Readily process-able, oil-resistant thermoplastic vulcanizates

Patent metadata

Field	Value
Publication number	US-12258471-B2
Application number	US-202117374395-A
Country	US
Kind code	B2
Filing date	Jul 13, 2021
Priority date	Dec 21, 2020
Publication date	Mar 25, 2025
Grant date	Mar 25, 2025

Abstract

Disclosed are thermoplastic vulcanizates comprising a plastic phase and a rubber phase and process for preparing such thermoplastic vulcanizates, wherein the plastic phase comprises a thermoplastic polymer and the rubber phase comprises a carboxylated nitrile rubber.

First claim

What is claimed is:

1. A thermoplastic vulcanizate comprising a plastic phase and a rubber phase, wherein
a) the plastic phase comprises from about 35 parts to about 60 parts by weight, based on 100 parts by weight of the plastic and rubber phases, of a plastic having a melting point of about 160° C. to about 260° C., wherein the plastic is a semi-crystalline engineering polyester,
b) the rubber phase comprises from about 65 parts to about 40 parts, by weight based on 100 parts by weight of the plastic and rubber phases, of a carboxylated nitrile rubber having reactive carboxylate groups; and
c) crosslinks the vulcanizate comprises formed by a reaction between an addition type curing agent and the reactive carboxylate groups in the carboxylated nitrile rubber, wherein the addition type curing agent is a compound comprising more than one oxazoline group.

2. A thermoplastic vulcanizate according to claim 1 , wherein the addition type curing agent is 2,2′-(1,3-phenylene)bis(2-oxazoline), or 2,2′-(1,4-phenylene)bis(2-oxazoline), or 2,2′-(2,6-pyridylene)bis(2-oxazoline), or mixtures thereof.

3. A thermoplastic vulcanizate according to claim 1 , wherein the addition type curing agent is 2,2′-(1,3-phenylene)bis(2-oxazoline).

4. A thermoplastic vulcanizate according to claim 1 , wherein the addition type curing agent is 2,2′-(1,3-phenylene)bis(2-oxazoline) and the curing agent is present in an amount of about 1 to about 4 parts by weight for every 100 parts by weight of the carboxylated nitrile rubber and the plastic.

5. A thermoplastic vulcanizate according to claim 4 , wherein the plastic phase comprises from about 50 parts to about 55 parts by weight, based on 100 parts by weight of the plastic and rubber phases, of the plastic, and the rubber phase comprises from about 50 parts to about 45 parts, by weight based on 100 parts by weight of the plastic and rubber phases, of the a carboxylated nitrile rubber.

6. A thermoplastic vulcanizate according to claim 5 , wherein the addition type curing agent is 2,2′-(1,3-phenylene)bis(2-oxazoline) and the curing agent is present in an amounts of about 2 to about 3 parts by weight for every 100 parts by weight of the carboxylated nitrile rubber and the plastic.

7. A thermoplastic vulcanizate according to claim 6 , wherein the plastic is a Poly(butylene terephthalate having a melting point of in the range of about 220° C. to about 230° C.

8. A thermoplastic vulcanizate according to claim 7 , comprising a polyethylene glycol ester plasticizer.

9. A thermoplastic vulcanizate according to claim 5 , wherein the addition type curing agent is 2,2′-(1,3-phenylene)bis(2-oxazoline) and the curing agent is present in an amounts of about 3 to about 5 parts by weight for every 100 parts by weight of the carboxylated nitrile rubber and the plastic.

10. A thermoplastic vulcanizate according to claim 9 , wherein the plastic is a Poly(butylene terephthalate having a melting point of in the range of about 220° C. to about 230° C.

11. A thermoplastic vulcanizate according to claim 10 , comprising a polyethylene glycol ester plasticizer.

12. A thermoplastic vulcanizate according to claim 5 , wherein
the plastic phase comprises from about 50 parts to about 55 parts by weight, based on 100 parts by weight of the plastic and rubber phases, of the plastic which is a Poly(butylene terephthalate having a melting point of in the range of about 220° C. to about 230° C.,
the rubber phase comprises from about 50 parts to about 45 parts, by weight based on 100 parts by weight of the plastic and rubber phases, of the a carboxylated nitrile rubber; and the thermoplastic vulcanizate further comprises
from 6 parts to 18 parts based on 100 parts by weight of the plastic and rubber phases of a polyethylene glycol ester plasticizer.

13. A thermoplastic vulcanizate comprising a plastic phase and a rubber phase, wherein
a) the plastic phase comprises from about 70 parts to about 80 parts by weight, based on 100 parts by weight of the plastic and rubber phases, of a plastic having a melting point of about 160° C. to about 260° C., wherein the plastic is a semi-crystalline engineering polyester, and
b) the rubber phase comprises from about 30 parts to about 20 parts, by weight based on 100 parts by weight of the plastic and rubber phases, of a carboxylated nitrile rubber having reactive carboxylate groups; and
c) the vulcanizate comprises crosslinks formed by a reaction between an addition type curing agent and the reactive carboxylate groups in the carboxylated nitrile rubber, wherein the addition type curing agent is a compound comprising more than one oxazoline group.

14. A thermoplastic vulcanizate according to claim 13 , wherein the addition type curing agent is 2,2′-(1,3-phenylene)bis(2-oxazoline) and the curing agent is present in an amounts of about 1 to about 5 parts by weight for every 100 parts by weight of the carboxylated nitrile rubber and the plastic.

15. A thermoplastic vulcanizate according to claim 14 , wherein the plastic is a Poly(butylene terephthalate having a melting point of in the range of about 220° C. to about 230° C.

16. A thermoplastic vulcanizate according to claim 15 , comprising a polyethylene glycol ester plasticizer.

17. A thermoplastic vulcanizate according to claim 13 , wherein the addition type curing agent is 2,2′-(1,3-phenylene)bis(2-oxazoline) and the curing agent is present in an amounts of about 2 to about 5 parts by weight for every 100 parts by weight of the carboxylated nitrile rubber and the plastic.

18. A thermoplastic vulcanizate according to claim 17 , wherein the plastic is a Poly(butylene terephthalate having a melting point of in the range of about 220° C. to about 230° C.

19. A thermoplastic vulcanizate according to claim 18 , comprising a polyethylene glycol ester plasticizer.

20. A thermoplastic vulcanizate according to claim 13 , wherein the thermoplastic vulcanizate further comprises
from 6 parts to 18 parts based on 100 parts by weight of the plastic and rubber phases of a polyethylene glycol ester plasticizer.

Assignees

• Parker Hannifin Corp

Inventors

• Abraham Tonson
• Jindal Aditya
• Mallamaci Michael P
• Wilson Taylor L

Classifications

• C08L2312/00

  Crosslinking · CPC title

• C08L2207/04

  Thermoplastic elastomer · CPC title

• C08L67/03

  the dicarboxylic acids and dihydroxy compounds having the carboxyl- and the hydroxy groups directly linked to aromatic rings · CPC title

• C08L13/00

  Compositions of rubbers containing carboxyl groups · CPC title

• B29K2105/0038

  Plasticisers · CPC title