Cement products and methods of making and using the same

Patent metadata

Field	Value
Publication number	US-9757493-B2
Application number	US-201615149986-A
Country	US
Kind code	B2
Filing date	May 9, 2016
Priority date	Aug 28, 2007
Publication date	Sep 12, 2017
Grant date	Sep 12, 2017

Abstract

Disclosed are cement products, methods of forming cement using the cement product, and methods of using the cement product in orthopedic and dental applications. Generally, the disclosed cement product includes a first component and a second component. The first component comprises a polymerizable resin comprising ethylenic unsaturated double bond, a suitable glycidyl group and/or a suitable isocyanate group. The second component includes a compound comprising more than one type of amine selected from the group consisting of primary amine, secondary amines, tertiary amines and quaternary amines. Alternatively, the second component includes a compound comprising a suitable mercapto (SH—) group, a hindered amine or a dimethylthiotoluenediamine (DMTDA). Optionally, the cement product includes a filler and/or a bioactive component to promote bone formation.

First claim

The invention claimed is:

1. A method of forming a cement product, the method comprising:
(i) mixing a first component and a second component, wherein:
the first component comprises a polymerizable resin that comprises two or more acrylate groups; and
the second component comprises a compound selected from the group consisting of putrescine (1,4-diaminobutane), spermidine, and spermine, and
wherein the first component, the second component, or both the first and second components comprise a bioceramic filler;

(ii) allowing the first component and second component to react with each other in a polymerization reaction at room temperature to produce an orthopedic or dental cement having a compressive strength of about 20 MPa to about 250 MPa, and
(iii) allowing the polymerization reaction mixture to set at about 37° C., wherein the polymerization reaction mixture does not exceed a maximum temperature of 60° C. for a period of one minute.

2. The method of claim 1 , wherein the polymerization reaction mixture does not exceed a maximum temperature of 50° C. for a period of one minute.

3. The method of claim 1 , wherein a dry-to-touch finish of the orthopedic or dental cement is achieved in about 30 minutes or less.

4. The method of claim 1 , wherein a dry-to-touch finish of the orthopedic or dental cement is achieved in about 15 minutes or less.

5. The method of claim 1 , wherein a dry-to-touch finish of the orthopedic or dental cement is achieved in about 10 minutes or less.

6. The method of claim 1 , wherein the second component is blended or grafted with (a) one or more amino acids selected from the group consisting of L-phenylalanine, L-tryptophan, L-arginine, L-cysteine, L-cysteine, L-tyrosine, L-lysine, L-histidine, (b) one or more derivatives of selected from the group of L-phenylalanine, L-tryptophan, L-arginine, L-cysteine, L-cysteine, L-tyrosine, L-lysine, and L-histidine derivatives, or (c) a combination of two or more of the amino acids or derivatives thereof of (a) and (b).

7. The method of claim 1 , wherein the first component comprises a compound selected from the group consisting of bisphenol A glycerolate di(meth)acrylate, non-alkoxylated trimethylpropane tri(meth)acrylate (TMPT(M)A), ethoxylated(15) TMPT(M)A, ethoxylated (9) TMPT(M)A, ethoxylated (6) TMPTA, ethoxylated (3) TMPTA, propoxylated (3) TMPT(M)A, propoxylated (6) TMPT(M)A, propoxylated (5) glycerol ethoxylated bisphenol-A-triacrylate, ethoxylated (2) bisphenol A diacrylate (E(2)BisDA), ethoxylated(4) bisphenol A diacrylate (E(4)BisDA), trimethylolpropane benzoate diacrylate, pentaerythritol triacrylate, pentaerythritoltetraacrylate, butanedioldiacrylate, hexanedioldiacrylate and mixtures thereof.

8. The method of claim 1 , wherein the first component comprises trimethylolpropane triacrylate.

9. The method of claim 1 , wherein the first component comprises non-alkoxylated pentaerythritol triacrylate.

10. The method of claim 1 , wherein the first component comprises E(2)BisDA, E(4)BisDA, trimethylolpropane benzoate diacrylate, 1,4-butandioldiacrylate, 1,3-butanedioldiacrylate, 1,6-hexanediol diacrylate, or a mixture thereof.

11. The method of claim 1 , wherein the second component further comprises one or more synthetic polyamine selected from the group consisting of 2-methyl-1,5-pentamethylenediamine, 2-ethyl-1,3-trimethylenediamine, N-(3-Aminopropyl)-1,3-propanediamine, diethylenetriamine (DETA), triethylenetetramine (TETA), and polyethyleneimine (PEI).

12. The method of claim 11 , wherein
the first component comprises trimethylolpropane triacrylate; and
the second component further comprises 2-methyl-1,5-pentamethylenediamine.

13. The method of claim 12 , wherein
the first component comprises bisphenol A diglycidyl ether 33-67% w/w, trimethylolpropane triacrylate 33-67% w/w, and, optionally, trimethylolpropane benzoate diacrylate 0-33% w/w; and
the second component comprises a mixture of spermidine in an amount of at least 33% w/w and 2-methyl-1,5-pentamethylenediamine in an amount up to 67% w/w.

14. The method of claim 1 , wherein
the first component comprises trimethylolpropane triacrylate; and
the second component further comprises a polyamine selected from the group consisting of 2 methyl-1,5-pentamethylenediamine, 2-ethyl-1,3-trimethylenediamine, or a combination thereof.

15. The method of claim 4 , wherein
the first component comprises sorbitol polyglycidyl ether 0-40% w/w, trimethylolpropane triacrylate in an amount up to 30% w/w, and 1,4-butanediol 0-20% w/w such that the weight percent of sorbitol polyglycidyl ether, the weight percent of trimethylolpropane triacrylate, and the weight percent of 1,4-butanediol total 100% w/w; and
the second component comprises spermidine 20-100% w/w and a second polyamine compound selected from the group consisting of 2-methyl-1,5-pentamethylenediamine and 2-ethyl-1,3-trimethylenediamine, in an amount up to 80% w/w.

16. The method of claim 1 , wherein the bioceramic filler comprises tricalcium phosphate (α-TCP, β-TCP), hydroxyapatite, calcium phosphate, or a mixture thereof.

17. The method of claim 1 , wherein the first component and/or the second component further comprises an initiator or catalyst.

18. The method of claim 17 , wherein the initiator is a photoinitiator selected from the group consisting of a quinone photoinitiator, 2-benzyl-2-(dimethylamino)-4′-morpholino-butyrophenone, or mixtures of 2-hydroxyethy-2-methyl-1-phenyl-1-propanone, and diphenyl(2,4,6-trimethylbenzyl)phosphine oxide.

19. The method of claim 17 , wherein the first component and/or the second component comprises a catalyst and the catalyst comprises a benzoyl peroxide (BPO) catalyst or an amine-containing catalyst.

20. The method of claim 1 , wherein the first component and the second component are each packaged in (i) a separate chamber of the same container or (ii) a separate container.

21. The method of claim 20 , wherein (i) the same container is adapted for injecting cement formed from the first and second component or (ii) each separate container is adapted for injecting cement formed from the first and second component.

Assignees

• Pioneer Surgical Tech Inc

Inventors

• Lin Juchui Ray
• Ahn Edward S
• Schlossberg Brian M

Classifications

• A61K6/887

  Compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds · CPC title

• A61K6/838

  Phosphorus compounds, e.g. apatite · CPC title

• A61K6/884

  comprising natural or synthetic resins · CPC title

• A61L24/04 Primary

  containing macromolecular materials · CPC title

• A61L2300/112

  Phosphorus-containing compounds, e.g. phosphates, phosphonates · CPC title