IP Library Granted Patent US 7,041,164
Granted Patent B2
US 7,041,164 · App. 10/323,865 · Granted May 9, 2006

Dental etch solutions

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Quick Facts
Patent No.
US 7,041,164
App. No.
10/323,865
Granted
May 9, 2006
Kind
B2
Abstract

Etching compositions, curable compositions, packaged products and methods of use for the treatment of bone substrate, i.e., teeth, are described. The etch solutions generally include an inorganic acid, an organic acid and either a solvent, a surfactant or mixtures thereof. The curable composites include reactive monomers and crosslinking agents that are effective to adhere to the surface of the treated substrate. The methods of the invention provide the ability to modify a bone or bone-like surface so that the curable composition, such as an adhesive resin, can be used in combination with a restorative material.

Claims (40)

1. A dental etching solution comprising

nitric acid;

an organic acid;

a solvent; and

water;

wherein the nitric acid concentration is between about 6 and about 8 parts by weight, the organic acid is present in amount from about 0.01 to about 20 parts by weight, the solvent is present in an amount from about 1 to about 50 parts by weight, the water being present in an amount to equal a total of 100 parts by weight of all components.

2. The dental etching solution of claim 1 , wherein the organic acid is selected from the group consisting of lactic acid, pyruvic acid, glycolic acid, chloroacetic acid, dichloroacetic acid, trichloroacetic acid, cyanoacetic acid, tartaric acid, succinic acid, glutaric acid, maleic acid, fumaric acid, malonic acid, citraconic acid, ortho-phthalic acid, meta-phthalic acid, para-phthalic acid, citric acid, tricarballyic acid, 1,3,5-pentanetricarboxylic acid and trimellitic acid.

3. The dental etching solution of claim 1 , wherein the solvent is selected from the group consisting of acetone, dimethyl sulfoxide, and ethanol.

4. The dental etching solution of claim 3 , wherein the solvent concentration is between about 10 and about 30 parts by weight.

5. The dental etching solution of claim 3 , wherein the solvent is ethanol.

6. The dental etching solution of claim 5 , wherein the solvent concentration is between about 10 and about 30 parts by weight.

7. A dental etching solution comprising

an inorganic acid;

succinic acid;

a solvent; and

water;

wherein the inorganic acid is present in an amount of from about 1 to about 10 parts by weight, the succinic acid is present in amount from about 0.01 to about 20 parts by weight, the solvent is present in an amount from about 1 to about 50 parts by weight, the water being present in an amount to equal a total of 100 parts by weight of all components.

8. The dental etching solution of claim 7 , wherein the succinic acid concentration is between about 1.0 and about 3.0 parts by weight.

9. The dental etching solution of claim 7 , wherein the inorganic acid is selected from the group consisting of nitric acid, sulfuric acid, hydrochloric acid and phosphoric acid.

10. The dental etching solution of claim 7 , wherein the solvent is selected from the group consisting of acetone, dimethyl sulfoxide, and ethanol.

11. The dental etching solution of claim 10 , wherein the solvent concentration is between about 10 and about 30 parts by weight.

12. The dental etching solution of claim 11 , wherein the solvent is ethanol.

13. The dental etching solution of claim 12 , wherein the solvent concentration is between about 10 and about 30 parts by weight.

14. The dental etching solution of claim 7 , further comprising an ethylenically unsaturated monomer.

15. The dental etching solution of claim 14 , wherein the ethylenically unsaturated monomer is selected from the group consisting of ethyleneglycol acrylate phosphate, ethyleneglycol methacrylate phosphate, 2-hydroxyethylacrylate, 2-hydroxyethylmethacrylate, 2-hydroxypropylacrylate, 3-hydroxypropylacrylate, 2-hydroxypropylmethacrylate, 3-hydroxypropylmethacrylate, 1,3-dihydroxypropylacrylate, 2,3-dihydroxypropylacrylate, 1,3-dihydroxypropylmethacrylate, 2,3-dihydroxypropylmethacrylate, acrylic acid, methacrylic acid, 2-trimethylammonium ethylmethacrylic chloride, 2-acrylamido-2-methylpropane-sulfonic acid, 2-methacrylamido-2-methylpropane-sulfonic acid, acrylamide, methacrylamide, 2-hydroxyethylacrylamide, 2-hydroxyethylmethacrylamide, N,N-bis(2-hydroxyethyl)acrylamide, N,N-bis(2-hydroxyethyl)methacrylamide, N-alkyl-N-hydroxyethyl acrylamides, N-alkyl-N-hydroxyethyl methacrylamides, 2-hydroxypropylacrylamide, 2-hydroxypropylmethacrylamide, 3-hydroxypropylacrylamide, 3-hydroxypropylmethacrylamide, methacrylamidopropyltrimethylammonium chloride, gylcerol monomethacrylate and glycerol monoacrylate.

16. The dental etching solution of claim 14 , wherein the ethylenically unsaturated monomer is present in an amount of from about 0.1 to about 10 parts by weight of the total of all components.

17. The dental etching solution of claim 14 , wherein the ethylenically unsaturated monomer is methacrylic acid.

18. A dental etching solution comprising

an inorganic acid;

an organic acid;

ethyleneglycol methacrylate phosphate;

a solvent; and

water;

wherein the inorganic acid is present in an amount of from about 1 to about 10 parts by weight, the organic acid is present in amount from about 0.01 to about 20 parts by weight, the ethyleneglycol methacrylate phosphate is present in an amount from about 5 part to about 30 parts by weight, the solvent is present in an amount from about 1 to about 50 parts by weight, the water being present in an amount to equal a total of 100 parts by weight of all components.

19. The dental etching solution of claim 18 , wherein the inorganic acid is selected from the group consisting of nitric acid, sulfuric acid, hydrochloric acid and phosphoric acid.

20. The dental etching solution of claim 18 , wherein the organic acid is selected from the group consisting of lactic acid, pyruvic acid, glycolic acid, chloroacetic acid, dichioroacetic acid, trichioroacetic acid, cyanoacetic acid, tartaric acid, succinic acid, glutaric acid, maleic acid, fumaric acid, malonic acid, citraconic acid, ortho-phthalic acid, meta-phthalic acid, para-phthalic acid, citric acid, tricarballyic acid, 1,3,5-pentanetricarboxylic acid and trimellitic acid.

21. The dental etching solution of claim 18 , wherein the solvent is selected from the group consisting of acetone, dimethyl sulfoxide, and ethanol.

22. The dental etching solution of claim 21 , wherein the solvent concentration is between about 10 and about 30 parts by weight.

23. The dental etching solution of claim 22 , wherein the solvent is ethanol.

24. The dental etching solution of claim 23 , wherein the solvent concentration is between about 10 and about 30 parts by weight.

Assignments (9)
CORRECTIVE ASSIGNMENT TO CORRECT THE NATURE OF CONVEYANCE PREVIOUSLY RECORDED ON REEL 67010 FRAME 306. ASSIGNOR(S) HEREBY CONFIRMS THE RELEASE OF SECURITY INTEREST. Recorded Apr 8, 2024
From: MARANON CAPITAL, L.P., AS AGENT
To: INTER-MED, INC.; APEX DENTAL MATERIALS, LLC
Reel/Frame 067029/0280 →
CORRECTIVE ASSIGNMENT TO CORRECT THE NATURE OF CONVEYANCE TO RELEASE OF SECURITY INTEREST PREVIOUSLY RECORDED ON REEL 67010 FRAME 306. ASSIGNOR(S) HEREBY CONFIRMS THE RELEASE OF SECURITY INTEREST. Recorded Apr 8, 2024
From: MARANON CAPITAL, L.P., AS AGENT
To: INTER-MED, INC.; APEX DENTAL MATERIALS, LLC
Reel/Frame 067028/0628 →
SECURITY INTEREST Recorded Apr 4, 2024
From: MARANON CAPITAL, L.P., AS AGENT
To: INTER-MED, INC.; APEX DENTAL MATERIALS, LLC
Reel/Frame 067010/0306 →
SECURITY INTEREST Recorded Apr 3, 2024
From: APEX DENTAL MATERIALS, LLC
To: BMO BANK N.A., AS ADMINISTRATIVE AGENT
Reel/Frame 066993/0455 →
RELEASE OF SECURITY INTEREST Recorded Apr 11, 2022
From: AVANTE MEZZANINE PARTNERS SBIC II, L.P.
To: APEX DENTAL MATERIALS, LLC
Reel/Frame 059558/0137 →
SECURITY INTEREST Recorded Apr 7, 2022
From: INTER-MED, INC.; APEX DENTAL MATERIALS, LLC
To: MARANON CAPITAL, L.P., AS ADMINISTRATIVE AGENT
Reel/Frame 059530/0599 →
SECURITY INTEREST Recorded Mar 28, 2019
From: APEX DENTAL MATERIALS, LLC
To: AVANTE MEZZANINE PARTNERS SBIC II, L.P.
Reel/Frame 048727/0504 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Mar 28, 2019
From: KANCA, JOHN, III
To: APEX DENTAL MATERIALS, LLC
Reel/Frame 048727/0456 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded May 22, 2003
From: KANCA, JOHN A. III
To: KANCA, JOHN A. III
Reel/Frame 014089/0198 →