US4578438A
Expired / Lapsed
US
⏱️ 0.0 years remaining
Preparation of resinous products
Assignee: Novartis Corp
•
Filing: 1985-03-11
•
Granted: 1986-03-25
•
Expires: 2005-03-11
Abstract
Abstract Water-dilutable resinous products are obtained by reacting (A) a resin having at least one phenolic hydroxyl group and a free position ortho and/or para to a phenolic hydroxyl group, and containing a residue formed by polymerization of a vinyl monomer in the resin or in a precursor thereof, (B) an aldehyde, and (C) sulphurous acid or an organic acid containing a primary or secondary amino group or a mercaptan group and a carboxylic, sulphonic or phosphonic acid group, or a water-soluble salt thereof. Aqueous compositions containing the resinous products and, if required, and aminoplast, a phenoplast or a blocked polyisocyanate, usually together with a minor amount of an organic solvent, are useful in the formation of surface coatings.
Inventors
- 👤 Christopher G. Demmer
- 👤 Roderick D. Hathaway
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-04 21:58
CPC Classifications
C; C09; C09D; C09D161/00; C09D161/34; C08; C08G; C08G14/00; C08G14/14; C08G8/00; C08G8/38; C09D161/04; C09D161/06; C09D161/14
Claims Analysis
Total Claims: 21
Claim 1
Independent Claim
84 words
A water-dilutable resinous product prepared by reacting together (A) a resin having at least one phenolic hydroxyl group and a free position ortho and/or para to a phenolic hydroxyl group, and containing a residue formed by polymerization of a vinyl monomer in the resin or in a precursor thereof, (B) an aldehyde, and (C) sulfurous acid or an organic acid containing a primary or secondary amino group or a mercaptan group and a carboxylic, sulfonic or phosphonic acid group, or a water-soluble salt thereof.
Claim 2
Dependent Claim
84 words
A water-dilutable resinous product prepared by reacting together (A) a resin having at least one phenolic hydroxyl group and a free position ortho and/or para to a phenolic hydroxyl group, and containing a residue formed by polymerization of a vinyl monomer in the resin or in a precursor thereof, (B) an aldehyde, and (C) sulfurous acid or an organic acid containing a primary or secondary amino group or a mercaptan group and a carboxylic, sulfonic or phosphonic acid group, or a water-soluble salt thereof.
Claim 3
Dependent Claim
18 words
A resinous product according to claim 1, in which (A) has from 1 to 4 phenolic hydroxyl groups.
Claim 4
Dependent Claim
21 words
A resinous product according to claim 1, in which (A) has a backbone derived from an epoxide resin or phenoxy resin.
Claim 5
Dependent Claim
18 words
A resinous product according to claim 1, in which (A) has a molecular weight from 1000 to 10,000.
Claim 6
Dependent Claim
49 words
A resinous product according to claim 1, in which (A) is a resin obtained by reacting en epoxide resin with a polyhydric phenol having a free position ortho and/or para to a phenolic hydroxyl group to produce a phenol-terminated resin and polymerizing a vinyl monomer in the phenol-terminated resin.
Claim 7
Dependent Claim
127 words
A resinous product according to claim 5, in which the epoxide resin has two terminal glycidyl groups directly attached to an atom or atoms of oxygen, nitrogen or sulfur, and the polyhydric phenol is a bisphenol of formula ##STR6## where each R 1 , which may be the same or different, represents a hydrogen atom, a halogen atom, an alkyl group of 1 to 4 carbon atoms, or an alkenyl group of 2 to 4 carbon atoms, with the proviso that at least one of the groups R 1 ortho to a phenolic hydroxyl group is a hydrogen atom, and X represents an alkylene or alkylidene group of 1 to 3 carbon atoms, a carbonyl or sulfonyl group, an oxygen or sulfur atom, or a valency bond.
Claim 8
Dependent Claim
55 words
A resinous product according to claim 1, in which (A) is a resin obtained by polymerizing a vinyl monomer in an epoxide resin having a secondary alcoholic hydroxyl group and reacting the resulting product with a polyhydric phenol having a free position ortho and/or para to a phenolic hydroxyl group to give a phenol-terminated resin.
Claim 9
Dependent Claim
106 words
A resinous product according to claim 7, in which the polyhydric phenol is a bisphenol of formula ##STR7## where each R 1 , which may be the same or different, represents a hydrogen atom, a halogen atom, an alkyl group of 1 to 4 carbon atoms, or an alkenyl group of 2 to 4 carbon atoms, with the proviso that at least one of the groups R 1 ortho to a phenolic hydroxyl group is a hydrogen atom, and X represents an alkylene or alkylidene group of 1 to 3 carbon atoms, a carbonyl or sulfonyl group, an oxygen or sulfur atom, or a valency bond.
Claim 10
Dependent Claim
65 words
A resinous product according to claim 5, in which the vinyl monomer, together with a free radical polymerization initiator, is mixed with the phenol-terminated resin or a solution thereof in an organic solvent, and the mixture is heated at a temperature of 60° to 200° C., the vinyl monomer being used in an amount to provide up to 50% by weight of the resin (A).
Claim 11
Dependent Claim
71 words
A resinous product according to claim 7, in which the vinyl monomer, together with a free radical polymerization initiator, is mixed with the epoxide resin having a secondary alcoholic hydroxyl group, or a solution thereof in an organic solvent, and the mixture is heated at a temperature of 60° to 200° C., the vinyl monomer being used in an amount to provide up to 50% by weight of the resin (A).
Claim 12
Dependent Claim
46 words
A resinous product according to claim 1, in which the vinyl monomer is a styrene; acrylic or methacrylic acid or an ester thereof; acrylamide, methacrylamide or a hydroxyalkyl derivative thereof; a vinyl ester of a carboxylic acid, or a mixture of two or more of these.
Claim 13
Dependent Claim
33 words
A resinous product according to claim 9, in which the polymerization initiator is a peroxide or an azo compound, present in an amount of 1 to 20% by weight of the vinyl monomer.
Claim 14
Dependent Claim
33 words
A resinous product according to claim 10, in which the polymerization initiator is a peroxide or an azo compound, present in an amount of 1 to 20% by weight of the vinyl monomer.
Claim 15
Dependent Claim
22 words
A resinous product according to claim 1, in which the aldehyde (B) is an aliphatic aldehyde having 1 to 6 carbon atoms.
Claim 16
Dependent Claim
45 words
A resinous product according to claim 1, in which (C) is a mercaptocarboxylic acid of formula HS--R.sup.7 --COOH IV where R 7 denotes an aliphatic, aromatic or araliphatic divalent group of 1 to 10 carbon atoms or such a group containing a carboxylic acid group.
Claim 17
Dependent Claim
219 words
A resinous product according to claim 1, in which (C) is an aminocarboxylic acid of formula ##STR8## where R 8 denotes an aliphatic, aromatic or araliphatic divalent group of 1 to 10 carbon atoms or such a group containing a carboxylic acid group, R 9 denotes a hydrogen atom, a group of formula ##STR9## an alkyl group of 1 to 6 carbon atoms or an alkyl group of 1 to 6 carbon atoms substituted by a carboxylic group or by a group of formula --CH(R 10 )OH or --CH(R 10 )OR 12 , with the proviso that R 8 and R 9 together contain not more than one carboxylic acid group, R 10 denotes a hydrogen atom, an alkyl group of 1 to 4 carbon atoms, or an aryl group of 6 to 10 carbon atoms, R 11 denotes a hydrogen atom, a carboxylic acid group, an alkyl group of 1 to 6 carbon atoms, or an alkyl group of 1 to 6 carbon atoms substituted by a carboxylic acid group or by a group of formula --CH(R 10 )OH or CH(R 10 )OR 12 , and R 12 denotes an alkyl group of 1 to 6 carbon atoms or an alkoxyalkyl group in which the alkoxy group and alkyl group each have from 1 to 6 carbon atoms.
Claim 18
Dependent Claim
22 words
A resinous product, according to claim 1, in which (C) is glycine, glutamic acid, aspartic acid, p-aminobenzoic acid, sarcosine or thioglycolic acid.
Claim 19
Dependent Claim
42 words
A resinous product, according to claim 1, in which (A), (B) and (C) are heated together in an inert solvent, in the presence of sufficient base to neutralise or partially neutralise any free acid, at a temperature of 60° to 180° C.
Claim 20
Dependent Claim
37 words
A resinous product according to claim 1, in which there are used 0.3 to 2.0 moles of (C) per mole of phenolic hydroxyl groups in (A) and 1.1 to 4.0 moles of (B) per mole of (C).
Claim 21
Dependent Claim
94 words
A heat-curable composition comprising 100 parts by weight of a product according to claim 1, calculated on its solids content and 2 to 200 parts by weight, calculated on its solids content, of an aminoplast, a phenol-formaldehyde resin, or a blocked polyisocyanate, the aminoplast or phenol-formaldehyde resin having at least 2 groups of formula --CH.sub.2 OR.sup.13 VII attached directly to an amidic nitrogen atom or atoms or directly attached to carbon atoms of a phenolic ring, where R 13 represents a hydrogen atom or an alkyl group of from 1 to 6 carbon atoms.
References Cited (Backward Citations)
US4308185A
Cited
US4362853A
Cited
US4396732A
Cited
GB2118936A
Cited
EP0098623A1
Cited
US4514547A
Cited
US4410675A
Cited
US4500691A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1989-03-24 | 1989-09-23 | 1990-03-25 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1993-03-24 | 1993-09-23 | 1994-03-25 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1997-03-24 | 1997-09-23 | 1998-03-25 | $7700.00 | Window Closed / Lapsed |