN CN92103391A patent/CN1049462C/en not_active Expired - Fee Related
Patent Citations (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3368917A (en) * | 1967-01-06 | 1968-02-13 | Deering Milliken Res Corp | Coated textile yarn |
Also Published As
Publication number | Publication date |
---|---|
JPH06505312A (en) | 1994-06-16 |
DE4106682A1 (en) | 1992-10-08 |
DE4106682C2 (en) | 1995-08-10 |
ES2057991T3 (en) | 1994-10-16 |
AU1460892A (en) | 1992-10-06 |
JP3383860B2 (en) | 2003-03-10 |
WO1992015747A1 (en) | 1992-09-17 |
CN1049462C (en) | 2000-02-16 |
DE69200321D1 (en) | 1994-09-15 |
DE69200321T2 (en) | 1995-02-09 |
CN1076977A (en) | 1993-10-06 |
EP0574507B1 (en) | 1994-08-10 |
EP0574507A1 (en) | 1993-12-22 |
BR9205704A (en) | 1994-08-02 |
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