FR2279780A1 - Thermostable imine-polyisocyanate polymers - prepd by reacting aromatic aldimine or ketimine, aromatic polyisocyanate and opt maleimide - Google Patents
Thermostable imine-polyisocyanate polymers - prepd by reacting aromatic aldimine or ketimine, aromatic polyisocyanate and opt maleimideInfo
- Publication number
- FR2279780A1 FR2279780A1 FR7425386A FR7425386A FR2279780A1 FR 2279780 A1 FR2279780 A1 FR 2279780A1 FR 7425386 A FR7425386 A FR 7425386A FR 7425386 A FR7425386 A FR 7425386A FR 2279780 A1 FR2279780 A1 FR 2279780A1
- Authority
- FR
- France
- Prior art keywords
- bis
- polyisocyanate
- polymers
- organic
- prepd
- 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.)
- Granted
Links
- 229920001228 polyisocyanate Polymers 0.000 title abstract 4
- 239000005056 polyisocyanate Substances 0.000 title abstract 4
- 229920000642 polymer Polymers 0.000 title abstract 4
- -1 aromatic aldimine Chemical class 0.000 title abstract 2
- PEEHTFAAVSWFBL-UHFFFAOYSA-N Maleimide Chemical compound O=C1NC(=O)C=C1 PEEHTFAAVSWFBL-UHFFFAOYSA-N 0.000 title 1
- 125000003118 aryl group Chemical group 0.000 title 1
- 150000004658 ketimines Chemical class 0.000 title 1
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical group C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 abstract 3
- 125000004432 carbon atom Chemical group C* 0.000 abstract 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 abstract 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 abstract 2
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 abstract 2
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical compound C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 abstract 2
- 150000002466 imines Chemical class 0.000 abstract 2
- 229920000412 polyarylene Polymers 0.000 abstract 2
- XQUPVDVFXZDTLT-UHFFFAOYSA-N 1-[4-[[4-(2,5-dioxopyrrol-1-yl)phenyl]methyl]phenyl]pyrrole-2,5-dione Chemical compound O=C1C=CC(=O)N1C(C=C1)=CC=C1CC1=CC=C(N2C(C=CC2=O)=O)C=C1 XQUPVDVFXZDTLT-UHFFFAOYSA-N 0.000 abstract 1
- RNPJJJURTTXJOG-UHFFFAOYSA-N 2-[(2-amino-4-benzylidenecyclohexa-1,5-dien-1-yl)methyl]-5-benzylidenecyclohexa-1,3-dien-1-amine Chemical compound C(C1=CC=CC=C1)=C1CC(=C(C=C1)CC1=C(CC(C=C1)=CC1=CC=CC=C1)N)N RNPJJJURTTXJOG-UHFFFAOYSA-N 0.000 abstract 1
- YBRVSVVVWCFQMG-UHFFFAOYSA-N 4,4'-diaminodiphenylmethane Chemical compound C1=CC(N)=CC=C1CC1=CC=C(N)C=C1 YBRVSVVVWCFQMG-UHFFFAOYSA-N 0.000 abstract 1
- 239000004642 Polyimide Substances 0.000 abstract 1
- 125000004429 atom Chemical group 0.000 abstract 1
- CZZYITDELCSZES-UHFFFAOYSA-N diphenylmethane Chemical compound C=1C=CC=CC=1CC1=CC=CC=C1 CZZYITDELCSZES-UHFFFAOYSA-N 0.000 abstract 1
- 238000010438 heat treatment Methods 0.000 abstract 1
- 150000003949 imides Chemical group 0.000 abstract 1
- 239000012212 insulator Substances 0.000 abstract 1
- 239000012948 isocyanate Substances 0.000 abstract 1
- UVEWQKMPXAHFST-UHFFFAOYSA-N n,1-diphenylmethanimine Chemical compound C=1C=CC=CC=1C=NC1=CC=CC=C1 UVEWQKMPXAHFST-UHFFFAOYSA-N 0.000 abstract 1
- 229920001721 polyimide Polymers 0.000 abstract 1
- 239000001294 propane Substances 0.000 abstract 1
- 239000007858 starting material Substances 0.000 abstract 1
- 125000001174 sulfone group Chemical group 0.000 abstract 1
- RUELTTOHQODFPA-UHFFFAOYSA-N toluene 2,6-diisocyanate Chemical compound CC1=C(N=C=O)C=CC=C1N=C=O RUELTTOHQODFPA-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
- 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
- C08G18/38—Low-molecular-weight compounds having heteroatoms other than oxygen
-
- 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
- C08G18/32—Polyhydroxy compounds; Polyamines; Hydroxyamines
- C08G18/3225—Polyamines
- C08G18/3253—Polyamines being in latent form
- C08G18/3256—Reaction products of polyamines with aldehydes or ketones
-
- 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
- C08G18/38—Low-molecular-weight compounds having heteroatoms other than oxygen
- C08G18/3819—Low-molecular-weight compounds having heteroatoms other than oxygen having nitrogen
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
Novel thermostable polymers are prepd. by heating at >=180 degrees C a mixt. of an imine of formula (I) B(N=CR-G)m (I) (where m >=1; B is m-valent is not >50C organic gp. which is bonded to the imide gp(s) by one or more C atoms belonging to one or several benzene rings; G is not >35C organic gp. G' bonded by a C atom of a benzene ring is a gp. G'-CR=-B1; is as B or if m = 2 may be a gp. G'-N-B2-(N=CR-G'-CR=N-B2)w-Q; G' is not >35C divalent gp. with its free valencies on 2C atoms of 1 or 2 benzene rings; B2 is a divalent gp. B; Q is N=CR-G'-CRO or NH2; R is H or a is not >35 C organic gp. or forms a divalent gp. with G1; w is 1-10) with a polyisocyanate of formula (II) E(NCO)s (II) (where s is >=2; E is an S-valent is not >35C organic gp. bonded to the NCO gps. via C atoms of one or several benzene rings). Ratio imine:NCO gps. is pref. 0.2-5. The imide-isocyanate polymers have good mechanical and electrical props. and are chemically inert at 200-300 degrees C. They may be used for plate or tube form insulators for transformers and self-lubricating gears, rings and supports. Maleimide-contg. polymers are used similarly. Suitable starting materials are e.g. (I) benzylidene-amino benzene; bis-(4-benzylidene-amino phenyl) methane, propane, sulphone, and ether; 2,6-bis-(benzylidene-amino), (salicylideneamino)-, and (furfurylideneamino)-pyridenes; and polyimines prepd. by condensing terephthaloaldehyde with bis-(4-aminophenyl)-methane; (II) p-benzene diisocyanate; 2,4- or 2,6-TDI, 4,4'-diisocyanatodiphenyl, diphenyl methane and diphenyl ether; naphthalene, 1,5-diisocynate; and polyarylene polyisocyanates derived from aniline-HCHO condensate (III) bis-maleimide and polyarylene polyimides derived from aniline-HCHO condensates.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR7425386A FR2279780A1 (en) | 1974-07-22 | 1974-07-22 | Thermostable imine-polyisocyanate polymers - prepd by reacting aromatic aldimine or ketimine, aromatic polyisocyanate and opt maleimide |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR7425386A FR2279780A1 (en) | 1974-07-22 | 1974-07-22 | Thermostable imine-polyisocyanate polymers - prepd by reacting aromatic aldimine or ketimine, aromatic polyisocyanate and opt maleimide |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| FR2279780A1 true FR2279780A1 (en) | 1976-02-20 |
| FR2279780B1 FR2279780B1 (en) | 1977-03-25 |
Family
ID=9141543
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FR7425386A Granted FR2279780A1 (en) | 1974-07-22 | 1974-07-22 | Thermostable imine-polyisocyanate polymers - prepd by reacting aromatic aldimine or ketimine, aromatic polyisocyanate and opt maleimide |
Country Status (1)
| Country | Link |
|---|---|
| FR (1) | FR2279780A1 (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0469751A1 (en) * | 1990-07-20 | 1992-02-05 | MITSUI TOATSU CHEMICALS, Inc. | Moisture curable polyurethane composition comprising polyaldimine |
-
1974
- 1974-07-22 FR FR7425386A patent/FR2279780A1/en active Granted
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0469751A1 (en) * | 1990-07-20 | 1992-02-05 | MITSUI TOATSU CHEMICALS, Inc. | Moisture curable polyurethane composition comprising polyaldimine |
Also Published As
| Publication number | Publication date |
|---|---|
| FR2279780B1 (en) | 1977-03-25 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| ST | Notification of lapse |