IP Library Granted Patent US 8,273,846
Granted Patent B2
US 8,273,846 · App. 12/168,957 · Granted Sep 25, 2012

Polyurethane and polyurethane urea elastomers based on polycarbonate polyols

Assignee: Bayer MaterialScience AG
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Quick Facts
Patent No.
US 8,273,846
App. No.
12/168,957
Granted
Sep 25, 2012
Kind
B2
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 (37)

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.

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.

Assignments (2)
CHANGE OF NAME Recorded Mar 30, 2016
From: BAYER MATERIALSCIENCE AG
To: COVESTRO DEUTSCHLAND AG
Reel/Frame 038399/0469 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jul 8, 2008
From: NEFZGER, HARTMUT, DR.; BARNES, JAMES-MICHAEL; SCHMIDT, MANFRED, DR.; KRAUSE, JENS, DR.
To: BAYER MATERIALSCIENCE AG
Reel/Frame 021202/0610 →
Priority Claims (1)
DE 10 2007 032 343 · Jul 11, 2007 · national
Continuity (1)
Related Publication 20090018256A1 · Jan 15, 2009