JPWO2021065094A1 - ポリブチレンテレフタレート樹脂組成物 - Google Patents
ポリブチレンテレフタレート樹脂組成物 Download PDFInfo
- Publication number
- JPWO2021065094A1 JPWO2021065094A1 JP2020553683A JP2020553683A JPWO2021065094A1 JP WO2021065094 A1 JPWO2021065094 A1 JP WO2021065094A1 JP 2020553683 A JP2020553683 A JP 2020553683A JP 2020553683 A JP2020553683 A JP 2020553683A JP WO2021065094 A1 JPWO2021065094 A1 JP WO2021065094A1
- Authority
- JP
- Japan
- Prior art keywords
- polybutylene terephthalate
- terephthalate resin
- amount
- carbodiimide
- resin composition
- 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
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- -1 Polybutylene terephthalate Polymers 0.000 title claims abstract description 176
- 229920001707 polybutylene terephthalate Polymers 0.000 title claims abstract description 105
- 239000011342 resin composition Substances 0.000 title claims abstract description 50
- 239000011347 resin Substances 0.000 claims abstract description 77
- 229920005989 resin Polymers 0.000 claims abstract description 77
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims abstract description 41
- 150000001875 compounds Chemical class 0.000 claims abstract description 35
- 150000001718 carbodiimides Chemical class 0.000 claims abstract description 27
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 34
- 238000012360 testing method Methods 0.000 claims description 9
- 230000014759 maintenance of location Effects 0.000 claims description 8
- 239000000155 melt Substances 0.000 claims description 7
- 230000001351 cycling effect Effects 0.000 claims description 4
- 125000000524 functional group Chemical group 0.000 claims description 2
- 230000007062 hydrolysis Effects 0.000 abstract description 19
- 238000006460 hydrolysis reaction Methods 0.000 abstract description 19
- 239000002253 acid Substances 0.000 description 16
- LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 14
- 235000014113 dietary fatty acids Nutrition 0.000 description 13
- 239000000194 fatty acid Substances 0.000 description 13
- 229930195729 fatty acid Natural products 0.000 description 13
- 238000005809 transesterification reaction Methods 0.000 description 13
- IISBACLAFKSPIT-UHFFFAOYSA-N Bisphenol A Natural products C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 12
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerol Natural products OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 12
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 11
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 10
- 125000002947 alkylene group Chemical group 0.000 description 10
- 239000000178 monomer Substances 0.000 description 10
- 235000011187 glycerol Nutrition 0.000 description 9
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
- 238000006243 chemical reaction Methods 0.000 description 8
- 150000002009 diols Chemical class 0.000 description 8
- 238000004898 kneading Methods 0.000 description 8
- 238000000034 method Methods 0.000 description 8
- 239000012763 reinforcing filler Substances 0.000 description 8
- 229930185605 Bisphenol Natural products 0.000 description 7
- 229920001634 Copolyester Polymers 0.000 description 7
- 125000004432 carbon atom Chemical group C* 0.000 description 7
- 230000000694 effects Effects 0.000 description 7
- VPWNQTHUCYMVMZ-UHFFFAOYSA-N 4,4'-sulfonyldiphenol Chemical class C1=CC(O)=CC=C1S(=O)(=O)C1=CC=C(O)C=C1 VPWNQTHUCYMVMZ-UHFFFAOYSA-N 0.000 description 6
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 6
- PXKLMJQFEQBVLD-UHFFFAOYSA-N bisphenol F Chemical compound C1=CC(O)=CC=C1CC1=CC=C(O)C=C1 PXKLMJQFEQBVLD-UHFFFAOYSA-N 0.000 description 6
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 6
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 6
- POULHZVOKOAJMA-UHFFFAOYSA-N dodecanoic acid Chemical compound CCCCCCCCCCCC(O)=O POULHZVOKOAJMA-UHFFFAOYSA-N 0.000 description 6
- 150000004665 fatty acids Chemical class 0.000 description 6
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 6
- 238000000465 moulding Methods 0.000 description 6
- ULQISTXYYBZJSJ-UHFFFAOYSA-N 12-hydroxyoctadecanoic acid Chemical compound CCCCCCC(O)CCCCCCCCCCC(O)=O ULQISTXYYBZJSJ-UHFFFAOYSA-N 0.000 description 5
- 239000004594 Masterbatch (MB) Substances 0.000 description 5
- 238000012644 addition polymerization Methods 0.000 description 5
- 229920001577 copolymer Polymers 0.000 description 5
- 229940105990 diglycerin Drugs 0.000 description 5
- GPLRAVKSCUXZTP-UHFFFAOYSA-N diglycerol Chemical compound OCC(O)COCC(O)CO GPLRAVKSCUXZTP-UHFFFAOYSA-N 0.000 description 5
- 150000002148 esters Chemical class 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- 239000008188 pellet Substances 0.000 description 5
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 4
- 235000021355 Stearic acid Nutrition 0.000 description 4
- 150000007513 acids Chemical class 0.000 description 4
- ADCOVFLJGNWWNZ-UHFFFAOYSA-N antimony trioxide Chemical compound O=[Sb]O[Sb]=O ADCOVFLJGNWWNZ-UHFFFAOYSA-N 0.000 description 4
- 239000007809 chemical reaction catalyst Substances 0.000 description 4
- 150000001991 dicarboxylic acids Chemical class 0.000 description 4
- UKMSUNONTOPOIO-UHFFFAOYSA-N docosanoic acid Chemical compound CCCCCCCCCCCCCCCCCCCCCC(O)=O UKMSUNONTOPOIO-UHFFFAOYSA-N 0.000 description 4
- QQVIHTHCMHWDBS-UHFFFAOYSA-N isophthalic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 description 4
- 238000002156 mixing Methods 0.000 description 4
- BDJRBEYXGGNYIS-UHFFFAOYSA-N nonanedioic acid Chemical compound OC(=O)CCCCCCCC(O)=O BDJRBEYXGGNYIS-UHFFFAOYSA-N 0.000 description 4
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 4
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 4
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 4
- 238000006116 polymerization reaction Methods 0.000 description 4
- YPFDHNVEDLHUCE-UHFFFAOYSA-N propane-1,3-diol Chemical compound OCCCO YPFDHNVEDLHUCE-UHFFFAOYSA-N 0.000 description 4
- CXMXRPHRNRROMY-UHFFFAOYSA-N sebacic acid Chemical compound OC(=O)CCCCCCCCC(O)=O CXMXRPHRNRROMY-UHFFFAOYSA-N 0.000 description 4
- 239000008117 stearic acid Substances 0.000 description 4
- TYFQFVWCELRYAO-UHFFFAOYSA-N suberic acid Chemical compound OC(=O)CCCCCCC(O)=O TYFQFVWCELRYAO-UHFFFAOYSA-N 0.000 description 4
- BDNKZNFMNDZQMI-UHFFFAOYSA-N 1,3-diisopropylcarbodiimide Chemical compound CC(C)N=C=NC(C)C BDNKZNFMNDZQMI-UHFFFAOYSA-N 0.000 description 3
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 3
- 239000005639 Lauric acid Substances 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000003963 antioxidant agent Substances 0.000 description 3
- 125000003118 aryl group Chemical group 0.000 description 3
- BGRWYRAHAFMIBJ-UHFFFAOYSA-N diisopropylcarbodiimide Natural products CC(C)NC(=O)NC(C)C BGRWYRAHAFMIBJ-UHFFFAOYSA-N 0.000 description 3
- 238000011156 evaluation Methods 0.000 description 3
- 150000002596 lactones Chemical class 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- 229910052698 phosphorus Inorganic materials 0.000 description 3
- 239000011574 phosphorus Substances 0.000 description 3
- 150000003609 titanium compounds Chemical class 0.000 description 3
- 238000011282 treatment Methods 0.000 description 3
- DCTMXCOHGKSXIZ-UHFFFAOYSA-N (R)-1,3-Octanediol Chemical compound CCCCCC(O)CCO DCTMXCOHGKSXIZ-UHFFFAOYSA-N 0.000 description 2
- 229940114072 12-hydroxystearic acid Drugs 0.000 description 2
- WSQZNZLOZXSBHA-UHFFFAOYSA-N 3,8-dioxabicyclo[8.2.2]tetradeca-1(12),10,13-triene-2,9-dione Chemical compound O=C1OCCCCOC(=O)C2=CC=C1C=C2 WSQZNZLOZXSBHA-UHFFFAOYSA-N 0.000 description 2
- YEJRWHAVMIAJKC-UHFFFAOYSA-N 4-Butyrolactone Chemical compound O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 description 2
- OZJPLYNZGCXSJM-UHFFFAOYSA-N 5-valerolactone Chemical compound O=C1CCCCO1 OZJPLYNZGCXSJM-UHFFFAOYSA-N 0.000 description 2
- 235000021357 Behenic acid Nutrition 0.000 description 2
- NIQCNGHVCWTJSM-UHFFFAOYSA-N Dimethyl phthalate Chemical compound COC(=O)C1=CC=CC=C1C(=O)OC NIQCNGHVCWTJSM-UHFFFAOYSA-N 0.000 description 2
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 2
- AEMRFAOFKBGASW-UHFFFAOYSA-N Glycolic acid Chemical compound OCC(O)=O AEMRFAOFKBGASW-UHFFFAOYSA-N 0.000 description 2
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 2
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 2
- YIMQCDZDWXUDCA-UHFFFAOYSA-N [4-(hydroxymethyl)cyclohexyl]methanol Chemical compound OCC1CCC(CO)CC1 YIMQCDZDWXUDCA-UHFFFAOYSA-N 0.000 description 2
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 2
- 125000002723 alicyclic group Chemical group 0.000 description 2
- 150000001335 aliphatic alkanes Chemical class 0.000 description 2
- 125000001931 aliphatic group Chemical group 0.000 description 2
- 125000005907 alkyl ester group Chemical group 0.000 description 2
- 150000001463 antimony compounds Chemical class 0.000 description 2
- 230000003078 antioxidant effect Effects 0.000 description 2
- 239000012298 atmosphere Substances 0.000 description 2
- 229940116226 behenic acid Drugs 0.000 description 2
- 230000036760 body temperature Effects 0.000 description 2
- YHWCPXVTRSHPNY-UHFFFAOYSA-N butan-1-olate;titanium(4+) Chemical compound [Ti+4].CCCC[O-].CCCC[O-].CCCC[O-].CCCC[O-] YHWCPXVTRSHPNY-UHFFFAOYSA-N 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- VNGOYPQMJFJDLV-UHFFFAOYSA-N dimethyl benzene-1,3-dicarboxylate Chemical compound COC(=O)C1=CC=CC(C(=O)OC)=C1 VNGOYPQMJFJDLV-UHFFFAOYSA-N 0.000 description 2
- 229920006351 engineering plastic Polymers 0.000 description 2
- 230000007613 environmental effect Effects 0.000 description 2
- 238000001125 extrusion Methods 0.000 description 2
- IPCSVZSSVZVIGE-UHFFFAOYSA-N hexadecanoic acid Chemical compound CCCCCCCCCCCCCCCC(O)=O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 description 2
- ACCCMOQWYVYDOT-UHFFFAOYSA-N hexane-1,1-diol Chemical compound CCCCCC(O)O ACCCMOQWYVYDOT-UHFFFAOYSA-N 0.000 description 2
- 125000005027 hydroxyaryl group Chemical group 0.000 description 2
- 230000001771 impaired effect Effects 0.000 description 2
- 239000000314 lubricant Substances 0.000 description 2
- IWYDHOAUDWTVEP-UHFFFAOYSA-N mandelic acid Chemical compound OC(=O)C(O)C1=CC=CC=C1 IWYDHOAUDWTVEP-UHFFFAOYSA-N 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- UTOPWMOLSKOLTQ-UHFFFAOYSA-N octacosanoic acid Chemical compound CCCCCCCCCCCCCCCCCCCCCCCCCCCC(O)=O UTOPWMOLSKOLTQ-UHFFFAOYSA-N 0.000 description 2
- OEIJHBUUFURJLI-UHFFFAOYSA-N octane-1,8-diol Chemical compound OCCCCCCCCO OEIJHBUUFURJLI-UHFFFAOYSA-N 0.000 description 2
- 150000003018 phosphorus compounds Chemical class 0.000 description 2
- 229910000073 phosphorus hydride Inorganic materials 0.000 description 2
- 230000000704 physical effect Effects 0.000 description 2
- CYIDZMCFTVVTJO-UHFFFAOYSA-N pyromellitic acid Chemical compound OC(=O)C1=CC(C(O)=O)=C(C(O)=O)C=C1C(O)=O CYIDZMCFTVVTJO-UHFFFAOYSA-N 0.000 description 2
- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 description 2
- 239000012321 sodium triacetoxyborohydride Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 238000005979 thermal decomposition reaction Methods 0.000 description 2
- 150000003606 tin compounds Chemical class 0.000 description 2
- VXUYXOFXAQZZMF-UHFFFAOYSA-N titanium(IV) isopropoxide Chemical compound CC(C)O[Ti](OC(C)C)(OC(C)C)OC(C)C VXUYXOFXAQZZMF-UHFFFAOYSA-N 0.000 description 2
- PWBHRVGYSMBMIO-UHFFFAOYSA-M tributylstannanylium;acetate Chemical compound CCCC[Sn](CCCC)(CCCC)OC(C)=O PWBHRVGYSMBMIO-UHFFFAOYSA-M 0.000 description 2
- ARCGXLSVLAOJQL-UHFFFAOYSA-N trimellitic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C(C(O)=O)=C1 ARCGXLSVLAOJQL-UHFFFAOYSA-N 0.000 description 2
- 229940088594 vitamin Drugs 0.000 description 2
- 229930003231 vitamin Natural products 0.000 description 2
- PAPBSGBWRJIAAV-UHFFFAOYSA-N ε-Caprolactone Chemical compound O=C1CCCCCO1 PAPBSGBWRJIAAV-UHFFFAOYSA-N 0.000 description 2
- SFUVLEGIZGPPNN-UHFFFAOYSA-N (2-pyridin-2-ylacetyl) 2-pyridin-2-ylacetate Chemical compound C=1C=CC=NC=1CC(=O)OC(=O)CC1=CC=CC=N1 SFUVLEGIZGPPNN-UHFFFAOYSA-N 0.000 description 1
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 1
- HCNHNBLSNVSJTJ-UHFFFAOYSA-N 1,1-Bis(4-hydroxyphenyl)ethane Chemical compound C=1C=C(O)C=CC=1C(C)C1=CC=C(O)C=C1 HCNHNBLSNVSJTJ-UHFFFAOYSA-N 0.000 description 1
- YKPAABNCNAGAAJ-UHFFFAOYSA-N 1,1-Bis(4-hydroxyphenyl)propane Chemical compound C=1C=C(O)C=CC=1C(CC)C1=CC=C(O)C=C1 YKPAABNCNAGAAJ-UHFFFAOYSA-N 0.000 description 1
- BOSWPVRACYJBSJ-UHFFFAOYSA-N 1,3-di(p-tolyl)carbodiimide Chemical compound C1=CC(C)=CC=C1N=C=NC1=CC=C(C)C=C1 BOSWPVRACYJBSJ-UHFFFAOYSA-N 0.000 description 1
- PXGZQGDTEZPERC-UHFFFAOYSA-N 1,4-cyclohexanedicarboxylic acid Chemical compound OC(=O)C1CCC(C(O)=O)CC1 PXGZQGDTEZPERC-UHFFFAOYSA-N 0.000 description 1
- RTBFRGCFXZNCOE-UHFFFAOYSA-N 1-methylsulfonylpiperidin-4-one Chemical compound CS(=O)(=O)N1CCC(=O)CC1 RTBFRGCFXZNCOE-UHFFFAOYSA-N 0.000 description 1
- VBICKXHEKHSIBG-UHFFFAOYSA-N 1-monostearoylglycerol Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCC(O)CO VBICKXHEKHSIBG-UHFFFAOYSA-N 0.000 description 1
- FUWVMBCPMRAWPG-UHFFFAOYSA-N 2,3-dihydroxypropyl 2-hydroxyoctadecanoate Chemical compound CCCCCCCCCCCCCCCCC(O)C(=O)OCC(O)CO FUWVMBCPMRAWPG-UHFFFAOYSA-N 0.000 description 1
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- 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
- ISPYQTSUDJAMAB-UHFFFAOYSA-N 2-chlorophenol Chemical compound OC1=CC=CC=C1Cl ISPYQTSUDJAMAB-UHFFFAOYSA-N 0.000 description 1
- WMRCTEPOPAZMMN-UHFFFAOYSA-N 2-undecylpropanedioic acid Chemical compound CCCCCCCCCCCC(C(O)=O)C(O)=O WMRCTEPOPAZMMN-UHFFFAOYSA-N 0.000 description 1
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- DUUKZBGYNMHUHO-UHFFFAOYSA-N 253MC0P0YV Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCC(O)COCC(O)CO DUUKZBGYNMHUHO-UHFFFAOYSA-N 0.000 description 1
- YMTYZTXUZLQUSF-UHFFFAOYSA-N 3,3'-Dimethylbisphenol A Chemical compound C1=C(O)C(C)=CC(C(C)(C)C=2C=C(C)C(O)=CC=2)=C1 YMTYZTXUZLQUSF-UHFFFAOYSA-N 0.000 description 1
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- HTVITOHKHWFJKO-UHFFFAOYSA-N Bisphenol B Chemical compound C=1C=C(O)C=CC=1C(C)(CC)C1=CC=C(O)C=C1 HTVITOHKHWFJKO-UHFFFAOYSA-N 0.000 description 1
- SDDLEVPIDBLVHC-UHFFFAOYSA-N Bisphenol Z Chemical compound C1=CC(O)=CC=C1C1(C=2C=CC(O)=CC=2)CCCCC1 SDDLEVPIDBLVHC-UHFFFAOYSA-N 0.000 description 1
- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 1
- VJLRMYYGLIZWKL-UHFFFAOYSA-N N(=C=O)C=1C(=C(C(=CC=1C(C)C)C(C)C)NN=C=N)C(C)C Chemical compound N(=C=O)C=1C(=C(C(=CC=1C(C)C)C(C)C)NN=C=N)C(C)C VJLRMYYGLIZWKL-UHFFFAOYSA-N 0.000 description 1
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Classifications
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/16—Nitrogen-containing compounds
- C08K5/29—Compounds containing one or more carbon-to-nitrogen double bonds
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- 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
- C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
- C08G63/02—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds
- C08G63/12—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds derived from polycarboxylic acids and polyhydroxy compounds
- C08G63/16—Dicarboxylic acids and dihydroxy compounds
- C08G63/18—Dicarboxylic acids and dihydroxy compounds the acids or hydroxy compounds containing carbocyclic rings
- C08G63/181—Acids containing aromatic rings
- C08G63/183—Terephthalic acids
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/04—Oxygen-containing compounds
- C08K5/09—Carboxylic acids; Metal salts thereof; Anhydrides thereof
- C08K5/098—Metal salts of carboxylic acids
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/04—Oxygen-containing compounds
- C08K5/10—Esters; Ether-esters
- C08K5/101—Esters; Ether-esters of monocarboxylic acids
- C08K5/103—Esters; Ether-esters of monocarboxylic acids with polyalcohols
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/04—Oxygen-containing compounds
- C08K5/13—Phenols; Phenolates
- C08K5/134—Phenols containing ester groups
- C08K5/1345—Carboxylic esters of phenolcarboxylic acids
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- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Compositions Of Macromolecular Compounds (AREA)
Abstract
本発明の目的は、少なくとも、(A)末端カルボキシル基量が1〜9meq/kg以下のポリブチレンテレフタレート樹脂と、(B)カルボジイミド化合物とを含有するポリブチレンテレフタレート樹脂組成物であって、該カルボジイミド化合物のカルボジイミド官能基量が該末端カルボキシル基量に対して4〜40当量であり、且つ該カルボジイミド化合物のカルボジイミド官能基量から該ポリブチレンテレフタレート樹脂の末端カルボキシル基量を減じた値が25meq/kg以上であるポリブチレンテレフタレート樹脂組成物、によって達成された。
Description
2. USCAR−2(5.6.2 Temperature/Humidity Cycling)Class5に準拠した冷熱サイクル試験においてTS保持率が80%以上である前記1記載の樹脂組成物。
3. ISO 11443により260℃で測定された溶融粘度が0.3kPa・s以下である前記1または2に記載の樹脂組成物。
4. (C)多価水酸基含有化合物を含有する前記1〜3の何れかに記載のポリブチレンテレフタレート樹脂組成物。
本発明のポリブチレンテレフタレート樹脂組成物は、少なくとも、(A)末端カルボキシル基量が1〜9meq/kgのポリブチレンテレフタレート樹脂と、(B)カルボジイミド化合物とを含有するポリブチレンテレフタレート樹脂組成物であって、該カルボジイミド化合物のカルボジイミド官能基量が該末端カルボキシル基量1当量に対して4〜40当量であることを特徴とする。
本発明の(A)ポリブチレンテレフタレート樹脂とは、テレフタル酸(テレフタル酸又はそのエステル形成誘導体)と、炭素数4のアルキレングリコール(1,4−ブタンジオール)又はそのエステル形成誘導体とを、少なくとも重合成分とする熱可塑性樹脂である。そして(A)ポリブチレンテレフタレート樹脂は、末端カルボキシル基量が1〜9meq/kgである。
本発明で用いられる(B)カルボジイミド化合物とは、分子中にカルボジイミド基(−N=C=N−)を有する化合物である。カルボジイミド化合物としては、主鎖が脂肪族の脂肪族カルボジイミド化合物、主鎖が脂環族の脂環族カルボジイミド化合物、主鎖が芳香族の芳香族カルボジイミド化合物のいずれも使用できるが、耐加水分解性の点で芳香族カルボジイミド化合物の使用が好ましい。
本発明においては、(C)多価水酸基含有化合物を添加することも好ましい。
(C)多価水酸基含有化合物は、一分子中に水酸基を2個以上有する化合物である。また、(C)多価水酸基含有化合物は、水酸基価が200〜1000であることが好ましい。
本発明の樹脂組成物には、本発明の効果を害さない範囲で、他の樹脂や強化用充填材、難燃剤、酸化防止剤、耐熱安定剤、紫外線吸収剤、帯電防止剤、染料や顔料等の着色剤、潤滑剤、可塑剤、結晶核剤等の従来公知の添加剤を含有させることができる。本発明においては、他の成分として、エステル交換反応触媒、エステル交換反応停止剤を含有させることが好ましい場合がある。
本発明のポリブチレンテレフタレート樹脂組成物からなる成形品は、USCAR−2(5.6.2 Temperature/Humidity Cycling)Class5に準拠した冷熱サイクル試験において、引張強さ保持率が80%以上であり、かつISO 11443により260℃で測定された溶融粘度が0.3kPa・s以下であることを特徴とする。
本発明のポリブチレンテレフタレート樹脂組成物は、そのClass5の温度環境でも十分に使用することができるレベルであることを示している。
本発明のポリブチレンテレフタレート樹脂組成物の調製法は特に限定されるものではなく、一般に樹脂組成物の調製法として公知の設備と方法を用いることができる。例えば、必要な成分を混合し、1軸又は2軸の押出機又はその他の溶融混練装置を使用して混練し、成形用ペレットとして調製することができる。
表1、2に記載の化合物は下記の通りである。
(A)ポリブチレンテレフタレート樹脂
A−1:ポリブチレンテレフタレート樹脂(固有粘度=1.14dL/g、末端カルボキシル基量=4meq/kg、ポリプラスチックス株式会社製)
A−2:ポリブチレンテレフタレート樹脂(固有粘度=1.14dL/g、末端カルボキシル基量=9meq/kg、ポリプラスチックス株式会社製)
A−3:ポリブチレンテレフタレート樹脂(固有粘度=0.95dL/g、末端カルボキシル基量=9meq/kg、ポリプラスチックス株式会社製)
A−4:ポリブチレンテレフタレート樹脂(固有粘度=1.14dL/g、末端カルボキシル基量=10meq/kg、ポリプラスチックス株式会社製)
A−5:ポリブチレンテレフタレート樹脂(固有粘度=0.83dL/g、末端カルボキシル基量=13meq/kg、ポリプラスチックス株式会社製)
B−1:スタバクゾールP100 カルボジイミド当量3625meq/kg(ランクセス株式会社製)
C−1:ヒドロキシステアリン酸グリセリル(水酸基価480、理研ビタミン株式会社製、「リケマールHC100」)
なお(C)多価水酸基含有化合物の水酸基価については、日本油化学会2.3.6.2−1996 ヒドロキシル価(ピリジン−無水酢酸法)により測定した。
フェノール系酸化防止剤:イルガノックス1010(BASF社製)
リン酸系酸化防止剤:アデカスタブPEP−36(アデカ社製)
硫黄系酸化防止剤:アデカスタブAO−412S(アデカ社製)滑剤:リケマールB74(理研ビタミン社製)
(A)ポリブチレンテレフタレート樹脂、(B)カルボジイミド化合物、その他の成分を、表1に示す配合組成で秤量後ドライブレンドし、二軸押出機(株式会社日本製鋼所製TEX−30)にて、表1に記載の押出混錬時の樹脂温度(℃)、スクリュー回転数を130rpm、押出量を12kg/hとして、溶融混練を行い、吐出されたストランド状の溶融樹脂を冷却し、ペレタイザーによりカッティングすることにより、樹脂組成物のペレット状サンプルを得た。次いで、このペレットを用いて以下の各種評価を行った。
末端カルボキシル基量は、本発明の樹脂組成物ペレットの粉砕試料をベンジルアルコール中215℃で10分間溶解後、0.01Nの水酸化ナトリウム水溶液にて滴定することにより求めた。この末端カルボキシル基量に対する測定結果と、混合するカルボジイミド官能基量の当量比を表1、2に示す。
カルボジイミド官能基量と末端カルボキシル基量との当量比=
カルボジイミド官能基量/末端カルボキシル基量
カルボジイミド化合物のカルボジイミド官能基量からポリブチレンテレフタレート樹脂の末端カルボキシル基量を減じた値は、ポリブチレンテレフタレート樹脂1kg当たりに混合するカルボジイミド官能基量からポリブチレンテレフタレート樹脂1kgに含まれる末端カルボキシル基量を減じた値として、次式により求めた。値を表1、2に示す。
カルボジイミド官能基量から末端カルボキシル基を減じた値(meq/PBT・kg)=ポリブチレンテレフタレート樹脂1kg当たりに混合するカルボジイミド官能基量−ポリブチレンテレフタレート樹脂1kgに含まれる末端カルボキシル基量
本発明の樹脂組成物のペレットを140℃で3時間乾燥後、ISO11443に準拠し、キャピログラフ1B(東洋精機製作所社製)を用いて、炉体温度260℃、キャピラリーφ1mm×20mmL、剪断速度1000sec−1にて測定した。単位はkPa・sである。結果を表1、2に示す。
本発明の樹脂組成物のペレットを140℃で3時間乾燥後、樹脂温度260℃、金型温度80℃、射出時間15秒、冷却時間15秒で、ISO3167引張り試験片を射出成形し、その試料をUSCAR−2(5.6.2 Temperature/Humidity Cycling)Class5に準拠し、1サイクルが−40℃(0.5時間)→85℃、85%RH(4時間)→175℃(1.5時間)である環境試験条件を40サイクル繰返し、冷熱サイクル試験した前後でISO527−1,2に準拠し引張り強さを測定した。結果を表1、2に示す。
引張強さ保持率(単位:%)=(処理後の引張強さ/処理前の引張強さ)×100
Claims (4)
- 少なくとも、(A)末端カルボキシル基量が1〜9meq/kg以下のポリブチレンテレフタレート樹脂(PBT)と、(B)カルボジイミド化合物とを含有するポリブチレンテレフタレート樹脂組成物であって、該カルボジイミド化合物のカルボジイミド官能基量が該ポリブチレンテレフタレート樹脂の末端カルボキシル基量1当量に対して4〜40当量であり、且つ該カルボジイミド化合物のカルボジイミド官能基量から該ポリブチレンテレフタレート樹脂の末端カルボキシル基量を減じた値が25meq/PBT・kg以上であるポリブチレンテレフタレート樹脂組成物。
- USCAR−2(5.6.2 Temperature/Humidity Cycling)Class5に準拠した冷熱サイクル試験においてTS保持率が80%以上である請求項1記載の樹脂組成物。
- ISO11443により260℃で測定された溶融粘度が0.3kPa・s以下である請求項1または2に記載の樹脂組成物。
- (C)多価水酸基含有化合物を含有する請求項1〜3の何れか1項に記載のポリブチレンテレフタレート樹脂組成物。
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