# US 10,370,480 B2 · Aging-resistant polyurethane seal

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- Number: US 10,370,480 B2
- Document ID: US10370480B2
- Status: Granted
- Kind: B2
- Application number: 15/506,916
- Filed: 2015-07-29
- Published: 2017-09-14
- Granted: 2019-08-06
- Earliest claimed: 2014-08-28
- Assignees: BASF SE
- Applicants: BASF SE
- Inventors: Stefan Bokern; Pierre Coppens; Patrick Bolze; Thomas Mathieu; Carola Melloh
- Web page: https://patentgrep.com/patent/US10370480B2

## CPC

- C08G 18/6696: {with compounds of group C08G18/36 or hydroxylated esters of higher fatty acids of C08G18/38}
- C08G 18/165: {covered by C08G18/18 and C08G18/24}
- C08G 18/18: containing secondary or tertiary amines or salts thereof
- C08G 18/20: Heterocyclic amines; Salts thereof
- C08G 18/246: {containing also tin-carbon bonds}
- C08G 18/3275: {containing two hydroxy groups}
- C08G 18/341: {Dicarboxylic acids, esters of polycarboxylic acids containing two carboxylic acid groups}
- C08G 18/36: Hydroxylated esters of higher fatty acids
- C08G 18/4812: {Mixtures of polyetherdiols with polyetherpolyols having at least three hydroxy groups}
- C08G 18/482: {Mixtures of polyethers containing at least one polyether containing nitrogen}
- C08G 18/4829: {Polyethers containing at least three hydroxy groups (C08G18/4833 - C08G18/5096 take precedence)}
- C08G 18/4837: {and other oxyalkylene units}
- C08G 18/4845: {containing oxypropylene or higher oxyalkylene end groups}
- C08G 18/5024: {containing primary and/or secondary amino groups}
- C08G 18/722: {Combination of two or more aliphatic and/or cycloaliphatic polyisocyanates}
- C08G 18/755: {and at least one isocyanate or isothiocyanate group linked to a secondary carbon atom of the cycloaliphatic ring, e.g. isophorone diisocyanate}
- C08G 18/792: {formed by oligomerisation of aliphatic and/or cycloaliphatic isocyanates or isothiocyanates}
- C08G 2190/00: Compositions for sealing or packing joints
- C08G: MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS

## Abstract

The invention relates to a method for producing seals made of polyurethane, in which (a) aliphatic polyisocyanate, (b) compounds containing at least two isocyanate-reactive groups, (c) catalysts, (d) antioxidants and/or light stabilizers, and, optionally, (e) blowing agents, and (f) auxiliary agents and/or additives are mixed to form a reaction mixture, and the reaction mixture is allowed to complete the reaction to form polyurethane. The seal made of polyurethane has a Shore A hardness of less than 90 and a density of at least 850 g/L. The polymeric compounds having groups reactive toward isocyanate include b1) polyetherols having a functionality of 2 to 4 and a hydroxyl number of 20 to 100 mg KOH/g, b2) hydrophobic polyols having an OH number of less than 180 mg KOH/g and a functionality of greater than 2 to 3, and b3) chain extenders.

## Claims

### Claim 1

A process for the production of polyurethane gaskets, the process comprising:
mixing:
(a) aliphatic polyisocyanate,
(b) compounds having at least two groups reactive toward isocyanates,
(c) catalysts, and
at least one of antioxidants and light stabilizers
to give a reaction mixture, and
allowing completion of the reaction mixture to give the polyurethane,
wherein the Shore A hardness of the polyurethane gasket is less than 90, the density of the polyurethane gasket is at least 850 g/L, and the compounds having at least two groups reactive toward isocyanate comprise b1) polyetherols with functionality from 2 to 4 and with hydroxy number from 20 to 100 mg KOH/g, b2) hydrophobic polyols with OH number smaller than 180 mg KOH/g and with functionality from greater than 2 to 3, b3) chain extenders, and b5) a compound with molar mass from 800 to 6000 g/mol and with average functionality from 2 to 4 and, as groups having functionality toward isocyanate, functional groups selected from the group consisting of —NH2, —NH—, and —OH groups, wherein at least one of the functional group is an NH2 group.

### Claim 2 (depends on 1)

The process according to claim 1, wherein the aliphatic polyisocyanate (a) comprises a mixture of monomeric and trimeric isophorone diisocyanate.

### Claim 3 (depends on 1)

The process according to claim 1, wherein the hydroxy number of the polyetherol b1) is from 25 to 50 mg KOH/g.

### Claim 4 (depends on 1)

The process according to claim 1, wherein the polyetherol b1) has, as alkylene oxide, ethylene oxide units and propylene oxide units, wherein the proportion of ethylene oxide units, based on the total weight of alkylene oxide units in the polyether polyol b1), is smaller than 30% by weight, and the proportion of primary OH groups is greater than 70%, based on the number of OH groups in the polyether polyol b1).

### Claim 5 (depends on 1)

The process according to claim 1, wherein the hydrophobic polyol b2) comprises at least one of castor oil, dehydrated castor oil, and alkoxylation products of castor oil or of dehydrated castor oil.

### Claim 6 (depends on 1)

The process according to claim 1, wherein the hydrophobic polyol b2) comprises a partially dehydrated castor oil.

### Claim 7 (depends on 1)

The process according to claim 1, wherein the chain extender b3) has aliphatically bonded OH groups, and its molar mass is less than 160 g/mol.

### Claim 8 (depends on 1)

The process according to claim 1, wherein the compounds (b) having at least two groups reactive toward isocyanates further comprise, alongside the compounds b1) to b3), a compound b4) with molar mass smaller than 150 g/mol and with average functionality from 2 to 3 and, as groups having functionality toward isocyanate, functional groups selected from the group consisting of —NH2, —NH—, and —OH groups, wherein at least one of the functional groups is an —NH2 group or an —NH— group.

### Claim 9

A process for the production of polyurethane gaskets, the process comprising:
mixing:
(a) aliphatic polyisocyanate,
(b) compounds having at least two groups reactive toward isocyanates,
(c) catalysts, and
at least one of antioxidants and light stabilizers
to give a reaction mixture, and
allowing completion of the reaction mixture to give the polyurethane,
wherein the Shore A hardness of the polyurethane gasket is less than 90, the density of the polyurethane gasket is at least 850 g/L, and the compounds having at least two groups reactive toward isocyanate comprise b1) polyetherols with functionality from 2 to 4 and with hydroxy number from 20 to 100 mg KOH/g, b2) hydrophobic polyols with OH number smaller than 180 mg KOH/g and with functionality from greater than 2 to 3, b3) chain extenders, a compound b4) with molar mass smaller than 150 g/mol and with average functionality from 2 to 3 and, as groups having functionality toward isocyanate, functional groups selected from the group consisting of —NH2, —NH—, and —OH groups, wherein at least one of the functional groups is an —NH2 group or an —NH— group, and a compound b5) with molar mass from 800 to 6000 g/mol and with average functionality from 2 to 4 and, as groups having functionality toward isocyanate, functional groups selected from the group consisting of —NH2, —NH—, and —OH groups, wherein at least one of the functional group is an NH2 group.

### Claim 10 (depends on 9)

The process according to claim 9, wherein the compounds (b) having at least two groups reactive toward isocyanates further comprise, alongside the compounds b1) to b5), a compound b6) with molar mass smaller than 400 g/mol and with hydroxy functionality from 3 to 6.

### Claim 11 (depends on 1)

The process according to claim 1, wherein catalysts are exclusively amine catalysts.

### Claim 12 (depends on 10)

The process according to claim 10, wherein, based on the total weight of components b1) to b6), the proportion of component b1) is from 50 to 90% by weight, the proportion of component b2) is from 5 to 25% by weight, the proportion of component b3) is from 1 to 7% by weight, the proportion of component b4) is from 1 to 5% by weight, the proportion of component b5) is from 3 to 10% by weight, and the proportion of component b6) is from 0 to 5% by weight.

### Claim 13 (depends on 1)

The process according to claim 1, further comprising mixing
(e) blowing agents, and
(f) auxiliaries and/or additional substances
to give the reaction mixture.

### Claim 14 (depends on 1)

A polyurethane gasket obtainable by a process according claim 1.

### Claim 15 (depends on 13)

The process according to claim 13, wherein the ratio in which components (a) to (f) are mixed is such that the isocyanate index is from 90 to 120.