# US 8,273,846 B2 · Polyurethane and polyurethane urea elastomers based on polycarbonate polyols

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- Number: US 8,273,846 B2
- Document ID: US8273846B2
- Status: Granted
- Kind: B2
- Application number: 12/168,957
- Filed: 2008-07-08
- Published: 2009-01-15
- Granted: 2012-09-25
- Earliest claimed: 2007-07-11
- Assignees: Bayer MaterialScience AG
- Inventors: Hartmut Nefzger; James-Michael Barnes; Manfred Schmidt; Jens Krause
- Web page: https://patentgrep.com/patent/US8273846B2

## 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 18/7678: {containing condensed aromatic rings}
- C08G: MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS

## Abstract

The present invention relates to high-quality polyurethane and polyurethane urea elastomers which exhibit unique combinations of processing characteristics, oxidation resistance, mechanical and mechanical/dynamic properties in particularly demanding applications. These polyurethane elastomers and polyurethane urea elastomers are based on novel polycarbonate polyols.

## Claims

### Claim 1

A polyurethane elastomer and/or polyurethane urea elastomer comprising the reaction product of
(I) NCO prepolymers having an NCO content of 3 to 15 wt. % and which comprise the reaction product of
(A) polycarbonate polyols having an OH number of 50 to 80 mg KOH/g and an average functionality of 1.9 to 2.2 which are obtained by reacting
(1) a mixture consisting essentially of
a) 15 wt. % to 85 wt. %, based on the mixture of a) and b), of one or more α,ω-alkanediols which have from 4 to 8 carbon atoms,
b) 15 wt. % to 85 wt. %, based on the mixture of a) and b), of a dodecanediol mixture which consists essentially of
(i) 30 to 50 wt. % of 1,12-dodecanediol,
(ii) 30 to 50 wt. % of undecandiol, and
(iii) 5-20 wt. % of one or more diols having from 6 to 10 carbon atoms, and
c) 0 to 10 wt. %, based on the total weight of the mixture of a), b) and c), of one or more alkanols having from 4 to 10 carbon atoms and hydroxyl functionalities of 1 or 3;
with
(2) a carbonyl component selected from the group consisting of diaryl carbonates, dialkyl carbonates and carbonyl chloride, and
(B) a polyisocyanate which is selected from the group consisting of 1,5-naphthalene diisocyanate, 2,4′-diphenylmethane diisocyanate, 4,4′-diphenylmethane diisocyanate, mixtures of 2,4′-diphenylmethane diisocyanate and 4,4′-diphenylmethane diisocyanate, carbodiimide-/uretonimine-modified diphenylmethane diisocyanate derivatives, polynuclear homologues of the diphenylmethane diisocyanate series, diisocyanatotoluenes, hexamethylene diisocyanate, isophorone diisocyanate and mixtures thereof, wherein (B) said polyisocyanate is present in a molar excess;
with
(II) a composition comprising:
(A′) one or more aliphatic diols having primary hydroxyl groups and number-average molecular weights of 62 to 202, and in amounts of 0 to 10 wt. %, based on the total weight of aliphatic diols, of one or more compounds selected from the group consisting of short-chain polyols with functionalities >2 to 4, higher-molecular-weight polyols with a functionality of 2 and polycarbonate polyols of (A), optionally, in the presence of water and/or further auxiliary substances and additives;
or
(B′) one or more aromatic diamine-type chain extenders selected from the group consisting of 4,4′-methylene-bis-(2-chloroaniline) (MBOCA), 3,3′,5,5′-tetraisopropyl-4,4′-diaminodiphenylmethane, 3,5-dimethyl-3′,5′-diisopropyl-4,4′-diaminophenylmethane, 3,5-diethyl-2,4-toluene diamine, 3,5-diethyl-2,6-toluene diamine (DETDA), 4,4′-methylene-bis-(3-chloro-2,6-diethylaniline), 3,5-dimethylthio-2,4-toluene diamine, 3,5-dimethylthio-2,6-toluene diamine, 3,5-diamino-4-chlorobenzoic acid isobutyl ester and mixtures thereof, optionally, in the presence of water and/or further auxiliary substances and additives.

### Claim 2

A process for the preparation of polyurethane elastomers and/or polyurethane urea elastomers, comprising reacting:
(I) NCO prepolymers having an NCO content of 3 to 15 wt. % and which comprise the reaction product of
(A) polycarbonate polyols having an OH number of 50 to 80 mg KOH/g and an average functionality of 1.9 to 2.2 which are obtained by reacting
(1) a mixture consisting essentially of
a) 15 wt. % to 85 wt. %, based on the mixture of a) and b), of one or more α,ω-alkanediols which have from 4 to 8 carbon atoms,
b) 15 wt. % to 85 wt. %, based on the mixture of a) and b), of a dodecanediol mixture which consists essentially of
(i) 30 to 50 wt. % of 1,12-dodecanediol,
(ii) 30 to 50 wt. % of undecandiol, and
(iii) 5-20 wt. % of one or more diols having from 6 to 10 carbon atoms, and
c) 0 to 10 wt. %, based on the total weight of the mixture of a), b) and c), of one or more alkanols having from 4 to 10 carbon atoms and hydroxyl functionalities of 1 or 3;
with
(2) a carbonyl component selected from the group consisting of diaryl carbonates, dialkyl carbonates and carbonyl chloride,
and
(B) a polyisocyanate which is selected from the group consisting of 1,5-naphthalene diisocyanate, 2,4′-diphenylmethane diisocyanate, 4,4′-diphenylmethane diisocyanate, mixtures of 2,4′-diphenylmethane diisocyanate and 4,4′-diphenylmethane diisocyanate, carbodiimide-/uretonimine-modified diphenylmethane diisocyanate derivatives, polynuclear homologues of the diphenylmethane diisocyanate series, diisocyanatotoluenes, hexamethylene diisocyanate, isophorone diisocyanate and mixtures thereof, wherein (B) said polyisocyanate is present in a molar excess;
with
(II) a composition comprising:
(A′) one or more aliphatic diols having primary hydroxyl groups and number-average molecular weights of 62 to 202, and in amounts of from 0 to 10 wt. %, based on the total weight of aliphatic diols, of one or more compounds selected from the group consisting of short-chain polyols with functionalities >2 to 4, higher-molecular-weight polyols with a functionality of 2 and polycarbonate polyols of (A), optionally, in the presence of water and/or further auxiliary substances and additives;
or
(B′) one or more aromatic diamine-type chain extenders selected from the group consisting of 4,4′-methylene-bis-(2-chloroaniline) (MBOCA), 3,3′,5,5′-tetraisopropyl-4,4′-diaminodiphenylmethane, 3,5-dimethyl-3′,5′-diisopropyl-4,4′-diaminophenylmethane, 3,5-diethyl-2,4-toluene diamine, 3,5-diethyl-2,6-toluene diamine (DETDA), 4,4′-methylene-bis-(3-chloro-2,6-diethylaniline), 3,5-dimethylthio-2,4-toluene diamine, 3,5-dimethylthio-2,6-toluene diamine, 3,5-diamino-4-chlorobenzoic acid isobutyl ester and mixtures thereof, optionally, in the presence of water and/or further auxiliary substances and additives.