Methods and compositions for curing a surface of an uncured polysulfide rubber

Patent metadata

Field	Value
Publication number	US-11292853-B2
Application number	US-202016797471-A
Country	US
Kind code	B2
Filing date	Feb 21, 2020
Priority date	Jul 20, 2017
Publication date	Apr 5, 2022
Grant date	Apr 5, 2022

Abstract

Disclosed are compositions comprising a liquid carrier, a polysulfide rubber curing agent, a metal cation, and an ionic liquid. Also disclosed are methods for curing a surface of an uncured polysulfide rubber. These methods involve applying the disclosed compositions to the surface of the uncured polysulfide rubber.

First claim

What is claimed is:

1. A method of curing a surface of an uncured polysulfide rubber, the method comprising contacting an uncured polysulfide rubber with a composition comprising a polysulfide rubber curing agent, a metal cation, an ionic liquid, and at least about 85% by weight of a liquid carrier based on the weight of the composition, wherein the liquid carrier is a C 1 -C 3 alcohol, fluorocarbon, aromatic hydrocarbon, hydrofluorocarbon, fluoroketone, or mixture thereof.

2. A method according to claim 1 , wherein the metal cation is Zn 2+ , Pb 2+ , Pb 4+ , Fe 2+ , Ca 2+ , Sb 2+ , Sb 5+ , As 3+ , As 5+ , Ba 2+ , Mn 4+ , Cr 3+ , Cu 2+ , Co 2+ , Mg 2+ , Se 4+ , or Te 4+ .

3. A method according to claim 1 , wherein the metal cation is Mg 2+ .

4. A method according to claim 1 , wherein the polysulfide rubber curing agent is a metal oxide, a metallic peroxide, an inorganic oxidizing agent, an organic oxidizing agent, a quinoid compound, a sulfur-containing compound, or mixture thereof.

5. A method according to claim 1 , wherein the polysulfide rubber curing agent is ZnO, PbO, FeO, CaO, Sb 2 O 3 , Sb 2 O 5 , As 2 O 3 , As 2 O 5 , BaO, Cr 2 O 3 , CuO, CoO, Pb 3 O 4 , MgO, ZnO 2 , PbO 2 , CaO 2 , MgO 2 , SeO 2 , TeO 2 , BaO 2 , NaBO 3 ·4H 2 O, MnO 2 , ZnCrO 4 , PbCrO 4 , K 2 CrO 4 , (NH 4 ) 2 Cr 2 O 7 , Na 2 CrO 4 , urea peroxide, t-butyl hydroperoxide, t-butyl perbenzoate, dinitrobenzene, trinitrobenzene, benzoyl peroxide, cumene hydroperoxide, stearoyl peroxide, lauroyl peroxide, methyl ethyl ketone peroxide, p-quinone dioxime, dimethylglyoxime, quinone, benzothiazyl disulfide, disulfiram, dinitrobenzene salt of mercaptobenzothiazole, mercaptobenzothiazole, or a mixture thereof.

6. A method according to claim 1 , wherein the composition comprises a mixture of ionic liquids.

7. A method according to any of claim 1 , wherein the ionic liquid has a melting point of from about −80° C. to about 200° C.

8. A method according to claim 1 , wherein the ionic liquid is
1,2,3-Trimethylimidazolium methyl sulfate;
1,2,3-Trimethylimidazolium trifluoromethanesulfonate;
1,2-Dimethyl-3-propylimidazolium bis(trifluoromethylsulfonyl)imide;
1,2-Dimethyl-3-propylimidazolium tris(trifluoromethylsulfonyl)methide;
1,3-Dimethylimidazolium methyl sulfate;
1-Allyl-3-methylimidazolium chloride;
1-Benzyl-3-methylimidazolium chloride;
1-Benzyl-3-methylimidazolium hexafluorophosphate;
1-Benzyl-3-methylimidazolium tetrafluoroborate;
1-Butyl-1-(3,3,4,4,5,5,6,6,7,7,8,8,8-tridecafluorooctyl)imidazolium hexafluorophosphate;
1-Butyl-1-methylpyrrolidinium bis(trifluoromethylsulfonyl)imide
1-Butyl-1-methylpyrrolidinium bromide;
1-Butyl-1-methylpyrrolidinium chloride;
1-Butyl-1-methylpyrrolidinium dicyanamide;
1-Butyl-1-methylpyrrolidinium tetrafluoroborate;
1-Butyl-2,3-dimethylimidazolium chloride;
1-Butyl-2,3-dimethylimidazolium hexafluorophosphate;
1-Butyl-2,3-dimethylimidazolium tetrafluoroborate;
1-Butyl-3-methylimidazolium 2-(2-methoxyethoxy)ethyl sulfate;
1-Butyl-3-methylimidazolium acetate;
1-Butyl-3-methylimidazolium bis(trifluoromethylsulfonyl)imide;
1-Butyl-3-methylimidazolium bromide;
1-Butyl-3-methylimidazolium chloride;
1-Butyl-3-methylimidazolium dicyanamide;
1-Butyl-3-methylimidazolium hexafluoroantimonate;
1-Butyl-3-methylimidazolium hexafluorophosphate
1-Butyl-3-methylimidazolium hydrogen sulfate;
1-Butyl-3-methylimidazolium methanesulfonate;
1-Butyl-3-methylimidazolium methyl sulfate;
1-Butyl-3-methylimidazolium nitrate;
1-Butyl-3-methylimidazolium octyl sulfate;
1-Butyl-3-methylimidazolium tetrachloroaluminate;
1-Butyl-3-methylimidazolium tetrafluoroborate;
1-Butyl-3-methylimidazolium thiocyanate;
1-Butyl-3-methylimidazolium tosylate;
1-Butyl-3-methylimidazolium trifluoromethanesulfonate;
1-Butyl-3-methylpyridinium bis(trifluoromethylsulfonyl)imide
1-Butyl-4-methylpyridinium bromide;
1-Butyl-4-methylpyridinium chloride;
1-Butyl-4-methylpyridinium hexafluorophosphate;
1-Butyl-4-methylpyridinium tetrafluoroborate;
1-Butylpyridinium bromide;
1-(3-Cyanopropyl)-3-methylimidazolium bis(trifluoromethylsulfonyl)amide;
1-(3-Cyanopropyl)-3-methylimidazolium chloride;
1-Dodecyl-3-methylimidazolium iodide;
1-Ethyl-2,3-dimethylimidazolium chloride;
1-Ethyl-2,3-dimethylimidazolium ethyl sulfate;
1-Ethyl-2,3-dimethylimidazolium trifluoromethanesulfonate;
1-Ethyl-3-methylimidazolium acetate;
1-Ethyl-3-methylimidazolium bis(pentafluoroethylsulfonyl)Imide;
1-Ethyl-3-methylimidazolium bis(trifluoromethylsulfonyl)Imide;
1-Ethyl-3-methylimidazolium bromide;
1-Ethyl-3-methylimidazolium chloride;
1-Ethyl-3-methylimidazolium dicyanamide;
1-Ethyl-3-methylimidazolium ethyl sulfate;
1-Ethyl-3-methylimidazolium hexafluorophosphate
1-Ethyl-3-methylimidazolium hydrogen sulfate;
1-Ethyl-3-methylimidazolium methanesulfonate;
1-Ethyl-3-methylimidazolium methyl sulfate;
1-Ethyl-3-methylimidazolium nitrate;
1-Ethyl-3-methylimidazolium tetrachloroaluminate;
1-Ethyl-3-methylimidazolium tetrafluoroborate;
1-Ethyl-3-methylimidazolium thiocyanate;
1-Ethyl-3-methylimidazolium tosylate;
1-Ethyl-3-methylimidazolium trifluoromethanesulfonate;
1-Ethyl-3-methylimidazolium 1,1,2,2-tetrafluoroethanesulfonate;
1-Hexyl-3-methylimidazolium chloride;
1-Hexyl-3-methylimidazolium hexafluorophosphate;
1-Hexyl-3-methylimidazolium tetrafluoroborate;
1-Hexyl-3-methylimidazolium trifluoromethanesulfonate;
1-Hexyl-3-methylimidazolium trifluoromethanesulfonate;
1-Methyl-3-(3,3,4,4,5,5,6,6,7,7,8,8,8-tridecafluorooctyl)imidazolium hexafluorophosphate;
1-Methyl-3-octylimidazolium chloride;
1-Methyl-3-octylimidazolium hexafluorophosphate;
1-Methyl-3-octylimidazolium tetrafluoroborate;
1-Methyl-3-octylimidazolium trifluoromethanesulfonate;
1-Methylimidazolium chloride;
1-Methylimidazolium hydrogen sulfate;
3-(Triphenylphosphonio)propane-1-sulfonate;
3-(Triphenylphosphonio)propane-1-sulfonic acid tosylate;
3-Methyl-1-propylpyridinium bis(trifluoromethylsulfonyl)imide;
4-(3-Butyl-1-imidazolio)-1-butanesulfonate;
4-(3-Butyl-1-imidazolio)-1-butanesulfonic acid triflate;
Methyl-trioctylammonium bis(trifluoromethylsulfonyl)imide;
Tetrabutylammonium benzoate;
Tetrabutylammonium bis(trifluoromethylsulfonyl)imide;
Tetrabutylammonium bromide;
Tetrabutylammonium chloride;
Tetrabutylammonium heptadecafluorooctanesulfonate
Tetrabutylammonium methanesulfonate;
Tetrabutylammonium nonafluorobutanesulfonate;
Tetrabutylphosphonium bromide;
Tetrabutylphosphonium chloride;
Tetrabutylphosphonium methanesulfonate;
Tetrabutylphosphonium p-toluenesulfonate;
Tetrabutylphosphonium tetrafluoroborate;
Tetraethylammonium trifluoroacetate;
Tetraethylammonium trifluoromethanesulfonate;
Tetraheptylammonium bromide;
Tetraheptylammonium chloride;
Tetrahexylammonium bromide;
Tetrahexylammonium iodide;
Tetrahexylammonium tetrafluoroborate;
Tetraoctylammonium bromide;
Tetraoctylammonium chloride;
Tetrapentylammonium bromide;
Tetrapentylammonium thiocyanate;
Tributylhexadecylphosphonium bromide;
Tributylmethylammonium methyl sulfate;
Triethylsulfonium bis(trifluoromethylsulfonyl)imide
Trihexyltetradecylphosphonium bis(2,4,4-trimethylpentyl)phosphinate;
Trihexyltetradecylphosphonium bis(trifluoromethylsulfonyl)amide;
Trihexyltetradecylphosphonium bromide;
Trihexyltetradecylphosphonium chloride;
Trihexyltetradecylphosphonium decanoate;
Trihexyltetradecylphosphonium dicyanamide;
Trihexyltetradecylphosphonium hexafluorophosphate;
Trihexyltetradecylphosphonium tetrafluoroborate;
Triisobutylmethylphosphonium tosylate;
Trioctylmethylammonium thiosalicylate;
α-Cyano-4-hydroxycinnamic acid butylamine salt; or
α-Cyano-4-hydroxycinnamic acid diethylamine salt.

9. A

Assignees

• Boeing Co

Inventors

• Flack Matthew Alexander
• Zweig Andrew M

Classifications

• C08J3/245 Primary

  Differential crosslinking of one polymer with one crosslinking type, e.g. surface crosslinking · CPC title

• C08J2381/04

  Polysulfides · CPC title

• C08K5/098

  Metal salts of carboxylic acids · CPC title

• C09K3/1012

  Sulfur-containing polymers, e.g. polysulfides · CPC title

• C08J2381/02

  Polythioethers; Polythioether-ethers · CPC title