# US 10,934,385 B1 · Polyurethane elastomers, bio-additive foam compositions > Agents: this data is available as JSON from the patentgrep API and MCP server — see https://patentgrep.com/llms.txt - Number: US 10,934,385 B1 - Document ID: US10934385B1 - Status: Granted - Kind: B1 - Application number: 17/015,808 - Filed: 2020-09-09 - Granted: 2021-03-02 - Earliest claimed: 2020-09-09 - Assignees: Evoco Limited - Applicants: Evoco Ltd. - Inventors: Jason James Robinson; Mustafa Abu Ghalia; Syed Muhammad Husainie - Web page: https://patentgrep.com/patent/US10934385B1 ## CPC - C08G 18/4238: {derived from dicarboxylic acids and dialcohols} - C08G 18/2081: {containing at least two non-condensed heterocyclic rings} - C08G 18/3206: {aliphatic} - C08G 18/3275: {containing two hydroxy groups} - C08G 18/4202: {Two or more polyesters of different physical or chemical nature (C08G18/44 takes precedence)} - 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} - C08G 63/16: Dicarboxylic acids and dihydroxy compounds - C08K 5/0041: {Optical brightening agents, organic pigments} - C08K 5/11: of acyclic polycarboxylic acids - C08G 2101/00: Manufacture of cellular products - C08G 2110/0066: ≥ 150kg/m3 - C08G 2410/00: Soles - C08G: MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS - 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 a bio-additive 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, and wherein the amount of bio-additive is from 1 percent by weight to 10 percent by weight. ### 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 40 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, wherein said bio-additive is present in an amount of from 1 percent by weight to 10 percent by weight 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, said bio-additive is present in an amount of from 1 percent by weight to 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, wherein said bio-additive is present in an amount of from 1 percent by weight to 10 percent by weight 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, a bio-additive 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 diethanolamine, 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 a bio-additive; 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 wherein said bio-additive is present in an amount of from 1 percent by weight to 10 percent by weight, 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.