US4065433A
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Process for the manufacture of polyaddition products containing imide groups
Assignee: Novartis Corp
•
Filing: 1974-12-18
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Granted: 1977-12-27
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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 alcohols in the presence of basic compounds. The preferred embodiment (E) relates to the use of catalysts as basic compounds. In particular, amines and alkali metal compounds can be used. A further embodiment (F) 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.
Inventors
- 👤 Albrecht Muller
- 👤 Theobald Haug
- 👤 Alfred Renner
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-24 23:16
CPC Classifications
C; C07; C07F; C07F9/00; C07F9/02; C07F9/547; C07F9/553; C07F9/5537; C08; C08G; C08G73/00; C08G73/06; C08G73/10; C08G73/12; C08G73/125; C08G73/126; C08G73/127
Claims Analysis
Total Claims: 63
Claim 1
Independent Claim
74 words
Process for the manufacture of polyaddition products containing imide groups, said process comprising reacting polyimides which contain, per molecule, at least two radicals of the general formula ##STR16## in which D denotes a divalent radical containing a carbon-carbon double bond, with polyhydric alcohols in the presence of basic compounds selected from the group consisting of primary polyamines, basic catalysts, and mixtures of primary polyamines and basic catalysts at temperatures between 50° and 280° C.
Claim 2
Dependent Claim
74 words
Process for the manufacture of polyaddition products containing imide groups, said process comprising reacting polyimides which contain, per molecule, at least two radicals of the general formula ##STR16## in which D denotes a divalent radical containing a carbon-carbon double bond, with polyhydric alcohols in the presence of basic compounds selected from the group consisting of primary polyamines, basic catalysts, and mixtures of primary polyamines and basic catalysts at temperatures between 50° and 280° C.
Claim 3
Dependent Claim
20 words
Process according to claim 1, wherein the reaction is allowed to take place at temperatures of 100° to 250° C.
Claim 4
Dependent Claim
32 words
Process according to claim 1, wherein polyimides with radicals of the formula (I), in which D represents a divalent radical of the formula ##STR17## wherein R denotes hydrogen or methyl, are employed.
Claim 5
Dependent Claim
21 words
Process according to claim 1, wherein polyimides which contain two or three radicals of the formula (I) per molecule are employed.
Claim 6
Dependent Claim
31 words
Process according to claim 1, wherein the polyimide employed is a compound of the general formula ##STR18## in which A denotes a divalent organic radical with 2 to 30 C atoms.
Claim 7
Dependent Claim
51 words
Process according to claim 5, wherein the polyimide employed is a compound of the formula (III) in which A denotes a radical of the formula ##STR19## wherein R 1 is one of the radicals --CH 2 --, ##STR20## --SO 2 --, --SO--, --S-- and --O-- and n is 0 or 1.
Claim 8
Dependent Claim
12 words
Process according to claim 6, wherein N,N'-4,4'-diphenylmethane-bis-maleimide is employed as the polyimide.
Claim 9
Dependent Claim
17 words
Process according to claim 1, wherein a dihydric or trihydric alcohol is employed as the polyhydric alcohol.
Claim 10
Dependent Claim
27 words
Process according to claim 1, wherein an unbranched or branched aliphatic alcohol with a total of 2 to 12 C atoms is employed as the polyhydric alcohol.
Claim 11
Dependent Claim
51 words
Process according to claim 1, wherein the polyhydric alcohol employed is a cycloaliphatic or cycloaliphatic-aliphatic alcohol with 1 or more cycloaliphatic nuclei, which can optionally contain oxygen, sulphur or sulphur-containing radicals as linking members, and wherein the hydroxyl groups can be bonded either to the aliphatic or to the cycloaliphatic radicals.
Claim 12
Dependent Claim
43 words
Process according to claim 10, wherein the polyhydric alcohol employed is a compound of the formula ##STR21## in which R 1 is one of the radicals --CH 2 --, ##STR22## --SO 2 --, --SO--, --S-- and --O-- and n is 0 or 1.
Claim 13
Dependent Claim
21 words
Process according to claim 1, wherein the polyhydric alcohol employed is a polyglycol ether of a polyhydric alcohol or polyhydric phenol.
Claim 14
Dependent Claim
61 words
Process according to claim 12, wherein the polyhydric alcohol employed is a compound of the formula HO--CH.sub.2 CH.sub.2 --O--R.sup.2 --(R.sup.1).sub.n 13 R.sup.2 --O--CH.sub.2 CH.sub.2 --OH (VI) in which R 2 denotes a phenylene or a cyclohexylene radical, R 1 is one of the radicals --CH 2 --, ##STR23## --SO 2 --, --SO--, --S-- and --O-- and n is 0 or 1.
Claim 15
Dependent Claim
14 words
Process according to claim 1, wherein a catalyst is employed as the basic compound.
Claim 16
Dependent Claim
28 words
Process according to claim 14, wherein the basic catalysts are employed in a concentration of 0.01 to 15% by weight, relative to the total amount of the reactants.
Claim 17
Dependent Claim
19 words
Process according to claim 14, wherein the catalysts are employed in a concentration of 0.05 to 10% by weight.
Claim 18
Dependent Claim
20 words
Process according to claim 14, wherein the catalysts employed are tertiary, secondary or mixed tertiary-secondary amines or quaternary ammonium compounds.
Claim 19
Dependent Claim
14 words
Process according to claim 14, wherein alkali metal compounds are employed as the catalysts.
Claim 20
Dependent Claim
35 words
Process according to claim 14, wherein the particular polyimide is reacted with the particular polyhydric alcohol in such a ratio as to provide 0.1 to 1 equivalent of polyhydric alcohol per 1 equivalent of polyimide.
Claim 21
Dependent Claim
10 words
Polyaddition products manufactured according to the process of claim 14.
Claim 22
Dependent Claim
65 words
Process according to claim 1, wherein the basic compounds employed are primary polyamines in such a ratio as to provide, per 1 equivalent of polyimide, such an amount of polyhydric alcohol and primary polyamine that the sum of the equivalents of said alcohol and said polyamine is 0.2 to 1.5 equivalents and the equivalent ratio of said alcohol to said polyamine is 1:4 to 4:1.
Claim 23
Dependent Claim
37 words
Process according to claim 21, wherein the reaction is allowed to take place using a ratio of the amounts to correspond to a ratio of equivalents of polyhydric alcohol to equivalents of polyamine of 1:2 to 4:1.
Claim 24
Dependent Claim
26 words
Process according to claim 21, wherein the primary polyamine employed is an aromatic or an araliphatic, di-primary or tri-primary, amine with 2 to 40 C atoms.
Claim 25
Dependent Claim
44 words
Process according to claim 21, wherein a compound of the formula ##STR24## in which R 1 is one of the radicals --CH 2 --, ##STR25## --SO 2 --, --SO--, --S-- and --O-- and n is 0 or 1 is employed as the primary polyamine.
Claim 26
Dependent Claim
10 words
Process according to claim 24, wherein that 4,4'-diaminodiphenylmethane is employed.
Claim 27
Dependent Claim
46 words
Process according to claim 21, wherein that the reaction is allowed to take place in the presence of basic catalysts which differ from the products produced during the reaction, in a concentration of 0.1 to 15% by weight relative to the total amount of the reactants.
Claim 28
Dependent Claim
21 words
Process according to claim 21, wherein that tertiary, secondary or mixed tertiary-secondary amines or quaternary ammonium compounds are employed as catalysts.
Claim 29
Dependent Claim
14 words
Process according to claim 21, wherein that alkali metal compounds are employed as catalysts.
Claim 30
Dependent Claim
19 words
Process according to claim 26, wherein the catalysts are employed in a concentration of 0.3 to 8% by weight.
Claim 31
Dependent Claim
25 words
Process according to claim 1, wherein it starts from a reaction mixture which in addition to the polyimides simultaneously contains polyhydric alcohols and primary polyamines.
Claim 32
Dependent Claim
58 words
Storage-stable, hot-curable mixtures, said mixtures comprising a) polyimides which contain, per molecule, at least two radicals of the general formula ##STR26## in which D denotes a divalent radical containing a carbon-carbon double bond, b) polyhydric phenols and c) basic compounds selected from the group consisting of primary polyamines, basic catalysts, and mixtures of primary polyamines and basic catalysts.
Claim 33
Dependent Claim
58 words
Storage-stable, hot-curable mixtures, said mixtures comprising a) polyimides which contain, per molecule, at least two radicals of the general formula ##STR26## in which D denotes a divalent radical containing a carbon-carbon double bond, b) polyhydric phenols and c) basic compounds selected from the group consisting of primary polyamines, basic catalysts, and mixtures of primary polyamines and basic catalysts.
Claim 34
Dependent Claim
31 words
Mixtures according to claim 31, which contains polyimides with radicals of the formula (I) in which D represents a divalent radical of the formula ##STR27## wherein R denotes hydrogen or methyl.
Claim 35
Dependent Claim
20 words
Mixtures according to claim 31, which contains polyimides which possess two or three radicals of the formula (I) per molecule.
Claim 36
Dependent Claim
31 words
Mixtures according to claim 32, which contains as the polyimide, a compound of the general formula ##STR28## in which A denotes a divalent organic radical with 2 to 30 C atoms.
Claim 37
Dependent Claim
51 words
Mixtures according to claim 34, which contain as the polyimide, a compound of the formula (III), in which A denotes a radical of the formula ##STR29## wherein R 1 represents one of the radicals --CH 2 , ##STR30## --SO 2 --, --SO--, --S-- and --O-- and n is 0 or 1.
Claim 38
Dependent Claim
11 words
Mixtures according to claim 35, which contain N,N'-4,4'-diphenylmethane-bis-maleimide as the polyimide.
Claim 39
Dependent Claim
16 words
Mixtures according to claim 31, which contains a dihydric or trihydric alcohol as the polyhydric alcohol.
Claim 40
Dependent Claim
26 words
Mixtures according to claim 31, which contains an unbranched or branched aliphatic alcohol with a total of 2 to 12 C atoms as the polyhydric alcohol.
Claim 41
Dependent Claim
61 words
Mixtures according to claim 31, which contain, as the polyhydric alcohol, a cycloaliphatic or cycloaliphatic-aliphatic alcohol with 1 or more cycloaliphatic nuclei or a cycloaliphatic or cycloaliphatic-aliphatic alcohol with 1 or more cycloaliphatic nucleii which contains oxygen, sulphur or sulphur-containing radicals as linking members, and wherein the hydroxyl groups can be bonded either to the aliphatic or to the cycloaliphatic radicals.
Claim 42
Dependent Claim
43 words
Mixtures according to claim 39, which contains as the polyhydric alcohol, a compound of the formula ##STR31## in which R 1 represents one of the radicals --CH 2 --, ##STR32## --SO 2 --, --SO--, --S-- or --O-- and n is 0 or 1.
Claim 43
Dependent Claim
21 words
Mixtures according to claim 31, which contains as the polyhydric alcohol, a polyglycol ether of a polyhydric alcohol or polyhydric phenol.
Claim 44
Dependent Claim
62 words
Mixtures according to claim 41, which contains as the polyhydric alcohol, a compound of the formula HO--CH.sub.2 CH.sub.2 --O--R.sup.2 --(R.sup.1).sub.n --R.sup.2 --O--CH.sub.2 CH.sub.2 --OH (VI) in which R 2 denotes a phenylene radical or a cyclohexylene radical, R 1 is one of the radicals --CH 2 --, ##STR33## ps --SO 2 --, --SO--, --S-- and --O-- and n is 0 and 1.
Claim 45
Dependent Claim
13 words
Mixtures according to claim 31, which contain a catalyst as the basic compound.
Claim 46
Dependent Claim
27 words
Mixtures according to claim 43, which contain the basic catalysts in a concentration of 0.01 to 15% by weight, relative to the total amount of the reactants.
Claim 47
Dependent Claim
19 words
Mixtures according to claim 43, which contain the basic catalysts in a concentration of 0.05 to 10% by weight.
Claim 48
Dependent Claim
19 words
Mixtures according to claim 43, which contain tertiary, secondary or mixed tertiary-secondary amines or quaternary ammonium compounds as catalysts.
Claim 49
Dependent Claim
12 words
Mixtures according to claim 43, which contain alkali metal compounds as catalysts.
Claim 50
Dependent Claim
34 words
Mixtures according to claim 43, which contain the particular polyimide and the particular polyhydric alcohol in such a ratio as to provide 0.1 to 1 equivalent of polyhydric alcohol per 1 equivalent of polyimide.
Claim 51
Dependent Claim
70 words
Mixture according to claim 31, said mixtures comprising primary polyamines as basic compounds wherein the reactants are present in such a ratio as to provide, per 1 equivalent of polyimide, such an amount of polyhydric alcohol and primary polyamine that the sum of the equivalents of said alcohol and said polyamine is 0.2 to 1.5 equivalents and the equivalent ratio of said alcohol to said polyamine is 1:4 to 4:1.
Claim 52
Dependent Claim
26 words
Mixtures according to claim 49, which contain an aromatic or an araliphatic, di-primary or tri-primary amine with 2 to 40 C atoms as the primary polyamine.
Claim 53
Dependent Claim
41 words
Mixtures according to claim 50, which contain a compound of the formula ##STR34## wherein R 1 is one of the radicals --CH 2 --, ##STR35## --SO 2 --, --SO--, --S-- --O-- and n is 0 or 1, as the primary polyamine.
Claim 54
Dependent Claim
8 words
Mixtures according to claim 51, which contains 4,4'-diaminodiphenylmethane.
Claim 55
Dependent Claim
35 words
Mixtures according to claim 49, which contain basic catalysts which differ from the products formed during the reaction, in a concentration of 0.1 to 15% by weight, relative to the total amount of the reactants.
Claim 56
Dependent Claim
19 words
Mixtures according to claim 53, which contains the basic catalysts in a concentration of 0.3 to 8% by weight.
Claim 57
Dependent Claim
19 words
Mixtures according to claim 53, which contains tertiary, secondary or mixed tertiary-secondary amines or quaternary ammonium compounds as catalysts.
Claim 58
Dependent Claim
13 words
Mixtures according to claim 53, said mixtures comprising alkali metal compounds as catalysts.
Claim 59
Dependent Claim
28 words
Mixtures according to claim 49, wherein the polyhydric alcohol and the polyamine are present in the mixtures in such amounts that the equivalent ratio is 1:2 to 4:1.
Claim 60
Dependent Claim
52 words
Process for the manufacture of polyaddition products containing imide groups, said process comprising reacting polyimides which contain, per molecule, at least two radicals of the formula (I) of claim 1 with polyhydric alcohols in the presence of primary polyamines and basic catalysts as basic compounds at temperatures between 50° and 280° C.
Claim 61
Dependent Claim
36 words
Storage-stable, hot-curable mixtures, said mixtures comprising a) polyimides which contain, per molecule, at least two radicals of the formula (I) of claim 1, b) polyhydric phenols and c) primary polyamines and basic catalysts as basic compounds.
Claim 62
Dependent Claim
56 words
Process according to claim 21, wherein first the reaction of the particular polyimide with the particular polyhydric alcohol 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 63
Dependent Claim
50 words
Process according to claim 21, wherein 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 alcohol, or the terminal reaction, is allowed to take place.
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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) | 1980-12-26 | 1981-06-27 | 1981-12-27 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1984-12-26 | 1985-06-27 | 1985-12-27 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1988-12-26 | 1989-06-27 | 1989-12-27 | $7700.00 | Window Closed / Lapsed |