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US 10,358,521 B2Granted
Durable hydrogen bonded hydrogels
AssigneeSupraPolix B.V.
InventorsJoris Wilhelmus Peeters, Tristan Mes, Henricus Marie Janssen, Anton Willem Bosman
Life of this patent
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Abstract
This disclosure relates to new injectable hydrogel materials that consist of water gellants comprising linear hydrophilic polymers that comprise hydrogen bonding units in the backbone combined with cross-linkable end groups, resulting in dynamic yet firm hydrogel materials that are easily processable, are highly elastic, show adhesive properties and are self-healing and are especially suitable for biomedical applications.
Claims15
A water gellant comprising a hydrophilic polymer backbone P, a cross-linkable group D that is able to cross-link with other groups D and a 4H-unit 4H, having the structure according to formula (A) or formula (B) or formula (C):
- D-[(4H)]b—[P-(4H)]n—[P]a-D (A)
- or
- {-(4H)b—[P-(4H)]n—[P]a-D-}q (B)
- or
- {-[4H]n—[P-D]q-} (C)
- wherein:
- n is in the range of 1 to 10;
- a is 0 or 1;
- b is 0 or 1;
- q is in the range of 1 to 10;
- D represents the group L-Z, wherein L is a linker moiety that is covalently linked to Z and is selected from (i) the group consisting of cyclic, linear or branched C1-C24 alkylene groups, C6-C24 arylene groups, C7-C24 alkarylene groups and C7-C24 arylalkylene groups and/or (ii) the group consisting of amino acid residues according to the formula (G):
- wherein W is a cyclic, linear or branched C1-C24 alkylene group;
- c is 0-3;
- Z is an aryl group that contains 2 to 6 hydroxy groups or Z is a thiol group;
- 4H represents the 4H-unit that has the general formula (3) or formula (4) and tautomers thereof:
- wherein X is nitrogen atom or a carbon atom bearing a substituent R8 and wherein R1, R2, R3 and R8 are independently selected from the group consisting of:
- (a) hydrogen;
- (b) C1-C20 alkyl;
- (c) C6-C12 aryl;
- (d) C7-C12 alkaryl;
- (e) C7-C12 alkylaryl;
- (f) polyester groups having the formula (5)
- wherein R4 and Y are independently selected from the group consisting of hydrogen and C1-C6 linear or branched alkyl, n is 1-6 and m is 10 to 100;
- (g) C1-C10 alkyl groups substituted with 1-4 ureido groups according to the formula (6)
- R5—NH—C(O)—NH— (6)
- wherein R5 is selected from the group consisting of hydrogen and C1-C6 linear or branched alkyl;
- (h) polyether groups having the formula (7)
- wherein Y, R6 and R7 are independently selected from the group consisting of hydrogen and C1-C6 linear or branched alkyl and o is 10-100;
- and
- wherein the 4H-unit is bonded to the polymer backbone P via R1 and R2 while R3 represents a side chain according to (a)-(h), or via R1 and R3 while R2 represents a side chain according to (a)-(h).
27 more elements
A water gellant produced by a process comprising:
- reacting a polymer component P—(F)v, a precursor of the 4H-unit according to the formula 4H*—(F)w and a cross-linking component (F)x-L-Z, wherein:
- 4H*—(F)w is represented by formula (11) or formula (12):
- wherein X is nitrogen atom or a carbon atom bearing a substituent R8 and wherein R1, R2, R3 and R8 are independently selected from the group consisting of:
- (g) hydrogen;
- (h) C1-C20 alkyl;
- (i) C6-C12 aryl;
- (j) C7-C12 alkaryl;
- (k) C7-C12 alkylaryl;
- (l) polyester groups having the formula (5)
- wherein R4 and Y are independently selected from the group consisting of hydrogen and C1-C6 linear or branched alkyl, n is 1-6 and m is 10 to 100;
- (m) C1-C10 alkyl groups substituted with 1-4 ureido groups according to the formula (6)
- R5—NH—C(O)—NH— (6)
- wherein R5 is selected from the group consisting of hydrogen and C1-C6 linear or branched alkyl;
- (n) polyether groups having the formula (7)
- wherein Y, R6 and R7 are independently selected from the group consisting of hydrogen and C1-C6 linear or branched alkyl and o is 10-100;
- and
- wherein the 4H-unit is bonded to the polymer backbone P via R1 and R2 while R3 represents a side chain according to (a)-(h), or via R1 and R3 while R2 represents a side chain according to (a)-(h);
- F represents a reactive end-group selected from the group consisting of hydroxy, amine, thiol, isocyanate, carboxylic acid, carboxylic ester, and combinations of these end groups;
- v is in the range of 1-4;
- w is in the range of 1-4;
- L represents a linker moiety that is covalently linked to Z and is selected from (i) the group consisting of cyclic, linear or branched C1-C24 alkylene groups, C6-C24 arylene groups, C7-C24 alkarylene groups and C7-C24 arylalkylene groups and/or (ii) the group consisting of amino acid residues according to the formula (G):
- wherein W is a cyclic, linear or branched C1-C24 alkylene group;
- c is 0-3;
- and
- Z represents a group that can cross-link and is selected from a thiol group and an aryl group that contains 2 to 6 hydroxy groups.
22 more elements
Dependencies are inferred from the claim text.