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US 10,377,847 B2Granted
Strong reversible hydrogels
AssigneeSupraPolix B.V.
InventorsTravis Wayne Baughman, Gaby Maria Leonarda Hoorne-Van Gemert, Henricus Marie Janssen, Egbert Willem Meijer, Anton Willem Bosman
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Abstract
The present invention relates to improved hydrogel materials using water gellants that are comprised of polymer backbones P to which hydrogen bonding 4H-units are covalently attached via a hydrophobic linker L. Optionally, the hydrogel contains additional ingredients or additives. These new reversible hydrogels can easily be fine-tuned in their mechanical performance and function and are especially suitable for biomedical applications.
Claims8
A process for preparing a water gellant, comprising:
- (a) covalently attaching a hydrophobic linker L to a hydrophilic polymer backbone P to form an amine functional prepolymer according to the formula:
- wherein:
- L is covalently attached to P by an activation reaction in which
- (i) P—(OH)n is first reacted with
- to produce
- and
- is reacted with a diamine,
- wherein:
- Q is an oxygen or a sulphur atom, and
- LG1 and LG2 are leaving groups selected from the group consisting of imidazole, triazole, halogen, N-hydroxysuccinimide, phenol, substituted phenol, and carboxylate, in which both leaving groups may be the same or different, and
- (b) chain extending the amine functional prepolymer with a difunctional compound whereby the reaction between an amine functional group on the amine functional prepolymer and a functional group on the difunctional compound results in a hydrogen bonding unit, wherein the difunctional compound is selected from:
- (i) diisocyanates, wherein the hydrogen bonding unit is a urea hydrogen bonding unit;
- (ii) dithioisocyanates, wherein the hydrogen bonding unit is a thiourea hydrogen bonding unit;
- (iii) diacid chlorides, wherein the hydrogen bonding unit is an amide hydrogen bonding unit;
- (iv) diesters, wherein the hydrogen bonding unit is an amide hydrogen bonding unit;
- (v) activated diesters, wherein the hydrogen bonding unit is an amide hydrogen bonding unit;
- (vi) diacryl amides, wherein the hydrogen bonding unit is an amide hydrogen bonding unit;
- and
- (vii) dimethacryl amides, wherein the hydrogen bonding unit is an amide hydrogen bonding unit;
- wherein:
- n is in the range of 1.8 to 2;
- RS1 and RS2 represent independently hydrogen or C1-C6 alkyl groups;
- P is a hydrophilic polymer having a solubility in water at least 1 g/L and has a molecular weight of 1,000 daltons to 100,000 daltons;
- and
- L is a hydrophobic linker selected from the group consisting of cyclic, linear or branched C2-C24 alkylene groups, C6-C24 arylene groups, C7-C24 alkarylene groups and C7-C24 arylalkylene groups, and wherein the alkylene groups, arylene groups, alkarylene groups and arylalkylene groups optionally comprise 1-5 heteroatoms selected from the group consisting of O, N and S.
22 more elements
Dependencies are inferred from the claim text.