EP1611157A2 - Cationic, oxidized polysaccharides in conditioning applications - Google Patents

Cationic, oxidized polysaccharides in conditioning applications

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Publication number
EP1611157A2
EP1611157A2 EP04750005A EP04750005A EP1611157A2 EP 1611157 A2 EP1611157 A2 EP 1611157A2 EP 04750005 A EP04750005 A EP 04750005A EP 04750005 A EP04750005 A EP 04750005A EP 1611157 A2 EP1611157 A2 EP 1611157A2
Authority
EP
European Patent Office
Prior art keywords
composition
cationic
polysaccharide
group
polymer
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.)
Withdrawn
Application number
EP04750005A
Other languages
German (de)
English (en)
French (fr)
Inventor
Paquita Erazo-Majewic
Jashawant J. Modi
Zu-Feng Xu
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.)
Hercules LLC
Original Assignee
Hercules LLC
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Filing date
Publication date
Application filed by Hercules LLC filed Critical Hercules LLC
Publication of EP1611157A2 publication Critical patent/EP1611157A2/en
Withdrawn legal-status Critical Current

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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
    • A61Q5/02—Preparations for cleaning the hair
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08B—POLYSACCHARIDES; DERIVATIVES THEREOF
    • C08B11/00—Preparation of cellulose ethers
    • C08B11/20—Post-etherification treatments of chemical or physical type, e.g. mixed etherification in two steps, including purification
    • 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
    • A61K8/72—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
    • A61K8/73—Polysaccharides
    • A61K8/731—Cellulose; Quaternized cellulose derivatives
    • 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
    • A61K8/737—Galactomannans, e.g. guar; Derivatives thereof
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q19/00—Preparations for care of the skin
    • 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
    • A61Q5/12—Preparations containing hair conditioners
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08B—POLYSACCHARIDES; DERIVATIVES THEREOF
    • C08B37/00—Preparation of polysaccharides not provided for in groups C08B1/00 - C08B35/00; Derivatives thereof
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
    • C11D3/16—Organic compounds
    • C11D3/20—Organic compounds containing oxygen
    • C11D3/22—Carbohydrates or derivatives thereof
    • C11D3/222—Natural or synthetic polysaccharides, e.g. cellulose, starch, gum, alginic acid or cyclodextrin
    • C11D3/227—Natural or synthetic polysaccharides, e.g. cellulose, starch, gum, alginic acid or cyclodextrin with nitrogen-containing groups
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
    • A61K2800/40—Chemical, physico-chemical or functional or structural properties of particular ingredients
    • A61K2800/54—Polymers characterized by specific structures/properties
    • A61K2800/542—Polymers characterized by specific structures/properties characterized by the charge
    • A61K2800/5426—Polymers characterized by specific structures/properties characterized by the charge cationic
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q19/00—Preparations for care of the skin
    • A61Q19/10—Washing or bathing preparations

Definitions

  • the present invention relates to use of cationic oxidized polysaccharide compositions in personal care and household compositions.
  • Cationic polysaccharides and other polymers have been used widely in personal care and household products to perform a function in the final product, ranging from thickening to conditioning of a substrate.
  • the substrate can be skin, hair, or textile material.
  • Cationic polysaccharides are used in haircare products to provide conditioning to the hair.
  • these same polymers can provide conditioning effects to the skin.
  • these same polymers can provide conditioning, softening, anti-pilling, color retention and antistatic characteristics to fabrics.
  • Hair conditioning agents perform their functions at the cuticle, or outer sheath of keratinized scales on the surface of the hair fiber.
  • the cuticle's scales are arranged in overlapping fashion like the shingles on a roof.
  • the cell structure of the cuticle is composed of an A layer, the exocuticle, and a B layer, the endocuticle.
  • the clear outer A layer composed of sulfur-containing proteins, protects the hair from chemical, physical, and environmental damage. Consequently, the condition of the cuticle determines the condition of the hair, and hair-conditioning products are directed toward enhancing and restoring the cuticle shaft layer.
  • An intact cuticle is responsible for the strength, shine, softness, smoothness, and manageability of hair.
  • llW ariGll.Q y: , idii bility measurements are typical test methods used to measure conditioning performance in shampoo and conditioner applications.
  • Commercial cationic conditioning polymers in the marketplace have been reported to reduce the wet combing force experienced on combing wet hair by 30%-50% relative to the shampoo containing no polymer.
  • High molecular weight cationic guar conditioning polymers available in the marketplace, have their drawbacks, such as incompatibility with surfactant systems used in shampoo, bodywash, conditioners, skin care, sun care, laundry products etc. In addition, they contribute to the final product viscosity, which may not be desirable. High molecular weight cationic guar polymers are also known to be difficult to disperse and dissolve in aqueous solution.
  • US Patent 6,210,689 Bl discloses the use of an amphoteric guar gum composition that contains cationic and anionic groups attached to its backbone for treating keratin substances.
  • This composition is used in aqueous systems of cosmetics such as shampoos, topical sprays, dental care products and products containing fragrances and/or antimicrobial agents.
  • US Patent 5,756,720 describes a process for producing a polygalactomannan composition having nonionic and cationic groups attached to the backbone. This patent describes the achievement of high optical clarity in cleansing surfactant formulations with this composition.
  • the hydroxypropyl cationic polygalactomannans of this composition have been found lacking in conditioning performance, as described in WO 99/36054.
  • US Patent 5,489,674 describes a process for preparing polygalactomannan gum and a polygalactomannan gum composition prepared by a specific process that includes aqueous alcohol processing.
  • the product is described as giving 85-100% transmittance at -waf e tei ffis"between- 500-600 nm at 0.5 part polymer in 100 parts of an aqueous solution. The use of this material in personal care applications is disclosed.
  • JP Application Hei 10 [1998] - 36403 discloses a cosmetic composition that uses a polygalactomannan degradation product that has 80% or higher of its molecular weight distribution within the range of 4,500 to 35,000 for use in hair and skin care products.
  • US Patent No. 5,480,984 and 6,054,511 disclose an aqueous, high solids low viscosity polysaccharide composition and a method of making the composition by reacting a polysaccharide and hydrogen peroxide oxidizing agent to produce a product with a solid content of about 20% to about 50% and a viscosity below 9500 mPa.s at 25°C.
  • Cellulose ethers, guar, and guar derivatives are disclosed as polysaccharides that have a wide variety of uses such as in cosmetics.
  • US Patent application serial number 20030199403 Al discloses a shampoo composition of a detersive surfactant, a cationic guar derivative, and an aqueous carrier.
  • the cationic guar derivative has a charge density of from about 1.25 meq/g to about 7 meq/g and a molecular weight of from about 10,000 to about 10,000,000.
  • Cationic HEC such as Ucare Polymer JR400TM having a high cationic substitution has been cited by the manufacturer as causing "buildup" problems after repeated use.
  • One manufacturer has recommended the use of cationic HEC having lower cationic substitution levels to eliminate buildup issues ("Cationic Conditioners that Revitalize Hair and Skin", Amerchol Product Literature, WSP801, July, 1998).
  • Buildup has been defined by this manufacturer as the binding of a polymer to a substrate, making it more difficult to remove the polymer from the substrate in subsequent cleansing treatments.
  • the present invention meets this need by providing cationic conditioning polymers that not only have good conditioning ⁇ jierfdHr ⁇ dbe lv itT ⁇ - r ⁇ 'ad"s'u Fa , ctant compatibility, but also are economical to formulate in compositions where clarity is not necessarily an issue.
  • the present invention relates to personal care and household compositions comprising at least one cationic, oxidized polysaccharide or derivative thereof having a weight average molecular weight (Mw) with a lower limit of 50,000 and an upper limit of 1,000,000 having aldehyde functionality at a level of at least 0.001 meq/gram.
  • Mw weight average molecular weight
  • the cationic, oxidized polysaccharide or derivative thereof can preferably have a Brookfield viscosity at 10 wt.% solids of the polysaccari.de at 25°C using a spindle 4 at 30 rpm with a lower limit of 30 cps and an upper limit of 20,000 cps, with the proviso that if the viscosity of the polysaccharide is above 20,000 cps, then the Brookfield viscosity is measured at a solids content of 10 wt.% at 25°C using a spindle 4 at 0.3 rpm has a lower limit of 20,000 cps and an upper limit of 2,000,000.
  • This viscosity range is particularly preferred with cationic, oxidized polygalactomannans.
  • This invention further relates to a method for making a personal care or household composition comprising adding a cationic, oxidized polysaccharide to a personal care or household composition containing at least one active ingredient other than the cationic, oxidized polysaccharide of this invention.
  • the cationic oxidized polysaccharides of this invention can deliver the conditioning or lubricating effect desired in cleansing products such as shampoos, two-in-one shampoos (i.e., cleans and conditions the hair), three-in-one shampoos (i.e., cleans, conditions, and delivers styling), conditioners, shower gels, liquid soaps, bodywash, styling products, shave gels/creams, body cleansers, and bar soaps.
  • the polymers of this invention deliver the conditioning or lubricating properties of good wet and dry combing force reduction to hair when incorporated into a broad range of cleansing shampoo surfactant systems where such properties are desired.
  • the polymers of this invention also deliver the ⁇ h iy SiI yr , &ririS tln
  • conditioning or lubricating effects are expected in surfactant-based household cleansing product formulations where conditioning performance is desired, such as dish detergents, laundry detergent, fabric softeners, and antistatic products.
  • Conditioning in fabric softeners and in laundry detergent refers to imparting a softer feel, anti-pilling, color retention to fabric and eliminating static effects.
  • the cationic functionality of the polysaccharide or derivatized polysaccharide can be added to the backbone by known methods.
  • the polysaccharide material can be reacted for a sufficient time and at a sufficient temperature with tertiary amino or quaternary ammonium alkylating reagents, such 2-dialkylaminoethyl chloride and quaternary ammonium compounds such as 3-chloro-2- hydroxypropyltrimethylammonium chloride, and 2,3-epoxy-propyltrimethylammonium chloride.
  • Preferred examples include glycidyltrialkylammonium salts and 3-halo-2- hydroxypropyltrialkylammonium salts such as glycidyltrimethylammonium chloride, glycidyltriethyla monium chloride, gylcidyltripropylammonium chloride, glycidylethyldimethylammonium chloride, glycidyldiethylmethylammonium chloride, and their corresponding bromides and iodides; 3-chloro-2- hydroxypropyltrimethylammonium chloride, 3-chloro-2- hydroxypropyltriethylammonium chloride, 3-chloro-2- hydroxypropyltripropylam onium chloride, 3-chloro-2- hydroxypropylethyldimethylammonium chloride, and their corresponding bromides and iodides; and quaternary ammonium compounds such as halides of imidazo
  • the cationic polysaccharides may also contain other substituent groups such as nonionic substituents , i.e., hydroxyalkyl wherein the alkyl represents a straight or branched hydrocarbon moiety having 1 to 30 carbon atoms (e.g., hydroxyethyl, hydroxypropyl, hydroxybutyl) or anionic substituents, such as carboxymethyl groups are optional.
  • nonionic substituents i.e., hydroxyalkyl wherein the alkyl represents a straight or branched hydrocarbon moiety having 1 to 30 carbon atoms (e.g., hydroxyethyl, hydroxypropyl, hydroxybutyl) or anionic substituents, such as carboxymethyl groups are optional.
  • substituents are linked to the polysaccharide polymer by the reaction with reagents such as (1) alkylene oxides (e.g., ethylene oxide, propylene oxide, f tyl ihl diii ⁇ diy a il ⁇ iroxyethyl groups, hydroxypropyl groups, or hydroxybutyl groups, or with (2) chloroniethyl acetic acid to obtain a carboxymethyl group.
  • alkylene oxides e.g., ethylene oxide, propylene oxide, f tyl ihl diii ⁇ diy a il ⁇ iroxyethyl groups, hydroxypropyl groups, or hydroxybutyl groups
  • chloroniethyl acetic acid to obtain a carboxymethyl group.
  • Polysaccharides can be oxidized by several known reagent and methods, such as
  • biochemical oxidants such as galactose oxidase
  • chemical oxidants such as hydrogen peroxide
  • a physical methods using high speed agitation and shearing machines (4) thermal methods, and (5) mixtures of these reagents and methods.
  • the cationic, oxidized polysaccharides used to make personal care or household compositions with good conditioning properties are preferably made by using oxidative reagent either alone or in combination with other reagents, including biochemical reagents, that reduce molecular weight and/or introduce oxidized functional groups.
  • oxidative reagent either alone or in combination with other reagents, including biochemical reagents, that reduce molecular weight and/or introduce oxidized functional groups.
  • Oxidative agents include any reagent that incorporates oxygen atoms into the polymer structure. Some oxidizing reagents can also act to reduce the molecular weight of the polymer. Examples of these dual function oxidizing agents are peroxides, peracids, persulfates, permanganates, perchlorates, hypochlorite, and oxygen. Examples of biochemical oxidative agents that do not reduce molecular weight are oxidases. Specific examples of oxidases useful in this invention are galactose oxidase, and other biochemical oxidizing agents known to those skilled in the art.
  • an oxidizing agent into the process for preparing the products of this invention has been found to be useful, in that cationic polymers prepared with the use of an oxidizing agent have greater solubility in a broader range of surfactant systems commonly used in personal care and household compositions than cationic polymers that have not been treated with an oxidizing agent.
  • incorporation of an oxidizing agent into the process for preparing the products that are used to make the personal care and household dbmpW i tl S ' tf ' t s-iWelI5n introduces aldehyde groups into the polymer composition. These polymers have been found to contain at least 0.001 milliequivalents aldehyde per gram (meq/g) of polysaccharide. The upper limit of the aldehyde content is about 1.0 meq/g.
  • the cationic, oxidized polysaccharide or derivative thereof generally has a cationic degree of substitution (DS) lower limit of about 0.001 and an upper limit of about 3.0.
  • the lower limit of the cationic DS is 0.01, and more preferably 0.05.
  • the upper limit of the cationic DS is 2.0, more preferably 1.0, and even more preferably 0.25.
  • the cationic, oxidized polysaccharide or derivative thereof of the present invention generally has a weight average molecular weight (Mw) with a lower limit of about 50,000 and an upper limit of about 1,000,000.
  • the lower limit of the Mw is about 75,000 and more preferably about 100,000.
  • the upper limit of the Mw preferably is about 600,000, more preferably about 300,000, and even more preferably about 150,000.
  • the personal care active ingredient must provide some benefit to the user's body.
  • Personal care products includes hair care, skincare, sun care, and oral care products. Examples of substances that may suitably be included, but not limited to, in the personal care products according to the present invention are as follows:
  • Skin coolants such as menthol, menthyl acetate, menthyl pyrrolidone carboxylate N-efhyl-p-menthane-3-carboxamide and other derivatives of menthol, which give rise to a tactile response in the form of a cooling sensation on the skin;
  • Emollients such as isopropylmyristate, silicone materials, mineral oils and vegetable oils which give rise to a tactile response in the form of an increase in skin lubricity;
  • Deodorants other than perfumes whose function is to reduce the level of or eliminate micro flora at the skin surface, especially those responsible for the development of body malodor. Precursors of deodorants other than perfume can also be used;
  • Antiperspirant actives whose function is to reduce or eliminate the appearance of perspiration at the skin surface
  • Moisturizing agents that keeps the skin moist by either adding moisture or preventing from evaporating from the skin
  • Sunscreen active ingredients that protect the skin and hair from UV and other harmful light rays from the sun.
  • a therapeutically effective amount will normally be from 0.01 to 10% by weight, preferable 0.1 to 5% by weight of the composition;
  • Hair treatment agents that conditions the hair, cleans the hair, detangles hair, acts as styling agent, volumizing and gloss agents, anti-dandruff agent, hair growth promoters, hair dyes and pigments, hair perfumes, hair relaxer, hair bleaching agent, hair moisturizer, hair oil treatment agent, and antifrizzing agent;
  • Oral care agents such as dentifrices and mouth washes, that clean, whiten, deodorize and protect the teeth and gum;
  • Shaving products such as creams, gels and lotions and razor blade lubricating strips
  • Tissue paper products such as moisturizing or cleansing tissues
  • Beauty aids such as foundation powders, lipsticks, and eye care
  • Textile products such as moisturizing and/or cleansing wipes, and diapers;
  • Nail care products such as nail polish.
  • the household care active ingredient must provide some benefit to the user.
  • substances that may suitably be included, but not limited to, according to the present invention are as follows:
  • Insect repellent agent whose function is to keep insects from a particular area or attacking skin
  • Bubble generating agent such as surfactants which generates foam or lather
  • Pet deodorizer such as pyrethrins which reduces pet odor
  • Pet shampoo agents and actives whose function is to remove dirt, foreign material and germs from the skin and hair surfaces and conditions the skin and hair;
  • Toilet bowl cleaning agents which removes stains, kills germs, and deodorizes
  • Vehicle cleaning actives which removes dirt, grease, etc. from vehicles and equipment;
  • composition according to the present invention can optionally also include, but not limited to, ingredients such as a l ⁇ l ' ⁇ pb'bfc ⁇ alivI s nlttidant, nutritional supplements, alpha or beta hydroxy acid, activity enhancer, emulsifiers, functional polymers, viscosifying agents (such as salts, i.e., NaCl, NH 4 C1 & KC1, water-soluble polymers, i.e., hydroxyethylcellulose, and fatty alcohols, i.e., cetyl alcohol; water-swellable materials, such as clay and silica), alcohols having 1-6 carbons, fats or fatty compounds (i.e., fatty amides and fatty acid esters and fatty
  • examples of functional polymers that can be used in blends with the cationic, oxidized polysaccharides or derivatives thereof of this invention include water-soluble polymers such as acrylic acid homopolymers such as Carbopol® product and anionic and amphoteric acrylic acid copolymers, vinylpyrrolidone homopolymers and cationic vinylpyrrolidone copolymers; nonionic, cationic, anionic, and amphoteric cellulosic polymers such as hydroxyethylcellulose, hydroxypropylcellulose, carboxymethylcellulose, hydroxypropylmethylcellulose, cationic hydroxyethylcellulose, cationic carboxymethylhydroxyethylcellulose, and cationic hydroxypropylcellulose; clay; acrylamide homopolymers and cationic, ( amphoteric, and hydrophobic acrylamide copolymers, polyethylene glycol polymers and copolymers, hydrophobic polyethers, hydrophobic polyetheracetals, hydrophobically
  • the silicone materials which can be used are, in particular, polyorganosiloxanes that are insoluble in the composition and can be in the form of polymers, oligomers, oils, waxes, resins, or gums.
  • the silicones are more particularly chosen from those having a boiling point of between 60°C. and 260°C, and even more particularly from:
  • cyclic silicones' containing from 3 to 7 and preferably from 4 to 5 silicon atoms.
  • cyclic silicones' containing from 3 to 7 and preferably from 4 to 5 silicon atoms.
  • These are, for example, octamethylcyclotetrasiloxane sold in particular under the name "Volatile Silicone 7207" by Union Carbide or
  • organosilicone compounds such as the mixture of octamethylcyclotetrasiloxane and tetratrimethylsilylpentaerythritol (50/50) and the mixture of octamethylcyclotetrasiloxane and oxy-l,r-bis(2,2,2 , ,2 , ,3,3'-hexatrimethylsilyloxy) neopentane;
  • linear volatile silicones having 2 to 9 silicon atoms and having a viscosity of less than or equal to 5xl0 "6 m 2 /s at 25°C.
  • An example is decamethyltetrasiloxane sold in particular under the name "SH 200" by Toray Silicone company. Silicones belonging to this category are also described in the article published in Cosmetics and Toiletries, Vol. 91, Jan. 76, pp. 27-32,
  • Non- volatile silicones and more particularly polyarylsiloxanes, polyalkylsiloxanes, polyalkylarylsiloxanes, silicone gums and resins, polyorganosiloxanes modified with organofunctional groups, and mixtures thereof, are preferably used.
  • Wa'drJorda iGle will ffie invention, the silicone polymers and resins which can be used are, in particular, polydiorganosiloxanes having high number-average molecular weights of between 200,000 and 1,000,000, used alone or as a mixture in a solvent.
  • This solvent can be chosen from volatile silicones, polydimethylsiloxane (PDMS) oils, polyphenylmethylsiloxane (PPMS) oils, isoparaffms, polyisobutylenes, methylene chloride, pentane, dodecane and tridecane, or mixtures thereof.
  • volatile silicones polydimethylsiloxane (PDMS) oils, polyphenylmethylsiloxane (PPMS) oils, isoparaffms, polyisobutylenes, methylene chloride, pentane, dodecane and tridecane, or mixtures thereof.
  • silicone polymers and resins are as follows: Polydimethylsiloxane, polydimethylsiloxanes/methylvinylsiloxane gums, polydimethylsiloxane/diphenylmethylsiloxane, polydimethylsiloxane/phenylmethylsiloxane, and polydimethylsiloxane/diphenylsiloxanemethylvinylsiloxane.
  • Products which can be used more particularly in accordance with the invention are mixtures such as:
  • the bath temperature was adjusted as necessary to maintain the ti tcWer ⁇ * f lt:i5 ⁇ p ⁇
  • An additional Caframo mixer Model RZR-1 was used with a 2" propeller blade at low speed in the bath to improve the oil circulation.
  • the stirrer speed was increased to ⁇ 100 rpm, as volume permitted, and l A of the total peroxide charge was added to the beaker using an appropriate size weighed hypodermic syringe, by injecting the peroxide through the saran covering.
  • the contents of the beaker was allowed to mix ⁇ 5 minutes.
  • the covering on the beaker was removed and very slowly l A of the total cationic polygalactomannan charge was sifted into the beaker while mixing.
  • the stirring speed of the stirrer was adjusted to maintain adequate vortex speed. Some lumping may occur, especially during the first polygalactomannan addition; however, small lumps will dissolve as viscosity increases.
  • the covering was replaced and mixing was continued at a temperature of 85-90°C until viscosity had decreased enough to permit the next polymer addition.
  • the wet comb and dry comb measurements were performed on an Instron instrument using mildly bleached European hair tresses that had been shampooed with a mild anionic surfactant-based shampoo or a nonionic surfactant shampoo.
  • the percent reduction in wet comb and dry comb energy is defined as shown in equation (1).
  • the energy needed to comb a tress after shampooing with a shampoo containing cationic polymer was subtracted from the energy needed to comb a tress that had been shampooed twice with 4.5 wt % sodium lauryl sulfate (SLS) solution. This remainder was then divided by the energy needed to comb the tress washed with the SLS solution. The value was multiplied by 100 and was called the percent reduction in combing force.
  • the percent reduction was typically a positive number if the cationic conditioning polymer conditions the hair.
  • EXAMPLE 1 The above-mentioned Standard Decomposition Method was used. About 935 grams of water was placed in a 1500 ml beaker and placed in an oil bath set at a temperature of about 120°C. The beaker was then heated to a temperature of about 85- 95°C in the oil bath and maintained at this temperature. A double 2" propeller blade mixer was inserted into the beaker and a small portion of N-Hance® 3205 cationic guar product (Hercules Incorporated, Wilmington, DE) was added while stirring. Then a small amount of peroxide was added to the beaker while continuing to mix.
  • N-Hance® 3205 cationic guar product Hercules Incorporated, Wilmington, DE
  • EXAMPLE 4 The same procedure used in Example 3 was followed in this Example 4 for . experiments M, N, and O series and noted in Table 3 except that (a) for experiment M, Jaguar® C-13-S cationic guar product (Rhodia Incorporated, Cranberry, N.J.) was used, (b) for experiment N, Jaguar® C-162 cationic hydroxypropyl guar product (Rhodia Inc ⁇ rp-6ra'tM, ''' C anbe ry ⁇ "N:'J'.”)' was used and (c) for experiment O, N-Hance® 3215 catiomc guar product (Hercules Incorporated, Wilmington, DE) degraded with heat only and no peroxide was used.
  • Example 2 The same preparation and procedure used for Example 2 were used in this Example 5 for experiments P, Q and R and were reported in Table 4.
  • Example 5 The same procedure used for experiments J, K, and L series in Example 3 was used for the experiments S, T, U, V, W, and X of this Example 6 and were reported in Table 5.
  • the tap water concentration is in gallons and all material concentrations are in pounds.
  • N-Hance 3215 water- wet cationic guar splits were used in place of N-Hance 3215 cationic guar powder and hydrochloric acid was used in place of fumaric acid to neutralize the cationic guar splits to a pH of 6.5, Sodium metabisulfite was added at the end of the reaction to decompose residual peroxide.
  • Experiment X was further treated with sodium hydroxide at pH 8 for 30 minutes, followed by neutralization with dilute hydrochloric acid.
  • the product from experiment V had an aldehyde content of 0.035 meq/gram and Mw of 61,000.
  • the product from experiment U had a molecular weight of 50,400.
  • Experiment Y all of the hydrogen peroxide and the malic acid were added after reactor heat up to 90°C.
  • the N-Hance cationic guar was added as a 20 % solids slurry to the "f ea f ⁇ rl'- ⁇ riM ea'cti rfpH Was maintained at 6, and sodium metabisulfite was added at the end of the reaction to decompose residual hydrogen peroxide.
  • the product of Experiment Y was further treated with a nitrogen sparge after pH adjustment to pH of 7, followed by addition of the preservative and additional acids to bring the pH to approximately 6.
  • Experiment Z the same procedure in experiment V was followed, using a high molecular weight cationic guar PRECURSOR 2 (cationic DS of 0.5), blended with fumaric acid.
  • Experiments AA and AB used high molecular weight cationic guar PRECURSOR 3 (999, 145 Dalton, cationic DS of 0.9), reacted at 90° C in a one stage reaction, adding the hydrogen peroxide to the water at temperature, followed by addition of the cationic guar. Sodium metabisulfite was added to destroy excess hydrogen peroxide.
  • the product prepared also had aldehyde functional groups on the low molecular weight cationic guar.
  • the sample was tested for aldehyde level with M Quant Formaldehyde Test strips available from EM Science of Gibbstown, NJ.
  • the polymer sample had 0 ppm formaldehyde.
  • the polymer solution was raised to about 90°C and 4.44 grams of 1.0 % peroxide solution were added.
  • the reaction was stopped with 0.2 g of sodium metabisulfite.
  • 17.6 g of 1.0 % hydrogen peroxide solution were added and stirred for about 60 minutes at about 90°C.
  • 0.34 g of sodium meta bisulfite was added and cooled.
  • the solution was preserved with 0.5 % Phenoxetol® and 0.18 % Nipasept® Sodium preservatives. Both preservatives are available from Clariant Corporation.
  • This sample had 10 ppm of aldehyde as per the strip test.
  • the sample had weight average molecular weight of 293,000 Dalton.
  • N-Hance 3000 polymer used in this example had cationic DS of about 0.06 and weight average molecular weight 923,655 Dalton.
  • 929g of water were heated to about 90°C in a silicone oil bath. 10.5 grams of 1.0 % active H 2 O 2 was added to the heated water.
  • 50 grams of N-Hance® 3000 polymer were added the water-peroxide mix and was maintained for about 110 minutes at 80 to 90°C. 0.19 grams of sodium meta bisulfite was added and mixed for an additional 10 minute and cooled.
  • the pH was adjusted to 6.5 with hydrochloric acid.
  • 10 grams of Germaben® II preservative and make-up water were added to adjust total batch size to 1000 g and mixed. This produced a 0O0"'g ⁇ anl''ba ' tch , with"S' % p ' blymer.
  • the final product had a weight average molecular weight of 418,000 Dalton.
  • Example 8a The procedure in steps 1-3 of Example 8a was followed. Once the desired viscosity was reached, the temperature was raised to 90°C to denature the enzyme and stop the reaction. The mixture was allowed to cool to ambient temperature, and 0.1 %
  • Kathon CG preservative was added to the reaction mixture.
  • the weight average molecular weight of the product was 67,000 Dalton.
  • the sample contained no aldehyde content as determined by the indirect iodometric titration method.
  • a product of 10 % total solids, with Mw of 40,000 was prepared.
  • the product had aldehyde groups on the low molecular weight cationic guar.
  • the procedure was as follows:
  • the aldehyde content of this sample as measured by the change in the ratio of galactose/mannose is 0.4 meq/gram.
  • conditioning agent cationic guar or cationic hydroxyethylcellulose
  • Examples 11, 12 and 14 demonstrate that cationic, oxidized guars and cationic, oxidized hydroxyethylcellulose materials of the invention improve detangling of both wet and dry hair, when compared with the shampoo containing no polymer in Example 10.
  • Example 14 demonstrates that the polymer of this invention derived from a cationic hydroxyethylcellulose polymer, prepared according to the procedure described in experiment AF in Example 7, Table 6, also gave better wet and dry combing performance than the no polymer control Example 10.
  • Example 15 is included as a comparative example for a low molecular weight cationic guar prepared by biochemical degradation, without an oxidative treatment, as described in Example 8d. Note, that this polymer gave improved wet and dry comb performance over the no polymer control example in Example 10; however, the shampoo developed a sediment over time.
  • Phase 1 Water was heated in a vessel to 80-90°C and HPMC was added while mixing.
  • Cationic, oxidized polysaccharide was added to the heated water while mixing at ⁇ 60-65°C.
  • the mixture was allowed to cool to 25-35°C while mixing.
  • Citric acid was added to the cooled mixture to lower the pH to 5.00 to 6.00
  • Phase 2 Rhodapex ES STD product was weighed into a separate tarred beaker. Phase 1 was added to Phase 2 while mixing. ""i ⁇ e"p.ri”was”re , -a ⁇ j"Us ⁇ e ⁇ to 5.0 to 5.5 with citric acid. The mixture was stirred for 30-60 minutes until homogeneous.
  • Phase 3 Amphosol CA product was added to the combined Phases 1 and 2 while mixing and stirred additionally for five-minutes after completion of mixing. Mixing was continued until homogeneous.
  • Phase 4 Sodium chloride solution(10wt%) was added to Phase 3 and stirred for 5 minutes. Glydant product was added mixed 15 minutes. The pH value of the shampoo was checked and, when necessary, the pH was re-adjusted to between 5.0 and 5.5. The shampoo was mixed 15 minutes when adjusted.
  • Rhodapex ES STD 30 % active (Rhodia Incorporated, Cranberry, N.J.)
  • conditioning agent cationic guar
  • cationic guar In a shampoo formulation, conditioning agent, cationic guar, was added to improve detangling of both wet hair and dry hair.
  • the current commercially available cationic guar can only be used at very low level, since it has a significant impact on the viscosity of the shampoo product.
  • shampoo was made 1) without the cationic guar, 2) with 0.2 % and 1.5 % commercially available N-Hance® 3215 cationic guar, and 3) with 1.5 % cationic, oxidized guar product of this invention.
  • Shampoo preparation A container of water was heated to 70°C by placing in a 70°C water-bath. Benecel® product was sifted into the heated water while mixing. Next, commercial N-Hance® 3215 product or polymer of this invention was added to the container while mixing. The solution that was formed was cooled to about 40°C, while mixing. The remainder of the ingredients of the shampoo was added to the container in the order listed. The shampoo pH was adjusted to about pH 5.5. The shampoo was cooled to room temperature while mixing.
  • the commercial N-Hance® 3215 product is a dry polymer with molecular weight of about 1 million. Because of its high molecular weight it has a significant effect on the viscosity of the conditioning shampoo.
  • Example 16 shampoo was made without a conditioning agent. It has a Brookfield viscosity of about 3,540 cps.
  • same shampoo made with 1.5 % N-Hance 3215 product has Brookfield LVT viscosity of 193,000 cps.
  • the conditioning shampoo was tested for its combing performance on a mildly bleached European virgin hair. A 12-inch hair tress weighing around 5 grams was used. In this study, reduction in combing energy was measured. Reduction in combing energy is an indirect measurement of conditioning performance of a polymer. As shown in Example 16, if conditioning polymer is not used in the shampoo, it takes more force to comb hair. A negative combing energy is an indication of hair entanglement and needs higher force or energy to comb the hair. At the polymer level of 0.2 %, the polymer of this invention (Example 19, Table 8) and the commercial polymer (Example 20, Table 8) provided about the same level of reduction in wet combing energy, 15.8 % and 17.1%, respectively.
  • Example 17 the polymer of this invention (Example 17) at 1.5 % polymer level provided significantly higher reduction in wet combing, 53.7 %.
  • a shampoo with 1.5 % commercial N-Hance® 3215 product was not tested, since it had viscosity significantly outside the shampoo viscosity range (Example 18).
  • the shampoo was made using " 'the procedure descr ⁇ b ' ed ' T ⁇ r " shampoos in Table 8.
  • the shampoo viscosity was about 11,000 cps with 1.5 % polymer of this invention, Example 32, compared to 32,000 cps for high molecular weight polymer, Example 31.
  • the polymer of the present invention in Example 32 had slightly better wet combing performance.
  • the conditioning shower gel in Table 12 was made first dispersing Benecel® MP943 product in water. Next N-Hance® 3196 product or the cationic polymer of this invention was added. And then the remainder of the ingredients of the shower gel were added in the order listed, while mixing well between each addition. Once all the ingredients are well mixed, shower gel pH was lowered to between 5.0 and 6.0 with citric acid. All viscosities were measured at 12 rpm, 25°C using Brookfield LVT viscometer.
  • Example 34 the commercial N-Hance® 3196 polymer could not be added at 1.5 % without a very significant increase in the viscosity, Example 34, Table 12.
  • the viscosity of the conditioning shower gel with commercial N-Hance 3196 polymer was 42,700 cps at 12 rpm as compared to a shower gel without the polymer having viscosity of only 460 cps, Example 33. With the polymer of the invention at a concentration of 1.5 %, the viscosity was only 3,380 cps, Example 35.
  • Examples 36, 37, and 34 show the effect of commercial N-Hance® 3196 polymer on shower gel viscosity when compared to Example 33 without the conditioning product polymer. The viscosity measurements were made at 12 rpm, 25°C using Brookfield LVT viscometer.
  • Lather drainage time is an indirect method of measuring lather stability. A longer drainage time is an indication of more stable and richer lather. A consumer perceives more stable lather as positive.
  • the lather drainage time was more than double for the shower gel with the polymer of this invention (Example 35) than that of shower gel without the polymer of the invention, Example 33.
  • Example 37 with 0.5 % of commercial N- Hance® 3196 cationic guar, almost the same viscosity was reached as with the polymer of this invention (Example 35) but me polymer of the present invention had over 20 % higher lather stability.
  • Lather Test This method was used for measuring the lather drainage time of a diluted shower gel to determine the influence of conditioning polymer on lather quality. Long drainage time indicate a rich, dense lather with good stability.
  • Funnel preferably plastic; 6" diameter, 7/8" ID neck, 5 V" high, with a horizontal wire
  • the polymer of the Invention in Example 35 of Table 12 was prepared by a method similar to the method described for experiment Z, in Table 5, Example 6, where N-Hance 3205 cationic guar was used in place of PRECURSOR 2 cationic guar.
  • the molecular weight of the final product was 550,000 Dalton, reduced from a molecular weight of 1,050,000 Dalton measured for the starting N-Hance 3205 cationic guar.
  • Viscosity of conditioning shower gel with commercial Jaguar® C162 was 41,400 cps at 12 rpm as compared to shower gel without the polymer having viscosity of only 555 cps. With the polymer of this invention, viscosity was only 3,320 cps, Example 40 with 2.0 % active polymer. The viscosity measurements were made at 12 rpm, 25°C using Brookfield LVT viscometer. The commercial Jaguar® C162 product was also tested at 0.2 % and 0.5 % active level, Examples 41 and 42. At 0.5 % level
  • Example 42 it reached the same viscosity as the formulation with 2.0 % polymer of this invention, Example 40.
  • the lather stability was measured using the method previously described. Lather drainage time for the shower gel in Example 40, the polymer of the invention, was more than double than that of shower gel without the polymer of invention (Example 38). The longer the drainage time, the more stable the lather.
  • Example 13 The polymer of Invention described in Example 40, Table 13 was made by a procedure similar to the procedure used for experiment Z in Example 6, Table 5, with substitution of Jaguar® 162 catiomc hydroxypropyl guar for PRECURSOR 2 cationic guar.
  • the product had a molecular weight of 555,532 Dalton, reduced from a starting molecular weight of 1,080,000 Dalton for the starting Jaguar C162 cationic hydroxypropyl guar.
  • Table 14 show the effect of concentration of commercial N-Hance® 3198 cationic guar on the viscosity of liquid soap and its lather stability.
  • Natrosol hydroxyefhyl cellulose was dispersed in water while mixing. Next 5 cationic guar (commercial N-Hance® 3198 or polymer of this invention) was added while mixing. The Ammonyx® 4002, Bioterge® AS40 and Emerest® ingredients were added in the order listed while mixing. The batch was mixed in an 80°C water-bath until the Emerest® ingredient dissolved. Next, the batch was removed from the water-bath and allowed to cool while mixing. The remaining ingredients were added while the batch 0 was cooling to room temperature. Table 14
  • Example 47 The polymer of invention used in Example 47, Table 14 was made by a procedure similar to the procedure used for experiment Z in Example 6, Table 5 with the substitution of N-Hance 3198 cationic guar for PRECURSOR 2.
  • Part B In a separate container Emerest® 2400 weighed and placed in the 80°C water bath. Remaining ingredients of Part B were added in the order listed while mixing.
  • Part A was slowly added to Part B while mixing. Temperature was maintained at
  • Part C Part C was added to Part A/B. Mixing was continued while cooling to
  • Viscosity was measured after 24 hours at 12 rpm, 25 °C using Brookfield® LVT viscometer.
  • Example 49 the skin lotion emulsion with commercially available N-Hance 3215 showed phase separation due to instability.
  • the lotion emulsion with polymer of this invention was not only stable but had viscosity of about 2,800 cps, having more body when dispensed.
  • Part A Weighed Drakeol in an 8 ozjar. Next jar was placed in a bath set at 70°C. The remaining ingredients of Part A were added in the order listed, while mixing. Mixing was continued for 30 minutes at 70°C.
  • Part B In a separate jar water was weighed and then placed in 70°C water-bath. Natrosol® polymer was added to water while mixing. Next remaining ingredients of Part B were added while mixing at 70°C.
  • Part C Premixed Part C. Part C was added to Part B once all ingredients in Part B were dissolved. Part B/C was then added to Part A once it had reached to 70°C while mixing. Mixing was continued for 30 minutes at 70°C.
  • Part D The above Part A B/C mixture was removed from the water bath and was allowed to cool to 50°C while mixing. Germaben II product was added once temperature reached 50°C. Mixing was continued until the sunscreen emulsion reached room temperature. '"The polymer o ' f the ' Ihvention in Example 53, Table 16, was prepared by process described in experiment U, Example 6, Table 5, substituting N-Hance 3198 polymer for N-Hance 3215.
  • Creamy, glossy, emulsions are desirable when formulating sun care lotions. It is also desirable to generate enough viscosity to prevent the lotion from dripping or having a runny consistency, but not be too thick and difficult to spread.
  • the sunscreen (Example 52) made with commercial cationic guar N-Hance® 3198 was slightly grainy and had off-white color in addition to being very high in viscosity.
  • the sunscreen made with product of this invention (Example 52) was not only comparable in viscosity to the sunscreen without the conditioning polymer (Example 51) but was also glossy, white and stable as Example 51.
  • the polymer of this invention was post-added at 0.2 % active level to commercially available Tide® liquid laundry detergent from Procter & Gamble Co. of Cincinnati, Ohio and to Wisk liquid laundry detergent from Unilever, Greenwich Comiecticut. 0.2 % of commercially available N-Hance® 3215 cationic guar was post-added to these laundry detergents.
  • the product of this invention had no effect on the viscosity of the original liquid laundry detergent and, it was also compatible (Examples 55 and 58).
  • the N-Hance® 3215 product was found to be not compatible (Examples 56 and 59).
  • Example 65 Body washes made with the polymer of the invention in Examples 65 and 66, Table 18, had lower viscosity as compared with commercially available N-Hance® 3000 product, Example 64.
  • Example 65 the polymer was made with peroxide degradation according to the procedure described for experiment AC in Example 6, Table 5.
  • Example 66 the polymer was made by sequential treatment with peroxide followed by enzyme degradation, as described in Example 8C.
  • Example 69 had much lower viscosity compared to the body wash made with PRECURSOR 3 (Example 67). In fact, the wash made with PRECURSOR 3 was almost like a gel.
  • the polymer of the invention used in Example 68 was made with peroxide degradation, as described in experiments AA and AB in Example 6, Table 5.
  • the polymer of invention used in Example 69 was made by sequential treatment with enzyme followed by peroxide degradation, as described in Example 8B.
  • Aii v ⁇ scosmes " we ⁇ e” measured at 12rpm, 2min of spindle rotation using Brookfield LVT. Samples were conditioned at 25°C.
  • Rhodapex® ES-STD Sodium Laureth (3) sulfate Rhodia, Cranberry, NJ
  • Rhodapex® ES-STD Sodium Laureth Rhodia Cranberry, NJ sulfate
  • Table 20 show the differences in composition between materials of the invention prepared by procedures in Examples 6, 7, or 8a, b, c versus Example 8d and versus the commercial high molecular weight cationic commercial polymers in the marketplace. Solutions of the polymers were analyzed using a method specific for detection of aldehyde groups (Analytical Biochemistry, 1983, 134, 499-504). The results from these tests are shown by the colorimetric test results in Table 20 as absorbance at 595 nm/gram polymer, or as milliequivalent aldehyde /gram polymer.
  • materials of the invention prepared by procedures in Examples 6, 7, or 8a-c produced materials having significant absorbance, as measured by the Purpald method [H. B. Hopps, Aldrichimica ACTA, 2000, 33(1), 28-30] This method is specific for detection of aldehydes. Negligible absorbance was ⁇ etecte ⁇ m materials by this method, that were prepared according to the procedure in Example 8d or in the starting cationic guar or other commercial cationic guar materials. These results indicate that materials prepared through treatments that include an oxidative agent, as a single reactive treatment, or in combination with hydrolytic enzyme treatment, will produce a low molecular weight material with a measurable amount of aldehyde groups on the polymer.
  • the level of aldehyde in some samples was quantified and a calibration equation was created to convert from Absorbance/gram to milliequivalent aldehyde/gram.
  • the level of aldehyde groups in the materials of the invention is at least 0.001 meq/g.
  • the calibration equation is shown in equation 2.
  • the meq/gram aldehyde values shown in Table 20 were determined from equation (2), with the exception of Example 8- 4, which was measured directly.
  • the aldehyde content was determined by sugar analysis of the acid-hydrolyzed guar product using HPLC, to obtain the ratio of galactose/mannose for the starting cationic guar precursor and the oxidized cationic guar product.
  • the aldehyde content of the oxidized cationic guar was 23%, corresponding to 0.41mmole aldehyde/gram polymer.
  • Test strips coHed '" wIth '' the Purpald reagent (E-M Science)were also used to measure aldehyde content in samples prepared by the methods in Examples 6 and 8a-c. These results are shown in Table 21 along with the viscosity data and MW data for the products of this invention. Combined together, the results in Tables 20 and 21 demonstrate that the products of this invention have an aldehyde content of at least O.OOlmeq/gram and the lower Brookfield viscosity limit for the products of this invention is 40cps at 30rpm, 25C, sp. 4 and the upper Brookfield viscosity limit is 2,000,000cps at 0.3rpm, 25C, sp.4.
  • the following examples demonstrate that the low molecular weight cationic oxidized polysaccharides of this invention can be incorporated into personal care formulations containing silicone materials, and the viscosities of the resulting products are significantly reduced when compared to the viscosities of silicone formulations containing high molecular weight commercial cationic polysaccharides available in the marketplace.
  • the silicone materials can be in the form of polymers or oligomers of a cyclosiloxane, linear siloxane, hydroxy terminated siloxane, comb or graft siloxane structure with polyol, amino, or other functional groups present in the siloxane structure.
  • An anionic shampoo formulation was used for these Experiments comprised of the ingredients in Table 22.
  • the formulation was prepared by mixing the surfactants and water at 60C for 1 hour, cooling the mixture to 35C and adding the silicone emulsion.
  • the shampoos contained GE Silicones emulsion SM555 at 0.5wt% silicone content.
  • the low molecular weight cationic guar from Example 6, Table 5, experiment Y was incorporated into the shampoo in Example 71-1 and compared with shampoos containing high MW commercial cationic guars in Examples 71-2 through 71-5 and with a commercial shampoo in Example 71-6. Viscosities of the shampoos were measured using a Brookfield LVT viscometer, sp. 4, at 0.3 and 30 rpm at room temperature.
  • the cationic oxidized polysaccharides of this invention and its binary and tertiary blends with other functional polymers e.g., chitosan, polyvinylpyrrolidone homopolymers and copolymers, acrylamide homopolymers and copolymers, high MW cationic hydroxyethylcellulose, high Mw cationic guars, and hydrophobic polymers (also known as associative polymers) can be designed to improve the formulation aesthetics(i.e., foaming), stability, delivery and deposition efficiency of conditioning oils such as silicones or other conditioning agents to hair, skin, and textile substrates.
  • functional polymers e.g., chitosan, polyvinylpyrrolidone homopolymers and copolymers, acrylamide homopolymers and copolymers, high MW cationic hydroxyethylcellulose, high Mw cationic guars, and hydrophobic polymers (also known as associative polymers) can be
  • blends may also improve delivery efficiency of other ingredients, such as antimicrobial compounds, antidandruff compounds, conditioning agents, fragrances, sunscreen actives, emmolients, moisturizers, medicaments such as anti-psoriasis medicines, styling aids such as polyvinylpyrrolidone copolymers, sizing agents, etc. to hair, skin, and textile substrates.
  • other ingredients such as antimicrobial compounds, antidandruff compounds, conditioning agents, fragrances, sunscreen actives, emmolients, moisturizers, medicaments such as anti-psoriasis medicines, styling aids such as polyvinylpyrrolidone copolymers, sizing agents, etc.
  • a 5% dispersion of chitosan (Vanson Incorporated, Redmond, Washington; 88% deacetylation, 1% viscosity: 660cps) was prepared by mixing 2.1 grams chitosan with a 6% dispersion of fumaric acid. Two blends were prepared using this dispersion:

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JP4933251B2 (ja) 2012-05-16
WO2004091557A2 (en) 2004-10-28
KR101118460B1 (ko) 2012-04-13
CA2519373A1 (en) 2004-10-28
CN1780857A (zh) 2006-05-31
WO2004091557A3 (en) 2005-01-27
JP2006522829A (ja) 2006-10-05
RU2005134392A (ru) 2006-06-10
KR20050120790A (ko) 2005-12-23
BRPI0409243A (pt) 2006-03-28
BRPI0409243B1 (pt) 2015-07-07
MXPA05010749A (es) 2005-12-15

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