IP Library Granted Patent US 12698394
Granted Patent B2
US 12698394 · App. 18/641,890 · Granted Aug 4, 2026

Composite material and its method of production

Inventors: Alexander Seifalian (London, GB); Stephen Hancock (London, GB)
Assignee: NANOREGMED LIMITED
C08L75/06A61L27/443A61L27/507A61L29/126C01B32/15C08G18/10C08G18/44C08G18/4841C08G18/7621C08G18/7671C08G18/831C08G18/833C08J5/005C08K3/04C08K3/041C08K3/042C08K3/043C08K3/044C08K3/045C08K3/046C08L75/00C08L75/02C08L75/04C08L75/08C08L75/10A61L2400/12A61L2430/14A61L2430/20
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Quick Facts
Patent No.
US 12698394
App. No.
18/641,890
Granted
Aug 4, 2026
Kind
B2
Abstract

A composite material that is a copolymer of at least (i) a functionalised carbon nanoparticle, (ii) a polyol, (iii) a compound comprising at least two isocyanate groups, wherein the functionalised carbon nanoparticle and the polyol are covalently bonded by a urethane and optionally a urea and/or an amide linkage, and a process for producing the same. The composite materials are suitable for use in moulded articles for implantation within a mammal.

Claims (21)

1 . A composite material obtained from a process comprising a step of polymerizing

(i) a functionalized carbon nanoparticle that is graphene oxide functionalized with primary amino groups,

(ii) a polyol selected from the group consisting of a polycarbonate diol and a polycaprolactone diol,

(iii) a methylenebisphenyl isocyanate compound comprising at least two isocyanate groups, and

(iv) optionally a chain extending compound comprising at least two primary amine groups,

wherein the process comprises preparing a mixture of (i) and (ii), heating the mixture to clarify the mixture, and thereafter adding (iii) to the clarified mixture and polymerizing (i), (ii) and (iii).

2 . The composite material according to claim 1 , wherein the chain extending compound is an aliphatic amine.

3 . The composite material according to claim 1 , wherein the composite material comprises a carbon nanoparticle moiety obtained from the functionalized carbon nanoparticle (i) and a polyol moiety obtained from the polyol (ii), wherein the carbon nanoparticle moiety is covalently bonded to the polyol moiety by a urethane linkage and a urea linkage or by a urethane linkage and an amide linkage.

4 . The composite material according to claim 1 , comprising a second step of adding a monoamine after completion of the step of polymerizing.

5 . The composite material according to claim 1 , wherein the primary amino groups are present on both the edge and the plane of the graphene oxide.

6 . The composite material according to claim 1 , wherein the functionalized carbon nanoparticle is made by a process comprising the steps of converting carboxylic acid moieties present on a graphene oxide nanoparticle into acyl chloride groups, reacting the acyl chloride groups with ammonium hydroxide to convert them into amido groups, and reducing the amido groups to primary amino groups.

7 . A composite material which is a copolymer of (i) a functionalized carbon nanoparticle which is graphene oxide functionalized with primary amine groups, (ii) a polyol selected from the group consisting of a polycarbonate diol and a polycaprolactone diol, (iii) a methylenebisphenyl isocyanate compound comprising at least two isocyanate groups, optionally (iv) a chain extending compound comprising at least two primary amine groups, and optionally (v) a monoamine,

wherein the functionalized carbon nanoparticle and the polyol are covalently bonded by a urethane linkage and a urea linkage or by a urethane linkage and an amide linkage,

wherein the copolymer is prepared by preparing a mixture of (i) and (ii), heating the mixture to clarify the mixture, and thereafter adding (iii) to the clarified mixture and polymerizing (i), (ii) and (iii).

8 . The composite material according to claim 7 , wherein the chain extending compound is selected from the group consisting of an aliphatic amine, an aliphatic carboxylic acid, an aliphatic alcohol, a functionalized silica nanoparticle, an amino acid, a peptide, and a polypeptide.

9 . The composite material according to claim 7 , wherein the primary amino groups and, where present, primary alcoholic groups, are present on both the edge and the plane of the graphene sheet.

10 . The composite material according to claim 7 , wherein the functionalized carbon nanoparticle is made by a process comprising the steps of converting carboxylic acid moieties present on a carbon nanoparticle into acyl chloride groups, reacting the acyl chloride groups with ammonium hydroxide to convert them into amido groups, and reducing the amido groups to primary amino groups.

11 . A molded article comprising the composite material of claim 1 .

12 . A molded article comprising the composite material of claim 7 .

13 . The composite material of claim 1 , wherein the mixture of (i) and (ii) is heated to a temperature of at least 80° C.

14 . The composite material of claim 7 , wherein the mixture of (i) and (ii) is heated to a temperature of at least 80° C.