GB748228A - Organic derivatives of tetravalent tin and compositions containing the same - Google Patents
Organic derivatives of tetravalent tin and compositions containing the sameInfo
- Publication number
- GB748228A GB748228A GB14189/53A GB1418953A GB748228A GB 748228 A GB748228 A GB 748228A GB 14189/53 A GB14189/53 A GB 14189/53A GB 1418953 A GB1418953 A GB 1418953A GB 748228 A GB748228 A GB 748228A
- Authority
- GB
- United Kingdom
- Prior art keywords
- tin
- diester
- acid
- linked
- atom
- 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
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 title abstract 6
- 239000000203 mixture Substances 0.000 title abstract 5
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 abstract 11
- -1 aralkyl radicals Chemical class 0.000 abstract 11
- 229910052718 tin Inorganic materials 0.000 abstract 9
- 150000005690 diesters Chemical class 0.000 abstract 7
- 125000004432 carbon atom Chemical group C* 0.000 abstract 5
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 abstract 4
- HDFRDWFLWVCOGP-UHFFFAOYSA-N carbonothioic O,S-acid Chemical compound OC(S)=O HDFRDWFLWVCOGP-UHFFFAOYSA-N 0.000 abstract 4
- 150000001875 compounds Chemical class 0.000 abstract 4
- JGFBRKRYDCGYKD-UHFFFAOYSA-N dibutyl(oxo)tin Chemical compound CCCC[Sn](=O)CCCC JGFBRKRYDCGYKD-UHFFFAOYSA-N 0.000 abstract 4
- CWERGRDVMFNCDR-UHFFFAOYSA-N thioglycolic acid Chemical compound OC(=O)CS CWERGRDVMFNCDR-UHFFFAOYSA-N 0.000 abstract 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 abstract 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 abstract 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 abstract 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 abstract 3
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 abstract 3
- BZHJMEDXRYGGRV-UHFFFAOYSA-N Vinyl chloride Chemical compound ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 abstract 3
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 abstract 3
- 239000007795 chemical reaction product Substances 0.000 abstract 3
- 229910052801 chlorine Inorganic materials 0.000 abstract 3
- 239000000460 chlorine Substances 0.000 abstract 3
- 229920001577 copolymer Polymers 0.000 abstract 3
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 abstract 3
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 abstract 2
- 125000000217 alkyl group Chemical group 0.000 abstract 2
- KZKQGUVWZYKJBN-UHFFFAOYSA-N methyl 5-methylsulfonylpyridine-3-carboxylate Chemical compound COC(=O)C1=CN=CC(S(C)(=O)=O)=C1 KZKQGUVWZYKJBN-UHFFFAOYSA-N 0.000 abstract 2
- 150000003254 radicals Chemical class 0.000 abstract 2
- 239000000376 reactant Substances 0.000 abstract 2
- 239000003381 stabilizer Substances 0.000 abstract 2
- 229910001887 tin oxide Inorganic materials 0.000 abstract 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 abstract 1
- SLRMQYXOBQWXCR-UHFFFAOYSA-N 2154-56-5 Chemical compound [CH2]C1=CC=CC=C1 SLRMQYXOBQWXCR-UHFFFAOYSA-N 0.000 abstract 1
- MQIUGAXCHLFZKX-UHFFFAOYSA-N Di-n-octyl phthalate Natural products CCCCCCCCOC(=O)C1=CC=CC=C1C(=O)OCCCCCCCC MQIUGAXCHLFZKX-UHFFFAOYSA-N 0.000 abstract 1
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 abstract 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 abstract 1
- 239000005977 Ethylene Substances 0.000 abstract 1
- YSMRWXYRXBRSND-UHFFFAOYSA-N TOTP Chemical compound CC1=CC=CC=C1OP(=O)(OC=1C(=CC=CC=1)C)OC1=CC=CC=C1C YSMRWXYRXBRSND-UHFFFAOYSA-N 0.000 abstract 1
- 239000003963 antioxidant agent Substances 0.000 abstract 1
- BJQHLKABXJIVAM-UHFFFAOYSA-N bis(2-ethylhexyl) phthalate Chemical compound CCCCC(CC)COC(=O)C1=CC=CC=C1C(=O)OCC(CC)CCCC BJQHLKABXJIVAM-UHFFFAOYSA-N 0.000 abstract 1
- DGAODIKUWGRDBO-UHFFFAOYSA-N butanethioic s-acid Chemical compound CCCC(O)=S DGAODIKUWGRDBO-UHFFFAOYSA-N 0.000 abstract 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 abstract 1
- 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 abstract 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 abstract 1
- 150000002334 glycols Chemical class 0.000 abstract 1
- 238000010438 heat treatment Methods 0.000 abstract 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 1
- 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 abstract 1
- 150000002894 organic compounds Chemical class 0.000 abstract 1
- 229920000915 polyvinyl chloride Polymers 0.000 abstract 1
- KOODSCBKXPPKHE-UHFFFAOYSA-N propanethioic s-acid Chemical compound CCC(S)=O KOODSCBKXPPKHE-UHFFFAOYSA-N 0.000 abstract 1
- 230000000087 stabilizing effect Effects 0.000 abstract 1
- 229920003002 synthetic resin Polymers 0.000 abstract 1
- 239000000057 synthetic resin Substances 0.000 abstract 1
Classifications
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Compositions Of Macromolecular Compounds (AREA)
Abstract
A resinous composition comprises a chlorine containing synthetic resin, e.g. a chlorine containing polyvinyl resin or a copolymer of vinyl chloride with vinyl acetate, vinylidene chloride or styrene, and as a stabilizer an organo-tin compound wherein 2 or 3 valences of the tin atom are linked to alkyl or aralkyl radicals and each remaining valence is linked to a sulphur atom of a radical of a diester derived from a mercapto carboxylic acid having from 2 to 4 carbon atoms and a glycol containing from 2 to 6 carbon atoms and obtained by reacting said diester with the required triorgano-tin monohalide, diorgano-tin dihalide or diorgano-tin oxide, the quantities of reactants being chosen so that both sulphur atoms of the diester residue are linked to a tin atom. In the examples, compositions are prepared containing a copolymer of vinyl chloride with vinyl acetate, dioctylphthalate and th reaction product of 1,2-propylene glycol thioglycolic acid diester with di-n-butyl-tin oxide having the formula <FORM:0748228/IV(a)/1> and a copolymer of vinyl chloride with vinyl acetate, commercial tricresyl phosphate and the reaction product of 1,4-butanediol thiopropionic acid diester with tribenzyl-tin chloride having the formula (C6H5CH2-)3Sn-(SCH2CH2COO CH2CH2CH2CH2OOCCH2CH2S) - Sn(- CH2C6H5)3 the said composition being soluble in a mixture of toluene and methyl ethyl ketone.ALSO:The invention comprises organo-tin compounds, wherein 2 or 3 valences of the tin atom are linked to alkyl or aralkyl radicals and each remaining valence of the tin atom is linked to a sulphur atom of a radical of a diester, said diester being formed from a mercapto-carboxylic acid having from 2 to 4 carbon atoms and a glycol containing from 2 to 6 carbon atoms, obtained by heating said glycol with the said mercapto-carboxylic acid to form the diester which is then reacted with the required triorgano-tin monohalide, di-organo tin dihalide or di-organo tin oxide, e.g. at an elevated temperature, the quantities of the reactants being chosen so that both sulphur atoms of the diester residue are linked to a tin atom. The alkyl radicals may be methyl, ethyl, butyl, octyl, dodecyl or octadecyl radicals, and a suitable aralkyl radical is the benzyl radical. Glycols mentioned are ethylene and 1,2-propylene glycol, and 1,4 - butanediol. Mercaptocarboxylic acids mentioned are thioglycollic, thiopropionic and thiobutyric acid. In the examples the following compounds are prepared :- <FORM:0748228/IV(a)/1> from the 1,2-propylene glycol diester with thioglycollic acid and di-n-butyl tin oxide, <FORM:0748228/IV(a)/2> from the ethylene glycol diester with thioglycollic acid and di-n-butyl tin oxide, and <FORM:0748228/IV(a)/3> from the 1,4-butanediol diester with b -thiopropionic acid and tribenzyl tin chloride. The Specification also states that when dibutyl tin oxide is reacted with the ethylene glycol diester of thioglycollic acid, the reaction product may contain a compound of the formula <FORM:0748228/IV(a)/4> in addition to the compound referred to in the examples. The organo-tin compounds may be used as antioxidants and are useful for stabilizing chlorine containing organic compounds, e.g. chlorinated paraffins having from 10 to 40 carbon atoms per molecule. A suitable quantity of stabilizer is 0.1 to 10 per cent by weight based on the compound to be stabilized.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US748228XA | 1952-05-23 | 1952-05-23 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB748228A true GB748228A (en) | 1956-04-25 |
Family
ID=22121890
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB14189/53A Expired GB748228A (en) | 1952-05-23 | 1953-05-20 | Organic derivatives of tetravalent tin and compositions containing the same |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB748228A (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3115509A (en) * | 1958-10-23 | 1963-12-24 | M & T Chemicals Inc | Chemical product and process |
| US7767740B2 (en) | 2005-05-05 | 2010-08-03 | Galata Chemicals, Llc | Alkyltin sulfanyl mercaptocarboxylates having terminal thiol groups |
-
1953
- 1953-05-20 GB GB14189/53A patent/GB748228A/en not_active Expired
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3115509A (en) * | 1958-10-23 | 1963-12-24 | M & T Chemicals Inc | Chemical product and process |
| US7767740B2 (en) | 2005-05-05 | 2010-08-03 | Galata Chemicals, Llc | Alkyltin sulfanyl mercaptocarboxylates having terminal thiol groups |
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