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US4665146A Expired / Lapsed US ⏱️ 0.0 years remaining

Amine-functional monoethylenic monomers, acrylic copolymers and aqueous coating compositions containing the same

Assignee: DeSoto Inc
•
Filing: 1986-05-22
•
Granted: 1987-05-12
•
Expires: 2006-05-22
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Abstract

Abstract Monoethylenically unsaturated polymerizable monomers carrying a plurality of ketimine-blocked primary amine groups are disclosed. These are preferably provided by reacting an organic diisocyanate with the single secondary amine group of a ketimine-blocked diprimary amine carrying a single secondary amino hydrogen atom and then reacting a monohydric acrylate with the other isocyanate group. These monomers are polymerizable to provide copolymers with other monoethylenically unsaturated monomers, and especially acrylate-functional monomers, in which the amine groups remain blocked. These amine groups become unblocked when the copolymers are dispersed in water to form various types of aqueous coating compositions.

Inventors

  • 👤 Anthony J. Tortorello
  • 👤 Joseph D. Lukanich

Bibliographic Details

Application Number —
Jurisdiction US
Data Source google_patents
Last Synchronized 2026-11-06 03:41
CPC Classifications
C; C08; C08F; C08F246/00; C08F220/00; C08F220/02; C08F220/10; C08F220/34; C08F220/36

Claims Analysis

Total Claims: 24
Claim 1
Independent Claim 28 words
A copolymer of monoethylenically unsaturated monomers comprising from 3% to 35% copolymerized monomer which is a monoethylenically unsaturated polymerizable monomer carrying a plurality of ketimine-blocked primary amine groups.
Claim 2
Dependent Claim 28 words
A copolymer of monoethylenically unsaturated monomers comprising from 3% to 35% copolymerized monomer which is a monoethylenically unsaturated polymerizable monomer carrying a plurality of ketimine-blocked primary amine groups.
Claim 3
Dependent Claim 35 words
A copolymer of monoethylenically unsaturated monomers as recited in claim 1 in which the monoethylenic unsaturation of said monomer carrying a plurality of ketimine-blocked primary amine groups is provided by the acrylate or methacrylate group.
Claim 4
Dependent Claim 24 words
A copolymer of monoethylenically unsaturated monomers as recited in claim 1 in which said ketimine-blocked primary amine groups are provided by diketimine-blocked diethylene triamine.
Claim 5
Dependent Claim 48 words
A copolymer of monoethylenically unsaturated monomers as recited in claim 1 in which said ketimine-blocked primary amine groups are provided by diketimine-blocked dialkylene triamine in which the alkylene groups contain from 2-4 carbon atoms, and said monomer carrying a plurality of ketimine-blocked primary amine groups contains acrylate unsaturation.
Claim 6
Dependent Claim 26 words
A copolymer of monoethylenically unsaturated monomers as recited in claim 1 in which said monomer carrying a plurality of ketimine-blocked primary amine groups is a urethane.
Claim 7
Dependent Claim 101 words
A copolymer of monethylenically unsaturated monomers comprising from 3% to 35% of copolymerized monomer which is a monoethylenically unsaturated polymerizable monomer carrying blocked primary amine groups and having the formula: ##STR2## in which: R 1 is a divalent organic aliphatic or aromatic molecule connecting the two isocyanate groups the residues of which are shown; R 2 is C 2 -C 4 alkylene; R 3 is a monoethylenically unsaturated carboxylic acid forming an ester with R 2 ; R 4 is C 2 -C 4 alkylene; and Z is the residue of an aliphatic ketone forming a ketimine with the nitrogen atom.
Claim 8
Dependent Claim 101 words
A copolymer of monethylenically unsaturated monomers comprising from 3% to 35% of copolymerized monomer which is a monoethylenically unsaturated polymerizable monomer carrying blocked primary amine groups and having the formula: ##STR2## in which: R 1 is a divalent organic aliphatic or aromatic molecule connecting the two isocyanate groups the residues of which are shown; R 2 is C 2 -C 4 alkylene; R 3 is a monoethylenically unsaturated carboxylic acid forming an ester with R 2 ; R 4 is C 2 -C 4 alkylene; and Z is the residue of an aliphatic ketone forming a ketimine with the nitrogen atom.
Claim 9
Dependent Claim 17 words
A copolymer of monoethylenically unsaturated monomers as recited in claim 6 in which R 2 is ethylene.
Claim 10
Dependent Claim 17 words
A copolymer of monoethylenically unsaturated monomers as recited in claim 6 in which R 4 is ethylene.
Claim 11
Dependent Claim 21 words
A copolymer of monoethylenically unsaturated monomers as recited in claim 6 in which R 3 is acrylic acid or methacrylic acid.
Claim 12
Dependent Claim 21 words
A copolymer of monoethylenically unsaturated monomers as recited in claim 8 in which R 3 is acrylic acid or methacrylic acid.
Claim 13
Dependent Claim 38 words
A copolymer of monoethylenically unsaturated monomers comprising from 3% to 35% of copolymerized monomer as recited in claim 6 in which R 2 is ethylene, R 4 is ethylene, and R 3 is acrylic acid or methacrylic acid.
Claim 14
Dependent Claim 21 words
A copolymer as recited in claim 6 comprising from 5% to 20% of copolymerized said monomer carrying blocked primary amine groups.
Claim 15
Dependent Claim 10 words
A copolymer as recited in claim 12 comprising acrylate-functional monomer.
Claim 16
Dependent Claim 15 words
A copolymer as recited in claim 1 made by solution copolymerization and comprising acrylate-functional monomer.
Claim 17
Dependent Claim 19 words
A copolymer as recited in claim 14 in which said copolymerization is carried out in water miscible organic solvent.
Claim 18
Dependent Claim 17 words
A copolymer as recited in claim 15 dispersed in water with the aid of a solubilizing acid.
Claim 19
Dependent Claim 18 words
An aqueous coating composition comprising the copolymer dispersion of claim 16 including a curing agent for said polymer.
Claim 20
Dependent Claim 23 words
A copolymer as recited in claim 15 comprising copolymerized monoethylenically unsaturated carboxylic acid dispersed in water with the aid of a volatile amine.
Claim 21
Dependent Claim 22 words
An electrocoating bath comprising the dispersion of claim 16 having a resin solids content in the range of from 3% to 20%.
Claim 22
Dependent Claim 18 words
An aqueous coating composition comprising the copolymer dispersion of claim 19 including a curing agent for said polymer.
Claim 23
Dependent Claim 23 words
An aqueous coating composition comprising the copolymer dispersion of claim 20 in which said curing agent for said polymer includes blocked isocyanate groups.
Claim 24
Dependent Claim 22 words
An electrocoating bath comprising the dispersion of claim 20 having a resin solids content in the range of from 3% to 20%.

References Cited (Backward Citations)

No citation records indexed.

USPTO Annuity & Maintenance Windows

Annuity Stage Window Opens Payment Deadline Surcharge Period Until Estimated Fee Status
3.5 Years (Year 4) 1990-05-11 1990-11-10 1991-05-12 $2000.00 Window Closed / Lapsed
7.5 Years (Year 8) 1994-05-11 1994-11-10 1995-05-12 $3760.00 Window Closed / Lapsed
11.5 Years (Year 12) 1998-05-11 1998-11-10 1999-05-12 $7700.00 Window Closed / Lapsed

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