TWI581807B - Paraffin mixture and manufacturing method thereof - Google Patents

Description

Alkane mixture and method of producing the same

The present invention relates to an alkane mixture which is suitable for use as a cosmetic or cleaning oil for skin and hair, and which is excellent in volatility and a method for producing the same.

Heretofore, as a hydrocarbon which is a volatile oil agent, a hydrocarbon having 6 to 12 carbon atoms, such as n-hexane, isohexane, cyclohexane, n-octane, isooctane, etc., is known. , n-decane, n-decane, isododecane, and the like. However, these volatile oils have a problem of lack of safety due to a flash point below 50 °C. In addition, in the case of using a volatile oil agent for a cosmetic or a cleansing oil for skin and hair, there is a problem that the skin or mucous membrane is highly irritating or because of volatility. The problem of high moisture and evapotranspiration from the surface of the living body exists.

On the other hand, hydrocarbons having a carbon number of 15 or more, such as n-pentadecane or isohexadecane, are expected to have an increase in the flash point or a decrease in irritation to the skin or mucous membrane due to a high molecular weight. However, since the oil content is easily left by the decrease in the volatility, there is a problem that the feeling of use when applied to the skin or hair is poor.

From these backgrounds, for example, a volatile oil having a high volatility, a high flash point, or a human body safety, for example, Patent Document 1 discloses a combination of hydrocarbons having a carbon number of 12 to 14 and carbon. A non-lanthanide composition of 13 to 16 hydrocarbons and non-volatile hydrocarbons. this Further, in the technical field of cosmetics, for example, Patent Document 2 discloses a method in which a cyclic oxime such as cyclomethoxane is used as a volatile component.

[Previous Technical Literature] [Patent Literature]

[Patent Document 1] Japanese Patent Publication No. 2011-503192

[Patent Document 2] JP-A-2009-286752

However, in the method of Patent Document 1, since the non-lanthanoid composition contains 2,2,4,6,6-pentamethylheptane, there is a so-called odor and the hair is coated. At the time, there is a problem that the feeling of discomfort such as discomfort is inferior, and it is not possible to use it as a cosmetic or a cleaning oil. Further, since the non-lanthanoid composition contains oil which is a non-volatile component, there is a problem that the volatility is low, and in the production step, since a plurality of types of oil are required to be mixed, there is a troublesome manufacturing process. The problem exists. On the other hand, although the method of the patent document 2 is excellent in volatility, since there is a concern about the safety of the human body or the environment, there is a problem that it is not preferable because it is used as a cosmetic or a cleaning oil.

Accordingly, an object of the present invention is to provide an alkane mixture which is suitable for use as a cosmetic or cleaning oil for skin and hair and which is excellent in volatility.

The present inventors have found that the above object can be attained by limiting the carbon number, boiling point range, and 2,2,4,6,6-pentamethylheptane content of the alkane to a specific range in the mixture of alkanes. In addition, methods for making the alkane mixtures of the present invention have also been successfully provided.

That is, the present invention comprises an alkane mixture of 12 to 16 carbon atoms having a boiling point range of 185 to 215 ° C and a content of 2,2,4,6,6-pentamethylheptane of less than 10 Mass % alkane mixture.

The process for producing the alkane mixture of the present invention comprises the following steps 1 to 4.

Step 1) A step of removing an unreacted component and a polymer having a carbon number of 20 or more from a polymerization reaction system of isobutylene and n-butene to obtain a polybutene mixture having a carbon number of 16 or less.

Step 2) a step of hydrogenating the polybutene mixture having a carbon number of 16 or less obtained in the step 1 to obtain an alkane mixture having a carbon number of 16 or less.

Step 3) The step of adsorbing the alkane mixture having a carbon number of 16 or less obtained in the step 2 by using the adsorbent to reduce the iron content to 10 ppm or less.

Step 4) The alkane mixture having a carbon number of 16 or less which has been subjected to the adsorption treatment in the step 3 is subjected to a vacuum distillation, and the step of distilling off 15% by mass or more with respect to the preparation amount.

The alkane mixture of the present invention has excellent volatility, high flash point or safety to human body, and also has an effect of being excellent in the feeling of use when applied to skin or hair. Therefore, the alkane mixture of the present invention is advantageously used as a raw material for skin and hair cosmetics, a washing oil agent or a pharmaceutical. For example, it is useful as a substitute for a cyclic quinone such as a cyclopentaoxane, and is excellent in safety and economy to the human body or the environment.

Further, the production method of the present invention can achieve the effect of easily producing the alkane mixture of the present invention.

Hereinafter, embodiments of the present invention will be described.

The alkane mixture of the present invention is a mixture of an alkane (saturated hydrocarbon) containing an isoalkane (differential saturated hydrocarbon) having a carbon number of 12 to 16, and may also contain a carbon number of 12 to 16 Chain saturated hydrocarbons. Further, in the alkane mixture of the present invention, hydrocarbons other than the saturated hydrocarbon having a carbon number of 12 to 16 may be contained to the extent that the object of the present invention is not violated, for example, unsaturated hydrocarbons containing a cyclic saturated hydrocarbon are contained. Hydrocarbons, etc. may also be used.

The alkane mixture of the present invention has a boiling point in the range of 185 to 215 ° C, preferably 186 to 210 ° C. When the boiling point of the alkane mixture is less than 185 ° C, the flash point will become low, which is not preferable in terms of safety. When the boiling point exceeds 215 ° C, the volatility is lowered, and the oil component tends to remain, so that the feeling of use when applied to the skin or hair is inferior. The boiling point can be measured by a distillation test based on JIS K2254. Further, the flash point of the alkane mixture of the present invention is preferably in the range of 61 to 70 ° C, preferably in the range of 62 to 67 ° C, in the sealing test based on JIS K2265, and is preferable in terms of safety.

The alkane mixture of the present invention has a content of 2,2,4,6,6-pentamethylheptane (hereinafter also referred to as isododecane.) of less than 10% by mass, preferably less than 8% by mass. More preferably, it is less than 5% by mass. When the content of isododecane in the mixture becomes 10% by mass or more, the boiling point will be lowered, which is not desirable in terms of safety, and since the odor will be enhanced, the feeling of use on the skin and hair will be lowered, Therefore, the use as a raw material such as cosmetics will be limited.

The alkane mixture of the present invention can be produced, for example, by a procedure comprising the following steps 1 to 4.

Step 1) A step of removing an unreacted component and a polymer having a carbon number of 20 or more from a polymerization reaction system of isobutylene and n-butene to obtain a polybutene mixture having a carbon number of 16 or less.

Step 2) a step of hydrogenating the polybutene mixture having a carbon number of 16 or less obtained in the step 1 to obtain an alkane mixture having a carbon number of 16 or less.

Step 3) The step of adsorbing the alkane mixture having a carbon number of 16 or less obtained in the step 2 by using the adsorbent to reduce the iron content to 10 ppm or less.

Step 4) The alkane mixture having a carbon number of 16 or less which has been subjected to the adsorption treatment in the step 3 is subjected to a vacuum distillation, and the step of distilling off 15% by mass or more with respect to the preparation amount.

The above steps 1 to 4 will be described in order below.

First, the polymerization reaction of isobutylene and n-butene used in the step 1 is a mixed gas of isobutylene and n-butene which is a C4 fraction among the fractions obtained by the cracking of petroleum brain, and a known method can be used, for example. It is obtained by a positive ion polymerization method using a catalyst. Therefore, in the polymerization system of isobutylene and n-butene, a mixture of polybutene (a copolymer of isobutylene and n-butene, a copolymer of isobutylene (co)) and a polymer of n-butene is used as carbon. a mixture of 8 or more unsaturated hydrocarbons), an unreacted component (isobutylene or n-butene contained in the mixed gas, etc.), a catalyst, and the like.

Isomers of 1-butene, cis-2-butene and trans-2-butene are present in n-butene. The mixed gas composition for obtaining a copolymer of isobutylene and n-butene is 15 to 80% by mass of isobutylene, 10 to 40% by mass of 1-butene, and cis-2-butene and trans-2- The total butene content is preferably from 10 to 60% by mass, more preferably from 15 to 70% by mass of isobutylene, from 15 to 40% by mass of 1-butene, and from cis-2-butene to trans-2-butylene. The total number of olefins is between 15 and 60% by mass, particularly preferably between 20 and 50% by mass of isobutylene, between 18 and 25% by mass of 1-butene, and between cis-2-butene and trans-2-butene. From 18 to 40% by mass. Further, the mixed gas may contain a component which does not react with the copolymerization reaction, such as isobutane or butane.

Examples of the catalyst used in the positive ion polymerization method include aluminum chloride, an acidic ion exchange resin, sulfuric acid, boron fluoride, and a complex thereof. Further, the polymerization reaction can be controlled by adding a salt group to the aforementioned catalyst. The polymerization can usually be carried out at 40 to 120 °C.

In the polymerization reaction system of isobutylene and n-butene, as described above, a polybutene mixture or an unreacted component which is a polymerization reaction product of isobutylene and n-butene is contained. In the step 1, the unreacted component and the polymer having 20 or more carbon atoms are removed from the polymerization reaction system to obtain a mixture of polybutene having a carbon number of 16 or less. In terms of the removal method, distillation is preferred. Examples of the method for the distillation include a single distillation method, a continuous distillation method, a steam distillation method, and a thin film distillation method, and these methods can be carried out singly or in combination. The material, shape, and type of the apparatus used for the distillation are not particularly limited, and examples thereof include a multi-stage tray distillation column having a distillation column or a disk-shaped holder filled with a filler such as a Raschig ring. Further, the number of theoretical plates indicating the separation energy of the distillation column is preferably 10 or more. Further, conditions such as the amount of feed to the distillation column, the reflux ratio, and the amount of withdrawal can be appropriately selected in accordance with the apparatus for performing distillation.

In the second step, the polybutene mixture having a carbon number of 16 or less obtained in the step 1 is hydrogenated to obtain a mixture of a hydrocarbon having a polybutene hydride, that is, an isoparaffin having 16 or less carbon atoms. Since the polybutene having a carbon number of 16 or less obtained in the step 1 has a double bond at the polymerization end, deterioration of coloring or the like may occur if stored for a long period of time. In order to solve such a problem, it is subjected to a hydrogenation reaction in the step 2 to become a hydrogen additive. The hydrogenation reaction may be carried out by using nickel or palladium or the like as a hydrogenation catalyst at a temperature of from 180 to 230 ° C, and the hydrogenation catalyst is brought into contact with hydrogen at a pressure of from 2 to 10 MPa. The degree of hydrogenation of the alkane mixture used to obtain the present invention is preferably 10 or less in terms of iodine value. Preferably, the degree of hydrogenation is judged to be 1 or less in terms of iodine value, and more preferably, the degree of hydrogenation is judged to be 0.1 or less in terms of iodine value. Once the iodine value exceeds 10, it is easy to carry out oxidation by heat and light, and it is easy to cause odor.

In the alkane mixture having a carbon number of 16 or less obtained in the second step, corrosion of the reaction apparatus due to the high acidity of the trace metal compound or the catalyst contained in the catalyst for the hydrogenation reaction may cause corrosion. The phenomenon of iron and other trace metals mixed in. These trace metals can have a detrimental effect on the odor or preservation stability of the alkane mixture. In the various types of trace metals, especially the incorporation of iron, the odor is caused by the distillation operation in the subsequent step of obtaining the alkane mixture of the present invention. The gas is worsened and becomes the cause of the bad smell. Therefore, for the purpose of suppressing coloration or odor, in the step 3, the alkane mixture having a carbon number of 16 or less is subjected to adsorption treatment using an adsorbent.

As the adsorbent, inorganic and organic adsorbents can be used, for example, clay, kaolin, talc, calcium carbonate, diatomaceous earth, zeolite, bentonite, acid clay, activated clay, vermiculite, tannin, molecular sieve, and Activated carbon, especially activated clay and clay, is more effective. These adsorbents may be used alone or in combination of two or more. The adsorbent is effective not only for physically removing trace metals and iron from the hydrogenation catalyst, but also for removing low molecular weight oxides which are decomposed by high temperature in hydrogenation and by-products, and after maintaining the distillation. The time-dependent stability of the products is more effective. The particle diameter of the adsorbent to be used is not particularly limited, but in the case of using the same type of adsorbent, it is preferred to combine two or more kinds of adsorbents having different particle diameters. The combination of the adsorbents can be appropriately selected in accordance with the dispersion of the pressure in the column in which the adsorbent is filled and the efficient treatment. When two or more types of adsorbents are used, the particle size is relatively the smallest, and the filling volume is 50 to 80% by volume compared with the column volume, which is effective for manufacturing.

The alkane mixture which has been subjected to the adsorption treatment in the step 3 has an iron content of 10 ppm or less and preferably 5 ppm or less. Once the iron content to be mixed exceeds 10 ppm, there is a problem that the odor in the subsequent distillation step becomes strong.

The alkane mixture which has been subjected to the adsorption treatment in the step 3 contains isododecane having a low flash point and an unpleasant odor. Therefore, in the step 4, the alkane mixture having a carbon number of 16 or less which has been subjected to the adsorption treatment in the step 3 is subjected to vacuum distillation, and is distilled off by 15% by mass or more with respect to the preparation amount before the vacuum distillation. More than 25 mass% is preferred. In addition, from the viewpoint of suppressing the decrease in the flash point of the alkane mixture, the distillation removal rate is preferably 40% by mass or less, and more preferably 35% by mass or less, based on the amount of the preparation before the vacuum distillation.

When the distillation in the vacuum distillation is performed, the distillation method and the distillation apparatus described in the above step 1 can be employed. The distillation condition is that the temperature of the liquid in the container is between 50 and 180 ° C, and is between 100 and 180 ° C. Preferably, the internal pressure of the container is between 0.5 and 80 kPa, preferably between 5 and 80 kPa. The isododecane or other low boilers (saturated hydrocarbons having a carbon number of 8, etc.) contained in the alkane mixture can be distilled off by the distillation step of this step.

The alkane mixture of the present invention comprising an isoalkane having a carbon number of 12 to 16 can be produced by the procedure comprising the above steps 1 to 4.

The alkane mixture of the present invention can be used as a solid and liquid cosmetic base material such as a base cosmetic, a cosmetic for makeup, a cosmetic for hair, and the like, and a volatile oil agent for various fragrances including perfumes can be used. It is even possible to use a multi-purpose solvent as a detergent and an odorless one. Further, it is very useful to use the composition of the alkane mixture of the present invention as a cosmetic composition. In addition, in the ring-shaped eucalyptus oil or isododecane, it is also very useful as a substitute for a representative volatile solvent, through sunscreen products such as cosmetics, hair care products, skin care products, sunscreen lotions, sweating agents, and body fragrance. In the preparation of the agent, the sunscreen, the medical cream, and the like, the alkane mixture of the present invention is mixed, and in addition to the effects of volatility, viscosity, and preservation stability, the functional items represented by the touch or the odor can also be excellent. Effect.

The cosmetic composition comprising the alkane mixture of the present invention can appropriately select the content of the alkane mixture in accordance with the purpose of the cosmetic preparation and the method of use thereof. In particular, in the case where the effect of the alkane mixture of the present invention is significantly exhibited, for example, the volatility is increased, or the dilution or compatibility of other cosmetic substrates is improved, the mixing amount may be used in accordance with the purpose of use. Although it is different, it is preferable to mix the alkane mixture of the present invention in the cosmetic composition in an amount of 5 to 90% by mass, preferably 10 to 70% by mass.

The cosmetic composition or the pharmaceutical composition comprising the alkane mixture of the present invention may further comprise an auxiliary agent and an additive, such as a surfactant, further comprising an oil component, a moisturizing agent, a pearl gloss wax, a thickener, and a tackifier. , fatty agents, stabilizers, water-soluble and oil-soluble polymers, fats, waxes, lecithins, phospholipids, biologically active substances, UV absorbers, UV scattering agents, organic and inorganic pigments, antioxidants, deodorization Agent, whitening agent, sweating agent, hair growth agent, anti-inflammatory town Pain, blood circulation promoter, anti-dandruff (anti-dandruff) agent, film forming agent, swelling agent, insect repellent, tyrosinase inhibitor (depigmenting agent), water-reducing solvent, solubilizing agent, antiseptic Agents, sesame oils, colorants, pH adjusters, chelating agents, and the like may also be used.

The cosmetic composition or the pharmaceutical composition comprising the alkane mixture of the present invention can be applied to various types of dosage forms, and can be applied, for example, to emulsions, creams, masks, massages, barrier creams, ultraviolet defense agents, and the like. . For example, the hair cosmetic can be provided in the form of a liquid, a cream, a latex, a gel, or a mousse, and can be applied as a gas gel spray, a pump spray, a foam spray, and a mist. It is very useful for combination products such as hair styling liquid, hair styling products, and hair oil, as well as hair conditioning products such as shampoo, moisturizing essence, permanent setting liquid, and hair conditioner.

Such a cosmetic composition or a pharmaceutical composition can be produced by emulsification or mixing. For example, a mixer such as a homogenizer, a homomixer, a mill, or the like can be used, or other principles such as high pressure or ultrasonic can be used. Mixer, emulsified or mixed.

[Examples]

Hereinafter, the present invention will be further specifically described by way of examples and comparative examples. The various physical property values in the respective examples were measured by the methods shown below.

<iodine price>

Based on the iodine value test method of JIS K0070.

<boiling point range>

Based on the distillation test method of JIS K2254.

<flash point>

Based on the closed flash point measurement method of JIS K2265.

<number average molecular weight>

The number average molecular weight (in terms of polystyrene) was measured using a GPC (gel permeation chromatography) measuring apparatus manufactured by Shimadzu Corporation.

<Method for analyzing the content of isododecane>

Using isododecane as a specimen, the elution position was confirmed by Shimadzu GC-14B gas chromatographic separation analysis, and the content of the compound corresponding to the elution position was measured.

‧ Gas chromatographic separation analysis conditions

Column: non-polar capillary column, 0.55mm, 30m, 5μm

Temperature: 80 ° C ~ 250 ° C, 10 ° C / min temperature analysis

<Iron content analysis>

After a predetermined amount of the sample was slowly burned in a platinum dish, the ash which was completely burned in the electric furnace was dissolved in concentrated hydrochloric acid to prepare a sample for measurement. Next, analysis was performed in accordance with a predetermined operation using an ICP emission analysis device. Further, although the analysis was performed after the end of step 3, for the comparative example 3 in which step 3 was not performed, the analysis was performed after the end of step 2.

<Odor evaluation test>

‧Functional test (marked as odor 1 in Table 1)

The functional test was conducted to evaluate the nature (unpleasant feeling and irritation) of the odor which is difficult to evaluate by the odor sensor.

‧ total odor (marked as odor 2 in Table 1)

An odor sensor manufactured by a new COSMOS motor company is used to inhale an odor component (volatile component) under measurement conditions, and the relative odor is measured by a change in resistance due to gas adsorption.

Specifically, 25 g of the measurement sample was placed in a two-cup 50 cc glass spiral bottle (covering the inner lid and sealed with a sealing tape), and the initial value was taken as a blank sample, and then a bottle of glass spiral bottle was placed at 40 ° C. In the constant temperature bath, it is allowed to stand for one month, while the other bottle of glass spiral bottle is exposed to the outside and is allowed to stand for one week. Then, the odor test according to the functional test (odor 1) and the use of the odor sensor are performed. The odor test (odor 2) of the odor sensor (the odor sensor manufactured by the new COSMOS Motor Co., Ltd.) was used to investigate the change from the initial value.

[Example 1]

The alkane mixture is produced by the following steps 1 to 4.

360 g of a mixed gas comprising an olefin mixed gas of carbon number 4 of 30% by mass of isobutylene, 18% by mass of 1-butene and 25% by mass of 2-butene and a butane gas of 27% by mass is prepared in an autoclave In the presence of an aluminum chloride catalyst, a polymerization reaction is carried out to obtain a polymerization reaction system of isobutylene and n-butene.

(step 1)

After the unreacted gas in the autoclave after the completion of the reaction was replaced with nitrogen, the polybutene mixture belonging to the polymerization mixture was extracted. Next, the catalyst is removed by a caustic alkali aqueous solution treatment and a water washing step. Next, the water-washed polybutene mixture was prepared in a 1-liter four-necked flask and heated in an oil bath. When the internal temperature was 40 ° C, nitrogen was bubbled to remove unreacted gas dissolved in the polybutene mixture. After the composition, when the internal temperature was 140 ° C and the degree of pressure reduction was 5 kPa, single distillation was performed. Thereby, a polymer having a carbon number of 20 or more is left as a distillation residue in the flask to obtain a polybutene mixture having a carbon number of 16 or less. This polybutene mixture has a number average molecular weight of about 185.

(Step 2)

The polybutene mixture was subjected to hydrogen addition at a hydrogen pressure of 3 MPa and 220 ° C in an autoclave using a hydrogenation catalyst (0.5% Pd supported alumina catalyst) at 10% by mass to obtain 160 g of an alkane mixture. . This alkane mixture has an iodine value of 0.1 and a number average molecular weight of about 180.

(Step 3)

To a glass cylinder with an outer diameter of 4 cm and a length of 30 cm, the attapulgite clay and the activated clay are first filled with attapulgite clay at a volume ratio of 50:50, and then filled with activated clay to complete the adsorption column. The alkane mixture obtained in step 2 is continuously fed from the lower part of the adsorption column at a flow rate of 1 ml per minute at 25 ° C to obtain trace metals from the catalyst and from the fabricated material. The compound is subjected to adsorption treatment. The iron content of the alkane mixture after the adsorption treatment is shown in Table 1.

(Step 4)

In the bottom container of the fifteen-stage OLDERSHOW multi-stage tray rectification column, 150 g of the adsorbed alkane mixture obtained in the step 3 was prepared, immersed in an oil bath, and started with dry nitrogen. Soak, avoid contact with air and heat until the liquid temperature in the container reaches 110 °C. When the temperature of the liquid in the vessel reached 110 ° C, the reflux ratio was set to 10 under reduced pressure (10 kPa), the outlet temperature of distillation was set to 95 ° C, and distillation under reduced pressure was carried out for 8 hours to distill off the total amount of preparation 25 quality%. Thereafter, dry nitrogen gas was again bubbled under reduced pressure to cool the liquid in the bottom vessel to obtain 112.5 g of an alkane mixture. The numerical results of various physical properties of the obtained alkane mixture are shown in Table 1.

[Example 2]

In the step 3 described in the first embodiment, the type of the adsorbent is changed to attapulgite clay and tannin (volume ratio: 70:30), and in step 4, except for the removal of 20% by mass of the preparation amount, The same operation as in Example 1 was carried out. In addition, the attapulgite clay is first filled and then filled with silicone to complete the adsorption column. The numerical results of various physical properties of the obtained alkane mixture are shown in Table 1.

[Example 3]

In the third step described in the first embodiment, the same operation as in the first embodiment was carried out except that the type of the adsorbent was changed to two kinds of attapulgite clays having different particle diameters. One of the attapulgite clays having different particle diameters has a particle diameter of from 840 μm to 1000 μm, and the other one has a particle diameter of from 200 μm to 480 μm. Firstly, the particle size is from 840 μm to 1000 μm, and the volume ratio of the adsorption column is filled with 20% to prepare, and then the remaining 80% ratio is filled with the particle diameter of 200 μm to 480 μm to complete the adsorption column. The numerical results of various physical properties of the obtained alkane mixture are shown in Table 1.

[Comparative Example 1]

In the same manner as in Example 1, except that the outflow temperature of the distillation was set to 70 ° C and the amount of preparation was 2% by mass. The result is An alkane mixture having a compound having a lower boiling point than the boiling point of isododecane is obtained. The content of isododecane in the obtained alkane mixture was 15% by mass. The result will be a strong unpleasant odor and a low flash point. The numerical results of various physical properties of the obtained alkane mixture are shown in Table 1.

[Comparative Example 2]

In the same manner as in Example 3 except that the discharge temperature of the distillation was set to 85 ° C, and 10% by mass of the preparation amount was distilled off, the same procedure as in Example 3 was carried out. The content of isododecane in the obtained alkane mixture was 10% by mass. The result will be a strong unique odor and a low flash point. The numerical results of various physical properties of the obtained alkane mixture are shown in Table 1.

[Examples 4 to 8]

In the step 4 described in the third embodiment, the same operation as in the third embodiment was carried out except that the distillation conditions were changed to the conditions shown in Table 1. The numerical results of various physical properties of the obtained alkane mixture are shown in Table 1.

[Comparative Example 3]

In the step 3 described in the first embodiment, the adsorption treatment of the metal compound by the adsorbent is not carried out, and in the step 4, the outflow temperature of the distillation is set to 90 ° C, and the preparation amount is distilled off. The same operation as in Example 1 was carried out except that 14% by mass was used. As a result, an alkane mixture having a strong unique odor and a low flash point is obtained. The numerical results of various physical properties of the obtained alkane mixture are shown in Table 1.

(Note 1) The presence or absence of the manufacturing steps, there are steps: ○, no steps: ×

(Note 2) Content: ratio (% by mass) to the total mixture of isododecane

(Note 3) Drying property: 0.1 g of each sample was applied to a 10 cm filter paper (manufactured by ADVANTEC Co., Ltd.), and the drying speed was measured. When the drying is completed within half of the time of the decamethyl pentoxide of the cyclic oxime, the blank sample is marked with "○", and the other is marked with "x".

(Note 4) Odor 1: Through the functional test to determine the presence or absence of unpleasant and irritating odor, there are: ×, none: ○

(Note 5) Odor 2: Total amount of odor measured by odor sensor (relative comparison value)

The boiling point and volatility of the alkane mixture obtained in Example 1, the feeling of use when applied to the hair, the feeling of use when applied to the skin surface, and the residual feeling of oil on the skin surface, and the conventional high volatility The various cosmetic oils of the ingredients are compared and summarized in Table 2.

Further, the order of volatility in Table 2 was carried out on a filter paper having a diameter of 110 mm, and the samples were each stretched at 0.1 g, and the mass dried over 2 hours was measured. It will be completely dry, the quality will become 0g, and it will be ranked from fast to slow.

The feeling of application to the skin and hair was evaluated by ten functional inspectors. The hair application feeling was 1 g using a hair bundle of a healthy Chinese, and an appropriate amount of each sample was taken and applied by hand. For the application of skin coating, 0.1 g of each sample was dropped onto the back of the hand by a pipette, and pushed and spread in the palm of the hand.

(Note 1) "MARUKASOL R" manufactured by Maruzen Petrochemical Co., Ltd.

[Cell number 12, flash point 48 ° C, isododecane content 95% by mass or more]

(Note 2) "SH-245" manufactured by Dow Corning Toray Co., Ltd. [flash point 77 ° C]

(Note 3) manufactured by Nippon Oil Co., Ltd., hydrogenated polybutene: PARLEAM 4

[Cell number 16, boiling point range is 220~252.5 °C, flash point 88 °C, content of isododecane 0% by mass]

As shown in Table 2, the alkane mixture of the present invention according to Example 1 is not only more excellent in volatility than the cyclic oxime, but also excellent in the use feeling of the oil alone, even in various makeups excellent in other volatility. When it is applied to hair and skin in the case of cosmetic use, it has been confirmed that it can impart a very good touch.

[hair and skin cosmetics]

The hair and skin cosmetics shown below were prepared using the alkane mixture of the present invention, and the respective preparations were evaluated. The evaluation was conducted by ten functional inspectors for their sense of use. Among all hair and skin cosmetics, it is very good as a substitute for a ring-shaped enamel, and a higher evaluation can be obtained than in the case of using isododecane.

(Hair oil)

The hair oil shown in Table 3 was compared with those using isododecane. As a result, the hair oil using the alkane mixture of the present invention is more excellent in hairdressing and more excellent in use than the use of isododecane.

(Note 1) "MARUKASOL R" manufactured by Maruzen Petrochemical Co., Ltd.

[Cell number 12, flash point 48 ° C, isododecane content 95% by mass or more]

(sunscreen)

The sunscreen oil as shown in Table 4 was evaluated in comparison with the use of a ring-shaped sputum. As a result, the sunscreen oil using the alkane mixture of the present invention can be used more prolonged and more excellent in use than a ring-shaped one.

(Note 1) "SH-245" made by Dow Corning Toray Co., Ltd.

(Note 2) "MQ resin" manufactured by Dow Corning Toray Co., Ltd.

(Sunscreen cosmetics)

The sunscreen cosmetic as shown in Table 5 was evaluated in comparison with those using isododecane. As a result, the sunscreen oil using the alkane mixture of the present invention can be used more prolonged and more excellent in use than the use of isododecane.

(Note 1) "MARUKASOL R" manufactured by Maruzen Petrochemical Co., Ltd.

(Note 2) "PARLEAM EX" manufactured by Nippon Oil Co., Ltd.

(Note 3) "MQ resin" manufactured by Dow Corning Toray Co., Ltd.

(Note 4) "SPP-M" manufactured by Suga Chemical Industry Co., Ltd.

(Note 5) "MZ-500" manufactured by Dihua Co., Ltd.

(waterproof mascara)

The waterproof mascara as shown in Table 6 was evaluated in comparison with the use of a ring-shaped sputum. As a result, the waterproof mascara using the alkane mixture of the present invention is quicker to dry and more excellent in use than the ring-shaped one.

(Note 1) "SH-245" made by Dow Corning Toray Co., Ltd.

(Note 2) "BALANCE CR" manufactured by AKZONOBEL Co., Ltd.

(lipstick)

Lipsticks as shown in Table 7 were compared with those using isododecane. As a result, the lipstick using the alkane mixture of the present invention is more excellent in skin intimacy and feeling of use than the use of isododecane.

[Table 7]

(Note 1) "MARUKASOL R" manufactured by Maruzen Petrochemical Co., Ltd.

(Note 2) "PARLEAM EX" manufactured by Nippon Oil Co., Ltd.

(Note 3) "MQ resin" manufactured by Dow Corning Toray Co., Ltd.

(Note 4) "SPP-M" manufactured by Suga Chemical Industry Co., Ltd.

(medicine lip balm)

The medicinal lip balm as shown in Table 8 was evaluated in comparison with those using isododecane. As a result, the medicinal lip balm using the alkane mixture of the present invention is more excellent in skin intimacy and feeling of use than the use of isododecane.

(Note 1) "SH-245" made by Dow Corning Toray Co., Ltd.

(nail care products)

The nail care product as shown in Table 9 was evaluated in comparison with the use of isododecane. As a result, the nail care product using the alkane mixture of the present invention is more excellent in the feeling of use than the use of isododecane.

(Note 1) "MARUKASOL R" manufactured by Maruzen Petrochemical Co., Ltd.

[Industrial availability]

The alkane mixture of the present invention is advantageously used as a raw material for a cosmetic, a cleaning oil or a pharmaceutical. In particular, it is useful as a raw material for an agent for skin and hair, for example, as a sunscreen product such as cosmetics, perfume, hair care products, skin care products, armor products, armor products, sunscreen lotion, sweating agent, body fragrance It is used as a raw material such as a lotion, sunscreen or medical cream. Further, the alkane mixture of the present invention can be utilized not only in the cosmetics or pharmaceutical industries, but also in other industries using volatile oil agents.

Claims (1)

A method for producing an alkane mixture comprising an isoalkane having 12 to 16 carbon atoms, a boiling point ranging from 185 to 215 ° C, and a content of 2,2,4,6,6-pentamethylheptane of less than 10 %, the method comprises the following steps 1 to 4: Step 1) removing unreacted components and a polymer having a carbon number of 20 or more from a polymerization reaction system of isobutylene and n-butene to obtain a polybutene mixture having a carbon number of 16 or less Step; Step 2) hydrogenating the polybutene mixture having a carbon number of 16 or less obtained in the step 1 to obtain an alkane mixture having a carbon number of 16 or less; and step 3) using the adsorbent to obtain the carbon number obtained in the step 2 a step of adsorbing the alkane mixture of 16 or less to reduce the iron fraction to 10 ppm or less; and step 4) subjecting the alkane mixture having the carbon number of 16 or less which has been subjected to the adsorption treatment in the step 3 to a vacuum distillation to perform relative distillation The amount of the alkane mixture before distillation under reduced pressure is distilled off by 15% by mass or more.