# US 11,306,177 B2 · Thermoplastic polyurethane

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- Number: US 11,306,177 B2
- Document ID: US11306177B2
- Status: Granted
- Kind: B2
- Application number: 16/481,709
- Filed: 2018-02-13
- Published: 2019-12-26
- Granted: 2022-04-19
- Earliest claimed: 2017-02-13
- Assignees: BASF SE
- Applicants: BASF SE
- Inventors: Nabarun Roy; Fin Lammers; Dirk Kempfert; Elmar Poeselt
- Web page: https://patentgrep.com/patent/US11306177B2

## CPC

- C08G 18/7671: {containing only one alkylene bisphenyl group}
- C08G 18/3206: {aliphatic}
- C08G 18/4216: {from mixtures or combinations of aromatic dicarboxylic acids and aliphatic dicarboxylic acids and dialcohols}
- C08G 18/6674: {with compounds of group C08G18/3203}
- C08G: MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS

## Abstract

The present invention relates to thermoplastic polyurethanes obtainable or obtained by reaction of at least one polyisocyanate composition, at least one chain extender (KV1) of general formula (I) and one further chain extender (KV2) selected from the group consisting of compounds having at least two isocyanate-reactive groups having a molecular weight of <500 g/mol, and at least one polyol composition. The present invention further relates to a production process for such thermoplastic polyurethanes and to the use of a thermoplastic polyurethane according to the invention or of a thermoplastic polyurethane obtainable or obtained by a process according to the invention for producing extrusion products, films and molded articles.

## Claims

### Claim 1

A thermoplastic polyurethane obtained by reaction of
at least a polyisocyanate composition;
hydroxyquinone bis(2-hydroxyethyl)ether as a first chain extender;
a polyol composition; and
a second chain extender,
wherein the second chain extender has at least two isocyanate-reactive groups and has a molecular weight of <500 g/mol, and
the second chain extender is a compound of general formula (II):
wherein
A is O, N(R3), S, or CH2,
Q is O, N(R3), S, or CH2,
R1 is CH2—(CH2)n—OH, CH(CH3)—CH2—OH, or OH,
R2 is CH2—(CH2)n—OH, CH(CH3)—CH2—OH, CH2—CH(CH3)—OH, or OH,
n is 0, 1, 2, 3, 4, 5 or 6, and
R3 is CH3, or CH2—CH3,
wherein
a molar ratio of hydroquinone bis(2-hydroxyethyl)ether to the second chain extender is in a range of 9:1 to 19:1; and
the polyol present in the polyol composition is a polyetherol.

### Claim 2 (depends on 1)

The thermoplastic polyurethane according to claim 1, wherein said polyetherol is a polytetrahydrofuran having a number-average molecular weight Mn in a range from 500 g/mol to 5000 g/mol.

### Claim 3 (depends on 1)

The thermoplastic polyurethane according to claim 1, wherein said polyetherol comprises a polytetrahydrofuran having a number-average molecular weight Mn in a range from 1501 g/mol to 3000 g/mol and a polytetrahydrofuran having a number-average molecular weight Mn in a range from 500 g/mol to 1500 g/mol.

### Claim 4 (depends on 1)

The thermoplastic polyurethane according to claim 1, wherein the polyisocyanate composition comprises an isocyanate selected from the group consisting of 3,3′-dimethyl-4,4′-diisocyanatobiphenyl, 1,5-naphthylene diisoctanate, p-phenylene diisocyanate, 4,4′-diphenylmethane diisocyanate and 2,4′-diphenylmethane diisocyanate.

### Claim 5 (depends on 1)

The thermoplastic polyurethane according to claim 1, wherein the polyisocyanate composition comprises a mixture of 4,4′-diphenylmethane diisocyanate and 2,4′-diphenylmethane diisocyanate.

### Claim 6

A process for producing a thermoplastic polyurethane, the process comprising: reacting
polyisocyanate composition;
hydroxyquinone bis(2-hydroxyethyl)ether as a first chain extender;
a polyol composition; and
a second chain extender,
wherein the second chain extender has at least two isocyanate-reactive groups and has a molecular weight of <500 g/mol and
the second chain extender is a compound of general formula (II):
wherein
A is O, N(R3), S, or CH2,
Q is O, N(R3), S, or CH2,
R1 is CH2—(CH2)n—OH, CH(CH3)—CH2—OH, or OH,
R2 is CH2—(CH2)n—OH, CH(CH3)—CH2—OH, CH2—CH(CH3)—OH, or OH,
n is 0, 1, 2, 3, 4, 5 or 6, and
R3 is CH3, or CH2—CH3,
wherein
a molar ratio of hydroquinone bis(2-hydroxyethyl)ether to the second chain extender is in a range of 9:1 to 19:1; and
the polyol present in the polyol composition is a polyetherol.

### Claim 7 (depends on 1)

An article, comprising the thermoplastic polyurethane according to claim 1, wherein the article is an extrusion product, a film or a molded article.

### Claim 8 (depends on 7)

The article according to claim 7, wherein the article is an extrusion product or a film, and the extrusion product or the film is reinforced with fillers.

### Claim 9 (depends on 1)

An article, comprising the thermoplastic polyurethane according to claim 1, wherein the article is a foamed film, a foamed molding, foamed particles or particle foams obtained therefrom.

### Claim 10 (depends on 9)

The article according to claim 9, wherein the article is reinforced with fillers.

### Claim 11 (depends on 1)

The thermoplastic polyurethane according to claim 1, where A and Q are each independently O, N(R3),or S.

### Claim 12 (depends on 1)

The thermoplastic polyurethane according to claim 1, wherein said second chain extender is resorcinol bis(2-hydroxyethyl)ether.

### Claim 13 (depends on 1)

The thermoplastic polyurethane according to claim 1, wherein said thermoplastic polyurethane has a room temperature tensile strength of 51 MPa to 52 MPa.

### Claim 14 (depends on 1)

The thermoplastic polyurethane according to claim 1, wherein said thermoplastic polyurethane has a room temperature elongation at break of 510% to 520%.

### Claim 15 (depends on 1)

The thermoplastic polyurethane according to claim 1, wherein an amount of said second chain extender is 5 to 10% based on a total amount of chain extender.

### Claim 16 (depends on 6)

The process according to claim 6, wherein an amount of said second chain extender is 5 to 10% based on a total amount of chain extender.