GB743304A - Tin compounds linked to esters of mercapto alcohols with dibasic acids and resins stabilized therewith - Google Patents
Tin compounds linked to esters of mercapto alcohols with dibasic acids and resins stabilized therewithInfo
- Publication number
- GB743304A GB743304A GB28511/53A GB2851153A GB743304A GB 743304 A GB743304 A GB 743304A GB 28511/53 A GB28511/53 A GB 28511/53A GB 2851153 A GB2851153 A GB 2851153A GB 743304 A GB743304 A GB 743304A
- Authority
- GB
- United Kingdom
- Prior art keywords
- mercapto
- carbon atoms
- organo
- acid
- tin
- 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
- 239000002253 acid Substances 0.000 title abstract 3
- 150000002148 esters Chemical class 0.000 title abstract 3
- 150000007513 acids Chemical class 0.000 title 1
- -1 mercapto alcohols Chemical class 0.000 title 1
- 229920005989 resin Polymers 0.000 title 1
- 239000011347 resin Substances 0.000 title 1
- 150000003606 tin compounds Chemical class 0.000 title 1
- 125000004432 carbon atom Chemical group C* 0.000 abstract 8
- 239000000203 mixture Substances 0.000 abstract 5
- RVEZZJVBDQCTEF-UHFFFAOYSA-N sulfenic acid Chemical compound SO RVEZZJVBDQCTEF-UHFFFAOYSA-N 0.000 abstract 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 abstract 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 abstract 3
- 150000001875 compounds Chemical class 0.000 abstract 3
- 229920001577 copolymer Polymers 0.000 abstract 3
- 150000005690 diesters Chemical class 0.000 abstract 3
- 239000003381 stabilizer Substances 0.000 abstract 3
- NEJMTSWXTZREOC-UHFFFAOYSA-N 4-sulfanylbutan-1-ol Chemical compound OCCCCS NEJMTSWXTZREOC-UHFFFAOYSA-N 0.000 abstract 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 abstract 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 abstract 2
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 abstract 2
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 abstract 2
- BZHJMEDXRYGGRV-UHFFFAOYSA-N Vinyl chloride Chemical compound ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 abstract 2
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 abstract 2
- 125000000217 alkyl group Chemical group 0.000 abstract 2
- 125000003118 aryl group Chemical group 0.000 abstract 2
- 150000001732 carboxylic acid derivatives Chemical class 0.000 abstract 2
- 229910052801 chlorine Inorganic materials 0.000 abstract 2
- 239000000460 chlorine Substances 0.000 abstract 2
- DNJIEGIFACGWOD-UHFFFAOYSA-N ethyl mercaptane Natural products CCS DNJIEGIFACGWOD-UHFFFAOYSA-N 0.000 abstract 2
- BDJRBEYXGGNYIS-UHFFFAOYSA-N nonanedioic acid Chemical compound OC(=O)CCCCCCCC(O)=O BDJRBEYXGGNYIS-UHFFFAOYSA-N 0.000 abstract 2
- DGVVWUTYPXICAM-UHFFFAOYSA-N β‐Mercaptoethanol Chemical compound OCCS DGVVWUTYPXICAM-UHFFFAOYSA-N 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
- MQIUGAXCHLFZKX-UHFFFAOYSA-N Di-n-octyl phthalate Natural products CCCCCCCCOC(=O)C1=CC=CC=C1C(=O)OCCCCCCCC MQIUGAXCHLFZKX-UHFFFAOYSA-N 0.000 abstract 1
- QMSJINZXKWISNT-UHFFFAOYSA-N SC(C)O.C1(=CC=C(C=C1)S(=O)(=O)O)C Chemical compound SC(C)O.C1(=CC=C(C=C1)S(=O)(=O)O)C QMSJINZXKWISNT-UHFFFAOYSA-N 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
- 235000011037 adipic acid Nutrition 0.000 abstract 1
- 239000001361 adipic acid Substances 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
- 125000004185 ester group Chemical group 0.000 abstract 1
- 150000004820 halides Chemical class 0.000 abstract 1
- 238000010438 heat treatment Methods 0.000 abstract 1
- 150000002894 organic compounds Chemical class 0.000 abstract 1
- 150000002896 organic halogen compounds Chemical class 0.000 abstract 1
- 239000012188 paraffin wax Substances 0.000 abstract 1
- 229920000915 polyvinyl chloride Polymers 0.000 abstract 1
- 238000002360 preparation method Methods 0.000 abstract 1
- 238000010992 reflux Methods 0.000 abstract 1
- 229910001887 tin oxide Inorganic materials 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)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Resinous compositions comprise a chlorine containing polyvinyl resin or a copolymer of vinyl chloride with vinyl acetate, vinylidene chloride or styrene and as a stabilizer an organotin compound of the general formula <FORM:0743304/IV(a)/1> wherein R represents an alkyl, aryl or hydroaromatic radical and -SXS- represents the residue of a diester formed from a mercaptoalcohol having 2 to 4 carbon atoms and a dibasic carboxylic acid-preferably an acid containing from 6 to 12 carbon atoms. In the examples (1) a composition is prepared containing a copolymer of vinyl chloride with vinyl acetate, dioctyl phthalate and an organo-tin compound of the formula <FORM:0743304/IV(a)/2> (2) a composition is prepared containing a similar copolymer, commercial tricresyl phosphate and an organo-tin compound of the formula <FORM:0743304/IV(a)/3> and the mixture may be dissolved in a mixture of toluene and methyl ethyl ketone.ALSO:The invention comprises organo-tin compounds of the general formulae <FORM:0743304/IV(a)/1> wherein R represents an alkyl, aryl or hydroaromatic radical and -SXS- represents the residue of a diester formed from a mercaptoalcohol having 2 to 4 carbon atoms and a dibasic carboxylic acid-preferably an acid containing from 6 to 12 carbon atoms, and the preparation thereof by esterifying a dibasic carboxylic acid with a mercapto-alcohol containing 2 to 4 carbon atoms and reacting the diester formed with the required organo-tin halide, organo-tin oxide or organo-stannonic acid-preferably by heating. The ester group may be derived from mercapto ethanol or 4-mercapto-n-butanol. In the examples compounds of the following formulae are prepared: <FORM:0743304/IV(a)/2> <FORM:0743304/IV(a)/3> The organo-tin compounds may be used as antioxidants and as stabilizers for halogenated organic compounds, e.g. a chlorine containing organic compound such as a chlorinated paraffin having from 10 to 40 carbon atoms. A suitable quantity of stabilizer that may be used is from 0.1 to 10 per cent based on the weight of the compound to be stabilized. Mercapto-substituted esters are prepared by esterifying a dibasic carboxylic acid, preferably one containing from 6 to 12 carbon atoms, with a mercapto-alcohol containing from 2 to 4 carbon atoms. In the examples esters are prepared by refluxing in the presence of p-toluene-sulphonic acid mercapto-ethanol and adipic acid, 4-mercapto-n-butanol and azelaic acid, and mercapto-ethanol and terephthalic acid.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US743304XA | 1952-10-16 | 1952-10-16 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB743304A true GB743304A (en) | 1956-01-11 |
Family
ID=22118981
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB28511/53A Expired GB743304A (en) | 1952-10-16 | 1953-10-15 | Tin compounds linked to esters of mercapto alcohols with dibasic acids and resins stabilized therewith |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB743304A (en) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1126604B (en) * | 1958-03-19 | 1962-03-29 | Inst Chemie Und Technologie De | Molding compound based on polyvinyl chloride, stabilized against the effects of heat and light |
| CN102558608A (en) * | 2010-12-27 | 2012-07-11 | 泰安市蓝天助剂有限公司 | Sebacic acid mercapto ethyl ester dimethyl tin heat stabilizing agent and preparation method thereof |
| WO2013064444A1 (en) | 2011-11-02 | 2013-05-10 | Versalis S.P.A | Compositions based on self-extinguishing expandable vinyl aromatic polymers |
| CN104710334A (en) * | 2013-12-13 | 2015-06-17 | 湖北南星化工总厂 | Metal thiolate compound for PVC stabilization and preparation method thereof |
-
1953
- 1953-10-15 GB GB28511/53A patent/GB743304A/en not_active Expired
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1126604B (en) * | 1958-03-19 | 1962-03-29 | Inst Chemie Und Technologie De | Molding compound based on polyvinyl chloride, stabilized against the effects of heat and light |
| CN102558608A (en) * | 2010-12-27 | 2012-07-11 | 泰安市蓝天助剂有限公司 | Sebacic acid mercapto ethyl ester dimethyl tin heat stabilizing agent and preparation method thereof |
| WO2013064444A1 (en) | 2011-11-02 | 2013-05-10 | Versalis S.P.A | Compositions based on self-extinguishing expandable vinyl aromatic polymers |
| CN104710334A (en) * | 2013-12-13 | 2015-06-17 | 湖北南星化工总厂 | Metal thiolate compound for PVC stabilization and preparation method thereof |
| CN104710334B (en) * | 2013-12-13 | 2017-01-25 | 湖北南星化工总厂 | Metal thiolate compound for PVC stabilization and preparation method thereof |
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