DE1952783A1 - Verfahren zur Hydrolysierung einer 1,2-Epoxyalkyl-Verbindung - Google Patents
Verfahren zur Hydrolysierung einer 1,2-Epoxyalkyl-VerbindungInfo
- Publication number
- DE1952783A1 DE1952783A1 DE19691952783 DE1952783A DE1952783A1 DE 1952783 A1 DE1952783 A1 DE 1952783A1 DE 19691952783 DE19691952783 DE 19691952783 DE 1952783 A DE1952783 A DE 1952783A DE 1952783 A1 DE1952783 A1 DE 1952783A1
- Authority
- DE
- Germany
- Prior art keywords
- compound
- bisphenol
- weight
- polyepoxide
- mixture
- 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
- 238000000034 method Methods 0.000 title claims description 23
- 150000001875 compounds Chemical class 0.000 title claims description 21
- 230000003301 hydrolyzing effect Effects 0.000 title claims description 5
- 229920000647 polyepoxide Polymers 0.000 claims description 53
- 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 claims description 39
- 239000000203 mixture Substances 0.000 claims description 28
- 239000007787 solid Substances 0.000 claims description 27
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 claims description 24
- 239000003822 epoxy resin Substances 0.000 claims description 16
- 239000007788 liquid Substances 0.000 claims description 16
- 238000006243 chemical reaction Methods 0.000 claims description 13
- 239000002904 solvent Substances 0.000 claims description 13
- GYZLOYUZLJXAJU-UHFFFAOYSA-N diglycidyl ether Chemical compound C1OC1COCC1CO1 GYZLOYUZLJXAJU-UHFFFAOYSA-N 0.000 claims description 12
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims description 10
- 238000004519 manufacturing process Methods 0.000 claims description 9
- 238000010438 heat treatment Methods 0.000 claims description 8
- 235000006408 oxalic acid Nutrition 0.000 claims description 8
- 239000002253 acid Substances 0.000 claims description 7
- 238000002360 preparation method Methods 0.000 claims description 6
- 238000000354 decomposition reaction Methods 0.000 claims description 5
- 235000014113 dietary fatty acids Nutrition 0.000 claims description 5
- 239000000194 fatty acid Substances 0.000 claims description 5
- 229930195729 fatty acid Natural products 0.000 claims description 5
- 150000004665 fatty acids Chemical class 0.000 claims description 5
- 150000002576 ketones Chemical class 0.000 claims description 5
- 229930185605 Bisphenol Natural products 0.000 claims description 4
- 125000003118 aryl group Chemical group 0.000 claims description 3
- 230000015572 biosynthetic process Effects 0.000 claims description 3
- 230000007717 exclusion Effects 0.000 claims description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims 2
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 claims 2
- 239000001294 propane Substances 0.000 claims 2
- 125000002029 aromatic hydrocarbon group Chemical group 0.000 claims 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 1
- 239000011877 solvent mixture Substances 0.000 claims 1
- 239000000047 product Substances 0.000 description 42
- 230000007062 hydrolysis Effects 0.000 description 24
- 238000006460 hydrolysis reaction Methods 0.000 description 24
- 239000004593 Epoxy Substances 0.000 description 18
- 229920005989 resin Polymers 0.000 description 14
- 239000011347 resin Substances 0.000 description 14
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 12
- 239000000126 substance Substances 0.000 description 11
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 10
- 239000000654 additive Substances 0.000 description 10
- 239000006185 dispersion Substances 0.000 description 8
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 238000005886 esterification reaction Methods 0.000 description 6
- 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 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- 239000003054 catalyst Substances 0.000 description 5
- 238000004821 distillation Methods 0.000 description 5
- 230000032050 esterification Effects 0.000 description 5
- 229910052757 nitrogen Inorganic materials 0.000 description 5
- 239000003973 paint Substances 0.000 description 5
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 4
- 230000000996 additive effect Effects 0.000 description 4
- 238000000576 coating method Methods 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- 230000009257 reactivity Effects 0.000 description 4
- 239000007858 starting material Substances 0.000 description 4
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 125000003700 epoxy group Chemical group 0.000 description 3
- 239000000049 pigment Substances 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 239000003981 vehicle Substances 0.000 description 3
- 239000008096 xylene Substances 0.000 description 3
- -1 2, 3-dihydroxypropoxy Chemical group 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 2
- 241000283986 Lepus Species 0.000 description 2
- 239000011248 coating agent Substances 0.000 description 2
- SWXVUIWOUIDPGS-UHFFFAOYSA-N diacetone alcohol Chemical compound CC(=O)CC(C)(C)O SWXVUIWOUIDPGS-UHFFFAOYSA-N 0.000 description 2
- 238000009472 formulation Methods 0.000 description 2
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 2
- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 description 2
- PFTAWBLQPZVEMU-DZGCQCFKSA-N (+)-catechin Chemical compound C1([C@H]2OC3=CC(O)=CC(O)=C3C[C@@H]2O)=CC=C(O)C(O)=C1 PFTAWBLQPZVEMU-DZGCQCFKSA-N 0.000 description 1
- YFBMUIMQJYESPZ-UHFFFAOYSA-N 3-phenoxy-1,2-propanediol Natural products C1C(OC(C)=O)CCC2(C)C3=CCC4(C)C(C(C)CCC(CC)C(C)C)CCC4(C)C3CCC21 YFBMUIMQJYESPZ-UHFFFAOYSA-N 0.000 description 1
- FNQIYTUXOKTMDM-UHFFFAOYSA-N 3-phenoxypropane-1,2-diol Chemical compound OCC(O)COC1=CC=CC=C1 FNQIYTUXOKTMDM-UHFFFAOYSA-N 0.000 description 1
- VPWNQTHUCYMVMZ-UHFFFAOYSA-N 4,4'-sulfonyldiphenol Chemical compound C1=CC(O)=CC=C1S(=O)(=O)C1=CC=C(O)C=C1 VPWNQTHUCYMVMZ-UHFFFAOYSA-N 0.000 description 1
- 241000272201 Columbiformes Species 0.000 description 1
- 241000196324 Embryophyta Species 0.000 description 1
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 1
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 1
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- FQYUMYWMJTYZTK-UHFFFAOYSA-N Phenyl glycidyl ether Chemical compound C1OC1COC1=CC=CC=C1 FQYUMYWMJTYZTK-UHFFFAOYSA-N 0.000 description 1
- 239000004952 Polyamide Substances 0.000 description 1
- JHWQMXKQJVAWKI-UHFFFAOYSA-N UNPD187286 Natural products OCC(O)CC1=CC=CC=C1 JHWQMXKQJVAWKI-UHFFFAOYSA-N 0.000 description 1
- 238000005903 acid hydrolysis reaction Methods 0.000 description 1
- 239000000853 adhesive Substances 0.000 description 1
- 230000001070 adhesive effect Effects 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- 239000011260 aqueous acid Substances 0.000 description 1
- 239000003849 aromatic solvent Substances 0.000 description 1
- 239000012298 atmosphere Substances 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- ADRVNXBAWSRFAJ-UHFFFAOYSA-N catechin Natural products OC1Cc2cc(O)cc(O)c2OC1c3ccc(O)c(O)c3 ADRVNXBAWSRFAJ-UHFFFAOYSA-N 0.000 description 1
- 235000005487 catechin Nutrition 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- 229950001002 cianidanol Drugs 0.000 description 1
- 239000004927 clay Substances 0.000 description 1
- 239000007859 condensation product Substances 0.000 description 1
- 150000001991 dicarboxylic acids Chemical class 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 238000007598 dipping method Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 150000002334 glycols Chemical class 0.000 description 1
- 230000005484 gravity Effects 0.000 description 1
- 239000012433 hydrogen halide Substances 0.000 description 1
- 229910000039 hydrogen halide Inorganic materials 0.000 description 1
- 238000007654 immersion Methods 0.000 description 1
- 238000010348 incorporation Methods 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 239000011872 intimate mixture Substances 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- WTFXARWRTYJXII-UHFFFAOYSA-N iron(2+);iron(3+);oxygen(2-) Chemical compound [O-2].[O-2].[O-2].[O-2].[Fe+2].[Fe+3].[Fe+3] WTFXARWRTYJXII-UHFFFAOYSA-N 0.000 description 1
- SZVJSHCCFOBDDC-UHFFFAOYSA-N iron(II,III) oxide Inorganic materials O=[Fe]O[Fe]O[Fe]=O SZVJSHCCFOBDDC-UHFFFAOYSA-N 0.000 description 1
- 235000021388 linseed oil Nutrition 0.000 description 1
- 239000000944 linseed oil Substances 0.000 description 1
- 239000004850 liquid epoxy resins (LERs) Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 125000000466 oxiranyl group Chemical group 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 229920000768 polyamine Polymers 0.000 description 1
- 150000008442 polyphenolic compounds Polymers 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 238000007142 ring opening reaction Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 239000000375 suspending agent Substances 0.000 description 1
- 230000009897 systematic effect Effects 0.000 description 1
- 239000004634 thermosetting polymer Substances 0.000 description 1
- 210000002700 urine Anatomy 0.000 description 1
- 238000009736 wetting 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
- C08G59/18—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
- C08G59/62—Alcohols or phenols
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
- C07C29/09—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by hydrolysis
- C07C29/10—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by hydrolysis of ethers, including cyclic ethers, e.g. oxiranes
- C07C29/103—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by hydrolysis of ethers, including cyclic ethers, e.g. oxiranes of cyclic ethers
- C07C29/106—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by hydrolysis of ethers, including cyclic ethers, e.g. oxiranes of cyclic ethers of oxiranes
-
- 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
-
- 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
- C08G59/4207—Polycarboxylic acids; Anhydrides, halides or low molecular weight esters thereof aliphatic
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L63/00—Compositions of epoxy resins; Compositions of derivatives of epoxy resins
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T428/00—Stock material or miscellaneous articles
- Y10T428/31504—Composite [nonstructural laminate]
- Y10T428/31511—Of epoxy ether
- Y10T428/31529—Next to metal
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Inorganic Chemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Epoxy Resins (AREA)
- Paints Or Removers (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Compositions Of Macromolecular Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US77085768A | 1968-10-25 | 1968-10-25 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1952783A1 true DE1952783A1 (de) | 1970-05-14 |
Family
ID=25089911
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19691952783 Pending DE1952783A1 (de) | 1968-10-25 | 1969-10-20 | Verfahren zur Hydrolysierung einer 1,2-Epoxyalkyl-Verbindung |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US3632836A (enExample) |
| JP (2) | JPS4928182B1 (enExample) |
| BE (1) | BE740749A (enExample) |
| BR (1) | BR6913610D0 (enExample) |
| DE (1) | DE1952783A1 (enExample) |
| FR (1) | FR2021531A1 (enExample) |
| GB (2) | GB1289810A (enExample) |
| NL (1) | NL6914516A (enExample) |
Families Citing this family (24)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IT967654B (it) * | 1972-09-20 | 1974-03-11 | Sir Soc Italiana Resine Spa | Procedimento perfezionato per la preparazione di resine epossino volacche liquide |
| IT967653B (it) * | 1972-09-20 | 1974-03-11 | Sir Soc Italiana Resine Spa | Procedimento per la preparazione di resine epossinovolacche solide |
| US4163087A (en) * | 1974-09-12 | 1979-07-31 | Politechnika Warszawska | Method for production of new thermal and chemical resistant polyurethane plastics |
| JPS5277810U (enExample) * | 1975-12-05 | 1977-06-10 | ||
| WO1982001878A1 (en) * | 1980-11-26 | 1982-06-10 | Dow Chemical Co | Method for preparing high molecular weight epoxy resins containing hydrolyzed glycidyl 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 |
| US4340713A (en) * | 1980-11-26 | 1982-07-20 | The Dow Chemical Company | Method for preparing high molecular weight epoxy resins containing hydrolyzed epoxy groups |
| US4374076A (en) * | 1981-10-09 | 1983-02-15 | Coors Porcelain Company | Method for making cast epoxy resin bodies and epoxy formulation therefor |
| US4404335A (en) * | 1982-08-16 | 1983-09-13 | The Dow Chemical Company | Hydrolyzing epoxy resins in absence of solvent and in presence of oxalic acid and a phosphonium compound |
| JPS59501667A (ja) * | 1982-08-16 | 1984-10-04 | ザ・ダウ・ケミカル・カンパニ− | 加水分解エポキシノボラック樹脂を含む３５゜ｃ以下の温度で硬化可能な被覆組成物 |
| US4530948A (en) * | 1982-08-16 | 1985-07-23 | The Dow Chemical Company | Room temperature coating compositions containing hydrolyzed epoxy novolac resins |
| US4721743A (en) * | 1985-03-25 | 1988-01-26 | The Dow Chemical Company | Non-thermoset thermally stable capped epoxy resin compositions |
| US4783509A (en) * | 1985-03-25 | 1988-11-08 | The Dow Chemical Company | Non-thermoset thermally stable capped epoxy resin compositions |
| GB8603701D0 (en) * | 1986-02-14 | 1986-03-19 | Dow Chemical Rheinwerk Gmbh | Epoxy resins |
| US4724253A (en) * | 1986-06-13 | 1988-02-09 | The Dow Chemical Company | Adducts of partially hydrolyzed epoxy resins and polyamines |
| US4777084A (en) * | 1987-10-08 | 1988-10-11 | Minnesota Mining And Manufacturing Company | Phenolic-modified epoxy adhesive including the reaction product of bisphenol A and the monoglycidyl ether of bisphenol A |
| HUE028588T2 (hu) | 2005-12-13 | 2016-12-28 | Incyte Holdings Corp | Heteroaril-szubsztituált pirrolo[2,3-b]piridinek és pirrolo[2,3-b]pirimidinek mint Janus-kináz inhibitorok |
| CA2792508C (en) | 2010-03-10 | 2018-01-16 | Incyte Corporation | Piperidin-4-yl azetidine derivatives as jak1 inhibitors |
| US8691807B2 (en) | 2011-06-20 | 2014-04-08 | Incyte Corporation | Azetidinyl phenyl, pyridyl or pyrazinyl carboxamide derivatives as JAK inhibitors |
| KR102242077B1 (ko) | 2012-11-15 | 2021-04-20 | 인사이트 홀딩스 코포레이션 | 룩솔리티니브의 서방성 제형 |
| MX376856B (es) | 2013-08-07 | 2025-03-07 | Incyte Holdings Corp | Formas de dosificacion de liberacion prolongada para un inhibidor de jak 1 (cinasa de janus 1). |
| 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 |
| CN115725055A (zh) * | 2021-08-31 | 2023-03-03 | 旭化成株式会社 | 环氧树脂组合物 |
-
1968
- 1968-10-25 US US3632836D patent/US3632836A/en not_active Expired - Lifetime
-
1969
- 1969-09-24 NL NL6914516A patent/NL6914516A/xx not_active Application Discontinuation
- 1969-10-16 FR FR6935486A patent/FR2021531A1/fr active Pending
- 1969-10-20 DE DE19691952783 patent/DE1952783A1/de active Pending
- 1969-10-24 BR BR21361069A patent/BR6913610D0/pt unknown
- 1969-10-24 BE BE740749D patent/BE740749A/xx not_active IP Right Cessation
- 1969-10-24 JP JP8517369A patent/JPS4928182B1/ja active Pending
- 1969-10-27 GB GB1289810D patent/GB1289810A/en not_active Expired
- 1969-10-27 GB GB5255969A patent/GB1287950A/en not_active Expired
-
1973
- 1973-08-03 JP JP8741973A patent/JPS5010613B1/ja active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| GB1287950A (enExample) | 1972-09-06 |
| BE740749A (enExample) | 1970-04-24 |
| US3632836A (en) | 1972-01-04 |
| GB1289810A (enExample) | 1972-09-20 |
| NL6914516A (enExample) | 1970-04-28 |
| BR6913610D0 (pt) | 1973-04-26 |
| FR2021531A1 (enExample) | 1970-07-24 |
| JPS4928182B1 (enExample) | 1974-07-24 |
| JPS5010613B1 (enExample) | 1975-04-23 |
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| Date | Code | Title | Description |
|---|---|---|---|
| E77 | Valid patent as to the heymanns-index 1977 |