# US 8,785,552 B2 · Solvent-free crosslinked polyrotaxane material and process for production of same > Agents: this data is available as JSON from the patentgrep API and MCP server — see https://patentgrep.com/llms.txt - Number: US 8,785,552 B2 - Document ID: US8785552B2 - Status: Granted - Kind: B2 - Application number: 13/054,923 - Filed: 2009-08-31 - Published: 2011-05-26 - Granted: 2014-07-22 - Earliest claimed: 2008-09-01 - Assignees: Advanced Softmaterials Inc. - Applicants: Yuki Hayashi; Toru Kobayashi; Junko Suda; Michiko Ito - Inventors: Yuki Hayashi; Toru Kobayashi; Junko Suda; Michiko Ito - Web page: https://patentgrep.com/patent/US8785552B2 ## CPC - C08G 63/912: {derived from hydroxycarboxylic acids} - C08G 18/10: Prepolymer processes involving reaction of isocyanates or isothiocyanates with compounds having active hydrogen in a first reaction step - C08G 18/4018: {Mixtures of compounds of group C08G18/42 with compounds of group C08G18/48} - C08G 18/4238: {derived from dicarboxylic acids and dialcohols} - C08G 18/4277: {Caprolactone and/or substituted caprolactone} - C08G 18/48: Polyethers - C08G 18/4833: {Polyethers containing oxyethylene units} - C08G 18/61: Polysiloxanes - C08G 18/757: {containing at least two isocyanate or isothiocyanate groups linked to the cycloaliphatic ring by means of an aliphatic group} - C08G 18/792: {formed by oligomerisation of aliphatic and/or cycloaliphatic isocyanates or isothiocyanates} - C08G 83/007: {Polyrotaxanes; Polycatenanes} - C08G: MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS ## Abstract A material comprising crosslinked polyrotaxanes which exhibits desired viscoelasticity, particularly stress-strain characteristics with a wide low-stress region, in spite of being free from solvent; and a process for production of the same. The material comprises a first polyrotaxane bearing first cyclic molecules and a second polyrotaxane bearing second cyclic molecules, and the first and second polyrotaxanes are crosslinked via the first and second cyclic molecules. The material is free from solvent and exhibits a stress of 2.0 MPa or below at 50% strain. ## Claims ### Claim 1 A material comprising a first polyrotaxane and a second polyrotaxane, wherein the first polyrotaxane comprises a first pseudopolyrotaxane, which has a first linear molecule and a first cyclic molecule(s) in which the first linear molecule is included in a cavity (cavities) of the first cyclic molecule(s) in a skewered manner, and first capping groups, each of which locates at each end of the first pseudopolyrotaxane in order to prevent the dissociation of the first cyclic molecule(s), the second polyrotaxane comprises a second pseudopolyrotaxane, which has a second linear molecule and a second cyclic molecule(s) in which the second linear molecule is included in a cavity (cavities) of the second cyclic molecule(s) in a skewered manner, and second capping groups, each of which locates at each end of the second pseudopolyrotaxane in order to prevent the dissociation of the second cyclic molecule(s), the first and second linear molecules are polyethylene glycol, the first and second polyrotaxanes are crosslinked with each other via the first and second cyclic molecules, each of the first and second cyclic molecules has a first active group and a second active group, respectively, the crosslinked body has a crosslinking moiety which is bound to the first cyclic molecule and the second cyclic molecule, the crosslinking moiety has a first reactive group and a second reactive group, each of which is reactive with the first active group and the second active group, respectively, and the crosslinking moiety has a polymeric moiety between the first and second reactive groups, the reactive group is selected from the group consisting of an isocyanate group, a thioisocyanate group, an oxirane group, an oxetane group, a carbodiimide group, a silanol group, an oxazoline group, and an aziridine group, the polymeric moiety comprises repeating units of 10 or more and/or has molecular weight of 1,000 or more, the material is free from solvent, and the material has a stress at 50% strain (δ50) of 2.0 MPa or less. ### Claim 2 (depends on 1) The material according to claim 1, wherein the material has a stress at 100% strain (δ100) of 2.5 MPa or less. ### Claim 3 (depends on 1) The material according to claim 1, wherein the material has breaking extension ratio of more than 100%. ### Claim 4 (depends on 1) The material according to claim 1, wherein a stress gradient ΔS, which is represented by (δ100-δ50)δ50, may be 1.0 or less. ### Claim 5 (depends on 1) The material according to claim 1, wherein δ50 ranges from 0.01 to 0.50 MPa, ΔS ranges from 0.02 to 0.30, and the breaking extension ratio is more than 800%. ### Claim 6 (depends on 1) The material according to claim 1, wherein δ50 ranges from 0.20 to 0.70 MPa, ΔS ranges from 0.15 to 0.70, and the breaking extension ratio ranges from more than 200% to 800%. ### Claim 7 (depends on 1) The material according to claim 1, wherein δ50 ranges from 0.60 to 2.0 MPa, ΔS ranges from 0.50 to 1.0, and the breaking extension ratio ranges from more than 100% to 200%. ### Claim 8 (depends on 1) The material according to claim 1, wherein each of the first and second reactive groups has two functional groups or more. ### Claim 9 (depends on 1) The material according to claim 1, wherein the polymeric moiety has a plurality of polymers and a linker moiety linking the plurality of polymers. ### Claim 10 (depends on 1) The material according to claim 1, wherein the polymeric moiety has a branched chain. ### Claim 11 (depends on 10) The material according to claim 10, wherein the branched chain is in any one of the plurality of polymers, and/or in the linker moiety. ### Claim 12 (depends on 1) The material according to claim 1, wherein the active group is derived from a group selected from the group consisting of —OH, —SH, —NH2, —COOH, —SO3H, and —PO4H. ### Claim 13 (depends on 8) The material according to claim 8, wherein the two functional groups or more is two groups or more selected from the group consisting of an isocyanate group, a thioisocyanate group, an oxirane group, an oxetane group, a carbodiimide group, a silanol group, an oxazoline group, and an aziridine group. ### Claim 14 (depends on 1) The material according to claim 1, wherein the polymeric moiety is polyether, polyester, polysiloxane, polycarbonate, poly(meth)acrylate or polyene, or copolymer thereof. ### Claim 15 (depends on 1) The material according to claim 1, wherein the active group is derived from an —OH group, the reactive group or the functional group is an isocyanate group, the polymeric moiety is polyether, polyester or polysiloxane. ### Claim 16 (depends on 2) The material according to claim 2, wherein the material has breaking extension ratio of more than 100%. ### Claim 17 (depends on 2) The material according to claim 2, wherein a stress gradient ΔS, which is represented by (δ100-δ50)/δ50, may be 1.0 or less. ### Claim 18 (depends on 2) The material according to claim 2, wherein δ50 ranges from 0.01 to 0.50 MPa, ΔS ranges from 0.02 to 0.30, and the breaking extension ratio is more than 800%. ### Claim 19 (depends on 2) The material according to claim 2, wherein δ50 ranges from 0.20 to 0.70 MPa, ΔS ranges from 0.15 to 0.70, and the breaking extension ratio ranges from more than 200% to 800%. ### Claim 20 (depends on 2) The material according to claim 2, wherein δ50 ranges from 0.60 to 2.0 MPa, ΔS ranges from 0.50 to 1.0, and the breaking extension ratio ranges from more than 100% to 200%. ### Claim 21 (depends on 2) The material according to claim 2, wherein each of the first and second cyclic molecules has a first active group and a second active group, respectively, the crosslinked body has a crosslinking moiety which is bound to the first cyclic molecule and the second cyclic molecule, the crosslinking moiety has a first reactive group and a second reactive group, each of which is reactive with the first active group and the second active group, respectively, and the crosslinking moiety has a polymeric moiety comprising repeating units of 10 or more between the first and second reactive groups. ### Claim 22 (depends on 21) The material according to claim 21, wherein the polymeric moiety has molecular weight of 1,000 or more.