USRE30810E - Carbofunctional sulfur and carboxylate bridged tin compounds - Google Patents
Carbofunctional sulfur and carboxylate bridged tin compounds Download PDFInfo
- Publication number
- USRE30810E USRE30810E US06/141,912 US14191280A USRE30810E US RE30810 E USRE30810 E US RE30810E US 14191280 A US14191280 A US 14191280A US RE30810 E USRE30810 E US RE30810E
- Authority
- US
- United States
- Prior art keywords
- compound according
- carbon atoms
- alkyl
- alkylene
- mercaptoethyl
- 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 - Lifetime
Links
- 229910052717 sulfur Inorganic materials 0.000 title claims abstract description 8
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 title claims abstract description 7
- 239000011593 sulfur Substances 0.000 title claims abstract description 7
- 150000007942 carboxylates Chemical class 0.000 title abstract description 3
- 150000003606 tin compounds Chemical class 0.000 title description 4
- 150000001875 compounds Chemical class 0.000 claims abstract description 80
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 75
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 28
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 17
- 150000002367 halogens Chemical class 0.000 claims abstract description 17
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical group [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 claims abstract description 13
- -1 --CH═CH-- Chemical group 0.000 claims description 42
- 239000002253 acid Substances 0.000 claims description 30
- 125000002947 alkylene group Chemical group 0.000 claims description 25
- 239000000203 mixture Substances 0.000 claims description 24
- 229920000642 polymer Polymers 0.000 claims description 17
- 125000005843 halogen group Chemical group 0.000 claims description 11
- 125000003342 alkenyl group Chemical group 0.000 claims description 10
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 10
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 10
- 125000005059 halophenyl group Chemical group 0.000 claims description 10
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 10
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 10
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims description 10
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims description 9
- BZHJMEDXRYGGRV-UHFFFAOYSA-N Vinyl chloride Chemical group ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 claims description 8
- 125000000732 arylene group Chemical group 0.000 claims description 8
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 8
- 229910052718 tin Inorganic materials 0.000 claims description 8
- 229910052739 hydrogen Inorganic materials 0.000 claims description 5
- 239000001257 hydrogen Substances 0.000 claims description 5
- 239000000460 chlorine Substances 0.000 claims description 4
- 229910052801 chlorine Inorganic materials 0.000 claims description 4
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 3
- 125000005037 alkyl phenyl group Chemical group 0.000 claims description 3
- 229920001971 elastomer Polymers 0.000 claims description 3
- 150000002431 hydrogen Chemical class 0.000 claims description 3
- 239000005060 rubber Substances 0.000 claims description 3
- 239000004801 Chlorinated PVC Substances 0.000 claims description 2
- 239000004709 Chlorinated polyethylene Substances 0.000 claims description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- 239000004793 Polystyrene Substances 0.000 claims description 2
- 229920000457 chlorinated polyvinyl chloride Polymers 0.000 claims description 2
- 229920002223 polystyrene Polymers 0.000 claims description 2
- 125000005020 hydroxyalkenyl group Chemical group 0.000 claims 2
- 125000001140 1,4-phenylene group Chemical group [H]C1=C([H])C([*:2])=C([H])C([H])=C1[*:1] 0.000 claims 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 1
- 229920000915 polyvinyl chloride Polymers 0.000 abstract description 5
- 239000004800 polyvinyl chloride Substances 0.000 abstract description 5
- 229920002554 vinyl polymer Polymers 0.000 abstract description 5
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 abstract description 3
- 229920001959 vinylidene polymer Polymers 0.000 abstract description 2
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 30
- 238000000034 method Methods 0.000 description 21
- 239000000047 product Substances 0.000 description 21
- 239000003921 oil Substances 0.000 description 20
- 235000019198 oils Nutrition 0.000 description 20
- 150000007513 acids Chemical class 0.000 description 17
- SDBQMGGFXXVCCV-UHFFFAOYSA-N bis(2-sulfanylethyl) hexanedioate Chemical compound SCCOC(=O)CCCCC(=O)OCCS SDBQMGGFXXVCCV-UHFFFAOYSA-N 0.000 description 17
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 14
- BHWWTWCFLZECFZ-UHFFFAOYSA-N 2-sulfanylethyl octanoate Chemical compound CCCCCCCC(=O)OCCS BHWWTWCFLZECFZ-UHFFFAOYSA-N 0.000 description 12
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 10
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 10
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical class CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- 239000003381 stabilizer Substances 0.000 description 9
- YFRLQYJXUZRYDN-UHFFFAOYSA-K trichloro(methyl)stannane Chemical compound C[Sn](Cl)(Cl)Cl YFRLQYJXUZRYDN-UHFFFAOYSA-K 0.000 description 8
- 239000012230 colorless oil Substances 0.000 description 7
- CSHCPECZJIEGJF-UHFFFAOYSA-N methyltin Chemical compound [Sn]C CSHCPECZJIEGJF-UHFFFAOYSA-N 0.000 description 7
- 239000011135 tin Substances 0.000 description 7
- WEMJWKKJHSZRQT-KTKRTIGZSA-N 2-sulfanylethyl (z)-octadec-9-enoate Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OCCS WEMJWKKJHSZRQT-KTKRTIGZSA-N 0.000 description 6
- 239000004593 Epoxy Substances 0.000 description 6
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 6
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 6
- WNLRTRBMVRJNCN-UHFFFAOYSA-L adipate(2-) Chemical compound [O-]C(=O)CCCCC([O-])=O WNLRTRBMVRJNCN-UHFFFAOYSA-L 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
- CWERGRDVMFNCDR-UHFFFAOYSA-N thioglycolic acid Chemical compound OC(=O)CS CWERGRDVMFNCDR-UHFFFAOYSA-N 0.000 description 6
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 6
- PKKGKUDPKRTKLJ-UHFFFAOYSA-L dichloro(dimethyl)stannane Chemical compound C[Sn](C)(Cl)Cl PKKGKUDPKRTKLJ-UHFFFAOYSA-L 0.000 description 5
- 150000002148 esters Chemical class 0.000 description 5
- 239000010410 layer Substances 0.000 description 5
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 5
- 230000035484 reaction time Effects 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- DGVVWUTYPXICAM-UHFFFAOYSA-N β‐Mercaptoethanol Chemical compound OCCS DGVVWUTYPXICAM-UHFFFAOYSA-N 0.000 description 5
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 4
- YMLFYGFCXGNERH-UHFFFAOYSA-K butyltin trichloride Chemical compound CCCC[Sn](Cl)(Cl)Cl YMLFYGFCXGNERH-UHFFFAOYSA-K 0.000 description 4
- 229910052793 cadmium Inorganic materials 0.000 description 4
- 239000007795 chemical reaction product Substances 0.000 description 4
- 229920001577 copolymer Polymers 0.000 description 4
- 239000011976 maleic acid Substances 0.000 description 4
- 239000003549 soybean oil Substances 0.000 description 4
- 235000012424 soybean oil Nutrition 0.000 description 4
- PADVGJLELBPBCZ-WAYWQWQTSA-N (Z)-2,3-bis(2-sulfanylethyl)but-2-enedioic acid Chemical compound SCC/C(C(=O)O)=C(\CCS)C(O)=O PADVGJLELBPBCZ-WAYWQWQTSA-N 0.000 description 3
- UHDGCPHLGDOIAH-UHFFFAOYSA-N 2-(2-sulfanylethylsulfanyl)propanoic acid Chemical compound OC(=O)C(C)SCCS UHDGCPHLGDOIAH-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical class C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- 125000004799 bromophenyl group Chemical group 0.000 description 3
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- WIHMDCQAEONXND-UHFFFAOYSA-M butyl-hydroxy-oxotin Chemical compound CCCC[Sn](O)=O WIHMDCQAEONXND-UHFFFAOYSA-M 0.000 description 3
- BDOSMKKIYDKNTQ-UHFFFAOYSA-N cadmium atom Chemical compound [Cd] BDOSMKKIYDKNTQ-UHFFFAOYSA-N 0.000 description 3
- 125000000068 chlorophenyl group Chemical group 0.000 description 3
- 235000014113 dietary fatty acids Nutrition 0.000 description 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
- WNVQCJNZEDLILP-UHFFFAOYSA-N dimethyl(oxo)tin Chemical compound C[Sn](C)=O WNVQCJNZEDLILP-UHFFFAOYSA-N 0.000 description 3
- DNJIEGIFACGWOD-UHFFFAOYSA-N ethyl mercaptane Natural products CCS DNJIEGIFACGWOD-UHFFFAOYSA-N 0.000 description 3
- 229930195729 fatty acid Natural products 0.000 description 3
- 239000000194 fatty acid Substances 0.000 description 3
- 150000004665 fatty acids Chemical class 0.000 description 3
- 125000001207 fluorophenyl group Chemical group 0.000 description 3
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 3
- 239000011133 lead Substances 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical class CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- BDJRBEYXGGNYIS-UHFFFAOYSA-N nonanedioic acid Chemical compound OC(=O)CCCCCCCC(O)=O BDJRBEYXGGNYIS-UHFFFAOYSA-N 0.000 description 3
- FBUKVWPVBMHYJY-UHFFFAOYSA-M nonanoate Chemical compound CCCCCCCCC([O-])=O FBUKVWPVBMHYJY-UHFFFAOYSA-M 0.000 description 3
- 239000004014 plasticizer Substances 0.000 description 3
- 229920005989 resin Polymers 0.000 description 3
- 239000011347 resin Substances 0.000 description 3
- IQBLWPLYPNOTJC-FPLPWBNLSA-N (z)-4-(2-ethylhexoxy)-4-oxobut-2-enoic acid Chemical compound CCCCC(CC)COC(=O)\C=C/C(O)=O IQBLWPLYPNOTJC-FPLPWBNLSA-N 0.000 description 2
- LEDJKFIAVLTWLG-UPHRSURJSA-N (z)-4-oxo-4-(2-sulfanylethoxy)but-2-enoic acid Chemical compound OC(=O)\C=C/C(=O)OCCS LEDJKFIAVLTWLG-UPHRSURJSA-N 0.000 description 2
- DHBXNPKRAUYBTH-UHFFFAOYSA-N 1,1-ethanedithiol Chemical compound CC(S)S DHBXNPKRAUYBTH-UHFFFAOYSA-N 0.000 description 2
- PVERQJVCDFCIDS-UHFFFAOYSA-N 2,4-bis(sulfanyl)butanoic acid Chemical compound OC(=O)C(S)CCS PVERQJVCDFCIDS-UHFFFAOYSA-N 0.000 description 2
- PMNLUUOXGOOLSP-UHFFFAOYSA-N 2-mercaptopropanoic acid Chemical compound CC(S)C(O)=O PMNLUUOXGOOLSP-UHFFFAOYSA-N 0.000 description 2
- DKIDEFUBRARXTE-UHFFFAOYSA-N 3-mercaptopropanoic acid Chemical compound OC(=O)CCS DKIDEFUBRARXTE-UHFFFAOYSA-N 0.000 description 2
- SHLSSLVZXJBVHE-UHFFFAOYSA-N 3-sulfanylpropan-1-ol Chemical compound OCCCS SHLSSLVZXJBVHE-UHFFFAOYSA-N 0.000 description 2
- NEJMTSWXTZREOC-UHFFFAOYSA-N 4-sulfanylbutan-1-ol Chemical compound OCCCCS NEJMTSWXTZREOC-UHFFFAOYSA-N 0.000 description 2
- VVWPSAPZUZXYCM-UHFFFAOYSA-N 9-methoxy-9-oxononanoic acid Chemical compound COC(=O)CCCCCCCC(O)=O VVWPSAPZUZXYCM-UHFFFAOYSA-N 0.000 description 2
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 2
- SOGAXMICEFXMKE-UHFFFAOYSA-N Butylmethacrylate Chemical compound CCCCOC(=O)C(C)=C SOGAXMICEFXMKE-UHFFFAOYSA-N 0.000 description 2
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 2
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 description 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- 125000002252 acyl group Chemical group 0.000 description 2
- 239000001361 adipic acid Substances 0.000 description 2
- 235000011037 adipic acid Nutrition 0.000 description 2
- 125000004429 atom Chemical group 0.000 description 2
- 229940067597 azelate Drugs 0.000 description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
- PXKLMJQFEQBVLD-UHFFFAOYSA-N bisphenol F Chemical compound C1=CC(O)=CC=C1CC1=CC=C(O)C=C1 PXKLMJQFEQBVLD-UHFFFAOYSA-N 0.000 description 2
- KEMMQQXISCWRIX-PAMPIZDHSA-N butane-1,4-diol (Z)-but-2-enedioic acid Chemical compound OCCCCO.OC(=O)\C=C/C(O)=O.OC(=O)\C=C/C(O)=O KEMMQQXISCWRIX-PAMPIZDHSA-N 0.000 description 2
- YWFUVTMPYOLBDB-UHFFFAOYSA-M butyl(chloro)tin;dihydrate Chemical compound O.O.CCCC[Sn]Cl YWFUVTMPYOLBDB-UHFFFAOYSA-M 0.000 description 2
- 239000011575 calcium Substances 0.000 description 2
- 239000004359 castor oil Chemical class 0.000 description 2
- 235000019438 castor oil Nutrition 0.000 description 2
- HGAZMNJKRQFZKS-UHFFFAOYSA-N chloroethene;ethenyl acetate Chemical compound ClC=C.CC(=O)OC=C HGAZMNJKRQFZKS-UHFFFAOYSA-N 0.000 description 2
- 239000003240 coconut oil Chemical class 0.000 description 2
- 235000019864 coconut oil Nutrition 0.000 description 2
- 235000012343 cottonseed oil Nutrition 0.000 description 2
- 239000002385 cottonseed oil Chemical class 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
- 150000002009 diols Chemical class 0.000 description 2
- POULHZVOKOAJMA-UHFFFAOYSA-N dodecanoic acid Chemical compound CCCCCCCCCCCC(O)=O POULHZVOKOAJMA-UHFFFAOYSA-N 0.000 description 2
- FJKIXWOMBXYWOQ-UHFFFAOYSA-N ethenoxyethane Chemical compound CCOC=C FJKIXWOMBXYWOQ-UHFFFAOYSA-N 0.000 description 2
- 229940093476 ethylene glycol Drugs 0.000 description 2
- XLYMOEINVGRTEX-UHFFFAOYSA-N fumaric acid monoethyl ester Natural products CCOC(=O)C=CC(O)=O XLYMOEINVGRTEX-UHFFFAOYSA-N 0.000 description 2
- ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Chemical class CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 description 2
- MNWFXJYAOYHMED-UHFFFAOYSA-N heptanoic acid Chemical compound CCCCCCC(O)=O MNWFXJYAOYHMED-UHFFFAOYSA-N 0.000 description 2
- IPCSVZSSVZVIGE-UHFFFAOYSA-N hexadecanoic acid Chemical compound CCCCCCCCCCCCCCCC(O)=O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 description 2
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 2
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- 239000000178 monomer Substances 0.000 description 2
- WWZKQHOCKIZLMA-UHFFFAOYSA-N octanoic acid Chemical compound CCCCCCCC(O)=O WWZKQHOCKIZLMA-UHFFFAOYSA-N 0.000 description 2
- 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 2
- 239000012044 organic layer Substances 0.000 description 2
- 235000006408 oxalic acid Nutrition 0.000 description 2
- LPNBBFKOUUSUDB-UHFFFAOYSA-N p-toluic acid Chemical compound CC1=CC=C(C(O)=O)C=C1 LPNBBFKOUUSUDB-UHFFFAOYSA-N 0.000 description 2
- WBHHMMIMDMUBKC-XLNAKTSKSA-N ricinelaidic acid Chemical compound CCCCCC[C@@H](O)C\C=C\CCCCCCCC(O)=O WBHHMMIMDMUBKC-XLNAKTSKSA-N 0.000 description 2
- 229940066675 ricinoleate Drugs 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- CXMXRPHRNRROMY-UHFFFAOYSA-N sebacic acid Chemical compound OC(=O)CCCCCCCCC(O)=O CXMXRPHRNRROMY-UHFFFAOYSA-N 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 229910052712 strontium Inorganic materials 0.000 description 2
- CIOAGBVUUVVLOB-UHFFFAOYSA-N strontium atom Chemical compound [Sr] CIOAGBVUUVVLOB-UHFFFAOYSA-N 0.000 description 2
- 239000003784 tall oil Substances 0.000 description 2
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 2
- LNJODFDQUBGMPB-UHFFFAOYSA-N (2-acetyloxy-3-sulfanylpropyl) acetate Chemical compound CC(=O)OCC(CS)OC(C)=O LNJODFDQUBGMPB-UHFFFAOYSA-N 0.000 description 1
- HQMGGACOVQNLQP-UHFFFAOYSA-N (2-octadecanoyloxy-3-sulfanylpropyl) octadecanoate Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCC(CS)OC(=O)CCCCCCCCCCCCCCCCC HQMGGACOVQNLQP-UHFFFAOYSA-N 0.000 description 1
- CTBVUIKPTXDELS-UHFFFAOYSA-N (2-octanoyloxy-3-sulfanylpropyl) octanoate Chemical compound CCCCCCCC(=O)OCC(CS)OC(=O)CCCCCCC CTBVUIKPTXDELS-UHFFFAOYSA-N 0.000 description 1
- OBETXYAYXDNJHR-SSDOTTSWSA-M (2r)-2-ethylhexanoate Chemical compound CCCC[C@@H](CC)C([O-])=O OBETXYAYXDNJHR-SSDOTTSWSA-M 0.000 description 1
- OYHQOLUKZRVURQ-NTGFUMLPSA-N (9Z,12Z)-9,10,12,13-tetratritiooctadeca-9,12-dienoic acid Chemical compound C(CCCCCCC\C(=C(/C\C(=C(/CCCCC)\[3H])\[3H])\[3H])\[3H])(=O)O OYHQOLUKZRVURQ-NTGFUMLPSA-N 0.000 description 1
- YSKIWPFLBFHYSA-BQYQJAHWSA-N (E)-2,3-bis(3-sulfanylpropyl)but-2-enedioic acid Chemical compound SCCC/C(C(=O)O)=C(/CCCS)C(O)=O YSKIWPFLBFHYSA-BQYQJAHWSA-N 0.000 description 1
- LEDJKFIAVLTWLG-OWOJBTEDSA-N (E)-4-oxo-4-(2-sulfanylethoxy)but-2-enoic acid Chemical compound OC(=O)\C=C\C(=O)OCCS LEDJKFIAVLTWLG-OWOJBTEDSA-N 0.000 description 1
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 1
- YOVSTVVTIBTBMW-KTKRTIGZSA-N (Z)-2,3-bis(4-sulfanylbutyl)but-2-enedioic acid Chemical compound SCCCC/C(C(=O)O)=C(\CCCCS)C(O)=O YOVSTVVTIBTBMW-KTKRTIGZSA-N 0.000 description 1
- KWZTYGPUVVZQSD-SPIKMXEPSA-N (Z)-but-2-enedioic acid decane-1,10-diol Chemical compound OC(=O)\C=C/C(O)=O.OC(=O)\C=C/C(O)=O.OCCCCCCCCCCO KWZTYGPUVVZQSD-SPIKMXEPSA-N 0.000 description 1
- MTKHTBWXSHYCGS-OWOJBTEDSA-N (e)-1-chloro-2-fluoroethene Chemical group F\C=C\Cl MTKHTBWXSHYCGS-OWOJBTEDSA-N 0.000 description 1
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- WGNAIPRQKMYVQT-UHFFFAOYSA-N hexanedioic acid propane-1,3-diol Chemical compound OCCCO.OC(=O)CCCCC(O)=O.OC(=O)CCCCC(O)=O WGNAIPRQKMYVQT-UHFFFAOYSA-N 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 229920001519 homopolymer Polymers 0.000 description 1
- 239000010514 hydrogenated cottonseed oil Chemical class 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- ONUFRYFLRFLSOM-UHFFFAOYSA-N lead;octadecanoic acid Chemical compound [Pb].CCCCCCCCCCCCCCCCCC(O)=O ONUFRYFLRFLSOM-UHFFFAOYSA-N 0.000 description 1
- 229940040452 linolenate Drugs 0.000 description 1
- 229960004488 linolenic acid Drugs 0.000 description 1
- KQQKGWQCNNTQJW-UHFFFAOYSA-N linolenic acid Natural products CC=CCCC=CCC=CCCCCCCCC(O)=O KQQKGWQCNNTQJW-UHFFFAOYSA-N 0.000 description 1
- 231100000053 low toxicity Toxicity 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- 150000002688 maleic acid derivatives Chemical class 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- AWJZTPWDQYFQPQ-UHFFFAOYSA-N methyl 2-chloroprop-2-enoate Chemical compound COC(=O)C(Cl)=C AWJZTPWDQYFQPQ-UHFFFAOYSA-N 0.000 description 1
- NKHAVTQWNUWKEO-IHWYPQMZSA-N methyl hydrogen fumarate Chemical compound COC(=O)\C=C/C(O)=O NKHAVTQWNUWKEO-IHWYPQMZSA-N 0.000 description 1
- WBYWAXJHAXSJNI-UHFFFAOYSA-N methyl p-hydroxycinnamate Natural products OC(=O)C=CC1=CC=CC=C1 WBYWAXJHAXSJNI-UHFFFAOYSA-N 0.000 description 1
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 1
- 238000003801 milling Methods 0.000 description 1
- 229940074369 monoethyl fumarate Drugs 0.000 description 1
- YWWHKOHZGJFMIE-UHFFFAOYSA-N monoethyl phthalate Chemical compound CCOC(=O)C1=CC=CC=C1C(O)=O YWWHKOHZGJFMIE-UHFFFAOYSA-N 0.000 description 1
- IBMRTYCHDPMBFN-UHFFFAOYSA-N monomethyl glutaric acid Chemical compound COC(=O)CCCC(O)=O IBMRTYCHDPMBFN-UHFFFAOYSA-N 0.000 description 1
- PJUIMOJAAPLTRJ-UHFFFAOYSA-N monothioglycerol Chemical compound OCC(O)CS PJUIMOJAAPLTRJ-UHFFFAOYSA-N 0.000 description 1
- WQEPLUUGTLDZJY-UHFFFAOYSA-N n-Pentadecanoic acid Natural products CCCCCCCCCCCCCCC(O)=O WQEPLUUGTLDZJY-UHFFFAOYSA-N 0.000 description 1
- RKISUIUJZGSLEV-UHFFFAOYSA-N n-[2-(octadecanoylamino)ethyl]octadecanamide Chemical compound CCCCCCCCCCCCCCCCCC(=O)NCCNC(=O)CCCCCCCCCCCCCCCCC RKISUIUJZGSLEV-UHFFFAOYSA-N 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- HNBDRPTVWVGKBR-UHFFFAOYSA-N n-pentanoic acid methyl ester Natural products CCCCC(=O)OC HNBDRPTVWVGKBR-UHFFFAOYSA-N 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 229920003052 natural elastomer Polymers 0.000 description 1
- 229920001194 natural rubber Polymers 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- ZWLPBLYKEWSWPD-UHFFFAOYSA-N o-toluic acid Chemical compound CC1=CC=CC=C1C(O)=O ZWLPBLYKEWSWPD-UHFFFAOYSA-N 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical class CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 1
- 229960002446 octanoic acid Drugs 0.000 description 1
- 229940049964 oleate Drugs 0.000 description 1
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 1
- 235000021313 oleic acid Nutrition 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 125000002524 organometallic group Chemical group 0.000 description 1
- 239000012188 paraffin wax Substances 0.000 description 1
- 239000000312 peanut oil Chemical class 0.000 description 1
- UCUUFSAXZMGPGH-UHFFFAOYSA-N penta-1,4-dien-3-one Chemical class C=CC(=O)C=C UCUUFSAXZMGPGH-UHFFFAOYSA-N 0.000 description 1
- 150000002976 peresters Chemical group 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 229940049953 phenylacetate Drugs 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- IUGYQRQAERSCNH-UHFFFAOYSA-N pivalic acid Chemical compound CC(C)(C)C(O)=O IUGYQRQAERSCNH-UHFFFAOYSA-N 0.000 description 1
- 239000004999 plastisol Substances 0.000 description 1
- 229920002620 polyvinyl fluoride Polymers 0.000 description 1
- 239000005033 polyvinylidene chloride Substances 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 229960003656 ricinoleic acid Drugs 0.000 description 1
- FEUQNCSVHBHROZ-UHFFFAOYSA-N ricinoleic acid Natural products CCCCCCC(O[Si](C)(C)C)CC=CCCCCCCCC(=O)OC FEUQNCSVHBHROZ-UHFFFAOYSA-N 0.000 description 1
- 238000005070 sampling Methods 0.000 description 1
- 229940116351 sebacate Drugs 0.000 description 1
- CXMXRPHRNRROMY-UHFFFAOYSA-L sebacate(2-) Chemical compound [O-]C(=O)CCCCCCCCC([O-])=O CXMXRPHRNRROMY-UHFFFAOYSA-L 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 101150035983 str1 gene Proteins 0.000 description 1
- JNCLGRVLJCCIMN-UHFFFAOYSA-L strontium;2-nonylphenolate Chemical compound [Sr+2].CCCCCCCCCC1=CC=CC=C1[O-].CCCCCCCCCC1=CC=CC=C1[O-] JNCLGRVLJCCIMN-UHFFFAOYSA-L 0.000 description 1
- JLPVTWQGBPMCLM-UHFFFAOYSA-L strontium;2-octylphenolate Chemical compound [Sr+2].CCCCCCCCC1=CC=CC=C1[O-].CCCCCCCCC1=CC=CC=C1[O-] JLPVTWQGBPMCLM-UHFFFAOYSA-L 0.000 description 1
- PAYWWSFIERYQOC-UHFFFAOYSA-L strontium;2-pentylphenolate Chemical compound [Sr+2].CCCCCC1=CC=CC=C1[O-].CCCCCC1=CC=CC=C1[O-] PAYWWSFIERYQOC-UHFFFAOYSA-L 0.000 description 1
- 125000004434 sulfur atom Chemical group 0.000 description 1
- 150000003464 sulfur compounds Chemical class 0.000 description 1
- 229920003051 synthetic elastomer Polymers 0.000 description 1
- 239000005061 synthetic rubber Substances 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- TUNFSRHWOTWDNC-HKGQFRNVSA-N tetradecanoic acid Chemical compound CCCCCCCCCCCCC[14C](O)=O TUNFSRHWOTWDNC-HKGQFRNVSA-N 0.000 description 1
- 229940071127 thioglycolate Drugs 0.000 description 1
- CWERGRDVMFNCDR-UHFFFAOYSA-M thioglycolate(1-) Chemical compound [O-]C(=O)CS CWERGRDVMFNCDR-UHFFFAOYSA-M 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- LDHQCZJRKDOVOX-UHFFFAOYSA-N trans-crotonic acid Natural products CC=CC(O)=O LDHQCZJRKDOVOX-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
- MEBRQLCKPRKBOH-UHFFFAOYSA-K trichloro(ethyl)stannane Chemical compound CC[Sn](Cl)(Cl)Cl MEBRQLCKPRKBOH-UHFFFAOYSA-K 0.000 description 1
- INTLMJZQCBRQAT-UHFFFAOYSA-K trichloro(octyl)stannane Chemical compound CCCCCCCC[Sn](Cl)(Cl)Cl INTLMJZQCBRQAT-UHFFFAOYSA-K 0.000 description 1
- UBOXGVDOUJQMTN-UHFFFAOYSA-N trichloroethylene Natural products ClCC(Cl)Cl UBOXGVDOUJQMTN-UHFFFAOYSA-N 0.000 description 1
- SBNYZUTZEUZATG-UHFFFAOYSA-K triiodo(methyl)stannane Chemical compound C[Sn](I)(I)I SBNYZUTZEUZATG-UHFFFAOYSA-K 0.000 description 1
- 238000009827 uniform distribution Methods 0.000 description 1
- 229940005605 valeric acid Drugs 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 229940117958 vinyl acetate Drugs 0.000 description 1
- KOZCZZVUFDCZGG-UHFFFAOYSA-N vinyl benzoate Chemical compound C=COC(=O)C1=CC=CC=C1 KOZCZZVUFDCZGG-UHFFFAOYSA-N 0.000 description 1
- FUSUHKVFWTUUBE-UHFFFAOYSA-N vinyl methyl ketone Natural products CC(=O)C=C FUSUHKVFWTUUBE-UHFFFAOYSA-N 0.000 description 1
- 239000008096 xylene Chemical class 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 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
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
- C08K5/58—Organo-tin compounds containing sulfur
-
- 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
Definitions
- the present invention relates to novel sulfur containing organotin compounds useful as stabilizers for polyvinyl chloride and other halogen containing polymers.
- organotin compounds having (1) at least two tin atoms linked by a bridge through sulfur, carboxylate groups or both, said bridge also containing at least two carbon atoms, (2) directly attached to the tin atoms one to two alkyl groups containing one to eight carbon atoms and (3) a mercaptoalkanol or derivative thereof directly attached to at least one of the tin atoms through the sulfur atom.
- the bridges can be described as consisting of --S ⁇ S--, ##STR1## and no other functions, e.g. there are no bis oxide, alcoholate or phenate groups in the bridge.
- the nature of the bridge is inconsequential so long as it contains at least two carbon atoms in the chain.
- the requisite chain carbon atoms may or may not include the carboxylate carbon atom or atoms.
- Z is any divalent organic radical which together with Q contains at least two carbon atoms, i.e. if both Q groups are --S-- then Z must have at least two carbon atoms, if one Q is ##STR4## then Z must contain at least one carbon atoms and if both Q groups are ##STR5## then Z may be zero (although Z can also contain one or more carbon atoms in this case also);
- R is alkyl of 1 to 8 carbon atoms
- x is 1 or 2 and the two x's can be the same or different.
- R 1 can be alkylene, arylene or substituted alkylene or arylene (preferably R 1 is unsubstituted alkylene or arylene),
- the compounds have the formula: ##STR6## where R is a monovalent alkyl radical of 1 to 8 carbon atoms, A is ##STR7## X where X is halogen of atomic weight 35 to 127, i.e., chlorine, bromine or iodine, ##STR8## with the proviso that at least one ##STR9## is in the molecule, d is 0 or 1, each R' when d is 0 is alkylene of 1 to 10 carbon atoms; each R' when d is 1 is alkylene of 2 to 10 carbon atoms, each R" when d is 1 is alkyl of 1 to 20, preferably 1 to 18, carbon atoms, ethylenically unsaturated aliphatic hydrocarbyl having 1 to 3 ethylenic double bonds and 2 to 19, preferably 2 to 17, carbon atoms, halo or hydroxy alkyl or alkenyl of 2 to 19, preferably 2 to 17 carbon atoms,
- R" when d is 0 is hydrogen, alkyl of 1 to 20, preferably 1 to 18 carbon atoms, ethylenically unsaturated aliphatic hydrocarbyl having 1 to 3 ethylenic double bonds and 2 to 19, preferably 2 to 18 carbon atoms, cycloalkyl of 5 to 6 carbon atoms, benzyl, phenyl or halophenyl, e.g., fluorophenyl, bromophenyl or chlorophenyl, x is 1 or 2, y is 1 or 2 and z is 1 or 2, the total
- phenylene or ##STR13## where t is 0 to 1 and R 11 and R 12 are hydrogen or alkyl, preferably t is 1 and R 11 and R 12 are both methyl, and compounds prepared by reacting a dialkytin oxide or alkyl stannoic acid with a compound of the formula. ##STR14##
- the grouping ##STR15## can be formed by reacting two moles of mercaptoethanol and one mole of maleic acid.
- the grouping ##STR16## can be formed by reacting two moles of thioglycolic acid or beta thiopropionic acid with one mole of a diol, e.g. ethylene glycol, diethylene glycol, propylene glycol, decamethylene glycol.
- the grouping ##STR17## can be formed by reacting two moles of a dicarboxylic acid, e.g. maleic acid, oxalic acid, succinic acid, adipic acid, terephthalic acid with one mole of a dihydric phenol, e.g. hydroquinone or a bisphenol, e.g. 4,4'-dihydroxydiphenyl, p,p'-diphenylolpropane (bisphenol A), bis (4-hydroxyphenyl) methane, etc.
- the compounds are useful to stabilize halogen containing vinyl and vinylidene resins, e.g. polyvinyl chloride.
- R examples of groups within R are methyl, ethyl, propyl, isopropyl, n-butyl, isobutyl, sec. butyl, t-butyl, amyl, hexyl, octyl, 2-ethylhexyl and isoctyl. Most preferably R is methyl.
- subgroups within R are (a) methyl and butyl and (b) methyl, butyl and octyl.
- R' (and also of R 6 ) groups are methylene, ethylene, propylene, trimethylene, tetramethylene, pentamethylene, octamethylene, hexamethylene, decamethylene, p-phenylene and m-phenylene.
- R 4 are the same as those mentioned for R' except that methylene is omitted.
- R 5 are nothing, methylene, ethylene, trimethylene, propylene, tetramethylene, pentamethylene, hexamethylene, octamethylene, --CH ⁇ CH-- (either cis or trans).
- the compounds of the present invention can be made in various ways such as those illustrated below, for example.
- the tin is added as the monoalkyltin trihalide, e.g., methyltin trichloride, methyltin tribromide, methyltin triiodide, ethyltin trichloride, sec. butyltin trichloride, butyltin tribromide or octyltin trichloride, the dialkyltin dihalide, e.g., dimethyltin dichloride, dimethyltin dibromide, dimethyltin diiodide, dipropyltin dichloride.
- the dialkyltin dihalide e.g., dimethyltin dichloride, dimethyltin dibromide, dimethyltin diiodide, dipropyltin dichloride.
- the amount of tin present as trimethyltin compound impurity should be less than 0.5%.
- mixtures of acids can be used, e.g., tall oil acids, palmitic acid-stearic acid mixtures ranging from 60:40 to 40:60; soybean oil acids, cottonseed oil acids, hydrogenated cottonseed oil acids, peanut oil acids, coconut oil acids, corn oil acids, castor oil acids, hydrogenated castor oil acids, lard acids, etc.
- sulfur compounds employed include thioalkanols such as 2-mercaptoethanol, 3-mercaptopropanol, 4-mercaptobutanol, 3-mercaptobutanol, 5-mercaptopentanol, 10-mercaptodecanol.
- Additional starting compounds of the formula ##STR20## include monothioglycerine dicaprylate, monothioglycerine diacetate, monothioglycerine distearate, monothioglycerine dioleate, monothioglycerine dilinoleate.
- the Z linkage in the compounds except when Z is --O-- can be formed by reacting a compound of the formula HZH with a compound of the formula: ##STR21## where Hal is a halogen, e.g., chlorine, bromide or iodine.
- Examples of compounds having the formula HZH are mercaptoethylmercaptopropionate, mercaptoethylthioglycolate, 3-mercaptopropylthioglycolate, 3-mercaptopropyl mercaptopropionate, mercaptoethylmercapto-butyrate, mercaptoethyl mercaptodecanoate, 10-mercaptodecylthioglycolate, 4-mercaptobutylmercaptopropionate, mercaptoethylthioglycolic acid mercaptoethyl ester, mercaptopropyl-thioglycolic acid mercaptoethyl ester, mercaptoethylthiogylcolic acid, mercaptopropyl ester, mercaptoethylmercaptopropionic acid mercaptoethyl ester, mercaptopropylmercaptopropionic acid mercapto
- the products of the invention can be prepared by reacting either an alkyl halotin dihydroxide, e.g., methyl chlorotin dihydroxide, butyl chlorotin dihydroxide, octylchlorotin dihydroxide, methyl bromotin dihydroxide or an alkyl stannoic acid, e.g., methyl stannoic acid, butylstannoic acid, octylstannoic acid with a compound of the formula: ##STR22##
- an alkyl stannoic acid e.g., methyl stannoic acid, butylstannoic acid, octylstannoic acid
- overbased product has the same uses as the other products of the invention. It is particularly surprising that overbased products can be made with dimethyltin oxide since while it is not soluble in many other materials, it is soluble in the compounds of the invention.
- the reaction can be carried out at a wide range of temperatures, e.g., room temperature to 100° C. usually at 25°-50° C.
- the reaction is usually carried out with water as a solvent, regardless of the procedure employed.
- water immiscible organic solvents e.g., aliphatic and aromatic hydrocarbons, e.g., hexane, octane, benzene, toluene, xylene, aliphatic carboxylic Acid esters, e.g., butyl acetate, propyl propionate, methyl valerate.
- the proportions of solvent are not critical and can vary widely.
- the refractive indices (R.I.) were measured at 25° C. unless otherwise indicated.
- Example 1 The procedure of Example 1 was followed replacing the bis(2-mercaptoethyl)adipate with 42 gm (0.25 mole) of mercaptoethylmercaptopropionate. Obtained is 295 gm of a pale yellow oil, bis(methyltin bis[2-mercaptoethylcaprylate])mercaptoethylmercaptopropionate, .[.D 25 .]. .Iadd.n D 25 .Iaddend. 1.5352.
- Example 1 The procedure of Example 1 was followed replacing the bis(2-mercaptoethyl)adipate with 59 gm (0.25 mole) of bis(2-mercaptoethyl)maleate. Obtained is 302 gm of a pale yellow oil, bis(methyl-tin bis[2-mercaptoethylcaprylate]mercaptoethyl) maleate. n D 25 1.5389.
- Example 2 The procedure of Example 1 was followed replacing the bis(2-mercaptoethyl)adipate with 52 gm (0.25 mole) of glycol bis(thioglycolate). Obtained is 299 gms of a nearly colorless oil, n D 25 1.5193.
- the product includes: ##STR25##
- Example 2 The procedure of Example 1 was followed replacing the bis(2-mercaptoethyl)adipate with 23 gm (0.25 mole) of thioglycolic acid. Obtained is 273 gms of a colorless oil n D 25 1.5404.
- the product includes: ##STR26##
- Example 2 The procedure of Example 1 was followed replacing the bis(2-mercaptoethyl)adipate with 29 gm (0.25 mole) of maleic acid. Obtained is 276 gm of yellow oil. n D 25 1.5371.
- the product includes: ##STR27##
- Example 2 The procedure of Example 1 was followed replacing the bis(2-mercaptoethyl)adipate with 41.5 gm (0.25 mole) 2-mercaptoethyl maleate. Obtained are 287 gms of a pale yellow oil, n D 25 1.5384.
- the product includes: ##STR31##
- Example 1 The procedure of Example 1 was followed replacing the 2-mercaptoethylcaprylate with 330 gm (1.0 mole) of 2-mercaptoethyloctadecylether. Obtained is 441 gm of a nearly colorless oil, containing bis(methyltin bis[2-mercaptoethyloctadecylether]-mercaptoethyl)adipate. n D 25 1.5149.
- Example 1 The procedure of Example 1 as followed replacing the 2-mercaptoethylcaprylate with 360 gm (0.0 mole) of monothioglycerine dicaprylate ester. Obtained is 458 gm of a yellow oil, containing bis(methyltin bis[thioglycerinedicaprylate]-2-mercapto-ethyl)adipate. n D 25 1.5160.
- Example 2 The procedure of Example 1 was followed replacing the bis(2-mercaptoethyl)adipate with 23.5 gm (0.25 mole) ethanedithiol. Obtained is 269 mg of a very odoriferous pale yellow oil, n D 25 1.5272 containing: ##STR32##
- Example 1 The procedure of Example 1 was followed replacing the 2-mercaptoethylcaprylate with 260 gm (1.0 mole) of 6-mercaptohexylcaprylate. Obtained is 366 gm of a pale yellow oil, n D 25 1.5202, mainly bis(methyltin bis[6-mercaptohexylcaprylate]-2-mercaptoethyl)adipate.
- Example 1 The procedure of Example 1 was followed replacing the bis(2-mercaptoethyl)adipate with 71.5 gm (0.25 mole) of tetramethylene glycol bis maleate. Obtained is 314 gm of a pale yellow oil. n D 25 1.5349, containing ##STR33##
- Example 9 The procedure of Example 9 was followed replacing the bis(2-mercaptoethyl)adipate with 38 gm (0.25 mole) of mercaptoethylthioglycolate. Obtained is 342 gm of a pale yellow oil, n D 25 1.5161, containing: ##STR34##
- Example 1 The procedure of Example 1 was followed replacing the monomethyltintrichloride with 141 gm (0.5 mole) of butyltintrichloride. Obtained is 330 gm of a pale yellow oil.
- the product is mainly bis(butyltin bis[2-mercaptoethyl caprylate]-2-mercaptoethyl)-adipate, n D 25 1.5210.
- Example 7 The procedure of Example 7 was followed replacing the methyltintrichloride with 141 gm (0.5 mole) of butyltintrichloride and the bis(2-mercaptoethyl)adipate with 59 gm (0.25 mole) of bis(2-mercaptoethyl)-maleate. Obtained is 280 gm of a nearly colorless oil, n D 25 1.5420, containing: ##STR36##
- Example 9 The procedure of Example 9 was followed, replacing the dimethyltindichloride with 75.5 gm (0.25 mole) of dibutyltindichloride, the methyltintrichloride with 70.5 gm (0.25 mole) of butyltintrichloride. Obtained is 402 gms of a yellow oil, n D 25 1.5077, containing: ##STR37##
- Example 1 The procedure of Example 1 was followed replacing the bis(2-mercaptoethyl) adipate with 41.5 g (0.25 mole) of terephthalic acid. Obtained is 286 gm of yellow oil. n D 25 1.5488. The product is in part ##STR40##
- Example 9 The procedure of Example 9 was followed replacing the bis(2-mercaptoethyl) adipate with 105 g (0.25 mole) of reaction product of bis phenol A 118 gms (0.5 mole) and 116 gms (1.0 mole) maleic acid. Obtained is 421 gm of amber oil. n D 25 1.5286.
- the reaction product contains ##STR41##
- the stabilizers of the present invention can be used with halogen-containing vinyl and vinylidene polymers, e.g., resins in which the halogen is attached directly to the carbon atoms.
- the polymer is a vinyl halide polymer, specifically a vinyl chloride polymer.
- the vinyl chloride polymer is made from monomers consisting of vinyl chloride alone or a mixture of monomers comprising at least 70% vinyl chloride by weight.
- vinyl chloride copolymers are stabilized, preferably the copolymer of vinyl chloride with an ethylenically unsaturated compound copolymerizable therewith contains at least 10% of polymerized vinyl chloride.
- chlorinated polyethylene having 14 to 75%, e.g., 27% chloride by weight, chlorinated natural and synthetic rubber, rubber hydrochloride, chlorinated polystyrene, chlorinated polyvinyl chloride, polyvinyl chloride, polyvinylidene chloride, polyvinyl bromide, polyvinyl fluoride, copolymers of vinyl chloride with 1 to 90%, preferably 1 to 30% of a copolymerizable ethylenically unsaturated material such as vinyl acetate, vinyl butyrate, vinyl benzoate, vinylidene, chloride, diethyl fumarate, diethyl maleate, other alkyl fumarates and maleates, vinyl propionate, methyl acrylate, 2-ethylhexylacrylate, butyl acrylate and other alkyl acrylates, methyl methacrylate, ethyl methacrylate, butyl methacrylate and other
- Typical copolymers include vinyl chloride-vinyl acetate (96:4 sold commercially as VYNW), vinyl chloride-vinylacetate (87:13), vinyl chloride-vinyl acetate-maleic anhydride (86:13:1), vinyl chloride-vinylidene chloride (95:5), vinyl chloride-diethyl fumarate (95:5), vinyl chloride-trichloroethylene (95:5), vinyl chloride-2-ethylhexyl acrylate (80:20).
- the stabilizers of the present invention can be incorporated with the polymer by admixing in an appropriate mill or mixer of by any of the other well-known methods which provide for uniform distribution throughout the polymer composition.
- mixing can be accomplished by milling on rolls at 100°-160° C.
- novel stabilizers there can also be incorporated with the resin, conventional additives such as plasticizers, pigments, fillers, dyes, ultraviolet light absorbing agents, densifying agents and the like.
- conventional additives such as plasticizers, pigments, fillers, dyes, ultraviolet light absorbing agents, densifying agents and the like.
- conventional and known tin stabilizers e.g., those disclosed in Kauder or Kugele et al or in Weisfeld U.S. Pat. No. 3,640,950, Leistner U.S. Pat. Nos. 2,870,119 and 2,870,182, Best U.S. Pat. No. 2,731,484, Stefl U.S. Pat. No. 2,731,482, and Mack U.S. Pat. No. 2,914,506, for example.
- the entire disclosures of all the patents mentioned in this paragraph are hereby incorporated by reference.
- plasticizer it is used in conventional amount, e.g., 10 to 150 parts per 100 parts of polymer.
- Typical plasticizers are di-2-ethylhexyl phthalate, dibutyl sebacate, dioctyl sebacate, tricresyl phosphate.
- the tin containing stabilizers of the invention are normally used in an amount of 0.01 to 10% by weight of the polymer, more preferably 0.2 to 5% of the tin compound is used by weight of the polymer.
- halogen containing polymer of a metal salt stabilizer there can also be incorporated 0.1 to 10 parts per 100 parts of the halogen containing polymer of a metal salt stabilizer.
- a metal salt stabilizer there can be used barium, strontium, calcium, cadmium, zinc, lead, tin, magnesium, cobalt, nickel, titanium and aluminum salts of phenols, aromatic carboxylic acids, fatty acids or epoxy fatty acids.
- Suitable salts include barium di(nonylphenolate), strontium di(nonylphenolate), strontium di(amylphenolate), barium di(octylphenolate), strontium di(octylphenolate), barium di(nonyl-o-cresolate), lead di(octylphenolate), cadmium-2-ethyl hexoate, cadmium laurate, cadmium stearate, zinc caprylate, cadmium caprate, barium stearate, barium-2-ethylhexoate, barium laurate, barium ricinoleate, lead stearate, aluminum stearate, magnesium stearate, calcium octoate, calcium stearate, cadmium naphthenate, cadmium benzoate, cadmium p-tert. butylbenzoate, barium octyl salicylate, cadmium epoxy
- plastisol formulations there is preferably also included from 0.1 to 10 parts per 100 parts of polymer of an epoxy vegetable oil such as epoxidized soybean oil or epoxidized tall oil, epoxy esters of fatty acids, e.g., isooctyl epoxystearate.
- an epoxy vegetable oil such as epoxidized soybean oil or epoxidized tall oil
- epoxy esters of fatty acids e.g., isooctyl epoxystearate.
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Abstract
Description
TABLE 1 __________________________________________________________________________ Tin Dynamic Mill Stability Product of Contained 380° F. 30/40 RPM(minutes) Example No. (mg) 1 2 3 4 5 6 7 8 9 10 __________________________________________________________________________ 1 40 10 10 9 7+ 6 5 4 2 2 2 2 40 10 9+ 9 8 6 5 4 3 1 1 3 40 10+ 10+ 10 9 8 7+ 5 3 2 2 5 40 9 8 7 5 4 3 3 2 2 1 7 40 9 8+ 8 7 6 5 4 3 2 1 8 40 8+ 8 7 6 5 4 4 3 2 2 9 40 10 10 9+ 8+ 7 6 5+ 4 3 2 * 40 9 8 7 6 5 5 4 2 2 2 __________________________________________________________________________ Color Scale: 10(white)-5(tanorange)-0(burn) *1/8 monomethyltin tris(isooctylthioglycolate) and 2/3 dimethyltin bis(isooctylthioglycolate)
Claims (20)
- 2. A compound according to claim 1 having formula (1). 3. A compound according to claim 2 wherein x and z are 1 and y is 2. 4. A compound according to claim 3 wherein one A attached to each tin atom is halogen of atomic weight 35 to 127, and the other A is ##STR50##
- 5. A compound according to claim 3 wherein all of the A groups are ##STR51##
- 6. A compound according to claim 2 wherein d is 0. 7. A compound according to claim 6 wherein x and z are 1 and y is 2. 8. A compound according to claim 2 wherein, z is 1 and the A groups are ##STR52##
- or halogen of atomic weight 35 to 127. 9. A compound according to claim 8 wherein Z is ##STR53##
- 10. A compound according to claim 9 wherein R" is alkyl or ethylenically unsaturated aliphatic hydrocarbyl. 11. A compound according to claim 10 wherein R4 is alkylene. 12. A compound according to claim 10 wherein R4 is p-phenylene. 13. A compound according to claim 10 wherein R4 is --CH═CH--. 14. A compound according to claim 8 wherein Z is ##STR54##
- 15. A compound according to claim 14 wherein R4 and R6 are both alkylene. 16. A compound according to claim 14 wherein R4 and R6 are both --CH═CH--. 17. A compound according to claim 14 wherein R4 and R6 are both ##STR55##
- 18. A compound according to claim 14 wherein R" is alkyl or ethylenically unsaturated aliphatic hydrocarbyl. 19. A compound according to claim 8 wherein Z is ##STR56##
- 20. A compound according to claim 8 wherein Z is ##STR57##
- 21. A compound according to claim 20 wherein R" is alkyl or ethylenically unsaturated aliphatic hydrocarbyl. 22. A compound according to claim 8 wherein Z is ##STR58##
- 23. A compound according to claim 22 wherein R" is alkyl or ethylenically unsaturated aliphatic hydrocarbyl. 24. A compound according to claim 23 wherein R5 is nothing or alkylene. 25. A compound according to claim 23 wherein R5 is --CH═CH--. 26. A compound according to claim 23 wherein R5 is phenylene. 27. A compound according to claim 8 wherein Z is ##STR59##
- 28. A compound according to claim 27 wherein R" is alkyl or ethylenically unsaturated aliphatic hydrocarbyl. 29. A compound according to claim 8 wherein Z is ##STR60##
- 30. A compound according to claim 29 wherein R" is alkyl or ethylenically unsaturated aliphatic hydrocarbyl. 31. A compound according to claim 8 wherein Z is ##STR61##
- 32. A compound according to claim 31 wherein R" is alkyl or ethylenically unsaturated aliphatic hydrocarbyl. 33. A compound according to claim 8 wherein Z is ##STR62##
- .Badd.where n is 2.Baddend.. .Badd..[..[.34. A compound according to claim 33 wherein n is 2..]..]..Baddend. 35. .[..[.A compound according to claim 8 wherein Z is ##STR63## .Badd.A sulfur containing organotin compound having the formula ##STR64##.Baddend. where R is a monovalent alkyl radical of 1 to 8 carbon atoms, each R' is alkylene of 2 to 10 carbon atoms each R" is alkyl of 1 to 20 carbon atoms, ethylenically unsaturated aliphatic hydrocarbyl having 1 to 3 ethylenic double bonds and 2 to 19 carbon atoms, halo or hydroxy alkyl of 2 to 19 carbon atoms, halo or hydroxyl alkenyl of 2 to 19 carbon atoms, cycloalkyl of 5 to 6 carbon atoms, benzyl, phenyl, alkylphenyl, halophenyl, ##STR65## where R'" is alkylene of 2 to 10 carbon atoms, R'"" is alkyl of 1 to 20 carbon atoms, alkenyl of 2 to 18 carbon atoms, halo of hydroxy alkyl or alkenyl of 2 to 18 carbon atoms, cycloalkyl of 5 to 6 carbon atoms, benzyl, phenyl or halophenyl, x is 1 or 2, y is 1 or 2 and the total of x+y is 3, R8 is alkylene of 2 to 10 carbon atoms or cyclohexane dimethylene, n is 1 or 2 or (2) an overbased compound prepared by reacting a dialkyltin oxide of alkylstannoic acid with a compound of the formula ##STR66##
- .36. A compound according to claim 35 wherein n is 1. 37. A compound according to claim 35 wherein R8 is alkylene of 2 to 10 carbon atoms. 38. A compound according to claim 8 wherein Z is ##STR67##
- 39. A compound according to claim 38 wherein R9 is (CH2)m where m is an integer from 0 to 8. 40. A compound according to claim 38 wherein R9 is --CH═CH--. 41. A compound according to claim 38 wherein R9 is ##STR68##
- 42. A compound according to claim 38 where R10 is ##STR69##
- 43. A compound according to claim .Badd..[.2.]..Baddend. .Iadd.42 .Iaddend.wherein R11 and R12 are methyl. 44. A compound according to claim 43 wherein R9 is (CH2)m where m is an integer of 0 to 8, --CH═CH--or phenylene. 45. A compound according to claim 2 wherein d is 1 and R" is alkyl, ethylenically unsaturated aliphatic hydrocarbyl or monohydroxy substituted monoethylenically unsaturated aliphatic hydrocarbyl. 46. A compound according to claim 45 wherein at least one of the A groups is ##STR70## and the balance of the A groups are ##STR71##
- or halogen of atomic weight 35 to 127. 47. A compound according to claim 46 wherein all of the A groups are ##STR72##
- 48. A compound according to claim 46 wherein at least one A group is halogen of atomic weight 35 to 127. 49. A compound according to claim 48 wherein the halogen is chlorine. 50. A compound according to claim 1 which is (2). 51. A compound according to claim 50 wherein R is methyl. 52. A compound according to claim 45 wherein R is methyl. 53. A compound according to claim 2 wherein R is methyl. 54. A halogen-containing polymer composition containing a compound according to claim 1 in an amount effective to heat stabilize the polymer. 55. A composition according to claim 54 wherein the halogen containing polymer is selected from the group consisting of vinyl chloride polymers, chlorinated polyethylene, chlorinated rubber, chlorinated polystyrene, chlorinated polyvinyl chloride and rubber hydrochloride.
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
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US06/141,912 USRE30810E (en) | 1974-11-15 | 1980-04-21 | Carbofunctional sulfur and carboxylate bridged tin compounds |
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US05/524,271 US3979359A (en) | 1974-11-15 | 1974-11-15 | Carbofunctional sulfur and carboxylate bridged tin compounds |
US05/940,450 USRE30032E (en) | 1974-11-15 | 1978-09-07 | Carbofunctional sulfur and carboxylate bridged tin compounds |
US06/141,912 USRE30810E (en) | 1974-11-15 | 1980-04-21 | Carbofunctional sulfur and carboxylate bridged tin compounds |
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US05/940,450 Reissue USRE30032E (en) | 1974-11-15 | 1978-09-07 | Carbofunctional sulfur and carboxylate bridged tin compounds |
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Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0129264A2 (en) * | 1983-05-18 | 1984-12-27 | Akzo N.V. | Organotin-containing composition for the stabilization of polymers or copolymers of vinyl chloride |
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EP0129264A2 (en) * | 1983-05-18 | 1984-12-27 | Akzo N.V. | Organotin-containing composition for the stabilization of polymers or copolymers of vinyl chloride |
EP0129264A3 (en) * | 1983-05-18 | 1985-04-10 | Akzo N.V. | Organotin-containing composition for the stabilization of polymers or copolymers of vinyl chloride |
US4546136A (en) | 1983-05-18 | 1985-10-08 | Akzo N.V. | Organotin-containing composition for the stabilization of polymers of vinyl chloride |
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