DE1034856B - Verfahren zum Haerten von Epoxyharzen - Google Patents
Verfahren zum Haerten von EpoxyharzenInfo
- Publication number
- DE1034856B DE1034856B DEU2688A DEU0002688A DE1034856B DE 1034856 B DE1034856 B DE 1034856B DE U2688 A DEU2688 A DE U2688A DE U0002688 A DEU0002688 A DE U0002688A DE 1034856 B DE1034856 B DE 1034856B
- Authority
- DE
- Germany
- Prior art keywords
- epoxy resins
- epoxy
- curing
- reaction
- bis
- 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.)
- Pending
Links
- 239000003822 epoxy resin Substances 0.000 title claims description 12
- 229920000647 polyepoxide Polymers 0.000 title claims description 12
- 238000000034 method Methods 0.000 title claims description 8
- LNEPOXFFQSENCJ-UHFFFAOYSA-N haloperidol Chemical compound C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 LNEPOXFFQSENCJ-UHFFFAOYSA-N 0.000 title claims description 7
- 239000003795 chemical substances by application Substances 0.000 claims description 16
- 229920000570 polyether Polymers 0.000 claims description 11
- 239000004721 Polyphenylene oxide Substances 0.000 claims description 9
- 125000003055 glycidyl group Chemical group C(C1CO1)* 0.000 claims description 9
- -1 amino compound Chemical class 0.000 claims description 7
- 150000001875 compounds Chemical class 0.000 claims description 7
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 claims description 6
- RPNUMPOLZDHAAY-UHFFFAOYSA-N Diethylenetriamine Chemical compound NCCNCCN RPNUMPOLZDHAAY-UHFFFAOYSA-N 0.000 claims description 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 2
- 150000005846 sugar alcohols Polymers 0.000 claims description 2
- 239000007795 chemical reaction product Substances 0.000 claims 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 1
- 125000001302 tertiary amino group Chemical group 0.000 claims 1
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 12
- 229920005989 resin Polymers 0.000 description 12
- 239000011347 resin Substances 0.000 description 12
- 150000001412 amines Chemical class 0.000 description 10
- 239000004593 Epoxy Substances 0.000 description 7
- 239000004848 polyfunctional curative Substances 0.000 description 7
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 6
- 238000002360 preparation method Methods 0.000 description 6
- 239000001294 propane Substances 0.000 description 6
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- 239000001257 hydrogen Substances 0.000 description 4
- 229910052739 hydrogen Inorganic materials 0.000 description 4
- 150000002825 nitriles Chemical class 0.000 description 4
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 3
- 238000005452 bending Methods 0.000 description 3
- 150000002989 phenols Chemical class 0.000 description 3
- 230000000704 physical effect Effects 0.000 description 3
- 229920000768 polyamine Polymers 0.000 description 3
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 2
- 125000003700 epoxy group Chemical group 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 235000011187 glycerol Nutrition 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- YPFDHNVEDLHUCE-UHFFFAOYSA-N propane-1,3-diol Chemical compound OCCCO YPFDHNVEDLHUCE-UHFFFAOYSA-N 0.000 description 2
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 1
- VILCJCGEZXAXTO-UHFFFAOYSA-N 2,2,2-tetramine Chemical compound NCCNCCNCCN VILCJCGEZXAXTO-UHFFFAOYSA-N 0.000 description 1
- 125000001731 2-cyanoethyl group Chemical group [H]C([H])(*)C([H])([H])C#N 0.000 description 1
- QISOBCMNUJQOJU-UHFFFAOYSA-N 4-bromo-1h-pyrazole-5-carboxylic acid Chemical compound OC(=O)C=1NN=CC=1Br QISOBCMNUJQOJU-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 1
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Natural products OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 1
- GYCMBHHDWRMZGG-UHFFFAOYSA-N Methylacrylonitrile Chemical compound CC(=C)C#N GYCMBHHDWRMZGG-UHFFFAOYSA-N 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- 239000000853 adhesive Substances 0.000 description 1
- 230000001070 adhesive effect Effects 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 239000001273 butane Substances 0.000 description 1
- KVNRLNFWIYMESJ-UHFFFAOYSA-N butyronitrile Chemical compound CCCC#N KVNRLNFWIYMESJ-UHFFFAOYSA-N 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- NKKMVIVFRUYPLQ-NSCUHMNNSA-N crotononitrile Chemical compound C\C=C\C#N NKKMVIVFRUYPLQ-NSCUHMNNSA-N 0.000 description 1
- 210000003298 dental enamel Anatomy 0.000 description 1
- GYZLOYUZLJXAJU-UHFFFAOYSA-N diglycidyl ether Chemical compound C1OC1COCC1CO1 GYZLOYUZLJXAJU-UHFFFAOYSA-N 0.000 description 1
- SZXQTJUDPRGNJN-UHFFFAOYSA-N dipropylene glycol Chemical compound OCCCOCCCO SZXQTJUDPRGNJN-UHFFFAOYSA-N 0.000 description 1
- VVVGBSBACSLYDS-UHFFFAOYSA-N ethene Chemical group C=C.C=C.C=C.C=C.C=C.C=C VVVGBSBACSLYDS-UHFFFAOYSA-N 0.000 description 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 239000001530 fumaric acid Substances 0.000 description 1
- 238000001879 gelation Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000001282 iso-butane Substances 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000000465 moulding Methods 0.000 description 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- 230000036632 reaction speed Effects 0.000 description 1
- 239000011342 resin composition Substances 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- FAGUFWYHJQFNRV-UHFFFAOYSA-N tetraethylenepentamine Chemical compound NCCNCCNCCNCCN FAGUFWYHJQFNRV-UHFFFAOYSA-N 0.000 description 1
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 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
- C08G59/18—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
- C08G59/50—Amines
- C08G59/54—Amino amides>
-
- 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
- C08G59/50—Amines
- C08G59/52—Amino carboxylic acids
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)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US345673A US2753323A (en) | 1953-03-30 | 1953-03-30 | Epoxy resins cured with an amine having at least one cyanoethyl group |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1034856B true DE1034856B (de) | 1958-07-24 |
Family
ID=23356001
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEU2688A Pending DE1034856B (de) | 1953-03-30 | 1954-03-27 | Verfahren zum Haerten von Epoxyharzen |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US2753323A (en, 2012) |
| BE (1) | BE527446A (en, 2012) |
| CH (1) | CH340342A (en, 2012) |
| DE (1) | DE1034856B (en, 2012) |
| FR (1) | FR1100182A (en, 2012) |
| GB (1) | GB761443A (en, 2012) |
| NL (2) | NL89473C (en, 2012) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0012293A1 (de) * | 1978-12-16 | 1980-06-25 | Bayer Ag | Cyanethylierte Polyamidamine als Härter für Polyepoxide |
Families Citing this family (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2988535A (en) * | 1955-12-21 | 1961-06-13 | Freed Transformer Co Inc | Curing of epoxide resins |
| US3091595A (en) * | 1956-03-22 | 1963-05-28 | Shell Oil Co | Cyano-substituted polyamides and their use as curing agents for polyepoxides |
| US3029227A (en) * | 1956-08-20 | 1962-04-10 | Minnesota Mining & Mfg | Cross-linking and cross-linking agents |
| NL230883A (en, 2012) * | 1957-08-28 | |||
| DE1072805B (de) * | 1958-01-03 | 1960-01-07 | Deutsche Solfvay- Werke Gesellschaft mit beschränkter Haftung, Solingen-Ohligs | Verfahren zum Härten von Epoxy harzen |
| US3043705A (en) * | 1958-05-08 | 1962-07-10 | Glidden Co | Coated metal articles and coating compositions therefor |
| US3247163A (en) * | 1960-10-14 | 1966-04-19 | Union Carbide Corp | Curable compositions of a polyepoxide and a reaction product of an amine and an acrylate |
| BE637054A (en, 2012) * | 1962-09-07 | |||
| US3326853A (en) * | 1962-12-31 | 1967-06-20 | Union Oil Co | Reaction product of a polyethoxyline monomer and an aminoamide |
| BE793258A (fr) * | 1971-12-23 | 1973-04-16 | Veba Chemie Ag | Procede pour la preparation de polymeres d'addition |
| JPS5247755B2 (en, 2012) | 1973-10-05 | 1977-12-05 | ||
| US4032482A (en) | 1974-03-25 | 1977-06-28 | Miyoshi Yushi Kabushiki Kaisha | Process for producing chelating resin and product produced thereby |
| US4324739A (en) * | 1979-04-10 | 1982-04-13 | Ciba-Geigy Corporation | Dimethylamino derivatives and their use |
| US4352913A (en) * | 1979-04-10 | 1982-10-05 | Ciba-Geigy Corporation | Dimethylamino derivatives and their use |
| US4294746A (en) * | 1980-06-17 | 1981-10-13 | Union Carbide Corporation | Stabilizers for cycloaliphatic epoxide containing compositions |
| JPS5874720A (ja) * | 1981-10-30 | 1983-05-06 | Hitachi Ltd | 耐熱性樹脂の製法 |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2500600A (en) * | 1948-02-28 | 1950-03-14 | Shell Dev | Compositions of matter containing epoxy ethers and diamines |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE474687A (en, 2012) * | 1945-07-13 | 1900-01-01 | ||
| BE489970A (en, 2012) * | 1948-07-05 | |||
| BE495432A (en, 2012) * | 1949-04-29 | 1900-01-01 |
-
0
- NL NLAANVRAGE7802793,B patent/NL186337B/xx unknown
- BE BE527446D patent/BE527446A/xx unknown
- NL NL89473D patent/NL89473C/xx active
-
1953
- 1953-03-30 US US345673A patent/US2753323A/en not_active Expired - Lifetime
-
1954
- 1954-03-16 FR FR1100182D patent/FR1100182A/fr not_active Expired
- 1954-03-22 GB GB8239/54A patent/GB761443A/en not_active Expired
- 1954-03-27 DE DEU2688A patent/DE1034856B/de active Pending
- 1954-03-29 CH CH340342D patent/CH340342A/de unknown
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2500600A (en) * | 1948-02-28 | 1950-03-14 | Shell Dev | Compositions of matter containing epoxy ethers and diamines |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0012293A1 (de) * | 1978-12-16 | 1980-06-25 | Bayer Ag | Cyanethylierte Polyamidamine als Härter für Polyepoxide |
Also Published As
| Publication number | Publication date |
|---|---|
| US2753323A (en) | 1956-07-03 |
| BE527446A (en, 2012) | |
| NL186337B (nl) | |
| NL89473C (en, 2012) | |
| GB761443A (en) | 1956-11-14 |
| FR1100182A (fr) | 1955-09-16 |
| CH340342A (de) | 1959-08-15 |
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