GB815839A - Process for making copolymers of monovinylbenzene compounds and unsaturated alkydresins - Google Patents
Process for making copolymers of monovinylbenzene compounds and unsaturated alkydresinsInfo
- Publication number
- GB815839A GB815839A GB3417256A GB3417256A GB815839A GB 815839 A GB815839 A GB 815839A GB 3417256 A GB3417256 A GB 3417256A GB 3417256 A GB3417256 A GB 3417256A GB 815839 A GB815839 A GB 815839A
- Authority
- GB
- United Kingdom
- Prior art keywords
- diisocyanate
- glycol
- per cent
- ethylene
- polyesters
- 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
- PPBRXRYQALVLMV-UHFFFAOYSA-N styrene Chemical class C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 title abstract 3
- 229920000180 Alkyd Polymers 0.000 title 1
- 229920001577 copolymer Polymers 0.000 title 1
- 229920000728 polyester Polymers 0.000 abstract 7
- 239000000203 mixture Substances 0.000 abstract 4
- 150000001991 dicarboxylic acids Chemical class 0.000 abstract 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 abstract 3
- 239000002253 acid Substances 0.000 abstract 2
- 230000001808 coupling Effects 0.000 abstract 2
- 238000010168 coupling process Methods 0.000 abstract 2
- 238000005859 coupling reaction Methods 0.000 abstract 2
- 239000000463 material Substances 0.000 abstract 2
- VNMOIBZLSJDQEO-UHFFFAOYSA-N 1,10-diisocyanatodecane Chemical compound O=C=NCCCCCCCCCCN=C=O VNMOIBZLSJDQEO-UHFFFAOYSA-N 0.000 abstract 1
- ZTNJGMFHJYGMDR-UHFFFAOYSA-N 1,2-diisocyanatoethane Chemical compound O=C=NCCN=C=O ZTNJGMFHJYGMDR-UHFFFAOYSA-N 0.000 abstract 1
- YPFDHNVEDLHUCE-UHFFFAOYSA-N 1,3-Propanediol Chemical compound OCCCO YPFDHNVEDLHUCE-UHFFFAOYSA-N 0.000 abstract 1
- IKYNWXNXXHWHLL-UHFFFAOYSA-N 1,3-diisocyanatopropane Chemical compound O=C=NCCCN=C=O IKYNWXNXXHWHLL-UHFFFAOYSA-N 0.000 abstract 1
- OVBFMUAFNIIQAL-UHFFFAOYSA-N 1,4-diisocyanatobutane Chemical compound O=C=NCCCCN=C=O OVBFMUAFNIIQAL-UHFFFAOYSA-N 0.000 abstract 1
- MGYMHQJELJYRQS-UHFFFAOYSA-N 1,4-epidioxy-p-menth-2-ene Chemical compound C1CC2(C)OOC1(C(C)C)C=C2 MGYMHQJELJYRQS-UHFFFAOYSA-N 0.000 abstract 1
- SBJCUZQNHOLYMD-UHFFFAOYSA-N 1,5-Naphthalene diisocyanate Chemical compound C1=CC=C2C(N=C=O)=CC=CC2=C1N=C=O SBJCUZQNHOLYMD-UHFFFAOYSA-N 0.000 abstract 1
- XXMIOPMDWAUFGU-UHFFFAOYSA-N 1,6-Hexanediol Chemical compound OCCCCCCO XXMIOPMDWAUFGU-UHFFFAOYSA-N 0.000 abstract 1
- KTZVZZJJVJQZHV-UHFFFAOYSA-N 1-chloro-4-ethenylbenzene Chemical compound ClC1=CC=C(C=C)C=C1 KTZVZZJJVJQZHV-UHFFFAOYSA-N 0.000 abstract 1
- OEVVKKAVYQFQNV-UHFFFAOYSA-N 1-ethenyl-2,4-dimethylbenzene Chemical compound CC1=CC=C(C=C)C(C)=C1 OEVVKKAVYQFQNV-UHFFFAOYSA-N 0.000 abstract 1
- JZHGRUMIRATHIU-UHFFFAOYSA-N 1-ethenyl-3-methylbenzene Chemical compound CC1=CC=CC(C=C)=C1 JZHGRUMIRATHIU-UHFFFAOYSA-N 0.000 abstract 1
- WHFHDVDXYKOSKI-UHFFFAOYSA-N 1-ethenyl-4-ethylbenzene Chemical compound CCC1=CC=C(C=C)C=C1 WHFHDVDXYKOSKI-UHFFFAOYSA-N 0.000 abstract 1
- JLBJTVDPSNHSKJ-UHFFFAOYSA-N 1-ethenyl-4-methylbenzene Chemical compound CC1=CC=C(C=C)C=C1 JLBJTVDPSNHSKJ-UHFFFAOYSA-N 0.000 abstract 1
- QQHQTCGEZWTSEJ-UHFFFAOYSA-N 1-ethenyl-4-propan-2-ylbenzene Chemical compound CC(C)C1=CC=C(C=C)C=C1 QQHQTCGEZWTSEJ-UHFFFAOYSA-N 0.000 abstract 1
- ULQISTXYYBZJSJ-UHFFFAOYSA-N 12-hydroxyoctadecanoic acid Chemical compound CCCCCCC(O)CCCCCCCCCCC(O)=O ULQISTXYYBZJSJ-UHFFFAOYSA-N 0.000 abstract 1
- 229940114072 12-hydroxystearic acid Drugs 0.000 abstract 1
- QPYKYDBKQYZEKG-UHFFFAOYSA-N 2,2-dimethylpropane-1,1-diol Chemical compound CC(C)(C)C(O)O QPYKYDBKQYZEKG-UHFFFAOYSA-N 0.000 abstract 1
- OMNYXCUDBQKCMU-UHFFFAOYSA-N 2,4-dichloro-1-ethenylbenzene Chemical compound ClC1=CC=C(C=C)C(Cl)=C1 OMNYXCUDBQKCMU-UHFFFAOYSA-N 0.000 abstract 1
- SZSWKGVWJBZNIH-UHFFFAOYSA-N 2-chloro-1-ethenyl-4-methylbenzene Chemical compound CC1=CC=C(C=C)C(Cl)=C1 SZSWKGVWJBZNIH-UHFFFAOYSA-N 0.000 abstract 1
- 239000004342 Benzoyl peroxide Substances 0.000 abstract 1
- VOVDIJKEHCRTNT-UHFFFAOYSA-N C(=O)=C(C(C)=O)CCCCCCC(C(C)=O)=C=O Chemical compound C(=O)=C(C(C)=O)CCCCCCC(C(C)=O)=C=O VOVDIJKEHCRTNT-UHFFFAOYSA-N 0.000 abstract 1
- KXUYLLDUGZHIOI-UHFFFAOYSA-N CC(=C=O)CCCCCCC(=C=O)C Chemical compound CC(=C=O)CCCCCCC(=C=O)C KXUYLLDUGZHIOI-UHFFFAOYSA-N 0.000 abstract 1
- GNEVIACKFGQMHB-UHFFFAOYSA-N Carbon suboxide Chemical compound O=C=C=C=O GNEVIACKFGQMHB-UHFFFAOYSA-N 0.000 abstract 1
- YQHLDYVWEZKEOX-UHFFFAOYSA-N Cumene hydroperoxide Chemical compound OOC(C)(C)C1=CC=CC=C1 YQHLDYVWEZKEOX-UHFFFAOYSA-N 0.000 abstract 1
- LSXWFXONGKSEMY-UHFFFAOYSA-N Di-tert-butyl peroxide Chemical compound CC(C)(C)OOC(C)(C)C LSXWFXONGKSEMY-UHFFFAOYSA-N 0.000 abstract 1
- WASQWSOJHCZDFK-UHFFFAOYSA-N Diketene Chemical compound C=C1CC(=O)O1 WASQWSOJHCZDFK-UHFFFAOYSA-N 0.000 abstract 1
- 239000004150 EU approved colour Substances 0.000 abstract 1
- RRAMGCGOFNQTLD-UHFFFAOYSA-N Hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 abstract 1
- 239000005057 Hexamethylene diisocyanate Substances 0.000 abstract 1
- OMPJBNCRMGITSC-UHFFFAOYSA-N Incidol Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 abstract 1
- WLJVNTCWHIRURA-UHFFFAOYSA-N Pimelic acid Chemical compound OC(=O)CCCCCC(O)=O WLJVNTCWHIRURA-UHFFFAOYSA-N 0.000 abstract 1
- CXMXRPHRNRROMY-UHFFFAOYSA-N Sebacic acid Chemical compound OC(=O)CCCCCCCCC(O)=O CXMXRPHRNRROMY-UHFFFAOYSA-N 0.000 abstract 1
- 150000007513 acids Chemical class 0.000 abstract 1
- 150000001298 alcohols Chemical class 0.000 abstract 1
- 150000008064 anhydrides Chemical class 0.000 abstract 1
- 150000001491 aromatic compounds Chemical class 0.000 abstract 1
- 150000001536 azelaic acids Chemical class 0.000 abstract 1
- 150000001555 benzenes Chemical class 0.000 abstract 1
- 235000019400 benzoyl peroxide Nutrition 0.000 abstract 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 abstract 1
- 238000005266 casting Methods 0.000 abstract 1
- 239000003054 catalyst Substances 0.000 abstract 1
- 239000007795 chemical reaction product Substances 0.000 abstract 1
- 239000003795 chemical substances by application Substances 0.000 abstract 1
- 150000001805 chlorine compounds Chemical class 0.000 abstract 1
- 239000011248 coating agent Substances 0.000 abstract 1
- 238000000576 coating method Methods 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 abstract 1
- FOTKYAAJKYLFFN-UHFFFAOYSA-N decane-1,10-diol Chemical compound OCCCCCCCCCCO FOTKYAAJKYLFFN-UHFFFAOYSA-N 0.000 abstract 1
- 125000005442 diisocyanate group Chemical group 0.000 abstract 1
- 230000000694 effects Effects 0.000 abstract 1
- 150000002148 esters Chemical class 0.000 abstract 1
- 239000000945 filler Substances 0.000 abstract 1
- 150000002334 glycols Chemical class 0.000 abstract 1
- 238000010438 heat treatment Methods 0.000 abstract 1
- 238000010030 laminating Methods 0.000 abstract 1
- 239000000314 lubricant Substances 0.000 abstract 1
- 239000003605 opacifier Substances 0.000 abstract 1
- 229940006093 opthalmologic coloring agents Diagnostic Drugs 0.000 abstract 1
- 125000000864 peroxy group Chemical group O(O*)* 0.000 abstract 1
- 150000003022 phthalic acids Chemical class 0.000 abstract 1
- 239000004014 plasticizer Substances 0.000 abstract 1
- 238000006116 polymerization reaction Methods 0.000 abstract 1
- 238000004382 potting Methods 0.000 abstract 1
- DNIAPMSPPWPWGF-UHFFFAOYSA-N propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 abstract 1
- 239000000376 reactant Substances 0.000 abstract 1
- 239000011347 resin Substances 0.000 abstract 1
- 229920005989 resin Polymers 0.000 abstract 1
- 239000011342 resin composition Substances 0.000 abstract 1
- 230000000630 rising Effects 0.000 abstract 1
- 239000002904 solvent Substances 0.000 abstract 1
- 150000003442 suberic acids Chemical class 0.000 abstract 1
- 150000003504 terephthalic acids Chemical class 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/67—Unsaturated compounds having active hydrogen
- C08G18/68—Unsaturated polyesters
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
- C08G63/02—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds
- C08G63/12—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds derived from polycarboxylic acids and polyhydroxy compounds
- C08G63/52—Polycarboxylic acids or polyhydroxy compounds in which at least one of the two components contains aliphatic unsaturation
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Macromonomer-Based Addition Polymer (AREA)
- Compositions Of Macromolecular Compounds (AREA)
Abstract
Tough, mouldable resin compositions are prepared by mixing (A) 60 to 99 per cent of at least one monovinyl aromatic compound of the benzene series and (B) 40 to 1 per cent of at least one polymerizable high molecular weight linear elastic polyester having a second order transition temperature below room temperature and which is the reaction product of a minor amount of (1) an organic diisocyanate or diketene and a major amount of (2) a lower molecular weight polyester derived from (a) a mixture of dicarboxylic acids comprising an ethylene-a ,b -dicarboxylic acid and (b) excess of at least one glycol, optionally mixed with (3) a polyester derived from glycols and dicarboxylic acids free from ethylenic unsaturations, the amount of ethylene-a ,b -dicarboxylic acid being 0.0845 to 1.5 per cent by weight of the composition and 1 to 3 mole. per cent of the acids, and heating to effect polymerization. Specified monovinyl compounds are styrene, p-methylstyrene, m-methylstyrene, p-ethylstyrene, p-isopropylstyrene, 2,4 - dimethylstyrene, p - chlorostyrene, 2-chloro - 4 - methylstyrene and 2,4 - dichlorostyrene which may be partially prepolymerized. The polyesters may be derived from maleic, fumaric, citraconic, chloromaleic, adipic, b -methyl adipic, pimelic, suberic, azelaic, sebacic, phthalic and terephthalic acids or their anhydrides, acid chlorides or esters of low molecular weight monohydric alcohols, and 1,2-propylene glycol, 2,2 - dimethyl propanediol - 1,3, ethylene glycol, trimethylene glycol, hexamethylene glycol and decamethylene glycol, at least one of the reactants preferably having a branched carbon chain. The polyesters may also comprise long chain hydroxy aliphatic carboxylic acid radicals, e.g. of 12-hydroxystearic acid. Specified coupling materials are ethylene diisocyanate, trimethylene diisocyanate, tetra-methylene diisocyanate, hexamethylene diisocyanate, decamethylene diisocyanate, meta-toluene diisocyanate, 1,5-naphthalene diisocyanate, 2,9-dimethyl - 1,9 - decadiene - 1,10 - dione, 3,10-dicarbonyl-2,11-dodecanedione and carbon sub-oxide. Preferably (B) is prepared by coupling saturated linear polyesters with polyesters containing a higher proportion of unsaturated dicarboxylic acid than the desired mean. The polymerizable compositions may contain plasticizers, mould lubricants, colouring agents, opacifiers, pearlescents and fillers and may be polymerized, optionally in the presence of nonreactive solvents and peroxy catalysts, e.g. benzoyl peroxide, cumene hydroperoxide, ascaridol and tert-butyl peroxide, on a rising temperature schedule. The compositions may be used as laminating resins, coating materials, casting and potting agents and for impregnating porous and fibrous structures.
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB815839A true GB815839A (en) | 1956-11-08 |
Family
ID=1743790
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB3417256A Expired GB815839A (en) | 1956-11-08 | Process for making copolymers of monovinylbenzene compounds and unsaturated alkydresins |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB815839A (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB2164345A (en) * | 1984-09-13 | 1986-03-19 | Armstrong World Ind Inc | Radiation crosslinkable coating composition |
| US5128385A (en) * | 1984-09-13 | 1992-07-07 | Armstrong World Industries, Inc. | Photocrosslinkable thermoplastic urethane coating system |
-
1956
- 1956-11-08 GB GB3417256A patent/GB815839A/en not_active Expired
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB2164345A (en) * | 1984-09-13 | 1986-03-19 | Armstrong World Ind Inc | Radiation crosslinkable coating composition |
| US5128385A (en) * | 1984-09-13 | 1992-07-07 | Armstrong World Industries, Inc. | Photocrosslinkable thermoplastic urethane coating system |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US3301743A (en) | Polyhydroxy polyacrylate esters of epoxidized phenol-formaldehyde novolac resins and laminates therefrom | |
| US4038341A (en) | Low profile additives in polyester systems | |
| US3466259A (en) | Thickened thermosetting vinyl ester resins | |
| GB913861A (en) | Flame-resistant polyester resinous compositions | |
| US4293686A (en) | Thermosetting polyester resin composition | |
| US3548030A (en) | Vinyl ester resins containing esterified secondary hydroxy groups | |
| US2902462A (en) | Polyester of a mixture of isomeric c10 dicarboxylic acids and process of making | |
| US2819248A (en) | Unsaturated polyester room temperature setting adhesive composition | |
| US3449276A (en) | Triple accelerator system for promoting the cure of free-radical catalyzed unsaturated polyester resins | |
| US2856378A (en) | Polymerizable unsaturated polyester resin compositions containing small amounts of certain saturated alkyd resins and process of preparing the same | |
| GB815839A (en) | Process for making copolymers of monovinylbenzene compounds and unsaturated alkydresins | |
| GB861852A (en) | Compositions capable of hardening throughout at room temperature and containing condensation products of ª:ª-unsaturated compounds with methylol-aminotriazine allyl ethers | |
| US3842142A (en) | Unsaturated polyester compositions | |
| US3249574A (en) | Polyester-vinyl monomer compositions containing hydrogen peroxide | |
| US3367994A (en) | Novel accelerator for unsaturated polyester resins | |
| US4276388A (en) | Molding resin composition | |
| US3196191A (en) | Halogen-containing polyester compositions | |
| US3631224A (en) | Unsaturated polyester resin molding powder | |
| US3957906A (en) | Chemically resistant polyester resins compositions | |
| US3592874A (en) | Unsaturated polyesters containing chemically incorporated cobalt | |
| US3044978A (en) | New addition polymers from monomeric vinyl compounds and unsaturated cross-linked polyester resins and a process for preparing the same | |
| US3814724A (en) | Polymerizable liquid compositions for unsaturated polyester resins | |
| US2890144A (en) | Composition comprising a vinyl monomer and a polyester of a polyhydric alcohol, an unsaturated acid, a saturated acid and a hexahalocyclopentadiene adduct and laminated article containing same | |
| US2882256A (en) | Copolymer of unsaturated polyester, styrene and dibutyl fumarate or dibutyl maleate and process of preparing same | |
| US2537375A (en) | Method of curing polyester resins |