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WO2010039145A1 - Procédé et concentré pour augmenter l'efficacité du pyrithione de zinc dans des produits de soins corporels - Google Patents

Procédé et concentré pour augmenter l'efficacité du pyrithione de zinc dans des produits de soins corporels Download PDF

Info

Publication number
WO2010039145A1
WO2010039145A1 PCT/US2008/078665 US2008078665W WO2010039145A1 WO 2010039145 A1 WO2010039145 A1 WO 2010039145A1 US 2008078665 W US2008078665 W US 2008078665W WO 2010039145 A1 WO2010039145 A1 WO 2010039145A1
Authority
WO
WIPO (PCT)
Prior art keywords
zpt
personal care
particle size
zinc pyrithione
ester
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/US2008/078665
Other languages
English (en)
Inventor
Kolazi S. Narayanan
Domingo Jon
Raymond Rigoletto
Roger L. Mcmullen
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 PCT/US2008/078665 priority Critical patent/WO2010039145A1/fr
Publication of WO2010039145A1 publication Critical patent/WO2010039145A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

Links

Classifications

    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q5/00—Preparations for care of the hair
    • A61Q5/006—Antidandruff preparations
    • 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
    • A61K8/49—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds
    • A61K8/4906—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with one nitrogen as the only hetero atom
    • A61K8/4933—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with one nitrogen as the only hetero atom having sulfur as an exocyclic substituent, e.g. pyridinethione
    • 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
    • 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
    • A61K8/817—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 single or double bond to nitrogen or by a heterocyclic ring containing nitrogen; Compositions or derivatives of such polymers, e.g. vinylimidazol, vinylcaprolactame, allylamines (Polyquaternium 6)
    • A61K8/8176—Homopolymers of N-vinyl-pyrrolidones. Compositions of derivatives of such polymers
    • 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
    • A61K8/91—Graft copolymers
    • 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
    • A61K8/922—Oils, fats or waxes; Derivatives thereof, e.g. hydrogenation products thereof of vegetable origin

Definitions

  • the present invention relates to the fungicide zinc pyrithione (ZPT) and more particularly, to a method and composition for increasing dispersabiiity and the deposition of particulate ZPT on the scalp for personal care products such as anti- dandruff shampoos, without adversely affecting its bioavailability, and while maintaining the cosmetic benefits of the shampoo application.
  • ZPT fungicide zinc pyrithione
  • ZPT zinc pyrithione
  • a suitable material for this purpose is zinc pyrithione (ZPT) which is a chelate of zinc ions and pyrithione.
  • ZPT particles tend to agglomerate in use which decreases their dispersabiiity, i.e., reduces their deposition and/or retention on the scalp during showering.
  • ZPT should deposit on the scalp itself to enhance its bioavailability rather than on the hair.
  • ZPT zinc pyrithione
  • a method for increasing the deposition of zinc pyrithione (ZPT) present in a personal care product without reducing its bioavailability and while maintaining the efficacy of such product comprises including in said product a polymer selected from the group consisting of: a) a powder blend of the partially neutralized alkyl ester of poly (methyl vinyl ether maieic acid) and polyvinyl pyrrolidone; b) an aqueous suspension of a water insoluble alkylated grafted vinyl pyrrolidone graft copolymer having a submicron particle size; and c) a unseed oil-modified dicarboxylic acid half-ester of maieic acid.
  • ZPT zinc pyrithione
  • this invention provides a concentrate comprising zinc pyrithione, at least one of the above-described polymers and a carrier.
  • a personal care product comprising zinc pyrithione, at least one of the above described polymers and optionally one or more personal care ingredients.
  • ZPT zinc pyrithione
  • specific polymers i.e., a polymer selected from a powder blend of the partially neutralized monobutyl ester of poly (methyl vinyl ether maieic acid) and polyvinyl pyrrolidone; an aqueous suspension of a water insoluble Ci 6 alkylated grafted vinyl pyrrolidone graft copolymer having a submicron particle size; and a linseed oil-modified dicarboxylic acid half-ester of maleic acid
  • the invention can also be practiced in conjunction with other actives besides zinc pyrithione, such as, for example, zinc/magnesium, copper, cadmium, barium, bismuth and zirconium pyrithiones, coai tar, salicylic acid, selenium sulfide, sulfur, and with other polymers
  • the zinc pyrithione can be present in a particle size of about 0.5- 5 ⁇ , preferably 0.8- 4 ⁇ , and most preferably 1-3 ⁇ .
  • a preferred polymer additive for ZPT dispersing is the sodium salt of alkyivinylether maleic acid half-ester copolymer (EasySperse ® ) (ISP) and polyvinyl pyrrolidone (PVP K-30), most preferably in a weight ratio of about 1 :1 to 1 :4, sold by ISP as EasySperse ® P-20.
  • EasySperse ® is described in U.S. Patent No. 6,158,803, the disclosure of which is hereby incorporated by reference in its entirety.
  • a powder blend of the partially neutralized monobutyl ester of poly (methyl vinyl ether maleic acid) and polyvinyl pyrro ⁇ done is employed.
  • Another suitable polymer to disperse or retain ZPT is milk of Ganex (ISP), which is an aqueous suspension of Ganex ® 216 (ISP) 1 a water-insoluble alkyl grafted polyvinyl pyrrolidone graft copolymer having a particle size at the submicron level.
  • ISP aqueous suspension of Ganex ® 216
  • M ⁇ k of Ganex is described in U.S. Patent No. 6,624,242, the disclosure of which is hereby incorporated by reference in its entirety.
  • an aqueous suspension of a water-insoiuble C- I ⁇ alkyl grafted polyvinyl pyrrolidone graft copolymer having a particle size at the submicron level is described in U.S. Patent No. 6,624,242, the disclosure of which is hereby incorporated by reference in its entirety.
  • Still another useful polymer herein is a partially netralized linseed oil- modified dicarboxylic acid half-ester of maleic acid.
  • This material is commercially available as a liquid from Ashland Chemical under the tradename Bomol 4N. This product is neutralized with 2-aminopropanol to a neutral pH.
  • the concentrate according to this invention includes ZPT, at least one of the above-described polymers and a suitable carrier.
  • a preferred suitable carrier is water.
  • the ZPT can be present in the concentrate in an amount of 1-55, preferably 5-50 and most preferably 10-40% by weight.
  • the concentrate can contain conventional adjuvants, e.g., suspending agents, defoamers and thickening agents, known in the art in amounts up to about 10% by weight.
  • the polymer can be present in the concentrate generally in an amount of
  • the polymer preferably can be present in an amount of about 0.1-10, more preferably 0.5-5, and most preferably 1-4% by weight.
  • the polymer preferably can be present in an amount of about 2-15, more preferably 3-12, and most preferably 4-10% by weight.
  • the polymer preferably can be present in an amount of about 0.1- 15, more preferably 0.5-12, and most preferably 1-10% by weight. The optimum amount of polymer present depends on, e.g., the polymer and active selected, the ZPT particle size, etc. and can readily be determined by one of ordinary skill in the art.
  • Personal care products according to this invention feature ZPT and at least one of the above-described polymers.
  • the ZPT can be present in an amount of 0.001-10, preferably 0.01-5 and more preferably 0.1-2% by weight.
  • anti-dandruff applications e.g., anti-dandruff shampoos
  • the polymer can be added to the personal care product by known techniques.
  • the polymer can be added directly to the ZPT containing personal care product, in a preferred embodiment, the concentrate of this invention is incorporated into the process for manufacturing the personal care product.
  • the following examples further illustrate the invention.
  • test shampoo matrix used to incorporate the various poiymeric dispersants with ZPT.
  • a second test shampoo matrix evaluated was a commercial shampoo matrix.
  • these formulations are merely representative and it is understood that the invention can be practiced, e.g., with other shampoos and personal care compositions containing various surfactants, blends of surfactants and adjuvants known in the art. See, for example, U. S. Patent No. 7,026,308, the disclosure of which is hereby incorporated by reference in its entirety.
  • Shampoo matrices containing bio-active materials and polymeric additives were prepared. Polymeric additives were first incorporated into commercial ZPT dispersions. The fortified commercial ZPT dispersions were then added and homogenized with the shampoo matrices. 1.83% Zinc pyrithione and 0.19% Ganex 216 fine suspension in water (10% solid) in shampoo base
  • 1.83% Zinc Pyrithione, 0.19% Ganex emuision and 89.83% shampoo base was formulated as follows: a premix oil was prepared by mixing 6.08 g zinc pyrithione (Arch 30% suspension concentrate) with 0.34% Ganex 216 fine suspension in water (pre-dispersed with EasySperse (ISP) in water) in a 10 ml vial. The pre-mixed sample was shaken vigorously and it was allowed to mix in a rotary wheel for four hours. 3.5 g of a shampoo matrix was weighed and added to a 50 ml container. 3.38 g of water and 45.03 g of a shampoo base were added to the container. This formulated sample was shaken vigorously and it was allowed to mix in a rotary wheel overnight. A homogeneous cloudy suspension was formed that separated over a weekend but was re-dispersible with moderate shaking.
  • Zinc pyrithione in 89.73% shampoo base (containing water) made up to 100% with water was formulated as follows: 3.35 g of ⁇ 55% zinc pyrithione concentrate (Arch chemicals), was weighed and added to a 50 ml container. 3.47 g of water and 45.01 g of shampoo base were also added to the container. This formulated sample was shaken vigorously and it was allowed to mix in a rotary wheel overnight. A homogeneous cloudy suspension was formed that separated over the weekend but was re-dispersible with moderate shaking.
  • Table 1 summarizes compositions prepared for evaluating dispersion stability and effects of improvement in accordance with this invention.

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  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Birds (AREA)
  • Epidemiology (AREA)
  • Chemical & Material Sciences (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Cosmetics (AREA)

Abstract

L'invention concerne un procédé pour augmenter le dépôt de pyrithione de zinc présent dans un produit de soins corporels sans réduire sa biodisponibilité et tout en conservant l'efficacité du produit. Le procédé comprend, en plus du pyrithione de zinc, un polymère sélectionné parmi un mélange pulvérulent d'un ester alkylique de poly(méthyl vinyl éther/acide maléique) partiellement neutralisé et de polyvinylpyrrolidone ; une suspension aqueuse d'un copolymère greffé de vinylpyrrolidone greffée alkylée insoluble dans l'eau ayant une taille de particules submicronique ; et un demi-ester d'acide maléique à fonction acide dicarboxylique modifié par de l'huile de lin partiellement neutralisé. La présente invention concerne en outre des concentrés et des produits de soins corporels contenant du pyrithione de zinc et au moins un des polymères décrits ci-dessus.
PCT/US2008/078665 2008-10-03 2008-10-03 Procédé et concentré pour augmenter l'efficacité du pyrithione de zinc dans des produits de soins corporels Ceased WO2010039145A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
PCT/US2008/078665 WO2010039145A1 (fr) 2008-10-03 2008-10-03 Procédé et concentré pour augmenter l'efficacité du pyrithione de zinc dans des produits de soins corporels

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
PCT/US2008/078665 WO2010039145A1 (fr) 2008-10-03 2008-10-03 Procédé et concentré pour augmenter l'efficacité du pyrithione de zinc dans des produits de soins corporels

Publications (1)

Publication Number Publication Date
WO2010039145A1 true WO2010039145A1 (fr) 2010-04-08

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Country Status (1)

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Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2014082846A1 (fr) * 2012-11-29 2014-06-05 Unilever Plc Composition de soins des cheveux
CN104812365A (zh) * 2012-11-29 2015-07-29 荷兰联合利华有限公司 头发护理组合物
US9556405B2 (en) 2012-11-29 2017-01-31 Conopco, Inc. Polymer structured aqueous detergent compositions
US10166173B2 (en) 2014-12-02 2019-01-01 Dow Global Technologies Llc Polyurethane microparticles coated with a zinc salt and methods for the preparation thereof
US20190091115A1 (en) * 2017-09-28 2019-03-28 The Procter & Gamble Company Conditioner compositions with polyacrylate microcapsules having improved long-lasting odor benefit

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6335312B1 (en) * 1997-10-14 2002-01-01 The Procter & Gamble Company Personal cleansing compositions comprising mid-chain branched surfactants
US20020011584A1 (en) * 2000-02-14 2002-01-31 Hirotaka Uchiyama Stable, aqueous compositions for treating surfaces, especially fabrics

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6335312B1 (en) * 1997-10-14 2002-01-01 The Procter & Gamble Company Personal cleansing compositions comprising mid-chain branched surfactants
US20020011584A1 (en) * 2000-02-14 2002-01-31 Hirotaka Uchiyama Stable, aqueous compositions for treating surfaces, especially fabrics

Cited By (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2014082846A1 (fr) * 2012-11-29 2014-06-05 Unilever Plc Composition de soins des cheveux
CN104812365A (zh) * 2012-11-29 2015-07-29 荷兰联合利华有限公司 头发护理组合物
JP2016500120A (ja) * 2012-11-29 2016-01-07 ユニリーバー・ナームローゼ・ベンノートシヤープ 毛髪ケア組成物
US9556405B2 (en) 2012-11-29 2017-01-31 Conopco, Inc. Polymer structured aqueous detergent compositions
US10166173B2 (en) 2014-12-02 2019-01-01 Dow Global Technologies Llc Polyurethane microparticles coated with a zinc salt and methods for the preparation thereof
US20190091115A1 (en) * 2017-09-28 2019-03-28 The Procter & Gamble Company Conditioner compositions with polyacrylate microcapsules having improved long-lasting odor benefit
EP3461470A1 (fr) * 2017-09-28 2019-04-03 The Procter & Gamble Company Compositions de conditionnement avec des microcapsules de polyacrylate présentant un avantage amélioré lié à une odeur de longue durée
WO2019067661A1 (fr) * 2017-09-28 2019-04-04 The Procter & Gamble Company Compositions de conditionneur comprenant des microcapsules de polyacrylate ayant une utilité liée à un parfum de longue durée
CN111148501A (zh) * 2017-09-28 2020-05-12 宝洁公司 具有改善持久气味有益效果的聚丙烯酸酯微胶囊的调理剂组合物
JP2020533361A (ja) * 2017-09-28 2020-11-19 ザ プロクター アンド ギャンブル カンパニーＴｈｅ Ｐｒｏｃｔｅｒ ＆ Ｇａｍｂｌｅ Ｃｏｍｐａｎｙ 改善された長続きする香り効果を有するポリアクリレートマイクロカプセルを含むコンディショナー組成物
JP7007464B2 (ja) 2017-09-28 2022-01-24 ザ プロクター アンド ギャンブル カンパニー 改善された長続きする香り効果を有するポリアクリレートマイクロカプセルを含むコンディショナー組成物

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