DE2104910A1 - Verfahren zur Herstellung von Polyaddukten auf der Basis von Epoxidharzen - Google Patents
Verfahren zur Herstellung von Polyaddukten auf der Basis von EpoxidharzenInfo
- Publication number
- DE2104910A1 DE2104910A1 DE19712104910 DE2104910A DE2104910A1 DE 2104910 A1 DE2104910 A1 DE 2104910A1 DE 19712104910 DE19712104910 DE 19712104910 DE 2104910 A DE2104910 A DE 2104910A DE 2104910 A1 DE2104910 A1 DE 2104910A1
- Authority
- DE
- Germany
- Prior art keywords
- oxide
- epoxy
- compounds
- production
- radicals
- 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 20
- 229920000647 polyepoxide Polymers 0.000 title claims description 20
- 238000004519 manufacturing process Methods 0.000 title claims description 13
- 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
- 238000000034 method Methods 0.000 title claims description 4
- 239000004593 Epoxy Substances 0.000 claims description 12
- 150000001875 compounds Chemical class 0.000 claims description 9
- -1 compound phosphine oxides Chemical class 0.000 claims description 5
- 125000003700 epoxy group Chemical group 0.000 claims description 4
- 125000003118 aryl group Chemical group 0.000 claims description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 3
- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 claims description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 2
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 238000001723 curing Methods 0.000 description 17
- ZMBHCYHQLYEYDV-UHFFFAOYSA-N trioctylphosphine oxide Chemical compound CCCCCCCCP(=O)(CCCCCCCC)CCCCCCCC ZMBHCYHQLYEYDV-UHFFFAOYSA-N 0.000 description 16
- 239000004848 polyfunctional curative Substances 0.000 description 14
- IISBACLAFKSPIT-UHFFFAOYSA-N Bisphenol A Natural products C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 9
- 229920005989 resin Polymers 0.000 description 6
- 239000011347 resin Substances 0.000 description 6
- LGRFSURHDFAFJT-UHFFFAOYSA-N Phthalic anhydride Natural products C1=CC=C2C(=O)OC(=O)C2=C1 LGRFSURHDFAFJT-UHFFFAOYSA-N 0.000 description 5
- 150000001412 amines Chemical class 0.000 description 5
- 229940106691 bisphenol a Drugs 0.000 description 5
- JHIWVOJDXOSYLW-UHFFFAOYSA-N butyl 2,2-difluorocyclopropane-1-carboxylate Chemical compound CCCCOC(=O)C1CC1(F)F JHIWVOJDXOSYLW-UHFFFAOYSA-N 0.000 description 5
- 239000007788 liquid Substances 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- 230000000694 effects Effects 0.000 description 4
- HVLLSGMXQDNUAL-UHFFFAOYSA-N triphenyl phosphite Chemical compound C=1C=CC=CC=1OP(OC=1C=CC=CC=1)OC1=CC=CC=C1 HVLLSGMXQDNUAL-UHFFFAOYSA-N 0.000 description 4
- 239000000654 additive Substances 0.000 description 3
- 238000002845 discoloration Methods 0.000 description 3
- 150000003512 tertiary amines Chemical class 0.000 description 3
- MUTGBJKUEZFXGO-OLQVQODUSA-N (3as,7ar)-3a,4,5,6,7,7a-hexahydro-2-benzofuran-1,3-dione Chemical compound C1CCC[C@@H]2C(=O)OC(=O)[C@@H]21 MUTGBJKUEZFXGO-OLQVQODUSA-N 0.000 description 2
- MNZAKDODWSQONA-UHFFFAOYSA-N 1-dibutylphosphorylbutane Chemical compound CCCCP(=O)(CCCC)CCCC MNZAKDODWSQONA-UHFFFAOYSA-N 0.000 description 2
- GEZGQQFKEOIGJS-UHFFFAOYSA-N 2-di(propan-2-yl)phosphorylpropane Chemical compound CC(C)P(=O)(C(C)C)C(C)C GEZGQQFKEOIGJS-UHFFFAOYSA-N 0.000 description 2
- 239000004606 Fillers/Extenders Substances 0.000 description 2
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 150000008065 acid anhydrides Chemical class 0.000 description 2
- 150000008064 anhydrides Chemical class 0.000 description 2
- 238000000576 coating method Methods 0.000 description 2
- LEFPWWWXFFNJAA-UHFFFAOYSA-N dicyclohexylphosphorylcyclohexane Chemical compound C1CCCCC1P(C1CCCCC1)(=O)C1CCCCC1 LEFPWWWXFFNJAA-UHFFFAOYSA-N 0.000 description 2
- ZJIPHXXDPROMEF-UHFFFAOYSA-N dihydroxyphosphanyl dihydrogen phosphite Chemical class OP(O)OP(O)O ZJIPHXXDPROMEF-UHFFFAOYSA-N 0.000 description 2
- WQAWEUZTDVWTDB-UHFFFAOYSA-N dimethyl(oxo)phosphanium Chemical compound C[P+](C)=O WQAWEUZTDVWTDB-UHFFFAOYSA-N 0.000 description 2
- MPQXHAGKBWFSNV-UHFFFAOYSA-N oxidophosphanium Chemical class [PH3]=O MPQXHAGKBWFSNV-UHFFFAOYSA-N 0.000 description 2
- 150000003003 phosphines Chemical class 0.000 description 2
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 2
- KIZGBMSFXOHDPW-UHFFFAOYSA-N 1-[bis(2-methylpropyl)phosphoryl]-2-methylpropane Chemical compound CC(C)CP(=O)(CC(C)C)CC(C)C KIZGBMSFXOHDPW-UHFFFAOYSA-N 0.000 description 1
- ZSSWXNPRLJLCDU-UHFFFAOYSA-N 1-diethylphosphorylethane Chemical compound CCP(=O)(CC)CC ZSSWXNPRLJLCDU-UHFFFAOYSA-N 0.000 description 1
- SIDULKZCBGMXJL-UHFFFAOYSA-N 1-dimethylphosphoryldodecane Chemical compound CCCCCCCCCCCCP(C)(C)=O SIDULKZCBGMXJL-UHFFFAOYSA-N 0.000 description 1
- ZFZIAYPKDVEXDG-UHFFFAOYSA-N 1-dimethylphosphoryloctadecane Chemical compound CCCCCCCCCCCCCCCCCCP(C)(C)=O ZFZIAYPKDVEXDG-UHFFFAOYSA-N 0.000 description 1
- LSCHYBAAWCZBDM-UHFFFAOYSA-N 1-dimethylphosphoryloctane Chemical compound CCCCCCCCP(C)(C)=O LSCHYBAAWCZBDM-UHFFFAOYSA-N 0.000 description 1
- XHOHEJRYAPSRPZ-UHFFFAOYSA-N 1-dioctadecylphosphoryloctadecane Chemical compound CCCCCCCCCCCCCCCCCCP(=O)(CCCCCCCCCCCCCCCCCC)CCCCCCCCCCCCCCCCCC XHOHEJRYAPSRPZ-UHFFFAOYSA-N 0.000 description 1
- SNZSAFILJOCMFM-UHFFFAOYSA-N 1-dipropylphosphorylpropane Chemical compound CCCP(=O)(CCC)CCC SNZSAFILJOCMFM-UHFFFAOYSA-N 0.000 description 1
- ZZSSCCQEJRAFTD-UHFFFAOYSA-N 1-octylphosphonoyloctane Chemical compound CCCCCCCCP(=O)CCCCCCCC ZZSSCCQEJRAFTD-UHFFFAOYSA-N 0.000 description 1
- AHDSRXYHVZECER-UHFFFAOYSA-N 2,4,6-tris[(dimethylamino)methyl]phenol Chemical compound CN(C)CC1=CC(CN(C)C)=C(O)C(CN(C)C)=C1 AHDSRXYHVZECER-UHFFFAOYSA-N 0.000 description 1
- LCFVJGUPQDGYKZ-UHFFFAOYSA-N Bisphenol A diglycidyl ether Chemical compound C=1C=C(OCC2OC2)C=CC=1C(C)(C)C(C=C1)=CC=C1OCC1CO1 LCFVJGUPQDGYKZ-UHFFFAOYSA-N 0.000 description 1
- MAHOCSYCIVHVPT-UHFFFAOYSA-N C(CCCCCCCCCCCCCCCCC)P(CCCCCCCCCCCCCCCCCC)=O Chemical compound C(CCCCCCCCCCCCCCCCC)P(CCCCCCCCCCCCCCCCCC)=O MAHOCSYCIVHVPT-UHFFFAOYSA-N 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- 229920000877 Melamine resin Polymers 0.000 description 1
- ZEYULRWCONMDRY-UHFFFAOYSA-N [butyl(phenyl)phosphoryl]benzene Chemical compound C=1C=CC=CC=1P(=O)(CCCC)C1=CC=CC=C1 ZEYULRWCONMDRY-UHFFFAOYSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000000853 adhesive Substances 0.000 description 1
- 230000001070 adhesive effect Effects 0.000 description 1
- 239000010425 asbestos Substances 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- FEYBQJQBTXMRPU-UHFFFAOYSA-N butyl(oxido)phosphanium Chemical group CCCC[PH2]=O FEYBQJQBTXMRPU-UHFFFAOYSA-N 0.000 description 1
- QYGNFNURXBPNIB-UHFFFAOYSA-N butylphosphonoylbenzene Chemical compound CCCCP(=O)C1=CC=CC=C1 QYGNFNURXBPNIB-UHFFFAOYSA-N 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- WDIIYWASEVHBBT-UHFFFAOYSA-N di(propan-2-yl)phosphane Chemical compound CC(C)PC(C)C WDIIYWASEVHBBT-UHFFFAOYSA-N 0.000 description 1
- RDLZJCXTAYHYHX-UHFFFAOYSA-N dibenzylphosphorylmethylbenzene Chemical compound C=1C=CC=CC=1CP(CC=1C=CC=CC=1)(=O)CC1=CC=CC=C1 RDLZJCXTAYHYHX-UHFFFAOYSA-N 0.000 description 1
- JMCNGFNJWDJIIV-UHFFFAOYSA-N dibutyl(oxo)phosphanium Chemical compound CCCC[P+](=O)CCCC JMCNGFNJWDJIIV-UHFFFAOYSA-N 0.000 description 1
- WCYAKKWAZWUWLP-UHFFFAOYSA-N dibutylphosphorylbenzene Chemical compound CCCCP(=O)(CCCC)C1=CC=CC=C1 WCYAKKWAZWUWLP-UHFFFAOYSA-N 0.000 description 1
- NLORAJAXZBEDKS-UHFFFAOYSA-N dicyclopentylphosphorylcyclopentane Chemical compound C1CCCC1P(C1CCCC1)(=O)C1CCCC1 NLORAJAXZBEDKS-UHFFFAOYSA-N 0.000 description 1
- IWQIEVOJUWFMSB-UHFFFAOYSA-N dihexylphosphane Chemical compound CCCCCCPCCCCCC IWQIEVOJUWFMSB-UHFFFAOYSA-N 0.000 description 1
- LRMLWYXJORUTBG-UHFFFAOYSA-N dimethylphosphorylmethane Chemical compound CP(C)(C)=O LRMLWYXJORUTBG-UHFFFAOYSA-N 0.000 description 1
- XROMZTPZKHMHRY-UHFFFAOYSA-N dimethylphosphorylmethylbenzene Chemical compound CP(C)(=O)CC1=CC=CC=C1 XROMZTPZKHMHRY-UHFFFAOYSA-N 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 238000013007 heat curing Methods 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 125000001183 hydrocarbyl group Chemical group 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 239000012948 isocyanate Substances 0.000 description 1
- 150000002513 isocyanates Chemical class 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 239000010445 mica Substances 0.000 description 1
- 229910052618 mica group Inorganic materials 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 239000002480 mineral oil Substances 0.000 description 1
- 235000010446 mineral oil Nutrition 0.000 description 1
- 230000000051 modifying effect Effects 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 239000005011 phenolic resin Substances 0.000 description 1
- 229920001568 phenolic resin Polymers 0.000 description 1
- 150000003018 phosphorus compounds Chemical class 0.000 description 1
- 229910000073 phosphorus hydride Inorganic materials 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 229920000768 polyamine Polymers 0.000 description 1
- 229910052895 riebeckite Inorganic materials 0.000 description 1
- 238000007493 shaping process Methods 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 239000011269 tar Substances 0.000 description 1
- IGNTWNVBGLNYDV-UHFFFAOYSA-N triisopropylphosphine Chemical compound CC(C)P(C(C)C)C(C)C IGNTWNVBGLNYDV-UHFFFAOYSA-N 0.000 description 1
- FIQMHBFVRAXMOP-UHFFFAOYSA-N triphenylphosphane oxide Chemical compound C=1C=CC=CC=1P(C=1C=CC=CC=1)(=O)C1=CC=CC=C1 FIQMHBFVRAXMOP-UHFFFAOYSA-N 0.000 description 1
- COIOYMYWGDAQPM-UHFFFAOYSA-N tris(2-methylphenyl)phosphane Chemical compound CC1=CC=CC=C1P(C=1C(=CC=CC=1)C)C1=CC=CC=C1C COIOYMYWGDAQPM-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
- C08G59/68—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 catalysts used
- C08G59/688—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 catalysts used containing phosphorus
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)
- Compositions Of Macromolecular Compounds (AREA)
Priority Applications (9)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19712104910 DE2104910A1 (de) | 1971-02-03 | 1971-02-03 | Verfahren zur Herstellung von Polyaddukten auf der Basis von Epoxidharzen |
| CH82672A CH568342A5 (OSRAM) | 1971-02-03 | 1972-01-20 | |
| GB396272A GB1355932A (en) | 1971-02-03 | 1972-01-27 | Process for the production of shaped and cured epoxide resins |
| NL7201199A NL7201199A (OSRAM) | 1971-02-03 | 1972-01-28 | |
| US00222695A US3759872A (en) | 1971-02-03 | 1972-02-01 | E accelerators process for the production of epoxide polyadducts with phosphine oxid |
| ES399406A ES399406A1 (es) | 1971-02-03 | 1972-02-02 | Procedimiento para la preparacion de poliaductos a base de resinas epoxidicas. |
| FR727203454A FR2124386B1 (OSRAM) | 1971-02-03 | 1972-02-02 | |
| CA133,740A CA957448A (en) | 1971-02-03 | 1972-02-02 | Process for the production of epoxide polyadducts |
| IT20128/72A IT947234B (it) | 1971-02-03 | 1972-02-02 | Processo per la preparazione di composti di poliaddizione a base di resine epossidiche |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19712104910 DE2104910A1 (de) | 1971-02-03 | 1971-02-03 | Verfahren zur Herstellung von Polyaddukten auf der Basis von Epoxidharzen |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2104910A1 true DE2104910A1 (de) | 1972-09-14 |
Family
ID=5797654
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19712104910 Pending DE2104910A1 (de) | 1971-02-03 | 1971-02-03 | Verfahren zur Herstellung von Polyaddukten auf der Basis von Epoxidharzen |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US3759872A (OSRAM) |
| CA (1) | CA957448A (OSRAM) |
| CH (1) | CH568342A5 (OSRAM) |
| DE (1) | DE2104910A1 (OSRAM) |
| ES (1) | ES399406A1 (OSRAM) |
| FR (1) | FR2124386B1 (OSRAM) |
| GB (1) | GB1355932A (OSRAM) |
| IT (1) | IT947234B (OSRAM) |
| NL (1) | NL7201199A (OSRAM) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE19800178B4 (de) * | 1997-01-08 | 2010-07-22 | Shin-Etsu Chemical Co., Ltd. | Gehärtetes Produkt einer Epoxyharzmasse zur Halbleitereinkapselung und dessen Verwendung |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4477645A (en) * | 1983-07-21 | 1984-10-16 | The Dow Chemical Company | Immobilized epoxy advancement initiators |
| US6297332B1 (en) | 1998-04-28 | 2001-10-02 | Mitsui Chemicals, Inc. | Epoxy-resin composition and use thereof |
| US6310147B1 (en) | 1998-05-21 | 2001-10-30 | Mitsui Chemicals, Inc. | Epoxy-resin composition and use thereof |
-
1971
- 1971-02-03 DE DE19712104910 patent/DE2104910A1/de active Pending
-
1972
- 1972-01-20 CH CH82672A patent/CH568342A5/xx not_active IP Right Cessation
- 1972-01-27 GB GB396272A patent/GB1355932A/en not_active Expired
- 1972-01-28 NL NL7201199A patent/NL7201199A/xx unknown
- 1972-02-01 US US00222695A patent/US3759872A/en not_active Expired - Lifetime
- 1972-02-02 ES ES399406A patent/ES399406A1/es not_active Expired
- 1972-02-02 FR FR727203454A patent/FR2124386B1/fr not_active Expired
- 1972-02-02 IT IT20128/72A patent/IT947234B/it active
- 1972-02-02 CA CA133,740A patent/CA957448A/en not_active Expired
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE19800178B4 (de) * | 1997-01-08 | 2010-07-22 | Shin-Etsu Chemical Co., Ltd. | Gehärtetes Produkt einer Epoxyharzmasse zur Halbleitereinkapselung und dessen Verwendung |
Also Published As
| Publication number | Publication date |
|---|---|
| CH568342A5 (OSRAM) | 1975-10-31 |
| ES399406A1 (es) | 1974-10-16 |
| GB1355932A (en) | 1974-06-12 |
| US3759872A (en) | 1973-09-18 |
| IT947234B (it) | 1973-05-21 |
| CA957448A (en) | 1974-11-05 |
| NL7201199A (OSRAM) | 1972-08-07 |
| FR2124386B1 (OSRAM) | 1974-06-28 |
| FR2124386A1 (OSRAM) | 1972-09-22 |
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