JP6082750B2 - ハロゲン化ポリマーの安定化組成物 - Google Patents
ハロゲン化ポリマーの安定化組成物 Download PDFInfo
- Publication number
- JP6082750B2 JP6082750B2 JP2014544784A JP2014544784A JP6082750B2 JP 6082750 B2 JP6082750 B2 JP 6082750B2 JP 2014544784 A JP2014544784 A JP 2014544784A JP 2014544784 A JP2014544784 A JP 2014544784A JP 6082750 B2 JP6082750 B2 JP 6082750B2
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- Japan
- Prior art keywords
- mono
- poly
- tin
- compound composition
- stabilizer
- Prior art date
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- 229920000642 polymer Polymers 0.000 title claims description 65
- 239000000203 mixture Substances 0.000 title claims description 52
- 229920000915 polyvinyl chloride Polymers 0.000 claims description 41
- 239000004800 polyvinyl chloride Substances 0.000 claims description 41
- 150000001875 compounds Chemical class 0.000 claims description 34
- 239000003381 stabilizer Substances 0.000 claims description 34
- 150000003839 salts Chemical class 0.000 claims description 31
- 229910052736 halogen Inorganic materials 0.000 claims description 27
- 150000002367 halogens Chemical class 0.000 claims description 27
- -1 alkyl tin Chemical compound 0.000 claims description 25
- 239000000463 material Substances 0.000 claims description 16
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 claims description 10
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 10
- 239000004014 plasticizer Substances 0.000 claims description 9
- 229920001577 copolymer Polymers 0.000 claims description 8
- 125000001183 hydrocarbyl group Chemical group 0.000 claims description 8
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 claims description 7
- 229920001519 homopolymer Polymers 0.000 claims description 7
- 239000007787 solid Substances 0.000 claims description 7
- WEMJWKKJHSZRQT-KTKRTIGZSA-N 2-sulfanylethyl (z)-octadec-9-enoate Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OCCS WEMJWKKJHSZRQT-KTKRTIGZSA-N 0.000 claims description 6
- XQQOPCNHFYPOLS-UHFFFAOYSA-N C(CS)OC(=O)C(C(C(=O)O)O)O Chemical compound C(CS)OC(=O)C(C(C(=O)O)O)O XQQOPCNHFYPOLS-UHFFFAOYSA-N 0.000 claims description 5
- 229920002125 Sokalan® Polymers 0.000 claims description 5
- BZHJMEDXRYGGRV-UHFFFAOYSA-N Vinyl chloride Chemical compound ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 claims description 5
- NPAIMXWXWPJRES-UHFFFAOYSA-N butyltin(3+) Chemical compound CCCC[Sn+3] NPAIMXWXWPJRES-UHFFFAOYSA-N 0.000 claims description 5
- ZMHZSHHZIKJFIR-UHFFFAOYSA-N octyltin Chemical compound CCCCCCCC[Sn] ZMHZSHHZIKJFIR-UHFFFAOYSA-N 0.000 claims description 5
- AYOHIQLKSOJJQH-UHFFFAOYSA-N dibutyltin Chemical compound CCCC[Sn]CCCC AYOHIQLKSOJJQH-UHFFFAOYSA-N 0.000 claims description 4
- 229920001444 polymaleic acid Polymers 0.000 claims description 4
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- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
- 229920001328 Polyvinylidene chloride Polymers 0.000 claims description 3
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 3
- LUZSPGQEISANPO-UHFFFAOYSA-N butyltin Chemical compound CCCC[Sn] LUZSPGQEISANPO-UHFFFAOYSA-N 0.000 claims description 3
- YAHBZWSDRFSFOO-UHFFFAOYSA-L dimethyltin(2+);2-(2-ethylhexoxy)-2-oxoethanethiolate Chemical compound CCCCC(CC)COC(=O)CS[Sn](C)(C)SCC(=O)OCC(CC)CCCC YAHBZWSDRFSFOO-UHFFFAOYSA-L 0.000 claims description 3
- 238000001035 drying Methods 0.000 claims description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims description 3
- 239000001257 hydrogen Substances 0.000 claims description 3
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- 230000004580 weight loss Effects 0.000 claims description 3
- 125000006659 (C1-C20) hydrocarbyl group Chemical group 0.000 claims description 2
- 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 claims description 2
- MMRNDUMAYOAQAM-UHFFFAOYSA-N C(CS)(=O)OCC(CCCC)CC.C(CCC)[Sn]CCCC Chemical compound C(CS)(=O)OCC(CCCC)CC.C(CCC)[Sn]CCCC MMRNDUMAYOAQAM-UHFFFAOYSA-N 0.000 claims description 2
- PWEVMPIIOJUPRI-UHFFFAOYSA-N dimethyltin Chemical compound C[Sn]C PWEVMPIIOJUPRI-UHFFFAOYSA-N 0.000 claims description 2
- OWXFBYWQHWEQOF-UHFFFAOYSA-N dimethyltin 2-ethylhexyl 2-sulfanylacetate Chemical compound C(CS)(=O)OCC(CCCC)CC.C[Sn]C OWXFBYWQHWEQOF-UHFFFAOYSA-N 0.000 claims description 2
- HGQSXVKHVMGQRG-UHFFFAOYSA-N dioctyltin Chemical compound CCCCCCCC[Sn]CCCCCCCC HGQSXVKHVMGQRG-UHFFFAOYSA-N 0.000 claims description 2
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- 229920002620 polyvinyl fluoride Polymers 0.000 claims description 2
- 229920002981 polyvinylidene fluoride Polymers 0.000 claims description 2
- 229920002845 Poly(methacrylic acid) Polymers 0.000 claims 2
- 239000002861 polymer material Substances 0.000 claims 2
- HZHREVFVFOBHSK-UHFFFAOYSA-L dioctyltin(2+);4-ethyl-2-sulfanyloctanoate Chemical compound CCCCC(CC)CC(S)C([O-])=O.CCCCC(CC)CC(S)C([O-])=O.CCCCCCCC[Sn+2]CCCCCCCC HZHREVFVFOBHSK-UHFFFAOYSA-L 0.000 claims 1
- 159000000000 sodium salts Chemical class 0.000 description 9
- 238000002156 mixing Methods 0.000 description 6
- 238000011105 stabilization Methods 0.000 description 6
- 238000009472 formulation Methods 0.000 description 5
- 239000000523 sample Substances 0.000 description 5
- 238000001542 size-exclusion chromatography Methods 0.000 description 5
- 230000006641 stabilisation Effects 0.000 description 5
- 0 CC=*N*(*)(N*)N* Chemical compound CC=*N*(*)(N*)N* 0.000 description 4
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 4
- BJQHLKABXJIVAM-UHFFFAOYSA-N bis(2-ethylhexyl) phthalate Chemical group CCCCC(CC)COC(=O)C1=CC=CC=C1C(=O)OCC(CC)CCCC BJQHLKABXJIVAM-UHFFFAOYSA-N 0.000 description 4
- 239000000654 additive Substances 0.000 description 3
- 239000012760 heat stabilizer Substances 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 229910052751 metal Inorganic materials 0.000 description 3
- 239000002184 metal Substances 0.000 description 3
- 239000002245 particle Substances 0.000 description 3
- 238000000926 separation method Methods 0.000 description 3
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 3
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- SOGAXMICEFXMKE-UHFFFAOYSA-N Butylmethacrylate Chemical compound CCCCOC(=O)C(C)=C SOGAXMICEFXMKE-UHFFFAOYSA-N 0.000 description 2
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 2
- 239000005977 Ethylene Substances 0.000 description 2
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 description 2
- 239000004793 Polystyrene Substances 0.000 description 2
- KGSDETDNNVQBKU-UHFFFAOYSA-K [Sn+3]C.CCCCC(CC)CC(S)C([O-])=O.CCCCC(CC)CC(S)C([O-])=O.CCCCC(CC)CC(S)C([O-])=O Chemical compound [Sn+3]C.CCCCC(CC)CC(S)C([O-])=O.CCCCC(CC)CC(S)C([O-])=O.CCCCC(CC)CC(S)C([O-])=O KGSDETDNNVQBKU-UHFFFAOYSA-K 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 230000001419 dependent effect Effects 0.000 description 2
- DOIRQSBPFJWKBE-UHFFFAOYSA-N dibutyl phthalate Chemical compound CCCCOC(=O)C1=CC=CC=C1C(=O)OCCCC DOIRQSBPFJWKBE-UHFFFAOYSA-N 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- FJKIXWOMBXYWOQ-UHFFFAOYSA-N ethenoxyethane Chemical compound CCOC=C FJKIXWOMBXYWOQ-UHFFFAOYSA-N 0.000 description 2
- 239000006260 foam Substances 0.000 description 2
- CSHCPECZJIEGJF-UHFFFAOYSA-N methyltin Chemical compound [Sn]C CSHCPECZJIEGJF-UHFFFAOYSA-N 0.000 description 2
- 239000000178 monomer Substances 0.000 description 2
- 229920001490 poly(butyl methacrylate) polymer Polymers 0.000 description 2
- 229920003229 poly(methyl methacrylate) Polymers 0.000 description 2
- 229920002959 polymer blend Polymers 0.000 description 2
- 239000004926 polymethyl methacrylate Substances 0.000 description 2
- 229920002223 polystyrene Polymers 0.000 description 2
- 229920005989 resin Polymers 0.000 description 2
- 239000011347 resin Substances 0.000 description 2
- 239000007921 spray Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 239000003039 volatile agent Substances 0.000 description 2
- 229920002818 (Hydroxyethyl)methacrylate Polymers 0.000 description 1
- KUIZKZHDMPERHR-UHFFFAOYSA-N 1-phenylprop-2-en-1-one Chemical compound C=CC(=O)C1=CC=CC=C1 KUIZKZHDMPERHR-UHFFFAOYSA-N 0.000 description 1
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 1
- JAHNSTQSQJOJLO-UHFFFAOYSA-N 2-(3-fluorophenyl)-1h-imidazole Chemical compound FC1=CC=CC(C=2NC=CN=2)=C1 JAHNSTQSQJOJLO-UHFFFAOYSA-N 0.000 description 1
- 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 1
- GOXQRTZXKQZDDN-UHFFFAOYSA-N 2-Ethylhexyl acrylate Chemical compound CCCCC(CC)COC(=O)C=C GOXQRTZXKQZDDN-UHFFFAOYSA-N 0.000 description 1
- XHZPRMZZQOIPDS-UHFFFAOYSA-N 2-Methyl-2-[(1-oxo-2-propenyl)amino]-1-propanesulfonic acid Chemical compound OS(=O)(=O)CC(C)(C)NC(=O)C=C XHZPRMZZQOIPDS-UHFFFAOYSA-N 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 1
- OYUNTGBISCIYPW-UHFFFAOYSA-N 2-chloroprop-2-enenitrile Chemical compound ClC(=C)C#N OYUNTGBISCIYPW-UHFFFAOYSA-N 0.000 description 1
- YDLAHBBJAGGIJZ-UHFFFAOYSA-N 2-sulfanylethyl acetate Chemical compound CC(=O)OCCS YDLAHBBJAGGIJZ-UHFFFAOYSA-N 0.000 description 1
- UHBAWOXYQROEIH-UHFFFAOYSA-N 3-chloro-4-(2-chlorobut-3-enoxy)but-1-ene Chemical compound C=CC(Cl)COCC(Cl)C=C UHBAWOXYQROEIH-UHFFFAOYSA-N 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- LHWLFCSLUZSWCG-UHFFFAOYSA-N C(CS)(=O)OCC(CCCC)CC.[Sn] Chemical class C(CS)(=O)OCC(CCCC)CC.[Sn] LHWLFCSLUZSWCG-UHFFFAOYSA-N 0.000 description 1
- WIVTXBIFTLNVCZ-UHFFFAOYSA-N CC(=C)C(=O)OCCP(=O)=O Chemical compound CC(=C)C(=O)OCCP(=O)=O WIVTXBIFTLNVCZ-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- IEPRKVQEAMIZSS-UHFFFAOYSA-N Di-Et ester-Fumaric acid Natural products CCOC(=O)C=CC(=O)OCC IEPRKVQEAMIZSS-UHFFFAOYSA-N 0.000 description 1
- MQIUGAXCHLFZKX-UHFFFAOYSA-N Di-n-octyl phthalate Natural products CCCCCCCCOC(=O)C1=CC=CC=C1C(=O)OCCCCCCCC MQIUGAXCHLFZKX-UHFFFAOYSA-N 0.000 description 1
- PYGXAGIECVVIOZ-UHFFFAOYSA-N Dibutyl decanedioate Chemical compound CCCCOC(=O)CCCCCCCCC(=O)OCCCC PYGXAGIECVVIOZ-UHFFFAOYSA-N 0.000 description 1
- IEPRKVQEAMIZSS-WAYWQWQTSA-N Diethyl maleate Chemical compound CCOC(=O)\C=C/C(=O)OCC IEPRKVQEAMIZSS-WAYWQWQTSA-N 0.000 description 1
- JIGUQPWFLRLWPJ-UHFFFAOYSA-N Ethyl acrylate Chemical compound CCOC(=O)C=C JIGUQPWFLRLWPJ-UHFFFAOYSA-N 0.000 description 1
- 239000004605 External Lubricant Substances 0.000 description 1
- KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 description 1
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- 239000004610 Internal Lubricant Substances 0.000 description 1
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 1
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- 230000002378 acidificating effect Effects 0.000 description 1
- XECAHXYUAAWDEL-UHFFFAOYSA-N acrylonitrile butadiene styrene Chemical compound C=CC=C.C=CC#N.C=CC1=CC=CC=C1 XECAHXYUAAWDEL-UHFFFAOYSA-N 0.000 description 1
- 239000004676 acrylonitrile butadiene styrene Substances 0.000 description 1
- 229920000122 acrylonitrile butadiene styrene Polymers 0.000 description 1
- WNLRTRBMVRJNCN-UHFFFAOYSA-L adipate(2-) Chemical compound [O-]C(=O)CCCCC([O-])=O WNLRTRBMVRJNCN-UHFFFAOYSA-L 0.000 description 1
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical class OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 1
- 230000032683 aging Effects 0.000 description 1
- 125000005250 alkyl acrylate group Chemical group 0.000 description 1
- 125000005907 alkyl ester group Chemical group 0.000 description 1
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- MIMDHDXOBDPUQW-UHFFFAOYSA-N dioctyl decanedioate Chemical compound CCCCCCCCOC(=O)CCCCCCCCC(=O)OCCCCCCCC MIMDHDXOBDPUQW-UHFFFAOYSA-N 0.000 description 1
- DSFINWFBOOONMM-UHFFFAOYSA-N dioctyltin;2-ethylhexyl 2-sulfanylacetate Chemical compound CCCCC(CC)COC(=O)CS.CCCCCCCC[Sn]CCCCCCCC DSFINWFBOOONMM-UHFFFAOYSA-N 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- NHOGGUYTANYCGQ-UHFFFAOYSA-N ethenoxybenzene Chemical compound C=COC1=CC=CC=C1 NHOGGUYTANYCGQ-UHFFFAOYSA-N 0.000 description 1
- MEGHWIAOTJPCHQ-UHFFFAOYSA-N ethenyl butanoate Chemical compound CCCC(=O)OC=C MEGHWIAOTJPCHQ-UHFFFAOYSA-N 0.000 description 1
- UIWXSTHGICQLQT-UHFFFAOYSA-N ethenyl propanoate Chemical compound CCC(=O)OC=C UIWXSTHGICQLQT-UHFFFAOYSA-N 0.000 description 1
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- PBZROIMXDZTJDF-UHFFFAOYSA-N hepta-1,6-dien-4-one Chemical compound C=CCC(=O)CC=C PBZROIMXDZTJDF-UHFFFAOYSA-N 0.000 description 1
- HJDQVQXEAZRSQI-UHFFFAOYSA-N hexanedioic acid;sodium Chemical compound [Na].[Na].OC(=O)CCCCC(O)=O HJDQVQXEAZRSQI-UHFFFAOYSA-N 0.000 description 1
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- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
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- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 1
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- AWJZTPWDQYFQPQ-UHFFFAOYSA-N methyl 2-chloroprop-2-enoate Chemical compound COC(=O)C(Cl)=C AWJZTPWDQYFQPQ-UHFFFAOYSA-N 0.000 description 1
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- PNJWIWWMYCMZRO-UHFFFAOYSA-N pent‐4‐en‐2‐one Natural products CC(=O)CC=C PNJWIWWMYCMZRO-UHFFFAOYSA-N 0.000 description 1
- 235000021317 phosphate Nutrition 0.000 description 1
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- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 239000012488 sample solution Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- KYKFCSHPTAVNJD-UHFFFAOYSA-L sodium adipate Chemical compound [Na+].[Na+].[O-]C(=O)CCCCC([O-])=O KYKFCSHPTAVNJD-UHFFFAOYSA-L 0.000 description 1
- 239000001601 sodium adipate Substances 0.000 description 1
- 235000011049 sodium adipate Nutrition 0.000 description 1
- 239000001509 sodium citrate Substances 0.000 description 1
- NLJMYIDDQXHKNR-UHFFFAOYSA-K sodium citrate Chemical compound O.O.[Na+].[Na+].[Na+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O NLJMYIDDQXHKNR-UHFFFAOYSA-K 0.000 description 1
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- 230000036962 time dependent Effects 0.000 description 1
- STCOOQWBFONSKY-UHFFFAOYSA-N tributyl phosphate Chemical compound CCCCOP(=O)(OCCCC)OCCCC STCOOQWBFONSKY-UHFFFAOYSA-N 0.000 description 1
- HRXKRNGNAMMEHJ-UHFFFAOYSA-K trisodium citrate Chemical class [Na+].[Na+].[Na+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O HRXKRNGNAMMEHJ-UHFFFAOYSA-K 0.000 description 1
- KOZCZZVUFDCZGG-UHFFFAOYSA-N vinyl benzoate Chemical compound C=COC(=O)C1=CC=CC=C1 KOZCZZVUFDCZGG-UHFFFAOYSA-N 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- FUSUHKVFWTUUBE-UHFFFAOYSA-N vinyl methyl ketone Natural products CC(=O)C=C FUSUHKVFWTUUBE-UHFFFAOYSA-N 0.000 description 1
- 229920001959 vinylidene polymer Polymers 0.000 description 1
- ZTWTYVWXUKTLCP-UHFFFAOYSA-N vinylphosphonic acid Chemical compound OP(O)(=O)C=C ZTWTYVWXUKTLCP-UHFFFAOYSA-N 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 239000003643 water by type Substances 0.000 description 1
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L27/00—Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a halogen; Compositions of derivatives of such polymers
- C08L27/02—Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a halogen; Compositions of derivatives of such polymers not modified by chemical after-treatment
- C08L27/04—Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a halogen; Compositions of derivatives of such polymers not modified by chemical after-treatment containing chlorine atoms
- C08L27/06—Homopolymers or copolymers of vinyl chloride
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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
- C08K5/56—Organo-metallic compounds, i.e. organic compounds containing a metal-to-carbon bond
- C08K5/57—Organo-tin compounds
- C08K5/58—Organo-tin compounds containing sulfur
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L27/00—Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a halogen; Compositions of derivatives of such polymers
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L27/00—Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a halogen; Compositions of derivatives of such polymers
- C08L27/22—Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a halogen; Compositions of derivatives of such polymers modified by chemical after-treatment
- C08L27/24—Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a halogen; Compositions of derivatives of such polymers modified by chemical after-treatment halogenated
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L33/00—Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides or nitriles thereof; Compositions of derivatives of such polymers
- C08L33/02—Homopolymers or copolymers of acids; Metal or ammonium salts thereof
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L35/00—Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a carboxyl radical, and containing at least one other carboxyl radical in the molecule, or of salts, anhydrides, esters, amides, imides or nitriles thereof; Compositions of derivatives of such polymers
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L2201/00—Properties
- C08L2201/08—Stabilised against heat, light or radiation or oxydation
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Description
a)40重量%を超えるハロゲン含有ポリマー材料と;
b)モノアルキルスズ安定化剤およびジアルキルスズ安定化剤の混合物を含む、0.01から5.0phrのアルキルスズ安定化剤と;
c)固体形態の0.01から5.0phrのポリマーポリ酸材料の塩と;
d)最終化合物組成物中で0.52wt%以上の水分レベルと
を含む安定化ハロゲン含有ポリマー化合物組成物が提供される。
・安定化剤A=27%モノメチルスズトリス(2−エチルヘキシルチオグリコレート)、73%ジメチルスズビス(2−エチルヘキシルチオグリコレート)
・安定化剤B=60%モノメチルスズトリス(2−エチルヘキシルチオグリコレート)、40%ジメチルスズビス(2−エチルヘキシルチオグリコレート)
・ポリマーポリ酸塩A=スプレー乾燥したACUMER(商標)1010(Rohm and Haas Company(The Dow Chemical Companyの完全所有子会社)の登録商標)。これは、ポリアクリル酸のナトリウム塩である。平均分子量(Mw)=2,000g/mol。
・ポリマーポリ酸塩B=スプレー乾燥したACUSOL(商標)425N(Rohm and Haas Company(The Dow Chemical Companyの完全所有子会社)の登録商標)。これは、ポリマレイン酸コポリアクリル酸のナトリウム塩である。平均分子量(Mw)=1,900g/mol。
Brabenderレオメータに、185℃に加熱した63グラムのcPVC配合物をチャージした。50rpmで混合しながら185℃にて加熱し、ホットcPVCサンプルを、指示した時間にて混合ボウルから取り出し、プレスし、5/8インチ×5/8インチのチップに打ち抜き(punched into)、時間の関数としてチャート上に配置した。各チップ(2分のチップ以外)の総色差(ΔE)を、Hunter Lab LabScan XE装置を用いて決定した。時間依存的ΔE進行を用いて、各cPVC配合物の熱安定性性能を評価した。総色差(ΔE)は、サンプルと基準とのL、a、b間の差を考慮した単一の値である。各ランにおける2分の時点にて集めたチップサンプルを基準として用いた。結果を表2に示す。
ポリマーポリ酸塩の分子量を、サイズ排除クロマトグラフィー(SEC)を用いて水中で決定した。Agilent 1100 Modelアイソクラチックポンプ、オートサンプラー、デガッサー(全てWaldbronn、Germany)およびWaters 410 Model示差屈折計(Milford、MA)からなる液体クロマトグラフ上にて、周囲温度で作動させて、分離を実行した。システム制御、データ収集およびデータ処理を、Cirrus(登録商標)ソフトウェアバージョン3.1(Polymer Laboratories(Varianの一部)、Church Stretton、UK)を用いて実行した。
連結させた2つの分析的PLaquagel−OH 30Aカラム(300×7.5mm ID)およびガードカラム(50×7.5mm ID)を用いて、SEC分離を実行した。SEC分離用に設定したカラム中に100μLのサンプル溶液を注入した。絶対分子量(g/mol)モル質量特性を、SEC−RI/MALDI−MSによって決定した。
cPVC化合物の水分レベルを、化合物中の他の揮発物が同じ量であるという仮定で、60分間予熱した150℃オーブン内で乾燥させた後の重量ロス(wt%)によって決定した。
Brabenderレオメータに、185℃に加熱した65グラムのPVC配合物をチャージした。60rpmで混合しながら185℃にて加熱し、ホットcPVCサンプルを、指示した時間にて混合ボウルから取り出し、プレスし、5/8インチ×5/8インチのチップに打ち抜き、時間の関数としてチャート上に配置した。チップのb値を、Hunter Lab LabScan XE装置を用いて測定した。結果を表4に示す。b値によりサンプル色の指標が与えられる。正のbは黄色であり、負のbは青色である。PVCは通常、プロセシング条件下で分解し、白色から黄色、茶色、続いて暗褐色に退色する。結果として、チップサンプルのb値は、時間の関数として、PVCの熱履歴が長くなると増大すると予想される。
PVC化合物の水分レベルを、化合物中の他の揮発物が同じ量であるという仮定で、60分間予熱した150℃オーブン内で乾燥させた後の重量ロス(wt%)によって決定した。
Claims (6)
- 安定化ハロゲン含有ポリマー化合物組成物であって:
(a)40重量%を超えるハロゲン化ポリマー材料と;
(b)下記式によって表されるモノおよびジアルキルスズメルカプタンの混合物を含む、0.01から5.0phrのアルキルスズ安定化剤と;
(c)固体形態の0.01から5.0phrのポリマーポリ酸の塩と;
(d)最終化合物組成物中で0.65wt%以上の水分レベルと、ここで前記水分レベルは、60分間予熱した150℃オーブン内で前記組成物を乾燥させた後の重量ロス(wt%)によって決定される;
を含む安定化ハロゲン含有ポリマー化合物組成物。 - ハロゲン化ポリマー材料は、ポリ(塩化ビニル)、ポリ(フッ化ビニル)、ポリ(塩化ビニリデン)、ポリ(フッ化ビニリデン)、塩素化ポリ(塩化ビニル)、塩素化ポリエチレン、塩化ビニルおよび塩化ビニリデンのコポリマー、またはこれらの混合物を含む、請求項1記載の安定化ハロゲン含有ポリマー化合物組成物。
- アルキルスズ安定化剤は、メチルスズ安定化剤、ブチルスズ安定化剤、オクチルスズ安定化剤、またはこれらの混合物を含む、請求項1記載の安定化ハロゲン含有ポリマー化合物組成物。
- アルキルスズ安定化剤は、モノおよびジメチルスズドデシルメルカプチド、モノおよびジメチルスズ2−エチルヘキシルチオグリコレート、モノおよびジメチルスズメルカプトエチルオレエートまたはメルカプトエチルタレート、モノおよびジブチルスズドデシルメルカプチド、モノおよびジブチルスズ2−エチルヘキシルチオグリコレート、モノおよびジブチルスズメルカプトエチルオレエートまたはメルカプトエチルタレート、モノおよびジオクチルスズドデシルメルカプチド、モノおよびジオクチルスズ2−エチルヘキシルチオグリコレート、ならびにモノおよびジオクチルスズメルカプトエチルオレエートまたはメルカプトエチルタレートを含む群から選択される、少なくとも1つのモノおよびジアルキルスズ安定化剤を含む、請求項3記載の安定化ハロゲン含有ポリマー化合物組成物。
- ポリマーポリ酸材料の塩は、ポリアクリル酸ホモポリマー、ポリアクリル酸コポリマー、ポリメタクリル酸ホモポリマー、ポリメタクリル酸コポリマー、ポリ(マレイン酸)ホモポリマー、またはポリ(マレイン酸)コポリマーの何れかの塩である、請求項1記載の安定化ハロゲン含有ポリマー化合物組成物。
- さらに、総組成物の10から60重量%の量の可塑剤を含む、請求項1記載の安定化ハロゲン含有ポリマー化合物組成物。
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US201161565112P | 2011-11-30 | 2011-11-30 | |
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PCT/US2012/066059 WO2013085714A1 (en) | 2011-11-30 | 2012-11-20 | Stabilized compositions of halogenated polymers |
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US20170260368A1 (en) * | 2016-03-08 | 2017-09-14 | Pmc Organometallix, Inc. | Methyl and Octyl Tin - REACH Compliant High Performance Stabilizer for PVC Film Manufacture |
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US5100946A (en) * | 1990-12-27 | 1992-03-31 | Atochem North America, Inc. | Stabilized halogen containing polymer compositions |
US6784230B1 (en) * | 1999-09-23 | 2004-08-31 | Rohm And Haas Company | Chlorinated vinyl resin/cellulosic blends: compositions, processes, composites, and articles therefrom |
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