CS253437B1 - A low-foaming surfactant and a pleasant scent - Google Patents

Abstract

The present invention relates to a nonionic surfactant which is prepared by alkylene oxidation of terpene alcohols linalool and dihydrolinalool and / or mixtures thereof. The surfactant has a low foaming and, in both concentrated and diluted form, has a pleasant odor. The surfactant can be used in the cosmetic industry and in the preparation of household chemistry.

Description

253437 3

BACKGROUND OF THE INVENTION The present invention relates to a surfactant having a low foaming and a pleasant odor, prepared by alkylating the terpene alcohols and / or mixtures thereof. In the synthesis of vitamin A, vitamin E, the pharmaceutical industry, and fragrances, cosmetics such as linalool, citral, citricone, geraniol, nerol, pseudojonone and some of their further derivatives are based. These are terpene alcohols, aldehydes and ketones, which are fragrant. The starting material of the virides and fragrances is dehydrolinalool (3,7-dimethyl-3-ol-6-ene-1-octine). From dehydroldehyde by hydrogenation on catalysts, in particular palladium, the alcohols lithanol (2,6-dimethyl-2,7-octadiene-6-ol) and di-hydrolinalool (2,6-dimethyl-2-octene-6- ol). The linalool allyl rearrangement results in more nerol and geraniol fragrances. Alcohol gelatin is the main component of rose oil. A mixture of isomeric alcohols differing in the bond of the double bond. The structural isomer of geraniol is linalool contained in le-vandal oil (O. Červinka, V. Dedek, M.Ferles: Organic Chemistry, SNTL Praha rok69).

Hydrogenation of dehydrolinalool to linalo-ol is very sensitive to the hydrogenation conditions. Although all the reaction conditions (Lindlar catalyst, low temperature, minimum hydrogen pressure, hydrogenation proceeds to the second stage on dihydrolinalool) are found to be optimal. By fractionation of the crude mixture, linalool is collected at the top of the column, as the main constituent of the rectification, and in the digestor there is a mixture of linalool and dihydrolinalool in the composition containing 20 to 70% by weight of dihydrolinalool.

Fractionation is already difficult due to the fact that the products are of oily consistency, high boiling point and a small difference between the boiling points of the two components. The lithium has a boiling point of 101.3 kPa (198-199 ° C) and 79.8 ° C at 1.32 kPa.

Dihydrolinalool has a boiling point at 101.3 kPa of 201 to 202 ° C and at 1.86 kPa 89 to 90 ° C (Handbook of Chemistry and Physies, Cleveland, USA - 1964; Chemisches Zentralblatt, 1966) to avoid darkening and distillation, distillation must be carried out under reduced pressure. Since linalool and dihydro-loolool have a boiling point difference of only about 4 ° C, high-efficiency distillation plants are needed to increase their production costs.

Effectively evaluating the linalool fraction of 20 to 70% by weight. dihydrolinaloolubolo the goal of this work. It has been found that the alkynoxidation of linalool, dihydrolinalool and / or mixtures thereof produces nonionic surfactants having a low foaming power and a pleasant odor.

It is an object of the present invention to provide a surfactant having a low foaming and a pleasant aroma based on alkyl polyglycol ethers of the general formula:

X

AND

O (CH-CH 2 O) n H

Where X is H or CH3 Y is -CH = CH2, -CH2-CH3n is an integer from 2 to 60, prepared by alkylene oxidation of terpene alcohols linalool, dihydrolinalool and / or or their mixtures. When in the general formula Y, -CH = iCH 2 is alkyleneoxidinally when Y is -CH 2 -CH 3 it is di-hydrolinalool. Also, the terpene alcohol may be a mixture of isomeric alcohols differing in the double bond position of the hydroxyl group (geraniol, nerol, citronelol). Initial raw materials may not exhibit specific qualities and may be of a technical nature and may contain by-products, whether from the production of starting materials or by-products of the reaction, or may contain substances, which I present! a combination of the said provinces.

The alkylene oxidation products are liquid, paste-like, solids, according to the type and type of bonded alkylene oxide. If the methyloxyran surfactant is used, the products have a liquid oily consistency. The use of oxirane produces products from liquid to solid, depending on the amount of oxirane bound. The resulting nonionic surfactants can be further modified by sulphation, phosphatation or combined with other surfactants coated with additives, depending on which application is contemplated. The products are characterized by a pleasant fragrance and surface-active properties in concentrated form as well as in their aqueous solution. A further advantage of the low foaming surfactant and the pleasant odor is that, in addition to reducing the surface tension of the water, it exhibits a wetting ability and surfactants containing methyloxirane have a good defoaming action. Further advantages are apparent from the examples. EXAMPLE 1 In a stainless steel autoclave, a melt tube was placed under a nitrogen atmosphere at a temperature of 135 + 5 ° C. 0.3 MPa and the use of an alkali catalyst KOH, an oxyethylated mixture consisting of 75 wt. of linalool and 25% of dihydrolinalool in 155 g of a mixture (1 mol) and 155 g of oxirane (3.5 moles). The amount of 6 bound oxirane was 50% by weight. The resulting slurry consistency product had a surface tension measured according to ČSN 1101 of 1 g.l -1 in distilled water and a temperature of 20 ° C 44.5 mNirr.

Penivosp was determined by the method described by the CSL. A. O. 208,350 and 37.5%. Wettability of 1 g / l in solution with sodium hydroxide solution. 30 g. I 1 according to methodology IN 66 6129 was 166 seconds.

The product in concentrated form as well as diluted in aqueous solution exhibited a fine odor. EXAMPLE 2 A surfactant sample was prepared as in Example 1. 155 g of a mixture of linalool and di-hydrolinalool (1 mol) of 30% w / w alumina and 70% w / w. dihydrolinaloolol oxylated with 440 g of oxirane (10 mol). The total amount of oxirane bound was 74% by weight. The resultant paste product had a surface tension of the aqueous solution with conc. The product in concentrated form and diluted aqueous solution showed a pleasant odor Example 3 A surfactant sample was prepared as in Example 1. 155 g of linalool mixture and di-hydrolinalool (1 mol) of the composition of Example 1 was oxyethylated with 880 g of oxirane (20 mol), the total amount of oxirane bound was 85.0% by weight. 1 g. I 1 and temperature 20 ° C 45.0 mNn 1. Foaming was 44.0%. The product in concentrated form as well as diluted in aqueous solution exhibited a pleasant flavor. EXAMPLE 4 A surfactant sample was prepared as in Example 1. 154 g of linalool (1 mol) were oxyethylated with 2640 g of oxirane (60 mol). The content of total bound oxirane was 95% by weight. The resulting product was a paste-like consistency, well soluble in water. The foaming power was 30.4%. Surface tension of aqueous solution 0 'conc. 1 g.h1 and a temperature of 20 ° C were 56.2 mNm -1. The product in concentrated form as well as diluted in aqueous solution showed a pleasant odor Example 5 as in Example 1. 154 g linalool (1 mol) oxypropylated with 1740 g of methyloxirane (30 moles) The total content of bound methyl loxirane was 91.8 wt% The product consisted of liquid consistency, insoluble in water, and the surface tension of this concentrated product measured at 20 ° C was 35.7 mNm The resulting effluent was found to have a defoaming potency of 78.3% according to the methodology described in AO 208 350. Example 6 A surfactant sample was prepared as in Example 1. 156 g of dihydrolinalool (1 mol) was oxyethylated with 440 g of oxirane (10 mol) and then oxypropylated with 350 g of methyl loxirane (6 mol) containing 46.5 wt.% of bound oxirane and 37.0 wt.% of bound bolipastic methyloxirate. kon The good water solubility was found to be 12.5%. Coating the aqueous solution with conc. 1 g at 1 ° C was 41.8 mNm -1. The product in concentrated form as well as dilute in aqueous solution exhibited a pleasant effect. Example 7 A surfactant sample was prepared as in Example 1. 156 g of dihydrolinalool (1 mole) was oxyethylated with 1100 g of oxirane (25 mgl), the product containing 87.5% by weight of bound oxirane had a good water-soluble content in the form of a waxy substance. The product in concentrated form as well as diluted in aqueous solution showed a pleasant odor. Example A surfactant sample was prepared as in Example 1. 156 g of dihydrolinalool (1 mol) were oxypropylated with 870 g of methyloxirane (15 mol). The resultant product, containing 84.8% by weight of product. the bound methyloxirate was a fluid consistency and was insoluble in water. The surface tension of the concentrated product measured at 20 [deg.] C. was 35.7 mNm < 1 >. < tb > ______________________________________ < tb > ______________________________________ < tb > ______________________________________ < tb >

Claims (1)

2 5 3 4 3 7 OBJECTIVE Low-foaming surfactant and alkyl polyglycolide-based surfactants: where X is H or CH3Y is -CH = CH2, -CH2-CH3n is an integer from 2 to 60, 0 {Ca CH 2 CH 2 CH 2 CH 2 CH-CH 2 -CH 2 -O-Y prepared by alkylene oxidation of terpene alcohols linalool, dihydrolinalool and / or mixtures thereof. CH3 CH3 Saverografla, n. P. Plant 7, Most Price 2.40 KSs