Fluoroelastomer composition

Patent metadata

Field	Value
Publication number	US-11220588-B2
Application number	US-201615578126-A
Country	US
Kind code	B2
Filing date	May 30, 2016
Priority date	May 29, 2015
Publication date	Jan 11, 2022
Grant date	Jan 11, 2022

Abstract

The invention pertains to a (per)fluoroelastomer composition comprising at least one (per)fluoroelastomer comprising iodine and/or bromine atoms, at least one polyunsaturated compound, at least one organic peroxide and at least one organic compound selected from the group consisting of (thio)urea compounds, cyclic addition products of ammonia or primary amine and aldehyde; (thio)carbamates.

First claim

The invention claimed is:

1. A (per)fluoroelastomer composition comprising:
at least one (per)fluoroelastomer [fluoroelastomer (A)], said fluoroelastomer (A) comprising iodine and/or bromine atoms and having a backbone comprising:
recurring units derived from tetrafluoroethylene (TFE);
recurring units derived from at least one perfluorinated monomer selected from the group consisting of:
PAVE monomers, wherein the PAVE monomers are perfluoroalkylvinylethers complying with formula CF 2 ═CFOR f1 in which R f1 is a C 1 -C 6 perfluoroalkyl; and
MOVE monomers, wherein the MOVE monomers are perfluoro-oxyalkylvinylethers complying with formula CF 2 ═CFOX 0 , in which X 0 is (i) a C 1 -C 12 perfluorooxyalkyl having one or more ether groups; or (ii) a group of formula -CF 2 OR f2 in which R f2 is a C 1 -C 6 perfluoroalkyl;

optionally, recurring units derived from vinylidene fluoride (VDF) in an amount of up to 30% by moles, with respect to the total moles of recurring units;
optionally, recurring units derived from at least one perfluorinated C 3 -C 8 alpha- olefin, in an amount of up to 5% moles, with respect to the total moles of recurring units;
optionally, recurring units derived from at least one fluorine-free alpha-olefin, in an amount of up to 10% moles, with respect to the total moles of recurring units; and
optionally, recurring units derived from at least one bis-olefin [bis-olefin (OF)];

from 0.5 to 5 weight parts, per 100 parts by weight of said fluoroelastomer (A), of at least one polyunsaturated compound selected from the group consisting of bis-olefins of formulae (OF-1), (OF-2) and (OF-3):

wherein j is an integer between 2 and 10, and R 1 , R 2 , R 3 , R 4 , equal or different from each other, are H, F or C 1-5 alkyl or (per)fluoroalkyl-group;

wherein each of A, equal or different from each other and at each occurrence, is independently selected from F, Cl, and H; each of B, equal or different from each other and at each occurrence, is independently selected from F, Cl, H and OR B , wherein R B is a branched or straight chain alkyl radical which can be partially, substantially or completely fluorinated or chlorinated; E is a divalent group having 2 to 10 carbon atoms, optionally fluorinated, which may be inserted with ether linkages;

wherein E, A and B have the same meaning as above defined; R 5 , R 6 , R 7 , equal or different from each other, are H, F or C 1-5 alkyl or (per)fluoroalkyl group
from 0.1 to 3 weight parts, per 100 parts by weight of said fluoroelastomer (A), of at least one organic peroxide;
from 0.1 to 10 weight parts, per 100 parts by weight of said fluoroelastomer (A), of at least one organic compound [compound (C)] selected from the group consisting of:
urea compounds of formula (U):

wherein E is O, and each of R u , equal to or different from each other, is independently selected from the group consisting of hydrogen and C 1 -C 6 hydrocarbon groups;
cyclic addition products of ammonia or primary amine and aldehyde; and
carbamates of formula (C):

wherein E is oxygen; R b is a C 1 -C 36 hydrocarbon group, and R e is H or a C 1 -C 6 alkyl group.

2. The (per)fluoroelastomer composition of claim 1 , wherein the polyunsaturated compound is present in the composition in an amount of at least 1 weight parts per 100 parts by weight of fluoroelastomer (A) and in an amount of less than 5 weight parts per 100 parts by weight of fluoroelastomer (A).

3. The (per)fluoroelastomer composition of claim 2 , wherein the polyunsaturated compound is present in the composition in an amount of at least 1.2 weight parts per 100 parts by weight of fluoroelastomer (A) and/or in an amount of less than 4 weight parts per 100 parts by weight of fluoroelastomer (A).

4. The (per)fluoroelastomer composition of claim 3 , wherein the polyunsaturated compound is present in the composition in an amount of less than 3 weight parts per 100 parts by weight of fluoroelastomer (A).

5. The (per)fluoroelastomer composition of claim 1 , wherein fluoroelastomer (A) is selected from those having a backbone comprising:
recurring units derived from TFE in an amount of 30 to 70% moles;
recurring units derived from at least one perfluorinated monomer selected from the group consisting of PAVE monomers and MOVE monomers, in an amount of 25 to 40% moles;
optionally, recurring units derived from VDF in an amount of 1 to 25% moles;
optionally, recurring units derived from ethylene (E) in an amount from 0 to 5% moles;
optionally, recurring units derived from hexafluoropropylene (HFP) in an amount from 0 to 5% moles; and
optionally, recurring units derived from at least one bis-olefin (OF).

6. The (per)fluoroelastomer composition of claim 5 , wherein fluoroelastomer (A) is selected from the group consisting of fluoroelastomers having any of the following monomer compositions (in mol %):
(i) tetrafluoroethylene (TFE) 50-80%, perfluoroalkyl vinyl ethers (PAVE) 20-50%, bis- olefin (OF) 0-5%;
(ii) tetrafluoroethylene (TFE) 20-70%, perfluoro-oxyalkylvinylether (MOVE) 30- 80%, perfluoroalkyl vinyl ethers (PAVE) 0-50%, bis-olefin (OF) 0-5%;
(iii) tetrafluoroethylene (TFE) 40-70%, perfluoroalkyl vinyl ethers (PAVE) 20-50%, vinylidene fluoride (VDF): 10-30%; bis-olefin (OF): 0-5%; hexafluoropropylene (HFP): 0-5%; and
(iv) tetrafluoroethylene (TFE) 40-69%, perfluoroalkyl vinyl ethers (PAVE) 20-49%, vinylidene fluoride (VDF): 10-30%; ethylene (E): 1-5%; bis-olefin (OF) 0-5%; hexafluoropropylene (HFP): 0-5%.

7. The (per)fluoroelastomer composition of claim 1 , wherein the organic peroxide is selected from the group consisting of dialkyl peroxides.

8. The (per)fluoroelastomer composition of claim 7 , wherein dialkyl peroxides are selected from di-tert-butyl peroxide, 2,5-dimethyl-2,5-bis(tert-butylperoxy)hexane, bis(1,1-diethylpropyl)peroxide, bis(1-ethyl -1-methylpropyl)peroxide, 1,1-diethylpropyl-1-ethy1-1-methylpropyl-peroxide, 2,5- dimethyl-2,5-bis(tert-amylperoxy)hexane; dicumyl peroxide; dibenzoyl peroxide; di-tert-butyl perbenzoate; and bis[1,3-dimethyl-3-(tert-butylperoxy)butyl] carbonate.

9. The (per)fluoroelastomer composition of claim 1 , wherein the amount of the organic peroxide is at least 0.5 weight parts per 100 parts by weight of fluoroelastomer (A) and less than 3 weight parts per 100 parts by weight of fluoroelastomer (A).

10. The (per)fluoroelastomer composition of claim 9 , wherein the amount of the organic peroxide is at least 0.8 weight parts per 100 parts by weight of fluoroelastomer (A) and/or less than 2.5 weight parts per 100 parts by weight of fluoroelastomer (A).

11. The (per)fluoroelastomer composition of claim 10 , wherein the amount of the organic peroxide is at less than 2 weight parts per 100 parts by weight of fluoroelastomer (A).

12. The (per)fluoroelastomer composition of claim 1 , wherein said urea compounds are selected from the group consisting of:
(i-A) ureas of formula (U-2):

wherein E′ is O; and/or
wherein said cyclic addi

Assignees

• Solvay Specialty Polymers It

Inventors

• Fantoni Matteo
• Avataneo Marco
• Bossolo Stefano

Classifications

• C08K5/3495

  condensed with carbocyclic rings · CPC title

• C08K5/405

  Thioureas; Derivatives thereof · CPC title

• C08K5/3492

  Triazines · CPC title

• C08K5/205

  Compounds containing [IMAGE cpc-sch-C08K-1010.gif] groups, e.g. carbamates · CPC title

• C08K5/0025 Primary

  Crosslinking or vulcanising agents; including accelerators · CPC title