# US 11,440,988 B2 · Polyuretdione-containing resin blend compositions

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- Number: US 11,440,988 B2
- Document ID: US11440988B2
- Status: Granted
- Kind: B2
- Application number: 15/933,511
- Filed: 2018-03-23
- Published: 2019-09-26
- Granted: 2022-09-13
- Earliest claimed: 2018-03-23
- Assignees: Covestro LLC; Covestro Deutschland AG
- Applicants: Covestro LLC; Covestro Deutschland AG
- Inventors: Alan Ekin; Florian Johannes Stempfle; Alan D. Bushmire
- Web page: https://patentgrep.com/patent/US11440988B2

## CPC

- C08G 18/027: {the polymeric products containing urethodione groups}
- C08G 18/1858: {having carbon-to-nitrogen double bonds}
- C08G 18/2027: {having two nitrogen atoms in the ring}
- C08G 18/2036: {having at least three nitrogen atoms in the ring}
- C08G 18/2072: {having at least three nitrogen atoms in the condensed ring system}
- C08G 18/42: Polycondensates having carboxylic or carbonic ester groups in the main chain
- C08G 18/4277: {Caprolactone and/or substituted caprolactone}
- C08G 18/44: Polycarbonates
- C08G 18/48: Polyethers
- C08G 18/6229: {Polymers of hydroxy groups containing esters of acrylic or methacrylic acid with aliphatic polyalcohols}
- C08G 18/7837: {containing allophanate groups}
- C08G 18/797: {containing carbodiimide and/or uretone-imine groups}
- C08G 18/798: {containing urethdione groups}
- C08K 5/31: Guanidine; Derivatives thereof
- C08K 5/3467: having more than two nitrogen atoms in the ring
- C09D 175/04: Polyurethanes
- C09J 175/04: Polyurethanes
- C07D 471/04: Ortho-condensed systems
- C08G 2190/00: Compositions for sealing or packing joints
- C08G: MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08K: Use of inorganic or non-macromolecular organic substances as compounding ingredients (paints, inks, varnishes, dyes, polishes, adhesives C09)
- 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)
- 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)
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)

## Abstract

The present invention provides a reaction mixture comprising a blend of a first isocyanate-based uretdione-containing resin and a second isocyanate-based uretdione-containing resin, a neutralized polyol and a tertiary amine catalyst, and optionally, an additive package selected from the group consisting of flow control additives, pigments (colorants), wetting agents, and solvents, wherein the first isocyanate and the second isocyanate are different. The first isocyanate-based uretdione-containing resin and the second isocyanate-based uretdione-containing resin may be cold blended or hot blended. Coatings, adhesives, castings, composites, and sealants made from hot blended formulations exhibit superior performance over those made from cold blended formulations.

## Claims

### Claim 1

A reaction mixture comprising:
a hot blend of a 1-isocyanato-3-isocyanatomethyl-3,5,5-trimethyl cyclohexane (isophorone diisocyanate or IPDI)-based uretdione-containing resin and a 1,6-hexamethylene diisocyanate (HDI)-based uretdione-containing resin, wherein the hot blend is at an IPDI-uretdione/HDI-uretdione weight ratio of from 92/8 to 45/55;
a neutralized polyester polyol comprising the reaction product of a polyester polyol and an acid scavenger; and
a tertiary amine catalyst comprising 1,8-diazabicyclo[5.4.0]undec-7-ene, and
optionally, a hydrocarbon solvent,
optionally, an additive package selected from the group consisting of flow control additives, pigments, wetting agents, and solvents.

### Claim 2 (depends on 1)

The reaction mixture according to claim 1, wherein the acid scavenger is covalently bonded to acidic groups within the polyester polyol and is selected from the group consisting of carbodiimides, anhydrides, epoxies, trialkylorthoformates, amine compounds, oxazolines, and combinations thereof.

### Claim 3 (depends on 1)

One of a coating, an adhesive, a casting, a composite, and a sealant comprising the reaction mixture according to claim 1.

### Claim 4 (depends on 1)

A method of applying the reaction mixture according to claim 1 to a substrate, wherein the method comprises at least one of spraying, dipping, flow coating, rolling, brushing, and pouring.

### Claim 5

A method of making an allophanate polymer comprising:
hot blending a 1-isocyanato-3-isocyanatomethyl-3,5,5-trimethyl cyclohexane (isophorone diisocyanate or IPDI)-based uretdione-containing resin and a 1,6-hexamethylene diisocyanate (HDI)-based uretdione-containing resin to form a resin blend, wherein the hot blending is at an IPDI-uretdione/HDI-uretdione weight ratio of from 92/8 to 45/55;
reacting the resin blend with a neutralized polyester polyol in the presence of a tertiary amine catalyst and optionally a hydrocarbon solvent,
optionally in the presence of an additive package selected from the group consisting of flow control additives, pigments, wetting agents, and solvents,
wherein the neutralized polyester polyol is the reaction product of a polyester polyol and an acid scavenger and wherein the tertiary amine catalyst is 1,8-diazabicyclo[5.4.0]undec-7-ene.

### Claim 6 (depends on 5)

The method according to claim 5, wherein the acid scavenger is covalently bonded to acidic groups within the polyester polyol and is selected from the group consisting of carbodiimides, anhydrides, epoxies, trialkylorthoformates, amine compounds, oxazolines, and combinations thereof.

### Claim 7 (depends on 5)

An allophanate polymer made according to the method of claim 5.

### Claim 8 (depends on 5)

One of a coating, an adhesive, a casting, a composite, and a sealant comprising the allophanate polymer made according to claim 5.

### Claim 9 (depends on 5)

A method of applying the allophanate polymer made according to claim 5 to a substrate, wherein the method comprises at least one of spraying, dipping, flow coating, rolling, brushing, and pouring.