# US 7,608,658 B2 · Amine-functionalized liquid polyisoprene > Agents: this data is available as JSON from the patentgrep API and MCP server — see https://patentgrep.com/llms.txt - Number: US 7,608,658 B2 - Document ID: US7608658B2 - Status: Granted - Kind: B2 - Application number: 12/267,086 - Filed: 2008-11-07 - Published: 2009-03-05 - Granted: 2009-10-27 - Earliest claimed: 2004-02-17 - Assignees: The Goodyear Tire & Rubber Company - Inventors: Michael Joseph Rachita; Vanessa Marika Guscoff; Lawson Gibson Wideman - Web page: https://patentgrep.com/patent/US7608658B2 ## CPC - B29C 67/246: {Moulding high reactive monomers or prepolymers, e.g. by reaction injection moulding [RIM], liquid injection moulding [LIM] (casting monomers B29C39/006, mixing construction B29B7/74)} - B29B 7/7495: {for mixing rubber} - C08C 19/25: Incorporating silicon atoms into the molecule - C08C 19/30: Addition of a reagent which reacts with a hetero atom or a group containing hetero atoms of the macromolecule - C08L 19/006: {Rubber characterised by functional groups, e.g. telechelic diene polymers} - C08K 5/5419: containing at least one Si—C bond - B29C: SHAPING OR JOINING OF PLASTICS; SHAPING OF MATERIAL IN A PLASTIC STATE, NOT OTHERWISE PROVIDED FOR; AFTER-TREATMENT OF THE SHAPED PRODUCTS, e.g. REPAIRING (making preforms B29B11/00; making laminated products by combining previously unconnected layers which become one product whose layers will remain together B32B37/00 - B32B41/00) - B29B: PREPARATION OR PRETREATMENT OF THE MATERIAL TO BE SHAPED; MAKING GRANULES OR PREFORMS; RECOVERY OF PLASTICS OR OTHER CONSTITUENTS OF WASTE MATERIAL CONTAINING PLASTICS - C08C: TREATMENT OR CHEMICAL MODIFICATION OF RUBBERS - C08L: COMPOSITIONS OF MACROMOLECULAR COMPOUNDS (compositions based on polymerisable monomers C08F, C08G; artificial filaments or fibres D01F; textile treating compositions D06) - C08K: Use of inorganic or non-macromolecular organic substances as compounding ingredients (paints, inks, varnishes, dyes, polishes, adhesives C09) ## Abstract This invention discloses a process for manufacturing an elastomeric article by liquid injection molding, said process comprising the steps of: (I) heating a curable composition comprised of (1) a liquid polymer comprised of repeat units that are derived from a conjugated diolefin monomer, wherein said liquid polymer has a weight average molecular weight which is within the range of 5,000 to 100,000, and wherein the liquid polymer is functionalized with an amine moiety, (2) a carbonyl inhibited platinum catalyst, and (3) a tetrakis(dialkyl siloxy) silane crosslinking agent, to a temperature which is within the range of 30° C. to 100° C.; (II) injecting the heated curable composition into a mold at a temperature which is within the range of 100° C. to 210° C. to produce the elastomeric article; and (III) removing the elastomeric article from the mold. ## Claims ### Claim 1 A cured elastomeric article made by a process which comprises: (I) heating a curable composition to a temperature which is within the range of 30° C. to 100° C., wherein the curable composition is comprised of (1) a liquid polymer comprised of repeat units that are derived from a conjugated diolefin monomer, wherein said liquid polymer has a weight average molecular weight which is within the range of 5,000 to 100,000, wherein the liquid polymer has a vinyl microstructure content of at least 15 percent, and wherein the liquid polymer is functionalized with an amine moiety, (2) a carbonyl inhibited platinum catalyst, and (3) a tetrakis(dialkyl siloxy) silane crosslinking agent; (II) injecting the heated curable composition into a mold at a temperature which is within the range of 100° C. to 210° C. to produce the elastomeric article; and (III) removing the elastomeric article from the mold. ### Claim 2 (depends on 1) A cured elastomeric article as specified in claim 1 wherein the tetrakis(dialkyl siloxy) silane crosslinking agent is present at a level which is within the range of 0.5 phr to 10 phr. ### Claim 3 (depends on 1) A cured elastomeric article as specified in claim 1 wherein the curable composition is cured in the mold at a temperature which is within the range of 120° C. to 180° C. ### Claim 4 (depends on 1) A cured elastomeric article as specified in claim 1 wherein the curable composition is void of oils. ### Claim 5 (depends on 1) A cured elastomeric article as specified in claim 1 wherein the curable composition is further comprised of 5 phr to 40 phr of a silica filler. ### Claim 6 (depends on 3) A cured elastomeric article as specified in claim 3 wherein the tetrakis(dialkyl siloxy) silane crosslinking agent is present at a level which is within the range of 2 phr to 5 phr. ### Claim 7 (depends on 1) A cured elastomeric article as specified in claim 1 wherein the liquid polymer has a weight average molecular weight which is within the range of 30,000 to 50,000. ### Claim 8 (depends on 7) A cured elastomeric article as specified in claim 7 wherein the liquid polymer has a vinyl microstructure content which is within the range of 15 percent to 20 percent. ### Claim 9 (depends on 1) A cured elastomeric article as specified in claim 1 wherein the liquid polymer is further comprised of repeat units that are derived from 1-ethenyl-4-(3-butenyl)benzene. ### Claim 10 (depends on 1) A cured elastomeric article as specified in claim 1 wherein the liquid polymer is functionalized with an amine moiety by incorporating into the polymer repeat units which are derived from at least one amine functionalized monomer of the structural formula: wherein R represents an alkyl group containing from 1 to about 10 carbon atoms or a hydrogen atom, and wherein R1 and R2 can be the same or different and represent hydrogen atoms or a moiety selected from the group consisting of wherein the R3 groups can be the same or different and represent alkyl groups containing from 1 to about 10 carbon atoms, aryl groups, allyl groups, and alkyloxy groups of the structural formula —(CH2)y—O—(CH2)z—CH3, wherein Z represents a nitrogen-containing heterocyclic compound, and wherein n, x, y and z represents integers from 1 to about 10, with the proviso that R1 and R2 cannot both be hydrogen atoms. ### Claim 11 (depends on 10) A cured elastomeric article as specified in claim 10 wherein wherein R1 and R2 can be the same or different and represent hydrogen atoms or a moiety of the formula: wherein x represents an integer from 1 to about 10, and wherein Z is selected from the group consisting of wherein R5 groups can be the same or different and represent a member selected from the group consisting of alkyl groups containing from 1 to about 10 carbon atoms, aryl groups, allyl groups, and alkoxy groups, and wherein Y represents oxygen, sulfur, or a methylene group. ### Claim 12 (depends on 10) A cured elastomeric article as specified in claim 10 wherein the amine functionalized monomer is incorporated into the liquid polymer at a level which is within the range of about 0.1 weight percent to about 5 weight percent. ### Claim 13 (depends on 10) A cured elastomeric article as specified in claim 10 wherein the amine functionalized monomer is incorporated into the liquid polymer at a level which is within the range of about 0.3 weight percent to about 3 weight percent. ### Claim 14 (depends on 10) A cured elastomeric article as specified in claim 10 wherein the amine functionalized monomer is incorporated into the liquid polymer at a level which is within the range of about 0.5 weight percent to about 1 weight percent. ### Claim 15 (depends on 10) A cured elastomeric article as specified in claim 10 wherein the amine functionalized monomer is incorporated into the liquid polymer at a level which is within the range of about 0.3 weight percent to about 3 weight percent and wherein the conjugated diolefin monomer is isoprene. ### Claim 16 (depends on 10) A cured elastomeric article as specified in claim 10 wherein the amine functionalized monomer is incorporated into the liquid polymer at a level which is within the range of about 0.3 weight percent to about 3 weight percent and wherein the liquid polymer is further comprised of repeat units which are derived from a vinyl aromatic monomer. ### Claim 17 (depends on 16) A cured elastomeric article as specified in claim 16 wherein the vinyl aromatic monomer is styrene. ### Claim 18 (depends on 10) A cured elastomeric article as specified in claim 10 wherein the amine functionalized monomer is incorporated into the liquid polymer at a level which is within the range of about 0.3 weight percent to about 3 weight and wherein R1 and R2 can be the same or different and represent hydrogen atoms or a moiety of the formula: wherein x represents an integer from 1 to about 10, and wherein n represents an integer from 1 to about 10. ### Claim 19 (depends on 10) A cured elastomeric article as specified in claim 10 wherein the amine functionalized monomer is incorporated into the liquid polymer at a level which is within the range of about 0.3 weight percent to about 3 weight percent and wherein R1 and R2 can be the same or different and represent hydrogen atoms or a moiety of the formula: wherein x represents an integer from 1 to about 10, and wherein R3 groups can be the same or different and represent alkyl groups containing from 1 to about 10 carbon atoms. ### Claim 20 (depends on 10) A cured elastomeric article as specified in claim 10 wherein the amine functionalized monomer is incorporated into the liquid polymer at a level which is within the range of about 0.3 weight percent to about 3 weight percent and wherein the liquid polymer is further comprised of repeat units that are derived from 1-ethenyl-4-(3-butenyl)benzene.