CA1202479A - Halogen-containing polymers stabilized with organic antimony compound and an ortho mercapto phenol compound - Google Patents
Halogen-containing polymers stabilized with organic antimony compound and an ortho mercapto phenol compoundInfo
- Publication number
- CA1202479A CA1202479A CA000435648A CA435648A CA1202479A CA 1202479 A CA1202479 A CA 1202479A CA 000435648 A CA000435648 A CA 000435648A CA 435648 A CA435648 A CA 435648A CA 1202479 A CA1202479 A CA 1202479A
- Authority
- CA
- Canada
- Prior art keywords
- organic
- alkyl
- compounds
- antimony
- group
- 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
- 150000001463 antimony compounds Chemical class 0.000 title claims abstract description 53
- 229920000642 polymer Polymers 0.000 title claims abstract description 47
- 150000001875 compounds Chemical class 0.000 title claims description 27
- 229910052736 halogen Inorganic materials 0.000 title claims description 21
- 150000002367 halogens Chemical class 0.000 title claims description 21
- VMKYTRPNOVFCGZ-UHFFFAOYSA-N 2-sulfanylphenol Chemical compound OC1=CC=CC=C1S VMKYTRPNOVFCGZ-UHFFFAOYSA-N 0.000 title description 6
- 239000000203 mixture Substances 0.000 claims abstract description 106
- 150000002894 organic compounds Chemical class 0.000 claims abstract description 50
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 39
- -1 MERCAPTO PHENOL COMPOUND Chemical class 0.000 claims abstract description 34
- 239000003381 stabilizer Substances 0.000 claims abstract description 34
- 125000003118 aryl group Chemical group 0.000 claims abstract description 33
- 229940058905 antimony compound for treatment of leishmaniasis and trypanosomiasis Drugs 0.000 claims abstract description 28
- 125000000217 alkyl group Chemical group 0.000 claims description 37
- 229920000620 organic polymer Polymers 0.000 claims description 32
- 229910052787 antimony Inorganic materials 0.000 claims description 29
- WATWJIUSRGPENY-UHFFFAOYSA-N antimony atom Chemical group [Sb] WATWJIUSRGPENY-UHFFFAOYSA-N 0.000 claims description 29
- 125000003342 alkenyl group Chemical group 0.000 claims description 23
- 125000004432 carbon atom Chemical group C* 0.000 claims description 22
- 125000003396 thiol group Chemical group [H]S* 0.000 claims description 21
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 20
- 229910052799 carbon Inorganic materials 0.000 claims description 20
- 229910052717 sulfur Inorganic materials 0.000 claims description 19
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 18
- 239000011593 sulfur Substances 0.000 claims description 18
- 101100495912 Arabidopsis thaliana CHR12 gene Proteins 0.000 claims description 16
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 15
- 125000002837 carbocyclic group Chemical group 0.000 claims description 12
- 125000002947 alkylene group Chemical group 0.000 claims description 11
- 125000004450 alkenylene group Chemical group 0.000 claims description 8
- 125000002877 alkyl aryl group Chemical group 0.000 claims description 7
- 150000005840 aryl radicals Chemical class 0.000 claims description 6
- 125000000732 arylene group Chemical group 0.000 claims description 6
- 230000006866 deterioration Effects 0.000 claims description 6
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 5
- 125000000392 cycloalkenyl group Chemical group 0.000 claims description 5
- 239000002253 acid Substances 0.000 claims description 4
- 229910052760 oxygen Inorganic materials 0.000 claims description 4
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 2
- 125000003545 alkoxy group Chemical group 0.000 claims description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 2
- 150000001735 carboxylic acids Chemical class 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 150000002431 hydrogen Chemical group 0.000 claims description 2
- 125000005358 mercaptoalkyl group Chemical group 0.000 claims description 2
- 239000001301 oxygen Substances 0.000 claims description 2
- RFEBDZANCVHDLP-UHFFFAOYSA-N 3-[(4-cyanophenyl)methylamino]-6-(trifluoromethyl)quinoxaline-2-carboxylic acid Chemical compound OC(=O)C1=NC2=CC=C(C(F)(F)F)C=C2N=C1NCC1=CC=C(C#N)C=C1 RFEBDZANCVHDLP-UHFFFAOYSA-N 0.000 claims 1
- YPMOSINXXHVZIL-UHFFFAOYSA-N sulfanylideneantimony Chemical compound [Sb]=S YPMOSINXXHVZIL-UHFFFAOYSA-N 0.000 claims 1
- PXQLVRUNWNTZOS-UHFFFAOYSA-N sulfanyl Chemical class [SH] PXQLVRUNWNTZOS-UHFFFAOYSA-N 0.000 abstract description 7
- 238000004519 manufacturing process Methods 0.000 abstract description 6
- 230000000087 stabilizing effect Effects 0.000 abstract description 3
- 230000002542 deteriorative effect Effects 0.000 abstract 1
- 229920002554 vinyl polymer Polymers 0.000 description 17
- UHOVQNZJYSORNB-UHFFFAOYSA-N monobenzene Natural products C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 15
- 229920001577 copolymer Polymers 0.000 description 14
- 229920001519 homopolymer Polymers 0.000 description 13
- 229920000915 polyvinyl chloride Polymers 0.000 description 9
- 239000000460 chlorine Substances 0.000 description 8
- 239000004800 polyvinyl chloride Substances 0.000 description 8
- 238000002845 discoloration Methods 0.000 description 7
- 230000006641 stabilisation Effects 0.000 description 6
- 238000011105 stabilization Methods 0.000 description 6
- 239000004215 Carbon black (E152) Substances 0.000 description 5
- 238000009472 formulation Methods 0.000 description 5
- 229930195733 hydrocarbon Natural products 0.000 description 5
- 229920002959 polymer blend Polymers 0.000 description 5
- BZHJMEDXRYGGRV-UHFFFAOYSA-N Vinyl chloride Chemical compound ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 description 4
- 238000000034 method Methods 0.000 description 4
- 239000011347 resin Substances 0.000 description 4
- 229920005989 resin Polymers 0.000 description 4
- 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 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 230000015556 catabolic process Effects 0.000 description 3
- 238000006731 degradation reaction Methods 0.000 description 3
- 239000000178 monomer Substances 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- ISGHUYCZFWLBRU-UHFFFAOYSA-N 2-[2-(2-sulfanylacetyl)oxyethoxy]ethyl 2-sulfanylacetate Chemical compound SCC(=O)OCCOCCOC(=O)CS ISGHUYCZFWLBRU-UHFFFAOYSA-N 0.000 description 2
- WEMJWKKJHSZRQT-KTKRTIGZSA-N 2-sulfanylethyl (z)-octadec-9-enoate Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OCCS WEMJWKKJHSZRQT-KTKRTIGZSA-N 0.000 description 2
- ORDRGXFSRBRQQG-UHFFFAOYSA-N 6-methylheptyl 2-sulfanylpropanoate Chemical compound CC(C)CCCCCOC(=O)C(C)S ORDRGXFSRBRQQG-UHFFFAOYSA-N 0.000 description 2
- SOGAXMICEFXMKE-UHFFFAOYSA-N Butylmethacrylate Chemical compound CCCCOC(=O)C(C)=C SOGAXMICEFXMKE-UHFFFAOYSA-N 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- 239000004709 Chlorinated polyethylene Substances 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
- 101001028025 Homo sapiens Mdm2-binding protein Proteins 0.000 description 2
- 101710185544 Maltose-binding periplasmic protein Proteins 0.000 description 2
- 101710175625 Maltose/maltodextrin-binding periplasmic protein Proteins 0.000 description 2
- 101710144262 Maltotriose-binding protein Proteins 0.000 description 2
- 102100037572 Mdm2-binding protein Human genes 0.000 description 2
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 description 2
- 239000004698 Polyethylene Substances 0.000 description 2
- 239000004793 Polystyrene Substances 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 2
- 239000003963 antioxidant agent Substances 0.000 description 2
- 235000006708 antioxidants Nutrition 0.000 description 2
- CJZGTCYPCWQAJB-UHFFFAOYSA-L calcium stearate Chemical compound [Ca+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O CJZGTCYPCWQAJB-UHFFFAOYSA-L 0.000 description 2
- 239000008116 calcium stearate Substances 0.000 description 2
- 235000013539 calcium stearate Nutrition 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 238000007796 conventional method Methods 0.000 description 2
- RWGFKTVRMDUZSP-UHFFFAOYSA-N cumene Chemical compound CC(C)C1=CC=CC=C1 RWGFKTVRMDUZSP-UHFFFAOYSA-N 0.000 description 2
- FJKIXWOMBXYWOQ-UHFFFAOYSA-N ethenoxyethane Chemical compound CCOC=C FJKIXWOMBXYWOQ-UHFFFAOYSA-N 0.000 description 2
- 239000003063 flame retardant Substances 0.000 description 2
- 150000002430 hydrocarbons Chemical class 0.000 description 2
- 230000007774 longterm Effects 0.000 description 2
- 239000000314 lubricant Substances 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 239000012188 paraffin wax Substances 0.000 description 2
- 239000004014 plasticizer Substances 0.000 description 2
- 229920003229 poly(methyl methacrylate) Polymers 0.000 description 2
- 229920000573 polyethylene Polymers 0.000 description 2
- 239000004926 polymethyl methacrylate Substances 0.000 description 2
- 229920002223 polystyrene Polymers 0.000 description 2
- 230000002035 prolonged effect Effects 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 2
- 229920002818 (Hydroxyethyl)methacrylate Polymers 0.000 description 1
- TXECTBGVEUDNSL-UHFFFAOYSA-N 1-acetyloxyprop-2-enyl acetate Chemical compound CC(=O)OC(C=C)OC(C)=O TXECTBGVEUDNSL-UHFFFAOYSA-N 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
- OBDBCTHEWRIQMB-UHFFFAOYSA-N 2,4-bis(sulfanyl)benzene-1,3,5-triol Chemical compound OC1=CC(O)=C(S)C(O)=C1S OBDBCTHEWRIQMB-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
- OYUNTGBISCIYPW-UHFFFAOYSA-N 2-chloroprop-2-enenitrile Chemical compound ClC(=C)C#N OYUNTGBISCIYPW-UHFFFAOYSA-N 0.000 description 1
- DKKWUPLGEDIICA-UHFFFAOYSA-N 2-sulfanylbenzene-1,3,5-triol Chemical compound OC1=CC(O)=C(S)C(O)=C1 DKKWUPLGEDIICA-UHFFFAOYSA-N 0.000 description 1
- UCVORQZRHHHDPS-UHFFFAOYSA-N 2-tert-butyl-4-methyl-6-sulfanylphenol Chemical compound CC1=CC(S)=C(O)C(C(C)(C)C)=C1 UCVORQZRHHHDPS-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
- KDWUXIZZRXCHEE-UHFFFAOYSA-N 3-sulfanylbenzene-1,2,4,5-tetrol Chemical compound OC1=CC(O)=C(O)C(S)=C1O KDWUXIZZRXCHEE-UHFFFAOYSA-N 0.000 description 1
- QDMMXVMPDPEYJK-UHFFFAOYSA-N 3-sulfanylbenzene-1,2,4-triol Chemical compound OC1=CC=C(O)C(S)=C1O QDMMXVMPDPEYJK-UHFFFAOYSA-N 0.000 description 1
- CXMBJBCPGQIVET-UHFFFAOYSA-N 3-sulfanylbenzene-1,2-diol Chemical compound OC1=CC=CC(S)=C1O CXMBJBCPGQIVET-UHFFFAOYSA-N 0.000 description 1
- LZHDMIAKNFGFBU-UHFFFAOYSA-N 4-nonyl-2-sulfanylphenol Chemical compound CCCCCCCCCC1=CC=C(O)C(S)=C1 LZHDMIAKNFGFBU-UHFFFAOYSA-N 0.000 description 1
- BUPMNUNSNHTOLV-UHFFFAOYSA-N 4-tert-butyl-2-sulfanylphenol Chemical compound CC(C)(C)C1=CC=C(O)C(S)=C1 BUPMNUNSNHTOLV-UHFFFAOYSA-N 0.000 description 1
- IUNVCWLKOOCPIT-UHFFFAOYSA-N 6-methylheptylsulfanyl 2-hydroxyacetate Chemical compound CC(C)CCCCCSOC(=O)CO IUNVCWLKOOCPIT-UHFFFAOYSA-N 0.000 description 1
- WQWKDENEJVGIFR-UHFFFAOYSA-N 6-sulfanylbenzene-1,2,4-triol Chemical compound OC1=CC(O)=C(O)C(S)=C1 WQWKDENEJVGIFR-UHFFFAOYSA-N 0.000 description 1
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- 239000004801 Chlorinated PVC Substances 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 229920000089 Cyclic olefin copolymer Polymers 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
- IEPRKVQEAMIZSS-WAYWQWQTSA-N Diethyl maleate Chemical compound CCOC(=O)\C=C/C(=O)OCC IEPRKVQEAMIZSS-WAYWQWQTSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- JIGUQPWFLRLWPJ-UHFFFAOYSA-N Ethyl acrylate Chemical compound CCOC(=O)C=C JIGUQPWFLRLWPJ-UHFFFAOYSA-N 0.000 description 1
- 229920006385 Geon Polymers 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- WOBHKFSMXKNTIM-UHFFFAOYSA-N Hydroxyethyl methacrylate Chemical compound CC(=C)C(=O)OCCO WOBHKFSMXKNTIM-UHFFFAOYSA-N 0.000 description 1
- 241001508691 Martes zibellina Species 0.000 description 1
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 1
- 239000002033 PVDF binder Substances 0.000 description 1
- 229920001328 Polyvinylidene chloride Polymers 0.000 description 1
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 description 1
- QYKIQEUNHZKYBP-UHFFFAOYSA-N Vinyl ether Chemical class C=COC=C QYKIQEUNHZKYBP-UHFFFAOYSA-N 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
- 239000000654 additive Substances 0.000 description 1
- 150000001336 alkenes Chemical class 0.000 description 1
- 125000005250 alkyl acrylate group Chemical group 0.000 description 1
- 230000003078 antioxidant effect Effects 0.000 description 1
- 239000002216 antistatic agent Substances 0.000 description 1
- CQEYYJKEWSMYFG-UHFFFAOYSA-N butyl acrylate Chemical compound CCCCOC(=O)C=C CQEYYJKEWSMYFG-UHFFFAOYSA-N 0.000 description 1
- 229910000019 calcium carbonate Inorganic materials 0.000 description 1
- 235000010216 calcium carbonate Nutrition 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- ALKXBQOWBSLLQP-IPZCTEOASA-N chloroethene;(e)-2,3-diethylbut-2-enedioic acid Chemical compound ClC=C.CC\C(C(O)=O)=C(\CC)C(O)=O ALKXBQOWBSLLQP-IPZCTEOASA-N 0.000 description 1
- SZOPAPBTRRMGMD-UHFFFAOYSA-N chloroethene;1,1,2-trichloroethene Chemical group ClC=C.ClC=C(Cl)Cl SZOPAPBTRRMGMD-UHFFFAOYSA-N 0.000 description 1
- DHZSIQDUYCWNSB-UHFFFAOYSA-N chloroethene;1,1-dichloroethene Chemical compound ClC=C.ClC(Cl)=C DHZSIQDUYCWNSB-UHFFFAOYSA-N 0.000 description 1
- BMZQPXKCLRADET-UHFFFAOYSA-N chloroethene;2-ethylhexyl prop-2-enoate Chemical compound ClC=C.CCCCC(CC)COC(=O)C=C BMZQPXKCLRADET-UHFFFAOYSA-N 0.000 description 1
- HGAZMNJKRQFZKS-UHFFFAOYSA-N chloroethene;ethenyl acetate Chemical compound ClC=C.CC(=O)OC=C HGAZMNJKRQFZKS-UHFFFAOYSA-N 0.000 description 1
- 239000003431 cross linking reagent Substances 0.000 description 1
- 229940117389 dichlorobenzene Drugs 0.000 description 1
- IEPRKVQEAMIZSS-AATRIKPKSA-N diethyl fumarate Chemical compound CCOC(=O)\C=C\C(=O)OCC IEPRKVQEAMIZSS-AATRIKPKSA-N 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 229920001971 elastomer Polymers 0.000 description 1
- 230000007613 environmental effect Effects 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
- SUPCQIBBMFXVTL-UHFFFAOYSA-N ethyl 2-methylprop-2-enoate Chemical compound CCOC(=O)C(C)=C SUPCQIBBMFXVTL-UHFFFAOYSA-N 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 239000010419 fine particle Substances 0.000 description 1
- ZTQSADJAYQOCDD-UHFFFAOYSA-N ginsenoside-Rd2 Natural products C1CC(C2(CCC3C(C)(C)C(OC4C(C(O)C(O)C(CO)O4)O)CCC3(C)C2CC2O)C)(C)C2C1C(C)(CCC=C(C)C)OC(C(C(O)C1O)O)OC1COC1OCC(O)C(O)C1O ZTQSADJAYQOCDD-UHFFFAOYSA-N 0.000 description 1
- PBZROIMXDZTJDF-UHFFFAOYSA-N hepta-1,6-dien-4-one Chemical compound C=CCC(=O)CC=C PBZROIMXDZTJDF-UHFFFAOYSA-N 0.000 description 1
- 125000001183 hydrocarbyl group Chemical group 0.000 description 1
- 150000002688 maleic acid derivatives Chemical class 0.000 description 1
- AWJZTPWDQYFQPQ-UHFFFAOYSA-N methyl 2-chloroprop-2-enoate Chemical compound COC(=O)C(Cl)=C AWJZTPWDQYFQPQ-UHFFFAOYSA-N 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 229920003052 natural elastomer Polymers 0.000 description 1
- 229920001194 natural rubber Polymers 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 1
- UCUUFSAXZMGPGH-UHFFFAOYSA-N penta-1,4-dien-3-one Chemical class C=CC(=O)C=C UCUUFSAXZMGPGH-UHFFFAOYSA-N 0.000 description 1
- PNJWIWWMYCMZRO-UHFFFAOYSA-N pent‐4‐en‐2‐one Natural products CC(=O)CC=C PNJWIWWMYCMZRO-UHFFFAOYSA-N 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 229920001490 poly(butyl methacrylate) polymer Polymers 0.000 description 1
- 229920002620 polyvinyl fluoride Polymers 0.000 description 1
- 239000005033 polyvinylidene chloride Substances 0.000 description 1
- 229920002981 polyvinylidene fluoride Polymers 0.000 description 1
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 239000005060 rubber Substances 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 238000007493 shaping process Methods 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 241000894007 species Species 0.000 description 1
- RVEZZJVBDQCTEF-UHFFFAOYSA-N sulfenic acid Chemical compound SO RVEZZJVBDQCTEF-UHFFFAOYSA-N 0.000 description 1
- 230000002195 synergetic effect Effects 0.000 description 1
- 229920003051 synthetic elastomer Polymers 0.000 description 1
- 239000005061 synthetic rubber Substances 0.000 description 1
- RMVRSNDYEFQCLF-UHFFFAOYSA-N thiophenol Substances SC1=CC=CC=C1 RMVRSNDYEFQCLF-UHFFFAOYSA-N 0.000 description 1
- 239000004408 titanium dioxide Substances 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
- FUSUHKVFWTUUBE-UHFFFAOYSA-N vinyl methyl ketone Natural products CC(=O)C=C FUSUHKVFWTUUBE-UHFFFAOYSA-N 0.000 description 1
- 239000001993 wax Substances 0.000 description 1
- 238000004383 yellowing Methods 0.000 description 1
Classifications
-
- 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
- C08K5/59—Arsenic- or antimony-containing compounds
-
- 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
- C08K5/36—Sulfur-, selenium-, or tellurium-containing compounds
- C08K5/37—Thiols
Landscapes
- 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)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US06/406,584 US4440891A (en) | 1982-08-09 | 1982-08-09 | Halogen-containing polymers stabilized with organic antimony compound and an ortho mercapto phenol compound |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1202479A true CA1202479A (en) | 1986-04-01 |
Family
ID=23608629
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA000435648A Expired CA1202479A (en) | 1982-08-09 | 1983-08-30 | Halogen-containing polymers stabilized with organic antimony compound and an ortho mercapto phenol compound |
Country Status (5)
| Country | Link |
|---|---|
| US (1) | US4440891A (en, 2012) |
| EP (1) | EP0134348A1 (en, 2012) |
| JP (1) | JPS6067549A (en, 2012) |
| AU (1) | AU560936B2 (en, 2012) |
| CA (1) | CA1202479A (en, 2012) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4558083A (en) * | 1981-02-26 | 1985-12-10 | Morton Thiokol, Inc. | Stabilizer compositions and polymers containing same |
| US4617334A (en) * | 1982-08-09 | 1986-10-14 | Morton Thiokol, Inc. | Stabilizer compositions for PVC |
| US4806270A (en) * | 1987-02-06 | 1989-02-21 | Synthetic Products Company | Stain-resistant antimony organic sulfur-containing compounds and vinyl halide resins containing same |
| CN103896815B (zh) * | 2014-03-26 | 2016-03-30 | 安徽师范大学 | 一种邻位巯基苯酚衍生物及其制备方法 |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB827393A (en) * | 1955-11-07 | 1960-02-03 | Metal & Thermit Corp | Stabilized vinyl chloride polymers |
| US3875084A (en) * | 1971-12-30 | 1975-04-01 | Hooker Chemical Corp | Polyvinyl halide thioether polymers |
| US4029618A (en) * | 1975-06-30 | 1977-06-14 | Dart Industries Inc. | Vinyl halide stabilizer compositions of antimony organic sulfur-containing compounds and ortho-dihydric phenols |
| EP0031295B1 (de) * | 1979-11-08 | 1983-05-18 | Ciba-Geigy Ag | Neue organische Antimon-Schwefel-Verbindungen, ihre Verwendung als Stabilisatoren für chlorhaltige Thermoplaste und die so stabilisierten Thermoplaste |
| EP0038773A3 (de) * | 1980-02-28 | 1982-06-09 | Ciba-Geigy Ag | Stabilisatorgemische aus Metallmercaptiden und o-Dihydroxyarylcarbonsäureester oder -tetrahalogenverbindungen und damit stabilisierte chlorhaltige Thermoplaste |
| US4314934A (en) * | 1981-02-26 | 1982-02-09 | Carstab Corporation | Organohalide polymers stabilized with an organotin compound and an ortho mercapto phenol compound |
-
1982
- 1982-08-09 US US06/406,584 patent/US4440891A/en not_active Expired - Fee Related
-
1983
- 1983-08-26 EP EP83304945A patent/EP0134348A1/en not_active Withdrawn
- 1983-08-30 CA CA000435648A patent/CA1202479A/en not_active Expired
- 1983-09-07 AU AU18785/83A patent/AU560936B2/en not_active Ceased
- 1983-09-09 JP JP58166420A patent/JPS6067549A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| AU560936B2 (en) | 1987-04-30 |
| AU1878583A (en) | 1985-03-14 |
| JPS6067549A (ja) | 1985-04-17 |
| EP0134348A1 (en) | 1985-03-20 |
| US4440891A (en) | 1984-04-03 |
| JPH0449577B2 (en, 2012) | 1992-08-11 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEX | Expiry |