JP2007231021A - Manufacturing method of alkylene glycol ether - Google Patents

Abstract

<P>PROBLEM TO BE SOLVED: To provide a manufacturing method of a low odorous compound exhibiting foam-increasing and thickening performances. <P>SOLUTION: The manufacturing method comprises reacting a raw material alcohol represented by general formula (2): R<SP>1</SP>OH (wherein R<SP>1</SP>is an 8-10C linear alkyl or alkenyl group) with propylene oxide and/or ethylene oxide using a basic catalyst and subsequently distilling out the raw material alcohol by a steam treatment, to thereby give a compound that is represented by general formula (1): R<SP>1</SP>O-(PO)<SB>n</SB>/(EO)<SB>m</SB>-R<SP>2</SP>(wherein R<SP>1</SP>is the same as above; PO is a propyleneoxy group; EO is an ethyleneoxy group; an average added mole number n is a numerical value of 1.5-3.0; an average added mole number m is a numerical value of 0-1.0; and R<SP>2</SP>is a hydrogen atom or a methyl group) and has a content of the raw material alcohol being decreased to at most 3,000 ppm. <P>COPYRIGHT: (C)2007,JPO&INPIT

Description

  The present invention relates to a method for producing a propyne oxide and / or an ethylene oxide adduct (alkylene glycol ether) of a low-odor alcohol having increased foaming and thickening performance.

  The cleaning composition is required to have various functions such as emulsifying power, solubilizing power, or cleaning power of soil components such as oil. In particular, hard surface cleaners such as dishwashers used by humans and body cleaners such as shampoos and body shampoos are different from industrial cleaners, and rich foaming and base odors when used. There is a demand for improvement in feeling of use such as lack of viscosity and moderate viscosity. On the other hand, it is important that industrial detergents have less foaming.

  Various foaming / thickening agents have been developed to improve the foamability and viscosity of the cleaning composition, and fatty acid alkanolamides and amides are used as general-purpose foaming / thickening agents. However, these nitrogen-containing compounds change with time such as hue depending on the blending conditions. In addition, fatty acid diethanolamide is suspected to be carcinogenic to nitroso compounds, which are impurities. For these reasons, a nitrogen-free thickening / foaming agent is desired.

Patent Document 1 describes a (poly) ethylene glycol alkyl ether in which 1 to 3 moles of ethylene oxide is added, starting from an alcohol having 8 to 12 carbon atoms, as a nitrogen-free thickening / foaming agent. Yes. However, a short-chain ethylene oxide adduct of about 1 to 3 mol contains a large amount (1% by weight or more) of unreacted alcohol. In addition, alcohol having 8 to 12 carbon atoms has a strong unpleasant odor, and particularly when a large amount of unreacted alcohol having 8 to 10 carbon atoms is present, the feeling of use as a cleaning composition is significantly lowered.
On the other hand, the alcohol can be removed by purification, but if the amount of alcohol exceeds several weight%, the production becomes complicated, which is not industrially preferable from the viewpoint of production cost. On the other hand, the amount of unreacted alcohol can be reduced by increasing the number of additions of ethylene oxide, but foaming properties are reduced when a large amount of ethylene oxide is added.

  As an example, Patent Document 2 describes an alkylene oxide adduct of an aliphatic alcohol whose odor is improved by introducing propylene oxide in addition to ethylene oxide. However, when this adduct is blended into a cleaning composition, the foaming property is low, and a cleaning composition having a low odor and good foaming property cannot be obtained.

  Patent Document 3 describes an alkylene oxide adduct of a higher aliphatic alcohol into which a short-chain propylene oxide is introduced. However, it is exclusively applied as an emulsifier or solubilizer, and no mention is made regarding odor and foaming properties.

  Similarly, Patent Document 4 describes an alkylene oxide adduct of an aliphatic alcohol into which a short-chain propylene oxide is introduced as a cleaning agent, but there is no description about odor or foaming property.

  Patent Document 5 and Patent Document 6 also describe polyoxyalkylene alkyl or alkenyl ether into which a short-chain propylene oxide is introduced as an industrial-use cleaning agent. However, only the detergency of industrial oil and iron powder is mentioned, and there is no description about odor and foaming property. In addition, there is no mention of dishwashing, skin or hair applications that require excellent foaming properties.

In any of the prior documents, there is no description about the raw material alcohol content.
Japanese Patent Laid-Open No. 2004-277585 JP 2003-226892 A JP 2004-98054 A JP 2002-226891 A JP-A-6-316682 JP 2003-13092 A

  An object of the present invention is to provide a method for producing a low-odor alkylene glycol ether having foam-enhancing and thickening performance.

The present invention uses a basic catalyst and has the general formula (2):
R ¹ OH (2)
(In the formula, R ¹ represents a linear alkyl group or alkenyl group having 8 to 10 carbon atoms)
After the reaction of propylene oxide and / or ethylene oxide with the raw material alcohol represented by the following, the raw material alcohol is distilled off by steam treatment, and the content of the raw material alcohol is reduced to 3000 ppm or less. Formula (1)
^{R 1 O- (PO) n /} (EO) m-R 2 (1)
(In the formula, R ¹ represents the same as above, PO represents a propyleneoxy group, EO represents an ethyleneoxy group, the average addition mole number n represents a number of 1.5 to 3.0, and average addition The number of moles m represents a number from 0 to 1.0, and R ² represents a hydrogen atom or a methyl group.)
A method for producing a compound represented by the formula [hereinafter referred to as “component (A)”] is provided:

  According to the present invention, a low-odor alkylene glycol ether having increased foaming and thickening performance can be obtained.

In the general formula (1) of the component (A), R ¹ is a linear alkyl group or alkenyl group having 8 to 10 carbon atoms, and a linear alkyl group is preferable from the viewpoint of low bromide. From the viewpoint of foaming properties, R ¹ preferably has 8 carbon atoms. In the case of mixed alkyl, R ¹ has 50 mol% or more, more preferably 80 mol% or more, and particularly preferably 98 mol% or more.
In the general formula (1) of the component (A), PO and EO may be block or random, but the block is preferable, and (PO) n / (EO) m is based on R ¹ O from the viewpoint of low bromide. More preferably, (PO) n and (EO) m are arranged in the order of blocks.

In the compound of the general formula (1) of the component (A), the average added mole numbers n and m are limited by the balance between odor and foamability. That is, if the average added mole numbers n and m are small, the content of the raw material alcohol increases and the odor increases. Even when the raw material alcohol is removed by purification, it is not preferable from the viewpoint of production cost. On the other hand, if the average added mole numbers n and m are large, the foam increase and the viscosity increase are lowered.
The average added mole number n indicates a number of 1.5 to 3.0, but 2.0 to 3.0, more preferably 2.0 to 2.8, particularly 2.3 to 2 in terms of odor and foamability. .8 is preferred. Moreover, 2.0-2.5 are preferable especially from a foamable viewpoint.
The average added mole number m represents a number of 0 to 1.0, but 0 is preferable from the viewpoint of foamability.
Further, n + m is preferably 1.5 to 4.0, more preferably 1.5 to 3.0, and particularly preferably 2.0 to 2.8 from the viewpoints of odor and foamability.

R ² in the general formula (1) represents a hydrogen atom or a methyl group, and is preferably a hydrogen atom.

  The component (A) is contained in the detergent composition in an amount of 0.1 to 20% by weight, more preferably 0.3 to 10% by weight, and particularly 0.5 to 5% by weight, in terms of foamability and economy. It is preferable from the viewpoint.

In the general formula (1), the compound in which n = m = 0 and R ² is a hydrogen atom is 3000 ppm or less in the component (A) from the viewpoint of low bromide, but is 2000 ppm or less, and further 1500 ppm. In the following, it is more preferably 1000 ppm or less, and particularly preferably 500 ppm or less.

A detergent composition can be prepared by adding the component (A) and a surfactant [component (B)] other than this.
The surfactant of component (B) is one or more surfactants selected from the group consisting of anionic surfactants, nonionic surfactants, amphoteric surfactants and cationic surfactants. Anionic surfactants, nonionic surfactants, and amphoteric surfactants are preferred, and anionic surfactants are particularly preferred. Specific examples include the following.

As the anionic surfactant, sulfuric acid type, sulfonic acid type, carboxylic acid type, phosphoric acid type and amino acid type are preferable, for example, alkyl sulfate, polyoxyalkylene alkyl ether sulfate, polyoxyalkylene alkenyl ether sulfate. Salt, sulfosuccinic acid alkyl ester salt, polyoxyalkylene sulfosuccinic acid alkyl ester salt, polyoxyalkylene alkyl phenyl ether sulfate, alkane sulfonate, acyl isethionate, acyl methyl taurate, higher fatty acid salt, polyoxyalkylene alkyl ether Examples thereof include acetates, alkyl phosphates, polyoxyalkylene alkyl ether phosphates, acyl glutamates, alanine derivatives, glycine derivatives, and arginine derivatives.
Among these, polyoxyethylene alkyl ether sulfate, polyoxyethylene alkenyl ether sulfate, alkyl sulfate, higher fatty acid salt, polyoxyalkylene alkyl ether acetate, alkyl phosphate, polyoxyalkylene alkyl ether phosphate Particularly preferred are those represented by general formula (3) or (4), and in particular phosphoric acid monoester represented by general formula (11) and phosphoric diester represented by general formula (12) And a phosphate ester surfactant having a weight ratio of (11) / (12) = 100/0 to 50/50.
R ³ -O (CH ₂ CH ₂ O) _p SO ₃ M (3)
R ⁴ -OSO ₃ M (4)
[Wherein R ³ represents an alkyl or alkenyl group having 10 to 18 carbon atoms, R ⁴ represents an alkyl group having 10 to 18 carbon atoms, M represents an alkali metal, alkaline earth metal, ammonium, alkanolamine or A basic amino acid is shown, p is an ethylene oxide average addition mole number, and shows the number of 1-5. ]

[Wherein R ¹¹ , R ¹² and R ¹³ each represent a linear or branched alkyl group or alkenyl group having 8 to 18 carbon atoms, and X ¹ , X ² and Y represent a hydrogen atom, an alkali metal atom, Alkaline earth metal atom, alkanolamine or ammonium is shown, and the average added mole numbers s, t and u are 0 to 5 respectively. ]

  Nonionic surfactants include polyoxyalkylene sorbitan fatty acid esters, polyoxyalkylene sorbite fatty acid esters, polyoxyalkylene glycerin fatty acid esters, polyoxyalkylene fatty acid esters, polyoxyalkylene alkyl ethers, polyoxyalkylenes Examples include alkylphenyl ethers, polyoxyalkylene (cured) castor oils, sucrose fatty acid esters, polyglycerin alkyl ethers, polyglycerin fatty acid esters, fatty acid alkanolamides, and alkyl glycosides. Of these, polyoxyalkylene alkyl ethers, alkyl glycosides, polyoxyalkylene C8-C20 fatty acid esters, polyoxyethylene sorbitan fatty acid esters, polyoxyethylene hydrogenated castor oil, and fatty acid alkanolamides are preferred, especially alkyl glycosides and fatty acid alkanols. Amides are preferred. Polyoxyalkylene alkyl ethers are preferably polyoxyethylene alkyl ether, polyoxypropylene alkyl ether, and polyoxyethylene / polyoxypropylene alkyl ether. As the alkyl glycosides, those having an alkyl group having 8 to 14 carbon atoms and a degree of condensation of sugar (such as glucose) of 1 to 2 are preferable. As the fatty acid alkanolamide, those having an acyl group having 8 to 18 carbon atoms, particularly 10 to 16 carbon atoms are preferable, and either a monoalkanolamide or a dialkanolamide may be used, but a hydroxyalkyl group having 2 to 3 carbon atoms may be used. What has is preferable. Specific examples of fatty acid alkanolamides include oleic acid diethanolamide, palm kernel oil fatty acid diethanolamide, coconut oil fatty acid diethanolamide, lauric acid diethanolamide, polyoxyethylene coconut oil fatty acid monoethanolamide, coconut oil fatty acid monoethanolamide, laurin Examples include acid monoisopropanolamide, lauric acid monoethanolamide, palm kernel oil fatty acid methylethanolamide, and coconut oil fatty acid methylethanolamide.

  Examples of amphoteric surfactants include betaine surfactants and amine oxide surfactants. Of these, betaine surfactants such as imidazoline betaines, alkyldimethylaminoacetic acid betaines, fatty acid amidopropyl betaines, sulfobetaines, and amine oxide surfactants such as alkyldimethylamine oxides are more preferred, and alkylcarboxymethylhydroxyethylimidazos. More preferred are sulfobetaines such as lithium betaine, fatty acid amidopropyl betaine, alkylhydroxysulfobetaine, alkylsulfobetaine, fatty acid amidopropylhydroxysulfobetaine and fatty acid amidopropylsulfobetaine, and alkyldimethylamine oxide. Compositions for tableware and body cleaners in which sulfobetaines such as alkylhydroxysulfobetaines, alkylsulfobetaines, fatty acid amidopropylhydroxysulfobetaines and fatty acid amidopropylsulfobetaines are required to have excellent foaming properties even in the presence of dirt, for example. In the case of the above, it is particularly preferable from the viewpoint of the foaming property not being impaired even when there is dirt, that is, from the viewpoint of foaming dirt resistance and from the viewpoint of thickening. Most preferred is alkylhydroxysulfobetaine. Fatty acid amidopropyl betaine and alkylhydroxysulfobetaine preferably have an alkyl group having 8 to 18 carbon atoms, particularly 10 to 16 carbon atoms, and particularly amide propyl betaine laurate, palm kernel fatty acid amidopropyl betaine, and coconut oil fatty acid. Amidopropyl betaine, lauryl hydroxysulfobetaine, lauryl sulfobetaine, coconut oil fatty acid amidopropyl hydroxysulfobetaine, coconut oil fatty acid amidopropylsulfobetaine and the like are preferable. Of these, lauryl hydroxysulfobetaine is most preferred. The alkyldimethylamine oxide preferably has an alkyl group having 8 to 18 carbon atoms, particularly 10 to 16 carbon atoms, and lauryldimethylamine oxide and myristyldimethylamine oxide are particularly preferable.

  As an example of the cationic surfactant, the following general formula (5) described in JP-A No. 2000-178146:

[Wherein, at least one of R ⁵ , R ⁶ , R ⁷ and R ⁸ is an alkoxy group having 12 to 28 carbon atoms in total, preferably a linear or branched alkoxy group having 16 to 28 carbon atoms, an alkenyloxy group. , An alkanoylamino group, an alkenoylamino group, an alkanoyl group or an alkanoyloxy group, a linear or branched alkyl group or alkenyl group which may be substituted, the remainder being a benzyl group, an alkyl group having 1 to 5 carbon atoms Represents a hydroxyalkyl group or a polyoxyethylene group having a total addition mole number of 10 or less, and Z ⁻ represents a halogen ion or an organic anion such as acetate, citrate, lactate, glycolate, phosphate, nitrate, sulfonate, sulfate, and alkylsulfate. Indicates selected from the group. ]
The quaternary ammonium salt represented by these is mentioned.

As a preferred example of the compound (5), at least one of R ⁵ , R ⁶ , R ⁷ and R ⁸ is an alkyl group which may be substituted with an alkoxy group having a total carbon number of 8 to 22, the remainder being , A methyl group, an ethyl group, or a benzyl group. More preferred specific examples include mono long-chain alkyltrimethylammonium chlorides such as stearyltrimethylammonium chloride and okdadecyloxypropyltrimethylammonium chloride, and dilong-chain alkyldimethylchlorides such as distearyldimethylammonium chloride and branched dialkyldimethylammonium chloride. Ammonium etc. are mentioned.

Component (B) is preferably contained in the cleaning composition in an amount of 3 to 50% by weight, more preferably 5 to 30% by weight, particularly 10 to 30% by weight from the viewpoint of foamability and economy.
The ratio of the components (A) and (B) is (A) / (B) = 1/200 to 10/1, more preferably 1/100 to 1/1, particularly 1/50 to 1/5 in weight ratio. 1/30 to 1/10 is preferable.

  Component (A) is preferably used as a thickening and foaming agent for a detergent composition used for skin or hair.

  The above thickening and foaming agent and cleaning composition are particularly suitable for body use such as skin or hair.

The said cleaning composition can contain an oily component, especially when it is for skin or hair.
Examples of the oil component include higher alcohols, silicones, and ester oils, hydrocarbons, glycerides, vegetable oils, animal oils, lanolin derivatives, higher fatty acid esters, and the like, and higher alcohols, ester oils, and / or silicones are preferable. Higher alcohols and / or silicones are particularly preferred.

  The cleaning composition further includes glycerin, humectant, cationic polymer, polysaccharide, polypeptide, pearlizing agent, solvent, liquid crystal forming base, dye, fragrance, propellant, edetacetate, citrate, etc. Chelating agents, pH adjusters, preservatives, antidandruff agents, and the like can be appropriately blended. Examples of the cationic polymer include cationized cellulose derivatives, cationic starches, and cationized guar gum derivatives. Examples of anti-dandruff agents include zinc pyrithione and piroctone olamine.

  The pH of the cleaning composition is preferably 3 to 10, particularly 4 to 9 at 25 ° C. when it is a 20-fold diluted solution.

In the method for producing component (A) of the present invention, in general formula (2), R ¹ is a linear alkyl group or alkenyl group having 8 to 10 carbon atoms, and a linear alkyl group is preferred from the viewpoint of low bromide. . From the viewpoint of foaming properties, R ¹ preferably has 8 carbon atoms. In the case of mixed alkyl, R ¹ has 50 mol% or more, more preferably 80 mol% or more, and particularly preferably 98 mol% or more.

  In the production method of component (A) of the present invention, propylene oxide and ethylene oxide may be block addition or random addition, but block addition is preferred. Further, from the viewpoint of low bromide, it is preferable to add propylene oxide to the raw material alcohol represented by the general formula (2) and then add ethylene oxide. Addition of only propylene oxide is also preferred. The average number of moles of propylene oxide added to the raw material alcohol represented by the general formula (2) is 1.5 to 3.0 moles from the viewpoint of low bromide and foaming properties, but 2.0 to 3. 0 mol is preferable, 2.0 to 2.8 mol is more preferable, and 2.3 to 2.8 mol is particularly preferable. Moreover, 2.0-2.5 mol is preferable especially from a foaming viewpoint. The average number of moles of ethylene oxide added to the raw material alcohol represented by the general formula (2) is 0 to 1.0 mole from the viewpoint of low bromide and foamability, but 0 mole is more preferred. In addition, the total average addition mole number of propylene oxide and ethylene oxide to the raw material alcohol represented by the general formula (2) is preferably 1.5 to 4.0 moles from the viewpoint of low bromide and foamability. More preferably, it is 0.5 to 3.0 mol, and particularly preferably 2.0 to 2.8 mol.

  In the production method of the component (A) of the present invention, the amount of the basic catalyst used is preferably 0.1 to 5 mol%, more preferably 0.1 to 2 mol% of the raw material alcohol represented by the general formula (2).

  A known general catalyst can be used as the basic catalyst, and is not particularly limited. Examples thereof include potassium hydroxide, sodium hydroxide, lithium hydroxide, sodium alkoxide and the like.

  The reaction temperature between the raw material alcohol and propylene oxide and / or ethylene oxide is 80 to 200 ° C., preferably 110 to 160 ° C., more preferably 110 to 130 ° C., and the reaction pressure is 0.1 to 0.8 MPa, preferably 0.1 to 0.6 MPa.

  The reaction product can be subjected to distillation as it is, but the basic catalyst can also be removed by distillation after removing the basic catalyst with a neutralizing agent or an adsorbent. The neutralizing agent and the adsorbent are not particularly limited, but the neutralizing agent is an organic acid such as acetic acid or lactic acid or the mineral acid such as phosphoric acid or sulfuric acid (single, mixed or combined), and the adsorbent is Kyo. Synthetic adsorbents such as Ward (Kyowa Chemical Co., Ltd.), activated clay, activated carbon, ion exchange resins, etc. (single, mixed, or combined use is also possible, and combined use with a neutralizing agent is also possible).

Raw alcohol is distilled off by steam treatment.
The steam treatment means that steam is blown into the reaction composition, and raw alcohol is distilled out of the system together with the steam.
Distillation and distillation can be carried out under normal pressure or reduced pressure, but generally it is more efficient to carry out under reduced pressure, and the burden on the equipment can be reduced.
The distillation conditions are as follows.
Temperature: 80-200 ° C, preferably 80-150 ° C.
Pressure: 27 kPa (200 torr) or less, preferably 6 kPa (45 torr) or less.
Water vapor amount: 0 to 50 parts by weight with respect to 100 parts by weight of the reaction composition.
The raw material alcohol content of the component (A) thus obtained is 3000 ppm or less from the viewpoint of low bromide, but is preferably 2000 ppm or less, more preferably 1500 ppm or less, still more preferably 1000 ppm or less, and particularly preferably 500 ppm or less.

Example 1
161-5.0 g (12.35 mol) of 1-octanol (Calcoal 0898, manufactured by Kao Corporation) and 6.9 g (0.12 mol) of potassium hydroxide were charged into an autoclave, dehydrated at 110 ° C. and 13.3 kPa, and then 120 ° C. Then, 1434 g (24.69 mol) of propylene oxide was added at 0.3 MPa to carry out the addition reaction.
After completion of the reaction, the mixture was aged at the same reaction temperature for 6 hours and then cooled to 80 ° C.
As a post-treatment, 55 g of a synthetic adsorbent (KYOWARD 600S, Kyowa Chemical Industry Co., Ltd.) was added to the obtained reaction composition and treated at 4.0 kPa for 1 hour, and then the catalyst was removed by filtration. The 1-octanol content of the obtained filtrate was 9000 ppm as determined by gas chromatography.
Subsequently, about 1000 g of the obtained filtrate, 1-octanol was distilled off by distillation under the conditions of 130 ° C. and 1.3 kPa. Further, steam treatment was performed by blowing 100 g of steam under the conditions of 145 ° C., 6.0 kPa, and 5 hours.
The 1-octanol content in the obtained product (alkylene glycol ether 1 shown in Table 1) was quantified by gas chromatography.

Example 2
In the same manner as in Example 1, alkylene glycol ethers 2 to 12 shown in Table 1 (product of the present invention) and Table 2 (comparative product) were obtained. Although the alkylene glycol ethers 2 to 5 were purified in the same manner as in Production Example 1, the alkylene glycol ethers 6 to 12 were only subjected to the catalyst removal by filtration shown in Production Example 1, and were not purified by distillation. The amount of raw material alcohol of the obtained alkylene glycol ether was quantified by gas chromatography.

Test Example Using the alkylene glycol ethers 1 to 12 and surfactants shown in Tables 1 and 2, a detergent composition was prepared by a conventional method, and the viscosity, foamability and odor were evaluated by the following methods. It was.
Viscosity measurement conditions are as follows. The results are shown in Tables 3 and 4.
(1) Viscometer with viscosity measurement B type viscometer (manufactured by Tokyo Keiki Co., Ltd.)
Rotor No. / Number of revolutions 1/12 rpm Measurement time 1 minute Temperature 30 ° C .: Measurement after putting a glass bottle containing a sample in a constant temperature bath of 30 ° C. ± 1 for 1 hour (2) Foaming property test and odor test Each cleaning agent described in Tables 3 and 4 1 ml of the composition was dropped on the palm of the hand, and the foaming properties and odor when the hands and arms were washed were evaluated according to the following evaluation criteria by 10 professional panelists.
(Foaming)
4: I felt that foamability was very good.
3: I felt that foamability was good.
2: I felt that foaming was normal.
1: I felt that foamability was not good.
The average score of 10 persons' evaluation was calculated | required, 3.6 or more was set as (double-circle), 2.6-3.5 was set as (circle), 1.6-2.5 was set as (triangle | delta), and 1.5 or less was set as x.
(smell)
4: No odor is observed.
3: A slight odor is recognized.
2: Odor is recognized.
1: Strong odor is recognized.
The average score of 10 persons' evaluation was calculated | required, 3.6 or more was set as (double-circle), 2.6-3.5 was set as (circle), 1.6-2.5 was set as (triangle | delta), and 1.5 or less was set as x.

(3) Stain resistance test Shown in Tables 3 and 4 on 15 g (20 cm) of Japanese female hair containing 15 g of tap water and coated with 0.1 mL of lanolin (manufactured by Sankei Sangyo Co., Ltd.) as a soil component. 1 mL of the obtained surfactant composition was taken and bubbled for 30 seconds. The generated foam was taken in a cylinder with a scale of 5 cm in diameter, and the amount of foaming (mL) was measured.

Reference example 1
A hair shampoo having the following composition was produced.
(Ingredient) (wt%)
Alkylene glycol ether 1 2.0
Polyoxyethylene (2) sodium lauryl ether sulfate * 15.0
Lauric acid diethanolamide 2.0
Cationic polymer ** 0.2
Silicone *** 1.0
Fragrance, methyl paraben
Purified water balance meter 100
*: Figures in parentheses indicate the average number of moles of ethylene oxide added **: Poise C-150L; manufactured by Kao Corporation **: Silicone BY22-060; manufactured by Toray Dow Corning Corporation This hair shampoo is foaming It had good properties, had no odor, and had an appropriate viscosity (2000 mPa · s).

Reference example 2
A body shampoo having the following composition was produced.
(Ingredient) (wt%)
Alkylene glycol ether 2 0.8
Laurate * 30.0
Amidopropyl betaine ** 2.0
Glycerin 3.0
Fragrance, methyl paraben
Purified water balance meter 100
*: Priory B-100; manufactured by Kao Corp. **: Anhitoal 20AB; manufactured by Kao Corp. This body shampoo has good foaming properties, has no odor, and has an appropriate viscosity (500 mPa · s). It was.

Reference example 3
A face wash having the following composition was produced.
(Ingredient) (wt%)
Alkylene glycol ether 1 1.0
Lauryl phosphate K salt 10.0
Lauric acid K salt 10.0
Myristic acid K salt 8.0
Palmitic acid K salt 8.0
Sorbitol 10.0
Fragrance, methyl paraben
Purified water balance meter 100.0
This facial cleanser had good foaming properties, had no odor, and had an appropriate viscosity (50000 mPa · s).

Reference example 4
A face wash having the following composition was produced.
(Ingredient) (wt%)
Alkylene glycol ether 1 1.0
Lauryl phosphate K salt 2.0
Polyoxyethylene (1) lauryl phosphate K salt * 5.0
Polyoxyethylene (2) sodium lauryl ether sulfate * 10.0
Lauryl hydroxysulfobetaine ** 3.0
Acrylic acid alkyl methacrylate copolymer *** 0.5
Ethylene glycol distearate2.0
Na ₂ SO ₄ 3.0
Fragrance, methyl paraben
Purified water balance meter 100.0
*: Figures in parentheses indicate the average number of moles of ethylene oxide added.
**: Anhitor 20HD: manufactured by Kao Corporation
***: Carbopol ETD2020; manufactured by BF Goodrich This facial cleanser has good foaming properties, has no odor, and has an appropriate viscosity (30000 mPa · s).

Reference Example 5
A hair shampoo having the following composition was produced.
(Ingredient) (wt%)
Alkylene glycol ether 13 0.6
Polyoxyethylene (1) Sodium lauryl ether sulfate * 13.8
Palm oil fatty acid amidopropyl betaine 1.2
Lauryl hydroxysulfobetaine 0.6
Cationic polymer ** 0.2
Silicone *** 2.0
Ethylene glycol distearyl ether 0.5
Fragrance, methyl paraben
Purified water balance meter 100
*: Figures in parentheses indicate the average number of moles of ethylene oxide added **: Jaguar C-13C; manufactured by Rhodia **: Silicone BY22-060; manufactured by Toray Dow Corning Co., Ltd. The stain resistance was good, there was no odor, and it had an appropriate viscosity (3000 mPa · s).

Reference Example 6
A hair shampoo having the following composition was produced.
(Ingredient) (wt%)
Alkylene glycol ether 13 0.8
Sodium lauryl ether sulfate 8.0
Polyoxyethylene (3) sodium lauryl ether sulfate * 8.0
Palm oil fatty acid monoethanolamide ** 0.6
Lauryl hydroxysulfobetaine 0.5
Cationic polymer *** 0.2
Silicone **** 2.0
Ethylene glycol distearyl ether 1.5
Fragrance, methyl paraben
Purified water balance meter 100
*: Figures in parentheses indicate the average number of moles of ethylene oxide added **: Aminone C-01S; manufactured by Shanghai Kao Chemical Co., Ltd. **: Polymer JR-400; manufactured by Dow Chemical Co., Ltd. ***: Silicone BY22-007 Manufactured by Toray Dow Corning Co., Ltd. This hair shampoo had good foaming and stain resistance, had no odor, and had an appropriate viscosity (6000 mPa · s).

Claims (2)

Using a basic catalyst, the general formula (2):
R ¹ OH (2)
(In the formula, R ¹ represents a linear alkyl group or alkenyl group having 8 to 10 carbon atoms)
After the reaction of propylene oxide and / or ethylene oxide with the raw material alcohol represented by the following, the raw material alcohol is distilled off by steam treatment, and the content of the raw material alcohol is reduced to 3000 ppm or less. Formula (1)
^{R 1 O- (PO) n /} (EO) m-R 2 (1)
(In the formula, R ¹ represents the same as above, PO represents a propyleneoxy group, EO represents an ethyleneoxy group, the average addition mole number n represents a number of 1.5 to 3.0, and average addition The number of moles m represents a number from 0 to 1.0, and R ² represents a hydrogen atom or a methyl group.)
The manufacturing method of the compound represented by these.   The production method according to claim 1, wherein propylene oxide is reacted with the raw material alcohol represented by the general formula (2).