KR20140139337A - Cationic gua gum modified with polymer having phosphorylcholine-like groups and silane groups, and their cosmetic Formulations - Google Patents

Cationic gua gum modified with polymer having phosphorylcholine-like groups and silane groups, and their cosmetic Formulations Download PDF

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KR20140139337A
KR20140139337A KR1020130059859A KR20130059859A KR20140139337A KR 20140139337 A KR20140139337 A KR 20140139337A KR 1020130059859 A KR1020130059859 A KR 1020130059859A KR 20130059859 A KR20130059859 A KR 20130059859A KR 20140139337 A KR20140139337 A KR 20140139337A
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guar gum
group
cationic
trimethylammonio
ethyl
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한인선
이매인
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주식회사 케이씨아이
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    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00Cosmetics or similar toiletry preparations
    • A61K8/02Cosmetics or similar toiletry preparations characterised by special physical form
    • A61K8/0216Solid or semisolid forms
    • A61K8/022Powders; Compacted Powders
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00Cosmetics or similar toiletry preparations
    • A61K8/18Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/55Phosphorus compounds
    • A61K8/553Phospholipids, e.g. lecithin
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00Cosmetics or similar toiletry preparations
    • A61K8/18Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/58Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing atoms other than carbon, hydrogen, halogen, oxygen, nitrogen, sulfur or phosphorus
    • A61K8/585Organosilicon compounds
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00Cosmetics or similar toiletry preparations
    • A61K8/18Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/72Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
    • A61K8/73Polysaccharides
    • A61K8/737Galactomannans, e.g. guar; Derivatives thereof
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00Cosmetics or similar toiletry preparations
    • A61K8/18Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/72Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
    • A61K8/90Block copolymers
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61QSPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q19/00Preparations for care of the skin
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61QSPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q5/00Preparations for care of the hair
    • A61Q5/12Preparations containing hair conditioners
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08BPOLYSACCHARIDES; DERIVATIVES THEREOF
    • C08B37/00Preparation of polysaccharides not provided for in groups C08B1/00 - C08B35/00; Derivatives thereof
    • C08B37/006Heteroglycans, i.e. polysaccharides having more than one sugar residue in the main chain in either alternating or less regular sequence; Gellans; Succinoglycans; Arabinogalactans; Tragacanth or gum tragacanth or traganth from Astragalus; Gum Karaya from Sterculia urens; Gum Ghatti from Anogeissus latifolia; Derivatives thereof
    • C08B37/0087Glucomannans or galactomannans; Tara or tara gum, i.e. D-mannose and D-galactose units, e.g. from Cesalpinia spinosa; Tamarind gum, i.e. D-galactose, D-glucose and D-xylose units, e.g. from Tamarindus indica; Gum Arabic, i.e. L-arabinose, L-rhamnose, D-galactose and D-glucuronic acid units, e.g. from Acacia Senegal or Acacia Seyal; Derivatives thereof
    • C08B37/0096Guar, guar gum, guar flour, guaran, i.e. (beta-1,4) linked D-mannose units in the main chain branched with D-galactose units in (alpha-1,6), e.g. from Cyamopsis Tetragonolobus; Derivatives thereof

Abstract

In the present invention, provided is a method for manufacturing cationic modified gua gums which comprises the steps of: preparing cationic gua gums; and turning the cationic gua gums into polymer having phosphorylcholine based groups and silane groups. The cationic modified gua gums of the present invention is turned into polymer having phosphorylcholine based groups and silane groups without using crosslinking agents like glyoxal and boron, and resolving the solubility problems for water, so that the cationic modified gua gums has improved moisturizing ability and excellent biocompatibility than conventional cationic gua gums. Accordingly, compositions for hair or skin care including the cationic modified gua gums can have improved moisturizing ability and protect the damaged skin and hair.

Description

[0001] The present invention relates to a cationic guar gum modified with a polymer having a phosphorylcholine group and a silane group, and a cosmetic composition containing the cationic guar gum modified with polymer having phosphorylcholine groups and silane groups,

[0001] The present invention relates to a cationic guar gum modified with a polymer having a phosphorylcholine group and a silane group, and a cosmetic composition containing the cationic guar gum modified with polymer having phosphorylcholine groups and silane groups,

Cationic macromolecular compounds such as cationic guar gum are widely used in various fields such as thickeners, adhesives, dispersants, emulsion stabilizers, and the like because they have hydrophilic properties and viscosity. In these applications, the cationic polymer compound is generally dissolved in a water or a mixed solvent containing water (hereinafter, also referred to as an aqueous solvent), and therefore, in consideration of solubility, .

However, since such a cationic polymer compound has a very high solubility in water or a water-based solvent, there is a problem that when the polymer is dissolved in water, the surface is instantaneously dissolved in water to form a lump, thereby preventing water from penetrating into the polymer It is difficult to use industrially. In order to solve this problem, existing products have been proposed to treat with glyoxal or boron (JP 2007-084680 A), but these raw materials are known to be harmful to the human body due to their strong toxicity There is a problem.

On the other hand, hair and scalp damage caused by environmental pollution, ultraviolet ray exposure, frequent perms or dyeing become serious, and it is possible to exhibit better moisture resistance at the time of applying and after hair application, and to provide a protective effect of improved damaged hair and scalp And there is a growing demand for new hair and skin products that can provide environmentally friendly and proper nutrition.

Phosphorylcholine-like group-containing polymers originate from a phospholipid-like structure derived from a biological membrane and are known to have excellent properties such as biocompatibility such as inactivation of blood components, non-adsorbability of biocompatibility, antifouling property and moisturizing property. In addition, studies on the synthesis and use of phospholipyrine analogues containing polymers for the purpose of developing bio-related materials utilizing their functions have been actively conducted.

Such a phospholiphenol-containing group-containing polymer includes a phosphorylcholine-group-containing monomer, especially 2- (methacryloyloxy) ethyl-2 '- (trimethylammonio) ethylphosphate [2- (methacryloyloxy) (hereinafter abbreviated as " MPC ") is a polymer which is structurally similar to phosphatidylcholine, which is a cell wall constituent, such as phospholipid, It is known that choline analogues are present to impart excellent biocompatibility and excellent moisturizing properties.

SUMMARY OF THE INVENTION The present invention has been made to solve the above problems, and it is an object of the present invention to provide a polymer having a phosphorylcholine group and a silane group, without using a crosslinking agent such as glyoxal or boron, And to provide a cationic modified guar gum capable of solving the solubility problem and a method for producing the same.

In addition, the composition exhibits improved moisturizing power and superior biocompatibility than conventional cationic guar gum compounds, and accordingly, the composition for hair and skin care containing the same also has a cationic degeneration which can have improved moisturizing power, Guar gum, a hair care composition containing the same, or a composition for skin care.

In order to solve the above-mentioned object of the present invention,

The present invention provides a method for preparing a cationic guar gum comprising: preparing a cationic guar gum; And modifying the cationic guar gum with a polymer having a phosphorylcholine group and a silane group. The present invention also provides a method for producing a cationically modified guar gum.

In addition, the above-mentioned phospholylcholine group and the polymer having a silane group provide a method for producing a cationic modified guar gum obtained by copolymerizing a phosphorylcholine-based compound represented by the following formula (1) and an organosilane having an unsaturated group.

[Chemical Formula (1)

Figure pat00001

In formula (1), X represents a divalent organic residue, and Z represents a hydrogen atom or R 5 -O-CO- (wherein R 5 represents a hydrogen atom, an alkyl group having 1 to 10 carbon atoms or a hydroxyalkyl group having 1 to 10 carbon atoms , And Y represents an alkyleneoxy group having 1 to 20 carbon atoms. R 1 represents a hydrogen atom or a hydrocarbon group of 1 to 5 carbon atoms; R 2 , R 3 and R 4 represent the same or different groups and represent a hydrogen atom, a hydrocarbon group of 1 to 6 carbon atoms, or a hydroxyhydrocarbon group; M is an integer of 1 to 20, and n is an integer of 2 to 5.)

The unsaturated group-containing organosilane may be at least one selected from the group consisting of (meth) acryloxypropyltrimethoxysilane, vinyltrimethoxysilane or vinyltriethoxysilane, Of the present invention.

Also provided is a method for producing cationic modified guar gum which is cationized by treating the cationic guar gum black water soluble guar gum with a cationizing agent.

In the copolymerization of the phosphorylcholine compound and the organosilane having an unsaturated group, the content of the phosphorylcholine compound based on the total monomer is 90 to 10% by weight, the content of the organosilane having an unsaturated group is 10 to 90% by weight, Modified guar gum.

The amount of the polymer having phosphorylcholine group and silane group is 0.05 to 10% by weight, based on the active ingredient, of the water-soluble guar gum.

In addition, the phospholylcholine-based compound may be at least one selected from the group consisting of 2 - ((meth) acryloyloxy) ethyl-2 '- (trimethylammonio) ethyl phosphate, 3 - ((meth) acryloyloxy) (Trimethylammonio) ethylphosphate, 4 - ((meth) acryloyloxy) butyl-2 '- (trimethylammonio) ethylphosphate, 5- 2 '- (trimethylammonio) ethylphosphate, 2 - ((meth) acryloyloxy) ethyl-2' - (triethylammonio) Ethyl (meth) acryloyloxy) ethyl-2 '- (tributylammonio) ethyl phosphate, ethyl 2- (Trimethylammonio) ethylphosphate, 2 - ((meth) acryloyloxy) butyl-2 '- (trimethylammonio) ethylphosphate, 2- 2 - ((meth) acryloyl (Vinyloxy) ethyl-2 '- (trimethylammonio) ethylphosphate, 2 - ((meth) acryloyloxy) hexyl- - (trimethylammonio) ethylphosphate, 2- (allyloxy) ethyl-2 '- (trimethylammonio) ethylphosphate, 2- (Trimethylammonio) ethylphosphate, 2- (p-vinylbenzyl) ethyl-2 '- (trimethylammonio) ethylphosphate, 2- Ethyl-2 '- (trimethylammonio) ethylphosphate, 2- (vinyloxycarbonyl) ethyl-2'- (trimethylammonio) ethylphosphate, 2- (allyloxycarbonyl) (Vinylcarbamoyl) ethyl-2 '- (trimethylammonio) ethyl phosphate, 2- (2-hydroxyethyl) ethyl phosphate, Allyloxy Ethyl) -2 '- (trimethylammonio) ethylphosphate, 2- (butanoyloxy) ethyl- (2'-trimethylammonioethylphosphoryl ethyl) fumarate, butyl- (2'-trimethylammonioethylphosphorylethyl) fumarate, hydroxyethyl- (2'- (2'-trimethylammonioethylphosphorylethyl) fumarate, hydroxyethyl (2-trimethylammonioethylphosphorylethyl) fumarate, '-Trimethylammonioethylphosphorylethyl) fmalate. The present invention also provides a method for producing a cationic modified guar gum.

The present invention also provides a cationic modified guar gum prepared by the above method.

Also provided is a cationic modified guar gum which is formulated in powder or sheet form.

The present invention also provides a hair or skin care composition comprising the cationic modified guar gum as an active ingredient.

In addition, the cationic modified guar gum in the composition provides 0.01 to 5% by weight, based on the total weight of the composition, of a composition for hair or skin care.

The modification of the polymer with a phosphorylcholine group and a silane group-containing polymer without using a crosslinking agent such as cationic modified guar gyoxal or boron according to the present invention can solve the problem of solubility in water But also has improved moisturizing power and superior biocompatibility than conventional cationic guar gum compounds, and accordingly, the composition for hair and skin care containing the same can also have improved moisture resistance, damage to damaged skin and damaged hair.

Hereinafter, the present invention will be described in detail with reference to examples. It should be understood, however, that there is no intention to limit the scope of protection of the present invention, even if there are definite and definitive expressions, since the following examples are merely intended to illustrate the present invention more clearly.

The cationic modified guar gum and the preparation method thereof according to an embodiment of the present invention include the steps of preparing a cationic guar gum and modifying the cationic guar gum with a polymer having a phosphorylcholine group and a silane group . By treating the cationic guar gum with a polymer having a phosphorylcholine group and a silane group, the dispersibility to water can be increased, and thus the problem of solubility in water can be solved. In addition, the inclusion of a phosphorylcholine group can increase biocompatibility, and can have a moisturizing effect and protection against damaged skin and damaged hair. The content of the polymer having a phosphorylcholine group and a silane group is not limited to a great extent. However, considering compatibility of biocompatibility, moisturizing ability and dispersing ability, 0.05 to 10.0 parts by weight of the active ingredient, which is a precursor of the cationic modified guar gum, By weight, more preferably from 0.1 to 5.0% by weight, particularly preferably from 1.0 to 3.0% by weight. It has excellent dispersibility and dissolution characteristics in the above range, and can provide a desired effect when added to a composition (see Examples described later).

First, cationic guar gum and its preparation method will be explained.

The cationic guar black is not limited but can be obtained by cationizing guar gum with a cationizing agent. And high molecular weight polysaccharides composed of guar black galactomannan, also known as guar gum. The water-soluble fraction of guar gum is referred to as guaran and is typically (1 → 6) -β-D-mannopyranosyl (α-D-galactopyranosyl) Unit (D-mannose). The ratio of D-galactose to D-mannose is 1: 2.

The cationization of the water-soluble guar gum can be carried out by reacting the water-soluble guar gum with a cationizing agent. Specific examples of the cationizing agent include glycidyltrialkylammonium salts such as glycidyltrimethylammonium chloride, glycidyltriethylammonium chloride, glycidyltrimethylammonium bromide and glycidyltriethylammonium bromide, And ammonium halide compounds such as halide, dimethyldiallylammonium chloride, methacryloyloxyethylenetrimethylammonium chloride, and 3-chloro-2-hydroxypropyltrimethylammonium chloride.

More preferably, the quaternary ammonium compound containing at least one epoxy group-containing quaternary ammonium compound is preferably a quaternary ammonium compound containing no phosphorylcholine-like group represented by the above formula (1) . Quaternary ammonium compounds containing an epoxy group improve the solubility of the copolymer and facilitate the hair adsorption of the copolymer and improve the hair conditioning effect of the copolymer. The type of the cationic agent is not particularly limited, and it is preferable that the cationic agent is an epoxyalkyltrialkylammonium halide in consideration of the conditioning effect of the copolymer and the commercial availability. In this case, the alkyl group of the epoxy alkyl has 2 to 20 carbon atoms, and the alkyl group of the trialkyl has 1 to 20 carbon atoms, and is more preferably the same or different. For example, epoxypropyltrimethylammonium chloride is preferred.

The cauterizing agent is not limited, but it is preferably used in an amount of 5 to 95 parts by weight, more preferably 10 to 80 parts by weight, per 100 parts by weight of the water-soluble guar gum, considering the conditioning effect of the copolymer and the compatibility with the polymer. To 60 parts by weight.

As the solvent used in the cationization reaction, a mixed solvent of a water-soluble organic solvent and water is preferable. The water-soluble organic solvent is not particularly limited as long as it is a homogeneous solution when mixed with water, and examples thereof include alcohols having 1 to 4 carbon atoms and acetone. Among them, alcohols having 1 to 4 carbon atoms are preferable, and specific examples thereof include methanol, ethanol, isopropanol, n-propanol, t-butyl alcohol and the like. The ratio of water in the mixed solvent is preferably from 12 to 30 mass%, more preferably from 12 to 20 mass% from the viewpoint of suppressing the side reaction and promoting the cationization reaction efficiently. The amount of the mixed solvent to be used is preferably 200 to 1,500 parts by mass with respect to 100 parts by mass of the water-soluble guar gum ether, from the viewpoint of avoiding localization of the cationization of the water-soluble guar gum and from the viewpoint of increasing the volume efficiency of the reactor, More preferably 300 to 800 parts by mass.

Examples of the alkali which can be used in the cationization reaction include alkali metal hydroxides such as sodium hydroxide, potassium hydroxide and lithium hydroxide. Of these, sodium hydroxide is preferable because it is inexpensive. The amount of the alkali to be used is preferably such that the content of alkali is 0.1 to 10% by mass with respect to the water-soluble guar gum ether.

The reaction between the water-soluble guar gum and the cationizing agent can be carried out, for example, by mixing the water-soluble guar gum, the mixed solvent and the alkali, stirring the mixture, adding a cationizing agent, . The reaction temperature at this time is usually in the range of 40 to 60 占 폚, preferably 45 to 55 占 폚, from the viewpoints of accelerating the reaction, shortening the reaction time, and avoiding the abrupt progress of the reaction . The reaction time varies depending on the reaction temperature and therefore can not be determined in a word, but is usually about 2 to 4 hours.

Next, a polymer having a phosphorylcholine group and a silane group and a method for producing the same will be described.

The polymer having the phosphorylcholine group and the silane group can be prepared by various methods. A form in which a phosphorylcholine group and a silane group are present in the compound structure is included in the present invention. The weight average molecular weight of the polymer is not particularly limited, but is preferably in the range of 10,000 to 2,000,000 from the viewpoint of solubility and moisture retention.

For example, it can be obtained by copolymerizing a phosphorylcholine-based compound having the following formula (1) and an organosilane having an unsaturated group. The content of the total monomers based on the phosphorylcholine compound is preferably from 90 to 10% by weight, and the content of the unsaturated group-containing organosilane is from 10 to 90% by weight. The moisture resistance and solubility can be particularly excellent within the above range.

[Chemical Formula (1)

Figure pat00002

Wherein X represents a divalent organic residue and Z represents a hydrogen atom or R 5 -O-CO- wherein R 5 represents a hydrogen atom, an alkyl group having 1 to 10 carbon atoms or a hydroxy group having 1 to 10 carbon atoms, Alkyl group), and Y represents an alkyleneoxy group having 1 to 20 carbon atoms. R 1 represents a hydrogen atom or a hydrocarbon group of 1 to 5 carbon atoms; R 2 , R 3 and R 4 represent the same or different groups and represent a hydrogen atom, a hydrocarbon group of 1 to 6 carbon atoms, or a hydroxyhydrocarbon group; M is an integer of 1 to 20, and n is an integer of 2 to 5.

More specifically, the formula (1) may be represented by the following formula (2).

(2)

Figure pat00003

In the above formula (2), Z represents a hydrogen atom or R 5 -O-CO- (wherein R 5 represents a hydrogen atom, an alkyl group having 1 to 10 carbon atoms or a hydroxyalkyl group having 1 to 10 carbon atoms) And an alkyleneoxy group having 1 to 20 carbon atoms. R 1 represents a hydrogen atom or a hydrocarbon group of 1 to 5 carbon atoms; R 2 , R 3 and R 4 represent the same or different groups and represent a hydrogen atom, a hydrocarbon group of 1 to 6 carbon atoms, or a hydroxyhydrocarbon group; M is an integer of 1 to 20, and n is an integer of 2 to 5.

Specific examples of the phospholylcholine-based compound include 2 - ((meth) acryloyloxy) ethyl-2 '- (trimethylammonio) ethyl phosphate, 3 - ((meth) acryloyloxy) ((Meth) acryloyloxy) butyl-2 '- (trimethylammonio) ethylphosphate, 5 - (Trimethylammonio) ethyl phosphate, 6 ((meth) acryloyloxy) hexyl-2 '- (trimethylammonio) ethylphosphate, 2- 2 - ((meth) acryloyloxy) ethyl-2 '(trimethylammonio) ethylphosphate, 2 - (Trimethylammonio) ethylphosphate, 2 - ((meth) acryloyloxy) butyl-2 '- (trimethylammonio) ethylphosphate, Ethyl phosphate, 2 - (( (Meth) acryloyloxy) pentyl-2 '- (trimethylammonio) ethylphosphate, 2- ((meth) acryloyloxy) hexyl- Ethyl-2 '- (trimethylammonio) ethylphosphate, 2- (allyloxy) ethyl-2'- (trimethylammonio) ethylphosphate, 2- (Trimethylammonio) ethylphosphate, 2- (p-vinylbenzoyloxy) ethyl-2 '-( trimethylammonio) ethylphosphate, 2- (Vinyloxycarbonyl) ethyl-2 '- (trimethylammonio) ethylphosphate, 2- (allyloxycarbonyl) ethyl-2' - (trimethylammonio) ethylphosphate, 2- (acryloylamino) ethyl-2 '- (trimethylammonio) ethylphosphate, 2- (vinylcarbonylamino) ethyl- pay (Trimethylammonio) ethylphosphate, 2- (butyryloxy) ethyl-2 '- (trimethylammonio) ethylphosphate, 2- (2'-trimethylammonioethylphosphorylethyl) fumarate, ethyl (2'-trimethylammonioethylphosphorylethyl) fumarate, ethyl (2'-trimethylammonioethylphosphorylethyl) fumarate, ethyl- (2'-trimethylammonioethylphosphorylethyl) fumarate, butyl (2'-trimethylammonioethylphosphorylethyl) , Hydroxyethyl- (2'-trimethylammonioethylphosphorylethyl) fmalate, and the like. In the present specification, the term " (meth) acrylic " means both " acrylic "

The phosphorylcholine monomer according to the present invention is not particularly limited, but it is preferable to use 2- (methacryloyloxy) ethyl-2 '- (trimethylammonio) ethylphosphate [2- (methacryloyloxy) ethyl- 2 '- (trimethylammonio) ethylphosphate, 2-methacryloyloxyethylphosphorylcholine (hereinafter abbreviated as MPC)] is preferable, but is not limited thereto.

In the unsaturated group-containing organosilane, the unsaturated group is not limited but may be acryl, vinyl, allyl, cycloalkene, and the like.

Preferably, the unsaturated organosilane may be of the general formula R1R2SiY2. R1 is an alkyl group having 2 to 15 carbon atoms having an unsaturated group or an alkoxy group having 2 to 15 carbon atoms having an unsaturated group, Y is a hydrolysable organic group, and R2 is R1 or Y. Examples of the type of R1 are many, and may be, for example, a (meth) acryloxyalkyl group or a (meth) acryloxyalkoxy group. It is also possible to use vinyl, allyl, butenyl, cyclohexenyl, cyclopentadienyl, cyclohexanedienyl, (meth) acryloxyalkyl groups (CH2 = CH (CH3) COO- (CH2) 3-, CH2 = C (CH3) COO-CH2- CH2O- (CH2) 3-, etc.). Preferably, R1 is a (meth) acryloxyalkyl group. The hydrolyzable group Y may be an alkoxy group of a methoxy, ethoxy or butoxy type, and may be an acyloxy group, a formyloxy group, An acetoxy group or a propionoxy group. Preferably, the unsaturated organosilane can be (meth) acryloxypropyltrimethoxysilane, vinyltrimethoxysilane, or vinyltriethoxysilane.

The radical polymerization initiator used for copolymerizing the phospholyl choline compound and the unsaturated group-containing organosilane is an azo initiator such as azobisisobutyronitrile (AIBN), azobisdimethylvaleronitrile Benzoyl peroxide, lauroyl peroxide, potassium persulfate, di (2ethylhexyl) peroxydicarbonate, di (sec-butyl) Di (secbutyl) peroxydicarbonate], di (isopropyl) peroxydicarbonate, di (cyclohexyl) peroxydicarbonate, di (cetyl) peroxydicarbonate, Peroxycarbonate such as carbonate (di (cetyl) peroxydicarbonate], di (n-propyl) peroxydicarbonate and the like. Commercial products of the polymerization initiator include Vazo 52G, Vazo 64G, Vazo 67G and Vazo 88G of Dupont Co., Ltd. The selection of the initiator depends on the half life time of each initiator and the boiling point of the organic solvent .

On the other hand, a solvent may be used in the polymerization reaction, and an appropriate solvent is selected according to the polymerization method. Suspension polymerization using an organic solvent as a reaction medium, reverse emulsion polymerization, precipitation polymerization, or solution polymerization using water as a reaction medium. The solvent is not limited, but may be used at a weight ratio of 1 to 30 times the total weight of the monomers. Examples of the organic solvent include toluene, benzene, cyclohexane, ethyl acetate, n-hexane, ethanol, n-propanol, isopropanol, t-butyl alcohol and methyl ethyl ketone. , And one or more organic solvents are mixed in an appropriate amount. For example, it can be used as a mixed solvent in a weight ratio of 1:99 to 99: 1.

In the copolymerization of the phosphorylcholine-based compound and the organosilane having an unsaturated group, additional monomers may be further used and copolymerized, without limitation. (Meth) acrylate, stearyl (meth) acrylate, 2-ethylhexyl (meth) acrylate, isopropyl (meth) acrylate, , And (meth) acrylic monomers such as cyclohexyl (meth) acrylate. Further, if necessary, it may further include an appropriate amount of a crosslinking agent and is not limited. Examples of the crosslinking agent include ethylene glycol diacrylate, ethylene glycol dimethacrylate, propylene glycol diacrylate, propylene glycol dimethacrylate Butylene glycol diacrylate, butylene glycol dimethacrylate, hexylene glycol diacrylate, hexylene glycol dimethacrylate, hexylene glycol dimethacrylate, dimethacrylate, diethylene glycol diacrylate, diethylene glycol dimethacrylate, triethylene glycol diacrylate, triethylene glycol dimethacrylate, triethylene glycol diacrylate, dimethacrylate), tetraethylene glycol diacryl But are not limited to, tetraethylene glycol diacrylate, tetraethylene glycol dimethacrylate, allyl acrylate, allyl methacrylate, methallyl acrylate, allyl ethacrylate, but are not limited to, allyl ethacrylate, ethallyl acrylate, methallyl methacrylate, diallyl phthalate, diallyl maleate, diallyl succinate, But are not limited to, triallyl phosphate, diallyl oxalate, diallyl malonate, diallyl citrate, diallyl fumarate, divinyl benzene ), Trivinyl bezene, vinyl crotonate, N, N-methylene-bis-acrylamide, Trimethylolpropane diallyl ether or trimethylolpropane triallyl ether, diallyl pentaerythritol ether, triallyl pentaerythritol ether, triallyl pentaerythritol ether, But are not limited to, tetraallyl pentaerythritol ether, diallyl sucrose ether, triallyl sucrose ether, tetraallyl sucrose ether, pentaallyl sucrose ether, sucroseether, hexaallyl sucrose ether, etc. These may be used alone or in combination.

Next, the cationic modified guar gum obtained by treating cationic guar gum with a phosphoryl choline-silane polymer will be described.

The method of reacting the cationic guar gum with the phosphorylcholine-silane polymer is not particularly limited, and conventional silane treatment methods can be applied. For example, a method of adding a phosphorylcholine-silane polymer to the prepared cationic guar gum (or a slurry thereof), reacting and then drying can be mentioned. The reaction temperature is not limited, and preferably from 20 to 80 캜, with stirring. The reaction time is not particularly limited, and can be appropriately selected depending on the reaction temperature, the purpose, and the like. Preferably from 5 minutes to 3 hours.

Next, a specific method for producing a cationic modified guar gum will be described.

First, alcohol and water are added to the reactor, water-soluble guar gum and a cationic agent are added thereto, and the mixture is stirred and dissolved at about 20 to 30 ° C. Thereafter, the aqueous base solution is added to the reactor, and after stirring, the temperature is raised to about 40 to 70 ° C. The reaction is terminated by adding an aqueous acid solution to the reaction mixture. After completion of the reaction, alcohol and distilled water are added to the reactor and stirred to dilute the reaction product, and the diluted reaction product is filtered and washed with water to obtain a cationic guar gum slurry.

The cationic guar gum compound thus obtained may be reacted with a phosphorylcholine-organosilane polymer in order to improve the dispersibility in water, and the resultant mixture may be filtered and dry-pulverized to finally produce a cationic modified guar gum. Cationic modified guar may also be obtained in black powder form. It is more preferable to formulate it in a sheet form. In the case of powder formulations, a dustproof mask should be used to prevent inhalation to human body when dust is used, and a moisture-proof packaging container is required to prevent clogging due to moisture absorption, which is disadvantageous for long-term storage. However, sheet formulations have the advantage that they do not blow dust and the moisture absorption rate is low, so that no separate moisture-proof packaging container is required.

Another object of the present invention can be attained by providing a composition for hair or skin care comprising the above-described amphoteric modified guar gum as an active ingredient.

First, a composition for hair care will be described.

The content of the cationic modified guar gum in the composition for hair care according to one embodiment of the present invention is not limited to a great extent, but it is preferably from 0.01 to 5% by weight based on the total weight of the composition, considering the feeling of use, More preferably 0.1 to 5% by weight, and most preferably 0.1 to 4% by weight. The quaternary ammonium cations containing an epoxy group impart excellent hair adsorption properties and impart excellent biocompatibility and excellent moisture retention by the phosphorylcholine-silane polymer denaturation treatment. Therefore, the quaternary ammonium cations are excellent in solubility, remarkably improved moisture resistance, .

 The composition for hair care of the present invention may be formulated with suitable carriers and additives such as surfactants, perfumes, opacifiers, combing aids, proteins, aerosol propellents, thickeners, gelling agents, ), And the like.

In addition, the composition for hair care of the present invention is not limited to its formulation and may be manufactured into various formulations including, for example, shampoo, rinse, hair fixing wax, hair conditioner and the like. In addition, the composition of the present invention can be used in a skin care product to provide a moisturizing and skin-protecting effect.

Next, the composition for skin care will be described.

The composition for skin care according to one embodiment of the present invention contains the above cationically modified guar gum as an active ingredient and the content of the skin care composition is not particularly limited, but it is preferably 0.01 to 2% by weight, Preferably 0.05 to 0.5% by weight. When it is included in the above-mentioned range, it is advantageous in feeling of use, moisturizing feeling, skin protection and the like.

Excellent biocompatibility and excellent moisture retention are imparted by the phospholipalline choline-silane polymer denaturation treatment, thereby exhibiting improved biocompatibility and solubility, remarkably improved moisture resistance, and a protective effect of damaged skin.

 The composition for skin care of the present invention may be formulated with suitable carriers and additives such as a surfactant, a perfume component, an opacifier, a combing aids, a protein, an aerosol propellents, a thickener, a gelling agent ), And the like.

In addition, the composition for skin care of the present invention is not limited to its formulation and may be manufactured into various formulations including, for example, milk lotion, cream, skin, conditioner for skin care, and the like. In addition, the composition of the present invention can be used in a hair care product to provide a moisturizing and skin protecting effect.

Hereinafter, the present invention will be described in more detail with reference to examples. However, the following examples are intended to explain the present invention more clearly and do not limit the scope of protection of the present invention.

Production Example 1-1 Preparation of MPC-silane (9: 1) polymer

The reactor was charged with 420 g of anhydrous ethanol and 45 g of MPC. The mixture was mixed with stirring, and then 5 g of MPTMS (Methacryloxypropyltrimethoxysilane, cas no 2530-85-0) was added. 0.7 g of AIBN was added as a radical initiator and nitrogen was injected at room temperature for 30 minutes. After that, the temperature of the reactor was raised to 50 to 65 ° C., and the reaction was continued for about 6 hours, after which 420 g of anhydrous ethanol was added to dilute the reaction product, and the diluted reaction product was filtered, And concentrated to adjust the ethanol content to 90%. 500 g of the final prepared MPC-silane polymer (active ingredient 10%) was obtained.

≪ Preparation Example 1-2 > Preparation of MPC-silane (7: 3) polymer

In Production Example 1-1, 500 g of an MPC-silane polymer (active ingredient 10%) was obtained in the same manner as in Example 1 except that 35 g of MPC and 15 g of MPTMS were used.

<Preparation Example 1-3> Preparation of MPC-silane (5: 5) polymer

In Production Example 1-1, 500 g of an MPC-silane polymer (active ingredient 10%) was obtained in the same manner as in Example 1 except that 25 g of MPC and 25 g of MPTMS were used.

Preparation Example 1-4 Preparation of MPC-Silane (3: 7) Polymer

In Production Example 1-1, 500 g of MPC-silane polymer (active ingredient 10%) was obtained in the same manner as in Example 1 except that 15 g of MPC and 35 g of MPTMS were used.

&Lt; Preparation Example 1-5 > Preparation of MPC-silane (1: 9) polymer

In Production Example 1-1, 500 g of MPC-silane polymer (active ingredient 10%) was obtained in the same manner as in Example 1 except that 5 g of MPC and 45 g of MPTMS were used.

Preparation Example 2 Preparation of cationic guar gum

1489 g of isopropyl alcohol and 165.5 g of distilled water were added to the reactor, followed by stirring and mixing. 450 g of guar gum was charged and stirred at about 25 캜 for 10 minutes. Then, 185 g of 2,3-epoxypropyltrimethylammonium chloride was added to the reactor, and the mixture was stirred for 15 minutes. 57 g of a sodium hydroxide aqueous solution having a concentration of about 10% was added to the reactor for 4 minutes and stirred for 20 minutes. Thereafter, the temperature of the reactor was raised to 50 to 55 ° C., and the reaction was maintained for about 6 hours. 17.5 g of glacial acetic acid was added to terminate the reaction. Thereafter, 1000 g of 90% aqueous isopropyl alcohol solution was added to the reactor to dilute the reaction product, and the diluted reaction product was filtered to obtain cationic guar gum.

Preparation Example 3-1 Preparation of cationic modified guar gum modified with MPC-silane (9: 1)

The cationic guar gum prepared in Preparation Example 2 was introduced into a reactor, and a 95% aqueous solution of isopropyl alcohol was added thereto. 45 g of the MPC-silane polymer (9: 1) prepared in Preparation Example 1-1 was added thereto, And reacted for about 1 hour to react, re-filter, and then dried to obtain a cationically modified guar gum modified with MPC-silane.

Preparation Example 3-2 Preparation of cationic modified guar gum modified with MPC-silane (7: 3)

Same as Production Example 3-1 except that the MPC-silane polymer (7: 3) prepared in Preparation Example 1-2 was used in place of the MPC-silane polymer (9: 1) prepared in Production Example 1-1 To give a cationic modified guar gum denatured with MPC-silane.

Preparation Example 3-3 Preparation of cationic modified guar gum modified with MPC-silane (5: 5)

Except that the MPC-silane polymer (5: 5) prepared in Preparation Example 1-3 was used in place of the MPC-silane polymer (9: 1) prepared in Production Example 1-1, To give a cationic modified guar gum denatured with MPC-silane.

PREPARATION EXAMPLE 3-4 Preparation of cationic modified guar gum modified with MPC-silane (3: 7)

Same as in Production Example 3-1 except that the MPC-silane polymer (3: 7) prepared in Preparation Example 1-4 was used instead of the MPC-silane polymer (9: 1) prepared in Production Example 1-1 To give a cationic modified guar gum denatured with MPC-silane.

PREPARATION EXAMPLE 3-5 Preparation of cationic modified guar gum modified with MPC-silane (1: 9)

Same as in Production Example 3-1 except that the MPC-silane polymer (1: 9) prepared in Preparation Example 1-5 was used instead of the MPC-silane polymer (9: 1) prepared in Production Example 1-1 To give a cationic modified guar gum denatured with MPC-silane.

PREPARATION EXAMPLE 3-6 Preparation of cationic modified guar gum modified with MPC-silane (9: 1)

A cationic modified guar gum modified with MPC-silane was obtained in the same manner as in Production Example 1-1 except that 90 g of the MPC-silane polymer (9: 1) prepared in Preparation Example 1-1 was used in place of 45 g of the polymer .

Preparation Example 3-7 Preparation of cationic modified guar gum modified with MPC-silane (9: 1)

A cationically modified guar gum modified with MPC-silane was obtained in the same manner as in Production Example 1-1 except that 135 g of the MPC-silane polymer (9: 1) prepared in Production Example 1-1 was used instead of 45 g of the polymer .

<Comparative Control 1> Preparation of unmodified cationic guar gum

The unmodified cationic guar gum of Preparation Example 2, which was not reacted with the MPC-silane polymer (9: 1) prepared from Preparation Example 1-1, was regarded as Comparative Control Example 1.

<Comparative Control Example 2> Boron-treated cationic guar gum

As comparative control 2, boron-treated cationic guar gum (Guarquat L80KC, KCI) was used.

[Evaluation of solubility and dispersibility]

(1) dispersion amount after 2 minutes

To a 100 mL beaker, 80 g of distilled water was added, and 0.5 g of the sample of <Preparation Example 3-1> to <Preparation Example 3-7> was placed at a height of 4 cm from the water surface. After 2 minutes from the end of the sample application, The ratio (%) of dispersed in water without remaining was evaluated, and this was regarded as a dispersion amount after 2 minutes. The results are shown in Table 1. Samples of Comparative Controls 1 and 2 were also measured in the same manner and shown in Table 1.

(2) Absorption time

80 g of distilled water was added to a 100 mL beaker and 0.5 g of the sample of <Preparation Example 3-1> to <Preparation Example 3-7> was placed at a height of 4 cm from the water surface. After the sample was completely charged, The time until absorption and settling was measured, and this was regarded as the complete absorption time. In addition, even if 300 seconds elapsed after the injection, the end which was not completely absorbed was regarded as the end point of the measurement, and the evaluation was made "300 seconds or more". The results are shown in Table 1.

Samples of Comparative Controls 1 and 2 were also measured in the same manner and shown in Table 1.

(3) Dispersion time

150 g of distilled water at 25 DEG C was added to a 200 mL toll beaker (outer diameter 6 cm), and the mixture was stirred by a stirring blade set on a SURIWAN MOTA (manufactured by HEIDOH Co.). A stirring turbine was set with a fan turbine type (2 paddles) of? 40 mm and the lower part of the blade was 2 cm above the lower part of the beaker. The stirring rotation speed was 400 rpm.

While stirring, 1.5 g of the sample of <Preparation Example 3-1> to <Preparation Example 3-7> was added, and immediately thereafter, stirring was continued in a water bath at 70 ° C. After the sample was put in, the time from when the sample was completely dispersed to a state where the mass was not visible to the naked eye was measured. The results are shown in Table 1.

Samples of Comparative Controls 1 and 2 were also measured in the same manner and shown in Table 1.

division Manufacturing example
3-1
Manufacturing example
3-2
Manufacturing example
3-3
Manufacturing example
3-4
Manufacturing example
3-5
Manufacturing example
3-6
Manufacturing example
3-7
Comparative Control Example 1 Comparative Control Example 2
Dispersion amount (%) after 2 minutes 100 100 100 90 90 100 100 10 100 Absorption time in seconds 20 13 15 130 150 7 5 300
More than
5
Dispersion time
(minute)
5 2 2 15 16 <1 <1 120 <1

Example 1: Preparation of composition for hair care

&Lt; Example 1-1 >

40.05 g of water was placed in a mixing vessel and 0.8 g of the cationic modified guar gum prepared in <Preparation Example 3-1> was added thereto while heating, followed by addition of 1 g of propylene glycol and heating at 75 ° C. 18 g of sodium lauryl sulfate, 17 g of sodium laureth sulfate, 2.5 g of cocofatty acid diethanolamide, 8 g of cocamido propyl betain, 3 g of aminopropylamine oxide, 0.5 g of Cetearyl alcohol, 2 g of disodium cocoamphodiacetate, 0.6 g of ethylene glycol distearate, 0.5 g of polyglyceryl- 2 g of polyglyceryl-2 caprate, 0.5 g of cyclopentasiloxane and dimethiconol, 1 g of dimethicone and 0.05 g of tetrasodium EDTA were put into the mixing vessel, The mixture was mixed at 75 DEG C for about 30 minutes until it became homogeneous, and then cooled to 45 DEG C. [ 0.05 g of Alantion, 0.05 g of Methyl chloroisothiazolinone and Methyl isothiazolinone, 0.1 g of DL-Panthenol, 0.5 g of citric acid and 0.5 g of Fragrance component ) Was added to the mixing vessel and mixed at 45 DEG C until uniform, thereby preparing 100 g of the hair care composition of the present invention.

&Lt; Example 1-2 >

The procedure of Example 1-1 was repeated except that the cationic modified guar gum prepared in Preparation Example 3-2 was used instead of the cationic modified guar gum prepared in Preparation Example 3-1.

&Lt; Example 1-3 >

The procedure of Example 1-1 was repeated except that the cationic modified guar gum prepared in Preparation Example 3-1 was replaced by the cationic modified guar gum prepared in Preparation Example 3-3.

&Lt; Example 1-4 >

The procedure of Example 1-1 was repeated, except that the cationic modified guar gum prepared in Preparation Example 3-1 was replaced by the cationic modified guar gum prepared in Preparation Example 3-4, instead of the cationic modified guar gum prepared in Preparation Example 3-1.

&Lt; Example 1-5 >

The procedure of Example 1-1 was repeated except that the cationic modified guar gum prepared in Preparation Example 3-1 was replaced by the cationic modified guar gum prepared in Preparation Example 3-5.

&Lt; Example 1-6 >

The procedure of Example 1-1 was repeated, except that the cationic modified guar gum prepared in Preparation Example 3-1 was replaced by the cationic modified guar gum prepared in Preparation Example 3-6, instead of the cationic modified guar gum prepared in Preparation Example 3-1.

<Example 1-7>

The procedure of Example 1-1 was repeated, except that the cationic modified guar gum prepared in Preparation Example 3-7 was used instead of the cationic modified guar gum prepared in Preparation Example 3-1.

&Lt; Comparative Example 1-1 >

The procedure of Example 1-1 was repeated except that the unmodified cationic guar gum of <Comparative Control Example 1> was used in place of the cationic modified guar gum prepared in <Preparation Example 3-1> 1.

&Lt; Comparative Example 1-2 >

The procedure of Example 1 was repeated except that the cationic guar gum prepared in Preparation Example 3-1 was replaced with boron-treated cationic guar gum (Guarquat L80KC, manufactured by KCI) of <Comparative Control Example 2> -1.

[ hair For care  Of the composition Damaged hair  Protection effect test]

The feeling of winding each of the manufactured hair care compositions, combing in a wet state, combing after drying,

The volume control of hair, the shine of the hair, etc. Through the panel test,

Respectively. The results are shown in Tables 2 to 6 below.

panel Example
1-1
Example
1-2
Example
1-3
Example
1-4
Example
1-5
Example
1-6
Example
1-7
Comparative Example
1-1
Comparative Example
1-2
PJH 8 8 8 8 10 10 10 5 5 MJL 8 8 8 8 8 8 10 5 3 LSY 8 8 5 5 8 8 8 3 5 LMI 5 5 5 5 5 8 8 3 3 SSM 8 10 8 8 8 10 10 5 5 MYS 8 5 5 5 8 8 8 3 3 HYA 5 5 5 5 5 8 8 3 3 KJH 8 8 8 8 8 8 10 5 5 YSS 10 10 10 8 8 10 10 5 3 KJK 10 10 10 8 8 10 10 5 5 Average 7.8 7.7 7.7 6.8 7.1 8.8 9.2 4.2 4.0

(10: very good / 8: good / 5: normal / 3: poor / 1: very bad)

panel Example
1-1
Example
1-2
Example
1-3
Example
1-4
Example
1-5
Example
1-6
Example
1-7
Comparative Example
1-1
Comparative Example
1-2
PJH 10 8 10 10 10 10 10 3 3 MJL 8 10 8 8 8 10 10 5 5 LSY 8 8 8 5 5 8 8 5 5 LMI 5 8 5 8 5 8 8 3 3 SSM 8 8 8 8 8 8 10 5 5 MYS 5 5 5 5 8 10 8 3 5 HYA 8 8 5 5 5 8 10 3 3 KJH 8 8 8 5 5 8 8 5 5 YSS 8 8 8 8 8 10 10 5 5 KJK 8 8 8 8 8 10 8 5 5 Average 7.6 7.9 7.3 7.0 7.0 9.0 9.0 4.2 4.4

Wet combing (10: Very good / 8: Good / 5: Normal / 3: Poor / 1: Very poor)

panel Example
1-1
Example
1-2
Example
1-3
Example
1-4
Example
1-5
Example
1-6
Example
1-7
Comparative Example
1-1
Comparative Example
1-2
PJH 8 8 8 8 10 10 10 5 5 MJL 8 8 8 10 8 8 8 5 5 LSY 5 5 5 5 5 8 8 5 5 LMI 8 8 5 8 8 8 8 5 5 SSM 8 8 8 5 5 10 10 5 5 MYS 5 5 5 5 5 8 8 5 5 HYA 8 8 5 5 8 8 10 3 5 KJH 5 5 8 5 5 8 8 5 5 YSS 8 8 5 8 5 8 8 3 5 KJK 10 8 8 8 8 8 8 5 3 Average 7.3 7.1 6.5 6.7 6.7 8.4 8.6 4.6 4.8

Combing after drying (10: very good / 8: good / 5: normal / 3: poor / 1: very bad)

panel Example
1-1
Example
1-2
Example
1-3
Example
1-4
Example
1-5
Example
1-6
Example
1-7
Comparative Example
1-1
Comparative Example
1-2
PJH 8 8 5 8 8 8 8 5 5 MJL 5 5 8 5 8 8 8 5 5 LSY 8 5 5 5 5 8 8 5 8 LMI 5 8 5 8 8 8 8 5 5 SSM 8 8 8 5 5 5 5 5 5 MYS 5 5 8 8 5 8 8 8 5 HYA 8 8 5 5 8 8 8 3 5 KJH 8 8 5 5 5 5 8 5 8 YSS 5 5 5 8 5 8 8 8 5 KJK 8 5 5 5 5 8 8 8 5 Average 6.8 6.5 5.9 6.2 6.2 7.4 7.7 5.7 5.6

Volume feeling of hair (10: Very good / 8: Good / 5: Normal / 3: Poor / 1: Very poor)

panel Example
1-1
Example
1-2
Example
1-3
Example
1-4
Example
1-5
Example
1-6
Example
1-7
Comparative Example
1-1
Comparative Example
1-2
PJH 10 8 8 8 8 10 10 5 5 MJL 8 8 8 8 8 8 10 5 5 LSY 8 8 8 5 8 8 8 5 3 LMI 8 8 5 8 8 10 8 5 5 SSM 8 8 8 8 5 8 8 5 5 MYS 5 8 8 8 8 8 8 5 5 HYA 8 8 8 8 8 8 8 3 5 KJH 8 5 5 5 5 8 8 5 5 YSS 8 5 5 8 8 8 8 3 5 KJK 8 8 5 8 10 8 10 5 3 Average 7.9 7.4 6.8 7.4 7.6 8.4 8.6 4.6 4.6

Hair gloss (10: Very good / 8: Good / 5: Normal / 3: Poor / 1: Very poor)

Example 2: Preparation of composition for skin care

&Lt; Example 2-1 >

81.91 g of water was placed in a mixing vessel and 0.25 g of the copolymer prepared in <Preparation Example 3-1> was added thereto while warming, 10 g of 1,3-butylene glycol was added and the mixture was heated to 75 ° C. 0.3 g of Glycerine Glycerylacrylate / acrylic acid copolymer, 2 g of Zantan gum (2%), 0.02 g of Disodium EDTA, 0.1 g of Methyl paraben, 0.15 g of Phenoxy ethanol, 0.02 g of Allantoin, 0.5 g of Methyl Glucoside (EO 10) 0.2 g of DL-Panthenol and 0.4 g of PEG-40 hydrogenated caster oil were put into the mixing vessel, mixed at 75 DEG C for about 30 minutes until uniform, and then cooled to 45 DEG C. [ Subsequently, 3.5 g of ethyl alcohol and 0.15 g of fragrance were added to the mixing vessel and mixed at 45 캜 until homogeneous to obtain 100 g of the skin care composition of the present invention.

&Lt; Example 2-2 >

The procedure of Example 2-1 was repeated, except that the cationic modified guar gum prepared in Preparation Example 3-2 was used instead of the cationic modified guar gum prepared in Preparation Example 3-1.

&Lt; Example 2-3 >

The procedure of Example 2-1 was repeated, except that the cationic modified guar gum prepared in Preparation Example 3-1 was replaced by the cationic modified guar gum prepared in Preparation Example 3-3.

<Example 2-4>

The procedure of Example 2-1 was repeated, except that the cationic modified guar gum prepared in Preparation Example 3-4 was used instead of the cationic modified guar gum prepared in Preparation Example 3-1.

<Example 2-5>

The procedure of Example 2-1 was repeated except that the cationic modified guar gum prepared in Preparation Example 3-1 was replaced with the cationic modified guar gum prepared in Preparation Example 3-5.

<Example 2-6>

The procedure of Example 2-1 was repeated except that the cationic modified guar gum prepared in Preparation Example 3-1 was used instead of the cationic modified guar gum prepared in Preparation Example 3-1.

<Example 2-7>

The procedure of Example 2-1 was repeated except that the cationic modified guar gum prepared in Preparation Example 3-1 was replaced by the cationic modified guar gum prepared in Preparation Example 3-7.

&Lt; Comparative Example 2-1 >

The procedure of Example 2-1 was repeated except that the unmodified cationic guar gum of <Comparative Control Example 1> was used in place of the cationic modified guar gum prepared in <Preparation Example 3-1> 1.

&Lt; Comparative Example 2-2 &

The procedure of Example 1-1 was repeated except that the cationic modified guar gum prepared in Preparation Example 3-1 was replaced with a boron-treated cationic guar gum (Guarquat L80KC, manufactured by KCI) of Comparative Control Example 2 .

[ skin For care  Effectiveness test of composition]

Sodium dodecyl sulfate, an anionic surfactant, is applied daily to the skin to induce skin irritation, which causes the skin to dry out, to cause erythema on the skin, and to lose moisture due to the skin barrier function deterioration. For each skin care composition The skin moisture increase rate, erythema and transdermal water loss were tested to confirm that the skin function was restored and maintained.

For the test method, 5% aqueous solution of sodium dodecyl sulfate was applied to the inside of the subject's skin for 5 minutes and dried at room temperature. After 1 hour, skin moisture, erythema and transdermal water loss were measured for initial measurement.

Each of the skin care compositions prepared after 2 hours and 6 hours after application of a 5% aqueous solution of sodium dodecyl sulfate (hereinafter referred to as SDS aqueous solution) to the inside of the subject's skin was applied twice. After repeated daily for 2 weeks, measure the skin moisture, erythema and transdermal water loss in each test site as the final measurement. The skin improvement effect is evaluated by comparing the initial measurement value with the final measurement value for each test site. The skin measurements for each were repeated 5 times, and the subjects were subjected to 10 persons of 20-40 years of age to obtain an average value.

Mexameter MX18, Corneometer CM825, and Tewameter TM300 from CK Electronic GmbH of Germany were used as the test apparatus, and the results are shown in Tables 7 to 9 below.

panel Example
2-1
Example
2-2
Example
2-3
Example
2-4
Example
2-5
Example
2-6
Example
2-7
Comparative Example
2-1
Comparative Example
2-2
control
Early
Measure
24.5 25.2 24.9 25.1 24.8 25.3 24.7 24.9 25.0 25.1
final
Measure
40.8 39.1 37.1 36.4 35.1 45.4 49.9 28.9 29.1 16.5
Skin moisture
Increment
16.3 13.9 12.2 11.3 10.3 20.1 25.2 4.0 4.1 -8.6
Growth rate 66.5% 55.2% 49.0% 45.0% 41.5% 79.5% 102% 16.1% 16.4% -34.3%

Skin moisture increase rate (control is better when SDS aqueous solution is applied and skin moisture increase rate is higher)

panel Example
2-1
Example
2-2
Example
2-3
Example
2-4
Example
2-5
Example
2-6
Example
2-7
Comparative Example
2-1
Comparative Example
2-2
control
Early
Measure
220 228 226 230 226 221 229 227 225 229
final
Measure
218 226 225 229 226 215 219 256 253 285
Erythema
Variation
-2 -2 -One -One 0 -6 -10 29 28 56
Growth rate -0.9% -0.9% -0.4% -0.4% 0% -2.7% -4.36% 12.8% 12.4% 24.5%

Increase rate of erythema (control is better when SDS solution is applied, with less erythema growth rate)

panel Example
2-1
Example
2-2
Example
2-3
Example
2-4
Example
2-5
Example
2-6
Example
2-7
Comparative Example
2-1
Comparative Example
2-2
control
Early
Measure
15.3 15.6 15.3 15.2 15.4 15.2 15.1 15.1 15.0 15.2
final
Measure
15.6 16.1 16.0 16.1 17.0 15.3 15.2 21.2 21.0 25.6
Skin moisture
Variation
0.3 0.5 0.7 0.9 1.6 0.1 0.1 6.1 6.0 10.4
Loss rate 2.0% 3.2% 4.6% 5.9% 10.4% 0.7% 0.7% 40.4% 40% 68.4%

Percutaneous water loss rate (control is better when only SDS aqueous solution is applied, the smaller the percutaneous water loss rate is)

While the present invention has been particularly shown and described with reference to exemplary embodiments thereof, it is to be understood that the invention is not limited to the disclosed exemplary embodiments, but, on the contrary, is intended to cover various modifications and equivalent arrangements included within the spirit and scope of the appended claims. In addition, many modifications may be made to adapt a particular situation and material to the teachings of the invention without departing from the essential scope thereof. Accordingly, the protection scope of the present invention should not be construed as being limited to the particular embodiments disclosed as the best mode contemplated for carrying out the invention but to cover all embodiments falling within the scope of the appended claims.

Claims (14)

Preparing a cationic guar gum; And
Modifying the cationic guar gum with a polymer having a phosphorylcholine group and a silane group; &Lt; / RTI &gt; wherein the cationic modified guar gum is obtained by the method of claim 1.
The method according to claim 1,
The polymer having a phosphorylcholine group and a silane group,
A process for producing a cationically modified guar gum obtained by copolymerizing a phosphorylcholine-based compound represented by the following formula (1) and an organosilane having an unsaturated group.
[Chemical Formula (1)
Figure pat00004

(Wherein X represents a divalent organic residue and Z represents a hydrogen atom or R 5 -O-CO- wherein R 5 represents a hydrogen atom, an alkyl group having 1 to 10 carbon atoms or a hydroxy group having 1 to 10 carbon atoms, R 1 represents a hydrogen atom or a hydrocarbon group having 1 to 5 carbon atoms, and R 2 , R 3 and R 4 are the same or different from each other and represent a hydrogen atom or an alkyl group having 1 to 20 carbon atoms, and Y represents an alkyleneoxy group having 1 to 20 carbon atoms. , M represents an integer of 1 to 20, and n represents an integer of 2 to 5.) In the formula, m represents an integer of 1 to 20, and n represents an integer of 2 to 5.)
3. The method of claim 2,
The unsaturated group-containing organosilane is preferably a cationic modified guar gum which is (meth) acryloxypropyltrimethoxysilane, vinyltrimethoxysilane or vinyltriethoxysilane. Way.
3. The method of claim 2,
Wherein the formula (1) is represented by the following formula (2).
(2)
Figure pat00005

(2), Z represents a hydrogen atom or R 5 -O-CO- (wherein R 5 represents a hydrogen atom, an alkyl group having 1 to 10 carbon atoms or a hydroxyalkyl group having 1 to 10 carbon atoms), Y represents R 1 is a hydrogen atom or a hydrocarbon group having 1 to 5 carbon atoms, R 2 , R 3 and R 4 are the same or different and each is a hydrogen atom, an alkylene group having 1 to 6 carbon atoms , M is an integer of 1 to 20, and n is an integer of 2 to 5.)
The method according to claim 1,
Wherein the cationic guar gum black water-soluble guar gum is cationized by treating with a cationizing agent to prepare a cationic modified guar gum.
3. The method of claim 2,
In the copolymerization of the phosphorylcholine-based compound and the unsaturated group-containing organosilane, the content of the phosphorylcholine-based compound as a whole monomer is 90 to 10% by weight and the content of the organosilane having an unsaturated group is 10 to 90% Method of manufacturing guar gum.
6. The method of claim 5,
Wherein the amount of the polymer having phosphorylcholine group and silane group used is 0.05 to 10.0% by weight as an effective component relative to the water-soluble guar gum.
3. The method of claim 2,
The phospholylcholine-based compound may be at least one selected from the group consisting of 2 - ((meth) acryloyloxy) ethyl-2 '- (trimethylammonio) ethyl phosphate, 3 - ((meth) acryloyloxy) (Trimethylammonio) ethylphosphate, 5 - ((meth) acryloyloxy) pentyl-2 '- (trimethylammonio) ethylphosphate, (Meth) acryloyloxy) ethyl-2 '- (triethylammonio) ethylphosphate, 2 - ((meth) acryloyloxy) , 2 - ((meth) acryloyloxy) ethyl-2 '(tributylammonio) ethylphosphate, 2- 2 - ((trimethylammonio) ethylphosphate, 2 - ((meth) acryloyloxy) propyl-2 ' ((Meth) acryloyloxy 2 '- (trimethylammonio) ethylphosphate, 2- ((meth) acryloyloxy) hexyl-2' (Trimethylammonio) ethyl phosphate, 2- (allyloxy) ethyl-2 '- (trimethylammonio) ethylphosphate, 2- (p-vinylbenzyloxy) ethyl-2 '- (trimethylammonio) ethylphosphate, 2- (styryloxy) ethyl- 2 '- (trimethylammonio) ethylphosphate, 2- (vinyloxycarbonyl) ethyl-2' - (trimethylammonio) ethylphosphate, 2- (allyloxycarbonyl) ethyl- (Trimethylammonio) ethylphosphate, 2- (acryloylamino) ethyl-2 '- (trimethylammonio) ethylphosphate, 2- Car 2'- (trimethylammonio) ethyl-2 '- (trimethylammonio) ethylphosphate, 2- (butanoyloxy) ethyl- (2'-trimethylammonioethylphosphorylethyl) fumarate, butyl- (2'-trimethylammonioethylphosphorylethyl) fumarate, hydroxyethyl- (2'-trimethyl Trimethylammonioethylphosphorylethyl) fumarate, hydroxy- (2 '-trimethylammonioethylphosphorylethyl) fumarate, butyl (2'- -Trimethylammonioethylphosphorylethyl) fumarate as a cationic modified guar gum.
A cationic modified guar gum prepared by the process of any one of claims 1 to 8.
10. The method of claim 9,
Cationic modified guar gum, formulated in powder or sheet form.
A hair care composition comprising the cationic modified guar gum of claim 9 as an active ingredient.
12. The method of claim 11,
Wherein the amount of cationic modified guar gum in the composition is 0.01 to 5% by weight based on the total weight of the composition.
A composition for skin care comprising the cationic modified guar gum of claim 9 as an active ingredient.
14. The method of claim 13,
Wherein the amount of cationic modified guar gum in the composition is 0.01 to 2% by weight based on the total weight of the composition.
KR1020130059859A 2013-05-27 2013-05-27 Cationic gua gum modified with polymer having phosphorylcholine-like groups and silane groups, and their cosmetic Formulations KR20140139337A (en)

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* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN109937500A (en) * 2017-02-03 2019-06-25 富士胶片和光纯药株式会社 Electrode of lithium cell adhesive composition and the electrode for having used the adhesive composition
WO2020213524A1 (en) * 2019-04-15 2020-10-22 日油株式会社 Phosphoryl-choline-group-containing vinyl monomer
CN114213554A (en) * 2021-12-31 2022-03-22 昆山京昆油田化学科技有限公司 Purification method of cationic guar gum
CN116099492A (en) * 2023-02-08 2023-05-12 杭州尚善若水环保科技有限公司 Mineral agent for water recovery system and preparation method and application thereof

Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN109937500A (en) * 2017-02-03 2019-06-25 富士胶片和光纯药株式会社 Electrode of lithium cell adhesive composition and the electrode for having used the adhesive composition
EP3579312A4 (en) * 2017-02-03 2020-01-08 FUJIFILM Wako Pure Chemical Corporation Binder agent composition for lithium battery electrode, and electrode using same
WO2020213524A1 (en) * 2019-04-15 2020-10-22 日油株式会社 Phosphoryl-choline-group-containing vinyl monomer
CN114213554A (en) * 2021-12-31 2022-03-22 昆山京昆油田化学科技有限公司 Purification method of cationic guar gum
CN116099492A (en) * 2023-02-08 2023-05-12 杭州尚善若水环保科技有限公司 Mineral agent for water recovery system and preparation method and application thereof
CN116099492B (en) * 2023-02-08 2023-09-12 杭州尚善若水环保科技有限公司 Mineral agent for water recovery system and preparation method and application thereof

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