IP Library Granted Patent US 11,395,792
Granted Patent B2
US 11,395,792 · App. 16/892,413 · Granted Jul 26, 2022

Oral care composition

Inventors: Juie Tanavade (Hillsborough, NJ); Marivi Ortiz-Suarez (Burlington, NJ); Alexandre Graet (New York, NY); Laurianne Timbart (Bensalem, PA)
Assignee: RHODIA OPERATIONS
A61K8/43A61K8/24A61K8/416A61K8/8147A61K8/8164A61Q11/00
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Quick Facts
Patent No.
US 11,395,792
App. No.
16/892,413
Granted
Jul 26, 2022
Kind
B2
Abstract

An oral care composition including an amphoteric surfactant or betaine, a copolymer, and an orally acceptable cationic antibacterial agent; and methods of using the oral care composition.

Claims (52)

1. An oral care composition comprising:

an orally acceptable carrier;

an amphoteric surfactant having a structure of formula (I):

wherein L is a substituted or unsubstituted (C 2 -C 4 ) alkylene,

n is an integer from 1 to 10,

R a and R b are independently C 1 -C 4 alkyl,

R c is substituted or unsubstituted C 1 -C 20 alkyl, and

Y is an anionic group;

an orally acceptable cationic antibacterial agent; and

a copolymer of i) an allyl phosphate compound; and ii) one or more α, β-ethylenically unsaturated co-monomers, at least one of which is other than an allyl-functional co-monomer,

wherein the allyl phosphate compound has the formula (A):

[CH 2 ═CH—CH 2 —O(R 1 O) a (R 2 O) b ] x P(O)(OM) 3-x   (A)

wherein

R 1 is a substituted or unsubstituted (C 2 -C 4 ) alkylene moiety;

R 2 is a substituted or unsubstituted (C 2 -C 4 ) alkylene moiety;

M is identical or different, hydrogen, alkali metal, ammonium, protonated alkyl amine, protonated alkanolamine, or protonated basic amino acid;

X is 1 or 2;

a is from 1 to 20; and

b is from 0 to 20.

2. The oral care composition of claim 1 , wherein Y is —C(O)O, or —S(O) 2 O.

3. The oral care composition of claim 1 , wherein n is 2, 3, or 4.

4. The oral care composition of claim 1 , wherein R a and R b are independently methyl or ethyl.

5. The oral care composition of claim 1 , wherein the amphoteric surfactant is selected from the group consisting of cocamidopropyl betaine, lauramidopropyl betaine, cocobetaine, cocamidopropyl hydroxysultaine, and combinations thereof.

6. The oral care composition of claim 1 , wherein R 1 and R 2 are independently substituted with a hydroxyl, alkoxyl, or aryloxyl moiety.

7. The oral care composition of claim 1 , wherein the one or more α, β-ethylenically unsaturated co-monomers comprise a moiety selected from the group consisting of maleic anhydride, maleic acid, itaconic anhydride, itaconic acid, and combinations thereof.

8. The oral care composition of claim 1 , wherein the orally acceptable cationic antibacterial agent is selected from the group consisting of chlorhexidine gluconate, cetyl pyridium chloride, quaternary ammonium surfactants, cationic amino acids, metal cations, and combinations thereof.

9. The oral care composition of claim 1 , wherein the copolymer is polymerized from a mixture comprising one or more α, β-ethylenically unsaturated maleimide phosphate co-monomers, and the one or more α, β-ethylenically unsaturated co-monomers.

10. The oral care composition of claim 9 , wherein one of the α, β-ethylenically unsaturated maleimide phosphate co-monomer has the formula (B),

wherein

R 1′ is a substituted or unsubstituted (C 2 -C 4 ) alkylene moiety;

R 2′ is a substituted or unsubstituted (C 2 -C 4 ) alkylene moiety;

M′ is identical or different, hydrogen, alkali metal, ammonium, protonated alkyl amine, protonated alkanolamine, or protonated basic amino acid;

X′ is 1 or 2;

a′ is from 1 to 20; and

b′ is from 0 to 20.

11. The oral care composition of claim 10 , wherein R 1′ and R 2′ are each independently substituted with a hydroxyl, alkoxyl, or aryloxyl moiety.

12. The oral care composition of claim 1 , wherein one of the α, β-ethylenically unsaturated co-monomers has the formula (E):

CH 2 ═C(R 2 ″)CH 2 O(R 3 ″)(OH)SO 3 M″  (E)

wherein

R 2 ″ is H or an alkyl radical,

R 3 ″ is a linear or branched divalent aliphatic radical which may be hydroxyl substituted,

and

M″ is alkali metal, ammonium, protonated alkyl amine, protonated alkanolamine, or protonated basic amino acid.

13. The oral care composition of claim 1 , wherein the one or more of the α, β-ethylenically unsaturated co-monomers are selected from the group consisting of allyl ethoxylate, allyl polyethoxylate, methallyl ethoxylate, methallyl polyethoxylate, sodium 1-allyloxy-2-hydroxypropyl sulfonate, sodium 2-acrylamido-2-methylpropane sulfonate, sodium vinyl sulfonate, sodium styrene sulfonate, acrylic acid, methacrylic acid, vinyl acetate, acrylate ester, methacrylate ester, maleate ester, styrene, and combinations thereof.

14. The oral care composition of claim 1 , wherein one of the α, β-ethylenically unsaturated co-monomers is a maleimide phosphate compound having a structure of

15. The oral care composition of claim 1 , wherein the allyl phosphate compound is of the formula (A-1)

wherein n is 1 to 20.

16. The oral care composition of claim 1 , further comprising an abrasive polishing material selected from the group consisting of a silica, an alumina, an orthophosphate, a polyphosphate, a hexametaphosphate, and combinations thereof.

17. The oral care composition of claim 1 , further comprising one or more additives selected from the group consisting of a polishing agent, a sudsing agent, a binder, a humectant, a medicinal agent, a sweetening agent, a flavor, a peroxide source, an alkali metal bicarbonate salt, a thickening agent, xylitol, sorbitol, a coloring agent, sodium carbonate, and combinations thereof.

18. The oral care composition of claim 1 , wherein the oral care composition is in a form of a toothpaste, tooth gel, dentifrice, tooth powder, prophy paste, mouthwash, rinse, tooth mousse, dental floss, chewing gum, soluble oral care strip or film for direct application or attachment to an oral surface, or lozenge.

19. A method of combating dental caries, erosion, hypersensitivity, and/or staining comprising using the oral care composition of claim 18 .

20. A method of treating or preventing dental caries, erosion, hypersensitivity, staining, or a combination thereof comprising using the oral care composition of claim 1 .

Assignments (3)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jan 26, 2024
From: RHODIA OPERATIONS
To: SPECIALTY OPERATIONS FRANCE
Reel/Frame 066374/0642 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Nov 7, 2023
From: RHODIA OPERATIONS
To: SPECIALTY OPERATIONS FRANCE
Reel/Frame 065488/0365 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Sep 2, 2020
From: TANAVADE, JUIE; ORTIZ-SUAREZ, MARIVI; TIMBART, LAURIANNE; GRAET, ALEXANDRE
To: RHODIA OPERATIONS
Reel/Frame 053678/0795 →