WO2024072728A1 - Compositions de stabilisant thermique à base de métaux mixtes - Google Patents
Compositions de stabilisant thermique à base de métaux mixtes Download PDFInfo
- Publication number
- WO2024072728A1 WO2024072728A1 PCT/US2023/033591 US2023033591W WO2024072728A1 WO 2024072728 A1 WO2024072728 A1 WO 2024072728A1 US 2023033591 W US2023033591 W US 2023033591W WO 2024072728 A1 WO2024072728 A1 WO 2024072728A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- zinc
- alkyltin
- compound
- composition
- mixtures
- Prior art date
Links
- 239000000203 mixture Substances 0.000 title claims abstract description 185
- 229910052751 metal Inorganic materials 0.000 title description 10
- 239000002184 metal Substances 0.000 title description 10
- 239000012760 heat stabilizer Substances 0.000 title description 9
- 150000001875 compounds Chemical class 0.000 claims abstract description 115
- 229910052725 zinc Inorganic materials 0.000 claims abstract description 92
- 239000011701 zinc Substances 0.000 claims abstract description 91
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims abstract description 89
- 239000003381 stabilizer Substances 0.000 claims abstract description 84
- -1 aromatic organic acids Chemical class 0.000 claims abstract description 37
- 239000007788 liquid Substances 0.000 claims abstract description 26
- 150000003751 zinc Chemical class 0.000 claims abstract description 16
- 235000005985 organic acids Nutrition 0.000 claims abstract description 15
- 230000007935 neutral effect Effects 0.000 claims abstract description 13
- 229920000642 polymer Polymers 0.000 claims description 49
- 229920000915 polyvinyl chloride Polymers 0.000 claims description 35
- 239000004800 polyvinyl chloride Substances 0.000 claims description 35
- 229910052736 halogen Inorganic materials 0.000 claims description 31
- 150000002367 halogens Chemical class 0.000 claims description 29
- 238000000034 method Methods 0.000 claims description 22
- IFNXAMCERSVZCV-UHFFFAOYSA-L zinc;2-ethylhexanoate Chemical compound [Zn+2].CCCCC(CC)C([O-])=O.CCCCC(CC)C([O-])=O IFNXAMCERSVZCV-UHFFFAOYSA-L 0.000 claims description 22
- 125000000217 alkyl group Chemical group 0.000 claims description 12
- 238000002156 mixing Methods 0.000 claims description 11
- 150000007942 carboxylates Chemical class 0.000 claims description 7
- 150000003568 thioethers Chemical class 0.000 claims description 7
- DKIDEFUBRARXTE-UHFFFAOYSA-N 3-mercaptopropanoic acid Chemical class OC(=O)CCS DKIDEFUBRARXTE-UHFFFAOYSA-N 0.000 claims description 6
- DXIALWHCMIXMAB-UHFFFAOYSA-L dibutyltin(2+);2-(2-ethylhexylsulfanyl)acetate Chemical compound CCCC[Sn+2]CCCC.CCCCC(CC)CSCC([O-])=O.CCCCC(CC)CSCC([O-])=O DXIALWHCMIXMAB-UHFFFAOYSA-L 0.000 claims description 6
- BILPJDUODHSEHZ-UHFFFAOYSA-N dimethyltin 2-ethylhexyl 2-sulfanylacetate Chemical compound C[Sn]C.CCCCC(CC)COC(=O)CS.CCCCC(CC)COC(=O)CS BILPJDUODHSEHZ-UHFFFAOYSA-N 0.000 claims description 6
- VXGIVDFKZKMKQO-UHFFFAOYSA-L dioctyltin isooctylthioglycolate Chemical compound CCCCC(CC)COC(=O)CS[Sn](CCCCCCCC)(CCCCCCCC)SCC(=O)OCC(CC)CCCC VXGIVDFKZKMKQO-UHFFFAOYSA-L 0.000 claims description 6
- 150000002148 esters Chemical class 0.000 claims description 6
- 150000002688 maleic acid derivatives Chemical class 0.000 claims description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 6
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 5
- VNTDZUDTQCZFKN-UHFFFAOYSA-L zinc 2,2-dimethyloctanoate Chemical compound [Zn++].CCCCCCC(C)(C)C([O-])=O.CCCCCCC(C)(C)C([O-])=O VNTDZUDTQCZFKN-UHFFFAOYSA-L 0.000 claims description 5
- 229940098697 zinc laurate Drugs 0.000 claims description 5
- GPYYEEJOMCKTPR-UHFFFAOYSA-L zinc;dodecanoate Chemical compound [Zn+2].CCCCCCCCCCCC([O-])=O.CCCCCCCCCCCC([O-])=O GPYYEEJOMCKTPR-UHFFFAOYSA-L 0.000 claims description 5
- 239000004801 Chlorinated PVC Substances 0.000 claims description 4
- 229920000457 chlorinated polyvinyl chloride Polymers 0.000 claims description 4
- CWERGRDVMFNCDR-UHFFFAOYSA-N thioglycolic acid Chemical class OC(=O)CS CWERGRDVMFNCDR-UHFFFAOYSA-N 0.000 claims description 4
- XDWXRAYGALQIFG-UHFFFAOYSA-L zinc;propanoate Chemical compound [Zn+2].CCC([O-])=O.CCC([O-])=O XDWXRAYGALQIFG-UHFFFAOYSA-L 0.000 claims description 4
- 229920001328 Polyvinylidene chloride Polymers 0.000 claims description 3
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 claims description 3
- 239000005033 polyvinylidene chloride Substances 0.000 claims description 3
- LPEBYPDZMWMCLZ-CVBJKYQLSA-L zinc;(z)-octadec-9-enoate Chemical compound [Zn+2].CCCCCCCC\C=C/CCCCCCCC([O-])=O.CCCCCCCC\C=C/CCCCCCCC([O-])=O LPEBYPDZMWMCLZ-CVBJKYQLSA-L 0.000 claims description 3
- WWZKQHOCKIZLMA-UHFFFAOYSA-N octanoic acid Chemical compound CCCCCCCC(O)=O WWZKQHOCKIZLMA-UHFFFAOYSA-N 0.000 claims 4
- WCRDXYSYPCEIAK-UHFFFAOYSA-N dibutylstannane Chemical compound CCCC[SnH2]CCCC WCRDXYSYPCEIAK-UHFFFAOYSA-N 0.000 claims 1
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 claims 1
- CHJMFFKHPHCQIJ-UHFFFAOYSA-L zinc;octanoate Chemical compound [Zn+2].CCCCCCCC([O-])=O.CCCCCCCC([O-])=O CHJMFFKHPHCQIJ-UHFFFAOYSA-L 0.000 claims 1
- 229920001577 copolymer Polymers 0.000 description 12
- BZHJMEDXRYGGRV-UHFFFAOYSA-N Vinyl chloride Chemical compound ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 description 10
- 238000013112 stability test Methods 0.000 description 9
- 238000012360 testing method Methods 0.000 description 8
- 150000003839 salts Chemical class 0.000 description 7
- 238000002845 discoloration Methods 0.000 description 6
- 238000009472 formulation Methods 0.000 description 6
- 239000000126 substance Substances 0.000 description 6
- 229920001519 homopolymer Polymers 0.000 description 4
- 238000005191 phase separation Methods 0.000 description 4
- 238000001556 precipitation Methods 0.000 description 4
- 238000002360 preparation method Methods 0.000 description 4
- 229920002554 vinyl polymer Polymers 0.000 description 4
- XOOUIPVCVHRTMJ-UHFFFAOYSA-L zinc stearate Chemical class [Zn+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O XOOUIPVCVHRTMJ-UHFFFAOYSA-L 0.000 description 4
- OWHSTLLOZWTNTQ-UHFFFAOYSA-N 2-ethylhexyl 2-sulfanylacetate Chemical class CCCCC(CC)COC(=O)CS OWHSTLLOZWTNTQ-UHFFFAOYSA-N 0.000 description 3
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 3
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 3
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 3
- 229910052791 calcium Inorganic materials 0.000 description 3
- 239000011575 calcium Substances 0.000 description 3
- 238000011161 development Methods 0.000 description 3
- 229910052749 magnesium Inorganic materials 0.000 description 3
- 239000011777 magnesium Substances 0.000 description 3
- 150000007524 organic acids Chemical class 0.000 description 3
- 229920005989 resin Polymers 0.000 description 3
- 239000011347 resin Substances 0.000 description 3
- 230000006641 stabilisation Effects 0.000 description 3
- 238000012430 stability testing Methods 0.000 description 3
- 238000011105 stabilization Methods 0.000 description 3
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 3
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 description 2
- VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical compound CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 description 2
- UIEPRGXIAZMHQC-UHFFFAOYSA-K 2-(2-ethylhexylsulfanyl)acetate methyltin(3+) Chemical compound [Sn+3]C.CCCCC(CC)CSCC([O-])=O.CCCCC(CC)CSCC([O-])=O.CCCCC(CC)CSCC([O-])=O UIEPRGXIAZMHQC-UHFFFAOYSA-K 0.000 description 2
- HHDNFMPQAVDNGA-UHFFFAOYSA-K 2-ethylhexyl 2-[butyl-bis[[2-(2-ethylhexoxy)-2-oxoethyl]sulfanyl]stannyl]sulfanylacetate Chemical compound CCCCC(CC)COC(=O)CS[Sn](CCCC)(SCC(=O)OCC(CC)CCCC)SCC(=O)OCC(CC)CCCC HHDNFMPQAVDNGA-UHFFFAOYSA-K 0.000 description 2
- HGINCPLSRVDWNT-UHFFFAOYSA-N Acrolein Chemical compound C=CC=O HGINCPLSRVDWNT-UHFFFAOYSA-N 0.000 description 2
- 239000004709 Chlorinated polyethylene Substances 0.000 description 2
- 229920002943 EPDM rubber Polymers 0.000 description 2
- UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 description 2
- 239000007983 Tris buffer Substances 0.000 description 2
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 description 2
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 239000003513 alkali Substances 0.000 description 2
- 150000001339 alkali metal compounds Chemical class 0.000 description 2
- 150000001341 alkaline earth metal compounds Chemical class 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- 239000000839 emulsion Substances 0.000 description 2
- 150000002576 ketones Chemical class 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 229920000638 styrene acrylonitrile Polymers 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- 229910052718 tin Inorganic materials 0.000 description 2
- GZCWPZJOEIAXRU-UHFFFAOYSA-N tin zinc Chemical compound [Zn].[Sn] GZCWPZJOEIAXRU-UHFFFAOYSA-N 0.000 description 2
- LGXVIGDEPROXKC-UHFFFAOYSA-N 1,1-dichloroethene Chemical compound ClC(Cl)=C LGXVIGDEPROXKC-UHFFFAOYSA-N 0.000 description 1
- FPBWSPZHCJXUBL-UHFFFAOYSA-N 1-chloro-1-fluoroethene Chemical group FC(Cl)=C FPBWSPZHCJXUBL-UHFFFAOYSA-N 0.000 description 1
- OZCMOJQQLBXBKI-UHFFFAOYSA-N 1-ethenoxy-2-methylpropane Chemical compound CC(C)COC=C OZCMOJQQLBXBKI-UHFFFAOYSA-N 0.000 description 1
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 1
- OEPOKWHJYJXUGD-UHFFFAOYSA-N 2-(3-phenylmethoxyphenyl)-1,3-thiazole-4-carbaldehyde Chemical compound O=CC1=CSC(C=2C=C(OCC=3C=CC=CC=3)C=CC=2)=N1 OEPOKWHJYJXUGD-UHFFFAOYSA-N 0.000 description 1
- VHKGIWUCVBAITR-UHFFFAOYSA-K 2-ethylhexyl 2-[bis[[2-(2-ethylhexoxy)-2-oxoethyl]sulfanyl]-octylstannyl]sulfanylacetate Chemical compound CCCCC(CC)COC(=O)CS[Sn](CCCCCCCC)(SCC(=O)OCC(CC)CCCC)SCC(=O)OCC(CC)CCCC VHKGIWUCVBAITR-UHFFFAOYSA-K 0.000 description 1
- VNPRJHMMOKDEDZ-UHFFFAOYSA-L 6-methylheptyl 2-[dibutyl-[2-(6-methylheptoxy)-2-oxoethyl]sulfanylstannyl]sulfanylacetate Chemical compound CC(C)CCCCCOC(=O)CS[Sn](CCCC)(CCCC)SCC(=O)OCCCCCC(C)C VNPRJHMMOKDEDZ-UHFFFAOYSA-L 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 239000004287 Dehydroacetic acid Substances 0.000 description 1
- IEPRKVQEAMIZSS-UHFFFAOYSA-N Di-Et ester-Fumaric acid Natural products CCOC(=O)C=CC(=O)OCC IEPRKVQEAMIZSS-UHFFFAOYSA-N 0.000 description 1
- IEPRKVQEAMIZSS-WAYWQWQTSA-N Diethyl maleate Chemical compound CCOC(=O)\C=C/C(=O)OCC IEPRKVQEAMIZSS-WAYWQWQTSA-N 0.000 description 1
- 239000004262 Ethyl gallate Substances 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 238000013019 agitation Methods 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 150000001299 aldehydes Chemical class 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 150000001336 alkenes Chemical class 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 229910052788 barium Inorganic materials 0.000 description 1
- DSAJWYNOEDNPEQ-UHFFFAOYSA-N barium atom Chemical compound [Ba] DSAJWYNOEDNPEQ-UHFFFAOYSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- NTXGQCSETZTARF-UHFFFAOYSA-N buta-1,3-diene;prop-2-enenitrile Chemical compound C=CC=C.C=CC#N NTXGQCSETZTARF-UHFFFAOYSA-N 0.000 description 1
- MTAZNLWOLGHBHU-UHFFFAOYSA-N butadiene-styrene rubber Chemical compound C=CC=C.C=CC1=CC=CC=C1 MTAZNLWOLGHBHU-UHFFFAOYSA-N 0.000 description 1
- 229910052793 cadmium Inorganic materials 0.000 description 1
- BDOSMKKIYDKNTQ-UHFFFAOYSA-N cadmium atom Chemical compound [Cd] BDOSMKKIYDKNTQ-UHFFFAOYSA-N 0.000 description 1
- AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 description 1
- 239000000920 calcium hydroxide Substances 0.000 description 1
- 229910001861 calcium hydroxide Inorganic materials 0.000 description 1
- BRPQOXSCLDDYGP-UHFFFAOYSA-N calcium oxide Chemical compound [O-2].[Ca+2] BRPQOXSCLDDYGP-UHFFFAOYSA-N 0.000 description 1
- 239000000292 calcium oxide Substances 0.000 description 1
- ODINCKMPIJJUCX-UHFFFAOYSA-N calcium oxide Inorganic materials [Ca]=O ODINCKMPIJJUCX-UHFFFAOYSA-N 0.000 description 1
- 238000003490 calendering Methods 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 238000013329 compounding Methods 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- MLUCVPSAIODCQM-NSCUHMNNSA-N crotonaldehyde Chemical compound C\C=C\C=O MLUCVPSAIODCQM-NSCUHMNNSA-N 0.000 description 1
- MLUCVPSAIODCQM-UHFFFAOYSA-N crotonaldehyde Natural products CC=CC=O MLUCVPSAIODCQM-UHFFFAOYSA-N 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- JEQRBTDTEKWZBW-UHFFFAOYSA-N dehydroacetic acid Chemical compound CC(=O)C1=C(O)OC(C)=CC1=O JEQRBTDTEKWZBW-UHFFFAOYSA-N 0.000 description 1
- 229940061632 dehydroacetic acid Drugs 0.000 description 1
- PGRHXDWITVMQBC-UHFFFAOYSA-N dehydroacetic acid Natural products CC(=O)C1C(=O)OC(C)=CC1=O PGRHXDWITVMQBC-UHFFFAOYSA-N 0.000 description 1
- 235000019258 dehydroacetic acid Nutrition 0.000 description 1
- 150000001991 dicarboxylic acids Chemical class 0.000 description 1
- IEPRKVQEAMIZSS-AATRIKPKSA-N diethyl fumarate Chemical compound CCOC(=O)\C=C\C(=O)OCC IEPRKVQEAMIZSS-AATRIKPKSA-N 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- CUHFNERITPIOBB-UHFFFAOYSA-L dimethyltin(2+);2-(2-ethylhexylsulfanyl)acetate Chemical compound C[Sn+2]C.CCCCC(CC)CSCC([O-])=O.CCCCC(CC)CSCC([O-])=O CUHFNERITPIOBB-UHFFFAOYSA-L 0.000 description 1
- BFMKFCLXZSUVPI-UHFFFAOYSA-N ethyl but-3-enoate Chemical compound CCOC(=O)CC=C BFMKFCLXZSUVPI-UHFFFAOYSA-N 0.000 description 1
- 238000001125 extrusion Methods 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 229920000578 graft copolymer Polymers 0.000 description 1
- PBZROIMXDZTJDF-UHFFFAOYSA-N hepta-1,6-dien-4-one Chemical compound C=CCC(=O)CC=C PBZROIMXDZTJDF-UHFFFAOYSA-N 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
- ZFSLODLOARCGLH-UHFFFAOYSA-N isocyanuric acid Chemical compound OC1=NC(O)=NC(O)=N1 ZFSLODLOARCGLH-UHFFFAOYSA-N 0.000 description 1
- LVHBHZANLOWSRM-UHFFFAOYSA-N itaconic acid Chemical class OC(=O)CC(=C)C(O)=O LVHBHZANLOWSRM-UHFFFAOYSA-N 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- XJRBAMWJDBPFIM-UHFFFAOYSA-N methyl vinyl ether Chemical compound COC=C XJRBAMWJDBPFIM-UHFFFAOYSA-N 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- 238000000465 moulding Methods 0.000 description 1
- WWZKQHOCKIZLMA-UHFFFAOYSA-M octanoate Chemical compound CCCCCCCC([O-])=O WWZKQHOCKIZLMA-UHFFFAOYSA-M 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 238000012805 post-processing Methods 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- SCUZVMOVTVSBLE-UHFFFAOYSA-N prop-2-enenitrile;styrene Chemical compound C=CC#N.C=CC1=CC=CC=C1 SCUZVMOVTVSBLE-UHFFFAOYSA-N 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 239000011342 resin composition Substances 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 230000000087 stabilizing effect Effects 0.000 description 1
- 229910052712 strontium Inorganic materials 0.000 description 1
- CIOAGBVUUVVLOB-UHFFFAOYSA-N strontium atom Chemical compound [Sr] CIOAGBVUUVVLOB-UHFFFAOYSA-N 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 125000004434 sulfur atom Chemical group 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 230000002195 synergetic effect Effects 0.000 description 1
- 238000005979 thermal decomposition reaction Methods 0.000 description 1
- 229920001169 thermoplastic Polymers 0.000 description 1
- 239000004416 thermosoftening plastic Substances 0.000 description 1
- CWERGRDVMFNCDR-UHFFFAOYSA-M thioglycolate(1-) Chemical class [O-]C(=O)CS CWERGRDVMFNCDR-UHFFFAOYSA-M 0.000 description 1
- 239000011135 tin Substances 0.000 description 1
- 229920001567 vinyl ester resin Polymers 0.000 description 1
- FUSUHKVFWTUUBE-UHFFFAOYSA-N vinyl methyl ketone Natural products CC(=O)C=C FUSUHKVFWTUUBE-UHFFFAOYSA-N 0.000 description 1
- 150000003752 zinc compounds Chemical class 0.000 description 1
- UGZADUVQMDAIAO-UHFFFAOYSA-L zinc hydroxide Chemical compound [OH-].[OH-].[Zn+2] UGZADUVQMDAIAO-UHFFFAOYSA-L 0.000 description 1
- 229940007718 zinc hydroxide Drugs 0.000 description 1
- 229910021511 zinc hydroxide Inorganic materials 0.000 description 1
- 239000011787 zinc oxide Substances 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
- C08K5/09—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
- C08K5/0008—Organic ingredients according to more than one of the "one dot" groups of C08K5/01 - C08K5/59
- C08K5/005—Stabilisers against oxidation, heat, light, ozone
-
- 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
- C08K5/0091—Complexes with metal-heteroatom-bonds
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/56—Organo-metallic compounds, i.e. organic compounds containing a metal-to-carbon bond
- C08K5/57—Organo-tin compounds
- C08K5/58—Organo-tin compounds containing sulfur
-
- 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
- C08K2201/00—Specific properties of additives
- C08K2201/014—Additives containing two or more different additives of the same subgroup in C08K
Definitions
- the invention relates to liquid, storage- stable mixed metal heat stabilizer compositions for protecting halogen-containing homo- and co-polymers against color development under elevated temperature and shear conditions.
- the stabilizers of this invention comprise an alkyltin composition and a zinc-containing compound.
- Alkyltin stabilizers are known to be particularly effective in preventing discoloration of halogen-containing polymers at elevated temperatures, for example, “PVC Degradation and Stabilization,” Wypich, George; ChemTec, Toronto 2008, p.321-335. “Handbook of Vinyl Formulating”, 2 nd edition; Grossman, Richard F.; Wiley & Sons, 2008, p. 92-107; “PVC Handbook”; Wilkes, Charles E., et al; Hanser, Cincinnati 2005, p.108-116; “PVC Additives”, 2 nd edition; Schiller, Michael; Hanser Publishing, 2022, p. 22-26.
- PVC Degradation and Stabilization Wypich, George; ChemTec, Toronto 2008, p.321-335.
- JP 54,154,441 discloses the preparation of heat stabilizers for halogen-containing resins where the stabilizers comprise four components: a) a zinc salt of an organic acid, b) at least one salt of organic acid or alkylphenol and the metal selected from barium, calcium, tin, magnesium or strontium, c) dehydroacetic acid or its sodium salts, and d) an isocyanurate.
- the high number of components differing in terms of mutual solubility prevents the formation of storagestable liquid stabilizers, since the resultant combination would either precipitate, separate or appear cloudy.
- Japanese Kokai No. 5237,956 discloses a stabilized halogen-containing resin composition containing an alkyltin compound and a specific metal salt.
- US Patent No. 4,358,555 discloses heat stabilizing blends for halogen-containing polymers, where the blends comprise a) at least one alkyltin mercaptide, b) at least one zinc mercaptoester, and c) at least one basic alkali or alkaline-earth metal compound. Also disclosed are heat stabilizer blends comprising a) at least one alkyltin mercaptide, b) at least one alkyltin sulfide or oxide, c) at least one zinc mercaptoester, and d) at least one basic alkali or alkaline-earth metal compound.
- the alkyltin sulfides or oxides are employed in the stabilizer compositions in amounts up to 50% of the combined weight of the alkyltin mercaptide and alkyltin sulfide or oxide present in the stabilizer compositions.
- metals include calcium and magnesium.
- zinc mercaptoesters include organozinc compounds having two mercaptoester groups, where each group was bonded to the zinc atom through the sulfur atom.
- US Patent No. 8,198,352 describes high purity monoalkyltin stabilizers, such as monooctyltin tris (2-ethylhexyl thioglycolate), where the mono-alkyltin compounds can be used in combination with solid metal salt co-stabilizers, including solid stearates of zinc, calcium or magnesium.
- solid metal salt co-stabilizers including solid stearates of zinc, calcium or magnesium.
- Similary US Patent Application 2005/0215674 covers stabilizers consisting of alkyltin components, calcium hydroxide and/or calcium oxide and a zine-containing component, sue as zinc oxide and/or zinc hydroxide or salts that are of very limited solubility in the alkyltin components and therefore those are added separately (as opposed to liquid one-packs) into PVC compounds.
- the invention relates to a stabilizer composition
- a stabilizer composition comprising 75.0% to 99.9 % by weight of an alkyltin composition comprising at least 25.0 wt% of a di-alkyltin compound; and 0.1% to 25.0% by weight of a zinc-containing compound selected from the group consisting of neutral and overbased zinc salts
- a neutral salt is formed by the complete (or stoichiometric) replacement of the hydrogen in an acid by zinc-containing base
- an overbased salt is formed by reacting an acid with an excess (or above stochiometric) amount of zinc-containing base] of C1-C24 linear, branched, cyclic aliphatic or aromatic organic acids, zinc diketonates, zinc alcoholates and mixtures thereof.
- the stabilizer composition of this invention is a storage-stable liquid having a viscosity of less than 1,500 cP at 25°C.
- the invention relates to a stabilized polymer composition
- a stabilized polymer composition comprising a halogen-containing homo- or co-polymer and a liquid, storage- stable stabilizer composition
- a liquid, storage- stable stabilizer composition comprising 75.0% to 99.9% by weight of a mixture of an alkyltin compound comprising at least 25.0 wt% of a di-alkyltin compound; and 0.1% to 25.0% by weight of an zinc- containing compound selected from the group consisting of neutral or overbased zinc salts of Ci- C24 linear, branched, cyclic aliphatic or aromatic organic acids, zinc diketonates, zinc alcoholates and mixtures thereof.
- the stabilizer composition is a storage- stable liquid having a viscosity of less than 1,500 cP at 25°C and is present in an amount from 0.01 to 10 parts by weight per 100 parts by weight of the halogen-containing polymer.
- the invention relates to a process comprising blending a stabilizer composition with a halogen-containing polymer, the stabilizer composition comprising 75.0% to 99.9% by weight of a mixture of an alkyltin compound comprising at least 25.0 wt% of a di-alkyltin compound; and 0.1% to 25.0% by weight of a zinc-containing compound selected from the group consisting of zinc salts of C1-C24 linear, branched, cyclic aliphatic or aromatic organic acids, zinc diketonates, zinc alcoholates and mixtures thereof.
- the stabilizer composition is a storage- stable liquid having a viscosity of less than 1,500 cP at 25°C.
- the invention relates to a process comprising blending 75.0% to 99.9% by weight of an alkyltin compound comprising at least 25.0 wt% of a di-alkyltin compound, and 0.1% to 25.0% by weight of an organozinc compound selected from the group consisting of neutral or overbased zinc salts of C1-C24 linear, branched, cyclic aliphatic or aromatic organic acids, zinc diketonates, zinc alcoholates and mixtures thereof, thereby forming a stabilizer composition which is a storage-stable liquid having a viscosity of less than 1,500 cP at 25°C; and blending the stabilizer composition with a halogen-containing polymer.
- an organozinc compound selected from the group consisting of neutral or overbased zinc salts of C1-C24 linear, branched, cyclic aliphatic or aromatic organic acids, zinc diketonates, zinc alcoholates and mixtures thereof
- the invention relates to a stabilizer composition
- a stabilizer composition comprising an alkyltin compound and a zinc-containing compound.
- the alkyltin composition contains at least 25.0 wt% of a di-alkyltin compound based on the weight of the alkyltin composition.
- the alkyltin composition contains at least 50.0 wt % of a di-alkyltin compound, and more preferably at least 80% of di-alkyltin compound.
- the di-alkyltin compound is selected from the group consisting of di-alkyltin mercaptoacetate esters, di-alkyltin carboxylates, di-alkyltin maleates, di-alkyltin sulfides, di- alkyltin diketonates, di-alkyltin alcoholates, di-alkyltin mercaptoethyl carboxylates (also known as dialkyltin reverse esters) and mixtures thereof. More preferably, the di-alkyltin compound is selected from dialkyltin bis(2-ethylhexyl mercaptoacetates).
- the alkyl groups of the di-alkyltin compound are selected from linear, branched or cyclic C1-C20 alkyls, preferably linear C1-C10 alkyl groups. Most preferably, the alkyl groups of the di-alkyltin compound are selected from methyl, n-butyl or n-octyl.
- the di-alkyltin compound is selected from the group consisting of di-n-butyltin bis(2-ethylhexylmercaptoacetate), di-methyltin bis(2-ethylhexylmercaptoacetate), di-n-octyltin bis(2-ethylhexylmercaptoacetate) and mixtures thereof.
- the alkyltin composition can comprise up to 100% of the di-alkyltin compound, however, the alkyltin composition may also optionally contain a mono-alkyltin compound.
- a monoalky Itin compound is present in the alkyltin composition, it is present in amounts of 0.1% up to 75% by weight, preferably up to 50% by weight of the alkyltin composition and more preferably up to 10% by weight of the alkyltin compound.
- the mono-alkyltin compound is selected from the group consisting of mono-alkyltin thioglycolate esters, mono-alkyltin carboxylates, mono-alkyltin maleates, mono-alkyltin sulfides, mono-alkyltin diketonates, mono- alkyltin alcoholates, mono-alkyltin 2-mercaptoethyl carboxylates and mixtures thereof.
- the alkyl groups of the mono-alkyltin compound are selected from linear, branched or cyclic C1-C20 alkyls, preferably linear C1-C10 alkyl groups.
- the alkyl groups of the mono-alkyltin compound are selected from methyl, n-butyl or n-octyl.
- the alkyltin composition is selected from the group consisting of mixtures of mono-n-butyltin tris(2- ethylhexylmercaptoacetate) and di-n-butyltin bis(2-ethylhexylmercaptoacetate), mixtures of mono-methyltin tris(2-ethylhexylmercaptoacetate) and dimethyltin bis(2- ethylhexylmercaptoacetate), and mixtures of mono-n-octylltin tris(2-ethylhexylmercaptoacetate) and di-n-octylltin bis(2-cthylhcxylmcrcaptoacctatc).
- the alkyltin composition is blended with a zinc-containing compound.
- the amount of the alkyltin composition in the stabilizer composition ranges from 75.0 to 99.9%, preferably from 80.0 to 95.0% by weight.
- the zinc-containing compound is selected from the group consisting of neutral or overbased zinc salts of C1-C24 linear, branched, cyclic aliphatic or aromatic organic acids, zinc diketonates, zinc alcoholates, their solutions in solvents, such as organic acids, esters, alcohols, ketones and mixtures thereof.
- the zinc-containing compound is selected from zinc n- octoate, zinc iso-octoate, zinc 2-ethylhexanoate, overbased zinc 2-ethylhexanoate, zinc neodecanoate, zinc propionate, zinc oleate and zinc laurate, including the overbased modifications of these salts, as shown in “Metal Carboxylates”; Mehrota, Ram C., et al., Academic Press, 1983. Peterangelo, S.C; Hart, R. T.; Clark, A. C. J. Phys. Chem B 2007, 111, pp. 7073-7077. More preferably, the organozinc compound is selected from zinc n-octoate, zinc 2-ethylhexanoate or zinc iso-octoate.
- the zinc-containing compound is blended with the alkyltin composition to form the homogeneous, liquid stabilizer composition.
- the amount of the zinc-containing compound in the stabilizer composition ranges from 0.1 to 25.0%, preferably from 5.0 to 20.0 % by weight. Blending is canned out at 15-80°C, preferably at ambient temperature for 0.5-10 hours, preferably about 1 hour.
- surfactants, diluents, antioxidants, lubricants and co- stabilizers can also be present in the stabilizer composition.
- analogous cadmium-containing compounds can be used instead of zinc- containing compounds.
- the stabilizer composition is a storage-stable, homogeneous liquid.
- storage- stable means that the composition possesses no visible precipitation, cloudiness or phase separation when measured 15 days after preparation, while being kept at each of 10, 25 and 80°C.
- Storage-stable also means that the stabilizer composition has a viscosity, measured at 25°C (Spindle 34 at 100 rpm) 15 days after preparation, of lower than 1 ,500 cP. Preferably, the measured viscosity is below 1,000 cP.
- Storage stability is an important property in the subject liquid heat stabilizer compositions. Inferior storage stability, as evidenced by visible precipitation, cloudiness or phase separation in the stabilizer composition causes maldistribution of the stabilizer in PVC and loss of stabilizer efficiency. Inferior storage stability, as evidenced by a viscosity higher than 1,500 cP causes higher motor loads and difficulties in metering such liquids via standard pumps.
- the invention relates to a stabilized polymer composition
- a stabilized polymer composition comprising a halogen-containing polymer and a liquid, storage-stable stabilizer composition comprising 75.0% to 99.9% by weight of an alkyltin composition comprising at least 25.0% by weight of a di-alkyltin compound; and 0.1% to 25.0% by weight of an zinc-containing compound selected from the group consisting of neutral or overbased zinc salts of C1-C24 linear, branched, cyclic aliphatic or aromatic organic acids, zinc diketonates, zinc alcoholates and mixtures thereof.
- the stabilizer composition is a storage-stable liquid having a viscosity of less than 1,500 cP at 25°C.
- the subject composition is useful as a stabilizer for halogen-containing polymers, including homopolymers and copolymers of vinyl halogens, post-halogenated polymers and copolymers of vinyl halogens, and halogenated polymers of olefins, such as ethylene, propylene, and 1 -butene.
- the halogen of such polymers can be fluorine, chlorine, bromine, iodine, or mixtures thereof.
- the polymer that is stabilized by the stabilizer compositions is poly(vinyl chloride) (“PVC”) or chlorinated poly(vinyl chloride) (“CPVC”).
- PVC poly(vinyl chloride)
- CPVC chlorinated poly(vinyl chloride)
- the PVC used can be obtained via polymerization in bulk or in suspension, in emulsion, in micro suspension, or in suspended emulsion.
- PVC is intended to include both homopolymers and copolymers of vinyl chloride, i.e., vinyl resins containing vinyl chloride units in their structure, e.g., copolymers of vinyl chloride and vinyl esters of aliphatic acids, in particular vinyl acetate; copolymers of vinyl chloride with esters of acrylic and methacrylic acid and with acrylonitrile; copolymers of vinyl chloride with diene compounds and unsaturated dicarboxylic acids or anhydrides thereof, such as copolymers of vinyl chloride with diethyl maleate, diethyl fumarate or maleic anhydride; post-chlorinated polymers and copolymers of vinyl chloride; copolymers of vinyl chloride and vinylidene chloride with unsaturated aldehydes, ketones and others, such as acrolein, crotonaldehyde, vinyl methyl ketone, vinyl methyl ether, vinyl isobutyl
- PVC as employed herein is also intended to include graft polymers of PVC with ethyl-vinyl acetate (“EVA”), acrylonitrile/butadiene-styrene (“ABS”), and meth- acrylatebutadiene (“MBS”).
- EVA ethyl-vinyl acetate
- ABS acrylonitrile/butadiene-styrene
- MFS meth- acrylatebutadiene
- Preferred substrates are also mixtures of the above-mentioned homopolymers and copolymers, preferably vinyl chloride homopolymers, with other thermoplastic and/or elastomeric polymers, more preferably blends with ABS, MBS, acrylonitrile butadiene (“NBR”), styrene-acrylonitrile (“SAN”), EVA, chlorinated polyethylene (“CPE”), poly(methyl methylacrylate), ethylene propylene diene monomer (“EPDM”), and polylactones.
- vinyl chloride homopolymers preferably vinyl chloride homopolymers
- other thermoplastic and/or elastomeric polymers more preferably blends with ABS, MBS, acrylonitrile butadiene (“NBR”), styrene-acrylonitrile (“SAN”), EVA, chlorinated polyethylene (“CPE”), poly(methyl methylacrylate), ethylene propylene diene monomer (“EPDM”), and polylactones.
- vinyl acetate, vinylidene dichloride, acrylonitrile, chlorofluoroethylene and/or the esters of acrylic, fumaric, maleic and/or itaconic acids are monomers that are copolymerizable with vinyl chloride.
- the halogen-containing polymer is selected from polyvinyl chloride, polyvinylidene chloride, chlorinated polyvinyl chloride or mixtures thereof. More preferably, the halogen-containing polymer is polyvinyl chloride.
- the content of the subject stabilizer composition within the stabilized polymer composition is typically between 0.01 parts and 10 parts by weight, preferably between about 0.1 and 7.0, and more preferably between 0.25 and 5.0 pails by weight per 100 pails by weight of the halogencontaining polymer.
- the subject stabilized polymer compositions have improved dynamic heat stability, as measured by the yellowness index test (“YI”) as defined in ASTM method E313.
- YI yellowness index test
- the stabilized polymer compositions have improved initial and mid-term dynamic heat stability.
- Initial and mid-term dynamic heat stability is an important consideration for halogenated polymers because it significantly affects post-processing whiteness of PVC articles.
- initial and mid-term stability is measured by the yellowness index within the first 15 minutes of the test.
- the invention relates to blending a halogen-containing polymer and the stabilizer composition.
- the stabilizer composition comprises 75.0% to 99.9% by weight of a mixture of an alkyltin composition comprising at least 25.0% by weight of a di-alkyltin compound; and 0.1% to 25.0% by weight of a zinc-containing compound selected from the group consisting of neutral or overbased zinc salts of C1-C24 linear, branched, cyclic aliphatic or aromatic organic acids, zinc diketonates, zinc alcoholates and mixtures thereof.
- the stabilizer composition is a storage-stable liquid having a viscosity of less than 1,500 cP at 25 °C. In this way, both the alkyltin composition and the zinc-containing compound are added to the halogen-containing polymer together at the same time, thereby imparting initial and mid-term heat stability.
- an alkyltin composition comprising at least 25.0% by weight of a di-alkyltin compound
- a zinc-containing compound selected from the group consisting of neutral or overbased zinc salts of C1-C24 linear, branched, cyclic aliphatic or aromatic organic acids, zinc diketonates, zinc alcoholates and mixtures thereof, thereby forming a stabilizer composition.
- the stabilizer composition is a storage-stable liquid having a viscosity of less than 1,500 cP at 25°C.
- the stabilizer composition is then blended with a halogen-containing polymer. In this way, both the alkyltin composition and the organozinc compound are added to the halogencontaining polymer together at the same time, thereby imparting initial and mid-term heat stability.
- the components of the stabilizer composition can be blended by a variety of processes well known to those skilled in the art, for example, by agitation, mixing and combinations thereof.
- the halogen-containing polymer and the stabilizer composition can also be blended by well-known processes, for example, by melt blending, dry blending, extrusion, molding, calendering and combinations thereof.
- Control example 1 is a mixture of mono-methyltin tris(2-ethylhexylmercaptoacetate) and dimethyltin bis(2-ethylhexylmercaptoacetate), having a content of the dimethyltin compound of greater than 70%, commercially available from Galata Chemicals as Mark 1900.
- Examples 2- 6 mixtures of Control Example 1 and overbased zinc 2-ethylhexanoate, commercially available from Galata Chemicals as Mark 552G (Zinc Salt), were blended for 1 hour at ambient temperature. The blends were then tested for storage stability.
- Storage stability was graded as “Passed” if after being maintained at each of 10, 25, and 80°C for 15 days, all the samples contained no visible precipitation, cloudiness or phase separation, and the blend Brookfield viscosity, measured at 25°C (Spindle 34 at 100 rpm), was lower than 1500 cP. Storage stability was designated as “Failed” if precipitation, cloudiness or phase separation was present, or if the blend viscosity was greater than 1 ,500 cP.
- Table 1 summarizes the relative percentages of Control Example 1 and Zinc Salt for Examples 2-6, and the corresponding test results.
- Control example 7 is a mixture of mono-n-octylltin tris(2-ethylhexylmercaptoacetate) and di-n-octyltin bis(2-ethylhexylmercaptoacetate), having a content of the di-n-octyltin compound of greater than 50%, commercially available from Galata Chemicals as Mark 17M0K.
- Examples 8-12 mixtures of Control example 7 and overbased zinc 2-ethylhexanoate, commercially available from Galata Chemicals as Mark 552G (Zinc Salt), were prepared as in Examples 2-6. Control example 7 and Examples 8-12 were then tested for storage stability as with Control example 1 and Examples 2-6.
- Table 2 summarizes the relative percentages of Control example 7 and overbased zinc 2- ethylhexanoate in Examples 8-12, and the corresponding viscosity and storage stability test results.
- Control example 13 is a mixture of di-n-butyltin bis(2-ethylhexylmercaptoacetate) and mono-n-butyltin tris(2-ethylhexylmercaptoacetate), having a content of the di-n-butyltin compound of greater than 90%, commercially available from Galata Chemicals as Mark 292.
- Examples 14- 18 mixtures of Control example 13 and overbased zinc 2-ethylhexanoate, commercially available from Galata Chemicals as Mark 552G (Zinc Salt), were prepared as with Examples 2-6.
- Control example 13 and Examples 14-18 were then tested for storage stability as with Examples 2-6.
- Table 3 summarizes compositions of Control Example 13 and Examples 14-18, and the corresponding viscosity and storage stability test results.
- Example 19-28 mixtures of Control example 1 and zinc-containing compounds at various concentrations were blended and then tested for storage stability as with Examples 2-6. Table d summarizes the relative percentages of Examples 19-28, and the corresponding test results.
- Rigid PVC compounds were prepared using the stabilizer formulations of Control example 1 and Examples 2-4.
- the stabilizers were loaded at the same weight level of 1.5 parts per hundred of PVC resin (“phr”).
- PVC compound test sample prepared according to the formulation described in table 8) was placed into a Brabender mixer operated at 190°C and 65 RPM. Sample chips were taken every 3 minutes.
- Heat stability of the PVC compounds was determined using a Hunter Lab colorimeter measuring Yellowness Index (YI) of the sample chips. Lower YI signifies lower discoloration as a result of thermal decomposition of PVC, and therefore, superior thermal stabilization. Results of the dynamic heat stability test are shown in Table 5.
- Samples of the subject stabilizers and a PVC compound were prepared for accelerated UV stability test by compounding a dry blend of the components in a two-roll mill, type W 150EP for 5 minutes at 177°C and 30 rpm roll speed. After 5 minutes, the milled rigid PVC sheets were taken off the instrument and flattened while still warm with a Ferro plate, to obtain a smooth, flat surface. Ten individual rigid sheet specimens were then cut to fit a standard 3”xl2” panel and secured by snap-in rings. The samples were then placed in a QUV Solar Eye accelerated weathering tester (manufactured by Q-Lab Corporation, Westlake, OH) and exposed to conditions under ASTM G-154 using a 340 nm UVA lamp.
- QUV Solar Eye accelerated weathering tester manufactured by Q-Lab Corporation, Westlake, OH
- the programmed QUV cycle consisted of 8 Hours of UV-light exposure 60°C, followed by 4 Hours of condensation at 50°C. Individual samples were taken at 500-hour intervals and measured for color development (Yellowness Index - YI) using a Hunter ColorQuest II Colorimeter (manufactured by Hunterlab, Reston, VA).
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Abstract
Composition de stabilisant comprenant 75,0 à 99,9 % en poids d'une composition d'alkylétain comprenant au moins 25,0 % en poids d'un composé de di-alkylétain ; et 0,1 à 25,0 % en poids d'un composé contenant du zinc choisi dans le groupe constitué par des sels de zinc neutres ou surbasiques d'acides organiques linéaires, ramifiés, cycliques, aliphatiques ou aromatiques en C1-C24, des dicétonates de zinc, des alcoolates de zinc et des mélanges de ceux-ci, la composition de stabilisant étant un liquide stable au stockage présentant une viscosité inférieure à 1 500 cP à 25°C.
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JPS54154441A (en) | 1978-05-26 | 1979-12-05 | Adeka Argus Chem Co Ltd | Halogen-containing resin composition |
US4358555A (en) | 1981-06-02 | 1982-11-09 | Carstab Corporation | Stabilizers for halogen containing polymers comprising alkyltin compounds, zinc mercaptoesters and basic alkali or alkaline earth metal compounds |
DE4141661A1 (de) * | 1990-12-20 | 1992-07-02 | Ciba Geigy Ag | Stabilisierte chlorhaltige polymere |
US5516827A (en) * | 1992-06-04 | 1996-05-14 | Ciba-Geigy Corporation | Stabilized, chlorine-containing polymer compositions |
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US8198352B2 (en) | 2008-05-15 | 2012-06-12 | Arkema France | High purity monoalkyltin compounds and uses thereof |
JP5237956B2 (ja) | 2006-10-23 | 2013-07-17 | ボシュ・アンド・ロム・インコーポレイテッド | 溝付き吸引ポンプのローラーヘッド・アセンブリ |
WO2014149894A1 (fr) * | 2013-03-15 | 2014-09-25 | Galata Chemicals Llc | Compositions de stabilisant métallique mixte |
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JPS54154441A (en) | 1978-05-26 | 1979-12-05 | Adeka Argus Chem Co Ltd | Halogen-containing resin composition |
US4358555A (en) | 1981-06-02 | 1982-11-09 | Carstab Corporation | Stabilizers for halogen containing polymers comprising alkyltin compounds, zinc mercaptoesters and basic alkali or alkaline earth metal compounds |
DE4141661A1 (de) * | 1990-12-20 | 1992-07-02 | Ciba Geigy Ag | Stabilisierte chlorhaltige polymere |
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JP5237956B2 (ja) | 2006-10-23 | 2013-07-17 | ボシュ・アンド・ロム・インコーポレイテッド | 溝付き吸引ポンプのローラーヘッド・アセンブリ |
US8198352B2 (en) | 2008-05-15 | 2012-06-12 | Arkema France | High purity monoalkyltin compounds and uses thereof |
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