IP Library › Granted Patent US 11,649,318
Granted Patent B2
US 11,649,318 · App. 16/621,506 · Granted May 16, 2023

Biocompatible materials

Inventors: Andrew Dove (Birmingham, GB); Andrew Weems (Birmingham, GB)
Assignee: 4D MEDICINE LIMITED
C08G18/755C08G18/3876C08G18/44C08G18/702C08G18/8166
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Quick Facts
Patent No.
US 11,649,318
App. No.
16/621,506
Granted
May 16, 2023
Kind
B2
Abstract

A resin composition, the resin composition comprising a prepolymer ( 209 ) and optionally one or more diluent(s) (FIG. 3 A), the prepolymer ( 209 ) comprising repeating units having at least one carbonate linkage and at least one unsaturated side-chain, the at least one optional diluent(s) comprising at least one unsaturated side-chain, wherein either or both of the prepolymer ( 209 ) and the at least one optional diluent(s) comprises at least one O═C—N linkage, preferably a urethane linkage.

Claims (32)

1. A resin composition, the resin composition comprising a prepolymer and at least one diluent, the prepolymer comprising repeating units having at least one carbonate linkage and at least one unsaturated side-chain, said at least one diluent(s) comprising at least one unsaturated side chain, wherein either the prepolymer comprises at least one O═C—N linkage or said at least one diluent comprises at least one O═C—N linkage but not both the prepolymer and said at least one diluent comprises at least one O═C—N linkage.

2. A resin composition according to claim 1 , wherein the prepolymer comprises at least one O═C—N linkage.

3. A resin composition according to claim 1 , wherein the at least one O═C—N linkage is a urethane linkage.

4. A resin composition according to claim 1 , the prepolymer comprising repeating units having at least one carbonate linkage, at least one urethane linkage, and at least one unsaturated side-chain.

5. A resin composition according to claim 2 , further comprising a cross-linker, the cross-linker comprising a moiety that is capable of reacting with the at least one unsaturated side-chain of the prepolymer and/or the at least one diluent.

6. A resin composition according to claim 5 , wherein the cross-linker has the formula (vi):

7. A resin composition according to claim 2 , wherein the at least one diluent comprises plural unsaturated side-chains.

8. A resin composition according to claim 2 , wherein the at least one diluent is selected from the following (ii) to (v):

9. A resin composition according to claim 1 , wherein the prepolymer has the formula (vii):

wherein R group is an aliphatic or an aromatic moiety, R 1 is an aliphatic or an aromatic moiety, R 2 is an aliphatic or an aromatic moiety, R 3 is an aliphatic or an aromatic moiety, and R 4 is an aliphatic or an aromatic moiety, and wherein x is a number that is less than one hundred.

10. A resin composition, the resin composition comprising a prepolymer, the prepolymer comprising repeating units having at least one carbonate linkage and at least one unsaturated side-chain, wherein the prepolymer comprises at least one O═C—N linkage and has the formula (viii):

wherein R group is an aliphatic or an aromatic moiety, R 1 is an aliphatic or an aromatic moiety, R 2 is an aliphatic or an aromatic moiety, R 3 is an aliphatic or an aromatic moiety, and R 4 is an aliphatic or an aromatic moiety, and wherein x is a number that is less than one hundred.

11. A resin composition according to claim 1 , wherein the prepolymer is fabricated from components comprising the formulae (ix):

wherein R group is an aliphatic or an aromatic moiety, R 1 is an aliphatic or an aromatic moiety, R 2 is an aliphatic or an aromatic moiety, R 3 is an aliphatic or an aromatic moiety, and R 4 is an aliphatic or an aromatic moiety, and wherein x is a number that is less than one hundred.

12. A resin composition according to claim 5 , wherein the prepolymer is present in a quantity of between 10 and 100 w/w % of the total composition, the diluent is present in a quantity of between 0 and 50 w/w % of the total composition, and the cross-linker is present in a quantity of between 0 and 50 w/w % of the total composition.

13. A cross-linked polymer comprising a resin composition of claim 1 which has been cross linked.

14. A method of fabricating a cross-linked polymer, the method comprising:

i. providing a resin composition according to claim 1 .

15. A method according to claim 14 , comprising:

ii. contacting the resin composition with a initiator; and

iii. providing an energy source to activate the initiator.

16. A method according to claim 15 , comprising contacting the resin composition with a photoinitiator and exposing the resin composition to a light source, for example, UV light.

17. A method according to claim 15 , wherein the initiator is present in a quantity of between 0 and 5 w/w% of the total composition.

18. A method according claim 15 , comprising forming the cross-linked polymer by stereolithography.

19. A method according to claim 15 , the method further comprising step iv. providing a reagent for halogenation of the at least one unsaturated side chain.

20. A method according to claim 15 , further comprising a further step selected from one or more of the following group:

step v. providing a reagent for alkylation of the at least one unsaturated side chain;

step vi. providing a reagent for functionalising the at least one unsaturated side chain with a hydrophobic moiety;

step vii. providing a reagent for functionalising the at least one unsaturated side chain with a cell adhesion moiety.

21. A resin composition according to claim 1 , wherein said at least one diluent comprises at least one O═C—N linkage.

22. A resin composition, the resin composition comprising a prepolymer and at least one diluent, said at least one diluent(s) comprising at least one unsaturated side chain and at least one O═C—N linkage, the prepolymer comprising repeating units having at least one carbonate linkage and at least one unsaturated side-chain, wherein the prepolymer is fabricated by polymerisation of monomer 202 ;

and wherein the prepolymer comprises the repeating unit shown in formula;

Assignments (3)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Dec 29, 2021
From: THE UNIVERSITY OF BIRMINGHAM
To: 4D MEDICINE LIMITED
Reel/Frame 058501/0653 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jul 2, 2020
From: THE UNIVERSITY OF WARWICK
To: THE UNIVERSITY OF BIRMINGHAM
Reel/Frame 053110/0886 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Dec 31, 2019
From: DOVE, ANDREW; WEEMS, ANDREW
To: THE UNIVERSITY OF WARWICK
Reel/Frame 051393/0413 →
Priority Claims (1)
GB 1709287 · Jun 12, 2017 · national
Continuity (1)
Related Publication 20200115490A1 · Apr 16, 2020