Process for the production of water and solvent-free nitrile rubbers

Patent metadata

Field	Value
Publication number	US-10858455-B2
Application number	US-201615254407-A
Country	US
Kind code	B2
Filing date	Sep 1, 2016
Priority date	Mar 25, 2010
Publication date	Dec 8, 2020
Grant date	Dec 8, 2020

Abstract

The present invention relates to specific water and solvent-free nitrile rubbers having specific functional groups and/or end groups, a process for the production thereof and the use thereof.

First claim

What is claimed is:

1. A nitrile rubber comprising:
(i) repeating units derived from:
at least one conjugated diene, and
at least one α,β-unsaturated nitrile, and

(ii) one or more structural element of the general formulae (I), (II), (III), (IV) or (V)

wherein:
Z represents H, branched or unbranched, saturated or one or more times unsaturated alkyl, saturated or one or more times unsaturated carbo- or heterocyclic residue, aryl, heteroaryl, heteroarylalkyl, alkoxy, aryloxy, heteroaryloxy, amino, amido, hydroxyimino, carbamoyl, akoxycarbonyl, F, CI, Br, I, hydroxy, phosphonato, phosphinato, alkylthio, arylthio, sulfanyl, sulfinyl, sulfono, sulfino, sulfeno, sulfonyl, sulfamoyl, silyl, silyloxy, nitril, carbonyl, carboxy, oxycarbonyl, oxysulfonyl, oxo, thioxo, borate, selenate, epoxy, cyanate, thiocyanate, isocyanate, thioisocyanate or isocyanide,
M represents repeating units derived from one or more monomers which are one or more times unsaturated, including conjugated or unconjugated dienes, alkynes and vinyl compounds, or a structural element derived from polymers comprising polyether, and polyalkylenoxides, polysiloxanes, polyols, polycarbonates, polyurethanes, polyisocyanates, polysaccharides, polyester or polyamides,
n and m are the same or different and are 0 to 10,000,
t is 0 or 1, if n=0, and equals 1, if n≠0,
X represents C(Z 2 ), N(Z), P(Z), P(═O)(Z), O, S, S(═O) or S(═O) 2 wherein Z has the same meaning as defined hereinabove,
R (a) in case that m≠0 has the same meaning as the residue Z, and
(b) in case that m=0, represents H, a branched or unbranched, saturated, one or more times unsaturated alkyl, a saturated, one or more times unsaturated carbo- or heterocyclic residue, aryl, heteroaryl, heteroarylalkyl, alkoxy, aryloxy, heteroaryloxy, amino, amido, carbamoyl, alkoxy, aryloxy, alkylthio, arylthio, sulfanyl, sulfinyl, sulfono, sulfino, sulfeno, sulfonyl, sulfamoyl, carbonyl, carboxy, oxycarbonyl, oxysulfonyl, oxo, thioxo, epoxy, cyanate, thiocyanate, isocyanate, thiosocyanate or isocyanide, and

the nitrile rubber has a combined content of water and volatile organic compounds of less than 1.25 wt %, wherein the content of water is less than 0.5 wt %, and the content of volatile organic compounds is less than 0.75 wt %, based on the mass of the nitrile rubber,
wherein the general structural elements (ii) comprise:

where
Z has the same meaning as in the general formula (I), and
R has the same meaning as in the general formula (II) for m=0, and
R and Z are alike or different, albeit in each case with the proviso that R and Z following homolytic fission of their bond to the respectively adjacent atom in the nitrile rubber each form a secondary, tertiary or aromatically stabilized radical.

2. The nitrile rubber pursuant to claim 1 , wherein the combined content of water and volatile organic compounds in the nitrile rubber is less than 0.75 wt %, wherein the content of water is less than 0.25 wt %, and the content of volatile organic compounds is less than 0.50 wt %, based on the mass of the nitrile rubber.

3. The nitrile rubber pursuant to claim 1 , wherein the combined content of water and volatile organic compounds in the nitrile rubber is less than 0.5 wt %, wherein the content of water is less than 0.1 wt %, and the content of volatile organic compounds is less than 0.4 wt %, based on the mass of the nitrile rubber.

4. The nitrile rubber pursuant to claim 1 , wherein the combined content of water and volatile organic compounds in the nitrile rubber is less than 0.2 wt %, wherein the content of water is less than 0.075 wt %, and the content of volatile organic compounds is less than 0.125 wt %, based on the mass of the nitrile rubber.

5. The nitrile rubber pursuant to claim 1 , wherein the repeating units are derived from at least one conjugated diene, at least one α,β-unsaturated nitrile, and one or more copolymerizable monomers.

6. The nitrile rubber pursuant to claim 1 , wherein:
the at least one conjugated diene comprises C 4 -C 6 conjugated diene; and
the at least one α,β-unsaturated nitrile comprises C 3 -C 5 α,β-unsaturated nitrile.

7. The nitrile rubber pursuant to claim 1 , wherein:
the at least one conjugated diene comprises 1,2-butadiene, 1,3-butadiene, isoprene, 2,3-dimethylbutadiene, piperylene or mixtures thereof; and
the at least one α,β-unsaturated nitrile comprises acrylonitrile, methacrylonitrile, ethacrylonitrile or mixtures thereof.

8. The nitrile rubber pursuant to claim 7 , wherein the repeating units further comprise one or more copolymerizable monomers selected from the group consisting of aromatic vinylmonomers, fluorine-containing vinyl monomers, copolymerizable anti-ageing monomers, non-conjugated dienes and alkynes, and copolymerizable monomers containing carboxyl groups.

9. The nitrile rubber pursuant to claim 8 , wherein the copolymerizable monomers are selected from the group consisting of styrene, α-methylstyrene, vinylpyridine, fluoroethyl vinyl ether, fluoropropyl vinyl ether, o-fluoromethylstyrene, vinyl pentafluorobenzoate, difluoroethylene, tetrafluoroethylene, N-(4-anilinophenyl)acrylamide, N-(4-anilinophenyl)methacrylamide, N-(4-anilinophenyl)cinnamides, N-(4-anilinophenyl)crotonamide, N-phenyl-4-(3-vinylbenzyloxy)aniline, N-phenyl-4-(4-vinylbenzyloxy)aniline, 4-cyanocyclohexene, 4-vinylcyclohexene, 1-butyne, 2-butyne, and copolymerizable monomers containing α,β-unsaturated monocarboxylic acids, their esters, α,β-unsaturated dicarboxylic acids, their monoesters or diesters, or their corresponding anhydrides or amides.

Assignees

• Arlanxeo Deutschland Gmbh

Inventors

• Paul Hanns-Ingolf
• Wagner Paul
• Feller Rolf
• Kirchhoff Jorg
• Lovegrove John
• Forner Florian
• Klimpel Michael
• Weuta Peter
• Brandau Sven

Classifications

• C08F236/12

  with nitriles · CPC title

• C08C2/00

  Treatment of rubber solutions · CPC title

• C08F6/10

  Removal of volatile materials, e.g. solvents {(C08F6/001, C08F6/003, C08F6/005, C08F6/006, C08F6/008, C08F6/02, C08F6/04 take precedence)} · CPC title

• C08C1/12 Primary

  by evaporation · CPC title

• C08L9/02

  Copolymers with acrylonitrile · CPC title