GB924459A - Modified unsaturated polyester resins - Google Patents
Modified unsaturated polyester resinsInfo
- Publication number
- GB924459A GB924459A GB428361A GB428361A GB924459A GB 924459 A GB924459 A GB 924459A GB 428361 A GB428361 A GB 428361A GB 428361 A GB428361 A GB 428361A GB 924459 A GB924459 A GB 924459A
- Authority
- GB
- United Kingdom
- Prior art keywords
- acid
- unsaturated
- glycol
- reacting
- 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
- 229920006337 unsaturated polyester resin Polymers 0.000 title 1
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 abstract 4
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 abstract 4
- 229920000728 polyester Polymers 0.000 abstract 4
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 abstract 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 abstract 3
- -1 ethylene- Chemical class 0.000 abstract 3
- HGINCPLSRVDWNT-UHFFFAOYSA-N Acrolein Chemical compound C=CC=O HGINCPLSRVDWNT-UHFFFAOYSA-N 0.000 abstract 2
- JIGUQPWFLRLWPJ-UHFFFAOYSA-N Ethyl acrylate Chemical compound CCOC(=O)C=C JIGUQPWFLRLWPJ-UHFFFAOYSA-N 0.000 abstract 2
- 229910052739 hydrogen Inorganic materials 0.000 abstract 2
- 239000001257 hydrogen Substances 0.000 abstract 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 2
- PNJWIWWMYCMZRO-UHFFFAOYSA-N pent‐4‐en‐2‐one Natural products CC(=O)CC=C PNJWIWWMYCMZRO-UHFFFAOYSA-N 0.000 abstract 2
- BJELTSYBAHKXRW-UHFFFAOYSA-N 2,4,6-triallyloxy-1,3,5-triazine Chemical compound C=CCOC1=NC(OCC=C)=NC(OCC=C)=N1 BJELTSYBAHKXRW-UHFFFAOYSA-N 0.000 abstract 1
- JAHNSTQSQJOJLO-UHFFFAOYSA-N 2-(3-fluorophenyl)-1h-imidazole Chemical compound FC1=CC=CC(C=2NC=CN=2)=C1 JAHNSTQSQJOJLO-UHFFFAOYSA-N 0.000 abstract 1
- DBCAQXHNJOFNGC-UHFFFAOYSA-N 4-bromo-1,1,1-trifluorobutane Chemical compound FC(F)(F)CCCBr DBCAQXHNJOFNGC-UHFFFAOYSA-N 0.000 abstract 1
- QISOBCMNUJQOJU-UHFFFAOYSA-N 4-bromo-1h-pyrazole-5-carboxylic acid Chemical compound OC(=O)C=1NN=CC=1Br QISOBCMNUJQOJU-UHFFFAOYSA-N 0.000 abstract 1
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 abstract 1
- 239000004641 Diallyl-phthalate Substances 0.000 abstract 1
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 abstract 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 abstract 1
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 abstract 1
- ROXDJICXVDEDBO-UHFFFAOYSA-D P(=O)(OCCCC)([O-])[O-].[V+5].C(CCC)OP(=O)([O-])[O-].C(CCC)OP(=O)([O-])[O-].C(CCC)OP(=O)([O-])[O-].C(CCC)OP(=O)([O-])[O-].[V+5] Chemical compound P(=O)(OCCCC)([O-])[O-].[V+5].C(CCC)OP(=O)([O-])[O-].C(CCC)OP(=O)([O-])[O-].C(CCC)OP(=O)([O-])[O-].C(CCC)OP(=O)([O-])[O-].[V+5] ROXDJICXVDEDBO-UHFFFAOYSA-D 0.000 abstract 1
- LGRFSURHDFAFJT-UHFFFAOYSA-N Phthalic anhydride Natural products C1=CC=C2C(=O)OC(=O)C2=C1 LGRFSURHDFAFJT-UHFFFAOYSA-N 0.000 abstract 1
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 abstract 1
- LVZGQWKTUCVPBQ-UHFFFAOYSA-N acetic acid;trifluoroborane Chemical compound CC(O)=O.FB(F)F LVZGQWKTUCVPBQ-UHFFFAOYSA-N 0.000 abstract 1
- 239000002253 acid Substances 0.000 abstract 1
- 239000003377 acid catalyst Substances 0.000 abstract 1
- 150000001299 aldehydes Chemical class 0.000 abstract 1
- 125000001931 aliphatic group Chemical group 0.000 abstract 1
- 125000000217 alkyl group Chemical group 0.000 abstract 1
- 125000003118 aryl group Chemical group 0.000 abstract 1
- ZPOLOEWJWXZUSP-WAYWQWQTSA-N bis(prop-2-enyl) (z)-but-2-enedioate Chemical compound C=CCOC(=O)\C=C/C(=O)OCC=C ZPOLOEWJWXZUSP-WAYWQWQTSA-N 0.000 abstract 1
- QUDWYFHPNIMBFC-UHFFFAOYSA-N bis(prop-2-enyl) benzene-1,2-dicarboxylate Chemical compound C=CCOC(=O)C1=CC=CC=C1C(=O)OCC=C QUDWYFHPNIMBFC-UHFFFAOYSA-N 0.000 abstract 1
- JHIWVOJDXOSYLW-UHFFFAOYSA-N butyl 2,2-difluorocyclopropane-1-carboxylate Chemical compound CCCCOC(=O)C1CC1(F)F JHIWVOJDXOSYLW-UHFFFAOYSA-N 0.000 abstract 1
- 239000003054 catalyst Substances 0.000 abstract 1
- 238000006243 chemical reaction Methods 0.000 abstract 1
- HNEGQIOMVPPMNR-IHWYPQMZSA-N citraconic acid Chemical compound OC(=O)C(/C)=C\C(O)=O HNEGQIOMVPPMNR-IHWYPQMZSA-N 0.000 abstract 1
- 229940018557 citraconic acid Drugs 0.000 abstract 1
- 238000010494 dissociation reaction Methods 0.000 abstract 1
- 230000005593 dissociations Effects 0.000 abstract 1
- STVZJERGLQHEKB-UHFFFAOYSA-N ethylene glycol dimethacrylate Substances CC(=C)C(=O)OCCOC(=O)C(C)=C STVZJERGLQHEKB-UHFFFAOYSA-N 0.000 abstract 1
- 150000002334 glycols Chemical class 0.000 abstract 1
- 239000003112 inhibitor Substances 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
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 abstract 1
- 239000000178 monomer Substances 0.000 abstract 1
- GEMHFKXPOCTAIP-UHFFFAOYSA-N n,n-dimethyl-n'-phenylcarbamimidoyl chloride Chemical compound CN(C)C(Cl)=NC1=CC=CC=C1 GEMHFKXPOCTAIP-UHFFFAOYSA-N 0.000 abstract 1
- BDJRBEYXGGNYIS-UHFFFAOYSA-N nonanedioic acid Chemical compound OC(=O)CCCCCCCC(O)=O BDJRBEYXGGNYIS-UHFFFAOYSA-N 0.000 abstract 1
- 150000002978 peroxides Chemical class 0.000 abstract 1
- 230000000379 polymerizing effect Effects 0.000 abstract 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 abstract 1
- 125000003258 trimethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])[*:1] 0.000 abstract 1
- 229920006305 unsaturated polyester Polymers 0.000 abstract 1
- 229910052720 vanadium Inorganic materials 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
- C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
- C08G63/66—Polyesters containing oxygen in the form of ether groups
- C08G63/668—Polyesters containing oxygen in the form of ether groups derived from polycarboxylic acids and polyhydroxy compounds
- C08G63/676—Polyesters containing oxygen in the form of ether groups derived from polycarboxylic acids and 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)
Abstract
The pot-life of an unsaturated polyester is increased by reacting it, under non-polymerizing conditions, with an a ,b -unsaturated aldehyde of formula <FORM:0924459/IV(a)/1> where R1 is hydrogen or an aliphatic or aromatic group and R2 is hydrogen or a lower alkyl group. Reaction is performed in the presence of an acid catalyst having a dissociation constant greater than 1x10-2 (e.g. p-toluene sulphonic acid or a boron trifluoride acetic acid complex) and, preferably, also an inhibitor (e.g. hydroquinone). The preferred polyesters are those obtained by reacting (a) an unsaturated a ,b -dicarboxylic acid, e.g. maleic, fumaric, itaconic or citraconic acid, (b) a saturated glycol, e.g. ethylene-, diethylene-, triethylene-, trimethylene, a -propylene or 1:3-butylene-glycol, and, possibly, also (c) a non-polymerizable dicarboxylic acid, e.g. succinic, adipic, sebacic, azelaic, phthalic, tetrahydrophthalic, carbic or chorendic acid. The modified polyesters are copolymerized with an unsaturated monomer (e.g. styrene, methyl methacrylate, ethyl acrylate, acrylonitrile, vinyl acetate, ethylene glycol dimethacrylate, diallyl phthalate, diallyl maleate or triallyl cyanurate) in the presence of a peroxide or hydroperoxide catalyst and possibly an accelerator (e.g. cobalt naphthenate, vanadium naphthenate or vanadium butyl phosphate). In examples polyesters obtained by reacting maleic anhydride, phthalic anhydride and either ethylene glycol or propylene glycol were reacted with acrolein and subsequently copolymerized with ethyl acrylate or styrene. The polyester may be inhibited with hydroquinone.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB428361A GB924459A (en) | 1961-02-04 | 1961-02-04 | Modified unsaturated polyester resins |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB428361A GB924459A (en) | 1961-02-04 | 1961-02-04 | Modified unsaturated polyester resins |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB924459A true GB924459A (en) | 1963-04-24 |
Family
ID=9774213
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB428361A Expired GB924459A (en) | 1961-02-04 | 1961-02-04 | Modified unsaturated polyester resins |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB924459A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR3030547A1 (en) * | 2014-12-22 | 2016-06-24 | Arkema France | LIQUID (METH) ACRYLIC SYRUP, PROCESS FOR THE IMPREGNATION OF A FIBROUS SUBSTRATE BY THE SAME, AND COMPOSITE MATERIAL OBTAINED AFTER POLYMERIZATION OF THE IMPREGNATION SYRUP |
-
1961
- 1961-02-04 GB GB428361A patent/GB924459A/en not_active Expired
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR3030547A1 (en) * | 2014-12-22 | 2016-06-24 | Arkema France | LIQUID (METH) ACRYLIC SYRUP, PROCESS FOR THE IMPREGNATION OF A FIBROUS SUBSTRATE BY THE SAME, AND COMPOSITE MATERIAL OBTAINED AFTER POLYMERIZATION OF THE IMPREGNATION SYRUP |
| WO2016102890A1 (en) * | 2014-12-22 | 2016-06-30 | Arkema France | Liquid (meth)acrylic syrup, method for impregnating a fibrous substrate with said syrup, and composite material produced after polymerisation of said impregnation syrup |
| US11186723B2 (en) | 2014-12-22 | 2021-11-30 | Arkema France | Liquid (meth)acrylic syrup, method for impregnating a fibrous substrate with said syrup, and composite material produced after polymerisation of said impregnation syrup |
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