# US 10,934,384 B1 · Polyurethane elastomer compositions, and processes thereof > Agents: this data is available as JSON from the patentgrep API and MCP server — see https://patentgrep.com/llms.txt - Number: US 10,934,384 B1 - Document ID: US10934384B1 - Status: Granted - Kind: B1 - Application number: 17/015,669 - Filed: 2020-09-09 - Granted: 2021-03-02 - Earliest claimed: 2020-09-09 - Assignees: Evoco Limited - Applicants: Evoco Ltd. - Inventors: Jason James Robinson; Guerino G. Sacripante; Radu Lucian Vicol; Mustafa Abu Ghalia; Ying Wang; Sanjoy Mullick - Web page: https://patentgrep.com/patent/US10934384B1 ## CPC - C08G 18/4238: {derived from dicarboxylic acids and dialcohols} - A43B 13/04: Plastics, rubber or vulcanised fibre - A43B 13/187: {Resiliency achieved by the features of the material, e.g. foam, non liquid materials} - A43B 17/14: made of sponge, rubber, or plastic materials - C08G 18/2063: {having two nitrogen atoms in the condensed ring system} - C08G 18/222: {metal compounds not provided for in groups C08G18/225 - C08G18/26} - C08G 18/3203: {Polyhydroxy compounds} - C08G 18/3206: {aliphatic} - C08G 18/3275: {containing two hydroxy groups} - C08G 18/664: {with compounds of group C08G18/3203} - C08G 18/6655: {with compounds of group C08G18/3271} - C08G 18/7671: {containing only one alkylene bisphenyl group} - C08K 5/11: of acyclic polycarboxylic acids - C08G 2110/0008: flexible - C08G 2110/0066: ≥ 150kg/m3 - C08G 2110/0083: prepared using water as the sole blowing agent - C08G 2190/00: Compositions for sealing or packing joints - C08G 2410/00: Soles - C08G: MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS - A43B: CHARACTERISTIC FEATURES OF FOOTWEAR; PARTS OF FOOTWEAR - C08K: Use of inorganic or non-macromolecular organic substances as compounding ingredients (paints, inks, varnishes, dyes, polishes, adhesives C09) ## Abstract A polyurethane elastomer composition of (a) an organic diisocyanate, (b) a polyester resin; (c) a chain extender comprised of a polyhydric alcohol, (d) a crosslinker, (e) a plasticizer, (f) a surfactant, (g) a blowing or foaming agent, and (h) an optional dye; and where the elastomer has, for example, a hardness value of, for example, from about 20 Asker C to about 60 Asker C, a tensile strength of, for example, from about 1 MPa to about 10 MPa, a resilience of, for example, from about 30 percent to about 60 percent, an elongation at break of from about 150 percent to about 700 percent, and a tear strength of, for example, from about 2 Newtons/millimeters2 to about 4 Newtons/millimeters2. ## Claims ### Claim 1 A polyurethane elastomer composition formed by mixing and then reacting a composition comprising (a) an organic diisocyanate, (b) a polyester resin, (c) a chain extender, (d) a crosslinker, (e) a plasticizer, (f) a surfactant, (g) an optional foaming agent, and (h) an optional colorant, and wherein said elastomer has a hardness value of from about 15 Asker C to about 60 Asker C, a tensile strength of from about 1 MPa to about 10 MPa, a resilience of from about 25 percent to about 60 percent, an elongation at break of from about 150 percent to 700 percent, and a tear strength of from 2 Newtons/millimeters to about 4 Newtons/millimeters, and wherein said polyester is a semi-crystalline polyester selected from the group consisting of poly(1,3-propylene-succinate), and copoly(1,3-propylene-succinate)-copoly(1,2-propylene-succinate). ### Claim 2 (depends on 1) The polyurethane elastomer in accordance with claim 1 wherein the bio-content of the polyurethane elastomer is from about 50 percent to about 90 percent, and further including a catalyst. ### Claim 3 (depends on 1) The polyurethane elastomer in accordance with claim 1 in the configuration of a foam, wherein the foaming agent is present, and the bio-content of the polyurethane elastomer foam is from about 70 percent to about 85 percent, and further including a catalyst. ### Claim 4 (depends on 1) The polyurethane elastomer in accordance with claim 1 wherein the melting point of said semi-crystalline resin is from about 15 degrees Centigrade to about 49 degrees Centigrade. ### Claim 5 (depends on 1) The polyurethane elastomer in accordance with claim 1 wherein the foaming agent is present, and wherein said organic diisocyanate is selected from the group consisting of diphenylmethane 4,4′-diisocyanate, isophorone diisocyanate, dicyclohexylmethane 4,4-diisocyanate, hexamethylene 1,6-diisocyanate, naphthalene 1,5-diisocyanate, and mixtures thereof, and further including a catalyst. ### Claim 6 (depends on 1) The polyurethane elastomer in accordance with claim 1 wherein said organic diisocyanate is methylenediphenyl diisocyanate. ### Claim 7 (depends on 1) The polyurethane elastomer in accordance with claim 1 wherein said plasticizer is selected from the group consisting of tributyl-citrate, triethyl-citrate, trimethyl-citrate, and an adipate. ### Claim 8 (depends on 1) The polyurethane elastomer in accordance with claim 1 wherein said surfactant is selected from the group consisting of a polyether-silicone oil, sodium dodecylbenzene sulfonate, sodium dodecylnaphthalene sulfate, adipic acid, polyvinyl alcohol, polyacrylic acid, methalose, methyl cellulose, and ethyl cellulose. ### Claim 9 (depends on 1) The polyurethane elastomer in accordance with claim 1 wherein said chain extender is selected from the group consisting of polyhydric alcohols, alkylene diols and alkylene glycols, and further including a catalyst. ### Claim 10 (depends on 1) The polyurethane elastomer in accordance with claim 1 wherein said crosslinker is selected from the group consisting of diethanolamine, glycerol, trimethylol propane, pentaerythritol, 1,2,4-butanetriol, thioglycolic acid, 2,6-dihydroxybenzoic acid, melamine, and mixtures thereof. ### Claim 11 (depends on 1) The polyurethane elastomer in accordance with claim 1 in the configuration of a foam, wherein said colorant is a dye present in an amount of from about 0.5 percent by weight to about 5 percent by weight, and wherein the foaming agent is present. ### Claim 12 (depends on 1) The polyurethane elastomer in accordance with claim 1 wherein said foaming agent is present, said elastomer possesses a hydrolytic stability of from about 80 percent to about 150 percent, possesses a resilience of from about 35 percent to about 60 percent, and has a compression set of from about 3 percent to about 6 percent. ### Claim 13 (depends on 1) The polyurethane elastomer in accordance with claim 1 wherein said plasticizer is tributyl citrate, said crosslinker is an amine, said chain extender is a propane diol, said foaming agent is present and is water or carbon dioxide, and said colorant is present and is comprised of a dye or a pigment. ### Claim 14 (depends on 1) The polyurethane elastomer in accordance with claim 1 in the configuration of a foam, and wherein said colorant is present in an amount of from about 0.5 percent by weight to about 5 percent by weight, and is comprised of a dye of black, cyan, magenta, yellow, green, red, orange, blue, white, purple or mixtures thereof; and wherein said foaming agent is present and is comprised of carbon dioxide or water. ### Claim 15 (depends on 1) The polyurethane elastomer composition in accordance with claim 1 wherein said polyester is poly(1,3-propylene-succinate), said plasticizer is tributyl citrate, said surfactant is a silicone component, and said organic diisocyanate is methylenediphenyl diisocyanate, said chain extender is 1,3-propanediol, said crosslinker is diethanolamine, said colorant is present, and is comprised of a dye. ### Claim 16 (depends on 1) The polyurethane elastomer composition in accordance with claim 1 wherein said polyester is poly(1,3-propylene-succinate), said organic diisocyanate is methylenediphenyl diisocyanate, said colorant is present, and is comprised of a component selected from the group consisting of a dye and a pigment, and said foaming agent is present. ### Claim 17 An article of manufacture comprising a polyurethane elastomer composition, said polyurethane elastomer composition is formed by mixing and then reacting a composition comprising (a) an organic diisocyanate, (b) a polyester resin, (c) a chain extender, (d) a crosslinker, (e) a plasticizer, (f) a surfactant, (g) an optional foaming agent, (h) an optional colorant, and an optional catalyst; and wherein said elastomer has a hardness value of from about 20 Asker C to about 60 Asker C, a tensile strength of from about 1 MPa to about 10 MPa, a resilience of from about 25 percent to about 60 percent, an elongation at break of from about 150 percent to 700 percent, and a tear strength of from about 2 Newtons/millimeters to about 4 Newtons/millimeters, and wherein said polyester is a semi-crystalline polyester selected from the group consisting of poly(1,3-propylene-succinate), and copoly(1,3-propylene-succinate)-copoly(1,2-propylene-succinate). ### Claim 18 (depends on 17) The article in accordance with claim 17 wherein said elastomer is an insole, a midsole, or a combination thereof, and said Asker C is from about 15 to about 40 Asker C, and said tensile strength is from about 2 MPa to about 3 MPa. ### Claim 19 (depends on 17) The article in accordance with claim 17 wherein said colorant is present and is comprised of a dye, a pigment, or mixtures thereof, and said foaming agent is present and is comprised of water. ### Claim 20 (depends on 17) The article in accordance with claim 17 wherein said plasticizer is tributyl citrate, said crosslinker is an amine, said chain extender is a propane diol, said foaming agent is present and is comprised of water or carbon dioxide, and said colorant is present and is comprised of a dye or a pigment. ### Claim 21 A process for the preparation of polyurethane elastomers comprising mixing of and then reacting (a) an organic diisocyanate, (b) a polyester resin, (c) a chain extender, (d) a crosslinker, (e) a plasticizer, (f) a surfactant, (g) a foaming agent, and (h) an optional colorant; and wherein said elastomer has a hardness value of from about 15 Asker C to about 60 Asker C, a tensile strength of from about 1 MPa to about 10 MPa, a resilience of from about 30 percent to about 60 percent, an elongation at break of from about 150 percent to 700 percent, and a tear strength of from 2 Newtons/millimeters to about 4 Newtons/millimeters, and wherein said polyester is a semi-crystalline polyester selected from the group consisting of poly(1,3-propylene-succinate), and copoly(1,3-propylene-succinate)-copoly(1,2-propylene-succinate). ### Claim 22 (depends on 21) The process in accordance with claim 21 where the polyurethane elastomer is an insole, a midsole, or a combination thereof, and optionally is a foam having a density of from about 0.25 gram/centimeter3 to about 0.55 gram/centimeter3, a bio-content of from about 70 to about 90 percent, and a compression set of from about 3 percent to about 6 percent and an elongation at break of from about 300 percent to 650 percent.