WO2018085037A1 - Textile materials containing dyed polyphenylene sulfide fibers and methods for producing the same - Google Patents
Textile materials containing dyed polyphenylene sulfide fibers and methods for producing the same Download PDFInfo
- Publication number
- WO2018085037A1 WO2018085037A1 PCT/US2017/056894 US2017056894W WO2018085037A1 WO 2018085037 A1 WO2018085037 A1 WO 2018085037A1 US 2017056894 W US2017056894 W US 2017056894W WO 2018085037 A1 WO2018085037 A1 WO 2018085037A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- textile material
- fibers
- polyphenylene sulfide
- dye
- disperse
- Prior art date
Links
- 239000000835 fiber Substances 0.000 title claims abstract description 127
- 239000004753 textile Substances 0.000 title claims abstract description 123
- 239000000463 material Substances 0.000 title claims abstract description 121
- 239000004734 Polyphenylene sulfide Substances 0.000 title claims abstract description 93
- 229920000069 polyphenylene sulfide Polymers 0.000 title claims abstract description 93
- 238000000034 method Methods 0.000 title claims abstract description 33
- 239000000975 dye Substances 0.000 claims abstract description 87
- 239000000986 disperse dye Substances 0.000 claims abstract description 65
- 239000007788 liquid Substances 0.000 claims abstract description 14
- 238000004043 dyeing Methods 0.000 claims abstract description 11
- 239000012298 atmosphere Substances 0.000 claims abstract description 10
- 238000010438 heat treatment Methods 0.000 claims abstract description 9
- 229920000642 polymer Polymers 0.000 claims description 27
- 239000000203 mixture Substances 0.000 claims description 26
- 229920002994 synthetic fiber Polymers 0.000 claims description 13
- 239000012209 synthetic fiber Substances 0.000 claims description 13
- 229920003043 Cellulose fiber Polymers 0.000 claims description 10
- 238000009835 boiling Methods 0.000 claims description 10
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 10
- 229920001169 thermoplastic Polymers 0.000 claims description 10
- 239000004416 thermosoftening plastic Substances 0.000 claims description 9
- 239000003518 caustics Substances 0.000 claims description 8
- 229920000728 polyester Polymers 0.000 claims description 7
- 150000007524 organic acids Chemical class 0.000 claims description 6
- 239000004952 Polyamide Substances 0.000 claims description 4
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 claims description 4
- 239000000987 azo dye Substances 0.000 claims description 4
- TXCDCPKCNAJMEE-UHFFFAOYSA-N dibenzofuran Chemical compound C1=CC=C2C3=CC=CC=C3OC2=C1 TXCDCPKCNAJMEE-UHFFFAOYSA-N 0.000 claims description 4
- 229920002647 polyamide Polymers 0.000 claims description 4
- 239000001000 anthraquinone dye Substances 0.000 claims description 3
- 239000003638 chemical reducing agent Substances 0.000 claims description 3
- UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 claims description 2
- XJHABGPPCLHLLV-UHFFFAOYSA-N benzo[de]isoquinoline-1,3-dione Chemical compound C1=CC(C(=O)NC2=O)=C3C2=CC=CC3=C1 XJHABGPPCLHLLV-UHFFFAOYSA-N 0.000 claims description 2
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 claims description 2
- 239000001005 nitro dye Substances 0.000 claims description 2
- 239000000080 wetting agent Substances 0.000 claims description 2
- 239000004744 fabric Substances 0.000 description 18
- -1 polyphenylene Polymers 0.000 description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
- 239000003063 flame retardant Substances 0.000 description 10
- 239000002609 medium Substances 0.000 description 10
- 239000000243 solution Substances 0.000 description 8
- RNFJDJUURJAICM-UHFFFAOYSA-N 2,2,4,4,6,6-hexaphenoxy-1,3,5-triaza-2$l^{5},4$l^{5},6$l^{5}-triphosphacyclohexa-1,3,5-triene Chemical compound N=1P(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP=1(OC=1C=CC=CC=1)OC1=CC=CC=C1 RNFJDJUURJAICM-UHFFFAOYSA-N 0.000 description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- ZDORFLXCSSFUIE-UHFFFAOYSA-N 2-[n-(2-acetyloxyethyl)-4-[(2-chloro-4-nitrophenyl)diazenyl]-3-(propanoylamino)anilino]ethyl acetate Chemical compound CCC(=O)NC1=CC(N(CCOC(C)=O)CCOC(C)=O)=CC=C1N=NC1=CC=C([N+]([O-])=O)C=C1Cl ZDORFLXCSSFUIE-UHFFFAOYSA-N 0.000 description 5
- BBFRYSKTTHYWQZ-UHFFFAOYSA-N 4-anilino-3-nitro-n-phenylbenzenesulfonamide Chemical compound [O-][N+](=O)C1=CC(S(=O)(=O)NC=2C=CC=CC=2)=CC=C1NC1=CC=CC=C1 BBFRYSKTTHYWQZ-UHFFFAOYSA-N 0.000 description 5
- 239000000984 vat dye Substances 0.000 description 5
- 229920000742 Cotton Polymers 0.000 description 4
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 4
- 239000004760 aramid Substances 0.000 description 4
- 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 4
- 238000004519 manufacturing process Methods 0.000 description 4
- 238000011282 treatment Methods 0.000 description 4
- RUKISNQKOIKZGT-UHFFFAOYSA-N 2-nitrodiphenylamine Chemical compound [O-][N+](=O)C1=CC=CC=C1NC1=CC=CC=C1 RUKISNQKOIKZGT-UHFFFAOYSA-N 0.000 description 3
- WBCXRDHKXHADQF-UHFFFAOYSA-N 4,11-diamino-2-(3-methoxypropyl)naphtho[2,3-f]isoindole-1,3,5,10-tetrone Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C(N)=C(C(N(CCCOC)C1=O)=O)C1=C2N WBCXRDHKXHADQF-UHFFFAOYSA-N 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- 229920000297 Rayon Polymers 0.000 description 3
- DWAQJAXMDSEUJJ-UHFFFAOYSA-M Sodium bisulfite Chemical compound [Na+].OS([O-])=O DWAQJAXMDSEUJJ-UHFFFAOYSA-M 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- 229920006231 aramid fiber Polymers 0.000 description 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
- 235000010267 sodium hydrogen sulphite Nutrition 0.000 description 3
- DYALWCKAJBVSBZ-UHFFFAOYSA-N 1-anilino-4,5-dihydroxy-8-nitroanthracene-9,10-dione Chemical compound C1=2C(=O)C(C(=CC=C3O)[N+]([O-])=O)=C3C(=O)C=2C(O)=CC=C1NC1=CC=CC=C1 DYALWCKAJBVSBZ-UHFFFAOYSA-N 0.000 description 2
- ROPYWXVRNREIQD-UHFFFAOYSA-N 2-[n-(2-cyanoethyl)-4-[(2,6-dichloro-4-nitrophenyl)diazenyl]anilino]ethyl acetate Chemical compound C1=CC(N(CCC#N)CCOC(=O)C)=CC=C1N=NC1=C(Cl)C=C([N+]([O-])=O)C=C1Cl ROPYWXVRNREIQD-UHFFFAOYSA-N 0.000 description 2
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 2
- 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 2
- 229920000265 Polyparaphenylene Polymers 0.000 description 2
- 235000011054 acetic acid Nutrition 0.000 description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
- 239000000969 carrier Substances 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
- DMBHHRLKUKUOEG-UHFFFAOYSA-N diphenylamine Chemical compound C=1C=CC=CC=1NC1=CC=CC=C1 DMBHHRLKUKUOEG-UHFFFAOYSA-N 0.000 description 2
- 239000006185 dispersion Substances 0.000 description 2
- 238000009826 distribution Methods 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 230000001747 exhibiting effect Effects 0.000 description 2
- 238000007654 immersion Methods 0.000 description 2
- 239000000155 melt Substances 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- QRKGKRSGMAWUMO-UHFFFAOYSA-N n-[2-[(2-bromo-4,6-dinitrophenyl)diazenyl]-5-(diethylamino)-4-methoxyphenyl]acetamide Chemical compound C1=C(OC)C(N(CC)CC)=CC(NC(C)=O)=C1N=NC1=C(Br)C=C([N+]([O-])=O)C=C1[N+]([O-])=O QRKGKRSGMAWUMO-UHFFFAOYSA-N 0.000 description 2
- 235000005985 organic acids Nutrition 0.000 description 2
- 229920005594 polymer fiber Polymers 0.000 description 2
- 239000002964 rayon Substances 0.000 description 2
- 239000004627 regenerated cellulose Substances 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 238000010998 test method Methods 0.000 description 2
- VOCYGZAHYQXJOF-UHFFFAOYSA-N 1,8-dihydroxy-4-[4-(2-hydroxyethyl)anilino]-5-nitroanthracene-9,10-dione Chemical compound C1=CC(CCO)=CC=C1NC1=CC=C(O)C2=C1C(=O)C1=C([N+]([O-])=O)C=CC(O)=C1C2=O VOCYGZAHYQXJOF-UHFFFAOYSA-N 0.000 description 1
- RQLMZSLFKGNXTO-UHFFFAOYSA-N 1-amino-4-hydroxy-2-(6-hydroxyhexoxy)anthracene-9,10-dione Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C(O)=CC(OCCCCCCO)=C2N RQLMZSLFKGNXTO-UHFFFAOYSA-N 0.000 description 1
- LCZVSXRMYJUNFX-UHFFFAOYSA-N 2-[2-(2-hydroxypropoxy)propoxy]propan-1-ol Chemical compound CC(O)COC(C)COC(C)CO LCZVSXRMYJUNFX-UHFFFAOYSA-N 0.000 description 1
- HXXLWTPFYWMBSC-UHFFFAOYSA-N 2-[3-chloro-4-[(2,6-dichloro-4-nitrophenyl)diazenyl]-n-(2-hydroxyethyl)anilino]ethanol Chemical compound ClC1=CC(N(CCO)CCO)=CC=C1N=NC1=C(Cl)C=C([N+]([O-])=O)C=C1Cl HXXLWTPFYWMBSC-UHFFFAOYSA-N 0.000 description 1
- YAOMDDRLRVOOIC-UHFFFAOYSA-N 2-[n-(2-acetyloxyethyl)-4-[(2-cyano-4-nitrophenyl)diazenyl]-3-methylanilino]ethyl acetate Chemical compound CC1=CC(N(CCOC(C)=O)CCOC(=O)C)=CC=C1N=NC1=CC=C([N+]([O-])=O)C=C1C#N YAOMDDRLRVOOIC-UHFFFAOYSA-N 0.000 description 1
- VGKYEIFFSOPYEW-UHFFFAOYSA-N 2-methyl-4-[(4-phenyldiazenylphenyl)diazenyl]phenol Chemical compound Cc1cc(ccc1O)N=Nc1ccc(cc1)N=Nc1ccccc1 VGKYEIFFSOPYEW-UHFFFAOYSA-N 0.000 description 1
- ZXXVVTBKBDDTSE-UHFFFAOYSA-N 3-[4-[(2-chloro-4-nitrophenyl)diazenyl]-n-(2-cyanoethyl)anilino]propanenitrile Chemical compound ClC1=CC([N+](=O)[O-])=CC=C1N=NC1=CC=C(N(CCC#N)CCC#N)C=C1 ZXXVVTBKBDDTSE-UHFFFAOYSA-N 0.000 description 1
- MUERWWKQVXXPML-UHFFFAOYSA-N 3-[n-(2-cyanoethyl)-4-[(2,6-dichloro-4-nitrophenyl)diazenyl]anilino]propanenitrile Chemical compound ClC1=CC([N+](=O)[O-])=CC(Cl)=C1N=NC1=CC=C(N(CCC#N)CCC#N)C=C1 MUERWWKQVXXPML-UHFFFAOYSA-N 0.000 description 1
- AIARLPIXVMHZLJ-UHFFFAOYSA-N 4,8-diamino-2-bromo-1,5-dihydroxyanthracene-9,10-dione Chemical compound O=C1C2=C(N)C=C(Br)C(O)=C2C(=O)C2=C1C(O)=CC=C2N AIARLPIXVMHZLJ-UHFFFAOYSA-N 0.000 description 1
- ALXCWDABTQQKAH-UHFFFAOYSA-N 4-(1-amino-4-hydroxy-9,10-dioxoanthracen-2-yl)oxy-n-(3-ethoxypropyl)benzenesulfonamide Chemical compound C1=CC(S(=O)(=O)NCCCOCC)=CC=C1OC1=CC(O)=C(C(=O)C=2C(=CC=CC=2)C2=O)C2=C1N ALXCWDABTQQKAH-UHFFFAOYSA-N 0.000 description 1
- BCPQALWAROJVLE-UHFFFAOYSA-N 4-(2,4-dinitroanilino)phenol Chemical compound C1=CC(O)=CC=C1NC1=CC=C([N+]([O-])=O)C=C1[N+]([O-])=O BCPQALWAROJVLE-UHFFFAOYSA-N 0.000 description 1
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
- SIFKXZAVMBSRMB-UHFFFAOYSA-N 4-(4-ethoxyanilino)-n,n-dimethyl-3-nitrobenzenesulfonamide Chemical compound C1=CC(OCC)=CC=C1NC1=CC=C(S(=O)(=O)N(C)C)C=C1[N+]([O-])=O SIFKXZAVMBSRMB-UHFFFAOYSA-N 0.000 description 1
- 239000005711 Benzoic acid Substances 0.000 description 1
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
- JHWNWJKBPDFINM-UHFFFAOYSA-N Laurolactam Chemical compound O=C1CCCCCCCCCCCN1 JHWNWJKBPDFINM-UHFFFAOYSA-N 0.000 description 1
- 229920000433 Lyocell Polymers 0.000 description 1
- 229920000877 Melamine resin Polymers 0.000 description 1
- 229920001407 Modal (textile) Polymers 0.000 description 1
- 229920000299 Nylon 12 Polymers 0.000 description 1
- 229920003189 Nylon 4,6 Polymers 0.000 description 1
- 229920002292 Nylon 6 Polymers 0.000 description 1
- 229920002302 Nylon 6,6 Polymers 0.000 description 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical group [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 1
- 239000004962 Polyamide-imide Substances 0.000 description 1
- 239000002202 Polyethylene glycol Substances 0.000 description 1
- 239000004372 Polyvinyl alcohol Substances 0.000 description 1
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 1
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
- NTZOUXAZCADJBZ-UHFFFAOYSA-N [4-[(4-hydroxy-9,10-dioxoanthracen-1-yl)amino]phenyl] methanesulfonate Chemical compound C1=CC(OS(=O)(=O)C)=CC=C1NC1=CC=C(O)C2=C1C(=O)C1=CC=CC=C1C2=O NTZOUXAZCADJBZ-UHFFFAOYSA-N 0.000 description 1
- 238000005299 abrasion Methods 0.000 description 1
- XREZMAAQVYVESP-UHFFFAOYSA-N acetyloxymethyl 2-[n-[2-(acetyloxymethoxy)-2-oxoethyl]-2-[2-[2-[bis[2-(acetyloxymethoxy)-2-oxoethyl]amino]-4-fluorophenoxy]ethoxy]-5-fluoroanilino]acetate Chemical compound CC(=O)OCOC(=O)CN(CC(=O)OCOC(C)=O)C1=CC(F)=CC=C1OCCOC1=CC=C(F)C=C1N(CC(=O)OCOC(C)=O)CC(=O)OCOC(C)=O XREZMAAQVYVESP-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 230000032683 aging Effects 0.000 description 1
- 239000012736 aqueous medium Substances 0.000 description 1
- 229920003235 aromatic polyamide Polymers 0.000 description 1
- 235000010233 benzoic acid Nutrition 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- 238000009792 diffusion process Methods 0.000 description 1
- SZXQTJUDPRGNJN-UHFFFAOYSA-N dipropylene glycol Chemical compound OCCCOCCCO SZXQTJUDPRGNJN-UHFFFAOYSA-N 0.000 description 1
- AQYFGWINIJJWBQ-UHFFFAOYSA-N dithiophen-2-yldiazene Chemical compound C1=CSC(N=NC=2SC=CC=2)=C1 AQYFGWINIJJWBQ-UHFFFAOYSA-N 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- IVJISJACKSSFGE-UHFFFAOYSA-N formaldehyde;1,3,5-triazine-2,4,6-triamine Chemical compound O=C.NC1=NC(N)=NC(N)=N1 IVJISJACKSSFGE-UHFFFAOYSA-N 0.000 description 1
- SLGWESQGEUXWJQ-UHFFFAOYSA-N formaldehyde;phenol Chemical compound O=C.OC1=CC=CC=C1 SLGWESQGEUXWJQ-UHFFFAOYSA-N 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 238000005470 impregnation Methods 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- BXIGAWRFDMDLTL-UHFFFAOYSA-N n-(4-amino-3-methoxy-9,10-dioxoanthracen-1-yl)-4-methylbenzenesulfonamide Chemical compound C=12C(=O)C3=CC=CC=C3C(=O)C2=C(N)C(OC)=CC=1NS(=O)(=O)C1=CC=C(C)C=C1 BXIGAWRFDMDLTL-UHFFFAOYSA-N 0.000 description 1
- LEGWLJGBFZBZSC-UHFFFAOYSA-N n-[2-[(2,6-dicyano-4-nitrophenyl)diazenyl]-5-(diethylamino)phenyl]acetamide Chemical compound CC(=O)NC1=CC(N(CC)CC)=CC=C1N=NC1=C(C#N)C=C([N+]([O-])=O)C=C1C#N LEGWLJGBFZBZSC-UHFFFAOYSA-N 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 230000035515 penetration Effects 0.000 description 1
- 229920001568 phenolic resin Polymers 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 229920002239 polyacrylonitrile Polymers 0.000 description 1
- 229920002312 polyamide-imide Polymers 0.000 description 1
- 229920002480 polybenzimidazole Polymers 0.000 description 1
- 229920001707 polybutylene terephthalate Polymers 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 229920000139 polyethylene terephthalate Polymers 0.000 description 1
- 239000005020 polyethylene terephthalate Substances 0.000 description 1
- 229920002215 polytrimethylene terephthalate Polymers 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 230000002787 reinforcement Effects 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000005063 solubilization Methods 0.000 description 1
- 230000007928 solubilization Effects 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1
- 238000009736 wetting Methods 0.000 description 1
- 229910052724 xenon Inorganic materials 0.000 description 1
- FHNFHKCVQCLJFQ-UHFFFAOYSA-N xenon atom Chemical compound [Xe] FHNFHKCVQCLJFQ-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
- D06P3/00—Special processes of dyeing or printing textiles, or dyeing leather, furs, or solid macromolecular substances in any form, classified according to the material treated
- D06P3/004—Special processes of dyeing or printing textiles, or dyeing leather, furs, or solid macromolecular substances in any form, classified according to the material treated using dispersed dyes
-
- D—TEXTILES; PAPER
- D01—NATURAL OR MAN-MADE THREADS OR FIBRES; SPINNING
- D01F—CHEMICAL FEATURES IN THE MANUFACTURE OF ARTIFICIAL FILAMENTS, THREADS, FIBRES, BRISTLES OR RIBBONS; APPARATUS SPECIALLY ADAPTED FOR THE MANUFACTURE OF CARBON FILAMENTS
- D01F1/00—General methods for the manufacture of artificial filaments or the like
- D01F1/02—Addition of substances to the spinning solution or to the melt
- D01F1/06—Dyes
-
- D—TEXTILES; PAPER
- D01—NATURAL OR MAN-MADE THREADS OR FIBRES; SPINNING
- D01F—CHEMICAL FEATURES IN THE MANUFACTURE OF ARTIFICIAL FILAMENTS, THREADS, FIBRES, BRISTLES OR RIBBONS; APPARATUS SPECIALLY ADAPTED FOR THE MANUFACTURE OF CARBON FILAMENTS
- D01F6/00—Monocomponent artificial filaments or the like of synthetic polymers; Manufacture thereof
- D01F6/58—Monocomponent artificial filaments or the like of synthetic polymers; Manufacture thereof from homopolycondensation products
- D01F6/76—Monocomponent artificial filaments or the like of synthetic polymers; Manufacture thereof from homopolycondensation products from other polycondensation products
- D01F6/765—Monocomponent artificial filaments or the like of synthetic polymers; Manufacture thereof from homopolycondensation products from other polycondensation products from polyarylene sulfides
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
- D06P1/00—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed
- D06P1/16—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed using dispersed, e.g. acetate, dyestuffs
- D06P1/19—Nitro dyes
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
- D06P3/00—Special processes of dyeing or printing textiles, or dyeing leather, furs, or solid macromolecular substances in any form, classified according to the material treated
- D06P3/82—Textiles which contain different kinds of fibres
- D06P3/8204—Textiles which contain different kinds of fibres fibres of different chemical nature
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
- D06P5/00—Other features in dyeing or printing textiles, or dyeing leather, furs, or solid macromolecular substances in any form
- D06P5/02—After-treatment
- D06P5/10—After-treatment with compounds containing metal
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
- D06P5/00—Other features in dyeing or printing textiles, or dyeing leather, furs, or solid macromolecular substances in any form
- D06P5/20—Physical treatments affecting dyeing, e.g. ultrasonic or electric
- D06P5/2066—Thermic treatments of textile materials
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
- D06P5/00—Other features in dyeing or printing textiles, or dyeing leather, furs, or solid macromolecular substances in any form
- D06P5/20—Physical treatments affecting dyeing, e.g. ultrasonic or electric
- D06P5/2066—Thermic treatments of textile materials
- D06P5/2077—Thermic treatments of textile materials after dyeing
Definitions
- This application relates to textile materials containing dyed
- polyphenylene sulfide fibers and methods for producing the same.
- Polyphenylene sulfide is a thermoplastic polymer that exhibits a number of desirable properties.
- polyphenyelne sulfide exhibits resistance to heat, various chemicals (e.g., acids, alkalis, and bleaches), mildew, aging, UV exposure (e.g., sunlight), and abrasion.
- various chemicals e.g., acids, alkalis, and bleaches
- mildew e.g., mildew
- aging e.g., UV exposure
- UV exposure e.g., sunlight
- the textile fibers made from the polymer have not found practical use in apparel or decorative textile applications.
- the main reason for this lack of use is that no practical means for dyeing polyphenylene sulfide polymers has been developed.
- the invention described in this applications seeks to provide such a method and the dyed polyphenylene sulfide fibers produced by such a method.
- the invention provides a textile material comprising a plurality of dyed polyphenylene sulfide fibers, wherein the
- polyphenylene sulfide fibers have a cross-sectional area
- the polyphenylene sulfide fibers comprise a disperse dye that is distributed substantially evenly across the cross-sectional area of the fibers
- the disperse dye is selected from the group consisting of disperse dyes having a molar mass of about 350 g/mol or more, disperse dyes comprising a nitro group, and mixtures thereof.
- the invention provides a method for dyeing polyphenylene sulfide fibers, the method comprising the steps of:
- a dye liquor comprising a liquid medium and a disperse dye selected from the group consisting of disperse dyes having a molar mass of about 350 g/mol or more, disperse dyes comprising a nitro group, and mixtures thereof;
- the invention provides a textile material comprising a plurality of dyed polyphenylene sulfide fibers.
- the textile material of this first embodiment can take any suitable form.
- the plurality of dyed polyphenylene sulfide fibers can be consolidated to provide a yarn.
- the yarn can contain other fibers in addition to the dyed polyphenylene sulfide fibers, as is described in further detail below.
- the plurality of dyed polyphenylene sulfide fibers can be consolidated into a nonwoven textile material.
- the textile material can also be a woven textile material comprising a plurality of interlaced yarns, at least one of which contains the dyed polyphenylene sulfide fibers.
- the textile material can also be a knit textile material comprising one or more interlooped yarns, at least one of which contains the dyed polyphenylene sulfide fibers.
- the dyed polyphenylene sulfide fibers can comprise any suitable polyphenylene sulfide polymer.
- the polyphenylene sulfide polymer can have any suitable molar mass.
- the polyphenylene sulfide polymer has a mass average molar mass of about 20,000 g/mol or more. More preferably, the polyphenylene sulfide polymer has a mass average molar mass of about 30,000 g/mol or more, about 40,000 g/mol or more, or about 50,000 g/mol or more.
- the polyphenylene sulfide polymer has a mass average molar mass of about 100,000 g/mol or less. More preferably, the polyphenylene sulfide polymer has a mass average molar mass of about 80,000 g/mol or less, about 70,000 g/mol or less, or about 60,000 g/mol or less. In a particularly preferred embodiment, the polyphenylene sulfide polymer has a mass average molar mass of about 40,000 g/mol to about 60,000 g/mol.
- the polyphenylene sulfide polymer can have any suitable melt viscosity.
- the polyphenylene sulfide polymer has a melt viscosity of about 1 ,000 poise or more when measured at 300 °C and an apparent shear rate of 400 s 1 in accordance with ASTM Test Method 3835. More preferably, the polyphenylene sulfide polymer has a melt viscosity of about 1 ,000 poise to about 3,000 poise or about 1 ,000 poise to about 2,200 poise when measured as described above.
- the polyphenylene sulfide polymer can exhibit any suitable degree of crystallinity.
- the percent crystallinity of the polyphenylene sulfide polymer is 10% or more. More preferably, the percent crystallinity of the polyphenylene sulfide polymer is about 20% or more, about 25% or more, or about 30% or more.
- the percent crystallinity of the polyphenylene sulfide polymer preferably is about 80% or less. More preferably, the percent crystallinity of the polyphenylene sulfide polymer is about 75% or less.
- the percent crystallinity of the polyphenylene sulfide polymer is from 10% to about 80%, about 20% to about 80%, or about 30% to about 75%.
- the dyed polyphenylene sulfide fibers of the textile material comprise at least one dye.
- the dye can be any suitable dye, but disperse dyes are particularly preferred.
- the dye is a disperse dye selected from the group consisting of disperse dyes having a molar mass of about 350 g/mol or more, disperse dyes comprising a nitro group, and mixtures thereof.
- the dye is a disperse dye selected from the group consisting of disperse dyes having a molar mass of about 400 g/mol or more, disperse dyes comprising a nitro group, and mixtures thereof.
- disperse dyes having a higher molar mass e.g., about 350 g/mol or more or about 400 g/mol or more
- a polar nature such as disperse dyes containing a nitro group
- dyes that do not possess either of these characteristics do not become sufficiently fixed in the polyphenylene sulfide fiber.
- the disperse dye preferably has a boiling point of 590 °C or more, more preferably about 600 °C or more.
- the disperse dye preferably has a flash point of 300 °C or more, more preferably about 310 °C or more.
- the disperse dye has a boiling point of 590 °C or more (e.g., about 600 °C or more) and a flash point of 300 °C or more (e.g., about 310 °C or more).
- the disperse dye can be any suitable disperse dye that possesses one or more of the characteristics described above.
- the disperse dye is selected from the group consisting of azo dyes (e.g., azothiophene dyes, azobenzothiazole dyes), diazo dyes, anthraquinone dyes, nitro dyes (e.g., nitrodiphenylamine dyes), quinoline dyes, dibenzofuran dyes, naphthalimide dyes (e.g., aminoketone dyes), and mixtures thereof.
- Specific disperse dyes that have been found useful in dyeing the polyphenylene sulfide fibers include, but are not limited to, C.I.
- Disperse Blue 165 C.I. Disperse Red 153, C.I. Disperse Brown 1 , C.I. Disperse Violet 33, C.I. Disperse Red 92, and C.I. Disperse Blue 87. Any of the above- mentioned dyes can be used in combination to produce polyphenylene sulfide fibers and textile materials exhibiting the desired color and shade.
- the disperse dye preferably is distributed substantially evenly throughout the thickness of the polyphenylene sulfide fibers. In other words, the disperse dye preferably is distributed substantially evenly across the cross-sectional area of the polyphenylene sulfide fibers. This distribution of the disperse dye within the polyphenylene sulfide fibers is believed to be unique. For example, prior attempts to dye polyphenylene sulfide fibers have relied upon surrounding the polyphenylene sulfide polymer with a sheath of an easily-dyed polymer (e.g., a polyamide).
- an easily-dyed polymer e.g., a polyamide
- the dye only penetrates and fixes in the sheath, and the polyphenylene sulfide polymer remains undyed (or contains very little dye at the interface between the polyphenylene polymer and the sheath).
- the distribution of the disperse dye through the thickness or across the cross-sectional area can be determined by any suitable technique. For example, individual polyphenylene sulfide fibers can be sectioned and the coloration of the fibers can be examined, for instance, using an optical microscope. When the coloration of the fibers is observed to be substantially even through the thickness or across the cross-sectional area of the fibers, one has confirmed that the dye is substantially evenly distributed through the thickness or across the cross-sectional area of the fiber.
- the textile material described above can contain other fibers in addition to the polyphenylene sulfide fibers.
- the textile material can further comprise any suitable natural fiber or synthetic fiber or combination of natural fibers and/or synthetic fibers.
- These additional fibers can be intimately blended with the polyphenylene sulfide fibers within the textile material.
- the textile material can be a yarn in which the polyphenylene sulfide fibers are intimately blended with, for example, cellulosic fibers.
- the additional fibers and the polyphenylene fibers can be present in separate elements within the textile material.
- the textile material can comprise a first yarn containing the polyphenylene sulfide fibers and a second yarn containing, for example, cellulosic fibers.
- the textile material can comprise any suitable natural or synthetic fiber(s) in addition to the polyphenylene sulfide fibers.
- the textile material further comprises cellulose fibers.
- the cellulose fibers used in such an embodiment can be natural cellulose fibers (e.g., cotton fibers), regenerated cellulose fibers, or any combination thereof. Suitable
- regenerated cellulose fibers include, but are not limited to, rayon fibers (e.g., viscose rayon fibers, high wet modulus rayon fibers, modal fibers, and polynosic fibers), lyocell fibers, and mixtures thereof.
- rayon fibers e.g., viscose rayon fibers, high wet modulus rayon fibers, modal fibers, and polynosic fibers
- lyocell fibers e.g., rayon fibers (e.g., viscose rayon fibers, high wet modulus rayon fibers, modal fibers, and polynosic fibers), lyocell fibers, and mixtures thereof.
- the textile material can further comprise a flame retardant that is added to improve the flame resistance of the cellulose fibers and the textile material containing the same.
- a flame retardant can be used.
- the flame retardant is a phosphorus-based flame retardant, such as the flame retardants based on tetrahydroxymethlphosphonium salts and condensates thereof.
- Suitable examples of such flame retardants include, but are not limited to, those flame retardants described in U.S. Patent No. 7,713,891 ; U.S. Patent No. 8,012,890; U.S. Patent No. 8,012,891 ; U.S. Patent No. 8,722,551 ; U.S. Patent No. 9,091 ,020; U.S. Patent No. 9,453,1 12; and U.S. Patent Application Publication No. US 2015/01 18931 A1 , each of which is hereby incorporated by reference.
- the textile material can also comprise synthetic fibers in addition to the polyphenylene sulfide fibers, such as thermoplastic synthetic fibers and/or inherent flame resistant fibers.
- Suitable thermoplastic synthetic fibers include, but are not necessarily limited to, polyester fibers (e.g., poly(ethylene terephthalate) fibers, polypropylene terephthalate) fibers, poly(trimethylene terephthalate) fibers), poly(butylene terephthalate) fibers, and blends thereof), polyamide fibers (e.g., nylon 6 fibers, nylon 6,6 fibers, nylon 4,6 fibers, and nylon 12 fibers), polyvinyl alcohol fibers, and combinations, mixtures, or blends thereof.
- the thermoplastic synthetic fibers are selected from the group consisting of polyester fibers, polyamide fibers, and mixtures thereof.
- the textile material comprises thermoplastic synthetic fibers
- the textile material can further comprise a flame retardant that is added to improve the flame resistance of the thermoplastic synthetic fibers and the textile material containing the same. Any flame retardant suitable for use with thermoplastic synthetic fibers can be used in such embodiments.
- the term "inherent flame resistant fibers" refers to synthetic fibers which, due to the chemical composition of the material from which they are made, exhibit flame resistance without the need for an additional flame retardant treatment.
- the inherent flame resistant fibers can be any suitable inherent flame resistant fibers, such as polyoxadiazole fibers,
- polysulfonamide fibers poly(benzimidazole) fibers, aramid fibers (e.g., mefa-aramid fibers and para-aramid fibers), polypyridobisimidazole fibers, polybenzylthiazole fibers, polybenzyloxazole fibers, melamine-formaldehyde polymer fibers, phenol- formaldehyde polymer fibers, oxidized polyacrylonitrile fibers, polyamide-imide fibers and combinations, mixtures, or blends thereof.
- the textile material comprises aramid fibers in addition to the polyphenylene sulfide fibers.
- the textile materials described above are believed to be well-suited for use in applications where the textile material must meet certain requirements for flame resistance.
- the textile material can be a fabric used in the manufacture of curtains or window treatments, which fabric should meet the most stringent requirements of NFPA 701 .
- the textile material can also be used in the manufacture of upholstery and furniture fabrics, automotive fabrics (e.g., woven, knit, or nonwoven textiles used in automotive applications), aircraft interiors, etc.
- the invention provides a method for dyeing polyphenylene sulfide fibers.
- the method generally comprises the steps of: (a) providing a textile material comprising polyphenylene sulfide fibers; (b) providing a dye liquor comprising a liquid medium and a disperse dye; (c) applying the dye liquor to the textile material; (d) heating the textile material under ambient atmosphere to a temperature sufficient to evaporate substantially all of the liquid medium from the textile material; and (e) heating the textile material under ambient atmosphere to a temperature sufficient to fix the disperse dye to the polyphenylene sulfide fibers.
- the textile material utilized in the method can be any suitable textile material comprising polyphenylene sulfide fibers, such as any of the textile materials described above.
- the dye liquor comprises a liquid medium and a disperse dye.
- the liquid medium can be any liquid medium suitable for use with disperse dyes.
- the liquid medium is an aqueous medium, such as water.
- the liquid medium can comprise a surfactant or wetting agent in order to improve wetting of the polyphenylene sulfide fibers with the dye liquor.
- the dye liquor has a pH of about 4 to about 7.5, more preferably about 5 to about 7.
- the disperse dye present in the dye liquor can be any of the disperse dyes discussed above in connection with the textile material of the invention.
- the dye liquor further comprises a volatile organic acid having a boiling point of about 100 °C to about 170 °C.
- volatile organic acids include, but are not limited to, acetic acid, formic acid, propionic acid, butyric acid, and mixtures thereof. While not wishing to be bound to any particular theory, it is believed that such volatile organic acids improve the color yield of the dyeing process, especially when the dye is fixed at temperatures of 180 °C or more. Further, with a boiling point of 100 °C to 170 °C, it is believed that the organic acid vaporizes during the dye fixation step and does not leave any harmful residue on the fibers.
- the dye liquor further comprises a dye carrier.
- Suitable dye carriers include, but are not limited to, propylene glycol, ethylene glycol, dipropylene glycol, tripropylene glycol, diethylene glycol, triethylene glycol, benzoic acid, triethanolamine, polyethylene oxide, polyethylene glycol, copolymers of ethylene oxide and propylene oxide, and mixtures thereof. While not wishing to be bound to any particular theory, it is believed that such dye carriers can assist in dye solubilization and/or dye penetration and diffusion into the
- the dye liquor can be applied to the textile material in any suitable fashion and using any suitable apparatus.
- the textile material is passed through a bath of the dye liquor so that it is saturated with the dye liquor.
- the textile material can be passed through one or more nip rollers, which apply pressure to the textile material and remove excess dye liquor before the drying step.
- the dye liquor can be sprayed directly onto the surface of the textile material.
- the textile material is heated under ambient atmosphere to a temperature sufficient to evaporate substantially all of the liquid medium (and any volatile organic acid and/or dye carrier in the dye liquor) from the textile material.
- the textile material can be heated to any suitable temperature in this step.
- the textile material is heated to a temperature greater than 40 °C, more preferably 100 °C, 130 °C, or 140 °C.
- the textile material is heated to a first temperature
- This dye fixation step preferably is performed under ambient atmosphere, meaning that the step is not performed in a closed system under elevated pressure.
- the textile material can be heated to any suitable temperature in order to fix the dye.
- the textile material is heated to a temperature of 160 °C or more. More preferably, the textile material is heated to a temperature of about 180 °C or more or about 190 °C or more.
- the textile material preferably is not heated to a temperature greater than 260 °C because such temperatures have been observed to cause adverse dye degradation.
- the textile material is heated to a temperature of about 180 °C to about 260 °C, more preferably about 190 °C to about 240 °C.
- the textile material can be further treated in order to remove and/or neutralize any unfixed disperse dye that remains on the textile material.
- the method described above further comprises the step of treating the textile material from step (e) with a caustic solution to remove or neutralize unfixed disperse dye on the textile material.
- the textile material can be treated with the caustic solution in any suitable manner.
- the textile material can be immersed in a bath of the caustic solution (maintained at a temperature of 40 °C to about 80 °C) for a sufficient amount of time to remove and/or neutralize the unfixed dye.
- the textile material can be impregnated with the caustic solution and then steamed.
- the caustic solution preferably comprises a reducing agent that is capable of reducing any unfixed disperse dye to an uncolored form.
- Suitable reducing agents include, but are not limited to, sodium bisulfite.
- the method described above can be modified in order to dye the additional fibers.
- the dye liquor can further comprise one or more vat dyes, which will dye the cellulose fibers.
- the method can also be preceded or succeeded by a series of steps that dye the additional fibers.
- the textile material comprises polyester fibers
- the textile material can be jet dyed using disperse dyes in order to impart the desired color and shade to the polyester fibers.
- the textile material can be jet dyed before or after dyeing in accordance with the method described above.
- the polyester fibers and the polyphenylene sulfide fibers can be dyed simultaneously using the method described above using one or more suitable disperse dyes.
- Table 1 Composition of dye liquors.
- Disperse Blue 291 is an azo dye containing two nitro groups. The molar mass of Disperse Blue 291 is 509 g/mol.
- Qualsperse Rubine 3BSK is a commercially available version of C.I. Disperse Red 167. Disperse Red 167 is an azo dye containing a nitro group. Disperse Red 167 has a molar mass of 505.9 g/mol, a boiling point of 713 °C, and a flash point of 385 °C.
- Qualsperse Blue BNS is a water dispersion of C.I. Disperse Blue 60.
- Disperse Blue 60 is an anthraquinone dye having a molar mass of 379 g/mol, a boiling point of 681 °C, and a flash point of 363 °C.
- Terasil Yellow GWL is a water dispersion of C.I. Disperse Yellow 42.
- Disperse Yellow 42 is a diphenylamine dye containing a nitro group. Disperse Yellow 42 has a molar mass of 369 g/mol, a boiling point of 548 °C, and a flash point of 285 °C.
- the nonwoven textile materials were dried at a temperature of approximately 120 °C (250 °F) to remove water and then placed in a lab convection oven set at (215 °C) 420 °F. The nonwoven textile materials were left in the oven for approximately 6 minutes.
- the nonwoven textile materials were then immersed in an aqueous solution containing 3% sodium hydroxide and 6% sodium bisulfite.
- the aqueous solution was maintained at a temperature of approximately 60 °C, and the nonwoven textile materials were left in the solution for approximately 20 minutes.
- the nonwoven textile materials were then rinsed with water several times and immersed in a 5% hydrogen peroxide solution.
- the hydrogen peroxide solution was maintained at a temperature of approximately 50 °C, and the nonwoven textile materials were left in the solution for approximately 10 minutes.
- the nonwoven textile materials were then rinsed with water several times and finally dried at a temperature of approximately 120 °C (250 °F).
- Disperse dyes used in treating nonwoven materials and their molar masses (in g/mol), boiling points (in °C), and flash points (in °C).
- the nonwoven textile materials dyed using the procedure described above exhibit excellent coloration.
- the polyphenylene sulfide fibers in the nonwoven showed a uniform coloration throughout the cross-section of the fibers, which is indicative of high color yield and excellent dye fixation.
- the dyed nonwoven textile materials also showed virtually no color loss after 5 washes. Further, the
- Knit fabrics made using a filament polyphenylene sulfide fiber were dyed in accordance with the procedure described above using some of the dye liquors described above. These dyed knit fabrics exhibited similar properties to the dyed nonwoven textile materials.
- Lumachrom Orange SCZ (C.I. Disperse Orange 30) 5.0
- the fabric was next immersed in an aqueous solution containing 3% sodium hydroxide and 6% sodium bisulfite. The fabric was then placed in a saturated steamer for approximately 3 minutes, followed by rinsing in hot water and immersion in a 6% hydrogen peroxide solution. The fabric was lastly rinsed in hot water.
- the resulting fabric had a bright orange color with uniform color appearance.
- the dyed fabric also exhibited good crocking fastness (dry crocking rating of 4-5), lightfastness, and washfastness.
Abstract
Description
Claims
Priority Applications (3)
Application Number | Priority Date | Filing Date | Title |
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EP17794139.0A EP3535442A1 (en) | 2016-11-07 | 2017-10-17 | Textile materials containing dyed polyphenylene sulfide fibers and methods for producing the same |
CA3042500A CA3042500C (en) | 2016-11-07 | 2017-10-17 | Textile materials containing dyed polyphenylene sulfide fibers and methods for producing the same |
ZA2019/02832A ZA201902832B (en) | 2016-11-07 | 2019-05-06 | Textile materials containing dyed polyphenylene sulfide fibers and methods for producing the same |
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US201662418731P | 2016-11-07 | 2016-11-07 | |
US62/418,731 | 2016-11-07 |
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WO2018085037A1 true WO2018085037A1 (en) | 2018-05-11 |
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PCT/US2017/056894 WO2018085037A1 (en) | 2016-11-07 | 2017-10-17 | Textile materials containing dyed polyphenylene sulfide fibers and methods for producing the same |
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US (1) | US20180127916A1 (en) |
EP (1) | EP3535442A1 (en) |
CA (1) | CA3042500C (en) |
WO (1) | WO2018085037A1 (en) |
ZA (1) | ZA201902832B (en) |
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US5447540A (en) * | 1992-01-30 | 1995-09-05 | Teijin Limited | Method of dyeing a high heat-resistant synthetic fiber material |
JP2004285517A (en) * | 2003-03-24 | 2004-10-14 | Toray Ind Inc | Underwear |
CN101512057B (en) * | 2006-09-21 | 2011-08-10 | 旭化成纤维株式会社 | Heat-resistant non-woven fabric |
US20130273799A1 (en) * | 2012-04-13 | 2013-10-17 | Ticona Llc | Polyarylene Sulfide Fibers and Composites Including the Fibers |
-
2017
- 2017-10-17 WO PCT/US2017/056894 patent/WO2018085037A1/en unknown
- 2017-10-17 CA CA3042500A patent/CA3042500C/en active Active
- 2017-10-17 US US15/785,772 patent/US20180127916A1/en not_active Abandoned
- 2017-10-17 EP EP17794139.0A patent/EP3535442A1/en not_active Withdrawn
-
2019
- 2019-05-06 ZA ZA2019/02832A patent/ZA201902832B/en unknown
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JPH01272883A (en) * | 1988-04-21 | 1989-10-31 | Teijin Ltd | Dyeing of polyphenylene sulfide fiber |
EP1375574A1 (en) * | 2001-02-21 | 2004-01-02 | Toray Industries, Inc. | Polyphenylene sulfide member and its manufacturing method |
JP2003278017A (en) * | 2002-03-22 | 2003-10-02 | Toray Ind Inc | Heat insulating liner |
US7713891B1 (en) | 2007-06-19 | 2010-05-11 | Milliken & Company | Flame resistant fabrics and process for making |
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WO2012148031A1 (en) * | 2011-04-29 | 2012-11-01 | 코오롱글로텍주식회사 | Polyphenylene sulfide fabric having outstanding dyeing properties and sunlight fastness, and a production method therefor |
US8722551B2 (en) | 2011-09-16 | 2014-05-13 | Milliken & Company | Flame retardant composition and textile material comprising the same |
US9453112B2 (en) | 2013-06-04 | 2016-09-27 | Milliken & Company | Phosphorus-containing polymer, article, and processes for producing the same |
US20150118931A1 (en) | 2013-10-25 | 2015-04-30 | Milliken & Company | Flame retardant precursors, polymers prepared from such precursors, and flame resistant fabrics treated with such polymers |
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CA3042500A1 (en) | 2018-05-11 |
US20180127916A1 (en) | 2018-05-10 |
CA3042500C (en) | 2021-08-31 |
ZA201902832B (en) | 2020-01-29 |
EP3535442A1 (en) | 2019-09-11 |
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