JPS6137388B2 - - Google Patents
Info
- Publication number
- JPS6137388B2 JPS6137388B2 JP57217085A JP21708582A JPS6137388B2 JP S6137388 B2 JPS6137388 B2 JP S6137388B2 JP 57217085 A JP57217085 A JP 57217085A JP 21708582 A JP21708582 A JP 21708582A JP S6137388 B2 JPS6137388 B2 JP S6137388B2
- Authority
- JP
- Japan
- Prior art keywords
- polyester
- acid
- weight
- polymer
- present
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- 229920000728 polyester Polymers 0.000 claims description 61
- 239000000835 fiber Substances 0.000 claims description 59
- 229920000642 polymer Polymers 0.000 claims description 40
- 239000000203 mixture Substances 0.000 claims description 26
- 229920000570 polyether Polymers 0.000 claims description 8
- 239000004721 Polyphenylene oxide Substances 0.000 claims description 7
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims description 6
- 239000002253 acid Substances 0.000 claims description 6
- 125000001931 aliphatic group Chemical group 0.000 claims description 3
- 125000003118 aryl group Chemical group 0.000 claims description 3
- 125000000542 sulfonic acid group Chemical group 0.000 claims description 3
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 claims 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 20
- -1 aromatic dicarboxylic acids Chemical class 0.000 description 17
- 238000000034 method Methods 0.000 description 17
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 15
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 14
- 239000000306 component Substances 0.000 description 14
- 238000010521 absorption reaction Methods 0.000 description 13
- 230000003373 anti-fouling effect Effects 0.000 description 13
- 229920002614 Polyether block amide Polymers 0.000 description 12
- 238000005108 dry cleaning Methods 0.000 description 11
- 230000000052 comparative effect Effects 0.000 description 9
- 239000004744 fabric Substances 0.000 description 9
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 8
- 239000002131 composite material Substances 0.000 description 8
- 238000005406 washing Methods 0.000 description 8
- 229920001281 polyalkylene Polymers 0.000 description 7
- 239000002202 Polyethylene glycol Substances 0.000 description 5
- 229910052783 alkali metal Inorganic materials 0.000 description 5
- 239000006185 dispersion Substances 0.000 description 5
- 229920001223 polyethylene glycol Polymers 0.000 description 5
- QQVIHTHCMHWDBS-UHFFFAOYSA-N isophthalic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 description 4
- 230000007935 neutral effect Effects 0.000 description 4
- 239000004952 Polyamide Substances 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- 101100409194 Rattus norvegicus Ppargc1b gene Proteins 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 229920001577 copolymer Polymers 0.000 description 3
- 239000003599 detergent Substances 0.000 description 3
- 150000001990 dicarboxylic acid derivatives Chemical class 0.000 description 3
- 150000001991 dicarboxylic acids Chemical class 0.000 description 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
- 150000002009 diols Chemical class 0.000 description 3
- 239000000975 dye Substances 0.000 description 3
- 238000004043 dyeing Methods 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 229920002647 polyamide Polymers 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- 238000009987 spinning Methods 0.000 description 3
- 238000010186 staining Methods 0.000 description 3
- 230000003068 static effect Effects 0.000 description 3
- 239000002759 woven fabric Substances 0.000 description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical group [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 2
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical class OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 2
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 2
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 2
- TWRXJAOTZQYOKJ-UHFFFAOYSA-L Magnesium chloride Chemical compound [Mg+2].[Cl-].[Cl-] TWRXJAOTZQYOKJ-UHFFFAOYSA-L 0.000 description 2
- 229920002292 Nylon 6 Polymers 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- 239000004698 Polyethylene Substances 0.000 description 2
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 2
- 229920001400 block copolymer Polymers 0.000 description 2
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 2
- 239000011248 coating agent Substances 0.000 description 2
- 238000000576 coating method Methods 0.000 description 2
- 239000008358 core component Substances 0.000 description 2
- DIOQZVSQGTUSAI-UHFFFAOYSA-N decane Chemical compound CCCCCCCCCC DIOQZVSQGTUSAI-UHFFFAOYSA-N 0.000 description 2
- MNNHAPBLZZVQHP-UHFFFAOYSA-N diammonium hydrogen phosphate Chemical compound [NH4+].[NH4+].OP([O-])([O-])=O MNNHAPBLZZVQHP-UHFFFAOYSA-N 0.000 description 2
- WOZVHXUHUFLZGK-UHFFFAOYSA-N dimethyl terephthalate Chemical compound COC(=O)C1=CC=C(C(=O)OC)C=C1 WOZVHXUHUFLZGK-UHFFFAOYSA-N 0.000 description 2
- GVGUFUZHNYFZLC-UHFFFAOYSA-N dodecyl benzenesulfonate;sodium Chemical compound [Na].CCCCCCCCCCCCOS(=O)(=O)C1=CC=CC=C1 GVGUFUZHNYFZLC-UHFFFAOYSA-N 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 230000005611 electricity Effects 0.000 description 2
- 239000000839 emulsion Substances 0.000 description 2
- JBKVHLHDHHXQEQ-UHFFFAOYSA-N epsilon-caprolactam Chemical compound O=C1CCCCCN1 JBKVHLHDHHXQEQ-UHFFFAOYSA-N 0.000 description 2
- 125000001033 ether group Chemical group 0.000 description 2
- 230000004927 fusion Effects 0.000 description 2
- 229910017053 inorganic salt Inorganic materials 0.000 description 2
- 229910052744 lithium Inorganic materials 0.000 description 2
- 239000005486 organic electrolyte Substances 0.000 description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
- 239000002530 phenolic antioxidant Substances 0.000 description 2
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 2
- 229920001515 polyalkylene glycol Polymers 0.000 description 2
- 229920000573 polyethylene Polymers 0.000 description 2
- 229920000139 polyethylene terephthalate Polymers 0.000 description 2
- 239000005020 polyethylene terephthalate Substances 0.000 description 2
- 229910052700 potassium Inorganic materials 0.000 description 2
- 239000011591 potassium Substances 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 229940080264 sodium dodecylbenzenesulfonate Drugs 0.000 description 2
- TYFQFVWCELRYAO-UHFFFAOYSA-N suberic acid Chemical compound OC(=O)CCCCCCC(O)=O TYFQFVWCELRYAO-UHFFFAOYSA-N 0.000 description 2
- 150000008054 sulfonate salts Chemical class 0.000 description 2
- LDMOEFOXLIZJOW-UHFFFAOYSA-N 1-dodecanesulfonic acid Chemical compound CCCCCCCCCCCCS(O)(=O)=O LDMOEFOXLIZJOW-UHFFFAOYSA-N 0.000 description 1
- RTBFRGCFXZNCOE-UHFFFAOYSA-N 1-methylsulfonylpiperidin-4-one Chemical compound CS(=O)(=O)N1CCC(=O)CC1 RTBFRGCFXZNCOE-UHFFFAOYSA-N 0.000 description 1
- KGRVJHAUYBGFFP-UHFFFAOYSA-N 2,2'-Methylenebis(4-methyl-6-tert-butylphenol) Chemical compound CC(C)(C)C1=CC(C)=CC(CC=2C(=C(C=C(C)C=2)C(C)(C)C)O)=C1O KGRVJHAUYBGFFP-UHFFFAOYSA-N 0.000 description 1
- WBIQQQGBSDOWNP-UHFFFAOYSA-N 2-dodecylbenzenesulfonic acid Chemical compound CCCCCCCCCCCCC1=CC=CC=C1S(O)(=O)=O WBIQQQGBSDOWNP-UHFFFAOYSA-N 0.000 description 1
- ZCXNPIWNNTXPSE-UHFFFAOYSA-N 2-sulfopentanedioic acid Chemical compound OC(=O)CCC(C(O)=O)S(O)(=O)=O ZCXNPIWNNTXPSE-UHFFFAOYSA-N 0.000 description 1
- RAADBCJYJHQQBI-UHFFFAOYSA-N 2-sulfoterephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C(S(O)(=O)=O)=C1 RAADBCJYJHQQBI-UHFFFAOYSA-N 0.000 description 1
- GPNYZBKIGXGYNU-UHFFFAOYSA-N 2-tert-butyl-6-[(3-tert-butyl-5-ethyl-2-hydroxyphenyl)methyl]-4-ethylphenol Chemical compound CC(C)(C)C1=CC(CC)=CC(CC=2C(=C(C=C(CC)C=2)C(C)(C)C)O)=C1O GPNYZBKIGXGYNU-UHFFFAOYSA-N 0.000 description 1
- PVXSFEGIHWMAOD-UHFFFAOYSA-N 2-tridecylbenzenesulfonic acid Chemical compound CCCCCCCCCCCCCC1=CC=CC=C1S(O)(=O)=O PVXSFEGIHWMAOD-UHFFFAOYSA-N 0.000 description 1
- YAKQEKJIYFCETJ-UHFFFAOYSA-N 3-sulfopentanedioic acid Chemical compound OC(=O)CC(S(O)(=O)=O)CC(O)=O YAKQEKJIYFCETJ-UHFFFAOYSA-N 0.000 description 1
- VSAWBBYYMBQKIK-UHFFFAOYSA-N 4-[[3,5-bis[(3,5-ditert-butyl-4-hydroxyphenyl)methyl]-2,4,6-trimethylphenyl]methyl]-2,6-ditert-butylphenol Chemical compound CC1=C(CC=2C=C(C(O)=C(C=2)C(C)(C)C)C(C)(C)C)C(C)=C(CC=2C=C(C(O)=C(C=2)C(C)(C)C)C(C)(C)C)C(C)=C1CC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 VSAWBBYYMBQKIK-UHFFFAOYSA-N 0.000 description 1
- VGCGTWKIEVDCQW-UHFFFAOYSA-N 4-[[3,5-bis[(3,5-ditert-butyl-4-hydroxyphenyl)methyl]-4,6,6-trimethylcyclohexa-2,4-dien-1-yl]methyl]-2,6-ditert-butylphenol Chemical compound CC=1C(=CC(C(C=1CC1=CC(=C(C(=C1)C(C)(C)C)O)C(C)(C)C)(C)C)CC1=CC(=C(C(=C1)C(C)(C)C)O)C(C)(C)C)CC1=CC(=C(C(=C1)C(C)(C)C)O)C(C)(C)C VGCGTWKIEVDCQW-UHFFFAOYSA-N 0.000 description 1
- WPTFZDRBJGXAMT-UHFFFAOYSA-N 4-nonylbenzenesulfonic acid Chemical compound CCCCCCCCCC1=CC=C(S(O)(=O)=O)C=C1 WPTFZDRBJGXAMT-UHFFFAOYSA-N 0.000 description 1
- CARJPEPCULYFFP-UHFFFAOYSA-N 5-Sulfo-1,3-benzenedicarboxylic acid Chemical compound OC(=O)C1=CC(C(O)=O)=CC(S(O)(=O)=O)=C1 CARJPEPCULYFFP-UHFFFAOYSA-N 0.000 description 1
- FITNAOAKVDEJHB-UHFFFAOYSA-N 6-azaniumylhexylazanium;benzene-1,3-dicarboxylate Chemical compound NCCCCCCN.OC(=O)C1=CC=CC(C(O)=O)=C1 FITNAOAKVDEJHB-UHFFFAOYSA-N 0.000 description 1
- UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- 229920000742 Cotton Polymers 0.000 description 1
- 239000005696 Diammonium phosphate Substances 0.000 description 1
- JSFUMBWFPQSADC-UHFFFAOYSA-N Disperse Blue 1 Chemical compound O=C1C2=C(N)C=CC(N)=C2C(=O)C2=C1C(N)=CC=C2N JSFUMBWFPQSADC-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- JHWNWJKBPDFINM-UHFFFAOYSA-N Laurolactam Chemical compound O=C1CCCCCCCCCCCN1 JHWNWJKBPDFINM-UHFFFAOYSA-N 0.000 description 1
- 229920000877 Melamine resin Polymers 0.000 description 1
- 239000004640 Melamine resin Substances 0.000 description 1
- BAVYZALUXZFZLV-UHFFFAOYSA-O Methylammonium ion Chemical compound [NH3+]C BAVYZALUXZFZLV-UHFFFAOYSA-O 0.000 description 1
- PQBAWAQIRZIWIV-UHFFFAOYSA-N N-methylpyridinium Chemical compound C[N+]1=CC=CC=C1 PQBAWAQIRZIWIV-UHFFFAOYSA-N 0.000 description 1
- 239000004677 Nylon Substances 0.000 description 1
- 229920000299 Nylon 12 Polymers 0.000 description 1
- 239000004743 Polypropylene Substances 0.000 description 1
- 239000011398 Portland cement Substances 0.000 description 1
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 1
- 229910006127 SO3X Inorganic materials 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- 235000021355 Stearic acid Nutrition 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 1
- ULUAUXLGCMPNKK-UHFFFAOYSA-N Sulfobutanedioic acid Chemical compound OC(=O)CC(C(O)=O)S(O)(=O)=O ULUAUXLGCMPNKK-UHFFFAOYSA-N 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 239000001361 adipic acid Substances 0.000 description 1
- 235000011037 adipic acid Nutrition 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- ZRSKSQHEOZFGLJ-UHFFFAOYSA-N ammonium adipate Chemical compound [NH4+].[NH4+].[O-]C(=O)CCCCC([O-])=O ZRSKSQHEOZFGLJ-UHFFFAOYSA-N 0.000 description 1
- 235000019293 ammonium adipate Nutrition 0.000 description 1
- BFNBIHQBYMNNAN-UHFFFAOYSA-N ammonium sulfate Chemical compound N.N.OS(O)(=O)=O BFNBIHQBYMNNAN-UHFFFAOYSA-N 0.000 description 1
- 229910052921 ammonium sulfate Inorganic materials 0.000 description 1
- 235000011130 ammonium sulphate Nutrition 0.000 description 1
- JFCQEDHGNNZCLN-UHFFFAOYSA-N anhydrous glutaric acid Natural products OC(=O)CCCC(O)=O JFCQEDHGNNZCLN-UHFFFAOYSA-N 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 230000003078 antioxidant effect Effects 0.000 description 1
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 1
- 239000001110 calcium chloride Substances 0.000 description 1
- 229910001628 calcium chloride Inorganic materials 0.000 description 1
- 235000011148 calcium chloride Nutrition 0.000 description 1
- 239000006229 carbon black Substances 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 206010061592 cardiac fibrillation Diseases 0.000 description 1
- 239000004927 clay Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000011109 contamination Methods 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- QYQADNCHXSEGJT-UHFFFAOYSA-N cyclohexane-1,1-dicarboxylate;hydron Chemical compound OC(=O)C1(C(O)=O)CCCCC1 QYQADNCHXSEGJT-UHFFFAOYSA-N 0.000 description 1
- YWJUZWOHLHBWQY-UHFFFAOYSA-N decanedioic acid;hexane-1,6-diamine Chemical compound NCCCCCCN.OC(=O)CCCCCCCCC(O)=O YWJUZWOHLHBWQY-UHFFFAOYSA-N 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 229910000388 diammonium phosphate Inorganic materials 0.000 description 1
- 235000019838 diammonium phosphate Nutrition 0.000 description 1
- SZXQTJUDPRGNJN-UHFFFAOYSA-N dipropylene glycol Chemical compound OCCCOCCCO SZXQTJUDPRGNJN-UHFFFAOYSA-N 0.000 description 1
- 239000000986 disperse dye Substances 0.000 description 1
- TUXJTJITXCHUEL-UHFFFAOYSA-N disperse red 11 Chemical compound C1=CC=C2C(=O)C3=C(N)C(OC)=CC(N)=C3C(=O)C2=C1 TUXJTJITXCHUEL-UHFFFAOYSA-N 0.000 description 1
- 229940060296 dodecylbenzenesulfonic acid Drugs 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000003792 electrolyte Substances 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 230000002600 fibrillogenic effect Effects 0.000 description 1
- 150000002334 glycols Chemical class 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- SSILHZFTFWOUJR-UHFFFAOYSA-N hexadecane-1-sulfonic acid Chemical compound CCCCCCCCCCCCCCCCS(O)(=O)=O SSILHZFTFWOUJR-UHFFFAOYSA-N 0.000 description 1
- XXMIOPMDWAUFGU-UHFFFAOYSA-N hexane-1,6-diol Chemical compound OCCCCCCO XXMIOPMDWAUFGU-UHFFFAOYSA-N 0.000 description 1
- 229920006017 homo-polyamide Polymers 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229920001477 hydrophilic polymer Polymers 0.000 description 1
- 230000002209 hydrophobic effect Effects 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- LVPMIMZXDYBCDF-UHFFFAOYSA-N isocinchomeronic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)N=C1 LVPMIMZXDYBCDF-UHFFFAOYSA-N 0.000 description 1
- 229910001629 magnesium chloride Inorganic materials 0.000 description 1
- 235000011147 magnesium chloride Nutrition 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000002074 melt spinning Methods 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 239000010705 motor oil Substances 0.000 description 1
- ABMFBCRYHDZLRD-UHFFFAOYSA-N naphthalene-1,4-dicarboxylic acid Chemical compound C1=CC=C2C(C(=O)O)=CC=C(C(O)=O)C2=C1 ABMFBCRYHDZLRD-UHFFFAOYSA-N 0.000 description 1
- PSZYNBSKGUBXEH-UHFFFAOYSA-N naphthalene-1-sulfonic acid Chemical compound C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1 PSZYNBSKGUBXEH-UHFFFAOYSA-N 0.000 description 1
- 229920001778 nylon Polymers 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 235000019198 oils Nutrition 0.000 description 1
- 239000004006 olive oil Substances 0.000 description 1
- 235000008390 olive oil Nutrition 0.000 description 1
- 239000012188 paraffin wax Substances 0.000 description 1
- 238000006068 polycondensation reaction Methods 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 230000000379 polymerizing effect Effects 0.000 description 1
- 229920001155 polypropylene Polymers 0.000 description 1
- GJAWHXHKYYXBSV-UHFFFAOYSA-N pyridinedicarboxylic acid Natural products OC(=O)C1=CC=CN=C1C(O)=O GJAWHXHKYYXBSV-UHFFFAOYSA-N 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 230000000717 retained effect Effects 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 235000002639 sodium chloride Nutrition 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- YXTFRJVQOWZDPP-UHFFFAOYSA-M sodium;3,5-dicarboxybenzenesulfonate Chemical compound [Na+].OC(=O)C1=CC(C(O)=O)=CC(S([O-])(=O)=O)=C1 YXTFRJVQOWZDPP-UHFFFAOYSA-M 0.000 description 1
- JSMHQMIPUOPQLR-UHFFFAOYSA-M sodium;dioctadecyl phosphate Chemical compound [Na+].CCCCCCCCCCCCCCCCCCOP([O-])(=O)OCCCCCCCCCCCCCCCCCC JSMHQMIPUOPQLR-UHFFFAOYSA-M 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 description 1
- 150000003460 sulfonic acids Chemical class 0.000 description 1
- 230000002522 swelling effect Effects 0.000 description 1
- CBXCPBUEXACCNR-UHFFFAOYSA-N tetraethylammonium Chemical compound CC[N+](CC)(CC)CC CBXCPBUEXACCNR-UHFFFAOYSA-N 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- ZMANZCXQSJIPKH-UHFFFAOYSA-O triethylammonium ion Chemical compound CC[NH+](CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-O 0.000 description 1
- NUBZKXFFIDEZKG-UHFFFAOYSA-K trisodium;5-sulfonatobenzene-1,3-dicarboxylate Chemical compound [Na+].[Na+].[Na+].[O-]C(=O)C1=CC(C([O-])=O)=CC(S([O-])(=O)=O)=C1 NUBZKXFFIDEZKG-UHFFFAOYSA-K 0.000 description 1
Landscapes
- Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
- Artificial Filaments (AREA)
- Multicomponent Fibers (AREA)
Description
本発明は、吸水、制電、防汚性を同時に有し、
しかも染色堅ろう度の良好な改質ポリエステル系
繊維に関する。
従来、ポリエステル系繊維は優れたイージーケ
ア性で広範囲に活用されているが、本質的に疎水
性であるため、吸水性がない、防汚性に乏しい、
静電気の発生が著しいなど、多くの問題点があつ
た。そのため業界では、各種ポリエチレングライ
コール系化合物をポリエステル系繊維に対し、何
らかの手段で付与せしめ、これらの問題点をカバ
ーしてきた。ところが、このような手段でもつ
て、吸水、制電、防汚性などの諸特性は付与でき
るようになつたが、反面、染色堅ろう度の低下が
大きくなつたり、ドライクリーニング時に再汚染
し、うす汚れた製品になるなど、新たな問題が生
じ、かかる欠点に対する改善要望が強くなつてい
る。
本発明は、かかる背景のもとに、染色堅ろう度
の低下やドライクリーニング時の再汚染のない、
吸水、制電、防汚性能を同時に有するポリエステ
ル系繊維を提供することを目的とするものであ
る。
本発明はかかる目的を達成するために、次の如
き構成をとる。
(1) ポリエーテルセグメントを有する重合体から
なる新水性組成物を含有するポリエステル系繊
維に、スルホン酸基またはスルホン酸塩を有す
る脂肪族または芳香族のジカルボン酸が、酸成
分中、10〜50モル%占めるポリエステル系重合
体層を繊維重量に対して0.05〜10重量%付着せ
しめてなる改質ポリエステル系繊維。
(2) ポリエステル系繊維がその芯部に新水性組成
物を含有してなるポリエステル系複合繊維であ
る特許請求の範囲第1項に記載の改質ポリエス
テル系繊維。
本発明は、上記の如き特定なポリエステル系繊
維に、特定な共重合体化合物を組み合わせること
により、はじめて優れた吸水性ならびに制電性、
防汚性の3種の性能を同時に、かつ耐久性よく発
揮せしめ得たものである。
本発明でいうポリエーテルセグメントを有する
重合体からなる親水性組成物とは、ポリアルキレ
ンエーテルとくにテレフタール酸ならびにポリエ
チレングリコールとエチレングリコールの共重合
体、ポリアルキレンエーテルとポリアミドのブロ
ツク共重合体などの親水性重合体に電解質物質を
含有せしめたものを意味するが、本発明の目的を
達成するためには、かかる親水性重合体としてと
くに、ポリアルキレンエーテルとポリアミドのブ
ロツク共重合体(ブロツクポリエーテルアミド)
が好ましい。
本発明でいうポリエーテルセグメントを有する
重合体からなる親水性組成物を含有するポリエス
テル系繊維とは、該親水性組成物を繊維表面に塗
布してなるポリエステル系繊維あるいは該親水性
組成物を通常のポリエステルと混合紡糸して得た
もの、あるいは、該親水性組成物とポリエステル
の混合物を鞘部に配し、芯部に未変性のポリエス
テルを配した複合繊維、さらには、芯部に該親水
性組成物とポリエステルの混合物を配し、鞘部に
未変性のポリエステルを配した複合繊維などがあ
げられる。かかるポリエステル系繊維はいずれも
本発明の目的を好適に達成する。
かかる繊維のなかでも前3者は、次の点で後者
に劣る傾向がある。
(1) 紡糸時の単糸間融着および未延伸糸のパツケ
ージ上での繊維間融着による野舒性。
(2) 複合繊維となした場合、芯成分と鞘成分との
密着性ならびに、延伸時、仮ヨリ加工時などの
後工程での剥離性による糸品位、特性。
(3) 分散染料で染色した場合の耐光堅ろう度。
したがつて本発明においては、上記ブロツクポ
リエーテルアミド組成物とポリエステルからなる
混合物が芯部、ポリエステルが鞘部であり、該芯
部の占める比率が5〜0重量%で、かつ該芯部に
含まれるブロツクポリエーテルアミド組成物中の
ポリアルキレンエーテル単位の繊維全体に占める
比率が0.05〜5重量%である、芯鞘型のポリエス
テル系複合繊維がとくに好ましい。
ブロツクポリエーテルアミド組成物とは、有機
電解質、フエノール系抗酸化剤を所定量含有した
ブロツクポリエーテルアミドのことである。ここ
でいう有機電解質とは、ドデシルベンゼンスルホ
ン酸、トリデシルベンゼンスルホン酸、ノニルベ
ンゼンスルホン酸、ヘキサデシルスルホン酸、ド
デシルスルホン酸などのスルホン酸とナトリウ
ム、カリウム、リチウムなどのアルカリ金属から
形成されるスルホン酸のアルカリ金属塩、ジステ
アリルリン酸ソーダなどのリン酸のアルカリ金属
塩、その他有機カルボン酸のアルカリ金属塩など
があり、なかでもドデシルベンゼンスルホン酸ソ
ーダなどのスルホン酸の金属塩が良好である。こ
の電解質の配合量は所望する制電能により適宜決
定される。
フエノール系抗酸化剤としては、たとえば、
1・3・5−トリメチル−2・4・6−トリ
(3・5−ジ−tert−ブチル−4−ヒドロキシベ
ンジル)ベンゼン、2・2′−メチレンビス(4−
メチル−6−tert−ブチルフエノール)、2・6
−ジ−tert−ブチル−P−クレゾール、2・2′−
メチレンビス(4−エチル−6−tert−ブチルフ
エノール)などのフエノール系水酸基の隣接位置
に立体障害を有する置換基のはいつたフエノール
系誘導体である。この抗酸化剤はブロツクポリエ
ーテルアミドの安定剤として配合されるものであ
り、とくに溶融紡糸時の熱に対して抗し得る程度
に配合されるが、その量はポリアルキレンエーテ
ル単位の量によつて決定される。
ブロツクポリエーテルアミドを構成するポリエ
ーテルとはポリアルキレンエーテルのことであ
り、ポリエチレンエーテル、ポリプロピレンエー
テル、ポリエチレンプロピレンエーテルなどのエ
チレンオキサイドおよび/またはプロピレンオキ
サイドの重合生成物である。これらポリエーテル
の分子量は1000以上、好ましくは3000〜8000のも
のがよく、なかでもポリエチレングリコールの使
用が最も適している。
一方、ブロツクポリエーテルアミドを構成する
ポリアミドは、ナイロン6、ナイロン8、ナイロ
ン12、ナイロン6・6、ナイロン6・10のような
ホモポリアミドあるいは、これら同志、または他
の共重合成分を含む共重合体でポリアミド形成成
分の重縮合反応により生成するホモまたはコポリ
アミドである。
本発明に特に好適なポリエステル系繊維はかか
るブロツクポリエーテルアミド組成物を含有する
ものであり、たとえば該組成物がポリアルキレン
エーテルセグメントの繊維全体に占める比率が
0.05〜5重量%となる如く、ブロツクポリエーテ
ルアミド組成物をポリエステルに混合せしめてな
る混合物を芯部とし、ポリエステルを鞘部とする
ことにより、優れた耐久性と良好な制電性を有す
るばかりでなく、通常のポリエステル糸と同等の
白度、耐熱性、耐光性、染色堅ろう性を有し、芯
部と鞘部の剥離が生じることがなく、かつフイプ
リル化による品質低下のないポリエステル繊維と
なし得る。
次に本発明に用いるスルホン酸基またはスルホ
ン酸塩を有する脂肪族または芳香族のジカルボン
酸が、酸成分中10〜50モル%を占めるポリエステ
ル系重合体(以下スルホポリエステル重合体とい
う)について説明する。
スルホとは−SO3X基を意味する。ただしX
は、水素またはナトリウム、カリウムおよびリチ
ウムのようなアルカリ金属カチオン、アルカリ土
類金属カチオン、アンモニウム、N−メチルピリ
ジニウム、メチルアンモニウム、トリエチルアン
モニウム、テトラエチルアンモニウムのような第
3級あるいは第4級窒素カチオンである。
本発明にいうスルホ置換ジカルボ酸とは、スル
ホコハク酸、2−スルホグルタル酸、3−スルホ
グルタル酸などのスルホ置換脂肪族ジカルボン
酸、5−スルホイソフタル酸、2−スルホテレフ
タル酸、5−スルホナフタレン−1・4−ジカボ
ン酸などのスルホ置換芳香族ジカルボン酸などを
意味する。
かかるスルホ置換ジカルボン酸以外の非スルホ
置換ジカルボン酸としては、コハク酸、アジピン
酸マレイン酸、グルタル酸、スベリン酸、1・4
−シクロヘキサンジカルボン酸などの脂肪族ジカ
ルボン酸、テレフタル酸、イソフタル酸、フタル
酸、1・4−ナフタレンジカルボン酸、1・5−
ピリジンジカルボン酸などの芳香族ジカルボン酸
があげられ、−方、該ポリエステル重合体のジオ
ール成分としては、エチレングリコール、プロピ
レングリコール、1・4−ブタンジオール、1・
5−ペンタンジオール、1・6−ヘキサンジオー
ル、ジエチレングリコール、ジプロピレングリコ
ールなどがある。
本発明のスルホポリエステル重合体は、上記ス
ルホ置換ジカルボン酸を全酸成分中10〜50モル%
含有するものであるが、更に15〜30モル%の範囲
で含有するものが好ましい。すなわち、酸成分
中、スルホ置換ジカルボン酸が、10モル%未満で
あれば、スルホポリエステル重合体が、本発明の
ポリエステル系繊維に対し、洗たく耐久性に優れ
た付着性を示すが、本発明の目的とする吸水、防
汚性能が不十分であり、一方、スルホ置換ジカル
ボン酸が、酸成分中50モル%を越える場合は、本
発明の目的の一つである吸水、防汚性能は優れる
が、洗たく耐久性に乏しくなる。
かかるスルホポリエステル重合体は水溶性、水
溶性に近い水分散性あるいは、エマルジヨン形態
をとり得るものなど、いずれでもよいが、本発明
の目的を十分に達成する上からはエマルジヨン形
態ないしは水分散形態をとり得るものの方が、本
発明のポリエステル系繊維に対する付着性、なら
びに付着したものの洗たく耐久性面から好まし
い。
かかるスルホポリエステル重合体は、通常のレ
ギユラーポリエステル系繊維に比較して本発明で
いうポリエステル系繊維に対しては付着耐久性が
良好である特徴を有し、吸水、防汚性能の耐久性
を向上する傾向を有するという特徴がある。かく
の如き特徴が生じる原因は明確でないが、本発明
のポリエステル系繊維が、通常のレギユラーポリ
エステル系繊維に比較して親水性ならびに水膨潤
性が大きく、該スルホポリエステル重合体との親
和性が高いことと、該重合体が該繊維内部へ浸入
しやすいことが耐久性向上につながるものと推察
する。また該スルホポリエステル重合体が水中で
の界面電位(ジーターポテンシヤル)が低い傾向
にあることも本発明のポリエステル系繊維との親
和性を高める原因であるとも推察できるが、いず
れにしても本発明にいうポリエステル系繊維とス
ルホポリエステル重合体との相溶性が高い点が、
本発明の大きな特徴である。
本発明はかかるスルホポリエステル重合体から
なる付着層を、ポリエーテルセグメントを有する
重合体からなる親水性組成物を含有するポリエス
テル系繊維に設けたものであるが、重要なことは
該重合体が繊維重量に対して0.05〜10重量%更に
は0.1〜2重量%付着したものが、本発明の目的
を達成する上で選択される。かかる付着層はいか
なる形で設けられてもよいが、本発明のポリエス
テル系繊維上では通常被膜形態をとり、場合によ
つては少なくとも部分的に該繊維内部に保持され
ている形態である。
本発明の利点は、特定なポリエステル系繊維
(特開昭48−27066、特開昭52−150392などのポリ
アルキレングリコールセグメントを有する重合体
層を繊維表面に有する吸水、制電、防汚性繊維)
の染色堅牢度の低下ならびにドライクリーニング
時の再汚染による黒ずみ欠点は各種の加工剤を用
いても、性能が相殺されたり、更に別の欠点の惹
起を促したりして至難であつたものを、容易な手
段により改善し得た点にある。
衣料用繊維は各種性能もさることながら、制電
性を有することが極めて重要な必須性能として考
えられており、たとえば本発明のスルホポリエス
テル重合体を通常のポリエステル系繊維に付与し
ても、制電性は得られず、衣料分野への適用には
大きな制約を受けざるを得ない問題があつた。
本発明者らはかかるスルホポリエステル重合体
が特にポリアルキレングリコールセグメントを有
する重合体とは各性能を相殺することなく相乗的
に作用することを究明し、しかも従来技術では予
想だにしなかつた染色堅牢度ならびにドライクリ
ーニング再汚染性の問題をも一挙に解決し得る事
実を知見したものである。
かかる本発明の改質ポリエステル系繊維は洗た
く耐久性に優れた、高レベルの吸水、制電、防汚
性能を有するだけではなく、ドライクリーニング
時の再汚染の少ない、しかも染色堅ろう度におい
てもすぐれた性能を発揮するものである。
次に本発明の改質ポリエステル系繊維を製造す
る方法について、その一例をあげて以下説明す
る。
本発明のポリエーテルセグメントを有する重合
体からなる親水性組成物を含有するポリエステル
系繊維は、通常の如く、該組成物をポリエステル
系繊維にコーテイングする方法あるいは該組成物
とポリエステルとを混合紡糸方式、複合紡糸方式
などの方法により形成される。
かかる繊維にスルホポリエステル重合体層を設
ける場合、該重合体を0.1〜100g/含有する処
理液で処理する。0.1g/未満では本発明の目的
が達成できず、また100g/を越えると、本発明
の目的は十分達成できるが、効果は平衡に達す
る。したがつて、それ以上の使用はコストを高め
るだけで、工業上不利である。
かかる処理液には必要に応じ、水溶性の無機塩
を0.1〜10g/添加してもよい。ここでいう、水
溶性の無機塩とは、硫酸ナトリウム、塩化ナトリ
ウム、硫酸アンモニウム、第二リン酸アンモニウ
ム、塩化カルシウム、塩化マグネシウム、塩化亜
塩などを意味する。これらの無機塩の併用によ
り、スルホポリエステル重合体の該ポリエステル
系繊維への付着性をさらに向上せしめうる。
また、該処理液のPHは中性ないしは酸性サイド
がよく、望ましくはPH3〜6が付着性向上、耐久
性向上の面で好ましい。
かかる液理液により、該ポリエステル系繊維上
に該重合体層を設ける方法としては、パツド−ド
ライ法、パツド−スチーム法、ならびに浴中で処
理する方法など、いずれの方法を採用してもよい
が、最も効果が認められる方法は、浴中処理法で
あり、60〜135℃の浴中で2〜60分間処理する。
この処理は染色と同時処理であつてもよい。次に
効果のある方法はパツド−スチーム法で、80℃以
上で2〜60分処理すれば、十分性能を付与するこ
とができる。
また、被処理物の形態としては、ステープル、
トウ、フイラメント、紡績糸、編物、織物、ウエ
ブなど、いずれの形態でもよいが、編織物が最も
処理しやすい。
以下、具体的に実施例で説明する。なお実施例
中に示す摩擦帯電圧、吸水性、防汚性、ドライク
リーニング時の再汚染性ならびに染色堅ろう度な
どの評価方法を以下に詳述する。
〔摩擦帯電圧〕
京大化研式ロータリースタテイクテスター(興
亜商会製)により、摩擦対象布としてあらかじめ
のり抜き、精練、漂白した木綿の平織カナキン3
号(目付100g/m2)を用い、ローター回転数
400rpm、印加電圧100V、温度20℃、相対湿度30
%の雰囲気中で測定した値である。
〔吸水性〕
JIS L−1079注射針法に準じた。
〔防汚性〕
AATCC 130−69に準拠した方法で、ロ紙上に
20cm×20cmの試料をのせ、モーターオイル、ダフ
ニトロニツクオイルSEA(出光興産製)を3
滴、同じ場所に3cmの高さから滴下し、1昼夜間
放置した後、中性洗剤1g/を含む家庭用洗濯
機で40℃で10分間洗濯を行い、次いで水洗、乾燥
する。かくして得られた試料を5tain標準板と比
較判定する。
〔洗濯耐久性〕
中性洗剤1g/を含んだ40℃の洗濯液中で家
庭用洗濯機で試料を洗濯した後、前述の摩擦帯電
圧、吸水性、防汚性などを評価する。洗濯なしを
L0とし、連続100分洗濯した場合をL10とする。
〔ドライクリーニング再汚染性〕
ステアリン酸25重量%、オリーブ油25重量%、
固形パラフイン25重量%、カーボンブラツク25重
量%からなる汚染剤を0.5g/−パークレン、粘
土50重量%、ポルトランドセメント20重量%、シ
リカゲル15重量%、n−デカン15重量%からなる
汚染剤を0.2g/−パークレンおよび中性洗剤を
2g/−パークレンになるように配合したパー
クレン液200c.c.をラウンダメータ用ポツトに入
れ、5cm×5mmの試料6枚を入れ、40℃で20分間
回転処理を行い、再汚染性を肉眼判定または光電
反射計を用い、処理前後の反射率を測定し、次式
で再汚染率を求める。
再汚染率(%)=R0−R1/R0×100
ここでR0は処理前の反射率(%)
R1は処理後の反射率(%)
〔染色堅ろう度:洗たく〕
JIS L−0844(A−)に準じた。
〔染色堅ろう度:湿摩擦〕
JIS L−0849に準じた。
実施例1、比較例1〜7
45%のポリエチレングリコールジアンモニウム
アジペート水溶液60重量部、85%のカプロラクタ
ム水溶液35重量部および40%のヘキサメチレンジ
アンモニウムイソフタレート水溶液5重量部を重
合して得たブロツクポリエーテルアミドにドデシ
ルベンゼンスルホン酸ソーダと1・5・5−トリ
メチル−2・4・6−トリ(3・5ジtert−ブチ
ル4−ヒドロキシベンジル)ベンゼンをそれぞれ
5重量%添加して得たブロツクポリエーテルアミ
ド組成物を極限粘度0.63のポリエチレンテレフタ
レートに7.0重量%混合したものを芯成分とな
し、一方通常の極限粘度0.63のポリエチレンテレ
フタレートを鞘成分として、芯対鞘の複合比が10
対90(重量比)の同心円複合糸を紡止し、150デ
ニール48フイラメントの延伸糸とした。
次に、かかるフイラメントを通常の仮撚り加工
糸となし、目付が200g/m2のツイル織物とした。
一方、5−スルホイソフタル酸ナトリウム塩
が、20モル%、テレフタル酸が80モル%からなる
ジカルボン酸成分とエチレングリコールが100モ
ル%であるジオール成分からなるスルホポリエス
テル重合体を10%水分散液となした。かかるスル
ホポリエステル重合体の10%水分散液を5g/
の水分散液にさらに希釈し(有効成分0.5g/
)、これにシー・アイ・デイスパース レツド
57を5%owf、第二リン酸アンモニウム塩を3
g/添加した液に前述のツイル織物を浴比が
1:50になるように浸漬し、室温から加熱昇温せ
しめ;130℃で60分間、浴中加熱処理を於こし
た。次にクーリング後、水洗乾燥、180℃×1分
間の仕上セツトを行い、次表に示すごとき、さら
つとしたドライタツチの良好な風合で洗たく耐久
性に優れた吸水、制電、防汚性能を有し、しかも
ドライクリーニングによる黒ずみ発生のない、染
色堅ろう度の良好な改質ポリエステル系繊維から
なる織物を得た(本実施例)。
次に比較として、本実施例中のスルホポリエス
テル重合体の代りに、ビス−フエールAのジメタ
クリレートにエチレンオキシドを20モル付加した
もの(比較例1)、テレフタル酸10重量%、エチ
レングリコール20重量%、分子量4000のポリエチ
レングリコール70重量%からなるポリエチレング
リコール変性のポリエステル系重合体(比較例
2)を各々、本実施例中のスルホポリエチレン重
合体と同量用い、あとは本実施例と同様に処理し
たが、いずれもドライクリーニング時の黒ずみ発
生、染色堅ろう度面で、本実施例よりも劣つたも
のとなつた。なお、本実施例中の改質ポリエステ
ル織物を、スルホポリエステル重合体で処理しな
い未加工品についても比較として次表に性能を示
した(比較例3)。
さらに比較として、通常のポリエステル系繊維
からなるツイル織物を用い、本実施例と同様のス
ルホポリエステル重合体で本実施例と同様に加工
したもの(比較例4)。また通常のポリエステル
系繊維からなるツイル織物を比較例1、2と同様
の重合体で処理したもの(比較例5、6)ならび
に通常のポリエステル系繊維からなる織物を、全
く加工しないもの(比較例7)についても、各々
の性能を次表に示した。
The present invention has water absorption, antistatic, and antifouling properties at the same time,
Moreover, it relates to a modified polyester fiber having good color fastness. Conventionally, polyester fibers have been widely used due to their excellent easy care properties, but because they are inherently hydrophobic, they do not have water absorbency or stain resistance.
There were many problems, such as the generation of static electricity. Therefore, in the industry, various polyethylene glycol compounds have been applied to polyester fibers by some means to overcome these problems. However, although it has become possible to impart various properties such as water absorption, antistatic properties, and stain resistance using these methods, on the other hand, there is a significant decrease in dye fastness, recontamination during dry cleaning, and thinning. New problems have arisen, such as dirty products, and there is a strong demand for improvements in these shortcomings. With this background in mind, the present invention has been developed to provide a method that does not reduce dye fastness or cause re-contamination during dry cleaning.
The object of the present invention is to provide a polyester fiber that has water absorption, antistatic, and antifouling properties at the same time. In order to achieve this object, the present invention has the following configuration. (1) Polyester fibers containing a new aqueous composition made of a polymer having polyether segments contain 10 to 50 aliphatic or aromatic dicarboxylic acids having sulfonic acid groups or sulfonate salts in the acid component. A modified polyester fiber having a polyester polymer layer of 0.05 to 10% by weight based on the weight of the fiber. (2) The modified polyester fiber according to claim 1, wherein the polyester fiber is a polyester composite fiber containing a new aqueous composition in its core. The present invention achieves excellent water absorption and antistatic properties by combining a specific copolymer compound with the above-mentioned specific polyester fiber.
It was able to exhibit three types of antifouling properties simultaneously and with good durability. In the present invention, the hydrophilic composition comprising a polymer having a polyether segment refers to a hydrophilic composition comprising a polyalkylene ether, particularly terephthalic acid, a copolymer of polyethylene glycol and ethylene glycol, and a block copolymer of polyalkylene ether and polyamide. In order to achieve the object of the present invention, block copolymers of polyalkylene ether and polyamide (block polyether amide) are particularly preferred as such hydrophilic polymers. )
is preferred. In the present invention, the polyester fiber containing a hydrophilic composition made of a polymer having a polyether segment refers to a polyester fiber obtained by coating the surface of the fiber with the hydrophilic composition or a polyester fiber containing the hydrophilic composition. or composite fibers in which a mixture of the hydrophilic composition and polyester is arranged in the sheath and an unmodified polyester in the core; Examples include composite fibers in which a mixture of a polyester composition and a polyester are used, and an unmodified polyester is placed in the sheath. Any such polyester fiber suitably achieves the object of the present invention. Among such fibers, the former three tend to be inferior to the latter in the following respects. (1) Unfiltered property due to fusion between single yarns during spinning and fusion between fibers on the package of undrawn yarn. (2) When made into a composite fiber, the yarn quality and properties are determined by the adhesion between the core component and sheath component, as well as the peelability in subsequent processes such as drawing and temporary twisting. (3) Light fastness when dyed with disperse dyes. Therefore, in the present invention, the mixture consisting of the block polyether amide composition and polyester is the core, the polyester is the sheath, the proportion of the core is 5 to 0% by weight, and Particularly preferred is a core-sheath type polyester composite fiber in which the proportion of polyalkylene ether units in the block polyether amide composition to the total fiber is 0.05 to 5% by weight. The block polyether amide composition is a block polyether amide containing a predetermined amount of an organic electrolyte and a phenolic antioxidant. The organic electrolyte mentioned here is formed from sulfonic acids such as dodecylbenzenesulfonic acid, tridecylbenzenesulfonic acid, nonylbenzenesulfonic acid, hexadecylsulfonic acid, and dodecylsulfonic acid, and alkali metals such as sodium, potassium, and lithium. There are alkali metal salts of sulfonic acid, alkali metal salts of phosphoric acid such as sodium distearyl phosphate, and alkali metal salts of other organic carboxylic acids, among which metal salts of sulfonic acid such as sodium dodecylbenzenesulfonate are good. be. The amount of this electrolyte to be blended is appropriately determined depending on the desired antistatic performance. Examples of phenolic antioxidants include:
1,3,5-trimethyl-2,4,6-tri(3,5-di-tert-butyl-4-hydroxybenzyl)benzene, 2,2'-methylenebis(4-
methyl-6-tert-butylphenol), 2.6
-di-tert-butyl-P-cresol, 2,2'-
It is a phenolic derivative having a sterically hindered substituent at a position adjacent to a phenolic hydroxyl group such as methylenebis(4-ethyl-6-tert-butylphenol). This antioxidant is blended as a stabilizer for the block polyether amide, and is blended to the extent that it can withstand the heat during melt spinning, but the amount depends on the amount of polyalkylene ether units. will be determined. The polyether constituting the block polyether amide is a polyalkylene ether, which is a polymerization product of ethylene oxide and/or propylene oxide such as polyethylene ether, polypropylene ether, and polyethylene propylene ether. The molecular weight of these polyethers is preferably 1,000 or more, preferably 3,000 to 8,000, and among them, polyethylene glycol is most suitable. On the other hand, the polyamide constituting block polyetheramide is homopolyamide such as nylon 6, nylon 8, nylon 12, nylon 6/6, nylon 6/10, or a copolyamide containing these or other copolymer components. It is a homo- or copolyamide produced by a polycondensation reaction of polyamide-forming components. Particularly suitable polyester fibers for the present invention are those containing such a block polyether amide composition, for example, in which the proportion of polyalkylene ether segments in the entire fiber is
By using a mixture of a block polyether amide composition mixed with polyester at a concentration of 0.05 to 5% by weight as the core and polyester as the sheath, it has excellent durability and good antistatic properties. It is a polyester fiber that has the same whiteness, heat resistance, light resistance, and dyeing fastness as ordinary polyester yarn, does not cause peeling of the core and sheath, and does not deteriorate in quality due to fibrillation. It can be done. Next, a polyester polymer (hereinafter referred to as sulfopolyester polymer) in which an aliphatic or aromatic dicarboxylic acid having a sulfonic acid group or a sulfonate salt accounts for 10 to 50 mol% of the acid component used in the present invention will be explained. . Sulfo means -SO3X group. However, X
is hydrogen or an alkali metal cation such as sodium, potassium and lithium, an alkaline earth metal cation, a tertiary or quaternary nitrogen cation such as ammonium, N-methylpyridinium, methylammonium, triethylammonium, tetraethylammonium. be. The sulfo-substituted dicarboxylic acids referred to in the present invention include sulfo-substituted aliphatic dicarboxylic acids such as sulfosuccinic acid, 2-sulfoglutaric acid, and 3-sulfoglutaric acid, 5-sulfoisophthalic acid, 2-sulfoterephthalic acid, and 5-sulfonaphthalene. It means a sulfo-substituted aromatic dicarboxylic acid such as -1,4-dicarboxylic acid. Non-sulfo-substituted dicarboxylic acids other than such sulfo-substituted dicarboxylic acids include succinic acid, adipic acid, maleic acid, glutaric acid, suberic acid, 1.4
-Aliphatic dicarboxylic acids such as cyclohexanedicarboxylic acid, terephthalic acid, isophthalic acid, phthalic acid, 1,4-naphthalenedicarboxylic acid, 1,5-
Examples of the diol component of the polyester polymer include aromatic dicarboxylic acids such as pyridine dicarboxylic acid, and examples of the diol component of the polyester polymer include ethylene glycol, propylene glycol, 1,4-butanediol, 1.
Examples include 5-pentanediol, 1,6-hexanediol, diethylene glycol, and dipropylene glycol. The sulfopolyester polymer of the present invention contains 10 to 50 mol% of the above sulfo-substituted dicarboxylic acid in the total acid component.
However, it is preferable that the content is further within the range of 15 to 30 mol%. That is, if the sulfo-substituted dicarboxylic acid in the acid component is less than 10 mol%, the sulfopolyester polymer exhibits excellent adhesion to the polyester fiber of the present invention, which is easy to wash and has excellent durability. If the desired water absorption and antifouling properties are insufficient, and on the other hand, if the sulfo-substituted dicarboxylic acid exceeds 50 mol% in the acid component, the water absorption and antifouling properties, which are one of the objectives of the present invention, may be excellent. , it becomes less durable when washed. Such sulfopolyester polymers may be water-soluble, water-dispersible close to water-soluble, or capable of taking the form of an emulsion, but from the standpoint of fully achieving the purpose of the present invention, it is preferable to use an emulsion form or a water-dispersion form. Those that can be used are preferable from the viewpoint of adhesion to the polyester fiber of the present invention and durability to wash the adhered materials. Such sulfopolyester polymers have a characteristic that they have better adhesion durability to the polyester fibers referred to in the present invention than ordinary regular polyester fibers, and have excellent durability in water absorption and antifouling performance. It is characterized by a tendency to improve. Although the cause of these characteristics is not clear, the polyester fibers of the present invention have greater hydrophilicity and water swelling properties than ordinary regular polyester fibers, and have a higher affinity with the sulfopolyester polymer. It is surmised that the high fiber resistance and the ease with which the polymer penetrates into the fibers lead to improved durability. In addition, it can be inferred that the fact that the sulfopolyester polymer tends to have a low interfacial potential (jeeter potential) in water is also a reason for the increased affinity with the polyester fiber of the present invention. The high compatibility between the polyester fiber and the sulfopolyester polymer is that
This is a major feature of the present invention. In the present invention, an adhesion layer made of such a sulfopolyester polymer is provided on a polyester fiber containing a hydrophilic composition made of a polymer having polyether segments. In order to achieve the object of the present invention, the adhesion is preferably 0.05 to 10% by weight, or even 0.1 to 2% by weight. Although such an adhesion layer may be provided in any form, it usually takes the form of a film on the polyester fiber of the present invention, and in some cases, it is at least partially retained within the fiber. The advantage of the present invention is that certain polyester fibers (such as JP-A-48-27066 and JP-A-52-150392, which have water-absorbing, antistatic, and antifouling fibers having a polymer layer having a polyalkylene glycol segment on the fiber surface) )
Decreased color fastness and darkening due to recontamination during dry cleaning have been extremely difficult to overcome even with the use of various processing agents, as the performance may be offset or other defects may occur. The problem could have been improved by easy means. In addition to various other performances, clothing fibers are considered to have antistatic properties as an extremely important and essential performance. Electricity could not be obtained, and there was a problem that the application to the clothing field had to be severely restricted. The present inventors have discovered that such sulfopolyester polymers act synergistically with polymers having polyalkylene glycol segments without canceling out their respective properties, and have also achieved color fastness that was unexpected in the prior art. This study revealed the fact that the problems of dry cleaning and dry cleaning recontamination can be solved all at once. The modified polyester fiber of the present invention not only has excellent washability and durability, and has high levels of water absorption, antistatic, and antifouling properties, but also has low recontamination during dry cleaning, and has excellent color fastness. It exhibits excellent performance. Next, the method for producing the modified polyester fiber of the present invention will be described below by giving one example. Polyester fibers containing a hydrophilic composition made of a polymer having a polyether segment of the present invention can be produced by a conventional method of coating a polyester fiber with the composition or a mixed spinning method of mixing the composition and polyester. It is formed by methods such as , composite spinning method, etc. When such a fiber is provided with a sulfopolyester polymer layer, it is treated with a treatment solution containing 0.1 to 100 g/g of the polymer. If it is less than 0.1 g/, the object of the present invention cannot be achieved, and if it exceeds 100 g/, the object of the present invention can be sufficiently achieved, but the effect reaches equilibrium. Therefore, further use will only increase the cost and is industrially disadvantageous. If necessary, 0.1 to 10 g of a water-soluble inorganic salt may be added to the treatment liquid. The water-soluble inorganic salt as used herein means sodium sulfate, sodium chloride, ammonium sulfate, diammonium phosphate, calcium chloride, magnesium chloride, subsalt chloride, and the like. By using these inorganic salts in combination, the adhesion of the sulfopolyester polymer to the polyester fibers can be further improved. Further, the pH of the treatment liquid is preferably neutral or acidic, and preferably PH 3 to 6 from the viewpoint of improving adhesion and durability. Any method may be used to form the polymer layer on the polyester fiber using the liquid, such as a pad-dry method, a pad-steam method, or a bath treatment method. However, the most effective method is the bath treatment method, which involves treatment in a bath at 60 to 135°C for 2 to 60 minutes.
This treatment may be carried out simultaneously with staining. The next most effective method is the pad steam method, which can provide sufficient performance if treated at 80°C or higher for 2 to 60 minutes. In addition, the forms of the objects to be processed include staples,
It may be in any form such as tow, filament, spun yarn, knitted fabric, woven fabric, or web, but knitted fabric is the easiest to process. Hereinafter, this will be specifically explained using examples. The evaluation methods for frictional charging voltage, water absorption, antifouling property, restaining property during dry cleaning, color fastness, etc. shown in Examples will be described in detail below. [Frictional electrification voltage] Using a Kyoto University Kaken type rotary static tester (manufactured by Koa Shokai), plain weave cotton Kanakin 3, which had been previously glued, scoured, and bleached, was used as the friction target fabric.
(Weight: 100g/m 2 ), rotor rotation speed
400rpm, applied voltage 100V, temperature 20℃, relative humidity 30
This is a value measured in a % atmosphere. [Water absorption] According to JIS L-1079 needle method. [Anti-fouling property] Applied to paper using a method compliant with AATCC 130-69.
Place a 20cm x 20cm sample on top and add 3 coats of motor oil and Daph Nitronic Oil SEA (manufactured by Idemitsu Kosan).
A drop was placed on the same spot from a height of 3 cm, left for a day and night, then washed in a household washing machine containing 1 g of neutral detergent at 40°C for 10 minutes, then washed with water and dried. The thus obtained sample is compared with a 5tain standard plate. [Washing durability] After washing the sample in a household washing machine in a 40°C washing solution containing 1 g of neutral detergent, the frictional charging voltage, water absorption, stain resistance, etc. described above were evaluated. No laundry
Let L be 0 , and let L be 10 when washing for 100 minutes continuously. [Dry cleaning restainability] Stearic acid 25% by weight, olive oil 25% by weight,
0.5 g of a staining agent consisting of 25% by weight of solid paraffin and 25% by weight of carbon black/0.2g of a staining agent consisting of 25% by weight of perchlorine, 50% by weight of clay, 20% by weight of Portland cement, 15% by weight of silica gel, and 15% by weight of n-decane. Pour 200 c.c. of perc.c. of perc.c., which is a combination of g/- percrene and a neutral detergent to give 2g/- perc., into a rounder meter pot, add 6 samples of 5 cm x 5 mm, and rotate at 40℃ for 20 minutes. The recontamination rate is determined with the naked eye or using a photoelectric reflectance meter, and the reflectance before and after treatment is measured, and the recontamination rate is calculated using the following formula. Recontamination rate (%) = R 0 - R 1 / R 0 × 100 where R 0 is the reflectance before treatment (%) R 1 is the reflectance after treatment (%) [Dyeing fastness: washable] JIS L -0844(A-). [Dye fastness: wet friction] According to JIS L-0849. Example 1, Comparative Examples 1 to 7 Obtained by polymerizing 60 parts by weight of 45% polyethylene glycol diammonium adipate aqueous solution, 35 parts by weight of 85% caprolactam aqueous solution, and 5 parts by weight of 40% hexamethylene diammonium isophthalate aqueous solution. Obtained by adding 5% by weight each of sodium dodecylbenzenesulfonate and 1,5,5-trimethyl-2,4,6-tri(3,5di-tert-butyl-4-hydroxybenzyl)benzene to block polyetheramide. A mixture of 7.0% by weight of a block polyether amide composition in polyethylene terephthalate with an intrinsic viscosity of 0.63 was used as the core component, while a normal polyethylene terephthalate with an intrinsic viscosity of 0.63 was used as the sheath component, and the composite ratio of core to sheath was 10.
A concentric composite yarn of 90 (weight ratio) was spun to obtain a drawn yarn of 150 denier 48 filaments. Next, the filament was made into ordinary false twisted yarn to make a twill fabric with a basis weight of 200 g/m 2 . On the other hand, a sulfopolyester polymer consisting of a dicarboxylic acid component consisting of 20 mol% of 5-sulfoisophthalic acid sodium salt, 80 mol% of terephthalic acid, and a diol component of 100 mol% of ethylene glycol was prepared in a 10% aqueous dispersion. I did it. 5 g/10% aqueous dispersion of such sulfopolyester polymer
(active ingredient 0.5g/
), C.I. Disperse Red
57 5% owf, diammonium phosphate salt 3
The above-mentioned twill fabric was immersed in the added solution at a bath ratio of 1:50, and the temperature was raised from room temperature; heat treatment was performed in the bath at 130° C. for 60 minutes. Next, after cooling, washing with water, drying, and finishing setting at 180°C for 1 minute are performed, as shown in the following table, to achieve a smooth, dry-touch texture that is easy to wash, with excellent water absorption, antistatic, and antifouling properties. A woven fabric made of a modified polyester fiber having a good color fastness and not causing darkening due to dry cleaning was obtained (this example). Next, as a comparison, instead of the sulfopolyester polymer in this example, 20 moles of ethylene oxide was added to dimethacrylate of Bis-Phale A (Comparative Example 1), 10% by weight of terephthalic acid, and 20% by weight of ethylene glycol. , a polyethylene glycol-modified polyester polymer (Comparative Example 2) consisting of 70% by weight of polyethylene glycol with a molecular weight of 4000 was used in the same amount as the sulfopolyethylene polymer in this example, and the rest was treated in the same manner as in this example. However, all of them were inferior to this example in terms of darkening during dry cleaning and color fastness. The following table also shows the performance of an unprocessed product of the modified polyester fabric in this example that was not treated with a sulfopolyester polymer (Comparative Example 3). Furthermore, as a comparison, a twill fabric made of ordinary polyester fibers was processed in the same manner as in this example with the same sulfopolyester polymer as in this example (Comparative Example 4). In addition, twill fabrics made of ordinary polyester fibers were treated with the same polymers as in Comparative Examples 1 and 2 (Comparative Examples 5 and 6), and woven fabrics made of ordinary polyester fibers were not treated at all (Comparative Examples 5 and 6). Regarding 7), the performance of each is shown in the table below.
【表】
実施例 2
実施例1と同様の改質ポリエステル織物を、シ
ー・アイ・デイスパース ブルー120、5%owf
からなる浴比1:50の液中で130℃×60分間染色
した。次に水洗−乾燥後、ジメチルテレフタレー
ト75モル%、イソフタル酸5モル%、5−スルホ
イソフタル酸ナトリウム塩が20モル%からなるジ
カルボン酸成分と、エチレングリコールが100モ
ル%、からなるスルホポリエステル重合体を20%
水分散液となし、かかる重合体を50g/の水分
散液にして、60゜シヨアーのマングルを用い、2
Kg/cm2のマングル圧下でピツクアツプが80%にな
るように絞り、130℃の高圧スチーマーにて10分
間スチーミング処理を施しドライタツチな風合
で、吸水、制電、防汚性にすぐれ、しかもドライ
クリーニング時の黒ずみ発生のない、染色堅ろう
度の良好な製品を得た(本実施例)。
次に比較として、本実施例中のスルホポリエス
テル重合体の代りに、メラミン系樹脂、アクリル
酸エステル系樹脂(比較例8、9)を用い、あと
は、本実施例と同様の条件で処理したが、いずれ
も、防汚性、制電性能が悪く、本発明の目的とす
る製品が得られなかつた。[Table] Example 2 The same modified polyester fabric as in Example 1 was used as C.I. Disperse Blue 120, 5% owf.
Dyeing was carried out at 130°C for 60 minutes in a bath ratio of 1:50. Next, after washing with water and drying, a sulfopolyester polymer consisting of a dicarboxylic acid component consisting of 75 mol% of dimethyl terephthalate, 5 mol% of isophthalic acid, and 20 mol% of sodium 5-sulfoisophthalate, and 100 mol% of ethylene glycol. 20%
The polymer was made into an aqueous dispersion at a concentration of 50 g/water, and a mangle with a 60° shore was used to make the polymer into an aqueous dispersion.
It is squeezed under mangle pressure of Kg/cm 2 so that the pick-up is 80%, and then steamed for 10 minutes in a high-pressure steamer at 130℃ to create a dry-touch texture with excellent water absorption, anti-static, and antifouling properties. A product with good color fastness without darkening during dry cleaning was obtained (this example). Next, as a comparison, melamine resin and acrylic ester resin (Comparative Examples 8 and 9) were used instead of the sulfopolyester polymer in this example, and the rest was treated under the same conditions as in this example. However, all of them had poor antifouling properties and antistatic properties, and the product aimed at by the present invention could not be obtained.
Claims (1)
なる親水性組成物を含有するポリエステル系繊維
に、スルホン酸基またはスルホン酸塩を有する脂
肪族または芳香族のジカルボン酸が、酸成分中、
10〜50モル%占めるポリエステル系重合体を、繊
維重量に対して0.05〜10重量%付着せしめてなる
改質ポリエステル系繊維。 2 ポリエステル系繊維がその芯部に該親水性組
成物を含有してなるポリエステル系繊維である特
許請求の範囲第1項記載の改質ポリエステル系繊
維。[Scope of Claims] 1 Polyester fibers containing a hydrophilic composition made of a polymer having polyether segments contain an aliphatic or aromatic dicarboxylic acid having a sulfonic acid group or a sulfonate in the acid component. ,
A modified polyester fiber made by adhering 0.05 to 10% by weight of a polyester polymer that accounts for 10 to 50 mol% based on the weight of the fiber. 2. The modified polyester fiber according to claim 1, wherein the polyester fiber contains the hydrophilic composition in its core.
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP57217085A JPS59106517A (en) | 1982-12-13 | 1982-12-13 | Modiifed polyester yarn |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP57217085A JPS59106517A (en) | 1982-12-13 | 1982-12-13 | Modiifed polyester yarn |
Publications (2)
Publication Number | Publication Date |
---|---|
JPS59106517A JPS59106517A (en) | 1984-06-20 |
JPS6137388B2 true JPS6137388B2 (en) | 1986-08-23 |
Family
ID=16698589
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP57217085A Granted JPS59106517A (en) | 1982-12-13 | 1982-12-13 | Modiifed polyester yarn |
Country Status (1)
Country | Link |
---|---|
JP (1) | JPS59106517A (en) |
Families Citing this family (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS60134070A (en) * | 1983-12-21 | 1985-07-17 | 東レ株式会社 | Production of modified polyester fiber |
JP2710306B2 (en) * | 1985-10-31 | 1998-02-10 | 東レ株式会社 | High moisture permeable waterproof fabric and method for producing the same |
US6238441B1 (en) | 1998-07-29 | 2001-05-29 | Burlington Industries, Inc. | Hydrophilic yarn dyed polyester process |
Citations (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS50107206A (en) * | 1974-02-06 | 1975-08-23 | ||
JPS55122020A (en) * | 1979-03-06 | 1980-09-19 | Toray Ind Inc | Antistatic conjugate fiber of polyester |
JPS55128017A (en) * | 1979-03-26 | 1980-10-03 | Toray Ind Inc | Antistatic conjugate fiber of readily dyeable polyester |
JPS55158333A (en) * | 1979-05-21 | 1980-12-09 | Toray Ind Inc | Ultrafine antistatic polyester composite fiber |
JPS55165917A (en) * | 1979-06-12 | 1980-12-24 | Toyobo Co Ltd | Preparation of hydrophilic polyester |
JPS57195121A (en) * | 1981-05-14 | 1982-11-30 | Ici America Inc | Anionic fiber material treating composition |
-
1982
- 1982-12-13 JP JP57217085A patent/JPS59106517A/en active Granted
Patent Citations (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS50107206A (en) * | 1974-02-06 | 1975-08-23 | ||
JPS55122020A (en) * | 1979-03-06 | 1980-09-19 | Toray Ind Inc | Antistatic conjugate fiber of polyester |
JPS55128017A (en) * | 1979-03-26 | 1980-10-03 | Toray Ind Inc | Antistatic conjugate fiber of readily dyeable polyester |
JPS55158333A (en) * | 1979-05-21 | 1980-12-09 | Toray Ind Inc | Ultrafine antistatic polyester composite fiber |
JPS55165917A (en) * | 1979-06-12 | 1980-12-24 | Toyobo Co Ltd | Preparation of hydrophilic polyester |
JPS57195121A (en) * | 1981-05-14 | 1982-11-30 | Ici America Inc | Anionic fiber material treating composition |
Also Published As
Publication number | Publication date |
---|---|
JPS59106517A (en) | 1984-06-20 |
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