DE2115918C3 - Verfahren zur Herstellung von Epoxydpolyaddukten - Google Patents
Verfahren zur Herstellung von EpoxydpolyadduktenInfo
- Publication number
- DE2115918C3 DE2115918C3 DE2115918A DE2115918A DE2115918C3 DE 2115918 C3 DE2115918 C3 DE 2115918C3 DE 2115918 A DE2115918 A DE 2115918A DE 2115918 A DE2115918 A DE 2115918A DE 2115918 C3 DE2115918 C3 DE 2115918C3
- Authority
- DE
- Germany
- Prior art keywords
- epoxy
- acid
- groups
- anhydride
- polycarboxylic
- 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
- 239000004593 Epoxy Substances 0.000 title claims description 40
- 238000000034 method Methods 0.000 title claims description 8
- 238000004519 manufacturing process Methods 0.000 title claims description 6
- 239000002253 acid Substances 0.000 claims description 30
- 125000003700 epoxy group Chemical group 0.000 claims description 25
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 claims description 23
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims description 22
- 150000008064 anhydrides Chemical class 0.000 claims description 15
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 14
- 150000002148 esters Chemical class 0.000 claims description 14
- 150000001875 compounds Chemical class 0.000 claims description 11
- 230000005855 radiation Effects 0.000 claims description 10
- 239000000178 monomer Substances 0.000 claims description 9
- 150000007513 acids Chemical class 0.000 claims description 7
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 claims description 6
- 150000008065 acid anhydrides Chemical class 0.000 claims description 6
- 239000000203 mixture Substances 0.000 claims description 6
- 150000002763 monocarboxylic acids Chemical class 0.000 claims description 6
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 claims description 5
- 238000010894 electron beam technology Methods 0.000 claims description 5
- 230000032050 esterification Effects 0.000 claims description 5
- 238000005886 esterification reaction Methods 0.000 claims description 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 4
- 229920003986 novolac Polymers 0.000 claims description 4
- -1 phenolic ethers Chemical class 0.000 claims description 4
- 238000006116 polymerization reaction Methods 0.000 claims description 4
- 239000003054 catalyst Substances 0.000 claims description 3
- 239000007859 condensation product Substances 0.000 claims description 3
- 239000003112 inhibitor Substances 0.000 claims description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 2
- 150000001491 aromatic compounds Chemical class 0.000 claims description 2
- LDHQCZJRKDOVOX-NSCUHMNNSA-N crotonic acid Chemical compound C\C=C\C(O)=O LDHQCZJRKDOVOX-NSCUHMNNSA-N 0.000 claims description 2
- 230000006735 deficit Effects 0.000 claims description 2
- 230000008030 elimination Effects 0.000 claims description 2
- 238000003379 elimination reaction Methods 0.000 claims description 2
- 229910000041 hydrogen chloride Inorganic materials 0.000 claims description 2
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 claims description 2
- LDHQCZJRKDOVOX-UHFFFAOYSA-N trans-crotonic acid Natural products CC=CC(O)=O LDHQCZJRKDOVOX-UHFFFAOYSA-N 0.000 claims description 2
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims 3
- 239000011541 reaction mixture Substances 0.000 claims 1
- 229920000647 polyepoxide Polymers 0.000 description 16
- 150000002924 oxiranes Chemical class 0.000 description 13
- LGRFSURHDFAFJT-UHFFFAOYSA-N Phthalic anhydride Natural products C1=CC=C2C(=O)OC(=O)C2=C1 LGRFSURHDFAFJT-UHFFFAOYSA-N 0.000 description 12
- JHIWVOJDXOSYLW-UHFFFAOYSA-N butyl 2,2-difluorocyclopropane-1-carboxylate Chemical compound CCCCOC(=O)C1CC1(F)F JHIWVOJDXOSYLW-UHFFFAOYSA-N 0.000 description 11
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 10
- 229920000728 polyester Polymers 0.000 description 10
- 229920005989 resin Polymers 0.000 description 9
- 239000011347 resin Substances 0.000 description 9
- 239000003822 epoxy resin Substances 0.000 description 7
- 150000002762 monocarboxylic acid derivatives Chemical class 0.000 description 7
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 5
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 4
- 230000001588 bifunctional effect Effects 0.000 description 4
- 238000000576 coating method Methods 0.000 description 4
- 230000000052 comparative effect Effects 0.000 description 4
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 4
- 239000011248 coating agent Substances 0.000 description 3
- SRPWOOOHEPICQU-UHFFFAOYSA-N trimellitic anhydride Chemical compound OC(=O)C1=CC=C2C(=O)OC(=O)C2=C1 SRPWOOOHEPICQU-UHFFFAOYSA-N 0.000 description 3
- QTWJRLJHJPIABL-UHFFFAOYSA-N 2-methylphenol;3-methylphenol;4-methylphenol Chemical compound CC1=CC=C(O)C=C1.CC1=CC=CC(O)=C1.CC1=CC=CC=C1O QTWJRLJHJPIABL-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- JIGUQPWFLRLWPJ-UHFFFAOYSA-N Ethyl acrylate Chemical compound CCOC(=O)C=C JIGUQPWFLRLWPJ-UHFFFAOYSA-N 0.000 description 2
- JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 description 2
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 2
- 150000001735 carboxylic acids Chemical class 0.000 description 2
- 229930003836 cresol Natural products 0.000 description 2
- 238000004132 cross linking Methods 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- PNJWIWWMYCMZRO-UHFFFAOYSA-N pent‐4‐en‐2‐one Natural products CC(=O)CC=C PNJWIWWMYCMZRO-UHFFFAOYSA-N 0.000 description 2
- HJWLCRVIBGQPNF-UHFFFAOYSA-N prop-2-enylbenzene Chemical compound C=CCC1=CC=CC=C1 HJWLCRVIBGQPNF-UHFFFAOYSA-N 0.000 description 2
- KDYFGRWQOYBRFD-UHFFFAOYSA-N succinic acid Chemical compound OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 2
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 2
- YJTKZCDBKVTVBY-UHFFFAOYSA-N 1,3-Diphenylbenzene Chemical group C1=CC=CC=C1C1=CC=CC(C=2C=CC=CC=2)=C1 YJTKZCDBKVTVBY-UHFFFAOYSA-N 0.000 description 1
- NJBCRXCAPCODGX-UHFFFAOYSA-N 2-methyl-n-(2-methylpropyl)propan-1-amine Chemical compound CC(C)CNCC(C)C NJBCRXCAPCODGX-UHFFFAOYSA-N 0.000 description 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- JLBJTVDPSNHSKJ-UHFFFAOYSA-N 4-Methylstyrene Chemical compound CC1=CC=C(C=C)C=C1 JLBJTVDPSNHSKJ-UHFFFAOYSA-N 0.000 description 1
- 239000004135 Bone phosphate Substances 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- BGNXCDMCOKJUMV-UHFFFAOYSA-N Tert-Butylhydroquinone Chemical compound CC(C)(C)C1=CC(O)=CC=C1O BGNXCDMCOKJUMV-UHFFFAOYSA-N 0.000 description 1
- 230000001133 acceleration Effects 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 239000001361 adipic acid Substances 0.000 description 1
- 235000011037 adipic acid Nutrition 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000011951 cationic catalyst Substances 0.000 description 1
- 239000011093 chipboard Substances 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 238000007334 copolymerization reaction Methods 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 239000011888 foil Substances 0.000 description 1
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 description 1
- 238000000465 moulding Methods 0.000 description 1
- 230000006855 networking Effects 0.000 description 1
- 238000010422 painting Methods 0.000 description 1
- 150000002978 peroxides Chemical class 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 229920000515 polycarbonate Polymers 0.000 description 1
- 239000004417 polycarbonate Substances 0.000 description 1
- BDAWXSQJJCIFIK-UHFFFAOYSA-N potassium methoxide Chemical compound [K+].[O-]C BDAWXSQJJCIFIK-UHFFFAOYSA-N 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000001384 succinic acid Substances 0.000 description 1
- 239000004250 tert-Butylhydroquinone Substances 0.000 description 1
- 235000019281 tert-butylhydroquinone Nutrition 0.000 description 1
- 230000008542 thermal sensitivity Effects 0.000 description 1
- 238000005809 transesterification reaction Methods 0.000 description 1
- 125000005270 trialkylamine group Chemical group 0.000 description 1
- 239000008096 xylene Substances 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
- C08G59/42—Polycarboxylic acids; Anhydrides, halides or low molecular weight esters thereof
- C08G59/4292—Polycarboxylic acids; Anhydrides, halides or low molecular weight esters thereof together with monocarboxylic acids
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F283/00—Macromolecular compounds obtained by polymerising monomers on to polymers provided for in subclass C08G
- C08F283/01—Macromolecular compounds obtained by polymerising monomers on to polymers provided for in subclass C08G on to unsaturated polyesters
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)
- Macromonomer-Based Addition Polymer (AREA)
Priority Applications (10)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2115918A DE2115918C3 (de) | 1971-04-01 | 1971-04-01 | Verfahren zur Herstellung von Epoxydpolyaddukten |
| AT217372A AT322218B (de) | 1971-04-01 | 1972-03-15 | Verfahren zur herstellung von vernetzten epoxydharzen |
| FR7210623A FR2136056A5 (enExample) | 1971-04-01 | 1972-03-27 | |
| IT22571/72A IT950886B (it) | 1971-04-01 | 1972-03-29 | Procedimento per l indurimento di resine esteree |
| CH481272A CH571547A5 (enExample) | 1971-04-01 | 1972-03-30 | |
| GB1515872A GB1382485A (en) | 1971-04-01 | 1972-03-30 | Process for hardening resins |
| CA138,624A CA975713A (en) | 1971-04-01 | 1972-03-30 | Process for hardening resins |
| ES401374A ES401374A1 (es) | 1971-04-01 | 1972-03-30 | Procedimiento para el endurecimiento de resinas de ester. |
| NLAANVRAGE7204426,A NL170634C (nl) | 1971-04-01 | 1972-04-01 | Werkwijze voor het harden met behulp van elektronenstralen van mengsels van epoxyesters en onverzadigde monomeren. |
| US05/702,352 US4101398A (en) | 1971-04-01 | 1976-07-02 | Process for hardening a resin which is the reaction product of an epoxy resin, an olefinically unsaturated monocarboxylic acid and a polycarboxylic acid anhydride unit |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2115918A DE2115918C3 (de) | 1971-04-01 | 1971-04-01 | Verfahren zur Herstellung von Epoxydpolyaddukten |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DE2115918A1 DE2115918A1 (de) | 1972-10-12 |
| DE2115918B2 DE2115918B2 (de) | 1974-07-18 |
| DE2115918C3 true DE2115918C3 (de) | 1980-04-24 |
Family
ID=5803588
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2115918A Expired DE2115918C3 (de) | 1971-04-01 | 1971-04-01 | Verfahren zur Herstellung von Epoxydpolyaddukten |
Country Status (10)
| Country | Link |
|---|---|
| US (1) | US4101398A (enExample) |
| AT (1) | AT322218B (enExample) |
| CA (1) | CA975713A (enExample) |
| CH (1) | CH571547A5 (enExample) |
| DE (1) | DE2115918C3 (enExample) |
| ES (1) | ES401374A1 (enExample) |
| FR (1) | FR2136056A5 (enExample) |
| GB (1) | GB1382485A (enExample) |
| IT (1) | IT950886B (enExample) |
| NL (1) | NL170634C (enExample) |
Families Citing this family (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4256828A (en) * | 1975-09-02 | 1981-03-17 | Minnesota Mining And Manufacturing Company | Photocopolymerizable compositions based on epoxy and hydroxyl-containing organic materials |
| CA1117690A (en) * | 1978-03-09 | 1982-02-02 | Kazys Sekmakas | Water soluble epoxy ester copolymers for sanitary can use |
| US4296011A (en) * | 1979-03-09 | 1981-10-20 | Desoto, Inc. | Epoxy ester copolymer aqueous dispersions |
| US4247659A (en) * | 1979-03-09 | 1981-01-27 | Desoto, Inc. | Epoxy ester copolymer soluble in water with the aid of an amine |
| JPS59126425A (ja) * | 1982-08-30 | 1984-07-21 | Japan Atom Energy Res Inst | 自己硬化性改質エポキシ樹脂組成物およびその水散体 |
| JPS61243869A (ja) * | 1985-04-19 | 1986-10-30 | Taiyo Ink Seizo Kk | レジストインキ組成物 |
| JPS63258975A (ja) * | 1986-12-26 | 1988-10-26 | Toshiba Corp | ソルダーレジストインキ組成物 |
| JPS6462375A (en) * | 1987-09-02 | 1989-03-08 | Arakawa Chem Ind | Liquid photosolder resist ink composition of alkali development type |
| GB2235925B (en) * | 1989-09-12 | 1992-09-30 | Sericol Group Ltd | Photocurable compositions |
| US6045857A (en) * | 1997-06-19 | 2000-04-04 | Macdermid Acumen, Inc. | Curable, water-borne one-component coating system using thermally labile hydrophillic groups |
| US6583198B2 (en) * | 1997-11-28 | 2003-06-24 | Hitachi Chemical Company, Ltd. | Photo curable resin composition and photosensitive element |
| CN111217988A (zh) * | 2019-12-31 | 2020-06-02 | 广东立邦长润发科技材料有限公司 | 一种可紫外光固化多官环氧丙烯酸酯及其制备方法 |
| CN114195953B (zh) * | 2021-12-16 | 2023-08-25 | 科之杰新材料集团浙江有限公司 | 一种低敏感高保水型聚羧酸减水剂及其制备方法 |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3564074A (en) * | 1966-11-28 | 1971-02-16 | Dow Chemical Co | Thermosetting vinyl resins reacted with dicarboxylic acid anhydrides |
| US3466259A (en) * | 1966-12-15 | 1969-09-09 | Dow Chemical Co | Thickened thermosetting vinyl ester resins |
| US3632861A (en) * | 1969-03-19 | 1972-01-04 | American Cyanamid Co | Vinyl ester resins from epoxides and isomerized hydroxy alkyl acrylates-aleic anhydride reaction product |
| US3683045A (en) * | 1970-12-02 | 1972-08-08 | Walton Leon Baldwin | Phenothiazine stabilized vinyl ester resins |
-
1971
- 1971-04-01 DE DE2115918A patent/DE2115918C3/de not_active Expired
-
1972
- 1972-03-15 AT AT217372A patent/AT322218B/de not_active IP Right Cessation
- 1972-03-27 FR FR7210623A patent/FR2136056A5/fr not_active Expired
- 1972-03-29 IT IT22571/72A patent/IT950886B/it active
- 1972-03-30 CA CA138,624A patent/CA975713A/en not_active Expired
- 1972-03-30 ES ES401374A patent/ES401374A1/es not_active Expired
- 1972-03-30 CH CH481272A patent/CH571547A5/xx not_active IP Right Cessation
- 1972-03-30 GB GB1515872A patent/GB1382485A/en not_active Expired
- 1972-04-01 NL NLAANVRAGE7204426,A patent/NL170634C/xx not_active IP Right Cessation
-
1976
- 1976-07-02 US US05/702,352 patent/US4101398A/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| NL7204426A (enExample) | 1972-10-03 |
| ES401374A1 (es) | 1975-02-16 |
| AT322218B (de) | 1975-05-12 |
| IT950886B (it) | 1973-06-20 |
| DE2115918A1 (de) | 1972-10-12 |
| CA975713A (en) | 1975-10-07 |
| US4101398A (en) | 1978-07-18 |
| GB1382485A (en) | 1975-02-05 |
| FR2136056A5 (enExample) | 1972-12-22 |
| DE2115918B2 (de) | 1974-07-18 |
| NL170634C (nl) | 1982-12-01 |
| NL170634B (nl) | 1982-07-01 |
| CH571547A5 (enExample) | 1976-01-15 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C3 | Grant after two publication steps (3rd publication) |