US4748255A
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Thermally adaptive polymers and prepolymers and methods of making them
Assignee: Thermal Science Inc
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Filing: 1987-07-27
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Granted: 1988-05-31
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Expires: 2007-07-27
Abstract
Abstract Reaction of an aromatic dianhydride with a polycyclic aromatic primary diamine at a controlled reaction rate yields a diamic acid dianhydride oligomer. The oligomer may be a precursor for an imide foam which forms at low temperature, has outstanding physical characteristics, and is extremely heat resistant. The diamic acid moiety may be converted to diimide, and other modifications of the oligomer are disclosed. Other derivatives of the oligomers are also disclosed.
Inventors
- 👤 John A. Parker
- 👤 Rubin Feldman
- 👤 Robert L. Bryant
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-04 16:05
CPC Classifications
C; C07; C07D; C07D493/00; C07D493/02; C07D493/08; C07D307/00; C07D307/77; C07D307/87; C07D307/89; C08; C08G; C08G18/00; C08G18/06; C08G18/28; C08G18/30; C08G18/38; C08G18/3819; C08G18/3821; C08G73/00; C08G73/06; C08G73/10; C08G73/1003; C08G73/1007; C08G73/1028; C08G73/1035; C08G73/1067
Claims Analysis
Total Claims: 42
Claim 1
Independent Claim
34 words
A solid oligomer including reactive terminal groups and two amic acid groups, each of said amic acid groups consisting of a carboxyl group and a singly substituted amide linkage attached to adjacent carbon atoms.
Claim 2
Dependent Claim
34 words
A solid oligomer including reactive terminal groups and two amic acid groups, each of said amic acid groups consisting of a carboxyl group and a singly substituted amide linkage attached to adjacent carbon atoms.
Claim 3
Dependent Claim
13 words
The oligomer of claim 1 wherein said oligomer includes at least four rings.
Claim 4
Dependent Claim
19 words
The oligomer of claim 2 wherein said oligomer has a molecular weight of from about 400 to about 1000.
Claim 5
Dependent Claim
25 words
The oligomer of claim 3 wherein said adjacent carbon atoms to which each of said amic acid groups is attached are members of a ring.
Claim 6
Dependent Claim
36 words
The oligomer of claim 4 wherein at least 90% of the molecular weight of said oligomer consists of atoms forming ring structures, or atoms attached directly to ring structures, or atoms forming said amic acid groups.
Claim 7
Dependent Claim
36 words
The oligomer of claim 1 wherein said oligomer is derived from a solution containing dimethylacetamide, has a molecular weight of from 600 to 1000, and has a softening temperature of from 20° C. to 80° C.
Claim 8
Dependent Claim
15 words
The oligomer of claim 1 wherein said terminal groups are both anhydrides or both amines.
Claim 9
Dependent Claim
36 words
The oligomer of claim 7 wherein said oligomer has the structure: ##STR2## where R is a substituted or unsubstituted alicyclic, polyalicyclic, aromatic or polyaromatic group and Ar is a substituted or unsubstituted aromatic or polyaromatic group.
Claim 10
Dependent Claim
43 words
The oligomer of claim 8 wherein Ar includes two aromatic rings, each nitrogen linkage shown in claim 8 being to a different one of said aromatic rings, each of said two aromatic rings being substituted in a position ortho to the nitrogen linkage.
Claim 11
Dependent Claim
25 words
The oligomer of claim 9 wherein each of said two aromatic rings is substituted, in a position ortho to the nitrogen linkage, by a halogen.
Claim 12
Dependent Claim
56 words
An oligomer, said oligomer including reactive terminal groups and two internal groups preformed in said oligomer, said internal groups being chosen from the group consisting of imide and amic acid, said internal groups each including a nitrogen atom attached to an aromatic ring, said aromatic ring being substituted in a position ortho to the nitrogen linkage.
Claim 13
Dependent Claim
56 words
An oligomer, said oligomer including reactive terminal groups and two internal groups preformed in said oligomer, said internal groups being chosen from the group consisting of imide and amic acid, said internal groups each including a nitrogen atom attached to an aromatic ring, said aromatic ring being substituted in a position ortho to the nitrogen linkage.
Claim 14
Dependent Claim
13 words
The oligomer of claim 11 wherein said oligomer includes at least four rings.
Claim 15
Dependent Claim
19 words
The oligomer of claim 12 wherein said oligomer has a molecular weight of from about 600 to about 1000.
Claim 16
Dependent Claim
29 words
The oligomer of claim 11 wherein at least 90% of the molecular weight of said oligomer consists of atoms forming ring structures, or atoms attached directly to ring structures.
Claim 17
Dependent Claim
28 words
The oligomer of claim 11 wherein said oligomer has a molecular weight of from 600 to 1000 and a softening temperature of from 20° C. to 80° C.
Claim 18
Dependent Claim
11 words
The oligomer of claim 13 wherein said terminal groups are anhydrides.
Claim 19
Dependent Claim
36 words
The oligomer of claim 16 wherein said oligomer has the structure: ##STR3## where R is a substituted or unsubstituted alicyclic, polyalicyclic, aromatic or polyaromatic group and Ar is a substituted or unsubstituted aromatic or polyaromatic group.
Claim 20
Dependent Claim
42 words
The oligomer of claim 17 wherein Ar includes two aromatic rings, each nitrogen linkage shown in claim 18 being to a different one of said aromatic rings, each of said aromatic rings being substituted in a position ortho to the nitrogen linkage.
Claim 21
Dependent Claim
24 words
The oligomer of claim 18 wherein each of said aromatic rings is substituted, in a position ortho to the nitrogen linkage, by a halogen.
Claim 22
Independent Claim
53 words
A method of producing an oligomer comprising reacting an aromatic or alicyclic dianhydride reactant with an aromatic primary diamine reactant, and controlling the reaction conditions to provide a substantially pure trimer consisting of two terminal parts derived from one of said reactants and a central part derived from the other of said reactants.
Claim 23
Independent Claim
53 words
A method of producing an oligomer comprising reacting an aromatic or alicyclic dianhydride reactant with an aromatic primary diamine reactant, and controlling the reaction conditions to provide a substantially pure trimer consisting of two terminal parts derived from one of said reactants and a central part derived from the other of said reactants.
Claim 24
Dependent Claim
45 words
The method of claim 20 wherein at least one of said reactants is carried by a solvent in which it is poorly soluble, said solvent comprising an acetamide, and wherein said trimer has a melting point of from about 20° C. to about 80° C.
Claim 25
Dependent Claim
17 words
The method of claim 20 wherein said oligomer includes amic acid groups at other than terminal positions.
Claim 26
Dependent Claim
25 words
The method of claim 22 including a further step of closing at least a substantial porportion of said amic acid groups to form imide rings.
Claim 27
Dependent Claim
19 words
The method of claim 20 wherein said reaction conditions are controlled to provide a timer having anhydride terminal parts.
Claim 28
Dependent Claim
12 words
A polyanhydride consisting essentially of the condensation product of a norbornene anhydride.
Claim 29
Dependent Claim
12 words
A polyanhydride consisting essentially of the condensation product of a norbornene anhydride.
Claim 30
Independent Claim
17 words
A method of forming a polyanhydride comprising polymerizing a norbornene anhydride in the presence of a catalyst.
Claim 31
Independent Claim
17 words
A method of forming a polyanhydride comprising polymerizing a norbornene anhydride in the presence of a catalyst.
Claim 32
Dependent Claim
20 words
The method of claim 26 wherein the norbornene anhydride is cis-5-norbornene-2,3-dicarboxylic acid anhydride and the catalyst is a Lewis acid.
Claim 33
Independent Claim
49 words
A method of producing an oligomer comprising reacting an aromatic or alicyclic polyanhydride reactant with an aromatic primary diamine reactant, the diamine reactant including two nitrogen atoms, each nitrogen atom being attached to an aromatic ring, said aromatic ring being substituted in a position ortho to the nitrogen atom.
Claim 34
Independent Claim
49 words
A method of producing an oligomer comprising reacting an aromatic or alicyclic polyanhydride reactant with an aromatic primary diamine reactant, the diamine reactant including two nitrogen atoms, each nitrogen atom being attached to an aromatic ring, said aromatic ring being substituted in a position ortho to the nitrogen atom.
Claim 35
Dependent Claim
15 words
The method of claim 28 wherein said diamine reactant is 3,3' dichloro 4,4' diamino diphenylmethane.
Claim 36
Dependent Claim
23 words
The method of claim 28 wherein at least one of said reactants is carried by a solvent in which it is poorly soluble.
Claim 37
Dependent Claim
46 words
The method of claim 28 wherein said dianhydride is at least partially suspended in a solvent, and the diamine is added slowly to assure that the reaction proceeds as a termination reaction, rather than as a chain-propagating reaction, thereby providing a trimer having anhydride terminal parts.
Claim 38
Independent Claim
59 words
A method of producing an oligomer comprising reacting an aromatic or alicyclic dianhydride reactant with a primary diamine reactant, and controlling the reaction conditions to provide an oligomer consisting of terminal parts derived from one of said reactants, said oligomer having a molecular weight of from 400 to 1000, and a step of recovering said oligomer as a solid.
Claim 39
Independent Claim
59 words
A method of producing an oligomer comprising reacting an aromatic or alicyclic dianhydride reactant with a primary diamine reactant, and controlling the reaction conditions to provide an oligomer consisting of terminal parts derived from one of said reactants, said oligomer having a molecular weight of from 400 to 1000, and a step of recovering said oligomer as a solid.
Claim 40
Dependent Claim
27 words
The method of claim 33 wherein said step of recovering said oligomer as a solid includes a step of mixing said oligomer with a water-insoluble ammonium polyphosphate.
Claim 41
Dependent Claim
45 words
The oligomer of claim 11 wherein said oligomer has the structure: ##STR4## where R is a substituted or unsubstituted alicyclic, polyalicyclic, aromatic or polyaromatic group and Ar includes two aromatic rings, each nitrogen linkage shown above being to a different one of said aromatic rings.
Claim 42
Dependent Claim
25 words
The oligomer of claim 34 wherein each of said two aromatic rings is substituted, in a position ortho to the nitrogen linkage, by a halogen.
References Cited (Backward Citations)
US3716519A
Cited
US3620987A
Cited
US3954710A
Cited
US3966652A
Cited
US4241193A
Cited
US4184021A
Cited
US4338427A
Cited
US4316843A
Cited
US4305796A
Cited
US4439381A
Cited
US4305796B1
Cited
US4360604A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1991-05-31 | 1991-11-30 | 1992-05-31 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1995-05-31 | 1995-11-30 | 1996-05-31 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1999-05-31 | 1999-11-30 | 2000-05-31 | $7700.00 | Window Closed / Lapsed |