JP2014218473A - Cosmetic base and cosmetic containing cosmetic base - Google Patents

Abstract

PROBLEM TO BE SOLVED: To provide a cosmetic base composed of a resin acid amide amine compound, especially a cosmetic base suitable for a cosmetic for hair to demand hairdressing performance and a cosmetic for skin to demand luster so that excellent hairdressing performance, setting performance, satisfactory consistency, natural luster, and moist feeling are given to hair, excellent luster and moist feeling can be given to skin, these effects are long-lasting because of easy staying on skin, and the cosmetic base can be also blended to an aqueous cosmetic preparation, and provide a hair cosmetic and a skin cosmetic blended with the cosmetic base.SOLUTION: A cosmetic base comprises an amide amine compound or a salt thereof represented by the following general formula (1) (in the formula, RCO represents a resin acid residue, Rrepresents an alkyl group having a carbon number of 1-3, and m is an integer of 2-4) obtained by reacting a resin acid and a diamine compound, and the cosmetic base is contained to make up a hair cosmetic and a skin cosmetic.

Description

  The present invention relates to a cosmetic base material comprising a resin acid amidoamine compound or a salt thereof, and more specifically, it has excellent setting properties and hair styling properties for hair, and also imparts flexibility, natural luster and moist feeling to hair. The present invention relates to a cosmetic base material comprising a novel amidoamine compound or a salt thereof capable of imparting an excellent gloss and moist feeling to the skin, and a cosmetic for hair and skin containing the cosmetic base material .

  Resin acid (also known as rosin or resin) obtained from rosin gives hair an excellent luster, styling, and setability, so it has traditionally been used in hair cosmetics, especially hair styling agents, hair setting agents, and eyelash cosmetics. Have been used (Patent Documents 1, 2, etc.). In addition, skin cosmetics have also been used in lip cosmetics such as lipsticks and lip balms and nail cosmetics such as nail polish for the purpose of imparting gloss (Patent Documents 3, 4, etc.). However, resin acid is insoluble in water and is difficult to use as a cosmetic because it is solid at room temperature. In most cases, it is dissolved in a large amount of fats and oils or converted into an ester derivative of a polyhydric alcohol. Used in cosmetics. However, there is a problem that when the water content is increased, the resin acid is hardened and the feeling during application is deteriorated.

  In addition, the main component of resin acid is abietic acid, but since it has a double bond in its chemical structure, it has the disadvantages that it easily undergoes oxidative discoloration and inferior stability over time of cosmetics. However, recently, this problem has been overcome by using hydrogenated resin acid (Patent Document 5).

  Conventionally, amidoamine compounds are often blended in hair cosmetics such as hair rinses, hair conditioners and hair setting agents. This is because the amidoamine compound is easy to be incorporated into various cosmetics such as water-based cosmetics and oily cosmetics, imparts smoothness, flexibility, slipperiness and antistatic properties to the hair, and the emulsifying properties of the amidoamine compounds are hair conditioners and hair rinses. This is because the effect of stabilizing the product is high. In general, as an amidoamine compound, a fatty acid having 7 to 21 carbon atoms combined with a diamine compound is used in cosmetics (Patent Document 6, etc.). A lanolin fatty acid is also proposed (Patent Document 7).

JP 2001-10933 A JP 2002-154932 A JP 2003-160434 A JP 2011-184317 A JP 2009-274990 A JP-A-10-182362 JP 2001-158663 A

  The present invention can impart flexibility and natural moist feeling to the hair while maintaining the properties of the resin acid that gives gloss and hair-styling properties, and gives the skin an excellent gloss and moist feeling. It is easy to stay on the hair and skin, has long-lasting effects, and can also be formulated into water-based cosmetics. In particular, it is a cosmetic base suitable for hair cosmetics that require hair styling and lip cosmetics that require gloss. An object of the present invention is to provide a cosmetic for hair and a skin for cosmetics containing the cosmetic base material.

  As a result of repeated researches to solve the above problems, the present inventors have increased the solubility in water when a resin acid is reacted with a diamine compound to form a resin acid amidoamine compound. Not only does it give hairstyling properties and setability to hair, it also gives a natural luster and moist feel that cannot be obtained with synthetic polymer setting agents, and is a property of amidoamine compounds. It is an excellent cosmetic base material for hair cosmetics that exhibits excellent flexibility and anti-static properties. It also gives the skin an excellent luster and moist feeling, and it is easy to stay on the skin and has a long-lasting effect. Therefore, it has been found that it is particularly excellent as a cosmetic base material for lip cosmetics, and the present invention has been completed.

（式中、Ｒ^１ＣＯは樹脂酸残基を表し、Ｒ^２は炭素数１〜３のアルキル基を表し、ｍは２〜４の整数である）
で表されるアミドアミン化合物またはその塩からなることを特徴とする化粧品基材を基本発明とするものであって、これを請求項１に係る発明とする。 That is, the present invention provides the following general formula (1)

(Wherein R ¹ CO represents a resin acid residue, R ² represents an alkyl group having 1 to 3 carbon atoms, and m is an integer of 2 to 4)
A cosmetic base material characterized by comprising an amidoamine compound represented by the formula (1) or a salt thereof is a basic invention, and this is the invention according to claim 1.

に示したように、その化学構造中に不飽和結合を有するものが多く、経時的に着色や着臭が進み、保存安定性が悪いという欠点がある。そのため、樹脂酸を水素添加して不飽和結合を減少させた水素添加樹脂酸（水添樹脂酸）が市販されている。本発明の化粧品基材でも、水素添加樹脂酸を用いたアミドアミン化合物は経時的安定性に優れるので、一般式（１）においてＲ^１ＣＯが水素添加樹脂酸残基であるものを請求項２に係わる発明とする。 Resin acid is obtained by distilling rosin, and mainly contains abietic acid, neoabietic acid, dihydroabietic acid, tetrahydroabietic acid, and other various abietic acid isomers. (7)

As shown in the above, there are many that have an unsaturated bond in the chemical structure, and there is a drawback that coloring and odor progress with time and storage stability is poor. Therefore, hydrogenated resin acids (hydrogenated resin acids) in which unsaturated bonds are reduced by hydrogenation of resin acids are commercially available. Even in the cosmetic base material of the present invention, since an amidoamine compound using a hydrogenated resin acid is excellent in stability over time, a compound in which R ¹ CO is a hydrogenated resin acid residue in the general formula (1) is defined in claim 2 The invention is concerned.

  The cosmetic base material comprising the resin acid amidoamine compound or a salt thereof of the present invention is excellent in setting properties and hair styling properties for hair, and has a high effect of imparting softness, natural luster and moist feeling to hair. When blended with a hair set agent, the effects of the present invention are remarkably exhibited. Accordingly, in the present invention, a cosmetic for hair comprising the cosmetic base material according to any one of claims 1 and 2 is defined as the invention according to claim 3.

  Invention of Claim 4 is cosmetics for hair of Claim 3 whose content of the cosmetic base material of Claim 1 or 2 is 0.05-10 mass%. The preferred range of the content of the cosmetic base material of the present invention in the cosmetics for hair varies depending on the type of hair cosmetics and the form of use, but usually 0.05 to 10% by mass with respect to the total mass of the hair cosmetics. preferable.

  In addition, the cosmetic base comprising the resin acid amidoamine compound of the present invention or a salt thereof has a high effect of imparting an excellent gloss and moist feeling to the skin. The effect of the present invention is remarkably exhibited. Accordingly, in the present invention, a skin cosmetic comprising the cosmetic base material according to any one of claims 1 and 2 is defined as the invention according to claim 5.

  Furthermore, since the cosmetic base material comprising the resin acid amidoamine compound of the present invention or a salt thereof, when incorporated into lip cosmetics such as lipsticks and lip balms, the gloss-imparting effect is remarkably exhibited. The invention according to claim 6 is a cosmetic product for lips.

  The invention according to claim 7 is characterized in that the content of the cosmetic base material according to claim 1 or 2 is 0.5 to 20% by mass, according to claim 5 or 6. Cosmetics. The preferred range of the content of the cosmetic base material of the present invention in the skin cosmetic varies depending on the type of skin cosmetic and the form of use, but usually 0.5 to 20 mass relative to the total mass of the skin cosmetic. % Is preferred.

  The cosmetic base material of the present invention imparts excellent hair styling properties and setability to the hair, and can also impart flexibility and good cohesiveness to the hair, and also contains a synthetic polymer and a hair styling agent or hair set. Natural luster and moist feeling that can not be obtained with the agent. In addition, it gives the skin an excellent luster and moist feeling, and since it tends to stay on the skin, these effects last for a long time. Furthermore, since the cosmetic base material of the present invention is in the form of amidoamine, it is easy to be blended in water-soluble cosmetics as well as oily cosmetics, and has good compatibility with various cosmetic raw materials. When blended into skin cosmetics, the above effects are exhibited.

The resin acid amidoamine compound constituting the cosmetic base material of the present invention is represented by the above general formula (1), but the resin acid constituting the R ¹ CO portion is obtained from pine resin (rosin) of the Pinaceae plant. It is a thing. Resin acid is a mixture of abietic acid, neoabietic acid, dihydroabietic acid, tetrahydroabietic acid, dehydroabietic acid, pimaric acid, isopimaric acid, etc. However, as a raw material for the cosmetic base material of the present invention, any resin acid or hydrogenated resin acid (hydrogenated resin acid) can be used. Arakawa Chemical Industries, Harima Sold by Kasei Co., Ltd.

〔式中、Ｒ^２およびｍは、前記一般式（１）に同じである〕
で表される。このようなジアミン化合物としては、ジエチルアミノエチルアミン、ジエチルアミノプロピルアミン、ジメチルアミノエチルアミン、ジメチルアミノプロピルアミンなどを挙げることができる。 The resin acid amidoamine compound represented by the general formula (1) is obtained by amidating the carboxy group of the resin acid with a diamine compound. The diamine compound is represented by the following general formula (8).

[Wherein R ² and m are the same as those in the general formula (1)]
It is represented by Examples of such diamine compounds include diethylaminoethylamine, diethylaminopropylamine, dimethylaminoethylamine, dimethylaminopropylamine and the like.

  The reaction between the resin acid and the diamine compound can be carried out by a known method for producing a fatty acid amidoamine such as Patent Document 7 and Japanese Patent Application Laid-Open No. 2004-75668. 8 to 1.5 mol of resin acid is reacted at a temperature of 170 to 200 ° C. for 8 to 20 hours.

  The reaction molar ratio of the resin acid to the diamine compound is within this range because the reaction rate of the diamine compound to the resin acid is extremely reduced even if the resin acid is less than 0.8 or 1.5 or more with respect to the diamine compound 1. Is preferable.

  Although the reaction temperature of a diamine compound and resin acid is 170-200 degreeC, 175-185 degreeC is more preferable. This is because the resin acid has a high melting point and hardly dissolves at 170 ° C. or lower, and if the reaction temperature is too high, the reaction product may be decomposed. If the reaction time is 8 hours or less, the reaction rate is low, so 8 hours or more are necessary, and preferably 14 to 16 hours. The reaction is preferably performed in a nitrogen atmosphere in order to suppress oxidation of the resin acid.

  An acid catalyst such as phosphoric acid can be added to the reaction, but if a large amount of acid catalyst is used, the nitrogen-carbon bond of the diamine compound may be cleaved and diamide may be produced, resulting in a decrease in the reaction rate. Since it varies depending on the type of raw material used in the reaction and the reaction temperature, when using a catalyst, it is necessary to determine the addition amount in advance by a test.

  Although the resin acid amidoamine compound is obtained in this manner, an unreacted diamine compound may remain even if the amount of the resin acid relative to the diamine compound is increased during the reaction. Some diamine compounds have skin irritation and are preferably purified to remove unreacted diamine compounds. As a solvent for purification, an organic solvent capable of separating a water-soluble diamine compound and dissolving a resin acid amidoamine compound is desirable. For example, 1-butanol or 2-methyl-1-propanol (isobutanol) is preferable. is there.

  In the purification, an organic solvent and water are added to the reaction solution of the resin acid and the diamine compound, the diamine compound is moved to the aqueous layer to remove the aqueous layer, and the organic layer containing the resin acid amidoamine compound is removed by concentration under reduced pressure or the like. It can be done by removing. After removing the solvent, depending on the purpose of use, water, an organic solvent, a water-containing organic solvent, or the like may be added to form an organic solution or aqueous solution of the resin acid amidoamine compound.

  Moreover, unreacted resin acid can be removed by column chromatography or the like to obtain a highly pure resin acid amidoamine compound. For example, the reaction product is dissolved in an organic solvent, passed through a silica gel column, developed with an organic solvent-water developing solvent, and the resin acid amidoamine purified by removing only the resin acid amidoamine fraction and removing the solvent. A compound can be obtained. This purification step may be performed after the above diamine compound removal operation. However, if the amount of water in the developing solvent is reduced during silica gel column purification, the diamine compound remains adsorbed on the silica gel and has low mobility. Therefore, the diamine compound can be separated from the resin acid amidoamine compound eluted earlier, and the operation of removing the diamine compound with the solvent can be omitted.

  The salt of the resin acid amidoamine compound can be obtained by adding an acid to the amidoamine compound and neutralizing it. Examples of acids for forming a salt include inorganic acids such as hydrochloric acid, sulfuric acid, and phosphoric acid, organic acids such as acetic acid, lactic acid, succinic acid, citric acid, malic acid, and acidic amino acids, and peptides having a free carboxy group. Etc.

〔式中、Ｒ^２およびｍは前記一般式（１）に同じである〕
で表される。 As described above, since the resin acid amidoamine compound is a mixture of abietic acid and its isomers as described above, it cannot be represented by one structural formula. For example, when abietic acid reacts with a diamine compound, The amidoamine compound has the following general formula (9)

[Wherein R ² and m are the same as those in the general formula (1)]
It is represented by

〔式中、Ｒ^２およびｍは前記一般式（１）に同じである〕
で表される。 When tetrahydroabietic acid, which is considered to be the main component in the hydrogenated resin acid, reacts with the diamine compound, the amidoamine compound is represented by the following general formula (10).

[Wherein R ² and m are the same as those in the general formula (1)]
It is represented by

〔式中、Ｒ^２およびｍは前記一般式（１）に同じで、Ｍ⁻ は一価の陰イオンを示す〕
で表される。 Furthermore, in the case of a salt of a reaction product of abietic acid and a diamine compound, the salt of the amidoamine compound is represented by the following general formula (11):

[Wherein R ² and m are the same as those in the general formula (1), and M ⁻ represents a monovalent anion]
It is represented by

  Examples of hair cosmetics to which the cosmetic base material of the present invention can be formulated include shampoos, hair rinses, hair conditioners, split hair coats, hair creams, hair styling agents, hair set sprays, hair styling gels, hair styling mousses, and permanent waves. Examples include first and second agents, hair dyes, hair dyes, hair nourishing and hair restorers, makeup cosmetics such as eyebrow and mascara, etc. The resin acid amidoamine compound of the present invention or a salt thereof is used for hair styling. Hair, hair conditioner, hair cream, hair conditioner, hair set spray, hair styling gel, hair styling mousse, etc. Cosmetic products are particularly preferred.

  The preferred range of the amount of the cosmetic base material of the present invention incorporated into the hair cosmetic product (content in the cosmetic product) varies depending on the type of hair cosmetic product and cannot be specifically limited. 05-10 mass% is preferable, and about 0.1-5 mass% is especially preferable in many cases. When the blending amount in the cosmetic for hair is less than the above range, there is a possibility that the effect of imparting hair styling property, setability, cohesiveness and flexibility, natural luster and moist feeling to the hair may not be sufficiently exhibited, Moreover, even if the blending amount of the cosmetic base material of the present invention is more than the above range, not only the improvement of the effect corresponding to the amount is observed, but also there is a possibility that the hair becomes sticky or the hair feels hard. However, some hair sticks and hair solids used for the purpose of solidifying hair have a blending amount of 10% by mass or more.

  Examples of skin cosmetics to which the cosmetic base material of the present invention can be formulated include creams, foundations, lipsticks, lip balms, lip glosses, etc. The resin acid amidoamine compounds of the present invention or their salts are glossy. Among these skin cosmetics, lip cosmetics such as lipstick, lip balm, and lip gloss are particularly preferable because of their high imparting effect.

  And since the preferable range of the blending amount (content in cosmetics) of the cosmetic base material of the present invention into the skin cosmetics differs depending on the type of skin cosmetics, it cannot be specifically limited. 0.5-20 mass% is preferable and especially about 1-15 mass% is preferable in many cases. When the blending amount in the skin cosmetic is less than the above range, the effect of imparting natural luster may not be expressed, and even if the blending amount of the cosmetic base material of the present invention exceeds the above range, In addition to not seeing an improvement in the effect, there is a risk of stickiness.

  Ingredients that can be blended in the hair cosmetics and skin cosmetics in combination with the cosmetic base material of the present invention include, for example, anionic surfactants, nonionic surfactants, amphoteric surfactants, and cationic surfactants. Synthetic polymers such as cationic polymers, amphoteric polymers, anionic polymers, semi-synthetic polymers, animal and vegetable oils, hydrocarbons, ester oils, higher alcohols, amino acids, thickeners, animal and plant extracts, silicones, antiseptics Protein hydrolyzates obtained by hydrolyzing proteins derived from agents, fragrances, animals and plants, and microorganisms, and esterified derivatives, quaternary ammonium derivatives, silylated derivatives, acylated derivatives and salts thereof, and the like. . In addition to these, other components can be appropriately added as long as the properties of the cosmetic base material of the present invention are not impaired.

  EXAMPLES Next, although an Example is given and this invention is demonstrated concretely, this invention is not limited only to those Examples. In addition, all% described in the Example etc. is the mass%. Moreover, in the Example containing the prescription of cosmetics, all compounding quantities are based on a mass part, and about the thing which a compounding quantity is not solid content amount, solid content concentration is shown in parenthesis after an ingredient name.

Example 1 Production of Hydrogenated Resin Acid Diethylaminoethylamide-1
In a 1-liter closed separable flask, 42 g of diethylaminoethylamine and 100 g of hydrogenated resin acid [Arakawa Chemical Industries, Ltd. Pine Crystal KR-85 (trade name)] (0.9 equivalents per 1 mol of diethylaminoethylamine) Then, 5.3 g of phosphoric acid (0.15 equivalent to 1 mol of diethylaminoethylamine) was added, the space above the solution was replaced with nitrogen, and stirring was continued at 180 ° C. for 15 hours to amidate. The reaction rate of diethylaminoethylamine with respect to the hydrogenated resin acid was 65%. The molecular weight of the hydrogenated resin acid is 306, which is the molecular weight of tetrahydroabietic acid, and the reaction rate of the diamine compound (diethylaminoethylamine) is determined by measuring the total nitrogen amount and amino nitrogen amount of the reaction solution before and after the reaction, respectively. The total nitrogen content and the amino nitrogen content were compared.

  Next, the reaction product was dissolved in a small amount of a mixed solvent of chloroform: methanol: water = 20: 3: 0.3, and 700 ml of silica gel [Wakosil C-200 (trade name) manufactured by Wako Pure Chemical Industries, Ltd.] was added. The sample was placed on a packed glass column having a diameter of 3 cm and a length of about 30 cm (the height of the silica gel was about 25 cm), and partition chromatography was performed with a developing solvent of chloroform: methanol: water = 20: 3: 0.3. Fractions from 400 ml to 1000 ml of the eluate were collected and the solvent was removed by concentration under reduced pressure to obtain 82 g of hydrogenated resin acid diethylaminoethylamide as a dry solid. In addition, confirmation of whether it was a developed fraction containing the target component by column chromatography was performed by thin layer chromatography using the same developing solvent as described above.

Example 2: Production of hydrogenated resin acid diethylaminoethylamide-2
In a sealed separable flask with a capacity of 1 liter, 38 g of diethylaminoethylamine, 100 g of hydrogenated resin acid [Arakawa Chemical Industries, Ltd. Pine Crystal KR-85 (trade name)] (1 equivalent per 1 mol of diethylaminoethylamine) and phosphorus The acid 4.8g (0.15 equivalent with respect to 1 mol of diethylaminoethylamine) was put, the space of the solution top was substituted with nitrogen, and stirring was continued at 180 degreeC for 15 hours, and it amidated. The reaction rate of diethylaminoethylamine with respect to the hydrogenated resin acid was 62%.

  Next, the temperature of the solution is gradually lowered and kept at 60 to 80 ° C. while stirring, 100 g of isobutanol and 100 g of water are added and homogenized, transferred to a separatory funnel, the reaction product is washed, Discharged. The operation of adding 100 g of water to the remaining isobutanol layer and discharging the aqueous layer after washing was repeated twice. Next, an appropriate amount of water is added to the washed solution and concentrated under reduced pressure.The addition of water and concentration under reduced pressure are repeated until there is no smell of isobutanol to remove isobutanol and moisture, and the hydrogenated resin acid is added as a dry solid. 110 g of a hydrogenated resin acid diethylaminoethylamide-hydrogenated resin acid mixture containing about 38% was obtained.

Example 3: Production of hydrogenated resin acid dimethylaminopropylamide-1
In a 1-liter sealed separable flask, 33 g of dimethylaminopropylamine and 100 g of hydrogenated resin acid [Pine Crystal KR-85 (trade name) manufactured by Arakawa Chemical Industries, Ltd.] (1 mol per 1 mol of dimethylaminopropylamine) Equivalent) and 3.8 g of phosphoric acid (0.12 equivalent to 1 mol of dimethylaminopropylamine), the space above the solution was replaced with nitrogen, and stirring was continued at 180 ° C. for 15 hours for amidation. The reaction rate of dimethylaminopropylamine to the hydrogenated resin acid was 67%.

  Next, the reaction product was dissolved in a small amount of a mixed solvent of chloroform: methanol: water = 20: 3: 0.3, and 700 ml of silica gel [Wakosil C-200 (trade name) manufactured by Wako Pure Chemical Industries, Ltd.] was added. The sample was placed on a packed glass column having a diameter of 3 cm and a length of about 30 cm (silica gel height of about 25 cm), and developed with a developing solvent of chloroform: methanol: water = 20: 3: 0.3. The 400 to 1000 ml fractions of the eluate were collected and the solvent was removed by concentration under reduced pressure to obtain 85 g of hydrogenated resin acid dimethylaminopropylamide as a dry solid.

Example 4: Production of hydrogenated resin acid dimethylaminopropylamide-2
In a 1-liter sealed separable flask, 31.7 g of dimethylaminopropylamine and 100 g of hydrogenated resin acid [Pine Crystal KR-85 (trade name) manufactured by Arakawa Chemical Industries, Ltd.] (for 1 mol of dimethylaminopropylamine) 0.95 equivalents) and 5.0 g of phosphoric acid (0.15 equivalents per mole of dimethylaminopropylamine), the space above the solution was replaced with nitrogen, and stirring was continued at 180 ° C. for 15 hours. Turned into. The reaction rate of dimethylaminopropylamine with respect to the hydrogenated resin acid was 66%.

  Next, the temperature of the solution is gradually lowered and kept at 60 to 80 ° C. while stirring, 100 g of isobutanol and 100 g of water are added and homogenized, transferred to a separatory funnel, the reaction solution is washed, and the aqueous layer portion is Discharged. The operation of adding 100 g of water to the remaining isobutanol layer and discharging the aqueous layer after washing was repeated twice. Next, an appropriate amount of water is added to the washed solution and concentrated under reduced pressure.Addition of water and concentration under reduced pressure are repeated until there is no odor of isobutanol to remove isobutanol and moisture, and the hydrogenated resin acid is reduced to a dry solid. 105 g of hydrogenated resin acid dimethylaminopropylamide containing 34% was obtained.

Example 5 Production of Glutamate of Resin Acid Diethylaminoethylamide 38 g of diethylaminoethylamine and 99 g of resin acid (1 equivalent to 1 mol of diethylaminoethylamine) and 4.8 g of phosphoric acid (diethylamino) were placed in a 1-liter sealed separable flask. 0.15 equivalents to 1 mol of ethylamine), the space above the solution was replaced with nitrogen, and agitation was continued at 180 ° C. for 16 hours. The reaction rate of diethylaminoethylamine to the resin acid was 60%. The molecular weight 302 of abietic acid was used as the molecular weight of the resin acid.

  Next, the temperature of the solution is gradually lowered and kept at 60 to 80 ° C. while stirring, 100 g of isobutanol and 100 g of water are added and homogenized, transferred to a separatory funnel, the reaction solution is washed, and the aqueous layer portion is Discharged. The operation of adding 100 g of water to the remaining isobutanol layer and discharging the aqueous layer after washing was repeated twice. Next, an aqueous solution of glutamic acid was added to this solution to adjust the pH of the solution to 7 to obtain a glutamic acid salt of resin acid diethylaminoethylamide. An appropriate amount of water was added to this solution and concentrated under reduced pressure. The addition of water and concentration under reduced pressure were repeated until the butanol smell disappeared. To this washed neutralized solution, glycerin and ethanol were added so that the resin acid diethylaminoethylamide was 50% by mass, glycerin 20% by mass, and ethanol 30% by mass, and the resin acid diethylaminoethylamide glutamic acid containing about 40% resin acid was added. 250 g of a salt glycerin-ethanol mixture was obtained.

Example 6 Production of Resin Acid Dimethylaminopropylamide In a 1-liter sealed separable flask, 33.8 g of dimethylaminopropylamine, 100 g of resin acid (1 equivalent per 1 mol of diethylaminoethylamine) and 4.8 g of phosphoric acid (0.15 equivalent relative to 1 mol of dimethylaminopropylamine) was added, and the space above the solution was replaced with nitrogen, and stirring was continued at 180 ° C. for 16 hours for amidation. The reaction rate of dimethylaminopropylamine with respect to the resin acid was 60%.

  Next, the temperature of the solution is gradually lowered and kept at 60 to 80 ° C. while stirring, 100 g of isobutanol and 100 g of water are added and homogenized, transferred to a separatory funnel, the reaction solution is washed, and the aqueous layer portion is Discharged. The operation of adding 100 g of water to the remaining isobutanol layer and discharging the aqueous layer after washing was repeated twice. Next, an appropriate amount of water was added to the washed solution and concentrated under reduced pressure. After adding isobutanol and water under reduced pressure until the smell of isobutanol disappeared, isobutanol and water were removed, and then 50 mass of dimethylaminoethylamide resin acid was added. %, 20% by mass of glycerin, and 30% by mass of ethanol, glycerin and ethanol were added to obtain 244 g of a glycerin-ethanol mixture of dimethylaminopropylamide resin acid containing about 38% resin acid.

Example 7 and Comparative Examples 1-2
A hair conditioner having the composition shown in Table 1 was prepared, applied to the hair, and the setting power (set retention rate) on the hair was examined, and the gloss, flexibility, moist feeling, and goodness of the hair after the treatment were evaluated. In Example 7, the hydrogenated resin acid diethylaminoethylamide produced in Example 1 was used. In Comparative Example 1, the hydrogenated resin acid used in the production of Example 1 was used instead of the resin acid amidoamine compound. In No. 2, stearic acid diethylaminoethylamide, which is an amidoamine compound generally used in cosmetics, is used.

  In Table 1, * 1 is Pine Crystal KR-85 (trade name) manufactured by Arakawa Chemical Industries, * 2 is Ayacol Aminamide 50E (trade name) manufactured by Seiwa Kasei Co., Ltd., * 3 is Nikko Chemicals ( Nikkor BS-20 (trade name) manufactured by Co., Ltd. * 4 is Seycept H (trade name) manufactured by Seiwa Kasei Co., Ltd.

  Prior to the treatment with the hair conditioner, the hair was washed with a 2% aqueous solution of polyoxyethylene (3) sodium lauryl ether sulfate to produce three hair bundles having a length of 12 cm and a weight of 2 g. In order to make the hair damage of this hair bundle constant, it is immersed in an aqueous solution containing 3% aqueous hydrogen peroxide and 1% ammonia at 30 ° C. for 30 minutes, bleached, washed with running tap water, and further ion exchanged. Rinse with water and dry with a hair dryer. After repeating this bleaching process 5 times, the hair bundle was subjected to the following test.

  1 g of each of the hair conditioners of Example 7 and Comparative Examples 1 and 2 was applied to each hair bundle, allowed to stand for 5 minutes, and then rinsed with running hot water. The hair bundle was wound around a rod having a diameter of 2 cm and dried in a dryer at 60 ° C. for 20 minutes. The hair bundle after drying was removed from the rod, the length of the hair bundle was measured, and the wave ratio was calculated by the following formula.

  Next, this hair bundle was stored vertically suspended in a desiccator at a temperature of 20 ° C. and a relative humidity of 40% for 8 hours, the length of the hair bundle was measured again, and the set retention rate was determined by the following formula. .

  In addition, 10 panelists gave the gloss, softness, moistness, and goodness of hair of each hair bundle to 2 panelists, 2 points for the best, and 0 points for the inferior one. I let you. These results are shown in Table 2, and the sensory evaluation value is an average value of 10 people.

  As shown in Table 2, the hair bundle treated with the hair conditioner of Example 7 containing hydrogenated resin acid diethylaminoethylamide was the hair conditioner of Comparative Example 1 containing hydrogenated resin acid or stearic acid diethylaminoethylamide. Compared to the hair bundle treated with the hair conditioner of Comparative Example 2 containing the same, the wave rate is high, and the set retention rate is close to 80% even after 8 hours, and diethylaminoethyl hydrogenated resin contained in Example 7 It was clear that amides had excellent setting properties for hair and the ability to maintain the setting force for a long time.

  In addition, in the sensory evaluation of the hair with respect to the gloss, flexibility, moist feeling, and goodness of the hair after the treatment, the hair treated with the hair conditioner of Example 7 is the hair conditioner of Comparative Example 1 or Comparative Example 2. The evaluation value was higher than that of the treated hair, and it was clear that the hydrogenated resin acid diethylaminoethylamide contained in Example 7 imparted excellent gloss, flexibility, moist feeling and cohesiveness to the hair. .

Example 8 and Comparative Examples 3-4
A hair setting agent having the composition shown in Table 3 was prepared and applied to the hair, and the gloss, flexibility, moist feeling, cohesiveness and hair re-styling property of the hair were evaluated. In Example 8, the hydrogenated resin acid diethylaminoethylamide produced in Example 2 was used, and in Comparative Example 3, the hydrogenated resin acid used in the production of Example 2 was used instead of the hydrogenated resin acid diethylaminoethylamide, In Comparative Example 4, a polymer substance (alkyl acrylate / diacetone acrylamide) copolymer AMP, which is generally used for hair setting agents, is used. The blending amount of the (alkyl acrylate / diacetone acrylamide) copolymer AMP in Comparative Example 4 is 7.5 times the blending amount of the hydrogenated resin acid diethylaminoethylamide in Example 8, but this amount is It is a common usage of the copolymer AMP (alkyl acrylate / diacetone acrylamide) for hair set purposes.

In Table 3, * 1 is already described, * 5 is Plus Size L-6010 (trade name) manufactured by Kyoyo Chemical Industry Co., Ltd., * 6 is SS-3408 (trade name) manufactured by Toray Dow Corning Co., Ltd. * 7: TRANSCUTOL CG (trade name) of Ikeda Bussan Co., Ltd. * 8: Promois WK-H (trade name) manufactured by Seiwa Kasei Co., Ltd. * 9: Sensiva SC50 JP (trade name) manufactured by Schulke & Mayr ).
It is.

  Prior to the treatment with the above hair setting agent, prepare three human head-shaped wigs, wash with 1% polyoxyethylene (3) sodium lauryl ether sodium sulfate solution, rinse thoroughly with running water, and excess water with a towel. After being wiped off, it was dried with warm air. Take each 2 g of the hair setting agent of Example 8 and Comparative Examples 3 to 4 in each of these head-shaped wigs, apply it to the hair, shape the hair, dry it with a hair dryer, Ten panelists were evaluated on the same evaluation criteria as in Example 7 for flexibility, moist feeling, and good quality.

Furthermore, this wig was allowed to stand at room temperature overnight, and after about 24 hours, the hair of each wig was trimmed again and 10 panelists evaluated the hair re-styling properties based on the following criteria. These results are shown in Table 4 as an average of 10 people.
Evaluation criteria for re-styling 3 points that are excellent in re-styling 2 points that re-styling is slightly recognized 2 points that weak re-hairing properties 1 point no re-hairing properties 0 points

  As shown in Table 4, with regard to the hair after treatment, the hair treated with the hair setting agent of Example 8 has a high evaluation value in any of the evaluation items of gloss, flexibility, moist feeling, and good quality. It was clear that the hydrogenated resin acid diethylaminoethylamide blended in Example 8 was highly effective in imparting good luster, flexibility, moist feeling and cohesiveness to the hair. In addition, many panelists treated the hair setting agent of Comparative Example 4 with flaking and felt firm, but the hair treated with the hair setting agent of Example 8 was naturally soft and moist. I answered.

  In addition, regarding the hair re-styling property after 24 hours, the evaluation value of the hair re-styling property of the hair treated with the hair setting agent of Example 8 is high, and diethylamino acid hydrogenated resin compounded in the hair setting agent of Example 8 is used. It was clear that ethylamide not only gave the hair a setting effect, but the effect lasted for a long time.

  The hydrogenated resin acid diethylaminoethylamide produced in Example 2 used in Example 8 contains about 38% by mass of unreacted hydrogenated resin acid. As is apparent from the results, the hair set of Comparative Example 3 in which the hydrogenated resin acid was blended with the hydrogenated resin acid was effective in imparting gloss, flexibility, moist feeling, cohesiveness and re-styling to the hair of the hydrogenated resin acid diethylaminoethylamide. As a result, the cosmetic base material comprising the resin acid amidoamine compound of the present invention, which is superior to the agent, exhibits the effect of the resin acid amidoamine compound without being affected by the presence of unreacted resin acid. It is clear from

Example 9 and Comparative Examples 4-5
A hair set lotion having the composition shown in Table 5 was prepared and applied to the hair to examine the set retention rate, and the gloss, flexibility, moist feeling and goodness (setability) of the hair were evaluated. In Example 9, the hydrogenated resin acid dimethylaminopropylamide produced in Example 4 was used, and in Comparative Example 5, the hydrogenated resin acid used in the production of Example 4 was used instead of the hydrogenated resin acid dimethylaminopropylamide. In Comparative Example 6, behenic acid dimethylaminopropylamide, which is generally used as an amidoamine compound, is used.

  In Table 5, * 1 and * 4 are already described, and * 10 is NIKKOL amidoamine MPB (trade name) manufactured by Nikko Chemicals.

  The treatment with the above-mentioned hair set lotion was carried out in the same manner as in Example 7, using a hair bundle having a length of 12 cm and a weight of 2 g. The hair bundle was wound around a rod having a diameter of 2 cm, and each rod was carried out. After dipping in the set lotions of Example 9 and Comparative Examples 5 to 10 for 10 seconds and blotting off the excess set lotion with a towel, the hair bundle was dried in a dryer at 60 ° C. for 20 minutes while being wound around the rod. After drying, the hair bundle was removed from the rod, the length of the hair bundle was measured, and the wave rate was calculated using the same calculation formula as in Example 7.

  Furthermore, this hair bundle was stored in a desiccator with a temperature of 20 ° C. and a relative humidity of 40%, vertically suspended for 8 hours, the length of the hair bundle was measured again, and the set retention rate was calculated using the same formula as in Example 7. Asked. Further, ten panelists were allowed to perform sensory evaluation on the same evaluation criteria as in Example 7 with respect to the flexibility of each hair bundle and the goodness of hair unity. These results are shown in Table 6, and the sensory evaluation value is an average value of 10 people.

  As shown in Table 6, the hair bundle treated with the hair set lotion of Example 9 containing hydrogenated resin acid dimethylaminopropylamide is the hair set lotion or behenic acid of Comparative Example 5 containing hydrogenated resin acid. Compared with the hair set lotion of Comparative Example 6 containing dimethylaminopropylamide, the wave ratio is high, and the wave retention is 80% or more even after 8 hours, and dimethyl hydrogenated resin acid contained in Example 9 It was clear that aminopropylamide had excellent setting properties for hair and the ability to maintain the setting properties for a long time.

  Also, in the sensory evaluation of hair, the hair treated with the hair set lotion of Example 9 is more glossy, flexible, moist, and coherent than the hair treated with the hair set lotion of Comparative Example 5 and Comparative Example 6. The hydrogenated resin acid dimethylaminopropylamide contained in Example 9 has an effect of imparting excellent luster, flexibility, moist feeling and cohesiveness to the hair. It was clear that it was expensive.

Example 10 and Comparative Example 7
A hair styling composition (hair liquid) having the composition shown in Table 7 was prepared and applied to the hair to evaluate the gloss, flexibility, moist feeling and cohesiveness of the hair. In Example 10, the glycerin-ethanol mixed solution of the resin acid diethylaminoethylamide glutamate produced in Example 5 was used, and in Comparative Example 7, an acrylic acid-based synthetic polymer was used instead of the resin acid amidoamine compound. The amount of the (alkyl acrylate / diacetone acrylamide) copolymer AMP used in Comparative Example 7 is larger than the amount of the resin acid amide amine compound of Example 10, but the blending amount of the (alkyl acrylate / diacetone acrylamide) copolymer AMP. Has increased the hair set to the desired amount.

  In Table 7, * 5 is already described, and * 11 is Euxyl PE 9010 (trade name) manufactured by Schulke & Mayr.

  About the above-mentioned hair styling, 5 male panelists were made to treat their hair once a day with the hair styling of Comparative Example 7 for the first 5 days and the hair styling of Example 10 for the next 5 days. . In addition, it was left to each panelist's judgment about the usage-amount of hair-styling, and the presence or absence of dryer drying. After using the hair styling material of Example 10 for 5 days (after the completion of the 10-day test), the gloss, flexibility, moist feeling and cohesiveness of the hair become better than when the hair styling material of Comparative Example 7 was used. It was answered whether it got worse or not changed. The results are shown in Table 8 with the number of respondents.

  As shown in Table 8, most panelists answered that after using the hair styling agent of Example 10, the hair was more glossy and flexible than before use, and the hair became easier to unite, As for the moist feeling, all panelists answered that after using the hair styling agent of Example 10, natural moistness was imparted. That is, it was clear that the resin acid diethylaminoethylamide glutamate contained in Example 10 has a high effect of imparting good luster, flexibility, moist feeling of natural feeling, and cohesiveness to the hair.

Example 11 and Comparative Examples 8-9
Lipsticks having the compositions shown in Table 9 were prepared and evaluated for smoothness during application, gloss after application and moist feeling. In Example 11, the hydrogenated resin acid diethylaminoethylamide produced in Example 1 was used. In Comparative Example 8, the hydrogenated resin acid used in the production of Example 1 was used instead of the resin acid amidoamine compound. In Example 9, instead of the resin acid amidoamine compound, diethylaminoethylamide stearate, which is a general amidoamine compound, is used.

  In Table 9, * 1 and * 2 have already been mentioned, * 12 is multi-wax W-445 (trade name) manufactured by Witco, * 13 is ceresin 76 (trade name) from Iwase Cosfa, and * 14 is Shin-Etsu. KF-96A-10cs (trade name) manufactured by Chemical Industry Co., Ltd., * 15 is KF-96H-10,000 cs (trade name) manufactured by Shin-Etsu Chemical Co., Ltd.

About the lipstick of Example 11 and Comparative Examples 8-9, the smoothness (goodness of elongation) when applied to the lips, and the gloss after application, moist feeling (moist feeling) to 10 panelists, Evaluation was made according to the following evaluation criteria. The results are shown in Table 10 as the average value of 10 people.
Evaluation criteria Feel strongly: 3 points Feel: 2 points Almost not felt: 1 point Not felt at all: 0 points

  As shown in Table 10, the lipstick of Example 11 is smoother and easier to stretch at the time of application than the lipstick of Comparative Example 8 and Comparative Example 9, and the evaluation result that it gives a glossy and moist feeling after application, It was clear that the hydrogenated resinic acid diethylaminoethylamide blended in the lipstick of Example 11 had an action of imparting smoothness, gloss and moist feeling (moist feeling) to the skin.

Example 12 and Comparative Examples 10-11
Lip gloss creams having the compositions shown in Table 11 were prepared and applied to the lips to evaluate the smoothness during application, the gloss after application and the moist feeling. In Example 12, the hydrogenated resin acid dimethylaminopropylamide produced in Example 4 was used, and in Comparative Example 10, the hydrogenated resin acid used in the production of Example 4 was used instead of the resin acid amidoamine compound. In Comparative Example 11, instead of the resin acid amidoamine compound, behenic acid dimethylaminopropylamide, which is a general amidoamine compound, is used.

  In Table 11, * 1, * 9, and * 10 have already been mentioned, * 16 is NIKKOL jojoba wax (trade name) manufactured by Nikko Chemicals, and * 17 is NIKKOL Decaglyn 5-SV (trade name) manufactured by Nikko Chemicals. (Trade name), * 18 is Sunsoft No. manufactured by Taiyo Kagaku Co., Ltd. 818SK (trade name), * 19 is Leopard KL (trade name) manufactured by Chiba Flour Milling Co., Ltd., and * 20 is Cosmall 222 (trade name) manufactured by Nisshin Oillio Group.

  For the lip gloss creams of Example 12 and Comparative Examples 10-11, the smoothness (goodness of elongation) when applied to the lips, and the gloss after application, moist feeling (moist feeling) to five panelists, Evaluation was performed based on the same evaluation criteria as in Example 11. The results are shown in Table 12 as the average value of five people.

  As shown in Table 12, the lip gloss cream of Example 12 is more easily stretched during application than the lip gloss creams of Comparative Example 10 and Comparative Example 11, and gives a glossy and moist feeling (moist feeling) after application. It was clear that the hydrogenated resin acid dimethylaminopropylamide blended in Example 12 had an effect of imparting skin, gloss and moist feeling (moist feeling).

  The hydrogenated resin acid dimethylaminopropylamide produced in Example 4 used in Example 12 contains about 34% by mass of unreacted hydrogenated resin acid. The results show that the effect of imparting gloss and moist feeling to the lips of the hydrogenated resin acid dimethylaminopropylamide is superior to the gloss slip cream of Comparative Example 10 containing the hydrogenated resin acid, and the resin acid amidoamine of the present invention. It is clear from this result that the cosmetic base made of the compound exhibits the effect of the resin acid amidoamine compound even when the unreacted resin acid is mixed.

Example 13 and Comparative Example 12
A transparent gloss balm having the composition shown in Table 13 was prepared and applied to the lips to evaluate the gloss and moist feeling (moist feeling) after application. In Example 13, the glycerin-ethanol mixed solution of resin acid dimethylaminopropylamide produced in Example 6 was used, and in Comparative Example 12, dimethylaminopropyl stearate, which is a general amidoamine compound, was used instead of the resin acid amidoamine compound. Amide is used.

  In Table 13, * 19 and * 20 have already been mentioned, * 21 is Aminamide 40MP (trade name) manufactured by Seiwa Kasei Co., Ltd., * 22 is High Coal K-350 (trade name) of Kaneda Corporation, * 23 Is Cosmelike SA-10 (trade name) manufactured by Daiichi Kogyo Seiyaku Co., Ltd., and * 24 is Sun White (P-200) (trade name) manufactured by Nikko Rica Co., Ltd.

  Regarding the transparent gloss lip balms of Example 13 and Comparative Example 12, five panelists were allowed to use the transparent gloss lip balm of Comparative Example 12 once a day for the first 5 days, and for the next 5 days. A transparent gloss balm was used. The number of daily use, usage interval, usage, etc. were left to the panelists. After using the transparent gloss balm of Example 13 for 5 days (after the completion of the test for 10 days), whether the gloss of the lips and the moist feeling were better than when using the transparent gloss balm of Comparative Example 12, The answer was whether it got worse or did not change. The results are shown in Table 14 by the number of respondents.

  As shown in Table 14, all panelists answered that after using the transparent gloss lip balm of Example 13, the gloss and moistness (moisturation) of the lips were better than before use. It was clear that the resin acid dimethylaminopropylamide blended in Example 13 had a high effect of imparting gloss and moist feeling (moist feeling) to the skin.

Example 14 and Comparative Examples 13-14
Eye shadows having the compositions shown in Table 15 were prepared and evaluated for adhesion (ease of staying) at the time of application, and gloss and moist feeling (moist feeling) after application. In Example 14, the hydrogenated resin acid diethylaminoethylamide produced in Example 1 was used. In Comparative Example 13, the hydrogenated resin acid used in the production of Example 1 was used instead of the resin acid amidoamine compound. In No. 14, stearic acid diethylaminoethylamide commonly used in cosmetics is used.

  In Table 15, * 1 and * 21 have already been mentioned, * 25 is SEPSOFT SP (trade name) manufactured by SEPPIC, * 26 is Colorona Magenta (trade name) manufactured by MERCK, and * 27 is Ronastar Nobel manufactured by MERCK. Sparks (trade name), * 28 is Dow Corning 200-350 Fluid (trade name) manufactured by DOW CORNING.

  For the eye shadows of Example 14 and Comparative Examples 13-14, five panelists showed adhesion (easy to stay on the skin) when applied to wrinkles, and gloss and moist feeling (moist feeling) after application. The same evaluation criteria as in Example 11 were used. The results are shown in Table 16 as an average value of 5 people.

  As shown in Table 16, the eye shadow of Example 14 is easier to adhere to the skin than the eye shadows of Comparative Example 13 and Comparative Example 14, and gives a glossy and moist feeling (moist feeling) after application. It was clear that the effect was high.

Gives hair excellent hair styling and setability, as well as flexibility and good cohesion, and has a natural luster and moist feel that cannot be obtained with hair styling and hair setting agents that contain synthetic polymers. And a cosmetic base material capable of imparting an excellent gloss and moist feeling to the skin and a cosmetic containing the same can be provided.

Claims (7)

The following general formula (1)

(Wherein R ¹ CO represents a resin acid residue, R ² represents an alkyl group having 1 to 3 carbon atoms, and m is an integer of 2 to 4)
A cosmetic base material comprising an amidoamine compound represented by the formula: The cosmetic base material according to claim 1, wherein, in the general formula (1), R ¹ CO is a hydrogenated resin acid residue. A cosmetic for hair comprising the cosmetic base material according to claim 1 or 2. The cosmetic for hair according to claim 3, wherein the content of the cosmetic base material according to claim 1 or 2 is 0.05 to 10% by mass. A cosmetic for skin comprising the cosmetic base material according to claim 1. The skin cosmetic according to claim 5, wherein the skin cosmetic is a lip cosmetic. The skin cosmetic according to any one of claims 5 and 6, wherein the content of the cosmetic base material according to claim 1 or 2 is 0.5 to 20% by mass.