Butyl rubber containing allylic alcohol

Patent metadata

Field	Value
Publication number	US-10822439-B2
Application number	US-201616063327-A
Country	US
Kind code	B2
Filing date	Dec 14, 2016
Priority date	Dec 17, 2015
Publication date	Nov 3, 2020
Grant date	Nov 3, 2020

Abstract

A process for producing an allylic alcohol functionalized butyl rubber involves contacting an epoxidized butyl rubber with benzoic acid, an analogue of benzoic acid or a C1-C7 alkanoic acid. The process and a polymer compound comprising the epoxidized butyl rubber and the benzoic acid, analogue of benzoic acid or a C1-C7 alkanoic acid provide a cost effective route to a polar functionalized butyl rubber, particularly to butyl rubber comprising allylic alcohol functional groups.

First claim

What is claimed is:

1. A process for producing an allylic alcohol functionalized butyl rubber, the process comprising contacting an epoxidized butyl rubber with benzoic acid, an analogue of benzoic acid or a C 1 -C 7 alkanoic acid in an absence of a solvent, wherein the benzoic acid or analogue of benzoic acid is a compound of formula (I):

where R 1 , R 2 , R 3 , R 4 and R 5 are independently hydrogen, methyl, ethyl, phenyl, chloro or bromo.

2. The process according to claim 1 , wherein the epoxidized butyl rubber is contacted with the benzoic acid or analogue of benzoic acid wherein the benzoic acid.

3. The process according to claim 1 , wherein the benzoic acid or analogue of benzoic acid comprises meta-chlorobenzoic acid.

4. The process according to claim 1 , wherein the epoxidized butyl rubber is contacted with the C 1 -C 7 alkanoic acid.

5. The process according to claim 4 , wherein the C 1 -C 7 alkanoic acid is a compound of formula (II):

where R 6 is hydrogen, methyl, ethyl, propyl, butyl, pentyl or hexyl.

6. The process according to claim 1 , wherein the allylic alcohol functionalized butyl rubber is produced from the epoxidized butyl rubber and the acid at a temperature of about 95° C. or greater.

7. The process according to claim 1 , wherein the epoxidized butyl rubber is contacted with the acid for an amount of time of about 10 minutes or greater.

8. The process according to claim 1 , wherein:
the benzoic acid or analogue of benzoic acid comprises meta-chlorobenzoic acid;
the C 1 -C 7 alkanoic acid is a compound of formula (II):

where R 6 is hydrogen, methyl, ethyl, propyl, butyl, pentyl or hexyl; and

the epoxidized butyl rubber comprises an isoolefin copolymer comprising repeating units derived from at least one isoolefin monomer and repeating units derived from at least one multiolefin monomer.

9. The process according to claim 8 , wherein:
the isoolefin monomer comprises isobutene and/or wherein the at least one multiolefin monomer comprises isoprene;
the butyl rubber is a non-halogenated butyl rubber;
the contacting is done at a temperature of about 140° C. to about 180° C., and for a period of time of about 10 minutes or greater.

10. The process according to claim 8 , wherein:
the isoolefin monomer comprises isobutene and/or wherein the at least one multiolefin monomer comprises isoprene;
the butyl rubber is a halogenated butyl rubber;
the contacting is done at a temperature of about 140° C. to about 180° C., and for a period of time of about 10 minutes or greater.

11. A process for producing an allylic alcohol functionalized butyl rubber, the process comprising:
epoxidizing a butyl rubber with peroxybenzoic acid, an analogue of peroxybenzoic acid or a C 1 -C 7 peroxyalkanoic acid in an absence of a solvent to form a polymer compound comprising the epoxidized butyl rubber and the benzoic acid, analogue of benzoic acid or C 1 -C 7 alkanoic acid, and
producing allylic alcohol functionalized butyl rubber in situ from the epoxidized butyl rubber and the benzoic acid, analogue of benzoic acid or C 1 -C 7 alkanoic acid,

wherein the peroxybenzoic acid or analogue of peroxybenzoic acid is a compound of formula (III):

where R 1 , R 2 , R 3 , R 4 and R 5 are independently hydrogen, methyl, ethyl, phenyl, chloro or bromo; and the benzoic acid or analogue of benzoic acid is a compound of formula (I):

where R 1 , R 2 , R 3 , R 4 and R 5 are independently hydrogen, methyl, ethyl, phenyl, chloro or bromo.

12. The process according to claim 11 , wherein the butyl rubber is a non-halogenated butyl rubber.

13. The process according to claim 11 , wherein the butyl rubber comprises an isoolefin copolymer comprising repeating units derived from at least one isoolefin monomer and repeating units derived from at least one multiolefin monomer.

14. The process according to claim 13 , wherein the isoolefin monomer comprises isobutene and/or wherein the at least one multiolefin monomer comprises isoprene.

15. The process according to claim 11 , wherein:
the butyl rubber is a non-halogenated; and
the butyl rubber comprises an isoolefin copolymer comprising repeating units derived from at least one isoolefin monomer and repeating units derived from at least one multiolefin monomer.

16. The process according to claim 15 , wherein the isoolefin monomer comprises isobutene and/or wherein the at least one multiolefin monomer comprises isoprene.

17. The process according to claim 11 , wherein:
the butyl rubber is a halogenated butyl rubber; and
optionally wherein the butyl rubber comprises an isoolefin copolymer comprising repeating units derived from at least one isoolefin monomer and repeating units derived from at least one multiolefin monomer.

18. A polymer compound comprising:
an epoxidized butyl rubber; and
an acid selected from benzoic acid or an analogue of benzoic acid, wherein the benzoic acid or analogue of benzoic acid is a compound of formula (I):

where R 1 , R 2 , R 3 , R 4 and R 5 are independently hydrogen, methyl, ethyl, phenyl, chloro or bromo.

19. The polymer compound according to claim 18 , wherein: the benzoic acid or analogue of benzoic acid comprises meta-chlorobenzoic acid.

20. The polymer compound according to any one of claim 18 produced by mixing the butyl rubber and the benzoic acid or the analogue of benzoic acid in an absence of solvent.

Assignees

• Arlanxeo Singapore Pte Ltd

Inventors

• Elliott Sarah
• Davidson Gregory J E
• Guo Sharon

Classifications

• C08L23/30

  by oxidation · CPC title

• C08L23/283

  Iso-olefin halogenated homopolymers or copolymers · CPC title

• C08L23/22

  Copolymers of isobutene; Butyl rubber; Homopolymers or copolymers of other iso-olefins · CPC title

• C08L9/00

  Compositions of homopolymers or copolymers of conjugated diene hydrocarbons · CPC title

• C08K5/14

  Peroxides · CPC title