WO2001064782B1 - Silica reinforced rubber compositions of improved processability and storage stability - Google Patents
Silica reinforced rubber compositions of improved processability and storage stabilityInfo
- Publication number
- WO2001064782B1 WO2001064782B1 PCT/US2001/006326 US0106326W WO0164782B1 WO 2001064782 B1 WO2001064782 B1 WO 2001064782B1 US 0106326 W US0106326 W US 0106326W WO 0164782 B1 WO0164782 B1 WO 0164782B1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- ether
- glycidyl
- silica
- organic compound
- diglycidyl
- Prior art date
Links
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 title claims abstract 32
- 239000000203 mixture Substances 0.000 title claims abstract 16
- 239000000377 silicon dioxide Substances 0.000 title claims abstract 16
- 229920001971 elastomer Polymers 0.000 title claims abstract 15
- 239000005060 rubber Substances 0.000 title claims abstract 15
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims abstract 21
- 150000002894 organic compounds Chemical class 0.000 claims abstract 18
- 239000004593 Epoxy Substances 0.000 claims abstract 11
- 238000000034 method Methods 0.000 claims abstract 10
- 150000003553 thiiranes Chemical class 0.000 claims abstract 9
- 125000000524 functional group Chemical group 0.000 claims abstract 8
- 239000000945 filler Substances 0.000 claims abstract 6
- 150000001412 amines Chemical class 0.000 claims abstract 4
- 150000002148 esters Chemical class 0.000 claims abstract 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract 4
- GYZLOYUZLJXAJU-UHFFFAOYSA-N diglycidyl ether Chemical group C1OC1COCC1CO1 GYZLOYUZLJXAJU-UHFFFAOYSA-N 0.000 claims 10
- -1 aliphatic polyol Chemical class 0.000 claims 9
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 claims 8
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 claims 6
- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 claims 6
- KAKZBPTYRLMSJV-UHFFFAOYSA-N vinyl-ethylene Natural products C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 claims 6
- 244000043261 Hevea brasiliensis Species 0.000 claims 4
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 claims 4
- 229920001577 copolymer Polymers 0.000 claims 4
- 125000003055 glycidyl group Chemical group C(C1CO1)* 0.000 claims 4
- 229920003052 natural elastomer Polymers 0.000 claims 4
- 229920001194 natural rubber Polymers 0.000 claims 4
- 229920001897 terpolymer Polymers 0.000 claims 4
- AOBIOSPNXBMOAT-UHFFFAOYSA-N 2-[2-(oxiran-2-ylmethoxy)ethoxymethyl]oxirane Chemical compound C1OC1COCCOCC1CO1 AOBIOSPNXBMOAT-UHFFFAOYSA-N 0.000 claims 3
- JLBJTVDPSNHSKJ-UHFFFAOYSA-N 4-Methylstyrene Chemical compound CC1=CC=C(C=C)C=C1 JLBJTVDPSNHSKJ-UHFFFAOYSA-N 0.000 claims 3
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims 3
- FQYUMYWMJTYZTK-UHFFFAOYSA-N Phenyl glycidyl ether Chemical compound C1OC1COC1=CC=CC=C1 FQYUMYWMJTYZTK-UHFFFAOYSA-N 0.000 claims 3
- XFUOBHWPTSIEOV-UHFFFAOYSA-N bis(oxiran-2-ylmethyl) cyclohexane-1,2-dicarboxylate Chemical compound C1CCCC(C(=O)OCC2OC2)C1C(=O)OCC1CO1 XFUOBHWPTSIEOV-UHFFFAOYSA-N 0.000 claims 3
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 claims 3
- 229920002857 polybutadiene Polymers 0.000 claims 3
- 229920000642 polymer Polymers 0.000 claims 3
- 229920001451 polypropylene glycol Polymers 0.000 claims 3
- NVZWEEGUWXZOKI-UHFFFAOYSA-N 1-ethenyl-2-methylbenzene Chemical compound CC1=CC=CC=C1C=C NVZWEEGUWXZOKI-UHFFFAOYSA-N 0.000 claims 2
- YSUQLAYJZDEMOT-UHFFFAOYSA-N 2-(butoxymethyl)oxirane Chemical compound CCCCOCC1CO1 YSUQLAYJZDEMOT-UHFFFAOYSA-N 0.000 claims 2
- NWLUZGJDEZBBRH-UHFFFAOYSA-N 2-(propan-2-yloxymethyl)oxirane Chemical compound CC(C)OCC1CO1 NWLUZGJDEZBBRH-UHFFFAOYSA-N 0.000 claims 2
- WNISWKAEAPQCJQ-UHFFFAOYSA-N 2-[(2-nonylphenoxy)methyl]oxirane Chemical compound CCCCCCCCCC1=CC=CC=C1OCC1OC1 WNISWKAEAPQCJQ-UHFFFAOYSA-N 0.000 claims 2
- CUFXMPWHOWYNSO-UHFFFAOYSA-N 2-[(4-methylphenoxy)methyl]oxirane Chemical compound C1=CC(C)=CC=C1OCC1OC1 CUFXMPWHOWYNSO-UHFFFAOYSA-N 0.000 claims 2
- HHRACYLRBOUBKM-UHFFFAOYSA-N 2-[(4-tert-butylphenoxy)methyl]oxirane Chemical compound C1=CC(C(C)(C)C)=CC=C1OCC1OC1 HHRACYLRBOUBKM-UHFFFAOYSA-N 0.000 claims 2
- JFDMLXYWGLECEY-UHFFFAOYSA-N 2-benzyloxirane Chemical compound C=1C=CC=CC=1CC1CO1 JFDMLXYWGLECEY-UHFFFAOYSA-N 0.000 claims 2
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 claims 2
- LCFVJGUPQDGYKZ-UHFFFAOYSA-N Bisphenol A diglycidyl ether Chemical compound C=1C=C(OCC2OC2)C=CC=1C(C)(C)C(C=C1)=CC=C1OCC1CO1 LCFVJGUPQDGYKZ-UHFFFAOYSA-N 0.000 claims 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 claims 2
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims 2
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 claims 2
- MTAZNLWOLGHBHU-UHFFFAOYSA-N butadiene-styrene rubber Chemical compound C=CC=C.C=CC1=CC=CC=C1 MTAZNLWOLGHBHU-UHFFFAOYSA-N 0.000 claims 2
- 239000006229 carbon black Substances 0.000 claims 2
- 239000004359 castor oil Substances 0.000 claims 2
- 235000019438 castor oil Nutrition 0.000 claims 2
- 239000007795 chemical reaction product Substances 0.000 claims 2
- 230000008878 coupling Effects 0.000 claims 2
- 238000010168 coupling process Methods 0.000 claims 2
- 238000005859 coupling reaction Methods 0.000 claims 2
- 239000000835 fiber Substances 0.000 claims 2
- ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 claims 2
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 claims 2
- JAYXSROKFZAHRQ-UHFFFAOYSA-N n,n-bis(oxiran-2-ylmethyl)aniline Chemical compound C1OC1CN(C=1C=CC=CC=1)CC1CO1 JAYXSROKFZAHRQ-UHFFFAOYSA-N 0.000 claims 2
- 239000003921 oil Substances 0.000 claims 2
- 150000001282 organosilanes Chemical class 0.000 claims 2
- YLNSNVGRSIOCEU-UHFFFAOYSA-N oxiran-2-ylmethyl butanoate Chemical compound CCCC(=O)OCC1CO1 YLNSNVGRSIOCEU-UHFFFAOYSA-N 0.000 claims 2
- 229920000559 poly(Bisphenol A-co-epichlorohydrin) Polymers 0.000 claims 2
- 229920005862 polyol Polymers 0.000 claims 2
- 239000000047 product Substances 0.000 claims 2
- CHUGKEQJSLOLHL-UHFFFAOYSA-N 2,2-Bis(bromomethyl)propane-1,3-diol Chemical compound OCC(CO)(CBr)CBr CHUGKEQJSLOLHL-UHFFFAOYSA-N 0.000 claims 1
- BBBUAWSVILPJLL-UHFFFAOYSA-N 2-(2-ethylhexoxymethyl)oxirane Chemical compound CCCCC(CC)COCC1CO1 BBBUAWSVILPJLL-UHFFFAOYSA-N 0.000 claims 1
- SPMYYWZTCLZLQV-UHFFFAOYSA-N 2-[[5-methoxy-2-[4-methoxy-2-(oxiran-2-ylmethyl)phenoxy]phenyl]methyl]oxirane Chemical compound C1OC1CC1=CC(OC)=CC=C1OC1=CC=C(OC)C=C1CC1CO1 SPMYYWZTCLZLQV-UHFFFAOYSA-N 0.000 claims 1
- FCZHJHKCOZGQJZ-UHFFFAOYSA-N 2-oct-7-enyloxirane Chemical compound C=CCCCCCCC1CO1 FCZHJHKCOZGQJZ-UHFFFAOYSA-N 0.000 claims 1
- MECNWXGGNCJFQJ-UHFFFAOYSA-N 3-piperidin-1-ylpropane-1,2-diol Chemical compound OCC(O)CN1CCCCC1 MECNWXGGNCJFQJ-UHFFFAOYSA-N 0.000 claims 1
- NHJIDZUQMHKGRE-UHFFFAOYSA-N 7-oxabicyclo[4.1.0]heptan-4-yl 2-(7-oxabicyclo[4.1.0]heptan-4-yl)acetate Chemical compound C1CC2OC2CC1OC(=O)CC1CC2OC2CC1 NHJIDZUQMHKGRE-UHFFFAOYSA-N 0.000 claims 1
- RSWGJHLUYNHPMX-UHFFFAOYSA-N Abietic-Saeure Natural products C12CCC(C(C)C)=CC2=CCC2C1(C)CCCC2(C)C(O)=O RSWGJHLUYNHPMX-UHFFFAOYSA-N 0.000 claims 1
- 229930185605 Bisphenol Natural products 0.000 claims 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 claims 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 claims 1
- VHOQXEIFYTTXJU-UHFFFAOYSA-N Isobutylene-isoprene copolymer Chemical compound CC(C)=C.CC(=C)C=C VHOQXEIFYTTXJU-UHFFFAOYSA-N 0.000 claims 1
- 239000006057 Non-nutritive feed additive Substances 0.000 claims 1
- 239000005062 Polybutadiene Substances 0.000 claims 1
- KHPCPRHQVVSZAH-HUOMCSJISA-N Rosin Natural products O(C/C=C/c1ccccc1)[C@H]1[C@H](O)[C@@H](O)[C@@H](O)[C@@H](CO)O1 KHPCPRHQVVSZAH-HUOMCSJISA-N 0.000 claims 1
- 229920002472 Starch Polymers 0.000 claims 1
- 239000002253 acid Substances 0.000 claims 1
- 150000001299 aldehydes Chemical class 0.000 claims 1
- 125000005250 alkyl acrylate group Chemical group 0.000 claims 1
- 125000000217 alkyl group Chemical group 0.000 claims 1
- 239000003963 antioxidant agent Substances 0.000 claims 1
- 239000004760 aramid Substances 0.000 claims 1
- 239000010692 aromatic oil Substances 0.000 claims 1
- 229920003235 aromatic polyamide Polymers 0.000 claims 1
- 239000000440 bentonite Substances 0.000 claims 1
- 229910000278 bentonite Inorganic materials 0.000 claims 1
- SVPXDRXYRYOSEX-UHFFFAOYSA-N bentoquatam Chemical compound O.O=[Si]=O.O=[Al]O[Al]=O SVPXDRXYRYOSEX-UHFFFAOYSA-N 0.000 claims 1
- KVBYPTUGEKVEIJ-UHFFFAOYSA-N benzene-1,3-diol;formaldehyde Chemical class O=C.OC1=CC=CC(O)=C1 KVBYPTUGEKVEIJ-UHFFFAOYSA-N 0.000 claims 1
- 229920005549 butyl rubber Polymers 0.000 claims 1
- 239000011575 calcium Substances 0.000 claims 1
- 229910052791 calcium Inorganic materials 0.000 claims 1
- 229910000019 calcium carbonate Inorganic materials 0.000 claims 1
- 239000004927 clay Substances 0.000 claims 1
- 229910052570 clay Inorganic materials 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 claims 1
- 238000004132 cross linking Methods 0.000 claims 1
- CFFOYHZILKHZDE-UHFFFAOYSA-N cyclohexylmethyl 7-oxabicyclo[4.1.0]heptane-4-carboxylate Chemical compound C1CC2OC2CC1C(=O)OCC1CCCCC1 CFFOYHZILKHZDE-UHFFFAOYSA-N 0.000 claims 1
- 229920003244 diene elastomer Polymers 0.000 claims 1
- 239000000539 dimer Substances 0.000 claims 1
- HQQADJVZYDDRJT-UHFFFAOYSA-N ethene;prop-1-ene Chemical group C=C.CC=C HQQADJVZYDDRJT-UHFFFAOYSA-N 0.000 claims 1
- OHNNZOOGWXZCPZ-UHFFFAOYSA-N exo-norbornene oxide Chemical compound C1CC2C3OC3C1C2 OHNNZOOGWXZCPZ-UHFFFAOYSA-N 0.000 claims 1
- 229910021485 fumed silica Inorganic materials 0.000 claims 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 claims 1
- 229910052909 inorganic silicate Inorganic materials 0.000 claims 1
- 239000010445 mica Substances 0.000 claims 1
- 229910052618 mica group Inorganic materials 0.000 claims 1
- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 claims 1
- QQWAKSKPSOFJFF-UHFFFAOYSA-N oxiran-2-ylmethyl 2,2-dimethyloctanoate Chemical compound CCCCCCC(C)(C)C(=O)OCC1CO1 QQWAKSKPSOFJFF-UHFFFAOYSA-N 0.000 claims 1
- 239000012188 paraffin wax Substances 0.000 claims 1
- XKJCHHZQLQNZHY-UHFFFAOYSA-N phthalimide Chemical compound C1=CC=C2C(=O)NC(=O)C2=C1 XKJCHHZQLQNZHY-UHFFFAOYSA-N 0.000 claims 1
- 229920000151 polyglycol Polymers 0.000 claims 1
- 239000010695 polyglycol Substances 0.000 claims 1
- 239000011347 resin Substances 0.000 claims 1
- 229920005989 resin Polymers 0.000 claims 1
- 239000008107 starch Substances 0.000 claims 1
- 235000019698 starch Nutrition 0.000 claims 1
- 229920003048 styrene butadiene rubber Polymers 0.000 claims 1
- 229920003051 synthetic elastomer Polymers 0.000 claims 1
- 229920001059 synthetic polymer Polymers 0.000 claims 1
- 239000000454 talc Substances 0.000 claims 1
- 229910052623 talc Inorganic materials 0.000 claims 1
- 239000004408 titanium dioxide Substances 0.000 claims 1
- KHPCPRHQVVSZAH-UHFFFAOYSA-N trans-cinnamyl beta-D-glucopyranoside Natural products OC1C(O)C(O)C(CO)OC1OCC=CC1=CC=CC=C1 KHPCPRHQVVSZAH-UHFFFAOYSA-N 0.000 claims 1
- VTHOKNTVYKTUPI-UHFFFAOYSA-N triethoxy-[3-(3-triethoxysilylpropyltetrasulfanyl)propyl]silane Chemical compound CCO[Si](OCC)(OCC)CCCSSSSCCC[Si](OCC)(OCC)OCC VTHOKNTVYKTUPI-UHFFFAOYSA-N 0.000 claims 1
- QXJQHYBHAIHNGG-UHFFFAOYSA-N trimethylolethane Chemical compound OCC(C)(CO)CO QXJQHYBHAIHNGG-UHFFFAOYSA-N 0.000 claims 1
- 235000013311 vegetables Nutrition 0.000 claims 1
- 239000001993 wax Substances 0.000 claims 1
- 125000003700 epoxy group Chemical group 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/04—Oxygen-containing compounds
- C08K5/15—Heterocyclic compounds having oxygen in the ring
- C08K5/151—Heterocyclic compounds having oxygen in the ring having one oxygen atom in the ring
- C08K5/1515—Three-membered rings
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B60—VEHICLES IN GENERAL
- B60C—VEHICLE TYRES; TYRE INFLATION; TYRE CHANGING; CONNECTING VALVES TO INFLATABLE ELASTIC BODIES IN GENERAL; DEVICES OR ARRANGEMENTS RELATED TO TYRES
- B60C1/00—Tyres characterised by the chemical composition or the physical arrangement or mixture of the composition
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B60—VEHICLES IN GENERAL
- B60C—VEHICLE TYRES; TYRE INFLATION; TYRE CHANGING; CONNECTING VALVES TO INFLATABLE ELASTIC BODIES IN GENERAL; DEVICES OR ARRANGEMENTS RELATED TO TYRES
- B60C1/00—Tyres characterised by the chemical composition or the physical arrangement or mixture of the composition
- B60C1/0008—Compositions of the inner liner
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B60—VEHICLES IN GENERAL
- B60C—VEHICLE TYRES; TYRE INFLATION; TYRE CHANGING; CONNECTING VALVES TO INFLATABLE ELASTIC BODIES IN GENERAL; DEVICES OR ARRANGEMENTS RELATED TO TYRES
- B60C1/00—Tyres characterised by the chemical composition or the physical arrangement or mixture of the composition
- B60C1/0016—Compositions of the tread
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B60—VEHICLES IN GENERAL
- B60C—VEHICLE TYRES; TYRE INFLATION; TYRE CHANGING; CONNECTING VALVES TO INFLATABLE ELASTIC BODIES IN GENERAL; DEVICES OR ARRANGEMENTS RELATED TO TYRES
- B60C1/00—Tyres characterised by the chemical composition or the physical arrangement or mixture of the composition
- B60C1/0025—Compositions of the sidewalls
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/04—Oxygen-containing compounds
- C08K5/10—Esters; Ether-esters
- C08K5/101—Esters; Ether-esters of monocarboxylic acids
- C08K5/103—Esters; Ether-esters of monocarboxylic acids with polyalcohols
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/36—Sulfur-, selenium-, or tellurium-containing compounds
- C08K5/45—Heterocyclic compounds having sulfur in the ring
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L21/00—Compositions of unspecified rubbers
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Mechanical Engineering (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Epoxy Resins (AREA)
- Processes Of Treating Macromolecular Substances (AREA)
Abstract
The disclosure relates to a process for improving the processability, storage stability and/or cure rate of an uncured silica reinforced rubber composition where silica comprises the major filler in the reinforced rubber composition, which comprises combining a mixture comprising, rubber, silica and at least one organic compound having a low molecular weight and a functional group wherein said functional group is at least an epoxy group, such as an epoxy/ether, epoxy/hydroxyl, epoxy/ester, epoxy/amine, ether/amine, episulfide, episulfide/ether, episulfide/hydroxyl, episulfide/ester functional group located in a terminal or sterically unhindered position in the molecule of said organic compound where the molecular weight of said organic compound having a low molecular weight is less than 7,000.
Claims
1. A process for improving the processability, storage stability and/or cure rate of an uncurβd silica reinforced rubber composition where silica comprises the major filler in said reinforced rubber composition, comprising combining a mixture comprising rubber, silica and at least one organic compound comprising an organic compound of relatively low molecular weight that contains at least one functional group, wherein said functional group is at least an epoxy functional group or episulfide functional group located in terminal or sterically unhindered positions in the molecule of said organic compound, where the molecular weight of said organic compound of relatively low molecular weight is less than about 7,000.
2. A process according to Claim 1 wherein the organic compound is N,N- diglycidylaniiine, N , N-d igiycidyl-4-glycidyl oxyaniline, polypropylene glycol diglycidyl ether, isopropylglycidylether, cyclohexylmethyI-3,4- epoxycylcohθxaπecarboxylate, diglycidyl-1 ,2-cyclohexanedicarboxylate, 2,3-epoxypropyl benzene, exo-2,3-epoxynorbornane, poly(bisphenol A- co-epichlorohydrin) glycidyl 4-methyoxy pheπyl ether, diglycidyl ether, poly (pheπylglycidyl ether)-co-formaldehyde, alkyl (Cβ - C12) glycidyl ethers, butyl glycidyl ether, cresyl glycidyl ether, phenyl glycidyl ether, nonyl phenyl glycidyl ether, p-tertiary butyl phenyl glycidyl ether, 2-ethylhexyl glycidyl ether, diglycidyl ether of 1 ,4-butanediol, diglycidyl ether of neopentyi glycol, diglycidyl ether of aliphatic polyol, polygiycidyl ether of castor oil, dimer acid diglycidyl ester, 1,2-epoxy-9-decene, -(2,3- epoxypropyl)phthalimide, the reavction product of resorcinol, formaldehyde, styrene and Bisphenol A, or a vinyl glycidyl chalcogenide and combinations thereof.
3. A process according to Claim 1 wherein said organic compound is present in an amount from about 0.1 to about 30 phr, and said silica is present in an amount greater than about 15 phr,
4. A process according to Claim 1 wherein said silica is precipitated silica or pyrogenic silica or combinations thereof and said mixture contains secondary fillers in lesser amounts than said silica, wherein said secondary fillers are carbon black, clay, mica, talc, inorganic silicates, bentonite, titanium dioxide, aramid pulp, short vegetable fibers, short synthetic polymer fibers, starch, calcium carbonate, or calcium sulfateor combinations thereof, and said organic compounds are present in an amount from about 0.1 to about 30 phr.
5. A process according to Claim 1 wherein said organic compounds are selected to improve processability and reduce the cure time of said rubber composition and are N,N-diglycidyl aniline, N , N-d iglycidyl-4- glycidyl oxyaniline, polypropylene glycol diglycidyl ether, diglycidyl- 1 ,2- cyclohexane dicarboxylate, exo-2,3-epoxynarbomane, poly (Bisphenol A- co-epichlorohydrin) glycidyl end-capped, glycidyl butyrate, glycidyl πeodecanoate, poly(phenylglycidylether)-co-formaldehyde, S^-epoxycyclohexylmethyl-S^-epoxycyclohexaπecarboxylate, the reaction product of resorcinol, formaldehyde, styrene and Bisphenol A diglycidylether polymer.
6. A process according to Claim 1 wherein said rubber is natural rubber, epoxidized natural rubber, methacrylated natural rubber, synthetic polyisoprene, polybutadiene, styrene butadiene copolymers, styrene/isoprene/butadiene copolymers, para or ortho methylstyrene/butadiene rubbers, isoprene/butadiene copolymers, para or ortho methyl styrene/butadiene/isoprene terpolymers, ethylene/propylene/diene rubbers, butyl rubber, isobutylene-isoprene copoly er and its halogeπated derivatives, brominated para-methyl styrene isobutyleπe rubber, butadiene/styrene/acrylonitrile terpolymers, isopreπe/styrene/acryloπitrile terpolymers, butadiene/acryloπitrile
co p o l y m e rs , i s o p re π e/ a c ryl o n itri l e co p o l y m e rs , butadieπe/isoprene/acrylonitrile terpolymers, butadiene-alkyl acrylate or methacrylate copolymers, styrene/butadiene/alkyl acrylate or alkyl methacrylate rubbers, modified styrene/butadiene or butadiene rubbers with silica or carbon black reactive functional groups, and combinations of the aforementioned rubbers with each other and/or with natural rubber.
7. A process according to Claim 6 wherein said rubber composition further includes processing aids, aromatic oils, napthenicoils, paraffin oils, rosin oils, antioxidants, antiozonants, waxes, fillers, resins, adhesions promoters, silica coupling systems, crosslinking systems or curing systems and combinations thereof.
8. A process according to Claim 7 wherein said silica coupling systems comprise polyfunctional organosilanes.
9. The process of Claim 8 wherein said polyfunctional organosilane comprises bis(3-triethoxysilylpropyl)tetrasulfide.
10. A rubber composition of matter comprising a mixture of rubber, silica as the major filler in said composition, and at least one organic compound comprising an organic compound of relatively low molecular weight, and containing at least one functional group, wherein said functional group is at least an epoxy, epoxy/ether, epoxy/hydroxyl, epoxy/ester, epoxy/amine, episulfide, episulfidθ/amine, episulfide/ether, episulfide/hydroxyl, or episulfide/ester functional group located in a terminal or sterically unhindered position in the molecule of said organic compound, or said
organic compound comprises, styrenated resorcinol formaldehyde epoxy polymer compound, or the reactiion products of said mixture, where the molecular weight of said organic compound having relatively low molecular weight is less than about 7,000.
11. A composition of the matter according to Claim 10 wherein the low molecular weight organic compound is N,N-diglycidyl aniline, N,-N- diglycidyl-4-glycidyl oxyaπiline, polypropylene glycol diglycidyl ether, isopropyl glycidyl ether, 3, 4-epoxycyclohexyl methyl -3,4- epoxycyclohexanecarboxylate, diglycidyl- 1 ,2-cyclohexane dicarboxylate, 2,3-epoxypropyl benzene, exo-2,3-epoxynorbomane, poly(bisphenol A-co-epichlorohydriπ) glycidyl end-capped, glycidyl butyrate, glycidyl neodecanoate, glycidyl 4-methoxy phenyl ether, 2-ethyl hexyl diglycidyl ether, poly (phenylglycidyl ether)-co- for aldehyde, cyclohexylmethyl-3,4-epoxycyclohexanecarboxylate, 3,4- epoxycyclohexylmethyl-3,4epoxyclohexanecarboxylate, alkyl (CB - C12) glycidyl ethers, butyl glycidyl ether, cresyl glycidyl ether, phenyl glycidyl ether, nonyl phenyl glycidyl ether, p-tertiary butyl phenyl glycidyl ether, diglycidyl ether of 1 ,4-butanediol, diglycidyl ether of neopentyl glycol, diglycidyl ether of cyclohexane dimethaπol, trimethylol ethane trigylcidyl ether, trimethylol propane triglycidyl ether, diglycidyl ether of dibromoneopentyl glycol, polyglycol diepoxide, polyglycidyl ether or aliphatic polyol, polyglycidyl ether of castor oil, dimeracid diglycidyl ester, 1 ^-epoxy-θ-decene.-^.S-epoxypropy phthalimide, the reaction product of resorcinol, formaldehyde and Bisphenol A diglycidylether polymer, or a vinyl glycidyl chalcogeπide and combinations thereof.
12. A composition of matter according to Claim 10, wherein said organic compound is present in an amount from about 0.1 to about 30 phr, and said silica is present in an amount greater than about 15 phr.
Priority Applications (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| AU2001241828A AU2001241828A1 (en) | 2000-02-28 | 2001-02-28 | Silica reinforced rubber compositions of improved processability and storage stability |
| EP01913134A EP1259565B1 (en) | 2000-02-28 | 2001-02-28 | Silica reinforced rubber compositions of improved processability and storage stability |
| BR0108839-4A BR0108839A (en) | 2000-02-28 | 2001-02-28 | Process for improving processability, storage stability and / or curing rate of the rubber composition reinforced with uncured silica, rubber composition of matter, and, article of manufacture |
| DE60136689T DE60136689D1 (en) | 2000-02-28 | 2001-02-28 | SILICATED ACID REINFORCED RUBBER COMPOSITION WITH IMPROVED PROCESSABILITY AND IMPROVED STORAGE STABILITY |
| JP2001564273A JP2003525333A (en) | 2000-02-28 | 2001-02-28 | Silica reinforced rubber composition with improved processability and storage stability |
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US51464100A | 2000-02-28 | 2000-02-28 | |
| US09/514,641 | 2000-02-29 | ||
| US09/571,503 US6482884B1 (en) | 2000-02-28 | 2000-05-15 | Silica reinforced rubber compositions of improved processability and storage stability |
| US09/571,503 | 2000-05-15 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| WO2001064782A1 WO2001064782A1 (en) | 2001-09-07 |
| WO2001064782B1 true WO2001064782B1 (en) | 2002-02-14 |
Family
ID=27737688
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PCT/US2001/006326 WO2001064782A1 (en) | 2000-02-28 | 2001-02-28 | Silica reinforced rubber compositions of improved processability and storage stability |
Country Status (7)
| Country | Link |
|---|---|
| US (3) | US6482884B1 (en) |
| EP (1) | EP1259565B1 (en) |
| JP (1) | JP2003525333A (en) |
| AT (1) | ATE415451T1 (en) |
| AU (1) | AU2001241828A1 (en) |
| BR (1) | BR0108839A (en) |
| WO (1) | WO2001064782A1 (en) |
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-
2000
- 2000-05-15 US US09/571,503 patent/US6482884B1/en not_active Expired - Fee Related
-
2001
- 2001-02-28 JP JP2001564273A patent/JP2003525333A/en active Pending
- 2001-02-28 BR BR0108839-4A patent/BR0108839A/en not_active Application Discontinuation
- 2001-02-28 AU AU2001241828A patent/AU2001241828A1/en not_active Abandoned
- 2001-02-28 EP EP01913134A patent/EP1259565B1/en not_active Expired - Lifetime
- 2001-02-28 WO PCT/US2001/006326 patent/WO2001064782A1/en active Application Filing
- 2001-02-28 AT AT01913134T patent/ATE415451T1/en not_active IP Right Cessation
-
2002
- 2002-09-06 US US10/235,920 patent/US6737466B2/en not_active Expired - Fee Related
- 2002-09-06 US US10/235,919 patent/US6822037B2/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| AU2001241828A1 (en) | 2001-09-12 |
| EP1259565A1 (en) | 2002-11-27 |
| US20030158317A1 (en) | 2003-08-21 |
| BR0108839A (en) | 2002-12-17 |
| JP2003525333A (en) | 2003-08-26 |
| WO2001064782A1 (en) | 2001-09-07 |
| US20030187110A1 (en) | 2003-10-02 |
| US6737466B2 (en) | 2004-05-18 |
| ATE415451T1 (en) | 2008-12-15 |
| US6482884B1 (en) | 2002-11-19 |
| EP1259565B1 (en) | 2008-11-26 |
| US6822037B2 (en) | 2004-11-23 |
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