Multi-component adhesive for producing an adhesive hydrogel

Patent metadata

Field	Value
Publication number	US-2016130484-A1
Application number	US-201414769299-A
Country	US
Kind code	A1
Filing date	Feb 21, 2014
Priority date	Feb 21, 2013
Publication date	May 12, 2016
Grant date	—

Abstract

The present invention primarily relates to a multicomponent adhesive for producing an adhesive hydrogel, comprising the compound defined below of the formula (I) and one, two, three, four or more further constituents. The invention further relates to the use of said multicomponent adhesive and corresponding methods for gluing two surfaces together. The present invention further relates to a method for producing a corresponding adhesive hydrogel. The invention also relates to a kit comprising a corresponding multicomponent adhesive and one or more further constituents. The invention also relates to articles which comprise a multicomponent adhesive according to the invention or an adhesive hydrogel produced therefrom.

First claim

1 . A multicomponent adhesive for producing an adhesive hydrogel, comprising
a) a first compound of the formula (I)

wherein
X is selected from the group consisting of SH, NH 2 and alpha,beta-unsaturated carbonyl groups, and
L is a linker which links the 1,2-dihydroxyphenyl unit with X, wherein the linker L is linked with the 1,2-dihydroxyphenyl unit in the 3 or 4 position;

and
b) at least one second compound containing at least one structural unit (II)
B-L′-Y  (II)

wherein in each of the structural units (II) independently of the meaning in other structural units (II)
B is a linkage point,
L′ is a linker, and
Y is selected from the group consisting of SH, NH 2 and alpha,beta-unsaturated carbonyl groups and can be reacted with the group X with formation of at least one covalent bond;

and
c) at least one of
(i) the second compound additionally comprising a residue Z, which independently of every other residue Z of another second compound is selected from the group consisting of SH, NH 2 and alpha,beta-unsaturated carbonyl groups and can be reacted with a group Y with formation of at least one covalent bond,
and
(ii) at least one third compound, which independently of another third compound comprises at least two structural units (III)
B′-L″-Z′  (III)

wherein in each of the structural units (III) independently of the meaning in other structural units (III)
B′ is a linkage point,
L″ is a linker, and
Z′ is selected from the group consisting of SH, NH 2 and alpha,beta-unsaturated carbonyl groups and can be reacted with a group Y with formation of at least one covalent bond.

2 . The multicomponent adhesive as claimed in claim 1 , further comprising at least one of
d) a buffer consisting of a buffer acid and a corresponding buffer base, where the pK B of the buffer base is not less than 2, and e) one or more bases with a pK B <1.

3 . The multicomponent adhesive as claimed in claim 1 , wherein the first compound of the formula (I) contains at least one cysteine unit.

4 . The multicomponent adhesive as claimed in claim 3 , wherein the first compound of the formula (I) contains at least one L-cysteine unit (formula X).

5 . The multicomponent adhesive as claimed in claim 1 , wherein at least one of
(i) the linker L of the first compound of the formula (I) is an organic molecule unit, the chain members whereof consisting of at least one of (a) exclusively carbon atoms and (b) carbon atoms and hetero atoms, (ii) the linker L′ in the structural unit B-L′-Y (II) is an organic molecule unit, the chain members whereof consisting of at least one of (a) exclusively carbon atoms and (b) carbon atoms and hetero atoms, and (iii) the linker L″ in the structural unit B′-L″-Z′ (III) is an organic molecule unit, the chain members whereof consisting of at least one of (a) exclusively carbon atoms and (b) carbon atoms and hetero atoms.

6 . The multicomponent adhesive as claimed in claim 1 , wherein the linker L in the first compound of the formula (I) contains at least one structural unit selected from the group consisting of glycine, alanine, valine, leucine, isoleucine, methionine, phenylalanine, tryptophan, proline, serine, threonine, cysteine, tyrosine, asparagine, glutamine, aspartic acid, glutamic acid, lysine, arginine and histidine.

7 . The multicomponent adhesive as claimed in claim 6 , wherein the linker L in the first compound of the formula (I) contains at least one structural unit selected from the group consisting of cysteine, alanine, lysine, proline, serine, tyrosine and threonine.

8 . The multicomponent adhesive as claimed in claim 1 , wherein the linker L in the first compound of the formula (I) contains at least one structural unit selected from the group of amino acid sequences consisting of alanine-lysine, lysine-proline, proline-serine, serine-tyrosine, tyrosine-proline, proline-proline, proline-threonine, alanine-lysine-proline, lysine-proline-serine, proline-serine-tyrosine, serine-tyrosine-proline, tyrosine-proline-proline, proline-proline-threonine, alanine-lysine-proline-serine (SEQ ID NO: 1), lysine-proline-serine-tyrosine (SEQ ID NO: 2), proline-serine-tyrosine-proline (SEQ ID NO: 3), serine-tyrosine-proline-proline (SEQ ID NO: 4), tyrosine-proline-proline-threonine (SEQ ID NO: 5), alanine-lysine-proline-serine-tyrosine (SEQ ID NO: 6), lysine-proline-serine-tyrosine-proline (SEQ ID NO: 7), proline-serine-tyrosine-proline-proline (SEQ ID NO: 8), serine-tyrosine-proline-proline-threonine (SEQ ID NO: 9), alanine-lysine-proline-serine-tyrosine-proline (SEQ ID NO: 10), lysine-proline-serine-tyrosine-proline-proline (SEQ ID NO: 11), proline-serine-tyrosine-proline-proline-threonine (SEQ ID NO: 12), alanine-lysine-proline-serine-tyrosine-proline-proline (SEQ ID NO: 13), lysine-proline-serine-tyrosine-proline-proline-threonine (SEQ ID NO: 14), and alanine-lysine-proline-serine-tyrosine-proline-proline-threonine (SEQ ID NO: 15)

9 . The multicomponent adhesive as claimed in claim 1 , wherein the first compound of the formula (I) has a structure according to the formula (IV)

10 . The multicomponent adhesive as claimed in claim 1 , wherein the structural unit (II) has the following structure (IIa):

wherein
n is a whole number greater than or equal to 1,
x is selected from the group consisting of 0, 1, 2, 3, 4, 5, 6, 7, and 8,
and
m is selected from the group consisting of 0, 1, 2, 3, 4, 5, 6, 7, and 8.

11 . The multicomponent adhesive as claimed in claim 1 , wherein the second compound (b) comprises at least one compound selected from compounds of the formula (V)

wherein
n in each of the four side chains independently of the meaning of n in the respective other side chains is a whole number greater than or equal to 1,
m in each of the four side chains independently of the meaning of m in the respective other side chains is selected from the group consisting of 0, 1, 2, 3, 4, 5, 6, 7, and 8,
and
Y in each of the four side chains independently of the meaning of Y in the respective other side chains is selected from the group consisting of SH, NH 2 and alpha,beta-unsaturated carbonyl groups and can be reacted with the group X with formation of at least one covalent bond.

12 . The multicomponent adhesive as claimed in claim 1 , wherein each of the structural units (III) has the following structure (IIIa):

wherein
o is a whole number greater than or equal to 1,
q is selected from the group consisting of 0, 1, 2, 3, 4, 5, 6, 7, and 8,
and
p is selected from the group consisting of 0, 1, 2, 3, 4, 5, 6, 7, and 8.

13 . The multicomponent adhesive as claimed in claim 1 , wherein the third compound comprising the at last two structural units (III) comprises at least one compound selected from the group of compounds according to formula (VII)

Assignees

• Fraunhofer Ges Forschung
• Tech Universität Darmstadt
• Johann Wolfgang Goethe Universität

Inventors

• Rischka Klaus
• Sader Robert
• Bargel Hendrik
• Kozielec Maria

Classifications

• A61L24/0031

  Hydrogels or hydrocolloids · CPC title

• A61L2430/12

  for dental implants or prostheses · CPC title

• C09J171/02 Primary

  Polyalkylene oxides · CPC title

• A61L24/06

  obtained by reactions only involving carbon-to-carbon unsaturated bonds {(A61L24/043, A61L24/046 take precedence)} · CPC title

• C08G65/2609

  containing aliphatic hydroxyl groups · CPC title