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;
a second component comprising a compound selected from the group consisting of putrescine (1,4-diaminobutane), spermidine, and spermine; and
a bioceramic filler;
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 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)Bis)A), ethoxylated(4) bisphenol A diacrylate (E(4)BisDA), trimethylolpropane benzoate diacrylate, pentaerythritol triacrylate, pentaerythritoltetraacrylate, butanedioldiacrylate, hexanedioldiacrylate and mixtures thereof.
3. The cement product of claim 1 , wherein the first component comprises trimethylolpropane triacrylate.
4. The cement product of claim 1 , wherein the first component comprises non-alkoxylated pentaerythritol triacrylate.
5. The cement product of claim 1 , wherein the first component comprises E(2)Bis)A, E(4)BisDA, trimethylolpropane benzoate diacrylate, 1,4-butandioldiacrylate, 1,3-butanedioldiacrylate, 1,6-hexanediol diacrylate, or a mixture thereof.
6. The cement product 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).
7. The cement product of claim 1 , wherein
the first component comprises trimethylolpropane triacrylate, and
the second component further comprises 2-methyl-1,5-pentamethylenediamine.
8. The cement product of claim 7 , 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.
9. The cement product 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.
10. The cement product of claim 9 , 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.
11. The cement product of claim 1 , wherein the bioceramic filler comprises tricalcium phosphate, hydroxyapatite, calcium phosphate, or a combination thereof.