# US 11,028,296 B2 · One component polyurethane dispersion for vinyl windows and other substrates

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- Number: US 11,028,296 B2
- Document ID: US11028296B2
- Status: Granted
- Kind: B2
- Application number: 15/948,263
- Filed: 2018-04-09
- Published: 2019-02-07
- Granted: 2021-06-08
- Earliest claimed: 2017-08-02
- Assignees: Covestro LLC; Covestro Deutschland AG
- Applicants: Covestro LLC; Covestro Deutschland AG
- Inventors: Stephanie Goldfein; Makoto Nakao; Lyubov Gindin; Hans Georg Grablowitz; Ronald Konitsney; Derick Henderson; Tina Kasardo; Philip Jones; Michael K. Jeffries
- Web page: https://patentgrep.com/patent/US11028296B2

## CPC

- C09J 175/04: Polyurethanes
- C08G 18/0823: {containing carboxylate salt groups or groups forming them}
- C08G 18/10: Prepolymer processes involving reaction of isocyanates or isothiocyanates with compounds having active hydrogen in a first reaction step
- C08G 18/283: {Compounds containing ether groups, e.g. oxyalkylated monohydroxy compounds}
- C08G 18/3206: {aliphatic}
- C08G 18/348: {Hydroxycarboxylic acids}
- C08G 18/4211: {derived from aromatic dicarboxylic acids and dialcohols}
- C08G 18/6505: {the low-molecular compounds being compounds of group C08G18/32 or polyamines of C08G18/38}
- C08G 18/6529: {Compounds of group C08G18/3225 or polyamines of C08G18/38}
- C08G 18/6603: {with compounds of group C08G18/32 or polyamines of C08G18/38}
- C08G 18/6659: {with compounds of group C08G18/34}
- C08G 18/758: {containing two or more cycloaliphatic rings}
- C09D 175/04: Polyurethanes
- C09D 175/06: from polyesters
- C08G 18/3203: {Polyhydroxy compounds}
- C08G 18/3225: {Polyamines}
- C08L 2201/52: Aqueous emulsion or latex, e.g. containing polymers of a glass transition temperature (Tg) below 20°C
- C09J: ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES (preparation of glue or gelatine C09H)
- 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)
- C08L: COMPOSITIONS OF MACROMOLECULAR COMPOUNDS (compositions based on polymerisable monomers C08F, C08G; artificial filaments or fibres D01F; textile treating compositions D06)

## Abstract

The present invention provides an aqueous polyurethane dispersion (PUD) comprising an amorphous polyester having a glass transition temperature (Tg) as determined by differential scanning calorimetry of less than −30° C.; wherein the aqueous polyurethane dispersion (PUD) has a glass transition temperature (Tg) as determined by differential scanning calorimetry (DSC) of 0° C. to 20° C. and a hard block content of greater than 50%. Coatings, adhesives, sealants, paints, primers and topcoats, made from the inventive aqueous polyurethane dispersion (PUD) pass detergent resistance testing according to the American Architectural Manufacturers Association's standard, AAMA 615-13, have a pencil hardness according to ASTM D3363 of at least 3H, and are particularly suited for use on low surface energy substrates such as vinyl and other surfaces including floors, windows, doors, window frames, door frames, window shutters, railing, gates, pillars, arbors, pergolas, trellises, gazebos, posts, fencing, pipes and fittings, wire and cable insulation, automobile components, credit cards, and siding.

## Claims

### Claim 1

An aqueous polyurethane dispersion (PUD) comprising the reaction product of:
(i) a polyisocyanate;
(iii) a compound comprising at least one isocyanate-reactive group and an anionic group or potentially anionic group;
(iv) an amorphous polyester having a glass transition temperature (Tg) as determined by differential scanning calorimetry (DSC) of less than −30° C. and comprising ortho-phthalic anhydride;
(v) water;
(vi) a mono functional polyalkylene ether;
(vii) a polyol having a molecular weight of less than <400 g/mol, and
(viii) a polyamine or amino alcohol having a molecular weight of 32 to 400 g/mol,
wherein the aqueous polyurethane dispersion (PUD) has a glass transition temperature (Tg) as determined by differential scanning calorimetry (DSC) of 0° C. to 20° C. and a hard block content of greater than 50%.

### Claim 2 (depends on 1)

The aqueous polyurethane dispersion (PUD) according to claim 1, wherein the amorphous polyester (iv) comprises ortho-phthalic anhydride and 1,6-hexanediol.

### Claim 3 (depends on 1)

The aqueous polyurethane dispersion (PUD) according to claim 1, wherein the dispersion has a hard block content of 50% to 60%.

### Claim 4 (depends on 1)

The aqueous polyurethane dispersion (PUD) according to claim 1, wherein the dispersion has a hard block content of greater than 55% to 60%.

### Claim 5 (depends on 1)

The aqueous polyurethane dispersion (PUD) according to claim 1, wherein the amorphous polyester (iv) has a molecular weight of 300 to 3000.

### Claim 6 (depends on 1)

The aqueous polyurethane dispersion (PUD) according to claim 1, wherein the amorphous polyester (iv) has a molecular weight of 1000.

### Claim 7 (depends on 1)

The aqueous polyurethane dispersion (PUD) according to claim 1, wherein the polyisocyanate (i) is selected from the group consisting of 1,6-hexamethylene diisocyanate (HDI), pentamethylene diisocyanate (PDI), isophorone diisocyanate (IPDI), 2,2,4- and 2,4,4-trimethyl-hexamethylene diisocyanate, isomeric bis-(4,4′-isocyanatocyclohexyl)methanes or mixtures thereof of any desired isomer content, 1,4-cyclohexylene diisocyanate, 1,4-phenylene diisocyanate, 2,4- and 2,6-toluene diisocyanate or hydrogenated 2,4- and 2,6-toluene diisocyanate, 1,5-naphthalene diisocyanate, 2,4′- and 4,4′-diphenylmethane diisocyanate, 1,3- and 1,4-bis-(2-isocyanato-prop-2-yl)-benzene (TMXDI), 1,3-bis(isocyanato-methyl)benzene (XDI), and (S)-alkyl 2,6-diisocyanato-hexanoates or (L)-alkyl 2,6-diisocyanatohexanoates.

### Claim 8 (depends on 1)

The aqueous polyurethane dispersion (PUD) according to claim 1, wherein the PUD comprises n-methyl-2-pyrrolidone (NMP).

### Claim 9 (depends on 1)

The aqueous polyurethane dispersion (PUD) according to claim 1, wherein the PUD is substantially free of n-methyl-2-pyrrolidone (NMP).

### Claim 10 (depends on 1)

One of a coating, an adhesive, a sealant, a paint, a primer, and a topcoat, comprising the aqueous polyurethane dispersion (PUD) according to claim 1.

### Claim 11 (depends on 10)

The one of a coating, an adhesive, a sealant, a paint, a primer, and a topcoat according to claim 10, wherein the one of a coating, an adhesive, a sealant, a paint, a primer, and a topcoat passes detergent resistance testing according to AAMA 615-13 with a minimum 90% gloss retention, a maximum color change of 5 delta E, with no blistering, with no loss of adhesion after testing and has a pencil hardness according to ASTM D3363 of at least 3H.

### Claim 12 (depends on 10)

The one of a coating, an adhesive, a sealant, a paint, a primer, and a topcoat according to claim 10, wherein the one of a coating, an adhesive, a sealant, a paint, a primer, and a topcoat exhibits no staining by betadine after four hours.

### Claim 13 (depends on 10)

The one of a coating, an adhesive, a sealant, a paint, a primer, and a topcoat according to claim 10, wherein the one of a coating, an adhesive, a sealant, a paint, a primer, and a topcoat passes humidity resistance testing according to ASTM D714 with no blistering.

### Claim 14 (depends on 10)

The one of a coating, an adhesive, a sealant, a paint, a primer, and a topcoat according to claim 10 having a pencil hardness according to ASTM D3363 of from 3H to 6H.

### Claim 15 (depends on 10)

A substrate having applied thereto the one of a coating, an adhesive, a sealant, a paint, a primer, and a topcoat according to claim 10.

### Claim 16 (depends on 15)

The substrate according to claim 15, wherein the substrate is selected from the group consisting of wood, polyamide (PA), polyethylene (PE), high-density polyethylene (HDPE), low-density polyethylene (LDPE), polyethylene terephthalate (PET), polytetrafluoroethylene (PTFE), polyester (PES), polypropylene (PP), polystyrene (PS), polyvinyl chloride (PVC), polyurethane (PU), thermoplastic polyurethane, epoxy, polycarbonate (PC), acrylonitrile butadiene styrene (ABS), polycarbonate/acrylonitrile butadiene styrene (PC/ABS), polyethylene/acrylonitrile butadiene styrene (PE/ABS), polymethyl methacrylate (PMMA), polybenzimidazole (PBI), polyoxymethylene (POM), concrete, masonry, textiles, metals, ceramics, composites, and glass.

### Claim 17 (depends on 15)

The substrate according to claim 15 wherein the substrate is selected from the group consisting of floors, windows, doors, window frames, door frames, window shutters, window surrounds railing, gates, pillars, arbors, pergolas, trellises, gazebos, posts, fencing, pipes and fittings, wire and cable insulation, automobile components, credit cards, cladding and siding.

### Claim 18

A coating comprising an aqueous polyurethane dispersion (PUD) comprising the reaction product of:
(i) a polyisocyanate;
(iii) a compound comprising at least one isocyanate-reactive group and an anionic group or potentially anionic group;
(iv) an amorphous polyester having a glass transition temperature (Tg) as determined by differential scanning calorimetry (DSC) of less than −30° C. and comprising ortho-phthalic anhydride;
(v) water;
(vi) a mono functional polyalkylene ether;
(vii) a polyol having a molecular weight of less than <400 g/mol, and
(viii) a polyamine or amino alcohol having a molecular weight of 32 to 400 g/mol,
wherein the aqueous polyurethane dispersion (PUD) has a glass transition temperature (Tg) as determined by differential scanning calorimetry (DSC) of 0° C. to 20° C. and a hard block content of greater than 50%,
wherein the coating passes detergent resistance testing according to AAMA 615-13 with a minimum 90% gloss retention, a maximum color change of 5 delta E, with no blistering and no loss of adhesion after testing,
wherein the coating exhibits no staining by betadine after four hours,
wherein the coating passes humidity resistance testing according to ASTM D714 with no blistering and
wherein the coating has a pencil hardness according to ASTM D3363 of at least 3H.

### Claim 19 (depends on 18)

The coating according to claim 18, wherein the amorphous polyester (iv) comprises ortho-phthalic anhydride and 1,6-hexanediol.

### Claim 20 (depends on 18)

The coating according to claim 18, wherein the PUD contains n-methyl-2-pyrrolidone (NMP).

### Claim 21 (depends on 18)

The coating according to claim 18, wherein the PUD is substantially free of n-methyl-2-pyrrolidone (NMP).

### Claim 22 (depends on 1)

The aqueous polyurethane dispersion (PUD) according to claim 1, wherein the reaction product further comprises one reactant selected from the group consisting of polyisocyanates, aziridines, and carbodiimides.

### Claim 23 (depends on 18)

The coating according to claim 18, wherein the aqueous polyurethane dispersion (PUD) comprises the reaction product further comprising one reactant selected from the group consisting of polyisocyanates, aziridines, and carbodiimides.

### Claim 24 (depends on 1)

The aqueous polyurethane dispersion (PUD) of claim 1 further comprising the reaction product of (ii) a polymeric polyol having a number average molecular weight of 400 to 8,000 g/mol.

### Claim 25 (depends on 18)

The paint or coating of claim 18 wherein the aqueous polyurethane dispersion (PUD) further comprises the reaction product of (ii) a polymeric polyol having a number average molecular weight of 400 to 8,000 g/mol.

### Claim 26 (depends on 15)

The substrate according to claim 15, wherein the substrate has a surface energy of from 12 mJ/m2 to 60 mJ/m2.

### Claim 27 (depends on 15)

The substrate according to claim 15, wherein the substrate has a surface energy of from 25 mJ/m2 to 45 mJ/m2.

### Claim 28 (depends on 15)

The substrate according to claim 15, wherein the substrate has a surface energy of 30 mJ/m2 to 40 mJ/m2.

### Claim 29 (depends on 1)

The aqueous polyurethane dispersion of claim 1, wherein component (viii) is present in the reaction product in an amount of 1% to 10% by weight of the reactants to make the polyurethane.