JPH05124928A - Cosmetic - Google Patents

Abstract

PURPOSE:To obtain a cosmetic having moisture-retention effect resistant to sweat, water washing, etc., free from stickiness to the skin and hair and giving moist feeling by compounding a specific phosphobetaine. CONSTITUTION:The objective cosmetic contains a phosphobetaine of formula I (Z is residue obtained by removing (m+n) x OH groups from monosaccharide, oligosaccharide, sugar alcohol or glycerol; R<1> to R<3> are alkyl, alkenyl or hydroxyalkyl; M<1> and M<2> are H or cation; (m) is >=0; (n) is >=1) [e.g. alpha-D- glucopyranose-1-[Z-hydroxy-3-(N,N-dimethyl-N-octadecylammonio) propyl]phosphate]. The phosphobetaine of formula I is preferably compounded in an amount of 0.5-10wt.% based on the cosmetic. The compound can be produced e.g. by reacting a phosphoric acid ester of formula 2 with an epoxy compound of formula 3. The cosmetic is especially suitable as a wash-off type rinse and body rinse.

Description

Detailed Description of the Invention

[0001]

BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to a cosmetic composition, and more particularly to a cosmetic composition which is less likely to lose its moisturizing effect due to perspiration, washing with water, etc., and which gives a moist feel to the skin and hair.

[0002]

2. Description of the Related Art Conventionally, various moisturizers having a protective effect on the skin and hair have been incorporated into cosmetics. However, these moisturizers are vulnerable to moisture such as perspiration, and in cosmetics of the type used in pools or rinsed off such as rinses and body rinses, their original effects are often not sufficiently exhibited. On the other hand, when a large amount of a moisturizer is added for the purpose of sufficiently retaining the skin and hair protecting effect even after washing off, there is a problem that stickiness or the like occurs and the usability deteriorates.

[0003]

SUMMARY OF THE INVENTION Therefore, the object of the present invention is to provide a cosmetic which is strong against moisture such as sweat, has a sufficient moisturizing effect even when washed off, does not cause stickiness, and gives a moist and good feeling. To provide.

[0004]

In view of the above situation, the inventors of the present invention have made extensive studies, and as a result, by adding phosphobetaine represented by the general formula (1) described below, the moisturizing effect is maintained even after washing, Moreover, they have found that a cosmetic having a good feeling in use can be obtained, and completed the present invention.

That is, the present invention provides a cosmetic material containing phosphobetaine represented by the following general formula (1).

[0006]

[Chemical 2]

At least one of R ¹ , R ² and R ³ represents an alkyl group or alkenyl group having 5 to 24 carbon atoms, or a hydroxyalkyl group or hydroxyalkenyl group having 1 to 4 carbon atoms, and the rest are the same or Differently represents a linear or branched alkyl group or alkenyl group having 1 to 24 carbon atoms which may have a hydrogen atom or a hydroxyl group. M ¹ and M ² are the same or different and each represents a hydrogen atom or a cation, m represents a number of 0 or more, and n represents a number of 1 or more. However, m + n does not exceed the number of hydroxyl groups respectively possessed by the monosaccharide, oligosaccharide, sugar alcohol or glycerin. ]

Z in the general formula (1), which represents phosphobetaine used in the cosmetics of the present invention, is m + n (m and n have the above meanings) derived from a monosaccharide, an oligosaccharide, a sugar alcohol or glycerin. A residue without a hydroxyl group, and examples of monosaccharides in this case include allose, altrose,
Examples thereof include glucose, mannose, gulose, idose, galactose, talose, fructose, inositol, ribose, arabinose, xylose, lyxose and ribulose. Examples of sugar alcohols include, for example, sorbitol, mannitol, galactitol, xylitol, arabinitol obtained by reducing monosaccharides,
Examples thereof include ribitol and maltitol and lactitol obtained by reducing oligosaccharides. Examples of oligosaccharides include maltooligosaccharides such as maltose, isomaltose, maltotriose, maltotetraose and maltoheptaose; cellooligosaccharides such as cyclodextrin and cellobiose; mannooligosaccharides, fructooligosaccharides,
Examples include sucrose and lactose. Further, the hydroxyl groups of these monosaccharides, sugar alcohols, and oligosaccharides may be modified with appropriate organic residues such as acylation, etherification, alkylene oxide addition, and acetalization, except for at least one hydroxyl group.

In the general formula (1), the linear alkyl group represented by R ¹ , R ² or R ³ is, for example, methyl, ethyl,
Propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, undecyl, dodecyl, tridecyl, tetradecyl, pentadecyl, hexadecyl,
Examples thereof include groups such as heptadecyl, octadecyl, nonadecyl, eicosyl, heneicosyl, docosyl, tricosyl, and tetracosyl; examples of the branched chain alkyl group include methylhexyl, ethylhexyl, methylheptyl, ethylheptyl, methylnonyl, methylundecenyl, and methylhepta. Examples thereof include groups such as decanyl, hexyldecyl and octyldecyl. Examples of the straight chain or branched chain alkenyl group include ethenyl, propenyl, butenyl, pentenyl, hexenyl, heptenyl, octenyl, nonenyl, decenyl, dodecenyl, undecenyl, tridecenyl, tetradecenyl, pentadecenyl,
Examples thereof include groups such as hexadecenyl, heptadecenyl, octadecenyl, nonadecenyl, eicosenyl, heneicocenyl, dococenyl, tricocenyl and tetracocenyl.

Examples of the linear or branched alkyl group substituted with a hydroxyl group include hydroxymethyl, hydroxyethyl, hydroxypropyl, hydroxybutyl, hydroxypentyl, hydroxyhexyl, hydroxyheptyl, hydroxyoctyl, hydroxynonyl, hydroxydecyl, Hydroxyundecyl, hydroxydodecyl, hydroxytridecyl, hydroxytetradecyl,
Hydroxypentadecyl, hydroxyhexadecyl, hydroxyheptadecyl, hydroxyoctadecyl, hydroxynonadecyl, hydroxyeicosyl, hydroxyheneicosyl, hydroxycosyl, hydroxytricosyl, hydroxytetracosyl, hydroxymethylhexyl, hydroxyethylhexyl, hydroxymethyl Examples include groups such as heptyl, hydroxyethylheptyl, hydroxymethylnonyl, hydroxymethylundecenyl, hydroxymethylheptadecanyl, hydroxyhexyldecyl, hydroxyoctyldecylbutyl. The linear or branched alkenyl group substituted with a hydroxyl group includes, for example, hydroxyethenyl, hydroxypropenyl, hydroxybutenyl, hydroxypentenyl, hydroxyhexenyl, hydroxyheptenyl, hydroxyoctenyl, hydroxynonenyl, hydroxydeenyl. Cenyl, hydroxydodecenyl, hydroxyundecenyl, hydroxytridecenyl, hydroxytetradecenyl, hydroxypentadecenyl, hydroxyhexadecenyl, hydroxyheptadecenyl, hydroxyoctadecenyl, hydroxy Examples thereof include groups such as nonadecenyl, hydroxyeicosenyl, hydroxyheneicosenyl, hydroxydocosenyl, hydroxytricosenyl, and hydroxytetracosenyl.

However, in the phosphobetaine (1) used in the present invention, at least one of R ¹ , R ² and R ³ is an alkyl or alkenyl group having 5 to 24 carbon atoms or a carbon number of the above groups. 1-4 hydroxyalkyl or hydroxyalkenyl groups.

Examples of the cationic group represented by M ¹ or M ² include alkali metal, ammonium group, alkylammonium group, acidic amino acid group, trialkanolamine and the like. Furthermore, m is a number of 0 or more, and n is 1.
Although it is the above number, m is preferably 0.

The phosphobetaine (1) of the present invention is produced, for example, according to the reaction formula shown below.

[0014]

[Chemical 3]

[Wherein Z, R ¹ , R ² , R ³ , M ¹ , M ² ,
m and n have the same meanings as described above, and X ⁻ represents an anion]

That is, the phosphobetaine (1) is obtained by reacting the phosphoric acid ester (2) with the epoxy compound (3). Here, as the phosphoric acid ester (2), for example, glucose-1-phosphoric acid, glucose-
6-phosphate, mannose-1-phosphate, mannose-6
-Phosphoric acid, galactose-1-phosphoric acid, galactose-
6-phosphate, fructose-1-phosphate, fructose-6-phosphate, fructose-1,6-diphosphate, ribose-1-phosphate, xylose-5-phosphate, inositol phosphate, sucrose phosphate , Maltose phosphate, maltotriose phosphate, maltotetraose phosphate, maltopentaose phosphate, maltohexaose phosphate, maltoheptaose phosphate, cyclodextrin phosphate, cellobiose phosphate, lactose phosphate, sorbitol phosphorus Examples thereof include inorganic salts or organic salts such as acids, mannitol phosphoric acid, galactitol phosphoric acid, xylitol phosphoric acid, arabinitol phosphoric acid, ribitol phosphoric acid, maltitol phosphoric acid and glycerophosphoric acid.

The other raw material, the epoxy compound (3), can be easily produced by a known method, for example, by reacting a corresponding trialkylamine or trialkenylamine with epihalohydrin.

X ⁻ in the general formula (3) is not particularly limited, but examples thereof include a halogen atom and an anion such as alkyl sulfate.

In order to carry out this reaction, for example, the phosphoric acid ester (2) and the epoxy compound (3) are mixed with a polar solvent such as water, methanol, ethanol, isopropanol, dimethylformamide, dimethylsulfoxide or a mixture thereof. The reaction may be performed at a temperature of 20 to 150 ° C., preferably 40 to 90 ° C. in the presence of a mixed solvent of one or more kinds, preferably water or a mixed solvent of water and a lower alcohol. The amount of the epoxy compound (3) used in this reaction may be appropriately set according to the numbers of m and n of the phosphobetaine (1) of the present invention to be produced, but usually the phosphorus of the phosphate ester (2) is used. Number of acid residues (m
+ N) is preferably 0.1 to 20 times mol.

In addition to phosphobetaine (1), the reaction product usually contains an inorganic salt as a by-product, an unreacted epoxy compound (3) or an epoxy ring-opened product thereof. The ratio of each component in this reaction product depends on the conditions such as the kinds of the starting phosphoric acid ester (2) and the epoxy compound (3) used, the reaction molar ratio thereof, the amount of the reaction solvent used, the reaction temperature and the like. .. Therefore, depending on the purpose of use, the reaction product can be used as it is, but when a higher-purity product is required, for example, a solvent fractionation method, a dialysis method,
It may be appropriately purified before use by a known method such as a recrystallization method, a partition chromatography, an ion exchange chromatography and a gel filtration method.

Phosphobetaine (1) thus obtained
Is 0.1 to 20% by weight, particularly 0.5
It is preferable to add 10 to 10% by weight.

In the cosmetic composition of the present invention, in addition to the phosphobetaine (1), ingredients used in ordinary cosmetic compositions, such as ethylene glycol, diethylene glycol, triethylene glycol and polyethylene glycols higher than that,
Propylene glycol, dipropylene glycol, higher polypropylene glycols, butylene glycols such as 1,3-butylene glycol and 1,4-butylene glycol, glycerin, diglycerin, further polyglycerins, sorbitol, mannitol, xylitol , Sugar alcohols such as maltitol, ethylene oxide (hereinafter abbreviated as EO) adduct of glycerins, propylene oxide (hereinafter abbreviated as PO) adduct, EO and PO adducts of sugar alcohols, galactose, glucose,
Monosaccharides such as fructose and EO and PO adducts thereof, polysaccharides such as maltose and lactose and EO and PO adducts thereof, liquid paraffin, squalane,
Hydrocarbons such as petrolatum and solid paraffin, olive oil,
Natural oils such as jojoba oil, evening primrose oil, coconut oil and beef tallow, isopropyl myristate, cetyl isooctanoate, ester oils such as neopentyl glycol dicaprate, silicone oils such as methyl silicone and methyl phenyl silicone, isostearic acid, olein Oily components such as higher fatty acids such as acids; POE alkyl ether, POE branched alkyl ether, POE sorbitan ester, POE
Surfactants such as glycerin fatty acid ester, POE hydrogenated castor oil, sorbitan ester, glycerin fatty acid ester, polyglycerin fatty acid ester; vitamins,
Antibacterial agents such as triclosan, trichlorocarban, etc., anti-inflammatory agents such as dipotassium glycyrrhizinate, tocopherol acetate, antidandruff agents such as zinc pyrithione, octopirox, activators, UV absorbers; preservatives such as methylparaben, butylparaben, etc. , Foaming agents such as alkylamine oxides and fatty acid alkanolamides, inorganic salts, viscosity modifiers such as polyethylene glycol stearate ethanol, pearling agents, perfumes, dyes, antioxidants;
Montmorillonite, saponite, hecklite, veegum,
Water-swelling clay minerals such as Kunibia and smecton; Others such as carrageenan, xanthan gum, sodium alginate, pullulan, methylcellulose, carboxymethylcellulose, hydroxyethylcellulose, hydroxypropylcellulose and other polysaccharides, carboxyvinyl polymers, polyvinylpyrrolidone and other synthetic polymers Polymer of
Titanium oxide, kaolin, mica, sericite, zinc flower,
An extender pigment such as talc and a pigment such as polymer powder such as polymethylmethacrylic acid and nylon powder can be appropriately blended within a range that does not impair the effects of the present invention.

The cosmetic of the present invention can be produced by a usual method, and its dosage form can be any dosage form such as liquid form, cream form, solid form, powder form, etc., but particularly liquid form. Alternatively, it is preferably creamy.

The cosmetic of the present invention has an excellent moisturizing effect,
Its effect is not easily impaired by perspiration, washing with water, etc., it is not sticky to the skin and hair, and imparts a moist feel and flexibility, and is particularly suitable as a rinse-type rinse and body rinse. ..

[0025]

The present invention will now be described with reference to reference examples and examples, but the present invention is not limited thereto.

Reference Example 1 35 g (0.1 mol) of α-D-glucose-1-phosphate monosodium salt tetrahydrate and 500 g of water were placed in a reactor.
Was charged and the temperature was raised to 60 ° C. Next, while maintaining the reaction system at 60 ° C., a solution prepared by dissolving 78 g (0.2 mol) of glycidyldimethyloctadecyl ammonium chloride in 200 g of a 30% ethanol aqueous solution was gradually added dropwise,
The reaction was carried out at 60 ° C for 15 hours. After completion of the reaction, the reaction solvent was removed under reduced pressure, and the residue was washed with 10 volumes of acetone to remove unreacted glycidyldimethyloctadecyl ammonium chloride and its epoxy ring-opened product. The resulting crude product was purified by recrystallization from ethanol until thin layer chromatography gave a single spot,
α-D-glucopyranose-1- [2-hydroxy-3
-(N, N-dimethyl-N-octadecylammonio)
33 g of propyl] phosphate (designated as compound 1) was obtained (isolation yield 54%).

Reference Example 2 50 g of disodium α-glycerophosphate (0.
23 mol), 500 g of water and 230 g of 1N hydrochloric acid,
The temperature was raised to 60 ° C. Next, while maintaining the reaction system at 60 ° C,
Glycidyl dimethylpentyl ammonium chloride 9
A solution prepared by dissolving 5.1 g (0.46 mol) in 400 g of a 30% ethanol aqueous solution is added dropwise over 5 hours. Then, the temperature was maintained at 60 ° C. and the reaction was performed for 15 hours. After completion of the reaction, the solvent was distilled off under reduced pressure, and the residue was washed with 10 volumes of acetone to remove unreacted glycidyl dimethylpentyl ammonium chloride and an epoxy ring-opened product thereof. The crude product obtained was washed with 80% aqueous ethanol and purified by thin layer chromatography to give a single spot, pure 2,3-dihydroxypropyl [2-hydroxy-3- (N, N- 25 g of dimethyl-N-pentylammonio) propyl] phosphate (designated as compound 2) was obtained (isolation yield 35%).

Reference Example 3 Sorbitol phosphate sodium salt 8.
9 g (0.032 mol) and 100 g of water were put, and it heated at 60 degreeC. Next, while maintaining the reaction system at 60 ° C., glycidyl dimethyl hexadecyl ammonium chloride 17.
A solution prepared by dissolving 4 g (0.048 mol) in 100 g of a 30% aqueous ethanol solution is added dropwise over 2 hours. afterwards,
The temperature was maintained at 60 ° C. and the reaction was performed for 10 hours. After completion of the reaction, the solvent was distilled off under reduced pressure, and the residue was washed with 10 times the amount of acetone to remove unreacted glycidyldimethylhexadecyl ammonium chloride and its epoxy ring-opened product.
The crude product obtained was washed with 90% aqueous ethanol and purified by thin layer chromatography to give a single spot, pure 2,3,4,5,6-pentahydroxyhexyl [2-hydroxy]. 5.6 g of -3- (N, N-dimethyl-N-hexadecylammonio) propyl] phosphate (designated as compound 3) was obtained (isolated yield 3
0%).

Reference Example 4 47 g of maltose phosphate disodium salt (0.
(1 mol), 400 g of water and 200 g of 1N hydrochloric acid were added, and the mixture was stirred and dissolved and the temperature was raised to 70 ° C. A solution prepared by dissolving 122 g (0.4 mol) of glycidyl dimethyldodecyl ammonium chloride in 300 g of water was gradually added dropwise thereto, and then reacted at 70 ° C. for 20 hours. After completion of the reaction, the reaction solvent was removed by freeze-drying the reaction solution. The obtained reaction product was washed with 10 times the amount of acetone to remove unreacted glycidyl dimethyldodecyl ammonium chloride and its epoxy ring-opened product. Then, it was purified by ion exchange chromatography (ion exchange resin: AG501-X8 manufactured by BIO RAD), and maltose [2-
Hydroxy-3- (N, N-dimethyl-N-dodecylammonio) propyl] phosphate (designated as compound 4)
35 g was obtained (isolation yield 51%).

Reference Example 5 105 g (0.3 mol) of α-D-glucose-1-phosphate monosodium salt and 500 g of water were placed in a reactor and the temperature was raised to 60 ° C. Next, while maintaining the reaction system at 60 ° C., a solution of 164 g (0.9 mol) of glycidyl-2-hydroxyethyldimethylammonium chloride in 150 g of water was gradually added dropwise, and then at 15 ° C. at 15 ° C.
Reacted for hours. After completion of the reaction, the reaction solvent was removed under reduced pressure, and the residue was washed with 10 volumes of ethanol to remove unreacted glycidyl-2-hydroxyethyldimethylammonium chloride and its epoxy ring-opened product. The obtained crude product was dissolved in 300 g of water and subjected to ion exchange chromatography (ion exchange resin: manufactured by BIO RAD).
AG501-X8) and purified by α-D-glucopyranose-1- [2-hydroxy-3- {N- (2-hydroxyethyl) -N, N-dimethylammonio} propyl] phosphate (Compound 5) ) 82 g (isolated yield 68%).

Reference Example 6 45 g (0.09 mol) of fructose-1,6-diphosphate trisodium salt hexahydrate and 200 g of water were placed in a reactor, stirred and dissolved, and the temperature was raised to 60 ° C. Glycidyl-2-
Hydroxyethyl dimethyl ammonium chloride 73
A solution prepared by dissolving g (0.4 mol) in 200 g of water was gradually added dropwise, and after the addition, reaction was carried out at 60 ° C. for 20 hours. After completion of the reaction, the reaction solvent was removed under reduced pressure, and the resulting residue was mixed with 1
It was washed three times with 0 times amount of ethanol to remove unreacted glycidyl-2-hydroxyethyldimethylammonium chloride and its epoxy ring-opened product. The obtained crude product was dissolved in 300 g of water and subjected to ion exchange chromatography (ion exchange resin: manufactured by BIORAD AG501-).
X8) and then fructose-1,6-di [2-
18.3 g of hydroxy-3- {N, N-dimethyl-N- (2-hydroxyethyl) ammonio} propyl] phosphate (designated as compound 6) was obtained (isolated yield 32
%).

Example 1 A hair rinse composition having the composition shown in Table 1 below was prepared, and its performance was evaluated by 10 Japanese female panelists who had never been subjected to cosmetic treatment such as cold perm or bleach. received. That is, 2 g of the shampooed hair was applied and allowed to spread, rinsed with running water at 40 ° C., dried with a towel and dried with a drier, and its performance was evaluated. The results are shown in Table 1. (Evaluation Criteria) (1) Flexibility ◎: Very soft. ○: Soft Δ: Neither hard nor soft. X: Hard (2) Stickiness ◎: Good feeling without stickiness. ○: Not sticky. Δ: Neither can be said. X: Sticky. (3) Moist feeling ◎: Very moist. ○: Moisturizes. Δ: Neither can be said. X: Not moisturized.

[0033]

[Table 1]

As a result, all the products of the present invention were excellent in the effect of imparting flexibility to the hair even after washing with water, and were not sticky and had a moist feel.

Example 2 A hair treatment having the composition shown below was prepared. 2-dodecyl hexadecyl trimethylammonium chloride 2 stearyl trimethyl ammonium chloride 2 compound 2 5 stearyl alcohol 5 lanolin 3 liquid paraffin 3 polypeptide (collagen hydrolyzate) 5 hydroxyethyl cellulose (1% aqueous solution viscosity 8,000 cp) 0.5 polyethylene (5) Oleyl ether 0.5 Methylparaben 0.2 Perfume 0.4 Water Balance total 100 (% by weight) This hair treatment has an excellent effect of imparting softness to hair even after washing, and is not sticky and has a moist feel. Was obtained.

Example 3 A body treatment having the composition shown below was prepared. 2-Hexyldecylphosphoric acid arginine salt 1 2-Ethylhexanoic acid diglyceride 20 2-Ethylhexanoic acid neopentyl glycol 20 Compound 3 5 N-Tris (hydroxymethyl) -isostearic acid amide 3 Olive oil 3 Squalane 3 Sorbitol 10 Diethylene glycol monoethyl Ether 10 fragrance, dye, proper amount of water, balance 100 (% by weight) This body treatment was excellent in moisturizing property even after washing off, and was not sticky and had a moist feel.

Example 4 A pack cosmetic having the following composition was prepared. Polyvinyl alcohol ^{* 1} 12 Polyethylene glycol 4000 2 Polyoxyethylene methyl glucoside (20 EO adduct) ^{* 2} 3 Compound 4 5 Squalane 3 Ethanol 7.7 Perfume 0.5 Preservative Suitable amount Sorbitan monostearate ^{* 3} 0.5 Monostearic acid Polyoxyethylene sorbitan (20EO adduct) ^{* 4} 0.2 Water balance 100 (% by weight) * 1 Gohsenol EG-30: Nippon Synthetic Chemical Industry Co., Ltd. * 2 Glucam E-20: Amakor Corporation * 3 Leodol SPS10 : Kao Co., Ltd. * 4 Leodoll TWS120: Kao Co., Ltd. This pack did not lose its moisturizing property due to sweat, was not sticky, and had a moist feeling.

Example 5 A lotion having the following formulation was prepared. Lactic acid 0.03 Sodium lactate 0.84 Compound 6 5 Glycerin 2 Polyoxyethylene oleyl ether (20EO adduct) 1 Ethanol 10 Perfume 0.3 Water Balance total 100 (% by weight) This lotion loses its moisturizing ability with sweat. It was not greasy, it was not sticky, and a moist feeling was obtained.

Example 6 A powder bath having the following formulation was prepared. Sodium hydrogen carbonate 67 Dextrin 30 Compound 1 2 Fragrance 0.5 Colorant 0.5 Total 100 (wt%) This powder bath was excellent in moisturizing effect on the skin and had a moist feeling.

Example 7 A solid bathing agent having the following formulation was prepared. Sodium hydrogen carbonate 37 Succinic acid 36 Dextrin 25 Compound 2 1.5 Fragrance 0.5 Total 100 (% by weight) This solid bath agent had an excellent moisturizing effect on the skin and gave a moist feeling.

─────────────────────────────────────────────────── ─── Continuation of the front page (51) Int.Cl. ⁵ Identification code Office reference number FI technical display location A61K 7/08 8615-4C 7/50 9051-4C

Claims (1)

[Claims] 1. A cosmetic comprising a phosphobetaine represented by the general formula (1). [Chemical 1] At least one of R ¹ , R ² and R ^{3 has 5 to 2} carbon atoms.
An alkyl group or an alkenyl group having 4 or 1 to 4 carbon atoms
4 represents a hydroxyalkyl group or a hydroxyalkenyl group, the rest of which may be the same or different and may have a hydrogen atom or a hydroxyl group, which may have a linear or branched carbon number of 1 to 1.
24 represents an alkyl group or an alkenyl group. M ¹ and M ² are the same or different and each represents a hydrogen atom or a cation, m represents a number of 0 or more, and n represents a number of 1 or more. However, m + n does not exceed the number of hydroxyl groups respectively possessed by the monosaccharide, oligosaccharide, sugar alcohol or glycerin. ]