Compositions and methods for crosslinking polymers in the presence of atmospheric oxygen

Patent metadata

Field	Value
Publication number	US-2017267832-A1
Application number	US-201515531755-A
Country	US
Kind code	A1
Filing date	Dec 3, 2015
Priority date	Dec 9, 2014
Publication date	Sep 21, 2017
Grant date	—

Abstract

An organic peroxide formulation comprises at least one organic peroxide, at least one drying oil, and at least one free radical trap. A process comprises curing mixtures that include at least one elastomer and the organic peroxide formulation in the presence of oxygen. Elastomer compositions, methods of manufacturing elastomer articles, and elastomer articles made from the elastomer compositions are also disclosed.

First claim

1 . An organic peroxide formulation comprising:
A) at least one organic peroxide, B) at least one drying oil, and C) at least one free radical trap, wherein the amounts of the at least one organic peroxide, the at least one drying oil and the at least one free radical trap are selected such that the formulation is capable of curing an elastomer composition in the full or partial presence of oxygen.

2 . The formulation of claim 1 , wherein the at least one drying oil is selected from the group consisting of: tung oil, hemp oil, linseed oil, poppy oil, walnut oil, sunflower oil, cottonseed oil, corn oil, soybean oil, sardine oil, herring oil, safflower oil, flax seed oil, perilla oil, and a combination thereof.

3 . (canceled)

4 . (canceled)

5 . The formulation of claim 1 , wherein the at least one organic peroxide is selected from the group consisting of dialkyl peroxides, diperoxyketals, mono-peroxy carbonates, cyclic ketone peroxides, diacyl peroxides, organosulfonyl peroxides, peroxyesters and peroxydicarbonates.

6 . The formulation of claim 1 , wherein the at least one free radical trap is selected from the group consisting of nitroxides and quinones.

7 . The formulation of claim 1 , wherein the at least one free radical trap is selected from the group consisting of 4-hydroxy TEMPO and MTBHQ.

8 . The formulation of claim 1 , wherein the at least one drying oil comprises tung oil and the at least one free radical trap comprises MTBHQ.

9 . An elastomer composition comprising:
A) at least one elastomer, B) at least one organic peroxide, C) at least one drying oil, and D) at least one free radical trap, wherein the elastomer composition is curable in the full or partial presence of oxygen.

10 . (canceled)

11 . (canceled)

12 . (canceled)

13 . The elastomer composition of claim 9 , wherein the at least one elastomer is selected from the group consisting of ethylene-propylene-diene terpolymer (EPDM), fluoroelastomers (FKM, FFKM, FVMQ), vinyl silicone rubber (VMQ), nitrile rubber (NBR), acrylonitrile-butadiene-styrene (ABS), styrene-butadiene rubber (SBR), styrene-butadiene-styrene block copolymers (SBS), polybutadiene rubber (BR), styrene-isoprene-styrene block copolymers (SIS), partially hydrogenated acrylonitrile butadiene (HNBR), natural rubber (NR), synthetic polyisoprene rubber (IR), neoprene rubber (CR), polychloroprene, bromobutyl rubber (BIIR), chlorobutyl rubber, and combinations thereof.

14 . (canceled)

15 . The elastomer composition of claim 9 further comprising at least one polymer, wherein the polymer is selected from the group consisting of: ethylene-propylene copolymer (EPM), poly(ethylene α-olefins), poly(ethylene-octene), poly(ethylene-hexene), poly(ethylene-butylene), poly(ethylene-heptene), poly(ethylene-butene), poly(ethylene) (PE), high-density polyethylene (HDPE), linear low-density polyethylene (LLDPE), low-density polyethylene (LDPE), poly(ethylene-vinyl acetate) (EVA), poly(ethylene acrylate) elastomer (e.g., Vamac® DP), polysulfide rubber, chlorinated poly(ethylene) (CM or CPE), polyurethane (AU, EU), vinylidene fluoride copolymers (CFM), silicone rubber (PMQ), poly(ethylene methylacrylate) (ACM), chlorosulfonated poly(ethylene) (CSM), fluorosilicone rubber (FVMQ), fluoroelastomer (FKM), and a combination thereof.

16 . The elastomer composition of claim 9 , wherein the at least one drying oil is selected from the group consisting of: tung oil, hemp oil, linseed oil, poppy oil, walnut oil, sunflower oil, cottonseed oil, corn oil, soybean oil, sardine oil, herring oil, safflower oil, flax seed oil, perilla oil, and a combination thereof.

17 . The elastomer composition of claim 9 , wherein the at least one organic peroxide is selected from the group consisting of dialkyl peroxides, diperoxyketals, mono-peroxy carbonates, cyclic ketone peroxides, diacyl peroxides, organosulfonyl peroxides, peroxyesters and peroxydicarbonates.

18 . The elastomer composition of claim 9 , wherein the at least one free radical trap is selected from the group consisting of 4-hydroxy-TEMPO and MTBHQ.

19 . An elastomeric article comprising a cured elastomer composition of claim 9 .

20 . (canceled)

21 . (canceled)

22 . (canceled)

23 . (canceled)

24 . (canceled)

25 . (canceled)

26 . A process for curing the elastomer composition of claim 9 , the process comprising:
curing an elastomer composition in the presence of oxygen, wherein the elastomer composition comprises at least one elastomer, at least one organic peroxide, at least one drying oil, and at least one free radical trap.

27 . (canceled)

28 . (canceled)

29 . (canceled)

30 . (canceled)

31 . A cured elastomer composition prepared by the process of claim 26 .

32 . An organic peroxide formulation comprising:
A) at least one organic peroxide, B) at least one drying oil, and C) at least one crosslinking coagent, D) at least one free radical trap, wherein the amounts of the at least one organic peroxide, the at least one drying oil and the at least one free radical trap are selected such that the formulation is capable of curing an elastomer composition in the full or partial presence of oxygen.

33 . The organic peroxide formulation of claim 32 , wherein the crosslinking coagent has functionality is selected from the following group: dimethacrylates, trimethyacrlyates, poly methacrylates, methacrylates, diacrylates, triacrylates, polyacrylates, acrylates, allylic, maleimide, metallic coagents, zinc dimethacrylate and zinc diacrylate.

34 . An organic peroxide formulation comprising:
A) at least one organic peroxide, B) at least one drying oil, and C) at least one sulfur containing compound, D) at least one free radical trap, wherein the amounts of the at least one organic peroxide, the at least one drying oil and the at least one free radical trap are selected such that the formulation is capable of curing an elastomer composition in the full or partial presence of oxygen.

35 . (canceled)

36 . A composition comprising tung oil, MTBHQ, N′N′phenylene-bismaleimide, and at least one peroxide selected from the group consisting of 1,1-di(t-butylperoxy)-3,3,5-trimethyl cyclohexane, t-butylperoxybenzoate, t-butylperoxy-2-ethylhexylmonoperoxycarbonate, dicumyl peroxide, m/p-di(t-butylperoxy)diisopropylbenzene, 2,5-dimethyl-2,5-di(t-butylperoxy) hexane, and t-butylcumylperoxide, and optionally inert filler.

37 . (canceled)

38 . (canceled)

39 . (canceled)

40 . (canceled)

Assignees

• Arkema Inc

Inventors

• Pavlek William P
• Dluzneski Peter R
• Palys Leonard H
• Despotopoulou Marina

Classifications

• C08L23/16

  Ethylene-propylene or ethylene-propylene-diene copolymers · CPC title

• C08K3/04

  Carbon · CPC title

• B29C35/0805

  using electromagnetic radiation · CPC title

• C08K5/47

  Thiazoles · CPC title

• C08J2423/08

  Copolymers of ethene (C08J2423/16 takes precedence) · CPC title