Initiator systems for initiating the polymerization of ethylenically unsaturated compounds and use thereof

• US 5,512,527 A
• Filed: 07/21/1994
• Issued: 04/30/1996
• Est. Priority Date: 11/27/1989
• Status: Expired due to Term

• Current Assignee: Biomet Deutschland GmbH (Zimmer Biomet Holdings, Inc.)
• Original Assignee: Henkel KGaA (Henkel AG & Co KGaA)
• Inventors: Ritter, Wolfgang
• Primary Examiner(s): PAL, ASOKKUMAR
• Application Number:
  US08/278,680
• Time in Patent Office: 649 Days
• Field of Search: 502/150, 502/172
• US Class Current: 502/150
• CPC Class Codes: A61K 6/64 Thermal radical initiators
• CPC Class Codes: C04B 26/04 obtained by reactions only involving carbon-to-carbon unsaturated bonds
• CPC Class Codes: C08F 4/54 together with other compounds thereof

Abstract

Described are initiator systems for initiating the polymerization of ethylenically unsaturated compounds, which systems have been based on oxygen-reactive organo-boron compounds present in combination with oxygen-resistant carriers; the initiator systems are characterized in that they contain oligoesters of lower hydroxycarboxylic acids as carriers. The invention further relates to the use of these initiator systems in adhesive systems in the technical field, but especially also in the areas of surgery and/or dentistry for curing body-resorbable or body-resistant adhesive agents, cements and/or filler compositions or for forming molded parts of synthetic materials.

Claims

1. A storage stable initiator system for initiating the polymerization of ethylenically unsaturated compounds consisting essentially of a mixture of an oxygen-reactive organoboron compound and an oxygen-resistant carrier consisting essentially of oligoesters of lower hydroxy carboxylic acids whereby polymerization initiation ability of the organoboron compound is preserved when exposed to air for at least several hours.

2. The initiator system according to claim 1 wherein said oligoesters consist essentially of residues of hydroxy carboxylic acids having from 2 to 10 carbon atoms.

3. The initiator system according to claim 1 wherein said carrier consists essentially of at least one member selected from the group consisting of hydroxy-group terminated oligoesters of the lower hydroxy carboxylic acids, and carboxyl-group terminated oligoesters of the lower hydroxy carboxylic acids.

4. The initiator system according to claim 1 wherein said carrier consists essentially of oligoesters of lower hydroxy carboxylic and chain terminated with at least one member selected from the group consisting of alcohols and carboxylic acids.

5. The initiator system according to claim 1 wherein said carrier consists essentially of oligoesters formed by the condensation of lower di- or trifunctional alcohols or combinations thereof with the hydroxy carboxylic acids.

6. The initiator system according to claim 1 wherein said carrier consists essentially of oligoesters formed by the condensation of polyfunctional alcohols or polyfunctional carboxylic acids with hydroxy carboxylic acids or their reactive derivatives in a molar ratio of from about 1:

1 to about 1;

10.

7. The initiator system according to claim 1 wherein said carrier consists essentially of low viscosity oligoesters having viscosities within a range of up to about 40,000 mPa'"'"'s at room temperature.

8. The initiator system according to claim 1 wherein the mixing ratios of carrier to the organoboron compound are such that the boron content of the initiator system is within the range of from about 0.5 to about 10% by weight.

9. The initiator system according to claim 1 wherein the initiator system containing the organoboron compounds is not self-igniting in air is capable of initiating the polymerization in the presence of air at room temperature or only moderately elevated temperature.

10. The initiator system according to claim 1 wherein the organoboron compounds which comprise alkyl or aryl groups also contain B-H bonds.

11. The initiator system according to claim 1 wherein said initiator contains at least one trialkylboron compound or at least one alkylboron hydride or a combination thereof.

12. The initiator system of claim 1 wherein the polymerization initiation ability of the mixture is preserved when exposed to air for at least 72 hours.

13. The initiator according to claim 2 wherein said hydroxycarboxylic acids have from 2 to 6 carbon atoms.

14. The initiator system according to claim 2 wherein said oligoesters are oligoesters of at least one member selected from the group consisting of glycolic acid and lactic acid.

15. The initiator system according to claim 4 wherein said alcohols are mono- or polyfunctional alcohols and said carboxylic acids are mono- or polyfunctional carboxylic acids.

16. The initiator system according to claim 5 wherein said oligoesters consist essentially of the condensation products of ethylene glycol or glycerol with hydroxy carboxylic acids or their reactive derivatives.

17. The initiator system according to claim 6 wherein said molar ratio is from about 1:

1 to about 1;

3.

18. The initiator system according to claim 7 wherein the upper limit of said viscosity is 25,000 mPa'"'"'s at room temperature.

19. The initiator system according to claim 18 wherein the oligoester consists essentially of the condensation product of at least one member selected from the group consisting of glycolic acid and lactic acid having a viscosity not higher than 25,000 mPa'"'"'s.

20. The initiator system according to claim 8 wherein said mixing ratio is such that the boron content is from about 1 to about 5% by weight.

21. The initiator system according to claim 11 wherein said alkylboron hydride is a dialkylboron hydride.