JPH01117811A - External preparation - Google Patents

Abstract

PURPOSE:To obtain an external preparation useful as skin cosmetic, hair cosmetic or drug for external use, having high skin affinity and excellent prolonging effects on moisture retention of skin, comprising a diacylglycerin containing acyl residues of a specific branched chain fatty acid and myristic acid. CONSTITUTION:The above external preparation obtained by blending an external preparation such as the above-mentioned cosmetic or drug with about 0.1-90wt.%, preferably 0.1-50wt.% diacylglycerin shown by formula I [one of R1-R3 is branched-chain fatty acid residue selected from group shown by formula II (m and n are 4-10 integer, m+n=14, having distribution with center at m=n=7), 5,7,7-trimethyl-2-(1,3,3-trimethylbutyl)-octanoic acid residue or 2- heptylundecanoic acid residue, remaining one is tetradecanoic acid (myristic acid) residue and the residue is H] as an active ingredient and having the above- mentioned effects such as good fit to the skin.

Description

[Detailed Description of the Invention] [Industrial Application Field] The present invention relates to an external preparation, and more specifically, it contains a specific diacylglycerin and has high skin affinity (good compatibility with the skin). The present invention also relates to external preparations such as skin cosmetics, hair cosmetics, and external medicines that have excellent long-lasting skin moisturizing effects.

[Conventional technology and its problems]

The stratum corneum of normal skin normally contains 10 to 30% water, maintaining its elasticity and flexibility, but when this drops to less than 10% due to environmental conditions, it becomes what is called dry skin. Become called. For example, symptoms such as cracks and chapping occur during dry winter months.

Additionally, as we age, the secretion of sebum decreases, making the skin prone to dryness and symptoms such as senile xeroderma, which causes itching and scaling.

As methods for solving these problems, there have conventionally been methods to enhance the skin hydration effect using humectants and methods to suppress transepidermal water loss (T, E, W, L,) using oils.

As examples of the former, moisturizers such as glycerin, propylene glycol, and sodium pyrrolidone carboxylate have been used, but when applied to the skin, the effects of these moisturizers are temporary and long-lasting. However, it had the disadvantage of being susceptible to external environmental conditions.

On the other hand, Vaseline ointment is a well-known example of the latter, but in order to increase its effectiveness, it is necessary to apply a large amount, resulting in an oily feeling, stickiness, and difficulty in absorbing the skin. It has an unpleasant feel, and conversely, if the amount applied is too small, the occlusion property is weak and it is not long-lasting.

[Means for solving problems]

In view of these circumstances, the present inventors have found that
As a result of intensive research to obtain an external preparation with excellent long-lasting skin moisturizing effects, we have developed a formulation that blends with diacylglycerin, which has acyl residues of specific branched saturated fatty acids and myristic acid (tetradecanoic acid), to improve its compatibility with the skin. The present invention was completed based on the discovery that the skin moisturizing effect is good and has an excellent long-lasting skin moisturizing effect.

That is, the present invention provides an external preparation characterized by containing diacylglycerin represented by the following general formula (H).

CHt OR+ CHORt...(1) CH2-
0-R3 [wherein, one of R+, Rz, and lh is (i) a methyl branched isostearic acid residue represented by the following formula, CH3(CH2) -CH(CHz) 1lCO-CI
(3 (In the formula, ■ and n are each integers of 4 to 10, m + n
=14, and has a distribution centered at n+=n-7. ) (u)54.7) a branched saturated fatty acid residue selected from the group consisting of: (u)54.7) a remethyl-2-(1,3,3-trimethylbutyl)-octanoic acid residue; (iii) a 2-hebutylundecanoic acid residue; One group represents a tetradecanoic acid residue, and the remainder represents hydrogen.] The diacylglycerin represented by the general formula (1) used in the present invention contains in one molecule the branched saturated fatty acid residue having 18 carbon atoms as described above. (isostearic acid residue) and tetradecanoic acid residue, and can be synthesized, for example, by the following method.

(1) Direct esterification of glycerin with fatty acids.

It is produced by a conventional method for producing acylglycerin from a branched saturated fatty acid having 18 carbon atoms, tetradecanoic acid (myristic acid), and glycerin. For example, a mixture of these acylglycerols is produced by blending equimolar amounts of the branched saturated fatty acids and myristic acid and glycerin, heating the mixture to 200 to 230°C, and removing the produced water under reduced pressure. A diacylglycerol fraction can be obtained by subjecting this product to distillation or column chromatography. However, this diacylglycerin is a random mixture; that is, diacylglycerin consisting only of branched saturated fatty acid residues, diacylglycerin consisting of branched saturated fatty acid residues and myristic acid residues, and diacylglycerin consisting only of myristic acid residues. Since it is a mixture, the desired diacylglycerin of the present invention can be obtained by a recrystallization method using a solvent such as hexane by utilizing the difference in melting point.

The branched saturated fatty acid having 18 carbon atoms used for producing the diacylglycerin of the present invention can be easily obtained from petrochemical raw materials or oleochemical raw materials.

That is, 5.7.7-dolimethyl-2-(1,3,3-tri,methylbutyl)-octanoic acid is converted into a branched aldehyde having 9 carbon atoms by the oxo reaction of isobutylene dimer,
Then, by aldol condensation of this aldehyde, the number of carbon atoms is 1.
It can be produced by preparing a branched unsaturated aldehyde of No. 8, followed by hydrogenation and oxidation, and this is commercially available, for example, from Nissan Chemical. 2-Hebutylundecanoic acid is produced by converting nonyl alcohol into the Guerbet reaction.
reaction) and then oxidation, and is commercially available from, for example, Mitsubishi Kasei.

Methyl branched isostearic acid is obtained, for example, as a by-product during the production of oleic acid dimer [for example, J. Amer, Oil Chell.

Soc., 51.522 (1974)), and is commercially available, for example, from Emery Company, USA.

(2) Reaction of reactive derivatives of fatty acids with monoglycerides.

As a more advantageous production method, either branched saturated fatty acid or myristic acid can be converted into a more reactive derivative and then esterified. One of the highly reactive derivatives is an acid halide of a fatty acid, and in a preferred example of this process, first, 1 to 5 mol, preferably 1 to 5 mol per mol of the branched saturated fatty acid, is added to the raw branched saturated fatty acid. 1 to 2 moles of a halogenating reagent such as thionyl chloride, thionyl bromide, phosphorus trichloride, etc. are reacted at 0 to 100"C, preferably 20 to 80°C, to form an acid halide.
.

200 ~ 1 mole of myristic acid and 1 mole of glycerin
Myristoylglycerin is obtained by heating to 230"C and removing the produced water under reduced pressure. By molecularly distilling this, monomyristoylglycerin is obtained. Therefore, the above-mentioned branched saturated fatty acid halide and branched saturated 0.5 to 3 moles, preferably 1 to 1.5 moles of monomyristoylglycerin per mole of fatty acid halide, and 1 to 3 moles, preferably 1 to 1.5 moles of pyridine, quinoline, etc. relative to the acid halide. For example, benzene, toluene, xylene,
50 in a suitable inert solvent such as hexane (1 to 10 times the volume, preferably 3 to 5 times the volume of the acid halide).
The reaction is carried out while heating and stirring at ~100°C, preferably 60-80°C. The desired diacylglycerin containing branched saturated fatty acid residues and myristic acid residues can be obtained by subjecting the produced acylglycerin from which the hydrogen halide amine salt has been removed to molecular distillation or column chromatography.

(3) Method using lipase.

As a more advantageous production method, it can be produced using lipase without using highly reactive derivatives. First, 1 mol of branched saturated fatty acid and 1 mol of glycerin are mixed into 200
Acylglycerin with branched saturated fatty acid residues is obtained by heating to ~230°C and the water produced is removed under reduced pressure, and monoacylglycerin with branched saturated fatty acid residues is obtained through molecular distillation. The desired diacylglycerol containing branched saturated fatty acid residues and myristic acid residues is obtained by blending equimolar amounts of this monoacylglycerol and myristic acid and performing an esterification reaction using lipase as a catalyst. Depending on the degree of esterification, molecular distillation is carried out as a post-treatment. For example, if the esterification rate of myristic acid is low, it is necessary to remove residual myristic acid and monoacylglycerol.

Moreover, the by-product of triazylglycerin can also be removed by molecular distillation column chromatography. When using a lipase as a catalyst, a lipase having α-position selectivity or a lipase selective for partial glycerides is most effective.

As shown in Table 1, the amount of diacylglycerin in the external preparation of the present invention can vary widely depending on the dosage form, but is generally 0.1 to 90% by weight, preferably 0.1 to 5% by weight.
It is in the range of 0% by weight.

On the other hand, raw materials other than water used in the present invention include oils, surfactants, humectants containing polyhydric alcohols, various medicinal agents, preservatives, fragrances, etc. that are usually applied to external preparations. Most of the ingredients are listed, and they are appropriately selected and blended depending on the purpose, use, dosage form, etc. For example, regarding oil content, solid fats such as stearic acid, myristic acid, cetanol, stearyl alcohol, cholesterol, petrolatum, etc., squalane, cholesteryl isostearate, jojoba oil, olive oil, neopentyl glycol capriate, liquid paraffin, etc. There is a typical liquid fat. On the other hand, regarding polyhydric alcohol,
Examples include glycerin, 1,3-butylene glycol, propylene glycol, dipropylene glycol, and polyethylene glycol. Furthermore, examples of the surfactant include polyoxyethylene hardened mustard oil, sorbitan fatty acid ester, polyoxyethylene sorbitan fatty acid ester, polyethylene glycol fatty acid ester, alkyl glyceryl ether, fatty acid salt, alkyl phosphate, and the like.

Further, external preparations to which the present invention is applied include ointments, creams, emulsions, lotions, etc., and the blending amounts shown in Table 1 below are usually suitable.

In addition, in Table 1, the blending ratio is in weight %.

Table 1 [Effects of the Invention] The diacylglycerin represented by the general formula (1) used in the present invention is liquid at room temperature, has excellent oxidative stability, has extremely low decomposition, is low in irritation, and has an excellent feel on the skin and hair. It is something that In other words, to simply obtain liquid diacylglycerin, it is sufficient to use an unsaturated fatty acid such as oleic acid as the fatty acid residue, or a short chain fatty acid such as octanoic acid, but if only unsaturated fatty acids are used, the oxidative stability However, when only short chain fatty acids are used, irritation becomes a problem.

In contrast, the diacylglycerin of the present invention, which simultaneously contains a branched saturated fatty acid residue having 18 carbon atoms and a tetradecanoic acid residue in one molecule, does not have these problems.

Since the external preparation of the present invention containing such diacylglycerin does not contain a crystalline component, it has good compatibility with the skin and has an excellent long-lasting skin moisturizing effect.

〔Example〕

EXAMPLES The present invention will be explained in more detail by showing examples below, but the present invention is not limited to these examples.

In addition, the method for producing monoacylglycerol of branched saturated fatty acids and myristic acid and the branched saturated fatty acid halide is also used as a reference example, and the method for producing diacylglycerol having branched saturated fatty acid residues and myristic acid residues according to the present invention. is shown as a synthesis example.

Reference example 1 A container equipped with a thermometer, reflux condenser, dropping funnel, and stirrer! 2
568 g (2.0 mol) of (5,7,7-)limethyl-2-(1,3,3-)limethylbutyl)octanoic acid (manufactured by Nissan Chemical Co., Ltd.) was charged into the reaction vessel No. 1, and stirred. Meanwhile, 286 g (2.4 mol) of thionyl chloride was added dropwise from a dropping funnel at room temperature under nitrogen gas ventilation. As the dropwise addition of thionyl chloride progressed, the reaction mixture turned colorless, pale yellow, and blackish brown, and at the same time, gas generation was observed. The temperature of the reaction mixture was kept at room temperature during the dropwise addition of thionyl chloride. After adding thionyl chloride dropwise over a period of about 3 hours, the reaction mixture was heated to 60-70°C in an oil bath for about 3 hours.
Saved time. After confirming that almost no gas generation was observed, low-boiling substances were distilled off under reduced pressure, and then vacuum distillation was performed.

112-120°C10,1-0.3mmHg fraction 5
8 g (yield 97%) of B was obtained. This one is 5.7.7-
Dolimethyl-2-(1,3,3-)limethylbutyl)
It was octanoyl chloride.

IR spectrum (liquid film method) 2970, 2920.2875.1795 (C=O stretching), 1480° 1390.1370, 1260,
1210,995,930,790°710,600c
m-'H'-NMR spectrum (CC14 solvent): C0,9(
s, 24H, Cjh) ■ Reference Example 2 Using a reaction vessel with a volume of Mal equipped with the same equipment as that used in Reference Example 1, isostearic acid (a methyl branched fatty acid represented by the following formula, manufactured by Emery Co., Ltd. in the United States) was prepared. , Emery
Reference Example 1: 520 g (4.4 mol) of thionyl chloride was added to 568 g (2.0 mol) of 875 isostearic acid.
reacted in the same way.

Cl5(CHz)-CH(CHz)lICOOHCH3 (in the formula, m and n are each integers of 4 to 10, m+n・
14, with a distribution centered at m=n=7.

) After the reaction, low-boiling substances were distilled off under reduced pressure to recover about 230 g of low-boiling substances believed to be thionyl chloride. Then, by vacuum distillation, 153-b-3. OmmHg fraction 454
g (yield 75%) was obtained.

This was methyl branched isostearic acid chloride.

IR spectrum (liquid film method) 2950, 2920.2550.1800 (C・0 stretching), 1460°1400, 13B0.950.7
20.680.590cm-'H'-NMR spectrum (CC14 solvent): C0,6""1.0 (m, C1
hCHz- and -C3-) 0 animals 3 1.0-1.5 (m, CHt) 1.5-2.
0 (m, -Cll-)CH3 2,77 (t, CIIzCOCl) Reference example 3 Thermometer, nitrogen capillary, reflux condenser (water separation tube material)
In a 21-volume reaction vessel equipped with a stirrer, 568 g (2.0 mol) of 2-hebutylundecanoic acid, 184 g (2.0 mol) of purified glycerin, and 1.2 g of calcium hydroxide were added.
g was charged, and esterification was performed at 230 to 240°C under nitrogen gas ventilation.

After about 10 hours, it was confirmed that almost no water was produced, and the vacuum distillation was switched to 210-220"C/1.
Unreacted glycerin was removed under conditions of 5 to 25 mmHg. After almost no distilled glycerin was observed, the reaction mixture was distilled using a thin-film molecular distiller, and 17
0~175°c 10.03~0. 246 g of a fraction with an O of 5 mmHg was obtained. This was a monoacylglycerol of 2-heptylundecanoic acid.

IR spectrum (liquid film method) 3440 (0 former abbreviation), 2960. 29
10. 2860. 1740 (C=0 expansion/contraction), 1
470.1370.1160.740cm-'H'-N
MR spectrum (CC1, solvent): C0,9 (t, 68
．． Cl, -) 1.1 to 1.6 (n+, 28H, -Cl2-)
0 2.7 (s, 2H, -0-H) 3.5-4.2 (m, 5H, CHz 0- and nC
Dan-0-) Hydroxyl value 311.8 (calculated value 312.
9) Reference Example 4 In a reaction vessel with a capacity of 21 equipped with the same equipment as used in Reference Example 3, 458 g (2.0 mol) of myristic acid, 184 g (2.0 mol) of purified glycerin, and 0.9 g of calcium hydroxide were added. 230-240 under nitrogen gas aeration.
The esterification reaction was carried out at °C for about 8 hours. Next, we switched to vacuum distillation and removed unreacted glycerin under the conditions of 210-220"C/15-25mdg. After no more distilled glycerin was observed, the reaction mixture was distilled using a thin film molecular distillation device. , 195-200℃, 0.03-0
．． 230 g of a fraction of 0.05 ma+Hg was obtained. This was monomyristoylglycerin.

Hydroxyl value: 370.3 (calculated value: 371.0) Synthesis Example 1 Equipped with a thermometer, dropping funnel, reflux condenser, and stirrer 3! 303 g (1 mol) of monomyristoylglycerin obtained in Reference Example 4, 10,100 O of benzene, and 87 g (1.1 mol) of pyridine were added in this order to a reaction vessel. The reaction mixture was stirred and nitrogen gas was bubbled through it. 50°C in an oil bath below
5 obtained in Reference Example 1 from a dropping funnel.
7.7-! -limethyl-2- (1,3,3-)diethylbutyl)octanoic acid chloride 291g (0,9
6 mol) was added dropwise over a period of about 3 hours while maintaining the temperature of the reaction mixture at about 50°C. After the completion of dripping, 60 to 80
℃ and continued stirring for about 5 hours. The white precipitate of pyridine hydrochloride in the reaction product was removed by filtration, and the resulting filtrate was subjected to solvent distillation under reduced pressure.
The product was heated at 190-200"C for about 5 hours under reduced pressure of mHg to completely remove the slight remaining acid chloride. The resulting product had a molecular weight of 5.7.7 - ) A mixture of diacylglycerin and triazylglycerin in which one or two molecules of diethyl-2-(1,3,3-)diethylbutyl)octanoic acid are acylated and unreacted monomyristoylglycerin.

This mixture was subjected to column chromatography (Wakogel B-10 (manufactured by Wako Pure Chemical Industries), hexane/diethyl ether = 707
30) and diacylglycerin fraction 3
60g was obtained. This substance is a colorless and transparent liquid. 5.7.7
-drimethyl-2-(1゜3.3-)diethylbutyl)
It is diacylglycerin with octanoic acid and myristic acid as fatty acid residues.

IR spectrum (liquid film method) 3500 (OH Shin 1i&), 2960.2930
．． 2850. 1740 (C=0 expansion/contraction), 1465
．． 1365.1160.720cm -'H'-NMR
Spectrum (CC14 solvent): δ2.9 (s, 18
．． -OH) 4.0 to 4.5 (m, 4H, -CI□-〇-)5.
1 (L IHI /C and -0H) Acid value 0.1 (calculated value O) Hydroxyl value 98.0 (calculated value 98.6) Synthesis example 2 Capacity 3 equipped with the same equipment as used in synthesis example 1 ! 303 g (1 mol) of monomyristoylglycerin obtained in Reference Example 4, 1500@Z of benzene, and 100 g (1.27 mol) of pyridine were added to the reaction vessel in this order. While stirring, the mixture was heated to 50°C in an oil bath under nitrogen gas flow, and 291 g (0.96 mol) of methyl branched isostearic acid chloride obtained in Reference Example 2 was added dropwise from the dropping funnel. After the addition was complete, the reaction mixture was kept at 50°C for about 3 hours and then at 70-80'C for about 8 hours. As a result of this heat treatment, the esterification reaction proceeded completely, and it was confirmed by the IR spectrum that no acid chloride was contained in the reaction mixture. 372 g of diacylglycerin prepared in the same manner as in Synthesis Example 1 and containing methyl branched isostearic acid and myristic acid as fatty acid residues, which is a colorless and transparent liquid.
I got it.

IR spectrum (liquid film method) 3480 (OH stretching), 2955.2930.2
850.1740 (C=0 expansion/contraction), 1465.13
65.1160.720cm"H'-NMR spectrum (Cc-14 solvent): δ0.9 (m, 98. CH
3) 1.2-1.6 (m, 49H, -C and 2-9-button)
2.3 (m, 48. Hz Co) 1
2.9 (s, LH, -0) 1) 4.0 to 4.5 (a+, 4H, -C and 10) 5.1
(m, LH,, >CH-OH) Acid value 0. l (calculated value O) Hydroxyl value 97.4 (calculated value 98.6) Synthesis Example 3 2-Hebutylundecane obtained in Reference Example 3 was placed in a reaction vessel with a capacity of 21 equipped with a thermometer, a reflux condenser, and a stirrer. Acid monoacylglycerin 359g (1 mol), myristic acid 27
4g (1,2 mol), commercially available lipase preparation Lipozy
80 g of me 3A (lipase of Mucor mle-hei origin immobilized on an anion exchange resin, manufactured by Novo Industries A.S.) was added. The mixture was heated to 50°C and stirred for 5 hours under reduced pressure of 100 to 300 mmHH to carry out an esterification reaction. After the reaction is completed, the lipase preparation is filtered, and the reaction product of the filtrate is 190-19
5°C, 0.03~0. Excess myristic acid and unreacted monoacylglycerin were distilled using a thin-film molecular distillation device under O5 mmHg conditions to remove excess myristic acid and unreacted monoacylglycerin, yielding 501 g of the desired diacylglycerin containing 2-hebutylundecanoic acid and myristic acid as residues. I got it.

IR spectrum (liquid film method) 3480 (OH stretching), 2960.2930.2
850.1740 (C=0 expansion/contraction), 1465.13
65.1160.720cm-'H'-NMR spectrum (CC1a solvent): δ0.9 (m, 98.C
1h) 1.2~1.6 (m, 50L CHt)2
．． 3'(m, 3H1'>CHCo -1CHz Co
)2.7 (s, IB, -0H) 4.0~4.5 (m, 411.CHz O)
5.1 (o+, 18.) Cdan-0H) Acid value 0
．． 1 (calculated value 0) Hydroxyl value 97.1 (calculated value 98.6) Example 1 (ointment) <Oil phase component> Vaseline 40% by weight Squalane 10 Diacylglycerin of the present invention obtained in Synthesis Example 2 20% by weight Butylparaben 0.1% Water phase component> Methylparaben 0.2% by weight Glycerin 10% Water Balance An ointment was prepared using the oil phase component and water phase component having the above composition according to the following manufacturing method.

<Manufacturing method> Methylparaben and glycerin are added to water and heated, and the aqueous phase is maintained at 70°C. On the other hand, other lipophilic components are mixed and heated to dissolve, and the oil phase is brought to 70°C.The oil phase is then added to the aqueous phase and emulsified in an emulsifier.

The ointment of the present invention was prepared by cooling the emulsion to a final temperature of 30° C. using a heat exchanger and then filling the emulsion.

The obtained ointment of the present invention was an external preparation with high skin affinity and excellent long-lasting skin moisturizing effect.

Example 2 (cream) <Oil phase components> Stearic acid 2 wt% cetanol l Cholesterol 1 Squalane 10 Jojoba oil 10 POE (40) Hydrogenated castor oil 0.5 Cetyl phosphoric acid 0.5 Sorbitan monostearate 2.0 Butyl paraben 0 ．．
1 <Aqueous phase components> Methylparaben 0.2% by weight Glycerin 10 1.3-Butylene glycol 5 Fragrance 0.1 Potassium hydroxide 0.1 Water
Balance A cream was prepared by the following manufacturing method using the oil phase component and water phase component having the above composition.

Production method> The above aqueous phase components are mixed, heated and dissolved, and the aqueous phase is maintained at 70°C.The above oil phase component is similarly heated and mixed at 70'C, and the above oil phase is added to the aqueous phase. and emulsify them using an emulsifying machine. The cream of the present invention was prepared by cooling the emulsion to a final temperature of 30°C using a heat exchanger and then filling the emulsion.

The obtained cream of the present invention was an external preparation with high skin affinity and excellent long-term skin moisturizing effect.

Example 3 (Emulsion) <Oil phase components> Setanol 1 wt% squalane 5 Olive oil 3 Jojoba oil 2 POE (10) Hydrogenated castor oil 1 wt% Sorbitan monostearate 1 Butylparaben 0.1 Water phase components> Methylparaben 0 .1% by weight Glycerin 2 1.3-Butylene glycol 2 Ethanol 3 Fragrance 0.1 Water Balance A milky lotion was prepared in the same manner as in Example 2 using the oil phase component and water phase component having the above composition.

The obtained emulsion of the present invention was an external preparation that had high skin affinity and excellent long-lasting skin moisturizing effect.

Example 4 (Lotion) Oil phase component> POE (60) Hydrogenated castor oil 1 Water phase component> Lactic acid Appropriate amount Sodium lactate Appropriate amount Glycerin 3% by weight 1.3-Butylene glycol 1.5 Polyethylene glycol 1500 0.5 Ethanol 1
0 Perfume 0.1 Water Balance A lotion was prepared by the following manufacturing method using the oil phase component and water phase component having the above composition.

Production method> Dissolve glycerin, 1.3-butylene glycol, polyethylene glycol 1500, lactic acid, sodium lactate, and ethanol in water to make it weakly acidic (pH 5 to 6). A lotion of the present invention was prepared by dissolving polyoxyethylene hydrogenated castor oil, the diacylglycerin of the present invention obtained in Synthesis Example 2, and a fragrance in this solution.

The obtained lotion of the present invention was an external preparation with high skin affinity and excellent long-term skin moisturizing effect.

Claims (1)

[Scope of Claims] An external preparation characterized by containing diacylglycerin represented by the following general formula (I). ▲There are mathematical formulas, chemical formulas, tables, etc.▼...(I) [In the formula, one of R_1, R_2, and R_3 is (i) a methyl branched isostearic acid residue represented by the following formula, ▲Mathematical formula, chemical formula , tables, etc. ▼ (In the formula, m and n are each integers from 4 to 10, and m+n
=14, and has a distribution centered at m=n=7. ) (ii) 5,7,7-trimethyl-2-(1,3,3-
(iii) branched saturated fatty acid residues selected from the group consisting of (trimethylbutyl)-octanoic acid residues, and (iii) 2-heptylundecanoic acid residues, one of which is a tetradecanoic acid residue and the rest of which are hydrogen. ]