Cement products and methods of making and using the same

Patent metadata

Field	Value
Publication number	US-9358319-B2
Application number	US-201414461138-A
Country	US
Kind code	B2
Filing date	Aug 15, 2014
Priority date	Aug 28, 2007
Publication date	Jun 7, 2016
Grant date	Jun 7, 2016

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. An orthopedic cement product comprising:
a first component comprising a polymerizable resin that comprises two or more acrylate groups in combination with a second polymerizable resin comprising three or more acrylate groups;
a second component comprising an aliphatic or aromatic polyamine having at least one secondary amine group selected from the group consisting of spermidine, spermine, diethylenetriamine, tetraethylenepentamine, pentaethylenehexamine, N-(3-aminopropyl)-1,3-propanediamine, and 2,6-diaminopurine; and
a bioceramic filler selected from the group consisting of tricalcium phosphate, hydroxyapatite, calcium phosphate, or a combination thereof;
wherein the first component and second component are capable of reacting with each other in a polymerization reaction to produce an orthopedic or dental cement,
wherein when the first component and second component are reacted together in a polymerization reaction at room temperature and allowed to set at about 37° C., the reaction does not exceed a maximum temperature of 60° C. for a period of one minute; and
wherein the cement product after setting has a compressive strength of about 20 MPa to about 250 MPa.

2. The cement product of claim 1 , wherein the first component comprises a di- or multi-acrylate selected from the group consisting of a 1,3-butanediol diacrylate, a 1,4-butanediol diacrylate, a 1,6-hexanediol diacrylate, a glycerol diacrylate, an ethyleneglycol diacrylate, a polyethyleneglycol diacrylate, a triethylene glycol diacrylate, a neopentyl glycol diacrylate, a propoxylated neopentylglycol diacrylate, a trimethylolpropane triacrylate, alkoxylated trimethylpropane triacrylate, trimethylolpropane benzoate diacrylate, a di-, tri-, or tetra-acrylate of pentaerythritol or dipentaerythritol, and combinations thereof.

3. The cement product of claim 1 , wherein the first filler comprises a trimethylolpropane triacrylate, alkoxylated trimethylpropane triacrylate, trimethylolpropane benzoate diacrylate, a di-, tri-, or tetra-acrylate of pentaerythritol or dipentaerythritol, or a combination thereof.

4. The cement product of claim 1 , wherein the bioceramic filler comprises tricalcium phosphate, hydroxyapatite, calcium phosphate, or a combination thereof.

5. An orthopedic cement product comprising:
a first component comprising a polymerizable resin that comprises an ethylenic unsaturated double bond and a functional group selected from the group consisting of a glycidyl ester group, a glycidyl ether group, an ester containing a glycidyl ether group, a carbonate containing a glycidyl ether group, or a combination thereof; and
a second component comprising a polyamine selected from the group consisting of propylenediamine, butylenetriamine, diethylenetriamine, tetraethylenepentamine, pentaethylenehexamine, N-(3-aminopropyl)-1,3-propanediamine, 2-methyl-1,5-pentamethylenediamine, 2-ethyl-1,3-trimethylenediamine, spermidine, spermine, putrescine, xylenediamine, tetrachloro-p-xylenediamine, methylenedianiline, N-methylpiperazine, hydroxyethylpiperazine, dimethylthiotoluenediamine, polyaniline, diaminodiphenylsulfone, p-diaminoazobenzene, 4,4′-diaminodiphenyl ether, menthanediamine, isophoronediamine, streptidine, stilbamidine, 2-deosystreptamine, lysine, polyaspartate, polyaspartic esters, guanidine, arginine, uracil, thymine, adenine, guanine, cytosine, xanthine, 2,4-diamino-6-hydroxypyrimidine, 2,6-diaminopurine, tryptophan, and mixtures thereof;
wherein the first component and second component are capable of reacting with each other in a polymerization reaction to produce an orthopedic or dental cement, and wherein when the first component and second component are reacted together in a polymerization reaction at room temperature and allowed to set at about 37° C., the reaction does not exceed a maximum temperature of 60° C. for a period of one minute; and
wherein the cement product after setting has a compressive strength of about 20 MPa to about 250 MPa.

6. The cement product of claim 5 , wherein the first component comprises a polymerizable resin selected from the group consisting of glycerol polyglycidyl ether, diglycidyl sebacate, diglycidyl azelate, diglycidyl pimelate, diglycidyl adipate, diglycidyl succinate, diglycidyl oxalate, 1,4-butanediol diglycidyl ether, polyglycidyl(meth)acrylate, poly[(phenyl glycidyl ether)co-formaldehyde], N,N-diglycidyl-4-glycidyloxyaniline ether, neopentyl glycol diglycidyl ether, bisphenol A diglycidyl ether, bisphenol A propoxylate (1 PO/phenol) diglycigyl ether, bisphenol F epoxy resin, a bisphenol A epoxy resin, sorbitol polyglycidyl ether, and trimethylolpropanetriglycidyl ether.

7. The cement product of claim 5 , wherein the second component comprises a polyamine selected from the group consisting of propylenediamine, butylenetriamine, diethylenetriamine, tetraethylenepentamine, pentaethylenehexamine, N-(3-aminopropyl)-1,3-propanediamine, 2-methyl-1,5-pentamethylenediamine, 2-ethyl-1,3-trimethylenediamine, spermidine, spermine, putrescine.

8. The cement product of claim 6 , wherein the second component comprises a polyamine selected from the group consisting of propylenediamine, butylenetriamine, diethylenetriamine, tetraethylenepentamine, pentaethylenehexamine, N-(3-aminopropyl)-1,3-propanediamine, 2-methyl-1,5-pentamethylenediamine, 2-ethyl-1,3-trimethylenediamine, spermidine, spermine, putrescine.

9. The cement product of claim 5 , wherein the cement further comprises a bioceramic filler.

10. The cement product of claim 5 , wherein the cement further comprises tricalcium phosphate, hydroxyapatite, calcium phosphate, or a combination thereof.

11. The cement product of claim 1 , wherein the first component comprises pentaerythritol tetraacrylate in combination with trimethylolpropane benzoate diacrylate, the second component comprises spermidine, and the cement further comprises tricalcium phosphate filler.

Assignees

• Pioneer Surgical Tech Inc

Inventors

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

Classifications

• A61K6/838

  Phosphorus compounds, e.g. apatite · CPC title

• A61K6/887

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

• A61K6/884

  comprising natural or synthetic resins · CPC title

• A61L2400/12

  Nanosized materials, e.g. nanofibres, nanoparticles, nanowires, nanotubes; Nanostructured surfaces · CPC title

• A61L2300/412

  Tissue-regenerating or healing or proliferative agents · CPC title