JPS6039360B2 - 新規オルガノ錫化合物 - Google Patents
新規オルガノ錫化合物Info
- Publication number
- JPS6039360B2 JPS6039360B2 JP54145568A JP14556879A JPS6039360B2 JP S6039360 B2 JPS6039360 B2 JP S6039360B2 JP 54145568 A JP54145568 A JP 54145568A JP 14556879 A JP14556879 A JP 14556879A JP S6039360 B2 JPS6039360 B2 JP S6039360B2
- Authority
- JP
- Japan
- Prior art keywords
- acid
- group
- mercaptoethyl
- mol
- carbon atoms
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- 150000001875 compounds Chemical class 0.000 title claims abstract description 104
- 239000002253 acid Substances 0.000 claims abstract description 90
- 229910052718 tin Inorganic materials 0.000 claims abstract description 31
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical group [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 claims abstract description 30
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 25
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims abstract description 13
- 125000001183 hydrocarbyl group Chemical group 0.000 claims abstract description 12
- 125000004434 sulfur atom Chemical group 0.000 claims abstract description 12
- 229910052719 titanium Inorganic materials 0.000 claims abstract description 12
- 229910052782 aluminium Inorganic materials 0.000 claims abstract description 11
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims abstract description 9
- 229910052698 phosphorus Inorganic materials 0.000 claims abstract description 8
- 229910052710 silicon Inorganic materials 0.000 claims abstract description 8
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 5
- 229910052796 boron Inorganic materials 0.000 claims abstract 4
- 150000002148 esters Chemical class 0.000 claims description 47
- 229910052739 hydrogen Inorganic materials 0.000 claims description 17
- 239000001257 hydrogen Substances 0.000 claims description 17
- 229910052717 sulfur Inorganic materials 0.000 claims description 17
- 125000000217 alkyl group Chemical group 0.000 claims description 14
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical group [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 claims description 13
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 11
- 239000010936 titanium Chemical group 0.000 claims description 11
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical group [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 claims description 9
- 239000000126 substance Substances 0.000 claims description 8
- 239000011593 sulfur Substances 0.000 claims description 8
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical group [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 claims description 7
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical group [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims description 6
- 150000002431 hydrogen Chemical group 0.000 claims description 6
- 229910052760 oxygen Inorganic materials 0.000 claims description 6
- 239000001301 oxygen Substances 0.000 claims description 6
- 239000011574 phosphorus Chemical group 0.000 claims description 6
- 239000010703 silicon Chemical group 0.000 claims description 6
- 125000002947 alkylene group Chemical group 0.000 claims description 5
- 125000003396 thiol group Chemical group [H]S* 0.000 claims description 5
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 4
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 3
- LSDPWZHWYPCBBB-UHFFFAOYSA-N Methanethiol Chemical compound SC LSDPWZHWYPCBBB-UHFFFAOYSA-N 0.000 claims description 3
- HDFRDWFLWVCOGP-UHFFFAOYSA-N carbonothioic O,S-acid Chemical compound OC(S)=O HDFRDWFLWVCOGP-UHFFFAOYSA-N 0.000 claims description 3
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 3
- 239000000460 chlorine Substances 0.000 claims description 3
- 229910052801 chlorine Inorganic materials 0.000 claims description 3
- 125000001142 dicarboxylic acid group Chemical group 0.000 claims description 3
- 229930195735 unsaturated hydrocarbon Natural products 0.000 claims description 3
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims description 2
- 229910052799 carbon Inorganic materials 0.000 claims description 2
- 150000002762 monocarboxylic acid derivatives Chemical class 0.000 claims description 2
- 150000005846 sugar alcohols Polymers 0.000 claims description 2
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical group [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 claims 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 1
- 238000003763 carbonization Methods 0.000 claims 1
- 239000003381 stabilizer Substances 0.000 abstract description 24
- 229920000642 polymer Polymers 0.000 abstract description 21
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract description 10
- 229920005989 resin Polymers 0.000 abstract description 7
- 239000011347 resin Substances 0.000 abstract description 7
- 229910052736 halogen Inorganic materials 0.000 abstract description 6
- 150000002367 halogens Chemical class 0.000 abstract description 6
- 125000004430 oxygen atom Chemical group O* 0.000 abstract description 6
- 239000005864 Sulphur Substances 0.000 abstract 1
- -1 shelf elements Chemical compound 0.000 description 109
- 239000011541 reaction mixture Substances 0.000 description 56
- 238000000034 method Methods 0.000 description 44
- BDJRBEYXGGNYIS-UHFFFAOYSA-N nonanedioic acid Chemical compound OC(=O)CCCCCCCC(O)=O BDJRBEYXGGNYIS-UHFFFAOYSA-N 0.000 description 38
- 229940067597 azelate Drugs 0.000 description 34
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 30
- 239000000203 mixture Substances 0.000 description 30
- 235000011114 ammonium hydroxide Nutrition 0.000 description 28
- 239000000908 ammonium hydroxide Substances 0.000 description 27
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 27
- UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 description 26
- 239000000539 dimer Substances 0.000 description 26
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 24
- DGVVWUTYPXICAM-UHFFFAOYSA-N β‐Mercaptoethanol Chemical compound OCCS DGVVWUTYPXICAM-UHFFFAOYSA-N 0.000 description 24
- 238000006243 chemical reaction Methods 0.000 description 20
- YMLFYGFCXGNERH-UHFFFAOYSA-K butyltin trichloride Chemical compound CCCC[Sn](Cl)(Cl)Cl YMLFYGFCXGNERH-UHFFFAOYSA-K 0.000 description 19
- 239000008346 aqueous phase Substances 0.000 description 18
- 239000007787 solid Substances 0.000 description 18
- 239000012074 organic phase Substances 0.000 description 17
- 150000007513 acids Chemical class 0.000 description 15
- LUZSPGQEISANPO-UHFFFAOYSA-N butyltin Chemical compound CCCC[Sn] LUZSPGQEISANPO-UHFFFAOYSA-N 0.000 description 15
- 150000004820 halides Chemical class 0.000 description 15
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 13
- BZHJMEDXRYGGRV-UHFFFAOYSA-N Vinyl chloride Chemical compound ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 description 13
- GRVFOGOEDUUMBP-UHFFFAOYSA-N sodium sulfide (anhydrous) Chemical compound [Na+].[Na+].[S-2] GRVFOGOEDUUMBP-UHFFFAOYSA-N 0.000 description 13
- 239000007983 Tris buffer Substances 0.000 description 12
- NPAIMXWXWPJRES-UHFFFAOYSA-N butyltin(3+) Chemical compound CCCC[Sn+3] NPAIMXWXWPJRES-UHFFFAOYSA-N 0.000 description 11
- 229910052979 sodium sulfide Inorganic materials 0.000 description 11
- CFQZKFWQLAHGSL-FNTYJUCDSA-N (3e,5e,7e,9e,11e,13e,15e,17e)-18-[(3e,5e,7e,9e,11e,13e,15e,17e)-18-[(3e,5e,7e,9e,11e,13e,15e)-octadeca-3,5,7,9,11,13,15,17-octaenoyl]oxyoctadeca-3,5,7,9,11,13,15,17-octaenoyl]oxyoctadeca-3,5,7,9,11,13,15,17-octaenoic acid Chemical compound OC(=O)C\C=C\C=C\C=C\C=C\C=C\C=C\C=C\C=C\OC(=O)C\C=C\C=C\C=C\C=C\C=C\C=C\C=C\C=C\OC(=O)C\C=C\C=C\C=C\C=C\C=C\C=C\C=C\C=C CFQZKFWQLAHGSL-FNTYJUCDSA-N 0.000 description 10
- RZBBHEJLECUBJT-UHFFFAOYSA-N 6-methylheptyl 2-sulfanylacetate Chemical compound CC(C)CCCCCOC(=O)CS RZBBHEJLECUBJT-UHFFFAOYSA-N 0.000 description 10
- 229910052783 alkali metal Inorganic materials 0.000 description 9
- 150000001340 alkali metals Chemical class 0.000 description 9
- 239000000047 product Substances 0.000 description 9
- 239000000243 solution Substances 0.000 description 9
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 9
- 238000007792 addition Methods 0.000 description 8
- 238000004519 manufacturing process Methods 0.000 description 8
- WLJVNTCWHIRURA-UHFFFAOYSA-N pimelic acid Chemical compound OC(=O)CCCCCC(O)=O WLJVNTCWHIRURA-UHFFFAOYSA-N 0.000 description 8
- 150000008117 polysulfides Polymers 0.000 description 8
- 238000010438 heat treatment Methods 0.000 description 7
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 6
- 238000009835 boiling Methods 0.000 description 6
- UTOVMEACOLCUCK-PLNGDYQASA-N butyl maleate Chemical compound CCCCOC(=O)\C=C/C(O)=O UTOVMEACOLCUCK-PLNGDYQASA-N 0.000 description 6
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 6
- 229920001577 copolymer Polymers 0.000 description 6
- 238000004821 distillation Methods 0.000 description 6
- DNJIEGIFACGWOD-UHFFFAOYSA-N ethyl mercaptane Natural products CCS DNJIEGIFACGWOD-UHFFFAOYSA-N 0.000 description 6
- JFCQEDHGNNZCLN-UHFFFAOYSA-N glutaric acid Chemical compound OC(=O)CCCC(O)=O JFCQEDHGNNZCLN-UHFFFAOYSA-N 0.000 description 6
- 239000007788 liquid Substances 0.000 description 6
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 6
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 6
- 239000005077 polysulfide Substances 0.000 description 6
- CXMXRPHRNRROMY-UHFFFAOYSA-N sebacic acid Chemical compound OC(=O)CCCCCCCCC(O)=O CXMXRPHRNRROMY-UHFFFAOYSA-N 0.000 description 6
- CWERGRDVMFNCDR-UHFFFAOYSA-M thioglycolate(1-) Chemical compound [O-]C(=O)CS CWERGRDVMFNCDR-UHFFFAOYSA-M 0.000 description 6
- RMVRSNDYEFQCLF-UHFFFAOYSA-N thiophenol Chemical compound SC1=CC=CC=C1 RMVRSNDYEFQCLF-UHFFFAOYSA-N 0.000 description 6
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 5
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 5
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 5
- 239000007864 aqueous solution Substances 0.000 description 5
- 229910052793 cadmium Inorganic materials 0.000 description 5
- 238000001816 cooling Methods 0.000 description 5
- PJUIMOJAAPLTRJ-UHFFFAOYSA-N monothioglycerol Chemical compound OCC(O)CS PJUIMOJAAPLTRJ-UHFFFAOYSA-N 0.000 description 5
- 239000003921 oil Substances 0.000 description 5
- 235000019198 oils Nutrition 0.000 description 5
- 150000007519 polyprotic acids Polymers 0.000 description 5
- 229920001021 polysulfide Polymers 0.000 description 5
- 125000001424 substituent group Chemical group 0.000 description 5
- PXQLVRUNWNTZOS-UHFFFAOYSA-N sulfanyl Chemical class [SH] PXQLVRUNWNTZOS-UHFFFAOYSA-N 0.000 description 5
- RGHNJXZEOKUKBD-SQOUGZDYSA-N D-gluconic acid Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C(O)=O RGHNJXZEOKUKBD-SQOUGZDYSA-N 0.000 description 4
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 4
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 4
- 150000004703 alkoxides Chemical class 0.000 description 4
- 239000002585 base Substances 0.000 description 4
- BDOSMKKIYDKNTQ-UHFFFAOYSA-N cadmium atom Chemical compound [Cd] BDOSMKKIYDKNTQ-UHFFFAOYSA-N 0.000 description 4
- QYQADNCHXSEGJT-UHFFFAOYSA-N cyclohexane-1,1-dicarboxylate;hydron Chemical compound OC(=O)C1(C(O)=O)CCCCC1 QYQADNCHXSEGJT-UHFFFAOYSA-N 0.000 description 4
- 235000014113 dietary fatty acids Nutrition 0.000 description 4
- WNAHIZMDSQCWRP-UHFFFAOYSA-N dodecane-1-thiol Chemical compound CCCCCCCCCCCCS WNAHIZMDSQCWRP-UHFFFAOYSA-N 0.000 description 4
- 239000000194 fatty acid Substances 0.000 description 4
- 229930195729 fatty acid Natural products 0.000 description 4
- QQVIHTHCMHWDBS-UHFFFAOYSA-N isophthalic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 description 4
- 229910052751 metal Inorganic materials 0.000 description 4
- 125000002347 octyl 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])[H] 0.000 description 4
- OJMIONKXNSYLSR-UHFFFAOYSA-N phosphorous acid Chemical compound OP(O)O OJMIONKXNSYLSR-UHFFFAOYSA-N 0.000 description 4
- 239000000376 reactant Substances 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- TYFQFVWCELRYAO-UHFFFAOYSA-N suberic acid Chemical compound OC(=O)CCCCCCC(O)=O TYFQFVWCELRYAO-UHFFFAOYSA-N 0.000 description 4
- 238000012360 testing method Methods 0.000 description 4
- 150000003606 tin compounds Chemical class 0.000 description 4
- CYTQBVOFDCPGCX-UHFFFAOYSA-N trimethyl phosphite Chemical compound COP(OC)OC CYTQBVOFDCPGCX-UHFFFAOYSA-N 0.000 description 4
- 229920002554 vinyl polymer Polymers 0.000 description 4
- RTBFRGCFXZNCOE-UHFFFAOYSA-N 1-methylsulfonylpiperidin-4-one Chemical compound CS(=O)(=O)N1CCC(=O)CC1 RTBFRGCFXZNCOE-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 3
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 3
- 239000001361 adipic acid Substances 0.000 description 3
- 235000011037 adipic acid Nutrition 0.000 description 3
- BJEPYKJPYRNKOW-UHFFFAOYSA-N alpha-hydroxysuccinic acid Natural products OC(=O)C(O)CC(O)=O BJEPYKJPYRNKOW-UHFFFAOYSA-N 0.000 description 3
- 150000008064 anhydrides Chemical class 0.000 description 3
- 229910052788 barium Inorganic materials 0.000 description 3
- DSAJWYNOEDNPEQ-UHFFFAOYSA-N barium atom Chemical compound [Ba] DSAJWYNOEDNPEQ-UHFFFAOYSA-N 0.000 description 3
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 3
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 3
- 239000006227 byproduct Substances 0.000 description 3
- KQTIIICEAUMSDG-UHFFFAOYSA-N carboxymethylsuccinic acid Natural products OC(=O)CC(C(O)=O)CC(O)=O KQTIIICEAUMSDG-UHFFFAOYSA-N 0.000 description 3
- RJGHQTVXGKYATR-UHFFFAOYSA-L dibutyl(dichloro)stannane Chemical compound CCCC[Sn](Cl)(Cl)CCCC RJGHQTVXGKYATR-UHFFFAOYSA-L 0.000 description 3
- 150000001991 dicarboxylic acids Chemical class 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 229920001519 homopolymer Polymers 0.000 description 3
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 3
- 239000011976 maleic acid Substances 0.000 description 3
- 239000002184 metal Substances 0.000 description 3
- LVHBHZANLOWSRM-UHFFFAOYSA-N methylenebutanedioic acid Natural products OC(=O)CC(=C)C(O)=O LVHBHZANLOWSRM-UHFFFAOYSA-N 0.000 description 3
- 238000002156 mixing Methods 0.000 description 3
- 150000002763 monocarboxylic acids Chemical class 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 239000004014 plasticizer Substances 0.000 description 3
- 229920000915 polyvinyl chloride Polymers 0.000 description 3
- 239000004800 polyvinyl chloride Substances 0.000 description 3
- 235000012424 soybean oil Nutrition 0.000 description 3
- 239000003549 soybean oil Substances 0.000 description 3
- 230000000087 stabilizing effect Effects 0.000 description 3
- KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 3
- 150000003568 thioethers Chemical class 0.000 description 3
- CWERGRDVMFNCDR-UHFFFAOYSA-N thioglycolic acid Chemical class OC(=O)CS CWERGRDVMFNCDR-UHFFFAOYSA-N 0.000 description 3
- BJEPYKJPYRNKOW-REOHCLBHSA-N (S)-malic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O BJEPYKJPYRNKOW-REOHCLBHSA-N 0.000 description 2
- VBSTXRUAXCTZBQ-UHFFFAOYSA-N 1-hexyl-4-phenylpiperazine Chemical compound C1CN(CCCCCC)CCN1C1=CC=CC=C1 VBSTXRUAXCTZBQ-UHFFFAOYSA-N 0.000 description 2
- XDOFQFKRPWOURC-UHFFFAOYSA-N 16-methylheptadecanoic acid Chemical compound CC(C)CCCCCCCCCCCCCCC(O)=O XDOFQFKRPWOURC-UHFFFAOYSA-N 0.000 description 2
- JAHNSTQSQJOJLO-UHFFFAOYSA-N 2-(3-fluorophenyl)-1h-imidazole Chemical compound FC1=CC=CC(C=2NC=CN=2)=C1 JAHNSTQSQJOJLO-UHFFFAOYSA-N 0.000 description 2
- 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 2
- DLLMHEDYJQACRM-UHFFFAOYSA-N 2-(carboxymethyldisulfanyl)acetic acid Chemical compound OC(=O)CSSCC(O)=O DLLMHEDYJQACRM-UHFFFAOYSA-N 0.000 description 2
- JAEJSNFTJMYIEF-UHFFFAOYSA-N 2-benzylpropanedioic acid Chemical compound OC(=O)C(C(O)=O)CC1=CC=CC=C1 JAEJSNFTJMYIEF-UHFFFAOYSA-N 0.000 description 2
- WXUAQHNMJWJLTG-UHFFFAOYSA-N 2-methylbutanedioic acid Chemical compound OC(=O)C(C)CC(O)=O WXUAQHNMJWJLTG-UHFFFAOYSA-N 0.000 description 2
- FRQQKWGDKVGLFI-UHFFFAOYSA-N 2-methylundecane-2-thiol Chemical compound CCCCCCCCCC(C)(C)S FRQQKWGDKVGLFI-UHFFFAOYSA-N 0.000 description 2
- KPGXRSRHYNQIFN-UHFFFAOYSA-N 2-oxoglutaric acid Chemical compound OC(=O)CCC(=O)C(O)=O KPGXRSRHYNQIFN-UHFFFAOYSA-N 0.000 description 2
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 2
- YCLSOMLVSHPPFV-UHFFFAOYSA-N 3-(2-carboxyethyldisulfanyl)propanoic acid Chemical compound OC(=O)CCSSCCC(O)=O YCLSOMLVSHPPFV-UHFFFAOYSA-N 0.000 description 2
- RSWGJHLUYNHPMX-UHFFFAOYSA-N Abietic-Saeure Natural products C12CCC(C(C)C)=CC2=CCC2C1(C)CCCC2(C)C(O)=O RSWGJHLUYNHPMX-UHFFFAOYSA-N 0.000 description 2
- SOGAXMICEFXMKE-UHFFFAOYSA-N Butylmethacrylate Chemical compound CCCCOC(=O)C(C)=C SOGAXMICEFXMKE-UHFFFAOYSA-N 0.000 description 2
- XKCYYVCNDLSTRW-UPHRSURJSA-N C(\C=C/C(=O)OCCS)(=S)OCCS Chemical compound C(\C=C/C(=O)OCCS)(=S)OCCS XKCYYVCNDLSTRW-UPHRSURJSA-N 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
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- LFQCEHFDDXELDD-UHFFFAOYSA-N tetramethyl orthosilicate Chemical compound CO[Si](OC)(OC)OC LFQCEHFDDXELDD-UHFFFAOYSA-N 0.000 description 1
- ZYCRSZQVMREWQH-UHFFFAOYSA-N tetraphosphorus hexasulfide Chemical compound S1P(S2)SP3SP1SP2S3 ZYCRSZQVMREWQH-UHFFFAOYSA-N 0.000 description 1
- 150000003566 thiocarboxylic acids Chemical class 0.000 description 1
- 235000019303 thiodipropionic acid Nutrition 0.000 description 1
- NJRXVEJTAYWCQJ-UHFFFAOYSA-N thiomalic acid Chemical compound OC(=O)CC(S)C(O)=O NJRXVEJTAYWCQJ-UHFFFAOYSA-N 0.000 description 1
- WQYSXVGEZYESBR-UHFFFAOYSA-N thiophosphoryl chloride Chemical compound ClP(Cl)(Cl)=S WQYSXVGEZYESBR-UHFFFAOYSA-N 0.000 description 1
- 150000003609 titanium compounds Chemical class 0.000 description 1
- 239000004408 titanium dioxide Substances 0.000 description 1
- XJDNKRIXUMDJCW-UHFFFAOYSA-J titanium tetrachloride Chemical compound Cl[Ti](Cl)(Cl)Cl XJDNKRIXUMDJCW-UHFFFAOYSA-J 0.000 description 1
- TXXHDPDFNKHHGW-ZPUQHVIOSA-N trans,trans-muconic acid Chemical compound OC(=O)\C=C\C=C\C(O)=O TXXHDPDFNKHHGW-ZPUQHVIOSA-N 0.000 description 1
- MAZWDMBCPDUFDJ-UHFFFAOYSA-N trans-Traumatinsaeure Natural products OC(=O)CCCCCCCCC=CC(O)=O MAZWDMBCPDUFDJ-UHFFFAOYSA-N 0.000 description 1
- 238000005809 transesterification reaction Methods 0.000 description 1
- YZVRVDPMGYFCGL-UHFFFAOYSA-N triacetyloxysilyl acetate Chemical compound CC(=O)O[Si](OC(C)=O)(OC(C)=O)OC(C)=O YZVRVDPMGYFCGL-UHFFFAOYSA-N 0.000 description 1
- BYQWEYFCJKJRHO-UHFFFAOYSA-K tribromo(butyl)stannane Chemical compound CCCC[Sn](Br)(Br)Br BYQWEYFCJKJRHO-UHFFFAOYSA-K 0.000 description 1
- SSGLIJVXYPSIEZ-UHFFFAOYSA-K tribromo(methyl)stannane Chemical compound C[Sn](Br)(Br)Br SSGLIJVXYPSIEZ-UHFFFAOYSA-K 0.000 description 1
- XTTGYFREQJCEML-UHFFFAOYSA-N tributyl phosphite Chemical compound CCCCOP(OCCCC)OCCCC XTTGYFREQJCEML-UHFFFAOYSA-N 0.000 description 1
- JSQJUDVTRRCSRU-UHFFFAOYSA-N tributyl(chloro)silane Chemical compound CCCC[Si](Cl)(CCCC)CCCC JSQJUDVTRRCSRU-UHFFFAOYSA-N 0.000 description 1
- PDFNMVKYZSDSLJ-UHFFFAOYSA-K trichloro(2-methylpropyl)stannane Chemical compound CC(C)C[Sn](Cl)(Cl)Cl PDFNMVKYZSDSLJ-UHFFFAOYSA-K 0.000 description 1
- QONBXEOLXRAITN-UHFFFAOYSA-K trichloro(dodecyl)stannane Chemical compound CCCCCCCCCCCC[Sn](Cl)(Cl)Cl QONBXEOLXRAITN-UHFFFAOYSA-K 0.000 description 1
- URNVMBADOXXKOA-UHFFFAOYSA-K trichloro(ethenyl)stannane Chemical compound Cl[Sn](Cl)(Cl)C=C URNVMBADOXXKOA-UHFFFAOYSA-K 0.000 description 1
- MEBRQLCKPRKBOH-UHFFFAOYSA-K trichloro(ethyl)stannane Chemical compound CC[Sn](Cl)(Cl)Cl MEBRQLCKPRKBOH-UHFFFAOYSA-K 0.000 description 1
- RCHUVCPBWWSUMC-UHFFFAOYSA-N trichloro(octyl)silane Chemical compound CCCCCCCC[Si](Cl)(Cl)Cl RCHUVCPBWWSUMC-UHFFFAOYSA-N 0.000 description 1
- INTLMJZQCBRQAT-UHFFFAOYSA-K trichloro(octyl)stannane Chemical compound CCCCCCCC[Sn](Cl)(Cl)Cl INTLMJZQCBRQAT-UHFFFAOYSA-K 0.000 description 1
- LLMLKXBRBOGFFA-UHFFFAOYSA-K trichloro-(4-methylphenyl)stannane Chemical compound CC1=CC=C([Sn](Cl)(Cl)Cl)C=C1 LLMLKXBRBOGFFA-UHFFFAOYSA-K 0.000 description 1
- UBOXGVDOUJQMTN-UHFFFAOYSA-N trichloroethylene Natural products ClCC(Cl)Cl UBOXGVDOUJQMTN-UHFFFAOYSA-N 0.000 description 1
- YSCVYRUCAPMZFG-UHFFFAOYSA-K trichlorotin Chemical compound Cl[Sn](Cl)Cl YSCVYRUCAPMZFG-UHFFFAOYSA-K 0.000 description 1
- IPBROXKVGHZHJV-UHFFFAOYSA-N tridecane-1-thiol Chemical compound CCCCCCCCCCCCCS IPBROXKVGHZHJV-UHFFFAOYSA-N 0.000 description 1
- JCVQKRGIASEUKR-UHFFFAOYSA-N triethoxy(phenyl)silane Chemical compound CCO[Si](OCC)(OCC)C1=CC=CC=C1 JCVQKRGIASEUKR-UHFFFAOYSA-N 0.000 description 1
- BDZBKCUKTQZUTL-UHFFFAOYSA-N triethyl phosphite Chemical compound CCOP(OCC)OCC BDZBKCUKTQZUTL-UHFFFAOYSA-N 0.000 description 1
- WVLBCYQITXONBZ-UHFFFAOYSA-N trimethyl phosphate Chemical compound COP(=O)(OC)OC WVLBCYQITXONBZ-UHFFFAOYSA-N 0.000 description 1
- NLSXASIDNWDYMI-UHFFFAOYSA-N triphenylsilanol Chemical compound C=1C=CC=CC=1[Si](C=1C=CC=CC=1)(O)C1=CC=CC=C1 NLSXASIDNWDYMI-UHFFFAOYSA-N 0.000 description 1
- QOPBTFMUVTXWFF-UHFFFAOYSA-N tripropyl phosphite Chemical compound CCCOP(OCCC)OCCC QOPBTFMUVTXWFF-UHFFFAOYSA-N 0.000 description 1
- 235000021122 unsaturated fatty acids Nutrition 0.000 description 1
- 150000004670 unsaturated fatty acids Chemical class 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- FUSUHKVFWTUUBE-UHFFFAOYSA-N vinyl methyl ketone Natural products CC(=O)C=C FUSUHKVFWTUUBE-UHFFFAOYSA-N 0.000 description 1
- 229920001959 vinylidene polymer Polymers 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 229940105125 zinc myristate Drugs 0.000 description 1
- CHJMFFKHPHCQIJ-UHFFFAOYSA-L zinc;octanoate Chemical compound [Zn+2].CCCCCCCC([O-])=O.CCCCCCCC([O-])=O CHJMFFKHPHCQIJ-UHFFFAOYSA-L 0.000 description 1
- GBFLQPIIIRJQLU-UHFFFAOYSA-L zinc;tetradecanoate Chemical compound [Zn+2].CCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCC([O-])=O GBFLQPIIIRJQLU-UHFFFAOYSA-L 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
- C08K5/56—Organo-metallic compounds, i.e. organic compounds containing a metal-to-carbon bond
- C08K5/57—Organo-tin compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/22—Tin compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/22—Tin compounds
- C07F7/226—Compounds with one or more Sn-S linkages
-
- 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
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L27/00—Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a halogen; Compositions of derivatives of such polymers
- C08L27/02—Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a halogen; Compositions of derivatives of such polymers not modified by chemical after-treatment
- C08L27/04—Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a halogen; Compositions of derivatives of such polymers not modified by chemical after-treatment containing chlorine atoms
- C08L27/06—Homopolymers or copolymers of vinyl chloride
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Polymers & Plastics (AREA)
- Medicinal Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- Biochemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Polyesters Or Polycarbonates (AREA)
- Heat-Exchange Devices With Radiators And Conduit Assemblies (AREA)
- Catalysts (AREA)
- Polymerisation Methods In General (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Steroid Compounds (AREA)
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US05/959,518 US4254017A (en) | 1978-11-13 | 1978-11-13 | Organotin mercaptoalkanol esters and alkoxides containing sulfide groups |
US959518 | 1978-11-13 |
Publications (2)
Publication Number | Publication Date |
---|---|
JPS5573695A JPS5573695A (en) | 1980-06-03 |
JPS6039360B2 true JPS6039360B2 (ja) | 1985-09-05 |
Family
ID=25502110
Family Applications (2)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP54145568A Expired JPS6039360B2 (ja) | 1978-11-13 | 1979-11-12 | 新規オルガノ錫化合物 |
JP60030681A Granted JPS60226891A (ja) | 1978-11-13 | 1985-02-20 | オルガノ錫化合物 |
Family Applications After (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP60030681A Granted JPS60226891A (ja) | 1978-11-13 | 1985-02-20 | オルガノ錫化合物 |
Country Status (20)
Families Citing this family (25)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4701486A (en) * | 1981-02-26 | 1987-10-20 | Morton Thiokol, Inc. | Stabilizer compositions for PVC resins |
US4558083A (en) * | 1981-02-26 | 1985-12-10 | Morton Thiokol, Inc. | Stabilizer compositions and polymers containing same |
US4314934A (en) * | 1981-02-26 | 1982-02-09 | Carstab Corporation | Organohalide polymers stabilized with an organotin compound and an ortho mercapto phenol compound |
US4988750A (en) * | 1981-07-17 | 1991-01-29 | Schering Ag | Non-toxic stabilizer for halogenated polymer |
US4576984A (en) * | 1982-02-04 | 1986-03-18 | Morton Thiokol, Inc. | Stabilizer compositions for PVC resins |
US4665114A (en) * | 1982-02-04 | 1987-05-12 | Morton Thiokol Inc. | Stabilizer compositions and polymers containing same |
US4788083A (en) * | 1986-03-27 | 1988-11-29 | Ashland Oil, Inc. | Tin or bismuth complex catalysts and trigger cure of coatings therewith |
GB8724049D0 (en) * | 1987-10-14 | 1987-11-18 | Kodak Ltd | Organotin compounds as anionic ionophores |
US4816593A (en) * | 1987-12-21 | 1989-03-28 | Cardinal Reserach & Development Co., Inc. | Heterocyclic organotin compounds |
US4981924A (en) * | 1989-09-11 | 1991-01-01 | Air Products And Chemicals, Inc. | Cationic electrodepositable compositions of blocked polyisocyanates and amine-epoxy resins containing diorganotin bis-mercaptides and bis-carboxylates as catalysts |
US5089645A (en) * | 1989-09-11 | 1992-02-18 | Air Products And Chemicals, Inc. | Hydroxyl-containing organotin catalysts for making polyurethanes |
US4987244A (en) * | 1989-09-11 | 1991-01-22 | Air Products And Chemicals, Inc. | Organotin catalysts for use in polyurethane systems |
US5089584A (en) * | 1989-10-20 | 1992-02-18 | Air Products And Chemicals, Inc. | Polymeric diorganotin catalysts for use in polyurethane systems |
US5089583A (en) * | 1989-10-20 | 1992-02-18 | Air Products And Chemicals, Inc. | Heterocyclic diorganotin catalysts for use in polyurethane systems |
US4981925A (en) * | 1989-10-20 | 1991-01-01 | Air Products And Chemicals, Inc. | Cationic electrodepositable compositions of partially-blocked polyisocyanates and amine-epoxy resins containing polymeric diorganotin catalysts |
US4978728A (en) * | 1989-10-20 | 1990-12-18 | Air Products And Chemicals, Inc. | Cationic electrodepositable compositions of partially-blocked polyisocyanates and amine-epoxy resins containing heterocyclic diorganotin catalysts |
US5145976A (en) * | 1989-10-20 | 1992-09-08 | Air Products And Chemicals, Inc. | Polymeric diorganotin catalysts for use in polyurethane systems |
US5149844A (en) * | 1989-10-20 | 1992-09-22 | Air Products And Chemicals, Inc. | Heterocyclic diorganotin catalysts for use in polyurethane systems |
US5284886A (en) * | 1989-10-31 | 1994-02-08 | Elf Atochem North America, Inc. | Non-toxic polymeric compositions stabilized with organosulfide antioxidants |
CA2001633C (en) * | 1989-11-06 | 1996-07-09 | M & T Chemicals Inc. | Antioxidant polyolefin compositions |
FR2656301B1 (fr) * | 1989-12-21 | 1993-05-21 | Poudres & Explosifs Ste Nale | Procede catalytique de synthese d'un alcool. procede de synthese du catalyseur et nouveaux complexes metalliques. |
US5034551A (en) * | 1990-04-23 | 1991-07-23 | Noramco, Inc. | Process for recovery of organotin esters from reaction mixtures containing the same and re-use of the recovered organotin compounds |
US5109046A (en) * | 1991-02-28 | 1992-04-28 | Atochem North America, Inc. | Liquid organotinthioalkanol stabilizer compositions and vinyl halide resin compositions containing the same |
US5725904A (en) * | 1995-06-02 | 1998-03-10 | Elf Atochem North America, Inc. | Liquid methyltin halide compositions |
CN103524789B (zh) * | 2013-08-29 | 2014-09-10 | 河南师范大学 | 一种硫醇基脂肪酸亚锡类pvc热稳定剂及其制备方法 |
Family Cites Families (16)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2731484A (en) * | 1950-06-27 | 1956-01-17 | Firestone Tire & Rubber Co | Preparation of organotin mercaptides |
US2872468A (en) * | 1952-10-16 | 1959-02-03 | Argus Chemical Lab Inc | Organic derivatives of tetravalent tin |
US2914506A (en) * | 1953-01-02 | 1959-11-24 | Carlisle Chemical Works | Halogen-containing resins stabilized with organo-tin mercapto compounds |
FR1091704A (fr) * | 1953-11-26 | 1955-04-14 | Metal & Thermit Corp | Procédé de fabrication de compositions résineuses stabilisees à base de chlorure de polyvinyle |
NL132370C (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) * | 1965-01-22 | 1900-01-01 | ||
US3565930A (en) * | 1967-12-19 | 1971-02-23 | Argus Chem | Organotin mercapto carboxylic acid ester sulfides |
US3565931A (en) * | 1967-12-19 | 1971-02-23 | Lawrence Robert Brecker | Process for preparing organotin mercapto carboxylic acid ester sulfides containing more than 18% tin |
GB1257018A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) * | 1968-02-23 | 1971-12-15 | ||
CA1052804A (en) * | 1974-03-08 | 1979-04-17 | Kenneth R. Molt | Organotin mercaptide process |
US4062881A (en) * | 1974-07-26 | 1977-12-13 | Cincinnati Milacron Chemicals, Inc. | Sulfide containing tin stabilizers |
US3979359A (en) * | 1974-11-15 | 1976-09-07 | Cincinnati Milacron Chemicals, Inc. | Carbofunctional sulfur and carboxylate bridged tin compounds |
GB1552774A (en) * | 1975-11-25 | 1979-09-19 | Akzo Nv | Organotin stabilizer compositions and polyvinyl resins stabilized therewith |
JPS52152446A (en) * | 1976-06-14 | 1977-12-17 | Adeka Argus Chem Co Ltd | Rubber-modified styrene resin compositions |
US4104292A (en) * | 1976-11-02 | 1978-08-01 | M&T Chemicals Inc. | Method for preparing organotin compounds |
US4124618A (en) * | 1976-11-02 | 1978-11-07 | M&T Chemicals Inc. | Method for preparing bis(organotin mercaptoalkanol ester) sulfides |
US4118371A (en) * | 1977-04-29 | 1978-10-03 | Cincinnati Milacron Chemicals Inc. | Organotin mercaptoalkanol ester sulfide stabilizers for PVC resins |
-
1978
- 1978-11-13 US US05/959,518 patent/US4254017A/en not_active Expired - Lifetime
-
1979
- 1979-10-17 IL IL58483A patent/IL58483A0/xx unknown
- 1979-10-29 ZA ZA00795779A patent/ZA795779B/xx unknown
- 1979-10-30 NZ NZ191967A patent/NZ191967A/xx unknown
- 1979-11-05 PT PT70414A patent/PT70414A/pt unknown
- 1979-11-09 EP EP79302520A patent/EP0011456B1/en not_active Expired
- 1979-11-09 CA CA339,513A patent/CA1126748A/en not_active Expired
- 1979-11-09 DE DE7979302520T patent/DE2966141D1/de not_active Expired
- 1979-11-09 AT AT79302520T patent/ATE4597T1/de active
- 1979-11-12 NO NO793658A patent/NO160372C/no unknown
- 1979-11-12 DK DK478179A patent/DK156006C/da not_active IP Right Cessation
- 1979-11-12 ES ES485870A patent/ES485870A0/es active Granted
- 1979-11-12 AU AU52732/79A patent/AU536132B2/en not_active Ceased
- 1979-11-12 JP JP54145568A patent/JPS6039360B2/ja not_active Expired
- 1979-11-12 KR KR1019790003945A patent/KR830002500B1/ko not_active Expired
- 1979-11-12 BR BR7907337A patent/BR7907337A/pt not_active IP Right Cessation
- 1979-11-13 PL PL21957279A patent/PL219572A1/xx unknown
- 1979-11-13 MX MX180025A patent/MX152914A/es unknown
-
1984
- 1984-01-05 SG SG16/84A patent/SG1684G/en unknown
-
1985
- 1985-02-20 JP JP60030681A patent/JPS60226891A/ja active Granted
- 1985-12-30 MY MY357/85A patent/MY8500357A/xx unknown
Also Published As
Publication number | Publication date |
---|---|
JPS60226891A (ja) | 1985-11-12 |
MY8500357A (en) | 1985-12-31 |
NO160372C (no) | 1989-04-12 |
JPH0129194B2 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1989-06-08 |
DK478179A (da) | 1980-05-14 |
ATE4597T1 (de) | 1983-09-15 |
NO160372B (no) | 1989-01-02 |
EP0011456A1 (en) | 1980-05-28 |
EP0011456B1 (en) | 1983-09-07 |
AU5273279A (en) | 1980-05-22 |
ES8100306A1 (es) | 1980-11-01 |
CA1126748A (en) | 1982-06-29 |
NO793658L (no) | 1980-05-14 |
DK156006B (da) | 1989-06-12 |
BR7907337A (pt) | 1980-07-15 |
ZA795779B (en) | 1980-10-29 |
NZ191967A (en) | 1982-03-16 |
ES485870A0 (es) | 1980-11-01 |
DE2966141D1 (en) | 1983-10-13 |
JPS5573695A (en) | 1980-06-03 |
MX152914A (es) | 1986-07-01 |
IL58483A0 (en) | 1980-01-31 |
US4254017A (en) | 1981-03-03 |
PL219572A1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1981-07-24 |
PT70414A (en) | 1979-12-01 |
AU536132B2 (en) | 1984-04-19 |
KR830001333A (en) | 1983-04-30 |
KR830002500B1 (ko) | 1983-10-27 |
DK156006C (da) | 1989-11-13 |
SG1684G (en) | 1985-02-01 |
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