IP Library Granted Patent US 10,799,610
Granted Patent B2
US 10,799,610 · App. 16/532,799 · Granted Oct 13, 2020

Cement products and methods of making and using the same

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Quick Facts
Patent No.
US 10,799,610
App. No.
16/532,799
Granted
Oct 13, 2020
Kind
B2
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.

Claims (19)

1. A method of treating a patient in need of treatment for a bone defect, comprising

(i) providing a first component and a second component, wherein the first component comprises a di-acrylate resin, a tri-acrylate resin, a tetra-acrylate resin or a combination thereof, and the second component comprises an aliphatic polyamine containing primary and secondary amine groups and not containing tertiary amine groups, wherein the ratio of primary to secondary amine groups in the aliphatic polyamine is 2, and wherein the first component and second component are capable of reacting with each other in a polymerization reaction to produce a cement;

(ii) mixing the first component and second component at room temperature to form a cement, wherein such mixing does not exceed a maximum temperature of 50° C. for a period of one minute;

(iii) flowing the cement into voids or crevices within the defective bone of the patient or in between the defective bone of the patient and tissue or an implant, and

(iv) allowing the cement to set and thereby repairing the bone defect in the patient;

wherein the cement has a viscosity suitable for injection through a 4 to 18 gauge needle,

wherein the time to 50% of maximum compression strength of the cement is about 1 hour, and

wherein the cement maintains at least from about 5% to about 50% of initial strength for at least 6 months.

2. 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.

3. The method of claim 2 , 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.

4. The method of claim 1 , wherein the patient has a bony defect or fracture.

5. The method of claim 4 , wherein the bony defect is due to osteoporosis, stress fracture, traumatic fracture, compression fracture, and combinations thereof.

6. The method of claim 5 , wherein the bone defect is a vertebral bone defect due to trauma or osteoporosis.

7. The method of claim 1 , wherein the patient is in need of an implant.

8. The method of claim 1 , wherein the first component comprises a combination of a di-acrylate resin and either a tri-acrylate resin or a tetra-acrylate resin.

9. The method of claim 1 , wherein the polyamine is spermidine.

10. The method of claim 1 , wherein the first component comprising a multi-functional acrylate is selected from the group consisting of ethoxylated (2) bisphenol A diacrylate, bisphenol A glycerolate (1-glycerol/phenol)diacrylate, diethyleneglycol diacrylate, dipropyleneglycol diacrylate, 1,3-butyleneglycol diacrylate, 1,4-butanediol diacrylate, 1,6-hexanediol diacrylate, trimethylolpropane benzoate diacrylate, glyceryl propoxy triacrylate, pentaerythritol triacrylate, pentaerythritol tetraacrylate, tris(2-hydroxyethyl)isocyanurate triacrylate, trimethylolpropane triacrylate, and mixtures thereof.

11. The method of claim 1 , wherein each of the first component and second component further comprise alpha-tricalcium phosphate having a particle size of 30 microns or less and wherein the amount of tricalcium phosphate is about 50% to about 80% by weight of the cement product.

12. The method of claim 1 , wherein the working time for the reaction between the first component and second component to produce a cement is about 10 minutes.

Assignments (8)
SECURITY INTEREST Recorded Aug 11, 2024
From: XTANT MEDICAL, INC.; BACTERIN INTERNATIONAL, INC.; X-SPINE SYSTEMS, INC.; SURGALIGN SPV, INC.; XTANT MEDICAL HOLDINGS, INC.
To: MIDCAP FUNDING IV TRUST
Reel/Frame 068539/0492 →
SECURITY INTEREST Recorded Aug 11, 2024
From: XTANT MEDICAL, INC.; BACTERIN INTERNATIONAL, INC.; X-SPINE SYSTEMS, INC.; SURGALIGN SPV, INC.; XTANT MEDICAL HOLDINGS, INC.
To: MIDCAP FINANCIAL TRUST
Reel/Frame 068539/0665 →
SECURITY AGREEMENT SUPPLEMENT (REVOLVING) Recorded Dec 22, 2023
From: XTANT MEDICAL HOLDINGS, INC.; XTANT MEDICAL, INC.; BACTERIN INTERNATIONAL, INC.; X-SPINE SYSTEMS, INC.
To: MIDCAP FUNDING IV TRUST
Reel/Frame 066095/0652 →
SECURITY AGREEMENT SUPPLEMENT (TERM) Recorded Dec 22, 2023
From: XTANT MEDICAL HOLDINGS, INC.; XTANT MEDICAL, INC.; BACTERIN INTERNATIONAL, INC.; X-SPINE SYSTEMS, INC.
To: MIDCAP FINANCIAL TRUST
Reel/Frame 066095/0635 →
MERGER Recorded Oct 19, 2023
From: PIONEER SURGICAL TECHNOLOGY, INC.
To: PIONEER SURGICAL TECHNOLOGY NEWCO, INC.
Reel/Frame 065287/0641 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Oct 11, 2023
From: PIONEER SURGICAL TECHNOLOGY NEWCO, INC.
To: XTANT MEDICAL HOLDINGS, INC.
Reel/Frame 065218/0590 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Aug 22, 2019
From: LIN, JUCHUI RAY; AHN, EDWARD S
To: PIONEER SURGICAL TECHNOLOGY, INC.
Reel/Frame 050130/0726 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Aug 22, 2019
From: SCHLOSSBERG, BRIAN M
To: PIONEER SURGICAL TECHNOLOGY, INC.
Reel/Frame 050130/0839 →