WO1999024538A1

WO1999024538A1 - Alkyl polyglycoside ether carboxylates

Info

Publication number: WO1999024538A1
Application number: PCT/US1998/023230
Authority: WO
Inventors: Norman Milstein; Barry A. Salka; Armin Wadle
Original assignee: Henkel Corporation; Henkel Kommanditgesellschaft Auf Aktien
Priority date: 1997-11-10
Filing date: 1998-11-09
Publication date: 1999-05-20
Also published as: AU1297199A

Abstract

A personal care product containing a surfactant corresponding to formula (I): R1O(R2O)b(Z)aOCH2COO-X+, wherein R¿1? is a monovalent organic radical having from about 6 to about 30 carbon atoms; R2 is a divalent alkylene radical having from 2 to 4 carbon atoms; Z is a saccharide residue having 5 or 6 carbon atoms; b is a number having a value from 0 to about 12; a is a number having a value from 1 to about 6; and X is an alkali metal ion.

Description

ALKYL POLYGLYCOSIDE ETHER CARBOXYLATES

Field of the Invention

The present invention generally relates to alkyl polyglycoside ether

carboxylates, their preparation, and to their use as surfactants.

Background of the Invention:

It is known that various surfactants have been found to be useful in

cleaning compositions, such as shower gels, shampoos, and light-duty

detergents such as dish washing detergents. In these types of compositions,

good foamability is a prerequisite. The most widely used surfactants in these

types of compositions are anionic surfactants such as alkyl sulfates, alkyl ether

sulfates, sulfonates, sulfosuccinates and sarcosinates.

Although the use of anionic surfactants in these compositions permits the

attainment of desirable properties, including good foamability, the degree of

foam stability leaves much to be desired. Foam stability relates to the ability of

the foam, once formed, to remain intact for extended periods of time, thus

enhancing the cleaning performance of the surfactant compositions.

It is sometimes advantageous to use mixtures of surfactants in cleaning

compositions when the surfactants can serve different functions, e.g., one

serving to improve foamability and another serving to adjust viscosity. However,

known surfactant mixtures typically provide a compromise between what can be

achieved with the surfactant ingredients alone. For example, a mixture of more costly surfactants such as amine oxides, betaines and alkanolamides which

provide good foamability by themselves, with less expensive surfactants which

provide poorer foamability will result in the formulation of a cleaning composition

having an intermediate degree of foamability and poor foam stability

Alkyl polyglycosides are used as nonionic surfactants and are

distinguished from other nonionic surfactants by their excellent detergent

properties and high ecotoxicological compatibility. For this reason, this class of

nonionic surfactants is acquiring increasing significance. They are generally

used in liquid formulations, for example, dishwashing detergents and hair

shampoos. However, because of their increased desirability as surface active

agents, there use as surfactants in many other types of products is growing

rapidly.

While the use of mixtures of anionic and nonionic surfactants in most

cases serves to further the objectives of both classes of surfactants, it would be

much more desirable, and significantly less costly to employ, a single compound

which would exhibit the favorable properties which are indigenous to both

anionic and nonionic surfactants.

Summary of the Invention:

The present invention provides a novel surfactant having general formula

R₁O(R₂O)_b(Z)_aOCH₂COO X⁺ I

wherein R< is a monovalent organic radical having from about 6 to about 30 carbon atoms; R₂ is a divalent alkylene radical having from 2 to 4 carbon atoms;

Z is a saccharide residue having 5 or 6 carbon atoms; b is a number having a

value from 0 to about 12; a is a number having a value from 1 to about 6; and

X is an alkali metal ion.

There is also provided a process for making novel surfactants involving:

(a) providing an alkyl polyglycoside having general formula II:

R₁O(R₂O)_b(Z)_a II

wherein R< is a monovalent organic radical having from about 6 to about 30

carbon atoms; R₂ is a divalent alkylene radical having from 2 to 4 carbon atoms;

Z is a saccharide residue having 5 or 6 carbon atoms; b is a number having a

value from 0 to about 12; a is a number having a value from 1 to about 6;

(b) providing a non-aqueous alkali metal compound;

(c) dispersing the alkyl polyglycoside in the nonaqueous alkali metal

compound to form a reaction mixture; and

(d) adding an acetate derivative to the reaction mixture to form a reaction

product.

Description of the Invention:

Other than in the operating examples, or where otherwise indicated, all

numbers expressing quantities of ingredients or reaction conditions are to be

understood as being modified in all instances by the term "about".

The alkyl polyglycosides which can be used in the compositions according

to the invention have the general formula II:

R R.OyZk II wherein R, is a monovalent organic radical having from about 6 to about 30

Z is a saccharide residue having 5 or 6 carbon atoms; b is a number having a

value from 0 to about 12; a is a number having a value from 1 to about 6.

Preferred alkyl polyglycosides which can be used in the compositions according

to the invention have the formula I wherein Z is a glucose residue and b is zero.

Such alkyl polyglycosides are commercially available, for example, as APG®,

GLUCOPON®, or PLANTAREN® surfactants from Henkel Corporation, Ambler,

PA, 19002. Examples of such surfactants include but are not limited to:

1. APG® 225 Surfactant - an alkyl polyglycoside in which the alkyl group

contains 8 to 10 carbon atoms and has an average degree of polymerization of

1.7.

2. GLUCOPON® 425 Surfactant - an alkyl polyglycoside in which the alkyl group

contains 8 to 16 carbon atoms and has an average degree of polymerization of 1.55.

3. GLUCOPON® 625 Surfactant - an alkyl polyglycoside in which the alkyl group

contains 12 to 16 carbon atoms and have an average degree of polymerization

of 1.6.

4. APG® 325 Surfactant - an alkyl polyglycoside in which the alkyl group

contains 9 to 11 carbon atoms and have an average degree of polymerization

of 1.6.

5. GLUCOPON® 600 Surfactant - an alkyl polyglycoside in which the alkyl group

contains 12 to 16 carbon atoms and have an average degree of polymerization of 1.4.

6. PLANTAREN® 2000 Surfactant - a C₈.₁₆ alkyl polyglycoside in which the alkyl

group contains 8 to 16 carbon atoms and has an average degree of

polymerization of 1.5.

7. PLANTAREN® 1300 Surfactant - a C₁₂.₁₆ alkyl polyglycoside in which the alkyl

group contains 12 to 16 carbon atoms and have an average degree of

polymerization of 1.6.

8. PLANTAREN® 1200 Surfactant - a C₁₂._1β alkylpolysaccharide in which the

alkyl group contains 12 to 16 carbon atoms and have an average degree of

polymerization of 1.4.

Other examples include alkyl polyglycoside surfactant compositions which

are comprised of mixtures of compounds of formula I wherein Z represents a

moiety derived from a reducing saccharide containing 5 or 6 carbon atoms; a is

a number having a value from 1 to about 6; b is zero; and R* is an alkyl radical

having from 8 to 20 carbon atoms. The compositions are characterized in that

they have increased surfactant properties and an HLB in the range of about 10

to about 16 and a non-Flory distribution of glycosides, which is comprised of a

mixture of an alkyl monoglycoside and a mixture of alkyl polyglycosides having

varying degrees of polymerization of 2 and higher in progressively decreasing

amounts, in which the amount by weight of polyglycoside having a degree of

polymerization of 2, or mixtures thereof with the polyglycoside having a degree

of polymerization of 3, predominate in relation to the amount of monoglycoside,

said composition having an average degree of polymerization of about 1.8 to about 3. Such compositions, also known as peaked alkyl polyglycosides, can be

prepared by separation of the monoglycoside from the original reaction mixture

of alkyl monoglycoside and alkyl polyglycosides after removal of the alcohol.

This separation may be carried out by molecular distillation and normally results

in the removal of about 70-95% by weight of the alkyl monoglycosides. After

removal of the alkyl monoglycosides, the relative distribution of the various

components, mono- and poly-glycosides, in the resulting product changes and

the concentration in the product of the polyglycosides relative to the

monoglycoside increases as well as the concentration of individual

polyglycosides to the total, i.e., DP2 and DP3 fractions in relation to the sum of

all DP fractions. Such compositions are disclosed in U.S. patent 5,266,690, the

entire contents of which are incorporated herein by reference.

Other alkyl polyglycosides which can be used in the compositions

according to the invention are those in which the alkyl moiety contains from 6 to

18 carbon atoms in which and the average carbon chain length of the

composition is from about 9 to about 14 comprising a mixture of two or more of

at least binary components of alkylpolyglycosides, wherein each binary

component is present in the mixture in relation to its average carbon chain length

in an amount effective to provide the surfactant composition with the average

carbon chain length of about 9 to about 14 and wherein at least one, or both

binary components, comprise a Flory distribution of polyglycosides derived from

an acid-catalyzed reaction of an alcohol containing 6-20 carbon atoms and a

suitable saccharide from which excess alcohol has been separated. A particularly preferred alkyl polyglycoside of formula II is one wherein R.,

is a monovalent organic radical having from 12 to 16 carbon atoms, b is zero,

and a is a number having a value of about 1.4.

According to one aspect of the invention, there is provided a novel

surfactant having general formula I:

R₁O(R₂O)_b(Z)_aOCH₂COO X⁺ I

wherein R^ is a monovalent organic radical having from about 6 to about 30

Z is a saccharide residue having 5 or 6 carbon atoms; b is a number having a

value from 0 to about 12; a is a number having a value from 1 to about 6; and

X is an alkali metal ion.

These novel surfactants possess both anionic and nonionic properties.

They provide superior levels of stable foam and act as viscosity builders when

used in various types of detergent compositions.

In a particularly preferred embodiment of the novel surfactant of formula

I, R_T is a monovalent organic radical having from 12 to 16 carbon atoms, b is

zero, and a is a number having a value of about 1.4.

Another aspect of the present invention provides a process for making the

above-disclosed novel surfactants. According to this aspect of the invention, the

alkyl polyglycosides of formula II are etherified by reaction with a chloroacetate

derivative such as, for example, sodium monochloroacetate. This reaction is

carried out in a non-aqueous medium in the presence of alkali metal ions,

preferably potassium or sodium ions. The alkali metal compound is preferably employed in the form of an oxide such as, for example, sodium ethoxide, sodium

hydroxide or potassium tert-butoxide.

In a preferred embodiment of the invention, about 1 mole of alkyl

polyglycoside is first reacted with from about 1 to about 2 moles, and most

preferably about 1 mole of alkali metal oxide to form a reaction mixture. This

reaction is preferably carried out at a temperature ranging from about 70 to

about 90°C, and most preferably about 80°C, and at a pH ranging from about 10

to about 14, and most preferably about 12.

Once the reaction mixture is formed, from about 1 to about 2 moles, and

preferably about 1 mole of a chloroacetate derivative is added to the reaction

mixture. Examples of suitable chloroacetate derivatives include, but are not

limited to, sodium monochloroacetate and ethyl chloroacetate. In a particularly

preferred embodiment, the chloroacetate derivative is sodium

monochloroacetate.

The chloroacetate derivative is added to the reaction mixture at a

temperature ranging from about 60 to about 70°C, and a pH ranging from about

12 to about 14.

A procedure for making the novel surfactant is as follows. An alkyl

polyglycoside is mixed with an organic reagent such as, for example, xylene or

toluene, and subsequently heated in order to azeotropically remove any water

contained in the alkyl polyglycoside, thus forming a mixture of anhydrous alkyl

polyglycoside and solvent. This mixture is then heated to a temperature of about

70°C at which time an alkali metal compound is added. A solvent such as, for example, ethanol may be added to the mixture in order to liquefy the mixture if

needed. The chloroacetate derivative is then added to the reaction mixture,

thereby etherifying the alkyl polyglycoside so as to form the novel surfactant of

formula I. According to another aspect of the invention, there is provided a cleaning

composition containing from about 20 to about 35% by weight, and preferably

from about 25 to about 30% by weight of the novel surfactant of formula I, based

on the weight of cleaning composition. The formulation of cleaning compositions

may vary widely. It is well known that detergent and cleaning compositions

contain surfactants and, in most cases, builders. While various surfactants,

builders and additives may be employed in combination with the novel surfactant

of formula I, the basis of this aspect of the invention is the presence of the

surfactant of formula I in a cleaning composition, in the above-disclosed

amounts.

The following example is illustrative of the process and composition of the

present invention and will be useful to one of ordinary skill in the art in practicing

the invention. However, the invention is in no way limited by these examples.

Example 1 A mixture of 650 grams (one mole) of a C₁₂.₁₆ alkyl polyglycoside having

an average degree of polymerization of 1.4 and 700 ml of toluene were heated

in order to azeotropically distill any water present in the alkyl polyglycoside,

using a Dean Stark trap. The temperature of the mixture rose from 85 °C to

110°C. The distillation required about 4 hours. The dry alkyl polyglycoside was clearly soluble in the toluene at room temperature. To this mixture, 485 grams

(one mole) of ethanolic sodium hydroxide was added, with agitation. When the

addition was complete, the reaction mixture was heated to about 60°C for about

1 hour, at which time 116.5 grams (one mole) of sodium monochloroacetate was

added, with stirring, and was refluxed for about 5 hours. Water was then added

in 200 ml increments while distilling, in 200 ml increments, the ternary azeotrope

(toluene/ethanol/water) until the pot temperature reached about 100°C and only

water remained in the product. This required about 8 hours. The distillate came

off as two layers: the top layer being rich in toluene, and the bottom layer being

rich in water. The top layer was used to azeotropically dry the next batch of alkyl

polyglycoside starting material, the distillate initially consisting of the ternary

azeotrope, toluene/ethanol/water, and finishing as the binary azeotrope,

toluene/water. Wet analysis data performed on the residue is found in Table I

below.

Table I

The alkyl polyglycoside ether carboxylates of the present invention may

also be employed in personal care products such as cosmetic and

pharmaceutical formulations. These personal care products include, for

example, hair shampoos, hair lotions, bubble baths, skin creams, lotions, and

ointments. Thus, according to another embodiment of the present invention, there is provided a personal care composition containing an alkyl polyglycoside

ether carboxylate in an amount of from about 0.1 to about 50% by weight,

preferably from about 1 to about 25% by weight, and most preferably from about

2 to about 15% by weight, based on the weight of the personal care composition.

Additional auxiliaries and additives which may also be employed in the

personal care compositions of the present invention include, but are not limited

to, mild surfactants, oily substances, emulsifiers, superfatting agents, pearly

luster waxes, stabilizers, consistency-imparting agents, thickeners, cationic

polymers, silicone compounds, biogenic active ingredients, anti-dandruff agents,

film forming agents, preservatives, hydrotropes, solubilizers, UV light protection

filters, insect repellents, artificial tanning agents, perfume oils, dyes, and the like.

Typical examples of mild, i.e., particularly skin-compatible surfactants are

fatty alcohol polyglycol ether sulfates, monoglyceride sulfates, mono- and/or

dialkylsulfosuccinates, fatty acid isethionates, fatty acid sarcosinates, fatty acid

taurides, fatty acid glutamates, ethercarboxylic acids, alkyl oligoglucosides, fatty

acid glucamides, alkylamidobetaines, and/or protein-fatty acid condensates, the

later preferably on the basis of wheat proteins.

As oily substances, for example, Guerbet alcohols on the basis of fatty

alcohols with 6 to 18, preferably 8 to 10 carbon atoms; esters of linear C₆-C₂₂

fatty acids with linear C₆-C₂₂ fatty alcohols; esters of branched C₆-C₁₃ carboxylic

acids with linear C₆-C₂₂ fatty alcohols; esters of linear C₆-C₂₂ fatty acids with

branched alcohols, especially 2-ethylhexanol; esters of linear and/or branched

fatty acids with polyhydric alcohols (for example, ethylene glycol, dimer diol, or trimer triol) and/or Guerbet alcohols; triglycerides on the basis of C₆-C₁₀ fatty

acids; esters of C₆-C₂₂ fatty alcohols and/or Guerbet alcohols with aromatic

carboxylic acids, especially benzoic acid; esters of C₂-C₁₂ dicarboxylic acids with

linear or branched alcohols with 1 to 22 carbon atoms or polyols with 2 to 10

carbon atoms and 2 to 6 hydroxyl groups; vegetable oils; branched primary

alcohols; substituted cyclohexanes; linear C₆-C₂₂ fatty alcohol carbonates;

Guerbet carbonates; esters of benzoic acid with linear and/or branched C₆-C₂₂

alcohols (e.g., FINSOLV® TN); dialkyi ethers; ring opening products of

epoxidized fatty acid esters with polyols; silicone oils; and/or aliphatic or

naphthenic hydrocarbons.

As emulsifiers, for example, nonionic surfactants from at least one of the

following groups come under consideration:

(1) Addition products of 2 to 30 moles ethylene oxide and/or 0 to 5 moles

propylene oxide to linear fatty alcohols with 8 to 22 C atoms, to fatty acids

with 12 to 22 C atoms and to alkylphenols with 8 to 15 C atoms in the

alkyl group;

(2) C_12/18 fatty acid mono- and diesters of addition products of 1 to 30 moles

ethylene oxide to glycerol;

(3) glycerol mono- and diesters and sorbitan mono- and diesters of saturated

and unsaturated fatty acids with 6 to 22 carbon atoms and their ethylene

oxide addition products;

(4) alkyl mono- and oligoglycosides with 8 to 22 carbon atoms in the alkyl

radical and their ethoxylated analogs; (5) addition products of 15 to 60 moles ethylene oxide to castor oil and/or

hardened castor oil;

(6) polyol esters and especially polyglycerol esters, e.g., polyglycerol poly-12-

hydroxystearate or polyglycerol dimerate. Also suitable are mixtures of

compounds from several of these classes of substances;

(7) addition products of 2 to 15 moles ethylene oxide to castor oil and/or

hardened castor oil;

(8) partial esters on the basis of linear, branched, unsaturated or saturated

C_6/22 fatty acids, ricinoleic acid, and 12-hydroxystearic acid and glycerol,

polyglycerol, pentaerythritol, dipentaerythritol, sugar alcohols (e.g.,

sorbitol), alkylglucosides (e.g., methylglucoside, butylglucoside,

laurylglucoside) as well as polyglucosides (e.g., cellulose);

(9) mono-, di-, and trialkyl phosphates as well as mono-, di-, and/or tri-PEG-

alkylphosphates;

(10) lanolin alcohols;

(11 ) polysiloxane-polyalkyl-polyether-copolymers or corresponding derivatives;

(12) mixed esters of pentaerythritol, fatty acids, citric acid, and fatty alcohol

according to German Patent (DE-PS) 1,165,574 and/or mixed esters of

fatty acids with 6 to 22 carbon atoms, methylglucose, and polyols,

preferably glycerol, as well as

(13) polyalkylene glycols.

The addition products of ethylene oxide and/or of propylene oxide to fatty

alcohols, fatty acids, alkylphenols, glycerol mono- and diesters, as well as sorbitanmono- and diesters of fatty acids or to castor oil represent known,

commercially available products. These are mixtures of homologs whose mean

degree of alkoxyiation corresponds to the ratio of ethylene oxide and/or

propylene oxide and substrate with which the addition reaction is performed.

C_12/18 fatty acid mono- and diesters of addition products of ethylene oxide to

glycerol are known as refatting agents for cosmetic preparations from DE-PS

2,024,051.

C_8/18 alkylmono- and -oligoglycosides, their preparation, and their use are

known from the state of the art. Their manufacture is accomplished in particular

by reacting glucose or oligosaccharides with primary alcohols with 8 to 18 C

atoms. It is true of the glycoside radical that both monoglycosides, in the case

of which a cyclic sugar radical is glucosidically bound to the fatty alcohol, and

oligomeric glycosides with a degree of oligomerization up to preferably about 8

are suitable. The degree of oligomerization is a statistical mean value, based on

a homolog distribution customary for such industrial products.

In addition, zwitterionic surfactants can be used as emulsifiers.

Zwitterionic surfactants are defined as surface-active compounds that carry in

the molecule at least one quaternary ammonium group and at least one

carboxylate and one sulfonate group. Particularly suitable zwitterionic

surfactants are the so-called betaines, such as N-alkyl-N,N-dimethylammonium

glycinate, for example coco alkyldimethylammonium glycinate; N-acylamino-

propyl-N,N-dimethylammonium glycinates, for example coco

acylaminopropyldimethylammonium glycinate; and 2-alkyl-3-carboxymethyl-3- hydroxyethylimidazolines with in each case 8 to 18 C atoms in the alkyl or acyl

group; as well as coco acylaminoethyl hydroxyethylcarboxymethyl glycinate.

Particularly preferred is the fatty acid amide derivative known under the CTFA

designation cocamidopropyl betaine. Also suitable as emulsifiers are ampholytic

surfactants. Ampholytic surfactants are defined as surface-active compounds

that, in addition to a C_8/18 alkyl- or -acyl group in the molecule contain at least

one free amino group and at least one -COOH- or SO₃H group and are capable

of forming internal salts. Examples of suitable ampholytic surfactants are N-

alkylglycines, N-alkylpropionic acids, N-alkylaminobutyric acids, N- alkyliminodipropionic acids, N-hydroxyethyl-N-alkylamidopropylglycine, N-

alkyltaurine, N-alkylsarcosine, 2-alkylaminopropionic acids and alkylaminoacetic

acids with, in each case, 8 to 18 C atoms in the alkyl group. Particularly

preferred ampholytic surfactants are N-coco-alkylaminopropionate, coco

acylamino-ethylamino-propionate, and C_12/18 acylsarcosine. In addition to the

ampholytic emulsifiers, quaternary emulsifiers also come under consideration,

wherein those of the type of the esterquats, preferably methylquaternized difatty

acid triethanolamine ester salts, are particularly preferred.

As superfatting agents, substances such as lanolin and lecithin as well

as polyethoxylated or acylated lanolin and lecithin derivatives, polyol fatty acid

esters, monoglycerides, and fatty acid alkanolamides may be used, wherein the

latter simultaneously serve as foam stabilizers.

As pearl luster waxes, the following come under consideration, for

example: alkylene glycol esters, especially ethylene glycol distearate; fatty acid alkanolamides; especially coco fatty acid diethanolamide; partial glycerides,

especially stearic acid monoglyceride; esters of polyfunctional, possibly hydroxy-

substituted carboxylic acids with fatty alcohols with 6 to 22 carbon atoms,

especially long-chain esters of tartaric acid; fats, for example fatty alcohols, fatty

ketones, fatty aldehydes, fatty ethers and fatty carbonates, containing a total of

at least 24 carbon atoms, especially laurone and distearyl ether; fatty acids such

as stearic acid, hydroxystearic acid, or behenic acid; ring opening products of

olefin epoxides with 12 to 22 carbon atoms with fatty alcohols with 12 to 22

carbon atoms and/or polyols with 2 to 15 carbon atoms and 2 to 10 hydroxyl

groups; and mixtures thereof.

As consistency-imparting agents, fatty alcohols with 12 to 22 and

preferably 16 to 18 carbon atoms as well as partial glycerides come under

consideration. Preferred is a combination of these substances with

alkyloligoglucosides and/or fatty acid-N-methylglucamides of the same chain

length and/or polyglycerolpoly-12-hydroxystearates. Suitable thickeners are,

for example, polysaccharides, especially xanthan gum, guar-guar, agar-agar,

alginates and tyloses, carboxymethylcelluloses and hydroxyethylcelluloses, also

high-molecular-weight polyethylene glycol mono- and diesters of fatty acids,

polyacrylates (e.g., CARBOPOLS® from Goodrich or SYNTHALENS® from

Sigma), polyacrylamides, polyvinyl alcohol and polyvinylpyrrolidone, surfactants

such as ethoxylated fatty acid glycerides, esters of fatty acids with polyols such

as pentaerythritol or trimethylolpropane, fatty alcohol ethoxylates, with narrow

homolog distribution or alkyloligoglycosides as well as electrolytes such as sodium chloride and ammonium chloride.

Suitable cationic polymers are, for example, cationic cellulose

derivatives, such as a quaternized hydroxyethylcellulose available from

Amerchol under the name of POLYMER JR 400®; cationic starches; copolymers

of diallylammonium salts and acrylamides; quaternized vinylpyrrolidone/

vinylimidazole polymers, such as LUVIQUAT® (BASF); condensation products

of polyglycols and amines; quaternized collagen polypeptides, such as

lauryldimonium hydroxypropyl hydrolyzed collagen (LAMEQUAT®/Gruenau);

quaternized wheat polypeptides, polyethylene imine; cationic silicone polymers,

e.g., amidomethicone; copolymers of adipic acid and dimethylamino-

hydroxypropyl diethylenetriamine (CARTARETINE®/ Sandoz); copolymers of

adipic acid with dimethyldiallylammonium chloride (MERQUAT®

550/Chemviron); polyaminopolyamides, for example as described in FR-A

2,252,840 and crosslinked water-soluble polymers; cationic chitin derivatives

such as quaternized chitosan, possibly with a microcrystalline distribution;

condensation products of dihaloalkylene such as dibromobutane with

bisdialkylamines, such as bis-dimethylamino-1 ,3-propane; cationic guar gums,

such as JAGUAR® CBS, JAGUAR® C-17, GUAGUAR® C-16 from Celanese

Corporation, quaternized ammonium salt polymers such as MIRAPOL® A-15,

MIRAPOL® AD-1 , MIRAPOL® AZ-1 from the Miranol company.

Suitable silicone compounds are, for example, dimethylpolysiloxanes,

methylphenylpolysiloxanes, cyclic silicones, as well as amino, fatty acid, alcohol,

polyether, epoxy, fluoro, glycoside, and/or alkyl-modified silicone compounds, which may exist in either liquid or resinous form at room temperature. Typical

examples of fats are glycerides; as waxes, beeswax, carnauba wax, candelilla

wax, montan wax, paraffin wax, or microwaxes, possibly in combination with

hydrophilic waxes, e.g., cetylstearyl alcohol or partial glycerides, come under

consideration. As stabilizers, metal salts of fatty acids, for example

magnesium, aluminum, and/or zinc stearate may be used. As biogenic active

ingredients, for example, tocopherol, tocopherol acetate, tocopherol palmitate,

ascorbic acid, deoxyribonucleic acid, retinol, bisabolol, allantoin, phytanetriol,

panthenol, AHA acids, amino acids, ceramides, pseudoceramides, essential oils,

plant extracts, and vitamin complexes may be understood. As anti-dandruff

agents, climbazole, octopirox, and zinc pyrithione may be used. Customary

film-forming agents are, for example, chitosan, microcrystalline chitosan,

quaternized chitosan, polyvinylpyrrolidone, vinylpyrrolidone-vinyl acetate

copolymers, polymers of the acrylic acid series, quaternary cellulose derivatives,

collagen, hyaluronic acids, and their salts and similar compounds. As swelling

agents for aqueous phases, montmorillonites, clay minerals, pemulen and alkyl-

modified carbol types (Goodrich) may be used.

UV light protective filters are defined as organic substances that are

capable of absorbing ultraviolet rays and releasing the energy taken up in the

form of longer-wave radiation, for example heat. UVB filters can be oil-soluble

or water-soluble. The following may be mentioned as examples of oil-soluble

substances:

• 3-benzylidenecamphor and derivatives thereof, e.g., 3-(4- methylbenzylidene)camphor;

• 4-aminobenzoic acid derivatives, preferably 4-(dimethylamino) benzoic

acid-2-ethylhexyl ester, 4-(dimethylamino) benzoic acid-2-octyl ester and

4-(dimethylamino) benzoic acid amyl ester;

• Esters of cinnamic acid, preferably 4-methoxycinnamic acid-2-ethylhexyl

ester, 4-methoxycinnamic acid isopentyl ester, 2-cyano-3-phenylcinnamic

acid-2-ethylhexyl ester (octocrylene);

• Esters of salicylic acid, preferably salicylic acid-2-ethylhexyl ester,

salicylic acid-4-isopropylbenzyl ester, salicylic acid homomenthyl ester;

• Derivatives of benzophenone, preferably 2-hydroxy-4-

methoxybenzophenone, 2-hydroxy-4-methoxy-4'-methylbenzophenone,

2,2'-dihydroxy-4-methoxybenzophenone;

• Esters of benzalmalonic acid, preferably 4-methoxy-benzmalonic acid di-

2-ethylhexyl ester;

• Triazine derivatives, such as 2,4,6-trianilino(p-carbo-2'-ethyl-1-hexyloxy)-

1 ,3,5-triazine and octyltriazone;

• Propane-1 ,3-diones, such as 1-(4-tert.-butylphenyl)-3-(4-

methoxyphenyl)propane-1 ,3-dione.

As water-soluble substances, the following may be considered:

• 2-Phenylbenzimidazole-5-sulfonic acids and the alkali, alkaline earth,

ammonium, alkylammonium, alkanolammonium and glucammonium salts

thereof;

• Sulfonic acid derivatives of benzophenones, preferably 2-hydroxy-4- methoxybenzophenone-5-sulfonic acids and salts thereof;

• Sulfonic acid derivatives of 3-benzylidenecamphor, for example, 4-(2-oxo-

3-bornylidenemethyl)benzenesulfonic acid and 2-methyl-5-(2-oxo-3-

bornylidene)sulfonic acid and salts thereof.

Typical UV-A filters especially include derivatives of benzoylmethane, for

example 1-(4'-tert-butylphenyl)-3-(4'-methoxyphenyl)propane-1 ,3-dione or 1-

phenyl-3-(4'-isopropylphenyl)-propane-1 ,3-dione. Naturally, the UV-A and UV-B

filters can also be used in mixtures. In addition to the soluble substances

mentioned, insoluble pigments, namely finely dispersed metal oxides or salts,

come under consideration for this purpose, for example titanium dioxide, zinc

oxide, iron oxide, aluminum oxide, cerium oxide, zirconium oxide, silicates (talc),

barium sulfate, and zinc stearate. The particles should have a mean diameter

of less than 100 nm, preferably between 5 and 50 nm and especially between

15 and 30 nm. They may have a spherical shape, but particles may also be

used which have an ellipsoidal shape or a shape that differs from the spherical

shape in some other way. In addition to the two above-mentioned groups of

primary light-protective substances, secondary light-protective substances of the

antioxidant type may be used, which intervene in the photochemical reaction

chain initiated when UV radiation enters the skin. Typical examples are

superoxide dismutase, tocopherols (vitamin E), and ascorbic acid (vitamin C).

Additional suitable UV light-protective filters can be taken from the review by P.

Finkel in SOFW-Journal 122:5423, 1966.

In addition, to improve the flow behavior, hydrotropes, for example ethanol, isopropyl alcohol, or polyols may be used. Polyols that come under

consideration here preferably contain 2 to 15 carbon atoms and at least two

hydroxyl groups. Typical examples are

• Glycerol;

• Alkylene glycols, such as ethylene glycol, diethylene glycol, propylene

glycol, butylene glycol, hexylene glycol, and polyethylene glycols with an

average molecular weight of 100 to 1 ,000 daltons;

• Technical oligoglycerol mixtures with an autocondensation degree of 1.5

to 10, for example technical diglycerol mixtures with a diglycerol content

of 40 to 50 wt%;

• Methylol compounds, especially trimethylolethane, trimethylolpropane,

trimethylolbutane, pentaerythritol, and dipentaerythritol;

• Lower alkyl glycosides, especially those with 1 to 8 carbon atoms in the

alkyl radical, for example methyl- and butylglycoside;

• Sugar alcohols with 5 to 12 carbon atoms, for example sorbitol or

mannitol;

• Sugars with 5 to 12 carbon atoms, for example glucose or sucrose;

• Amino sugars, for example glucamine.

Suitable preservatives, for example, include phenoxyethanol,

formaldehyde solution, parabens, pentanediol, or sorbic acid. Suitable insect

repellents include, for example, N,N-diethyl-m-toluamide, 1 ,2-pentanediol, or

Insect Repellent 3535; a suitable artificial tanning agent is dihydroxyacetone.

Suitable perfume oils may include the extracts of flowers (lavender, roses, jasmine, carnations), stems and leaves (geranium, patchouli, petitgrain),

fruits (anise, coriander, caraway, juniper), fruit peelings (bergamot, lemon,

orange), roots (mace, angelica, celery, cardamom, costus, iris, sweet flag),

woods (sandalwood, guaiac wood, cedarwood, rosewood), herbs and grasses

(tarragon, lemongrass, salvia, thyme), needles and branches (fir, spruce, pine,

larch), resins and balsams (galbanum, elemi, benzoin, myrrh, olibanum,

opoponax). Also, animal raw materials come under consideration, such as

musk, civet, and castoreum. As synthetic or semisynthetic perfume oils,

ambroxane, eugenol, isoeugenol, citronellal, hydroxycitronellal, geraniol,

citronellol, geranyl acetate, citral, ionone, and methylionone come under

consideration.

As coloring materials, substances suitable and approved for cosmetic

purposes can be used, as summarized for example in the publication "Cosmetic

coloring materials" from the Dyestuffs Committee of the German Research

Association, Verlag Chemie, Weinheim, 1984, pp. 81-106. These coloring

materials are usually used in concentrations of 0.001 to 0.1 wt%, based on the

total mixture.

The amount of auxiliaries and additives that may be employed can range

from about 1 to about 50% by weight, and preferably from about 5 to about 40%

by weight, based on the weight of the personal care composition. The

production of the personal care composition may take place using any

customary cold or hot processes; preferably the phase inversion temperature

method. The present invention will be better understood from the examples which

follow, all of which are intended to be illustrative only, and are not meant to

unduly limit the scope of the invention in any way.

EXAMPLES

Claims

What is claimed is:

1. A personal care product comprising from about 0.1 to about 50% by weight of a surfactant corresponding to formula I:

R₁O(R₂O)_b(Z)_aOCH₂COO X⁺ I wherein R₁ is a monovalent organic radical having from about 6 to about 30 carbon atoms; R₂ is a divalent alkylene radical having from 2 to 4 carbon atoms; Z is a saccharide residue having 5 or 6 carbon atoms; b is a number having a value from 0 to about 12; a is a number having a value from 1 to about 6; and X is an alkali metal ion.

2. The product of claim 1 wherein in formula I, R is a monovalent organic radical having from 12 to 16 carbon atoms, b is zero, and a is a number having a value of about 1.4.

3. The product of claim 1 wherein the surfactant is present in the product in an amount of from about 1 to about 25% by weight, based on the weight of the product.

4. A process for making a novel surfactant comprising:

(a) providing an alkyl polyglycoside having general formula II:

R₁O(R₂O)_b(Z)_a II wherein R^ is a monovalent organic radical having from about 6 to about 30 carbon atoms; R₂ is a divalent alkylene radical having from 2 to 4 carbon atoms; Z is a saccharide residue having 5 or 6 carbon atoms; b is a number having a value from 0 to about 12; a is a number having a value from 1 to about 6;

(b) providing a non-aqueous alkali metal compound;

(c) dispersing the alkyl polyglycoside in the nonaqueous alkali metal compound to form a reaction mixture; and

(d) adding a chloroacetate derivative to the reaction mixture to form the novel surfactant.

5. The process of claim 4 wherein in formula II, R₁ is a monovalent organic radical having from 12 to 16 carbon atoms, b is zero, and a is a number having a value of about 1.4.

6. The process of claim 4 wherein the alkali metal compound is selected from the group consisting of sodium ethoxide, sodium hydroxide, potassium tert- butoxide and mixtures thereof.

7. The process of claim 4 wherein the chloroacetate derivative is selected from the group consisting of sodium monochloroacetate, ethyl chloroacetate and mixtures thereof.

8. The process of claim 7 wherein the chloroacetate derivative is sodium monochloroacetate.

9. The product of the process of claim 4.

10. The product of the process of claim 5.

11. The product of the process of claim 6.

12. The product of the process of claim 7.

13. The product of the process of claim 8.

14. A cleaning composition comprising from about 20 to about 35% by weight, based on the weight of the cleaning composition, of a surfactant having formula I:

R₁O(R₂O)_b(Z)_aOCH₂COO X⁺ I wherein R╬▓ is a monovalent organic radical having from about 6 to about 30 carbon atoms; R₂ is a divalent alkylene radical having from 2 to 4 carbon atoms; Z is a saccharide residue having 5 or 6 carbon atoms; b is a number having a value from 0 to about 12; a is a number having a value from 1 to about 6; and X is an alkali metal ion.