Cement products and methods of making and using the same
View Patent ↗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.
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.