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US4308367A
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Hydroxyl-containing compositions and their polymerization
Assignee: BASF Corp
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Filing: 1979-01-19
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Granted: 1981-12-29
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Expires: 1999-01-19
Abstract
Abstract Polymerizable compositions comprise (a) a compound containing in the same molecule both at least one phenolic hydroxyl group and at least two groups chosen from allyl, methallyl, and 1-propenyl groups, e.g., 2,2-bis(3-allyl-4-hydroxyphenyl)propane or bis(3-(1-propenyl)-4-hydroxyphenyl)methane, (b) a compound containing at least two mercaptan groups per molecule, e.g., pentaerythritol tetrathioglycollate, and (c) a heat-activated crosslinking agent for phenol-aldehyde novolac resins. The compositions are caused to polymerize by the action of irradiation of free-radical catalysts. The polymers so obtained, containing more than one phenolic hydroxyl group, can be subsequently crosslinked in situ by heating. The compositions are useful in various two-stage operations, such as the production of multilayer printed circuits. Polymerizable compositions may also comprise (d) a compound as (a) but containing at least two phenolic hydroxyl groups, (e) a compound containing more than two mercaptan groups per molecule. On irradiation or on heating in the presence of a catalyst, preferably a free-radical catalyst, these compositions crosslink, they are useful as adhesives in forming coatings on polar substrates.
Inventors
- 👤 George E. Green
- 👤 Abdul-Cader Zahir
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-25 22:36
CPC Classifications
G; G03; G03F; G03F7/00; G03F7/004; G03F7/027; G03F7/0275; Y; Y10; Y10T; Y10T428/00; Y10T428/31504; Y10T428/31551; Y10T428/31627; Y10T428/31645; Y10T428/31678; Y10T428/31688; Y10T428/31692; Y10T428/31855; Y10T428/31859; Y10T428/31877
Claims Analysis
Total Claims: 19
Claim 1
Independent Claim
96 words
A polymerizable composition comprising: (a) a polyhydric phenol which contains in the same molecule both at least two phenolic hydroxyl groups and at least two groups selected from allyl, methallyl, and 1-propenyl groups; (b) a mercaptan which contains at least two mercaptan groups per molecule, such that the polyhydric phenol provides a total of 0.4 to 2.4 equivalents selected from allyl, methallyl, and 1-propenyl group per equivalent of mercaptan group; and (c) an effective amount of a heat-activated crosslinking agent for phenol-aldehyde novolac resins selected from the group consisting of epoxide resins and sources of formaldehyde.
Claim 2
Dependent Claim
96 words
A polymerizable composition comprising: (a) a polyhydric phenol which contains in the same molecule both at least two phenolic hydroxyl groups and at least two groups selected from allyl, methallyl, and 1-propenyl groups; (b) a mercaptan which contains at least two mercaptan groups per molecule, such that the polyhydric phenol provides a total of 0.4 to 2.4 equivalents selected from allyl, methallyl, and 1-propenyl group per equivalent of mercaptan group; and (c) an effective amount of a heat-activated crosslinking agent for phenol-aldehyde novolac resins selected from the group consisting of epoxide resins and sources of formaldehyde.
Claim 3
Dependent Claim
33 words
A composition of claim 1, in which each group chosen from allyl, methallyl, and 1-propenyl groups of the polyhydric phenol is attached to a carbon atom which forms part of an aromatic nucleus.
Claim 4
Dependent Claim
41 words
A composition of claim 1, in which each group chosen from allyl, methallyl, and 1-propenyl groups of the polyhydric phenol is attached to an oxygen atom which is directly attached to a carbon atom which forms part of an aromatic nucleus.
Claim 5
Dependent Claim
25 words
A composition of claim 1, in which the polyhydric phenol is partially etherified with at least two groups chosen from allyl, methallyl, and 1-propenyl groups.
Claim 6
Dependent Claim
29 words
A composition of claim 1, wherein the mercaptan is an ester of a monomercaptan-carboxylic acid with a polyhydric alcohol or of a monomercaptan monohydric alcohol with a polycarboxylic acid.
Claim 7
Dependent Claim
120 words
A composition of claim 1 wherein the mercaptan is of the formula XIII ##STR14## where d and e each represent zero or 1 but are not the same, f is an integer of from 1 to 6, R 9 represents a divalent radical, linked through a carbon atom or carbon atoms thereof to the indicated --O-- or --CO-- units, R 10 represents a divalent organic radical, linked through a carbon atom or carbon atoms thereof to the indicated -SH group and --O-- or --CO-- unit, and R 11 represents an organic radical, which must contain at least one -SH group when f is 1, linked through a carbon atom or carbon atoms thereof to the indicated --O-- or --CO-- unit.
Claim 8
Dependent Claim
107 words
A composition of claim 1 wherein the mercaptan is of the formula XIV ##STR15## where R 12 represents the radical of a polyhydric alcohol after removal of (j+k) alcoholic hydroxyl groups, each R 13 denotes an alkylene group containing a chain of at least 2 and at most 6 carbon atoms between consecutive oxygen atoms, R 14 represents an aliphatic radical of 1 to 6 carbon atoms, containing at least one mercaptan group, g is a positive integer, h is zero or 1, j is zero or a positive integer such that (j+k) is at most 6, and k is an integer of from 2 to 6.
Claim 9
Dependent Claim
86 words
A composition of claim 1 wherein the mercaptan is of the formula XVII ##STR16## where each R 15 denotes an alkylene hydrocarbon group containing from 2 to 4 carbon atoms, R 16 denotes --H, --CH 3 , or --C 2 H 5 , n is integer which has an average value of at least 1, and either p is zero, in which case q and r are each also zero, or p or 1, in which case q is zero or 1 and r is 1.
Claim 10
Dependent Claim
81 words
A composition of claim 1 wherein the mercaptan is of the formula XVIII ##STR17## where each R 17 represents --H or --CH 3 , R 18 represents --CN, --COOH, --CONH 2 , --COOR 19 , --C 6 H 5 , or --OCOR 19 , where R 19 is an alkyl group of one to eight carbon atoms, t is an integer of at least one, u is zero or a positive integer, and s is an integer of more than one.
Claim 11
Dependent Claim
33 words
A composition of claim 1 wherein the mercaptan is of the formula XX ##STR18## where each R 17 represents --H or --CH 3 and x is an integer of from 1 to 4.
Claim 12
Dependent Claim
50 words
A composition of claim 1, wherein the mercaptan is of the formula XXI ##STR19## each R 8 denotes --CH 2 --, (CH 2 ) 2 --, or --CH(CH 3 )--, each R 17 denotes --H or --CH 3 , and R 20 denotes --H or a group --COR 8 SH.
Claim 13
Dependent Claim
10 words
A composition of claim 1, which also contains a photoinitiator.
Claim 14
Dependent Claim
11 words
A composition of claim 1, which also contains a free-radical catalyst.
Claim 15
Dependent Claim
18 words
A composition of claim 1, wherein the polyhydric phenol is 2,2-bis(3-allyl-4-hydroxylphenyl) propane and the mercaptan is pentaerythritol tetrathioglycollate.
Claim 16
Dependent Claim
30 words
A composition of claim 1, wherein the polyhydric phenol is 2,2-bis(3-allyl-4-hydroxyphenyl) propane and the mercaptan is the tris (3-mercapto-2-hydroxypropyl) ether of a polyoxypropylenetriol of an average molecular weight of 800.
Claim 17
Dependent Claim
94 words
A polymerizable composition comprising: (f) a monohydric phenol which contains in the same molecule both one phenolic hydroxyl group and at least two groups selected from allyl, methallyl, and 1-propenyl groups; (g) a mercaptan which contains at least two mercaptan groups per molecule, such that the monohydric phenol provides a total of 0.4 to 2.4 equivalents selected from allyl, methallyl and 1-propenyl groups per equivalent of mercaptan group; and (h) an effective amount of a heat-activated crosslinking agent for phenol-aldehyde novolac resins selected from the group consisting of epoxide resins and sources of formaldehyde.
Claim 18
Dependent Claim
94 words
A polymerizable composition comprising: (f) a monohydric phenol which contains in the same molecule both one phenolic hydroxyl group and at least two groups selected from allyl, methallyl, and 1-propenyl groups; (g) a mercaptan which contains at least two mercaptan groups per molecule, such that the monohydric phenol provides a total of 0.4 to 2.4 equivalents selected from allyl, methallyl and 1-propenyl groups per equivalent of mercaptan group; and (h) an effective amount of a heat-activated crosslinking agent for phenol-aldehyde novolac resins selected from the group consisting of epoxide resins and sources of formaldehyde.
Claim 19
Dependent Claim
31 words
A composition of claim 16, wherein the monohydric phenol is a phenol substituted in the aromatic nucleus or nuclei by at least two groups selected from allyl, methallyl, and 1-propenyl groups.
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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) | 1984-12-28 | 1985-06-29 | 1985-12-29 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1988-12-28 | 1989-06-29 | 1989-12-29 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1992-12-28 | 1993-06-29 | 1993-12-29 | $7700.00 | Window Closed / Lapsed |