JPH07267815A - Nonionic glycolipid activator-containing composition - Google Patents

Abstract

PURPOSE: To obtain a new personal product composition containing a nonionic aldobionamide as a surfactant and having good foaming and stable foam and used for soaps, cleansing agent for face washing or body, tooth pastes, shampoo, etc. CONSTITUTION: This personal product composition comprises a detergent containing at least one kind of aldobionamide as a surfactant, having good foaming, excellent in foam stability, having product stability and capable of using for skin, tooth, hair, etc. A lactobionamide of formula I (R1 and R2 are each H, an aliphatic hydrocarbon, an aromatic and an alicyclic, amino acid ester or etheramine, with the proviso that R1 and R2 are simultaneously not H) or maltobionamide of formula II is preferably used as the aldobinamide of the surfactant. A surface-active agent other than aldobionamide is preferably used with the above surfactant. The active agent includes especially preferably a fatty acid soap, an alkyl ether sulfate, an alkylethoxylate, an alkylglyceryl ether sulfonate, methylacyltaurate or an N-acylglutamate.

Description

Detailed Description of the Invention

[0001]

The present invention contains a specific glycolipid,
New personal product composition. More specifically, the present invention relates to compositions that include nonionic aldobionamide as a surfactant in the composition.

[0002] As used herein, a personal product is intended to mean a product applied to human skin, teeth or hair for cosmetic, cleaning and beautifying purposes. Such compositions include, but are not limited to, personal cleansing soaps, face and body wash liquid detergents, toothpastes, antiperspirants and deodorants, shaving foams, creams and soaps, shower gels, cosmetics and shampoo products. Included in.

[0003]

Most activators currently used in personal products are of petrochemical origin. With increasing interest in environmental issues due to the use of petrochemicals and rising prices of these petrochemicals, there is a need to obtain activators from renewable resources.

These naturally derived compounds represent a source of renewable raw materials that are synthetically flexible, inexpensive, optically pure and environmentally friendly.

A series of active agents based on carbohydrates have been proposed. These are broadly divided into several groups, including alkyl polyglucosides and N-polyhydroxyalkyl fatty acid amides.

US Pat. No. 5,009,814 has the formula: X--CH ₂ (R ₂ ) N--CO--R _{1 where} R ₁ is alkyl and R ₂ is hydrogen, alkyl or alkyl hydroxide, X is a polyhydroxy group] is used to teach the use of N-polyhydroxyalkyl fatty acid amides as thickeners in aqueous activator systems. Note that in N-polyhydroxyalkyl fatty acid amides, the polyhydroxy group X is attached to the nitrogen atom via a methylene group rather than a carbonyl group. These compounds are obtained by reacting a monosaccharide sugar amine with a fatty acid alkyl ester.

WO 92/06172 teaches the construction of liquid detergent compositions containing polyhydroxy acid amides. There are about 20 related applications that mention various compositions containing the polyhydroxyamides of US Pat. No. 5,009,814.

French patent application 82/05005 (publication 2,523,96
2) have the general _{formula: HO-CH 2 (CHOH)} m -CONH-R [ wherein, m is 2 to 6, R is a 6-18 linear or branched alkyl group having a carbon] line with a Teaches amides. It is said that these activators have low foaming properties, and in order to maintain sufficient solubility, they must be ethoxylated or propoxylated by a conventional method.

Walden US Pat. No. 2,752,334 teaches compounds which are the reaction products of aldonic acids (eg lactobionic acid) with aliphatic amines. This compound is
It is said to be useful as an emulsifier in food compositions.

[0010] Williams et al. Archives of Biochem. And B
iophysics, 195 (1): 145-151 (1979) discloses glycolipids obtained by linking aldobionic acid with an alkylamine through an amide bond. These compounds are said to form micelles like all active agents, but for the use of these compounds in personal product compositions:
There is no disclosure or suggestion.

[0011]

One of the problems with conventional activator substitutes derived from petrochemicals is their low foaming tendency and low solubility in aqueous systems.

[0012]

SUMMARY OF THE INVENTION We have now found that personal product compositions based on aldovionamide have acceptable foaming tendency and foam stability, as well as acceptable product stability. I found it.

In the present specification, aldbionamide is defined as an amide (or aldobionolactone) of aldobionic acid, and aldbionic acid means that an aldehyde group (generally located at the C ₁ position of sugar) is a carboxylic acid. It is defined as a sugar substance (in any cyclized sugar) which is substituted with and is cyclized to aldonolactone upon dehydration.
Aldionamides may be derived from disaccharides (lactobionamide or maltobionamide etc.), may be based on more than two sugar units, and may be polysaccharides having an aldehyde group at the terminal sugar unit. Good. However, it should be of at least 2 sugar units,
It has a lesser tendency for such substances to be tightly packed in the solid phase, is more water soluble than linear saccharides (eg gluconamide or glucoheptone amide) and allows for a more stable composition formation Because.

According to the invention there is provided a personal product composition comprising at least one aldobionamide as an active agent.

The aldobionamides used in the compositions of the present invention have the desired properties such as critical micelle concentration, Kraft point, foamability, detergency, and other well known nonionic activities of petrochemical origin. Agents (eg Neodol from Shell)
Alkylation activator based on [registered trademark] series) or higher. This indicates that they are viable, environmentally friendly alternatives to the use of traditional non-ionic activators. Aldionamides also have lower Kraft points and greater solubility than their linear monosaccharide counterparts.

Without wishing to be bound by the theory below, the low solubility of aldobionamides leads to sugar structures that prevent the close packing that is typical of linear monosaccharide aldonamides such as gluconamide. Believed to be based. The high number of hydroxyl groups may also help the aldobionamides become more water soluble.

While the lyotropic liquid crystal phase obtained with the lactobionamide activator is stable up to 90 ° C.,
It is interesting to note that the ethoxylated activator is much more sensitive at this temperature (H ₁ phase with C ₁₂ EO melts at 37 ° C.). The high temperature stability of the lyotropic mesophase made of lactobionamide is a reflection of the relatively insensitive temperature head of this carbohydrate. This property can be used to advantage in products where the phase structure must be maintained over a wide temperature range.

The aldobionamides used in the composition of the present invention are preferably disaccharides, more preferably compounds based on lactobionamide or maltobionamide. Other aldobionamides (disaccharides) that may be used include cellobionamide, meribionamide and gentiobionamide.

A particularly preferred aldobionamide for use in the composition of the present invention has the general formula:

[0020]

[Chemical 3]

[Wherein R ₁ and R ₂ are the same or different and are hydrogen, an aliphatic hydrocarbon group (for example, an alkyl group which may contain a hetero atom such as N, O or S, and an alkene group). Or an alkoxylated alkyl chain such as an ethoxylated or propoxylated alkyl group; preferably an alkyl group having 8 to 24 carbon atoms, more preferably 10 to 18 carbon atoms), an aromatic group (substituted or unsubstituted) Aryl groups and arenes), alicyclic groups, amino acid esters, ether amines and mixtures thereof, but R ₁ and R ₂ are not hydrogen at the same time. is there.

Other preferred aldobionamides have the general formula:

[0023]

[Chemical 4]

[Wherein R ₁ and R ₂ are the same or different and are hydrogen, an aliphatic hydrocarbon group (for example, an alkyl group and an alkene group which may contain a hetero atom such as N, O or S). Or an alkoxylated alkyl chain such as an ethoxylated or propoxylated alkyl group; preferably an alkyl group having 8 to 24 carbon atoms, more preferably 10 to 18 carbon atoms), an aromatic group (substituted or unsubstituted) Aryl groups and arenes), alicyclic groups, amino acid esters, ether amines and mixtures thereof, but R ₁ and R ₂ are not hydrogen at the same time]. .

Suitable aliphatic hydrocarbon radicals include methyl, ethyl, amyl, hexyl, heptyl, nonyl, decyl,
Includes saturated or unsaturated groups including, but not limited to, undecyl, dodecyl, tridecyl, tetradecyl, pentadecyl, hexadecyl, heptadecyl and octadecyl and allyl, undecenyl, oleyl, linoleyl, linolenyl, propenyl and heptenyl.

Suitable aromatic groups include benzyl. Suitable aliphatic-aromatic mixed groups include phenethyl and vinylbenzyl. Suitable alicyclic groups include cyclopentyl and cyclohexyl.

These preferred compositions are suitable for use in personal cleansing soaps, face and body wash liquid detergents, toothpastes, antiperspirants and deodorants, shaving foams, creams and soaps, shower gels, cosmetic and shampoo products. ing. In this particular embodiment, additional components are present as described in more detail below. In the preferred embodiments of the invention described below, all amounts are expressed in weight percent unless otherwise indicated.

Active Agent Typically, the compositions of the present invention comprise aldobionamide as a co-active agent and at least one other active agent.

[0029] Preferably, the other active agent comprises a fatty acid soap. The presence of fatty acid soap is particularly preferred when embodying the present invention in the form of toilet soap. Fatty acid soaps are typically alkali metal or alkanol ammonium salts of aliphatic alkane or alkene monocarboxylic acids. Sodium, potassium, mono-, di- and tri-ethanol ammonium cations or combinations thereof are suitable for the purposes of the present invention. This soap is well known as the alkali metal salt of a natural or synthetic fatty acid (alkanoic or alkenoic) of about 8 to 22 carbon atoms, preferably 12 to about 18 carbon atoms. These can be expressed as carboxylic acid alkali metal salts of acrylic hydrocarbons having about 12 to 22 carbon atoms.

Examples of suitable soaps for use are Caswell et al. US Pat. No. 4,695,395 and Barrett US Pat. No. 4,260,5.
Found in issue 07. Both of these are incorporated herein by reference.

When the present invention is used as a soap-based solid detergent, fatty acid soap is generally contained in the composition in an amount of more than 25%, usually 30 to 95%. Suitable amounts of soap range from 40 to 70% by weight of the composition. Solid detergents based on other activators may also contain 0 to 50 wt% soap. Generally, C ₈ to C ₂₄ fatty acids are included in the composition of 5
Occupy ~ 60%.

The fatty acid soap used in the liquid face-wash and body-wash detergents is the same as described above for the solid detergent.

In a more preferred embodiment of the composition of the present invention, in addition to aldobionamide or soap, anionic, nonionic, cationic, zwitterionic, zwitterionic substances, or mixtures thereof are used. It also includes other active agents of choice. For these, the above-mentioned U.S. Pat.
5,395 or Inman, US Pat. No. 4,854,333, which are hereby incorporated by reference.

Suitable synthetic activators are alkyl ether sulfates, alkyl ethoxylates, alkyl glyceryl ether sulfonates, methyl acyl taurates, N-acyl glutamate, acyl isethionates, anionic acyl sarcosinates, methyl glucose esters, Protein condensate, ethoxylated alkyl sulfate,
Alkyl polyglycosides, alkyl amine oxides, betaines, sulteines, alkyl sulfosuccinates, and mixtures thereof.

One of the particularly preferred non-soap anion agents is the C ₈ to C ₂₂ alkyl isethionates.
The ester is obtained by the reaction between an alkali metal isethionate and a C ₈ to C ₂₂ mixed fatty acid. The non-soap activator may comprise 0-50% of the composition.

It is also desirable to include an appropriate amount of C ₈ to C ₂₂ free fatty acids in the composition, especially bar soaps and skin cleansers. These act as superfatting agents or skin feel and creaminess enhancers. When present, free fatty acids comprise 1-40% of the composition.

The preferred salt to be added to the soap composition is simply unsubstituted sodium isethionate. It is comprised between 0.1 and 50%, preferably between 0.5 and 25%, more preferably between 2 and about 15% by weight of the composition.

Other softening co-activators which it is desirable to use include:
The betaine compounds or ether sulfates already mentioned are included. These are also 0.1 to 50% of the composition,
Preferably 0.5 to 25% is included.

The sulfate ester activator is 0.1 to 45%, preferably 25 to 45%, of the composition as a monoester, and 0.01 to 10% of the composition as a diester, preferably
Include at a level of 0.01-5%.

The preferred toothpaste of the present invention is 0
~ 1.5 wt% anionic activator. In a more preferred product, the amount of anionic active agent comprises 0 to 1% by weight, most preferably 0 to 0.75% by weight. The toothpaste of the present invention may contain other active agents, especially nonionic active agents.

The bar soap according to the present invention is preferably 30-.
Contains 95% fatty acid soap and at least 1% aldobionamide.

Liquid cleaning compositions to be applied to human skin or hair preferably contain at least 1% of aldobionamide and fatty acid soaps, alkyl ether sulphates, alkyl ethoxylates, alkyl glyceryl ether sulphonates, methylacyl taurates. , N-acyl glutamate, acyl isethionate, anionic acyl sarcosinate, methyl glucose ester, protein condensate, ethoxylated alkyl sulfate, alkyl polyglycoside, alkyl amine oxide, betaine, sulteine, alkyl sulfosuccinate, N- Polyhydroxyalkyl fatty acid amide, and at least 1% of an activator selected from the group consisting of mixtures thereof.

Wetting agents, emollients and polymeric skin feel enhancement
Agent As described above, another aspect of the present invention is a face-washing or body-washing composition. Examples of such cleaning compositions are found, for example, in Small et al., U.S. Pat. No. 4,812,253 and Fujisawa, U.S. Pat. No. 4,526,710. Both of these are incorporated herein by reference.

Generally, such face-washing or body-washing compositions contain humectants, emollients and polymeric skin feel enhancers.

This humectant provides the benefit of moisturizing the skin and improves softness. The term is often used synonymously with emollients and is used to describe substances that provide a smooth and soft sensation on the skin surface.

It is said that there are two methods for reducing the water loss from the stratum corneum. One of them is to provide an occlusive layer on the skin surface to reduce the evaporation rate. The second method is to add a non-occlusive hygroscopic substance that retains water to the stratum corneum and use this moisture in the stratum corneum to change its physical properties and obtain the desired effect as a cosmetic product. Non-occlusive humectants also have the meaning of improving the lubricity of the skin.

Both occlusive and non-occlusive humectants can be added to the compositions of this invention.

Preferred wetting agents include long chain fatty acids, liquid water soluble polyols, glycerin, propylene glycol,
Sorbitol, polyethylene glycol, ethoxylated / propoxylated ethers of methyl glucose (eg,
methyl gluceth-20) and ethoxylated / propoxylated ethers of lanolin alcohol (eg Solulan-75 (T
M)).

Particularly preferred humectants are coco and tallow fatty acids. Other preferred humectants are non-occlusive liquid water-soluble polyols and essential amino acid compounds that are naturally present in the skin.

Other preferred non-occlusive humectants are those naturally present in the stratum corneum of the skin, such as sodium pyrrolidonecarboxylate, lactic acid, urea, L-proline, guanidine and pyrrolidone. Examples of other non-occlusive humectants are hexadecyl, myristyl, isodecyl or isopropyl esters of adipic acid, lactic acid, oleic acid, stearic acid, isostearic acid, myristic acid or linolenic acid. In addition, there are corresponding alcohol esters (isostearoyl-2 lactylate sodium, capryl lactylate sodium), hydrogenated proteins, collagen-derived proteins, aloe vera gel and acetamide MEA.

Preferred occlusive humectants include petrolatum, mineral oil, beeswax, silicones, lanolin and oil soluble lanolin derivatives, saturated and unsaturated fatty alcohols (such as behenyl alcohol), squalene and squalane, almond oil, peanut oil, wheat. Embryo oil, linseed oil, jojoba oil, apricot kernel oil, walnut, coconut, pistachio nut, sesame seed,
Rapeseed, cade oil, corn oil, peach kernel oil, poppy seed oil, pine oil, camphor oil, soybean oil, avocado oil, safflower oil, coconut oil, hazelnut oil, olive oil, grape seed oil, sunflower seed oil, etc. There are various animal and vegetable oils of.

Other examples of these two types of wetting agents are "Emo
llients-a Critical Evaluation, "by J. Mausner, C
osmetics & Toiletries, May 1981.
This document is incorporated herein by reference.

It is desirable that the composition further comprises a substance that provides a smooth and soft sensation on the skin surface.

Preferred auxiliaries for providing a smooth and soft sensation on the skin surface are the cationic, anionic, zwitterionic and nonionic polymers used in the cosmetics field. The reduction in skin irritation evaluated by the patch test for cationic and nonionic polymers is shown in "Polym
er UR for Skin Care "Bulletin, by Union Carbide, 19
Specified in 77. Cationic ones are preferable to other products because they have a good effect on improving skin sensation.

The amount of the auxiliaries found to be useful in the compositions of the present invention to provide a smooth and soft sensation on the skin surface is from about 0.01% to about 5%, preferably from about 0.3% to about 4%. Is. In solid compositions with less than 5.5% soap, these polymers are used at levels of 2-5%, preferably 3% or higher.

Other polymeric auxiliaries that provide a smooth and soft sensation on high molecular weight skin surfaces include non-ionic guar gums such as Merquats 100 and 500 manufactured by the Applicant, Jaguar C-14 from Stein Hall. -S, Mirapol A15 from Miranol Chemical, Galctasol 811 from Henkel, etc. can be used. These polymers also provide the additional benefit of enhancing creamy foaming.

Suitable nonionic polymers are:
It includes nonionic polysaccharides such as nonionic hydroxypropyl guar gum provided by Celanese. Particularly preferred nonionic hydroxypropyl guar gum material is Jaguar ^R HP-60 having about 0.6 molecular degree of substitution. Other usable nonionics include cellulosic nonionic polymers such as HEC and CMC.

The cationic polymers used in the present invention also provide the desired silky, soft and slippery feel. The preferred range for the present invention is 0.1 to the composition.
5%. There is reason to believe that positively charged cationic polymers bind to the negatively charged sites on the skin and make the skin feel soft after use. Without being bound by any theory, it is said that the higher the charge density of the cationic polymer, the more effective it is in improving the skin feel.

Other suitable cationic polymers include:
There are copolymers of dimethylaminoethylmethacrylate and acrylamide, and copolymers of dimethyldiallylammonium chloride and acrylamide. The ratio of these copolymers to the cationic neutral monomers is chosen so that they have a cationic charge. The further cationic polymers other suitable, there is a cationic starch, e.g. Staley Company manufacturing Sta-Lok ^R 300 and 400.

A more complete listing of cationic polymers that may be used in the present invention is set forth in US Pat. No. 4,438,095 (Grollier / alles) issued Mar. 20, 1984. This disclosure is incorporated herein by reference. Some of the more preferred cationic substances are the above-mentioned Grol
See the third column section 2, the fifth column section 8, the eighth column section 10 and the ninth column lines 10-15 of the lier / alles patent. This disclosure is also incorporated herein by reference.

Silicone Another optional ingredient suitable in the present invention is a non-volatile silicone fluid.

The non-volatile silicone fluid may be a polyalkyl siloxane, polyaryl siloxane or polyether siloxane copolymer, and may comprise about 0.1% to about 10.0%, preferably about 0.5% to about 5.0%. Exists at a standard. Mixtures of these liquids may be used and are rather preferred in certain embodiments. The dispersed silicone particles should also be insoluble in the product matrix. The term "insoluble" as used herein has such a meaning.

Substantially non-volatile polyalkylsiloxane fluids that can be used include, for example, viscosity ranges from about 5 to about 600,
Includes 000 cSt (25 ° C) dimethyl polysiloxane. These siloxanes are available from General Electric Company, for example.
As a Viscasil series or from Dow Corning
Available as Corning 200 series. The viscosity of siloxane is Dow Corning CorporateTest Method CTM0004.
It can be measured with a glass capillary viscometer as specified in (July 20, 1970). The viscosities of such preferred siloxanes range from about 350 to about 100,000 cSt.

Substantially non-volatile polyether siloxane copolymers which can be used are, for example, dimethylpolysiloxane-modified polypropylene oxide (Dow Corning DC-1248).
Etc.), but ethylene oxide and ethylene oxide / propylene oxide mixtures can also be used.

Suitable silicone fluids include Green's US Pat. No. 2,826,551, Drakoff's US Pat. No. 3,946,500 (June 22, 1976), Pader's US Pat. No. 4,364,837 and Woolston's British Patent. 849,4
It is described in No. 33. All of which are incorporated herein by reference. The Silicon Compounds distributed by Petrarch Systems, Inc. in 1984 are also incorporated herein by reference. This document makes a very good list of suitable silicone materials.

Another silicone material that can be used is silicone rubber. Petrarch For Silicone Rubber
U.S. Pat. No. 4,152,416 to Spitzer et al. (1979
May 1st), and Noll, Chemistry and Technology of
Silicones, New York, Academic Press, 1968. For useful silicone rubbers, see GeneralEle
ctric Silicone Rubber Product Data Sheets SE 30, S
It is also described in E 33, SE 54 and SE 76. All of which are incorporated herein by reference. "Silicone rubber" material refers to high molecular weight polydiorganosiloxanes having a molecular weight of from about 200,000 to about 1,000,000. Specific examples include polydimethylsiloxane, polydimethylsiloxane / methylvinylsiloxane copolymers, polydimethylsiloxane / diphenyl / methylvinylsiloxane copolymers, and mixtures thereof. Mixtures of silicone fluid and silicone rubber are also useful in the present invention.

Thickeners and Suspending Agents The compositions of the present invention may optionally further comprise binders, thickening agents and / or suspending agents.

When the present invention is embodied as a shampoo composition containing a compound such as selenium sulfide which is said to be useful for combating dandruff, as a toothpaste, as a cosmetic base, or as a shower gel. Is especially important to

Suitable suspending agents include various acyl derivative substances and mixtures thereof. Among them are 16 carbon atoms
There are ethylene glycol esters of ~ 22 fatty acids. Suitable suspending agents include ethylene glycol stearate (mono and diesters). Preferred alkanolamides include stearic monoethanolamide, stearic diethanolamide and stearic monoisopropanolamide. Still other long-chain acyl derivatives include long-chain esters of long-chain fatty acids (stearyl stearate, cetyl palmitate, etc.), glyceryl esters (glyceryl distearate) and long-chain esters of long-chain alkanolamides (stearamid DEA). Distearate, stearamide MEA stearate, etc.).

Still other suitable suspensions include:
There are alkyl (16-22 carbon atoms) dimethylamine oxides such as stearyl dimethylamine oxide. When the composition contains an amine oxide or a long-chain acyl derivative as a surfactant, these components also have a suspending function, and it may not be necessary to additionally add a suspending agent.

Xanthan gum is another agent used to suspend selenium sulfide and the like that may be added to the compositions of this invention. This biosynthetic rubber substance is commercially available and is a heteropolysaccharide having a molecular weight of 1 million or more. It is said to contain D-glucose, D-mannose and D-glucuronate in a molar ratio of 2.8: 2.0: 2.0. This polysaccharide is partially acetylated with an acetylation degree of 4.7%. Additional information about this drug can be found in Whistler, Roy L. Ind.
ustrial Gums-Polysaccharides and Their Derivati
ves, New York: Academic Press, 1973. Kelco, a division of Merck & Co., offers xanthan gum as Keltrol®.

A particularly suitable suspension system contains about 0.05% of the composition.
To about 1.0%, preferably about 0.2% to about 0.4% xanthan gum present at a level of about 0.1% to about 3.0% of the composition.
, Preferably with magnesium alumina silicate (Al ₂ Mg ₈ Si ₂ ) present at a level of about 0.5% to about 2.0%. Magnesium alumina silicate is naturally present in smectite minerals such as cholerinite, saponite and sapphire. Purified magnesium alumina silicate suitable for use is veegum (T
It is easily obtained as M). Mixtures of the respective suspending agents are also suitable in the composition according to the invention.

[0073] Other useful thickening agent, such as is sold manufactured by BFGoodrich Co. Carbopol ^R (registered trademark), a crosslinked polyacrylate.

Another optional ingredient used in the composition of the present invention is an amide. The amide used in the composition of the invention may be any fatty acid alkanolamide known to be used in shampoos. Generally, 8 carbon atoms
Mono- and diethanolamides of fatty acids having .about.24. Preferred is coconut monoethanolamide,
Lauric monoethanolamide and mixtures thereof. The amide is present at a level of about 1% to about 10% of the composition.

The composition may also include certain nonionic polymeric materials used in low doses to aid particle dispersion. These can be very diverse, but include cellulosic materials such as hydroxylpropylmethylcellulose, carboxymethylcellulose, hydroxyethylcellulose and sodium carboxymethylcellulose, and mixtures thereof. There are many others, including alginate, polyacrylic acid, polyethylene glycol and starch. For nonionic polymers, Whistler, Roy L. ed. Industrial Gums, Academ
ic Press, 1973 and edited by Robert L. Davidson, Handbook o
f Water-Soluble Gums and Resins, McGraw-Hill, 1980
Are discussed in detail in. These books are incorporated herein by reference.

When a nonionic polymeric material is included, it may comprise from about 0.001% to about 0.1%, preferably about 0.001% of the composition.
It is present at a level of 2% to about 0.05%. Hydroxylpropylmethyl cellulose is the preferred polymer.

In cosmetic compositions, it is usual to include a polymeric thickening agent in an amount suitable for controlling the concentration of the composition for convenient distribution on the body surface. Examples of polymer thickeners include anionic cellulosic materials such as sodium carboxymethylcellulose, anionic polymers such as carboxyvinyl polymers (eg Carbomer 940 and 941), nonionic cellulosic materials such as methylcellulose and hydroxypropylmethylcellulose, Po
Cationic cellulosic materials such as lymer JR 400, Jaguar C
Cationic rubber substances such as 13 S, gum arabic, tragacanth gum, locust bean gum, other gums such as guar gum and carrageenan, proteins such as albumin and protein hydrolysates, bentonite, hectorite, magnesium alumina silicate or sodium alumina. Contains clay silicates. Generally, the thickener is present at a level of from 0.05% to 5%, preferably 0.1% to 1% by weight of the composition.

A large number of binders and thickeners are used for toothpaste. Preferred are sodium carboxymethyl cellulose, crosslinked polyacrylates and xanthan gum. In addition to these, there are natural rubber binders such as tragacanth gum, karaya gum, gum arabic, Irish moss, alginate and carrageenan. Silica thickeners include silica airgel and various precipitated silicas. It is also possible to use mixtures of binders and thickeners. The amount of binder and thickener included in a toothpaste is generally between 0.1 and 15% by weight.

Sunscreen Agents Various conventional sunscreen agents, such as US Pat. No. 4,919,93, which is hereby incorporated by reference.
4 (Deckner et al.) Can be used in the compositions of the present invention.

Sunscreen agents include, for example, p-aminobenzoic acid, its salts or derivatives, anthranitrate, salicylates, cinnamic acid derivatives, di- or trihydroxycinnamic acid derivatives, diphenylbutadiene and stilbene. Hydrocarbons, dibenzalacetone and benzalacetophenone, naphthalsulfonate, dihydroxynaphthoic acid and its salts, hydroxydiphenylsulfonate, coumarin derivatives, quinine salts, quinoline derivatives, hydroxy- or methoxy-substituted benzophenones, uric acid or viluric acid.
d), tannic acid and its derivatives, hydroquinone and benzoquinone.

Minor Components and Variants The compositions of the present invention include various other non-essential optional ingredients suitable for facilitating formulation of the compositions or for making them aesthetically and / or cosmetically acceptable. You can
Each of the above components are typically from about 0.01 to about 10 of the composition.
%, Preferably about 0.5 to about 5.0%.

The compositions of the present invention may also optionally contain a preservative to prevent microbial spoilage.

Examples of preservatives include (i) ethanol, benzoic acid, sodium benzoate, sorbic acid, potassium sorbate, sodium propionate, methyl, ethyl, propyl and butyl esters of p-hydroxybenzoic acid, 2-Bromo-2-nitropropane-1,3-diol, phenoxyethanol, dibromodicyanobutane, formalin and Triclos
Chemical preservatives such as an. The amount of chemical preservatives optionally added to the composition of the invention is usually 0.05 to 5% by weight, preferably 0.01 to 2% by weight, this amount being sufficient to inhibit the growth of microorganisms. To be selected.

(Ii) Water activity depressants such as glycerol, propylene glycol, sorbitol, sugars and salts of alkali metal halides, sulfates and carboxylates. If a water activity depressant is used, it is added to the composition of the invention in an amount sufficient to reduce the water activity from 1 to less than 0.9, preferably less than 0.85, and most preferably less than 0.8. Yeast, fungi and fungi do not grow at the lowest of the above values.

The composition of the present invention may also contain other optional additives conventionally used in compositions for topical application to human skin or hair.

One example of an optional additive is an excipient, the choice of which depends on the required product form of the composition. When an excipient is added, it is typically selected from among diluents, dispersants and carriers for the dialkyl or dialkenyl phosphate salts, thereby ensuring that the composition is applied to the skin. In doing so ensure that the salt is evenly distributed.

The compositions of the present invention may contain water as an excipient together with one or more other cosmetically acceptable excipients.

Excipients other than water which may be used in the compositions of the present invention may include emollients, solvents, humectants-thickeners or liquids or solids as powders. The following are examples of each of the various excipients described above that can be used alone or as a mixture of multiple species.

Emollients: stearyl alcohol, glyceryl monolaurate, glyceryl monoricinoleate, glyceryl monostearate, propane-1,2-
Diol, butane-1,3-diol, docosane-1,
2-diol, mink oil, cetyl alcohol, isopropyl isostearate, stearic acid, isobutyl palmitate, isocetyl stearate, oleyl alcohol, isopropyl laurate, hexyl laurate, decyl oleate, octadecane-2-ol, isocetyl. Silicone oils such as alcohol, eicosanyl alcohol, behenyl alcohol, cetyl palmitate, dimethyl polysiloxane, di-n-butyl sebacate, isopropyl myristate, isopropyl palmitate, isopropyl stearate, butyl stearate, polyethylene glycol, triethylene glycol, Lanolin, cocoa butter, corn oil, cottonseed oil, beef tallow, lard, olive oil, palm kernel oil, rapeseed oil, safflower oil, soybean oil, sunflower oil, goji Oil, palm oil, peanut oil, castor oil, acetylated lanolin alcohols, petroleum,
Mineral oil, butyl myristate, isostearic acid, palmitic acid, isopropyl linoleate, lauryl lactate, myristyl lactate, decyl oleate, myristyl myristate, etc.

Propellant: trichlorofluoromethane, dichlorodifluoromethane, dichlorotetrafluoromethane, monochlorodifluoromethane, trichlorotrifluoromethane, propane, butane, isobutane, dimethyl ether, carbon dioxide, nitrous oxide, nitrogen, air and the like.

Solvent: Ethyl alcohol, methylene chloride, isopropanol, acetone, castor oil, ethylene glycol monoethyl ether, diethylene glycol monobutyl ether, diethylene glycol monoethyl ether, dimethyl sulfoxide, dimethylformamide, tetrahydrofuran and the like.

Moisturizers: glycerin, sorbitol, sodium 2-pyrrolidone-5-carboxylate, soluble collagen, dibutyl phthalate, gelatin and the like.

Powders: chalk, talc, fuller's earth, kaolin, starch, rubber, colloidal silicon dioxide, sodium polyacrylate, tetraalkyl and / or trialkylaryl ammonium smectites, chemically modified magnesium aluminum silicate, organic Modified montmorillonite clay, hydrated aluminum silicate, fumed silica, carboxyvinyl polymer, sodium carboxymethyl cellulose, ethylene glycol monostearate, etc.

The cosmetically acceptable excipients, which are optionally present, usually make up 0.01 to 99.9% by weight of the composition, preferably 59 to 98% by weight. Excipients may make up the balance of the composition in the absence of other cosmetic additives.

Toothpaste compositions usually contain an abrasive gel (eg calcium carbonate), an oral therapeutic agent (eg a fluorine-containing compound), a co-active substance, a flavoring agent, a sweetener, a humectant, and a binding or thickening gel. . Moisturizers that can be used include
Includes glycerol, sorbitol syrup, polyethylene glycol, lactitol, xylitol and hydrogenated corn syrup. The total amount of humectant present is usually 10-85% by weight of the toothpaste composition.

Preferred conditioner compositions are those containing conditioning agents such as those described in US Pat. No. 4,913,828 (eg, alkylamine compounds).

The concept of an axillary deodorant / antiperspirant composition is described in US Pat. Nos. 4,919,934 (Deckner), 4,9, which are incorporated herein by reference.
44,937 (McCall) and 4,943.
No. 4,938 (Patini). The composition as described above usually comprises a cosmetic composition in the form of a stick (gel or wax), the composition usually comprising one or more liquid base materials (eg water, fatty acids and fatty alcohol esters, water-insoluble ethers and alcohols). , Polyorganosiloxanes); solidifying agents for solidifying liquid bases; and active ingredients such as antibacterial or antifungal agents (for deodorant activity) or astringent metal salts (for antiperspirant activity) . These compositions are hardeners, reinforcing agents,
Emollients, colorants, fragrances, emulsifiers and fillers may also be included. The composition of the invention is similar to that described above and comprises at least one aldobionamide.

Typical Composition One typical shampoo composition according to the present invention consists of the following ingredients:

(1) Aldionamide 5 to 15% (2) Anionic synergistic (complementary) activator 0 to 10% (3) Amphoteric synergistic activator 0 to 10% (4) Lauramide MEA 0 to 5 % (5) Thickener 0-5% (6) Fragrance 0-2% (7) Preservative 0-1% (8) Water Up to 100% One typical shaving cream composition according to the invention is It consists of ingredients.

(1) Stearic acid 20-40% (2) Coconut oil or fatty acid 6-10% (3) Aldionamide 1-45% (4) Glycerol 5-15% (5) Potassium hydroxide 2-6 % (6) Sodium hydroxide 1-3% (7) Vegetable oil or mineral oil 1-5% (8) Water up to 100% One typical brushless shaving cream composition according to the invention consists of the following ingredients.

(1) Glyceryl monostearyl 10-35% (2) Mineral oil 5-15% (3) Aldionamide 1-45% (4) Glycerol 1-45% (5) Water up to 100% 1 according to the invention 1 One typical shaving lotion composition consists of the following ingredients.

(1) Cellulose alkali ether 70-75% (2) Glycerol 3-10% (3) Aldionamide 1-5% (4) Mineral oil 10-20 (5) Water up to 100% One according to the invention A typical shower gel composition consists of the following components.

(1) Sodium cocoyl isothionate 5-10% (2) Sodium lauryl sulfonate ether 2-5% (3) Aldionamide 1-45% (4) Coconut amide propyl betaine 8-15% (5 ) Ethylene glycol distearate 4-10% (6) Isopropyl palmitate 0.5-1% (7) Wetting component 0.25-0.5% (8) Preservative 0.05-0.1% (9) ) Sodium chloride 3-5% (10) Water up to 100% One typical bar soap composition according to the invention consists of the following components.

(1) C _{8 to} C ₂₄ fatty acid 5 to 60% (2) aldobionamide 1 to 45% (3) coactivator other than aldonamide 0 to 50% (4) alkyl or aryl sulfate or Sulfonate 0-5% (5) Wetting agent (eg sorbitol or glycerin) 0.1-10% (6) Water-soluble polymer (eg cellulose) 0-10% (7) Sequestering agent (eg citrate) 0.1-0.5% (8) Dye <0.1% (9) Optical brightness improver <0.1% (10) Whitening agent 0.1-0.4% (11) Fragrance 0. 1-2.0% (12) Water Up to 100% One typical face-body cleanser composition according to the present invention consists of the following ingredients.

(1) C _{8 to} C ₂₄ fatty acid salt (eg triethanolamine) 1 to 45% (2) aldobionamide 10 to 75% (3) alkyl or aryl sulphate or sulfonate 0 to 20% (4) Co-active surfactants (e.g. cocoamidobetaine) 1-15% (5) Wetting agents (e.g. citrate) 0.1-15% (6) Refatting alcohols 0.5-5% (7) ) Water-soluble polymer 0-10% (8) Thickener 0-15% (9) Conditioner (eg quaternized cellulose) 0-0.5% (10) Sequestering agent (eg citrate) 0.1 0.4% (11) Dye <0.1% (12) Optical brightness improver <0.1% (13) Whitening agent 0.1-0.4% (14) Fragrance 0.1-3 0.0% (15) Preservative 0 .2% (16) One typical dentifrice compositions according to the invention to 100% water consists of the following components.

(1) Synthetic surfactant (sodium lauryl sulfonate 1.5% (2) Aldionamide 1-10% (3) Alkyl or aryl sulfonate or sulfonate 0-1% (4) Polishing powder (eg Silicic acid / CaCO ₃ ) 20 to 55% (5) Active ingredient (for example, pyrophosphate) 0.1 to 2% (6) Wetting agent (glycerin, sorbitol) 10 to 45% (7) Thickener (cellulose derivative ) 0-3% (8) Sequestering agent (for example, citrate) 0.1-0.4% (9) Fragrance 0.5-2% (10) Sweetener <0.5% (11) Dye < 0.1% (12) Water up to 100%

[0107]

The present invention will be described in more detail by the following examples. These examples are merely illustrative of the invention and are not intended to limit the invention.

Method for producing N-alkyl lactobionamides
Method Synthesis of N-alkyl lactobionamides As shown below, commercially available lactobiono-1,5-lactone and various linear alkyls, either in anhydrous DMF, in methanol, or without solvent (neat). N-alkyl lactobionamides were synthesized by reacting with amines.

[0109]

[Chemical 5]

Method using dimethylformamide as a solvent:
The method involved dissolving lactobiono-1,5-lactone in a minimum amount of anhydrous DMF at 80 ° C., followed by addition of 1 equivalent of alkylamine. Although this method gave good yields, the product was colored and required repeated washings with solvent.

Method using methanol as solvent: US Pat. No. 2,752,334 (National Di)
The method described in ary) was carried out. Lactobiono-1,
5-Lactone and the alkylamines were refluxed in methanol and the corresponding colored product was isolated in moderate yield. Decontamination of the product required continuous washing with solvent.

Solventless method: 90% of excess alkylamines and lactobiono-1,5-lactone with vigorous stirring.
Heated at ~ 100 ° C. The colored product was isolated in moderate yields.

Specific examples of each of these methods are described in more detail below.

Alternative to N-tetradecyl lactobionamide
Synthesis: Lactobiono-1,5-lactone (400 mL) in a 5 L three-necked round bottom flask equipped with a condenser and mechanical stirrer.
g) was dissolved in warm methanol (3.5 L, 50-55 ° C) and then melted tetradecylamine (1.0 eq, 2
72 g) was added. The reaction was cooled to room temperature and then stirred overnight for complete crystallization. The desired white product was filtered off and recrystallized from methanol. The isolated yield was 91% (550 g). The methanol filtrate is N-
It contained a mixture of tetradecyl lactobionamide and tetradecyl ammonium lactobionate.

Further N-alkylaldonamides were isolated using the method described above.

Example 1: N-decyl lactobionamide
Preparation 20 g (1 eq) Lactobiono-1,5-lactone was dissolved in 40 ml anhydrous DMF at 75-80 ° C and 8.8
g (1 equivalent) of decylamine was added. The reaction was maintained at 75-80 ° C for 30 minutes with stirring. The reaction was cooled and ethyl ether (150 ml) was added, then the product was filtered off and washed with ethyl ether (2 x 100 m).
It was washed with l). Recrystallization from methanol / ethyl ether gave the desired product in 80% yield.

Example 2: N-dodecyl lactobionamide
Preparation of 30 g (1 equivalent) of Lactobiono-1,5-lactone was dissolved in 70 ml of anhydrous DMF at 75-80 ° C.
5.85 g (1 eq) dodecylamine was added and the reaction mixture was kept stirring at 70-80 ° C. for 30 minutes. The reaction solution was cooled and ethyl ether (200 ml) was added. The product was filtered off and washed with ethyl ether (2 x 150 m
After washing with l), recrystallization from MeOH gave the desired product in 90% yield.

Example 3: N-tetradecyl lactobiona
Preparation of Mido Lactobiono-1,5-lactone (20 g, 1 eq) was dissolved in 60 ml of anhydrous DMF at 65 ° C., 12.5 g of tetradecylamine (1 eq) was added and the reaction was stirred at 65 ° C. Stir for 30 minutes. The reaction mixture was cooled and ethyl ether (2 x 150 ml) was added. The product was filtered off and washed with ethyl ether. Recrystallization from methanol gave the desired product in 92% yield.

Example 4: N-hexadecyl lactobiona
Preparation of amide A method similar to Example 3 was used, using 10 g (1 eq) of Lactobiono-1,5-lactone and 7.1 g (1 eq) hexadecylamine. Recrystallization from MeOH gave the desired product in 90% yield.

Example 5: N-propyl lactobionamide
Preparation of 5 g (1 equivalent) of 8 Lactobiono-1,5-lactone
It was dissolved in 20 ml of anhydrous DMF at 0 ° C and 0.86 g (1
Eq) propylamine was added. The reaction solution was stirred at 80 ° C. for 30 minutes. After removing the solvent, the residue was washed with ethyl ether (2 x 50 ml). Recrystallization from MeOH / ethyl ether gave the desired product in 80% yield.

Example 6: N-pentyl lactobionamide
Preparation of Lactobiono-1,5-lactone (5 g, 1 eq) and amylamine (1.41 g, 1 eq) were heated in 30 ml anhydrous methanol and refluxed for 1 hour. A small amount of activated carbon was added, and the mixture was filtered while hot. The solvent was removed and the residue was washed with ethyl ether then acetone and dried. Yield is 5
It was 0%.

Example 7: N-octyl lactobionamide
Preparation of Lactobiono-1,5-lactone (10 g, 1 eq) and octylamine (7.6 g, 2 eq) were heated to 90 ° C. for 30 minutes with vigorous stirring. The reaction was cooled and washed with ethyl ether (2 x 150 ml). MeOH
/ Recrystallized twice from ethyl ether to give the desired product in 80% yield.

Example 8: N-dodecyl lactobionamide
Preparation of 20 g of Lactobiono-1,5-lactone and 11 g (1
(Eq.) Dodecylamine was dissolved in 200 ml of methanol by heating to reflux temperature. The reaction mixture was stirred at room temperature overnight. The product was filtered off and methanol (100 m
l) then washed with ethyl ether (2 x 75 ml). Recrystallization from MeOH gave the desired product in 57% yield.

Example 9: N-lactobionil dodecyl
Preparation of ricinate 9.0 g of dodecyl glycinate hydrochloride was dissolved in 50 ml of anhydrous methanol by gentle heating to give 16 ml of
After adding 2.0 M methanolic ammonia,
0.9 g (1 equivalent) of Lactobiono-1,5-lactone was added. The reaction mixture was heated under reflux for 2.0 hours, activated carbon was added, and the mixture was hot filtered. The solvent was removed, the product was washed with ethyl ether and dried in a vacuum oven at 40 ° C. with P ₂ O ₅ to give the desired product in about 75% yield.

Example 10; N-lactobionyldodecyl
In a procedure similar to that described above for β-alanate dodecyl glycinate, 3.0 g of dodecyl β-alanine hydrochloride was added to lactobiono-.
Formed by reacting 3.45 g of 1,5-lactone in anhydrous methanol. The yield was about 70%.

Example 11: N-decyloxypropyl la
Was dissolved lactobiono-1,5-lactone 50g in Kutobionamido 400ml of methanol (50-55 ° C.), decyloxy propylamine [Adogen (R) 180,3
1.6 g, 1 eq] was added. The reaction was cooled to room temperature and stirred overnight. Acetone 4 after removing the solvent (250 ml)
00 ml was added. The product was filtered, washed with acetone and dried in a vacuum oven at 40 ° C. Yield is about 80%
Met.

Example 12: Preparation of cocolactobionamide Lactobiono-in methanol (2.3 l, 50 ° C).
1,5-Lactone (400 g, 1 eq) was dissolved with stirring to give cocoamine [Adogen ™ 160-D
(R) 211,8 g, 1 eq] was added slowly over 10 minutes. After the addition was complete, the reaction mixture was stirred for an additional 10 minutes, after which the solution was sheeted with a small amount of cocolactobionamide and left overnight with stirring at room temperature. The product is filtered, washed twice with hot acetone, 40 ° C.
Dried in a vacuum oven. The yield was 394 g.

Example 13: Preparation of tallow lactobionamide Lactobiono-in methanol (1.3 l , 45 ° C)
1,5-Lactone (200 g, 1 eq) was dissolved with stirring to give tallow amine [Adogen ™ 170-D
(R) 144, 7 g, 1 equivalent] was slowly added in several portions. After the addition was complete, the reaction mixture was stirred at room temperature overnight. The product was filtered, washed with isopropanol then acetone and dried in a vacuum oven at 40 ° C. Yield is 2
It was 70 g.

Example 14: of oleyl lactobionamide
Lactobiono in manufactured methanol (400 ml, 50 ° C)
1,5-Lactone (100 g, 1 eq) was dissolved and oleylamine [Adogen ™ 127-D, 76.
1 g, 1 eq] was added slowly. After the addition was complete, the reaction mixture was stirred at room temperature overnight. The product was filtered, washed twice with acetone and dried in a vacuum oven at 40 ° C. The yield was 130 g.

Example 15; N-dodecyl-N-methylra
Preparation of ctobionamide Lactobiono-in methanol (30 ml, 50 ° C)
1,5-lactone (8.7 g, 1 equivalent) was dissolved and N-
Dodecylmethylamine (5 g, 1 eq) was added. The reaction mixture was stirred at room temperature overnight. The solvent was removed, the product was washed with acetone and dried in a vacuum oven at 40 ° C.
The yield was 12 g.

Examples 16-19; Surfactant Activity To determine the effectiveness of these compounds as surfactants, the various physical properties of surfactants related to how good they were. Characteristics [ie CMC,
Craft point, height of lather, Zein solubility (Zein d
and the cleaning power] was measured. In particular,
These properties were compared to those of known and commonly used nonionic ethoxylated surfactants. The results of these various measurements are described below as Examples 16-19.

Example 16; Critical Micelle Concentration (CMC) CMC is defined as the concentration of surfactant that begins to form micelles in solution. In particular, substances containing both hydrophobic and hydrophilic groups (eg surfactants) tend to distort the structure of the solvent containing them (ie water) and thus increase the free energy of the system.

As a result, these substances concentrate on the surface,
Orientation there directs the hydrophobic groups of those materials away from the solvent, minimizing the free energy of the solution. Another means of minimizing free energy is to interface in a cluster or micelle with a hydrophobic group lining the cluster and a hydrophilic group lining the cluster and a hydrophilic group lining the solvent. This can be achieved by aggregation of active molecules.

The CMC value is the Wilhemy plate method (Wi
It is determined by measuring the surface tension using a hemi plate method). While not wishing to be in theory, low CMC is a measure of surface activity (ie, one surfactant has a lower CMC than the other).
If so, the surfactant having a low CMC has stronger surface activity).

In this connection, a low CMC is a high CM.
It is believed that the same surfactant effect as C surfactant is exhibited and that a smaller amount of surfactant is required.

The CMC of various surfactants was measured, and the results are as follows.

[0137]

[Table 1]

As the table above shows, the CMC values of N-decyl and tetradecyl lactobionamide were found to be comparable to those of N-dodecyl-β-D-glucoside and heptaethoxylated dodecyl alcohol.

These values show that the lactobionamide surfactant is comparable to other widely used nonionic surfactants.

Example 17: Kraft point Above a certain temperature, the surfactant begins to form micelles instead of precipitates, which temperature is called the Kraft point (Tk) and the solubility of the surfactant at this temperature is It will be equal to its CMC.

The Kraft point was determined by preparing a 1% dispersion of surfactant in water. If the surfactant was soluble at room temperature, the solution was cooled to 0 ° C. If the surfactant did not precipitate, its Kraft point was considered to be below 0 ° C. If precipitated, the solution was heated slowly with stirring in a water bath. The temperature at which the precipitate dissolved was determined as the Kraft point.

If the Kraft point was above room temperature, the solution was first heated rapidly until all the surfactant had dissolved.
It was then cooled until precipitation occurred and then gradually heated and the Kraft point determined by the above method.

Although not in theory, the low Kraft point is believed to indicate a more soluble surfactant in aqueous systems.

The Kraft points for various lactobionamides are shown below:

[0145]

[Table 2]

From this table it can be seen that the C ₁₀ chain length surfactants have better surface activity properties at low temperatures than their C ₁₂ and C ₁₄ counterparts.

Example 18: Foam Height Foam plays an important role in many household items. Foam is one of the important factors that determines the commercial value of products such as shampoo and soap. Similarly, the acceptance of household items is closely related to the quality and feel (psychological aspect) of the foam it produces.

Most of the data on surfactant foams are based on the Ross-Miles method (GD Am. Soc. For T).
esting Material Method D1173-53, Philadelphia, PA.
(1953); Oil & Soap (1958) 62: 1260), and the foam activity of these surfactants was also obtained using this method.

In the Ross-Miles method, 20 pipettes with a specific size of 2.9-mm-id orifice were used.
0 mL of the surfactant solution is dropped 90 cm onto 50 mL of the same surfactant solution in a cylindrical container maintained at a predetermined temperature (eg 60 ° C.) with a water jacket. The height of bubbles generated in this cylindrical container was measured immediately after all the solutions flowed out from the pipette (initial height) and for a predetermined time (generally 5
Min) and measure again later.

Using this method, foam productivity (initial height)
And foam stability (height after 10 minutes). All foams were made in water at 45 ° C. with a hardness of 120 ppm. Bubble height is expressed in mm.

The initial foam height and foam stability (height after 10 minutes) for various surfactants and mixtures thereof are shown below.

[0152]

[Table 3]

As can be seen from the table above, C ₁₄ lactobionamide and the C ₁₄ and C ₁₂ lactobionamide mixture showed the best foam stability.

It should be noted that other types of nonionic surfactants usually do not provide such foam stability.

Example 19: Paired cyclic aldobionamides
Linear saccharides To show that the aldobionamides of the present invention (ie, having at least two saccharide units) are superior to linear saccharides (eg, glucurnamide), C ₁₀ , C ₁₂ and C ₁₄ measures the Krafft point of Gurukunamaido and compared them with the Krafft point of the C _10, C ₁₂ and C ₁₄ lactobionate na amide. Specifically, 1
g of surfactant was measured in 99 g of water (1% surfactant solution). The results are shown below.

[0156]

[Table 4]

The structure of glucurnamide is as follows:

[0158]

[Chemical 6]

Wherein R ₁ and R ₂ are as defined for the aldobionamides of this invention.

From the table above, it can be seen that the Kraft point of lactobionamide (ie, an index of solubility) is significantly lower than that of glucurnamide of the same chain length.

Without being bound by theory, it appears that linear glucurnamide is more tightly folded and, as a result, at least partially correlates with the fact that it is less soluble in solution. . A low craft point is also associated with a high yield.

Example 20: Glucunamide and Lacquer
Shampoo with Tobionamide To further demonstrate the difference in solubility between the aldobionamides of the present invention and the linear saccharides (eg, glucurnamide), shampoos having the following composition were made.

[0163]

[Table 5]

Cocolactobionamide 4% and 8% respectively
Compositions (A) and (B) containing were homogeneous viscous liquid shampoos. On the other hand, the composition (C) containing N-dodecyl-glucurnamide was a cloudy non-viscous liquid shampoo due to precipitation of N-dodecyl-glucurnamide. This is probably due to the high craft temperature.

It was also confirmed that lactobionamide was readily soluble until reaching 8%. On the other hand, 4% of glucurnamide was not soluble.

Continuation of front page (51) Int.Cl. ⁶ Identification number Internal reference number FI Technical indication location C07H 15/04 D C11D 1/68 (72) Inventor Vijayan Haryachian United States, New Jersey, County of Esetx, West South Orange Avenue 420 (72) Inventor Michael Matsusalo New York 10920, Congers, Dover Road 39

Claims (13)

[Claims] 1. A personal product composition comprising at least one aldobionamide as an active agent. 2. The following general formula: [Wherein R ₁ and R ₂ are the same or different and are selected from the group consisting of hydrogen, aliphatic hydrocarbon groups, aromatic groups, alicyclic groups, amino acid esters, ether amines and mixtures thereof. Wherein R ₁ and R ₂ are not hydrogen at the same time]. 3. The following general formula: [Wherein R ₁ and R ₂ are the same or different and are selected from the group consisting of hydrogen, aliphatic hydrocarbon groups, aromatic groups, alicyclic groups, amino acid esters, ether amines and mixtures thereof. Wherein R ₁ and R ₂ are not hydrogen at the same time]. 4. A composition according to claim 1, comprising aldobionamide and at least one activator other than aldobionamide. 5. The activator other than the at least one aldobionamide is fatty acid soap, alkyl ether sulfate, alkyl ethoxylate, alkyl glyceryl ether sulfonate, methyl acyl taurate, N-acyl glutamate, acyl isethionate. , Anionic acyl sarcosinates, methyl glucose esters, protein condensates, ethoxylated alkyl sulfates, alkyl polyglycosides, alkyl amine oxides, betaines, sulteines, alkyl sulfosuccinates, N-polyhydroxyalkyl fatty acid amides, and mixtures thereof. A composition according to claim 4 selected from the group consisting of: 6. The composition of claim 5, further comprising free fatty acids. 7. The composition of claim 1, further comprising one or more humectants, polymeric skin sensation aids and emollients. 8. The humectant is a long-chain fatty acid, a liquid water-soluble polyol, glycerin, propylene glycol, sorbitol, polyethylene glycol, an ethoxylated / propoxylated ether of methyl glucose, an ethoxylated / propoxylated ether of lanolin alcohol, and pyrrolidone. Sodium carboxylate, lactic acid, urea, L-proline,
Guanidine and pyrrolidone, adipic acid, lactic acid, oleic acid, stearic acid, isostearic acid, hexadecyl, myristyl, isodecyl or isopropyl ester of myristic acid or linolenic acid, corresponding alcohol ester, hydrogenated protein, collagen-derived protein, aloe vera gel, acetamide MEA, petrolatum, mineral oil, beeswax, silicone, lanolin and oil-soluble lanolin derivatives, saturated and unsaturated fatty alcohols, squalene and squalane, almond oil, peanut oil, wheat germ oil, linseed oil, jojoba oil, apricot kernel oil, Walnut, coconut, pistachio, sesame, rapeseed, cade oil, corn oil, peach kernel oil, poppy seed oil, pine oil, camphor oil, soybean oil, avocado oil, safflower oil, coconut oil, hazelnut oil, olive oil The composition of claim 7 selected from the group consisting of :, grape seed oil, and sunflower seed oil. 9. The polymeric skin sensation aid is a nonionic polysaccharide, a copolymer of dimethylaminoethyl methacrylate and acrylamide, a copolymer of dimethyldiallylammonium chloride and acrylamide [a neutral monomer unit of a cationic monomer]. The composition is selected such that the copolymer has a cationic charge], cationic starch, and mixtures thereof. 10. The composition of claim 1 further comprising one or more polyalkyl siloxanes, polyaryl siloxanes, polyalkylaryl siloxanes or polyether siloxane copolymers and silicone rubber from about 0.1% to about 10.0%. object. 11. Further one or more kinds of chalk, talc,
Fuller's earth, kaolin, starch, rubber, colloidal silicon dioxide, sodium polyacrylate, tetraalkyl and / or trialkylaryl ammonium smectite, chemically modified magnesium alumina silicate, organic modified montmorillonite clay, hydrated aluminum silicate A composition according to claim 1, comprising: fumed silica, carboxyvinyl polymer, sodium carboxymethyl cellulose and ethylene glycol monostearate. 12. 30-95% fatty acid soap and at least
The bar of claim 1 containing 1% aldobionamide. 13. At least 1% of aldobionamide, and fatty acid soap, alkyl ether sulfate, alkyl ethoxylate, alkyl glyceryl ether sulfonate, methyl acyl taurate, N-acyl glutamate, acyl isethionate, anionic acyl. Sarcosinate, methyl glucose ester, protein condensate, ethoxylated alkyl sulfate, alkyl polyglycoside, alkyl amine oxide, betaine,
Containing at least 1% of an active agent selected from the group consisting of sultaine, alkyl sulfosuccinates, N-polyhydroxyalkyl fatty acid amides, and mixtures thereof,
A liquid cleansing composition according to claim 1 for human skin or hair.