GB1499215A - Catalysis of amine curable polymers by high dielectric constant compounds - Google Patents
Catalysis of amine curable polymers by high dielectric constant compoundsInfo
- Publication number
- GB1499215A GB1499215A GB2300375A GB2300375A GB1499215A GB 1499215 A GB1499215 A GB 1499215A GB 2300375 A GB2300375 A GB 2300375A GB 2300375 A GB2300375 A GB 2300375A GB 1499215 A GB1499215 A GB 1499215A
- Authority
- GB
- United Kingdom
- Prior art keywords
- polymers
- complex
- prepolymer
- curing agent
- sodium
- 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
- 229920000642 polymer Polymers 0.000 title abstract 10
- 150000001412 amines Chemical class 0.000 title abstract 3
- 150000001875 compounds Chemical class 0.000 title abstract 2
- 238000006555 catalytic reaction Methods 0.000 title 1
- -1 C3R Amine Chemical class 0.000 abstract 4
- 239000003795 chemical substances by application Substances 0.000 abstract 4
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 abstract 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 abstract 3
- 150000003839 salts Chemical class 0.000 abstract 3
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 abstract 2
- 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 abstract 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 abstract 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 abstract 2
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 abstract 2
- 150000003842 bromide salts Chemical class 0.000 abstract 2
- 150000003841 chloride salts Chemical class 0.000 abstract 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 abstract 2
- 150000004985 diamines Chemical class 0.000 abstract 2
- 150000004694 iodide salts Chemical class 0.000 abstract 2
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 abstract 2
- KWGKDLIKAYFUFQ-UHFFFAOYSA-M lithium chloride Chemical compound [Li+].[Cl-] KWGKDLIKAYFUFQ-UHFFFAOYSA-M 0.000 abstract 2
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 abstract 2
- 229910052708 sodium Inorganic materials 0.000 abstract 2
- 239000011734 sodium Substances 0.000 abstract 2
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 abstract 1
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 abstract 1
- KEDYYXYVCZMXCI-UHFFFAOYSA-N 4-[3-(4-aminophenyl)butan-2-yl]aniline Chemical compound C=1C=C(N)C=CC=1C(C)C(C)C1=CC=C(N)C=C1 KEDYYXYVCZMXCI-UHFFFAOYSA-N 0.000 abstract 1
- QGMGHALXLXKCBD-UHFFFAOYSA-N 4-amino-n-(2-aminophenyl)benzamide Chemical compound C1=CC(N)=CC=C1C(=O)NC1=CC=CC=C1N QGMGHALXLXKCBD-UHFFFAOYSA-N 0.000 abstract 1
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 abstract 1
- 229930185605 Bisphenol Natural products 0.000 abstract 1
- 239000004215 Carbon black (E152) Substances 0.000 abstract 1
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 abstract 1
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 abstract 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 abstract 1
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 abstract 1
- 239000005642 Oleic acid Substances 0.000 abstract 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 abstract 1
- 239000002253 acid Substances 0.000 abstract 1
- 125000004018 acid anhydride group Chemical group 0.000 abstract 1
- BTGRAWJCKBQKAO-UHFFFAOYSA-N adiponitrile Chemical compound N#CCCCCC#N BTGRAWJCKBQKAO-UHFFFAOYSA-N 0.000 abstract 1
- 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 abstract 1
- 239000001273 butane Substances 0.000 abstract 1
- 229910052792 caesium Inorganic materials 0.000 abstract 1
- TVFDJXOCXUVLDH-UHFFFAOYSA-N caesium atom Chemical compound [Cs] TVFDJXOCXUVLDH-UHFFFAOYSA-N 0.000 abstract 1
- 230000003197 catalytic effect Effects 0.000 abstract 1
- KXZJHVJKXJLBKO-UHFFFAOYSA-N chembl1408157 Chemical compound N=1C2=CC=CC=C2C(C(=O)O)=CC=1C1=CC=C(O)C=C1 KXZJHVJKXJLBKO-UHFFFAOYSA-N 0.000 abstract 1
- DENRZWYUOJLTMF-UHFFFAOYSA-N diethyl sulfate Chemical compound CCOS(=O)(=O)OCC DENRZWYUOJLTMF-UHFFFAOYSA-N 0.000 abstract 1
- 239000004205 dimethyl polysiloxane Substances 0.000 abstract 1
- 229960001760 dimethyl sulfoxide Drugs 0.000 abstract 1
- WNAHIZMDSQCWRP-UHFFFAOYSA-N dodecane-1-thiol Chemical compound CCCCCCCCCCCCS WNAHIZMDSQCWRP-UHFFFAOYSA-N 0.000 abstract 1
- 239000003822 epoxy resin Substances 0.000 abstract 1
- 150000004820 halides Chemical class 0.000 abstract 1
- 229910052736 halogen Inorganic materials 0.000 abstract 1
- 150000002367 halogens Chemical class 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
- 229930195733 hydrocarbon Natural products 0.000 abstract 1
- 150000002430 hydrocarbons Chemical class 0.000 abstract 1
- 239000012948 isocyanate Substances 0.000 abstract 1
- 150000002513 isocyanates Chemical class 0.000 abstract 1
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 abstract 1
- 229910052744 lithium Inorganic materials 0.000 abstract 1
- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 abstract 1
- OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 abstract 1
- 150000002823 nitrates Chemical class 0.000 abstract 1
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 abstract 1
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 abstract 1
- 239000000049 pigment Substances 0.000 abstract 1
- 229920000435 poly(dimethylsiloxane) Polymers 0.000 abstract 1
- 229920000647 polyepoxide Polymers 0.000 abstract 1
- 229920001225 polyester resin Polymers 0.000 abstract 1
- 239000004645 polyester resin Substances 0.000 abstract 1
- 229920001296 polysiloxane Polymers 0.000 abstract 1
- 229910052700 potassium Inorganic materials 0.000 abstract 1
- 239000011591 potassium Substances 0.000 abstract 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 abstract 1
- 229910052701 rubidium Inorganic materials 0.000 abstract 1
- IGLNJRXAVVLDKE-UHFFFAOYSA-N rubidium atom Chemical compound [Rb] IGLNJRXAVVLDKE-UHFFFAOYSA-N 0.000 abstract 1
- 239000011780 sodium chloride Substances 0.000 abstract 1
- STCOOQWBFONSKY-UHFFFAOYSA-N tributyl phosphate Chemical compound CCCCOP(=O)(OCCCC)OCCCC STCOOQWBFONSKY-UHFFFAOYSA-N 0.000 abstract 1
- XTTGYFREQJCEML-UHFFFAOYSA-N tributyl phosphite Chemical compound CCCCOP(OCCCC)OCCCC XTTGYFREQJCEML-UHFFFAOYSA-N 0.000 abstract 1
- DQWPFSLDHJDLRL-UHFFFAOYSA-N triethyl phosphate Chemical compound CCOP(=O)(OCC)OCC DQWPFSLDHJDLRL-UHFFFAOYSA-N 0.000 abstract 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
- C08G59/50—Amines
- C08G59/5093—Complexes of amines
-
- 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
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/08—Processes
- C08G18/10—Prepolymer processes involving reaction of isocyanates or isothiocyanates with compounds having active hydrogen in a first reaction step
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Polyurethanes Or Polyureas (AREA)
Abstract
1499215 Curing amine curable polymers FIRESTONE TIRE & RUBBER CO 23 May 1975 [5 June 1974 12 Aug 1974] 23003/75 Heading C3R Amine curable polymers or prepolymers selected from (a) urethane containing free isocyanate groups, epoxy resins, polymers containing acid halide or haloformate groups and polymers containing acid anhydride groups or (b) halogen-containing hydrocarbon polymers, chlorosulphonated polymers and organopolysiloxanes are cured with a curing agent in amounts of 100 parts of polymer or prepolymer and in the case of group (a), 0À8 to 1À2 equivalents based on diamine of curing agent and in the case of group (b) 0À0005 to 0À05 equivalents based on diamine of curing agent based upon the active groups of the polymer or prepolymer, the curing agent being selected from a complex of 4,41-methylene dianiline and a salt selected from the chlorides, bromides, iodides and nitrates of sodium and lithium and sodium cyanide and a complex of racemic 2,3-di(4- aminophenyl)butane and a salt selected from the chlorides, bromides and iodides of sodium, potassium, rubidium and cesium, the ratio of the dianiline or butane to the salt in the complex being 3 moles per mole, and from 0À1 to 35 parts of a catalytic compound having a dielectric constant of at least 2À0 and a relatively slow reaction rate (defined) with amines and isocyanates and being selected from tributyl phosphate (preferred), triethylphosphate, tributyl phosphite, oleic acid, dimethyl sulphoxide, dodecyl mercaptan, benzaldehyde, adiponitrile, nitrobenzene, cyclohexanone, N,N<SP>1</SP>-dimethylbenzylamine, acetic anhydride, a low M.W. epichlorohydrin/bisphenol adduct, a low M.W. polyester resin containing a black pigment therein, polydimethylsiloxane, pyridine, diethyl sulphate and dimethylformamide. Most preferably the polymer or prepolymer is a urethane prepolymer containing free isocyanate group and the complex is one of 4,41-methylene dianiline and sodium chloride or lithium chloride. Curing is preferably conducted at a temperature of from 80‹ to 140‹ C.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US47636974A | 1974-06-05 | 1974-06-05 | |
| US49650474A | 1974-08-12 | 1974-08-12 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1499215A true GB1499215A (en) | 1978-01-25 |
Family
ID=27045161
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB2300375A Expired GB1499215A (en) | 1974-06-05 | 1975-05-23 | Catalysis of amine curable polymers by high dielectric constant compounds |
Country Status (6)
| Country | Link |
|---|---|
| JP (1) | JPS561330B2 (en) |
| CA (1) | CA1065995A (en) |
| DE (1) | DE2524083C2 (en) |
| FR (1) | FR2273838A1 (en) |
| GB (1) | GB1499215A (en) |
| IT (1) | IT1036151B (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN115466389A (en) * | 2022-09-13 | 2022-12-13 | 中国人民解放军国防科技大学 | A kind of low-temperature fast-curing hydroxyl-containing structural cyanate resin and preparation method thereof |
| CN115701420A (en) * | 2021-08-02 | 2023-02-10 | 中国石油化工股份有限公司 | Method for improving fatty acid amide synthesis reaction charging coefficient |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| SE7605306L (en) * | 1975-05-16 | 1976-11-17 | Firestone Tire & Rubber Co | WITH AMIN CURTAINABLE POLYMER |
| JPH0379892A (en) * | 1989-08-21 | 1991-04-04 | Yoshihisa Miura | Ferrule with chuck |
| US6287080B1 (en) * | 1999-11-15 | 2001-09-11 | General Electric Company | Elastomeric formulation used in the construction of lightweight aircraft engine fan blades |
| CA2636738C (en) | 2006-01-13 | 2016-11-08 | Swagelok Company | Fitting with adapted engaging surfaces |
| BR112018005209B1 (en) * | 2015-09-25 | 2022-03-22 | Lanxess Solution Us Inc | Method of preparing a polyurethane elastomer |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3755261A (en) * | 1972-05-01 | 1973-08-28 | Du Pont | Curing of amine curable polymers diamines with complexes of selected and alkali metal salts |
-
1975
- 1975-05-23 GB GB2300375A patent/GB1499215A/en not_active Expired
- 1975-05-29 FR FR7516823A patent/FR2273838A1/en active Granted
- 1975-05-30 CA CA228,111A patent/CA1065995A/en not_active Expired
- 1975-05-30 DE DE19752524083 patent/DE2524083C2/en not_active Expired
- 1975-06-04 IT IT6841875A patent/IT1036151B/en active
- 1975-06-04 JP JP6661375A patent/JPS561330B2/ja not_active Expired
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN115701420A (en) * | 2021-08-02 | 2023-02-10 | 中国石油化工股份有限公司 | Method for improving fatty acid amide synthesis reaction charging coefficient |
| CN115466389A (en) * | 2022-09-13 | 2022-12-13 | 中国人民解放军国防科技大学 | A kind of low-temperature fast-curing hydroxyl-containing structural cyanate resin and preparation method thereof |
| CN115466389B (en) * | 2022-09-13 | 2023-07-25 | 中国人民解放军国防科技大学 | Low-temperature rapid-curing hydroxyl-structure-containing cyanate resin and preparation method thereof |
Also Published As
| Publication number | Publication date |
|---|---|
| FR2273838A1 (en) | 1976-01-02 |
| JPS5130297A (en) | 1976-03-15 |
| JPS561330B2 (en) | 1981-01-13 |
| DE2524083C2 (en) | 1986-09-11 |
| CA1065995A (en) | 1979-11-06 |
| FR2273838B1 (en) | 1979-04-13 |
| DE2524083A1 (en) | 1976-01-15 |
| IT1036151B (en) | 1979-10-30 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PS | Patent sealed | ||
| PCNP | Patent ceased through non-payment of renewal fee |