DE3839418A1 - STABILIZED POLYMER COMPOSITIONS - Google Patents
STABILIZED POLYMER COMPOSITIONSInfo
- Publication number
- DE3839418A1 DE3839418A1 DE3839418A DE3839418A DE3839418A1 DE 3839418 A1 DE3839418 A1 DE 3839418A1 DE 3839418 A DE3839418 A DE 3839418A DE 3839418 A DE3839418 A DE 3839418A DE 3839418 A1 DE3839418 A1 DE 3839418A1
- Authority
- DE
- Germany
- Prior art keywords
- parts
- acid
- composition
- component
- tert
- 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.)
- Withdrawn
Links
- 239000000203 mixture Substances 0.000 title claims abstract description 73
- 229920000642 polymer Polymers 0.000 title claims abstract description 17
- -1 unsaturated fatty acid esters Chemical class 0.000 claims abstract description 50
- 239000004014 plasticizer Substances 0.000 claims abstract description 23
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims abstract description 18
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 claims abstract description 11
- YODZTKMDCQEPHD-UHFFFAOYSA-N thiodiglycol Chemical compound OCCSCCO YODZTKMDCQEPHD-UHFFFAOYSA-N 0.000 claims abstract description 10
- 235000010233 benzoic acid Nutrition 0.000 claims abstract description 9
- 229910052791 calcium Inorganic materials 0.000 claims abstract description 9
- 229920001169 thermoplastic Polymers 0.000 claims abstract description 9
- ZDFKSZDMHJHQHS-UHFFFAOYSA-N 2-tert-butylbenzoic acid Chemical compound CC(C)(C)C1=CC=CC=C1C(O)=O ZDFKSZDMHJHQHS-UHFFFAOYSA-N 0.000 claims abstract description 8
- 239000005711 Benzoic acid Substances 0.000 claims abstract description 8
- 125000001931 aliphatic group Chemical group 0.000 claims abstract description 8
- 239000004416 thermosoftening plastic Substances 0.000 claims abstract description 8
- 229910052788 barium Inorganic materials 0.000 claims abstract description 7
- 235000021122 unsaturated fatty acids Nutrition 0.000 claims abstract description 4
- 150000002148 esters Chemical class 0.000 claims description 14
- 150000003839 salts Chemical class 0.000 claims description 14
- 239000003381 stabilizer Substances 0.000 claims description 14
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 7
- 239000000460 chlorine Substances 0.000 claims description 7
- 229910052801 chlorine Inorganic materials 0.000 claims description 7
- 229920001577 copolymer Polymers 0.000 claims description 6
- UKMSUNONTOPOIO-UHFFFAOYSA-N docosanoic acid Chemical compound CCCCCCCCCCCCCCCCCCCCCC(O)=O UKMSUNONTOPOIO-UHFFFAOYSA-N 0.000 claims description 6
- POULHZVOKOAJMA-UHFFFAOYSA-N dodecanoic acid Chemical compound CCCCCCCCCCCC(O)=O POULHZVOKOAJMA-UHFFFAOYSA-N 0.000 claims description 6
- BZHJMEDXRYGGRV-UHFFFAOYSA-N Vinyl chloride Chemical compound ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 claims description 5
- BDJRBEYXGGNYIS-UHFFFAOYSA-N nonanedioic acid Chemical compound OC(=O)CCCCCCCC(O)=O BDJRBEYXGGNYIS-UHFFFAOYSA-N 0.000 claims description 5
- 125000005498 phthalate group Chemical class 0.000 claims description 5
- 125000005591 trimellitate group Chemical group 0.000 claims description 5
- 150000001875 compounds Chemical class 0.000 claims description 4
- LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 4
- 229920001519 homopolymer Polymers 0.000 claims description 4
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 claims description 4
- 229920000728 polyester Polymers 0.000 claims description 4
- XOOUIPVCVHRTMJ-UHFFFAOYSA-L zinc stearate Chemical compound [Zn+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O XOOUIPVCVHRTMJ-UHFFFAOYSA-L 0.000 claims description 4
- 235000021357 Behenic acid Nutrition 0.000 claims description 3
- 235000021355 Stearic acid Nutrition 0.000 claims description 3
- 229940116226 behenic acid Drugs 0.000 claims description 3
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 claims description 3
- 150000003233 pyrroles Chemical class 0.000 claims description 3
- 235000012424 soybean oil Nutrition 0.000 claims description 3
- 239000003549 soybean oil Substances 0.000 claims description 3
- OBETXYAYXDNJHR-SSDOTTSWSA-M (2r)-2-ethylhexanoate Chemical compound CCCC[C@@H](CC)C([O-])=O OBETXYAYXDNJHR-SSDOTTSWSA-M 0.000 claims description 2
- VVEFXKUGUXUOSZ-UHFFFAOYSA-N (4-tert-butylphenyl)-(2,4-dihydroxyphenyl)methanone Chemical compound C1=CC(C(C)(C)C)=CC=C1C(=O)C1=CC=C(O)C=C1O VVEFXKUGUXUOSZ-UHFFFAOYSA-N 0.000 claims description 2
- ZXDDPOHVAMWLBH-UHFFFAOYSA-N 2,4-Dihydroxybenzophenone Chemical compound OC1=CC(O)=CC=C1C(=O)C1=CC=CC=C1 ZXDDPOHVAMWLBH-UHFFFAOYSA-N 0.000 claims description 2
- 229910019142 PO4 Inorganic materials 0.000 claims description 2
- WNLRTRBMVRJNCN-UHFFFAOYSA-L adipate(2-) Chemical compound [O-]C(=O)CCCCC([O-])=O WNLRTRBMVRJNCN-UHFFFAOYSA-L 0.000 claims description 2
- OBETXYAYXDNJHR-UHFFFAOYSA-N alpha-ethylcaproic acid Natural products CCCCC(CC)C(O)=O OBETXYAYXDNJHR-UHFFFAOYSA-N 0.000 claims description 2
- 150000008280 chlorinated hydrocarbons Chemical class 0.000 claims description 2
- 229930195733 hydrocarbon Natural products 0.000 claims description 2
- 150000002430 hydrocarbons Chemical class 0.000 claims description 2
- OJMIONKXNSYLSR-UHFFFAOYSA-N phosphorous acid Chemical compound OP(O)O OJMIONKXNSYLSR-UHFFFAOYSA-N 0.000 claims description 2
- CHJMFFKHPHCQIJ-UHFFFAOYSA-L zinc;octanoate Chemical compound [Zn+2].CCCCCCCC([O-])=O.CCCCCCCC([O-])=O CHJMFFKHPHCQIJ-UHFFFAOYSA-L 0.000 claims 2
- 239000004287 Dehydroacetic acid Substances 0.000 claims 1
- 239000005639 Lauric acid Substances 0.000 claims 1
- 229940067597 azelate Drugs 0.000 claims 1
- 235000019258 dehydroacetic acid Nutrition 0.000 claims 1
- JEQRBTDTEKWZBW-UHFFFAOYSA-N dehydroacetic acid Chemical compound CC(=O)C1=C(O)OC(C)=CC1=O JEQRBTDTEKWZBW-UHFFFAOYSA-N 0.000 claims 1
- 229940061632 dehydroacetic acid Drugs 0.000 claims 1
- PGRHXDWITVMQBC-UHFFFAOYSA-N dehydroacetic acid Natural products CC(=O)C1C(=O)OC(C)=CC1=O PGRHXDWITVMQBC-UHFFFAOYSA-N 0.000 claims 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 claims 1
- 235000021317 phosphate Nutrition 0.000 claims 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 claims 1
- 229940116351 sebacate Drugs 0.000 claims 1
- CXMXRPHRNRROMY-UHFFFAOYSA-L sebacate(2-) Chemical compound [O-]C(=O)CCCCCCCCC([O-])=O CXMXRPHRNRROMY-UHFFFAOYSA-L 0.000 claims 1
- 239000008117 stearic acid Substances 0.000 claims 1
- 239000011701 zinc Substances 0.000 claims 1
- JDLYKQWJXAQNNS-UHFFFAOYSA-L zinc;dibenzoate Chemical compound [Zn+2].[O-]C(=O)C1=CC=CC=C1.[O-]C(=O)C1=CC=CC=C1 JDLYKQWJXAQNNS-UHFFFAOYSA-L 0.000 claims 1
- 239000011575 calcium Substances 0.000 abstract description 10
- 239000002253 acid Substances 0.000 abstract description 7
- 235000013305 food Nutrition 0.000 abstract description 2
- 238000004806 packaging method and process Methods 0.000 abstract description 2
- 238000002360 preparation method Methods 0.000 abstract description 2
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 abstract 1
- WDJHALXBUFZDSR-UHFFFAOYSA-M acetoacetate Chemical compound CC(=O)CC([O-])=O WDJHALXBUFZDSR-UHFFFAOYSA-M 0.000 abstract 1
- DSAJWYNOEDNPEQ-UHFFFAOYSA-N barium atom Chemical compound [Ba] DSAJWYNOEDNPEQ-UHFFFAOYSA-N 0.000 abstract 1
- 159000000003 magnesium salts Chemical class 0.000 abstract 1
- 150000003751 zinc Chemical class 0.000 abstract 1
- 238000002156 mixing Methods 0.000 description 8
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 7
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- BJQHLKABXJIVAM-UHFFFAOYSA-N bis(2-ethylhexyl) phthalate Chemical compound CCCCC(CC)COC(=O)C1=CC=CC=C1C(=O)OCC(CC)CCCC BJQHLKABXJIVAM-UHFFFAOYSA-N 0.000 description 6
- 150000007942 carboxylates Chemical class 0.000 description 6
- 229940071127 thioglycolate Drugs 0.000 description 6
- 125000005474 octanoate group Chemical group 0.000 description 5
- AQSJGOWTSHOLKH-UHFFFAOYSA-N phosphite(3-) Chemical class [O-]P([O-])[O-] AQSJGOWTSHOLKH-UHFFFAOYSA-N 0.000 description 5
- ULQISTXYYBZJSJ-UHFFFAOYSA-N 12-hydroxyoctadecanoic acid Chemical compound CCCCCCC(O)CCCCCCCCCCC(O)=O ULQISTXYYBZJSJ-UHFFFAOYSA-N 0.000 description 4
- LAIUFBWHERIJIH-UHFFFAOYSA-N 3-Methylheptane Chemical compound CCCCC(C)CC LAIUFBWHERIJIH-UHFFFAOYSA-N 0.000 description 4
- 239000007983 Tris buffer Substances 0.000 description 4
- 239000000654 additive Substances 0.000 description 4
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 4
- 150000001298 alcohols Chemical class 0.000 description 4
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 4
- SNRUBQQJIBEYMU-UHFFFAOYSA-N dodecane Chemical group CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 4
- GLDOVTGHNKAZLK-UHFFFAOYSA-N octadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCO GLDOVTGHNKAZLK-UHFFFAOYSA-N 0.000 description 4
- CXMXRPHRNRROMY-UHFFFAOYSA-N sebacic acid Chemical compound OC(=O)CCCCCCCCC(O)=O CXMXRPHRNRROMY-UHFFFAOYSA-N 0.000 description 4
- KGRVJHAUYBGFFP-UHFFFAOYSA-N 2,2'-Methylenebis(4-methyl-6-tert-butylphenol) Chemical compound CC(C)(C)C1=CC(C)=CC(CC=2C(=C(C=C(C)C=2)C(C)(C)C)O)=C1O KGRVJHAUYBGFFP-UHFFFAOYSA-N 0.000 description 3
- YPIFGDQKSSMYHQ-UHFFFAOYSA-M 7,7-dimethyloctanoate Chemical compound CC(C)(C)CCCCCC([O-])=O YPIFGDQKSSMYHQ-UHFFFAOYSA-M 0.000 description 3
- IRIAEXORFWYRCZ-UHFFFAOYSA-N Butylbenzyl phthalate Chemical group CCCCOC(=O)C1=CC=CC=C1C(=O)OCC1=CC=CC=C1 IRIAEXORFWYRCZ-UHFFFAOYSA-N 0.000 description 3
- 125000004432 carbon atom Chemical group C* 0.000 description 3
- XXMIOPMDWAUFGU-UHFFFAOYSA-N hexane-1,6-diol Chemical compound OCCCCCCO XXMIOPMDWAUFGU-UHFFFAOYSA-N 0.000 description 3
- 150000002763 monocarboxylic acids Chemical class 0.000 description 3
- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 description 3
- 239000004033 plastic Substances 0.000 description 3
- 229920003023 plastic Polymers 0.000 description 3
- 125000002889 tridecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 2
- BVUXDWXKPROUDO-UHFFFAOYSA-N 2,6-di-tert-butyl-4-ethylphenol Chemical compound CCC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 BVUXDWXKPROUDO-UHFFFAOYSA-N 0.000 description 2
- KIHBGTRZFAVZRV-UHFFFAOYSA-N 2-Hydroxyoctadecanoic acid Natural products CCCCCCCCCCCCCCCCC(O)C(O)=O KIHBGTRZFAVZRV-UHFFFAOYSA-N 0.000 description 2
- YIWUKEYIRIRTPP-UHFFFAOYSA-N 2-ethylhexan-1-ol Chemical compound CCCCC(CC)CO YIWUKEYIRIRTPP-UHFFFAOYSA-N 0.000 description 2
- PZRWFKGUFWPFID-UHFFFAOYSA-N 3,9-dioctadecoxy-2,4,8,10-tetraoxa-3,9-diphosphaspiro[5.5]undecane Chemical compound C1OP(OCCCCCCCCCCCCCCCCCC)OCC21COP(OCCCCCCCCCCCCCCCCCC)OC2 PZRWFKGUFWPFID-UHFFFAOYSA-N 0.000 description 2
- WPMYUUITDBHVQZ-UHFFFAOYSA-N 3-(3,5-ditert-butyl-4-hydroxyphenyl)propanoic acid Chemical compound CC(C)(C)C1=CC(CCC(O)=O)=CC(C(C)(C)C)=C1O WPMYUUITDBHVQZ-UHFFFAOYSA-N 0.000 description 2
- 239000004803 Di-2ethylhexylphthalate Substances 0.000 description 2
- MQIUGAXCHLFZKX-UHFFFAOYSA-N Di-n-octyl phthalate Natural products CCCCCCCCOC(=O)C1=CC=CC=C1C(=O)OCCCCCCCC MQIUGAXCHLFZKX-UHFFFAOYSA-N 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
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerol Natural products OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
- 229920001944 Plastisol Polymers 0.000 description 2
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 2
- KRADHMIOFJQKEZ-UHFFFAOYSA-N Tri-2-ethylhexyl trimellitate Chemical compound CCCCC(CC)COC(=O)C1=CC=C(C(=O)OCC(CC)CCCC)C(C(=O)OCC(CC)CCCC)=C1 KRADHMIOFJQKEZ-UHFFFAOYSA-N 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- 239000003963 antioxidant agent Substances 0.000 description 2
- UKMSUNONTOPOIO-UHFFFAOYSA-M behenate Chemical compound CCCCCCCCCCCCCCCCCCCCCC([O-])=O UKMSUNONTOPOIO-UHFFFAOYSA-M 0.000 description 2
- 229940116224 behenate Drugs 0.000 description 2
- 229940050390 benzoate Drugs 0.000 description 2
- SAOKZLXYCUGLFA-UHFFFAOYSA-N bis(2-ethylhexyl) adipate Chemical compound CCCCC(CC)COC(=O)CCCCC(=O)OCC(CC)CCCC SAOKZLXYCUGLFA-UHFFFAOYSA-N 0.000 description 2
- AYWLCKHHUFBVGJ-UHFFFAOYSA-N bis(7-methyloctyl) hexanedioate Chemical compound CC(C)CCCCCCOC(=O)CCCCC(=O)OCCCCCCC(C)C AYWLCKHHUFBVGJ-UHFFFAOYSA-N 0.000 description 2
- 150000001991 dicarboxylic acids Chemical class 0.000 description 2
- 235000014113 dietary fatty acids Nutrition 0.000 description 2
- 150000002009 diols Chemical class 0.000 description 2
- POULHZVOKOAJMA-UHFFFAOYSA-M dodecanoate Chemical compound CCCCCCCCCCCC([O-])=O POULHZVOKOAJMA-UHFFFAOYSA-M 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
- 230000000694 effects Effects 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 239000000194 fatty acid Substances 0.000 description 2
- 229930195729 fatty acid Natural products 0.000 description 2
- 239000000945 filler Substances 0.000 description 2
- 239000004615 ingredient Substances 0.000 description 2
- 229940070765 laurate Drugs 0.000 description 2
- 239000000314 lubricant Substances 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 125000001421 myristyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 2
- 150000003014 phosphoric acid esters Chemical class 0.000 description 2
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 2
- 239000000049 pigment Substances 0.000 description 2
- 239000004999 plastisol Substances 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- 230000006641 stabilisation Effects 0.000 description 2
- 238000011105 stabilization Methods 0.000 description 2
- 150000005846 sugar alcohols Polymers 0.000 description 2
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 2
- WBSRIXCTCFFHEF-UHFFFAOYSA-N (3,5-ditert-butyl-4-hydroxyphenyl)methyl-ethoxyphosphinic acid Chemical compound CCOP(O)(=O)CC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 WBSRIXCTCFFHEF-UHFFFAOYSA-N 0.000 description 1
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 description 1
- YJTKZCDBKVTVBY-UHFFFAOYSA-N 1,3-Diphenylbenzene Chemical group C1=CC=CC=C1C1=CC=CC(C=2C=CC=CC=2)=C1 YJTKZCDBKVTVBY-UHFFFAOYSA-N 0.000 description 1
- 150000005208 1,4-dihydroxybenzenes Chemical class 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
- 229940114072 12-hydroxystearic acid Drugs 0.000 description 1
- HECLRDQVFMWTQS-RGOKHQFPSA-N 1755-01-7 Chemical compound C1[C@H]2[C@@H]3CC=C[C@@H]3[C@@H]1C=C2 HECLRDQVFMWTQS-RGOKHQFPSA-N 0.000 description 1
- UUAIOYWXCDLHKT-UHFFFAOYSA-N 2,4,6-tricyclohexylphenol Chemical compound OC1=C(C2CCCCC2)C=C(C2CCCCC2)C=C1C1CCCCC1 UUAIOYWXCDLHKT-UHFFFAOYSA-N 0.000 description 1
- KPZBEZVZFBDKCG-UHFFFAOYSA-N 2,4-dibutylphenol Chemical compound CCCCC1=CC=C(O)C(CCCC)=C1 KPZBEZVZFBDKCG-UHFFFAOYSA-N 0.000 description 1
- OPLCSTZDXXUYDU-UHFFFAOYSA-N 2,4-dimethyl-6-tert-butylphenol Chemical compound CC1=CC(C)=C(O)C(C(C)(C)C)=C1 OPLCSTZDXXUYDU-UHFFFAOYSA-N 0.000 description 1
- LXWZXEJDKYWBOW-UHFFFAOYSA-N 2,4-ditert-butyl-6-[(3,5-ditert-butyl-2-hydroxyphenyl)methyl]phenol Chemical compound CC(C)(C)C1=CC(C(C)(C)C)=CC(CC=2C(=C(C=C(C=2)C(C)(C)C)C(C)(C)C)O)=C1O LXWZXEJDKYWBOW-UHFFFAOYSA-N 0.000 description 1
- DXCHWXWXYPEZKM-UHFFFAOYSA-N 2,4-ditert-butyl-6-[1-(3,5-ditert-butyl-2-hydroxyphenyl)ethyl]phenol Chemical compound C=1C(C(C)(C)C)=CC(C(C)(C)C)=C(O)C=1C(C)C1=CC(C(C)(C)C)=CC(C(C)(C)C)=C1O DXCHWXWXYPEZKM-UHFFFAOYSA-N 0.000 description 1
- CZNRFEXEPBITDS-UHFFFAOYSA-N 2,5-bis(2-methylbutan-2-yl)benzene-1,4-diol Chemical compound CCC(C)(C)C1=CC(O)=C(C(C)(C)CC)C=C1O CZNRFEXEPBITDS-UHFFFAOYSA-N 0.000 description 1
- JZODKRWQWUWGCD-UHFFFAOYSA-N 2,5-di-tert-butylbenzene-1,4-diol Chemical compound CC(C)(C)C1=CC(O)=C(C(C)(C)C)C=C1O JZODKRWQWUWGCD-UHFFFAOYSA-N 0.000 description 1
- LKALLEFLBKHPTQ-UHFFFAOYSA-N 2,6-bis[(3-tert-butyl-2-hydroxy-5-methylphenyl)methyl]-4-methylphenol Chemical compound OC=1C(CC=2C(=C(C=C(C)C=2)C(C)(C)C)O)=CC(C)=CC=1CC1=CC(C)=CC(C(C)(C)C)=C1O LKALLEFLBKHPTQ-UHFFFAOYSA-N 0.000 description 1
- SLUKQUGVTITNSY-UHFFFAOYSA-N 2,6-di-tert-butyl-4-methoxyphenol Chemical compound COC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 SLUKQUGVTITNSY-UHFFFAOYSA-N 0.000 description 1
- FRAQIHUDFAFXHT-UHFFFAOYSA-N 2,6-dicyclopentyl-4-methylphenol Chemical compound OC=1C(C2CCCC2)=CC(C)=CC=1C1CCCC1 FRAQIHUDFAFXHT-UHFFFAOYSA-N 0.000 description 1
- SAJFQHPVIYPPEY-UHFFFAOYSA-N 2,6-ditert-butyl-4-(dioctadecoxyphosphorylmethyl)phenol Chemical compound CCCCCCCCCCCCCCCCCCOP(=O)(OCCCCCCCCCCCCCCCCCC)CC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 SAJFQHPVIYPPEY-UHFFFAOYSA-N 0.000 description 1
- SCXYLTWTWUGEAA-UHFFFAOYSA-N 2,6-ditert-butyl-4-(methoxymethyl)phenol Chemical compound COCC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 SCXYLTWTWUGEAA-UHFFFAOYSA-N 0.000 description 1
- UDFARPRXWMDFQU-UHFFFAOYSA-N 2,6-ditert-butyl-4-[(3,5-ditert-butyl-4-hydroxyphenyl)methylsulfanylmethyl]phenol Chemical compound CC(C)(C)C1=C(O)C(C(C)(C)C)=CC(CSCC=2C=C(C(O)=C(C=2)C(C)(C)C)C(C)(C)C)=C1 UDFARPRXWMDFQU-UHFFFAOYSA-N 0.000 description 1
- VMKMZRBPOSNUMX-UHFFFAOYSA-N 2-(1-hydroxypropan-2-yloxy)propan-1-ol Chemical compound OCC(C)OC(C)CO VMKMZRBPOSNUMX-UHFFFAOYSA-N 0.000 description 1
- LBOGPIWNHXHYHN-UHFFFAOYSA-N 2-(2-hydroxy-5-octylphenyl)sulfanyl-4-octylphenol Chemical compound CCCCCCCCC1=CC=C(O)C(SC=2C(=CC=C(CCCCCCCC)C=2)O)=C1 LBOGPIWNHXHYHN-UHFFFAOYSA-N 0.000 description 1
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- GIPDEPRRXIBGNF-KTKRTIGZSA-N oxolan-2-ylmethyl (z)-octadec-9-enoate Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OCC1CCCO1 GIPDEPRRXIBGNF-KTKRTIGZSA-N 0.000 description 1
- IPCSVZSSVZVIGE-UHFFFAOYSA-N palmitic acid group Chemical group C(CCCCCCCCCCCCCCC)(=O)O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 description 1
- 125000000913 palmityl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 229920005862 polyol Polymers 0.000 description 1
- 229920000098 polyolefin Polymers 0.000 description 1
- 150000003077 polyols Chemical class 0.000 description 1
- 239000004800 polyvinyl chloride Substances 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- 235000013772 propylene glycol Nutrition 0.000 description 1
- 229910052895 riebeckite Inorganic materials 0.000 description 1
- 238000007493 shaping process Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 230000003068 static effect Effects 0.000 description 1
- 229940114926 stearate Drugs 0.000 description 1
- 125000004079 stearyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])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])[H] 0.000 description 1
- 230000000475 sunscreen effect Effects 0.000 description 1
- 239000000516 sunscreening agent Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- KKEYFWRCBNTPAC-UHFFFAOYSA-L terephthalate(2-) Chemical compound [O-]C(=O)C1=CC=C(C([O-])=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-L 0.000 description 1
- 229940072958 tetrahydrofurfuryl oleate Drugs 0.000 description 1
- 230000008646 thermal stress Effects 0.000 description 1
- 150000003568 thioethers Chemical group 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- KFUSEUYYWQURPO-OWOJBTEDSA-N trans-1,2-dichloroethene Chemical group Cl\C=C\Cl KFUSEUYYWQURPO-OWOJBTEDSA-N 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- STCOOQWBFONSKY-UHFFFAOYSA-N tributyl phosphate Chemical compound CCCCOP(=O)(OCCCC)OCCCC STCOOQWBFONSKY-UHFFFAOYSA-N 0.000 description 1
- 229960001147 triclofos Drugs 0.000 description 1
- FICPQAZLPKLOLH-UHFFFAOYSA-N tricyclohexyl phosphite Chemical compound C1CCCCC1OP(OC1CCCCC1)OC1CCCCC1 FICPQAZLPKLOLH-UHFFFAOYSA-N 0.000 description 1
- XZZNDPSIHUTMOC-UHFFFAOYSA-N triphenyl phosphate Chemical compound C=1C=CC=CC=1OP(OC=1C=CC=CC=1)(=O)OC1=CC=CC=C1 XZZNDPSIHUTMOC-UHFFFAOYSA-N 0.000 description 1
- IGQFKXMQIMEIJV-UHFFFAOYSA-N tris(11-methyldodecyl) benzene-1,2,4-tricarboxylate Chemical compound CC(C)CCCCCCCCCCOC(=O)C1=CC=C(C(=O)OCCCCCCCCCCC(C)C)C(C(=O)OCCCCCCCCCCC(C)C)=C1 IGQFKXMQIMEIJV-UHFFFAOYSA-N 0.000 description 1
- KOWVWXQNQNCRRS-UHFFFAOYSA-N tris(2,4-dimethylphenyl) phosphate Chemical compound CC1=CC(C)=CC=C1OP(=O)(OC=1C(=CC(C)=CC=1)C)OC1=CC=C(C)C=C1C KOWVWXQNQNCRRS-UHFFFAOYSA-N 0.000 description 1
- WDRCVXGINNJWPH-UHFFFAOYSA-N tris(6-methylheptyl) benzene-1,2,4-tricarboxylate Chemical compound CC(C)CCCCCOC(=O)C1=CC=C(C(=O)OCCCCCC(C)C)C(C(=O)OCCCCCC(C)C)=C1 WDRCVXGINNJWPH-UHFFFAOYSA-N 0.000 description 1
- FJFYFBRNDHRTHL-UHFFFAOYSA-N tris(8-methylnonyl) benzene-1,2,4-tricarboxylate Chemical compound CC(C)CCCCCCCOC(=O)C1=CC=C(C(=O)OCCCCCCCC(C)C)C(C(=O)OCCCCCCCC(C)C)=C1 FJFYFBRNDHRTHL-UHFFFAOYSA-N 0.000 description 1
- 125000005023 xylyl group Chemical group 0.000 description 1
- 229910052725 zinc Inorganic materials 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
- C08K5/04—Oxygen-containing compounds
- C08K5/15—Heterocyclic compounds having oxygen in the ring
- C08K5/151—Heterocyclic compounds having oxygen in the ring having one oxygen atom in the ring
- C08K5/1515—Three-membered rings
-
- 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
- C08K5/04—Oxygen-containing compounds
- C08K5/09—Carboxylic acids; Metal salts thereof; Anhydrides thereof
- C08K5/098—Metal salts of carboxylic acids
-
- 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
- C08K5/372—Sulfides, e.g. R-(S)x-R'
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
Description
Die vorliegende Erfindung betrifft stabilisierte Zusammensetzungen aus chlorhaltigen Thermoplasten, die einen organischen Weichmacher sowie Thiodiethylenglykolbis-acetoacetat, epoxidierte ungesättigte Fettsäureester, ein Zn-Carboxylat und gegebenenfalls ein Ca-, Ba- oder/und Mg- Carboxylat als Stabilisatoren enthalten.The present invention relates to stabilized compositions Chlorinated thermoplastics containing an organic plasticizer as well Thiodiethylene glycol bis-acetoacetate, epoxidized unsaturated fatty acid esters, a Zn carboxylate and optionally a Ca, Ba or / and Mg Carboxylate as stabilizers included.
Aus der US-A 43 27 000 sind Stabilisatorgemische aus β-Ketocarbonsäureestern von Di- und Polyolen mit Thioetherstruktur und metallhaltigen Stabilisatoren, z. B. Ca- und Zn-Carboxylaten, bekannt. Diese Gemische zeigen an sich gute Stabilisatorwirkung in chlorhaltigen Thermoplasten, z. B. in PVC und PVC enthaltenden Polymeren. Als Beispiel für die genannten β-Ketocarbonsäureester ist darin unter anderen das Thiodiethylenglykol-bis-acetoacetat beschrieben. Trotz der an sich interessanten Eigenschaften der in der US-A 43 27 000 beschriebenen Stabilisatoren konnten letztere bisher nicht kommerzialisiert werden, da ihre Wirkung für praktische Belange doch nicht ausreichend war. Insbesondere vergilbten die damit stabilisierten Polymeren etwas zu stark, vor allem bei längerer thermischer Belastung. Außerdem ließ die Transparenz der mit Hilfe der stabilisierten Polymeren hergestellten Artikel zu wünschen übrig. Diese Feststellungen gelten auch für die beiden konkret in den Applikationsbeispielen A und B der US-A 43 27 000 beschriebenen Stabilisatormischungen, vor allem auch hinsichtlich Anfangsfarbe und Farbhaltung. Ähnliche Zusammensetzungen sind auch aus der JP-A 54-11 948 bekannt, die jedoch zusätzlich noch freie aromatische Carbonsäuren enthalten. Keine der beiden genannten Veröffentlichungen beschreibt stabilisierte PVC-Zusammensetzungen, die einen Weichmacher enthalten. Sie lehren daher nur die Stabilisierung von Hart-PVC. Letzteres unterscheidet sich aber von weichmacherhaltigem grundlegend in der Morpholo gie.From US-A 43 27 000 are stabilizer mixtures of β- ketocarboxylic acid esters of diols and polyols with thioether structure and metal-containing stabilizers, eg. As Ca and Zn carboxylates known. These mixtures show good stabilizer effect in chlorine-containing thermoplastics, for. B. in PVC and PVC-containing polymers. As an example of the β- ketocarboxylic acid esters mentioned, it is described, inter alia, thiodiethylene glycol bis-acetoacetate. Despite the intrinsically interesting properties of the stabilizers described in US-A 43 27 000, the latter could not be commercialized, since their effect was not sufficient for practical purposes. In particular, the polymers stabilized with it yellowed somewhat too strongly, especially during prolonged thermal stress. In addition, the transparency of the articles made using the stabilized polymers left something to be desired. These findings also apply to the two stabilizer mixtures described concretely in Application Examples A and B of US Pat. No. 4,327,000, especially with regard to initial color and color retention. Similar compositions are also known from JP-A 54-11 948, which, however, additionally contain free aromatic carboxylic acids. Neither of these publications describes stabilized PVC compositions containing a plasticizer. They therefore teach only the stabilization of rigid PVC. The latter differs from plasticizer-based fundamentally in the morphology.
Es wurde nun gefunden, daß die Eigenschaften von Stabilisatormischungen, die in der US-A 43 27 000 beschriebene Bestandteile enthalten, derart verbessert werden können, daß sie für einen großtechnischen Einsatz in Frage kommen, und daß sie sich besonders gut für die Stabilisierung von weichmacherhaltigen chlorhaltigen Thermoplasten eignen. Diese Verbesserung kann überraschenderweise dadurch erreicht werden, daß ein ganz bestimmter β-Ketocarbonsäureester mit Zn- und gegebenenfalls Ca-, Ba- oder/und Mg-Carboxylat-Primärstabilisatoren in ganz bestimmten Konzentrationen und Mischungsverhältnissen kombiniert wird.It has now been found that the properties of stabilizer mixtures containing ingredients described in US-A 43 27 000 can be improved so that they are suitable for industrial use in question, and that they are particularly well for the stabilization of plasticizer-containing chlorine-containing thermoplastics are suitable. Surprisingly, this improvement can be achieved by combining a very specific β- ketocarboxylic acid ester with Zn and optionally Ca, Ba or / and Mg carboxylate primary stabilizers in very specific concentrations and mixing ratios.
Die vorliegende Erfindung betrifft stabilisierte Polymerzusammensetzungen, dieThe present invention relates to stabilized polymer compositions, the
- a) 100 Teile eines chlorhaltigen Thermoplasten,a) 100 parts of a chlorine-containing thermoplastic,
- b) 0,7-2 Teile Thiodienthylenglykol-bis-acetoacetat der Formel (H₃CCOCH₂COOCH₂CH₂)₂S,b) 0.7-2 parts Thiodienthylenglykol-bis-acetoacetate of the formula (H₃CCOCH₂COOCH₂CH₂) ₂S,
- c) 0-0,5 Teile mindestens eines Ca-, Ba- oder/und Mg-Salzes einer aliphatischen C₈-C₂₄-Monocarbonsäure oder -Hydroxymonocarbonsäure oder der Benzoesäure oder tert.-Butylbenzoesäure,c) 0-0.5 parts of at least one Ca, Ba or / and Mg salt of a aliphatic C₈-C₂₄ monocarboxylic acid or hydroxy-monocarboxylic acid or benzoic acid or tert-butylbenzoic acid,
- d) 0,01-0,2 Teile mindestens eines Zn-Salzes einer aliphatischen C₈-C₂₄-Monocarbonsäure oder -Hydroxymonocarbonsäure oder der Benzoesäure oder tert.-Butylbenzoesäure,d) 0.01-0.2 parts of at least one Zn salt of an aliphatic C₈-C₂₄ monocarboxylic acid or hydroxymonocarboxylic acid or benzoic acid or tert-butylbenzoic acid,
- e) 3-10 Teile von epoxidierten ungesättigten Fettsäureestern, unde) 3-10 parts of epoxidized unsaturated fatty acid esters, and
- f) 10-70 Teile mindestens eines organischen Weichmachersf) 10-70 parts of at least one organic plasticizer
enthalten.contain.
Thiodiethylenglykol-bis-acetoacetat (Komponente b) ist vorzugsweise in einer Menge von 0,7-1,5, insbesondere 0,8-1,3 Teilen, vor allem etwa 1 Teil, enthalten.Thiodiethylene glycol bis-acetoacetate (component b) is preferably in an amount of 0.7-1.5, especially 0.8-1.3 parts, especially about 1 part, included.
Die Komponente c) ist vorzugsweise in einer Konzentration von 0-0,4, z. B. 0-0,35 Teilen vorhanden. Bevorzugt enthalten die erfindungsgemäßen Zusammensetzungen eine Komponente c) (Konzentration<0). Die Komponente c) ist dann z. B. in einer Menge von 0,001-0,5, vorzugsweise 0,01-0,5, insbesondere 0,05-0,4, vor allem 0,1-0,35 Teilen vorhanden. Mit Mengen von 0,05-0,15 Teilen werden ebenfalls sehr gute Ergebnisse erzielt.The component c) is preferably in a concentration of 0-0.4, z. B. 0-0.35 parts available. Preferably, the inventive Compositions a component c) (concentration <0). The component c) is then z. B. in an amount of 0.001-0.5, preferably 0.01-0.5, especially 0.05-0.4, especially 0.1-0.35 parts present. With Quantities of 0.05-0.15 parts are also very good results achieved.
Die Komponente c) ist ein Ca-, Ba- oder Mg-Salz oder eine Mischung aus solchen Salzen, vorzugsweise ein Ca- oder Mg-, insbesondere ein Ca-Salz, einer aliphatischen C₈-C₂₄-Monocarbonsäure oder -Hydroxymonocarbonsäure oder der Benzoesäure oder tert.-Butylbenzoesäure.Component c) is a Ca, Ba or Mg salt or a mixture of such salts, preferably a Ca or Mg, in particular a Ca salt, an aliphatic C₈-C₂₄ monocarboxylic acid or hydroxy-monocarboxylic acid or benzoic acid or tert-butylbenzoic acid.
Die aliphatischen Monocarbonsäuren bzw. Hydroxycarbonsäuren sind gesättigt oder ungesättigt und weisen insbesondere 8-22 C-Atome auf. Als Hydroxycarbonsäure ist vor allem Hydroxystearinsäure, z. B. 12-Hydroxystearinsäure, zu nennen. Von den Monocarbonsäuren sind die 2-Ethylhexan-, Neodecan-, Laurin-, Stearin- und Behensäure bevorzugt. Bevorzugt ist die Komponente c) Ca-, Ba- oder/und Mg-, vorzugsweise Ca- oder/und Mg-, insbesondere Ca-Octoat (Salz der 2-Ethylenhexansäure), -Laurat, -Stearat- oder -Behenat. Selbstverständlich sind auch Mischungen von Salzen verschiedener Säuren einsetzbar.The aliphatic monocarboxylic acids or hydroxycarboxylic acids are saturated or unsaturated and have in particular 8-22 C atoms. When Hydroxycarboxylic acid is especially hydroxystearic acid, eg. B. 12-hydroxystearic acid, to call. Of the monocarboxylic acids are the 2-ethylhexane, Neodecane, lauric, stearic and behenic acid are preferred. Preferably, the Component c) Ca, Ba or / and Mg, preferably Ca and / or Mg, especially Ca-octoate (salt of 2-ethylene-hexanoic acid), laurate, stearate or behenate. Of course, also mixtures of salts various acids can be used.
Die Komponente d) ist vorzugsweise in einer Menge von 0,05-0,2, insbesondere 0,1-0,2 Teilen enthalten. Sie ist das Zn-Salz einer aliphatischen C₈-C₂₄-Monocarbonsäure oder -Hydroxycarbonsäure oder der Benzoesäure oder tert.-Butylbenzoesäure. Die aliphatischen Monocarbonsäuren bzw. Hydroxycarbonsäuren sind gesättigt oder ungesättigt und weisen insbesondere 8-22 C-Atome auf. Als Hydroxycarbonsäure ist vor allem Hydroxystearinsäure, z. B. 12-Hydroxystearinsäure, zu nennen. Von den Monocarbonsäuren sind die 2-Ethylhexan-, Laurin-, Stearin- und Behensäure bevorzugt. Bevorzugt wird als Komponente d) Zn-Octoat (Salz der 2-Ethylhexansäure), basisches Zn-Octoat, Zn-Stearat, -Neodecanoat, -Laurat, -Behenat oder -Benzoat, insbesondere Zn-Octoat, basisches Zn-Octoat, Zn-Neodecanoat, Zn-Stearat oder Zn-Benzoat, eingesetzt. Dabei wird Zn-Stearat besonders bevorzugt in einer Menge von etwa 0,2 Teilen, Zn-Octoat von etwa 0,1 Teil und basisches Zn-Octoat von etwa 0,05 Teilen verwendet.The component d) is preferably in an amount of 0.05-0.2, in particular 0.1-0.2 parts included. It is the Zn salt of an aliphatic C₈-C₂₄ monocarboxylic acid or hydroxycarboxylic acid or benzoic acid or tert-butylbenzoic acid. The aliphatic monocarboxylic acids or hydroxycarboxylic acids are saturated or unsaturated and have in particular 8-22 C atoms on. Hydroxycarboxylic acid is mainly hydroxystearic acid, z. As 12-hydroxystearic, to call. Of the monocarboxylic acids are the preferred 2-ethylhexane, lauric, stearic and behenic acid. Prefers is as component d) Zn-octoate (salt of 2-ethylhexanoic acid), basic Zn octoate, Zn stearate, neodecanoate, laurate, behenate or benzoate, in particular Zn octoate, basic Zn octoate, Zn neodecanoate, Zn stearate or Zn benzoate used. In this case, Zn-stearate is particularly preferred in an amount of about 0.2 part, Zn octoate of about 0.1 part and basic Zn octoate of about 0.05 parts.
Komponente e) liegt insbesondere in einer Menge von 4-7, vor allem etwa 5 Teilen, vor. Sie ist vorzugsweise epoxidiertes Sojabohnenöl. Component e) is in particular in an amount of 4-7, especially about 5 parts, before. It is preferably epoxidized soybean oil.
Die Komponente f) ist in den erfindungsgemäßen Zusammensetzungen vorzugsweise in einer Menge von 15-70, z. B. 15-60, insbesondere 20-50, Teilen enthalten. Epoxidierte Fettsäureester (Komponente e) werden häufig ebenfalls als Weichmacher bezeichnet. Es ist zu betonen, daß diese Ester von der vorliegenden Definition der Komponente f) (Weichmacher) nicht umfaßt sind. Die Komponenten e) und f) sind daher verschieden.Component f) is in the compositions according to the invention preferably in an amount of 15-70, e.g. B. 15-60, especially 20-50, Parts included. Epoxidized fatty acid esters (component e) become common also referred to as plasticizer. It should be emphasized that these esters from the present definition of component f) (plasticizer) not are included. The components e) and f) are therefore different.
Als organische Weichmacher kommen beispielsweise solche aus den folgenden Gruppen in Betracht:Examples of organic plasticizers are those from the following Groups:
A) Phthalate (Phthalsäureester)
Beispiele für solche Weichmacher sind Dimethyl-, Diethyl-, Dibutyl-,
Dihexyl-, Di-2-ethylhexyl-, Di-n-octyl-, Di-iso-octyl-, Di-iso-nonyl-,
Di-iso-decyl-, Di-iso-tridecyl-, Dicyclohexyl-, Di-methylcyclohexyl-,
Dimethylglycol-, Dibutylglycol-, Benzylbutyl- und Diphenyl-phthalat sowie
Mischungen von Phthalaten wie C₇-C₉- und C₉-C₁₁-Alkylphthalate aus
überwiegend linearen Alkoholen, C₆-C₁₀-n-Alkylphthalate und C₈-C₁₀-n-
Alkylphthalate. Bevorzugt sind davon Dibutyl-, Dihexyl-, Di-2-ethyl-
hexyl-, Di-n-octyl-, Di-iso-octyl-, Di-iso-nonyl-, Di-iso-decyl-,
Di-iso-tridecyl- und Benzylbutyl-phthalat sowie die genannten Mischungen
von Alkylphthalaten. Besonders bevorzugt ist Di-2-ethylhexylphthalat
(DOP).A) phthalates (phthalates)
Examples of such plasticizers are dimethyl, diethyl, dibutyl, dihexyl, di-2-ethylhexyl, di-n-octyl, di-iso-octyl, di-iso-nonyl, di-iso-decyl -, di-iso-tridecyl-, dicyclohexyl-, di-methylcyclohexyl-, dimethylglycol-, dibutylglycol-, benzylbutyl- and diphenyl phthalate and mixtures of phthalates such as C₇-C₉- and C₉-C₁₁-alkyl phthalates of predominantly linear alcohols, C₆ C₁₀-n-alkyl phthalates and C₈-C₁₀ n-alkyl phthalates. Of these, dibutyl, dihexyl, di-2-ethylhexyl, di-n-octyl, di-iso-octyl, di-iso-nonyl, di-isodecyl, di-iso are preferred. tridecyl and benzyl butyl phthalate and the said mixtures of alkyl phthalates. Particularly preferred is di-2-ethylhexyl phthalate (DOP).
B) Ester aliphatischer Dicarbonsäuren, insbesondere Ester von Adipin-,
Azelain- und Sebazinsäure
Beispiele für solche Weichmacher sind Di-2-ethylhexyladipat, Di-iso-
octyladipat (Gemisch), Di-iso-nonyladipat (Gemisch), Di-iso-decyladipat
(Gemisch), Benzylbutyladipat, Benzyloctyladipat, Di-2-ethylhexylazelat,
Di-2-ethylhexylsebacat und Di-iso-decylsebacat (Gemisch). Bevorzugt sind
Di-2-ethylhexyladipat und Di-iso-octyladipat.B) esters of aliphatic dicarboxylic acids, especially esters of adipic, azelaic and sebacic acid
Examples of such plasticizers are di-2-ethylhexyl adipate, diisoctyl adipate (mixture), di-iso-nonyl adipate (mixture), di-isodecyl adipate (mixture), benzyl butyl adipate, benzyloctyl adipate, di-2-ethylhexyl azelate, di-iso-nonyl adipate. 2-ethylhexyl sebacate and diisodecyl sebacate (mixture). Preference is given to di-2-ethylhexyl adipate and di-iso-octyl adipate.
C) Trimellithsäureester,
beispielsweise Tri-2-ethylhexyltrimellithat, Tri-iso-decyltrimellithat
(Gemisch), Tri-iso-tridecyltrimellithat, Tri-iso-octyltrimellithat
(Gemisch) sowie Tri-C₆-C₈-alkyl, Tri-C₆-C₁₀-alkyl-, Tri-C₇-C₉-alkyl- und
Tri-C₉-C₁₁-alkyl-trimellithate. Die letztgenannten Trimellithate
entstehen durch Veresterung der Trimellithsäure mit den entsprechenden
Alkanolgemischen. Bevorzugte Trimellithate sind Tri-2-ethylhexyl-trimellithat
und die genannten Trimellithate aus Alkanolgemischen.C) trimellitic acid ester,
For example, tri-2-ethylhexyl trimellitate, tri-iso-decyl trimellitate (mixture), tri-iso-tridecyl trimellitate, tri-iso-octyl trimellitate (mixture) and tri-C₆-C₈-alkyl, tri-C₆-C₁₀-alkyl, tri C₇-C₉-alkyl and tri-C₉-C₁₁-alkyl trimellitate. The latter trimellitates are formed by esterification of Trimellithsäure with the corresponding alkanol mixtures. Preferred trimellitates are tri-2-ethylhexyl trimellitate and the said trimellitates of alkanol mixtures.
D) Polyester (Polymerweichmacher)
Eine Definition dieser Weichmacher und Beispiele für solche sind im
"Plastics Additives Handbook", Herausgeber H. Gächter und H. Müller,
Hanser Publishers, 1985, Seite 284, Kapital 5.7.10 sowie in
"PVC Technology", Herausgeber W.V. Titow, 4th. Ed., Elsevier Publ.,
1984, Seiten 165-170 angegeben. Die gebräuchlichsten Ausgangsmaterialien
für die Herstellung der Polyesterweichmacher sind: Dicarbonsäuren wie
Adipin-, Phthal-, Azelain- und Sebacinsäure; Diole wie 1,2-Propandiol,
1,3-Butandiol, 1,4-Butandiol, 1,6-Hexandiol, Neopentylglycol und Di-ethylenglykol;
Monocarbonsäuren wie Essig-, Capron-, Capryl-, Laurin-,
Myristin-, Palmitin-, Stearin-, Pelargon- und Benzoesäure; monofunktionelle
Alkohole wie Isooctanol, 2-Ethylhexanol, Isodecanol sowie C₇-C₉-
Alkanol- und C₉-C₁₁-Alkanolgemische. Besonders vorteilhaft sind Polyesterweichmacher
aus den genannten Dicarbonsäuren und monofunktionellen
Alkoholen.D) polyester (polymer plasticizer)
A definition of these plasticizers and examples of such are in the "Plastics Additives Handbook," editors H. Gächter and H. Muller, Hanser Publishers, 1985, page 284, chapter 5.7.10 and in "PVC Technology", publisher WV Titow, 4th. Ed., Elsevier Publ., 1984, pp. 165-170. The most common starting materials for the preparation of polyester plasticizers are: dicarboxylic acids such as adipic, phthalic, azelaic and sebacic acid; Diols such as 1,2-propanediol, 1,3-butanediol, 1,4-butanediol, 1,6-hexanediol, neopentyl glycol and di-ethylene glycol; Monocarboxylic acids such as acetic, caproic, caprylic, lauric, myristic, palmitic, stearic, pelargonic and benzoic acids; monofunctional alcohols such as isooctanol, 2-ethylhexanol, isodecanol and C₇-C₉- alkanol and C₉-C₁₁-alkanol mixtures. Particularly advantageous are polyester plasticizers from the mentioned dicarboxylic acids and monofunctional alcohols.
E) Phosphorsäureester
Eine Difinition dieser Ester ist im vorstehend genannten "Plastics
Additives Handbook" auf Seite 271, Kapitel 5.7.2 zu finden. Beispiele
für solche Phosphorsäureester sind Tributylphosphat, Tri-2-ethylbutylphosphat,
Tri-2-ethylhexylphosphat, Trichlorethylphosphat, 2-Ethyl
hexyl-di-phenylphosphat, Kresyldiphenylphosphat, Triphenylphosphat,
Trikresylphosphat und Trixylenylphosphat. Bevorzugt ist Tri-2-ethyl
hexyl-phosphat.E) phosphoric acid ester
A Difinition of these esters can be found in the aforementioned "Plastics Additives Handbook" on page 271, chapter 5.7.2. Examples of such phosphoric acid esters are tributyl phosphate, tri-2-ethylbutyl phosphate, tri-2-ethylhexyl phosphate, trichloroethyl phosphate, 2-ethylhexyl di-phenyl phosphate, cresyl diphenyl phosphate, triphenyl phosphate, tricresyl phosphate and trixylenyl phosphate. Preferred is tri-2-ethylhexyl phosphate.
F) Chlorierte Kohlenwasserstoffe (Paraffine)F) chlorinated hydrocarbons (paraffins)
G) KohlenwasserstoffeG) hydrocarbons
H) Monoester, z. B. Butyloleat, Phenoxyethyloleat, Tetrahydrofurfuryloleat und Alkylsulfonsäureester.H) monoester, z. B. butyl oleate, phenoxyethyl oleate, tetrahydrofurfuryl oleate and alkylsulfonic acid esters.
I) Glycolester, z. B. Diglykolbenzoate.I) glycol esters, e.g. B. diglycatedzoates.
Definitionen und Beispiele für Weichmacher der Gruppen F) bis I) sind den
folgenden Handbüchern zu entnehmen:
"Plastics Additives Handbook", Herausgeber H. Gächter und H. Müller,
Hanser Publishers, 1985, Seite 284, Kapitel 5.7.11 (Gruppe F)), und
Kapitel 5.7.13 (Gruppe G)).
"PVC Technology", Herausgeber W.V. Titow, 4th. Ed., Elsevier Publishers,
1984, Seiten 171-173, Kapitel 6.10.2 (Gruppe F)), Seite 174,
Kapitel 6.10.5 (Gruppe G)), Seite 173, Kapitel 6.10.3 (Gruppe H)) und
Seiten 173-174, Kapitel 6.10.4 (Gruppe I)).Definitions and examples of plasticizers of groups F) to I) can be found in the following manuals:
"Plastics Additives Handbook", editors H. Gächter and H. Müller, Hanser Publishers, 1985, page 284, chapter 5.7.11 (group F)), and chapter 5.7.13 (group G)).
"PVC Technology", publisher WV Titow, 4th. Ed., Elsevier Publishers, 1984, pages 171-173, Chapter 6.10.2 (Group F)), page 174, Chapter 6.10.5 (Group G)), page 173, Chapter 6.10.3 (Group H)) and pages 173-174, Chapter 6.10.4 (Group I)).
Besonders bevorzugt sind Weichmacher aus den Gruppen A) bis E), insbesondere A) bis C), vor allem die in diesen Gruppen als bevorzugt herausgestellten Weichmacher. Besonders günstig ist Di-2-ethylhexylphthalat (DOP).Particularly preferred are plasticizers from groups A) to E), in particular A) to C), especially those in these groups as preferred exposed plasticizer. Di-2-ethylhexyl phthalate is particularly favorable (DOP).
Bei den erfindungsgemäß stabilisierten chlorhaltigen thermoplastischen Polymeren (Komponente a) handelt es sich insbesondere um Vinylchlorid- Homopolymere (PVC), Mischpolymere des Vinylchlorids mit ungesättigten Comonomeren (PVC-Copolymere), Mischungen der genannten Polymeren untereinander oder Mischungen der genannten Polymeren mit anderen Homo- oder Mischpolymerisaten.In the inventively stabilized chlorine-containing thermoplastic Polymers (component a) are in particular vinyl chloride Homopolymers (PVC), mixed polymers of vinyl chloride with unsaturated Comonomers (PVC copolymers), mixtures of the polymers mentioned with one another or mixtures of said polymers with other homo- or copolymers.
Von den Vinylchloridhomo- und -copolymeren sind besonders Suspensions-
und Massepolymere sowie Emulsionspolymere zu erwähnen. Als Comonomere für
die Copolymerisate kommen z. B. in Frage:
Vinylacetat, Vinylidenchlorid, Transdichlorethylen, Ethylen, Propylen,
Butylen, Maleinsäure, Acrylsäure, Fumarsäure, Itaconsäure. Weitere
geeignete chlorhaltige Polymere sind nachchloriertes PVC und chlorierte
Polyolefine, ferner Pfropfpolymerisate von PVC mit ABS, EVA und MBS. Als
Mischungen seien insbesondere solche von PVC-Homo- oder Copolymeren mit
ABS, NBR, NAR, SAN und EVA genannt.
Of the vinyl chloride homopolymers and copolymers, particular mention should be made of suspension and bulk polymers and emulsion polymers. As comonomers for the copolymers z. B. in question:
Vinyl acetate, vinylidene chloride, transdichlorethylene, ethylene, propylene, butylene, maleic acid, acrylic acid, fumaric acid, itaconic acid. Other suitable chlorine-containing polymers are post-chlorinated PVC and chlorinated polyolefins, and also graft polymers of PVC with ABS, EVA and MBS. Mixtures which may be mentioned in particular those of PVC homo- or copolymers with ABS, NBR, NAR, SAN and EVA.
Die erfindungsgemäßen Zusammensetzungen können auch weitere, für chlorhaltige Thermoplasten übliche Stabilisatoren enthalten. So enthalten sie beispielsweise 0-3 Teile, insbesondere 0-1,5, vor allem 0-1 Teile eines oder mehrerer Phosphite. Solche Phosphite können in einer Menge von 0,01-3, insbesondere 0,01-1,5, z. B. 0,01-1, bevorzugt 0,1-0,6, z. B. 0,2-0,5 Teilen enthalten sein. Beispiele für derartige Phosphite sind etwa solche der FormelnThe compositions according to the invention may also contain further, for Chlorinated thermoplastics contain conventional stabilizers. So included for example, 0-3 parts, especially 0-1.5, especially 0-1 parts one or more phosphites. Such phosphites can be in one Amount of 0.01-3, especially 0.01-1.5, z. B. 0.01-1, preferably 0.1-0.6, z. B. 0.2-0.5 parts may be included. Examples of such phosphites are some of the formulas
worin R¹, R² und R³ gleich oder verschieden sind und C₆-C₁₈-Alkyl, C₆-C₁₈-Alkenyl, einen substituierten oder unsubstituierten Phenylrest oder C₅-C₇-Cycloalkyl bedeuten.wherein R¹, R² and R³ are the same or different and C₆-C₁₈-alkyl, C₆-C₁₈ alkenyl, a substituted or unsubstituted phenyl radical or C₅-C₇ cycloalkyl.
Bedeuten R¹, R² und R³ C₆-C₁₈-Alkyl, so handelt es sich dabei z. B. um n-Hexyl, n-Octyl, n-Nonyl, Decyl, Dodecyl, Tetradecyl, Hexadecyl oder Octadecyl. Bevorzugt sind Alkylgruppen mit 8 bis 18 C-Atomen.Mean R¹, R² and R³ C₆-C₁₈-alkyl, so it is z. B. order n-hexyl, n-octyl, n-nonyl, decyl, dodecyl, tetradecyl, hexadecyl or Octadecyl. Preference is given to alkyl groups having 8 to 18 carbon atoms.
Als substituiertes Phenyl bedeuten R¹, R² und R³ beispielsweise Tolyl, Ethylphenyl, Xylyl, Cumyl, Cymyl, Kresyl, 4-Methoxyphenyl, 2,4-Di methoxyphenyl, Ethoxyphenyl, Butoxyphenyl, p-n-Octylphenyl, p-n-Nonyl phenyl oder p-n-Dodecylphenyl.As substituted phenyl, R¹, R² and R³ are, for example, tolyl, Ethylphenyl, xylyl, cumyl, cymyl, cresyl, 4-methoxyphenyl, 2,4-di methoxyphenyl, ethoxyphenyl, butoxyphenyl, p-n-octylphenyl, p-n-nonyl phenyl or p-n-dodecylphenyl.
Besonders geeignete Phosphite sind Trioctyl-, Tridecyl-, Tridodecyl-, Tritetradecyl, Tristearyl-, Trioleyl-, Triphenyl-, Trikresyl-, Tris-p- nonylphenyl- oder Tricyclohexylphosphit und besonders bevorzugt sind die Aryl-Dialkyl- sowie die Alkyl-Diaryl-Phosphite, wie z. B. Phenyldidecyl-, (2,4-Di-tert.-butylphenyl)-di-dodecylphosphit, (2,6-Di-tert.-butyl phenyl)-di-dodecylphosphit und die Dialkyl- und Diaryl-pentaerythrit-di- phosphite, wie Distearylpentaerythrit-diphosphit.Particularly suitable phosphites are trioctyl, tridecyl, tridodecyl, Tritetradecyl, tristearyl, trioleyl, triphenyl, tricresyl, tris-p nonylphenyl or tricyclohexyl phosphite and particularly preferred are the Aryl-dialkyl and the alkyl-diaryl-phosphites, such as. Phenyldidecyl, (2,4-di-tert-butylphenyl) -di-dodecyl phosphite, (2,6-di-tert-butyl phenyl) -di-dodecyl phosphite and the dialkyl- and diaryl-pentaerythritol-di- phosphites, such as distearyl pentaerythritol diphosphite.
Bevorzugte organische Phosphite sind Distearyl-pentaerythrit-diphosphit, Trisnonylphenylphosphit und Phenyl-didecyl-phosphit. Preferred organic phosphites are distearyl pentaerythritol diphosphite, Trisnonylphenyl phosphite and phenyl didecyl phosphite.
Ferner können in den erfindungsgemäßen Zusammensetzungen weitere bekannte Costabilisatoren enthalten sein, beispielsweise 0-2, insbesondere 0-1,5 Teile. Sie sind dann vorzugsweise in einer Menge von 0,01-2, insbesondere 0,05-1,5, z. B. 0,1-1, vor allem 0,1-0,5 Teilen vorhanden. Als derartige Costabilisatoren seien Aminocrotonsäureester, Dehydracetsäure, 1,3-Diketoverbindungen, 2,4-Dihydroxybenzophenon, 2,4-Dihydroxy- 4′-tert.-butylbenzophenon und Pyrrolderivate genannt, wobei letztere bevorzugt sind.Furthermore, in the compositions according to the invention further contain known costabilizers, for example 0-2, in particular 0-1.5 parts. They are then preferably in an amount of 0.01-2, in particular 0.05-1.5, z. B. 0.1-1, especially 0.1-0.5 parts available. As such costabilizers aminocrotonic, dehydroacetic, 1,3-diketo compounds, 2,4-dihydroxybenzophenone, 2,4-dihydroxy 4'-tert-butylbenzophenone and pyrrole derivatives mentioned, the latter are preferred.
Als Aminocrotonsäureester kommen insbesondere die Ester mit einwertigen geradkettigen C₈-C₂₀-, insbesondere C₁₂-C₁₈-Alkoholen und/oder mit 1,3- bzw. 1,4-Butandiol und/oder 1,2-Dipropylenglykol und/oder Thiodiethylenglykol in Betracht.Particularly suitable aminocrotonic esters are the esters with monohydric straight-chain C₈-C₂₀-, in particular C₁₂-C₁₈ alcohols and / or with 1,3- or 1,4-butanediol and / or 1,2-dipropylene glycol and / or thiodiethylene glycol into consideration.
Als Costabilisatoren verwendbare 1,3-Diketoverbindungen sind insbesondere jene, die in der DE-B 26 00 516 und EP-A 35 268 beschrieben sind, z. B. solche der im Patentanspruch der DE-B 26 00 516 angegebenen Formel. Bevorzugte 1,3-Diketoverbindungen sind Benzoylstearoyl-methan, 2-Benzoyl acetessigsäurealkyl(z. B. etyhl)-ester und Triacylmethane.In particular, 1,3-diketo compounds useful as costabilizers are those described in DE-B 26 00 516 and EP-A 35 268, z. B. those of the claim of DE-B 26 00 516 given formula. Preferred 1,3-diketo compounds are benzoylstearoylmethane, 2-benzoyl acetoacetic acid alkyl (eg etyhl) esters and triacylmethanes.
Als Pyrrol-Costabilisatoren sind jene besonders zu erwähnen, die in der EP-A 22 087 und der GB-A 20 78 761 beschrieben sind, z. B. der dort angegebenen Formel I, vorzugsweise jene Pyrrolderivate, die in den Ansprüchen 2-9 der EP-A 22 087 definiert sind. Als Beispiel sei 2-Methyl- 3-cyclohexyloxycarbonyl-4-phenyl-1H-pyrrol genannt.As Pyrrol Costabilisatoren those are particularly to be mentioned, which in the EP-A 22 087 and GB-A 20 78 761 are described, for. B. the there given formula I, preferably those pyrrole derivatives which in the Claims 2-9 of EP-A 22 087 are defined. As an example, let 2-methyl Called 3-cyclohexyloxycarbonyl-4-phenyl-1H-pyrrole.
Ferner können die erfindungsgemäßen Zusammensetzungen neben den vorstehend genannten fakultativen Costabilisatoren oder an deren Stelle noch weitere fakultative Bestandteile enthalten, z. B. Organozinnstabilisatoren, wie z. B. Butylthiostannonsäure, Mono-[n-octyl]-zinn-tris-[iso octyl-thioglykolat], Di-n-octyl-zinn-bis-[isooctyl-thioglykolat], Di-butylzinnsulfid, Di-butyl-zinn-thioglykolat oder Mono-[butyl]-zinnsulfid sowie Mono-[methyl]-zinn-tris-[alkyl-thioglykolat], Mono-[n- butyl]-zinn-tris-[alkyl-thioglykolat], Mono-[carb-n-butoxy-ethyl]-zinn- tris-[alkyl-thioglykolat], Bis-[methyl]-zinn-bis-[alkyl-thioglykolat], Bis-[n-butyl]-zinn-bis-[alkyl-thioglykolat], Bis-[carb-n-butoxyethyl]- zinn-bis-[alkyl-thioglykolat], Mono-[methyl]-zinn-bis-[alkylthiopro pionat], Mono-[n-butyl]-zinn-tris-[alkyl-thiopropionat], Mono-[carb-n- butoxy-ethyl]-zinn-tris-[alkyl-thiopropionat], Bis-[methyl]-zinn-bis- [alkyl-thiopropionat], Bis-[n-butyl]-zinn-bis-[alkyl-thiopropionat], Bis-[carb-n-butoxy-ethyl]-zinn-bis-[alkyl-thiopropionat], wobei Alkyl beispielsweise 2-Ethylhexyl, Dodecyl, Tridecyl oder Tetradecyl bedeutet, und auch Organozinncarboxylate, insbesondere Maleinate oder Halbestermaleinate, oder Mischungen der vorgenannten Organozinnstabilisatoren, oder organische Antimonverbindungen, wie Antimon-tris-[isooctyl-thio- glykolat] (Isooctyl=2-Ethylhexyl).Furthermore, the compositions according to the invention in addition to the above facultative co-stabilizers or in their place contain additional optional ingredients, e.g. B. organotin stabilizers, such as Butylthiostannonic acid, mono- [n-octyl] -tin-tris- [iso octyl-thioglycolate], di-n-octyl-tin-bis- [isooctyl-thioglycolate], Di-butyltin sulfide, di-butyl-tin thioglycolate or mono- [butyl] -tin sulfide as well as mono- [methyl] -tin-tris- [alkyl-thioglycolate], mono- [n- butyl] -tin-tris [alkyl-thioglycolate], mono [carb-n-butoxy-ethyl] -tin tris [alkyl thioglycolate], bis [methyl] tin bis [alkyl thioglycolate], Bis- [n-butyl] -tin bis [alkyl thioglycolate], bis [carb-n-butoxyethyl] - tin bis [alkyl thioglycolate], mono [methyl] tin bis [alkylthiopro mono- [n-butyl] -tin tris- [alkylthiopropionate], mono- [carb-n-] butoxy-ethyl] -tin-tris [alkyl-thiopropionate], bis [methyl] -tin-bis- [alkyl-thiopropionate], bis [n-butyl] -tin-bis [alkylthiopropionate], Bis- [carb-n-butoxy-ethyl] -tin-bis [alkylthiopropionate], wherein alkyl for example, 2-ethylhexyl, dodecyl, tridecyl or tetradecyl, and also organotin carboxylates, in particular maleinates or half-ester maleates, or mixtures of the aforementioned organotin stabilizers, or organic antimony compounds, such as antimony tris [isooctylthio] glycolate] (isooctyl = 2-ethylhexyl).
Ferner können die erfindungsgemäßen Zusammensetzungen übliche Antioxidantien enthalten. Beispiele dafür sind:Furthermore, the compositions according to the invention may contain conventional antioxidants contain. Examples are:
1.1. Alkylierte Monophenole,
z. B. 2,6-Di-tert.butyl-4-methylphenol,
2-Tert.butyl-4,6-dimethylphenol, 2,6-Di-tert.butyl-4-ethylphenol,
2,6-Di-tert.butyl-4-n-butylphenol, 2,6-Di-tert.butyl-4-i-butylphenol,
2,6-Di-cyclopentyl-4-methylphenol, 2-( α-Methylcyclohexyl)-4,6-dimethylphenol,
2,6-Di-octadecyl-4-methylphenol, 2,4,6-Tri-cyclohexylphenol,
2,6-Di-tert.butyl-4-methoxymethylphenol.1.1. Alkylated monophenols,
z. For example, 2,6-di-tert-butyl-4-methylphenol, 2-tert-butyl-4,6-dimethylphenol, 2,6-di-tert-butyl-4-ethylphenol, 2,6-di-tert. butyl-4-n-butylphenol, 2,6-di-tert-butyl-4-i-butylphenol, 2,6-di-cyclopentyl-4-methylphenol, 2- ( α- methylcyclohexyl) -4,6-dimethylphenol, 2,6-di-octadecyl-4-methylphenol, 2,4,6-tri-cyclohexylphenol, 2,6-di-tert-butyl-4-methoxymethylphenol.
1.2. Alkylierte Hydrochinone,
z. B. 2,6-Di-tert.butyl-4-methoxyphenol,
2,5-Di-tert.butyl-hydrochinon, 2,5-Di-tert.amyl-hydrochinon, 2,6-Di-
phenyl-4-octadecyloxyphenol.1.2. Alkylated hydroquinones,
z. B. 2,6-di-tert-butyl-4-methoxyphenol, 2,5-di-tert-butyl-hydroquinone, 2,5-di-tert-amyl-hydroquinone, 2,6-diphenyl-4- octadecyloxyphenol.
1.3. Hydroxylierte Thiodiphenylether,
z. B. 2,2′-Thio-bis-(6-tert.-
butyl-4-methylphenol), 2,2′-Thio-bis-(4-octylphenol), 4,4′-Thio-bis-(6-
tert.butyl-3-methylphenol), 4,4′-Thio-bis-(6-tert.butyl-2-methylphenol).1.3. Hydroxylated thiodiphenyl ethers,
z. B. 2,2'-thio-bis (6-tert-butyl-4-methylphenol), 2,2'-thio-bis (4-octylphenol), 4,4'-thio-bis (6 tert-butyl-3-methylphenol), 4,4'-thio-bis (6-tert-butyl-2-methylphenol).
1.4. Alkyliden-Bisphenole,
z. B. 2,2′-Methylen-bis-(6-tert.butyl-4-methyl
phenol), 2,2′-Methylen-bis-(6-tert.butyl-4-ethylphenol), 2,2′-Methylen-
bis-[4-methyl-6-( α-methylcyclohexyl)-phenol], 2,2′-Methylen-bis-(4-
methyl-6-cyclohexylphenol), 2,2′-Methylen-bis-(6-nonyl-4-methylphenol),
2,2′-Methylen-bis-(4,6-di-tert.butylphenol), 2,2′-Ethyliden-bis-(4,6-di-
tert.butylphenol), 2,2′-Ethyliden-bis-(6-tert.butyl-4-isobutylphenol),
2,2′-Methylen-bis-[6-( α-methylbenzyl)-4-nonylphenol], 2,2′-Methylen-
bis-[6-( a,α-dimethylbenzyl)-4-nonylphenol], 4,4′-Methylen-bis-(2,6-di-
tert.butylphenol), 4,4′-Methylen-bis-(6-tert.butyl-2-methylphenol),
1,1-Bis-(5-tert.butyl-4-hydroxy-2-methylphenyl)-butan, 2,6-Di-(3-
tert.butyl-5-methyl-2-hydroxybenzyl)-4-methylphenol, 1,1,3-Tris-(5-
tert.butyl-4-hydroxy-2-methylphenyl)-butan, 1,1-Bis-(5-tert.butyl-4-
hydroxy-2-methylphenyl)-3-n-dodecylmercaptobutan, Ethylenglycol-bis-
[3,3-bis-(3′-tert.butyl-4′-hydroxyphenyl)-butyrat], Di-(3-tert.butyl-4-
hydroxy-5-methylphenyl)-dicyclopentadien, Di-[2-(3′-tert.butyl-2′-
hydroxy-5′-methyl-benzyl)-6-tert.butyl-4-methyl-phenyl]-terephthalat-.1.4. Alkylidene bisphenols,
z. 2,2'-methylenebis (6-tert-butyl-4-methylphenol), 2,2'-methylenebis (6-tert-butyl-4-ethylphenol), Methylenebis [4-methyl-6- ( α- methylcyclohexyl) phenol], 2,2'-methylenebis (4-methyl-6-cyclohexylphenol), 2,2'-methylene-bis (6 nonyl-4-methylphenol), 2,2'-methylenebis (4,6-di-tert-butylphenol), 2,2'-ethylidene-bis (4,6-di-tert-butylphenol), 2,2'-ethylidenebis (6-tert-butyl-4-isobutylphenol), 2,2'-methylenebis [6- ( α- methylbenzyl) -4-nonylphenol], 2,2'-methylene - bis- [6- (a, α-dimethylbenzyl) -4-nonylphenol], 4,4'-methylenebis (2,6-di-tert-butylphenol), 4,4'-methylene-bis- ( 6-tert-butyl-2-methylphenol), 1,1-bis- (5-tert-butyl-4-hydroxy-2-methylphenyl) -butane, 2,6-di- (3-tert-butyl-5- methyl-2-hydroxybenzyl) -4-methylphenol, 1,1,3-tris (5-tert-butyl-4-hydroxy-2-methylphenyl) butane, 1,1-bis (5-tert-butyl) 4-hydroxy-2-methylphenyl) -3-n-dodecylmercaptobutane, ethylene glycol bis [3,3-bis (3'-tert-butyl-4'-hydroxyphenyl) butyrate], di- (3-tert. butyl-4-hydrox y-5-methylphenyl) dicyclopentadiene, di- [2- (3'-tert-butyl-2'-hydroxy-5'-methylbenzyl) -6-tert-butyl-4-methylphenyl] terephthalate ,
1.5. Benzylverbindungen,
z. B. 1,3,5-Tri-(3,5-di-tert.butyl-4-hydroxy
benzyl)-2,4,6-trimethylbenzol, Di-(3,5-di-tert.butyl-4-hydroxyben
zyl)-sulfid, 3,5-Di-tert.butyl-4-hydroxybenzyl-mercaptoessigsäure-isooctylester,
Bis-(4-tert.butyl-3-hydroxy-2,6-dimethylbenzyl)dithiol-
terephthalat, 1,3,5-Tris-(3,5-di-tert.butyl-4-hydroxybenzyl)-isocyanurat,
1,3,5-Tris-(4-tert.butyl-3-hydroxy-2,6-dimethylbenzyl)-isocyanurat,
3,5-Di-tert.butyl-4-hydroxybenzyl-phosphonsäure-dioctadecylester,
3,5-Di-tert.butyl-4-hydroxybenzyl-phosphonsäure-monoethylester,
Calcium-salz.1.5. benzyl,
z. B. 1,3,5-tri (3,5-di-tert-butyl-4-hydroxybenzyl) -2,4,6-trimethylbenzene, di- (3,5-di-tert-butyl-4- hydroxybenzyl) sulfide, 3,5-di-tert-butyl-4-hydroxybenzyl-mercaptoacetic acid isooctyl ester, bis (4-tert-butyl-3-hydroxy-2,6-dimethylbenzyl) dithiol terephthalate, 1.3 , 5-Tris (3,5-di-tert-butyl-4-hydroxybenzyl) isocyanurate, 1,3,5-tris (4-tert-butyl-3-hydroxy-2,6-dimethylbenzyl) isocyanurate , 3,5-di-tert-butyl-4-hydroxybenzyl-phosphonic dioctadecyl ester, 3,5-di-tert-butyl-4-hydroxybenzyl-phosphonic acid monoethyl ester, calcium salt.
1.6. Acylaminophenole,
z. B. 4-Hydroxy-laurinsäureanilid, 4-Hydroxy
stearinsäureanilid, 2,4-Bis-octylmercapto-6-(3,5-di-tert.butyl-4-hydroxy
anilino)-s-triazin, N-(3,5-di-tert.butyl-4-hydroxyphenyl)-carbaminsäure
octylester.1.6. Acylaminophenols
z. 4-hydroxy-lauric acid anilide, 4-hydroxy-stearic acid anilide, 2,4-bis-octylmercapto-6- (3,5-di-tert-butyl-4-hydroxyanilino) -s-triazine, N- (3,5 di-tert-butyl-4-hydroxyphenyl) -carbamic acid octyl ester.
1.7. Ester der β-(3,5-Di-tert.butyl-4-hydroxyphenyl)-propionsäure
mit ein- oder mehrwertigen Alkoholen, wie z. B. mit Methanol, Octadecanol,
1,6-Hexandiol, Neopentylglycol, Thiodiethylenglycol, Diethylenglycol,
Triethylenglycol, Pentaerythrit, Tris-hydroxyethyl-isocyanurat, Di-
hydroxyethyl-oxalsäurediamid.1.7. Esters of β- (3,5-di-tert-butyl-4-hydroxyphenyl) -propionic acid
with monohydric or polyhydric alcohols, such as. With methanol, octadecanol, 1,6-hexanediol, neopentyl glycol, thiodiethylene glycol, diethylene glycol, triethylene glycol, pentaerythritol, tris-hydroxyethyl isocyanurate, di-hydroxyethyl-oxalic acid diamide.
1.8. Ester der β-(5-tert.Butyl-4-hydroxy-3-methylphenyl)-propion
säure
mit ein- oder mehrwertigen Alkoholen, wie z. B. mit Methanol,
Octadecanol, 1,6-Hexandiol, Neopentylglycol, Thiodiethylenglycol, Di
ethylenglycol, Triethylenglycol, Pentaerythrit, Tris-hydroxyethyl-isocyanurat,
Di-hydroxyethyl-oxyalsäurediamid.1.8. Esters of β- (5-tert-butyl-4-hydroxy-3-methylphenyl) -propionic acid
with monohydric or polyhydric alcohols, such as. Example, with methanol, octadecanol, 1,6-hexanediol, neopentyl glycol, thiodiethylene glycol, diethylene glycol, triethylene glycol, pentaerythritol, tris-hydroxyethyl isocyanurate, di-hydroxyethyl-oxyalsäurediamid.
1.9. Amide der β-(3,5-Di-tert.butyl-4-hydroxyphenyl)-propionsäure,
wie z. B. N,N′-Di-(3,5-di-tert.butyl-4-hydroxyphenylpropionyl)-hexamethylendia-min,
N,N′-Di-(3,5-di-tert.butyl-4-hydroxyphenylpropionyl)-
trimethylendiamin, N,N′-Di-(3,5-di-tert.butyl-4-hydroxyphenylpropionyl)-
hydrazin.1.9. Amides of β- (3,5-di-tert-butyl-4-hydroxyphenyl) -propionic acid,
such as N, N'-di- (3,5-di-tert-butyl-4-hydroxyphenylpropionyl) -hexamethylenediamine, N, N'-di- (3,5-di-tert-butyl-4-hydroxyphenylpropionyl ) - trimethylenediamine, N, N'-di- (3,5-di-tert-butyl-4-hydroxyphenylpropionyl) hydrazine.
Je nach Verwendungszweck können in die erfindungsgemäßen Zusammensetzungen außerdem noch weitere übliche Zusätze eingearbeitet werden, wie z. B. Gleitmittel (z. B. Montanwachse oder Glycerinester), Fettsäureester, Paraffine, Füllstoffe, Ruß, Asbest, Kaolin, Talk, Glasfasern, optische Aufheller, Pigmente, Lichtstabilisatoren, UV-Absorber, Flammschutzmittel oder/und Antistatika, insbesondere Gleitmittel, Pigmente, Verarbeitungshilfen, Füllstoffe, Antioxidantien und/oder Lichtschutz mittel.Depending on the intended use, in the compositions according to the invention In addition, other common additives are incorporated, such as Lubricants (eg montan waxes or glycerol esters), fatty acid esters, Paraffins, fillers, carbon black, asbestos, kaolin, talc, glass fibers, optical brighteners, pigments, light stabilizers, UV absorbers, flame retardants or / and antistatic agents, especially lubricants, pigments, Processing aids, fillers, antioxidants and / or sunscreen medium.
Vorzugsweise enthalten die erfindungsgemäßen Zusammensetzungen keine freien aromatischen Carbonsäuren, insbesondere solche nicht, wie sie in der JP-A 54-11 948 als Komponente (d) beschrieben sind.Preferably, the compositions according to the invention contain no free aromatic carboxylic acids, especially those not as in JP-A 54-11 948 are described as component (d).
Die erfindungsgemäßen Zusammensetzungen können nach den dafür gebräuchlichen Formgebungsverfahren, z. B. durch Extrusion, Spritzgießen, Kalandrieren oder "slush mold"-Verfahren (Pulver oder Plastisol) zu Formteilen verarbeitet werden. Auch die Verwendung als Plastisole ist möglich. Bevorzugt werden daraus PVC-Folien für Lebensmittelverpackungen hergestellt.The compositions according to the invention can be used according to the customary ones Shaping process, for. B. by extrusion, injection molding, Calendering or "slush mold" process (powder or plastisol) Molded parts are processed. Also, the use as plastisols is possible. Preference is given to PVC films for food packaging manufactured.
Die nachfolgenden Beispiele dienen der weiteren Erläuterung der Erfindung. Teile und Prozente beziehen sich darin sowie in der übrigen Beschreibung und in den Patentansprüchen auf das Gewicht, sofern nichts anderes angegeben ist.The following examples serve to further illustrate the invention. Parts and percentages are in it and in the rest Description and in the claims on the weight, if nothing another is indicated.
Folgende PVC-Zusammensetzungen werden durch Vermischen der einzelnen Komponenten hergestellt (Mengenangabe in Gew.-Teilen): The following PVC compositions are prepared by mixing the individual Components produced (quantity in parts by weight):
Die in Tabelle 1 angeführten Mischungen werden auf einem Mischwalzwerk 5 Minuten bei 180°C gewalzt. Vom gebildeten 0,3 mm dicken Walzfell werden Folienmuster in einem Testofen (®Mathis Thermotakter Typ LTF-ST) bei 180°C thermisch belastet. Nach in der Tabelle 2 angegebenen Zeitintervallen wird jeweils an einem Prüfmuster der Yellowness-Index (YI) nach ASTM D 1925-70 bestimmt (hohe YI-Werte bedeuten starke Verfärbung und damit geringe Stabilität).The mixtures listed in Table 1 are on a mixing mill Rolled at 180 ° C for 5 minutes. From the formed 0.3 mm thick rolled skin Foil samples in a test oven (®Mathis thermostatic type LTF-ST) at 180 ° C thermally stressed. After in the table 2 indicated time intervals each time the yellowness index (YI) is checked on a test sample ASTM D 1925-70 determined (high YI values indicate strong discoloration and thus low stability).
Die in Tabelle 1 angeführten Mischungen werden auf einem Mischwalzwerk 5 Minuten bei 180°C gewalzt. Das erhaltene Walzfell wird während 3 Minuten bei 180°C und 150 bar zu einer 3 mm dicken Platte verpreßt. An dieser wird ebenfalls der Yellowness Index (YI) wie vorstehend beschrieben bestimmt. Die erhaltenen Werte sind Tabelle 3 zu entnehmen.The mixtures listed in Table 1 are on a mixing mill Rolled at 180 ° C for 5 minutes. The resulting rolled fur is during Pressed for 3 minutes at 180 ° C and 150 bar to a 3 mm thick plate. On this also becomes the yellowness index (YI) as described above certainly. The values obtained are shown in Table 3.
Es werden folgende PVC-Zusammensetzungen durch Vermischen der einzelnen Komponenten hergestellt (Mengenangabe in Gew.-Teilen): The following PVC compositions are prepared by mixing the individual Components produced (quantity in parts by weight):
Vorzugsweise werden die Zusammensetzungen gemäß Beispielen 1-8 und Vergleichsformulierungen in der Weise hergestellt, daß die Metallcarboxylate mit ESO, Di-isodecyl-phenylphosphit und Shellsol A zu einer Stabilisatormischung vermischt werden. Diese wird dann zusammen mit dem Thiodiethylenglykol-bis-acetoacetat und dem Weichmacher (Dioctylphthalat) in das PVC eingeleitet.Preferably, the compositions according to Examples 1-8 and Comparative formulations prepared in such a way that the metal carboxylates with ESO, di-isodecyl-phenyl phosphite and Shellsol A to a Stabilizer mixture are mixed. This is then together with the Thiodiethylene glycol bis-acetoacetate and the plasticizer (dioctyl phthalate) introduced into the PVC.
Die in Tabelle 4 angeführten Mischungen werden wie für die Beispiele 1-4 beschrieben zu einem Walzfell verarbeitet, letzteres thermisch belastet und dessen Yellowness-Index in 5 Minuten-Intervallen bestimmt. Die Ergebnisse sind in Tabelle 5 zusammengefaßt. The mixtures listed in Table 4 become as for Examples 1-4 described processed to a rolled fur, the latter thermally loaded and its yellowness index determined at 5 minute intervals. The Results are summarized in Table 5.
Die Mischungen gemäß Tabelle 4 werden außerdem wie für die Beispiele 1-4 beschrieben zu einer Preßplatte verarbeitet und der YI der letzteren bestimmt. Die Werte sind Tabelle 6 zu entnehmen.The mixtures according to Table 4 are also as for the examples 1-4 described processed to a press plate and the YI the the latter determined. The values are shown in Table 6.
Es werden folgende PVC-Zusammensetzungen durch Vermischen der einzelnen Komponenten hergestellt (Mengenangabe in Gew.-Teilen): The following PVC compositions are prepared by mixing the individual Components produced (quantity in parts by weight):
Die in Tabelle 7 angeführten Mischungen werden wie für die Beispiele 1-4 beschrieben zu einem Walzfell verarbeitet, letzteres wie dort beschrieben thermisch belastet und dessen Yellowness-Index (YI) in 5 Minuten-Intervallen bestimmt. Die Ergebnisse sind in Tabelle 8 zusammengefaßt.The mixtures listed in Table 7 are as for Examples 1-4 described processed into a rolled fur, the latter as described there thermally loaded and its yellowness index (YI) at 5 minute intervals certainly. The results are summarized in Table 8.
Die Mischungen gemäß Tabelle 7 werden außerdem wie für die Beispiele 1-4 beschrieben zu einer Preßplatte verarbeitet und der Yellowness-Index der letzteren bestimmt. Die erhaltenen Werte sind in Tabelle 9 angegeben. The mixtures according to Table 7 are also as for the examples 1-4 described processed to a press plate and the Yellowness index of the latter determined. The values obtained are in Table 9 indicated.
Es werden folgende PVC-Zusammensetzungen durch Vermischen der einzelnen Komponenten hergestellt (Mengenangabe in Gew.- Teilen):The following PVC compositions are mixed of the individual components (quantity in parts by weight) Divide):
Die in Tabelle 10 angeführten Zusammensetzungen werden auf einem Mischwalzwerk 10 Minuten bei 190°C gewalzt. Vom gebildeten 0,3 mm dicken Walzfell werden Folienmuster in einem Testofen (®Mathis Termotakter LTF-ST) bei 190°C thermisch belastet. Der Yellowness-Index (YI) der Prüfmuster wird wie für die Beispiele 1-4 angegeben bestimmt. Die erhaltenen Resultate sind in Tabelle 11 zusammengefaßt. The compositions listed in Table 10 are on a mixing mill Rolled for 10 minutes at 190 ° C. From the formed 0.3 mm thick Rolled skin becomes film samples in a test oven (®Mathis Termotakter LTF-ST) at 190 ° C thermally stressed. The yellowness index (YI) the test specimen is determined as specified for Examples 1-4. The results obtained are summarized in Table 11.
Die Zusammensetzungen gemäß Tabelle 10 werden außerdem wie für die Beispiele 1-4 beschrieben zu einer Preßplatte verarbeitet und der Yellowness-Index der letzteren bestimmt. Die erhaltenen Werte sind aus Tabelle 12 ersichtlich.The compositions according to Table 10 are also used as for the Examples 1-4 described processed to a press plate and the Yellowness index of the latter determined. The values obtained are off Table 12 can be seen.
Durch Vermischen der einzelnen Komponenten wird folgende PVC-Zusammensetzung hergestellt:By mixing the individual components, the following PVC composition made:
100 Gew.-Teile S-PVC (K-Wert 64)
15 Gew.-Teile Dioctylphthalat
0,04 Gew.-Teile Zn-Neodecanoat
0,7 Gew.-Teile Thiodiethylenglykol-bis-acetaoacetat
5 Gew.-Teile Epoxidiertes Sojabohnenöl (ESO)
0,3 Gew.-Teile 2-Methyl-3-cyclohexyloxycarbonyl-4-phenyl-1H-pyrrol100 parts by weight S-PVC (K value 64)
15 parts by weight of dioctyl phthalate
0.04 parts by weight Zn neodecanoate
0.7 parts by weight of thiodiethylene glycol bis-acetoacetate
5 parts by weight of epoxidized soybean oil (ESO)
0.3 part by weight of 2-methyl-3-cyclohexyloxycarbonyl-4-phenyl-1H-pyrrole
Diese Zusammensetzung wird wie für die Beispiele 1-4 beschrieben zu einem Walzfell verarbeitet, letzteres wie dort beschrieben thermisch belastet und dessen Yellowness-Index in 5-Minuten-Intervallen bestimmt. Die folgenden YI-Werte werden erhalten:This composition becomes as described for Examples 1-4 Walzfell processed, the latter as described there thermally loaded and its yellowness index determined at 5-minute intervals. The following YI values are obtained:
Claims (17)
- a) 100 Teile eines chlorhaltigen Thermoplasten,
- b) 0,7-2 Teile Thiodiethylenglykol-bis-acetoacetat der Formel (H₃CCOCH₂COOCH₂CH₂)₂S,
- c) 0-0,5 Teile mindestens eines Ca-, Ba- oder/und Mg-Salzes einer aliphatischen C₈-C₂₄-Monocarbonsäure oder -Hydroxymonocarbonsäure oder der Benzoesäure oder tert.-Butylbenzoesäure,
- d) 0,01-0,2 Teile mindestens eines Zn-Salzes einer aliphatischen C₈-C₂₄-Monocarbonsäure oder -Hydroxymonocarbonsäure oder der Benzoesäure oder tert.-Butylbenzoesäure,
- e) 3-10 Teile von epoxidierten ungesättigten Fettsäureestern, und
- f) 10-70 Teile mindestens eines organischen Weichmachers.
- a) 100 parts of a chlorine-containing thermoplastic,
- b) 0.7-2 parts of thiodiethylene glycol bis-acetoacetate of the formula (H₃CCOCH₂COOCH₂CH₂) ₂S,
- c) 0-0.5 parts of at least one Ca, Ba or / and Mg salt of an aliphatic C₈-C₂₄ monocarboxylic acid or hydroxymonocarboxylic acid or benzoic acid or tert-butylbenzoic acid,
- d) 0.01-0.2 parts of at least one Zn salt of an aliphatic C₈-C₂₄ monocarboxylic acid or hydroxymonocarboxylic acid or benzoic acid or tert-butylbenzoic acid,
- e) 3-10 parts of epoxidized unsaturated fatty acid esters, and
- f) 10-70 parts of at least one organic plasticizer.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH458787 | 1987-11-25 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE3839418A1 true DE3839418A1 (en) | 1989-06-08 |
Family
ID=4278872
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE3839418A Withdrawn DE3839418A1 (en) | 1987-11-25 | 1988-11-22 | STABILIZED POLYMER COMPOSITIONS |
Country Status (5)
| Country | Link |
|---|---|
| JP (1) | JPH01168747A (en) |
| DE (1) | DE3839418A1 (en) |
| FR (1) | FR2623514B1 (en) |
| GB (1) | GB2212808B (en) |
| IT (1) | IT1227542B (en) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2004052977A1 (en) * | 2002-12-06 | 2004-06-24 | Cognis Brasil Ltda. | Plasticized poly vinyl chloride compositions |
| WO2004052978A1 (en) * | 2002-12-06 | 2004-06-24 | Cognis Brasil Ltda. | Plasticizer compositions for nitrocellulose based resins |
| US20090286912A1 (en) * | 2008-05-09 | 2009-11-19 | Invista North America S.A R.L. | MANUFACTURE AND USE OF ALKYL p-TOLUATES |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0421933B1 (en) | 1989-10-06 | 1996-06-12 | Ciba-Geigy Ag | Stabilized chlorinated polymer compositions |
| US6362264B1 (en) * | 1996-12-20 | 2002-03-26 | Ck Witco Corporation | Stabilizer for food contact and medical grade PVC |
| JP2003246903A (en) * | 2002-02-25 | 2003-09-05 | Kubota Corp | Polyvinyl chloride resin composition |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4327000A (en) * | 1979-04-05 | 1982-04-27 | Ciba-Geigy Corporation | Stabilizer mixtures for stabilizing chlorinated thermoplastics |
| GB2192004B (en) * | 1986-06-25 | 1989-12-13 | Ciba Geigy Ag | Stabilized polymer compositions |
-
1988
- 1988-11-22 GB GB8827234A patent/GB2212808B/en not_active Expired - Lifetime
- 1988-11-22 DE DE3839418A patent/DE3839418A1/en not_active Withdrawn
- 1988-11-24 FR FR888815334A patent/FR2623514B1/en not_active Expired - Lifetime
- 1988-11-24 IT IT8822720A patent/IT1227542B/en active
- 1988-11-25 JP JP63297976A patent/JPH01168747A/en active Pending
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2004052977A1 (en) * | 2002-12-06 | 2004-06-24 | Cognis Brasil Ltda. | Plasticized poly vinyl chloride compositions |
| WO2004052978A1 (en) * | 2002-12-06 | 2004-06-24 | Cognis Brasil Ltda. | Plasticizer compositions for nitrocellulose based resins |
| US7700675B2 (en) | 2002-12-06 | 2010-04-20 | Cognis Brazil Ltda | Plasticized poly vinyl chloride compositions |
| US20090286912A1 (en) * | 2008-05-09 | 2009-11-19 | Invista North America S.A R.L. | MANUFACTURE AND USE OF ALKYL p-TOLUATES |
| US8895773B2 (en) * | 2008-05-09 | 2014-11-25 | Invista North America S.A.R.L. | Manufacture and use of alkyl p-toluates |
Also Published As
| Publication number | Publication date |
|---|---|
| GB8827234D0 (en) | 1988-12-29 |
| IT8822720A0 (en) | 1988-11-24 |
| GB2212808A (en) | 1989-08-02 |
| JPH01168747A (en) | 1989-07-04 |
| IT1227542B (en) | 1991-04-15 |
| FR2623514A1 (en) | 1989-05-26 |
| FR2623514B1 (en) | 1991-08-23 |
| GB2212808B (en) | 1991-11-06 |
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