# US 5,349,041 A · Water dilutable, polyester polyols and their use in coating compositions

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- Number: US 5,349,041 A
- Document ID: US5349041A
- Status: Granted
- Kind: A
- Application number: 08/061,640
- Filed: 1993-05-12
- Granted: 1994-09-20
- Earliest claimed: 1992-05-19
- Assignees: Bayer Aktiengesellschaft
- Inventors: Harald Blum; Lothar Kahl; Nusret Yuva; Manfred Bock
- Web page: https://patentgrep.com/patent/US5349041A

## CPC

- C09K 3/1021: {Polyurethanes or derivatives thereof}
- C08G 18/0823: {containing carboxylate salt groups or groups forming them}
- C08G 18/44: Polycarbonates
- C08G 18/6659: {with compounds of group C08G18/34}
- C09D 175/04: Polyurethanes
- C08G 2190/00: Compositions for sealing or packing joints
- C09K 2200/0645: obtained otherwise than by reactions involving carbon-to-carbon unsaturated bonds
- C09K 2200/0655: Polyesters
- Y10S 528/904: Isocyanate polymer having stated hydrophilic or hydrophobic property
- C09K: MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C08G: MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C09D: COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR (cosmetics A61K; processes for applying liquids or other fluent materials to surfaces, in general, B05D; staining wood B27K5/02; glazes or vitreous enamels C03C; natural resins, French polish, drying-oils, driers, turpentine, per se, C09F; polishing compositions other than French polish, ski waxes C09G; adhesives or use of materials as adhesives C09J; materials for sealing or packing joints or covers C09K3/10; materials for stopping leaks C09K3/12; processes for the electrolytic or electrophoretic production of coatings C25D)
- Y10S: TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS

## Abstract

The present invention relates to water dilutable, urethane group-containing polyester polyols having an acid number of 6 to 45 mg KOH/g, wherein 25 to 100% of the acid groups are neutralized by bases, a hydroxyl number of 20 to 250 mg KOH/g, a molecular weight (M.sub.w) of 2,000 to 150,000 and a urethane content (--NH--CO--O--) of 2 to 16% by weight, wherein the polyester polyol is the at least partly neutralized reaction product of a) 35 to 90% by weight of branched polyester polyols having a hydroxyl number of 40 to 600 and prepared from a1) 0 to 60% by weight of monocarboxylic acids, a2) 6 to 65% by weight of di- and/or tricarboxylic acids or their anhydrides, a3) 10 to 70% by weight of alcohols, a4) 0 to 35% by weight of monoalcohols, a5) 0 to 30% by weight of hydroxycarboxylic acids, aminocarboxylic acids, lactones, lactams and aminoalcohols and a6) 0 to 45% by weight of polycarbonate polyols, b) 0.5 to 8.5% by weight of hydroxycarboxylic acids c) 0 to 15% by weight of compounds containing OH, NH and/or NH.sub.2 groups and having a molecular weight of 32 to 500, d) 3 to 33% by weight of compounds containing isocyanate groups and having a molecular weight of 168 to 2,000 and e) 0 to 45% by weight of polycarbonate polyols, wherein the percentages of a) to e) and a1) to a6) add up to 100% and wherein the urethane group-containing polyester polyols contain 1 to 25% by weight of carbonate groups (--0--CO--O--) incorporated through components e) and/or a6).

## Claims

### Claim 1

A water dilutable, urethane group-containing polyester polyol having an acid number of 6 to 45 mg KOH/g, wherein 25 to 100% of the acid groups are neutralized by bases, a hydroxyl number of 20 to 250 mg KOH/g, a molecular weight (M.sub.w) of 2,000 to 150,000 and a urethane content (--NH--CO--O--) of 2 to 16% by weight, wherein the polyester polyol comprises the at least partly neutralized reaction product of
a) 35 to 90% by weight of one or more branched polyester polyols having a hydroxyl number of 40 to 600 and comprising the reaction product of
a1) 0 to 60% by weight of one or more monocarboxylic acids having 6 to 22 carbon atoms,
a2) 6 to 65% by weight of one or more di- and/or tricarboxylic acids or their anhydrides,
a3) 10 to 70% by weight of one or more alcohols having two and/or more hydroxyl groups,
a4) 0 to 35% by weight of one or more monoalcohols,
a5) 0 to 30% by weight of one or more hydroxycarboxylic acids, aminocarboxylic acids, lactones, lactams and aminoalcohols and
a6) 0 to 45% by weight of one or more polycarbonate polyols having a molecular weight of 450 to 16,000,
b) 0.5 to 8.5% by weight of one or more hydroxycarboxylic acids
c) 0 to 15% by weight of one or more compounds containing at least one OH, NH and/or NH.sub.2 group and having a molecular weight of 32 to 500,
d) 3 to 33% by weight of one or more compounds containing at least two isocyanate groups and having a molecular weight of 168 to 2,000 and
e) 0 to 45% by weight of one or more polycarbonate polyols having a molecular weight of 450 to 16,000,
wherein the percentages of a) to e) and a1) to a6) add up to 100% and wherein the urethane group-containing polyester polyols contain 1 to 25% by weight of carbonate groups (--O--CO--O--) incorporated through components e) and/or a6).

### Claim 2

A water dilutable, urethane group-containing polyester polyol having an acid number of 9 to 35 mg KOH/g, wherein 45 to 100% of the acid groups are neutralized by bases, a hydroxyl number of 35 to 220 mg KOH/g, a molecular weight (M.sub.w) of 3,500 to 70,000 and a urethane content (--NH--CO--O--) of 3.5 to 13.5% by weight, wherein the polyester polyol comprises the at least partly neutralized reaction product of
a) 41 to 86% by weight of one or more branched polyester polyols having a hydroxyl number of 50 to 450 and comprising the reaction product of
a1) 0 to 55% by weight of one or more monocarboxylic acids having 7 to 18 carbon atoms,
a2) 11 to 58% by weight of one or more di- and/or tricarboxylic acids or their anhydrides,
a3) 17 to 63% by weight of one or more alcohols having two and/or more hydroxyl groups,
a4) 0 to 15% by weight of one or more monoalcohols and
a5) 0 to 20% by weight of one or more hydroxycarboxylic acids, aminocarboxylic acids, lactones, lactams and aminoalcohols,
b) 1.5 to 7.0% by weight of 2,2-bis(hydroxymethyl)alkanoic acid,
c) 0 to 10% by weight of one or more compounds containing at least one OH, NH and/or NH.sub.2 group and having a molecular weight of 32 to 500,
d) 5 to 26% by weight of one or more compounds containing at least two isocyanate groups and having a molecular weight of 168 to 2,000 and
e) 5 to 40% by weight of one or more polycarbonate polyols having a molecular weight of 450 to 16 000,
wherein the percentages of a) to e) and a1) to a5) add up to 100% and wherein the urethane group-containing polyester polyols contain 1 to 25% by weight of carbonate groups (--O--CO--O--) incorporated through component e).

### Claim 3

A water dilutable, urethane group-containing polyester polyol having an acid number of 9 to 35 mg KOH/g, wherein 45 to 100% of the acid groups are neutralized by bases, a hydroxyl number of 35 to 220 mg KOH/g, a molecular weight (M.sub.w) of 3,500 to 70,000 and a urethane content (--NH--CO--O--) of 3.5 to 13.5% by weight, wherein the polyester polyol comprises the at least partly neutralized reaction product of
a) 41 to 86% by weight of one or more branched polyester polyols having a hydroxyl number of 50 to 450 and comprising the reaction product of
a1) 0 to 45% by weight of one or more monocarboxylic acids having 7 to 18 carbon atoms,
a2) 11 to 55% by weight of one or more di- and/or tricarboxylic acids or their anhydrides,
a3) 14 to 60% by weight of one or more alcohols having two and/or more hydroxyl groups,
a4) 0 to 15% by weight of one or more monoalcohols,
a5) 0 to 20% by weight of one or more hydroxycarboxylic acids, aminocarboxylic acids, lactones, lactams and aminoalcohols and
a6) 5 to 45% by weight of one or more polycarbonate polyols having a molecular weight of 450 to 16,000,
b) 1.5 to 7.0% by weight of 2,2-bis(hydroxymethyl)alkanoic acid,
c) 0 to 10% by weight of one or more compounds containing at least one OH, NH and/or NH.sub.2 group and having a molecular weight of 32 to 500 and
d) 5 to 26% by weight of one or more compounds containing at least two isocyanate groups and having a molecular weight of 168 to 2,000,
wherein the percentages of a) to d) and a1) to a6) add up to 100% and wherein the urethane group-containing polyester polyols contain 1 to 25% by weight of carbonate groups (--O--CO--O--) incorporated through component a6).

### Claim 4

A water dilutable binder which comprises
A) 30 to 98% by weight of a water dilutable, urethane group-containing polyester polyol having an acid number of 6 to 45 mg KOH/g, wherein 25 to 100% of the acid groups are neutralized by bases, a hydroxyl number of 20 to 250 mg KOH/g, a molecular weight (M.sub.w) of 2,000 to 150,000 and a urethane content (--NH--CO--O--) of 2 to 16% by weight, wherein the polyester polyol comprises the at least partly neutralized reaction product of
a) 35 to 90% by weight of one or more branched polyester polyols having a hydroxyl number of 40 to 600 and comprising the reaction product of
a1) 0 to 60% by weight of one or more monocarboxylic acids having 6 to 22 carbon atoms,
a2) 6 to 65% by weight of one or more di- and/or tricarboxylic acids or their anhydrides,
a3) 10 to 70% by weight of one or more alcohols having two and/or more hydroxyl groups,
a4) 0 to 35% by weight of one or more monoalcohols,
a5) 0 to 30% by weight of one or more hydroxycarboxylic acids, aminocarboxylic acids, lactones, lactams and aminoalcohols and
a6) 0 to 45% by weight of one or more polycarbonate polyols having a molecular weight of 450 to 16,000,
b) 0.5 to 8.5% by weight of one or more hydroxycarboxylic acids
c) 0 to 15% by weight of one or more compounds containing at least one OH, NH and/or NH.sub.2 group and having a molecular weight of 32 to 500,
d) 3 to 33% by weight of one or more compounds containing at least two isocyanate groups and having a molecular weight of 168 to 2,000 and
e) 0 to 45% by weight of one or more polycarbonate polyols having a molecular weight of 450 to 16,000, and
B) 2 to 70% by weight of one or more cross-linking agents, wherein the percentages of a) to e) and a1) to a6) add up to 100%, the urethane group-containing polyester polyols contain 1 to 25% by weight of carbonate groups (--O--CO--O--) incorporated through components e) and/or a6) and the percentages of A) and B) are based on the solids content of A) and B).

### Claim 5 (depends on 4)

The water dilutable binder of claim 4 wherein component B) comprises an aminoplast resin.

### Claim 6 (depends on 5)

The water dilutable binder of claim 5 wherein component B) comprises a polyisocyanate having blocked isocyanate groups.

### Claim 7 (depends on 5)

The water dilutable binder of claim 5 wherein component B) comprises a polyisocyanate having free isocyanate groups.

### Claim 8 (depends on 5)

A coating or jointing composition containing the water dilutable binder of claim 5 and optionally other hydroxyl group-containing resins.