Organic compounds -- part of the class 532-570 series – Organic compounds – Oxygen containing
Reexamination Certificate
2001-08-31
2004-01-27
Rotman, Alan L. (Department: 1625)
Organic compounds -- part of the class 532-570 series
Organic compounds
Oxygen containing
Reexamination Certificate
active
06683222
ABSTRACT:
BACKGROUND OF THE INVENTION
1. Field of the Invention
The present invention relates to a polyether-polyol compound and a polyglycerol alkyl ether, an ester obtained by using the polyether-polyol compound or the polyglycerol alkyl ether, and a composition comprising the polyether-polyol compound, the polyglycerol alkyl ether or the ester.
2. Discussion of the Related Art
Conventionally, a polyether-polyol compound is prepared by carrying out an addition reaction of an alcohol with an epoxy compound, or a condensation reaction of a polyhydric alcohol at a high-temperature of 200° C. or more in the presence of a catalyst. The polyether-polyol compound formed by such reactions is mainly a linear compound. For instance, the structure of a polyglycerol, a kind of the polyether-polyol compound, can be generally represented as follows.
In the polyether-polyol compound having such a structure, as the degree of polymerization increases, the number of secondary hydroxyl group positioned in the inner part of the molecule increases, while the number of hydroxyl group positioned at a terminal of the molecule stays the time. The hydroxyl groups other than those at a terminal of this polyether-polyol compound have a low reactivity due to steric hindrance. Therefore, when the polyether-polyol compound is utilized, for instance, as a crosslinking agent for the resin, excess energy must be applied by such means of heating, thereby causing such problems as coloration.
In addition, the above-mentioned polyglycerol is esterified with a fatty acid to be mainly utilized as surfactants for foods. In the esterification, while the reaction rapidly progresses at a terminal hydroxyl group, the reaction is delayed at a central hydroxyl group. Therefore, especially severe conditions are required to prepare a lipophilic ester by adding a large amount of a fatty acid, thereby undesirably making the flavor and hue poor.
Nonionic surfactants can be utilized for a wide variety of purposes such as emulsification, solubilization, permeation, dispersion and washing. Widely used nonionic surfactants include glycerol fatty acid esters, sorbitan fatty acid esters, polyoxyethylene sorbitan fatty acid esters, polyethylene glycol fatty acid esters, polyoxyethylene alkyl ethers, polyoxyethylene alkylphenyl ethers, polyoxyethylene hardening castor oil derivatives, and the like. These nonionic surfactants can be classified into ester-type, ether-type and ester-ether-type by the binding modes of the lipophilic group moiety with the hydrophilic group moiety. Among them, ether-type surfactants are favorably utilized owing to their excellent stability against hydrolysis. As the hydrophilic group of the ether-type surfactant, polyoxyethylene is generally used. While the polyoxyethylene has an advantage of facilitation in the chain extension, there may arise such problems that harmful dioxane is formed during preparation, that formalin is generated by oxidation, and that the liquid becomes acidic.
In order to overcome the problems, ether-type surfactants having a polyglycerol having high safety as a hydrophilic group have been developed. For instance, Japanese Patent Laid-Open No. Sho 62-210049 discloses an ether obtained from di-, tri-, or tetraglycerol and a higher alcohol, and Japanese Patent Laid-Open No. Hei 9-188755 discloses a process for preparing a polyglycerol alkyl ether. However, conventional polyglycerols including those mentioned above have a linear structure, and they are composed of a mixture of polyglycerols having different degrees of polymerization. Therefore, a polyglycerol alkyl ether having a branched structure has not yet known.
Specifically, the conventionally known polyglycerol is a polyglycerol having a linear structure such as tetra-, hexa-, and decaglycerol, and its degree of polymerization is calculated on the basis of the hydroxyl value. Therefore, each polyglycerol does not mainly comprise tetra-, hexa-, and decamer of glycerol as indicated by its name, and each of them is composed of a mixture of polyglycerol comprising monomer to decal- or more 'mers of glycerol. When an alkyl ether is prepared by using the conventional polyglycerol, the resulting product would undesirably be composed of a mixture of various kinds of alkyl ethers. In addition, an alternative process for preparing a polyglycerol alkyl ether includes a process comprising carrying out a condensation reaction of glycidol or epichlorohydrin with an aliphatic alcohol. However, the degree of condensation of the resulting polyglycerol is adjusted by the amount of glycidol or epichlorohydrin added, so that one composed of a single degree of condensation cannot be obtained. The resulting polyglycerol alkyl ether obtained by these processes is composed of a mixture of components having different glycerol chain lengths, so that the compound does not exhibit the function inherently owned by the polyglycerol alkyl ether, rendering it necessary to use a large amount of the polyglycerol alkyl ether to achieve its purpose.
On the other hand, a polyglycerol fatty acid ester is a nonionic surfactant having high safety which is approved as a food additive, and is widely used in fields other than foods such as cosmetics and detergents. A polyglycerol which is used as a raw material for the presently commercially available polyglycerol fatty acid ester is prepared by polymerizing a glycerol-related compound such as glycerol, glycidol or epichlorohydrin. The polyglycerol formed by this reaction is a linear polyglycerol as mentioned above, and this linear polyglycerol is used in the preparation of the linear fatty acid ester by means of esterification with a fatty acid ester, which the resulting ester is presently used as a surfactant.
Generally, the shape of the hydrophilic moiety of the hydrophilic surfactant has a large effect on its performance. In order that the surfactant exhibits its effects, the surfactant must be adsorbed to the interface and cover its entire surface. In the polyglycerol fatty acid ester having linear polyglycerol moiety represented by the formula mentioned above as a hydrophilic group, the ester also takes a linear form. When the ester adsorbs to the interface, the area occupied by the adsorbed portion is a small value, approximating the cross-sectional area of the ester. Therefore, in order to exhibit its surfactant ability sufficiently, the interface must be covered completely, thereby consuming a large amount of a surfactant. Consequently, lowering of product values such as causing roughened skin when applied to cosmetics, and impairing flavors when applied to foods.
An object of the present invention is to provide a novel polyether-polyol compound, a polyglycerol alkyl ether and an ester having excellent emulsification, solubilization, dispersion, detergency, foaming strength or the like, of a polyglycerol, and a composition comprising the polyether-polyol compound, the polyglycerol alkyl ether or the ester.
These and other objects of the present invention will be apparent from the following description.
SUMMARY OF THE INVENTION
According to the present invention, there are provided:
(1) a polyether-polyol compound represented by the compositional formula:
C
3n
H
6n+2
O
2n+
,
wherein n is an integer of 4 or more,
wherein the polyether-polyol compound has a total number of 1,2-diol unit and 1,3-diol unit of [(n/2)+1] in a case where n is an even number of 4 or more, or a total number of 1,2-diol unit and 1,3-diol unit of [((n−1)/2)+1] and one hydroxyl group which is not involved in the units in a case where n is an odd number of 5 or more;
(2) a polyglycerol alkyl ether, a part of hydroxyl groups in a polyglycerol being substituted by an alkyl group, wherein the polyglycerol is the polyether polyol compound of item (1) above;
(3) an ester prepared by the process comprising reacting the polyether-polyol compound of item (1) above or the polyglycerol alkyl ether of item (2) above with a fatty acid; and
(4) a composition comprising the polyether-polyol compound of item (1) ab
Nakamura Takeshi
Yamashita Masatsugu
Birch & Stewart Kolasch & Birch, LLP
Reyes Hector M
Rotman Alan L.
Taiyo Kagaku Co., Ltd.
LandOfFree
Polyether-polyol compound does not yet have a rating. At this time, there are no reviews or comments for this patent.
If you have personal experience with Polyether-polyol compound, we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Polyether-polyol compound will most certainly appreciate the feedback.
Profile ID: LFUS-PAI-O-3205807