US20080116645A1 - Solventless liquid isoprene compounds - Google Patents
Solventless liquid isoprene compounds Download PDFInfo
- Publication number
- US20080116645A1 US20080116645A1 US12/021,001 US2100108A US2008116645A1 US 20080116645 A1 US20080116645 A1 US 20080116645A1 US 2100108 A US2100108 A US 2100108A US 2008116645 A1 US2008116645 A1 US 2008116645A1
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- Prior art keywords
- gasket
- sealing member
- compound
- curing
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- Prior art date
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- 239000007788 liquid Substances 0.000 title claims abstract description 46
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical class CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 title claims abstract description 17
- 150000001875 compounds Chemical class 0.000 claims abstract description 71
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 29
- 229920003049 isoprene rubber Polymers 0.000 claims abstract description 24
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims abstract description 15
- 229910052717 sulfur Inorganic materials 0.000 claims abstract description 15
- 239000011593 sulfur Substances 0.000 claims abstract description 15
- -1 isoprene compound Chemical class 0.000 claims abstract description 11
- 239000002904 solvent Substances 0.000 claims abstract description 9
- 238000000034 method Methods 0.000 claims description 20
- 238000007789 sealing Methods 0.000 claims description 20
- 238000013023 gasketing Methods 0.000 claims description 15
- 238000001746 injection moulding Methods 0.000 claims description 14
- 238000001721 transfer moulding Methods 0.000 claims description 14
- 229920001971 elastomer Polymers 0.000 claims description 12
- 239000000463 material Substances 0.000 claims description 9
- 239000005060 rubber Substances 0.000 claims description 8
- 239000007787 solid Substances 0.000 claims description 6
- 150000002978 peroxides Chemical group 0.000 claims description 5
- 230000009969 flowable effect Effects 0.000 claims description 4
- 241001441571 Hiodontidae Species 0.000 claims description 3
- 239000000203 mixture Substances 0.000 claims description 2
- 238000007493 shaping process Methods 0.000 claims 4
- 239000012778 molding material Substances 0.000 claims 2
- 229920001195 polyisoprene Polymers 0.000 claims 1
- 229920000642 polymer Polymers 0.000 claims 1
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 12
- 239000000126 substance Substances 0.000 description 8
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 7
- DMWVYCCGCQPJEA-UHFFFAOYSA-N 2,5-bis(tert-butylperoxy)-2,5-dimethylhexane Chemical compound CC(C)(C)OOC(C)(C)CCC(C)(C)OOC(C)(C)C DMWVYCCGCQPJEA-UHFFFAOYSA-N 0.000 description 6
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 6
- 239000011787 zinc oxide Substances 0.000 description 6
- 239000000945 filler Substances 0.000 description 5
- 239000010734 process oil Substances 0.000 description 5
- 239000003963 antioxidant agent Substances 0.000 description 4
- 239000000806 elastomer Substances 0.000 description 4
- 239000004615 ingredient Substances 0.000 description 4
- 239000002184 metal Substances 0.000 description 4
- 229910052751 metal Inorganic materials 0.000 description 4
- 239000003921 oil Substances 0.000 description 4
- 235000019198 oils Nutrition 0.000 description 4
- 229920001296 polysiloxane Polymers 0.000 description 4
- 239000012190 activator Substances 0.000 description 3
- 239000003086 colorant Substances 0.000 description 3
- 238000013329 compounding Methods 0.000 description 3
- 239000012530 fluid Substances 0.000 description 3
- 239000004033 plastic Substances 0.000 description 3
- 229920003023 plastic Polymers 0.000 description 3
- 239000004014 plasticizer Substances 0.000 description 3
- 239000000377 silicon dioxide Substances 0.000 description 3
- KOMNUTZXSVSERR-UHFFFAOYSA-N 1,3,5-tris(prop-2-enyl)-1,3,5-triazinane-2,4,6-trione Chemical compound C=CCN1C(=O)N(CC=C)C(=O)N(CC=C)C1=O KOMNUTZXSVSERR-UHFFFAOYSA-N 0.000 description 2
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 2
- BWGNESOTFCXPMA-UHFFFAOYSA-N Dihydrogen disulfide Chemical compound SS BWGNESOTFCXPMA-UHFFFAOYSA-N 0.000 description 2
- 235000021355 Stearic acid Nutrition 0.000 description 2
- DAKWPKUUDNSNPN-UHFFFAOYSA-N Trimethylolpropane triacrylate Chemical compound C=CC(=O)OCC(CC)(COC(=O)C=C)COC(=O)C=C DAKWPKUUDNSNPN-UHFFFAOYSA-N 0.000 description 2
- OKKRPWIIYQTPQF-UHFFFAOYSA-N Trimethylolpropane trimethacrylate Chemical compound CC(=C)C(=O)OCC(CC)(COC(=O)C(C)=C)COC(=O)C(C)=C OKKRPWIIYQTPQF-UHFFFAOYSA-N 0.000 description 2
- 230000003078 antioxidant effect Effects 0.000 description 2
- 230000008901 benefit Effects 0.000 description 2
- 239000007767 bonding agent Substances 0.000 description 2
- 239000006229 carbon black Substances 0.000 description 2
- 239000011248 coating agent Substances 0.000 description 2
- 238000000576 coating method Methods 0.000 description 2
- 238000004132 cross linking Methods 0.000 description 2
- AFZSMODLJJCVPP-UHFFFAOYSA-N dibenzothiazol-2-yl disulfide Chemical compound C1=CC=C2SC(SSC=3SC4=CC=CC=C4N=3)=NC2=C1 AFZSMODLJJCVPP-UHFFFAOYSA-N 0.000 description 2
- DMBHHRLKUKUOEG-UHFFFAOYSA-N diphenylamine Chemical compound C=1C=CC=CC=1NC1=CC=CC=C1 DMBHHRLKUKUOEG-UHFFFAOYSA-N 0.000 description 2
- 239000003623 enhancer Substances 0.000 description 2
- FWDBOZPQNFPOLF-UHFFFAOYSA-N ethenyl(triethoxy)silane Chemical compound CCO[Si](OCC)(OCC)C=C FWDBOZPQNFPOLF-UHFFFAOYSA-N 0.000 description 2
- VKYKSIONXSXAKP-UHFFFAOYSA-N hexamethylenetetramine Chemical compound C1N(C2)CN3CN1CN2C3 VKYKSIONXSXAKP-UHFFFAOYSA-N 0.000 description 2
- 229910044991 metal oxide Inorganic materials 0.000 description 2
- 150000004706 metal oxides Chemical class 0.000 description 2
- OFHMODDLBXETIK-UHFFFAOYSA-N methyl 2,3-dichloropropanoate Chemical compound COC(=O)C(Cl)CCl OFHMODDLBXETIK-UHFFFAOYSA-N 0.000 description 2
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 2
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 2
- 239000003208 petroleum Substances 0.000 description 2
- 239000000049 pigment Substances 0.000 description 2
- 239000008117 stearic acid Substances 0.000 description 2
- KUAZQDVKQLNFPE-UHFFFAOYSA-N thiram Chemical compound CN(C)C(=S)SSC(=S)N(C)C KUAZQDVKQLNFPE-UHFFFAOYSA-N 0.000 description 2
- 229960002447 thiram Drugs 0.000 description 2
- YXIWHUQXZSMYRE-UHFFFAOYSA-N 1,3-benzothiazole-2-thiol Chemical class C1=CC=C2SC(S)=NC2=C1 YXIWHUQXZSMYRE-UHFFFAOYSA-N 0.000 description 1
- 241000239290 Araneae Species 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 239000006057 Non-nutritive feed additive Substances 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- 239000003125 aqueous solvent Substances 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 239000011324 bead Substances 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 230000005540 biological transmission Effects 0.000 description 1
- 239000001055 blue pigment Substances 0.000 description 1
- 239000004927 clay Substances 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- UEZWYKZHXASYJN-UHFFFAOYSA-N cyclohexylthiophthalimide Chemical compound O=C1C2=CC=CC=C2C(=O)N1SC1CCCCC1 UEZWYKZHXASYJN-UHFFFAOYSA-N 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- 239000012990 dithiocarbamate Substances 0.000 description 1
- 150000004659 dithiocarbamates Chemical class 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 239000004744 fabric Substances 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 239000012847 fine chemical Substances 0.000 description 1
- 239000003517 fume Substances 0.000 description 1
- 229910021485 fumed silica Inorganic materials 0.000 description 1
- 239000012208 gear oil Substances 0.000 description 1
- 150000002357 guanidines Chemical class 0.000 description 1
- 239000012760 heat stabilizer Substances 0.000 description 1
- 235000010299 hexamethylene tetramine Nutrition 0.000 description 1
- 239000004312 hexamethylene tetramine Substances 0.000 description 1
- 229920001519 homopolymer Polymers 0.000 description 1
- 230000002209 hydrophobic effect Effects 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 239000001023 inorganic pigment Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 239000010705 motor oil Substances 0.000 description 1
- 238000000465 moulding Methods 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 238000012856 packing Methods 0.000 description 1
- 239000010690 paraffinic oil Substances 0.000 description 1
- AQSJGOWTSHOLKH-UHFFFAOYSA-N phosphite(3-) Chemical class [O-]P([O-])[O-] AQSJGOWTSHOLKH-UHFFFAOYSA-N 0.000 description 1
- 150000004714 phosphonium salts Chemical class 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 235000013824 polyphenols Nutrition 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 description 1
- 230000029058 respiratory gaseous exchange Effects 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 238000007650 screen-printing Methods 0.000 description 1
- 150000003335 secondary amines Chemical class 0.000 description 1
- QAZLUNIWYYOJPC-UHFFFAOYSA-M sulfenamide Chemical compound [Cl-].COC1=C(C)C=[N+]2C3=NC4=CC=C(OC)C=C4N3SCC2=C1C QAZLUNIWYYOJPC-UHFFFAOYSA-M 0.000 description 1
- 229940096522 trimethylolpropane triacrylate Drugs 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L9/00—Compositions of homopolymers or copolymers of conjugated diene hydrocarbons
Definitions
- This invention relates in general to elastomeric compositions, and in particular to compounds made with a liquid isoprene rubber.
- Liquid isoprene rubbers are conventionally used in a minor amount as a plasticizer or processing aid in combination with a solid elastomer in preparing a rubber compound. It has not previously been thought to use a liquid isoprene rubber as the base elastomer for making a compound, and then to cure the liquid isoprene rubber.
- Rubber compounds are conventionally made by mixing the elastomer(s) and other chemicals together in an organic solvent, or in an aqueous solvent to prepare an emulsion. It has not previously been thought to prepare a liquid isoprene rubber compound without the use of a solvent, and there has been no suggestion how to prepare the compound in a solventless process. Such a process is contrary to the conventional thinking.
- this invention relates to a solventless liquid isoprene compound.
- the compound includes a liquid isoprene rubber.
- the compound also includes a curing agent selected from sulfur and/or sulfur donors.
- the curing agent is present in an amount of at least about 3% by weight of the compound.
- the compound contains substantially no solvent.
- this invention relates to a solventless liquid isoprene compound.
- the compound includes a liquid isoprene rubber.
- the compound also includes a nonsulfur curing agent.
- the curing agent is present in an amount of at least about 5% by weight of the compound.
- the compound contains substantially no solvent.
- liquid isoprene compounds of the invention use liquid isoprene rubbers as the base material for the compounds. Surprisingly, the compounds are made with substantially no solvent, e.g., not more than about 2% solvent. It has been discovered that liquid isoprene compounds having excellent properties can be made without solvent by using an increased amount of curing agent compared to conventional methods.
- the solventless liquid isoprene compounds of the invention contain a liquid isoprene rubber, a curing agent, and optionally other curing chemicals and other compounding ingredients as described below.
- the liquid isoprene rubber can be any suitable type of liquid isoprene-containing rubber.
- One nonlimiting example is Claprene® L-1R-30, L-1R-50 or L-1R-503 manufactured by Kuraray Co., Ltd., Kashima, Japan.
- the liquid isoprene rubber is present in an amount between about 40% and about 97% weight of the compound.
- a solid isoprene rubber having a Mooney value of not more than about 75 it may be desirable to add to the compound a solid isoprene rubber having a Mooney value of not more than about 75.
- a low Mooney isoprene rubber can be added to improve the physical properties of the liquid isoprene rubber without substantial loss in its flowability and processability.
- the amount of the solid isoprene rubber is not more than about 49% by weight of the total rubber.
- the curing agent can be any type suitable for curing the liquid isoprene rubber.
- Some typical curing agents include sulfur, sulfur donors, and nonsulfur curing agents such as peroxides, metal oxides, difunctional resins, and amines.
- Sulfur donors include sulfur-containing chemicals such as tetramethylthiuram disulfide (TMTD), dipentamethylenethiuram hexasulfide (DPTH), bis(2,2′-benzothiazolyl)disulfide or benzothiazyldisulfide (MBTS), and dimorpholinyl disulfide (DTDM).
- TMTD tetramethylthiuram disulfide
- DPTH dipentamethylenethiuram hexasulfide
- MBTS bis(2,2′-benzothiazolyl)disulfide
- DTDM dimorpholinyl disulfide
- Any suitable type of sulfur can be used.
- a nonlimiting example of a suitable sulfur is Spider® brand sulfur manufactured by C. P. Hall, Chicago, Ill.
- peroxide curing agent Any suitable type of peroxide curing agent can be used.
- peroxide curing agents are Varox® DBPH-50, a 50% 2,5-dimethyl-2,5-di(t-butyl-peroxyl) hexane manufactured by R.T. Vanderbilt Co., Norwalk, Conn.; Vul-Cup® 40KE manufactured by Hercules, Inc., Wilmington, Deleware; Cadox® TS-50 manufactured by Akzo Chemical, Chicago, Ill.; and MEK (methyl ethyl ketone) peroxides.
- the liquid isoprene compounds contain an increased amount of curing agent compared to conventional rubber compounds.
- the curing agent is a sulfur and/or a sulfur donor
- the curing agent is usually present in an amount of at least about 3% by weight of the compound, and preferably between about 3% and about 10%.
- the curing agent is a nonsulfur curing agent
- the curing agent is usually present in an amount of at least about 5% by weight of the compound, and preferably between about 5% and about 12%.
- the compounds can also optionally include other curing chemicals, such as activators, crosslinking enhancers, accelerators, and/or retarders. Any suitable type of activator can be used. Some nonlimiting examples of activators are zinc oxide, stearic acid, combinations of zinc oxide and stearic acid, other metal oxides, other fatty acids, and phosphonium salts.
- crosslinking enhancer can be used.
- TAIC triallyl isocyanurate
- Ricon® 152 a homopolymer of butadiene (MW 2,900), which is manufactured by Sartomer, Exton, Pa.
- SR-351 trimethylol propane triacrylate, manufactured by Sartomer, Exton, Pa.
- B5405 which is 75% SR-350 (trimethylol propane trimethacrylate) and 25% inert filler acting as a carrier.
- any suitable type of accelerator can be used.
- accelerators are hexamethylenetetramine, mercaptobenzothiazoles, sulfenamides, thiurams, dithiocarbamates, and guanidines.
- any suitable type of retarder can optionally be used.
- Some nonlimiting examples of retarders are organic acids and anhydrides, cyclohexylthiophthalimide, and sulfenamide.
- the compounds can also optionally include other compounding ingredients, such as fillers, bonding agents, antidegradants, process oils, plasticizers, coloring agents, or other desirable ingredients.
- suitable type of filler can be used.
- Some typical fillers are carbon black, silica, and clay.
- Nonlimiting examples of suitable fillers include Sterling® 6630 carbon black, manufactured by Cabot Corporation, Alpharetta, Ga.; FK140 or FK160 silica manufactured by Degussa AG, Dusseldorf, Germany; and CAB-O-SIL® TS-530, a hydrophobic fumed silica, manufactured by Cabot Corp.
- bonding agents useful in the compounds are resorcinol (1,3-dihydroxybenzene); and A-151, a vinyl triethoxy silane, which is manufactured by Huayuan Fine Chemicals, Wuhan, China.
- antioxidants any suitable type of antidegradant can be used, such as antioxidants, antiozonants, and heat stabilizers.
- Some typical antioxidants are secondary amines, phenolics, and phosphites.
- a nonlimiting example of a suitable antioxidant is Naugard® 445 antioxidant, which is a 4,4′-di(alpha, alpha-dimethyl-benzyl)diphenylamine, manufactured by Uniroyal Chemical Co., Waterbury, Conn.
- process oil can be used, such as petroleum oils or vegetable oils.
- process oils include Sunpar® 2280 paraffinic oil, manufactured by Nippon Sun Oil K.K., Japan; and Chevron ParaLux® Process Oil 6001R, a highly saturated white paraffinic process oil with very low aromatic content, manufactured by ChevronTexaco Corp., San Ramon, Calif.
- plasticizer can be used, such as petroleum oils.
- a coloring agent can be added to the compounds.
- coloring agents are man-made mineral pigments such as the Geode® series (e.g., Geode® V-11633 Kelly Green); and the NEOLOR® series of inorganic pigments (e.g., NEOLOR® Red S), both manufactured by Ferro Corp., Cleveland, Ohio.
- the solventless liquid isoprene compounds can be processed in any suitable manner.
- the chemicals are mixed together using any suitable mixing equipment, such as planetary mixers (e.g., Ross mixers), internal mixers, two-roll mills, open roll mills or the like.
- the mixed compound is then applied, pressed, or molded depending on the particular use.
- the compound is cured using any suitable time and temperature profile.
- the compound is cured at a temperature between about 300° F. and about 400° F. for a time between about 3 minutes and about 20 minutes.
- the compound can be further post cured if desired or necessary, e.g., for 2 to 14 days at 70° F. to 400° F.
- the compounds of the invention can be used in many different applications.
- the compounds are flowable so that they can take the place of materials such as liquid silicones in many applications.
- the compounds have a viscosity not more than about 50% greater than that of liquid silicones, more preferably not more than about 25% greater, and most preferably not more than about 10% greater.
- the compounds are impermeable to fluids, so their use is beneficial in applications where it is desired to limit the flow of fluids, such as in engine seals to limit the flow of VOC's through the engine.
- the compounds are also easier to process than liquid silicones.
- the flowability of the compounds allows them to be applied instead of molded, which can save the costs typically associated with molding.
- the compounds can also be molded if desired, and their use is not limited to flowable applications.
- sealing members e.g., gaskets, O-rings, packings or the like
- sealing members e.g., gaskets, O-rings, packings or the like
- the compounds can be used for cure in place gasketing (CIPG), inject in place gasketing (IJPG), and form in place gasketing (FIPG). They can be applied robotically thereby resulting in a dispensed sealing bead.
- the compounds are suitable for making thin seals such as thin layered gaskets, and for making intricate seals and gaskets. They can be used to fill intricate channels in a metal plate.
- a thin gasket can be injection molded onto a plastic or metal carrier.
- the compounds can be used in liquid injection molding (LIM), transfer molding (TM), injection molding.
- LIM liquid injection molding
- TM transfer molding
- injection molding injection molding
- the compounds can be used to make rubber-coated metal (RCM) products and rubber-coated plastic products.
- RCM rubber-coated metal
- the compounds cure and bond well to the metal and plastic.
- the compounds can be used as a screen printing material. Because of their low viscosity, lower pressures are required during the forming process which allows for complicated manufacturing using pressure sensitive material as an integral part of the forming process.
- the compounds can be used as a fabric coating in many different applications, e.g., as a coating on airbags or interior portions of airplanes.
- the compounds can be used as a repair material, e.g., to fill in little holes in bumpers.
- the compounds are solventless, they can be easily applied by workers without the hazards of breathing in fumes.
- the compounds can be applied by any suitable method.
- the compounds can be applied and will cure at room temperature.
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- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Paints Or Removers (AREA)
Abstract
In one embodiment, this invention relates to a solventless liquid isoprene compound. The compound includes a liquid isoprene rubber. The compound also includes a curing agent selected from sulfur and/or sulfur donors. The curing agent is present in an amount of at least about 3% by weight of the compound. The compound contains substantially no solvent. In another embodiment, this invention relates to a solventless liquid isoprene compound. The compound includes a liquid isoprene rubber. The compound also includes a nonsulfur curing agent. The curing agent is present in an amount of at least about 5% by weight of the compound. The compound contains substantially no solvent.
Description
- This application claims the benefit of U.S. provisional application Ser. No. 60/342,239, filed Dec. 21, 2001.
- This invention relates in general to elastomeric compositions, and in particular to compounds made with a liquid isoprene rubber.
- Liquid isoprene rubbers are conventionally used in a minor amount as a plasticizer or processing aid in combination with a solid elastomer in preparing a rubber compound. It has not previously been thought to use a liquid isoprene rubber as the base elastomer for making a compound, and then to cure the liquid isoprene rubber.
- Rubber compounds are conventionally made by mixing the elastomer(s) and other chemicals together in an organic solvent, or in an aqueous solvent to prepare an emulsion. It has not previously been thought to prepare a liquid isoprene rubber compound without the use of a solvent, and there has been no suggestion how to prepare the compound in a solventless process. Such a process is contrary to the conventional thinking.
- In one embodiment, this invention relates to a solventless liquid isoprene compound. The compound includes a liquid isoprene rubber. The compound also includes a curing agent selected from sulfur and/or sulfur donors. The curing agent is present in an amount of at least about 3% by weight of the compound. The compound contains substantially no solvent.
- In another embodiment, this invention relates to a solventless liquid isoprene compound. The compound includes a liquid isoprene rubber. The compound also includes a nonsulfur curing agent. The curing agent is present in an amount of at least about 5% by weight of the compound. The compound contains substantially no solvent.
- Various objects and advantages of this invention will become apparent to those skilled in the art from the following detailed description of the preferred embodiment.
- The liquid isoprene compounds of the invention use liquid isoprene rubbers as the base material for the compounds. Surprisingly, the compounds are made with substantially no solvent, e.g., not more than about 2% solvent. It has been discovered that liquid isoprene compounds having excellent properties can be made without solvent by using an increased amount of curing agent compared to conventional methods.
- The solventless liquid isoprene compounds of the invention contain a liquid isoprene rubber, a curing agent, and optionally other curing chemicals and other compounding ingredients as described below.
- The Liquid Isoprene Rubber
- The liquid isoprene rubber can be any suitable type of liquid isoprene-containing rubber. One nonlimiting example is Claprene® L-1R-30, L-1R-50 or L-1R-503 manufactured by Kuraray Co., Ltd., Kashima, Japan. Preferably, the liquid isoprene rubber is present in an amount between about 40% and about 97% weight of the compound.
- Optional Solid Elastomer
- In some applications, it may be desirable to add to the compound a solid isoprene rubber having a Mooney value of not more than about 75. A low Mooney isoprene rubber can be added to improve the physical properties of the liquid isoprene rubber without substantial loss in its flowability and processability. Preferably, the amount of the solid isoprene rubber is not more than about 49% by weight of the total rubber.
- The Curing Agent
- The curing agent (vulcanizing agent) can be any type suitable for curing the liquid isoprene rubber. Some typical curing agents include sulfur, sulfur donors, and nonsulfur curing agents such as peroxides, metal oxides, difunctional resins, and amines. Sulfur donors include sulfur-containing chemicals such as tetramethylthiuram disulfide (TMTD), dipentamethylenethiuram hexasulfide (DPTH), bis(2,2′-benzothiazolyl)disulfide or benzothiazyldisulfide (MBTS), and dimorpholinyl disulfide (DTDM).
- Any suitable type of sulfur can be used. A nonlimiting example of a suitable sulfur is Spider® brand sulfur manufactured by C. P. Hall, Chicago, Ill.
- Any suitable type of peroxide curing agent can be used. Some nonlimiting is examples of peroxide curing agents are Varox® DBPH-50, a 50% 2,5-dimethyl-2,5-di(t-butyl-peroxyl) hexane manufactured by R.T. Vanderbilt Co., Norwalk, Conn.; Vul-Cup® 40KE manufactured by Hercules, Inc., Wilmington, Deleware; Cadox® TS-50 manufactured by Akzo Chemical, Chicago, Ill.; and MEK (methyl ethyl ketone) peroxides.
- The liquid isoprene compounds contain an increased amount of curing agent compared to conventional rubber compounds. When the curing agent is a sulfur and/or a sulfur donor, the curing agent is usually present in an amount of at least about 3% by weight of the compound, and preferably between about 3% and about 10%. When the curing agent is a nonsulfur curing agent, the curing agent is usually present in an amount of at least about 5% by weight of the compound, and preferably between about 5% and about 12%.
- Other Curing Chemicals
- The compounds can also optionally include other curing chemicals, such as activators, crosslinking enhancers, accelerators, and/or retarders. Any suitable type of activator can be used. Some nonlimiting examples of activators are zinc oxide, stearic acid, combinations of zinc oxide and stearic acid, other metal oxides, other fatty acids, and phosphonium salts.
- Any suitable type of crosslinking enhancer can be used. Some nonlimiting examples are TAIC (triallyl isocyanurate), which is manufactured by companies such as Nippon Kasei Chemical, Iwaki, Japan, and Aldrich Chemical Co., Milwaukee, Wis.; Ricon® 152, a homopolymer of butadiene (MW 2,900), which is manufactured by Sartomer, Exton, Pa.; SR-351, trimethylol propane triacrylate, manufactured by Sartomer, Exton, Pa.; and B5405, which is 75% SR-350 (trimethylol propane trimethacrylate) and 25% inert filler acting as a carrier.
- If desirable, any suitable type of accelerator can be used. Some nonlimiting examples of accelerators are hexamethylenetetramine, mercaptobenzothiazoles, sulfenamides, thiurams, dithiocarbamates, and guanidines. Also, any suitable type of retarder can optionally be used. Some nonlimiting examples of retarders are organic acids and anhydrides, cyclohexylthiophthalimide, and sulfenamide.
- Other Compounding Ingredients
- The compounds can also optionally include other compounding ingredients, such as fillers, bonding agents, antidegradants, process oils, plasticizers, coloring agents, or other desirable ingredients. Any suitable type of filler can be used. Some typical fillers are carbon black, silica, and clay. Nonlimiting examples of suitable fillers include Sterling® 6630 carbon black, manufactured by Cabot Corporation, Alpharetta, Ga.; FK140 or FK160 silica manufactured by Degussa AG, Dusseldorf, Germany; and CAB-O-SIL® TS-530, a hydrophobic fumed silica, manufactured by Cabot Corp.
- Some nonlimiting examples of bonding agents useful in the compounds are resorcinol (1,3-dihydroxybenzene); and A-151, a vinyl triethoxy silane, which is manufactured by Huayuan Fine Chemicals, Wuhan, China.
- Any suitable type of antidegradant can be used, such as antioxidants, antiozonants, and heat stabilizers. Some typical antioxidants are secondary amines, phenolics, and phosphites. A nonlimiting example of a suitable antioxidant is Naugard® 445 antioxidant, which is a 4,4′-di(alpha, alpha-dimethyl-benzyl)diphenylamine, manufactured by Uniroyal Chemical Co., Waterbury, Conn.
- Any suitable type of process oil can be used, such as petroleum oils or vegetable oils. Some nonlimiting examples of process oils include Sunpar® 2280 paraffinic oil, manufactured by Nippon Sun Oil K.K., Japan; and Chevron ParaLux® Process Oil 6001R, a highly saturated white paraffinic process oil with very low aromatic content, manufactured by ChevronTexaco Corp., San Ramon, Calif. Also, any suitable type of plasticizer can be used, such as petroleum oils.
- Optionally, a coloring agent can be added to the compounds. Some nonlimiting examples of coloring agents are man-made mineral pigments such as the Geode® series (e.g., Geode® V-11633 Kelly Green); and the NEOLOR® series of inorganic pigments (e.g., NEOLOR® Red S), both manufactured by Ferro Corp., Cleveland, Ohio.
- Processing
- The solventless liquid isoprene compounds can be processed in any suitable manner. Typically, the chemicals are mixed together using any suitable mixing equipment, such as planetary mixers (e.g., Ross mixers), internal mixers, two-roll mills, open roll mills or the like. The mixed compound is then applied, pressed, or molded depending on the particular use. Then, the compound is cured using any suitable time and temperature profile. Typically, the compound is cured at a temperature between about 300° F. and about 400° F. for a time between about 3 minutes and about 20 minutes. The compound can be further post cured if desired or necessary, e.g., for 2 to 14 days at 70° F. to 400° F.
- Applications
- The compounds of the invention can be used in many different applications. Advantageously, the compounds are flowable so that they can take the place of materials such as liquid silicones in many applications. Preferably, the compounds have a viscosity not more than about 50% greater than that of liquid silicones, more preferably not more than about 25% greater, and most preferably not more than about 10% greater, Unlike liquid silicones, the compounds are impermeable to fluids, so their use is beneficial in applications where it is desired to limit the flow of fluids, such as in engine seals to limit the flow of VOC's through the engine. The compounds are also easier to process than liquid silicones. The flowability of the compounds allows them to be applied instead of molded, which can save the costs typically associated with molding. Of course, the compounds can also be molded if desired, and their use is not limited to flowable applications.
- Some nonlimiting examples of typical applications include use as sealing members (e.g., gaskets, O-rings, packings or the like) which can be used in many different applications, such as sealing with respect to engine oil, gear oil, transmission oil, or power steering fluid. For example, the compounds can be used for cure in place gasketing (CIPG), inject in place gasketing (IJPG), and form in place gasketing (FIPG). They can be applied robotically thereby resulting in a dispensed sealing bead.
- The compounds are suitable for making thin seals such as thin layered gaskets, and for making intricate seals and gaskets. They can be used to fill intricate channels in a metal plate. A thin gasket can be injection molded onto a plastic or metal carrier.
- The compounds can be used in liquid injection molding (LIM), transfer molding (TM), injection molding.
- The compounds can be used to make rubber-coated metal (RCM) products and rubber-coated plastic products. The compounds cure and bond well to the metal and plastic.
- The compounds can be used as a screen printing material. Because of their low viscosity, lower pressures are required during the forming process which allows for complicated manufacturing using pressure sensitive material as an integral part of the forming process.
- The compounds can be used as a fabric coating in many different applications, e.g., as a coating on airbags or interior portions of airplanes. The compounds can be used as a repair material, e.g., to fill in little holes in bumpers.
- Since the compounds are solventless, they can be easily applied by workers without the hazards of breathing in fumes. The compounds can be applied by any suitable method. The compounds can be applied and will cure at room temperature.
- Some nonlimiting examples of compounds according to the invention were prepared as follows:
Liquid IsopreneRubber 100.0 (IR 30) Varox DBPH 8.0 ZnO 1.5 -
IR 30 50 50 50 Silica 25 — — 6630 — 25 25 Varox 4 4 4 ZnO 0.75 0.75 0.75 Pigment 0.5 — — Ricon 152 — — 1.0 -
IR 30 50.0 50 6630 15.0 25 Varox 4.0 2 ZnO 0.90 0.9 B5405 1.0 1.0 -
IR 30 50 50 ZnO 0.9 0.9 Varox 2 2 FK 140 12 12 B5405 1 1 Blue Pigment 1 1 Rincon 152 2 TS-561 1.2 - In accordance with the provisions of the patent statutes, the principle and mode of operation of this invention have been explained and illustrated in its preferred embodiment. However, it must be understood that this invention may be practiced otherwise than as specifically explained and illustrated without departing from its spirit or scope.
Claims (33)
1. A solventless liquid isoprene compound comprising:
a liquid isoprene rubber, polymer molecules thereof having a backbone consisting of polyisoprene; and
a curing agent selected from the group consisting of sulfur, sulfur donors, and mixtures thereof, where the curing agent is present in an amount of at least about 3% by weight of the compound;
the compound containing substantially no solvent.
2. A compound according to claim 1 wherein the curing agent is present in an amount between about 3% and about 10% by weight of the compound.
3. A compound according to claim 1 wherein the liquid isoprene rubber is present in an amount of at least about 40% by weight of the compound.
4. A compound according to claim 1 additionally comprising a solid isoprene rubber having a Mooney value of not more than about 75, wherein the solid isoprene rubber is present in an amount of not more than about 49% by weight of the total rubber.
5. A compound according to claim 1 which is readily flowable between about 23° C. and about 150° C.
6. A flowable compound according to claim 1 which can be curable at room or elevated temperature.
7. A compound according to claim 1 which is used as a curing material for a sealing member.
8. A compound according to claim 1 which is used as a curing material for a gasket selected from the group consisting of in place gasketing (CIPG), inject in place gasketing (IJPG), and form in place gasketing (FIPG).
9. A compound according to claim 1 which is used as a molding material selected from the group consisting of liquid injection molding (LIM), transfer molding (TM), and injection molding.
10-16. (canceled)
17. A compound according to claim 10 which is used as a curing material for a sealing member.
18. A compound according to claim 10 which is used as a curing material for a gasket selected from the group consisting of in place gasketing (CIPG), inject in place gasketing (IJPG), and form in place gasketing (FIPG).
19. A compound according to claim 10 which is used as a molding material selected from the group consisting of liquid injection molding (LIM), transfer molding (TM), and injection molding.
20. (canceled)
21. A sealing member made by a process comprising curing the solventless liquid isoprene compound according to claim 1 .
22. A sealing member according to claim 21 , wherein the sealing member is a gasket.
23. A gasket according to claim 22 , wherein the gasket is a cure in place gasket (CIPG), an inject in place gasket (IJPG), or a form in place gasket (FIPG).
24. A gasket according to claim 22 , wherein the gasket is a gasket formed by liquid injection molding (LIM), a gasket formed by transfer molding (TM), or a gasket formed by injection molding.
25. A sealing member according to claim 21 , wherein the sealing member is an O-ring.
26. A sealing member made by a process comprising curing the solventless liquid isoprene compound according to claim 10.
27. A sealing member according to claim 26 , wherein the nonsulfur curing agent is a peroxide curing agent.
28. A sealing member according to claim 26 , wherein the sealing member is a gasket.
29. A gasket according to claim 28 , wherein the gasket is a cure in place gasket (CIPG), an inject in place gasket (IJPG), or a form in place gasket (FIPG).
30. A gasket according to claim 28 , wherein the gasket is a gasket formed by liquid injection molding (LIM), a gasket formed by transfer molding (TM), or a gasket formed by injection molding.
31. A sealing member according to claim 26 , wherein the sealing member is an O-ring.
32. A process for making a sealing member, comprising shaping and curing the solventless liquid isoprene compound according to claim 1 .
33. A process according to claim 32 , comprising shaping and curing by a method selected from the group consisting of cure in place gasketing (CIPG), inject in place gasketing (IJPG), and form in place gasketing (FIPG).
34. A process according to claim 32 , wherein the sealing member is shaped by a method selected from the group consisting of liquid injection molding (LIM), transfer molding (TM), and injection molding.
35. A process according to claim 32 , comprising curing at a temperature between 300° F. and 400° F.
36. A process for making a sealing member comprising shaping and curing the solventless liquid isoprene compound according to claim 10.
37. A process according to claim 36 , comprising shaping and curing by a method selected from the group consisting of cure in place gasketing (CIPG), inject in place gasketing (IJPG), and form in place gasketing (FIPG).
38. A process according to claim 36 , wherein the sealing member is shaped by a method selected from the group consisting of liquid injection molding (LIM), transfer molding (TM), and injection molding.
39. A process according to claim 36 , comprising curing at a temperature between 300° F. and 400° F.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US12/021,001 US20080116645A1 (en) | 2001-12-21 | 2008-01-28 | Solventless liquid isoprene compounds |
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US34223901P | 2001-12-21 | 2001-12-21 | |
| US10/329,064 US7335807B2 (en) | 2001-12-21 | 2002-12-23 | Solventless liquid isoprene compounds |
| US12/021,001 US20080116645A1 (en) | 2001-12-21 | 2008-01-28 | Solventless liquid isoprene compounds |
Related Parent Applications (1)
| Application Number | Title | Priority Date | Filing Date |
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| US10/329,064 Division US7335807B2 (en) | 2001-12-21 | 2002-12-23 | Solventless liquid isoprene compounds |
Publications (1)
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| US20080116645A1 true US20080116645A1 (en) | 2008-05-22 |
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| US12/021,001 Abandoned US20080116645A1 (en) | 2001-12-21 | 2008-01-28 | Solventless liquid isoprene compounds |
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Families Citing this family (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1666512B1 (en) | 2004-12-03 | 2008-10-08 | Lanxess Inc. | Liquid alpha-Olefin vinyl acetate compounds |
| US8394896B2 (en) * | 2004-12-06 | 2013-03-12 | Lanxess Inc. | Liquid α-olefin vinyl acetate compounds |
| US8110266B2 (en) | 2007-02-08 | 2012-02-07 | Allegiance Corporation | Glove coating and manufacturing process |
| US20080306200A1 (en) * | 2007-06-11 | 2008-12-11 | Seong Fong Chen | Antistatic gloves and process for making same |
| BRPI0821878A2 (en) * | 2008-01-04 | 2019-09-10 | Bard Inc C R | synthetic polyisoprene latex curing methods and non-resident urinary drainage catheter |
| NZ587607A (en) | 2008-03-14 | 2012-08-31 | Allegiance Corp | Elastomer dispersion comprising a dispersed elastomer and accelerator in an aqueous phase and latex materials produced therefrom |
| CA2729673A1 (en) * | 2008-06-30 | 2010-01-07 | C.R. Bard, Inc. | Polyurethane/polyisoprene blend catheter |
| US20100099932A1 (en) * | 2008-10-21 | 2010-04-22 | Ecoprene Llc | Isoprene Compositions and Methods of Use |
| US8575257B2 (en) | 2011-06-15 | 2013-11-05 | Lion Copolymer, Llc | Fire retardant brominated rubber polymeric composition and method for making |
| US8962722B2 (en) | 2011-06-15 | 2015-02-24 | Lion Copolymer Geismar, Llc | Solvent-less liquid ethylene propylene diene monomer rubber compound and method of making |
| WO2012174492A1 (en) | 2011-06-15 | 2012-12-20 | Lion Copolymer, Llc | Durable substrate coating and process for making |
| US9267019B2 (en) | 2011-06-15 | 2016-02-23 | Lion Copolymer Holdings, Llc | Functionalized silica for silica wet masterbatches and styrene butadiene rubber compositions |
| US9574055B2 (en) | 2012-02-02 | 2017-02-21 | Lion Copolymer Holdings, Llc | Compatibilized silica with a plurality of silanes and a polymer silica-reinforced masterbatch |
| US8835536B2 (en) | 2012-02-02 | 2014-09-16 | Lion Copolymer Holdings, Llc | Highly silica loaded styrene butadiene rubber masterbatch |
| US8741987B2 (en) | 2012-02-02 | 2014-06-03 | Lion Copolymer Holdings, Llc | Polymer silica-reinforced masterbatch with nanomaterial |
Citations (39)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3931074A (en) * | 1974-03-14 | 1976-01-06 | Monsanto Company | Modifiers for high nitrile polymers |
| US4048261A (en) * | 1975-11-10 | 1977-09-13 | The B. F. Goodrich Company | Vulcanizable compositions of a halogen-containing polymer and a diene-nitrile rubber having active halogen cure sites |
| US4355139A (en) * | 1980-03-10 | 1982-10-19 | Monsanto Company | Compatibilized polymer blends |
| US4421884A (en) * | 1981-08-11 | 1983-12-20 | Nippon Zeon Co. Ltd. | Oil-resistant rubber composition |
| US4486480A (en) * | 1981-12-30 | 1984-12-04 | Toyoda Gosei Co., Ltd. | Rubber hose comprising a liquid nitrile-butadiene copolymer incorporated into a partially hydrogenated unsaturated acrylonitrile-butadiene copolymer |
| US4654404A (en) * | 1984-11-21 | 1987-03-31 | Nippon Zeon Co., Ltd. | Oil-resistant rubber composition |
| US4696984A (en) * | 1985-06-05 | 1987-09-29 | Enichem Elastomeri, S.P.A. | Isoprene polymerization process |
| US4833195A (en) * | 1987-07-20 | 1989-05-23 | Bp Performance Polymers, Inc. | High flow drapable polymer compositions |
| US4843128A (en) * | 1986-05-23 | 1989-06-27 | Uniroyal Chemical Company, Inc. | Elastomeric composition having increased ozone resistance |
| US4921912A (en) * | 1986-02-03 | 1990-05-01 | Ciba-Geigy Corporation | Epoxy resin composition containing acrylic oligomer, amine and amine-terminated nitrile rubber |
| US4960829A (en) * | 1986-05-23 | 1990-10-02 | Uniroyal Chemical Company, Inc. | Elastomeric composition |
| US5000981A (en) * | 1988-01-25 | 1991-03-19 | The B. F. Goodrich Company | Compositions of elastomer-coated fibers |
| US5068275A (en) * | 1990-02-01 | 1991-11-26 | Polysar Rubber Corporation | Plasticized hydrogenated nitrile rubber |
| US5080942A (en) * | 1990-05-23 | 1992-01-14 | Minnesota Mining And Manufacturing Company | High stretch elastomeric pre-stretched tubes |
| US5087668A (en) * | 1990-10-19 | 1992-02-11 | The Goodyear Tire & Rubber Company | Rubber blend and tire with tread thereof |
| US5149895A (en) * | 1990-01-16 | 1992-09-22 | Mobil Oil Corporation | Vulcanizable liquid compositions |
| US5239000A (en) * | 1991-06-21 | 1993-08-24 | Yukong Limited | Thermoplastic elastomer and process for preparation |
| US5288937A (en) * | 1990-01-16 | 1994-02-22 | Mobil Oil Corporation | Vulcanizable liquid compositions |
| US5510548A (en) * | 1995-02-03 | 1996-04-23 | Mobil Oil Corporation | Vulcanizable liquid compositions |
| US5548028A (en) * | 1995-02-24 | 1996-08-20 | E. I. Du Pont De Nemours And Company | Curable elastomeric blend with vulcanized fluoroelastomer |
| US5551707A (en) * | 1995-06-06 | 1996-09-03 | Freudenberg-Nok General Partnership | Multi-material seal ring |
| US5633341A (en) * | 1992-08-17 | 1997-05-27 | Ciba Geigy Corporation | At room temperature crosslinkable compositions, and methods of their manufacture and use |
| US5677402A (en) * | 1995-09-22 | 1997-10-14 | The Goodyear Tire & Rubber Company | Process for preparing 3,4-polyisoprene rubber |
| US5844047A (en) * | 1993-07-16 | 1998-12-01 | Ciba Specialty Chemicals Corporation | Single component, heat curing compositions which are stable when stored at room temperature and which comprise polymers containing anhydride groups and powdered crosslinking agents, and their method of manufacture and use |
| US5844021A (en) * | 1991-08-23 | 1998-12-01 | The Whitaker Corporation | Sealant compositions and sealed electrical connectors |
| US5912288A (en) * | 1995-03-13 | 1999-06-15 | Nichias Corporation | Vulcanized rubber composition |
| US5958530A (en) * | 1989-03-17 | 1999-09-28 | Uniroyal Chemical Company, Inc. | Method of making extruded polyethlyene pipes |
| US6066690A (en) * | 1995-09-29 | 2000-05-23 | Sunstar Giken Kabushiki Kaisha | Heat-vulcanizable rubber composition |
| US6070634A (en) * | 1997-09-23 | 2000-06-06 | The Goodyear Tire & Rubber Company | Tire with tread made with liquid block copolymer |
| US6120869A (en) * | 1994-11-09 | 2000-09-19 | Carlisle Companies Inc. | Pressure sensitive tape for forming water-tight field joints in rubber membranes |
| US6162847A (en) * | 1997-02-12 | 2000-12-19 | Freudenberg-Nok General Partnership | Preparing NBR rubber seal products with phosphite and phosphate additives |
| US6204320B1 (en) * | 1999-02-12 | 2001-03-20 | The Goodyear Tire & Rubber Company | Liquid isoprene-butadiene rubber |
| US6214922B1 (en) * | 1998-03-06 | 2001-04-10 | Bayer Inc. | Nitrile polymer vulcanizate and process for the production thereof |
| US6232403B1 (en) * | 1998-12-22 | 2001-05-15 | Firma Carl Freudenberg | Elastomer material |
| US6238787B1 (en) * | 1997-10-01 | 2001-05-29 | Park-Ohio Industries | Method of attaching a strip to a rubber molded part |
| US6265474B1 (en) * | 1998-04-03 | 2001-07-24 | Freudenberg-Nok General Partnership | Nitrile butadiene rubber composition |
| US6268056B1 (en) * | 1998-03-23 | 2001-07-31 | Freudenberg-Nok General Partnership | Seal assembly with new resin stabilized adhesive composition to bond an insert member to the elastomeric seal material |
| US6291374B1 (en) * | 1994-10-13 | 2001-09-18 | World Properties, Inc. | Polybutadiene and polyisoprene based thermosetting compositions and method of manufacture |
| US6638632B2 (en) * | 2000-07-31 | 2003-10-28 | Bridgestone Corporation | Rubber composition for elastic member and elastic member using same |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS585350A (en) * | 1981-07-01 | 1983-01-12 | Pijiyon Kk | Method for reducing content of n-nitroso compound in rubber goods |
| JPS5962652A (en) * | 1982-10-04 | 1984-04-10 | Tokuyama Soda Co Ltd | Crosslinking method for isoprene rubber |
| JPH044242A (en) * | 1990-04-23 | 1992-01-08 | Sumitomo Rubber Ind Ltd | Formed rubber article having anisotropic strength |
| JPH0577846A (en) * | 1991-07-24 | 1993-03-30 | Polytec Design:Kk | Rubber plug of medical vessel |
| JP3044112B2 (en) * | 1991-12-27 | 2000-05-22 | 住友ゴム工業株式会社 | Marine structural materials |
| JP3391572B2 (en) * | 1994-10-05 | 2003-03-31 | 住友ゴム工業株式会社 | Rubber composition for tire |
| JPH08253739A (en) * | 1995-01-19 | 1996-10-01 | Sumitomo Bakelite Co Ltd | Thermosetting adhesive tape and its production |
| JP3220620B2 (en) * | 1995-05-26 | 2001-10-22 | 松下電器産業株式会社 | Aluminum electrolytic capacitor |
-
2002
- 2002-12-23 US US10/329,064 patent/US7335807B2/en not_active Expired - Fee Related
-
2008
- 2008-01-28 US US12/021,001 patent/US20080116645A1/en not_active Abandoned
Patent Citations (42)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3931074A (en) * | 1974-03-14 | 1976-01-06 | Monsanto Company | Modifiers for high nitrile polymers |
| US4048261A (en) * | 1975-11-10 | 1977-09-13 | The B. F. Goodrich Company | Vulcanizable compositions of a halogen-containing polymer and a diene-nitrile rubber having active halogen cure sites |
| US4355139A (en) * | 1980-03-10 | 1982-10-19 | Monsanto Company | Compatibilized polymer blends |
| US4421884A (en) * | 1981-08-11 | 1983-12-20 | Nippon Zeon Co. Ltd. | Oil-resistant rubber composition |
| US4486480A (en) * | 1981-12-30 | 1984-12-04 | Toyoda Gosei Co., Ltd. | Rubber hose comprising a liquid nitrile-butadiene copolymer incorporated into a partially hydrogenated unsaturated acrylonitrile-butadiene copolymer |
| US4654404A (en) * | 1984-11-21 | 1987-03-31 | Nippon Zeon Co., Ltd. | Oil-resistant rubber composition |
| US4696984A (en) * | 1985-06-05 | 1987-09-29 | Enichem Elastomeri, S.P.A. | Isoprene polymerization process |
| US4921912A (en) * | 1986-02-03 | 1990-05-01 | Ciba-Geigy Corporation | Epoxy resin composition containing acrylic oligomer, amine and amine-terminated nitrile rubber |
| US4843128A (en) * | 1986-05-23 | 1989-06-27 | Uniroyal Chemical Company, Inc. | Elastomeric composition having increased ozone resistance |
| US4960829A (en) * | 1986-05-23 | 1990-10-02 | Uniroyal Chemical Company, Inc. | Elastomeric composition |
| US4833195A (en) * | 1987-07-20 | 1989-05-23 | Bp Performance Polymers, Inc. | High flow drapable polymer compositions |
| US5000981A (en) * | 1988-01-25 | 1991-03-19 | The B. F. Goodrich Company | Compositions of elastomer-coated fibers |
| US5958530A (en) * | 1989-03-17 | 1999-09-28 | Uniroyal Chemical Company, Inc. | Method of making extruded polyethlyene pipes |
| US5545783A (en) * | 1990-01-16 | 1996-08-13 | Mobil Oil Corporation | Vulcanizable liquid compositions |
| US5625100A (en) * | 1990-01-16 | 1997-04-29 | Mobil Oil Company | Vulcanizable liquid compositions |
| US5149895A (en) * | 1990-01-16 | 1992-09-22 | Mobil Oil Corporation | Vulcanizable liquid compositions |
| US5387730A (en) * | 1990-01-16 | 1995-02-07 | Mobil Oil Corporation | Vulcanizable liquid compositions |
| US5288937A (en) * | 1990-01-16 | 1994-02-22 | Mobil Oil Corporation | Vulcanizable liquid compositions |
| US5068275A (en) * | 1990-02-01 | 1991-11-26 | Polysar Rubber Corporation | Plasticized hydrogenated nitrile rubber |
| US5080942A (en) * | 1990-05-23 | 1992-01-14 | Minnesota Mining And Manufacturing Company | High stretch elastomeric pre-stretched tubes |
| US5087668A (en) * | 1990-10-19 | 1992-02-11 | The Goodyear Tire & Rubber Company | Rubber blend and tire with tread thereof |
| US5239000A (en) * | 1991-06-21 | 1993-08-24 | Yukong Limited | Thermoplastic elastomer and process for preparation |
| US5844021A (en) * | 1991-08-23 | 1998-12-01 | The Whitaker Corporation | Sealant compositions and sealed electrical connectors |
| US5633341A (en) * | 1992-08-17 | 1997-05-27 | Ciba Geigy Corporation | At room temperature crosslinkable compositions, and methods of their manufacture and use |
| US5844047A (en) * | 1993-07-16 | 1998-12-01 | Ciba Specialty Chemicals Corporation | Single component, heat curing compositions which are stable when stored at room temperature and which comprise polymers containing anhydride groups and powdered crosslinking agents, and their method of manufacture and use |
| US6291374B1 (en) * | 1994-10-13 | 2001-09-18 | World Properties, Inc. | Polybutadiene and polyisoprene based thermosetting compositions and method of manufacture |
| US6120869A (en) * | 1994-11-09 | 2000-09-19 | Carlisle Companies Inc. | Pressure sensitive tape for forming water-tight field joints in rubber membranes |
| US5510548A (en) * | 1995-02-03 | 1996-04-23 | Mobil Oil Corporation | Vulcanizable liquid compositions |
| US5548028A (en) * | 1995-02-24 | 1996-08-20 | E. I. Du Pont De Nemours And Company | Curable elastomeric blend with vulcanized fluoroelastomer |
| US5912288A (en) * | 1995-03-13 | 1999-06-15 | Nichias Corporation | Vulcanized rubber composition |
| US5551707A (en) * | 1995-06-06 | 1996-09-03 | Freudenberg-Nok General Partnership | Multi-material seal ring |
| US5677402A (en) * | 1995-09-22 | 1997-10-14 | The Goodyear Tire & Rubber Company | Process for preparing 3,4-polyisoprene rubber |
| US6066690A (en) * | 1995-09-29 | 2000-05-23 | Sunstar Giken Kabushiki Kaisha | Heat-vulcanizable rubber composition |
| US6162847A (en) * | 1997-02-12 | 2000-12-19 | Freudenberg-Nok General Partnership | Preparing NBR rubber seal products with phosphite and phosphate additives |
| US6070634A (en) * | 1997-09-23 | 2000-06-06 | The Goodyear Tire & Rubber Company | Tire with tread made with liquid block copolymer |
| US6238787B1 (en) * | 1997-10-01 | 2001-05-29 | Park-Ohio Industries | Method of attaching a strip to a rubber molded part |
| US6214922B1 (en) * | 1998-03-06 | 2001-04-10 | Bayer Inc. | Nitrile polymer vulcanizate and process for the production thereof |
| US6268056B1 (en) * | 1998-03-23 | 2001-07-31 | Freudenberg-Nok General Partnership | Seal assembly with new resin stabilized adhesive composition to bond an insert member to the elastomeric seal material |
| US6265474B1 (en) * | 1998-04-03 | 2001-07-24 | Freudenberg-Nok General Partnership | Nitrile butadiene rubber composition |
| US6232403B1 (en) * | 1998-12-22 | 2001-05-15 | Firma Carl Freudenberg | Elastomer material |
| US6204320B1 (en) * | 1999-02-12 | 2001-03-20 | The Goodyear Tire & Rubber Company | Liquid isoprene-butadiene rubber |
| US6638632B2 (en) * | 2000-07-31 | 2003-10-28 | Bridgestone Corporation | Rubber composition for elastic member and elastic member using same |
Also Published As
| Publication number | Publication date |
|---|---|
| US20030139524A1 (en) | 2003-07-24 |
| US7335807B2 (en) | 2008-02-26 |
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