CA1215193A - Hydrolyzing epoxy resins in absence of solvent and in presence of oxalic acid and a phosphonium compound - Google Patents
Hydrolyzing epoxy resins in absence of solvent and in presence of oxalic acid and a phosphonium compoundInfo
- Publication number
- CA1215193A CA1215193A CA000434684A CA434684A CA1215193A CA 1215193 A CA1215193 A CA 1215193A CA 000434684 A CA000434684 A CA 000434684A CA 434684 A CA434684 A CA 434684A CA 1215193 A CA1215193 A CA 1215193A
- Authority
- CA
- Canada
- Prior art keywords
- catalyst
- epoxy
- epoxy resin
- hour
- mole
- 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
- 229920000647 polyepoxide Polymers 0.000 title claims abstract description 33
- 239000003822 epoxy resin Substances 0.000 title claims abstract description 32
- -1 phosphonium compound Chemical class 0.000 title claims abstract description 8
- 230000003301 hydrolyzing effect Effects 0.000 title claims abstract description 6
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 title claims description 12
- 235000006408 oxalic acid Nutrition 0.000 title claims description 4
- 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 abstract description 9
- 239000002904 solvent Substances 0.000 title description 4
- 239000003054 catalyst Substances 0.000 claims abstract description 39
- 238000000034 method Methods 0.000 claims abstract description 14
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 13
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims abstract description 6
- 239000003960 organic solvent Substances 0.000 claims abstract description 6
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims abstract description 4
- 230000003197 catalytic effect Effects 0.000 claims abstract description 3
- 238000006243 chemical reaction Methods 0.000 claims abstract description 3
- 150000002118 epoxides Chemical class 0.000 claims description 7
- 125000004432 carbon atom Chemical group C* 0.000 claims description 3
- SRWLXBHGOYPTCM-UHFFFAOYSA-M acetic acid;ethyl(triphenyl)phosphanium;acetate Chemical compound CC(O)=O.CC([O-])=O.C=1C=CC=CC=1[P+](C=1C=CC=CC=1)(CC)C1=CC=CC=C1 SRWLXBHGOYPTCM-UHFFFAOYSA-M 0.000 claims description 2
- 239000008199 coating composition Substances 0.000 abstract description 6
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 34
- 229910052757 nitrogen Inorganic materials 0.000 description 17
- 239000004593 Epoxy Substances 0.000 description 14
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Natural products CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 10
- 238000000576 coating method Methods 0.000 description 10
- 239000000047 product Substances 0.000 description 10
- 229920005989 resin Polymers 0.000 description 10
- 239000011347 resin Substances 0.000 description 10
- 239000011248 coating agent Substances 0.000 description 9
- 125000003700 epoxy group Chemical group 0.000 description 9
- 238000012360 testing method Methods 0.000 description 7
- 229960000583 acetic acid Drugs 0.000 description 5
- 239000003795 chemical substances by application Substances 0.000 description 5
- 238000002474 experimental method Methods 0.000 description 4
- 239000012362 glacial acetic acid Substances 0.000 description 4
- 230000007062 hydrolysis Effects 0.000 description 4
- 238000006460 hydrolysis reaction Methods 0.000 description 4
- 229920003986 novolac Polymers 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- GYZLOYUZLJXAJU-UHFFFAOYSA-N diglycidyl ether Chemical compound C1OC1COCC1CO1 GYZLOYUZLJXAJU-UHFFFAOYSA-N 0.000 description 3
- 229910052739 hydrogen Inorganic materials 0.000 description 3
- 239000000758 substrate Substances 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 239000003377 acid catalyst Substances 0.000 description 2
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 2
- 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 2
- 239000010960 cold rolled steel Substances 0.000 description 2
- SLGWESQGEUXWJQ-UHFFFAOYSA-N formaldehyde;phenol Chemical group O=C.OC1=CC=CC=C1 SLGWESQGEUXWJQ-UHFFFAOYSA-N 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- BDJRBEYXGGNYIS-UHFFFAOYSA-N nonanedioic acid Chemical compound OC(=O)CCCCCCCC(O)=O BDJRBEYXGGNYIS-UHFFFAOYSA-N 0.000 description 2
- 229920001568 phenolic resin Polymers 0.000 description 2
- XYFCBTPGUUZFHI-UHFFFAOYSA-O phosphonium Chemical compound [PH4+] XYFCBTPGUUZFHI-UHFFFAOYSA-O 0.000 description 2
- WLJVNTCWHIRURA-UHFFFAOYSA-N pimelic acid Chemical compound OC(=O)CCCCCC(O)=O WLJVNTCWHIRURA-UHFFFAOYSA-N 0.000 description 2
- CXMXRPHRNRROMY-UHFFFAOYSA-N sebacic acid Chemical compound OC(=O)CCCCCCCCC(O)=O CXMXRPHRNRROMY-UHFFFAOYSA-N 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- TYFQFVWCELRYAO-UHFFFAOYSA-N suberic acid Chemical compound OC(=O)CCCCCCC(O)=O TYFQFVWCELRYAO-UHFFFAOYSA-N 0.000 description 2
- GFZMLBWMGBLIDI-UHFFFAOYSA-M tetrabutylphosphanium;acetate Chemical compound CC([O-])=O.CCCC[P+](CCCC)(CCCC)CCCC GFZMLBWMGBLIDI-UHFFFAOYSA-M 0.000 description 2
- LHENQXAPVKABON-UHFFFAOYSA-N 1-methoxypropan-1-ol Chemical compound CCC(O)OC LHENQXAPVKABON-UHFFFAOYSA-N 0.000 description 1
- RTBFRGCFXZNCOE-UHFFFAOYSA-N 1-methylsulfonylpiperidin-4-one Chemical compound CS(=O)(=O)N1CCC(=O)CC1 RTBFRGCFXZNCOE-UHFFFAOYSA-N 0.000 description 1
- ZRYCRPNCXLQHPN-UHFFFAOYSA-N 3-hydroxy-2-methylbenzaldehyde Chemical compound CC1=C(O)C=CC=C1C=O ZRYCRPNCXLQHPN-UHFFFAOYSA-N 0.000 description 1
- VPWNQTHUCYMVMZ-UHFFFAOYSA-N 4,4'-sulfonyldiphenol Chemical class C1=CC(O)=CC=C1S(=O)(=O)C1=CC=C(O)C=C1 VPWNQTHUCYMVMZ-UHFFFAOYSA-N 0.000 description 1
- WFCQTAXSWSWIHS-UHFFFAOYSA-N 4-[bis(4-hydroxyphenyl)methyl]phenol Chemical compound C1=CC(O)=CC=C1C(C=1C=CC(O)=CC=1)C1=CC=C(O)C=C1 WFCQTAXSWSWIHS-UHFFFAOYSA-N 0.000 description 1
- 229930185605 Bisphenol Natural products 0.000 description 1
- 229910000831 Steel Inorganic materials 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 1
- 229920001807 Urea-formaldehyde Polymers 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000001361 adipic acid Substances 0.000 description 1
- 235000011037 adipic acid Nutrition 0.000 description 1
- GZCGUPFRVQAUEE-SLPGGIOYSA-N aldehydo-D-glucose Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C=O GZCGUPFRVQAUEE-SLPGGIOYSA-N 0.000 description 1
- 150000007824 aliphatic compounds Chemical class 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- JFCQEDHGNNZCLN-UHFFFAOYSA-N anhydrous glutaric acid Natural products OC(=O)CCCC(O)=O JFCQEDHGNNZCLN-UHFFFAOYSA-N 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 150000001491 aromatic compounds Chemical class 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 235000013351 cheese Nutrition 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 150000001991 dicarboxylic acids Chemical class 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- HZZUMXSLPJFMCB-UHFFFAOYSA-M ethyl(triphenyl)phosphanium;acetate Chemical compound CC([O-])=O.C=1C=CC=CC=1[P+](C=1C=CC=CC=1)(CC)C1=CC=CC=C1 HZZUMXSLPJFMCB-UHFFFAOYSA-M 0.000 description 1
- JHYNXXDQQHTCHJ-UHFFFAOYSA-M ethyl(triphenyl)phosphanium;bromide Chemical compound [Br-].C=1C=CC=CC=1[P+](C=1C=CC=CC=1)(CC)C1=CC=CC=C1 JHYNXXDQQHTCHJ-UHFFFAOYSA-M 0.000 description 1
- NJXBVBPTDHBAID-UHFFFAOYSA-M ethyl(triphenyl)phosphanium;chloride Chemical compound [Cl-].C=1C=CC=CC=1[P+](C=1C=CC=CC=1)(CC)C1=CC=CC=C1 NJXBVBPTDHBAID-UHFFFAOYSA-M 0.000 description 1
- SLAFUPJSGFVWPP-UHFFFAOYSA-M ethyl(triphenyl)phosphanium;iodide Chemical compound [I-].C=1C=CC=CC=1[P+](C=1C=CC=CC=1)(CC)C1=CC=CC=C1 SLAFUPJSGFVWPP-UHFFFAOYSA-M 0.000 description 1
- 239000004744 fabric Substances 0.000 description 1
- WSFSSNUMVMOOMR-UHFFFAOYSA-N formaldehyde Substances O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 150000004677 hydrates Chemical class 0.000 description 1
- 230000006698 induction Effects 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 150000004010 onium ions Chemical class 0.000 description 1
- 235000020030 perry Nutrition 0.000 description 1
- BZDGQUJIIQRTNH-UHFFFAOYSA-N phosphanium;acetic acid;acetate Chemical compound [PH4+].CC(O)=O.CC([O-])=O BZDGQUJIIQRTNH-UHFFFAOYSA-N 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 239000010959 steel Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- VCENTMAPZCSHBO-UHFFFAOYSA-L tetrabutylphosphanium diacetate Chemical compound CC([O-])=O.CC([O-])=O.CCCC[P+](CCCC)(CCCC)CCCC.CCCC[P+](CCCC)(CCCC)CCCC VCENTMAPZCSHBO-UHFFFAOYSA-L 0.000 description 1
- IBWGNZVCJVLSHB-UHFFFAOYSA-M tetrabutylphosphanium;chloride Chemical compound [Cl-].CCCC[P+](CCCC)(CCCC)CCCC IBWGNZVCJVLSHB-UHFFFAOYSA-M 0.000 description 1
- CCIYPTIBRAUPLQ-UHFFFAOYSA-M tetrabutylphosphanium;iodide Chemical compound [I-].CCCC[P+](CCCC)(CCCC)CCCC CCIYPTIBRAUPLQ-UHFFFAOYSA-M 0.000 description 1
- 238000005406 washing Methods 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
- C08G59/14—Polycondensates modified by chemical after-treatment
-
- 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
- C08G59/14—Polycondensates modified by chemical after-treatment
- C08G59/1405—Polycondensates modified by chemical after-treatment with inorganic compounds
- C08G59/1427—Polycondensates modified by chemical after-treatment with inorganic compounds with water, e.g. hydrolysis
Landscapes
- Chemical & Material Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Inorganic Chemistry (AREA)
- Epoxy Resins (AREA)
- Paints Or Removers (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Polyesters Or Polycarbonates (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US408,348 | 1982-08-16 | ||
| US06/408,348 US4404335A (en) | 1982-08-16 | 1982-08-16 | Hydrolyzing epoxy resins in absence of solvent and in presence of oxalic acid and a phosphonium compound |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1215193A true CA1215193A (en) | 1986-12-09 |
Family
ID=23615909
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA000434684A Expired CA1215193A (en) | 1982-08-16 | 1983-08-16 | Hydrolyzing epoxy resins in absence of solvent and in presence of oxalic acid and a phosphonium compound |
Country Status (15)
| Country | Link |
|---|---|
| US (1) | US4404335A (OSRAM) |
| EP (1) | EP0116594B1 (OSRAM) |
| JP (1) | JPS59501666A (OSRAM) |
| KR (1) | KR910006812B1 (OSRAM) |
| AU (1) | AU555147B2 (OSRAM) |
| CA (1) | CA1215193A (OSRAM) |
| DE (1) | DE3379051D1 (OSRAM) |
| DK (1) | DK190184A (OSRAM) |
| ES (1) | ES8505702A1 (OSRAM) |
| GB (1) | GB2127828B (OSRAM) |
| IT (1) | IT1163886B (OSRAM) |
| MY (1) | MY8700078A (OSRAM) |
| NZ (1) | NZ205292A (OSRAM) |
| SG (1) | SG69086G (OSRAM) |
| WO (1) | WO1984000766A1 (OSRAM) |
Families Citing this family (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4724253A (en) * | 1986-06-13 | 1988-02-09 | The Dow Chemical Company | Adducts of partially hydrolyzed epoxy resins and polyamines |
| JPH04270721A (ja) * | 1991-02-26 | 1992-09-28 | Yuka Shell Epoxy Kk | 高反応性高分子量エポキシ樹脂の製造方法 |
| USH1439H (en) * | 1993-10-18 | 1995-05-02 | The Dow Chemical Company | Method to increase the level of α-glycol in liquid epoxy resin |
| PT2474545T (pt) | 2005-12-13 | 2017-02-14 | Incyte Holdings Corp | Pirrolo[2,3-b]piridinas e pirrolo[2,3-b]pirimidinas substituídas com heteroarilo como inibidores de janus quinase |
| BR112012013526A2 (pt) | 2009-12-09 | 2015-09-15 | Dow Global Technologies Llc | composição de resina de dióxido de divinilareno hidrolisada, composição de resina de dióxido de divinilareno hidrolisada curável, processo para hidrolisar uma resina epóxi de divinilareno e processo para preparar uma composição de resina de dióxido de divinilareno hidrolisada curável |
| PE20130038A1 (es) | 2010-03-10 | 2013-01-28 | Incyte Corp | Derivados de piperidin-4-il azetidina como inhibidores de jak1 |
| EA201490042A1 (ru) | 2011-06-20 | 2014-10-30 | Инсайт Корпорейшн | Азетидинил-фенил-, пиридил- или пиразинилкарбоксамидные производные как ингибиторы jak |
| TWI761825B (zh) | 2012-11-15 | 2022-04-21 | 美商英塞特控股公司 | 盧梭利替尼之緩釋性劑型 |
| WO2015021153A1 (en) | 2013-08-07 | 2015-02-12 | Incyte Corporation | Sustained release dosage forms for a jak1 inhibitor |
| WO2015148039A1 (en) | 2014-03-24 | 2015-10-01 | Dow Global Technologies Llc | Partially hydrolyzed epoxy resin compositions |
| US11833155B2 (en) | 2020-06-03 | 2023-12-05 | Incyte Corporation | Combination therapy for treatment of myeloproliferative neoplasms |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3405093A (en) * | 1966-12-05 | 1968-10-08 | Dow Chemical Co | Process for hydrolyzing polyepoxide resins |
| US3632836A (en) * | 1968-10-25 | 1972-01-04 | Dow Chemical Co | Solid curable polyepoxides modified with hydrolyzed liquid polyepoxides |
| US3787508A (en) * | 1968-10-25 | 1974-01-22 | Dow Chemical Co | Solid,curable polyepoxides modified with hydrolyzed liquid polyepoxides |
| US3991028A (en) * | 1970-08-05 | 1976-11-09 | Ppg Industries, Inc. | Hydrolyzed polyepoxide dispersions |
| US3891525A (en) * | 1970-08-05 | 1975-06-24 | Ppg Industries Inc | Method of electro-depositing compositions containing hydrolyzed polyepoxides |
| US4145324A (en) * | 1977-02-09 | 1979-03-20 | Mobil Oil Corporation | Coatings based on hydrolyzed epoxy resins |
| US4340713A (en) * | 1980-11-26 | 1982-07-20 | The Dow Chemical Company | Method for preparing high molecular weight epoxy resins containing hydrolyzed epoxy groups |
| US4358577A (en) * | 1980-11-26 | 1982-11-09 | The Dow Chemical Company | Method for preparing high molecular weight epoxy resins containing hydrolyzed epoxy groups |
-
1982
- 1982-08-16 US US06/408,348 patent/US4404335A/en not_active Expired - Lifetime
-
1983
- 1983-08-04 JP JP58502727A patent/JPS59501666A/ja active Granted
- 1983-08-04 EP EP83902674A patent/EP0116594B1/en not_active Expired
- 1983-08-04 AU AU18833/83A patent/AU555147B2/en not_active Ceased
- 1983-08-04 DE DE8383902674T patent/DE3379051D1/de not_active Expired
- 1983-08-04 WO PCT/US1983/001197 patent/WO1984000766A1/en not_active Ceased
- 1983-08-11 IT IT22514/83A patent/IT1163886B/it active
- 1983-08-12 ES ES524928A patent/ES8505702A1/es not_active Expired
- 1983-08-16 GB GB08322029A patent/GB2127828B/en not_active Expired
- 1983-08-16 CA CA000434684A patent/CA1215193A/en not_active Expired
- 1983-08-16 NZ NZ205292A patent/NZ205292A/en unknown
- 1983-08-16 KR KR1019830003810A patent/KR910006812B1/ko not_active Expired
-
1984
- 1984-04-12 DK DK190184A patent/DK190184A/da not_active Application Discontinuation
-
1986
- 1986-08-20 SG SG690/86A patent/SG69086G/en unknown
-
1987
- 1987-12-30 MY MY78/87A patent/MY8700078A/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| KR840005826A (ko) | 1984-11-19 |
| KR910006812B1 (ko) | 1991-09-02 |
| MY8700078A (en) | 1987-12-31 |
| DK190184D0 (da) | 1984-04-12 |
| ES524928A0 (es) | 1985-01-01 |
| EP0116594A4 (en) | 1985-02-28 |
| WO1984000766A1 (en) | 1984-03-01 |
| NZ205292A (en) | 1986-07-11 |
| GB2127828A (en) | 1984-04-18 |
| GB2127828B (en) | 1985-11-13 |
| AU1883383A (en) | 1984-03-07 |
| EP0116594A1 (en) | 1984-08-29 |
| ES8505702A1 (es) | 1985-01-01 |
| JPS6326765B2 (OSRAM) | 1988-05-31 |
| AU555147B2 (en) | 1986-09-11 |
| US4404335A (en) | 1983-09-13 |
| SG69086G (en) | 1987-03-27 |
| DK190184A (da) | 1984-04-12 |
| IT1163886B (it) | 1987-04-08 |
| GB8322029D0 (en) | 1983-09-21 |
| EP0116594B1 (en) | 1989-01-25 |
| JPS59501666A (ja) | 1984-10-04 |
| DE3379051D1 (en) | 1989-03-02 |
| IT8322514A0 (it) | 1983-08-11 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US4358578A (en) | Process for reacting a phenol with an epoxy compound | |
| CA1215193A (en) | Hydrolyzing epoxy resins in absence of solvent and in presence of oxalic acid and a phosphonium compound | |
| US6346582B1 (en) | Glycidation of carboxy polyester and tertiary C monocarboxyic acid (glycidyl ester) | |
| US3978027A (en) | Process for reacting a phenol with an epoxy compound | |
| CA2035622A1 (en) | Precatalyzed catalyst compositions, process for preparing epoxy resins, curable compositions, articles resulting from curing the resultant compositions | |
| EP0379943B1 (en) | Process for preparation of high-molecular-weight epoxy dimer acid ester resin | |
| JPS5817776B2 (ja) | 被覆の製造法 | |
| EP0082572B1 (en) | Polyglycidyl ethers, their preparation and their use in curable compositions | |
| US5223558A (en) | Process for preparation of high-molecular-weight epoxy dimer acid ester resin | |
| CN87107409A (zh) | 含聚环氧化物和环氧合成催化剂的组合物及制备合成环氧树脂的方法 | |
| US4528356A (en) | Process for preparing higher molecular weight epoxy resins | |
| US4137220A (en) | Preparation of novolak epoxy resins | |
| EP1538147B1 (en) | Method of producing glycidyl 2-hydroxyisobutyrate | |
| US3892684A (en) | Clear flexibilized epoxy resins | |
| JPH11181047A (ja) | エポキシ樹脂の製造方法 | |
| EP0501575A2 (en) | A process for the preparation of highly reactive, high-molecular weight epoxy resins | |
| US4474935A (en) | Stable precatalyzed saturated epoxy resin compositions | |
| NO161377B (no) | Fremgangsmaate for delvis hydrolyse av epoksyharpiks i naervaer av en katalysator. | |
| GB2075512A (en) | Curing agents for epoxy resins | |
| JP3517933B2 (ja) | エポキシ基含有ポリヒドロキシポリエ−テル樹脂及びその樹脂組成物 | |
| WO1984000767A1 (en) | Coating compositions containing a hydrolyzed epoxy novolac resin | |
| US2998398A (en) | Resinous polyhydric phenol | |
| US20120309933A1 (en) | Divinylarene dioxide resins | |
| JPH08183838A (ja) | フェノール誘導体およびその製造方法 |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEX | Expiry |