US4111907A
Expired / Lapsed
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Photopolymerizable ketones
Assignee: BASF Corp
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Filing: 1976-10-28
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Granted: 1978-09-05
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Expires: 1996-10-28
Abstract
Abstract The modified advanced epoxide resins described, having an average molecular weight of up to 50,000, can be photopolymerized without the need to include photosensitizers. They may be prepared by reaction of a diepoxide ##STR1## with a keto group-containing dihydric phenol ##STR2## to form the advanced epoxide resin ##STR3## followed by condensation with an aldehyde RCHO to yield ##STR4## In the above formulae, R is an organic group which preferably has ethylenic unsaturation or heterocyclic aromaticity in conjugation with the indicated ethylenic double bond; R 1 is the divalent residue linking two epoxide groups; R 2 is preferably a hydrogen atom but may be an organic group, halogen, or cyano; R 3 is a trivalent aromatic or heterocyclic group, especially a group ##STR5## If desired, other dihydric phenols can be employed with that containing a keto group, and condensation with the aldehyde may be carried out so that only some groups --COCH 2 R 2 undergo reaction.
Inventors
- 👤 George Edward Green
- 👤 Bernard Peter Stark
- 👤 John Sidney Waterhouse
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-01 21:11
CPC Classifications
C; C08; C08G; C08G59/00; C08G59/14; C08G59/1433; C08G59/1438; C08G59/02; C08G59/04; C08G59/06; C08G59/066; G; G03; G03F; G03F7/00; G03F7/004; G03F7/038; G03F7/0388; Y; Y10; Y10T; Y10T428/00; Y10T428/31504; Y10T428/31511
Claims Analysis
Total Claims: 20
Claim 1
Independent Claim
172 words
An unsaturated ketone of the formula ##STR22## where R represents a monovalent alkenyl, aralkenyl, cycloalkenyl, cycloalkylalkenyl, cycloalkenylalkenyl, heterocyclic or heterocyclic-alkenyl group of up to 20 carbon atoms having ethylenic unsaturation or heterocyclic aromaticity in conjugation with the indicated ethylenic double bond, R 1 represents a carbon-carbon bond or a divalent, optionally substituted or interrupted, hydrocarbyl residue, R 2 represents a hydrogen, chlorine, or bromine atom, a cyano group, or an aliphatic, aromatic, cycloaliphatic, araliphatic, cycloaliphatic-aliphatic, heterocyclic or heterocyclic-aliphatic group of 1 to 10 carbon atoms, R 3 represents a trivalent aromatic or heterocyclic group bound directly through three carbon atoms thereof to the two indicated ##STR23## and the indicated --COCR 2 ═CHR groups, R 4 represents the residue, free of any substituent of formula --COCH 2 R 2 or --COCR 2 ═CHR, of a dihydric phenol after removal of both phenolic hydroxyl groups, and a, b, and c each represent zero or an integer such that the average molecular weight of the unsaturated ketone of formula I is from 500 to 50,000.
Claim 2
Dependent Claim
172 words
An unsaturated ketone of the formula ##STR22## where R represents a monovalent alkenyl, aralkenyl, cycloalkenyl, cycloalkylalkenyl, cycloalkenylalkenyl, heterocyclic or heterocyclic-alkenyl group of up to 20 carbon atoms having ethylenic unsaturation or heterocyclic aromaticity in conjugation with the indicated ethylenic double bond, R 1 represents a carbon-carbon bond or a divalent, optionally substituted or interrupted, hydrocarbyl residue, R 2 represents a hydrogen, chlorine, or bromine atom, a cyano group, or an aliphatic, aromatic, cycloaliphatic, araliphatic, cycloaliphatic-aliphatic, heterocyclic or heterocyclic-aliphatic group of 1 to 10 carbon atoms, R 3 represents a trivalent aromatic or heterocyclic group bound directly through three carbon atoms thereof to the two indicated ##STR23## and the indicated --COCR 2 ═CHR groups, R 4 represents the residue, free of any substituent of formula --COCH 2 R 2 or --COCR 2 ═CHR, of a dihydric phenol after removal of both phenolic hydroxyl groups, and a, b, and c each represent zero or an integer such that the average molecular weight of the unsaturated ketone of formula I is from 500 to 50,000.
Claim 3
Dependent Claim
31 words
A ketone of claim 1, in which R is an aralkenyl, heterocyclic or heterocyclic-alkenyl group consisting only of carbon and hydrogen atoms and, where appropriate, hetero nitrogen, oxygen, or sulfur atoms.
Claim 4
Dependent Claim
29 words
A ketone of claim 1, in which R 1 represents a residue where both the epoxide groups were present in glycidyl groups attached to oxygen, nitrogen, or sulfur atoms.
Claim 5
Dependent Claim
94 words
A ketone of claim 3, in which R 1 denotes a chain of carbon atoms containing a grouping ##STR24## where R 7 and R 8 individually are each a hydrogen atom, an alkyl group of 1 to 4 carbon atoms, or a phenyl group, and conjointly denote a polymethylene chain of 2 to 4 methylene groups, R 9 and R 10 are each a hydrogen atom, an alkyl group of 1 to 4 carbon atoms, or a phenyl group, and j and k are each zero, 1, or 2, but cannot both be zero.
Claim 6
Dependent Claim
44 words
A ketone of claim 1, in which R 3 represents a group of from 5 to 20 carbon atoms and containing one or two benzenoid rings or heterocyclic rings which have (4 n + 2) π-electrons, where n is the number of said rings.
Claim 7
Dependent Claim
106 words
A ketone of claim 5, in which R 3 represents a group of formula ##STR25## wherein R 6 represents a halogen atom, an alkyl, aryl, or aralkyl group of 1 to 8 carbon atoms, or a group of formula --COCR 2 ═CHR A represents a carbon-carbon bond, an oxygen or sulfur atom, a carbonyl, sulfonyl, or sulfinyl group, or a divalent aliphatic, aromatic, or araliphatic group of 1 to 10 carbon atoms, e represents 0 or an integer of from 1 to 3, f represents 0 or an integer of from 1 to 4, g represents 0 or 1, and h represents 0, 1, or 2.
Claim 8
Dependent Claim
23 words
A ketone according to claim 6, in which R 3 is a group of formula ##STR26## and b, and c, each represent 0.
Claim 9
Dependent Claim
25 words
A ketone according to claim 1, in which a, b, and c are each such that the average molecular weight is from 2000 to 10,000.
Claim 10
Dependent Claim
34 words
A process for the preparation of an unsaturated ketone as claimed in claim 1, which comprises condensation of an advanced epoxide resin of formula ##STR27## with an aldehyde of formula R -- CHO XIII
Claim 11
Dependent Claim
15 words
the process of claim 9, carried out in the presence of an acidic dehydration catalyst.
Claim 12
Dependent Claim
15 words
The process of claim 9, carried out in the presence of a basic condensation catalyst.
Claim 13
Dependent Claim
19 words
The process of claim 9, carried out in the presence of an excess of the aldehyde of formula XIII.
Claim 14
Dependent Claim
30 words
A process for the preparation of an unsaturated ketone as claimed in claim 1, which comprises advancement of a diepoxide of formula, ##STR28## with a dihydric phenol of formula ##STR29##
Claim 15
Dependent Claim
18 words
The process of claim 13, in which there is also used a dihydric phenol of formula HO--R.sup.4 --OH
Claim 16
Dependent Claim
17 words
The process of claim 13, carried out in the presence of a catalyst for advancing epoxide resins.
Claim 17
Dependent Claim
14 words
The process of claim 15, in which the catalyst is a quaternary ammonium salt.
Claim 18
Dependent Claim
21 words
A plate, sensitive to actinic radiation, comprising a support carrying a layer of an unsaturated ketone as claimed in claim 1.
Claim 19
Dependent Claim
15 words
A plate according to claim 17, which further carries a heat-curing agent for epoxide resins.
Claim 20
Dependent Claim
36 words
A plate according to claim 18, in which the curing agent is a polycarboxylic acid anhydride, dicyandiamide, a boron difluoride chelate, or is a complex of a tertiary amine with boron trifluoride or with boron trichloride.
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) | 1981-09-04 | 1982-03-06 | 1982-09-05 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1985-09-04 | 1986-03-06 | 1986-09-05 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1989-09-04 | 1990-03-06 | 1990-09-05 | $7700.00 | Window Closed / Lapsed |