JPS6138943B2 - - Google Patents
Info
- Publication number
- JPS6138943B2 JPS6138943B2 JP56033598A JP3359881A JPS6138943B2 JP S6138943 B2 JPS6138943 B2 JP S6138943B2 JP 56033598 A JP56033598 A JP 56033598A JP 3359881 A JP3359881 A JP 3359881A JP S6138943 B2 JPS6138943 B2 JP S6138943B2
- Authority
- JP
- Japan
- Prior art keywords
- acid
- vinyl chloride
- compounds
- zinc
- present
- 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.)
- Expired
Links
- 229920005989 resin Polymers 0.000 claims description 14
- 239000011347 resin Substances 0.000 claims description 14
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims description 13
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 8
- 239000000460 chlorine Substances 0.000 claims description 8
- 229910052801 chlorine Inorganic materials 0.000 claims description 8
- TXBCBTDQIULDIA-UHFFFAOYSA-N 2-[[3-hydroxy-2,2-bis(hydroxymethyl)propoxy]methyl]-2-(hydroxymethyl)propane-1,3-diol Chemical compound OCC(CO)(CO)COCC(CO)(CO)CO TXBCBTDQIULDIA-UHFFFAOYSA-N 0.000 claims description 7
- 238000006243 chemical reaction Methods 0.000 claims description 7
- GDVKFRBCXAPAQJ-UHFFFAOYSA-A dialuminum;hexamagnesium;carbonate;hexadecahydroxide Chemical compound [OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[Mg+2].[Mg+2].[Mg+2].[Mg+2].[Mg+2].[Mg+2].[Al+3].[Al+3].[O-]C([O-])=O GDVKFRBCXAPAQJ-UHFFFAOYSA-A 0.000 claims description 7
- 229960001545 hydrotalcite Drugs 0.000 claims description 7
- 229910001701 hydrotalcite Inorganic materials 0.000 claims description 7
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 claims description 4
- 239000011701 zinc Substances 0.000 claims description 4
- 229910052725 zinc Inorganic materials 0.000 claims description 4
- -1 zinc fatty acid Chemical class 0.000 claims description 4
- 238000000034 method Methods 0.000 claims description 3
- 239000011667 zinc carbonate Substances 0.000 claims description 2
- 229910000010 zinc carbonate Inorganic materials 0.000 claims description 2
- 235000004416 zinc carbonate Nutrition 0.000 claims description 2
- 239000011787 zinc oxide Substances 0.000 claims description 2
- FMRLDPWIRHBCCC-UHFFFAOYSA-L Zinc carbonate Chemical compound [Zn+2].[O-]C([O-])=O FMRLDPWIRHBCCC-UHFFFAOYSA-L 0.000 claims 1
- 235000014113 dietary fatty acids Nutrition 0.000 claims 1
- 229930195729 fatty acid Natural products 0.000 claims 1
- 239000000194 fatty acid Substances 0.000 claims 1
- 230000000087 stabilizing effect Effects 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 description 14
- 239000003381 stabilizer Substances 0.000 description 13
- 229920001577 copolymer Polymers 0.000 description 11
- 239000000203 mixture Substances 0.000 description 9
- 150000003752 zinc compounds Chemical class 0.000 description 6
- 239000002253 acid Substances 0.000 description 5
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 4
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 4
- 230000000694 effects Effects 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
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 3
- 150000008065 acid anhydrides Chemical class 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 150000002148 esters Chemical class 0.000 description 3
- 239000002994 raw material Substances 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
- 229920002554 vinyl polymer Polymers 0.000 description 3
- BJEPYKJPYRNKOW-REOHCLBHSA-N (S)-malic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O BJEPYKJPYRNKOW-REOHCLBHSA-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
- XDOFQFKRPWOURC-UHFFFAOYSA-N 16-methylheptadecanoic acid Chemical compound CC(C)CCCCCCCCCCCCCCC(O)=O XDOFQFKRPWOURC-UHFFFAOYSA-N 0.000 description 2
- JAHNSTQSQJOJLO-UHFFFAOYSA-N 2-(3-fluorophenyl)-1h-imidazole Chemical compound FC1=CC=CC(C=2NC=CN=2)=C1 JAHNSTQSQJOJLO-UHFFFAOYSA-N 0.000 description 2
- 229910018072 Al 2 O 3 Inorganic materials 0.000 description 2
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 2
- 239000004593 Epoxy Substances 0.000 description 2
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 2
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 2
- BZHJMEDXRYGGRV-UHFFFAOYSA-N Vinyl chloride Chemical compound ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 239000001361 adipic acid Substances 0.000 description 2
- 235000011037 adipic acid Nutrition 0.000 description 2
- BJEPYKJPYRNKOW-UHFFFAOYSA-N alpha-hydroxysuccinic acid Natural products OC(=O)C(O)CC(O)=O BJEPYKJPYRNKOW-UHFFFAOYSA-N 0.000 description 2
- JFCQEDHGNNZCLN-UHFFFAOYSA-N anhydrous glutaric acid Natural products OC(=O)CCCC(O)=O JFCQEDHGNNZCLN-UHFFFAOYSA-N 0.000 description 2
- 239000003963 antioxidant agent Substances 0.000 description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 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
- 230000006866 deterioration Effects 0.000 description 2
- 150000001991 dicarboxylic acids Chemical class 0.000 description 2
- POULHZVOKOAJMA-UHFFFAOYSA-N dodecanoic acid Chemical compound CCCCCCCCCCCC(O)=O POULHZVOKOAJMA-UHFFFAOYSA-N 0.000 description 2
- 238000009472 formulation Methods 0.000 description 2
- 150000004678 hydrides Chemical class 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- 150000002484 inorganic compounds Chemical class 0.000 description 2
- 229910010272 inorganic material Inorganic materials 0.000 description 2
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 2
- 239000011976 maleic acid Substances 0.000 description 2
- 239000001630 malic acid Substances 0.000 description 2
- 235000011090 malic acid Nutrition 0.000 description 2
- LVHBHZANLOWSRM-UHFFFAOYSA-N methylenebutanedioic acid Natural products OC(=O)CC(=C)C(O)=O LVHBHZANLOWSRM-UHFFFAOYSA-N 0.000 description 2
- 150000002763 monocarboxylic acids Chemical class 0.000 description 2
- 239000004014 plasticizer Substances 0.000 description 2
- 239000000843 powder Substances 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
- YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 2
- 230000006641 stabilisation Effects 0.000 description 2
- 238000011105 stabilization Methods 0.000 description 2
- 229920003002 synthetic resin Polymers 0.000 description 2
- 239000000057 synthetic resin Substances 0.000 description 2
- 239000011975 tartaric acid Substances 0.000 description 2
- 235000002906 tartaric acid Nutrition 0.000 description 2
- 229920001897 terpolymer Polymers 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
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 2
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 1
- LRQGFQDEQPZDQC-UHFFFAOYSA-N 1-Phenyl-1,3-eicosanedione Chemical compound CCCCCCCCCCCCCCCCCC(=O)CC(=O)C1=CC=CC=C1 LRQGFQDEQPZDQC-UHFFFAOYSA-N 0.000 description 1
- GGSRTHRSSCWGGK-UHFFFAOYSA-L 2,2-dibutyl-5-hydroxy-1,3,2-dioxastannepane-4,7-dione Chemical compound CCCC[Sn]1(CCCC)OC(=O)CC(O)C(=O)O1 GGSRTHRSSCWGGK-UHFFFAOYSA-L 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
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 1
- IKCLCGXPQILATA-UHFFFAOYSA-N 2-chlorobenzoic acid Chemical compound OC(=O)C1=CC=CC=C1Cl IKCLCGXPQILATA-UHFFFAOYSA-N 0.000 description 1
- IKEHOXWJQXIQAG-UHFFFAOYSA-N 2-tert-butyl-4-methylphenol Chemical compound CC1=CC=C(O)C(C(C)(C)C)=C1 IKEHOXWJQXIQAG-UHFFFAOYSA-N 0.000 description 1
- XOUQAVYLRNOXDO-UHFFFAOYSA-N 2-tert-butyl-5-methylphenol Chemical compound CC1=CC=C(C(C)(C)C)C(O)=C1 XOUQAVYLRNOXDO-UHFFFAOYSA-N 0.000 description 1
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 description 1
- 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 1
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 description 1
- 239000005711 Benzoic acid Substances 0.000 description 1
- NLZUEZXRPGMBCV-UHFFFAOYSA-N Butylhydroxytoluene Chemical compound CC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 NLZUEZXRPGMBCV-UHFFFAOYSA-N 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- 239000004709 Chlorinated polyethylene Substances 0.000 description 1
- IVRFYNSETZKRSJ-UHFFFAOYSA-N ClC=C.N#CC=CC=CC1=CC=CC=C1 Chemical compound ClC=C.N#CC=CC=CC1=CC=CC=C1 IVRFYNSETZKRSJ-UHFFFAOYSA-N 0.000 description 1
- 239000005639 Lauric acid Substances 0.000 description 1
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 1
- 239000006057 Non-nutritive feed additive Substances 0.000 description 1
- 239000005642 Oleic acid Substances 0.000 description 1
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 description 1
- GGQQSMYKSQDPFR-UHFFFAOYSA-N P([O-])([O-])[O-].[Cd+2].[Ba+2] Chemical compound P([O-])([O-])[O-].[Cd+2].[Ba+2] GGQQSMYKSQDPFR-UHFFFAOYSA-N 0.000 description 1
- 239000004743 Polypropylene Substances 0.000 description 1
- 229920001328 Polyvinylidene chloride Polymers 0.000 description 1
- 235000021355 Stearic acid Nutrition 0.000 description 1
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 1
- 229920002433 Vinyl chloride-vinyl acetate copolymer Polymers 0.000 description 1
- BGYHLZZASRKEJE-UHFFFAOYSA-N [3-[3-(3,5-ditert-butyl-4-hydroxyphenyl)propanoyloxy]-2,2-bis[3-(3,5-ditert-butyl-4-hydroxyphenyl)propanoyloxymethyl]propyl] 3-(3,5-ditert-butyl-4-hydroxyphenyl)propanoate Chemical compound CC(C)(C)C1=C(O)C(C(C)(C)C)=CC(CCC(=O)OCC(COC(=O)CCC=2C=C(C(O)=C(C=2)C(C)(C)C)C(C)(C)C)(COC(=O)CCC=2C=C(C(O)=C(C=2)C(C)(C)C)C(C)(C)C)COC(=O)CCC=2C=C(C(O)=C(C=2)C(C)(C)C)C(C)(C)C)=C1 BGYHLZZASRKEJE-UHFFFAOYSA-N 0.000 description 1
- XKTYGFMHWGOIND-UHFFFAOYSA-N [Cl].ClC=C Chemical compound [Cl].ClC=C XKTYGFMHWGOIND-UHFFFAOYSA-N 0.000 description 1
- PGTXKIZLOWULDJ-UHFFFAOYSA-N [Mg].[Zn] Chemical compound [Mg].[Zn] PGTXKIZLOWULDJ-UHFFFAOYSA-N 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical class COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 1
- 230000003078 antioxidant effect Effects 0.000 description 1
- 239000002216 antistatic agent Substances 0.000 description 1
- 229910052788 barium Inorganic materials 0.000 description 1
- DSAJWYNOEDNPEQ-UHFFFAOYSA-N barium atom Chemical compound [Ba] DSAJWYNOEDNPEQ-UHFFFAOYSA-N 0.000 description 1
- 235000010233 benzoic acid Nutrition 0.000 description 1
- 229920001400 block copolymer Polymers 0.000 description 1
- 229910052793 cadmium Inorganic materials 0.000 description 1
- BDOSMKKIYDKNTQ-UHFFFAOYSA-N cadmium atom Chemical compound [Cd] BDOSMKKIYDKNTQ-UHFFFAOYSA-N 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- ZJPJECQPVMSILT-UHFFFAOYSA-N chloroethene 3-(2-phenylethenyl)furan-2,5-dione Chemical compound ClC=C.O=C1OC(=O)C(C=CC=2C=CC=CC=2)=C1 ZJPJECQPVMSILT-UHFFFAOYSA-N 0.000 description 1
- IEJNAGSUKYCWCR-UHFFFAOYSA-N chloroethene;1,1-dichloroethene;ethenyl acetate Chemical compound ClC=C.ClC(Cl)=C.CC(=O)OC=C IEJNAGSUKYCWCR-UHFFFAOYSA-N 0.000 description 1
- KRGNPJFAKZHQPS-UHFFFAOYSA-N chloroethene;ethene Chemical group C=C.ClC=C KRGNPJFAKZHQPS-UHFFFAOYSA-N 0.000 description 1
- SQNNHEYXAJPPKH-UHFFFAOYSA-N chloroethene;prop-2-enoic acid Chemical compound ClC=C.OC(=O)C=C SQNNHEYXAJPPKH-UHFFFAOYSA-N 0.000 description 1
- 235000015165 citric acid Nutrition 0.000 description 1
- 238000004581 coalescence Methods 0.000 description 1
- 238000007033 dehydrochlorination reaction Methods 0.000 description 1
- NZZIMKJIVMHWJC-UHFFFAOYSA-N dibenzoylmethane Chemical compound C=1C=CC=CC=1C(=O)CC(=O)C1=CC=CC=C1 NZZIMKJIVMHWJC-UHFFFAOYSA-N 0.000 description 1
- 238000002845 discoloration Methods 0.000 description 1
- 229920001971 elastomer Polymers 0.000 description 1
- DPUOLQHDNGRHBS-KTKRTIGZSA-N erucic acid Chemical class CCCCCCCC\C=C/CCCCCCCCCCCC(O)=O DPUOLQHDNGRHBS-KTKRTIGZSA-N 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- 229920001038 ethylene copolymer Polymers 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 229920000578 graft copolymer Polymers 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- WYKDTBMIJGOJAN-UHFFFAOYSA-N heptatriacontane-18,20-dione Chemical compound CCCCCCCCCCCCCCCCCC(=O)CC(=O)CCCCCCCCCCCCCCCCC WYKDTBMIJGOJAN-UHFFFAOYSA-N 0.000 description 1
- 230000001771 impaired effect Effects 0.000 description 1
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 1
- 238000004898 kneading Methods 0.000 description 1
- 239000004310 lactic acid Substances 0.000 description 1
- 235000014655 lactic acid Nutrition 0.000 description 1
- OCWMFVJKFWXKNZ-UHFFFAOYSA-L lead(2+);oxygen(2-);sulfate Chemical compound [O-2].[O-2].[O-2].[Pb+2].[Pb+2].[Pb+2].[Pb+2].[O-]S([O-])(=O)=O OCWMFVJKFWXKNZ-UHFFFAOYSA-L 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 239000002075 main ingredient Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- SJOCPYUKFOTDAN-ZSOIEALJSA-N methyl (4z)-4-hydroxyimino-6,6-dimethyl-3-methylsulfanyl-5,7-dihydro-2-benzothiophene-1-carboxylate Chemical compound C1C(C)(C)C\C(=N\O)C=2C1=C(C(=O)OC)SC=2SC SJOCPYUKFOTDAN-ZSOIEALJSA-N 0.000 description 1
- 238000000465 moulding Methods 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
- WWZKQHOCKIZLMA-UHFFFAOYSA-N octanoic acid Chemical compound CCCCCCCC(O)=O WWZKQHOCKIZLMA-UHFFFAOYSA-N 0.000 description 1
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 1
- 150000002889 oleic acids Chemical class 0.000 description 1
- IWDCLRJOBJJRNH-UHFFFAOYSA-N p-cresol Chemical class CC1=CC=C(O)C=C1 IWDCLRJOBJJRNH-UHFFFAOYSA-N 0.000 description 1
- FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 229920002285 poly(styrene-co-acrylonitrile) Polymers 0.000 description 1
- 229920005671 poly(vinyl chloride-propylene) Polymers 0.000 description 1
- 229920005862 polyol Polymers 0.000 description 1
- 150000003077 polyols Chemical class 0.000 description 1
- 229920001155 polypropylene Polymers 0.000 description 1
- 229920000915 polyvinyl chloride Polymers 0.000 description 1
- 239000004800 polyvinyl chloride Substances 0.000 description 1
- 239000005033 polyvinylidene chloride Substances 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 238000003672 processing method Methods 0.000 description 1
- 239000012744 reinforcing agent Substances 0.000 description 1
- WBHHMMIMDMUBKC-XLNAKTSKSA-N ricinelaidic acid Chemical compound CCCCCC[C@@H](O)C\C=C\CCCCCCCC(O)=O WBHHMMIMDMUBKC-XLNAKTSKSA-N 0.000 description 1
- 229960003656 ricinoleic acid Drugs 0.000 description 1
- FEUQNCSVHBHROZ-UHFFFAOYSA-N ricinoleic acid Natural products CCCCCCC(O[Si](C)(C)C)CC=CCCCCCCCC(=O)OC FEUQNCSVHBHROZ-UHFFFAOYSA-N 0.000 description 1
- 229960004889 salicylic acid Drugs 0.000 description 1
- 239000000344 soap Substances 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 150000003606 tin compounds Chemical class 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- PCHQDTOLHOFHHK-UHFFFAOYSA-L zinc;hydrogen carbonate Chemical compound [Zn+2].OC([O-])=O.OC([O-])=O PCHQDTOLHOFHHK-UHFFFAOYSA-L 0.000 description 1
Landscapes
- Compositions Of Macromolecular Compounds (AREA)
Description
本発明は含塩素樹脂の安定化に関するものであ
る。更に詳しくはジペンタエリスリトールとジカ
ルボン酸との反応縮合物、亜鉛化合物およびハイ
ドロタルサイトを主体に添加することを特徴とす
る含塩素樹脂の安定化に関することである。
含塩素樹脂は加工時の加熱により脱塩化水素反
応を伴つた劣化現象を示す。一般にこれ等劣化を
防止する目的で、硬質系では安定剤として三塩基
性硫酸鉛や二塩基性ステアリン酸鉛を主体とした
所謂鉛系配合が組まれ、又ジブチルスズマレート
系安定剤を主体とした有機スズ系配合が組まれて
来た。
一方可塑剤を多量に使用出来得る系ではバリウ
ム―カドミウム―亜リン酸エステル系の安定剤が
主体となつて配合が組まれてきた。これ等の安定
剤は加工性、耐熱性、耐侯性等経験的に非常に優
れていることが確認されているが、鉛、カドミウ
ム等の有害物質や高価な有機スズ化合物を使用し
ていると云うことから必ずしも好ましい安定剤系
とは言い難い。それらの安定剤系を代替する新し
い安定剤としてバリウム、カルシウムあるいはマ
グネシウム―亜鉛系の安定剤が提唱され、実用化
されているが、これらの系において亜鉛は含塩素
樹脂に混合（練）し加熱すると「亜鉛ヤケ」を起
し、成形加工することすら難かしいことが、しば
しば起る。発明者等はこれ等の問題を解決する目
的で、これ等有害な化合物や高価な化合物を含ま
ない安定剤を種々検討した結果、特願昭51―
130999、同昭52―46968及び同昭52―60019に示し
たポリオールの部分エステル化合物が「亜鉛ヤ
ケ」防止効果が顕著であることを見出し、特願昭
53―141441に有効な発明として提起した。更に特
願昭54―23645に於て、初期色調を改良し実用性
を増した発明をも完成した。本来含塩素樹脂に対
する添加剤は主原料たる樹脂に対して異物であ
り、異物は少ない程その樹脂の物性、特性を損な
わないものである。その意味で安定剤等の副原料
の添加量の低減化が必要であろう。このことに鑑
み本発明者等は鋭意検討を重ねた結果ジペンタエ
リスリトールとジカルボン酸との反応縮合物とハ
イドロタルサイトを亜鉛化合物と併用することに
より「亜鉛ヤケ」防止を相乗的に増大させ驚異的
な熱安定性効果を発揮することを見い出した。即
ちジペンタエリスリトールとジカルボン酸との反
応縮合物とハイドロタルサイトと亜鉛化合物とを
併用して飛躍的に熱安定性が向上することから安
定剤添加量の低減化が可能になり、経済的有効性
と主原料たる樹脂の特性への影響を最小限におさ
えることが可能となり本発明を完成した。
本発明に於いては他の耐熱性向上に有効な化合
物、例えばエポキシ化合物、酸化防止剤等も併用
することができる。
本発明における含塩素樹脂としては次のような
ものをあげることが出来る。
ポリ塩化ビニル、ポリ塩化ビニリデン、塩素化
ポリエチレン、塩素化ポリプロビレン、塩化ゴ
ム、塩化ビニル―酢酸ビニル共重合体、塩化ビニ
ル―エチレン共重合体、塩化ビニル―プロビレン
共重合体、塩化ビニル―スチレン共重合体、塩化
ビニル―イソブチレン共重合体、塩化ビニル―塩
化ビニリデン共重合体、塩化ビニル―スチレン―
無水マレイン酸三元共重合体、塩化ビニル―スチ
レン―アクリロニトリル共重合体、塩化ビニル―
ブタジエン共重合体、塩化ビニル―イソブレン共
重合体、塩化ビニル―塩素化プロビレン共重合
体、塩化ビニル―塩化ビニリデン―酢酸ビニル三
元共重合体、塩化ビニル―アクリル酸エステル共
重合体、塩化ビニル―マレイン酸エステル共重合
体、塩化ビニル―メタクリル酸エステル共重合
体、塩化ビニル―アクリルニトリル共重合体、塩
化ビニル―各種ビニルエーテル共重合体などの含
塩素合成樹脂及びそれ等相互のあるいは他の塩素
を含まない合成樹脂とのブレンド品、ブロツク共
重合体、グラフト共重合体などをあげることが出
来る。
本発明におけるジペンタエリスリトールとジカ
ルボン酸との反応縮合物は、ジペンタエリスリト
ールとジカルボン酸あるいはそれ等のエステル、
酸ハライド及び酸無水物より成る群より選ばれた
少くとも１種とを反応させることにより得られる
水酸基含有率10乃至40％の反応縮合物である。エ
ステル化に用いるジカルボン酸及びエステル、酸
ハイライド及び酸無水物について以下に具体例を
示す。ジカルボン酸としてはマロン酸、コハク
酸、マレイン酸、アジピン酸、グルタル酸、イタ
コン酸、リンゴ酸、酒石酸、フタル酸、イソフタ
ル酸、テレフタル酸等であり又それらのエステ
ル、酸ハイライド及び酸無水物である。
本発明で用いられる亜鉛化合物の例を具体的に
示す。即ち酸化亜鉛、炭酸亜鉛、塩基性炭酸亜鉛
等の無機化合物及びモノカルボン酸あるいはポリ
カルボン酸との金属石鹸が用いられる。モノカル
ボン酸の例としては酢酸、乳酸、オクチル酸、ラ
ウリン酸、オレイン酸、ステアリン酸、イソステ
アリン酸、リシノレイン酸、、安息香酸、パラ第
三級ブチル安息香酸、クロル安息香酸、サルチル
酸、アクリル酸、メタアクリル酸等であり、ポリ
カルボン酸の例としてはマロン酸、コハク酸、マ
レイン酸、アジピン酸、グルタル酸、イタコン
酸、リンゴ酸、酒石酸、クエン酸、フタル酸、イ
ソフタル酸、テレフタル酸、トリメリツト酸、ピ
ロメリツト酸等である。
本発明で用いるハイドロタルサイトは一般式
XAl2O3・YMgO・CO2・Ｚ（H2O）の組成を持つ
た無機化合物であり、一般にAl2O3とMgOの比率
により特性が異なる。本発明を完成するに当り協
和化学工業株式会社より市販されているDHT―
4A（Al2O3とMgOの比は１対４とされている）
を用いた。
本発明において上記した化合物以外で、一般に
安定剤として各種知られた化合物を併用しても本
発明の特徴を損うことはない。ここで使用され得
るエポキシ化合物としてはエポキシ化植物油、エ
ポキシ化オレイン酸エステル類、エポキシ化エル
シン酸エステル類、エピクロルヒドリン―ビスフ
エノール化合物類、エピクロルヒドリン―ポリク
レゾール化合物類、エピクロルヒドリンレゾルシ
ン化合物等がある。
又酸化防止剤としては、ヒドロキシル基が少な
くとも１個の三級あるいは二級アルキル基により
ヒンダードされたフエノール基を同一分子内に１
個乃至４個持つ化合物の群から選ばれた化合物
で、その具体的例としては、スチレン化パラクレ
ゾール、2.6―ジ第三級ブチル４―メチルフエノ
ール、ブチル化アニソール、4.4′―メチレンビス
（６―第３級ブチル３―メチルフエノール）、
2.2′―メチレンビス（６―第３級ブチル―４―メ
チルフエノール）、１，３，５―トリメチル―
２，４，６―トリス（3.5―ジ第三級ブチル―４
―ヒドロキシベンジル）ベンゼン、テトラキス
〔３―（４―ヒドロキシ―3.5―ジ第三級ブチルフ
エニル）プロピオニルオキシメチル〕メタンなど
である。
本発明にはその用途、加工法、成型法等によつ
て可塑剤、滑剤、加工助剤、耐侯性改良剤、帯電
防止剤、防曇剤、強化剤、充填剤、顔料等が併用
される。
又初期着色改良剤としては特公昭52―47949特
許請求の範囲に含まれる化合物を挙げることがで
きるが、より実用的なものとしてジベンゾイルメ
タン、ベンゾイルステアロイルメタン、ジステア
ロイルメタン等である。
本発明を説明するのに用いたジペンタエリスリ
トールとジカルボン酸との反応縮合物について第
１表に示した。
The present invention relates to stabilization of chlorinated resins. More specifically, the present invention relates to stabilization of chlorine-containing resins characterized by mainly adding a reaction condensate of dipentaerythritol and dicarboxylic acid, a zinc compound, and hydrotalcite. Chlorine-containing resins exhibit deterioration phenomena accompanied by dehydrochlorination reactions due to heating during processing. Generally, in order to prevent such deterioration, hard systems are formulated with so-called lead-based formulations mainly containing tribasic lead sulfate and dibasic lead stearate as stabilizers, and also containing dibutyltin malate-based stabilizers as the main stabilizers. Organic tin-based formulations have been developed. On the other hand, in systems where a large amount of plasticizer can be used, barium-cadmium-phosphite stabilizers have been used as the main ingredient. It has been empirically confirmed that these stabilizers have excellent processability, heat resistance, weather resistance, etc., but they contain harmful substances such as lead and cadmium and expensive organic tin compounds. For this reason, it is difficult to say that it is necessarily a preferable stabilizer system. Barium, calcium, or magnesium-zinc stabilizers have been proposed and put into practical use as new stabilizers to replace those stabilizer systems, but in these systems, zinc is mixed (kneaded) with chlorine-containing resin and heated. This often causes ``zinc burn'' and makes it difficult to process. In order to solve these problems, the inventors investigated various stabilizers that do not contain these harmful or expensive compounds, and as a result, they filed a patent application filed in 1973.
It was discovered that the polyol partial ester compounds shown in No. 130999, No. 130999, No. 1983-46968, and No. 52-60019 had a remarkable effect on preventing "zinc discoloration", and a patent application No. 130999 was filed.
53-141441 as a valid invention. Furthermore, in a patent application filed in 1972-23645, he completed an invention that improved the initial color tone and increased its practicality. Essentially, additives for chlorine-containing resins are foreign substances to the resin, which is the main raw material, and the less foreign substances there are, the less the physical properties and characteristics of the resin will be impaired. In this sense, it will be necessary to reduce the amount of auxiliary raw materials such as stabilizers. In view of this, the inventors of the present invention have conducted extensive studies and have surprisingly been able to synergistically increase the prevention of "zinc tan" by using a reaction condensate of dipentaerythritol and dicarboxylic acid and hydrotalcite in combination with a zinc compound. It has been found that this material exhibits a thermal stability effect. In other words, by using a reaction condensate of dipentaerythritol and dicarboxylic acid in combination with hydrotalcite and a zinc compound, thermal stability is dramatically improved, making it possible to reduce the amount of stabilizer added, making it economically effective. The present invention has been completed by making it possible to minimize the effect on the properties of the resin, which is the main raw material. In the present invention, other compounds effective in improving heat resistance, such as epoxy compounds and antioxidants, can also be used. Examples of the chlorine-containing resin in the present invention include the following. Polyvinyl chloride, polyvinylidene chloride, chlorinated polyethylene, chlorinated polypropylene, chlorinated rubber, vinyl chloride-vinyl acetate copolymer, vinyl chloride-ethylene copolymer, vinyl chloride-propylene copolymer, vinyl chloride-styrene copolymer Coalescence, vinyl chloride-isobutylene copolymer, vinyl chloride-vinylidene chloride copolymer, vinyl chloride-styrene-
Maleic anhydride terpolymer, vinyl chloride-styrene-acrylonitrile copolymer, vinyl chloride-
Butadiene copolymer, vinyl chloride-isobrene copolymer, vinyl chloride-chlorinated propylene copolymer, vinyl chloride-vinylidene chloride-vinyl acetate terpolymer, vinyl chloride-acrylic acid ester copolymer, vinyl chloride- Chlorine-containing synthetic resins such as maleate ester copolymers, vinyl chloride-methacrylate ester copolymers, vinyl chloride-acrylonitrile copolymers, vinyl chloride-various vinyl ether copolymers, and their mutual or other chlorine Blend products with synthetic resins that do not contain the same, block copolymers, graft copolymers, etc. can be mentioned. The reaction condensate of dipentaerythritol and dicarboxylic acid in the present invention includes dipentaerythritol and dicarboxylic acid or an ester thereof,
It is a reaction condensate having a hydroxyl group content of 10 to 40% obtained by reacting at least one selected from the group consisting of acid halides and acid anhydrides. Specific examples of dicarboxylic acids, esters, acid hydrides, and acid anhydrides used in esterification are shown below. Dicarboxylic acids include malonic acid, succinic acid, maleic acid, adipic acid, glutaric acid, itaconic acid, malic acid, tartaric acid, phthalic acid, isophthalic acid, terephthalic acid, and their esters, acid hydrides, and acid anhydrides. be. Specific examples of zinc compounds used in the present invention are shown below. That is, metal soaps containing inorganic compounds such as zinc oxide, zinc carbonate, basic zinc carbonate, and monocarboxylic acids or polycarboxylic acids are used. Examples of monocarboxylic acids are acetic acid, lactic acid, octylic acid, lauric acid, oleic acid, stearic acid, isostearic acid, ricinoleic acid, benzoic acid, para-tert-butylbenzoic acid, chlorobenzoic acid, salicylic acid, and acrylic acid. , methacrylic acid, etc. Examples of polycarboxylic acids include malonic acid, succinic acid, maleic acid, adipic acid, glutaric acid, itaconic acid, malic acid, tartaric acid, citric acid, phthalic acid, isophthalic acid, terephthalic acid, These include trimellitic acid and pyromellitic acid. The hydrotalcite used in the present invention has the general formula
It is an inorganic compound with a composition of XAl 2 O 3・YMgO ・CO 2・Z (H 2 O), and its properties generally vary depending on the ratio of Al 2 O 3 and MgO. In completing the present invention, DHT commercially available from Kyowa Chemical Industry Co., Ltd.
4A (The ratio of Al 2 O 3 and MgO is said to be 1:4)
was used. In the present invention, in addition to the above-mentioned compounds, various compounds generally known as stabilizers may be used in combination without impairing the characteristics of the present invention. Epoxy compounds that can be used here include epoxidized vegetable oils, epoxidized oleic acid esters, epoxidized erucic acid esters, epichlorohydrin-bisphenol compounds, epichlorohydrin-polycresol compounds, epichlorohydrin resorcinol compounds, and the like. In addition, as an antioxidant, one phenol group in which the hydroxyl group is hindered by at least one tertiary or secondary alkyl group is used in the same molecule.
Compounds selected from the group of compounds having from 1 to 4 atoms, including styrenated para-cresol, 2.6-di-tert-butyl 4-methylphenol, butylated anisole, 4.4'-methylenebis(6- tertiary butyl 3-methylphenol),
2.2'-methylenebis(6-tertiary butyl-4-methylphenol), 1,3,5-trimethyl-
2,4,6-tris(3.5-ditert-butyl-4
-hydroxybenzyl)benzene, tetrakis[3-(4-hydroxy-3.5-di-tert-butylphenyl)propionyloxymethyl]methane, etc. Depending on the purpose, processing method, molding method, etc. of the present invention, plasticizers, lubricants, processing aids, weather resistance improvers, antistatic agents, antifogging agents, reinforcing agents, fillers, pigments, etc. may be used in combination. . Examples of the initial color improver include compounds included in the claims of Japanese Patent Publication No. 52-47949, and more practical examples include dibenzoylmethane, benzoylstearoylmethane, and distearoylmethane. Table 1 shows the reaction condensate of dipentaerythritol and dicarboxylic acid used to explain the present invention.
【表】
本発明の優れた効果について実施例をもつて説
明するが本発明はこれらの実施例によつて限定さ
れるものではない。
実施例 １
塩化ビニル樹脂粉末〔住友化学工業株式会社製
スミリツトSX―7GK〕100重量部と亜鉛化合
物、第１表記載縮合物、ハイドロタルサイト及び
他の化合物を混合した組成物を６インチ２本ロー
ルで、180℃５分混練しシートを作成した。その
シートを190℃オーブン中で耐熱試験を行い第２
表の結果を得た。[Table] The excellent effects of the present invention will be explained with examples, but the present invention is not limited by these examples. Example 1 Two 6-inch bottles of a composition prepared by mixing 100 parts by weight of vinyl chloride resin powder [Sumiritto SX-7GK manufactured by Sumitomo Chemical Co., Ltd.] with a zinc compound, a condensate listed in Table 1, hydrotalcite, and other compounds were prepared. The mixture was kneaded with a roll for 5 minutes at 180°C to form a sheet. The sheet was then subjected to a heat resistance test in an oven at 190°C.
Obtained the results in the table.
【表】
実施例 ２
エチレン―酢酸ビニル―塩化ビニルグラフトマ
―樹脂〔東洋曹達株式会社製リユーロンHI―
Ｅ―２〕100重量部及び実施例１と同様な化合物
を混合した組成物を６インチ２本ロールで170℃
５分混練しシートを作成した。そのシートを190
℃オーブン中で耐熱試験を行い第３表の結果を得
た。[Table] Example 2 Ethylene-vinyl acetate-vinyl chloride graftomer resin [Lieuron HI manufactured by Toyo Soda Co., Ltd.]
E-2] A composition prepared by mixing 100 parts by weight and the same compound as in Example 1 was heated at 170°C using two 6-inch rolls.
The mixture was kneaded for 5 minutes to form a sheet. 190 that sheet
A heat resistance test was conducted in a °C oven and the results shown in Table 3 were obtained.
【表】
実施例 ３
塩化ビニル樹脂粉末〔住友化学工業株式会社製
スミリツトSX―11F〕100重量部と亜鉛化合
物、第１表記載化合物、ハイドロタルサイト及び
他の化合物を混合した組成物を６インチ２本ロー
ルで、165℃５分間混練しシートを作成した。そ
のシートを180℃オーブン中で耐熱試験を行い第
４表の結果を得た。[Table] Example 3 A composition prepared by mixing 100 parts by weight of vinyl chloride resin powder [Sumiritto SX-11F manufactured by Sumitomo Chemical Co., Ltd.], a zinc compound, a compound listed in Table 1, hydrotalcite, and other compounds was mixed into a 6-inch film. A sheet was prepared by kneading with two rolls at 165°C for 5 minutes. The sheet was subjected to a heat resistance test in an oven at 180°C, and the results shown in Table 4 were obtained.
Claims (1)
反応縮合物 酸化亜鉛、炭酸亜鉛または脂肪酸亜鉛 ハイドロタルサイトを添加することを特徴と
する含塩素樹脂の安定化法。[Claims] 1. A method for stabilizing a chlorine-containing resin, which comprises adding to the chlorine-containing resin a reaction condensate of dipentaerythritol and dicarboxylic acid, zinc oxide, zinc carbonate, or zinc fatty acid, and hydrotalcite.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP56033598A JPS57147552A (en) | 1981-03-09 | 1981-03-09 | Stabilizing method of chlorine-containing resin |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP56033598A JPS57147552A (en) | 1981-03-09 | 1981-03-09 | Stabilizing method of chlorine-containing resin |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS57147552A JPS57147552A (en) | 1982-09-11 |
| JPS6138943B2 true JPS6138943B2 (en) | 1986-09-01 |
Family
ID=12390919
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP56033598A Granted JPS57147552A (en) | 1981-03-09 | 1981-03-09 | Stabilizing method of chlorine-containing resin |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS57147552A (en) |
Families Citing this family (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5984946A (en) * | 1982-11-04 | 1984-05-16 | Nissan Fuero Yuki Kagaku Kk | Halogen-containing resin composition |
| JPS60168745A (en) * | 1984-02-13 | 1985-09-02 | Hitachi Cable Ltd | Vinyl composition |
| JPS61111349A (en) * | 1984-11-06 | 1986-05-29 | Mitsubishi Monsanto Chem Co | Vinyl chloride resin composition for molding anti-fogging agricultural film |
| JP3379691B2 (en) * | 1997-12-22 | 2003-02-24 | 日本製紙株式会社 | Chlorinated polyolefin composition with good stability |
| KR100584167B1 (en) | 1999-02-05 | 2006-05-26 | 토다 고교 가부시끼가이샤 | Mg-Al-Based hydrotalcite type particles, chlorine-containing resin composition and process for producing the particles |
| CN102124052B (en) | 2008-06-16 | 2013-12-25 | 可乐丽股份有限公司 | Polyvinyl chloride resin composition and manufacturing method thereof |
| KR20110030585A (en) | 2008-06-16 | 2011-03-23 | 가부시키가이샤 구라레 | Polyvinyl chloride resin composition and method for producing the same |
| CN102124053B (en) | 2008-06-18 | 2014-01-01 | 可乐丽股份有限公司 | Polyvinyl chloride resin composition and manufacturing method thereof |
| JPWO2009157401A1 (en) | 2008-06-23 | 2011-12-15 | 株式会社クラレ | Polyvinyl chloride resin composition and method for producing the same |
| JP5480150B2 (en) | 2008-10-08 | 2014-04-23 | 株式会社クラレ | Polyvinyl chloride resin composition and method for producing the same |
| EP2371899B1 (en) | 2008-12-26 | 2015-08-12 | Kuraray Co., Ltd. | Polyvinyl chloride resin composition and manufacturing method therefor |
| WO2011093487A1 (en) | 2010-02-01 | 2011-08-04 | 株式会社クラレ | Thermostabilizer for polyvinyl chloride, polyvinyl chloride resin composition, and method for producing the same |
| US9163138B2 (en) | 2011-09-22 | 2015-10-20 | Kuraray Co., Ltd. | Halogen-containing resin composition, production process therefor and molded article therefrom |
-
1981
- 1981-03-09 JP JP56033598A patent/JPS57147552A/en active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS57147552A (en) | 1982-09-11 |
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