JP4697859B2 - 樹脂用可塑剤および樹脂組成物 - Google Patents
樹脂用可塑剤および樹脂組成物 Download PDFInfo
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- JP4697859B2 JP4697859B2 JP2005065081A JP2005065081A JP4697859B2 JP 4697859 B2 JP4697859 B2 JP 4697859B2 JP 2005065081 A JP2005065081 A JP 2005065081A JP 2005065081 A JP2005065081 A JP 2005065081A JP 4697859 B2 JP4697859 B2 JP 4697859B2
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- Prior art keywords
- acid
- plasticizer
- resin
- glycol
- polyester resin
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- 239000004014 plasticizer Substances 0.000 title claims description 44
- 229920005989 resin Polymers 0.000 title claims description 40
- 239000011347 resin Substances 0.000 title claims description 40
- 239000011342 resin composition Substances 0.000 title claims description 22
- LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 46
- -1 alkylene glycol monoalkyl ether Chemical class 0.000 claims description 31
- 125000004432 carbon atom Chemical group C* 0.000 claims description 22
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 claims description 17
- 229920001223 polyethylene glycol Polymers 0.000 claims description 17
- 238000006243 chemical reaction Methods 0.000 claims description 16
- 229920000747 poly(lactic acid) Polymers 0.000 claims description 16
- 239000004626 polylactic acid Substances 0.000 claims description 16
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims description 14
- 229920001225 polyester resin Polymers 0.000 claims description 14
- 239000004645 polyester resin Substances 0.000 claims description 14
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 claims description 12
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 claims description 11
- 125000002947 alkylene group Chemical group 0.000 claims description 9
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 claims description 9
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 claims description 9
- 239000000203 mixture Substances 0.000 claims description 9
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 claims description 8
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 8
- 125000000217 alkyl group Chemical group 0.000 claims description 7
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 claims description 6
- 239000001361 adipic acid Substances 0.000 claims description 6
- 235000011037 adipic acid Nutrition 0.000 claims description 6
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 claims description 6
- 125000004450 alkenylene group Chemical group 0.000 claims description 4
- 150000001875 compounds Chemical class 0.000 claims description 4
- 239000001530 fumaric acid Substances 0.000 claims description 3
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 claims description 3
- 239000011976 maleic acid Substances 0.000 claims description 3
- 150000008065 acid anhydrides Chemical class 0.000 claims description 2
- BMRWNKZVCUKKSR-UHFFFAOYSA-N butane-1,2-diol Chemical compound CCC(O)CO BMRWNKZVCUKKSR-UHFFFAOYSA-N 0.000 claims description 2
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 67
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 41
- 238000005886 esterification reaction Methods 0.000 description 25
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 20
- 239000007795 chemical reaction product Substances 0.000 description 19
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 16
- 238000012360 testing method Methods 0.000 description 16
- 239000002202 Polyethylene glycol Substances 0.000 description 15
- 229940028356 diethylene glycol monobutyl ether Drugs 0.000 description 13
- JCGNDDUYTRNOFT-UHFFFAOYSA-N oxolane-2,4-dione Chemical compound O=C1COC(=O)C1 JCGNDDUYTRNOFT-UHFFFAOYSA-N 0.000 description 13
- 238000000034 method Methods 0.000 description 12
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 10
- 239000003513 alkali Substances 0.000 description 10
- 238000011156 evaluation Methods 0.000 description 10
- 238000004042 decolorization Methods 0.000 description 8
- DNIAPMSPPWPWGF-UHFFFAOYSA-N monopropylene glycol Natural products CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 8
- 238000000746 purification Methods 0.000 description 8
- 230000000740 bleeding effect Effects 0.000 description 7
- 238000006116 polymerization reaction Methods 0.000 description 7
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 6
- 230000000052 comparative effect Effects 0.000 description 6
- 229920001577 copolymer Polymers 0.000 description 5
- 238000000465 moulding Methods 0.000 description 5
- 229920003023 plastic Polymers 0.000 description 5
- 239000004033 plastic Substances 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- 238000004898 kneading Methods 0.000 description 4
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 4
- 238000002156 mixing Methods 0.000 description 4
- 229920000642 polymer Polymers 0.000 description 4
- 229920006324 polyoxymethylene Polymers 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- CXMXRPHRNRROMY-UHFFFAOYSA-N sebacic acid Chemical compound OC(=O)CCCCCCCCC(O)=O CXMXRPHRNRROMY-UHFFFAOYSA-N 0.000 description 4
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 4
- 229920002554 vinyl polymer Polymers 0.000 description 4
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 3
- WFSMVVDJSNMRAR-UHFFFAOYSA-N 2-[2-(2-ethoxyethoxy)ethoxy]ethanol Chemical compound CCOCCOCCOCCO WFSMVVDJSNMRAR-UHFFFAOYSA-N 0.000 description 3
- POAOYUHQDCAZBD-UHFFFAOYSA-N 2-butoxyethanol Chemical compound CCCCOCCO POAOYUHQDCAZBD-UHFFFAOYSA-N 0.000 description 3
- 229920000178 Acrylic resin Polymers 0.000 description 3
- 239000004925 Acrylic resin Substances 0.000 description 3
- 229930182556 Polyacetal Natural products 0.000 description 3
- 125000001931 aliphatic group Chemical group 0.000 description 3
- 239000012461 cellulose resin Substances 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 229920001519 homopolymer Polymers 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 description 3
- 229920002961 polybutylene succinate Polymers 0.000 description 3
- 239000004631 polybutylene succinate Substances 0.000 description 3
- UQDJGEHQDNVPGU-UHFFFAOYSA-N serine phosphoethanolamine Chemical compound [NH3+]CCOP([O-])(=O)OCC([NH3+])C([O-])=O UQDJGEHQDNVPGU-UHFFFAOYSA-N 0.000 description 3
- 239000001384 succinic acid Substances 0.000 description 3
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 2
- DURPTKYDGMDSBL-UHFFFAOYSA-N 1-butoxybutane Chemical compound CCCCOCCCC DURPTKYDGMDSBL-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
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 2
- YIWUKEYIRIRTPP-UHFFFAOYSA-N 2-ethylhexan-1-ol Chemical compound CCCCC(CC)CO YIWUKEYIRIRTPP-UHFFFAOYSA-N 0.000 description 2
- WXUAQHNMJWJLTG-UHFFFAOYSA-N 2-methylbutanedioic acid Chemical compound OC(=O)C(C)CC(O)=O WXUAQHNMJWJLTG-UHFFFAOYSA-N 0.000 description 2
- YEJRWHAVMIAJKC-UHFFFAOYSA-N 4-Butyrolactone Chemical compound O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 description 2
- KWSLGOVYXMQPPX-UHFFFAOYSA-N 5-[3-(trifluoromethyl)phenyl]-2h-tetrazole Chemical compound FC(F)(F)C1=CC=CC(C2=NNN=N2)=C1 KWSLGOVYXMQPPX-UHFFFAOYSA-N 0.000 description 2
- OZJPLYNZGCXSJM-UHFFFAOYSA-N 5-valerolactone Chemical compound O=C1CCCCO1 OZJPLYNZGCXSJM-UHFFFAOYSA-N 0.000 description 2
- QZCLKYGREBVARF-UHFFFAOYSA-N Acetyl tributyl citrate Chemical compound CCCCOC(=O)CC(C(=O)OCCCC)(OC(C)=O)CC(=O)OCCCC QZCLKYGREBVARF-UHFFFAOYSA-N 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
- AEMRFAOFKBGASW-UHFFFAOYSA-N Glycolic acid Chemical compound OCC(O)=O AEMRFAOFKBGASW-UHFFFAOYSA-N 0.000 description 2
- 239000004698 Polyethylene Substances 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
- 239000000654 additive Substances 0.000 description 2
- JFCQEDHGNNZCLN-UHFFFAOYSA-N anhydrous glutaric acid Natural products OC(=O)CCCC(O)=O JFCQEDHGNNZCLN-UHFFFAOYSA-N 0.000 description 2
- 239000012298 atmosphere Substances 0.000 description 2
- 229920006167 biodegradable resin Polymers 0.000 description 2
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 238000002425 crystallisation Methods 0.000 description 2
- 230000008025 crystallization Effects 0.000 description 2
- SZXQTJUDPRGNJN-UHFFFAOYSA-N dipropylene glycol Chemical compound OCCCOCCCO SZXQTJUDPRGNJN-UHFFFAOYSA-N 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- JJOJFIHJIRWASH-UHFFFAOYSA-N icosanedioic acid Chemical compound OC(=O)CCCCCCCCCCCCCCCCCCC(O)=O JJOJFIHJIRWASH-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
- 239000004310 lactic acid Substances 0.000 description 2
- 235000014655 lactic acid Nutrition 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- BDJRBEYXGGNYIS-UHFFFAOYSA-N nonanedioic acid Chemical compound OC(=O)CCCCCCCC(O)=O BDJRBEYXGGNYIS-UHFFFAOYSA-N 0.000 description 2
- OEIJHBUUFURJLI-UHFFFAOYSA-N octane-1,8-diol Chemical compound OCCCCCCCCO OEIJHBUUFURJLI-UHFFFAOYSA-N 0.000 description 2
- 230000000704 physical effect Effects 0.000 description 2
- WLJVNTCWHIRURA-UHFFFAOYSA-N pimelic acid Chemical compound OC(=O)CCCCCC(O)=O WLJVNTCWHIRURA-UHFFFAOYSA-N 0.000 description 2
- 239000013502 plastic waste Substances 0.000 description 2
- 229920006122 polyamide resin Polymers 0.000 description 2
- 229920009537 polybutylene succinate adipate Polymers 0.000 description 2
- 229920001610 polycaprolactone Polymers 0.000 description 2
- 239000004632 polycaprolactone Substances 0.000 description 2
- 229920000728 polyester Polymers 0.000 description 2
- 229920000573 polyethylene Polymers 0.000 description 2
- 229920005672 polyolefin resin Polymers 0.000 description 2
- 229920001451 polypropylene glycol Polymers 0.000 description 2
- 229920000915 polyvinyl chloride Polymers 0.000 description 2
- 239000004800 polyvinyl chloride Substances 0.000 description 2
- 229910001379 sodium hypophosphite Inorganic materials 0.000 description 2
- TYFQFVWCELRYAO-UHFFFAOYSA-N suberic acid Chemical compound OC(=O)CCCCCCC(O)=O TYFQFVWCELRYAO-UHFFFAOYSA-N 0.000 description 2
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 2
- JLGLQAWTXXGVEM-UHFFFAOYSA-N triethylene glycol monomethyl ether Chemical compound COCCOCCOCCO JLGLQAWTXXGVEM-UHFFFAOYSA-N 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- DNIAPMSPPWPWGF-VKHMYHEASA-N (+)-propylene glycol Chemical compound C[C@H](O)CO DNIAPMSPPWPWGF-VKHMYHEASA-N 0.000 description 1
- JNYAEWCLZODPBN-JGWLITMVSA-N (2r,3r,4s)-2-[(1r)-1,2-dihydroxyethyl]oxolane-3,4-diol Chemical compound OC[C@@H](O)[C@H]1OC[C@H](O)[C@H]1O JNYAEWCLZODPBN-JGWLITMVSA-N 0.000 description 1
- 229940015975 1,2-hexanediol Drugs 0.000 description 1
- YPFDHNVEDLHUCE-UHFFFAOYSA-N 1,3-propanediol Substances OCCCO YPFDHNVEDLHUCE-UHFFFAOYSA-N 0.000 description 1
- 229940035437 1,3-propanediol Drugs 0.000 description 1
- RKDVKSZUMVYZHH-UHFFFAOYSA-N 1,4-dioxane-2,5-dione Chemical compound O=C1COC(=O)CO1 RKDVKSZUMVYZHH-UHFFFAOYSA-N 0.000 description 1
- QWOZZTWBWQMEPD-UHFFFAOYSA-N 1-(2-ethoxypropoxy)propan-2-ol Chemical compound CCOC(C)COCC(C)O QWOZZTWBWQMEPD-UHFFFAOYSA-N 0.000 description 1
- VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical compound CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 description 1
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- WVUYYXUATWMVIT-UHFFFAOYSA-N 1-bromo-4-ethoxybenzene Chemical compound CCOC1=CC=C(Br)C=C1 WVUYYXUATWMVIT-UHFFFAOYSA-N 0.000 description 1
- RWNUSVWFHDHRCJ-UHFFFAOYSA-N 1-butoxypropan-2-ol Chemical compound CCCCOCC(C)O RWNUSVWFHDHRCJ-UHFFFAOYSA-N 0.000 description 1
- JOLQKTGDSGKSKJ-UHFFFAOYSA-N 1-ethoxypropan-2-ol Chemical compound CCOCC(C)O JOLQKTGDSGKSKJ-UHFFFAOYSA-N 0.000 description 1
- FDCJDKXCCYFOCV-UHFFFAOYSA-N 1-hexadecoxyhexadecane Chemical compound CCCCCCCCCCCCCCCCOCCCCCCCCCCCCCCCC FDCJDKXCCYFOCV-UHFFFAOYSA-N 0.000 description 1
- ARXJGSRGQADJSQ-UHFFFAOYSA-N 1-methoxypropan-2-ol Chemical compound COCC(C)O ARXJGSRGQADJSQ-UHFFFAOYSA-N 0.000 description 1
- QFGCFKJIPBRJGM-UHFFFAOYSA-N 12-[(2-methylpropan-2-yl)oxy]-12-oxododecanoic acid Chemical compound CC(C)(C)OC(=O)CCCCCCCCCCC(O)=O QFGCFKJIPBRJGM-UHFFFAOYSA-N 0.000 description 1
- KJDGGLOKWHMBOX-UHFFFAOYSA-N 2,2,3-trimethylbutanedioic acid Chemical compound OC(=O)C(C)C(C)(C)C(O)=O KJDGGLOKWHMBOX-UHFFFAOYSA-N 0.000 description 1
- BTUDGPVTCYNYLK-UHFFFAOYSA-N 2,2-dimethylglutaric acid Chemical compound OC(=O)C(C)(C)CCC(O)=O BTUDGPVTCYNYLK-UHFFFAOYSA-N 0.000 description 1
- BTVZFIIHBJWMOG-UHFFFAOYSA-N 2,2-dimethylhexanedioic acid Chemical compound OC(=O)C(C)(C)CCCC(O)=O BTVZFIIHBJWMOG-UHFFFAOYSA-N 0.000 description 1
- GOHPTLYPQCTZSE-UHFFFAOYSA-N 2,2-dimethylsuccinic acid Chemical compound OC(=O)C(C)(C)CC(O)=O GOHPTLYPQCTZSE-UHFFFAOYSA-N 0.000 description 1
- VIWYMIDWAOZEAZ-UHFFFAOYSA-N 2,4-dimethylpentanedioic acid Chemical compound OC(=O)C(C)CC(C)C(O)=O VIWYMIDWAOZEAZ-UHFFFAOYSA-N 0.000 description 1
- UVNSFSOKRSZVEZ-UHFFFAOYSA-N 2-(2-decoxyethoxy)ethanol Chemical compound CCCCCCCCCCOCCOCCO UVNSFSOKRSZVEZ-UHFFFAOYSA-N 0.000 description 1
- AZLWQVJVINEILY-UHFFFAOYSA-N 2-(2-dodecoxyethoxy)ethanol Chemical compound CCCCCCCCCCCCOCCOCCO AZLWQVJVINEILY-UHFFFAOYSA-N 0.000 description 1
- OHJYHAOODFPJOD-UHFFFAOYSA-N 2-(2-ethylhexoxy)ethanol Chemical compound CCCCC(CC)COCCO OHJYHAOODFPJOD-UHFFFAOYSA-N 0.000 description 1
- GZMAAYIALGURDQ-UHFFFAOYSA-N 2-(2-hexoxyethoxy)ethanol Chemical compound CCCCCCOCCOCCO GZMAAYIALGURDQ-UHFFFAOYSA-N 0.000 description 1
- SBASXUCJHJRPEV-UHFFFAOYSA-N 2-(2-methoxyethoxy)ethanol Chemical compound COCCOCCO SBASXUCJHJRPEV-UHFFFAOYSA-N 0.000 description 1
- NDSYZZUVPRGESW-UHFFFAOYSA-N 2-(2-octoxyethoxy)ethanol Chemical compound CCCCCCCCOCCOCCO NDSYZZUVPRGESW-UHFFFAOYSA-N 0.000 description 1
- DJCYDDALXPHSHR-UHFFFAOYSA-N 2-(2-propoxyethoxy)ethanol Chemical compound CCCOCCOCCO DJCYDDALXPHSHR-UHFFFAOYSA-N 0.000 description 1
- XYVAYAJYLWYJJN-UHFFFAOYSA-N 2-(2-propoxypropoxy)propan-1-ol Chemical compound CCCOC(C)COC(C)CO XYVAYAJYLWYJJN-UHFFFAOYSA-N 0.000 description 1
- WNRNXKWTIJWZFQ-UHFFFAOYSA-N 2-(2-tetradecoxyethoxy)ethanol Chemical compound CCCCCCCCCCCCCCOCCOCCO WNRNXKWTIJWZFQ-UHFFFAOYSA-N 0.000 description 1
- OEPOKWHJYJXUGD-UHFFFAOYSA-N 2-(3-phenylmethoxyphenyl)-1,3-thiazole-4-carbaldehyde Chemical compound O=CC1=CSC(C=2C=C(OCC=3C=CC=CC=3)C=CC=2)=N1 OEPOKWHJYJXUGD-UHFFFAOYSA-N 0.000 description 1
- OADIZUFHUPTFAG-UHFFFAOYSA-N 2-[2-(2-ethylhexoxy)ethoxy]ethanol Chemical compound CCCCC(CC)COCCOCCO OADIZUFHUPTFAG-UHFFFAOYSA-N 0.000 description 1
- RGICCULPCWNRAB-UHFFFAOYSA-N 2-[2-(2-hexoxyethoxy)ethoxy]ethanol Chemical compound CCCCCCOCCOCCOCCO RGICCULPCWNRAB-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
- WAEVWDZKMBQDEJ-UHFFFAOYSA-N 2-[2-(2-methoxypropoxy)propoxy]propan-1-ol Chemical compound COC(C)COC(C)COC(C)CO WAEVWDZKMBQDEJ-UHFFFAOYSA-N 0.000 description 1
- XIVLVYLYOMHUGB-UHFFFAOYSA-N 2-[2-(2-octoxyethoxy)ethoxy]ethanol Chemical compound CCCCCCCCOCCOCCOCCO XIVLVYLYOMHUGB-UHFFFAOYSA-N 0.000 description 1
- KCBPVRDDYVJQHA-UHFFFAOYSA-N 2-[2-(2-propoxyethoxy)ethoxy]ethanol Chemical compound CCCOCCOCCOCCO KCBPVRDDYVJQHA-UHFFFAOYSA-N 0.000 description 1
- GSKKPNMVOYDARW-UHFFFAOYSA-N 2-[2-[2-(2-ethylhexoxy)ethoxy]ethoxy]ethanol Chemical compound CCCCC(CC)COCCOCCOCCO GSKKPNMVOYDARW-UHFFFAOYSA-N 0.000 description 1
- CBVDPTYIDMQDEO-UHFFFAOYSA-N 2-decoxyethanol Chemical compound CCCCCCCCCCOCCO CBVDPTYIDMQDEO-UHFFFAOYSA-N 0.000 description 1
- FDYJJKHDNNVUDR-UHFFFAOYSA-N 2-ethyl-2-methylbutanedioic acid Chemical compound CCC(C)(C(O)=O)CC(O)=O FDYJJKHDNNVUDR-UHFFFAOYSA-N 0.000 description 1
- UPGSWASWQBLSKZ-UHFFFAOYSA-N 2-hexoxyethanol Chemical compound CCCCCCOCCO UPGSWASWQBLSKZ-UHFFFAOYSA-N 0.000 description 1
- RFVNOJDQRGSOEL-UHFFFAOYSA-N 2-hydroxyethyl octadecanoate Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCCO RFVNOJDQRGSOEL-UHFFFAOYSA-N 0.000 description 1
- NYHNVHGFPZAZGA-UHFFFAOYSA-N 2-hydroxyhexanoic acid Chemical compound CCCCC(O)C(O)=O NYHNVHGFPZAZGA-UHFFFAOYSA-N 0.000 description 1
- JRHWHSJDIILJAT-UHFFFAOYSA-N 2-hydroxypentanoic acid Chemical compound CCCC(O)C(O)=O JRHWHSJDIILJAT-UHFFFAOYSA-N 0.000 description 1
- FWQNYUYRXNWOOM-UHFFFAOYSA-N 2-nonylpropanedioic acid Chemical class CCCCCCCCCC(C(O)=O)C(O)=O FWQNYUYRXNWOOM-UHFFFAOYSA-N 0.000 description 1
- ZQCIMPBZCZUDJM-UHFFFAOYSA-N 2-octoxyethanol Chemical compound CCCCCCCCOCCO ZQCIMPBZCZUDJM-UHFFFAOYSA-N 0.000 description 1
- YEYKMVJDLWJFOA-UHFFFAOYSA-N 2-propoxyethanol Chemical compound CCCOCCO YEYKMVJDLWJFOA-UHFFFAOYSA-N 0.000 description 1
- ALKCLFLTXBBMMP-UHFFFAOYSA-N 3,7-dimethylocta-1,6-dien-3-yl hexanoate Chemical compound CCCCCC(=O)OC(C)(C=C)CCC=C(C)C ALKCLFLTXBBMMP-UHFFFAOYSA-N 0.000 description 1
- QCAHUFWKIQLBNB-UHFFFAOYSA-N 3-(3-methoxypropoxy)propan-1-ol Chemical compound COCCCOCCCO QCAHUFWKIQLBNB-UHFFFAOYSA-N 0.000 description 1
- ALRHLSYJTWAHJZ-UHFFFAOYSA-N 3-hydroxypropionic acid Chemical compound OCCC(O)=O ALRHLSYJTWAHJZ-UHFFFAOYSA-N 0.000 description 1
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- QYQADNCHXSEGJT-UHFFFAOYSA-N cyclohexane-1,1-dicarboxylate;hydron Chemical compound OC(=O)C1(C(O)=O)CCCCC1 QYQADNCHXSEGJT-UHFFFAOYSA-N 0.000 description 1
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- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
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Landscapes
- Compositions Of Macromolecular Compounds (AREA)
- Polyesters Or Polycarbonates (AREA)
Description
式(1):R1−(OR2)m−OCO−R3−CO−[O−(R4O)n−CO−R3’−CO]k−O−(R2’O)m’−R1’[式中、R1、R1’は水素原子、炭素数1〜16のアルキル基(但し、R1、R1’が共に水素原子となることはない。)、R2、R2’、R4は炭素数1〜8のアルキレン基、R3、R3’は炭素数1〜12のアルキレン基、又はアルケニレン基、kは1〜10の整数、n、m、m’は1〜50の整数を表す。]で表される化合物を主成分とする樹脂用可塑剤。および当該樹脂用可塑剤を含有してなる樹脂組成物に関する。
以下に実施例を挙げて、本発明を更に詳細に説明するが、本発明はこれに限定されるものではない。
実施例1と同様の反応装置を用いて、アジピン酸102.2g(0.70モル)、1,4−ブタンジオール31.5g(0.35モル)、トルエン53gおよび35%硫酸3.0gを加え、110〜120℃に加熱し、生成水を系外に除きながらエステル化反応を行った。理論量の水が生成後、2−エチルヘキサノール93.6g(0.71モル)を加え、120〜130℃に加熱し、理論量の水が生成するまで引続きエステル化反応を行った。これを冷却し、アルカリ洗浄、水洗浄後、トルエンおよび過剰のアルコールを減圧除去し、活性炭で脱色処理を行い、160.0gの反応生成物aを得た。
実施例1と同様の反応装置を用いて、実施例2のジエチレングリコールモノブチルエーテルをトリエチレングリコール201.0g(1.34モル)に替えた以外は実施例2と同様に、反応、精製を行い、289.1gの反応生成物bを得た。
実施例1と同様の反応装置を用いて、コハク酸42.5g(0.36モル)、エチレングリコール11.2g(0.18モル)、トルエン30gおよび35%硫酸1.5gを加え、110〜120℃に加熱し、生成水を系外に除きながらエステル化反応を行った。理論量の水が生成後、ポリエチレングリコールモノステアレート(平均重合度n=45)856.1g(0.38モル)を加え、120〜130℃に加熱し、理論量の水が生成するまで引続きエステル化反応を行った。これを冷却し、アルカリ洗浄、水洗浄後、トルエンおよび過剰のアルコールを減圧除去し、活性炭で脱色処理を行い、664.3gの反応生成物cを得た。
実施例1と同様の反応装置を用いて、実施例2のポリエチレングリコール#200をポリエチレングリコール#3000(平均重合度n=68)1920.0g(0.64モル)に替えた以外は実施例2と同様に、反応、精製を行い、1414.9gの反応生成物dを得た。
実施例1と同様の反応装置を用いて、1,18−オクタデカンジカルボン酸123.3g(0.36モル)、エチレングリコール11.2g(0.18モル)、トルエン30gおよび35%硫酸1.5gを加え、110〜120℃に加熱し、生成水を系外に除きながらエステル化反応を行った。理論量の水が生成後、ジエチレングリコールモノブチルエーテル61.4g(0.38モル)を加え、120〜130℃に加熱し、理論量の水が生成するまで引続きエステル化反応を行った。これを冷却し、アルカリ洗浄、水洗浄後、トルエンおよび過剰のアルコールを減圧除去し、活性炭で脱色処理を行い、136.7gの反応生成物eを得た。
実施例1と同様の反応装置を用いて、コハク酸42.5g(0.36モル)、1,10−デカンジオール31.4g(0.18モル)、トルエン30gおよび35%硫酸1.5gを加え、110〜120℃に加熱し、生成水を系外に除きながらエステル化反応を行った。理論量の水が生成後、ジエチレングリコールモノブチルエーテル61.4g(0.38モル)を加え、120〜130℃に加熱し、理論量の水が生成するまで引続きエステル化反応を行った。これを冷却し、アルカリ洗浄、水洗浄後、トルエンおよび過剰のアルコールを減圧除去し、活性炭で脱色処理を行い、95.3gの反応生成物fを得た。
樹脂100重量部に対し所定量の可塑剤を加え、設定温度190℃でブラベンダー(ブラベンダー社製)を用いて溶融混練し、樹脂組成物を得た。この樹脂組成物を180℃、冷却温度25℃で圧縮成形し、所定の試験シートおよびフィルムを作成した。この試験シートおよびフィルムを用いて透明性評価、柔軟性評価およびブリード性評価を行なった。
2枚のガラス板に挟んだ、厚さ約200μmの試験フィルムを作成し、ヘーズメーター(スガ試験機社製)を用いて試験フィルムのヘーズ値を測定した。
厚さ1.5mm(縦100mm、横50mm)の試験シートを作成し、硬さ試験機(JIS K6301 JA型硬度計)を用いて試験シートの硬度を測定した。尚、本試験機でのポリエチレン(住友化学社製)シートの硬度は77であった。
厚さ1.5mm(縦100mm、横50mm)の試験シートを作成し、この試験シートを50℃、50RH%雰囲気下で2週間放置した後、下記評価を行なった。
(1)目視評価:試験シート表面への可塑剤のブリードアウトの有無を目視で評価した。○ブリードアウトなし、△ややブリードアウトあり、×ブリードアウトあり。
(2)減少率:試験シート表面からブリードアウトした可塑剤を拭き取った後、試験シート重量を測定し、試験前からの重量減少率を測定した。
(3)外観濁り:試験シートの透明性を目視で評価した。○濁りなし、△やや濁りあり、×濁りあり又は白色化。
Claims (6)
- 式(1):R1−(OR2)m−OCO−R3−CO−[O−(R4O)n−CO−R3’−CO]k−O−(R2’O)m’−R1’[式中、R1、R1’は水素原子、炭素数1〜16のアルキル基(但し、R1、R1’が共に水素原子となることはない。)、R2、R2’、R4は炭素数1〜8のアルキレン基、R3、R3’は炭素数1〜12のアルキレン基、又はアルケニレン基、kは1〜10の整数、n、m、m’は1〜50の整数を表す。]で表される化合物を主成分とするポリエステル樹脂用可塑剤。
- (a)(ポリ)アルキレングリコールモノアルキルエーテル、(b)マロン酸、コハク酸、アジピン酸、フマル酸、マレイン酸及びこれらの酸無水物からなる群から選ばれる少なくとも1種類のジカルボン酸類(c)分子量1000以下の(ポリ)エチレングリコール、1,2−ブタンジオール、ジエチレングリコール、1,4−ブタンジオールからなる群から選ばれる少なくとも1種類のグリコール類の反応により得られる化合物を主成分とするポリエステル樹脂用可塑剤。
- 前記ポリエステル樹脂がポリ乳酸系樹脂であることを特徴とする請求項1記載のポリエステル樹脂用可塑剤。
- 前記ポリエステル樹脂がポリ乳酸系樹脂であることを特徴とする請求項2記載のポリエステル樹脂用可塑剤。
- 請求項1または2記載のポリエステル用樹脂可塑剤を含有してなるポリエステル樹脂組成物。
- 前記ポリエステル樹脂組成物がポリ乳酸系樹脂組成物であることを特徴とする請求項5記載のポリエステル樹脂組成物。
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WO2009013847A1 (ja) * | 2007-07-26 | 2009-01-29 | Kawasaki Kasei Chemicals Ltd. | ポリ乳酸樹脂組成物 |
JP5312812B2 (ja) | 2008-01-23 | 2013-10-09 | 株式会社Adeka | セルロース系樹脂組成物およびセルロース系樹脂フィルム |
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KR101455528B1 (ko) | 2013-05-07 | 2014-10-27 | 최면천 | 폴리락트산의 개질제, 폴리락트산 개질제 제조방법, 이를 이용한 폴리락트산 개질방법, 개질된 폴리락트산을 이용한 생분해성 발포체 조성물 및 생분해성 발포체 조성물을 이용한 신발용 발포체 |
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