CH668266A5 - SURFACTANT MIXTURES. - Google Patents

Description

DESCRIPTION The present invention relates to mixtures of surface-active compounds which are used in particular in the manufacture of shampoos.

The new compound mixtures correspond to Formula I.

R- (0C3H6) m_ (0C2H4) n-0S03M (I),

wherein

R is a mixture of terminally bound aliphatic hydrocarbon groups, of which at least 70 mol

Is hydrocarbon groups, of which at least 70 mole percent branched 1-decyl, the remainder containing 8 to 12 carbon atoms, aliphatic radicals,

m is a number from 2 to 13,

5 n is a number from 6 to 15 and M is a cation.

Preference is given to the mixtures of the formula I in which R is at least 90 mol percent branched 1-decyl,

m 3 to 12,

io n 6 to 13 and

M is a cation from the group of alkali metals, alkaline earth metals, mono-, di-, tri- or tetra-C, ^ - alkylammonium or mono-, di- or tri-alkanol-C2.4-ammonium. The mixtures of the formula I, 15 in which

R at least 95 mole percent branched 1-decyl,

m 3 to 10,

n 6 to 12 and

M is a cation from the group consisting of sodium, potassium, ammonium, ammonium, mono-, di-, tri- or tetra-C 1-4 -alkylammonium or mono-, di- or tri-C2-alkanolammonium.

The mixtures of the formula I in which

R at least 95 mole percent branched 1-decyl, 25 of which are mainly trimethyl-l-heptyl,

m 3 to 9,

n 8 to 12 and

M is a sodium, potassium, ammonium, mono-, di- or tri-C2 ^ -alkanolammonium.

30 Among these compounds are again those of the formula iso-Ci0H2i- (OC3H6) m- (OC2H4) n-OSO3Na,

35 where m = 6 and n = 12,

m = 3 and n = 9,

m = 3 and n = 6,

m = 6 and n = 6 or 40 m = 9 and n = 9 mean, particularly preferred.

The compounds of formula I can be prepared in a manner familiar to those skilled in the art, e.g. by propoxylation of an alcohol of the formula R-OH and subsequent ethoxylation, sulfation and neutralization.

The alkoxylations are generally carried out in the presence of a catalyst, e.g. B. an alkali metal hydroxide or alkaline earth metal oxide. It is often advantageous to carry out the alkoxylation in the presence of a reducing compound, e.g. B. sodium borohydride to prevent excessive discoloration of the reaction mass.

For propoxylation, the calculated amount of propylene oxide is added to the pressure vessel containing the alcohol R-OH and allowed to react to constant pressure, whereupon 55 is added to the calculated amount of ethylene oxide and is also left to react until the pressure is constant. Finally, the alkoxylation product with a weak acid, e.g. B. Acetic acid added to neutralize the basic catalyst.

60 A medium degree of alkoxy is achieved by the alkoxylation, which means that not every molecule of the formula I contains exactly the same number of propylene oxide and ethylene oxide residues. As long as the average degree of alkoxylation is within the specified limits for m and n, statistical fluctuations are not important for the properties of the resulting surfactants. The alkoxylations are carried out analogously to known procedures with regard to temperature and pressure, and preferably under anhydrous conditions

3rd

668 266

gene performed. The alkyl polyalkoxides obtained are then processed in a known manner e.g. sulfated (esterified) with sulfuric acid, sulfamic acid, chlorosulfonic acid or sulfur trioxide and neutralized with a suitable agent (according to M). Chlorosulfonic acid has proven to be a very suitable sulfation agent. The sulfation is preferably carried out after drying the ether alcohol intermediate by applying a vacuum, and with exclusion of oxygen (flushing with nitrogen before evacuation), the chlorosulfonic acid being metered in at about 10 to 20 mol percent excess under normal pressure, under a nitrogen atmosphere. The reaction temperature should not exceed 35 ° C, which can be easily maintained by careful metering. After the addition of the chlorosulfonic acid has ended, the mixture is left to react for a further 1 to 2 hours, whereupon the reaction mass is discharged onto ice and e.g. is neutralized to pH 6.5 to 7 with sodium hydroxide.

The new compounds of formula I are excellent surfactants, e.g. B. can be used as emulsifiers, dispersants, detergents or wetting agents in the textile, leather, paper, paint, cosmetics and rubber industries. They can also be used as emulsifiers in the production of insecticides and agrochemicals, as additives in petroleum products, hydraulic fluids, lubricants, in the photo industry and in the food industry.

The ether sulfates of the present invention are particularly useful as wetting agents in shampoo compositions. Here they are used not only to improve the cleaning effect and foam properties, but also to prevent irritation of the scalp and eyes; they enable the production of extremely mild shampoos with excellent skin tolerance.

The shampoos contain between about 5 and 50 percent by weight ether sulfates of the formula I, preferably they contain between about 5 and 40, in particular between 10 and 30 percent by weight of such a compound mixture. The ether sulfates according to the invention can completely or only partially replace the wetting agents usually used in shampoos. In addition to the compounds of the formula I, the shampoo preferably no longer contains any further surfactants.

In addition to the compounds of the formula I, the shampoo may contain other additives, e.g. Fatty alkanolamides for increased foam formation and foam stabilization and for ensuring a viscosity that can be used for cosmetic purposes. A suitable monoalkano-lamide is e.g. B. coconut monoethanolamide, suitable dialkanola mides are e.g. Lauryl diethanolamide and coconut diethanola mid.

Conditioning agents can also be added to the shampoo, e.g. quaternary ammonium compounds such as dimethyl-di-stearyl-ammonium chloride and cationic polymers, e.g. Cartaretin F 23 (Sandoz AG) and Polymer JR (Union Carbide). Such additives improve the compatibility and treatment with damaged hair and reduce the static charge of the hair dried after washing.

In order to improve the shine of the washed hair, an oil can be added to the shampoo, for example a silicone oil (dimethylpolysiloxane or another commercially available polysiloxane), olive oil or a light mineral oil.

The water content of the shampoo composition depends on the desired consistency of the end product: viscous, lotion or gel-like. To correct the viscosity, an inorganic salt, e.g. B. sodium chloride, are added. Other possible additives are e.g. B. fragrances, non-toxic dyes, preservatives, light stabilizers and anti-dandruff.

In the following examples, parts are parts by weight and percentages are percentages by weight. The temperatures 5 are given in degrees Celsius.

example 1

io Preparation of iso-Ci0H2i- (OC3H6) 6- (OC2H4) i2-O-SO3Na.

327 parts of commercially available decyl alcohol (a mixture of primary aliphatic alcohols with 90 mol% branched 1-decanol, boiling temperature from 216 to 223 °, viscosity to 20 ° 22.5 centistoke (10_6m2-s_1), from Exxon Cem. 'S Co .), 6.5 parts of potassium hydroxide and 0.21 part of sodium borohydride are evacuated twice with stirring to 60 mbar and deaerated at 60 ° with nitrogen. The mixture is then evacuated to 66 mbar, heated to 155 ° with stirring and 720 parts of propylene oxide are slowly introduced so that the pressure in the reaction vessel 20 slowly reaches atmospheric pressure.

Allow to react until the pressure in the reaction vessel remains at a constant value for 30 minutes.

It is cooled to 60 °; evacuated and flushed twice with nitrogen, evacuated again to 66 mbar and added 1092 parts of ethylene oxide under the conditions given above 25, allowed to react further, cooled to 120 °, evacuated to at least 60 mbar for at least one hour to remove excess ethylene oxide, cooled 60 °, adds nitrogen to atmospheric pressure, neutralizes with 6.3 parts of glacial acetic acid and thus receives 30 a clear, light yellow liquid of the formula

ÌSO-Cl0H21- (OC3H6) 6- (OC2H4) l2-OH,

which turns milky white when it cools and finally separates out a white precipitate.

258.8 parts of the product thus obtained are flushed in nitrogen for 10 minutes, placed under vacuum, at 60 °

heated (in order to remove any water present), cooled again to room temperature, 40 40 parts of chlorosulfonic acid were slowly added while stirring, the temperature being said to be between 30 and 35 °, the mixture was stirred for a further 90 minutes, and the resulting mass was unloaded on ice and then neutralized a 50% solution of sodium hydroxide solution to pH 7 to 7.5. So much water is then added that a 40-50% 45% mixture is formed.

Example 2

50 According to the instructions of the first example, the compound mixtures of the following formulas can be prepared with correspondingly calculated amounts of propylene oxide and ethylene oxide.

55 a) iso-Ci0H2i- (OC3H6) 3- (OC2H4) 9-OSO3Na,

b) iso-Ci0H2i- (OC3H6) 3- (OC2H4) 6-OSO3Na,

c) iso-Ci0H2i- (OC3H6) 6- (OC2H4) 6-OSO3Na and

60

d) iso-Ci0H2i- (OC3H6) 9- (OC2H4) 9-SO3Na.

65

Example 3

Typical shampoo concentrations are composed as follows (percentage composition)

668266

4th

A

B

C.

Y compound mixture from Example 1

(41.7% active ingredient)

32.0

40.0

-

Connection mixture from Example 2

40.7% active substance)

-

-

35.0

Laurylamide diethanolamine

6.0

2.0

5.0

Sulfobetaine * (45% active substance,

Trade name «Sultaine»)

-

6.0

-

dye

0.2

0.2

0.2

Fragrance

0.2

0.2

0.2

Water -

61.6

51.6

59.4

pH (with citric acid or NaOH

set)

6.0

6.0

7.0

*Formula

+ ÇH3

R - CO - NH ~ (CH2) 3 - N - CH2CH - CH2 - SO3

CH3 OH

R-CO- = rest of cocoic acid

Claims (7)

668266 2nd PATENT CLAIMS 1. Surfactant mixtures of the formula I. R- (0C3H6) m- (0C2H4) n-0SO3M (I), wherein R is a mixture of terminally bound aliphatic hydrocarbon groups, of which at least 70 mole percent branched 1-decyl, the remainder containing 8 to 12 carbon atoms, aliphatic radicals, m is a number from 2 to 13, n is a number from 6 to 15 and M is a cation. 2. surfactant mixtures of formula I, according to claim 1, wherein R at least 90 mole percent branched 1-decyl, m 3 to 12, n 6 to 13 and M is a cation from the group of the alkali metals, alkaline earth metals, mono-, di-, tri- or tetra-C 1-4 -alkylammonium or mono-, di- or tri-alkanol-C2_4-ammonium. 3. surfactant mixtures of formula I, according to claim 1, wherein R at least 95 mole percent branched 1-decyl, m 3 to 10, n 6 to 12 and M is a cation from the group sodium, potassium, ammonium, mono-, di-, tri- or tetra-C 1-4 -alkylammonium or mono-, di- or tri-C2-4-alkanolammonium. 4. surfactant mixtures of formula I, according to claim 1, wherein R at least 95 mole percent branched 1-decyl, mainly trimethyl-l-heptyl, m 3 to 9, n 8 to 12 and M is a sodium, potassium, ammonium, mono-, di- or tri-CM-alkanolammonium ion. 5. The surfactant mixtures according to claim 4 of the formula iso-Ci0H2i- (OC2H6) m- (OC2H4) n-OSO3Na, where m = 6 and n = 12, m = 3 and n = 9, m = 3 and n = 6, m = 6 and n = 6 or m = 9 and n = 9. 6. Shampoo, which contains 5 to 50 percent by weight of a compound mixture according to one of the preceding claims as the main surfactant component. 7. shampoo according to claim 6, with 5 to 40, in particular 10 to 30% of a surfactant mixture of the formula I.