Drug – bio-affecting and body treating compositions – Live hair or scalp treating compositions
Reexamination Certificate
1998-10-28
2002-05-14
Page, Thurman K. (Department: 1615)
Drug, bio-affecting and body treating compositions
Live hair or scalp treating compositions
C424S061000, C424S063000, C424S073000, C514S012200, C514S013800, C514S017400, C514S772400, C514S723000
Reexamination Certificate
active
06387359
ABSTRACT:
FIELD OF THE INVENTION
The present invention relates to an acyl-neutral amino acid polyglycerin ester, and more perticularly to an N-long chain acyl-neutral amino acid polyglycerin ester in which at least one or more N-long chain acyl-neutral amino acid molecules are bonded via ester bonding to one molecule of polyglycerin having a degree of glycerin polymerization of 4 or more, and to a nonionic surfactant composition comprising, as an active ingredient, at least one kind of such esters and a cosmetic composition or a percutaneous preparation comprising, as a nonionic surfactant ingredient, at least one kind of such esters in an effective amount.
Incidentally, the acyl-neutral amino acid polyglycerin ester is, as can be seen from its structural formula given later, a nonionic compound, and shows surface activity (emulsifying activity). For these reasons it is a kind of nonionic surfactant.
BACKGROUND OF THE INVENTION
Heretofore, anionic surfactants as used in soap emulsification in the past have been generally used as surfactants in producing emulsified products such as cosmetic compositions, percutaneous preparations, and the like, but, recently, ethylene oxide-based nonionic surfactants have become used popularly for that purpose. However, the safety of ethylene oxide-based nonionic surfactants is considered problematic in that they often irritate sensitive skins. Many consumers who take an increasing interest in the safety of products therefore desire ethylene oxide-free nonionic surfactants. In particular, they desire products of natural materials.
As nonionic surfactants which are less irritative or the like, and therefore highly safe are widely known polyglycerin fatty acid esters which are esterified products of polyglycerins with fatty acids.
As is well known, fatty acids are natural substances, and polyglycerins are condensation products of glycerin which is also a natural substance. Polyglycerin fatty acid esters are preferred to ethylene oxide-based nonionic surfactants in view of their safety, and the former can be produced easily on an industrial scale. However, conventional polyglycerin fatty acid esters cannot, when used in cosmetic compositions such as milky lotion, cream and the like or in percutaneous preparations, be always sensorially satisfactory, as they are often sticky or the like.
On the other hand, as less irritative and highly safe natural surfactants are widely used N-long chain acyl-neutral amino acids which are acylated products of amino acids with fatty acids. Some compounds wherein such N-long chain acyl-neutral amino acids are introduced, are known as nonionic surfactants usable as emulsifiers, etc. For example, in Japanese Patent Publication (
kokoku
) No. 62991/1979, it is disclosed that alcohol esters of N-long chain acyl-neutral amino acids are favorable as surfactants in the Perfume and cosmetic field. Alcohols referred to therein include polyalcohols, polyoxyalkylene-polyalcohols, etc. For example, mono(N-lauroyl-N-methyl-&bgr;-alanine) glycerin ester, di(N-lauroyl-N-methyl-&bgr;-alanine) glycerin ester and others described in the examples in the patent publication are among those N-long chain acyl-neutral amino acid glycerin esters noted above, and their safety is good.
Though having good safety, however, those monoglycerin and diglycerin esters are still problematic in that, when used in cosmetic compositions or percutaneous preparations, they can not be always satisfactory for the sensorial feel. For example, in actual use of such cosmetic compositions or percutaneous preparations comprising such esters, they are poorly spread on the skin and they are not smooth and are poorly compatible with the skin while giving little refreshing feel when they are applied to the skin, whereas they are often sticky and give little refreshing feel, after they have been applied to the skin.
In that situation of the prior art, now are desired nonionic surfactants which can be more excellent emulsifier and are safer and which, when incorporated into cosmetic compositions or percutaneous preparations, can provide sensorially satisfactory compositions or preparations.
SUMMARY OF THE INVENTION
The object of the present invention is to provide nonionic surfactants which are safer than conventional ones and which feel good in their use.
Given that situation noted above, the present inventors have assiduously studied and, as a result, have found that, when an N-long chain acyl-neutral amino acid polyglycerin ester composed of a polyglycerin having a degree of polymerization of not smaller than 4 and an N-long chain acyl-neutral amino acid having a long chain acyl group with from 6 to 22 carbon atoms is used as an emulsifier or the like in cosmetic composions or percutaneous preparations, its gives a good feel in use of those cosmetic compositions or percutaneous preparations. On the basis of these findings, they have completed the present invention.
Specifically, the invention relates to an N-long chain acyl-neutral amino acid polyglycerin ester, which is composed of a polyglycerin having a degree of glycerin polymerization of not smaller than 4 and an N-long chain acyl-neutral amino acid having an acyl group with from 6 to 22 carbon atoms, and which is represented by the following general formula (I):
wherein at least one of plural X's represents an N-long chain acyl-neutral amino acid residue, and the remaining X's each independently represent a hydrogen atom or an N-long chain acyl-neutral amino acid residue, and n represents an integer of not smaller than 2, and wherein the acyl group in each N-long chain acyl-neutral amino acid residue is a straight-chain or branched-chain and saturated or unsaturated acyl group having from 6 to 22 carbon atoms.
The present invention relates also to a nonionic sufactant composition comprising, as an active ingredient, at least one kind of such N-long chain acyl-neutral amino acid polyglycerin ester in an effective amount as well as to a cosmetic composition and a percutaneous preparation comprising, as a nonionic surfactant ingredient, at least one kind of such N-long chain acyl-neutral amino acid polyglycerin ester in an effective amount.
DETAILED DESCRIPTION OF THE INVENTION
The invention will be described in detail hereinunder.
The long chain acyl group in the N-long chain acyl-neutral amino acid polyglycerin ester of the present invention is a straight-chain or branched-chain, saturated or unsaturated one having from 6 to 22 carbon atoms. As preferred examples of the acyl group may be mentioned acyl groups derivable from capric acid, lauric acid, myristic acid, palmitic acid, stearic acid, behenic acid, linolic acid, linolenic acid, oleic acid, isostearic acid, 2-ethylhexanoic acid, coconut oil fatty acids, beef tallow fatty acids, hardened beef tallow fatty acids, etc.
The neutral amino acid (residue) is not specifically limited, and includes, for example, glycine, alanine, valine, leucine, isoleucine, serine, threonine, proline, &bgr;-alanine, aminobutyric acid, sarcosine, N-methyl-&bgr;-alanine, etc. Especially preferred are glycine, alanine, &bgr;-alanine, aminobutyric acid, sarcosine and N-methyl-&bgr;-alanine.
The polyglycerin should have a degree of glycerin polymerization of not smaller than 4, and preferably from 4 to 10. Polyglycerins having a degree of glycerin polymerization of 3 or less are undesirable, since their esters could not give a good sensual feel.
One or more molecules of the N-long chain acyl-neutral amino acid may be introduced into one molecule of the polyglycerin via ester bonding. For example, tetraglycerin has 6 esterifiable hydroxyl groups in one molecule, in which a part or all of those hydroxyl groups may be esterified with the N-long chain acyl-neutral amino acid. Various types of nonionic surfactants having different HLB (hydrophile-lipophile balance) values can be produced, for example, by properly varying the degree of polymerization of the polyglycerin to be modified and also the number of molecules of the acyl-neutral amino acid to be bonded thereto, in accordance wit
Funakubo Toshihiko
Ichikawa Tomomichi
Ishii Hiroji
Koyama Masako
Ajinomoto Co. Inc.
Page Thurman K.
Tran S.
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