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US4038251A
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Process for the manufacture of polyaddition products containing imide groups by reaction of polymaleimides with polyhydric phenols using amine catalyst
Assignee: Novartis Corp
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Filing: 1974-12-18
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Granted: 1977-07-26
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Expires: 1994-12-18
Abstract
Abstract According to the invention, polyaddition products containing imide groups are manufactured by reacting certain polyimides (preferably maleimides) with polyhydric phenols in the presence of basic compounds. The preferred embodiment (A) relates to the use of catalysts as basic compounds. In particular, tertiary, secondary or mixed tertiary-secondary amines can be used. A further embodiment (B) relates to the use of primary polyamines as basic compounds. In the latter case, the polyamine participates in the polyaddition mechanism, that is to say the molecules are incorporated into the polyaddition products. In this latter case, catalysts can also be used additionally. The invention can be utilized particularly in the fields of surface protection, the electrical industry, laminating processes and the manufacture of foamed plastics, and in the building industry.
Inventors
- 👤 Imre Forgo
- 👤 Bruno Schreiber
- 👤 Alfred Renner
- 👤 Theobald Haug
- 👤 Andre Schmitter
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-29 22:26
CPC Classifications
C; C08; C08G; C08G73/00; C08G73/06; C08G73/10; C08G73/12; C08G73/126; C08G73/127; C08G73/125
Claims Analysis
Total Claims: 52
Claim 1
Independent Claim
47 words
Process for the manufacture of polyaddition products containing imide groups, wherein polyamides which contain, per molecule, at least two radicals of the formula ##STR15## wherein R is hydrogen or methyl, are reacted with polyhydric phenols in the presence of amines at temperatures between 50° and 280° C.
Claim 2
Dependent Claim
47 words
Process for the manufacture of polyaddition products containing imide groups, wherein polyamides which contain, per molecule, at least two radicals of the formula ##STR15## wherein R is hydrogen or methyl, are reacted with polyhydric phenols in the presence of amines at temperatures between 50° and 280° C.
Claim 3
Dependent Claim
22 words
Process according to claim 1, characterised in that the reaction is allowed to take place at temperatures of 150 to 250° C.
Claim 4
Dependent Claim
23 words
Process according to claim 1, characterised in that polyimides which contain two or three radicals of the formula (I) per molecule are employed.
Claim 5
Dependent Claim
33 words
Process according to claim 1, characterised in that the polyimide employed is a compound of the general formula ##STR16## in which A denotes a divalent organic radical with 2 to 30 C atoms.
Claim 6
Dependent Claim
53 words
Process according to claim 4, characterised in that the polyimide employed is a compound of the formula (III) in which A denotes a radical of the formula ##STR17## wherein R 1 represents one of the radicals --CH 2 --, ##STR18## --SO 2 --, --SO--, --S-- and --O-- and n is 0 or 1.
Claim 7
Dependent Claim
14 words
Process according to claim 5, characterised in that N,N'-4,4'-diphenylmethane-bis-maleimide is employed as the polyimide.
Claim 8
Dependent Claim
17 words
Process according to claim 1, characterised in that hydroquinone or resorcinol is employed as the polyhydric phenol.
Claim 9
Dependent Claim
19 words
Process according to claim 1, characterised in that the polyhydric phenol employed is a compound of the formula ##STR19##
Claim 10
Dependent Claim
12 words
Process according to claim 8, characterised in that bisphenol A is employed.
Claim 11
Dependent Claim
16 words
Process according to claim 1, characterised in that a novolac is employed as the polyhydric phenol.
Claim 12
Dependent Claim
13 words
Process according to claim 1, characterised in that the amine is a catalyst.
Claim 13
Dependent Claim
29 words
Process according to claim 11, characterised in that the catalysts are employed in a concentration of 0.1 to 10% by weight, relative to the total amount of the reactants.
Claim 14
Dependent Claim
21 words
Process according to claim 11, characterised in that the catalysts are employed in a concentration of 0.5 to 5.0% by weight.
Claim 15
Dependent Claim
18 words
Process according to claim 11, characterised in that the catalysts employed are tertiary, secondary or mixed tertiary-secondary amines.
Claim 16
Dependent Claim
37 words
Process according to claim 11, characterised in that the particular polyimide is reacted with the particular polyhydric phenol in such a ratio as to provide 0.3 to 1 equivalent of polyhydric phenol per 1 equivalent of polyimide.
Claim 17
Dependent Claim
10 words
Polyaddition products manufactured acording to the process of claim 11.
Claim 18
Dependent Claim
63 words
Process according to claim 1, characterised in that the amines employed are primary polyamines in such a ratio as to provide, per 1 equivalent of polyimide, such an amount of polyhydric phenol and primary polyamine that the sum of the last two substances is 0.4 to 1.5 equivalents and the equivalent ratio of the polyhydric phenol to the polyamine is 0.5:1 to 4:1.
Claim 19
Dependent Claim
39 words
Process according to claim 17, characterised in that the reaction is allowed to take place using a ratio of the amounts to correspond to a ratio of equivalents of polyhydric phenol to equivalents of polyamine of 1:1 to 4:1.
Claim 20
Dependent Claim
28 words
Process according to claim 17, characterised in that the primary polyamine employed is an aromatic or an araliphatic, di-primary or tri-primary, amine with 2 to 40 C atoms.
Claim 21
Dependent Claim
20 words
Process according to claim 17, characterised in that a compound of the formula ##STR20## is employed as the primary polyamine.
Claim 22
Dependent Claim
11 words
Process according to claim 20, characterised in that 4,4'-diaminodiphenylmethane is employed.
Claim 23
Dependent Claim
46 words
Process according to claim 17, characterised in that the reaction is allowed to take place in the presence of catalysts which differ from the products produced during the reaction, in a concentration of 0.2 to 10% by weight, relative to the total amount of the reactants.
Claim 24
Dependent Claim
18 words
Process according to claim 22, characterised in that tertiary, secondary or mixed tertiary-secondary amines are employed as catalysts.
Claim 25
Dependent Claim
21 words
Process according to claim 22, characterised in that the catalysts are employed in a concentration of 0.5 to 5% by weight.
Claim 26
Dependent Claim
27 words
Process according to claim 17, characterised in that it starts from a reaction mixture which in addition to the polyimides simultaneously contains polyhydric phenols and primary polyamines.
Claim 27
Dependent Claim
58 words
Process according to claim 17, characterised in that first the reaction of the particular polyimide with the particular polyhydric phenol is allowed to take place completely or partially, in the presence of a catalyst, and thereafter the reaction of the reaction mixture, thus obtained, with the particular primary polyamine, or the terminal reaction, is allowed to take place.
Claim 28
Dependent Claim
52 words
Process according to claim 17, characterised in that first the reaction of the particular polyimide with the particular primary polyamine is allowed to take place completely or partially, and thereafter the reaction of the reaction mixture, thus obtained, with the particular polyhydric phenol, or the terminal reaction, is allowed to take place.
Claim 29
Dependent Claim
10 words
Polyaddition products manufactured by the process according to claim 17.
Claim 30
Dependent Claim
31 words
Storage-stable, hot-curable mixtures, which contain (a) polyimides which contain, per molecule, at least two radicals of the formula ##STR21## wherein R is hydrogen or methyl, (b) polyhydric phenols and (c) amines.
Claim 31
Dependent Claim
31 words
Storage-stable, hot-curable mixtures, which contain (a) polyimides which contain, per molecule, at least two radicals of the formula ##STR21## wherein R is hydrogen or methyl, (b) polyhydric phenols and (c) amines.
Claim 32
Dependent Claim
23 words
Mixtures according to claim 29, characterised in that they contain polyimides which possess two or three radicals of the formula (I) per molecule.
Claim 33
Dependent Claim
34 words
Mixtures according to claim 29, characterised in that they contain, as the polyimide, a compound of the general formula ##STR22## in which A denotes a divalent organic radical with 2 to 30 C atoms.
Claim 34
Dependent Claim
54 words
Mixtures according to claim 31, characterised in that they contain, as the polyimide, a compound of the formula (III), in which A denotes a radical of the formula ##STR23## wherein R 1 represents one of the radicals --CH 2 , ##STR24## --SO 2 --, --SO--, --S-- and --O-- and n is 0 or 1.
Claim 35
Dependent Claim
14 words
Mixtures according to claim 32, characterised in that they contain N,N'-4,4'-diphenylmethane-bis-maleimide as the polyimide.
Claim 36
Dependent Claim
17 words
Mixtures according to claim 29, characterised in that they contain hydroquinone or resorcinol as the polyhydric phenol.
Claim 37
Dependent Claim
20 words
Mixtures according to claim 29, characterised in that they contain, as the polyhydric phenol, a compound of the formula ##STR25##
Claim 38
Dependent Claim
12 words
Mixtures according to claim 35, characterised in that they contain bisphenol A.
Claim 39
Dependent Claim
19 words
Mixtures according to claim 29, characterised in that they contain a novolac as the polyhydric, mononuclear or polynuclear phenol.
Claim 40
Dependent Claim
13 words
Mixtures according to claim 29, characterized in that the amine is a catalyst.
Claim 41
Dependent Claim
29 words
Mixtures according to claim 38, characterised in that they contain the catalysts in a concentration of 0.1 to 10% by weight, relative to the total amount of the reactants.
Claim 42
Dependent Claim
21 words
Mixtures according to claim 38, characterised in that they contain the catalysts in a concentration of 0.5 to 5.0% by weight.
Claim 43
Dependent Claim
18 words
Mixtures according to claim 38, characterised in that they contain tertiary, secondary or mixed tertiary-secondary amines as catalysts.
Claim 44
Dependent Claim
37 words
Mixtures according to claim 38, characterised in that they contain the particular polyimide and the particular polyhydric phenol in such a ratio as to provide 0.3 to 1 equivalent of polyhydric phenol per 1 equivalent of polyimide.
Claim 45
Dependent Claim
67 words
Mixtures according to claim 29, characterised in that they contain primary polyamines and that the reactants are present in such a ratio as to provide, per 1 equivalent of polyamide, such an amount of polyhydric phenol and primary polyamine that the sum of the last two substances is 0.4 to 1.5 equivalents and the equivalent ratio of the polyhydric phenol to the polyamine is 0.5:1 to 4:1.
Claim 46
Dependent Claim
29 words
Mixtures according to claim 43, characterised in that they contain an aromatic or an araliphatic, di-primary or tri-primary amine with 2 to 40 C atoms as the primary polyamine.
Claim 47
Dependent Claim
20 words
Mixtures according to claim 44, characterised in that they contain a compound of the formula ##STR26## as the primary polyamine.
Claim 48
Dependent Claim
11 words
Mixtures according to claim 45, characterised in that they contain 4,4'-diaminodiphenylmethane.
Claim 49
Dependent Claim
38 words
Mixtures according to claim 43, characterised in that they additionally contain catalysts which differ from the products produced during the reaction, in a concentration of 0.2 to 10% by weight, relative to the total amount of the reactants.
Claim 50
Dependent Claim
21 words
Mixtures according to claim 47, characterised in that they contain the catalysts in a concentration of 0.5 to 5% by weight.
Claim 51
Dependent Claim
18 words
Mixtures according to claim 47, characterised in that they contain tertiary, secondary or mixed tertiary-secondary amines as catalysts.
Claim 52
Dependent Claim
30 words
Mixtures according to claim 43, characterised in that the polyhydric phenol and the polyamine are present in the mixtures in such amounts that the equivalent ratio is 1:1 to 4:1.
References Cited (Backward Citations)
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1980-07-25 | 1981-01-24 | 1981-07-26 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1984-07-25 | 1985-01-24 | 1985-07-26 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1988-07-25 | 1989-01-24 | 1989-07-26 | $7700.00 | Window Closed / Lapsed |