Amino acid carbamate complexes

Patent metadata

Field	Value
Publication number	US-10857083-B2
Application number	US-201816216533-A
Country	US
Kind code	B2
Filing date	Dec 11, 2018
Priority date	Dec 19, 2017
Publication date	Dec 8, 2020
Grant date	Dec 8, 2020

Abstract

Disclosed herein are amino acid carbamate complexes, methods of synthesis thereof, oral care compositions comprising the same, and methods of making and using thereof.

First claim

The invention claimed is:

1. An oral care composition comprising an amino acid carbamate complex of the formula M + [amino acid-carbamate] − which comprises an amino acid carbamate anion and a counterion M, wherein M is a metal cation or an amino acid cation, and wherein the composition is selected from a dentifrice, toothpaste, tooth powder, tooth gel, or mouthwash, and wherein the complex is present in an amount of 0.05 to 10% by weight of the composition.

2. The composition of claim 1 , wherein M is the amino acid cation.

3. The composition of claim 1 , wherein M is the amino acid cation wherein the amino acid is selected from the group consisting of glycine, arginine, lysine, histidine, alanine, valine, leucine, isoleucine, phenylalanine, tryptophan, glutamic acid, aspartic acid, glutamine, asparagine, serine, threonine, cysteine, methionine, proline, and tyrosine.

4. The composition of claim 1 , wherein the amino acid carbamate is a carbamate of an amino acid selected from the group consisting of glycine, arginine, lysine, histidine, alanine, valine, leucine, isoleucine, phenylalanine, tryptophan, glutamic acid, aspartic acid, glutamine, asparagine, serine, threonine, cysteine, methionine, proline, and tyrosine.

5. The composition of claim 1 , wherein the complex has the formula [glycine] + [glycine carbamate] − , [lysine] + [lysine carbamate] − , [arginine] + [arginine carbamate] − , Na + [arginine carbamate] − , Na + [lysine carbamate] − or Na + [glycine carbamate] − .

6. The composition of claim 1 , wherein the composition comprises an effective amount of a fluoride ion source.

7. The composition of claim 1 , wherein the composition comprises an abrasive.

8. The composition of claim 1 , wherein the composition comprises a surfactant.

9. A method of making the amino acid carbamate complex of claim 1 , comprising the steps of (1) dissolving or suspending an amino acid, in free base or salt form, and a source of the cation M, in water to form a mixture, (2) adding to the mixture a carbon dioxide, in gaseous or solid form, (3) maintaining the pH of the solution above pH 8.0, optionally by adding an inorganic base, and (4) obtaining the resultant complex.

10. The method of claim 9 , wherein the amino acid is arginine in free base form.

11. The method of claim 9 , wherein the pH of the solution is maintained at pH 8.5 or above.

12. The method of claim 9 , wherein the inorganic base is added to maintain the pH of the solution, optionally wherein the base is selected from an oxide, hydroxide, carbonate or bicarbonate of an alkali metal or alkaline earth metal.

13. The method of claim 12 , wherein the base is selected from sodium hydroxide, potassium hydroxide, lithium hydroxide, sodium bicarbonate, potassium bicarbonate, lithium bicarbonate, sodium carbonate, potassium carbonate, lithium carbonate, sodium oxide, potassium oxide, or lithium oxide.

14. The method of claim 9 , wherein the mixture of water, source of the cation M, and amino acid of step (1) is heated prior to the addition of carbon dioxide of step (2).

15. The method of claim 14 , wherein the mixture is heated to a temperature of at least 50° C., or at least 60° C., at least 70° C., or at least 80° C.

16. A method of making the oral care composition of claim 1 , comprising adding an arginine/arginine carbamate complex obtained by the method according to claim 9 to a oral care base composition, and further adding additional oral care excipients or ingredients to produce an oral care composition.

17. A method to reduce acid erosion of the enamel, clean the teeth, reduce bacterially-generated biofilm and plaque, reduce gingivitis, inhibit tooth decay and formation of cavities, and reduce dentinal hypersensitivity, comprising applying the composition according to claim 1 to the teeth or oral cavity of a person in need thereof.

18. The method of claim 9 , wherein the pH of the solution is maintained at pH 9.0 or above, pH 9.5 or above, or about pH 9.0.

19. The method of claim 14 , wherein the mixture is heated to a temperature of from 50-90° C., from 60-90° C., from 70-90° C., from 80-90° C., or about 70° C.

Assignees

• Colgate Palmolive Co

Inventors

• Pan Long
• Wu Donghui
• Subramanyam Ravi
• Shen Hongwei
• Cheng Chi-Yuan
• Brinzari Tatiana

Classifications

• C07C271/06

  Esters of carbamic acids · CPC title

• A61K8/445

  aromatic, i.e. the carboxylic acid directly linked to the aromatic ring · CPC title

• A61K8/492

  having condensed rings, e.g. indol · CPC title

• A61K8/4946

  Imidazoles or their condensed derivatives, e.g. benzimidazoles · CPC title

• C07C279/14

  being further substituted by carboxyl groups · CPC title