IP Library Granted Patent US 12698472
Granted Patent B2
US 12698472 · App. 17/621,734 · Granted Aug 4, 2026

Hydrogels

Inventors: Julieta I. Paez (Saarbrücken, DE); Aleeza Farrukh (Irvine, CA); Aránzazu del Campo (Mainz-Bretzenheim, DE)
Assignee: Leibniz-Institut für Neue Materialien gemeinnützige GmbH
C12N5/0012C08J3/075C08J3/246C12N5/0062C12N5/0656C08J2300/206C08J2371/02
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Quick Facts
Patent No.
US 12698472
App. No.
17/621,734
Granted
Aug 4, 2026
Kind
B2
Abstract

A process for preparing a hydrogel includes a) preparing a composition comprising a 1 ) at least one macromer comprising as functional groups at least two thiol groups, and a 2 ) at least one macromer comprising as functional groups at least two aromatic or heteroaromatic groups each substituted by at least one sulfonyl group, wherein at least one component a 1 ) or a 2 ) has at least three of the functional groups; and b) reacting the two macromers a 1 ) and a 2 ) via the functional groups to form a hydrogel.

Claims (33)

1 . A process for preparing a hydrogel, comprising:

a) preparing a composition comprising:

a1) at least one macromer comprising as functional groups at least two thiol groups,

a2) at least one macromer comprising as functional groups at least two aromatic or heteroaromatic groups each substituted by at least one sulfonyl group, wherein the at least one macromer a1) or the at least one macromer a2) has at least three of the respective functional groups; and

b) reacting the the at least one macromer a1) and the at least one macromer a2) via the respective functional groups to form a hydrogel,

wherein the functional groups of the at least one macromer a2) are functional groups of the formula (1):

wherein:

Ar is an electron-deficient aryl group or electron-deficient heteroaryl group;

M is the connection to the macromer;

R 1 is N(R 2 ) 2 , a straight-chain alkyl group having 1 to 20 C atoms or a branched or cyclic alkyl group having 3 to 20 C atoms, or an alkenyl or alkynyl group having 2 to 20 C atoms or a branched or cyclic alkyl group having 3 to 20 C atoms, wherein the alkyl, alkenyl or alkynyl group may be substituted in each case by one or more radicals R 2 and where one or more nonadjacent CH 2 groups may be replaced by O, NR 2 , S, R 2 C═CR 2 , C≡C, C═O, C(═O)O or C(═O)NR 2 , or is an aryl group or heteroaryl group which may be substituted in each case by one or more radicals R 2 ;

R 2 , identical or different at each occurrence, is H, D, F, Cl, Br, I, N(R 3 ) 2 , CN, NO 2 , OR 3 , SR 3 , C(═O)OR 3 , C(═O) N(R 3 ) 2 , C(═O) R 3 , a straight-chain alkyl group having 1 to 20 C atoms or an alkenyl or alkynyl group having 2 to 20 C atoms or a branched or cyclic alkyl group having 3 to 20 C atoms, wherein the alkyl, alkenyl or alkynyl group may be substituted in each case by one or more radicals R 3 , where one or more nonadjacent CH 2 groups may be replaced by R 3 C═CR 3 , C≡C, C═O, NR 3 , O, S, C(═O)O or C(═O)NR 3 , or is an aryl group or heteroaryl group which may be substituted in each case by one or more radicals R 3 ; and

R 3 , identical or different at each occurrence, is H, D, F, OH, or an aliphatic, aromatic and/or heteroaromatic organic radical in which one or more H atoms may also be replaced by F.

2 . The process as claimed in claim 1 , wherein each of the at least one macromers a1) and a2) have an average molar mass of less than 500 kDa.

3 . The process as claimed in claim 1 , wherein each of the at least one macromers a1) and a2) contain 2, 3, 4, 5, 6, 7, 8, 9 or 10 of the respective functional groups.

4 . The process as claimed in claim 1 , wherein each of the at least one macromers a1) and a2) are based on poly(meth)acrylates, poly(meth)acrylamides, poly(meth)acrylic acid, polyHPMA, polyHEMA, polyethylene glycol, polyvinyl alcohol, polyurethane, polyvinylpyrrolidone, polyamides, poly(amido-amines), polyesters, polylactides, polyglycolic acid, poly(lactide-co-glycolide), polyanhydrides, poly(ortho)esters, polyacetals, poloxamers, poly-2-oxazolines, polyphosphazenes, polyglycerol, polyamines, polycarbonates, polyglutamic acid, polyaspartic acid, polyphosphonates, DNA, RNA, gelatin, polyhydroxyalkanoates, poly-gamma-glutamic acid, proteins, peptides, or polysaccharides.

5 . The process as claimed in claim 1 , wherein Ar is selected from the group consisting of nitrobenzenes, benzaldehydes, benzonitriles, benzoic esters, pyridines, pyrimidines, pyrazines, pyridazines, triazines, tetrazines, oxazoles, isoxazole, thiazoles, isothiazole, oxadiazoles, 1,2,3-thiadiazole, 1,2,4-thiadiazole, 1,2,5-thiadiazole, 1,3,4-thiadiazole, imidazole, pyrazole, triazoles, tetrazole, quinolines, isoquinolines, benzimidazole, benzoxazole, benzothiazole, benzopyridazine, benzopyrimidine, quinoxaline, benzotriazole, naphthalimide, purine, pteridine, indolizine and benzothiadiazole, wherein Ar may be substituted in each case additionally by one or more groups R 2 .

6 . The process as claimed in claim 1 , wherein a macromer content of the composition is 1 to 30 wt % based on the at least one macromer a1) and the at least one macromer a2).

7 . The process as claimed in claim 1 , wherein gelling takes place under physiological conditions.

8 . A hydrogel obtained as claimed in claim 1 .

9 . A composition for preparing a hydrogel, comprising components a1) and a2) as claimed in claim 1 .

10 . A kit for preparing a hydrogel, comprising components a1) and a2) as claimed in claim 1 .

11 . The process as claimed in claim 1 , wherein each of the at least one macromers a1) and a2) is based on block copolymers of ethylene oxide (PEG) and propylene oxide (PPG).

12 . The process as claimed in claim 1 , wherein each of the at least one macromers a1) and a2) is based on polylysine or polyethylenimine.

13 . The process as claimed in claim 1 , wherein each of the at least one macromers a1) and a2) is based on poly-gamma-glutamic acid.

14 . The process as claimed in claim 1 , wherein each of the at least one macromers a1) and a2) is based on collagens, VPM, albumin or fibrin.

15 . The process as claimed in claim 1 , wherein each of the at least one macromers a1) and a2) is based on agarose, chitin, chitosan, chondroitin, mannan, inulin, dextran, cellulose, alginates or hyaluronic acid.

16 . A process, comprising:

preparing a hydrogel as claimed in claim 1 ; and

encapsulating cells in the hydrogel.

17 . A process, comprising:

preparing a hydrogel as claimed in claim 1 ; and

injecting the hydrogel into an organism, 3D printing with the hydrogel, or transporting an active ingredient to cells with the hydrogel.

18 . The process as claimed in claim 1 , wherein R 3 , identical or different at each occurrence, is a straight-chain alkyl group having 1 to 20 C atoms in which one or more H atoms may also be replaced by F.