IP Library › Granted Patent US 8,022,155
Granted Patent B2
US 8,022,155 · App. 11/918,513 · Granted Sep 20, 2011

Polymerized molded body

Assignee: Technische Universitat Wien
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Quick Facts
Patent No.
US 8,022,155
App. No.
11/918,513
Granted
Sep 20, 2011
Kind
B2
Abstract

The invention relates to polymerizable compositions which comprise 10-80% by weight of a reactive diluent based on acrylic acid or methacrylic acid derivatives, and 10-50% by weight of a monomer of the indicated chemical formula which is liquid or which can be dissolved in the formulation. The formula may contain amino acid residues or peptide sequences, especially such that are specific of the collagen. These structural elements allow the enzymatic degradation of the polymers of the inventive composition.

Claims (29)

1. A method for producing a polymerizate, said method comprising:

A) preparing a polymerization-curable composition by mixing 10 to 80% by weight of component a) with 10 to 50% by weight of component b)

wherein

component a) is a reactive diluent based on acrylic acid or methacrylic acid derivatives, and component b) is a liquid gelatin hydrolysate or a gelatin hydrolysate soluble in the reactive diluent, said liquid gelatin hydrolysate or gelatin hydrolysate soluble in the reactive diluent substituted with a radical of the formula

wherein

R 2 is H or —CH 3 ;

Z 1 is —O—(CH 2 ) x —CO—, —O—(CH 2 —CH 2 —O) x —CH 2 —CO—, —O—(CH 2 —CH 2 —O) x —CO—CH 2 —CH 2 —, —O—(CH 2 —CH 2 —O) x —OC—CH═CH—CO—, —O—CH 2 —CH(OH)—CH 2 —, or —O—(CH 2 —CH 2 —O) x —CH 2 —CH(OH)—CH 2 —;

Z 2 is —O—(CH 2 ) X —O—, —O—(CH 2 —CH 2 —O) x —, —O—CH 2 —CH(OH)—CH 2 —O—, or —O—CH 2 —CH(OH)—CH 2 —O—(CH 2 —CH 2 —O) x —;

x is 1 to 20;

said liquid gelatin hydrolysate or gelatin hydrolysate soluble in the reactive diluent having a molecular weight of up to 10,000 Da; and

B) polymerizing the polymerization-curable composition, in a mold or in layers, into a polymerizate having an E-modulus of more than 1,000 MPa.

2. The method of claim 1 , wherein in step B), the polymerization-curable composition is polymerized by radiation with ultraviolet or visible light.

3. The method according to claim 1 , wherein the component a) is acrylic acid (2-(2-ethoxy)ethoxy)ethyl ester, diisopropylacrylamide, diisobutylacrylamide, acrylic acid 2-(butylcarbamoyloxy)ethyl ester, hydroxyethylmethacrylate, polyethylene glycol diacrylate, trimethylolpropane triacrylate, or a mixture thereof.

4. The method according to claim 1 , wherein the component b) comprises a methacryloylated gelatin hydrolysate.

5. The method according to claim 1 , wherein the component b) comprises peptides comprising the sequence arginine-glycine-aspartic acid (RGD).

6. The method according to claim 1 , wherein 2 hydroxy-1-[4-(2-hydroxyethoxy)phenyl]-2-methyl-1-propanone or phenyl-bis(2,4,6-trimethylbenzoyl)phosphine oxide is added to the polymerization-curable composition as an initiator.

7. The method according to claim 1 , wherein campherquinone is added to the polymerization-curable composition as an initiator and one or more of dimethylaniline, triethanolamine or methyl diethanolamine is added to said polymerization-curable composition as a co-initiator.

8. The method according to claim 1 , wherein hydroxyapatite, tricalcium phosphate, bone meal, or keratin fibers is added to the polymerization-curable composition as filler.

9. The method according to claim 1 , wherein the components of the composition are dissolved in organic solvents comprising a water content of <10%.

10. A molded article prepared according to claim 1 , wherein the molded article has a cellular structure having a pore diameter between 150 μm and 500 μm.

11. A molded article prepared according to claim 1 , wherein a surface of the molded article comprises a coating of hydroxyapatite.

12. A molded article prepared according to claim 1 , wherein a surface of the molded article comprises covalently attached proteins, peptides, amino acids, or oligonucleotides.

13. The molded article according to claim 12 , wherein the proteins are selected from the group consisting of bone morphogenic proteins (BMP), cytokines, growth factors and cell differentiation factors, collagens, and collagen fragments.

14. The method according to claim 1 , wherein the components of the polymerization-curable composition are dissolved in organic solvents comprising a water content of less than about 1%.

15. The method according to claim 1 , wherein the components of the polymerization-curable composition are dissolved in organic solvents comprising a water content of less than about 0.1%.

16. The method of claim 1 , wherein the polymerizate obtained in step B) has an E-modulus of more than 1,500 MPa.

17. The method of claim 16 , wherein the polymerizate has an E-modulus of more than 2,000 MPa.

18. The method of claim 17 , wherein the polymerizate has an E-modulus of more than 5,000 MPa.

19. The method of claim 18 , wherein the polymerizate has an E-modulus of more than 10,000 MPa.

Assignments (1)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Oct 26, 2007
From: LISKA, ROBERT; SCHUSTER, MONIKA; STAMPFL, JURGEN; GRUBER, HEINRICH; VARGA, FRANZ
To: TECHNISCHE UNIVERSITAT WIEN
Reel/Frame 020037/0645 →
Priority Claims (1)
AT A 626/2005 · Apr 14, 2005 · national
Continuity (1)
Related Publication 20080287565A1 · Nov 20, 2008