Methods for making and using skin moisturizing preparations

A cationic dextran polymer with quaternary ammonium groups is used in a skin moisturizing formulation to address the need for cost-effective moisture retention in skin care products, offering a viable alternative to high-cost humectants.

JP7763189B2Active Publication Date: 2025-10-31ROHM & HAAS CO +2
View PDF 5 Cites 0 Cited by

Patent Information

Application Number
JP2022571131
Authority / Receiving Office
JP · JP
Patent Type
Patents
Current Assignee / Owner
Priority Date
2020-06-23
Filing Date
2021-06-18
Publication Date
2025-10-31
Estimated Expiration
2041-06-18

AI Technical Summary

Technical Problem

There is a need for effective and lower-cost moisturizing materials in skin care formulations that can absorb and retain moisture, as existing humectants like hyaluronic acid are limited by high cost and usage in premium products.

Method used

A method involving a dermatologically acceptable vehicle combined with a cationic dextran polymer functionalized with a quaternary ammonium group to form a skin moisturizing formulation, which includes 0.05 to 10% of the moisturizing agent by weight.

Benefits of technology

The formulation effectively moisturizes the skin by absorbing and retaining moisture, providing a cost-effective alternative to high-cost humectants, suitable for various skin care products including leave-on formulations.

✦ Generated by Eureka AI based on patent content.

Smart Images

  • Figure 0007763189000001
    Figure 0007763189000001
  • Figure 0007763189000002
    Figure 0007763189000002
  • Figure 0007763189000003
    Figure 0007763189000003
Patent Text Reader

Abstract

A method of making a skin moisturizing formulation is provided, the method comprising: providing a dermatologically acceptable vehicle; selecting a skin moisturizing agent based on its ability to absorb and retain moisture, wherein the selected skin moisturizing agent is a cationic dextran polymer including a dextran polymer functionalized with a quaternary ammonium group; providing the selected skin moisturizing agent; and combining the dermatologically acceptable vehicle and the skin moisturizing agent to form a skin moisturizing formulation, wherein the skin moisturizing formulation contains 0.05 to 10% by weight of the skin moisturizing agent based on the weight of the skin moisturizing formulation. A method of moisturizing skin is also provided.
Need to check novelty before this filing date? Find Prior Art

Description

[Technical Field]

[0001] The present invention relates to a method of making a skin moisturizing formulation. Specifically, the present invention relates to a method of making a skin moisturizing formulation, comprising: providing a dermatologically acceptable vehicle; selecting a skin moisturizer based on its ability to absorb and retain moisture, wherein the selected skin moisturizer is a cationic dextran polymer including a dextran polymer functionalized with a quaternary ammonium group; providing the selected skin moisturizer; and combining the dermatologically acceptable vehicle and the skin moisturizer to form a skin moisturizing formulation, wherein the skin moisturizing formulation contains 0.05 to 10% by weight of the skin moisturizing agent based on the weight of the skin moisturizing formulation. [Background technology]

[0002] Since most consumers suffer from dry skin to some extent, moisturizing ingredients are important components in many skin care formulations. A good moisturizer can reduce sensitive and dry skin, decrease skin irritation, and slow the aging process. There are two general classes of materials used to combat dry skin: occlusive agents and humectants. Occlusive agents, such as petrolatum and silicone oil, function to inhibit the loss of skin's natural moisture by forming a barrier between the epidermis and the surrounding environment. Humectants, which are hygroscopic substances that form hydrogen bonds with water molecules, hydrate the skin by attracting water molecules from the environment to the skin, thereby helping to moisturize dry skin.

[0003] Commonly used humectants include hyaluronic acid and sodium hyaluronate, biopolymers found in mammalian connective, epithelial, and neural tissues. Hyaluronic acid is a high-molecular-weight (1,000 kDa–3,000 kDa) anionic polysaccharide composed of repeating disaccharide units of D-glucuronic acid and n-acetyl-D-glucosamine. Compared to other humectants, hyaluronic acid is less affected by the environment. Due to its high hygroscopicity (capable of absorbing 1,000 times its own weight in water) and non-greasy feel, hyaluronic acid is one of the most common and highly desirable humectants in skin care formulations. Nevertheless, due to its high cost, its use is limited to premium skin care leave-on products.

[0004] One alternative type of skin moisturizing material is disclosed by Au et al. in U.S. Patent Application Publication No. 20120295983. Au et al. teach a composition comprising a cationic ammonium compound and a metal chelating agent, where the metal chelating agent prevents the generation of nitrogen-containing groups from the cationic ammonium compound in the composition.

[0005] Nevertheless, there is a continuing need for effective, lower cost moisturizing materials useful in skin care formulations. Summary of the Invention

[0006] The present invention provides a method of making a skin moisturizing formulation, the method comprising: providing a dermatologically acceptable vehicle; selecting a skin moisturizing agent based on its ability to absorb and retain moisture, wherein the selected skin moisturizing agent is a cationic dextran polymer including a dextran polymer functionalized with a quaternary ammonium group; providing the selected skin moisturizing agent; and combining the dermatologically acceptable vehicle and the skin moisturizing agent to form a skin moisturizing formulation, wherein the skin moisturizing formulation contains 0.05 to 10% by weight of the skin moisturizing agent based on the weight of the skin moisturizing formulation.

[0007] The present invention provides a skin moisturizing formulation prepared according to the method of the present invention.

[0008] The present invention provides a method of moisturizing skin, comprising providing a skin moisturizing formulation prepared according to the method of the present invention and applying the skin moisturizing formulation to mammalian skin. DETAILED DESCRIPTION OF THE INVENTION

[0009] The inventors have surprisingly discovered an effective method of making a skin moisturizing formulation, wherein the resulting skin moisturizing formulation comprises a skin moisturizer, the skin moisturizer being selected based on its ability to absorb and retain moisture.

[0010] Unless otherwise indicated, ratios, percentages, parts, etc. are by weight.

[0011] As used herein, unless otherwise specified, "molecular weight" or M w The phrase "weight average molecular weight" refers to weight average molecular weight as determined conventionally using gel permeation chromatography (GPC) and dextran standards. GPC techniques are described in detail in "Modern Size Exclusion Chromatography," W.W. Yau, J.J. Kirkland, D.D.Bly; Wiley-Interscience, 1979, and in "A Guide to Materials Characterization and Chemical Analysis," J.P. Sibilia; VCH, 1988, pp. 81-84. Molecular weights are reported herein in units of Daltons, or equivalently, g / mol.

[0012] The term "dermatologically acceptable" as used herein and in the appended claims refers to ingredients typically used for topical application to the skin, and is intended to emphasize that materials that are toxic when present in amounts typically found in skin care compositions are not contemplated as part of the present invention.

[0013] Preferably, the skin moisturizing formulation prepared by the method of the present invention is selected from the group consisting of leave-on formulations and rinse-off formulations. More preferably, the skin moisturizing formulation prepared by the method of the present invention is selected from the group consisting of lotions (e.g., moisturizing lotions), creams (e.g., blemish balm (BB) creams, dynamic do-all (DD) creams, anti-wrinkle creams), serums, gels, gel creams, roll-on formulations, sticks, mousses, sprays (aerosol or non-aerosol), fabrics or wipes (e.g., formulations applied to nonwovens), toners, masks, sunscreens, color cosmetics, foundations, powders, antiperspirants, lipsticks, lip glosses, deodorants, baby care formulations, hand sanitizers, hand soaps, body washes, facial cleansers, and soap bars. Most preferably, the skin moisturizing formulation prepared by the method of the present invention is a leave-on formulation selected from the group consisting of color cosmetics, sunscreens, lotions, and creams.

[0014] Preferably, the method for preparing the skin moisturizing formulation of the present invention includes providing a dermatologically acceptable vehicle, selecting a skin moisturizer based on its ability to absorb and retain moisture, where the selected skin moisturizer is a cationic dextran polymer including a dextran polymer functionalized with a quaternary ammonium group, providing the selected skin moisturizer, and combining the dermatologically acceptable vehicle and the skin moisturizer to form a skin moisturizing formulation, the skin moisturizing formulation containing 0.05 to 10 wt.% of the skin moisturizer based on the weight of the skin moisturizing formulation. Preferably, the ability of the skin moisturizer to absorb and retain moisture is determined based on the experimental procedures described herein in the Examples.

[0015] Preferably, the method for making the skin moisturizing formulation of the present invention comprises providing a dermatologically acceptable vehicle, the dermatologically acceptable vehicle comprising at least one of water, an emollient, a fatty acid, a fatty alcohol, a thickener, and a combination thereof. More preferably, the method for making the skin moisturizing formulation of the present invention comprises providing a dermatologically acceptable vehicle, the dermatologically acceptable vehicle comprising at least one of water, an emollient, a fatty acid, a fatty alcohol, a thickener, and a combination thereof, the dermatologically acceptable vehicle being in the form of an emulsion, cream, aqueous solution, oil, ointment, paste, gel, lotion, milk, foam, suspension, or powder. Most preferably, the method of making the skin moisturizing formulation of the present invention comprises providing a dermatologically acceptable vehicle, the dermatologically acceptable vehicle comprising at least one of water, an emollient, a fatty acid, a fatty alcohol, a thickener, and combinations thereof, the dermatologically acceptable vehicle being in the form of an emulsion, a cream, an aqueous solution, an oil, an ointment, a gel, a lotion, a milk, a foam, and a suspension.

[0016] Preferably, the method for preparing the skin moisturizing formulation of the present invention comprises providing a dermatologically acceptable vehicle, and the formed skin moisturizing formulation contains 1 to 99.95 wt % (preferably 70 to 95 wt %, more preferably 80 to 90 wt %) of the dermatologically acceptable vehicle based on the weight of the skin moisturizing formulation.

[0017] When the dermatologically acceptable vehicle provided contains water, the resulting skin moisturizing formulation preferably contains 5 to 95 wt % (preferably 20 to 70 wt %, more preferably 35 to 60 wt %) of water based on the weight of the skin moisturizing formulation.

[0018] Preferably, the dermatologically acceptable vehicle provided contains an emollient, and the emollient material used may be in the form of silicone oil, natural or synthetic ester, and hydrocarbon. Preferably, when the dermatologically acceptable vehicle provided contains an emollient, the formed skin moisturizing formulation preferably contains 0.1 to 95 wt % (more preferably 1 to 50 wt %) of the emollient based on the weight of the skin moisturizing formulation.

[0019] Silicone oils can be divided into volatile silicones and non-volatile silicones. Volatile silicone oils are silicones that have a measurable vapor pressure at ambient temperature. Such volatile silicone oils are preferably selected from cyclic (cyclomethicone) or linear polydimethylsiloxanes containing 3 to 9 (preferably 4 to 5) silicone atoms per molecule. Non-volatile silicone oils include polyalkylsiloxanes, polyalkylarylsiloxanes, and polyethersiloxane copolymers. Such non-volatile silicone oils include, for example, those having a viscosity of 5 x 10 at 25°C. -6 ~0.1m 2 / s (preferably 1 × 10 at 25 °C) -5 ~4×10 -4 m 2 Polydimethylsiloxanes having a viscosity of 1000 psi / s are also suitable. Another class of non-volatile silicones are emulsifying and non-emulsifying silicone elastomers (e.g., dimethicone / vinyl dimethicone crosspolymers available from Dow Silicones). Yet another class of non-volatile silicones are waxes (e.g., dimethicone PEG-8 laurate).

[0020] Ester emollients include (i) alkyl esters of saturated fatty acids having 10 to 24 carbon atoms (e.g., behenyl neopentanoate, isononyl isonanonoate, isopropyl myristate, and octyl stearate), (ii) ether-esters such as fatty acid esters of ethoxylated saturated fatty alcohols, (iii) polyhydric alcohol esters (e.g., ethylene glycol mono- and di-fatty acid esters, diethylene glycol mono- and di-fatty acid esters, polyethylene glycol mono- and di-fatty acid esters, propylene glycol mono- and di-fatty acid esters, polypropylene glycol monostearate, ethoxylated propylene glycol monostearate, glyceryl mono- and di-fatty acid esters, poly (iv) wax esters (e.g., beeswax, spermaceti, and tribehenin wax); (v) sugar esters or fatty acids (e.g., sucrose polybehenate and sucrose polycottenitate); (vi) glycerol polyfatty acid esters, ethoxylated glyceryl monostearate, 1,3-butylene glycol monostearate, 1,3-butylene glycol distearate, polyoxyethylene polyol fatty acid esters, sorbitan fatty acid esters, and polyoxyethylene sorbitan fatty acid esters are satisfactory polyhydric alcohol esters; (vii) wax esters (e.g., beeswax, spermaceti, and tribehenin wax); (viii) sugar esters or fatty acids (e.g., sucrose polybehenate and sucrose polycottenitate); (vi) natural ester emollients, including those based on mono-, di-, and triglycerides (e.g., sunflower seed oil, coconut oil, cottonseed oil, borage oil, borage seed oil, evening primrose oil, castor and hydrogenated castor oil, rice bran oil, soybean oil, olive oil, safflower oil, shea butter, jojoba oil, and combinations thereof); and (vii) animal-derived emollients (e.g., lanolin oil and lanolin derivatives).

[0021] Examples of hydrocarbons include petrolatum, mineral oil, squalane, squalene, isohexadecane, isododecane, C 10~26 Alkane, C 11~13 Mention may be made of isoparaffins, polybutenes, and mixtures thereof.

[0022] Fatty acids include those having 10 to 36 carbon atoms per molecule (e.g., pelargonic acid, lauric acid, myristic acid, palmitic acid, oleic acid, linoleic acid, linolenic acid, stearic acid, isostearic acid, hydroxystearic acid, and behenic acid).

[0023] Fatty alcohols can include those having 10 to 36 carbon atoms per molecule (eg, stearyl alcohol, lauryl alcohol, myristyl alcohol, cetyl alcohol, and oleyl alcohol).

[0024] Examples of thickeners include salts (e.g., sodium chloride), acrylates (e.g., acrylate copolymers and crosslinked acrylates), polyacrylamides, cellulose or cellulose derivatives (e.g., sodium carboxymethylcellulose, hydroxypropylmethylcellulose, hydroxypropylcellulose, hydroxyethylcellulose, ethylcellulose, and hydroxyethylmethylcellulose), natural gums (e.g., guar, xanthan, sclerotium, carrageenan, pectin), and inorganic substances (e.g., clays such as bentonite and hectorite, fumed silica, talc, calcium carbonate, and silicates such as magnesium aluminum silicate). The amount of thickener contained in the skin moisturizing formulation may be in the range of 0.0001 to 10 wt. % (preferably 0.001 to 1 wt. %, more preferably 0.01 to 0.5 wt. %) based on the weight of the skin moisturizing formulation.

[0025] Preferably, the method for making a skin moisturizing formulation of the present invention comprises selecting a skin moisturizer based on its ability to absorb and retain water, wherein the selected skin moisturizer is a cationic dextran polymer, including a dextran polymer functionalized with a quaternary ammonium group. More preferably, the method for making a skin moisturizing formulation of the present invention comprises selecting a skin moisturizer based on its ability to absorb and retain water, wherein the selected skin moisturizer is a cationic dextran polymer, including a dextran polymer functionalized with a quaternary ammonium group, wherein the skin moisturizer has a Kjeldahl nitrogen content, TKN, corrected for ash and volatiles (measured using a Buchi KjelMaster K-375 autoanalyzer and corrected for volatiles and ash, measured as described in ASTM Method D-2364), of 0.5 to 4.0 wt. % (preferably, 0.75 to 3.25 wt. %, more preferably, 0.9 to 2.6 wt. %, and most preferably, 1.0 to 2.0 wt. %).

[0026] Preferably, the method of making the skin moisturizing formulation of the present invention comprises selecting a skin moisturizer based on its ability to absorb and retain water, wherein the selected skin moisturizer is a cationic dextran polymer, including a dextran polymer functionalized with a quaternary ammonium group, the dextran polymer having a weight average molecular weight M of 75,000 to 2,000,000 daltons (preferably 100,000 to 1,000,000 daltons, more preferably 125,000 to 750,000 daltons, even more preferably 130,000 to 600,000 daltons, and most preferably 145,000 to 525,000 daltons). W It has.

[0027] Preferably, the method of making the skin moisturizing formulation of the present invention comprises selecting a skin moisturizer based on its ability to absorb and retain moisture, wherein the selected skin moisturizer is a cationic dextran polymer, including a dextran polymer functionalized with quaternary ammonium groups, and wherein the dextran polymer is a branched dextran polymer. More preferably, the method for preparing the skin moisturizing formulation of the present invention includes selecting a skin moisturizer based on its ability to absorb and retain moisture, wherein the selected skin moisturizer is a cationic dextran polymer, including a dextran polymer functionalized with a quaternary ammonium group, the dextran polymer including a branched dextran polymer, the branched dextran polymer including a plurality of glucose structural units, wherein 90 to 98 mol % (preferably 92.5 to 97.5 mol %, more preferably 93 to 97 mol %, and most preferably 94 to 96 mol %) of the glucose structural units are connected by α-D-1,6 bonds and 2 to 10 mol % (preferably 2.5 to 7.5 mol %, more preferably 3 to 7 mol %, and most preferably 4 to 6 mol %) of the glucose structural units are connected by α-1,3 bonds. Most preferably, the method for making the skin moisturizing formulation of the present invention comprises selecting a skin moisturizer based on its ability to absorb and retain moisture, wherein the selected skin moisturizer is a cationic dextran polymer comprising a dextran polymer functionalized with a quaternary ammonium group, the dextran polymer being a branched dextran polymer comprising a plurality of glucose structural units, wherein 90 to 98 mol % (preferably 92.5 to 97.5 mol %, more preferably 93 to 97 mol %, and most preferably 94 to 96 mol %) of the glucose structural units are connected by α-D-1,6 bonds and 2 to 10 mol % (preferably 2.5 to 7.5 mol %, more preferably 3 to 7 mol %, and most preferably 4 to 6 mol %) of the glucose structural units are connected by α-1,3 bonds, according to formula (i):

[0028] [ka] In the formula, R is hydrogen, C 1~4Alkyl and hydroxy C 1~4 The alkyl groups are selected from dextran polymer backbones with an average branch length of no more than 3 anhydroglucose units.

[0029] Preferably, the method for making the skin moisturizing preparation of the present invention comprises selecting a skin moisturizing agent based on its ability to absorb and retain moisture, and the selected skin moisturizing agent is a cationic dextran polymer, comprising a dextran polymer functionalized with quaternary ammonium groups, and the dextran polymer contains less than 0.01 wt% alternan based on the weight of the dextran polymer.More preferably, the method for making the skin moisturizing preparation of the present invention comprises selecting a skin moisturizing agent based on its ability to absorb and retain moisture, and the selected skin moisturizing agent is a cationic dextran polymer, comprising a dextran polymer functionalized with quaternary ammonium groups, and the dextran polymer contains less than 0.001 wt% alternan based on the weight of the dextran polymer.Most preferably, the method for making the skin moisturizing preparation of the present invention comprises selecting a skin moisturizing agent based on its ability to absorb and retain moisture, and the selected skin moisturizing agent is a cationic dextran polymer, comprising a dextran polymer functionalized with quaternary ammonium groups, and the dextran polymer contains less than detectable alternan.

[0030] Preferably, the method of making the skin moisturizing formulation of the present invention comprises selecting a skin moisturizer based on its ability to absorb and retain moisture, wherein the selected skin moisturizer is a cationic dextran polymer comprising a dextran polymer functionalized with a quaternary ammonium group, wherein the quaternary ammonium moiety is selected from the group consisting of at least one of the following: (a) a dextran crosslinking group of formula (A):

[0031] [ka] and (b) a quaternary ammonium group of formula (B)

[0032] [ka] During the ceremony,

[0033] [ka] are the pendant oxygens on the dextran polymer, and each R 1 are independently substituted or unsubstituted C 1~6 alkyl groups ("substituted" means that the group in question contains at least one of a halogen, a hydroxy group, an amino group, or a carboxy group) (preferably, each R 1 are independently unsubstituted C 1~6 alkyl groups, and more preferably, each R 1 are independently selected from the group consisting of methyl, ethyl, propyl, isopropyl, butyl, isobutyl, tert-butyl, sec-butyl, pentyl, isopentyl, neopentyl, hexyl, and isohexyl, and even more preferably, each R 1 are independently selected from the group consisting of methyl, ethyl, propyl, isopropyl, butyl, isobutyl, tert-butyl, and sec-butyl groups, and even more preferably, each R 1 are independently selected from the group consisting of methyl, ethyl, propyl, and isopropyl groups, and even more preferably, each R 1 are independently selected from the group consisting of methyl and ethyl groups, and most preferably, each R 1 is a methyl group), and each R 2 independently, C 1~6 alkanediyl groups (preferably, each R 2 independently, C 1~4 alkanediyl groups, and more preferably, each R 2 independently, C 1~2 alkanediyl groups, and most preferably each R 2 is a -CH2- group), and Y is a divalent bridging group (preferably, Y is C1~6 Alkanediyl group and -R 3 -OR 4 - groups, and more preferably, Y is a divalent bridging group selected from the group consisting of -R 3 -OR 4 -), R 3 and R 4 independently, C 1~6 alkanediyl groups (preferably R 3 and R 4 independently, C 1~4 alkanediyl groups, more preferably R 3 and R 4 independently, C 1~3 alkanediyl groups, most preferably R 3 and R 4 are both -CH2CH2- groups) (preferably, R 3 and R 4 are the same), and X is a divalent linking group that attaches the quaternary ammonium moiety to a pendant oxygen on the dextran polymer (preferably, X is selected from divalent hydrocarbon groups, which may be optionally substituted (e.g., with hydroxy, alkoxy, ether groups); more preferably, X is -CHCH(OR 6 )CH2- group (wherein, R 6 is hydrogen and C 1~4 alkyl groups), most preferably X is a -CHCH(OH)CH- group), and each R 5 independently, C 1~22 alkyl groups (preferably, each R 5 independently, C 1~3 Alkyl groups and C 6~22 alkyl groups, and more preferably, each R 5 are independently selected from the group consisting of methyl, ethyl, and lauryl groups, and most preferably, each R 5 is a methyl group).

[0034] More preferably, the method of making the skin moisturizing formulation of the present invention comprises selecting a skin moisturizer based on its ability to absorb and retain moisture, wherein the selected skin moisturizer is a cationic dextran polymer comprising a dextran polymer functionalized with a quaternary ammonium group, wherein the quaternary ammonium moiety is selected from the group consisting of at least one of (a) a dextran crosslinking group of formula (A) and (b) a quaternary ammonium group of formula (B), wherein the dextran crosslinking group of formula (A) is of formula (C):

[0035] [ka] The quaternary ammonium group of formula (B) is of formula (D):

[0036] [ka] During the ceremony,

[0037] [ka] are the pendant oxygens on the dextran polymer, and each R 1 are independently substituted or unsubstituted C 1~6 alkyl groups ("substituted" means that the group in question contains at least one moiety selected from halogen, hydroxy, amino, or carboxy groups) (preferably, each R 1 are independently unsubstituted C 1~6 alkyl groups, and more preferably, each R 1 are independently selected from the group consisting of methyl, ethyl, propyl, isopropyl, butyl, isobutyl, tert-butyl, sec-butyl, pentyl, isopentyl, neopentyl, hexyl, and isohexyl, and even more preferably, each R 1 are independently selected from the group consisting of methyl, ethyl, propyl, isopropyl, butyl, isobutyl, tert-butyl, and sec-butyl groups, and even more preferably, each R 1are independently selected from the group consisting of methyl, ethyl, propyl, and isopropyl groups, and even more preferably, each R 1 are independently selected from the group consisting of methyl and ethyl groups, and most preferably, each R 1 is a methyl group), and each R 2 independently, C 1~6 alkanediyl groups (preferably, each R 2 is C 1~4 More preferably, each R 2 is C 1~2 alkanediyl groups, and most preferably, each R 2 is a -CH2- group), and R 3 and R 4 independently, C 1~6 alkanediyl groups (preferably R 3 and R 4 independently, C 1~4 alkanediyl groups, more preferably R 3 and R 4 independently, C 1-3 alkanediyl groups, most preferably a -CH2CH2- group) (preferably R 3 and R 4 are the same), and each R 6 is hydrogen and C 1~4 alkyl groups (preferably R 6 is hydrogen), and each R 7 are independently selected from the group consisting of a methyl group, an ethyl group, and a lauryl group (preferably a methyl group).

[0038] Even more preferably, the method of making the skin moisturizing formulation of the present invention comprises selecting a skin moisturizer based on its ability to absorb and retain moisture, wherein the selected skin moisturizer is a cationic dextran polymer comprising a dextran polymer functionalized with a quaternary ammonium group, wherein the quaternary ammonium moiety is selected from the group consisting of at least one of: (a) a dextran crosslinking group of formula (A) and (b) a quaternary ammonium group of formula (B), wherein the dextran crosslinking group of formula (A) is

[0039] [ka] and mixtures thereof, and the quaternary ammonium group of formula (B) is of formula (D), wherein:

[0040] [ka] are the pendant oxygens on the dextran polymer, and each R 6 is hydrogen and C 1~4 alkyl groups (preferably R 6 is hydrogen), and each R 7 are independently selected from the group consisting of a methyl group, an ethyl group, and a lauryl group (preferably a methyl group).

[0041] Most preferably, the method of making the skin moisturizing formulation of the present invention comprises selecting a skin moisturizer based on its ability to absorb and retain moisture, wherein the selected skin moisturizer is a cationic dextran polymer comprising a dextran polymer functionalized with a quaternary ammonium group, the quaternary ammonium moiety being selected from the group consisting of (b) a quaternary ammonium group of formula (D), wherein:

[0042] [ka] are the pendant oxygens on the dextran polymer, and each R 6 is hydrogen and C 1~4alkyl groups (preferably R 6 is hydrogen), and each R 7 are independently selected from the group consisting of a methyl group, an ethyl group, and a lauryl group (preferably a methyl group).

[0043] Preferably, the method of making the skin moisturizing formulation of the present invention comprises selecting a skin moisturizer based on its ability to absorb and retain moisture, wherein the selected skin moisturizer is a cationic dextran polymer, including a dextran polymer functionalized with a quaternary ammonium group, and wherein the provided skin moisturizer comprises <0.001 meg / gram (preferably <0.0001 meq / gram, more preferably less than 0.00001 meq / gram, and most preferably below the detectable limit) of aldehyde functional groups.

[0044] Preferably, the method of making the skin moisturizing formulation of the present invention comprises selecting a skin moisturizer based on its ability to absorb and retain moisture, wherein the selected skin moisturizer is a cationic dextran polymer, including a dextran polymer functionalized with a quaternary ammonium group, and wherein the provided skin moisturizer comprises <0.1% (preferably <0.01%, more preferably less than 0.001%, and most preferably below the detectable limit) β-1,4 linkages between individual glucose units in the deposition aid polymer.

[0045] Preferably, the method of making the skin moisturizing formulation of the present invention comprises selecting a skin moisturizer based on its ability to absorb and retain moisture, wherein the selected skin moisturizer is a cationic dextran polymer, including a dextran polymer functionalized with a quaternary ammonium group, and wherein the provided skin moisturizer comprises <0.1% (preferably <0.01%, more preferably less than 0.001%, and most preferably below the detectable limit) β-1,3 linkages between individual glucose units in the deposition aid polymer.

[0046] Preferably, the method of making the skin moisturizing formulation of the present invention comprises selecting a skin moisturizer based on its ability to absorb and retain moisture, wherein the selected skin moisturizer is a cationic dextran polymer comprising a dextran polymer functionalized with a quaternary ammonium group, and wherein the provided skin moisturizer comprises a silicone containing <0.001 meq / gram (preferably <0.0001 meq / gram, more preferably less than 0.00001 meq / gram, most preferably below the detectable limit) of functional groups.

[0047] Preferably, the method of making the skin moisturizing formulation of the present invention comprises selecting a skin moisturizer based on its ability to absorb and retain moisture, wherein the selected skin moisturizer is a cationic dextran polymer, including a dextran polymer functionalized with a quaternary ammonium group, and wherein the provided skin moisturizer comprises <0.1 mol % (preferably, 0 to <0.01 mol %, more preferably, 0 to less than 0.001 mol %, and most preferably, 0 to below the detection limit) of reactive siloxane structural units, wherein the reactive siloxane structural units comprise Si—O moieties. More preferably, the method of making the skin moisturizing formulation of the present invention comprises selecting a skin moisturizer based on its ability to absorb and retain moisture, wherein the selected skin moisturizer is a cationic dextran polymer, including a dextran polymer functionalized with a quaternary ammonium group, wherein the provided skin moisturizer comprises <0.1 mol % (preferably, 0 to <0.01 mol %, more preferably, 0 to less than 0.001 mol %, and most preferably, 0 to below the limit of detection) of reactive siloxane structural units, wherein the reactive siloxane structural units comprise Si—O moieties, wherein the reactive siloxane is a polymer that may contain one or more functional moieties selected from the group consisting of amino, amido, alkoxy, hydroxy, polyether, carboxy, hydride, mercapto, phosphate sulfate, and / or quaternary ammonium moieties, wherein these moieties may be directly attached to the siloxane backbone (i.e., pendant) via divalent alkylene groups or may be part of the backbone.

[0048] Preferably, the method of making the skin moisturizing formulation of the present invention includes selecting a skin moisturizing agent based on its ability to absorb and retain moisture, wherein the selected skin moisturizing agent is a cationic dextran polymer, including a dextran polymer functionalized with a quaternary ammonium group, and the formed skin moisturizing formulation comprises 0.05 to 10 wt. % (preferably, 0.1 to 5 wt. %, more preferably, 0.2 to 2.5 wt. %, and most preferably, 0.35 to 1.5 wt. %) of the provided skin moisturizing agent, based on the weight of the skin moisturizing formulation.

[0049] Preferably, the method for making the skin moisturizing formulations of the present invention includes the step of adding an absorbent, anti-aging agent, anti-foaming agent, antibacterial agent, antioxidant (e.g., butylated hydroxytoluene), antistatic agent, astringent active agent, bioactive agent, bleaching agent, dermatologically acceptable personal care cleansing surfactant, chelating agent, colorant, desquamation promoter, emulsifier, enzyme, herbal extract, film former, foaming agent, foam booster, fragrance, hard particles, inorganic particles, oil, emollient, humectant, lubricant, natural ingredient, opacifier, pearlizing agent, chemical or physical exfoliant, penetrating agent, providing an additional ingredient selected from the group consisting of pH adjusters, thickeners, pigments, dyes, botanical extracts, preservatives (e.g., benzoic acid, sorbic acid, phenoxyethanol), propellants, proteins / amino acids, peptides, salts, sensory modifiers, silicone feel modifiers, skin lightening agents, anti-acne agents, anti-inflammatory agents, skin soothing agents, slip agents, soaps, soft particles, sun care agents, suspending agents, vitamins, waxes, and mixtures thereof; and combining the additional ingredient with a dermatologically acceptable vehicle and a skin moisturizer to form a skin moisturizing formulation.

[0050] Preferably, the method for making the skin moisturizing formulation of the present invention further comprises providing an antimicrobial agent and combining the antimicrobial agent with a dermatologically acceptable vehicle and a skin moisturizer to form a skin moisturizing formulation. More preferably, the method for making the skin moisturizing formulation of the present invention further comprises providing an antimicrobial agent and combining the antimicrobial agent with a dermatologically acceptable vehicle and a skin moisturizer to form a skin moisturizing formulation, wherein the antimicrobial agent is selected from the group consisting of phenoxyethanol, benzoic acid, benzyl alcohol, sodium benzoate, DMDM ​​hydantoin, 2-ethylhexylglyceryl ether, and isothiazolinone (e.g., methylchloroisothiazolinone, methylisothiazolinone).

[0051] Preferably, the method for making a skin moisturizing formulation of the present invention further comprises providing an antioxidant and combining the antioxidant with a dermatologically acceptable vehicle and a skin moisturizer to form a skin moisturizing formulation (preferably, the formed skin moisturizing formulation contains 0.000001 to 10 wt % of the antioxidant based on the weight of the skin moisturizing formulation). More preferably, the method for making a skin cleansing formulation of the present invention further comprises providing an antioxidant and combining the antioxidant with a dermatologically acceptable vehicle and a skin moisturizer to form a skin moisturizing formulation, the antioxidant being selected from the group consisting of butylated hydroxytoluene, lipoic acid, vitamins, herbal extracts (e.g., green tea), retinoxytrimethylsilane, dehydroepiandrosterone (DHEA), and combinations thereof (preferably, the formed skin moisturizing formulation contains 0.000001 to 10 wt % of the antioxidant based on the weight of the skin moisturizing formulation).

[0052] Preferably, the method of making the skin moisturizing formulation of the present invention further comprises providing an astringent active and combining the astringent active with a dermatologically acceptable vehicle and a skin moisturizer to form a skin moisturizing formulation (preferably, the formed skin moisturizing formulation comprises 0.5 to 50% by weight of the astringent active, based on the weight of the skin moisturizing formulation). More preferably, the method of making a skin moisturizing formulation of the present invention further comprises providing an astringent active and combining the astringent active with a dermatologically acceptable vehicle and a skin moisturizer to form a skin moisturizing formulation (preferably, the formed skin moisturizing formulation comprises 0.5 to 50% by weight of the astringent active, based on the weight of the skin moisturizing formulation), wherein the astringent active is selected from the group consisting of alcohol, citric acid, salicylic acid, alpha hydroxy acids, beta hydroxy acids (AHA acids), witch hazel, rose water, aloe vera, other herbal extracts, aluminum chlorohydrate, aluminum chlorhydrex, aluminum zirconium chlorohydrex glycinate, aluminum sulfate, zinc sulfate, zirconium and aluminum chlorohydroglycinate, zirconium hydroxychloride, zirconium and aluminum lactate, zinc phenolsulfonate, and mixtures thereof.

[0053] Preferably, the method of making a skin moisturizing formulation of the present invention further comprises providing a dermatologically acceptable personal care cleansing surfactant, and combining the dermatologically acceptable personal care cleansing surfactant with a dermatologically acceptable vehicle and a skin moisturizer to form a skin moisturizing formulation (preferably, the formed skin moisturizing formulation comprises 0.01 to 80 wt % (preferably, 5 to 50 wt %, more preferably, 7.5 to 35 wt %, and most preferably, 10 to 20 wt %) of the dermatologically acceptable personal care cleansing surfactant based on the weight of the skin moisturizing formulation). More preferably, the method of making a skin moisturizing formulation of the present invention further comprises providing a dermatologically acceptable personal care cleansing surfactant, and combining the dermatologically acceptable personal care cleansing surfactant with a dermatologically acceptable vehicle and a skin moisturizing agent to form a skin moisturizing formulation (preferably, the formed skin moisturizing formulation comprises 0.01 to 80 wt % (preferably, 5 to 50 wt %, more preferably, 7.5 to 35 wt %, and most preferably, 10 to 20 wt %) of the dermatologically acceptable personal care cleansing surfactant based on the weight of the skin moisturizing formulation), wherein the dermatologically acceptable personal care cleansing surfactant is selected from the group consisting of alkyl polyglucosides (e.g., lauryl glucoside, coco-glucoside, decyl glucoside), glycinates (e.g., Sodium cocoyl glycinate), glycolipids (e.g., sophorolipid, lamolipid), sultaine, surfactin, betaine (e.g., alkyl betaines such as cetyl betaine and amido betaines such as cocamidopropyl betaine), taurate (e.g., sodium methyl methyl cocoyl taurate), glutamate (e.g., sodium cocoyl glutamate), sarcosinate (e.g., sodium lauroyl sarcosinate), isethionate (e.g., sodium cocoyl isethionate, sodium lauroyl methyl isethionate), sulfoacetate (e.g., sodium lauryl sulfoacetate), alaninate (e.g., sodium cocoyl alaninate), amphoacetate (e.g., sodium cocoamphoacetate), sulfate (e.g., sodium laureth sulfate), sulfonate (e.g., C.14~16 sodium olefin sulfonate), succinates (e.g., disodium lauryl sulfosuccinate), and mixtures thereof.

[0054] Preferably, the method of making the skin moisturizing formulation of the present invention further comprises providing a colorant and combining the colorant with a dermatologically acceptable vehicle and a skin moisturizing agent to form a skin moisturizing formulation (preferably, the formed skin moisturizing formulation comprises 0.05 to 5 wt % (preferably, 0.1 to 3 wt %) of the colorant based on the weight of the skin moisturizing formulation).

[0055] Preferably, the method for preparing a skin moisturizing formulation of the present invention further comprises providing a desquamation promoter and combining the desquamation promoter with a dermatologically acceptable vehicle and a skin moisturizer to form a skin moisturizing formulation (preferably, the formed skin moisturizing formulation contains 0.01 to 15 wt. % of the desquamation promoter based on the weight of the skin moisturizing formulation). More preferably, the method for preparing a skin moisturizing formulation of the present invention further comprises providing a desquamation promoter and combining the desquamation promoter with a dermatologically acceptable vehicle and a skin moisturizer to form a skin moisturizing formulation (preferably, the formed skin moisturizing formulation contains 0.01 to 15 wt. % of the desquamation promoter based on the weight of the skin moisturizing formulation), the desquamation promoter being selected from the group consisting of alpha-hydroxycarboxylic acids and beta-hydroxycarboxylic acids, and mixtures thereof (e.g., glycolic acid, lactic acid, malic acid, salicylic acid, and mixtures thereof). These acids may be used as the free acid or as salts thereof and C 1-30 It can exist as an alkyl or aryl ester, as well as a lactone formed from removal of water to form a cyclic or linear lactone structure.

[0056] Preferably, the method of making a skin moisturizing formulation of the present invention further comprises providing an enzyme and combining the enzyme with a dermatologically acceptable vehicle and a skin moisturizer to form a skin moisturizing formulation. More preferably, the method of making a skin moisturizing formulation of the present invention further comprises providing an enzyme and combining the enzyme with a dermatologically acceptable vehicle and a skin moisturizer to form a skin moisturizing formulation, wherein the enzyme is selected from the group consisting of amylases, oxidases, proteases, lipases, and mixtures thereof.

[0057] Preferably, the method for making the skin moisturizing formulation of the present invention further comprises providing an herbal extract and combining the herbal extract with a dermatologically acceptable vehicle and a skin moisturizer to form a skin moisturizing formulation. More preferably, the method for making the skin moisturizing formulation of the present invention further comprises providing an herbal extract and combining the herbal extract with a dermatologically acceptable vehicle and a skin moisturizer to form a skin moisturizing formulation, wherein the herbal extract is selected from the group consisting of green tea, soybean, rice, yarrow, almond, chamomile, licorice, aloe vera, grapeseed, Satsuma mandarin, willow bark, sage, thyme, rosemary, pomegranate, and mixtures thereof.

[0058] Preferably, the method of making a skin moisturizing formulation of the present invention further comprises providing a fragrance and combining the fragrance with a dermatologically acceptable vehicle and a skin moisturizer to form a skin moisturizing formulation (preferably, the formed skin moisturizing formulation comprises 0.000001 to 10 wt % (preferably, 0.00001 to 5 wt %, more preferably 0.0001 to 2 wt %) of fragrance based on the weight of the skin moisturizing formulation). More preferably, the method of making a skin moisturizing formulation of the present invention further comprises providing a fragrance and combining the fragrance with a dermatologically acceptable vehicle and a skin moisturizer to form a skin moisturizing formulation (preferably, the formed skin moisturizing formulation comprises 0.000001 to 10 wt % (preferably, 0.00001 to 5 wt %, more preferably 0.0001 to 2 wt %) of fragrance based on the weight of the skin moisturizing formulation), wherein the fragrance is selected from the group consisting of terpenes and terpene derivatives (e.g., myrcene, dihydromyrcenol, citral, tagetone, cis-geranic acid, citronellic acid, aldehydes, alcohols, esters, ketones, natural fragrances (e.g., essential oils), derivatives thereof, mixtures thereof, etc.).

[0059] Preferably, the method of making the skin moisturizing formulation of the present invention further comprises providing a humectant and combining the humectant with a dermatologically acceptable vehicle and a skin moisturizer to form the skin moisturizing formulation. More preferably, the method of making a skin moisturizing formulation of the present invention further comprises providing a humectant and combining the humectant with a dermatologically acceptable vehicle and a skin moisturizer to form the skin moisturizing formulation, wherein the humectant is selected from the group consisting of glycerin, sorbitol, xylitol, maltitol, honey, monoglycerides, lecithin, hyaluronic acid, sodium hyaluronate, urea, allantoin, alpha hydroxy acids, sodium PCA, hydrolyzed wheat / baobab / rice protein, amino acids, chitosan, seaweed, glycolipids, fatty alcohols, fatty acids, polysaccharides, sorbitan esters, polysorbates (e.g., polysorbate 20, polysorbate 40, polysorbate 60, and polysorbate 80), diols (e.g., propylene glycol), diol analogs, triols, triol analogs, polymeric polyols, cationic polymeric polyols, cationic polymers, starch, cellulose, and mixtures thereof.

[0060] Preferably, the method for making the skin moisturizing formulation of the present invention further comprises providing a pH adjusting agent and combining the pH adjusting agent with a dermatologically acceptable vehicle and a skin moisturizing agent to form a skin moisturizing formulation. More preferably, the method for making the skin moisturizing formulation of the present invention further comprises providing a pH adjusting agent and combining the pH adjusting agent with a dermatologically acceptable vehicle and a skin moisturizing agent to form a skin moisturizing formulation, wherein the pH of the skin moisturizing formulation is adjusted to 4.5 to 9 (preferably 5 to 8, most preferably 6 to 7). Most preferably, the method of making the skin moisturizing formulation of the present invention further comprises providing a pH adjusting agent and combining the pH adjusting agent with a dermatologically acceptable vehicle and a skin moisturizing agent to form a skin moisturizing formulation, wherein the pH of the skin moisturizing formulation is adjusted to 4.5 to 9 (preferably 5 to 8, most preferably 6 to 7), and the pH adjusting agent is selected from the group consisting of citric acid, lactic acid, hydrochloric acid, aminoethylpropanediol, triethanolamine, monoethanolamine, sodium hydroxide, potassium hydroxide, and amino-2-methyl-1-propanol.

[0061] Preferably, the method of making the skin moisturizing formulation of the present invention further comprises providing a preservative and combining the preservative with a dermatologically acceptable vehicle and a skin moisturizer to form a skin moisturizing formulation (preferably, the formed skin moisturizing formulation comprises 0.01 to 2% by weight of the preservative, based on the weight of the skin moisturizing formulation). More preferably, the method of making a skin moisturizing formulation of the present invention further comprises providing a preservative and combining the preservative with a dermatologically acceptable vehicle and a skin moisturizer to form a skin moisturizing formulation (preferably, the formed skin moisturizing formulation comprises 0.01 to 2 wt. % of the preservative, based on the weight of the skin moisturizing formulation), wherein the preservative is selected from the group consisting of phenoxyethanol, methylparaben, propylparaben, imidazolidinyl urea, benzoic acid and its salts, sorbic acid and its salts, phenoxyethanol, dimethyloldimethylhydantoin, ethylenediaminetetraacetic acid (EDTA), sodium dehydroacetate, methylchloroisothiazolinone, methylisothiazolinone, iodopropyne butylcarbamate, and benzyl alcohol.

[0062] Preferably, the method of making the skin moisturizing formulation of the present invention further comprises providing a skin lightening agent and combining the skin lightening agent with a dermatologically acceptable vehicle and a skin moisturizing agent to form a skin moisturizing formulation (preferably, the formed skin moisturizing formulation comprises 0.1 to 10 wt % (preferably, 0.5 to 2 wt %) of the skin lightening agent based on the weight of the skin moisturizing formulation). More preferably, the method for making a skin moisturizing formulation of the present invention further comprises providing a skin lightening agent and combining the skin lightening agent with a dermatologically acceptable vehicle and a skin moisturizing agent to form a skin moisturizing formulation (preferably, the formed skin moisturizing formulation comprises 0.1 to 10 wt % (preferably, 0.5 to 2 wt %) of the skin lightening agent based on the weight of the skin moisturizing formulation), wherein the skin lightening agent is selected from the group consisting of plant extracts (e.g., licorice extract, bearberry extract), alpha hydroxy acids, niacinamide, arbutin, azelaic acid, kojic acid, ferulic acid, 12-hydroxystearic acid, hydroquinone, retinol, retinoids, resorcinol, and derivatives including 4-substituted resorcinols, and mixtures thereof).

[0063] Preferably, the method of making the skin moisturizing formulation of the present invention further comprises providing a soap and combining the soap with a dermatologically acceptable vehicle and a skin moisturizer to form a skin moisturizing formulation. More preferably, the method of making the skin moisturizing formulation of the present invention further comprises providing a soap and combining the soap with a dermatologically acceptable vehicle and a skin moisturizer to form a skin moisturizing formulation, the soap being selected from the group consisting of sodium stearate, sodium laurate, sodium tallowate, sodium palmitate, potassium stearate, potassium laurate, potassium tallowate, potassium palmitate, and mixtures thereof.

[0064] Preferably, the method of making the skin moisturizing formulation of the present invention further comprises providing a suncare agent and combining the suncare agent with a dermatologically acceptable vehicle and a skin moisturizing agent to form a skin moisturizing formulation (preferably, the formed skin moisturizing formulation comprises 0.1 to 30 wt % (preferably, 2 to 20 wt %, more preferably 4 to 10 wt %) of the suncare agent based on the weight of the skin moisturizing formulation).More preferably, the method of making a skin moisturizing formulation of the present invention further comprises providing a suncare agent, and combining the suncare agent with a dermatologically acceptable vehicle and a skin moisturizer to form a skin moisturizing formulation (preferably, the formed skin moisturizing formulation comprises 0.1 to 30 wt % (preferably, 2 to 20 wt %, more preferably, 4 to 10 wt %) of the suncare agent based on the weight of the skin moisturizing formulation), the suncare agent being selected from the group consisting of red petrolatum, titanium dioxide, zinc oxide, 1-(4-methoxyphenol)-3-(4-tert-butylphenyl)propane-1,3-dione, 2-hydroxy-4-methoxybenzophenone, dioxybenzone, sulisobenzone, menthyl anthranilate, para-aminobenzoic acid, amyl paradimethylaminobenzoate, octyl paradimethylaminobenzoate, ethyl 4-bis(hydroxypropyl)para-aminobenzoate, polyethylene glycol (PEG-25) para- ... Pyr) aminobenzoate, diethanolamine para-methyoxycinnamate, 2-ethoxyethyl para-methoxycinnamate, ethylhexyl para-methoxycinnamate, octyl para-methoxycinnamate, isoamyl para-methoxycinnamate, 2-ethylhexyl-2-cyano-3,3-diphenyl-acrylate, 2-ethylhexyl-2-cyano-3,3-diphenyl-2-propenoate, 2-ethylhexyl-2-hydroxybenzoate, homomethyl salicylate ester, glyceryl aminobenzoate, triethanolamine salicylate, diguaroyl trioleate, lawsone with dihydroxyacetone, 2-phenylbenzimidazole-5-sulfonic acid, 4-methylbenzylidine camphor, avobenzone, triazines, benzotriazoles, vinyl group-containing amides, cinnamic acid amides, sulfonated benzimidazoles, 3,3,5-trimethylcyclohexyl 2-hydroxybenzoate, and mixtures thereof.

[0065] Preferably, the method of making a skin moisturizing formulation of the present invention further comprises providing a vitamin and combining the vitamin with a dermatologically acceptable vehicle and a skin moisturizer to form a skin moisturizing formulation (preferably, the formed skin moisturizing formulation comprises 0.001 to 10 wt % (preferably, 0.01 to 1 wt %, more preferably 0.1 to 0.5 wt %) of the vitamin based on the weight of the skin moisturizing formulation). More preferably, the method of making a skin moisturizing formulation of the present invention further comprises providing a vitamin and combining the vitamin with a dermatologically acceptable vehicle and a skin moisturizer to form a skin moisturizing formulation (preferably, the formed skin moisturizing formulation contains 0.001 to 10 wt % (preferably, 0.01 to 1 wt %, more preferably 0.1 to 0.5 wt %) of the vitamin based on the weight of the skin moisturizing formulation), wherein the vitamin is selected from the group consisting of vitamin A (retinol), vitamin B (niacinamide), vitamin C, vitamin E, folic acid, biotin, derivatives thereof (e.g., ascorbyl tetraisopalmitate, magnesium ascorbyl phosphate, ascorbyl glycoside, tocopheryl acetate, tocopheryl palmitate, tocopheryl linoleate, DL-panthenol), and mixtures thereof).

[0066] Preferably, the skin moisturizing formulation prepared according to the method of making a skin moisturizing formulation of the present invention comprises <0.0001% by weight (more preferably, <0.00001% by weight, more preferably below the detectable limit) of a metal chelating agent selected from the group consisting of: (i) a metal chelating agent comprising an amino group and at least five carboxylate groups; (ii) a metal chelating agent comprising an amino group and at least four phosphonate groups; and (iii) a mixture of (i) and (ii).

[0067] Preferably, the method of moisturizing skin (preferably reducing the visibility of fine lines and wrinkles) of the present invention comprises providing a skin moisturizing formulation prepared according to the method of making a skin moisturizing formulation of the present invention, and applying the skin moisturizing formulation to mammalian skin (preferably, the skin is dry skin, and preferably, the mammalian skin is human skin).

[0068] Some embodiments of the present invention are described in detail in the following examples.

[0069] Example S1: Synthesis of cationic dextran polymer A 500 mL four-neck round-bottom flask equipped with a rubber ceramic cap, a nitrogen inlet, a pressure-equalizing dropping funnel, a stirring paddle and motor, a subsurface thermocouple connected to a J-KEM controller, and a Friedrichs condenser connected to a mineral oil bubbler was charged with 21.4% aqueous dextran solution (132.6 g, Dextran Products Limited) and deionized water (10.0 g). The dropping funnel was charged with 70% aqueous glycidyltrimethylammonium chloride solution (27.23 g; QUAB® 151, available from SKW QUAB Chemicals). The contents of the flask were stirred. While stirring the contents, the apparatus was purged with nitrogen to remove any oxygen trapped in the system. The nitrogen flow rate was approximately 1 bubble per second. The mixture was purged with nitrogen while stirring for 1 hour. Using a plastic syringe, 25% aqueous sodium hydroxide (4.77 g) was added to the contents of the flask over several minutes while stirring under nitrogen. The contents of the flask were then allowed to stir under nitrogen for 30 minutes. The contents of the addition funnel were then added dropwise to the contents of the flask over 5 minutes under nitrogen with continued stirring. After the contents of the addition funnel were transferred to the contents of the flask, the mixture was allowed to stir for 5 minutes. Heat was then applied to the contents of the flask with a heating mantle controlled using a J-KEM controller set at 55°C. The contents of the flask were heated to 55°C and maintained for 105 minutes. The contents of the flask were then cooled to room temperature while maintaining positive nitrogen pressure within the flask. When the contents of the flask reached room temperature, glacial acetic acid (3.00 g) was added dropwise to the contents of the flask via syringe, and the mixture was stirred for 10 minutes. The polymer was recovered by non-solvent precipitation of this aqueous solution with methanol. A Waring blender was charged with methanol (700 mL) and the polymer solution (20 mL) was added slowly and continuously at a moderate mixing speed. Upon the onset of clouding of the methanol non-solvent, the precipitated polymer was recovered by filtration through a set of nested #40 and #80 US standard sieve screens. Fresh methanol was charged to the Waring blender to continue the non-solvent precipitation of the remaining aqueous polymer solution. The recovered polymer was briefly air-dried and then dried overnight in a vacuum oven at 50°C.The product, cationic dextran polymer, was a white solid (35.0 g) with a volatile content of 4.45% and an ash content of 1.85% (as sodium chloride). Volatiles and ash were measured as described in ASTM Method D-2364. The Kjeldahl nitrogen content was measured using a Buchi KjelMaster K-375 autoanalyzer and found to be 1.827% (corrected for volatiles and ash), corresponding to a degree of trimethylammonium substitution of 0.263.

[0070] In vitro moisturizing The following procedure was used to evaluate the in vitro moisture retention of the materials. 1. Weigh a blank aluminum dish and record the weight as W0. 2. Weigh 2.0 g of the test material into an aluminum dish and record the total weight of the material and the aluminum dish as W1. 3. Place the aluminum dish containing the test material in a preheated oven at 105°C for 3 hours. 4. After 3 hours, remove the aluminum pan with the material to be tested from the oven and immediately weigh as W2. 5. The aluminum pan with the material to be tested is placed in a first test chamber at constant temperature and humidity of 45°C and 90% relative humidity for 40 hours. 6. After 40 hours, remove the aluminum pan with the material to be tested from the first test chamber and immediately weigh as W3. 7. The aluminum tray with the material to be tested is placed in a second test chamber with a constant temperature and humidity of 22°C and 55% relative humidity, and the weight of the aluminum tray with the material to be tested is measured every hour for 7 or 8 hours, as follows: W4, W5, W6, W7, W8, W9, W10, W11, W12, W13, W14, W15, W16, W17, W18, W19, W20, W21, W22, W23, W24, W25, W26, W27, W28, W29, W30, W31, W32, W33, W34, W35, W36, W37, W38, W39, W40, W41, W42, W43, W44, W45, W46, W47, W48, W49, W50, W51, W5 10 , and W 11 Record as.

[0071] Calculations from measurements include: Weight of fresh sample of material = W1-W0 Weight of dry sample = W2 - W0 Weight of water saturated sample = W3-W0 Maximum amount of absorbed water after 0 hours (%) = 100 × [(W3-W0) / (W2-W0)] Remaining absorbed water after 1 hour (%) = 100 × [(W4-W0) / (W2-W0)] Remaining absorbed water after 2 hours (%) = 100 × [(W5-W0) / (W2-W0)] Remaining absorbed water after 3 hours (%) = 100 × [(W6-W0) / (W2-W0)] Remaining absorbed water after 4 hours (%) = 100 × [(W7-W0) / (W2-W0)] Remaining absorbed water after 5 hours (%) = 100 × [(W8-W0) / (W2-W0)] Remaining absorbed water after 6 hours (%) = 100 × [(W9-W0) / (W2-W0)] Remaining absorbed water after 7 hours (%) = 100 × [(W 10 -W0) / (W2-W0)]

[0072] The higher the weight percent or water absorption and the slower the release of water to the atmosphere, the better the moisture retention performance of the tested material. The results of the in vitro moisture retention test of the polymer produced according to Example S1 are compared with the results obtained for two benchmark materials in Tables 1 and 2.

[0073] [Table 1]

[0074] [Table 2]

Claims

1. 1. A method of making a skin moisturizing formulation, comprising: providing a dermatologically acceptable vehicle; selecting a skin moisturizer based on its ability to absorb and retain moisture, wherein the selected skin moisturizer is a cationic dextran polymer including a dextran polymer functionalized with a quaternary ammonium group; providing said selected skin moisturizer; combining said dermatologically acceptable vehicle and said skin moisturizer to form a skin moisturizing formulation; Including, the skin moisturizing formulation contains 0.05 to 10 wt. % of the skin moisturizing agent based on the weight of the skin moisturizing formulation; the skin moisturizing formulation is a leave-on skin care formulation selected from the group consisting of color cosmetics, lotions, sunscreens, and creams; the dermatologically acceptable vehicle is selected from the group consisting of aqueous emulsions; the selected skin moisturizer has a Kjeldahl nitrogen content (TKN), corrected for ash and volatile matter, of 1.0 to 4.0 wt. %; the dextran polymer is a branched dextran polymer; The method wherein the dextran polymer has a weight average molecular weight of 145,000 to 525,000 daltons.

2. 1. A method for moisturizing skin, comprising: providing a skin moisturizing formulation prepared according to the method of claim 1; applying the skin moisturizing formulation to the skin of a non-human mammal; A method comprising:

Citation Information

Patent Citations

  • Acne-removing facial cleanser

    CN109157451A

  • Cationized dextran derivative, its production and use

    JP1982005701A

  • Cationized dextran derivative and its production and use

    JP1982070101A

  • Cationized dextran derivative / polyuronic acid polyelectrolyte complex and its use

    JP1986064701A

  • Gelling dextran ether

    JP2018511684A