# US 2020/0399418 A1 · Polyurethane-based polymer material having excellent resistance to heat distortion and elongation at tear

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- Number: US 2020/0399418 A1
- Document ID: US20200399418A1
- Status: Published application
- Kind: A1
- Application number: 16/971,987
- Filed: 2019-02-11
- Published: 2020-12-24
- Earliest claimed: 2018-02-22
- Assignees: BASF SE
- Applicants: BASF SE
- Inventors: Andreas Emge; Andre Meyer; Berend Eling; Stefan Auffarth
- Web page: https://patentgrep.com/patent/US20200399418A1

## CPC

- C08G 18/0885: {using additives, e.g. absorbing agents}
- C08G 18/7664: {containing alkylene polyphenyl groups}
- C08F 283/006: {on to polymers provided for in C08G18/00 (C08F283/004 takes precedence)}
- C08G 18/225: {of alkali or alkaline earth metals}
- C08G 18/3206: {aliphatic}
- C08G 18/36: Hydroxylated esters of higher fatty acids
- C08G 18/4816: {mixtures of two or more polyetherpolyols having at least three hydroxy groups}
- C08G 18/4829: {Polyethers containing at least three hydroxy groups (C08G18/4833 - C08G18/5096 take precedence)}
- C08G 18/6696: {with compounds of group C08G18/36 or hydroxylated esters of higher fatty acids of C08G18/38}
- C08G 18/725: {Combination of polyisocyanates of C08G18/78 with other polyisocyanates}
- C08G 18/797: {containing carbodiimide and/or uretone-imine groups}
- C08K 9/06: with silicon-containing compounds
- C08G: MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08F: MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08K: Use of inorganic or non-macromolecular organic substances as compounding ingredients (paints, inks, varnishes, dyes, polishes, adhesives C09)

## Abstract

The present disclosure relates to processes for the production of a polyurethane material, where (a) di- and/or polyisocyanates, (b) compounds which have hydrogen atoms reactive toward isocyanate groups and which do not include compounds having carbon-carbon double bonds, (c) compounds including at least one carbon-carbon double bond, (d) optionally catalyst that accelerates the urethane reaction, and (e) optionally other auxiliaries and additives are mixed to give a reaction mixture and the mixture is hardened at temperatures above 120° C. The present disclosure further relates to a polyurethane material obtainable by this process, and also to the use of the polyurethane material, in particular of a polyurethane fiber-composite material as structural components.

## Claims

### Claim 1

A process for the production of a polyurethane material with a heat-deflection temperature of at least 130° C. in three-point bending with 0.45 MPa outer fiber stress in accordance with DIN EN ISO 75, the process comprising:
mixing components comprising:
a. di- and/or polyisocyanates,
b. compounds having hydrogen atoms reactive toward isocyanate groups, where the compounds having hydrogen atoms reactive toward isocyanate groups comprise no compounds having carbon-carbon double bonds,
c. compounds comprising at least one carbon-carbon double bond,
d. optionally a catalyst that accelerates a urethane reaction, and
e. optionally other auxiliaries and additives,
to give a reaction mixture, and
hardening the reaction mixture at temperatures above 120° C., where:
the compounds b) having hydrogen atoms reactive toward isocyanate groups have, per molecule, an average of at least 1.5 hydrogen groups reactive toward isocyanate and
the compounds (c) comprising at least one carbon-carbon double bond comprise compounds (c1) comprising at least one carbon-carbon double bond and at least one group selected from groups reactive toward isocyanate and isocyanate groups and/or compounds (c2) comprising at least two carbon-carbon double bonds, and
where the reaction mixture has been stabilized by addition of a free-radical inhibitor such that when the components are mixed at room temperature and the reaction mixture is injected into a metal mold with dimensions of 20 cm×30 cm×0.4 cm controlled to a temperature of 80° C. and is demolded after 60 minutes and cooled to room temperature, the heat-deflection temperature of the polyurethane material in three-point bending with 0.45 MPa outer fiber stress in accordance with DIN EN ISO 75 is at least 25° C. lower than the heat-deflection temperature of an identically produced polyurethane material which is heat-conditioned for a further 120 minutes at 150° C. in an oven after the production process and then is cooled to room temperature.

### Claim 2 (depends on 1)

The process according to claim 1, wherein an impact resistance of the polyurethane material in accordance with DIN EN ISO 179-1/1fU is above 25 kJ/m2.

### Claim 3 (depends on 1)

The process according to claim 1, wherein an equivalence ratio of isocyanate groups of the di- and/or polyisocyanates (a) to the hydrogen atoms reactive toward isocyanate is 0.7 to 1.4.

### Claim 4 (depends on 1)

The process according to claim 1, wherein a proportion of an entirety of the compounds (c1) and (c2), based on a total quantity of compounds (c), is 5 to 100 mol %.

### Claim 5 (depends on 1)

The process according to claim 1, wherein a molar mass of the compound (c) is below 1000 g/mol.

### Claim 6 (depends on 1)

The process according to claim 1, wherein the compounds (c1) and (c2) have, based on the carbon-carbon double bonds, 60 to 100% of terminal carbon-carbon double bonds.

### Claim 7 (depends on 1)

The process according to claim 1, wherein the di- and/or polyisocyanates (a) comprise at least 50 mol % of isocyanates with functionality of 2.

### Claim 8 (depends on 1)

The process according to claim 1, wherein the di- and/or polyisocyanates (a) comprise 2,4′-MDI, 4,4′-MDI or a mixture of these components, optionally also with MDI homologs having a larger number of rings.

### Claim 9 (depends on 1)

The process according to claim 1, wherein the reaction mixture comprises 0.001 to 1.0% by weight of the free-radical inhibitor.

### Claim 10 (depends on 1)

The process according to claim 1, wherein the reaction mixture further comprises basic catalysts.

### Claim 11 (depends on 1)

The process according to claim 1, wherein a proportion of the compounds (c) having carbon-carbon double bond, based on a total weight of components (a) to (e), is 10 to 70% by weight.

### Claim 12 (depends on 1)

The process according to claim 1, wherein the compounds (b) having hydrogen atoms reactive toward isocyanate groups comprising no compounds having carbon-carbon double bonds, comprise higher-molecular-weight compounds having hydrogen atoms reactive toward isocyanate and molar mass of 300 g/mol and above, and the higher-molecular-weight compounds having hydrogen atoms reactive toward isocyanate comprise at least one hydroxy-functional compound having hydrophobic groups.

### Claim 13 (depends on 1)

The process according to claim 1, wherein a reaction of the reaction mixture is conducted in a first stage for at least 10 minutes at temperatures below 120° C. and then the reaction mixture is hardened at temperatures above 150° C.

### Claim 14 (depends on 1)

The process according to claim 1, wherein the polyurethane material is a polyurethane fiber-composite material, where the reaction mixture is used to wet a fiber material and then the reaction mixture is hardened to give the polyurethane fiber-composite material.

### Claim 15 (depends on 1)

A polyurethane material obtainable by a process according to claim 1.