WO2008014379A1 - Oral care compositions - Google Patents

Oral care compositions Download PDF

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Publication number
WO2008014379A1
WO2008014379A1 PCT/US2007/074429 US2007074429W WO2008014379A1 WO 2008014379 A1 WO2008014379 A1 WO 2008014379A1 US 2007074429 W US2007074429 W US 2007074429W WO 2008014379 A1 WO2008014379 A1 WO 2008014379A1
Authority
WO
WIPO (PCT)
Prior art keywords
oral care
antibacterial agent
care composition
vinyl ether
surface active
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Ceased
Application number
PCT/US2007/074429
Other languages
French (fr)
Inventor
William E. Prosise
Jay Hilsenbeck
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
ISP Investments LLC
Original Assignee
ISP Investments LLC
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by ISP Investments LLC filed Critical ISP Investments LLC
Priority to US12/374,423 priority Critical patent/US20100150849A1/en
Priority to GB0822914A priority patent/GB2453072B/en
Publication of WO2008014379A1 publication Critical patent/WO2008014379A1/en
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

Links

Classifications

    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
    • A61K8/34—Alcohols
    • A61K8/347—Phenols
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/72—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
    • A61K8/81—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds
    • A61K8/8164—Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a carboxyl radical, and containing at least one other carboxyl radical in the molecule, or of salts, anhydrides, esters, amides, imides or nitriles thereof; Compositions of derivatives of such polymers, e.g. poly (methyl vinyl ether-co-maleic anhydride)
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/075—Ethers or acetals
    • A61K31/085—Ethers or acetals having an ether linkage to aromatic ring nuclear carbon
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/72—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
    • A61K8/73—Polysaccharides
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/92—Oils, fats or waxes; Derivatives thereof, e.g. hydrogenation products thereof
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q11/00—Preparations for care of the teeth, of the oral cavity or of dentures; Dentifrices, e.g. toothpastes; Mouth rinses

Definitions

  • This invention relates to oral care compositions, such as toothpaste compositions, and more particularly to such compositions containing a copolymer of an alkylvinyl ether and maleic acid or maieic anhydride, e.g., Gantrez ® S-97 (ISP), and an additive which is a surface active vegetable gum as an effective antibacterial enhancing agent (AEA) for a non-cationic antibacterial agent, e.g., triciosan.
  • the compositions exhibit high uptake and retention of the antibacteriai agent on teeth.
  • compositions comprising non-cationic antibacterial agents and copolymers of maleic acid or maleic anhydride and an alkyl vinyl ether, e.g., methylvinyl ether-mateic acid anhydride, and other poiycarboxylates are well known in the art. See, for example, U.S.
  • compositions comprising a copolymer of an alkylvinyl ether and maleic acid or maleic anhydride, a surface active vegetable gum and a non-cationic antibacterial agent exhibit unexpectedly high uptake and retention of the non-cationic antibacterial agent on teeth.
  • oral care compositions comprising a copolymer of an alkyl vinyl ether and maleic acid or anhydride, a surface active vegetable gum and a non-cationic antibacterial agent.
  • the oral care compositions exhibit increased uptake and retention of the non-cationic antibacterial agent on application to teeth.
  • a method of enhancing the uptake and/or retention of a non-cationic antibacterial agent on teeth comprising delivering said non-cationic antimicrobial agent to the teeth in combination with a copolymer of maleic acid or maleic anhydride and an aikyl vinyl ether and a surface active vegetable gum.
  • FIG. 1 shows the procedure used for testing the efficacy of uptake/retention of the non-cationic antibacterial agent triclosan on mucin-coated HAP disks.
  • FIG. 2 is a graphical representation of uptake and retention of triclosan from a composition of maleic acid-methyl vinyl ether polymer and surface active vegetable gum, i.e., gum arabic (invention) vs. a control containing a maleic acid-methyl vinyl ether copolymer and no surface active vegetable gum.
  • the invention is described hereinafter with respect to preferred embodiments thereof, e.g., a maleic acid or maleic anhydride alkyl vinyl ether copolymer in combination with the non-cationic antibacterial agent triclosan and the surface active vegetable gum arabic, the invention can also be practiced in connection with other non-cationic antibacterial agents such as thymol, phenol and other phenolics and with other surface active vegetable gums such as hydroxypropylmethylcellulose or karaya gum.
  • non-cationic antibacterial agents such as thymol, phenol and other phenolics
  • surface active vegetable gums such as hydroxypropylmethylcellulose or karaya gum.
  • the oral care compositions can contain up to about 10 % by weight of the maleic acid or maleic anhydride alkyl vinyl ether copolymers.
  • the maleic acid or maleic anhydride alkyl vinyl ether copolymers can be present in an amount of 0.1-5 wt%, preferably 0.5-3 wt%.
  • the non-cationic antibacterial agent can be present in an amount of about
  • the surface active vegetable gum can be present in an amount of about
  • the oral care composition can take the form of any conventional oral care composition.
  • the oral care composition can be in the form of a denture adhesive, a mouth wash, a lozenge, chewing gum and the like.
  • the specific viscosity (SV) of the maleic acid or maleic anhydride alkyl vinyl ether copolymers can be in the range of 0.1 to about 10, preferably 0.1-6 and more preferably 0.2-6.
  • specific viscosity refers to the viscosity of the alkyl vinyl ether maleic anhydride copolymer in a suitable solvent divided by the viscosity of the solvent.
  • the non-cationic antibacterial agent is present in the presence of a known surface active agent such as sodium lauryl sulfate.
  • a known surface active agent such as sodium lauryl sulfate.
  • Other surface active agents normally used in oral care compositions can also be used.
  • An example is Poloxamers, A preferred Poloxamer is Poloxamer 407 available from BASF Corp.
  • compositions of this invention can contain a bimodal blend of such copolymers having specific viscosities in the ranges of 2-10 and 0.1-2 respectively.
  • FIG. 1 The procedure used for testing the efficacy of the compositions of the invention is shown in FIG. 1.
  • FIG. 2 The results of such testing are shown in FIG. 2 which demonstrate that the gum arabic containing oral care compositions of this invention exhibit increased uptake and retention of the non-cationic antibacterial agent triclosan as compared to the control.

Landscapes

  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Veterinary Medicine (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Epidemiology (AREA)
  • Birds (AREA)
  • Chemical & Material Sciences (AREA)
  • Emergency Medicine (AREA)
  • Oral & Maxillofacial Surgery (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Medicinal Chemistry (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Cosmetics (AREA)

Abstract

An oral care composition comprising a copolymer of an alkyl vinyl ether and maleic acid or anhydride, a surface active vegetable gum, and a non-cationic antibacterial agent. The composition exhibits increased uptake and retention of the non-cationic antibacterial agent on application to teeth.

Description

ORAL CARE COMPOSITIONS
CROSS-REFERENCE TO RELATED APPLICATIONS
[0001] The present application claims the benefit of U.S. Provisional Application
Serial No. 60/833,498, filed on July 26, 2006, the disclosure of which is hereby incorporated by reference in its entirety.
FIELD OF THE INVENTION
[0002] This invention relates to oral care compositions, such as toothpaste compositions, and more particularly to such compositions containing a copolymer of an alkylvinyl ether and maleic acid or maieic anhydride, e.g., Gantrez® S-97 (ISP), and an additive which is a surface active vegetable gum as an effective antibacterial enhancing agent (AEA) for a non-cationic antibacterial agent, e.g., triciosan. The compositions exhibit high uptake and retention of the antibacteriai agent on teeth.
BACKGROUND OF THE INVENTION
[0003] Oral care compositions comprising non-cationic antibacterial agents and copolymers of maleic acid or maleic anhydride and an alkyl vinyl ether, e.g., methylvinyl ether-mateic acid anhydride, and other poiycarboxylates are well known in the art. See, for example, U.S. Patents 6,692,725; 5,776,435; 5,686,064; 5,582,816; 5,538,715; 5,531 ,982; 5,496,540; 5,472,685; 5,466,437; 5,453,265; 5,368,844; 5,356,615; 5,344,641 ; 5,334,325; 5,312,618; 5,294,431 ; 5,292,526; 5,288,480; 5,279,813; 5,275,805; 5,273,741 ; 5,260,062; 5,256,401 ; 5,192,531 ; 5,192,530; 5,188,821 ; 5,180,578; 5,178,851 ; 5,167,951 ; 5,156,835; 5,135,738; 5,080,887; 5,037,637; 5,032,386; and 4,894,220.
[0004] However, none of these patented compositions exhibit a particularly high uptake and retention of the antibacterial agent on teeth. It would be desirable for improved dental health to provide oral care compositions with enhanced uptake and retention of an antibacterial agent on teeth. Accordingly, it is an object of this invention to improve the efficacy of oral care compositions containing a non-cationic antibacterial agent. SUMMARY OF THE INVENTION
[0005] We have discovered that oral care compositions comprising a copolymer of an alkylvinyl ether and maleic acid or maleic anhydride, a surface active vegetable gum and a non-cationic antibacterial agent exhibit unexpectedly high uptake and retention of the non-cationic antibacterial agent on teeth.
[0006] In accordance with this invention, there is provided oral care compositions comprising a copolymer of an alkyl vinyl ether and maleic acid or anhydride, a surface active vegetable gum and a non-cationic antibacterial agent. The oral care compositions exhibit increased uptake and retention of the non-cationic antibacterial agent on application to teeth.
[0007] In another embodiment of the invention, there is provided a method of enhancing the uptake and/or retention of a non-cationic antibacterial agent on teeth, the method comprising delivering said non-cationic antimicrobial agent to the teeth in combination with a copolymer of maleic acid or maleic anhydride and an aikyl vinyl ether and a surface active vegetable gum.
BRIEF DESCRIPTION OF THE FIGURES
[0008] FIG. 1 shows the procedure used for testing the efficacy of uptake/retention of the non-cationic antibacterial agent triclosan on mucin-coated HAP disks.
[0009] FIG. 2 is a graphical representation of uptake and retention of triclosan from a composition of maleic acid-methyl vinyl ether polymer and surface active vegetable gum, i.e., gum arabic (invention) vs. a control containing a maleic acid-methyl vinyl ether copolymer and no surface active vegetable gum.
DETAILED DESCRIPTION OF THE INVENTION
[0010] While the invention is described hereinafter with respect to preferred embodiments thereof, e.g., a maleic acid or maleic anhydride alkyl vinyl ether copolymer in combination with the non-cationic antibacterial agent triclosan and the surface active vegetable gum arabic, the invention can also be practiced in connection with other non-cationic antibacterial agents such as thymol, phenol and other phenolics and with other surface active vegetable gums such as hydroxypropylmethylcellulose or karaya gum.
[0011] The oral care compositions can contain up to about 10 % by weight of the maleic acid or maleic anhydride alkyl vinyl ether copolymers. In toothpastes, the maleic acid or maleic anhydride alkyl vinyl ether copolymers can be present in an amount of 0.1-5 wt%, preferably 0.5-3 wt%.
[0012] The non-cationic antibacterial agent can be present in an amount of about
0.01-5 wt%, preferably 0.1-4 wt% and more preferably 0.2-3 wt%.
[0013] The surface active vegetable gum can be present in an amount of about
0.001-5 wt%, preferably 0.01-4 wt% and more preferably 0.05-3 wt%.
[0014] The oral care composition can take the form of any conventional oral care composition. In addition to toothpastes, the oral care composition can be in the form of a denture adhesive, a mouth wash, a lozenge, chewing gum and the like.
[0015] The specific viscosity (SV) of the maleic acid or maleic anhydride alkyl vinyl ether copolymers can be in the range of 0.1 to about 10, preferably 0.1-6 and more preferably 0.2-6. As used herein, "specific viscosity" refers to the viscosity of the alkyl vinyl ether maleic anhydride copolymer in a suitable solvent divided by the viscosity of the solvent.
[0016] In a particularly preferred embodiment, the non-cationic antibacterial agent is present in the presence of a known surface active agent such as sodium lauryl sulfate. Other surface active agents normally used in oral care compositions can also be used. An example is Poloxamers, A preferred Poloxamer is Poloxamer 407 available from BASF Corp.
[0017] In yet another embodiment, this invention can be practiced in conjunction with multimodel blends of copolymers of maleic acid or maleic anhydride and an alcylvinylether as described more fully in commonly assigned PCT International Application entitled "ORAL CARE COMPOSITIONS" filed on even date herewith, the disclosure of which is hereby incorporated by reference in its entirety. For example, compositions of this invention can contain a bimodal blend of such copolymers having specific viscosities in the ranges of 2-10 and 0.1-2 respectively.
EXAMPLE
Toothpaste (TYP) Mixtures for Triclosan Uptake and Retention Tests
Stock T/P Mixture without abrasives:
Add: 61.0O g Water
20.00 g 70% Sorbitol
13.00 g Propylene glycol
2.46 g Sodium lauryl sulfate
0.30 g Non-cationic antibacterial {triclosan)
1.00 g Ethanol
0.24 g NaF
1.80 g Maleic acid-vinyl ether copolymer* (Gantrez-97)
0.20 g Gum Arabic**
*suitably present in an amount of 0.01-5% by wt in the composition. **0.1 to 1% by wt.
[0018] The procedure used for testing the efficacy of the compositions of the invention is shown in FIG. 1. The results of such testing are shown in FIG. 2 which demonstrate that the gum arabic containing oral care compositions of this invention exhibit increased uptake and retention of the non-cationic antibacterial agent triclosan as compared to the control.

Claims

CLAIMS What is claimed:
1. An oral care composition comprising: a) a copolymer of an alkyl vinyl ether and maJeic acid or anhydride b) a surface active vegetable gum, and c) a non-cationic antibacterial agent, wherein said composition exhibits increased uptake and retention of said antibacterial agent to teeth.
2. The oral care composition of claim 1 in wherein said aikyl vinyl ether is methyl vinyl ether.
3. The oral care composition of claim 1 wherein said non-cationic antibacterial agent is triclosan.
4. The oral care composition of claim 1 wherein said surface active vegetable gum is gum Arabic.
5. The oral care composition of claim 1 wherein said copolymer is present in an amount of 0.01-5 wt%, and said substance is an amount of about 0.1-1 wt%.
6. The orai care composition of claim 1 wherein said non-cationic antibacterial agent is present in an amount of about 0.1-1 wt%.
7. The oral care composition of claim 1 wherein said surface active vegetable gum is present in an amount of 0.01-10 wt%.
8. An oral care composition comprising a copolymer of maleic anhydride or maleic acid and a methyl vinyl ether, triclosan and gum acacia.
9. A method of enhancing the uptake and/or retention of a non-cationic antibacterial agent on teeth, said method comprising delivering said non-cationic antimicrobial agent to said teeth in combination with a copolymer of maleic acid or maleic anhydride and an aiky! vinyl ether and a surface active vegetable gum.
PCT/US2007/074429 2006-07-26 2007-07-26 Oral care compositions Ceased WO2008014379A1 (en)

Priority Applications (2)

Application Number Priority Date Filing Date Title
US12/374,423 US20100150849A1 (en) 2006-07-26 2007-07-26 Oral Care Compositions
GB0822914A GB2453072B (en) 2006-07-26 2007-07-26 Oral care compositions

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US83349806P 2006-07-26 2006-07-26
US60/833,498 2006-07-26

Publications (1)

Publication Number Publication Date
WO2008014379A1 true WO2008014379A1 (en) 2008-01-31

Family

ID=38981802

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/US2007/074429 Ceased WO2008014379A1 (en) 2006-07-26 2007-07-26 Oral care compositions

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US (1) US20100150849A1 (en)
GB (1) GB2453072B (en)
WO (1) WO2008014379A1 (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US9855200B2 (en) 2009-05-26 2018-01-02 Colgate-Palmolive Company Oral care formulations that enhance amount of soluble zinc

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP2758025B1 (en) 2011-07-12 2018-09-26 Unilever N.V. Toothpaste comprising calcium based abrasives

Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5334375A (en) * 1988-12-29 1994-08-02 Colgate Palmolive Company Antibacterial antiplaque oral composition

Family Cites Families (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6214320B1 (en) * 1990-10-09 2001-04-10 Colgate-Palmolive Company Oral compositions containing anticalculus and antiplaque agents
US5395867A (en) * 1993-03-01 1995-03-07 Isp Investments Inc. Denture adhesive
US5298534A (en) * 1993-03-01 1994-03-29 Isp Investments Inc. Denture adhesive
US6136298A (en) * 1994-07-14 2000-10-24 Colgate-Palmolive Company Process for inhibiting S. mutans and caries
US8974772B2 (en) * 2004-12-28 2015-03-10 Colgate-Palmolive Company Two phase toothpaste composition
US20060140882A1 (en) * 2004-12-29 2006-06-29 Tambs Gary E Two phase whitening oral care composition

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5334375A (en) * 1988-12-29 1994-08-02 Colgate Palmolive Company Antibacterial antiplaque oral composition

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US9855200B2 (en) 2009-05-26 2018-01-02 Colgate-Palmolive Company Oral care formulations that enhance amount of soluble zinc

Also Published As

Publication number Publication date
US20100150849A1 (en) 2010-06-17
GB0822914D0 (en) 2009-01-28
GB2453072B (en) 2011-03-02
GB2453072A (en) 2009-03-25

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