Polysaccharide derivative

Details Polysaccharide derivative Polysaccharide derivative

2001-12-03

2003-04-01

Barts, Samuel (Department: 1623)

Organic compounds -- part of the class 532-570 series

Organic compounds

Carbohydrates or derivatives

C536S004100, C536S018500, C536S017200, C536S123100, C536S124000, C536S017600, C536S097000

Reexamination Certificate

active

06541614

ABSTRACT:

This is the National Phase Application of PCT/JP00/03485, filed May 31, 2000.
1. Technical Field
This invention relates to novel polysaccharide derivatives, specifically novel polysaccharide derivatives having such unique thickening action that the viscosity thereof increases at a higher temperature than at room temperature and also having a high stabilizing action for hydrophobic substances contained in water, a process for their production, and an aqueous composition containing the polysaccharide derivative.
2. Background Art
Cellulose ethers such as methylcellulose and hydroxyethylcellulose or polyacrylic acid compounds such as “Carbopol” are widely used as a thickener, i.e. one of the important ingredients of cosmetic preparations, toiletry products and the like.
These thickeners, however, have such a rheological characteristic that the viscosity thereof decreases at a high temperature. These thickeners hence are accompanied with such problems that no sufficient viscosity is obtainable when applied for showering agents, bath preparations or the like used in a high-temperature environment such as bathroom, or when the thickeners are used in a larger amount in these products to provide a certain viscosity, the viscosity of the product increases during storage at room temperature, which makes dispensing the products from containers difficult or handling the products inconvenient.
An object of the present invention is, therefore, to provide a thickener having such a Theological characteristic that the viscosity increases at a high temperature, for example, when used in warm water or on the skin, but decreases at room temperature.
3. Disclosure of the Invention
The present inventors have found that novel polysaccharide derivatives, in which the hydrogen atoms of the hydroxyl groups of polysaccharides are substituted with specific polyoxyalkylene-containing groups, have such unique Theological characteristic as described above, an excellent water solubility and improved handling property at low temperatures, and provide a sufficient thickening property at high temperatures, for example, when used in warm water or on the skin, and thus are extremely useful as a thickener and a stabilizer for various toiletry products such as bath preparations, massaging cosmetic preparations, shower preparations, skin care preparations, hair washing preparations, body washing preparations, garment detergents, garment finishing agents and hard surface cleaning agents.
Specifically, the present invention provides a polysaccharide derivative derived from a polysaccharide or a derivative thereof by substituting a part or all of the hydrogen atoms of the hydroxyl groups of the polysaccharide or the derivative thereof with the following substituent groups (A):
(A) groups represented by the following formula:
 —E
1
—(OA)
n
—E
2
—R  (1)
wherein E
1
represents a linear or branched, divalent, saturated C
1-6
hydrocarbon group which may be substituted with one or more hydroxyl groups or oxo groups, n represents a number of from 8 to 300, n numbers of As may be the same or different and each independently represents a linear or branched, divalent, saturated C
1-6
hydrocarbon group, E
2
represents an ether bond or an oxycarbonyl group (—OCO— or —COO—), and R represents a linear or branched C
4-30
alkyl group which may be substituted with one or more hydroxyl groups,
wherein the hydrogen atom(s) in one or more hydroxy groups in each of the substituent groups (A) may be further substituted with the substituent groups (A) as defined above, as wells a process for their production.
Further, the present invention provides a thickener and an emulsifier, each of which comprises the above-described polysaccharide derivative.
Furthermore, the present invention also provides an aqueous composition comprising the above-described polysaccharide derivative.
Best Modes for Carrying Out the Invention
For example, when a cellulose is used as the polysaccharide or the derivative thereof, the recurring unit of the polysaccharide derivative according to the invention can be represented by the following formula:
wherein R may be the same or different and each independently represents a group selected from (1) hydrogen, methyl, ethyl, hydroxyethyl or hydroxypropyl or the like, (2) a polyoxyalkylene-containing substituent group (A), (3) a sulfoalkyl group (B), (4) a carboxyalkyl group (C), and (5) a cationic substituent group (D); Q may be the same or different and each independently represents a C
2-4
alkylene group; a, b and c may be the same or different and each independently represent a number of from 0 to 10; and wherein the groups QO and R, as well as a, b and c in the same recurring unit or in the different recurring units may be the same or different; and wherein one or more hydroxyl groups in each of the substituent groups (A)~(D) may be further substituted with the other substituent groups (A)~(D), with the proviso that at least one of the Rs is substituent group (A).
As E
1
in the formula (1) representing the polyoxyalkylene-containing substituent (A), those having 2 or 3 carbon atoms are preferred. Specifically, ethylene, propylene, trimethylene, 2-hydroxytrimethylene, 1-hydroxymethylethylene, 1-oxoethylene, 1-oxotrimethylene and 1-methyl-2-oxoethylene are preferred.
As A in the formula (1), those having 2 to 3 carbon atoms are preferred. Specifically, ethylene, propylene and trimethylene are preferred. The polymerization degree of (—OA—) as indicated by n is preferably 8 to 120, particularly 10 to 60, in view of thickening effect and emulsion stabilizing action. The “n” number of “A”s may be the same or different. The letter “n” as used herein means an average molar number of (OA). While E
2
represents an ether bond or an oxycarbonyl group, an oxycarbonyl group is preferred.
As R in the formula (1), linear or branched alkyl groups having 5 to 25 carbon atoms, especially 6 to 20 carbon atoms are preferred. From the viewpoint of stability, alkyl groups, especially linear alkyl groups are preferred. Specifically, octyl, decyl, dodecyl, tetradecyl, hexadecyl, octadecyl, isostearyl and the like are preferred.
The degree of substitution with the substituent groups (A) in the polysaccharide derivative according to the present invention is preferably in a range of from 0.0001 to 1.0, more preferably in a range of from 0.0005 to 0.5, particularly preferably in a range of from 0.001 to 0.1 per constituent monosaccharide residual group.
In addition to the substituent groups (A), the polysaccharide derivative according to the present invention may be further substituted with one or more groups selected from the substituent groups (B), (C) and (D) described below. In addition, the hydrogen atom(s) in one or more hydroxyl group(s) contained in each of the substituent groups (A) to (D) may be further substituted with the substituent groups (A) to (D).
(B) C
1-5
sulfoalkyl groups or salts thereof, each of which may be substituted with one or more hydroxyl groups:
Illustrative examples of the substituent groups (B) are 2-sulfoethyl, 3-sulfopropyl, 3-sulfo-2-hydroxypropyl, and 2-sulfo-1-(hydroxymethyl)ethyl. Among these, 3-sulfo-2-hydroxypropyl is preferred from the viewpoint of stability and production. All or some of these substituent groups (B) may be in the form of salts with Group 1 or Group 2 elements such as Na, K, Ca or Mg or an organic cation such as amine or ammonium ion. The degree of substitution with these substituents (B) is preferably in a range of from 0 to 1.0, more preferably in a range of from 0 to 0.8, particularly preferably in a range of from 0 to 0.5 per constituent monosaccharide residual group.
(C) C
2-6
carboxyalkyl groups or salts thereof, each of which may be substituted with one or more hydroxyl groups:
Illustrative examples of the substituent groups (C) are carboxymethyl, carboxyethyl, carboxypropyl, carboxybutyl and carboxypentyl. Among these, carboxymethyl is preferred from the viewpoint of stability and production. All or some of these substituent groups (C) may be in the form

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