JPWO2009139087A1 - 共重合ポリエーテルポリアミド樹脂 - Google Patents
共重合ポリエーテルポリアミド樹脂 Download PDFInfo
- Publication number
- JPWO2009139087A1 JPWO2009139087A1 JP2010511855A JP2010511855A JPWO2009139087A1 JP WO2009139087 A1 JPWO2009139087 A1 JP WO2009139087A1 JP 2010511855 A JP2010511855 A JP 2010511855A JP 2010511855 A JP2010511855 A JP 2010511855A JP WO2009139087 A1 JPWO2009139087 A1 JP WO2009139087A1
- Authority
- JP
- Japan
- Prior art keywords
- polyamide resin
- polyether polyamide
- formula
- woven
- knitted fabric
- 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.)
- Granted
Links
- 239000004721 Polyphenylene oxide Substances 0.000 title claims abstract description 100
- 229920000570 polyether Polymers 0.000 title claims abstract description 100
- 229920006122 polyamide resin Polymers 0.000 title claims abstract description 73
- 229920001577 copolymer Polymers 0.000 title claims abstract description 37
- -1 diamine compound Chemical class 0.000 claims abstract description 83
- 239000004744 fabric Substances 0.000 claims abstract description 55
- 239000011248 coating agent Substances 0.000 claims abstract description 33
- 238000000576 coating method Methods 0.000 claims abstract description 31
- 239000004952 Polyamide Substances 0.000 claims abstract description 10
- 229920002647 polyamide Polymers 0.000 claims abstract description 10
- 125000004432 carbon atom Chemical group C* 0.000 claims description 36
- 125000002947 alkylene group Chemical group 0.000 claims description 21
- 150000002430 hydrocarbons Chemical group 0.000 claims description 19
- 229930195733 hydrocarbon Natural products 0.000 claims description 18
- 239000004215 Carbon black (E152) Substances 0.000 claims description 17
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims description 15
- 125000001931 aliphatic group Chemical group 0.000 claims description 8
- 125000005647 linker group Chemical group 0.000 claims description 6
- 125000002723 alicyclic group Chemical group 0.000 claims description 5
- 239000000853 adhesive Substances 0.000 claims description 4
- 230000001070 adhesive effect Effects 0.000 claims description 4
- 238000005470 impregnation Methods 0.000 claims description 4
- 239000000565 sealant Substances 0.000 claims 1
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 68
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 64
- 229920000642 polymer Polymers 0.000 description 54
- NBIIXXVUZAFLBC-UHFFFAOYSA-N phosphoric acid Substances OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 35
- 239000001361 adipic acid Substances 0.000 description 34
- 235000011037 adipic acid Nutrition 0.000 description 34
- 229910001873 dinitrogen Inorganic materials 0.000 description 32
- 150000001412 amines Chemical class 0.000 description 31
- 229920005989 resin Polymers 0.000 description 30
- 239000011347 resin Substances 0.000 description 30
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 27
- 229910052757 nitrogen Inorganic materials 0.000 description 23
- 239000000835 fiber Substances 0.000 description 22
- 238000006116 polymerization reaction Methods 0.000 description 22
- 239000002759 woven fabric Substances 0.000 description 22
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 18
- JBKVHLHDHHXQEQ-UHFFFAOYSA-N epsilon-caprolactam Chemical compound O=C1CCCCCN1 JBKVHLHDHHXQEQ-UHFFFAOYSA-N 0.000 description 18
- SLXKOJJOQWFEFD-UHFFFAOYSA-N 6-aminohexanoic acid Chemical compound NCCCCCC(O)=O SLXKOJJOQWFEFD-UHFFFAOYSA-N 0.000 description 17
- 229960002684 aminocaproic acid Drugs 0.000 description 17
- 238000006243 chemical reaction Methods 0.000 description 17
- 150000004985 diamines Chemical class 0.000 description 16
- 229920001971 elastomer Polymers 0.000 description 16
- 239000005060 rubber Substances 0.000 description 16
- 239000007864 aqueous solution Substances 0.000 description 13
- 150000001875 compounds Chemical class 0.000 description 13
- 230000035699 permeability Effects 0.000 description 12
- 230000000052 comparative effect Effects 0.000 description 11
- 239000002253 acid Substances 0.000 description 10
- 239000003963 antioxidant agent Substances 0.000 description 9
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 9
- 238000000034 method Methods 0.000 description 9
- 239000003795 chemical substances by application Substances 0.000 description 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 7
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 6
- 239000007983 Tris buffer Substances 0.000 description 6
- 125000003277 amino group Chemical group 0.000 description 6
- 230000003078 antioxidant effect Effects 0.000 description 6
- 235000014113 dietary fatty acids Nutrition 0.000 description 6
- 239000000194 fatty acid Substances 0.000 description 6
- 229930195729 fatty acid Natural products 0.000 description 6
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 5
- QRUDEWIWKLJBPS-UHFFFAOYSA-N benzotriazole Chemical compound C1=CC=C2N[N][N]C2=C1 QRUDEWIWKLJBPS-UHFFFAOYSA-N 0.000 description 5
- 239000012964 benzotriazole Substances 0.000 description 5
- 238000001035 drying Methods 0.000 description 5
- 150000004665 fatty acids Chemical class 0.000 description 5
- 239000003063 flame retardant Substances 0.000 description 5
- 230000006872 improvement Effects 0.000 description 5
- 238000002844 melting Methods 0.000 description 5
- 230000008018 melting Effects 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 4
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- 150000007513 acids Chemical class 0.000 description 4
- 239000000539 dimer Substances 0.000 description 4
- TVIDDXQYHWJXFK-UHFFFAOYSA-N dodecanedioic acid Chemical compound OC(=O)CCCCCCCCCCC(O)=O TVIDDXQYHWJXFK-UHFFFAOYSA-N 0.000 description 4
- LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 4
- NAQMVNRVTILPCV-UHFFFAOYSA-N hexane-1,6-diamine Chemical compound NCCCCCCN NAQMVNRVTILPCV-UHFFFAOYSA-N 0.000 description 4
- 239000004611 light stabiliser Substances 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- 239000000178 monomer Substances 0.000 description 4
- BDJRBEYXGGNYIS-UHFFFAOYSA-N nonanedioic acid Chemical compound OC(=O)CCCCCCCC(O)=O BDJRBEYXGGNYIS-UHFFFAOYSA-N 0.000 description 4
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 4
- 239000012188 paraffin wax Substances 0.000 description 4
- WLJVNTCWHIRURA-UHFFFAOYSA-N pimelic acid Chemical compound OC(=O)CCCCCC(O)=O WLJVNTCWHIRURA-UHFFFAOYSA-N 0.000 description 4
- 230000008569 process Effects 0.000 description 4
- 150000003839 salts Chemical class 0.000 description 4
- CXMXRPHRNRROMY-UHFFFAOYSA-N sebacic acid Chemical compound OC(=O)CCCCCCCCC(O)=O CXMXRPHRNRROMY-UHFFFAOYSA-N 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- TYFQFVWCELRYAO-UHFFFAOYSA-N suberic acid Chemical compound OC(=O)CCCCCCC(O)=O TYFQFVWCELRYAO-UHFFFAOYSA-N 0.000 description 4
- 229920002994 synthetic fiber Polymers 0.000 description 4
- 239000012209 synthetic fiber Substances 0.000 description 4
- HVLLSGMXQDNUAL-UHFFFAOYSA-N triphenyl phosphite Chemical compound C=1C=CC=CC=1OP(OC=1C=CC=CC=1)OC1=CC=CC=C1 HVLLSGMXQDNUAL-UHFFFAOYSA-N 0.000 description 4
- 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 3
- 229920002302 Nylon 6,6 Polymers 0.000 description 3
- ABLZXFCXXLZCGV-UHFFFAOYSA-N Phosphorous acid Chemical compound OP(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 description 3
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 3
- 239000000654 additive Substances 0.000 description 3
- 125000003118 aryl group Chemical group 0.000 description 3
- 230000007423 decrease Effects 0.000 description 3
- 150000002148 esters Chemical class 0.000 description 3
- 239000007789 gas Substances 0.000 description 3
- 239000011521 glass Substances 0.000 description 3
- 239000000314 lubricant Substances 0.000 description 3
- 229910052751 metal Inorganic materials 0.000 description 3
- 239000002184 metal Substances 0.000 description 3
- 239000012046 mixed solvent Substances 0.000 description 3
- 229910052698 phosphorus Inorganic materials 0.000 description 3
- 239000011574 phosphorus Substances 0.000 description 3
- 229920000728 polyester Polymers 0.000 description 3
- 229920001296 polysiloxane Polymers 0.000 description 3
- 239000012488 sample solution Substances 0.000 description 3
- 238000007789 sealing Methods 0.000 description 3
- 238000009958 sewing Methods 0.000 description 3
- 238000003860 storage Methods 0.000 description 3
- 238000010345 tape casting Methods 0.000 description 3
- QPFMBZIOSGYJDE-UHFFFAOYSA-N 1,1,2,2-tetrachloroethane Chemical compound ClC(Cl)C(Cl)Cl QPFMBZIOSGYJDE-UHFFFAOYSA-N 0.000 description 2
- RTBFRGCFXZNCOE-UHFFFAOYSA-N 1-methylsulfonylpiperidin-4-one Chemical compound CS(=O)(=O)N1CCC(=O)CC1 RTBFRGCFXZNCOE-UHFFFAOYSA-N 0.000 description 2
- PBLZLIFKVPJDCO-UHFFFAOYSA-N 12-aminododecanoic acid Chemical compound NCCCCCCCCCCCC(O)=O PBLZLIFKVPJDCO-UHFFFAOYSA-N 0.000 description 2
- YEVQZPWSVWZAOB-UHFFFAOYSA-N 2-(bromomethyl)-1-iodo-4-(trifluoromethyl)benzene Chemical compound FC(F)(F)C1=CC=C(I)C(CBr)=C1 YEVQZPWSVWZAOB-UHFFFAOYSA-N 0.000 description 2
- QSRJVOOOWGXUDY-UHFFFAOYSA-N 2-[2-[2-[3-(3-tert-butyl-4-hydroxy-5-methylphenyl)propanoyloxy]ethoxy]ethoxy]ethyl 3-(3-tert-butyl-4-hydroxy-5-methylphenyl)propanoate Chemical compound CC(C)(C)C1=C(O)C(C)=CC(CCC(=O)OCCOCCOCCOC(=O)CCC=2C=C(C(O)=C(C)C=2)C(C)(C)C)=C1 QSRJVOOOWGXUDY-UHFFFAOYSA-N 0.000 description 2
- 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 2
- 239000004114 Ammonium polyphosphate Substances 0.000 description 2
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- 229920002134 Carboxymethyl cellulose Polymers 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- PYVHTIWHNXTVPF-UHFFFAOYSA-N F.F.F.F.C=C Chemical compound F.F.F.F.C=C PYVHTIWHNXTVPF-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- UQSXHKLRYXJYBZ-UHFFFAOYSA-N Iron oxide Chemical compound [Fe]=O UQSXHKLRYXJYBZ-UHFFFAOYSA-N 0.000 description 2
- JHWNWJKBPDFINM-UHFFFAOYSA-N Laurolactam Chemical compound O=C1CCCCCCCCCCCN1 JHWNWJKBPDFINM-UHFFFAOYSA-N 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- 229910019142 PO4 Inorganic materials 0.000 description 2
- QLZHNIAADXEJJP-UHFFFAOYSA-N Phenylphosphonic acid Chemical compound OP(O)(=O)C1=CC=CC=C1 QLZHNIAADXEJJP-UHFFFAOYSA-N 0.000 description 2
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 2
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 2
- 239000004809 Teflon Substances 0.000 description 2
- 229920006362 Teflon® Polymers 0.000 description 2
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 2
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 2
- 150000001299 aldehydes Chemical class 0.000 description 2
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 2
- 229910052782 aluminium Inorganic materials 0.000 description 2
- WNROFYMDJYEPJX-UHFFFAOYSA-K aluminium hydroxide Chemical compound [OH-].[OH-].[OH-].[Al+3] WNROFYMDJYEPJX-UHFFFAOYSA-K 0.000 description 2
- 235000019826 ammonium polyphosphate Nutrition 0.000 description 2
- 229920001276 ammonium polyphosphate Polymers 0.000 description 2
- JFCQEDHGNNZCLN-UHFFFAOYSA-N anhydrous glutaric acid Natural products OC(=O)CCCC(O)=O JFCQEDHGNNZCLN-UHFFFAOYSA-N 0.000 description 2
- LJCFOYOSGPHIOO-UHFFFAOYSA-N antimony pentoxide Chemical compound O=[Sb](=O)O[Sb](=O)=O LJCFOYOSGPHIOO-UHFFFAOYSA-N 0.000 description 2
- ADCOVFLJGNWWNZ-UHFFFAOYSA-N antimony trioxide Chemical compound O=[Sb]O[Sb]=O ADCOVFLJGNWWNZ-UHFFFAOYSA-N 0.000 description 2
- 239000002216 antistatic agent Substances 0.000 description 2
- 239000004760 aramid Substances 0.000 description 2
- TZCXTZWJZNENPQ-UHFFFAOYSA-L barium sulfate Chemical compound [Ba+2].[O-]S([O-])(=O)=O TZCXTZWJZNENPQ-UHFFFAOYSA-L 0.000 description 2
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 description 2
- 239000012965 benzophenone Substances 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 2
- 229910052791 calcium Inorganic materials 0.000 description 2
- 239000011575 calcium Substances 0.000 description 2
- OSGAYBCDTDRGGQ-UHFFFAOYSA-L calcium sulfate Chemical compound [Ca+2].[O-]S([O-])(=O)=O OSGAYBCDTDRGGQ-UHFFFAOYSA-L 0.000 description 2
- GBAOBIBJACZTNA-UHFFFAOYSA-L calcium sulfite Chemical compound [Ca+2].[O-]S([O-])=O GBAOBIBJACZTNA-UHFFFAOYSA-L 0.000 description 2
- 235000010261 calcium sulphite Nutrition 0.000 description 2
- 239000001768 carboxy methyl cellulose Substances 0.000 description 2
- 235000010948 carboxy methyl cellulose Nutrition 0.000 description 2
- 150000001732 carboxylic acid derivatives Chemical group 0.000 description 2
- 239000008112 carboxymethyl-cellulose Substances 0.000 description 2
- 239000004927 clay Substances 0.000 description 2
- 150000001991 dicarboxylic acids Chemical class 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
- UKMSUNONTOPOIO-UHFFFAOYSA-N docosanoic acid Chemical compound CCCCCCCCCCCCCCCCCCCCCC(O)=O UKMSUNONTOPOIO-UHFFFAOYSA-N 0.000 description 2
- POULHZVOKOAJMA-UHFFFAOYSA-N dodecanoic acid Chemical compound CCCCCCCCCCCC(O)=O POULHZVOKOAJMA-UHFFFAOYSA-N 0.000 description 2
- 239000000945 filler Substances 0.000 description 2
- 230000009477 glass transition Effects 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- BXWNKGSJHAJOGX-UHFFFAOYSA-N hexadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCO BXWNKGSJHAJOGX-UHFFFAOYSA-N 0.000 description 2
- IPCSVZSSVZVIGE-UHFFFAOYSA-N hexadecanoic acid Chemical compound CCCCCCCCCCCCCCCC(O)=O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 description 2
- VKOBVWXKNCXXDE-UHFFFAOYSA-N icosanoic acid Chemical compound CCCCCCCCCCCCCCCCCCCC(O)=O VKOBVWXKNCXXDE-UHFFFAOYSA-N 0.000 description 2
- QQVIHTHCMHWDBS-UHFFFAOYSA-N isophthalic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 description 2
- 150000003951 lactams Chemical class 0.000 description 2
- 229910052749 magnesium Inorganic materials 0.000 description 2
- 239000011777 magnesium Substances 0.000 description 2
- ZQKXQUJXLSSJCH-UHFFFAOYSA-N melamine cyanurate Chemical compound NC1=NC(N)=NC(N)=N1.O=C1NC(=O)NC(=O)N1 ZQKXQUJXLSSJCH-UHFFFAOYSA-N 0.000 description 2
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- 229910052759 nickel Inorganic materials 0.000 description 2
- GLDOVTGHNKAZLK-UHFFFAOYSA-N octadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCO GLDOVTGHNKAZLK-UHFFFAOYSA-N 0.000 description 2
- 235000006408 oxalic acid Nutrition 0.000 description 2
- KJFMBFZCATUALV-UHFFFAOYSA-N phenolphthalein Chemical compound C1=CC(O)=CC=C1C1(C=2C=CC(O)=CC=2)C2=CC=CC=C2C(=O)O1 KJFMBFZCATUALV-UHFFFAOYSA-N 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- ZQBAKBUEJOMQEX-UHFFFAOYSA-N phenyl salicylate Chemical compound OC1=CC=CC=C1C(=O)OC1=CC=CC=C1 ZQBAKBUEJOMQEX-UHFFFAOYSA-N 0.000 description 2
- 235000021317 phosphate Nutrition 0.000 description 2
- ACVYVLVWPXVTIT-UHFFFAOYSA-N phosphinic acid Chemical compound O[PH2]=O ACVYVLVWPXVTIT-UHFFFAOYSA-N 0.000 description 2
- 150000003014 phosphoric acid esters Chemical class 0.000 description 2
- XFZRQAZGUOTJCS-UHFFFAOYSA-N phosphoric acid;1,3,5-triazine-2,4,6-triamine Chemical compound OP(O)(O)=O.NC1=NC(N)=NC(N)=N1 XFZRQAZGUOTJCS-UHFFFAOYSA-N 0.000 description 2
- 229920001451 polypropylene glycol Polymers 0.000 description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 2
- 239000008262 pumice Substances 0.000 description 2
- KIDHWZJUCRJVML-UHFFFAOYSA-N putrescine Chemical compound NCCCCN KIDHWZJUCRJVML-UHFFFAOYSA-N 0.000 description 2
- JZWFDVDETGFGFC-UHFFFAOYSA-N salacetamide Chemical group CC(=O)NC(=O)C1=CC=CC=C1O JZWFDVDETGFGFC-UHFFFAOYSA-N 0.000 description 2
- 229910052712 strontium Inorganic materials 0.000 description 2
- 239000011593 sulfur Substances 0.000 description 2
- 229910052717 sulfur Inorganic materials 0.000 description 2
- 229920003051 synthetic elastomer Polymers 0.000 description 2
- 229920003002 synthetic resin Polymers 0.000 description 2
- 239000000057 synthetic resin Substances 0.000 description 2
- 239000005061 synthetic rubber Substances 0.000 description 2
- 238000009864 tensile test Methods 0.000 description 2
- XOLBLPGZBRYERU-UHFFFAOYSA-N tin dioxide Chemical compound O=[Sn]=O XOLBLPGZBRYERU-UHFFFAOYSA-N 0.000 description 2
- 150000003852 triazoles Chemical class 0.000 description 2
- XFNJVJPLKCPIBV-UHFFFAOYSA-N trimethylenediamine Chemical compound NCCCN XFNJVJPLKCPIBV-UHFFFAOYSA-N 0.000 description 2
- 238000009941 weaving Methods 0.000 description 2
- KJYSXRBJOSZLEL-UHFFFAOYSA-N (2,4-ditert-butylphenyl) 3,5-ditert-butyl-4-hydroxybenzoate Chemical compound CC(C)(C)C1=CC(C(C)(C)C)=CC=C1OC(=O)C1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 KJYSXRBJOSZLEL-UHFFFAOYSA-N 0.000 description 1
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- NZNAAUDJKMURFU-UHFFFAOYSA-N tetrakis(2,2,6,6-tetramethylpiperidin-4-yl) butane-1,2,3,4-tetracarboxylate Chemical compound C1C(C)(C)NC(C)(C)CC1OC(=O)CC(C(=O)OC1CC(C)(C)NC(C)(C)C1)C(C(=O)OC1CC(C)(C)NC(C)(C)C1)CC(=O)OC1CC(C)(C)NC(C)(C)C1 NZNAAUDJKMURFU-UHFFFAOYSA-N 0.000 description 1
- CIWAOCMKRKRDME-UHFFFAOYSA-N tetrasodium dioxido-oxo-stibonatooxy-lambda5-stibane Chemical compound [Na+].[Na+].[Na+].[Na+].[O-][Sb]([O-])(=O)O[Sb]([O-])([O-])=O CIWAOCMKRKRDME-UHFFFAOYSA-N 0.000 description 1
- 229920001169 thermoplastic Polymers 0.000 description 1
- 239000004416 thermosoftening plastic Substances 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- 229910052718 tin Inorganic materials 0.000 description 1
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
- 238000004448 titration Methods 0.000 description 1
- 150000003626 triacylglycerols Chemical class 0.000 description 1
- STCOOQWBFONSKY-UHFFFAOYSA-N tributyl phosphate Chemical compound CCCCOP(=O)(OCCCC)OCCCC STCOOQWBFONSKY-UHFFFAOYSA-N 0.000 description 1
- IVIIAEVMQHEPAY-UHFFFAOYSA-N tridodecyl phosphite Chemical compound CCCCCCCCCCCCOP(OCCCCCCCCCCCC)OCCCCCCCCCCCC IVIIAEVMQHEPAY-UHFFFAOYSA-N 0.000 description 1
- 150000005691 triesters Chemical class 0.000 description 1
- DQWPFSLDHJDLRL-UHFFFAOYSA-N triethyl phosphate Chemical compound CCOP(=O)(OCC)OCC DQWPFSLDHJDLRL-UHFFFAOYSA-N 0.000 description 1
- BDZBKCUKTQZUTL-UHFFFAOYSA-N triethyl phosphite Chemical compound CCOP(OCC)OCC BDZBKCUKTQZUTL-UHFFFAOYSA-N 0.000 description 1
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1
- WVLBCYQITXONBZ-UHFFFAOYSA-N trimethyl phosphate Chemical class COP(=O)(OC)OC WVLBCYQITXONBZ-UHFFFAOYSA-N 0.000 description 1
- CNUJLMSKURPSHE-UHFFFAOYSA-N trioctadecyl phosphite Chemical compound CCCCCCCCCCCCCCCCCCOP(OCCCCCCCCCCCCCCCCCC)OCCCCCCCCCCCCCCCCCC CNUJLMSKURPSHE-UHFFFAOYSA-N 0.000 description 1
- QOQNJVLFFRMJTQ-UHFFFAOYSA-N trioctyl phosphite Chemical compound CCCCCCCCOP(OCCCCCCCC)OCCCCCCCC QOQNJVLFFRMJTQ-UHFFFAOYSA-N 0.000 description 1
- XZZNDPSIHUTMOC-UHFFFAOYSA-N triphenyl phosphate Chemical compound C=1C=CC=CC=1OP(OC=1C=CC=CC=1)(=O)OC1=CC=CC=C1 XZZNDPSIHUTMOC-UHFFFAOYSA-N 0.000 description 1
- PYFJQRSJTZCTPX-UHFFFAOYSA-N tris(2,3-ditert-butylphenyl) phosphite Chemical compound CC(C)(C)C1=CC=CC(OP(OC=2C(=C(C=CC=2)C(C)(C)C)C(C)(C)C)OC=2C(=C(C=CC=2)C(C)(C)C)C(C)(C)C)=C1C(C)(C)C PYFJQRSJTZCTPX-UHFFFAOYSA-N 0.000 description 1
- KOWVWXQNQNCRRS-UHFFFAOYSA-N tris(2,4-dimethylphenyl) phosphate Chemical compound CC1=CC(C)=CC=C1OP(=O)(OC=1C(=CC(C)=CC=1)C)OC1=CC=C(C)C=C1C KOWVWXQNQNCRRS-UHFFFAOYSA-N 0.000 description 1
- WTLBZVNBAKMVDP-UHFFFAOYSA-N tris(2-butoxyethyl) phosphate Chemical compound CCCCOCCOP(=O)(OCCOCCCC)OCCOCCCC WTLBZVNBAKMVDP-UHFFFAOYSA-N 0.000 description 1
- MGMXGCZJYUCMGY-UHFFFAOYSA-N tris(4-nonylphenyl) phosphite Chemical compound C1=CC(CCCCCCCCC)=CC=C1OP(OC=1C=CC(CCCCCCCCC)=CC=1)OC1=CC=C(CCCCCCCCC)C=C1 MGMXGCZJYUCMGY-UHFFFAOYSA-N 0.000 description 1
- JZNDMMGBXUYFNQ-UHFFFAOYSA-N tris(dodecylsulfanyl)phosphane Chemical compound CCCCCCCCCCCCSP(SCCCCCCCCCCCC)SCCCCCCCCCCCC JZNDMMGBXUYFNQ-UHFFFAOYSA-N 0.000 description 1
- QQBLOZGVRHAYGT-UHFFFAOYSA-N tris-decyl phosphite Chemical compound CCCCCCCCCCOP(OCCCCCCCCCC)OCCCCCCCCCC QQBLOZGVRHAYGT-UHFFFAOYSA-N 0.000 description 1
- BSVBQGMMJUBVOD-UHFFFAOYSA-N trisodium borate Chemical compound [Na+].[Na+].[Na+].[O-]B([O-])[O-] BSVBQGMMJUBVOD-UHFFFAOYSA-N 0.000 description 1
- RYFMWSXOAZQYPI-UHFFFAOYSA-K trisodium phosphate Chemical compound [Na+].[Na+].[Na+].[O-]P([O-])([O-])=O RYFMWSXOAZQYPI-UHFFFAOYSA-K 0.000 description 1
- NCPXQVVMIXIKTN-UHFFFAOYSA-N trisodium;phosphite Chemical compound [Na+].[Na+].[Na+].[O-]P([O-])[O-] NCPXQVVMIXIKTN-UHFFFAOYSA-N 0.000 description 1
- BIKXLKXABVUSMH-UHFFFAOYSA-N trizinc;diborate Chemical compound [Zn+2].[Zn+2].[Zn+2].[O-]B([O-])[O-].[O-]B([O-])[O-] BIKXLKXABVUSMH-UHFFFAOYSA-N 0.000 description 1
- WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical compound [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 description 1
- 229920000785 ultra high molecular weight polyethylene Polymers 0.000 description 1
- KLNPWTHGTVSSEU-UHFFFAOYSA-N undecane-1,11-diamine Chemical compound NCCCCCCCCCCCN KLNPWTHGTVSSEU-UHFFFAOYSA-N 0.000 description 1
- PZMFITAWSPYPDV-UHFFFAOYSA-N undecane-2,4-dione Chemical compound CCCCCCCC(=O)CC(C)=O PZMFITAWSPYPDV-UHFFFAOYSA-N 0.000 description 1
- 150000004670 unsaturated fatty acids Chemical class 0.000 description 1
- 235000021122 unsaturated fatty acids Nutrition 0.000 description 1
- 239000003981 vehicle Substances 0.000 description 1
- 239000001993 wax Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
- PZRXQXJGIQEYOG-UHFFFAOYSA-N zinc;oxido(oxo)borane Chemical compound [Zn+2].[O-]B=O.[O-]B=O PZRXQXJGIQEYOG-UHFFFAOYSA-N 0.000 description 1
- 229910001928 zirconium oxide Inorganic materials 0.000 description 1
- 229910000859 α-Fe Inorganic materials 0.000 description 1
Classifications
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- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
- D06M15/00—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment
- D06M15/19—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment with synthetic macromolecular compounds
- D06M15/37—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
- D06M15/59—Polyamides; Polyimides
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G69/00—Macromolecular compounds obtained by reactions forming a carboxylic amide link in the main chain of the macromolecule
- C08G69/40—Polyamides containing oxygen in the form of ether groups
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J5/00—Manufacture of articles or shaped materials containing macromolecular substances
- C08J5/04—Reinforcing macromolecular compounds with loose or coherent fibrous material
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D177/00—Coating compositions based on polyamides obtained by reactions forming a carboxylic amide link in the main chain; Coating compositions based on derivatives of such polymers
- C09D177/06—Polyamides derived from polyamines and polycarboxylic acids
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06N—WALL, FLOOR, OR LIKE COVERING MATERIALS, e.g. LINOLEUM, OILCLOTH, ARTIFICIAL LEATHER, ROOFING FELT, CONSISTING OF A FIBROUS WEB COATED WITH A LAYER OF MACROMOLECULAR MATERIAL; FLEXIBLE SHEET MATERIAL NOT OTHERWISE PROVIDED FOR
- D06N3/00—Artificial leather, oilcloth or other material obtained by covering fibrous webs with macromolecular material, e.g. resins, rubber or derivatives thereof
- D06N3/12—Artificial leather, oilcloth or other material obtained by covering fibrous webs with macromolecular material, e.g. resins, rubber or derivatives thereof with macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds, e.g. gelatine proteins
- D06N3/125—Artificial leather, oilcloth or other material obtained by covering fibrous webs with macromolecular material, e.g. resins, rubber or derivatives thereof with macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds, e.g. gelatine proteins with polyamides
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B60—VEHICLES IN GENERAL
- B60R—VEHICLES, VEHICLE FITTINGS, OR VEHICLE PARTS, NOT OTHERWISE PROVIDED FOR
- B60R21/00—Arrangements or fittings on vehicles for protecting or preventing injuries to occupants or pedestrians in case of accidents or other traffic risks
- B60R21/02—Occupant safety arrangements or fittings, e.g. crash pads
- B60R21/16—Inflatable occupant restraints or confinements designed to inflate upon impact or impending impact, e.g. air bags
- B60R21/23—Inflatable members
- B60R21/235—Inflatable members characterised by their material
- B60R2021/23504—Inflatable members characterised by their material characterised by material
- B60R2021/23509—Fabric
- B60R2021/23514—Fabric coated fabric
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J2377/00—Characterised by the use of polyamides obtained by reactions forming a carboxylic amide link in the main chain; Derivatives of such polymers
- C08J2377/06—Polyamides derived from polyamines and polycarboxylic acids
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- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T442/00—Fabric [woven, knitted, or nonwoven textile or cloth, etc.]
- Y10T442/20—Coated or impregnated woven, knit, or nonwoven fabric which is not [a] associated with another preformed layer or fiber layer or, [b] with respect to woven and knit, characterized, respectively, by a particular or differential weave or knit, wherein the coating or impregnation is neither a foamed material nor a free metal or alloy layer
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- Y10T442/00—Fabric [woven, knitted, or nonwoven textile or cloth, etc.]
- Y10T442/20—Coated or impregnated woven, knit, or nonwoven fabric which is not [a] associated with another preformed layer or fiber layer or, [b] with respect to woven and knit, characterized, respectively, by a particular or differential weave or knit, wherein the coating or impregnation is neither a foamed material nor a free metal or alloy layer
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- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T442/00—Fabric [woven, knitted, or nonwoven textile or cloth, etc.]
- Y10T442/20—Coated or impregnated woven, knit, or nonwoven fabric which is not [a] associated with another preformed layer or fiber layer or, [b] with respect to woven and knit, characterized, respectively, by a particular or differential weave or knit, wherein the coating or impregnation is neither a foamed material nor a free metal or alloy layer
- Y10T442/2762—Coated or impregnated natural fiber fabric [e.g., cotton, wool, silk, linen, etc.]
- Y10T442/277—Coated or impregnated cellulosic fiber fabric
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- Wood Science & Technology (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Dispersion Chemistry (AREA)
- Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
- Polyamides (AREA)
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Abstract
Description
[1] 共重合ポリエーテルポリアミド樹脂の伸度が1000%以上で、弾性率が15MPa以下であることを特徴とする織編物へのコーティングもしくは含浸用共重合ポリエーテルポリアミド樹脂。
[2] 前記共重合ポリエーテルポリアミド樹脂が、下記(化式1)で表されるポリエーテルジアミン化合物と下記(化式2)で表されるジカルボン酸化合物とから構成されたポリエーテルポリアミドからなるソフトセグメント及び、下記(化式3)で表されるアミノカルボン酸化合物及び/又は下記(化式4)で表されるラクタム化合物から構成されたポリアミドからなるハードセグメントが結合されてなることを特徴とする[1]に記載の織編物へのコーティングもしくは含浸用共重合ポリエーテルポリアミド樹脂。
[但し、R2は、炭化水素鎖を含む連結基を表わす]
[3] 前記(化式1)のポリエーテルジアミン化合物が下記(化式5)で表されるポリエーテルジアミン化合物であり、該ポリエーテルジアミン化合物の数平均分子量が700〜1200であり、ソフトセグメントが該共重合ポリエーテルポリアミド樹脂総量に対して70〜85質量%の量にて用いられ、かつ該共重合ポリエーテルポリアミド樹脂の還元粘度が1.3以上である、[2]に記載の織編物へのコーティングもしくは含浸用共重合ポリエーテルポリアミド樹脂。
[4] 前記(化式2)のジカルボン酸化合物が脂肪族ジカルボン酸もしくは脂環族ジカルボン酸である[2]または[3]に記載の織編物へのコーティングもしくは含浸用共重合ポリエーテルポリアミド樹脂。
[5] 前記(化式2)のR1が炭素原子数1〜20のアルキレン基を表わす[2]〜[4]のいずれかに記載の織編物へのコーティングもしくは含浸用共重合ポリエーテルポリアミド樹脂。
[6] 前記(化式3)のR2が炭素原子数2〜20のアルキレン基を表わす[2]〜[5]のいずれかに記載の織編物へのコーティングもしくは含浸用共重合ポリエーテルポリアミド樹脂。
[7] 前記(化式4)のR3が炭素原子数3〜20のアルキレン基を表わす[2]〜[6]のいずれかに記載の織編物へのコーティングもしくは含浸用共重合ポリエーテルポリアミド樹脂。
[8] [1]〜[7]のいずれかに記載の織編物へのコーティングもしくは含浸用共重合ポリエーテルポリアミド樹脂をコーティング剤として用いたエアバッグ用基布。
[9] [1]〜[7]のいずれかに記載の織編物へのコーティングもしくは含浸用共重合ポリエーテルポリアミド樹脂をシール剤として用いたエアバッグ。
[10] [1]〜[7]のいずれかに記載の織編物へのコーティングもしくは含浸用共重合ポリエーテルポリアミド樹脂を接着剤として用いたエアバッグ。
上記(化式1)のポリエーテルジアミン化合物の数平均分子量、ソフトセグメントの共重合ポリエーテルポリアミド樹脂総量に対する割合及び該共重合ポリエーテルポリアミド樹脂の還元粘度が上記範囲であることより、該共重合ポリエーテルポリアミド樹脂を少なくとも片面に塗布したエアバッグ用織物の滑脱抵抗値及び引裂強力値が共に塗布前の織物に対して1.8倍以上となり、所望の性能を得られる。
カバーファクター
=(経糸繊度(dtex)×0.9)1/2×経糸密度(本/2.54cm)
+(緯糸繊度(dtex)×0.9)1/2×緯糸密度(本/2.54cm)・・・(式1)
1.還元粘度(ηsp/c)
共重合ポリエーテルポリアミド樹脂約0.05gを25mLのフェノール/テトラクロロエタン混合溶媒(重量比:6/4)に溶解し、得られた試料溶液についてオストワルド粘度計を用いて30℃で測定した。
2.末端アミノ基濃度([NH2];単位はeq/ton)
共重合ポリエーテルポリアミド樹脂約0.6gを50mLのフェノール/エタノール混合溶媒(容量比:4/1)に溶解し、さらに20mLの蒸留水/エタノール混合溶媒(容量比:3/2)を加え、得られた試料溶液に、指示薬としてメチルオレンジを加えて、N/10塩酸で滴定した。
3.末端カルボキシル基濃度([COOH];単位はeq/ton)
共重合ポリエーテルポリアミド樹脂約0.2gを10mLのベンジルアルコールに加熱溶解し、さらに10mLのクロロホルムを加え、得られた試料溶液に、指示薬としてフェノールフタレインを加えて、N/25水酸化カリウム−エタノール溶液で滴定した。
4.数平均分子量(Mn)
数平均分子量(Mn)は、末端アミノ基濃度([NH2])及び末端カルボキシル基濃度([COOH])を用い、(式2)により求めた。
数平均分子量(Mn)=2×1000000
÷(末端アミノ基濃度[NH2]+末端カルボキシル基濃度[COOH])・・・(式2)
5.融点(Tm)及びガラス転移温度(Tg)
Tm及びTgはティー・エイ・インスツルメント・ジャパン(株)製示差走査熱量計DSC−Q100を用いて窒素雰囲気下で測定した。室温から220℃まで10℃/minの速度で昇温し(昇温ファーストランと呼ぶ)、220℃で3分保持したのち、−80℃まで10℃/minの速度で降温し(降温ファーストランと呼ぶ)、次に220℃まで10℃/minの速度で昇温した(昇温セカンドランと呼ぶ)。得られたDSCチャートの昇温セカンドランの吸熱ピーク温度をTmとし、ガラス転移点からTgも算出した。
6.組成
共重合ポリエーテルポリアミド樹脂15mgを重ギ酸に溶解し、BRUKER製AVANCE500フーリエ変換核磁気共鳴装置を用いて、室温で測定したプロトンNMRスペクトルから各成分の組成を求めた。
7.樹脂伸度
共重合ポリエーテルポリアミド樹脂を固形分20%の水系樹脂とし、この水系樹脂をテフロン(登録商標)シートで作製した枠内に流し込み、2日間、自然乾燥して、厚み約1mmの一様な厚さの皮膜を作成した。得られた皮膜を長方形に切断(幅10mm、長さ約50mm)して、引張試験機でチャック間10mm、引張速度10mm/minで引張試験を行い、破断時の伸度を測定した。
8.樹脂弾性率(ヤング率)
共重合ポリエーテルポリアミド樹脂を固形分20%の水系樹脂とし、この水系樹脂をテフロン(登録商標)シートで作製した枠内に流し込み、2日間、自然乾燥して、厚み約1mmの一様な厚さの皮膜を作成した。得られた皮膜を長方形に切断(幅10mm、長さ約50mm)して、引張試験機でチャック間10mm、引張速度10mm/minで引張試験を行い、弾性率(ヤング率)を測定した。
9.通気度
100kPa圧力下での通気度を高圧通気度測定機(OEMシステム(株)製)を用いて測定した。
10.滑脱抵抗力上昇率
ASTM D6479により測定した。
滑脱抵抗力上昇率は(式3)より求めた。
滑脱抵抗力上昇率(倍)=(塗布後滑脱抵抗力経+塗布後滑脱抵抗力緯)
÷(塗布前滑脱抵抗力経+塗布前滑脱抵抗力緯)・・・(式3)
11.引裂強力上昇率
JIS L1096 8.15.2 中央値荷重により測定した。
引裂強力上昇率は(式4)より求めた。
引裂強力上昇率(倍)=(塗布後引裂強力経+塗布後引裂強力緯)
÷(塗布前引裂強力経+塗布前引裂強力緯)・・・(式4)
攪拌機、温調計、圧力計、窒素ガス導入口、縮合水排出口及び圧力調整装置を備えた容積約5Lの反応容器にポリエーテルジアミン(HUNTSMAN社製のジェファーミンED900、全アミン:2.16meq/g)1005.45g、アジピン酸(AA)158.68g、ε−カプロラクタム(ε−CL)375.00g及びリン酸水溶液(63.2g/L)22.5mLを仕込み、容器内を十分窒素置換した後、0.5時かけて230℃まで昇温し、さらに230℃で4.0時間重合を行った。その後、1.5時間減圧で重合を行うことでポリマーを得た。その後、230℃のまま圧力調整装置により1.0時間かけて容器内を減圧し、さらに230℃で0.5時間重合を行い、ポリマーを得た。得られたポリマーは、淡黄色でよく伸び、ゴム弾性を有していた。得られたポリマーの特性を評価し表1に示した。
攪拌機、温調計、窒素ガス導入口、そして縮合水排出口を備えた容積約500mLの反応容器にポリエーテルジアミン(HUNTSMAN社製のジェファーミンED900、全アミン:2.16meq/g)134.06g、アジピン酸(AA)21.16g、6−アミノヘキサン酸(6−AHA)57.96g及びリン酸水溶液(63.2g/L)3mLを仕込み、容器内を十分窒素置換した後、窒素ガスを流速150mL/分で供給しながら0.5時間かけて230℃まで昇温し、さらに230℃で8.5時間重合を行い、ポリマーを得た。得られたポリマーは、淡黄色でよく伸び、ゴム弾性を有していた。得られたポリマーの特性を評価し表1に示した。
攪拌機、温調計、窒素ガス導入口、そして縮合水排出口を備えた容積約500mLの反応容器にポリエーテルジアミン(HUNTSMAN社製のジェファーミンED600、全アミン:3.21meq/g)101.89g、ポリエーテルジアミン(HUNTSMAN社製のジェファーミンED900、全アミン:2.16meq/g)32.17g、アジピン酸(AA)28.98g、ε−カプロラクタム(ε−CL)50.00g及びリン酸水溶液(63.2g/L)3mLを仕込み、容器内を十分窒素置換した後、窒素ガスを流速150mL/分で供給しながら0.5時間かけて230℃まで昇温し、さらに230℃で8.0時間重合を行い、ポリマーを得た。得られたポリマーは、淡黄色でよく伸び、ゴム弾性を有していた。得られたポリマーの特性を評価し表1に示した。
攪拌機、温調計、窒素ガス導入口、そして縮合水排出口を備えた容積約500mLの反応容器にポリエーテルジアミン(HUNTSMAN社製のジェファーミンED900、全アミン:2.16meq/g)116.36g、ポリエーテルジアミン(HUNTSMAN社製のジェファーミンED2003、全アミン:1.00meq/g)8.76g、アジピン酸(AA)19.00g、ε−カプロラクタム(ε−CL)60.00g及びリン酸水溶液(63.2g/L)3mLを仕込み、容器内を十分窒素置換した後、窒素ガスを流速150mL/分で供給しながら0.5時間かけて230℃まで昇温し、さらに230℃で8.5時間重合を行い、ポリマーを得た。得られたポリマーは、淡黄色でよく伸び、ゴム弾性を有していた。得られたポリマーの特性を評価し表1に示した。
攪拌機、温調計、窒素ガス導入口、そして縮合水排出口を備えた容積約500mLの反応容器にポリエーテルジアミン(HUNTSMAN社製のジェファーミンED900、全アミン:2.16meq/g)112.61g、ポリエーテルジアミン(HUNTSMAN社製のジェファーミンED2003、全アミン:1.00meq/g)21.45g、アジピン酸(AA)19.34g、ε−カプロラクタム(ε−CL)50.00g及びリン酸水溶液(63.2g/L)3mLを仕込み、容器内を十分窒素置換した後、窒素ガスを流速150mL/分で供給しながら0.5時間かけて230℃まで昇温し、さらに230℃で8.0時間重合を行い、ポリマーを得た。得られたポリマーは、淡黄色でよく伸び、ゴム弾性を有していた。得られたポリマーの特性を評価し表1に示した。
攪拌機、温調計、窒素ガス導入口、そして縮合水排出口を備えた容積約500mLの反応容器にポリエーテルジアミン(HUNTSMAN社製のジェファーミンED900、全アミン:2.16meq/g)85.98g、ポリエーテルジアミン(HUNTSMAN社製のジェファーミンED2003、全アミン:1.00meq/g)30.21g、アジピン酸(AA)15.78g、ε−カプロラクタム(ε−CL)70.00g及びリン酸水溶液(63.2g/L)3mLを仕込み、容器内を十分窒素置換した後、窒素ガスを流速150mL/分で供給しながら0.5時間かけて230℃まで昇温し、さらに230℃で9.0時間重合を行い、ポリマーを得た。得られたポリマーは、淡黄色でよく伸び、ゴム弾性を有していた。得られたポリマーの特性を評価し表1に示した。
攪拌機、温調計、窒素ガス導入口、そして縮合水排出口を備えた容積約500mLの反応容器にポリエーテルジアミン(HUNTSMAN社製のジェファーミンED900、全アミン:2.16meq/g)104.50g、ポリエーテルジアミン(HUNTSMAN社製のジェファーミンED2003、全アミン:1.00meq/g)36.71g、アジピン酸(AA)19.17g、ε−カプロラクタム(ε−CL)42.00g及びリン酸水溶液(63.2g/L)3mLを仕込み、容器内を十分窒素置換した後、窒素ガスを流速150mL/分で供給しながら0.5時間かけて230℃まで昇温し、さらに230℃で9.0時間重合を行い、ポリマーを得た。得られたポリマーは、淡黄色でよく伸び、ゴム弾性を有していた。得られたポリマーの特性を評価し表1に示した。
攪拌機、温調計、圧力計、窒素ガス導入口、縮合水排出口及び圧力調整装置を備えた容積約500mLの反応容器にポリエーテルジアミン(HUNTSMAN社製のジェファーミンED900、全アミン:2.16meq/g)134.06g、アジピン酸(AA)21.16g、6−アミノヘキサン酸(6−AHA)57.96g、ヒンダードフェノール系酸化防止剤(チバ・スペシャルティ・ケミカルズ社製のトリエチレングリコール−ビス〔3−(3−t−ブチル−5−メチル−4−ヒドロキシフェニル)プロピオネート〕、Irganox245)0.4g及びリン酸水溶液(63.2g/L)3mLを仕込み、容器内を十分窒素置換した後、窒素ガスを流速150mL/分で供給しながら0.5時間かけて230℃まで昇温し、さらに230℃で2.5時間重合を行った。その後、230℃のまま窒素ガスの供給を止め、真空ポンプにより1.0時間かけて容器内を減圧し、さらに230℃で1.0時間重合を行い、ポリマーを得た。得られたポリマーは、淡黄色でよく伸び、ゴム弾性を有していた。得られたポリマーの特性を評価し表1に示した。
攪拌機、温調計、圧力計、窒素ガス導入口、縮合水排出口及び圧力調整装置を備えた容積約500mLの反応容器にポリエーテルジアミン(HUNTSMAN社製のジェファーミンED900、全アミン:2.16meq/g)134.06g、アジピン酸(AA)21.16g、6−アミノヘキサン酸(6−AHA)57.96g、ヒンダードフェノール系酸化防止剤(チバ・スペシャルティ・ケミカルズ社製のペンタエリスリチル−テトラキス〔3−(3,5−ジ−t−4−ヒドロキシフェニル)プロピオネート、Irganox1010)0.4g及びリン酸水溶液(63.2g/L)3mLを仕込み、容器内を十分窒素置換した後、窒素ガスを流速150mL/分で供給しながら0.5時間かけて230℃まで昇温し、さらに230℃で2.5時間重合を行った。その後、230℃のまま窒素ガスの供給を止め、真空ポンプにより1.0時間かけて容器内を減圧し、さらに230℃で1.0時間重合を行い、ポリマーを得た。得られたポリマーは、淡黄色でよく伸び、ゴム弾性を有していた。得られたポリマーの特性を評価し表1に示した。
攪拌機、温調計、圧力計、窒素ガス導入口、縮合水排出口及び圧力調整装置を備えた容積約500mLの反応容器にポリエーテルジアミン(HUNTSMAN社製のジェファーミンED900、全アミン:2.16meq/g)134.06g、アジピン酸(AA)21.16g、6−アミノヘキサン酸(6−AHA)57.96g、ヒンダードフェノール系酸化防止剤(チバ・スペシャルティ・ケミカルズ社製のN,N'−ヘキサメチレンビス(3,5−ジ−t−ブチル−4−ヒドロキシ−ヒドロシンナマミド)、Irganox1098)0.4g及びリン酸水溶液(63.2g/L)3mLを仕込み、容器内を十分窒素置換した後、窒素ガスを流速150mL/分で供給しながら0.5時間かけて230℃まで昇温し、さらに230℃で2.5時間重合を行った。その後、230℃のまま窒素ガスの供給を止め、真空ポンプにより1.0時間かけて容器内を減圧し、さらに230℃で1.0時間重合を行い、ポリマーを得た。得られたポリマーは、淡黄色でよく伸び、ゴム弾性を有していた。得られたポリマーの特性を評価し表1に示した。
攪拌機、温調計、圧力計、窒素ガス導入口、縮合水排出口及び圧力調整装置を備えた容積約500mLの反応容器にポリエーテルジアミン(HUNTSMAN社製のジェファーミンED900、全アミン:2.16meq/g)134.06g、アジピン酸(AA)21.16g、6−アミノヘキサン酸(6−AHA)57.96g、ヒンダードフェノール系酸化防止剤(チバ・スペシャルティ・ケミカルズ社製の1,3,5−トリメチル−2,4,6−トリス(3,5−ジ−t−ブチル−4−ヒドロキシベンジル)ベンゼン、Irganox1330)0.4g及びリン酸水溶液(63.2g/L)3mLを仕込み、容器内を十分窒素置換した後、窒素ガスを流速150mL/分で供給しながら0.5時間かけて230℃まで昇温し、さらに230℃で2.5時間重合を行った。その後、230℃のまま窒素ガスの供給を止め、真空ポンプにより1.0時間かけて容器内を減圧し、さらに230℃で1.0時間重合を行い、ポリマーを得た。得られたポリマーは、淡黄色でよく伸び、ゴム弾性を有していた。得られたポリマーの特性を評価し表1に示した。
実施例1〜11のポリマーをそれぞれ、実施例12〜22へ供した。実施例1〜11のポリマーを固形分20%の水系樹脂として作製し、カルボキシメチルセルロースを該水系樹脂に対して1wt%追加し、粘度を25dPa・s(リオン株式会社製ビスコテスターVT−04Fで測定)に調整した。また、総繊度が400dtex、108フィラメントのポリアミド66繊維を平織りにてウオータージェットルームにて製織後、沸水にて収縮加工し、110℃で乾燥仕上げをし、経密度63本/2.54cm、緯密度61本/2.54cmの織物を得た。この織物に該水系樹脂をナイフコートにて塗布し、乾燥後の樹脂量を4g/m2にした織物の特性を評価し表2に示した。
攪拌機、温調計、圧力計、窒素ガス導入口、縮合水排出口及び圧力調整装置を備えた容積約500mLの反応容器にポリエーテルジアミン(HUNTSMAN社製のジェファーミンED600、全アミン:3.21meq/g)110.48g、アジピン酸(AA)25.91g、6−アミノヘキサン酸(6−AHA)81.15g及びリン酸水溶液(63.2g/L)3mLを仕込み、容器内を十分窒素置換した後、窒素ガスを流速150mL/分で供給しながら0.5時間かけて230℃まで昇温し、さらに230℃で4.5時間重合を行った。その後、230℃のまま窒素ガスの供給を止め、真空ポンプにより0.5時間かけて容器内を減圧し、さらに230℃で2時間重合を行い、ポリマーを得た。得られたポリマーは、淡黄色で比較的伸び、ゴム弾性を有していた。得られたポリマーの特性を評価し表3に示した。
攪拌機、温調計、窒素ガス導入口、そして縮合水排出口を備えた容積約500mLの反応容器にポリエーテルジアミン(HUNTSMAN社製のジェファーミンED900、全アミン:2.16meq/g)107.25g、アジピン酸(AA)16.93g、6−アミノヘキサン酸(6−AHA)92.74g及びリン酸水溶液(63.2g/L)3mLを仕込み、容器内を十分窒素置換した後、窒素ガスを流速150mL/分で供給しながら0.5時間かけて230℃まで昇温し、さらに230℃で9.0時間重合を行い、ポリマーを得た。得られたポリマーは、淡黄色でよく伸び、ゴム弾性を有していた。得られたポリマーの特性を評価し表3に示した。
攪拌機、温調計、窒素ガス導入口、そして縮合水排出口を備えた容積約500mLの反応容器にポリエーテルジアミン(HUNTSMAN社製のジェファーミンED900、全アミン:2.16meq/g)125.12g、アジピン酸(AA)19.75g、6−アミノヘキサン酸(6−AHA)69.56g及びリン酸水溶液(63.2g/L)3mLを仕込み、容器内を十分窒素置換した後、窒素ガスを流速150mL/分で供給しながら0.5時間かけて230℃まで昇温し、さらに230℃で3.0時間重合を行い、ポリマーを得た。得られたポリマーは、淡黄色でよく伸び、ゴム弾性を有していた。得られたポリマーの特性を評価し表3に示した。
攪拌機、温調計、窒素ガス導入口、そして縮合水排出口を備えた容積約500mLの反応容器にポリエーテルジアミン(HUNTSMAN社製のジェファーミンED900、全アミン:2.16meq/g)141.30g、ポリエーテルジアミン(HUNTSMAN社製のジェファーミンED2003、全アミン:1.00meq/g)10.64g、アジピン酸(AA)23.08g、ε−カプロラクタム(ε−CL)30.00g及びリン酸水溶液(63.2g/L)3mLを仕込み、容器内を十分窒素置換した後、窒素ガスを流速150mL/分で供給しながら0.5時間かけて230℃まで昇温し、さらに230℃で8.0時間重合を行い、ポリマーを得た。得られたポリマーは、ゴム弾性を有していた。得られたポリマーの特性を評価し表3に示した。
攪拌機、温調計、窒素ガス導入口、そして縮合水排出口を備えた容積約500mLの反応容器にポリエーテルジアミン(HUNTSMAN社製のジェファーミンED900、全アミン:2.16meq/g)93.84g、ポリエーテルジアミン(HUNTSMAN社製のジェファーミンED2003、全アミン:1.00meq/g)40.22g、アジピン酸(AA)17.75g、ε−カプロラクタム(ε−CL)50.00g及びリン酸水溶液(63.2g/L)3mLを仕込み、容器内を十分窒素置換した後、窒素ガスを流速150mL/分で供給しながら0.5時間かけて230℃まで昇温し、さらに230℃で8.0時間重合を行い、ポリマーを得た。得られたポリマーは、淡黄色でよく伸び、ゴム弾性を有していたが、融点がダブルピークとなり相分離傾向を示したため、その後の評価を中止した。得られたポリマーの特性を評価し表3に示した。
比較例1〜4のポリマーをそれぞれ、比較例6〜9へ供した。比較例1〜4のポリマーを固形分20%の水系樹脂として作製し、カルボキシメチルセルロースを該水系樹脂に対して1wt%追加し、粘度を25dPa・s(リオン株式会社製ビスコテスターVT−04Fで測定)に調整した。また、総繊度が400dtex、108フィラメントのポリアミド66繊維を平織りにてウオータージェットルームにて製織後、沸水にて収縮加工し、110℃で乾燥仕上げをし、経密度58本/2.54cm、緯密度56本/2.54cmの織物を得た。この織物に該水系樹脂をナイフコートにて塗布し、乾燥後の樹脂量を4g/m2にした織物の特性を評価し表4に示した。
Claims (10)
- 共重合ポリエーテルポリアミド樹脂の伸度が1000%以上で、弾性率が15MPa以下であることを特徴とする織編物へのコーティングもしくは含浸用共重合ポリエーテルポリアミド樹脂。
- 前記共重合ポリエーテルポリアミド樹脂が、下記(化式1)で表されるポリエーテルジアミン化合物と下記(化式2)で表されるジカルボン酸化合物とから構成されたポリエーテルポリアミドからなるソフトセグメント及び、下記(化式3)で表されるアミノカルボン酸化合物及び/又は下記(化式4)で表されるラクタム化合物から構成されたポリアミドからなるハードセグメントが結合されてなることを特徴とする請求項1に記載の織編物へのコーティングもしくは含浸用共重合ポリエーテルポリアミド樹脂。
[但し、R2は、炭化水素鎖を含む連結基を表わす]
- 前記(化式2)のジカルボン酸化合物が脂肪族ジカルボン酸もしくは脂環族ジカルボン酸である請求項2または3に記載の織編物へのコーティングもしくは含浸用共重合ポリエーテルポリアミド樹脂。
- 前記(化式2)のR1が炭素原子数1〜20のアルキレン基を表わす請求項2〜4のいずれかに記載の織編物へのコーティングもしくは含浸用共重合ポリエーテルポリアミド樹脂。
- 前記(化式3)のR2が炭素原子数2〜20のアルキレン基を表わす請求項2〜5のいずれかに記載の織編物へのコーティングもしくは含浸用共重合ポリエーテルポリアミド樹脂。
- 前記(化式4)のR3が炭素原子数3〜20のアルキレン基を表わす請求項2〜6のいずれかに記載の織編物へのコーティングもしくは含浸用共重合ポリエーテルポリアミド樹脂。
- 請求項1〜7のいずれかに記載の織編物へのコーティングもしくは含浸用共重合ポリエーテルポリアミド樹脂をコーティング剤として用いたエアバッグ用基布。
- 請求項1〜7のいずれかに記載の織編物へのコーティングもしくは含浸用共重合ポリエーテルポリアミド樹脂をシール剤として用いたエアバッグ。
- 請求項1〜7のいずれかに記載の織編物へのコーティングもしくは含浸用共重合ポリエーテルポリアミド樹脂を接着剤として用いたエアバッグ。
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EP (1) | EP2284311B1 (ja) |
JP (1) | JP5440497B2 (ja) |
CN (1) | CN101965422B (ja) |
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JP5435328B2 (ja) * | 2007-12-07 | 2014-03-05 | 東洋紡株式会社 | エアバッグ用織物 |
KR101492303B1 (ko) * | 2007-12-07 | 2015-02-11 | 도요보 가부시키가이샤 | 에어백용 포백 |
US8541321B2 (en) | 2008-05-15 | 2013-09-24 | Toyo Boseki Kabushiki Kaisha | Copolymerized polyether polyamide resin |
EP2169110B1 (de) * | 2008-09-25 | 2013-06-05 | Trevira Gmbh | Flammhemmende Hohlfaser mit silikonfreier Weichgriffausrüstung umfassend einen Polyether und ein Fettsäurecondensationsprodukt |
JP5177085B2 (ja) * | 2009-06-10 | 2013-04-03 | 東洋紡株式会社 | エアバッグ用織物 |
CN101735451B (zh) * | 2009-12-11 | 2012-09-19 | 东华大学 | 一种聚酰胺热塑性弹性体的生产方法 |
JPWO2013047652A1 (ja) * | 2011-09-28 | 2015-03-26 | 豊田合成株式会社 | エアバッグ基布用塗料及びエアバッグ基布 |
JP6164086B2 (ja) * | 2012-03-06 | 2017-07-19 | 東洋紡株式会社 | 共重合ポリエーテルポリアミド樹脂組成物 |
US20130281589A1 (en) * | 2012-04-23 | 2013-10-24 | E I Du Pont De Nemours And Company | Thermoplastic polyamide composition |
WO2014027651A1 (ja) * | 2012-08-14 | 2014-02-20 | 三菱瓦斯化学株式会社 | ポリエーテルポリアミド組成物 |
CN105026639B (zh) | 2013-03-19 | 2018-04-20 | 东洋纺株式会社 | 安全气囊用织物 |
WO2016181471A1 (ja) * | 2015-05-11 | 2016-11-17 | 株式会社カネカ | ポリアミドエラストマー、医療機器及びポリアミドエラストマーの製造方法 |
WO2016181472A1 (ja) * | 2015-05-11 | 2016-11-17 | 株式会社カネカ | ポリアミドエラストマー、医療機器及びポリアミドエラストマーの製造方法 |
WO2017146018A1 (ja) * | 2016-02-23 | 2017-08-31 | 宇部興産株式会社 | ポリアミドエラストマー組成物並びにこれよりなる繊維及び成形体 |
CN107915839A (zh) * | 2016-10-11 | 2018-04-17 | 东丽先端材料研究开发(中国)有限公司 | 一种聚酰胺及其制备方法 |
US11326024B2 (en) | 2016-11-10 | 2022-05-10 | Kaneka Corporation | Polyamide resin, molded body, laminate, medical device, and polyamide resin production method |
WO2018088497A1 (ja) * | 2016-11-10 | 2018-05-17 | 株式会社カネカ | ポリアミド系樹脂、成形体、積層体、医療機器、及びポリアミド系樹脂の製造方法 |
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JP5435328B2 (ja) | 2007-12-07 | 2014-03-05 | 東洋紡株式会社 | エアバッグ用織物 |
US8541321B2 (en) | 2008-05-15 | 2013-09-24 | Toyo Boseki Kabushiki Kaisha | Copolymerized polyether polyamide resin |
-
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- 2008-10-16 JP JP2010511855A patent/JP5440497B2/ja active Active
- 2008-10-16 EP EP20080874278 patent/EP2284311B1/en active Active
- 2008-10-16 CN CN2008801278905A patent/CN101965422B/zh not_active Expired - Fee Related
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JP5440497B2 (ja) | 2014-03-12 |
CN101965422B (zh) | 2013-04-10 |
US20110014833A1 (en) | 2011-01-20 |
EP2284311B1 (en) | 2014-01-08 |
US8541321B2 (en) | 2013-09-24 |
CN101965422A (zh) | 2011-02-02 |
EP2284311A4 (en) | 2012-04-11 |
EP2284311A1 (en) | 2011-02-16 |
WO2009139087A1 (ja) | 2009-11-19 |
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