Pasty two-component polymethacrylate bone cement

Patent metadata

Field	Value
Publication number	US-10507261-B2
Application number	US-201715615209-A
Country	US
Kind code	B2
Filing date	Jun 6, 2017
Priority date	Jun 7, 2016
Publication date	Dec 17, 2019
Grant date	Dec 17, 2019

Abstract

A pasty two-component polymethacrylate bone cement comprising a pasty component A, containing
AI at least one distillable methacrylate monomer for radical polymerisation; AII at least one polymer soluble in AI; AIII at least one particulate polymer with a particle size of no more than 500 μm that is not soluble in AI; AIV at least one radical stabiliser; and AV at least one aromatic amine accelerator;

and a pasty component B, containing
BI dibenzoyl peroxide; BII at least one substance that is not subject to radical polymerisation and is liquid at room temperature, whereby the solubility of dibenzoyl peroxide in this substance at room temperature is less than 5.0% by weight and, whereby the weight fraction of liquid substance BII in the self-curing cement dough is less than 2.0% by weight. Also disclosed is a method for producing a self-curing bone cement dough using the pasty two-component polymethacrylate bone cement.

First claim

The invention claimed is:

1. Pasty two-component polymethacrylate bone cement comprising a pasty component A, comprising:
AI at least one distillable methacrylate monomer for radical polymerisation;
AII at least one polymer that is soluble in AI;
AIII at least one particulate polymer with a particle size of no more than 500 μm that is not soluble in AI;
AIV at least one radical stabiliser; and
AV at least one accelerator from the group of aromatic amines;
and
a pasty component B, consisting of:
BI dibenzoyl peroxide; and
BII at least one substance that is not subject to radical polymerisation and is liquid at room temperature, whereby the solubility of dibenzoyl peroxide in this substance at room temperature is less than 5.0% by weight; and
optionally at least one color pigment that is insoluble in liquid substance BII; and
whereby the weight fraction of liquid substance BII in the self-curing cement dough thus formed after the mixing of pasty component A with pasty component B is completed is less than 2.0% by weight.

2. Pasty two-component polymethacrylate bone cement according to claim 1 , wherein
pasty component A contains
AI 20-60 wt. % of the at least one distillable methacrylate monomer for radical polymerisation;
AII 15-45 wt. % of the at least one polymer that is soluble in AI;
AIII 15-45 wt. % of the at least one particulate polymer with a particle size of at most 500 μm that is not soluble in AI.

3. Pasty two-component polymethacrylate bone cement according to claim 1 , wherein
the weight ratio of dibenzoyl peroxide BI and liquid substance BII is more than or equal to 1:1.

4. Pasty two-component polymethacrylate bone cement according to claim 1 , wherein
the weight ratio of pasty component A and pasty component B is more than or equal to 96 to 4.

5. Pasty two-component polymethacrylate bone cement according to claim 1 , wherein
BII is selected from water, glycerol, diglycerol, glycerol-tri-octoate, glycerol-tri-decanoate, polyethylene glycol, sebacinc acid dibutylester, and mixtures thereof.

6. Pasty two-component polymethacrylate bone cement according to claim 1 , wherein
BI dibenzoyl peroxide has a sieved fraction with a grain size of less than or equal to 63 μm.

7. Pasty two-component polymethacrylate bone cement according to claim 1 , wherein the accelerator AV is selected from the group consisting of N,N-dimethyl-p-toluidine, N,N-bis-hydroxyethyl-p-toluidine, and N,N-dimethyl-p-hydroxyethyl-aniline.

8. Pasty two-component polymethacrylate bone cement according to claim 1 , wherein
AI the methacrylate monomer is selected from the group consisting of methylmethacrylate and ethylene glycol dimethacrylate.

9. Pasty two-component polymethacrylate bone cement according to claim 1 , wherein
polymer AII is selected from the group of polymethylmethacrylate copolymers.

10. Pasty two-component polymethacrylate bone cement according to claim 9 , wherein
polymer AII is selected from the group consisting of polymethylmethacrylate-co-methylacrylate and polymethylmethacrylate-co-styrene.

11. Pasty two-component polymethacrylate bone cement according to claim 1 , wherein
AII is selected from the group consisting of cross-linked polymethylmethacrylate and cross-linked polymethylmethacrylate-co-methylacrylate.

12. Pasty two-component polymethacrylate bone cement according to claim 1 , wherein
the radical stabiliser AIV is selected from the group consisting of p-benzoquinone, o-benzoquinone, 2,5-di-t-butylhydroquinone, p-hydroquinone and phenothiazine.

13. Pasty two-component polymethacrylate bone cement according to claim 1 , wherein pasty component A contains, as excipients, one or substances selected from the group consisting of methacrylate-soluble colourants, methacrylate-insoluble colour pigments, pyrogenic silicon dioxide, and methacrylic amide.

14. Pasty two-component polymethacrylate bone cement according to claim 1 , wherein
pasty component A contains one or more pharmaceutical agent(s) selected from the group consisting of antibiotics, hormones, growth factors, and antiphlogistic agents.

15. Pasty two-component polymethacrylate bone cement according to claim 1 , wherein
pasty component A contains at least one radiopaquer selected from the group consisting of zirconium dioxide, barium sulfate, tantalum, and biocompatible calcium salts.

16. Pasty two-component polymethacrylate bone cement according to claim 1 , wherein
a colour pigment that is insoluble in liquid substance BII is suspended in pasty component B.

17. Method for producing a self-curing bone cement using the two-component polymethacrylate bone cement according to claim 1 , comprising mixing pasty component A and pasty component B at a weight ratio of more than or equal to 96 to 4.

18. Method of using the pasty two-component polymethacrylate bone cement according to claim 1 for the production of a means for fixation of total articular endoprostheses and revision articular endoprostheses.

19. Method of using a pasty two-component polymethacrylate bone cement according to claim 1 for the production of a means for vertebroplasty, for kyphoplasty, for femoral neck augmentation, and for the production of spacers.

20. Method of using the pasty two-component polymethacrylate bone cement according to claim 1 for the production of local agent release systems.

21. Pasty two-component polymethacrylate bone cement according to claim 1 , wherein liquid substance BII is selected from the group consisting of glycerol, diglycerol, glycerol-tri-octoate, glycerol-tri-decanoate, polyethylene glycol, sebacic acid dibutylester, mixed glycerol-triesters of octanoic acid and decanoic acid, and mixtures thereof.

Assignees

• Heraeus Medical Gmbh

Inventors

• Vogt Sebastian
• Kluge Thomas

Classifications

• A61L24/06 Primary

  obtained by reactions only involving carbon-to-carbon unsaturated bonds {(A61L24/043, A61L24/046 take precedence)} · CPC title

• A61L27/16

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

• C08F265/06

  Polymerisation of acrylate or methacrylate esters on to polymers thereof · CPC title

• A61L24/0021 Primary

  Plasticisers · CPC title

• A61K47/32

  Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds, e.g. carbomers {, poly(meth)acrylates, or polyvinyl pyrrolidone} · CPC title