JP2001323297A - Thickening and foam-increasing agent and method for producing the same and detergent composition containing the same - Google Patents

Abstract

PROBLEM TO BE SOLVED: To obtain a detergent auxiliary excellent in thickening property, foam-increasing property, stability at a low temperature and having slight temperature dependence and high safety. SOLUTION: This thickening and foam-increasing agent composed of an alkanolamide represented by the general formula (1) [wherein R1 represents a straight-chain or branched chain 7-21C alkyl group, alkenyl group or hydroxyalkyl group; R2 represents a straight-chain or branched chain 1-3C alkyl group; (R3)s each represent a straight-chain or branched chain 2-3C alkylene group and they may be same or different; (n) is an arbitrary number of 0-20.] is used as the detergent auxiliary.

Description

DETAILED DESCRIPTION OF THE INVENTION

[0001]

BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to a thickening / foaming agent, a method for producing the same, and a detergent composition containing the same, and more particularly, to an amphoteric surfactant, a nonionic surfactant and an anionic surfactant. The present invention relates to a thickening / foaming agent for a detergent containing an activator, a method for producing the same, and a detergent composition containing the same.

[0002] In the present invention, the term "thickening / foaming agent" refers to a compound having at least both properties of thickening and foaming properties.

[0003]

2. Description of the Related Art In general, in detergents such as shampoos and body cleansing agents, surfactant components used as main bases have relatively low viscosities. In order to adjust the viscosity of the product to an easily manageable value, a thickener is blended. Also,
When a surfactant is used as a detergent, foaming properties are required, but a surfactant alone often cannot provide sufficient foaming properties, and a foaming agent is separately used as an auxiliary agent. I was

[0004] Conventionally, as a thickening / foaming agent having characteristics having both viscosity increasing properties and foam increasing properties, fatty acid monoethanolamide, fatty acid diethanolamide, or polyoxyethylene (hereinafter abbreviated as POE) fatty acid ester has been used. And the like.

However, the fatty acid monoethanolamide itself has a high melting point, and therefore has poor solubility when formulated into a detergent. When the amount of the fatty acid monoethanolamide is large or when stored at a low temperature, it becomes cloudy. It has a disadvantage that it causes stains and, in turn, separates and poses a problem in terms of the stability of the detergent.

Fatty acid diethanolamide has a lower melting point than fatty acid monoethanolamide, so that it has excellent handleability and solubility at the time of blending. However, the amount of fatty acid diethanolamide added is increased to obtain the required viscosity and foamability. It was still not sufficient as a thickening / foaming agent.

Further, ester types such as POE fatty acid esters have good low-temperature stability, but have drawbacks in temperature dependence such as a large change in viscosity with temperature.

[0008] Accordingly, there has been a demand for the development of a thickening / foaming agent having good handling properties, excellent viscosity, foaming properties, low-temperature stability, and low temperature dependency.

[0009]

Means for Solving the Problems In view of the above-mentioned situation, the present inventors have found that even if the amount of addition is not increased, the viscosity, foaming property, low-temperature stability are excellent, the temperature dependency is small, and the safety is improved. As a result of intensive studies as to whether or not a highly-potent cleaning agent can be obtained, it was found that an alkanolamide derived from a specific amine achieves the above object, and the present invention has been completed.

That is, the present invention provides a thickening / foaming agent comprising an alkanolamide represented by the general formula (1), a method for producing the same, and a detergent composition containing the same.

[0011]

Embedded image [In the formula, R ₁ represents a linear or branched alkyl group having 7 to 21 carbon atoms, an alkenyl group, or a hydroxyalkyl group. R ₂ represents a linear or branched alkyl group having 1 to 3 carbon atoms. R ₃ represents a linear or branched chain alkylene group having 2 to 3 carbon atoms, n number of R ₃ may be the same or different. n shows the arbitrary number of 0-20. The production method according to claim 2 is a method for producing a thickening / foaming agent represented by the general formula (1) according to claim 1, wherein the fatty acid or the fatty acid represented by the following general formula (2) is used. A fatty acid alkyl ester is reacted with an amine represented by the following general formula (3), or a fatty acid or a fatty acid alkyl ester represented by the following general formula (2) is reacted with an amine represented by the following general formula (3) And a reaction product obtained by the reaction is further reacted with an alkylene oxide represented by the following general formula (4).

[0012]

Embedded image [Wherein, R ₁ represents a linear or branched alkyl group having 7 to 21 carbon atoms, an alkenyl group, or a hydroxyalkyl group;
R ₄ is a hydrogen atom or an alkyl group having 1 to 3 carbon atoms. ]

Embedded image [In the formula, R ₂ represents a linear or branched alkyl group having 1 to 3 carbon atoms. ]

Embedded image [Wherein, R ₃ represents a linear or branched alkylene group having 2 to 3 carbon atoms. ]

[0013]

BEST MODE FOR CARRYING OUT THE INVENTION Hereinafter, a method for producing an alkanolamide represented by the general formula (1) will be described in detail.

The alkanolamide represented by the general formula (1) is obtained by converting a fatty acid or a fatty acid alkyl ester represented by the general formula (2) with an amine represented by the general formula (3) without using a catalyst or an alkali catalyst. Alternatively, it can be obtained by reacting in the presence of an acid catalyst. Further, if necessary, it can be obtained by reacting the alkylene oxide represented by the general formula (4) in the presence of a generally used alkali catalyst or acid catalyst. The following is a specific example of this reaction.

[0015]

Embedded image

Embedded image

The fatty acid or fatty acid alkyl ester represented by the general formula (2) used in the present invention includes caprylic acid, capric acid, decanoic acid, lauric acid,
Examples thereof include myristic acid, palmitic acid, stearic acid, hydroxystearic acid, oleic acid, isostearic acid, and methyl, ethyl, and isopropyl esters thereof, and a mixture thereof can also be used.

As the amine represented by the general formula (3), N-methylethanolamine, N-ethylethanolamine, N-propylethanolamine, N-isopropylethanolamine and the like can be considered.

The amidation of the compound of the present invention can be carried out without using a catalyst. If necessary, an alkali catalyst such as sodium methylate, sodium hydroxide or potassium hydroxide, an acid catalyst or a metal catalyst can be used. it can. Its usage is
0.0 to fatty acid or fatty acid alkyl ester
It is preferably from 0.1 to 3.0% by weight.

The reaction temperature is preferably from 80 to 200 ° C. from the viewpoint of suppressing amide esters or esters as by-products, more preferably from 90 to 180 ° C., and the reaction time is sufficient up to 12 hours. It is preferable that water or lower alcohol produced as a by-product be distilled off with an inert gas such as nitrogen. The molar ratio (3) / (2) of the fatty acid or fatty acid alkyl ester represented by the general formula (2) and the amine represented by the general formula (3) is preferably 0.8 to 2.0 in terms of economy. Preferably, 1.0 to 1.5 is more preferable.

Since the reaction between the fatty acid or fatty acid alkyl ester represented by the general formula (2) and the amine represented by the general formula (3) proceeds almost quantitatively, the end product of the reaction can be used as it is. However, if necessary, a method in which amines are distilled off under reduced pressure, or water is added at 80 ° C.
As described above, it is also possible to perform oil-water separation and dehydrate under reduced pressure.

The alkanolamide obtained by the above-mentioned method can be further added to an alkylene oxide represented by the general formula (4).

By adding an alkylene oxide, the effect of low-temperature fluidity is improved.

Examples of the alkylene oxide represented by the general formula (4) include ethylene oxide and propylene oxide. In this case, the addition amount of the alkylene oxide is 0 per mole of the alkanolamide compound obtained by the condensation reaction of the general formulas (2) and (3).
２０20 mol. If it is more than 20 mol, the viscosity may be hindered, which is not preferable.

The conditions for the addition reaction of the alkylene oxide represented by the general formula (4) to the amidated compound are not particularly limited. Examples of the catalyst include alkali catalysts such as sodium hydroxide and potassium hydroxide, and trifluoride. Boron,
The reaction is carried out using an acid catalyst such as magnesium oxide, and the reaction temperature is 2
The temperature is preferably 0 to 180 ° C, more preferably 80 to 150 ° C. If it exceeds 180 ° C., it causes decomposition of the amide portion, formation of an ester component, and coloring. In addition, it is enough to react for 1 to 10 hours.

The alkanolamide of the present invention represented by the general formula (1) is liquid even at room temperature, so that it has excellent handling properties and has an excellent viscosity increase with respect to a coexisting surfactant.
Shows foam-increasing properties and has a low melting point per se, so it has excellent low-temperature stability, so it is used not only as a cleanser for hair, body and tableware, but also for various cleansing agents such as facial cleanser and house cleaner. It can be suitably used.

The detergent composition of the present invention contains an alkanolamide represented by the general formula (1) as an essential component, and its content is 0.1 to 50% by weight. It is preferable in terms of good foamability, and more preferably 0.5 to 30% by weight.

As the main cleaning active ingredient used in the cleaning composition of the present invention, one or more of anionic, cationic, amphoteric or nonionic active agents can be used. Alkyl sulfate, polyoxyethylene alkyl ether sulfate, alkylbenzene sulfonate, higher fatty acid salt, α-olefin sulfonate, alkyl sulfonate, N-alkylamide alkanol sulfate, N-alkanoyl Ethanolamide sulfate, fatty acid glyceride sulfate,
Alkyl glyceryl ether sulfate, alkyl phosphate, alkyl ether phosphate, alkyl ether carboxylate, sulfosuccinate surfactant, taurine surfactant, sarcosine surfactant, isethionate surfactant, N -Acyl acidic amino acid-based surfactants and the like. Examples of the cationic property include alkyltrimethylammonium chloride and dialkyldimethylammonium chloride. As amphoteric betaine-based or imidazoline-based, sulfobetaine-based, amine oxide-based, as nonionic polyoxyethylene alkyl ether, polyoxyethylene fatty acid ester,
Fatty acid monoglyceride, fatty acid sorbitan ester,
Alkyl polyglycosides and the like. One or more of these surfactants may be mixed.

[0028]

The alkanolamide represented by the general formula (1) has excellent thickening and foaming properties, and is itself easy to handle because of its good handling properties. It is useful in various fields such as cleaning agents. Further, the production method of the present invention can obtain an alkanolamide represented by the general formula (1) under mild reaction conditions using easily available raw materials.

[0029]

EXAMPLES Hereinafter, the present invention will be described specifically with reference to Examples, but the present invention is not limited to these Examples. The percentages in the examples are on a weight basis unless otherwise specified.

Production Example 1 [N-methyl lauric acid monoeta
Synthesis of noramide] 200.3 g (1.0 mol) of lauric acid was charged and dissolved by heating to 80 ° C. under a nitrogen stream, 90.1 g (1.2 mol) of N-methylethanolamine was added, and the mixture was aged at 150 ° C. for 6 hours. did. After cooling to 80 ° C., the pressure inside the reaction system was gradually reduced, and the temperature was raised to 150 ° C. to distill off unreacted amine. As a result, 237 g of a yellow transparent liquid was obtained. This was designated as additive 1.

[0031]Production Example 2 [Polyoxyethylene (2) N-
Synthesis of methyl lauric acid monoethanolamide] N-methyl lauric acid monoethanol alcohol described in Production Example 1
Transfer 237 g of amide to an autoclave and add potassium hydroxide
0.3g as catalyst, pressure 2.0kg / cm ²,temperature
At 120 ° C, 88 g of ethylene oxide was reacted.
Polyoxyethylene (2) N-methyl laurate
325 g of noethanolamide were obtained. Add this to additive 2
did.

Production Example 3 [Polyoxypropylene (2)
Lioxyethylene (1) N-ethyl laurate monoeta
Synthesis of noramide] 200.3 g (1.0 mol) of lauric acid was charged, and dissolved by heating to 80 ° C. under a nitrogen stream, and 107.0 g (1.2 mol) of N-ethylethanolamine was added thereto, followed by 150 ° C.
For 6 hours. After cooling to 80 ° C., the pressure inside the reaction system was gradually reduced to 150 ° C., and unreacted amine was distilled off. This was put in an autoclave, and potassium hydroxide was added to 0.1 ml.
3 g as a catalyst, pressure 2.0 kg / cm ² , temperature 120
After reacting 44 g of ethylene oxide under the condition of ° C., subsequently reacting with 116 g of propylene oxide,
Polyoxypropylene (2) Polyoxyethylene (1)
431 g of N-ethyl lauric acid monoethanolamide was obtained. This was designated as additive 3.

Production Example 4 [Polyoxypropylene (3)
Lioxyethylene (5) N-methyl myristate monoe
Synthesis of tanolamide ] 229.5 g (1.0 mol) of myristic acid was charged,
The temperature was raised to 80 ° C. under a nitrogen stream, and 91.0 g (1.2 mol) of N-methylethanolamine was added.
Aged for hours. After cooling to 80 ° C., 200 g of water was charged.
Stir and mix for 0 minutes. The mixture was allowed to stand at 90 ° C. for 30 minutes to remove the lower layer water, and dehydrated at 110 ° C. under reduced pressure. This was put into an autoclave and reacted with 220 g of ethylene oxide under the conditions of a pressure of 2.0 kg / cm ² and a temperature of 120 ° C. using 0.3 g of sodium hydroxide as a catalyst, and subsequently reacted with 174 g of propylene oxide, 681 g of propylene (3) polyoxyethylene (5) N-methyl myristate monoethanolamide was obtained. This was designated as additive 4.

Production Example 5 [Polyoxypropylene (3) N
-Synthesis of methyl coconut fatty acid monoethanolamide ] 206.3 g (1.0 mol) of coconut fatty acid was charged,
The temperature was raised to 80 ° C under a nitrogen stream, and 91.0 g (1.2 mol) of N-methylethanolamine was added.
Aged for hours. After cooling to 80 ° C., the pressure inside the reaction system was gradually reduced, and the temperature was raised to 150 ° C. to distill off unreacted amine. This was put in an autoclave and the pressure was 2.0 kg / cm ² and the temperature was 1 with 0.3 g of sodium hydroxide as a catalyst.
The mixture was reacted with 174 g of propylene oxide at 20 ° C. to obtain 438 g of polyoxypropylene (3) N-methyl coconut fatty acid monoethanolamide. This was designated as additive 5.

Example 1 A viscosity increasing test was carried out in a 20% aqueous solution of sodium polyoxyethylene (3) lauryl ether sulfate. The composition is shown in Table 1 below.

[0036]

[Table 1] The measurement method was measured using a BM type viscometer. The viscosity results at measurement temperatures of 10, 25 and 40 ° C. are shown in [Table 2], [Table 3],
It is shown in [Table 4].

As a comparative example, the same thickening test was carried out using lauric acid diethanolamide, lauric acid monoethanolamide, and polyethylene glycol distearate (average molecular weight: 6000).

[0038]

[Table 2]

[0039]

[Table 3]

[0040]

[Table 4]

Example 2 A foam increasing test was carried out in a 20% aqueous solution of sodium polyoxyethylene (3) lauryl ether sulfate. The composition is shown in Table 5 below.

[0042]

[Table 5] The measuring method was measured according to the Weeks method. Keeping the thermostat at 25 ° C, 200g of 0.1% surfactant concentration aqueous solution
Was gently put into a measuring cylinder so that no foam was formed. After stirring at 2500 rpm for 60 seconds, the foam volume (ml) (total volume-drain amount) after 5 minutes was measured. The test was performed twice for each sample, and the average was determined. The results are shown in [Table 6].

[0043]

[Table 6]

Example 3 A low-temperature stability test was carried out in a 20% aqueous solution of sodium polyoxyethylene (3) lauryl ether sulfate. The composition is shown in [Table 7] below.

[0045]

[Table 7] The measurement was taken in a 50 ml test tube, and the sample was taken at a temperature of 0 ° C for 2 minutes.
After storing for a week, the appearance was observed. The results are shown in [Table 8].

[0046]

[Table 8]

The following is an example of the formulation of a detergent to which the thickening / foaming agent of the present invention has been added.

Formulation Example 1 (Shampoo) A shampoo having the composition shown in Table 9 below was prepared. The obtained shampoo was excellent in foaming property and detergency, had an appropriate viscosity, and was good in feeling without squeaking.

[0049]

[Table 9]

Formulation Example 2 (Body Shampoo) A body shampoo shown in the following [Table 10] was prepared. The obtained body shampoo was excellent in foaming properties, had an appropriate viscosity, and had a very good fresh feeling after use.

[0051]

[Table 10]

Formulation Example 3 (Dishwashing detergent) A dishwashing detergent shown in the following [Table 11] was prepared. The obtained dishwashing detergent was excellent in foaming properties, washing properties, and rinsing properties, had an appropriate viscosity, and was good in feeling and without slimy feeling.

[0053]

[Table 11]

[0054]

──────────────────────────────────────────────────続 き Continued on the front page (51) Int.Cl. ⁷ Identification symbol FI Theme court ゛ (Reference) C07C 233/18 C07C 233/18 233/20 233/20 C08G 65/08 C08G 65/08 C09K 3/00 103 C09K 3/00 103H F-term (reference) 4C083 AC122 AC482 AC641 AC642 AC782 AC792 AD132 CC23 CC38 EE06 FF01 4H003 AB15 AB31 AC13 BA12 DA02 DA17 EB04 EB07 EB22 EB42 ED02 FA18 FA30 4H006 AA02 AC41 AC43 AC53 BA01 BC02

Claims (3)

[Claims] 1. A thickening / foaming agent comprising an alkanolamide represented by the following general formula (1). Embedded image [In the formula, R ₁ represents a linear or branched alkyl group having 7 to 21 carbon atoms, an alkenyl group, or a hydroxyalkyl group.
R ₂ represents a linear or branched alkyl group having 1 to 3 carbon atoms. R ₃ represents a linear or branched chain alkylene group having 2 to 3 carbon atoms, n number of R ₃ may be the same or different.
n shows the arbitrary number of 0-20. ] 2. A method for producing a thickening / foaming agent comprising an alkanolamide represented by the general formula (1) according to claim 1, wherein the fatty acid or the fatty acid is represented by the following general formula (2): An alkyl ester is reacted with an amine represented by the following general formula (3), or a fatty acid or a fatty acid alkyl ester represented by the following general formula (2) is reacted with the following general formula (3)
Wherein the reaction product obtained by the reaction is further reacted with an alkylene oxide represented by the following general formula (4). Method. Embedded image [Wherein, R ₁ represents a linear or branched alkyl group having 7 to 21 carbon atoms, an alkenyl group, or a hydroxyalkyl group;
R ₄ is a hydrogen atom or an alkyl group having 1 to 3 carbon atoms. [Chemical formula 3] [In the formula, R ₂ represents a linear or branched alkyl group having 1 to 3 carbon atoms. [Formula 4] [Wherein, R ₃ represents a linear or branched alkylene group having 2 to 3 carbon atoms. ] 3. A cleaning composition comprising the thickening / foaming agent according to claim 1.