GB1105437A - Polyimides and method of making same - Google Patents
Polyimides and method of making sameInfo
- Publication number
- GB1105437A GB1105437A GB2964966A GB2964966A GB1105437A GB 1105437 A GB1105437 A GB 1105437A GB 2964966 A GB2964966 A GB 2964966A GB 2964966 A GB2964966 A GB 2964966A GB 1105437 A GB1105437 A GB 1105437A
- Authority
- GB
- United Kingdom
- Prior art keywords
- diisocyanate
- tetracarboxylic
- polyimide
- solvent
- carbon atoms
- 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
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
- C08G73/00—Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00
- C08G73/06—Polycondensates having nitrogen-containing heterocyclic rings in the main chain of the macromolecule
- C08G73/10—Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors
- C08G73/1003—Preparatory processes
- C08G73/1035—Preparatory processes from tetracarboxylic acids or derivatives and diisocyanates
-
- 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
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/30—Low-molecular-weight compounds
- C08G18/34—Carboxylic acids; Esters thereof with monohydroxyl compounds
- C08G18/343—Polycarboxylic acids having at least three carboxylic acid groups
- C08G18/346—Polycarboxylic acids having at least three carboxylic acid groups having four carboxylic acid groups
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Macromolecular Compounds Obtained By Forming Nitrogen-Containing Linkages In General (AREA)
- Polyurethanes Or Polyureas (AREA)
- Drilling And Exploitation, And Mining Machines And Methods (AREA)
- Polyamides (AREA)
- Paints Or Removers (AREA)
Abstract
Polyimides may be produced by reacting a diisocyanate of formula O=C=N-R-N=C=O where R is an organic radical of at least 2 carbon atoms with an equimolar proportion of a compound containing 2 pairs of carboxyl groups linked to carbon atoms in the same organic radical, the carboxyl groups of each pair being separated by no more than 3 carbon atoms, or an imide-forming derivative thereof. The tetravalent organic radical should contain at least 2 carbon atoms. Diisocyanates specified include hexamethylene diisocyanate, dodecamethylene diisocyanate, diphenyl methane - 4,41 - diisocyanate, diphenyl ether - 4,41 - diisocyanate, toluylene diisocyanate, 2-phenyl-benzoxazole - 5,41 - diisocyanate and 1,1 - diphenyl cyclohexane - 41,411 - diisocyanate. Tetracarboxylic compounds specified include: pyromellitic, cyclopentadiene, tetracarboxylic, benzophenone - 3,31,4,41 - tetracarboxylic, diphenyloxadiazole - 1,3,4 - 3,31,4,41 - tetracarboxylic, naphthalene - 1,4,5,8 - tetracarboxylic and diphenyl ether - 3,31,4,41 - tetracarboxylic acids, dianhydrides thereof and mixtures of acids and anhydrides. The reaction takes place in a solvent, e.g. dimethyl acetamide, N-methylpyrrolidone, dimethyl sulphoxide or dimethyl formamide at atmospheric or reduced pressure. In an example, N-methyl pyrrolidone is mixed with acetone as solvent. The reaction temperature may be 50-350 DEG C. and the reactants may be in a thin layer. A cross-linked polyimide may be produced by replacing part of the diisocyanate with an equivalent quantity of an isocyanate of functionality greater than 2. Suitable compounds include triphenylmethane-4,41,411 - triisocyanate, diphenylether - 2,4,41-triisocyanate, triphenylphosphate - 4,41,411 - triisocyanate and polyphenylene polymethylene polyisocyanate. The polyimide may be obtained by evaporating the solvent or by adding a non-solvent, e.g. benzene. The products may be made into films. In a particular embodiment the polyimide is prepared at below 80 DEG C. and has a molecular weight of 1000-10,000. This reactive polyimide may be stabilized by blocking the end-groups, e.g. with caprolactone or phenol for isocyanate groups. It may later be heated above 100 DEG C., optionally in the presence of further dianhydride or isocyanate to give a higher molecular weight polyimide.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH932165A CH466924A (en) | 1965-07-02 | 1965-07-02 | Polyimide manufacturing process |
| CH1448565A CH472453A (en) | 1965-07-02 | 1965-10-20 | Polyimide manufacturing process |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1105437A true GB1105437A (en) | 1968-03-06 |
Family
ID=25704626
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB2964966A Expired GB1105437A (en) | 1965-07-02 | 1966-07-01 | Polyimides and method of making same |
Country Status (12)
| Country | Link |
|---|---|
| JP (1) | JPS544993B1 (en) |
| AT (1) | AT269480B (en) |
| BE (1) | BE683559A (en) |
| CH (2) | CH466924A (en) |
| DE (1) | DE1645363A1 (en) |
| DK (1) | DK127070B (en) |
| ES (1) | ES328647A1 (en) |
| GB (1) | GB1105437A (en) |
| LU (1) | LU51453A1 (en) |
| NL (1) | NL6609214A (en) |
| NO (1) | NO128576B (en) |
| SE (1) | SE355024B (en) |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5110897A (en) * | 1974-07-16 | 1976-01-28 | Sumitomo Electric Industries | |
| US3952084A (en) * | 1974-05-03 | 1976-04-20 | Westinghouse Electric Corporation | Polyimide and polyamide-imide precursors prepared from esters, dianhydrides, and diisocyanates |
| FR2482116A1 (en) * | 1980-04-07 | 1981-11-13 | Gen Electric | POLYETHER-IMIDE RESIN, COATING COMPOSITION CONTAINING THE RESIN, AND ISOLATED ELECTRIC CONDUCTORS USING THE SAME |
| DE3420929A1 (en) * | 1984-04-18 | 1985-11-07 | Nitto Electric Industrial Co., Ltd., Ibaraki, Osaka | SPHERICAL POROESES POLYIMIDE POWDER AND METHOD FOR THE PRODUCTION THEREOF |
| US11753517B2 (en) | 2019-12-12 | 2023-09-12 | Raytheon Company | Dispensable polyimide aerogel prepolymer, method of making the same, method of using the same, and substrate comprising patterned polyimide aerogel |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3853813A (en) * | 1973-05-24 | 1974-12-10 | Westinghouse Electric Corp | Polyimide precursor and method and composition for preparing it |
| US3833544A (en) * | 1973-06-22 | 1974-09-03 | Gen Electric | Method for making polyetherimides |
| JPS57129903A (en) * | 1981-02-06 | 1982-08-12 | Henriku Gesuta Niisutorem Peru | Sebo mechanism |
| JPS62126601U (en) * | 1986-01-31 | 1987-08-11 | ||
| JPH08278161A (en) * | 1995-02-10 | 1996-10-22 | Ckd Corp | Cylinder unit |
| JP2006028073A (en) * | 2004-07-15 | 2006-02-02 | Toyobo Co Ltd | Diisocyanate compound and polyamide-imide resin |
-
1965
- 1965-07-02 CH CH932165A patent/CH466924A/en unknown
- 1965-10-20 CH CH1448565A patent/CH472453A/en not_active IP Right Cessation
-
1966
- 1966-06-21 NO NO16358266A patent/NO128576B/no unknown
- 1966-06-29 DE DE19661645363 patent/DE1645363A1/en active Pending
- 1966-07-01 AT AT631566A patent/AT269480B/en active
- 1966-07-01 LU LU51453A patent/LU51453A1/xx unknown
- 1966-07-01 GB GB2964966A patent/GB1105437A/en not_active Expired
- 1966-07-01 NL NL6609214A patent/NL6609214A/xx unknown
- 1966-07-01 BE BE683559D patent/BE683559A/xx unknown
- 1966-07-01 SE SE1136770A patent/SE355024B/xx unknown
- 1966-07-01 DK DK341466A patent/DK127070B/en unknown
- 1966-07-02 ES ES0328647A patent/ES328647A1/en not_active Expired
- 1966-07-02 JP JP4270366A patent/JPS544993B1/ja active Pending
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3952084A (en) * | 1974-05-03 | 1976-04-20 | Westinghouse Electric Corporation | Polyimide and polyamide-imide precursors prepared from esters, dianhydrides, and diisocyanates |
| JPS5110897A (en) * | 1974-07-16 | 1976-01-28 | Sumitomo Electric Industries | |
| JPS5615647B2 (en) * | 1974-07-16 | 1981-04-11 | ||
| FR2482116A1 (en) * | 1980-04-07 | 1981-11-13 | Gen Electric | POLYETHER-IMIDE RESIN, COATING COMPOSITION CONTAINING THE RESIN, AND ISOLATED ELECTRIC CONDUCTORS USING THE SAME |
| DE3420929A1 (en) * | 1984-04-18 | 1985-11-07 | Nitto Electric Industrial Co., Ltd., Ibaraki, Osaka | SPHERICAL POROESES POLYIMIDE POWDER AND METHOD FOR THE PRODUCTION THEREOF |
| US11753517B2 (en) | 2019-12-12 | 2023-09-12 | Raytheon Company | Dispensable polyimide aerogel prepolymer, method of making the same, method of using the same, and substrate comprising patterned polyimide aerogel |
Also Published As
| Publication number | Publication date |
|---|---|
| SE355024B (en) | 1973-04-02 |
| NL6609214A (en) | 1967-01-03 |
| AT269480B (en) | 1969-03-25 |
| JPS544993B1 (en) | 1979-03-12 |
| BE683559A (en) | 1967-01-03 |
| ES328647A1 (en) | 1967-04-16 |
| LU51453A1 (en) | 1966-09-01 |
| NO128576B (en) | 1973-12-10 |
| CH466924A (en) | 1968-12-31 |
| CH472453A (en) | 1969-05-15 |
| DE1645363A1 (en) | 1970-12-10 |
| DK127070B (en) | 1973-09-17 |
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