CA1202749A - Preparation of epoxy resins - Google Patents
Preparation of epoxy resinsInfo
- Publication number
- CA1202749A CA1202749A CA000436535A CA436535A CA1202749A CA 1202749 A CA1202749 A CA 1202749A CA 000436535 A CA000436535 A CA 000436535A CA 436535 A CA436535 A CA 436535A CA 1202749 A CA1202749 A CA 1202749A
- Authority
- CA
- Canada
- Prior art keywords
- compound
- percent
- per molecule
- hydroxyl group
- reaction
- 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
- 239000003822 epoxy resin Substances 0.000 title abstract description 7
- 229920000647 polyepoxide Polymers 0.000 title abstract description 7
- 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 4
- 238000002360 preparation method Methods 0.000 title description 3
- 238000006243 chemical reaction Methods 0.000 claims abstract description 47
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 36
- 239000011541 reaction mixture Substances 0.000 claims abstract description 34
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 27
- 150000001875 compounds Chemical class 0.000 claims abstract description 22
- 125000003118 aryl group Chemical group 0.000 claims abstract description 20
- 238000000034 method Methods 0.000 claims abstract description 18
- 239000002904 solvent Substances 0.000 claims abstract description 16
- 238000009835 boiling Methods 0.000 claims abstract description 15
- 150000008044 alkali metal hydroxides Chemical class 0.000 claims abstract description 13
- 150000004982 aromatic amines Chemical group 0.000 claims abstract description 13
- 125000003055 glycidyl group Chemical group C(C1CO1)* 0.000 claims abstract description 6
- 238000004519 manufacturing process Methods 0.000 claims abstract description 5
- 239000007864 aqueous solution Substances 0.000 claims abstract description 4
- 239000003960 organic solvent Substances 0.000 claims abstract description 4
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical group [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 92
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 claims description 33
- 235000013824 polyphenols Nutrition 0.000 claims description 14
- 229920003986 novolac Polymers 0.000 claims description 12
- 239000000203 mixture Substances 0.000 claims description 8
- 150000008442 polyphenolic compounds Chemical class 0.000 claims description 5
- 229920005989 resin Polymers 0.000 claims description 5
- 239000011347 resin Substances 0.000 claims description 5
- 150000003333 secondary alcohols Chemical group 0.000 claims description 4
- LJBWJFWNFUKAGS-UHFFFAOYSA-N 2-[bis(2-hydroxyphenyl)methyl]phenol Chemical compound OC1=CC=CC=C1C(C=1C(=CC=CC=1)O)C1=CC=CC=C1O LJBWJFWNFUKAGS-UHFFFAOYSA-N 0.000 claims description 3
- HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical compound OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 claims description 3
- SLGWESQGEUXWJQ-UHFFFAOYSA-N formaldehyde;phenol Chemical compound O=C.OC1=CC=CC=C1 SLGWESQGEUXWJQ-UHFFFAOYSA-N 0.000 claims description 3
- 125000005843 halogen group Chemical group 0.000 claims description 3
- 229920001568 phenolic resin Polymers 0.000 claims description 3
- YBRVSVVVWCFQMG-UHFFFAOYSA-N 4,4'-diaminodiphenylmethane Chemical group C1=CC(N)=CC=C1CC1=CC=C(N)C=C1 YBRVSVVVWCFQMG-UHFFFAOYSA-N 0.000 claims description 2
- 229930185605 Bisphenol Natural products 0.000 claims description 2
- VCCBEIPGXKNHFW-UHFFFAOYSA-N biphenyl-4,4'-diol Chemical group C1=CC(O)=CC=C1C1=CC=C(O)C=C1 VCCBEIPGXKNHFW-UHFFFAOYSA-N 0.000 claims description 2
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical group C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 claims description 2
- 239000004215 Carbon black (E152) Chemical group 0.000 claims 2
- 229930195733 hydrocarbon Chemical group 0.000 claims 2
- 150000002430 hydrocarbons Chemical group 0.000 claims 2
- ZRYCRPNCXLQHPN-UHFFFAOYSA-N 3-hydroxy-2-methylbenzaldehyde Chemical compound CC1=C(O)C=CC=C1C=O ZRYCRPNCXLQHPN-UHFFFAOYSA-N 0.000 claims 1
- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 claims 1
- 239000000306 component Substances 0.000 abstract description 16
- 150000004820 halides Chemical class 0.000 abstract description 3
- 229910052783 alkali metal Inorganic materials 0.000 abstract 1
- 150000001340 alkali metals Chemical class 0.000 abstract 1
- 150000002989 phenols Chemical class 0.000 description 18
- ARXJGSRGQADJSQ-UHFFFAOYSA-N 1-methoxypropan-2-ol Chemical compound COCC(C)O ARXJGSRGQADJSQ-UHFFFAOYSA-N 0.000 description 15
- 125000001183 hydrocarbyl group Chemical group 0.000 description 14
- 125000004432 carbon atom Chemical group C* 0.000 description 13
- 150000002118 epoxides Chemical class 0.000 description 13
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 12
- 239000000047 product Substances 0.000 description 12
- 229910052739 hydrogen Inorganic materials 0.000 description 10
- 239000001257 hydrogen Substances 0.000 description 10
- 238000002474 experimental method Methods 0.000 description 7
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 6
- -1 HYDROXYL GROUP Chemical group 0.000 description 6
- 230000015572 biosynthetic process Effects 0.000 description 5
- 230000000052 comparative effect Effects 0.000 description 5
- WSFSSNUMVMOOMR-UHFFFAOYSA-N formaldehyde Substances O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 5
- 238000005755 formation reaction Methods 0.000 description 5
- 150000002431 hydrogen Chemical group 0.000 description 5
- 229920000642 polymer Polymers 0.000 description 5
- 150000003839 salts Chemical class 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 4
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 4
- 229940126062 Compound A Drugs 0.000 description 4
- NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 description 4
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 4
- 229910052794 bromium Inorganic materials 0.000 description 4
- 239000000460 chlorine Substances 0.000 description 4
- 229910052801 chlorine Inorganic materials 0.000 description 4
- 239000012071 phase Substances 0.000 description 4
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- 125000000217 alkyl group Chemical group 0.000 description 3
- 239000003518 caustics Substances 0.000 description 3
- 229960005150 glycerol Drugs 0.000 description 3
- 235000011187 glycerol Nutrition 0.000 description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 3
- 239000012074 organic phase Substances 0.000 description 3
- LHENQXAPVKABON-UHFFFAOYSA-N 1-methoxypropan-1-ol Chemical compound CCC(O)OC LHENQXAPVKABON-UHFFFAOYSA-N 0.000 description 2
- IVIDDMGBRCPGLJ-UHFFFAOYSA-N 2,3-bis(oxiran-2-ylmethoxy)propan-1-ol Chemical compound C1OC1COC(CO)COCC1CO1 IVIDDMGBRCPGLJ-UHFFFAOYSA-N 0.000 description 2
- SSZWWUDQMAHNAQ-UHFFFAOYSA-N 3-chloropropane-1,2-diol Chemical compound OCC(O)CCl SSZWWUDQMAHNAQ-UHFFFAOYSA-N 0.000 description 2
- CTKINSOISVBQLD-UHFFFAOYSA-N Glycidol Chemical compound OCC1CO1 CTKINSOISVBQLD-UHFFFAOYSA-N 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- 125000003277 amino group Chemical group 0.000 description 2
- 239000008346 aqueous phase Substances 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 229910052736 halogen Chemical group 0.000 description 2
- 150000002367 halogens Chemical group 0.000 description 2
- 150000002500 ions Chemical class 0.000 description 2
- 229910000000 metal hydroxide Inorganic materials 0.000 description 2
- 150000004692 metal hydroxides Chemical class 0.000 description 2
- DNIAPMSPPWPWGF-UHFFFAOYSA-N monopropylene glycol Natural products CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 2
- 229920000768 polyamine Polymers 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- YLXUCOBYEXOGLZ-UHFFFAOYSA-N 1-butoxycyclohexa-2,4-dien-1-ol Chemical compound CCCCOC1(O)CC=CC=C1 YLXUCOBYEXOGLZ-UHFFFAOYSA-N 0.000 description 1
- UYVDGHOUPDJWAZ-UHFFFAOYSA-N 1-methoxypropan-2-ol Chemical compound COCC(C)O.COCC(C)O UYVDGHOUPDJWAZ-UHFFFAOYSA-N 0.000 description 1
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 1
- 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 1
- KFZMGEQAYNKOFK-UHFFFAOYSA-N 2-propanol Substances CC(C)O KFZMGEQAYNKOFK-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
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-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
- 241001397173 Kali <angiosperm> Species 0.000 description 1
- CKRZKMFTZCFYGB-UHFFFAOYSA-N N-phenylhydroxylamine Chemical compound ONC1=CC=CC=C1 CKRZKMFTZCFYGB-UHFFFAOYSA-N 0.000 description 1
- KEBVIYLGAUAZBP-UHFFFAOYSA-N NC=1C(C(C=CC1)(C)O)C Chemical compound NC=1C(C(C=CC1)(C)O)C KEBVIYLGAUAZBP-UHFFFAOYSA-N 0.000 description 1
- 101100409194 Rattus norvegicus Ppargc1b gene Proteins 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 238000005119 centrifugation Methods 0.000 description 1
- 229930003836 cresol Natural products 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- GYZLOYUZLJXAJU-UHFFFAOYSA-N diglycidyl ether Chemical class C1OC1COCC1CO1 GYZLOYUZLJXAJU-UHFFFAOYSA-N 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- ZZUFCTLCJUWOSV-UHFFFAOYSA-N furosemide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC(C(O)=O)=C1NCC1=CC=CO1 ZZUFCTLCJUWOSV-UHFFFAOYSA-N 0.000 description 1
- 125000005842 heteroatom Chemical group 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- SGFJJNBUMXQSMU-PDBXOOCHSA-N oxiran-2-ylmethyl (9z,12z,15z)-octadeca-9,12,15-trienoate Chemical class CC\C=C/C\C=C/C\C=C/CCCCCCCC(=O)OCC1CO1 SGFJJNBUMXQSMU-PDBXOOCHSA-N 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 150000003138 primary alcohols Chemical class 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- LVTJOONKWUXEFR-FZRMHRINSA-N protoneodioscin Natural products O(C[C@@H](CC[C@]1(O)[C@H](C)[C@@H]2[C@]3(C)[C@H]([C@H]4[C@@H]([C@]5(C)C(=CC4)C[C@@H](O[C@@H]4[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@@H](O)[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@H](CO)O4)CC5)CC3)C[C@@H]2O1)C)[C@H]1[C@H](O)[C@H](O)[C@H](O)[C@@H](CO)O1 LVTJOONKWUXEFR-FZRMHRINSA-N 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 230000036647 reaction Effects 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 238000010626 work up procedure Methods 0.000 description 1
- NWONKYPBYAMBJT-UHFFFAOYSA-L zinc sulfate Chemical compound [Zn+2].[O-]S([O-])(=O)=O NWONKYPBYAMBJT-UHFFFAOYSA-L 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
- C08G59/02—Polycondensates containing more than one epoxy group per molecule
- C08G59/10—Polycondensates containing more than one epoxy group per molecule of polyamines with epihalohydrins or precursors thereof
-
- 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
- C08G59/02—Polycondensates containing more than one epoxy group per molecule
- C08G59/04—Polycondensates containing more than one epoxy group per molecule of polyhydroxy compounds with epihalohydrins or precursors thereof
- C08G59/06—Polycondensates containing more than one epoxy group per molecule of polyhydroxy compounds with epihalohydrins or precursors thereof of polyhydric phenols
- C08G59/063—Polycondensates containing more than one epoxy group per molecule of polyhydroxy compounds with epihalohydrins or precursors thereof of polyhydric phenols with epihalohydrins
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Epoxy Compounds (AREA)
- Epoxy Resins (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US41701582A | 1982-09-13 | 1982-09-13 | |
| US417,015 | 1982-09-13 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1202749A true CA1202749A (en) | 1986-04-01 |
Family
ID=23652246
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA000436535A Expired CA1202749A (en) | 1982-09-13 | 1983-09-12 | Preparation of epoxy resins |
Country Status (12)
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5624976A (en) * | 1994-03-25 | 1997-04-29 | Dentsply Gmbh | Dental filling composition and method |
| US5876210A (en) | 1994-04-22 | 1999-03-02 | Dentsply G.M.B.H. | Dental polymer product |
| US5998499A (en) | 1994-03-25 | 1999-12-07 | Dentsply G.M.B.H. | Liquid crystalline (meth)acrylate compounds, composition and method |
| US6353061B1 (en) | 1993-05-26 | 2002-03-05 | Dentsply Gmbh | α, ω-methacrylate terminated macromonomer compounds |
| US6369164B1 (en) | 1993-05-26 | 2002-04-09 | Dentsply G.M.B.H. | Polymerizable compounds and compositions |
Families Citing this family (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4559272A (en) * | 1984-05-09 | 1985-12-17 | Hughes Aircraft Company | Heat curable polyglycidyl aromatic amine encapsulants |
| US4661644A (en) * | 1985-09-09 | 1987-04-28 | The Dow Chemical Company | Brominated epoxyaromatic compounds |
| EP0251431B1 (en) * | 1986-06-24 | 1993-07-28 | Mitsui Petrochemical Industries, Ltd. | Epoxy resin |
| CA1293837C (en) * | 1986-10-14 | 1991-12-31 | Ha Q. Pham | Preparation of epoxy resins |
| US5219513A (en) * | 1989-08-17 | 1993-06-15 | Centro Sviluppo Settori Impiego S.R.L. | Process for preparing structural, heat-insulating shaped bodies, and bodies obtained thereby |
| JP3315436B2 (ja) * | 1992-06-19 | 2002-08-19 | ジャパンエポキシレジン株式会社 | ビフェノール骨格含有エポキシ樹脂の製造方法 |
| RU2130452C1 (ru) * | 1997-07-29 | 1999-05-20 | Научно-исследовательский институт полимерных материалов | Способ получения глицидола |
| JP4836062B2 (ja) * | 2000-12-26 | 2011-12-14 | 小西化学工業株式会社 | ビスフェノールジアルキルエーテル類の製造方法 |
| US6794478B2 (en) | 2001-09-28 | 2004-09-21 | Dainippon Ink And Chemicals, Inc. | Preparing epoxy resin by distilling two fractions to recover and reuse epihalohydrin without glycidol |
| JP5827098B2 (ja) * | 2011-10-18 | 2015-12-02 | 株式会社Adeka | ポリグリシジルチオエーテルの製造方法 |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NL205753A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) * | 1955-03-28 | |||
| US2951822A (en) * | 1956-11-23 | 1960-09-06 | Union Carbide Corp | Preparation of polyglycidyl aromatic amines and resinous compositions made therefrom |
| DE1518119C2 (de) * | 1965-01-02 | 1973-10-31 | Reichhold-Albert Chemie Ag, 2000 Hamburg | Verfahren zur Herstellung von 2 2 Bis (phenylol) propan di glycidyl ather |
| JPS609034B2 (ja) * | 1973-10-09 | 1985-03-07 | ヘキスト アクチエンゲゼルシヤフト | 改良された性質を有する１価又は多価フエノ−ルのグリシジルエ−テルの製造法 |
| IT1051397B (it) * | 1975-12-19 | 1981-04-21 | S I R S P A | Procedimento per la preparazione di resine novolacche epossidate |
| JPS5335999A (en) * | 1976-09-16 | 1978-04-03 | Nissin Electric Co Ltd | Capacitor |
| GB2001991B (en) * | 1977-06-30 | 1982-01-06 | Shell Int Research | Preparation of polyglycidyl ethers of polyhydric phenols |
| GB2120659B (en) * | 1982-04-28 | 1985-12-04 | Sumitomo Chemical Co | Process for producing glycidyl ethers of monohydric polyhydric phenols |
-
1983
- 1983-09-08 NZ NZ205522A patent/NZ205522A/en unknown
- 1983-09-08 AU AU18950/83A patent/AU568601B2/en not_active Expired
- 1983-09-09 EP EP83108908A patent/EP0103282B1/en not_active Expired - Lifetime
- 1983-09-09 ZA ZA836705A patent/ZA836705B/xx unknown
- 1983-09-09 DE DE8383108908T patent/DE3381876D1/de not_active Expired - Lifetime
- 1983-09-12 BR BR8305034A patent/BR8305034A/pt not_active IP Right Cessation
- 1983-09-12 ES ES525538A patent/ES525538A0/es active Granted
- 1983-09-12 CA CA000436535A patent/CA1202749A/en not_active Expired
- 1983-09-12 GB GB08324338A patent/GB2128185B/en not_active Expired
- 1983-09-13 JP JP58169116A patent/JPS5973578A/ja active Granted
-
1986
- 1986-08-20 SG SG689/86A patent/SG68986G/en unknown
-
1987
- 1987-12-30 MY MY81/87A patent/MY8700081A/xx unknown
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6339114B1 (en) | 1993-05-26 | 2002-01-15 | Dentsply Detrey Gmbh | Liquid crystalline (meth)acrylate compounds, composition and method |
| US6353061B1 (en) | 1993-05-26 | 2002-03-05 | Dentsply Gmbh | α, ω-methacrylate terminated macromonomer compounds |
| US6369164B1 (en) | 1993-05-26 | 2002-04-09 | Dentsply G.M.B.H. | Polymerizable compounds and compositions |
| US5624976A (en) * | 1994-03-25 | 1997-04-29 | Dentsply Gmbh | Dental filling composition and method |
| US5998499A (en) | 1994-03-25 | 1999-12-07 | Dentsply G.M.B.H. | Liquid crystalline (meth)acrylate compounds, composition and method |
| US5876210A (en) | 1994-04-22 | 1999-03-02 | Dentsply G.M.B.H. | Dental polymer product |
Also Published As
| Publication number | Publication date |
|---|---|
| GB2128185B (en) | 1985-12-18 |
| AU1895083A (en) | 1984-03-22 |
| EP0103282A3 (en) | 1987-05-13 |
| GB2128185A (en) | 1984-04-26 |
| ZA836705B (en) | 1985-04-24 |
| JPS5973578A (ja) | 1984-04-25 |
| BR8305034A (pt) | 1984-04-24 |
| EP0103282A2 (en) | 1984-03-21 |
| MY8700081A (en) | 1987-12-31 |
| AU568601B2 (en) | 1988-01-07 |
| NZ205522A (en) | 1987-04-30 |
| DE3381876D1 (de) | 1990-10-18 |
| ES8503345A1 (es) | 1985-02-16 |
| GB8324338D0 (en) | 1983-10-12 |
| SG68986G (en) | 1987-02-27 |
| ES525538A0 (es) | 1985-02-16 |
| EP0103282B1 (en) | 1990-09-12 |
| JPH024224B2 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1990-01-26 |
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