GB897726A - A process for the manufacture of hardened artificial resin materials and compositions therefor - Google Patents
A process for the manufacture of hardened artificial resin materials and compositions thereforInfo
- Publication number
- GB897726A GB897726A GB27256/58A GB2725658A GB897726A GB 897726 A GB897726 A GB 897726A GB 27256/58 A GB27256/58 A GB 27256/58A GB 2725658 A GB2725658 A GB 2725658A GB 897726 A GB897726 A GB 897726A
- Authority
- GB
- United Kingdom
- Prior art keywords
- acrylamide
- acid
- copolymerization
- cyclohexyl
- butyl
- 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
- 239000000203 mixture Substances 0.000 title abstract 4
- 239000000463 material Substances 0.000 title abstract 2
- 238000004519 manufacturing process Methods 0.000 title 1
- 238000000034 method Methods 0.000 title 1
- 239000011347 resin Substances 0.000 title 1
- 229920005989 resin Polymers 0.000 title 1
- -1 hydrocarbon radical Chemical class 0.000 abstract 5
- 150000001875 compounds Chemical class 0.000 abstract 4
- 238000007334 copolymerization reaction Methods 0.000 abstract 4
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 abstract 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 abstract 3
- 150000001408 amides Chemical class 0.000 abstract 3
- 229920001577 copolymer Polymers 0.000 abstract 3
- 239000000047 product Substances 0.000 abstract 3
- 125000001302 tertiary amino group Chemical group 0.000 abstract 3
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 abstract 2
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 abstract 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 abstract 2
- SOGAXMICEFXMKE-UHFFFAOYSA-N Butylmethacrylate Chemical compound CCCCOC(=O)C(C)=C SOGAXMICEFXMKE-UHFFFAOYSA-N 0.000 abstract 2
- REWIWCKGGYQQPK-UHFFFAOYSA-N N-cyclohexyl-N-(2-hydroxypropyl)prop-2-enamide Chemical compound C1(CCCCC1)N(C(C=C)=O)CC(C)O REWIWCKGGYQQPK-UHFFFAOYSA-N 0.000 abstract 2
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 abstract 2
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 abstract 2
- ZDZQUEQQGOQGRY-UHFFFAOYSA-N [[4,6-bis[bis(hydroxymethyl)amino]-1,3,5-triazin-2-yl]-(hydroxymethyl)amino]methanol;prop-2-enamide Chemical compound NC(=O)C=C.NC(=O)C=C.NC(=O)C=C.OCN(CO)C1=NC(N(CO)CO)=NC(N(CO)CO)=N1 ZDZQUEQQGOQGRY-UHFFFAOYSA-N 0.000 abstract 2
- 239000007795 chemical reaction product Substances 0.000 abstract 2
- DOIRQSBPFJWKBE-UHFFFAOYSA-N dibutyl phthalate Chemical compound CCCCOC(=O)C1=CC=CC=C1C(=O)OCCCC DOIRQSBPFJWKBE-UHFFFAOYSA-N 0.000 abstract 2
- 235000014113 dietary fatty acids Nutrition 0.000 abstract 2
- 239000003822 epoxy resin Substances 0.000 abstract 2
- 239000000194 fatty acid Substances 0.000 abstract 2
- 229930195729 fatty acid Natural products 0.000 abstract 2
- DCAYPVUWAIABOU-UHFFFAOYSA-N hexadecane Chemical compound CCCCCCCCCCCCCCCC DCAYPVUWAIABOU-UHFFFAOYSA-N 0.000 abstract 2
- 125000005395 methacrylic acid group Chemical group 0.000 abstract 2
- DLJMSHXCPBXOKX-UHFFFAOYSA-N n,n-dibutylprop-2-enamide Chemical class CCCCN(C(=O)C=C)CCCC DLJMSHXCPBXOKX-UHFFFAOYSA-N 0.000 abstract 2
- GFOCCLOYMMHTIU-UHFFFAOYSA-N n-[3-(diethylamino)propyl]prop-2-enamide Chemical compound CCN(CC)CCCNC(=O)C=C GFOCCLOYMMHTIU-UHFFFAOYSA-N 0.000 abstract 2
- RZJRJXONCZWCBN-UHFFFAOYSA-N octadecane Chemical compound CCCCCCCCCCCCCCCCCC RZJRJXONCZWCBN-UHFFFAOYSA-N 0.000 abstract 2
- 229920000647 polyepoxide Polymers 0.000 abstract 2
- 239000000843 powder Substances 0.000 abstract 2
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 abstract 1
- KRHOKZHVSQKTJI-BJBXXJATSA-N (1S,3R,8R,9S,11R)-2,2-dichloro-3,7,7,11-tetramethyl-10-oxatetracyclo[6.5.0.01,3.09,11]tridecane Chemical compound CC1(C)CCC[C@@]2(C)C(Cl)(Cl)[C@]22CC[C@@](C)(O3)[C@@H]3[C@@H]21 KRHOKZHVSQKTJI-BJBXXJATSA-N 0.000 abstract 1
- MUTGBJKUEZFXGO-OLQVQODUSA-N (3as,7ar)-3a,4,5,6,7,7a-hexahydro-2-benzofuran-1,3-dione Chemical compound C1CCC[C@@H]2C(=O)OC(=O)[C@@H]21 MUTGBJKUEZFXGO-OLQVQODUSA-N 0.000 abstract 1
- KMOUUZVZFBCRAM-OLQVQODUSA-N (3as,7ar)-3a,4,7,7a-tetrahydro-2-benzofuran-1,3-dione Chemical compound C1C=CC[C@@H]2C(=O)OC(=O)[C@@H]21 KMOUUZVZFBCRAM-OLQVQODUSA-N 0.000 abstract 1
- VILCJCGEZXAXTO-UHFFFAOYSA-N 2,2,2-tetramine Chemical compound NCCNCCNCCN VILCJCGEZXAXTO-UHFFFAOYSA-N 0.000 abstract 1
- AHDSRXYHVZECER-UHFFFAOYSA-N 2,4,6-tris[(dimethylamino)methyl]phenol Chemical compound CN(C)CC1=CC(CN(C)C)=C(O)C(CN(C)C)=C1 AHDSRXYHVZECER-UHFFFAOYSA-N 0.000 abstract 1
- CFVWNXQPGQOHRJ-UHFFFAOYSA-N 2-methylpropyl prop-2-enoate Chemical compound CC(C)COC(=O)C=C CFVWNXQPGQOHRJ-UHFFFAOYSA-N 0.000 abstract 1
- 239000005995 Aluminium silicate Substances 0.000 abstract 1
- 239000004215 Carbon black (E152) Substances 0.000 abstract 1
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 abstract 1
- JIGUQPWFLRLWPJ-UHFFFAOYSA-N Ethyl acrylate Chemical compound CCOC(=O)C=C JIGUQPWFLRLWPJ-UHFFFAOYSA-N 0.000 abstract 1
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 abstract 1
- 239000004606 Fillers/Extenders Substances 0.000 abstract 1
- IGFHQQFPSIBGKE-UHFFFAOYSA-N Nonylphenol Natural products CCCCCCCCCC1=CC=C(O)C=C1 IGFHQQFPSIBGKE-UHFFFAOYSA-N 0.000 abstract 1
- HDSBZMRLPLPFLQ-UHFFFAOYSA-N Propylene glycol alginate Chemical compound OC1C(O)C(OC)OC(C(O)=O)C1OC1C(O)C(O)C(C)C(C(=O)OCC(C)O)O1 HDSBZMRLPLPFLQ-UHFFFAOYSA-N 0.000 abstract 1
- 239000002253 acid Substances 0.000 abstract 1
- 150000001336 alkenes Chemical class 0.000 abstract 1
- 235000012211 aluminium silicate Nutrition 0.000 abstract 1
- 150000008064 anhydrides Chemical class 0.000 abstract 1
- 239000010425 asbestos Substances 0.000 abstract 1
- JHIWVOJDXOSYLW-UHFFFAOYSA-N butyl 2,2-difluorocyclopropane-1-carboxylate Chemical compound CCCCOC(=O)C1CC1(F)F JHIWVOJDXOSYLW-UHFFFAOYSA-N 0.000 abstract 1
- 229910052799 carbon Inorganic materials 0.000 abstract 1
- 125000004432 carbon atom Chemical group C* 0.000 abstract 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 abstract 1
- 239000003795 chemical substances by application Substances 0.000 abstract 1
- LDHQCZJRKDOVOX-NSCUHMNNSA-N crotonic acid Chemical class C\C=C\C(O)=O LDHQCZJRKDOVOX-NSCUHMNNSA-N 0.000 abstract 1
- 150000004985 diamines Chemical class 0.000 abstract 1
- 239000000839 emulsion Substances 0.000 abstract 1
- 150000002148 esters Chemical class 0.000 abstract 1
- 150000002170 ethers Chemical class 0.000 abstract 1
- 150000004665 fatty acids Chemical class 0.000 abstract 1
- SLGWESQGEUXWJQ-UHFFFAOYSA-N formaldehyde;phenol Chemical compound O=C.OC1=CC=CC=C1 SLGWESQGEUXWJQ-UHFFFAOYSA-N 0.000 abstract 1
- 235000011087 fumaric acid Nutrition 0.000 abstract 1
- 150000002238 fumaric acids Chemical class 0.000 abstract 1
- 239000011521 glass Substances 0.000 abstract 1
- 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 abstract 1
- FLBJFXNAEMSXGL-UHFFFAOYSA-N het anhydride Chemical compound O=C1OC(=O)C2C1C1(Cl)C(Cl)=C(Cl)C2(Cl)C1(Cl)Cl FLBJFXNAEMSXGL-UHFFFAOYSA-N 0.000 abstract 1
- 125000000623 heterocyclic group Chemical group 0.000 abstract 1
- 229930195733 hydrocarbon Natural products 0.000 abstract 1
- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 abstract 1
- 239000010985 leather Substances 0.000 abstract 1
- 150000002689 maleic acids Chemical class 0.000 abstract 1
- FQPSGWSUVKBHSU-UHFFFAOYSA-N methacrylamide Chemical class CC(=C)C(N)=O FQPSGWSUVKBHSU-UHFFFAOYSA-N 0.000 abstract 1
- 239000003607 modifier Substances 0.000 abstract 1
- PMJFVKWBSWWAKT-UHFFFAOYSA-N n-cyclohexylprop-2-enamide Chemical class C=CC(=O)NC1CCCCC1 PMJFVKWBSWWAKT-UHFFFAOYSA-N 0.000 abstract 1
- XFHJDMUEHUHAJW-UHFFFAOYSA-N n-tert-butylprop-2-enamide Chemical compound CC(C)(C)NC(=O)C=C XFHJDMUEHUHAJW-UHFFFAOYSA-N 0.000 abstract 1
- 229910052757 nitrogen Inorganic materials 0.000 abstract 1
- 125000004433 nitrogen atom Chemical group N* 0.000 abstract 1
- SNQQPOLDUKLAAF-UHFFFAOYSA-N nonylphenol Chemical compound CCCCCCCCCC1=CC=CC=C1O SNQQPOLDUKLAAF-UHFFFAOYSA-N 0.000 abstract 1
- 229920003986 novolac Polymers 0.000 abstract 1
- 229940038384 octadecane Drugs 0.000 abstract 1
- 150000002924 oxiranes Chemical group 0.000 abstract 1
- 239000000123 paper Substances 0.000 abstract 1
- PNJWIWWMYCMZRO-UHFFFAOYSA-N pent‐4‐en‐2‐one Natural products CC(=O)CC=C PNJWIWWMYCMZRO-UHFFFAOYSA-N 0.000 abstract 1
- 229920001568 phenolic resin Polymers 0.000 abstract 1
- 239000004014 plasticizer Substances 0.000 abstract 1
- 230000000379 polymerizing effect Effects 0.000 abstract 1
- 235000010409 propane-1,2-diol alginate Nutrition 0.000 abstract 1
- 239000000770 propane-1,2-diol alginate Substances 0.000 abstract 1
- 239000010453 quartz Substances 0.000 abstract 1
- 229910052895 riebeckite Inorganic materials 0.000 abstract 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 abstract 1
- 239000004575 stone Substances 0.000 abstract 1
- 239000004753 textile Substances 0.000 abstract 1
- 229960001124 trientine Drugs 0.000 abstract 1
- 229920001567 vinyl ester resin Polymers 0.000 abstract 1
- 229920002554 vinyl polymer Polymers 0.000 abstract 1
Classifications
-
- 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
- C08F20/00—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride, ester, amide, imide or nitrile thereof
- C08F20/62—Monocarboxylic acids having ten or more carbon atoms; Derivatives 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
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L57/00—Compositions of unspecified polymers obtained by reactions only involving carbon-to-carbon unsaturated bonds
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J2363/00—Characterised by the use of epoxy resins; Derivatives of epoxy resins
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)
- Compositions Of Macromolecular Compounds (AREA)
Abstract
A hardenable composition comprises an epoxy resin which is substantially free from carboxyl groups and contains n epoxide groups calculated on the molecular weight, where n represents a whole or fractional number greater than 1, and a copolymerization product obtained by polymerizing at least one compound containing at least one polymerizable carbon-to-carbon double bond and at least one tertiary amino group of the formula -NR1R2 in which R1 and R2 each represent a hydrocarbon radical of 1 to 6 carbon atoms which may be substituted or may be linked together to form with the nitrogen atom a heterocyclic ring, jointly with at least one non-basic amide of a copolymerizable acid, and the content of the component containing a tertiary amino group in the copolymerization product being less than 40% by weight. As materials containing basic tertiary amino groups there are suitable such compounds as are specified for the copolymer curing agents of Specification 897,985. As copolymerizable non-basic amides there are specified amides of acryl, methacrylic fumaric and crotonic acids, e.g. N-methyl ethyl butyl ter. octyl- and cyclohexyl acrylamides, N,N-dimethyl or dibutyl acrylamides or methacrylamides, N;N-di(b -hydroxyethyl)acrylamide, N-cyclohexyl-N-2-hydroxypropylacrylamide and hexamethylolmelamine triacrylic acid amide. The copolymers may also contain a third copolymerization component such as a vinyl ester, vinyl halide, vinyl alkyl ketone, vinylaryl compound, esters of acrylic acid, methacrylic, a -chloracrylic, crotonic, itaconic, maleic or fumaric acids, acrylic acid itself or polymerizable olefins. The copolymers may be used together with such compounds as triethylene tetramine, N:N-diethylpropylene diamine, tris-(dimethylaminomethyl)phenol, 4,41-diaminodiphenylmethane, phthalic, tetrahydrophthalic or hexahydrophthalic anhydride, methylendomethylenetetrahydrophthalic anhydride or hexachloroendomethylene-tetrahydrophthalic anhydride. As modifiers there can be added to the compositions epoxy-dodecane, hexadecane or octadecane or epoxidized fatty acids or fatty acid esters. Plasticizers such as dibutyl phthalate and extenders such as quartz powder, kaolin, stone powder, glass or asbestos fibres may be added. For use in treating leather, paper or textiles the compositions may be used in the form of an emulsion, for example, with hydrolyzed PVA, propylene glycol alginate and a nonyl-phenol/ethylene oxide reaction product. In the examples the copolymerization products obtained from (1) N-diethylaminopropylacrylamide, N-tertiary butyl acrylamide and ethyl acrylate; (2) N-tert.-octylacrylamide and N-diethylaminophenyl acrylamide; (3) N-dimethylaminoethyl vinyl ether; (4) N-diethylaminoethyl crotonate, butyl methacrylate and di-butyl acrylamide; (5) N-diethylaminopropyl acrylamide, N-cyclohexyl-N-(2-hydroxypropyl)-acrylamide, and isobutyl acrylate; (6) diethylaminopropyl acrylamide and hexamethylolmelamine triacrylic acid amide. Epoxy resins employed are the polyglycidyl ethers of 4,41-dihydroxydiphenyl dimethyl methane, ethylene glycol, butylene glycol; reaction products of epichlorhydrin with terephthalic acid, a phenolformaldehyde novolak or aniline. Specification 816,630 also is referred to.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH4975557 | 1957-08-23 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB897726A true GB897726A (en) | 1962-05-30 |
Family
ID=4516795
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB27256/58A Expired GB897726A (en) | 1957-08-23 | 1958-08-25 | A process for the manufacture of hardened artificial resin materials and compositions therefor |
| GB27255/58A Expired GB897985A (en) | 1957-08-23 | 1958-08-25 | A process for the manufacture of hardened artificial resin materials and compositions therefor |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB27255/58A Expired GB897985A (en) | 1957-08-23 | 1958-08-25 | A process for the manufacture of hardened artificial resin materials and compositions therefor |
Country Status (6)
| Country | Link |
|---|---|
| BE (2) | BE570570A (en) |
| CH (1) | CH49755A (en) |
| DE (2) | DE1106492B (en) |
| FR (2) | FR1211575A (en) |
| GB (2) | GB897726A (en) |
| NL (5) | NL6408449A (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3385809A (en) * | 1965-09-03 | 1968-05-28 | Richardson Co | Fat acid amides of nu, nu-dialkyl (alkylene diamines) as curing agents for epoxy resi |
| US3538185A (en) * | 1967-08-10 | 1970-11-03 | Dow Chemical Co | Coating compositions containing vinyl polymers with pendant alkylenimine group and epoxy resins |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1120133B (en) * | 1959-01-23 | 1961-12-21 | Ciba Geigy | Process for accelerating the hardening of polyepoxy compounds by means of anhydride polybasic carboxylic acids |
| US3467611A (en) * | 1966-01-07 | 1969-09-16 | Du Pont | Mixture of aqueous emulsions |
| JPS5428960B1 (en) * | 1968-01-22 | 1979-09-20 | ||
| GB1555781A (en) * | 1975-08-27 | 1979-11-14 | Pollution Preventing Res | Methods for producing dibasic fatty acid |
| CA1086445A (en) * | 1976-02-23 | 1980-09-23 | Changkiu K. Riew | Thermoplastic, thermosetting elastomeric compositions and methods for making the same |
| US5013791A (en) * | 1987-12-30 | 1991-05-07 | Ppg Industries, Inc. | Beta-hydroxyalkylamide cured acid polymer/polyepoxide powder coating |
| US4889890A (en) * | 1987-12-30 | 1989-12-26 | Ppg Industries, Inc. | Powder coating curing system containing a beta-hydroxyalkylamide |
| EP3118234A1 (en) | 2015-07-15 | 2017-01-18 | ALLNEX AUSTRIA GmbH | Coating compositions |
-
0
- NL NL110443D patent/NL110443C/xx active
- BE BE570571D patent/BE570571A/xx unknown
- NL NL110442D patent/NL110442C/xx active
- NL NL230770D patent/NL230770A/xx unknown
- BE BE570570D patent/BE570570A/xx unknown
-
1909
- 1909-10-25 CH CH49755A patent/CH49755A/en unknown
-
1958
- 1958-08-21 FR FR1211575D patent/FR1211575A/en not_active Expired
- 1958-08-21 FR FR1211576D patent/FR1211576A/en not_active Expired
- 1958-08-22 DE DEC17391A patent/DE1106492B/en active Pending
- 1958-08-22 DE DEC17390A patent/DE1085667B/en active Pending
- 1958-08-25 GB GB27256/58A patent/GB897726A/en not_active Expired
- 1958-08-25 GB GB27255/58A patent/GB897985A/en not_active Expired
-
1964
- 1964-07-23 NL NL6408449A patent/NL6408449A/xx unknown
- 1964-07-23 NL NL6408445A patent/NL6408445A/xx unknown
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3385809A (en) * | 1965-09-03 | 1968-05-28 | Richardson Co | Fat acid amides of nu, nu-dialkyl (alkylene diamines) as curing agents for epoxy resi |
| US3538185A (en) * | 1967-08-10 | 1970-11-03 | Dow Chemical Co | Coating compositions containing vinyl polymers with pendant alkylenimine group and epoxy resins |
Also Published As
| Publication number | Publication date |
|---|---|
| BE570570A (en) | |
| NL6408445A (en) | 1964-10-12 |
| NL6408449A (en) | 1964-10-12 |
| FR1211576A (en) | 1960-03-17 |
| GB897985A (en) | 1962-06-06 |
| NL230770A (en) | |
| DE1106492B (en) | 1961-05-10 |
| CH49755A (en) | 1911-03-16 |
| NL110443C (en) | |
| FR1211575A (en) | 1960-03-17 |
| NL110442C (en) | |
| DE1085667B (en) | 1960-07-21 |
| BE570571A (en) |
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