GB2079295A - A Stabilizing Composition for Homopolymers and/or Copolymers of Vinyl Chloride - Google Patents
A Stabilizing Composition for Homopolymers and/or Copolymers of Vinyl Chloride Download PDFInfo
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- GB2079295A GB2079295A GB8118086A GB8118086A GB2079295A GB 2079295 A GB2079295 A GB 2079295A GB 8118086 A GB8118086 A GB 8118086A GB 8118086 A GB8118086 A GB 8118086A GB 2079295 A GB2079295 A GB 2079295A
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- stabilizing composition
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- 239000000203 mixture Substances 0.000 title claims abstract description 69
- 230000000087 stabilizing effect Effects 0.000 title claims abstract description 42
- BZHJMEDXRYGGRV-UHFFFAOYSA-N Vinyl chloride Chemical compound ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 title claims abstract description 18
- 229920001577 copolymer Polymers 0.000 title claims description 21
- 229920001519 homopolymer Polymers 0.000 title claims description 14
- OJMIONKXNSYLSR-UHFFFAOYSA-N phosphorous acid Chemical compound OP(O)O OJMIONKXNSYLSR-UHFFFAOYSA-N 0.000 claims abstract description 20
- 150000001875 compounds Chemical class 0.000 claims abstract description 16
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 7
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 7
- 239000001301 oxygen Substances 0.000 claims abstract description 7
- 239000007983 Tris buffer Substances 0.000 claims abstract description 5
- 125000004432 carbon atom Chemical group C* 0.000 claims description 13
- 150000002148 esters Chemical class 0.000 claims description 10
- 239000004014 plasticizer Substances 0.000 claims description 9
- 125000000217 alkyl group Chemical group 0.000 claims description 8
- 125000002947 alkylene group Chemical group 0.000 claims description 8
- 125000003118 aryl group Chemical group 0.000 claims description 6
- 239000000314 lubricant Substances 0.000 claims description 6
- CDPYVLUFLWFDRJ-UHFFFAOYSA-N tris[2-(1-phenylethyl)phenyl] phosphite Chemical compound C=1C=CC=C(OP(OC=2C(=CC=CC=2)C(C)C=2C=CC=CC=2)OC=2C(=CC=CC=2)C(C)C=2C=CC=CC=2)C=1C(C)C1=CC=CC=C1 CDPYVLUFLWFDRJ-UHFFFAOYSA-N 0.000 claims description 6
- 239000004593 Epoxy Substances 0.000 claims description 5
- 125000002877 alkyl aryl group Chemical group 0.000 claims description 5
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 4
- 125000000732 arylene group Chemical group 0.000 claims description 4
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 4
- 125000003342 alkenyl group Chemical group 0.000 claims description 3
- HDFRDWFLWVCOGP-UHFFFAOYSA-N carbonothioic O,S-acid Chemical class OC(S)=O HDFRDWFLWVCOGP-UHFFFAOYSA-N 0.000 claims description 3
- 125000004122 cyclic group Chemical group 0.000 claims description 3
- -1 isooctyl Chemical group 0.000 claims description 3
- 239000002530 phenolic antioxidant Substances 0.000 claims description 3
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 2
- 125000006350 alkyl thio alkyl group Chemical group 0.000 claims description 2
- VUYGWRPNDGLGLN-UHFFFAOYSA-K antimony(3+);2-(sulfanylmethyl)hexanoate Chemical compound [Sb+3].CCCCC(CS)C([O-])=O.CCCCC(CS)C([O-])=O.CCCCC(CS)C([O-])=O VUYGWRPNDGLGLN-UHFFFAOYSA-K 0.000 claims description 2
- 125000002993 cycloalkylene group Chemical group 0.000 claims description 2
- 230000002708 enhancing effect Effects 0.000 claims description 2
- 125000000623 heterocyclic group Chemical group 0.000 claims description 2
- 125000005649 substituted arylene group Chemical group 0.000 claims description 2
- 150000003573 thiols Chemical class 0.000 claims description 2
- 125000001183 hydrocarbyl group Chemical group 0.000 claims 2
- 239000002270 dispersing agent Substances 0.000 claims 1
- 229920000642 polymer Polymers 0.000 abstract description 14
- 239000004615 ingredient Substances 0.000 abstract description 9
- OATORLCCIQBWBF-UHFFFAOYSA-K 6-methylheptyl 2-bis[[2-(6-methylheptoxy)-2-oxoethyl]sulfanyl]stibanylsulfanylacetate Chemical compound [Sb+3].CC(C)CCCCCOC(=O)C[S-].CC(C)CCCCCOC(=O)C[S-].CC(C)CCCCCOC(=O)C[S-] OATORLCCIQBWBF-UHFFFAOYSA-K 0.000 abstract description 7
- 239000000126 substance Substances 0.000 abstract description 3
- 230000000704 physical effect Effects 0.000 abstract description 2
- 239000004800 polyvinyl chloride Substances 0.000 description 14
- 229920000915 polyvinyl chloride Polymers 0.000 description 14
- 150000002894 organic compounds Chemical class 0.000 description 9
- 239000000047 product Substances 0.000 description 9
- 239000003381 stabilizer Substances 0.000 description 7
- 239000000463 material Substances 0.000 description 6
- 238000002156 mixing Methods 0.000 description 6
- AQSJGOWTSHOLKH-UHFFFAOYSA-N phosphite(3-) Chemical class [O-]P([O-])[O-] AQSJGOWTSHOLKH-UHFFFAOYSA-N 0.000 description 5
- 230000002195 synergetic effect Effects 0.000 description 5
- 239000011888 foil Substances 0.000 description 4
- 230000006872 improvement Effects 0.000 description 4
- HVLLSGMXQDNUAL-UHFFFAOYSA-N triphenyl phosphite Chemical compound C=1C=CC=CC=1OP(OC=1C=CC=CC=1)OC1=CC=CC=C1 HVLLSGMXQDNUAL-UHFFFAOYSA-N 0.000 description 4
- 230000003078 antioxidant effect Effects 0.000 description 3
- 150000001735 carboxylic acids Chemical class 0.000 description 3
- ZJIPHXXDPROMEF-UHFFFAOYSA-N dihydroxyphosphanyl dihydrogen phosphite Chemical class OP(O)OP(O)O ZJIPHXXDPROMEF-UHFFFAOYSA-N 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 150000002430 hydrocarbons Chemical class 0.000 description 3
- 239000000049 pigment Substances 0.000 description 3
- 229920002959 polymer blend Polymers 0.000 description 3
- 239000003017 thermal stabilizer Substances 0.000 description 3
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 2
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-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
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 2
- 239000005864 Sulphur Substances 0.000 description 2
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 2
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 2
- 150000001342 alkaline earth metals Chemical class 0.000 description 2
- 239000003963 antioxidant agent Substances 0.000 description 2
- 235000006708 antioxidants Nutrition 0.000 description 2
- 239000002216 antistatic agent Substances 0.000 description 2
- 239000006185 dispersion Substances 0.000 description 2
- 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 239000000945 filler Substances 0.000 description 2
- 239000012530 fluid Substances 0.000 description 2
- 239000008187 granular material Substances 0.000 description 2
- 230000008642 heat stress Effects 0.000 description 2
- 238000000265 homogenisation Methods 0.000 description 2
- 230000001050 lubricating effect Effects 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- 230000005012 migration Effects 0.000 description 2
- 238000013508 migration Methods 0.000 description 2
- 230000000051 modifying effect Effects 0.000 description 2
- 229920003023 plastic Polymers 0.000 description 2
- 239000004033 plastic Substances 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 230000006641 stabilisation Effects 0.000 description 2
- 238000011105 stabilization Methods 0.000 description 2
- 238000003860 storage Methods 0.000 description 2
- 239000000758 substrate Substances 0.000 description 2
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
- CLVGYDACJAFBPF-UHFFFAOYSA-N (2,3-didodecylphenyl) dihydrogen phosphite Chemical compound CCCCCCCCCCCCC1=CC=CC(OP(O)O)=C1CCCCCCCCCCCC CLVGYDACJAFBPF-UHFFFAOYSA-N 0.000 description 1
- CLNSNXOIVDERHH-UHFFFAOYSA-N 12,12,12-triphenyldodecyl dihydrogen phosphite Chemical compound C1=CC=C(C=C1)C(CCCCCCCCCCCOP(O)O)(C2=CC=CC=C2)C3=CC=CC=C3 CLNSNXOIVDERHH-UHFFFAOYSA-N 0.000 description 1
- YEQHNTCMAVPEKP-UHFFFAOYSA-N 6-methylheptyl diphenyl phosphite Chemical compound C=1C=CC=CC=1OP(OCCCCCC(C)C)OC1=CC=CC=C1 YEQHNTCMAVPEKP-UHFFFAOYSA-N 0.000 description 1
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 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
- XBPIJNMQCFCDJG-UHFFFAOYSA-K C1(CCCCC1)C(C(=O)[O-])(C)S.C1(CCCCC1)C(C(=O)[O-])(C)S.C1(CCCCC1)C(C(=O)[O-])(C)S.[Sb+3] Chemical compound C1(CCCCC1)C(C(=O)[O-])(C)S.C1(CCCCC1)C(C(=O)[O-])(C)S.C1(CCCCC1)C(C(=O)[O-])(C)S.[Sb+3] XBPIJNMQCFCDJG-UHFFFAOYSA-K 0.000 description 1
- XGFLOVWHYYRSSU-UHFFFAOYSA-K C1(CCCCC1)C(C(=O)[O-])CS.C1(CCCCC1)C(C(=O)[O-])CS.C1(CCCCC1)C(C(=O)[O-])CS.[Sb+3] Chemical compound C1(CCCCC1)C(C(=O)[O-])CS.C1(CCCCC1)C(C(=O)[O-])CS.C1(CCCCC1)C(C(=O)[O-])CS.[Sb+3] XGFLOVWHYYRSSU-UHFFFAOYSA-K 0.000 description 1
- YPIOYKWKZYRDPI-UHFFFAOYSA-K C1(CCCCC1)SCC(=O)[O-].C1(CCCCC1)SCC(=O)[O-].C1(CCCCC1)SCC(=O)[O-].[Sb+3] Chemical compound C1(CCCCC1)SCC(=O)[O-].C1(CCCCC1)SCC(=O)[O-].C1(CCCCC1)SCC(=O)[O-].[Sb+3] YPIOYKWKZYRDPI-UHFFFAOYSA-K 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical class [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- 244000068988 Glycine max Species 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical class [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 description 1
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- 229920001944 Plastisol Polymers 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- 235000019486 Sunflower oil Nutrition 0.000 description 1
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 1
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical class [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- QJTGDHSQDUCUJF-UHFFFAOYSA-K [Sb+3].CC(C)CCCCCC(CS)C([O-])=O.CC(C)CCCCCC(CS)C([O-])=O.CC(C)CCCCCC(CS)C([O-])=O Chemical compound [Sb+3].CC(C)CCCCCC(CS)C([O-])=O.CC(C)CCCCCC(CS)C([O-])=O.CC(C)CCCCCC(CS)C([O-])=O QJTGDHSQDUCUJF-UHFFFAOYSA-K 0.000 description 1
- RNKRHLUBFQLLKE-UHFFFAOYSA-K [Sb+3].CCCCCCCCCCCCSCC([O-])=O.CCCCCCCCCCCCSCC([O-])=O.CCCCCCCCCCCCSCC([O-])=O Chemical compound [Sb+3].CCCCCCCCCCCCSCC([O-])=O.CCCCCCCCCCCCSCC([O-])=O.CCCCCCCCCCCCSCC([O-])=O RNKRHLUBFQLLKE-UHFFFAOYSA-K 0.000 description 1
- 239000006096 absorbing agent Substances 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 239000012298 atmosphere Substances 0.000 description 1
- 229910052788 barium Inorganic materials 0.000 description 1
- DSAJWYNOEDNPEQ-UHFFFAOYSA-N barium atom Chemical class [Ba] DSAJWYNOEDNPEQ-UHFFFAOYSA-N 0.000 description 1
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 description 1
- 239000012965 benzophenone Substances 0.000 description 1
- VQLYBLABXAHUDN-UHFFFAOYSA-N bis(4-fluorophenyl)-methyl-(1,2,4-triazol-1-ylmethyl)silane;methyl n-(1h-benzimidazol-2-yl)carbamate Chemical compound C1=CC=C2NC(NC(=O)OC)=NC2=C1.C=1C=C(F)C=CC=1[Si](C=1C=CC(F)=CC=1)(C)CN1C=NC=N1 VQLYBLABXAHUDN-UHFFFAOYSA-N 0.000 description 1
- DQXBYHZEEUGOBF-UHFFFAOYSA-N but-3-enoic acid;ethene Chemical compound C=C.OC(=O)CC=C DQXBYHZEEUGOBF-UHFFFAOYSA-N 0.000 description 1
- MGFFVSDRCRVHLC-UHFFFAOYSA-N butyl 3-sulfanylpropanoate Chemical compound CCCCOC(=O)CCS MGFFVSDRCRVHLC-UHFFFAOYSA-N 0.000 description 1
- CQEYYJKEWSMYFG-UHFFFAOYSA-N butyl acrylate Chemical compound CCCCOC(=O)C=C CQEYYJKEWSMYFG-UHFFFAOYSA-N 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229910052793 cadmium Inorganic materials 0.000 description 1
- BDOSMKKIYDKNTQ-UHFFFAOYSA-N cadmium atom Chemical class [Cd] BDOSMKKIYDKNTQ-UHFFFAOYSA-N 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 239000011575 calcium Chemical class 0.000 description 1
- 150000007942 carboxylates Chemical class 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 230000009920 chelation Effects 0.000 description 1
- 229920005556 chlorobutyl Polymers 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 239000007857 degradation product Substances 0.000 description 1
- 230000006866 deterioration Effects 0.000 description 1
- 150000001993 dienes Chemical class 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- 229920001971 elastomer Polymers 0.000 description 1
- 239000000806 elastomer Substances 0.000 description 1
- 238000005516 engineering process Methods 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
- 239000005038 ethylene vinyl acetate Substances 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 239000001530 fumaric acid Substances 0.000 description 1
- 230000036541 health Effects 0.000 description 1
- 239000012760 heat stabilizer Substances 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 238000001746 injection moulding Methods 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 239000011777 magnesium Chemical class 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 1
- 150000002903 organophosphorus compounds Chemical class 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 1
- 235000021317 phosphate Nutrition 0.000 description 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 239000004999 plastisol Substances 0.000 description 1
- 229920001200 poly(ethylene-vinyl acetate) Polymers 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 229920000151 polyglycol Polymers 0.000 description 1
- 239000010695 polyglycol Substances 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
- 230000005855 radiation Effects 0.000 description 1
- 238000005096 rolling process Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000000344 soap Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000003549 soybean oil Substances 0.000 description 1
- 235000012424 soybean oil Nutrition 0.000 description 1
- 230000003068 static effect Effects 0.000 description 1
- 239000002600 sunflower oil Substances 0.000 description 1
- 239000004753 textile Substances 0.000 description 1
- 150000003566 thiocarboxylic acids Chemical class 0.000 description 1
- 239000004408 titanium dioxide Substances 0.000 description 1
- 238000002834 transmittance Methods 0.000 description 1
- FICPQAZLPKLOLH-UHFFFAOYSA-N tricyclohexyl phosphite Chemical compound C1CCCCC1OP(OC1CCCCC1)OC1CCCCC1 FICPQAZLPKLOLH-UHFFFAOYSA-N 0.000 description 1
- IVIIAEVMQHEPAY-UHFFFAOYSA-N tridodecyl phosphite Chemical compound CCCCCCCCCCCCOP(OCCCCCCCCCCCC)OCCCCCCCCCCCC IVIIAEVMQHEPAY-UHFFFAOYSA-N 0.000 description 1
- FMTQZINCFVSZPQ-UHFFFAOYSA-N tris(oxolan-2-ylmethyl) phosphite Chemical compound C1CCOC1COP(OCC1OCCC1)OCC1CCCO1 FMTQZINCFVSZPQ-UHFFFAOYSA-N 0.000 description 1
- 229920001567 vinyl ester resin Polymers 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Chemical class 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
- C08K5/49—Phosphorus-containing compounds
- C08K5/51—Phosphorus bound to oxygen
- C08K5/52—Phosphorus bound to oxygen only
- C08K5/524—Esters of phosphorous acids, e.g. of H3PO3
-
- 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
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)
Abstract
The stabilizing composition consists of an organic antimonous compound with Sb-S bond, for example, antimony-tris (isooctyl mercapto-acetate), and an organic phosphite, for example, mixed tris (1- phenylethy-phenyl) phosphite. Known ingredients for improving the chemical and physical properties of the stabilized polymer may also be present. The stabilizing compositions synergistically enhance the thermal stability of vinyl chloride polymers while simultaneously improving their stability to light and oxygen and resistance to weathering.
Description
SPECIFICATION
A Stabilizing Composition for Homopolymers and/or Copolymers of Vinyl Chloride.
The invention relates to a stabilizing composition for homopolymers and/or copolymers of vinyl chloride providing enhanced resistance to heat, light, oxygen and to weathering, in which the synergistic effect of an antimonous organic compound in combination with an organic phosphite is used. The employment of antimonous organic compounds as heat stabilizers for vinyl chloride polymers is known and their application to hard and soft polyvinyl chloride and mixtures has been described. For example, in U.S. Patent 2 680 726 employment of antimonous esters of mercaptocarboxylic acids is disclosed and in U.S.
Patent 2 684 956 employment of antimonous mercaptides is mentioned.
Multicomponent stabilizing systems containing antimonous organic compounds with an Sb-S bond and other ingredients of various chemical composition are also described, which ingredients improve the application properties of antimonous stabilizers. West German Patent 2 454 986 includes compositions based on antimonous mercaptides and salts of alkaline earth metals with carboxylic or thiocarboxylic acids. Analogous compositions are also the subject of the Belgian
Patent 866 428.
The stabilizing compositions mentioned including alkaline phosphates of the Me3PO4 type are found in U.S. Patent 3 919 168.
Improvements in the stabilizing effect of antimonous organic compounds is also achieved by the presence of alkylated dihydric phenols (West German Patent 2 629 202).
West German Patent 2 704 487 describes a three component stabilizing composition containing antimony-tris (iso-octyl mercaptoacetate), a hydrogen chloride acceptor and organic compounds with chelation properties.
The employement of phosphorus-containing compounds in the processing of plastic materials is also known and organic phosphorus compounds have been successfully used in the processing of plastic materials and elastomers for some time.
Organic phosphites-derivatives of phosphorous acid are particulacly widely used. They are used mainly as antioxidants, but in the case of chlorinecontaining polymers they can also be used as secondary thermal stabilizers. The synergistic effect of thermal stabilizers being based on their ability to bond degradation products of primary metallic stabilizers which catalytically accelerate polymer decomposition.
There are also described systems of organic phosphites with thermal stabilizers based on organic salts of alkaline earth metals, barium, cadmium, calcium, magnesium, zinc, or with organo-tin compounds (U.S. Patent 2 564 646,
British Patent 803 081, West German Patent
1 262 590, U.S. Patent 3 919 165, West German
Patent 1 175 874).
In practice the combination of metallic soaps with an organic phosphite and epoxy plasticizer has become one of the standard stabilizing systems for polyvinylchloride (U.S. Patent 2 997 454, Belgian Patent 595 409).
Four-component compositions are also known in which an antioxidant is added to the foregoing system (West German Patent 1149 164, British
Patent 841 890), optionally with a hydrocarbon solvent (Belgian Patent 621 848).
Mixtures of triphenyl phosphite with plumbous carboxylates are disclosed in U.S. Patent 2752319.
Antimonous organic compounds with an Sb-S bond are comparable with organo-tin sulphurcontaining stabilizers as far as heat-stabilizing efficiency is concerned but low resistance to oxygen and aerial humidity during storage remains a disadvantage.
The combination of organo-tin stabilizers and organic phosphites have the antioxidative effect of the phosphites but there is no improvement of the heat-stabilizing effect of tin-containing stabilizers.
The compositions described above improve the thermal and possibly oxidative resistance of vinyl chloride polymers, but they do not affect resistance to light or oxygen and aerial humidity.
These disadvantages are eliminated to a substantial degree according to the invention by a stabilizing composition for homopolymers and/or copolymers of vinyl chloride for enhancing their resistance to heat, light, oxygen and to weathering, containing 50 to 95% by weight of an organic antimonous compound Sb-S bond and 5 to 50% by weight of an organic phosphite.
Optionally, the compositions may be combined with known ingredients for improving the chemical and physical properties of the stabilized polymers.
Suitable organic antimonous compounds may be described by the general formula: SbX3 where X stands for a residue of esters of mercapto-carboxylic acids of the type SR2COOR or a residue of a thiol of the type SR1, and where
R1 stands for alkyl with 1 to 1 8 carbon atoms, cycloalkyl with 5 to 7 carbon atoms, aryl, alkylaryl, alkoxyalkyl or alkyl-thioalkyl with 3 to 20 carbon atoms or substituted derivatives, and
R2 stands for alkylene with 1 to 6 carbon atoms, arylene, aryl-alkylene or substituted derivatives.
Of the alkylene residues R1 the most frequent are methylene and ethylene, R2 can be methyl, isopropyl, butyl, isooctyl, dodecyl, 2-alkoxyethyl or 2-alkyl thioethyl.
Antimony-tris (isooctyl mercaptoacetate), antimony-tris (dodecyl mercaptide), antimonytris(butyl-3-mercaptopropionate), antimony-tris (dodecyl mercaptoacetate), antimony-tris (cyclohexyl mercaptoacetate), antimony-tris (cyclohexyl-3-mercaptopropionate), antimony-tris (2-ethyl-hexy-3-mercaptopropionate) or mixtures of these compounds are typical examples of sulphur-containing antimonous compounds.
Suitable organic phosphites may be described by the general formula:
where R1, R2, R3 stand for the same or different substitued or non-substituted hydrocarbon residues with 1 to 40 carbon atoms and may comprise alkyl, aryl, alkylaryl, arylalkyl, alkenyl and cyclic or heterocyclic groups.
For example, tridodecyl phosphite, triphenyl phosphite, tricresyl phosphite, triphenyldodecyl phosphite, tris (nonylpheny) phosphite, tricyclohexylphosphite, tri(tetrahydrofurfuryl) phosphite, isooctyldiphenyl phosphite, mixed tris (1 -phenylethylphenyl) phosphite, di-dodecylphenyl phosphite, alkyl bis (octylpheny) phosphite are typical of these compounds.
Organic diphosphites based on pentaerythritol of the general formula:
may also be used in the invention, where X, Y stand, for the same or different hydrocarbon residues with 1 to 30 carbon atoms and may comprise alkyl, aryl, alkylaryl, arylalkyl, cycloalkyl or alkenyl groups.
These compounds are represented, for example, by 4,9-di-(2-ethylhexyloxa)-3,5,8, 10- tetraoxa-4,9-diphospha-spiro [5,5] undecane and 4,9-di [4-( 1,1 -dimethylbenzyl) phenoxy]-3,5,8, 10- tetraoxa-4,9-diphospho-spiro [5,5] u ndecane.
Also suitable are cyclic organic diphosphites characterized by the general formula
where Y stands for a substituted or non
substituted arylene, alkylene or cycloalkylene
group and X stands for a substituted or non
substituted alkylene, alkoxyalkyiene or arylene
group, for example,1,2,-bis(1,3,2 dioxaphospholanyl)-1 ,2 dioxiethane.
The composition suggested can contain further
ingredients favourably affecting homogeneity of
polymer mixture, for example, for improving the
dispersion of the stabilizing system in the
polymer, providing a lubricating effect, adjusting
flow properties of the melt and modifying
mechanical properties of the final products.
For this purpose up to 40% by weight of an epoxy plasticizer of the type epoxidated esters of fatty acids of soybean or sunflower oil, and up to 30% by weight of a phenolic anti-oxidant of the type 2,6-di-tert. butyl-4methyl phenol, or 2,6-ditert. butyl-4-alkyl phenol with an alkyl group having 30 to 50 carbon atoms can be added to the composition.
Improvements in the dispersion of stabilizing fir composition in the polymer base may be achieved according to the invention by the addition of esters of multipbasic acids, polymeric plasticizers based on polyglycols or polyesters, optionally of higher alcohols and/or ingredients providing lubricating or modifying effects.
The compositions described have a number of advantageous properties which are achieved at certain component ratios which are also mutually compatible.
The compositions are advantageously prepared by intensive mixing of all components at elevated temperatures of 40 to 1000C for 30 to 60 minutes. Single components of the composition can, nevertheless, be added directly to the polymer mixture without preceding homogenization.
Stabilizing compositions according to the invention are added to homopolymers and/or copolymers of vinyl chloride in an amount of 0.1 to 10 parts by weight, preferably 0.2 to 4 parts by weight per 100 parts by weight of the polymer.
As typical copolymers, there may be mentioned copolymers of vinyl chloride with vinyl esters of carboxylic acids, for example, vinyl acetate, vinyl propionate, vinyl butyrate, with esters of unsaturated carboxylic acids, for example, methacrylate, butyl acrylate, methyl methacrylate, with styrene, propylene, with dienes, for example, butadiene, acrylonitrile, and with esters of maleic or fumaric acid.
A significant group of vinyl chloride copolymers are formed from polymers and copolymers inoculated with vinyl chloride, for example, vinyl chloride inoculated copolymer of ethylene-vinyl acetate or chlorinated butyl rubber.
Polymer mixtures or materials based on homopolymers or copolymers of vinyl chloride stabilized with compositions according to the invention can contain further known ingredients such as plasticizers, fillers, lubricants, pigments, or antistatic admixtures, which ingredients improve processing and the final properties of the product.
The stabilizing compositions according to the invention have a number of advantages. In the presence of the antimonous sulphur-containing organic compound, the synergistic effect also manifests itself, in addition to the antioxidative action of the organic phosphite, in a substantial enhancement of thermal stability and a simultaneous improvement in the light stability of .
the final polymer. The synergistic effect of the components of the stabilizing composition means that a smaller amount thereof may be employed which is reflected in reduced stabilization costs.
The compositions are characterized by higher stability in storage and manipulation when compared with antimonous compounds alone, because admixture with an organic phosphite positively influences the stability of the liquid composition and prevents the separation of a solid fraction. Single components of the composition are mutually readily miscible and do not form boundaries between phases.
As a result of the high thermal stability of the stabilized composition no volatile products arise during processing, which may adversely affect the working environment. Thus, the present of an organic phosphite in the composition together with an organic antimonous compound decreases any risk there may be to health.
The compositions according to the invention are economically advantageous and single components are technically easily accessible.
Materials containing homopolymers or copolymers of vinyl chloride stabilized with compositions according to the invention have higher thermal stability than analogous materials containing the currently used metallic stabilizers.
Excellent thermal stability ensures safe processing under particular working conditions.
The protection afforded by the organic phosphites against the influence of light, oxygen and weathering, which manifests itself simultaneously, leads to the enhanced utility of stabilized materials and to the prolongation of the service life of final products.
The stabilizing compositions according to the invention are usable in the various applications of softened, non-softened and tough polyvinyl chloride and plastisols, as processed by current technology.
Compositions containing an antimonous organic compound with an SbS bond and an organic phosphite are characterized by good compatibility with the polymer and with all common additives. Thus, no migration of components takes place in the course of processing or in the final products as indicated by colour stability and high surface quality.
Single components of the stabilizing composition are extractible with difficulty. They are hydrolytically and thermally stable and when used with homopolymers or copolymers of vinyl chloride, no loss of the active compound takes place.
Further advantages as weli as methods of carrying out the invention are apparent from the following examples.
Example 1
A stabilizing composition containing 80% by weight of antimony-tris(isooctyl mercaptoacetate) and 20% by weight of mixed tris(1 -phenylethylphenyl) phosphite was prepared by intensive mixing of components for 30 minutes at a temperature of 800C.
The composition was used in an amount of 1 part by weight for the stabilization of 100 parts by weight of suspended poly-vinyl chloride containing 1 part by weight of lubricant. A foil was prepared from the powdered mixture by homogenization using a double roll at a temperature of 1 800 C, and subsequently exposed to static heat stress at a temperature of 180"C in the atmosphere.
The efficiency of the stabilizing composition was compared with the effect of antimonytris(isooctyl mercaptoacetate) alone in polyvinyl chloride, prepared under the same conditions.
The synergistic effect of the stabilizing composition manifest itself in a 25% enhancement of the thermal stability of the polyvinyl chloride compared with the antimonous organic compound alone. The light stability and weather resistance of the polyvinyl chloride was also simultaneously improved by 800 hours exposure in a Xenotest 450.
Example 2
Stabilizing compositions containing 90% by weight of antimony-tris(isooctyl mercaptoacetate) and 10% by weight of a dialkylaryl phosphite (A) and 10% by weight of a diphosphite based on pentaerythritoi (B) were prepared by the method described in the Example 1.
The compositions were added in an amount of 1 part by weight to 100 parts by weight of polyvinyl chloride containing 0.5 parts by weight of lubricant.
On the basis of a change in foil colour, where the foil was exposed to the effect of heat stress and light radiation, higher efficiency of compositions A and B was found compared with analogous polyvinyl chloride stabilized with antimonous or organo-tin stabilizers alone.
Example 3
Granules for injection moulding soles were prepared by mixing in a fluid mixer a softened mixture containing 100 parts by weight of polyvinyl chloride, 70 parts by weight of plasticizers of the ester type, 4 parts by weight parts of an epoxy plasticizer, 5 parts by weight of pigments and colorants and 0.6 parts by weight of a stabilizing composition consisting of 70% by weight of antimony-tris (isooctyl-3mercaptopropionate) and 30% by weight of mixed tris( 1 -phenylethyl-phenyl) phosphite.
The products were characterized by satisfactory thermal stability, a good quality surface and by good mechanical and processing properties.
Example 4
Pigmented mixtures were prepared, the mixtures containing 100 parts by weight of tough polyvinyl chloride modified by vinyl chloride inoculated with an ethylene/vinyl acetate copolymer, 2 parts by weight of lubricants, 0.3 parts by weight of a UVabsorber of the benzophenone type, 3 parts by weight of finely ground limestone, 2.5 parts by weight of titanium dioxide and 1.2 parts by weight of a stabilizing composition consisting of 78% by weight of antimony-tris(butyl-3-mercaptopropionate), 20% by weight of an aikylaryl phosphite and 2% by weight of a phenolic antioxidant.
Granules for pressed profiles for external applications in the building industry where then prepared from a powdered pre-mixture at the granulating (production) line after mixing in a fluid mixer, and the final products were exposed to conditions of weathering. The products were found to possess excellent light and weathering resistance, good colour stability and could be processed safely. No deterioration in surface quality, loss of lustre or migration of ingredients was found to have taken place either.
Example 5
A softened mixture was prepared, the mixture containing 100 parts by weight of polyvinyl chloride, 50 parts by weight of plasticizers of the ester type, 5 parts by weight of an epoxy compound, 0.5 parts by weight of lubricant, 0.2 parts by weight of a UV-absorber and 0.6 parts by weight of a stabilizing composition containing 60% by weight of antimony-tris(cyclohexyl-2mercaptopropionate) and 40% by weight of mixed tris( 1 -phenylethyl-phenyl)-phosphite.
A transparent foil prepared by rolling after mixing was found to have a light transmittance of 89% and could be used for technical purposes, for covering articles and temporarily storing objects.
The stabilizing system ensured safe processing and the possibility of re-processing of waste material, in addition to conferring useful properties on the final polymer product.
Example 6
Polyvinyl chloride paste with antistatic properties was prepared by direct mixing of 100 parts by weight of a paste-forming polyvinyl chloride, 100 parts by weight of plasticizers of the ester type, 4 parts by weight of pigments and fillers, 8 parts by weight of an antistatic agent and 1.2 parts by weight of a stabilizing composition consisting of 30% by weight of antimonytris(isooctylmercaptoacetate) and 20% by weight of mixed tris(1-phenyl-ethyl-phenyl) phosphite.
The paste was used for coating onto a textiie substrate when the presence of the stabilizing composition ensured safe processing even at high levels of the antistatic agent.
The final product was characterized by high colour stability, a surface of good quality and by good adhesion to the textile substrate.
Claims (14)
1. A stabilizing composition for homopolymers and/or copolymers of vinyl chloride for enhancing their resistance to heat, light, oxygen and to weathering, containing 50 to 95% by weight of an organic antimonous compound with Sb-S bond and 5 to 50% by weight of an organic phosphite.
2. A stabilizing composition according to Claim 1, in which the organic antimonous compound has the general formula
Sb X3 where X stands for a residue of esters of mercaptocarboxylic acids of the type SR2COOR1 or a residue of a thiol of the type SR1, and where R1 stands for alkyl with 1 to 18 carbon atoms, cycloalkyl with 5 to 7 carbon atoms, aryl, X alkylaryl, alkoxyalkyl or alkylthioalkyl with 3 to 29 carbon atoms or substituted derivatives, and R2 is alkylene with 1 to 6 carbon atoms, arylene, ary!alkylene or substituted derivatives.
3. A stabilizing composition according to Claim 2 in which the organic antimonous compound is antimony-tris (isooctyl m ercaptoacetate)
4. A stabilizing composition according to Claim 2 in which the organic antimonous compound is antimony-tris (butyl-3-mercaptopropionate).
5. A stabilizing composition according to any one of the preceding claims in which the organic phosphite has the general formula
where R1, R2, R3 stand for the same or different substituted or non-substituted hydrocarbon residues with 1 to 40 carbon atoms.
6. A stabilizing composition according to Claim 5 in which R1, R2, R3 stand for alkyl, aryl, arylalkyl, alkenyl, cyclic or heterocyclic groups.
7. A stabilizing composition according to Claim 5 or 6 in which the organic phosphite is mixed tris (1 -phenylethyl-phenyl) phosphite.
8. A stabilizing compositionaccording to any one of Claims 1 to 4, in which the organic phosphite has the general formula
where X and Y stand for the same or different hydrocarbon residues with 1 to 30 carbon atoms.
9. A stabilizing composition according to Claim 8 in which X and Y stand for alkyl, aryl, alkylaryl, arylalkyl, cycloalkyl or aikenyl groups.
10. A stabilizing composition according to any one of Claims 1 to 4, in which the organic phosphite has the general formula
where Y stands for substituted or non-substituted arylene, alkylene or cycloalkylene groups and X stands for substituted or non-substituted alkylene' alkoxy-alkylene or arylene groups.
11. A homopolyrner and/or copolymer of vinyl chloride containing a stabilizing composition according to any one of the preceding claims.
12. A homopolymer and/or copolymer according to Claim 11 in which the stabilizing composition is present in an amount of 0.1 to 10 parts by weight.
13. A homopolymer and/or copolymer according to Claim 11 or 12 in which up to 40% by weight of an epoxy plasticizer is present.
14. A homopolymer and/or copolymer according to Claim 11 or 12 in which up to 30% by weight of a phenolic antioxidant is present.
1 5. A homopolymer and/or copolymer according to any one of Claims 11 to 14 in which a dispersant and/or lubricant is present.
1 6. A stabilizing composition according to
Claim 1 substantially as hereinbefore described in any one of Examples 1 to 6.
1 7. A homopolymer and/or copolymer of vinyl chloride containing a stabilizing composition according to Claim 16.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CS804178A CS218623B1 (en) | 1980-06-13 | 1980-06-13 | Stabilized composition for homopolymeres and/or vinylchloride copolymeres |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB2079295A true GB2079295A (en) | 1982-01-20 |
Family
ID=5383929
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB8118086A Withdrawn GB2079295A (en) | 1980-06-13 | 1981-06-12 | A Stabilizing Composition for Homopolymers and/or Copolymers of Vinyl Chloride |
Country Status (8)
| Country | Link |
|---|---|
| JP (1) | JPS5730750A (en) |
| CS (1) | CS218623B1 (en) |
| DD (1) | DD160882A3 (en) |
| DE (1) | DE3123035A1 (en) |
| FR (1) | FR2484429A1 (en) |
| GB (1) | GB2079295A (en) |
| IT (1) | IT1137592B (en) |
| NL (1) | NL8102849A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN116199988A (en) * | 2023-03-27 | 2023-06-02 | 厦门恒美达科技有限公司 | Anti-aging modified plastic and preparation method thereof |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA1190037A (en) * | 1980-10-07 | 1985-07-09 | Albert R. Miller | Stabilizers for vinyl chloride polymers |
-
1980
- 1980-06-13 CS CS804178A patent/CS218623B1/en unknown
-
1981
- 1981-06-10 DE DE19813123035 patent/DE3123035A1/en not_active Withdrawn
- 1981-06-12 NL NL8102849A patent/NL8102849A/en not_active Application Discontinuation
- 1981-06-12 GB GB8118086A patent/GB2079295A/en not_active Withdrawn
- 1981-06-12 IT IT22300/81A patent/IT1137592B/en active
- 1981-06-12 FR FR8111597A patent/FR2484429A1/en active Granted
- 1981-06-12 DD DD81231023A patent/DD160882A3/en not_active IP Right Cessation
- 1981-06-12 JP JP8972781A patent/JPS5730750A/en active Pending
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN116199988A (en) * | 2023-03-27 | 2023-06-02 | 厦门恒美达科技有限公司 | Anti-aging modified plastic and preparation method thereof |
| CN116199988B (en) * | 2023-03-27 | 2024-03-22 | 厦门恒美达科技有限公司 | Anti-aging modified plastic and preparation method thereof |
Also Published As
| Publication number | Publication date |
|---|---|
| DD160882A3 (en) | 1984-06-13 |
| IT1137592B (en) | 1986-09-10 |
| DE3123035A1 (en) | 1982-03-25 |
| FR2484429B3 (en) | 1983-04-01 |
| CS218623B1 (en) | 1983-02-25 |
| JPS5730750A (en) | 1982-02-19 |
| IT8122300A0 (en) | 1981-06-12 |
| FR2484429A1 (en) | 1981-12-18 |
| NL8102849A (en) | 1982-01-04 |
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