# US 2024/0199802 A1 · Polycarbonate diol composition

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- Number: US 2024/0199802 A1
- Document ID: US20240199802A1
- Status: Published application
- Kind: A1
- Application number: 18/285,980
- Filed: 2022-04-20
- Published: 2024-06-20
- Earliest claimed: 2021-04-21
- Assignees: Asahi Kasei Kabushiki Kaisha
- Applicants: Asahi Kasei Kabushiki Kaisha
- Inventors: Eriko HOSHINO; Yasufumi KAWAI
- Web page: https://patentgrep.com/patent/US20240199802A1

## CPC

- C08G 64/0208: {saturated}
- C08G 18/10: Prepolymer processes involving reaction of isocyanates or isothiocyanates with compounds having active hydrogen in a first reaction step
- C08G 18/44: Polycarbonates
- C08G 18/7671: {containing only one alkylene bisphenyl group}
- C08G 63/64: Polyesters containing both carboxylic ester groups and carbonate groups
- C08G 64/183: {containing polyether sequences}
- C09D 175/06: from polyesters
- D06N 3/14: with polyurethanes
- D06N 3/146: {characterised by the macromolecular diols used}
- D06N 2203/068: Polyurethanes
- D06N 2211/28: Artificial leather
- 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)
- D06N: WALL, FLOOR, OR LIKE COVERING MATERIALS, e.g. LINOLEUM, OILCLOTH, ARTIFICIAL LEATHER, ROOFING FELT, CONSISTING OF A FIBROUS WEB COATED WITH A LAYER OF MACROMOLECULAR MATERIAL; FLEXIBLE SHEET MATERIAL NOT OTHERWISE PROVIDED FOR

## Abstract

A polycarbonate diol composition comprising a repeating structural unit represented by the following general formula (I), further comprising at least one repeating structural unit selected from the group consisting of repeating structural units represented by the following general formulas (II) to (IV), and satisfying specific conditions.

## Claims

### Claim 1

A polycarbonate diol composition comprising a repeating structural unit represented by the following general formula (I), further comprising at least one repeating structural unit selected from the group consisting of a repeating structural unit represented by the following general formula (II), a repeating structural unit represented by the following general formula (III), and a repeating structural unit represented by the following general formula (IV), and satisfying the following expression (Expression 1):
R11—O—CO—O (I)
wherein R11 is a divalent linear, branched or cyclic aliphatic, or aromatic hydrocarbon group having 2 or more and 15 or less carbon atoms, the hydrocarbon group optionally having a hetero atom, and R11 when present in plural are the same as or different from each other,
wherein R21 is a divalent linear, branched or cyclic aliphatic, or aromatic hydrocarbon group having 2 or more and 20 or less carbon atoms, and R21 when present in plural are the same as or different from each other; and n21 is any integer,
R31—O—CO (III)
wherein R31 is a divalent linear, branched or cyclic aliphatic, or aromatic hydrocarbon group having 2 or more and 20 or less carbon atoms, and R31 when present in plural are the same as or different from each other,
CO—R41—CO—O—R42—O (IV)
wherein R41 and R42 are each independently a divalent linear, branched or cyclic aliphatic, or aromatic hydrocarbon group having 2 or more and 20 or less carbon atoms, and R41 and R42 when present in plural are the same as or different from each other,
xy≥3.7×α(α=22.4×Mn−0.41) (Expression 1)
wherein x is a proportion of the content (% by mass) of the repeating structural unit represented by the general formula (I) based on the total mass (% by mass) of the repeating structural units represented by the general formulas (I) to (IV), y is an amount of the polycarbonate diol composition titrated (mL) in a cloud point titration method, and Mn is a number-average molecular weight of the polycarbonate diol composition.

### Claim 2

A polycarbonate diol composition comprising a repeating structural unit represented by the following general formula (I) and further comprising at least one repeating structural unit selected from the group consisting of a repeating structural unit represented by the following general formula (II), a repeating structural unit represented by the following general formula (III), and a repeating structural unit represented by the following general formula (IV), wherein based on the total mass of the repeating structural units represented by the general formulas (I) to (IV), a content of the repeating structural unit represented by the general formula (I) is 40% by mass or more, and an amount titrated in a cloud point titration method is 4.0 mL or more and 9.5 mL or less:
R11—O—CO—O (I)
wherein R11 is a divalent linear, branched or cyclic aliphatic, or aromatic hydrocarbon group having 2 or more and 15 or less carbon atoms, the hydrocarbon group optionally having a hetero atom, and R11 when present in plural are the same as or different from each other,
wherein R21 is a divalent linear, branched or cyclic aliphatic, or aromatic hydrocarbon group having 2 or more and 20 or less carbon atoms, and R21 when present in plural are the same as or different from each other; and n21 is any integer,
R31—O—CO (III)
wherein R31 is a divalent linear, branched or cyclic aliphatic, or aromatic hydrocarbon group having 2 or more and 20 or less carbon atoms, and R31 when present in plural are the same as or different from each other,
CO—R41—CO—O—R42—O (IV)
wherein R41 and R42 are each independently a divalent linear, branched or cyclic aliphatic, or aromatic hydrocarbon group having 2 or more and 20 or less carbon atoms, and R41 and R42 when present in plural are the same as or different from each other.

### Claim 3 (depends on 1)

The polycarbonate diol composition according to claim 1, wherein based on the total mass of the repeating structural units represented by the general formulas (I) to (IV), a content of the repeating structural unit represented by the general formula (I) is 5% by mass or more and 95% by mass or less.

### Claim 4 (depends on 1)

The polycarbonate diol composition according to claim 1, wherein based on the total mass of the repeating structural units represented by the general formulas (I) to (IV), a content of the repeating structural unit represented by the general formula (I) is 40% by mass or more and 90% by mass or less.

### Claim 5 (depends on 1)

The polycarbonate diol composition according to claim 1, wherein an acid value is 0.001 mg-KOH/g or more and 0.8 mg-KOH/g or less.

### Claim 6 (depends on 1)

The polycarbonate diol composition according to claim 1, wherein a peroxide content is 10 meq/kg or less.

### Claim 7 (depends on 1)

The polycarbonate diol composition according to claim 1, wherein a Hazen color number value (APHA value) in accordance with JIS K0071-1 (2017) is 100 or less.

### Claim 8 (depends on 1)

The polycarbonate diol composition according to claim 1, wherein among the repeating structural units represented by the general formulas (II) to (IV), an average value of the number of repeats of the repeating structural unit represented by the general formula (II), represented by n21, is 15 or larger.

### Claim 9 (depends on 1)

The polycarbonate diol composition according to claim 1, comprising at least a repeating structural unit represented by the general formula (II) or (IV) among the repeating structural unis represented by the general formulas (II) to (IV).

### Claim 10 (depends on 1)

The polycarbonate diol composition according to claim 1, comprising at least a repeating structural unit represented by the general formula (II) among the repeating structural unis represented by the general formulas (II) to (IV).

### Claim 11 (depends on 1)

A polyurethane prepared using the polycarbonate diol composition according to claim 1.

### Claim 12 (depends on 11)

The polyurethane according to claim 11, wherein, with respect to a stress at 100% stretch according to a tensile test of the polyurethane, ΔM calculated by the following expression (B) is 1.0 or more and 19.0 or less:
ΔM=M1−M2 (B)
wherein M1 represents a stress at 100% stretch in a tensile test under a −20° C. condition, and M2 represents a stress at 100% stretch in a tensile test under a 23° C. condition.

### Claim 13 (depends on 11)

A synthetic leather comprising the polyurethane according to claim 11.

### Claim 14 (depends on 2)

The polycarbonate diol composition according to claim 2, wherein based on the total mass of the repeating structural units represented by the general formulas (I) to (IV), a content of the repeating structural unit represented by the general formula (I) is 40% by mass or more and 90% by mass or less.

### Claim 15 (depends on 3)

The polycarbonate diol composition according to claim 3, wherein based on the total mass of the repeating structural units represented by the general formulas (I) to (IV), a content of the repeating structural unit represented by the general formula (I) is 40% by mass or more and 90% by mass or less.

### Claim 16 (depends on 2)

The polycarbonate diol composition according to claim 2, wherein an acid value is 0.001 mg-KOH/g or more and 0.8 mg-KOH/g or less.

### Claim 17 (depends on 3)

The polycarbonate diol composition according to claim 3, wherein an acid value is 0.001 mg-KOH/g or more and 0.8 mg-KOH/g or less.

### Claim 18 (depends on 4)

The polycarbonate diol composition according to claim 4, wherein an acid value is 0.001 mg-KOH/g or more and 0.8 mg-KOH/g or less.

### Claim 19 (depends on 14)

The polycarbonate diol composition according to claim 14, wherein an acid value is 0.001 mg-KOH/g or more and 0.8 mg-KOH/g or less.

### Claim 20 (depends on 15)

The polycarbonate diol composition according to claim 15, wherein an acid value is 0.001 mg-KOH/g or more and 0.8 mg-KOH/g or less.