GB855025A - Improvements in and relating to polymerisable epoxide compositions - Google Patents
Improvements in and relating to polymerisable epoxide compositionsInfo
- Publication number
- GB855025A GB855025A GB3250658A GB3250658A GB855025A GB 855025 A GB855025 A GB 855025A GB 3250658 A GB3250658 A GB 3250658A GB 3250658 A GB3250658 A GB 3250658A GB 855025 A GB855025 A GB 855025A
- Authority
- GB
- United Kingdom
- Prior art keywords
- acid
- anhydride
- mixtures
- anhydrides
- acids
- 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 7
- 150000002118 epoxides Chemical class 0.000 title 1
- 150000008064 anhydrides Chemical class 0.000 abstract 5
- 239000002253 acid Substances 0.000 abstract 4
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 abstract 4
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 abstract 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 abstract 3
- -1 nitro, chloro, iodo Chemical group 0.000 abstract 3
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 abstract 2
- 239000003054 catalyst Substances 0.000 abstract 2
- 150000001875 compounds Chemical class 0.000 abstract 2
- 125000003700 epoxy group Chemical group 0.000 abstract 2
- CXMXRPHRNRROMY-UHFFFAOYSA-N sebacic acid Chemical compound OC(=O)CCCCCCCCC(O)=O CXMXRPHRNRROMY-UHFFFAOYSA-N 0.000 abstract 2
- MYRTYDVEIRVNKP-UHFFFAOYSA-N 1,2-Divinylbenzene Chemical compound C=CC1=CC=CC=C1C=C MYRTYDVEIRVNKP-UHFFFAOYSA-N 0.000 abstract 1
- PRJNEUBECVAVAG-UHFFFAOYSA-N 1,3-bis(ethenyl)benzene Chemical compound C=CC1=CC=CC(C=C)=C1 PRJNEUBECVAVAG-UHFFFAOYSA-N 0.000 abstract 1
- RTBFRGCFXZNCOE-UHFFFAOYSA-N 1-methylsulfonylpiperidin-4-one Chemical compound CS(=O)(=O)N1CCC(=O)CC1 RTBFRGCFXZNCOE-UHFFFAOYSA-N 0.000 abstract 1
- FALRKNHUBBKYCC-UHFFFAOYSA-N 2-(chloromethyl)pyridine-3-carbonitrile Chemical compound ClCC1=NC=CC=C1C#N FALRKNHUBBKYCC-UHFFFAOYSA-N 0.000 abstract 1
- CDAWCLOXVUBKRW-UHFFFAOYSA-N 2-aminophenol Chemical class NC1=CC=CC=C1O CDAWCLOXVUBKRW-UHFFFAOYSA-N 0.000 abstract 1
- BAFMBHJRYJBYQD-UHFFFAOYSA-N 2-ethyl-3-phenyloxirane Chemical compound CCC1OC1C1=CC=CC=C1 BAFMBHJRYJBYQD-UHFFFAOYSA-N 0.000 abstract 1
- IMANPMSNXXRXGK-UHFFFAOYSA-N C(=C)C12C(C3C(C=C1)(C=C)O3)O2 Chemical compound C(=C)C12C(C3C(C=C1)(C=C)O3)O2 IMANPMSNXXRXGK-UHFFFAOYSA-N 0.000 abstract 1
- 239000002841 Lewis acid Substances 0.000 abstract 1
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 abstract 1
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 abstract 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 abstract 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 abstract 1
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical class OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 abstract 1
- 150000008065 acid anhydrides Chemical class 0.000 abstract 1
- 150000007513 acids Chemical class 0.000 abstract 1
- 235000011037 adipic acid Nutrition 0.000 abstract 1
- 239000001361 adipic acid Substances 0.000 abstract 1
- 150000001298 alcohols Chemical class 0.000 abstract 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 abstract 1
- 150000001412 amines Chemical class 0.000 abstract 1
- JFCQEDHGNNZCLN-UHFFFAOYSA-N anhydrous glutaric acid Natural products OC(=O)CCCC(O)=O JFCQEDHGNNZCLN-UHFFFAOYSA-N 0.000 abstract 1
- 125000001246 bromo group Chemical group Br* 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
- 125000004432 carbon atom Chemical group C* 0.000 abstract 1
- 150000001735 carboxylic acids Chemical class 0.000 abstract 1
- 238000000576 coating method Methods 0.000 abstract 1
- 125000004122 cyclic group Chemical group 0.000 abstract 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 abstract 1
- 238000010438 heat treatment Methods 0.000 abstract 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 1
- 239000012535 impurity Substances 0.000 abstract 1
- 229910052500 inorganic mineral Inorganic materials 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
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 abstract 1
- 229910001507 metal halide Inorganic materials 0.000 abstract 1
- 239000011707 mineral Substances 0.000 abstract 1
- 239000003960 organic solvent Substances 0.000 abstract 1
- PGMYKACGEOXYJE-UHFFFAOYSA-N pentyl acetate Chemical class CCCCCOC(C)=O PGMYKACGEOXYJE-UHFFFAOYSA-N 0.000 abstract 1
- 239000004848 polyfunctional curative Substances 0.000 abstract 1
- 239000011347 resin Substances 0.000 abstract 1
- 229920005989 resin Polymers 0.000 abstract 1
- 239000002904 solvent Substances 0.000 abstract 1
- 229940014800 succinic anhydride Drugs 0.000 abstract 1
- 235000011149 sulphuric acid Nutrition 0.000 abstract 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 abstract 1
- 239000008096 xylene Substances 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
- C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
- C08G59/02—Polycondensates containing more than one epoxy group per molecule
- C08G59/027—Polycondensates containing more than one epoxy group per molecule obtained by epoxidation of unsaturated precursor, e.g. polymer or monomer
-
- 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
- C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
- C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
- C08G59/20—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the epoxy compounds used
- C08G59/22—Di-epoxy compounds
- C08G59/24—Di-epoxy compounds carbocyclic
- C08G59/245—Di-epoxy compounds carbocyclic aromatic
-
- 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
- C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
- C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
- C08G59/40—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the curing agents used
- C08G59/42—Polycarboxylic acids; Anhydrides, halides or low molecular weight esters thereof
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Epoxy Resins (AREA)
- Epoxy Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
A polymerizable composition comprises o, m or p-divinyl benzene dioxide and a polycarboxylic acid anhydride in an amount having 0,2 to 3 carboxyl equivalents per epoxy group; a polycarboxylic acid compound may also be present in amount having up to 1 carboxyl group per epoxy group, the total number not exceeding 3 and the acid always providing fewer carboxyl equivalents than the anhydride. The compositions are converted to hard, infusible resins by heating to 25 to 250 DEG C., if desired in the presence of catalysts. The polycarboxylic anhydrides may be of the formula XCO.O.CO, where X is 2 or more carbon atoms connected by single or double bonds and which may contain hydroxyl, nitro, chloro, iodo, bromo, and cyclic groups, as well as interconnecting oxydicarbonyl groups. Mixtures of anhydrides may be used. Many examples are given. The poly carboxylic acids are of the same classes and the acid compounds include poylhydric alcohol esters which contain more than one carboxyl group per molecule. The catalysts include mineral acids, sulphuric acids, metal halide Lewis acids, alkali metal hydroxides and amines, including aminophenols. They may be added as solutions in organic solvents. The uncured or partially cured compositions may be dissolved in solvents, e.g. xylene, methyl isobutyl ketone, butyl, ethyl and amyl acetates and toluene, particularly for applying surface coatings which are subsequently heat cured. In the examples, the dioxides are mixtures of the three isomers containing ethyl styrene oxide as main impurity. The hardeners are phthalic, succinic, glutonic, polyadipic and chlorendic anhydrides, mixtures of phthalic anhydric and sebacic acid, maleic anhydride and adipic acid, polyadipic anhydride and maleic acid, and of glutaric acid and the adduct of 1 mol of glycerol with 3 mols of succinic anhydride.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB3250658A GB855025A (en) | 1958-10-11 | 1958-10-11 | Improvements in and relating to polymerisable epoxide compositions |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB3250658A GB855025A (en) | 1958-10-11 | 1958-10-11 | Improvements in and relating to polymerisable epoxide compositions |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB855025A true GB855025A (en) | 1960-11-30 |
Family
ID=10339646
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB3250658A Expired GB855025A (en) | 1958-10-11 | 1958-10-11 | Improvements in and relating to polymerisable epoxide compositions |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB855025A (en) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2011103014A1 (en) | 2010-02-19 | 2011-08-25 | Dow Global Technologies Llc | Divinylarene dioxide resin compositions |
| WO2011146580A2 (en) | 2010-05-21 | 2011-11-24 | Dow Global Technologies Llc | Curable compositions |
| CN102432835A (en) * | 2010-06-29 | 2012-05-02 | 陶氏环球技术有限公司 | Curable compositions |
| WO2012158291A1 (en) * | 2011-05-13 | 2012-11-22 | Dow Global Technologies Llc | Insulation formulations |
-
1958
- 1958-10-11 GB GB3250658A patent/GB855025A/en not_active Expired
Cited By (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2011103014A1 (en) | 2010-02-19 | 2011-08-25 | Dow Global Technologies Llc | Divinylarene dioxide resin compositions |
| US9359468B2 (en) | 2010-02-19 | 2016-06-07 | Blue Cube Ip Llc | Divinylarene dioxide resin compositions |
| WO2011146580A2 (en) | 2010-05-21 | 2011-11-24 | Dow Global Technologies Llc | Curable compositions |
| WO2011146580A3 (en) * | 2010-05-21 | 2012-04-05 | Dow Global Technologies Llc | Curable compositions |
| RU2581832C2 (en) * | 2010-05-21 | 2016-04-20 | БЛЮ КЬЮБ АйПи ЭлЭлСи | Curable compositions |
| CN102432835A (en) * | 2010-06-29 | 2012-05-02 | 陶氏环球技术有限公司 | Curable compositions |
| WO2012158291A1 (en) * | 2011-05-13 | 2012-11-22 | Dow Global Technologies Llc | Insulation formulations |
| JP2014520172A (en) * | 2011-05-13 | 2014-08-21 | ダウ グローバル テクノロジーズ エルエルシー | Insulation compound |
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