Process for producing elastomers

Patent metadata

Field	Value
Publication number	US-11312812-B2
Application number	US-201716341223-A
Country	US
Kind code	B2
Filing date	Oct 10, 2017
Priority date	Oct 12, 2016
Publication date	Apr 26, 2022
Grant date	Apr 26, 2022

Abstract

The present invention describes a process for producing an elastomer, preferably a polyurethane-containing elastomer, by reacting a polyol component (A) comprising at least one polyether carbonate polyol (A-1) containing carbon-carbon double bonds with a component (B) which is reactive with OH groups and contains at least one compound reactive toward OH groups, preferably an isocyanate component (B-1) containing NCO groups, in the presence of a free-radical initiator (C), preferably at least one peroxide (C-1), and optionally a catalyst (D), where the molar ratio of the OH-reactive groups of component (B) reactive with groups, to the OH groups of the polyol component (A) containing carbon-carbon double bonds, is greater than 1.0. It further relates to elastomers obtainable by such a process, preferably polyurethane elastomers, the use thereof, and two-component systems for production of elastomers, preferably polyurethane elastomers.

First claim

The invention claimed is:

1. A process for preparing an elastomer, comprising:
i) reacting (A) a polyol component comprising (A-1) at least one polyethercarbonate polyol containing carbon-carbon double bonds with (B) an OH group-reactive component containing at least one compound reactive toward OH groups, to give a reaction product, optionally in the presence of (D) a catalyst, and
ii) crosslinking the reaction product obtained in i), in the presence of (C) at least one free-radical initiator,
wherein the molar ratio of the OH-reactive groups in the OH group-reactive component (B) to the OH groups of the polyol component (A) containing carbon-carbon double bonds is greater than 1.0.

2. The process as claimed in claim 1 , wherein component (B) which comprises at least one compound reactive toward OH groups is (B-1) an isocyanate-containing component.

3. The process as claimed in claim 1 , wherein (C) the free-radical initiator comprises (C1) at least one peroxide initiator which comprises at least one of dibenzoyl peroxide, dilauroyl peroxide, acetylacetone peroxide, cyclohexanone peroxide, methyl ethyl ketone peroxide, methyl isobutyl ketone peroxide, cumene hydroperoxide, tert-butyl hydroperoxide, di(2-tert-butylperoxyisopropyl)benzene, tert-butyl cumyl peroxide, di-tert-amyl peroxide, di-tert-butyl peroxide, dicumyl peroxide, 2,5-dimethyl-2,5-di-(tert-butylperoxy)hexane, 1,1-di(tert-butylperoxy)-3,3,5-trimethylcyclohexane, 1,1-di(tert-butylperoxy)cyclohexane, 2,5-dimethyl-2,5-di(2-ethylhexanoylperoxy)-hexane, tert-butyl peroxybenzoate, tert-butyl peroxy-3,5,5-trimethylhexanoate, tert-butyl peroxy-2-ethylhexanoate, tert-butyl monoperoxymaleate, di(4-tert-butylcyclohexyl) peroxydicarbonate, tert-butyl peroxy-2-ethylhexylcarbonate, tert-butyl peroxyisopropylcarbonate, 1,3 1,4-bis(tert-butylperoxyisopropyl)benzene, t-butyl cumyl peroxide, 2,5-di(t-butylperoxy)-2,5-dimethylhexane, n-butyl 4,4′-di(t-butylperoxy)valerate, 1,1′-di(tert-butylperoxy)-3,3,5-trimethyl-cyclohexane, di(2,4-dichlorobenzoyl) peroxide, tert-butyl peroxybenzoate, butyl 4,4-di-(tert-butylperoxy)valerate, 2,5-dimethyl-2,5-di(tert-butylperoxy)-hex-3-yne, 2,2′-azodiisobutyronitrile, and di-tert-butyl peroxide.

4. The process as claimed in claim 1 , wherein (A-1) the polyethercarbonate polyol containing carbon-carbon double bonds has a content of carbon-carbon double bonds of 0.5% by weight to 17.0% by weight.

5. The process as claimed in claim 1 , wherein (A-1) the polyethercarbonate polyol containing carbon-carbon double bonds has a CO 2 content of 0.5% by weight to 50% by weight.

6. The process as claimed in claim 1 , wherein (A-1) the polyethercarbonate polyol containing carbon-carbon double bonds is obtained by addition of an alkylene oxide, at least one monomer containing carbon-carbon double bonds and CO 2 onto an H-functional starter compound in the presence of a double metal cyanide catalyst.

7. The process as claimed in claim 6 , wherein the monomer containing at least one carbon-carbon double bond comprises at least one of the monomers comprising
(a) allyl glycidyl ether, vinylcyclohexene oxide, cyclooctadiene monoepoxide, cyclododecatriene monoepoxide, butadiene monoepoxide, isoprene monoepoxide, limonene oxide, 1,4-divinylbenzene monoepoxide, 1,3-divinylbenzene monoepoxide, glycidyl esters of unsaturated fatty acids, partly epoxidized fats and oils and/or mixtures thereof;
(b) alkylene oxide with double bond of the general formula (IX):

wherein R 1 to R 3 are independently hydrogen, halogen, substituted C 1 -C 22 alkyl, unsubstituted C 1 -C 22 alkyl, substituted C 6 -C 12 aryl, or unsubstituted C 6 -C 12 aryl;
(c) cyclic anhydride which correspond to the formula (X), (XI) or (XII):

wherein R 1 to R 10 are independently hydrogen, halogen, substituted C 1 -C 22 alkyl, unsubstituted C 1 -C 22 alkyl, substituted C 6 -C 12 aryl, or unsubstituted C 6 -C 12 aryl; and
(d) 4-cyclohexene-1,2-dioic anhydride, 4-methyl-4-cyclohexene-1,2-dioic anhydride, 5,6-norbornene-2,3-dioic anhydride, allyl-5,6-norbornene-2,3-dioic anhydride, dodecenylsuccinic anhydride, tetradecenylsuccinic anhydride, hexadecenylsuccinic anhydride and octadecenylsuccinic anhydride.

8. The process as claimed in claim 7 , wherein the at least one monomer containing at least one carbon-carbon double bonds comprises at least one of
(a) allyl glycidyl ether, vinylcyclohexene oxide and limonene oxide,
(b) glycidyl acrylate and glycidyl methacrylate,
(c) maleic anhydride and itaconic anhydride, and
(d) 4-cyclohexene-1,2-dioic anhydride and 5,6-norbornene-2,3-dioic anhydride.

9. The process as claimed in claim 2 , wherein (B-1) the isocyanate-containing component comprises at least one of an aliphatic, a cycloaliphatic and/or an aromatic isocyanate.

10. The process as claimed in claim 1 , wherein, in step i), at least one catalyst (D) for the reaction of the polyol component (A) with an OH group-reactive compound (B), is added.

11. An elastomer obtained by the process as claimed in claim 1 .

12. Rubber, a sealing compound, a gasket, an adhesive, a varnish, or a shaped body which comprises the elastomer of claim 11 .

13. The process as claimed in claim 4 , wherein (A-1) the polyethercarbonate polyol containing carbon-carbon double bonds has a content of carbon-carbon double bonds of 1.0% by weight to 6.0% by weight.

14. The process as claimed in claim 5 , wherein (A-1) the polyethercarbonate polyol containing carbon-carbon double bonds has a CO 2 content of 5% by weight to 25% by weight.

15. The process as claimed in claim 1 , wherein the molar ratio of the OH-reactive groups in the OH group-reactive component (B) to the OH groups of the polyol component (A) containing carbon-carbon double bonds is 1.1 to less than 2.0.

16. The process as claimed in claim 1 , wherein the molar ratio of the OH-reactive groups in the OH group-reactive component (B) to the OH groups of the polyol component (A) containing carbon-carbon double bonds is 1.2 to 1.6.

Assignees

• Covestro Deutschland Ag

Inventors

• Norwig Jochen
• Marker Volker
• Langanke Jens
• Wolf Aurel
• Gürtler Christoph
• Wagner Philipp Nicholas
• Kessler Florian

Classifications

• C08G18/222

  metal compounds not provided for in groups C08G18/225 - C08G18/26 · CPC title

• C08G18/6705

  Unsaturated polymers not provided for in the groups C08G18/671, C08G18/6795, C08G18/68 or C08G18/69 · CPC title

• C08G18/6644

  having at least three hydroxy groups · CPC title

• C09D175/04

  Polyurethanes · CPC title

• C08G18/82 Primary

  Post-polymerisation treatment · CPC title