DE961659C - Verfahren zur Herstellung von harzartigen Massen - Google Patents
Verfahren zur Herstellung von harzartigen MassenInfo
- Publication number
- DE961659C DE961659C DEN2853A DEN0002853A DE961659C DE 961659 C DE961659 C DE 961659C DE N2853 A DEN2853 A DE N2853A DE N0002853 A DEN0002853 A DE N0002853A DE 961659 C DE961659 C DE 961659C
- Authority
- DE
- Germany
- Prior art keywords
- alkenyl
- groups
- epoxyalkyl
- polymerization
- compounds
- 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
- 238000000034 method Methods 0.000 title claims description 17
- 238000004519 manufacturing process Methods 0.000 title claims description 7
- 125000003342 alkenyl group Chemical group 0.000 claims description 16
- 238000006116 polymerization reaction Methods 0.000 claims description 16
- 150000001875 compounds Chemical class 0.000 claims description 14
- 239000003054 catalyst Substances 0.000 claims description 13
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 12
- 150000001335 aliphatic alkanes Chemical class 0.000 claims description 8
- -1 alkenyl halides Chemical class 0.000 claims description 8
- 239000007858 starting material Substances 0.000 claims description 8
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 5
- 229910052799 carbon Inorganic materials 0.000 claims description 5
- 125000004432 carbon atom Chemical group C* 0.000 claims description 5
- 150000002170 ethers Chemical class 0.000 claims description 5
- 150000004820 halides Chemical class 0.000 claims description 5
- 238000000576 coating method Methods 0.000 claims description 4
- 150000002978 peroxides Chemical class 0.000 claims description 4
- 238000005727 Friedel-Crafts reaction Methods 0.000 claims description 3
- 150000001735 carboxylic acids Chemical class 0.000 claims description 2
- 239000007795 chemical reaction product Substances 0.000 claims description 2
- 239000011248 coating agent Substances 0.000 claims description 2
- 238000000465 moulding Methods 0.000 claims description 2
- 125000005394 methallyl group Chemical group 0.000 claims 1
- 238000006068 polycondensation reaction Methods 0.000 description 14
- 229920000642 polymer Polymers 0.000 description 13
- 239000000243 solution Substances 0.000 description 13
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 12
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- 239000010410 layer Substances 0.000 description 10
- 239000000047 product Substances 0.000 description 10
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 9
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 8
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 8
- 229910052751 metal Inorganic materials 0.000 description 8
- 239000002184 metal Substances 0.000 description 8
- 125000003700 epoxy group Chemical group 0.000 description 7
- 239000000203 mixture Substances 0.000 description 7
- 239000000178 monomer Substances 0.000 description 6
- 150000003839 salts Chemical class 0.000 description 6
- 239000002253 acid Substances 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 5
- 150000005690 diesters Chemical class 0.000 description 5
- 238000010438 heat treatment Methods 0.000 description 5
- 239000001294 propane Substances 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- 238000009835 boiling Methods 0.000 description 4
- 150000002148 esters Chemical class 0.000 description 4
- 125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 description 4
- HPGGPRDJHPYFRM-UHFFFAOYSA-J tin(iv) chloride Chemical compound Cl[Sn](Cl)(Cl)Cl HPGGPRDJHPYFRM-UHFFFAOYSA-J 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 239000004342 Benzoyl peroxide Substances 0.000 description 3
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 description 3
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical class CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 3
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 3
- 239000004593 Epoxy Substances 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 235000019400 benzoyl peroxide Nutrition 0.000 description 3
- 150000001721 carbon Chemical group 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 229920006395 saturated elastomer Polymers 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- ATVJXMYDOSMEPO-UHFFFAOYSA-N 3-prop-2-enoxyprop-1-ene Chemical compound C=CCOCC=C ATVJXMYDOSMEPO-UHFFFAOYSA-N 0.000 description 2
- OSDWBNJEKMUWAV-UHFFFAOYSA-N Allyl chloride Chemical compound ClCC=C OSDWBNJEKMUWAV-UHFFFAOYSA-N 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- XXROGKLTLUQVRX-UHFFFAOYSA-N allyl alcohol Chemical compound OCC=C XXROGKLTLUQVRX-UHFFFAOYSA-N 0.000 description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 2
- 230000001427 coherent effect Effects 0.000 description 2
- 238000009833 condensation Methods 0.000 description 2
- 230000005494 condensation Effects 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 230000002349 favourable effect Effects 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 210000004905 finger nail Anatomy 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 229910000039 hydrogen halide Inorganic materials 0.000 description 2
- 239000012433 hydrogen halide Substances 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- 150000002763 monocarboxylic acids Chemical class 0.000 description 2
- 230000007935 neutral effect Effects 0.000 description 2
- 125000004430 oxygen atom Chemical group O* 0.000 description 2
- KJFMBFZCATUALV-UHFFFAOYSA-N phenolphthalein Chemical compound C1=CC(O)=CC=C1C1(C=2C=CC(O)=CC=2)C2=CC=CC=C2C(=O)O1 KJFMBFZCATUALV-UHFFFAOYSA-N 0.000 description 2
- XNGIFLGASWRNHJ-UHFFFAOYSA-L phthalate(2-) Chemical compound [O-]C(=O)C1=CC=CC=C1C([O-])=O XNGIFLGASWRNHJ-UHFFFAOYSA-L 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 1
- DURPTKYDGMDSBL-UHFFFAOYSA-N 1-butoxybutane Chemical compound CCCCOCCCC DURPTKYDGMDSBL-UHFFFAOYSA-N 0.000 description 1
- UIYHUUARNKRKGV-UHFFFAOYSA-N 2-prop-2-enoxycarbonylbenzoic acid Chemical compound OC(=O)C1=CC=CC=C1C(=O)OCC=C UIYHUUARNKRKGV-UHFFFAOYSA-N 0.000 description 1
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- CTKINSOISVBQLD-UHFFFAOYSA-N Glycidol Chemical compound OCC1CO1 CTKINSOISVBQLD-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 description 1
- 239000005642 Oleic acid Substances 0.000 description 1
- LGRFSURHDFAFJT-UHFFFAOYSA-N Phthalic anhydride Natural products C1=CC=C2C(=O)OC(=O)C2=C1 LGRFSURHDFAFJT-UHFFFAOYSA-N 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 239000012670 alkaline solution Substances 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- JHIWVOJDXOSYLW-UHFFFAOYSA-N butyl 2,2-difluorocyclopropane-1-carboxylate Chemical compound CCCCOC(=O)C1CC1(F)F JHIWVOJDXOSYLW-UHFFFAOYSA-N 0.000 description 1
- 238000006482 condensation reaction Methods 0.000 description 1
- 150000001991 dicarboxylic acids Chemical class 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- OTGHWLKHGCENJV-UHFFFAOYSA-N glycidic acid Chemical compound OC(=O)C1CO1 OTGHWLKHGCENJV-UHFFFAOYSA-N 0.000 description 1
- 150000002366 halogen compounds Chemical class 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000012528 membrane Substances 0.000 description 1
- 229910001507 metal halide Inorganic materials 0.000 description 1
- 150000005309 metal halides Chemical class 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical group CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 1
- 210000000282 nail Anatomy 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-M phenolate Chemical compound [O-]C1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-M 0.000 description 1
- 229940031826 phenolate Drugs 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 229920000570 polyether Polymers 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 229920003002 synthetic resin Polymers 0.000 description 1
- 239000000057 synthetic resin Substances 0.000 description 1
- 238000005292 vacuum distillation 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
- C08G59/02—Polycondensates containing more than one epoxy group per molecule
- C08G59/12—Polycondensates containing more than one epoxy group per molecule of polycarboxylic acids with epihalohydrins or precursors thereof
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D303/00—Compounds containing three-membered rings having one oxygen atom as the only ring hetero atom
- C07D303/02—Compounds containing oxirane rings
- C07D303/12—Compounds containing oxirane rings with hydrocarbon radicals, substituted by singly or doubly bound oxygen atoms
- C07D303/16—Compounds containing oxirane rings with hydrocarbon radicals, substituted by singly or doubly bound oxygen atoms by esterified hydroxyl radicals
-
- 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
- C08F18/00—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by an acyloxy radical of a saturated carboxylic acid, of carbonic acid or of a haloformic acid
- C08F18/02—Esters of monocarboxylic acids
- C08F18/04—Vinyl esters
- C08F18/08—Vinyl acetate
-
- 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
- C08F2/00—Processes of polymerisation
-
- 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
-
- 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
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S260/00—Chemistry of carbon compounds
- Y10S260/15—Antistatic agents not otherwise provided for
-
- 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
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S260/00—Chemistry of carbon compounds
- Y10S260/28—Peroxide
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Epoxy Resins (AREA)
- Epoxy Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US677114A US2476922A (en) | 1946-06-15 | 1946-06-15 | Glycidyl allyl phthalate and related mixed esters together with polymers thereof |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE961659C true DE961659C (de) | 1957-04-11 |
Family
ID=24717390
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEN2853A Expired DE961659C (de) | 1946-06-15 | 1950-10-03 | Verfahren zur Herstellung von harzartigen Massen |
Country Status (4)
| Country | Link |
|---|---|
| US (1) | US2476922A (en, 2012) |
| DE (1) | DE961659C (en, 2012) |
| FR (1) | FR947925A (en, 2012) |
| NL (2) | NL69137C (en, 2012) |
Families Citing this family (30)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2603625A (en) * | 1946-09-05 | 1952-07-15 | Olin Mathieson | Copolymers of dichlorostyrene and certain esters of olefin polycarboxylic acids |
| US2680109A (en) * | 1947-02-28 | 1954-06-01 | Columbia Southern Chem Corp | Allyl-2, 3-epoxybutyrate |
| US2580901A (en) * | 1948-06-19 | 1952-01-01 | American Cyanamid Co | Copolymer of styrene, glycidyl acrylate, and glycidyl methacrylate |
| US2556075A (en) * | 1948-06-19 | 1951-06-05 | American Cyanamid Co | Method of polymerizing glycidyl compounds |
| US2585506A (en) * | 1948-06-21 | 1952-02-12 | Shell Dev | Stabilization of halogen-containing organic materials |
| US2654717A (en) * | 1948-10-29 | 1953-10-06 | Chessie E Rehberg | Curing polymers of monoethylenic ethers and ether-esters |
| NL72274C (en, 2012) * | 1949-07-26 | 1952-06-16 | ||
| US2606810A (en) * | 1949-09-28 | 1952-08-12 | American Cyanamid Co | Treatment of wool-containing textile materials and products thereof |
| US2555500A (en) * | 1949-11-04 | 1951-06-05 | Canadian Ind | Copolymers of 4-vinylcyclohexene dioxide |
| US2698308A (en) * | 1950-12-04 | 1954-12-28 | Devoe & Raynolds Co | Epoxide esters |
| DE969174C (de) * | 1952-06-15 | 1958-05-08 | Henkel & Cie Gmbh | Verfahren zur Herstellung von als Weichmacher fuer Phenoplaste und Cellulosederivate geeigneten Estern |
| US2781333A (en) * | 1952-09-10 | 1957-02-12 | American Cyanamid Co | Polymerizable compositions containing polyglycidyl esters of polycarboxylic acids |
| US2865897A (en) * | 1952-09-20 | 1958-12-23 | Henkel & Compagnie G M B H | Epoxy alkyl esters of polybasic aromatic carboxylic acids and process of making same |
| DE968500C (de) * | 1952-09-26 | 1958-02-27 | Henkel & Cie Gmbh | Klebmittel zur Verklebung von Werkstoffen |
| US2870170A (en) * | 1953-12-08 | 1959-01-20 | Shell Dev | Esters of epoxy-substituted polycarboxylic acids and epoxy-substituted alcohols |
| BE535560A (en, 2012) * | 1954-02-11 | |||
| BE552679A (en, 2012) * | 1955-11-17 | |||
| US3096313A (en) * | 1958-05-20 | 1963-07-02 | Du Pont | Copolymer of methyl methacrylate and glycidyl methacrylate |
| US3043813A (en) * | 1958-10-03 | 1962-07-10 | Union Carbide Corp | Polymer of alkenyl epoxycyclopentyl ethers |
| US3031439A (en) * | 1958-11-06 | 1962-04-24 | Union Carbide Corp | Co-polymerization of alkylene oxide and vinyl epoxy compounds |
| US3122568A (en) * | 1959-05-22 | 1964-02-25 | Union Carbide Corp | Epoxy esters of polycarboxylic acids |
| US3041291A (en) * | 1959-09-23 | 1962-06-26 | Union Carbide Corp | Polymerization of epoxides |
| US3062769A (en) * | 1959-11-24 | 1962-11-06 | Nat Distillers Chem Corp | Diallyl 2, 5-diphenyladipate and compositions prepared therefrom |
| US3158591A (en) * | 1960-01-26 | 1964-11-24 | Hercules Powder Co Ltd | Copolymers of epihalohydrins and ethylenically unsaturated epoxides |
| US3155638A (en) * | 1960-06-22 | 1964-11-03 | Allied Chem | Process for epoxidation of ethylenically unsaturated compounds |
| US3225115A (en) * | 1960-12-28 | 1965-12-21 | Union Carbide Corp | Curable compositions containing epoxy alcohol, unsaturated polycarboxylic acid and unsaturated monomer |
| US3417064A (en) * | 1963-05-27 | 1968-12-17 | Union Carbide Corp | Polymers of 1,2-alkylene oxides |
| US3285893A (en) * | 1964-09-17 | 1966-11-15 | Hercules Inc | Cross linked elastomeric fibers from copolymers of epihalohydrins and ethylenically unsaturated mono-epoxides |
| US3285870A (en) * | 1964-09-17 | 1966-11-15 | Hercules Inc | Copolymers of epihalohydrins and glycidyl esters of ethylenically unsaturated acids |
| IT1273617B (it) * | 1995-05-05 | 1997-07-08 | Enichem Spa | Poliolefine modificate con un estere glicidilico insaturo |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE575750C (de) * | 1931-08-06 | 1933-08-22 | Georg Frank Dr | Verfahren zur Herstellung von Polyglyciden |
| US2314039A (en) * | 1940-09-30 | 1943-03-16 | Shell Dev | Process for the production of epoxide ethers |
| DE749512C (de) * | 1938-08-23 | 1944-11-24 | Verfahren zur Herstellung von haertbaren Kunstharzen | |
| CH236894A (fr) * | 1939-04-22 | 1945-03-15 | Bell Telephone Mfg | Installation de transmission télégraphique en fac-similé. |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2224849A (en) * | 1937-11-06 | 1940-12-17 | Shell Dev | Process and products relating to glycidols |
| US2335813A (en) * | 1938-05-25 | 1943-11-30 | Gen Aniline & Film Corp | Production of carboxylic acid esters of monochlorhydrins |
| US2399214A (en) * | 1943-06-15 | 1946-04-30 | Shell Dev | Convertible alkyd resins |
-
0
- NL NL64140D patent/NL64140C/xx active
- NL NL69137D patent/NL69137C/xx active
-
1946
- 1946-06-15 US US677114A patent/US2476922A/en not_active Expired - Lifetime
-
1947
- 1947-06-16 FR FR947925D patent/FR947925A/fr not_active Expired
-
1950
- 1950-10-03 DE DEN2853A patent/DE961659C/de not_active Expired
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE575750C (de) * | 1931-08-06 | 1933-08-22 | Georg Frank Dr | Verfahren zur Herstellung von Polyglyciden |
| DE749512C (de) * | 1938-08-23 | 1944-11-24 | Verfahren zur Herstellung von haertbaren Kunstharzen | |
| CH236894A (fr) * | 1939-04-22 | 1945-03-15 | Bell Telephone Mfg | Installation de transmission télégraphique en fac-similé. |
| US2314039A (en) * | 1940-09-30 | 1943-03-16 | Shell Dev | Process for the production of epoxide ethers |
Also Published As
| Publication number | Publication date |
|---|---|
| NL69137C (en, 2012) | |
| US2476922A (en) | 1949-07-19 |
| FR947925A (fr) | 1949-07-18 |
| NL64140C (en, 2012) |
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