IP Library Granted Patent US 6,908,953
Granted Patent B2
US 6,908,953 · App. 10/389,814 · Granted Jun 21, 2005

Polymerizable compositions based on epoxides

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Quick Facts
Patent No.
US 6,908,953
App. No.
10/389,814
Granted
Jun 21, 2005
Kind
B2
Abstract

The present invention is directed to polymerizable dental compositions containing (a) 3 to 80 wt. % of cycloaliphatic epoxides; b) 0 to 80 wt. % of an epoxide or a mixture of epoxides which are different from a); c) 3 to 85 wt. % of a filler material; d) 0.01 to 25 wt. % of initiators, inhibitors and/or accelerators; e) 0 to 25 wt. % of auxiliary agents, the individual percentages of which are in relation to the total weight. The new polymerizable agents are particularly suited as dental material.

Claims (35)

1. A method for making a dental composition, comprising the steps of:

providing a polymerizable storable one-component dental composition comprising

(a) 3 to 80 wt. % of an epoxide or a mixture of epoxides of the general formula:

suitable for a dental composition, in which,

Z denotes an aliphatic, cycloaliphatic or aromatic radical having 1 to 22 carbon atoms or a combination of these radicals, wherein one or more carbon atoms can be replaced by O, C═O, —O(C═O)—, SiR 2 and/or NR, wherein at least one carbon atom must be replaced by SiR 2 , and wherein R is an aliphatic radical having 1 to 7 carbon atoms, wherein one or more carbon atoms can be replaced by O, C═O and/or —O(C═O)—,

A denotes an aliphatic, cycloaliphatic or aromatic radical having 1 to 18 carbon atoms or a combination of these radicals, wherein one or more carbon atoms can be replaced by O, C═O, —O(C═O)—, SiR 2 and/or NR, wherein R is an aliphatic radical having 1 to 7 carbon atoms, in which one or more carbon atoms can be replaced by O, C═O and/or —O(C═O)—,

B 1 , B 2 , D and E independently of one another denote a hydrogen atom or an aliphatic radical having 1 to 9 carbon atoms, wherein one or more carbon atoms can be replaced by O, C═O, —O(C═O)—, SiR 2 and/or NR, wherein R is an aliphatic radical having 1 to 7 carbon atoms, in which one or more carbon atoms can be replaced by O, C═O and/or —O(C═O)—,

n denotes 2-7,

m denotes 1-10,

p denotes 1-5, and

q denotes 1-5

(b) 0 to 80 wt. % of an epoxide or a mixture of epoxides which differ from (a),

(c) 3 to 85 wt. % of dental fillers,

(d) 0.01 to 25 wt. % of initiators and retardants or accelerators,

(e) 0 to 25 wt. % of auxiliaries, the percentage data in each case being based on the total weight of the composition, and

curing the polymerizable storable one-component dental composition by irradiating the composition by UV or visible light.

2. The method of claim 1 , wherein component (a) is selected from the group consisting of the following epoxides:

i) 2,2-bis[4,1-phenylenoxy-3,1-propanediyl-1,1,3,3,-tetramethyldisiloxanyl-1,2-ethanediyl-3,4-epoxycyclohexyl]propylidene

ii) 2,2-bis{4,1-phenylenoxy-3,1-propanediyl-[3,5,7-tris(ethanediyl-3,4-epoxycyclohexyl)-1,3,5,7-tetramethylcyclotetrasiloxanyl]}propylidene

iii) bis(methanediyl-oxy-3,1-propanediyl-1,1,3,3-tetramethyldisiloxanediyl-1,2-ethanedlyl-3,4-epoxycylclohexyl)tricyclo[5.2.1.0 2,6 ]decane

iv) bis(methanedyil-oxy-(3-propanediyl-3,5,7-tris(2,1-ethanediyl-3,4-epoxycyclohexyl)-1,3,5,7-tetramethylcyclotetrasiloxanyl)-tricyclo[5.2.1.0 2,6 ]decane

v) 1,1,1-tris[methanediyl-oxy-1,3-propanediyl-1,1,3,3-tetramethyldisiloxanediyl-1,2-ethanediyl-3,4-epoxycyclohexyl]propane

vi) 1,1,1-Tris[methanediyl-oxy-3,1-propanediyl-3,5,7-tris(2,1-ethanediyl-3,4-epoxycyclohexyl)-1,3,5,7-tetramethylcyclotetrasiloxanyl]propane

vii) 1,1,1-tris[methanediyl-oxy-bis(ethanediyloxy)-propanediyl-1,1,3,3-tetramethyldisiloxanyl-1,2-ethanediyl-3,4-epoxycyclohexyl]propane

viii) 1,1,1-tris[methanediyl-oxy-bis(ethanediyloxy)-propanediyl-3,5,7-tris(2,1-ethanediyl-3,4-epoxycyclohexyl)-1,3,5,7-tetramethylcyclotetrasiloxanyl]propane

ix) α,ω-bis[3,4-epoxycyclohexylethanediyl-1,1,3,3-tetra-methyldisiloxanyl-3,1-propanediyl]polytetrahydrofiran

x) α,ω-bis(3-propanediyl-3,5,7-tris(2,1-ethanediyl-3,4-epoxycyclohexyl)-1,3,5,7-tetramethylcyclotetrasiloxanyl)polytetrahydrofuran

xi) 1,3,5,7-tetrakis(2,1-ethanediyl-3,4-epoxycyclohexyl)-1,3,5,7-tetramethylcyclotetrasiloxane

xii) 1,3,5,7,9-pentakis(2,1-ethanediyl-3,4-epoxycyclohexyl)-1,3,5,7,9-pentamethylcyclopentasiloxane

xiii)methylbis[2-(7-oxabicyclo[4.1.0]hept-3 yl)ethyl]phenylsilane

3. The method of claim 1 , wherein component (b) is selected from the group consisting of: 3,4-epoxycyclohexylmethyl 3,4-epoxycyclohexanecarboxylate, 3,4-epoxy-6-methylcyclohexyl 3,4-epoxy-6-methyl cyclohexanecarboxylate, dicyclopentadiene dioxide, bis(3,4-epoxycyclohexylmethyl) adipate, 1,1,3,3-tetramethyl-1,3-bis(ethanediyl-3,4-epoxycyclohexyl)disiloxane and low molecular weight siloxanes functionalized with cycloaliphatic epoxides.

4. The method of claim 1 , wherein the filler of component (c) is selected from the group consisting of: quartz, ground glasses, silica gels, and silicic acids or granules thereof.

5. The method of claim 1 , wherein the retardants, accelerators and/or initiators are selected from the group consisting of: Lewis acids, Broensted acids, and compounds from which such acids are formed by irradiation with UV light or visible light or by heat and/or pressure.

6. The method of claim 1 , wherein said auxiliary is selected from the group consisting of: diols, diluents, stabilizers, inhibitors and pigments.

7. The method of claim 1 , wherein Z has 1 to 18 carbon atoms.

Assignments (1)
MERGER Recorded Feb 27, 2012
From: 3M ESPE AG
To: 3M DEUTSCHLAND GMBH
Reel/Frame 027762/0754 →