Curable silicone impression materials with high tear strength and low consistency

• US 7,968,645 B2
• Filed: 05/07/2004
• Issued: 06/28/2011
• Est. Priority Date: 05/09/2003
• Status: Expired due to Fees

• Current Assignee: 3M Deutschland GmbH (3M Company)
• Original Assignee: 3M ESPE AG (3M Company)
• Inventors: Strauss, Franziska, Hoffmann, Henning, Zech, Joachim W., Steiger, Wolf, Bissinger, Peter
• Primary Examiner(s): Gulakowski; Randy
• Assistant Examiner(s): Loewe; Robert
• Application Number:
  US10/554,989
• Publication Number:
  US 20070060717A1
• Time in Patent Office: 2,608 Days
• Field of Search: 524/588, 524/862, 525/478
• US Class Current: 524/588
• CPC Class Codes: A61K 6/90 Compositions for taking dental impressions
• CPC Class Codes: C08G 77/12 containing silicon bound to hydrogen C08G77/045 takes precedence
• CPC Class Codes: C08G 77/14 containing silicon bound to oxygen-containing groups C08G77/045 takes precedence
• CPC Class Codes: C08G 77/20 containing silicon bound to unsaturated aliphatic groups C08G77/045 takes precedence
• CPC Class Codes: C08G 77/26 nitrogen-containing groups
• CPC Class Codes: C08G 77/70 Siloxanes defined by use of the MDTQ nomenclature
• CPC Class Codes: C08K 5/54 Silicon-containing compounds C08K5/0091 takes precedence
• CPC Class Codes: C08L 83/00 Compositions of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon only; Compositions of derivatives of such polymers
• CPC Class Codes: C08L 83/04 Polysiloxanes

Abstract

The invention relates to curable silicone compositions which contain silane based crosslinkers and a mixture of different organopolysiloxanes. The compositions are particularly suitable as curable impression materials in dental applications.

Claims

1. A curable material comprising:

component (A) comprising at least two different types of organopolysiloxanes, (A1) having a viscosity value of 10 to 1,000 mPa-s, and (A2) having a viscosity value of 500 to 45,000 mPa-s, with at least two ethylenically unsaturated groups per molecule, with the proviso that the component (A) siloxanes do not comprise aromatic groups;

component (B) comprising organohydrogenpolysiloxane having about 1.0 to about 1.7 wt.- % silicon-bonded hydrogen and with at least three SiH groups per molecule;

component (D) comprising a catalyst for promoting the reaction between (A) and (B);

component (F) comprising filler; and

component (H) comprising at least one silane with at least two alkenyl groups per molecule, wherein said at least one silane is selected from the group consisting of compounds that can be represented by the general formula (III);

(R¹)_m(R²)_3-mSi-A-Si—

(R¹)_n(R²)_3-n 

 

(III)

wherein;

R¹and R² and n can be independently selected from each other;

R¹is a linear, branched or cyclic, monovalent, ethylenically unsaturated substituent which can undergo an addition reaction with SiH-groups and has 2 to 12 carbon atoms;

R² is a monovalent radical without groups that can undergo an addition reaction with SiH-groups or have a detrimental influence on such a reaction;

A is a bivalent, linear, branched or alicyclic, heterocyclic, aromatic or heteroaromatic group with 1 to 10,000 carbon atoms which can contain nitrogen or oxygen atoms;

n is 2 or 3; and

m is 2 or 3;

wherein the consistency of the curable material according to ISO 4823 is greater than 35 mm; and

with the proviso that the curable material does not comprise an added organopolysiloxane having a group with an ethylenically unsaturated double bond located at a non-terminal monomeric unit.

2. The material according to claim 1, wherein the viscosity of at least one of the organopolysiloxanes of component (A) is at least twice the viscosity of another organopolysiloxane of component (A).

3. The material according to claim 1 comprising:

5-70 wt.- % components (A), (B), and (H) combined;

0-40 wt.- % organopolysiloxane without reactive groups;

0.00005-0.05 wt.- % catalyst (D), calculated as elemental platinum and relative to the total weight of the material;

0-10 wt.- % hydrophilizing agents;

10-90 wt.- % component (F);

0-5 wt.- % conventional dental additives, adjuvants and colorants; and

0.1-50 wt.- % component (H).

4. The material according claim 3 comprising:

10-60 wt.- % components (A), (B), and (H) combined;

0-20 wt.- % organopolysiloxane without reactive groups;

0.0002-0.04 wt.- % catalyst (D), calculated as elemental platinum and relative to the overall weight of the material;

0-2 wt- % hydrophilizing agent;

30-80 wt.- % component (F);

0-2 wt.- % conventional dental additives, adjuvants and colorants; and

0.1-20 wt.- % component (H).

5. The material according claim 1, wherein the quantities of components (A), (B) and (H) are selected such that 0.5 to 10 mol SiH units in component (B) are present per mol of unsaturated double bond in components (A) and (H).

6. The material according to claim 1 wherein, said material is prepared from two pasty compositions in the form of a base paste and a catalyst paste, wherein the entire amount of said organohydrogenpolysiloxane is present in the base paste, and the entire amount of said catalyst is present in the catalyst paste, and the remaining components are distributed between the two pastes.

7. The material according to claim 6, wherein the volume ratio of base paste to catalyst paste in the material is 10:

1 to 1;

10.

8. The material according to claim 1, wherein component A comprises at least three different types of organopolysiloxanes, each with a different viscosity and one organopolysiloxane has a higher viscosity than the other two.

9. The material according to claim 1 wherein the curable material is a dental impression material.

10. A curable material comprising:

component (A) comprising at least two different types of organopolysiloxanes, (A1) having a viscosity value of 10 to 1,000 mPa-s, and (A2) having a viscosity value of 500 to 45,000 mPa-s, with at least two ethylenically unsaturated groups per molecule, with the proviso that the component (A) siloxanes do not comprise aromatic groups;

component (B) comprising organohydrogenpolysiloxane having about 1.0 to about 1.7 wt.- % silicon-bonded hydrogen and with at least three SiH groups per molecule;

component (D) comprising a catalyst for promoting the reaction between (A) and (B);

component (F) comprising filler; and

component (H) comprising at least one silane with at least two alkenyl groups per molecule, wherein said at least one silane is selected from the group consisting of compounds that can be represented by the general formula (III);

(R¹)_m(R²)_3-mSi-A-Si—

(R¹)_n(R²)_3-n 

 

(III)

wherein;

R¹ and R² and n can be independently selected from each other;

R¹ is a linear, branched or cyclic, monovalent, ethylenically unsaturated substituent which can undergo an addition reaction with SiH-groups and has 2 to 12 carbon atoms;

R² is a monovalent radical without groups that can undergo an addition reaction with SiH-groups or have a detrimental influence on such a reaction;

A is a bivalent, linear, branched or alicyclic, heterocyclic, aromatic or heteroaromatic group with 1 to 10,000 carbon atoms which can contain nitrogen or oxygen atoms;

n is 2 or 3; and

m is 2 or 3;

wherein the consistency of the curable material according to ISO 4823 is greater than 35 mm;

wherein, upon curing, the material has a Shore A hardness of no greater than about 70; and

with the proviso that the curable material does not comprise an added organopolysiloxane having a group with an ethylenically unsaturated double bond located at a non-terminal monomeric unit.

11. The material according to claim 10 wherein the curable material is a dental impression material.

12. A curable material comprising:

component (A) comprising at least two different types of organopolysiloxanes, (A1) having a viscosity value of 10 to 1,000 mPa-s, and (A2) having a viscosity value of 500 to 45,000 mPa-s, with at least two ethylenically unsaturated groups per molecule, with the proviso that the component (A) siloxanes do not comprise aromatic groups;

component (B) comprising organohydrogenpolysiloxane having about 1.0 to about 1.7 wt.- % silicon-bonded hydrogen and with at least three SiH groups per molecule;

component (D) comprising a catalyst for promoting the reaction between (A) and (B);

component (F) comprising filler; and

component (H) comprising at least one silane with at least two alkenyl groups per molecule, wherein said at least one silane is selected from the group consisting of compounds that can be represented by the general formula (III);

(R¹)_m(R²)_3-mSi-A-Si—

(R¹)_n(R²)_3-n 

 

(III)

wherein;

R¹ and R² and n can be independently selected from each other;

R¹ is a linear, branched or cyclic, monovalent, ethylenically unsaturated substituent which can undergo an addition reaction with SiH-groups and has 2 to 12 carbon atoms;

R² is a monovalent radical without groups that can undergo an addition reaction with SiH-groups or have a detrimental influence on such a reaction;

A is a bivalent, linear, branched or alicyclic, heterocyclic, aromatic or heteroaromatic group with 1 to 10,000 carbon atoms which can contain nitrogen or oxygen atoms;

n is 2 or 3; and

m is 2 or 3;

wherein the consistency of the curable material according to ISO 4823 is greater than 35 mm;

wherein, upon curing, the material has an elongation at break value of 70 to 300%; and

with the proviso that the curable material does not comprise an added organopolysiloxane having a group with an ethylenically unsaturated double bond located at a non-terminal monomeric unit.

13. The curable material of claim 12, wherein, upon curing, the material has a Shore A hardness of no greater than about 70.

14. A curable material comprising:

component (A) consisting of two different types of organopolysiloxanes, (A1) having a viscosity value of 10 to 1,000 mPa-s, and (A2) having a viscosity value of 500 to 45,000 mPa-s, with at least two ethylenically unsaturated groups per molecule, with the proviso that the component (A) siloxanes do not comprise aromatic groups;

component (B) comprising organohydrogenpolysiloxane having about 1.0 to about 1.7 wt.- % silicon-bonded hydrogen and with at least three SiH groups per molecule;

component (D) comprising a catalyst for promoting the reaction between (A) and (B);

component (F) comprising filler; and

component (H) comprising at least one silane with at least two alkenyl groups per molecule;

wherein the consistency of the curable material according to ISO 4823 is greater than 35 mm;

wherein, upon curing, the material has an elongation at break value of 70 to 300%; and

with the proviso that the curable material does not comprise an added organopolysiloxane having a group with an ethylenically unsaturated double bond located at a non-terminal monomeric unit.

15. The curable material of claim 14, wherein, upon curing, the material has a Shore A hardness of no greater than about 70.