US4296219A
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Bismide-ether compounds, compositions thereof, and method of producing same
Assignee: Hitachi Ltd
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Filing: 1979-01-22
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Granted: 1981-10-20
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Expires: 1999-01-22
Abstract
Abstract A bisimide-ether compound having the general formula is obtained by reacting an ethylenically unsaturated dicarboxylic acid anhydride, a diamine compound and a phenolic compound having in the molecule at least two hydroxyl groups, or by reacting a prepolymer of the anhydride and diamine compound with the phenolic compound: <IMAGE> wherein R1 is a group containing at least two carbon atoms, R2 is a group containing at least two carbon atoms, R'2 is a group containing at least two carbon atoms and a carbon-carbon double bond, R3 is an aromatic group, the nitrogen atoms of the imide rings being directly connected to different carbon atoms of the group R1, the carbonyl groups of the imide rings being directly connected to different carbon atoms of the group R2 or R'2, the oxygen atoms between the groups R2 and R3 being directly connected to an aromatic nucleus of the group R3, and n is an integer of zero, one or more than 1.
Inventors
- 👤 Akio Takahashi
- 👤 Yutaka Itoh
- 👤 Motoyo Wajima
- 👤 Hirosada Morishita
- 👤 Akio Nishikawa
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-05 20:23
CPC Classifications
C; C07; C07D; C07D207/00; C07D207/02; C07D207/44; C07D207/444; C07D207/448; C08; C08G; C08G73/00; C08G73/06; C08G73/10; C08G73/12; C08G73/121
Claims Analysis
Total Claims: 46
Claim 1
Independent Claim
159 words
A bisimide-ether compound having the general formula: ##STR11## wherein R 1 is a group containing at least two carbon atoms, the nitrogen atoms of the imide rings being directly connected to different carbon atoms of the group R 1 , R 2 is a group containing at least two carbon atoms, the carbonyl groups of the imide rings being directly connected to different carbon atoms of the group R 2 , R' 2 is a group containing at least two carbon atoms and a carbon-carbon double bond, R 3 is an aromatic group, the oxygen atoms between the groups R 2 and R 3 being directly connected to different carbon atoms of the aromatic nucleus of the group R 3 , and n is an integer of zero, 1 or larger than 1, the bisimide ether compound being soluble in an organic solvent having a boiling point not higher than 130° C. at normal temperature and under normal pressure.
Claim 2
Dependent Claim
159 words
A bisimide-ether compound having the general formula: ##STR11## wherein R 1 is a group containing at least two carbon atoms, the nitrogen atoms of the imide rings being directly connected to different carbon atoms of the group R 1 , R 2 is a group containing at least two carbon atoms, the carbonyl groups of the imide rings being directly connected to different carbon atoms of the group R 2 , R' 2 is a group containing at least two carbon atoms and a carbon-carbon double bond, R 3 is an aromatic group, the oxygen atoms between the groups R 2 and R 3 being directly connected to different carbon atoms of the aromatic nucleus of the group R 3 , and n is an integer of zero, 1 or larger than 1, the bisimide ether compound being soluble in an organic solvent having a boiling point not higher than 130° C. at normal temperature and under normal pressure.
Claim 3
Dependent Claim
20 words
A bisimide-ether compound according to claim 1, wherein R 1 is an aromatic group containing at least one aromatic nucleus.
Claim 4
Dependent Claim
12 words
A bisimide-ether compound according to claim 1, wherein R 2 is ##STR12##
Claim 5
Dependent Claim
30 words
A bisimide-ether compound according to claim 1, wherein R 3 is a residue of a phenol resin having at least one free hydroxyl group directly connected to an aromatic nucleus.
Claim 6
Dependent Claim
27 words
A solvent-soluble thermosetting resin according to claim 4, wherein the phenol resin is a novolac type phenol resin polymer having a softening point lower than 170° C.
Claim 7
Independent Claim
222 words
A method of producing a bisimide-ether compound which comprises heating a mixture of an ethylenically unsaturated dicarboxylic acid anhydride, an organic diamine and a phenolic compound containing at least two hydroxyl groups directly connected to different carbon atoms of an aromatic nucleus of the compound, said phenolic compound having a softening point lower than 170° C., at an elevated temperature for a time sufficient to provide at least 10% by weight, based on the mixture, of a bisimide-ether compound having the general formula: ##STR13## wherein R 1 is a residual group of the diamine containing at least two carbon atoms, the nitrogen atoms of the imide rings being directly connected to different carbon atoms of the group R 1 , R 2 is a residual group of the dicarboxylic acid anhydride containing at least two carbon atoms, the carbonyl groups of the imide rings being directly connected to different carbon atoms of the group R 2 or R' 2 , R' 2 is a group containing at least two carbon atoms and a carbon-carbon double bond, R 3 is a residual group of the phenolic compound, and n is an integer of zero, 1 or larger than 1, the bisimide-ether compound being soluble in an organic solvent having a boiling point lower than 130° C. at normal temperature and under normal pressure.
Claim 8
Independent Claim
222 words
A method of producing a bisimide-ether compound which comprises heating a mixture of an ethylenically unsaturated dicarboxylic acid anhydride, an organic diamine and a phenolic compound containing at least two hydroxyl groups directly connected to different carbon atoms of an aromatic nucleus of the compound, said phenolic compound having a softening point lower than 170° C., at an elevated temperature for a time sufficient to provide at least 10% by weight, based on the mixture, of a bisimide-ether compound having the general formula: ##STR13## wherein R 1 is a residual group of the diamine containing at least two carbon atoms, the nitrogen atoms of the imide rings being directly connected to different carbon atoms of the group R 1 , R 2 is a residual group of the dicarboxylic acid anhydride containing at least two carbon atoms, the carbonyl groups of the imide rings being directly connected to different carbon atoms of the group R 2 or R' 2 , R' 2 is a group containing at least two carbon atoms and a carbon-carbon double bond, R 3 is a residual group of the phenolic compound, and n is an integer of zero, 1 or larger than 1, the bisimide-ether compound being soluble in an organic solvent having a boiling point lower than 130° C. at normal temperature and under normal pressure.
Claim 9
Dependent Claim
19 words
A method according to claim 6, wherein R 1 is an aromatic group containing at least one aromatic nucleus.
Claim 10
Dependent Claim
11 words
A method according to claim 6, wherein R 2 is ##STR14##
Claim 11
Dependent Claim
30 words
A method according to claim 6, wherein R 3 is a residue of a phenol resin and contains at least one free hydroxyl group directly connected to an aromatic nucleus.
Claim 12
Dependent Claim
16 words
A method according to claim 9, wherein the phenol resin is a novolac type phenol resin.
Claim 13
Dependent Claim
19 words
A method according to claim 6, wherein the heating of the mixture is conducted at 100° to 200° C.
Claim 14
Dependent Claim
25 words
A method according to claim 6, wherein an amount of the diamine is 0.3 to 2 mole per 1 mole of the dicarboxylic acid anhydride.
Claim 15
Dependent Claim
23 words
A method according to claim 6, wherein an amount of the phenolic compound is 30 to 70% by weight based on the mixture.
Claim 16
Dependent Claim
31 words
A method according to claim 6, wherein the heating of the mixture is conducted in the presence of 0.1 to 2% by weight, based on the mixture, of an imidazole compound.
Claim 17
Independent Claim
214 words
A method of producing a bisimide-ether compound, which comprises heating a mixture of a bisimide represented by the general formula: ##STR15## wherein R 1 is a group containing at least two carbon atoms, the nitrogen atoms being directly connected to different carbon atoms of the group R 1 , and R' 2 is a group containing at least two carbon atoms and a carbon-carbon double bond, the carbonyl groups of the imide rings being directly connected to different carbon atoms of the group R' 2 , and a phenolic compound having at least two hydroxyl groups directly connected to different carbon atoms of an aromatic nucleus of the phenolic compound at an elevated temperature for a time sufficient to produce at least 10% by weight, based on the mixture, of a bisimide-ether compound having the general formula: ##STR16## wherein R 1 has the same meaning as defined above, R 2 is a group derived from the group R' 2 by combining the hydroxyl groups of the phenol compound therewith, R 3 is a residue of the phenol compound, and n is an integer of zero, 1 or larger than 1, the bisimide-ether compound being soluble in an organic solvent having a boiling point lower than 130° C. at normal temperature and under normal pressure.
Claim 18
Independent Claim
214 words
A method of producing a bisimide-ether compound, which comprises heating a mixture of a bisimide represented by the general formula: ##STR15## wherein R 1 is a group containing at least two carbon atoms, the nitrogen atoms being directly connected to different carbon atoms of the group R 1 , and R' 2 is a group containing at least two carbon atoms and a carbon-carbon double bond, the carbonyl groups of the imide rings being directly connected to different carbon atoms of the group R' 2 , and a phenolic compound having at least two hydroxyl groups directly connected to different carbon atoms of an aromatic nucleus of the phenolic compound at an elevated temperature for a time sufficient to produce at least 10% by weight, based on the mixture, of a bisimide-ether compound having the general formula: ##STR16## wherein R 1 has the same meaning as defined above, R 2 is a group derived from the group R' 2 by combining the hydroxyl groups of the phenol compound therewith, R 3 is a residue of the phenol compound, and n is an integer of zero, 1 or larger than 1, the bisimide-ether compound being soluble in an organic solvent having a boiling point lower than 130° C. at normal temperature and under normal pressure.
Claim 19
Dependent Claim
19 words
A method according to claim 15, wherein R 1 is an aromatic group containing at least one aromatic nucleus.
Claim 20
Dependent Claim
11 words
A method according to claim 15, wherein R 2 is ##STR17##
Claim 21
Dependent Claim
30 words
A method according to claim 15, wherein R 3 is a residue of a phenol resin and contains at least one free hydroxyl group directly connected to an aromatic nucleus.
Claim 22
Dependent Claim
22 words
A method according to claim 17, wherein the phenol resin is a novolac type phenol resin containing more than two hydroxyl groups.
Claim 23
Dependent Claim
19 words
A method according to claim 15, wherein the heating of the mixture is conducted at 100° to 200° C.
Claim 24
Dependent Claim
34 words
A method according to claim 15, wherein the heating of the mixture is conducted in the presence of an imidazole compound in an amount of 0.1 to 2% by weight based on the mixture.
Claim 25
Dependent Claim
162 words
A solvent-soluble thermosetting resin composition comprising a bisimide-ether compound having the general formula: ##STR18## wherein R 1 is a group containing at least two carbon atoms, the nitrogen atoms of the imide rings being directly connected to different carbon atoms of the group R 1 , R 2 is a group containing at least two carbon atoms, R' 2 is a group containing at least two carbon atoms and a carbon-carbon double bond, the carbonyl groups of the imide rings being directly connected to different carbon atoms of the group R 2 or R' 2 , R 3 is an aromatic group containing at least one aromatic nucleus, the oxygen atoms between the groups R 2 and R 3 being directly connected to different carbon atoms of an aromatic nucleus, and n is an integer of zero, 1 or larger than 1, the bisimide-ether compound being soluble in an organic solvent having a boiling point lower than 130° C. and a hardener.
Claim 26
Dependent Claim
162 words
A solvent-soluble thermosetting resin composition comprising a bisimide-ether compound having the general formula: ##STR18## wherein R 1 is a group containing at least two carbon atoms, the nitrogen atoms of the imide rings being directly connected to different carbon atoms of the group R 1 , R 2 is a group containing at least two carbon atoms, R' 2 is a group containing at least two carbon atoms and a carbon-carbon double bond, the carbonyl groups of the imide rings being directly connected to different carbon atoms of the group R 2 or R' 2 , R 3 is an aromatic group containing at least one aromatic nucleus, the oxygen atoms between the groups R 2 and R 3 being directly connected to different carbon atoms of an aromatic nucleus, and n is an integer of zero, 1 or larger than 1, the bisimide-ether compound being soluble in an organic solvent having a boiling point lower than 130° C. and a hardener.
Claim 27
Dependent Claim
22 words
A solvent-soluble thermosetting resin composition according to claim 22, wherein R 1 is an aromatic group containing at least one aromatic nucleus.
Claim 28
Dependent Claim
14 words
A solvent-soluble thermosetting resin composition according to claim 22, wherein R 2 is ##STR19##
Claim 29
Dependent Claim
32 words
A solvent-soluble thermosetting resin composition according to claim 22, wherein R 3 is a residue of a phenol resin containing at least one free hydroxyl group directly connected to an aromatic nucleus.
Claim 30
Dependent Claim
28 words
A solvent-soluble thermosetting resin composition according to claim 25, wherein the phenol resin is a novolac type phenol resin polymer having a softening point lower than 170° C.
Claim 31
Dependent Claim
169 words
A solvent-soluble thermosetting resin composition comprising a bisimide-ether compound having the general formula: ##STR20## wherein R 1 is a group containing at least two carbon atoms, the nitrogen atoms of the imide rings being directly connected to different carbon atoms of the group R 1 , R 2 is a group containing at least two carbon atoms, R' 2 is a group containing at least two carbon atoms and a carbon-carbon double bond, the carbonyl groups of the imide rings being directly connected to different carbon atoms of the group R 2 or R' 2 , R 3 is an aromatic group containing at least one aromatic nucleus, the oxygen atoms between the groups R 2 and R 3 being directly connected to different carbon atoms of an aromatic nucleus, and n is an integer of zero, 1 or larger than 1, the bisimide-ether compound being soluble in an organic solvent having a boiling point lower than 130° C., and an epoxy resin having at least two epoxy groups.
Claim 32
Dependent Claim
169 words
A solvent-soluble thermosetting resin composition comprising a bisimide-ether compound having the general formula: ##STR20## wherein R 1 is a group containing at least two carbon atoms, the nitrogen atoms of the imide rings being directly connected to different carbon atoms of the group R 1 , R 2 is a group containing at least two carbon atoms, R' 2 is a group containing at least two carbon atoms and a carbon-carbon double bond, the carbonyl groups of the imide rings being directly connected to different carbon atoms of the group R 2 or R' 2 , R 3 is an aromatic group containing at least one aromatic nucleus, the oxygen atoms between the groups R 2 and R 3 being directly connected to different carbon atoms of an aromatic nucleus, and n is an integer of zero, 1 or larger than 1, the bisimide-ether compound being soluble in an organic solvent having a boiling point lower than 130° C., and an epoxy resin having at least two epoxy groups.
Claim 33
Dependent Claim
28 words
A solvent-soluble thermosetting resin composition according to claim 27, which further contains an imidazole compound in an amount of 0.1 to 2% by weight based on the composition.
Claim 34
Dependent Claim
26 words
A solvent-soluble thermosetting resin composition according to claim 27, wherein an amount of the epoxy resin is 30 to 60% by weight based on the composition.
Claim 35
Independent Claim
228 words
A method of producing a solvent-soluble thermosetting resin, which comprises heating, in the presence of an epoxy resin containing at least two epoxy groups, a mixture of a bisimide represented by the general formula: ##STR21## wherein R 1 is a group containing at least two carbon atoms, the nitrogen atoms being directly connected to different carbon atoms of the group R 1 , and R' 2 is a group containing at least two carbon atoms and a carbon-carbon double bond, the carbonyl groups of the imide rings being directly connected to different carbon atoms of the group R' 2 , and a phenolic compound containing at least two hydroxyl groups directly connected to different carbon atoms of an aromatic nucleus of the phenolic compound at an elevated temperature for a time sufficient to produce at least 10% by weight, based on the mixture, of a bisimide-ether compound having the general formula: ##STR22## wherein R 1 has the same meaning as defined above, R 2 is a group derived from the group R' 2 by combining the hydroxyl groups of the phenol compound therewith, R 3 is a residue of the phenol compound, and n is an integer of zero, 1 or larger than 1, the bisimide-ether compound being soluble in an organic solvent having a boiling point lower than 130° C. at normal temperature and under normal pressure.
Claim 36
Independent Claim
228 words
A method of producing a solvent-soluble thermosetting resin, which comprises heating, in the presence of an epoxy resin containing at least two epoxy groups, a mixture of a bisimide represented by the general formula: ##STR21## wherein R 1 is a group containing at least two carbon atoms, the nitrogen atoms being directly connected to different carbon atoms of the group R 1 , and R' 2 is a group containing at least two carbon atoms and a carbon-carbon double bond, the carbonyl groups of the imide rings being directly connected to different carbon atoms of the group R' 2 , and a phenolic compound containing at least two hydroxyl groups directly connected to different carbon atoms of an aromatic nucleus of the phenolic compound at an elevated temperature for a time sufficient to produce at least 10% by weight, based on the mixture, of a bisimide-ether compound having the general formula: ##STR22## wherein R 1 has the same meaning as defined above, R 2 is a group derived from the group R' 2 by combining the hydroxyl groups of the phenol compound therewith, R 3 is a residue of the phenol compound, and n is an integer of zero, 1 or larger than 1, the bisimide-ether compound being soluble in an organic solvent having a boiling point lower than 130° C. at normal temperature and under normal pressure.
Claim 37
Dependent Claim
19 words
A method according to claim 30, wherein R 1 is an aromatic group having at least one aromatic nucleus.
Claim 38
Dependent Claim
11 words
A method according to claim 30, wherein R 2 is ##STR23##
Claim 39
Dependent Claim
30 words
A method according to claim 30, wherein R 3 is a residue of a phenol resin and has at least one free hydroxyl group directly connected to an aromatic nucleus.
Claim 40
Dependent Claim
22 words
A method according to claim 30, wherein the phenol resin is a novolac type phenol resin having more than two hydroxyl groups.
Claim 41
Dependent Claim
19 words
A method according to claim 30, wherein the heating of the mixture is conducted at 100° to 200° C.
Claim 42
Dependent Claim
23 words
A method according to claim 30, wherein an amount of the phenolic compound is 30 to 70% by weight based on the mixture.
Claim 43
Dependent Claim
31 words
A method according to claim 30, wherein the heating of the mixture is conducted in the presence of 0.1 to 2% by weight, based on the mixture, of an imidazole compound.
Claim 44
Dependent Claim
18 words
A method according to claim 6 or claim 15 wherein n is an integer not greater than 10.
Claim 45
Dependent Claim
43 words
A method according to claim 15 or claim 30, wherein the bisimide is N,N'-4,4'-diphenylether bismaleimide; N,N'-4,4'-diphenylmethane bismaleimide or N,N'-3,3'-4,4'-dichlorodiphenylmethane bismaleimide and the phenolic compound is a phenolic novolac resin having an average number of hydroxyl groups of 3 or more or para-hydroxyl polystyrene.
Claim 46
Dependent Claim
16 words
A bisimide-ether compound according to claim 1, wherein n is an integer not greater than 10.
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USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1984-10-19 | 1985-04-20 | 1985-10-20 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1988-10-19 | 1989-04-20 | 1989-10-20 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1992-10-19 | 1993-04-20 | 1993-10-20 | $7700.00 | Window Closed / Lapsed |