Method for producing a multiple bond-containing prepolymer as elastomer precursor

Patent metadata

Field	Value
Publication number	US-11098153-B2
Application number	US-201716341219-A
Country	US
Kind code	B2
Filing date	Oct 10, 2017
Priority date	Oct 12, 2016
Publication date	Aug 24, 2021
Grant date	Aug 24, 2021

Abstract

The present invention relates to a method for producing a prepolymer that contains carbon-carbon multiple bonds, a polyol component A) being reacted with component B) that contains isocyanate groups and the polyol component comprising a polyether carbonate polyol that contains carbon-carbon multiple bonds.

First claim

The invention claimed is:

1. A process for preparing a prepolymer containing carbon-carbon multiple bonds, comprising reacting a polyol component A which comprises a polyethercarbonate polyol containing carbon-carbon multiple bonds, with an isocyanate-containing component B which comprises at least one polyisocyanate B1 having an average molar NCO functionality of 2.0 to 2.2 and at least one polyisocyanate B2 having an average molar NCO functionality of 2.8 to 3.2,
and the content of carbon-carbon multiple bonds in the polyethercarbonate polyol is from 0.5% by weight to 17.0% by weight.

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

3. The process as claimed in claim 1 , wherein the polyethercarbonate polyol containing carbon-carbon multiple bonds has a carbon dioxide content of 3% by weight to 50% by weight.

4. The process as claimed in claim 2 , wherein the monomer containing at least one carbon-carbon multiple 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 , R2 and R 3 are each independently hydrogen, halogen, substituted C1-C22 alkyl, unsubstituted C1-C22 alkyl, substituted C6-C12 aryl, or unsubstituted C6-C12 aryl
(c) cyclic anhydrides which correspond to the general formula (X), (XI) or (XII):

wherein R 1 to R 10 are each independently hydrogen, halogen, substituted C1-C22 alkyl, unsubstituted C1-C22 alkyl, or substituted C6-C12 aryl, or unsubstituted C6-C12 aryl,
(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
and
(e) alkylene oxides with substituents having carbon-carbon triple bonds.

5. The process as claimed in claim 4 , wherein the at least one monomer containing at least one carbon-carbon multiple bond 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,
(d) 4-cyclohexene-1,2-dioic anhydride and 5,6-norbornene-2,3-dioic anhydride
and
(e) glycidyl propargyl ether.

6. The process as claimed in claim 1 , wherein the isocyanate-containing component B comprises at least 2 polyisocyanates selected from hexamethylene diisocyanate, diphenylmethane diisocyanate, toluene diisocyanate, the trimerization or higher oligomerization products thereof, and adducts thereof.

7. The process as claimed in claim 1 , wherein the polyisocyanates B1 and B2 comprise a mixture of a diisocyanate monomer and a diisocyanate trimer.

8. The process as claimed in claim 1 , wherein an NCO index in the preparation of the prepolymer is 0.95 to 1.20.

9. A prepolymer containing carbon-carbon multiple bonds, obtainable by a process as claimed in claim 1 .

10. A prepolymer as claimed in claim 9 having a content of carbon-carbon multiple bonds 0.5% by weight of to 15.0% by weight.

11. A process for producing an elastomer, comprising the steps of:
a-1) providing a prepolymer as claimed in claim 9 ,
and
b-1) crosslinking the prepolymer.

12. A process for producing an elastomer, comprising the steps of:
a-2) providing a prepolymer prepared by a process as claimed in claim 1 ,
and
b-2) crosslinking the prepolymer.

13. An elastomer obtainable by a process as claimed in claim claim 12 .

14. The process as claimed in claim 1 , wherein said polyol component A comprises a polyethercarbonate polyol containing carbon-carbon double bonds.

15. The process as claimed in claim 1 , wherein said isocyanate-containing compound B has an average molar functionality of from 2.40 to 2.80.

16. The process as claimed in claim 3 , wherein the polyethercarbonate polyol containing carbon-carbon multiple bonds has a carbon dioxide content of 5 to 25% by weight.

17. The prepolymer as claimed in claim 9 , wherein the carbon-carbon multiple bonds are carbon-carbon double bonds.

18. The prepolymer as claimed in claim 10 having a content of carbon-carbon multiple bonds of 1.0% by weight to 6.0% by weight.

19. The prepolymer as claimed in claim 10 having a content of carbon-carbon multiple bonds of 1.5% by weight to 3.0% by weight.

20. The process as claimed in claim 7 , wherein the diisocyanate monomer comprises diphenylmethane diisocyanate and/or toluene diisocyanate, and the diisocyanate trimer comprises a hexamethylene diisocyanate based trimer.

Assignees

• Covestro Deutschland Ag

Inventors

• Subhani Muhammad Afzal
• Koehler Burkhard
• Leitner Walter
• Müller Thomas Ernst
• Gürtler Christoph

Classifications

• C08G64/34

  and cyclic ethers · CPC title

• C08G18/792

  formed by oligomerisation of aliphatic and/or cycloaliphatic isocyanates or isothiocyanates · CPC title

• C08G18/64

  Macromolecular compounds not provided for by groups C08G18/42 - C08G18/63 · CPC title

• C08G18/12 Primary

  using two or more compounds having active hydrogen in the first polymerisation step · CPC title

• C08G18/7621

  being toluene diisocyanate including isomer mixtures · CPC title