GB1008845A - Polymer stabilizer and polymer composition stabilized therewith - Google Patents
Polymer stabilizer and polymer composition stabilized therewithInfo
- Publication number
- GB1008845A GB1008845A GB19002A GB1900262A GB1008845A GB 1008845 A GB1008845 A GB 1008845A GB 19002 A GB19002 A GB 19002A GB 1900262 A GB1900262 A GB 1900262A GB 1008845 A GB1008845 A GB 1008845A
- Authority
- GB
- United Kingdom
- Prior art keywords
- acid
- group
- mercapto
- esters
- compound
- 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
- 239000000203 mixture Substances 0.000 title abstract 3
- 229920000642 polymer Polymers 0.000 title abstract 3
- 239000003381 stabilizer Substances 0.000 title abstract 2
- 150000001875 compounds Chemical class 0.000 abstract 10
- -1 mercapto compound Chemical class 0.000 abstract 10
- 239000002253 acid Substances 0.000 abstract 7
- 125000003118 aryl group Chemical group 0.000 abstract 6
- 150000002148 esters Chemical class 0.000 abstract 6
- 125000002723 alicyclic group Chemical group 0.000 abstract 5
- 125000001931 aliphatic group Chemical group 0.000 abstract 5
- PXQLVRUNWNTZOS-UHFFFAOYSA-N sulfanyl Chemical class [SH] PXQLVRUNWNTZOS-UHFFFAOYSA-N 0.000 abstract 4
- 229920001577 copolymer Polymers 0.000 abstract 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 abstract 3
- BGFHMYJZJZLMHW-UHFFFAOYSA-N 4-[2-[[2-(1-benzothiophen-3-yl)-9-propan-2-ylpurin-6-yl]amino]ethyl]phenol Chemical group N1=C(C=2C3=CC=CC=C3SC=2)N=C2N(C(C)C)C=NC2=C1NCCC1=CC=C(O)C=C1 BGFHMYJZJZLMHW-UHFFFAOYSA-N 0.000 abstract 2
- 239000004215 Carbon black (E152) Substances 0.000 abstract 2
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 abstract 2
- LSDPWZHWYPCBBB-UHFFFAOYSA-N Methanethiol Chemical compound SC LSDPWZHWYPCBBB-UHFFFAOYSA-N 0.000 abstract 2
- 125000000217 alkyl group Chemical group 0.000 abstract 2
- 125000004432 carbon atom Chemical group C* 0.000 abstract 2
- 229930195733 hydrocarbon Natural products 0.000 abstract 2
- 229910052739 hydrogen Inorganic materials 0.000 abstract 2
- 239000001257 hydrogen Substances 0.000 abstract 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 2
- 239000000178 monomer Substances 0.000 abstract 2
- 229920000915 polyvinyl chloride Polymers 0.000 abstract 2
- 239000004800 polyvinyl chloride Substances 0.000 abstract 2
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 abstract 2
- QFIBRXURBRPXDR-UHFFFAOYSA-N 2-(2-phenoxyethoxy)ethanethiol Chemical compound SCCOCCOC1=CC=CC=C1 QFIBRXURBRPXDR-UHFFFAOYSA-N 0.000 abstract 1
- OEPOKWHJYJXUGD-UHFFFAOYSA-N 2-(3-phenylmethoxyphenyl)-1,3-thiazole-4-carbaldehyde Chemical compound O=CC1=CSC(C=2C=C(OCC=3C=CC=CC=3)C=CC=2)=N1 OEPOKWHJYJXUGD-UHFFFAOYSA-N 0.000 abstract 1
- VSZSIEBALNXIFG-UHFFFAOYSA-N 2-hydroxyethyl 2,2-bis(sulfanyl)acetate Chemical compound OCCOC(=O)C(S)S VSZSIEBALNXIFG-UHFFFAOYSA-N 0.000 abstract 1
- WGZWXVFLOUVQLH-UHFFFAOYSA-N 2-phenoxyethanethiol Chemical compound SCCOC1=CC=CC=C1 WGZWXVFLOUVQLH-UHFFFAOYSA-N 0.000 abstract 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 abstract 1
- 125000006539 C12 alkyl 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
- 239000004801 Chlorinated PVC Substances 0.000 abstract 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 abstract 1
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical class S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 abstract 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 abstract 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 1
- 239000004698 Polyethylene Substances 0.000 abstract 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 abstract 1
- NQHAZTDQFIYTQD-UHFFFAOYSA-N SOS Chemical class SOS NQHAZTDQFIYTQD-UHFFFAOYSA-N 0.000 abstract 1
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 abstract 1
- BZHJMEDXRYGGRV-UHFFFAOYSA-N Vinyl chloride Chemical compound ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 abstract 1
- 150000007513 acids Chemical class 0.000 abstract 1
- 150000001298 alcohols Chemical class 0.000 abstract 1
- 150000004703 alkoxides Chemical class 0.000 abstract 1
- 125000002877 alkyl aryl group Chemical group 0.000 abstract 1
- UIJGNTRUPZPVNG-UHFFFAOYSA-N benzenecarbothioic s-acid Chemical compound SC(=O)C1=CC=CC=C1 UIJGNTRUPZPVNG-UHFFFAOYSA-N 0.000 abstract 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 abstract 1
- UENWRTRMUIOCKN-UHFFFAOYSA-N benzyl thiol Chemical compound SCC1=CC=CC=C1 UENWRTRMUIOCKN-UHFFFAOYSA-N 0.000 abstract 1
- 230000015572 biosynthetic process Effects 0.000 abstract 1
- 150000007942 carboxylates Chemical group 0.000 abstract 1
- 229920000457 chlorinated polyvinyl chloride Polymers 0.000 abstract 1
- 239000000460 chlorine Substances 0.000 abstract 1
- 229910052801 chlorine Inorganic materials 0.000 abstract 1
- HNEGQIOMVPPMNR-IHWYPQMZSA-N citraconic acid Chemical class OC(=O)C(/C)=C\C(O)=O HNEGQIOMVPPMNR-IHWYPQMZSA-N 0.000 abstract 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 abstract 1
- 125000002704 decyl 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])* 0.000 abstract 1
- 150000001991 dicarboxylic acids Chemical class 0.000 abstract 1
- 235000014113 dietary fatty acids Nutrition 0.000 abstract 1
- WNAHIZMDSQCWRP-UHFFFAOYSA-N dodecane-1-thiol Chemical compound CCCCCCCCCCCCS WNAHIZMDSQCWRP-UHFFFAOYSA-N 0.000 abstract 1
- 229920001971 elastomer Polymers 0.000 abstract 1
- 239000000194 fatty acid Substances 0.000 abstract 1
- 229930195729 fatty acid Natural products 0.000 abstract 1
- 150000004665 fatty acids Chemical class 0.000 abstract 1
- 239000001530 fumaric acid Substances 0.000 abstract 1
- 150000004820 halides Chemical class 0.000 abstract 1
- 229920006158 high molecular weight polymer Polymers 0.000 abstract 1
- 125000001183 hydrocarbyl group Chemical group 0.000 abstract 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 abstract 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 abstract 1
- 239000011976 maleic acid Substances 0.000 abstract 1
- 150000002762 monocarboxylic acid derivatives Chemical class 0.000 abstract 1
- 150000002763 monocarboxylic acids Chemical class 0.000 abstract 1
- PJUIMOJAAPLTRJ-UHFFFAOYSA-N monothioglycerol Chemical compound OCC(O)CS PJUIMOJAAPLTRJ-UHFFFAOYSA-N 0.000 abstract 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 1
- 229920002857 polybutadiene Polymers 0.000 abstract 1
- 229920000573 polyethylene Polymers 0.000 abstract 1
- 229920006395 saturated elastomer Polymers 0.000 abstract 1
- YODZTKMDCQEPHD-UHFFFAOYSA-N thiodiglycol Chemical compound OCCSCCO YODZTKMDCQEPHD-UHFFFAOYSA-N 0.000 abstract 1
- 229940035024 thioglycerol Drugs 0.000 abstract 1
- CWERGRDVMFNCDR-UHFFFAOYSA-N thioglycolic acid Chemical compound OC(=O)CS CWERGRDVMFNCDR-UHFFFAOYSA-N 0.000 abstract 1
- 150000003606 tin compounds Chemical class 0.000 abstract 1
- 229910001887 tin oxide Inorganic materials 0.000 abstract 1
- QHGNHLZPVBIIPX-UHFFFAOYSA-N tin(ii) oxide Chemical class [Sn]=O QHGNHLZPVBIIPX-UHFFFAOYSA-N 0.000 abstract 1
- 125000003944 tolyl group Chemical group 0.000 abstract 1
- DGVVWUTYPXICAM-UHFFFAOYSA-N β‐Mercaptoethanol Chemical compound OCCS DGVVWUTYPXICAM-UHFFFAOYSA-N 0.000 abstract 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
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/22—Tin compounds
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Compositions Of Macromolecular Compounds (AREA)
Abstract
A stabilizer for high molecular weight polymers of ethylenically unsaturated monomers including chlorine-containing monomers comprises at least one of each of the compounds of the general formulae:- <FORM:1008845/C3/1> <FORM:1008845/C3/2> <FORM:1008845/C3/3> in admixture of from 40% to 70% by weight of (I), from 15% to 30% by weight of (II), and from 15% to 30% by weight of (III), wherein R is an aliphatic, aromatic or alicyclic group, SR1 is the residue of a mercapto compound, R2 is a monovalent hydrocarbon radical, each of the groups R3 and R4 is hydrogen or methyl, and R5 is an alkyl, aryl or alicyclic group (see Division C2). Polymers specified are polyvinyl chloride, copolymers of polyvinyl chloride and vinyl acetate, copolymers of vinyl chloride and vinylidene chloride, rubber hydrochloride and post-chlorinated polyvinyl chloride, polyethylene, polypropylene, ethylene-propylene co-polymers, propylene-butylene co-polymers and all cis-1 : 4-polybutadienes.ALSO:A mixture of compounds of the general formulaae <FORM:1008845/C2/1> <FORM:1008845/C2/2> <FORM:1008845/C2/3> is prepared by reacting in amounts which theoretically would give rise to a mixture of from 40 to 70%, preferably 60%, by weight of a compound or compounds of the general formula (I), from 15 to 30%, preferably 20% by weight of a compound or compounds of the general formula (II), and from 15 to 30%, preferably 20% by weight of a compound or compounds of the general formula (III), one or more diorgano tin oxides, halides or alkoxides with: (A) one or more mercaptans, mercaptides, mercapto alcohols, mercapto ethers, esters of a mercapto alcohol, esters of a mercapto acid and/or one or more thiolic acids; (B) one or more monocarboxylic acids, and (C) one or more monoesters of an unsaturated dicarboxylic acid; wherein R is an aliphatic, aromatic or alicyclic group, SR1 is the residue of a Group (A) compound, R2 is a monovalent hydrocarbon radical, R3 and R4 are each hydrogen or methyl, and R5 is an alkyl, aryl or alicyclic group. The diorganolin compound is preferably a dihydrocarbon tin compound; the hydrocarbon groups may be a C3 to C12 alkyl group, allyl, benzyl, phenyl, tolyl or cyclohexyl group. The mercaptan is preferably an aliphatic mercaptan having from 8 to 18 carbon atoms, e.g. decyl or dodecyl mercaptan. Aromatic mercaptans may also be used in the formation of the group SR1, e.g. thionapthol, thiobenzyl alcohol, phenoxy ethyl mercaptan, and phenoxyethoxyethyl mercaptan. Suitable mercapto alcohols are monothioethyleneglycol, monothiopropylene glycol, thioglycerol and thiodiethylene glycol, and esters of these alcohols in which the hydroxyl groups are esterified by an aliphatic, aromatic or alicyclic saturated or unsaturated monocarboxylic acid, e.g. thioglycol-2-ethyl hexoic acid ester. Mercapto acid esters are suitably the esters of thioglycollic acid, and generally the esters of mono- and di-basic aliphatic and aromatic mercapto acids. The two groups SR1 may together constitute the residue of an ethylene glycol diester of a mercapto acid, e.g. ethylene glycol dimercaptoacetate. A particularly suitable thioic acid is thiobenzoic acid. The group R2COO- may constitute the residue of a fatty acid, preferably having from 7 to 30, especially 10 to 30, carbon atoms. This group may also be the residue of an aryl or alkaryl carbonxylic acid. The group O2CCR3=CR4COOR5 may be constituted by an a ,b -unsaturated carboxylate group, e.g. mono-esters of maleic acid, fumaric acid, mesaconic and citraconic acids.
Priority Applications (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| NL134429D NL134429C (en) | 1962-05-17 | ||
| NL292845D NL292845A (en) | 1962-05-17 | ||
| GB19002A GB1008845A (en) | 1962-05-17 | 1962-05-17 | Polymer stabilizer and polymer composition stabilized therewith |
| DES85221A DE1226578B (en) | 1962-05-17 | 1963-05-15 | Process for the production of stabilizers for polyvinyl chloride and its copolymers |
| FR935276A FR1359490A (en) | 1962-05-17 | 1963-05-17 | Stabilizer for high polymers |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB19002A GB1008845A (en) | 1962-05-17 | 1962-05-17 | Polymer stabilizer and polymer composition stabilized therewith |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1008845A true GB1008845A (en) | 1965-11-03 |
Family
ID=10122102
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB19002A Expired GB1008845A (en) | 1962-05-17 | 1962-05-17 | Polymer stabilizer and polymer composition stabilized therewith |
Country Status (3)
| Country | Link |
|---|---|
| DE (1) | DE1226578B (en) |
| GB (1) | GB1008845A (en) |
| NL (2) | NL292845A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0015241A1 (en) * | 1979-02-22 | 1980-09-03 | Ciba-Geigy Ag | Mixtures consisting of an organo-tin alcoholate and an organo-tin mercaptide; their use as stabilizers for chlorinated polymers |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4988750A (en) * | 1981-07-17 | 1991-01-29 | Schering Ag | Non-toxic stabilizer for halogenated polymer |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1020333B (en) * | 1952-05-14 | 1957-12-05 | Argus Chemical Lab Inc | Process for the production of new organotin compounds |
| DE1020334B (en) * | 1952-05-14 | 1957-12-05 | Argus Chemical Lab Inc | Process for the production of new organotin compounds |
| GB740397A (en) * | 1952-05-20 | 1955-11-09 | Argus Chemical Lab Inc | Organic derivatives of tetravalent tin and compositions containing the same |
| DE1020335B (en) * | 1952-05-23 | 1957-12-05 | Argus Chemical Lab Inc | Process for the production of new organotin compounds |
| DE1020337B (en) * | 1952-09-08 | 1957-12-05 | Argus Chemical Lab Inc | Process for the production of new organotin compounds |
| DE1020338B (en) * | 1952-10-16 | 1957-12-05 | Argus Chemical Lab Inc | Process for the production of new organotin compounds |
| DE1020331B (en) * | 1953-01-02 | 1957-12-05 | Advance Produktion G M B H Deu | Process for the production of new organotin compounds |
| DE1020332B (en) * | 1953-05-09 | 1957-12-05 | Argus Chemical Lab Inc | Process for the production of new organotin compounds |
-
0
- NL NL134429D patent/NL134429C/xx active
- NL NL292845D patent/NL292845A/xx unknown
-
1962
- 1962-05-17 GB GB19002A patent/GB1008845A/en not_active Expired
-
1963
- 1963-05-15 DE DES85221A patent/DE1226578B/en active Pending
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0015241A1 (en) * | 1979-02-22 | 1980-09-03 | Ciba-Geigy Ag | Mixtures consisting of an organo-tin alcoholate and an organo-tin mercaptide; their use as stabilizers for chlorinated polymers |
| US4611012A (en) * | 1979-02-22 | 1986-09-09 | Ciba-Geigy Corporation | Mixtures of organo-tin compounds |
| US4698368A (en) * | 1979-02-22 | 1987-10-06 | Ciba-Geigy Corporation | Mixtures of organo-tin compounds |
Also Published As
| Publication number | Publication date |
|---|---|
| NL292845A (en) | |
| DE1226578B (en) | 1966-10-13 |
| NL134429C (en) |
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