Search

CN-117425680-B - Organopolysiloxane-modified cyclodextrin compound and cosmetic containing the same

CN117425680BCN 117425680 BCN117425680 BCN 117425680BCN-117425680-B

Abstract

An organopolysiloxane-modified cyclodextrin compound represented by the following formula (1) [ wherein R is a hydrogen atom, by the following formula (2) (wherein R 1 is a group selected from an alkyl group having 1 to 8 carbon atoms, a fluoro-substituted alkyl group having 1 to 8 carbon atoms, and an aryl group having 6 to 12 carbon atoms, n is an integer of 1 to 10, a is an integer of 0 to 3 ], or by the following formula (3) (wherein X is an organic group having a valence of 2, and is a bonding end bonded to a hydroxyl group of another saccharide unit). The ratio of the number of moles of hydrogen atoms N H , the number of moles of the group represented by the above formula (2) N S , and the number of moles of the group represented by the above formula (3) N L is N H ：N S ：N L ＝0.5～2.5：0.3～2.0：0.1～0.5,N H +N S +N L =3.0.

Inventors

  • KAMEI MASANAO

Assignees

  • 信越化学工业株式会社

Dates

Publication Date
20260508
Application Date
20220603
Priority Date
20210608

Claims (8)

  1. 1. An organopolysiloxane-modified cyclodextrin compound composed of a saccharide unit represented by the following formula (1), [ Chemical 1] Wherein R is independently a hydrogen atom, a group represented by the following formula (2), or a group represented by the following formula (3), [ Chemical 2] Wherein R 1 is independently a group selected from the group consisting of an alkyl group having 1 to 8 carbon atoms, a fluorine-substituted alkyl group having 1 to 8 carbon atoms, an aryl group having 6 to 12 carbon atoms, and an aralkyl group having 7 to 12 carbon atoms, n is an integer of 1 to 10, a is an integer of 0 to 3, [ Chemical 3] Wherein X is a bond terminal to be bonded to a hydroxyl group of another sugar unit selected from the group consisting of a C1-10 aliphatic hydrocarbon group having 2 atoms, a C6-20 aromatic hydrocarbon group, a C2 hydrocarbon group represented by the following formula and a C2 organic group represented by the following formula (4), [ Chemical 4] Wherein X 1 is independently a C1-10 aliphatic C6-20 hydrocarbon group, sx is a C2 organopolysiloxane residue represented by the following formula (5), p is a number of 1-5, [ Chemical 5] Wherein R 2 is independently a group selected from the group consisting of an alkyl group having 1 to 8 carbon atoms, a fluorine-substituted alkyl group having 1 to 8 carbon atoms, an aryl group having 6 to 12 carbon atoms, and an aralkyl group having 7 to 12 carbon atoms, b is independently 2 to 4, c is independently an integer of 2 to 12, d is an integer of 0 to 200, e is independently 0 to 40, The ratio of the number of moles of hydrogen atoms N H , the number of moles of groups represented by the formula (2) N S , and the number of moles of groups represented by the formula (3) N L in 1 mole of the organopolysiloxane-modified cyclodextrin compound is N H ：N S ：N L ＝0.5～2.5：0.3～2.0：0.1～0.5,N H +N S +N L =3.0.
  2. 2. The organopolysiloxane-modified cyclodextrin compound according to claim 1, wherein X is a group selected from 2-valent hydrocarbon groups represented by the following formula, [ Chemical 6] 。
  3. 3. The organopolysiloxane-modified cyclodextrin compound according to claim 1 or 2, wherein the saccharide unit of formula (1) is derived from a cyclodextrin compound selected from the group consisting of alpha-cyclodextrin, beta-cyclodextrin, and gamma-cyclodextrin, and derivatives of these cyclodextrins having hydroxyethyl group or hydroxypropyl group.
  4. 4. The organopolysiloxane-modified cyclodextrin compound according to claim 1 or 2, wherein in the formula (2), n=3, r 1 is methyl.
  5. 5. A cosmetic comprising the organopolysiloxane-modified cyclodextrin compound according to any one of claims 1 to 4, wherein the cosmetic contains 0.05 to 20% by mass of the cyclodextrin compound.
  6. 6. The cosmetic according to claim 5, further comprising water in the form of an emulsion.
  7. 7. The cosmetic according to claim 5 or 6, further comprising 1 or more selected from silicone oils, hydrocarbon oils, ester oils, glyceride oils and ultraviolet absorbers.
  8. 8. The cosmetic according to claim 5 or 6, which is a cosmetic further comprising a powder, and is in a liquid, paste or solid form.

Description

Organopolysiloxane-modified cyclodextrin compound and cosmetic containing the same Technical Field The present invention relates to organopolysiloxane-modified cyclodextrin compounds and cosmetic compositions containing the same. Background The cyclodextrin has a doughnut-shaped structure, is lipophilic on the inner side and hydrophilic on the outer side, and has inclusion property capable of accommodating various active substances in the cavity. Therefore, the poorly soluble substances are solubilized and the stability in products is improved, and therefore, they are widely used in products such as pharmaceuticals, foods, cosmetics, fibers, and paints. Cyclodextrin is added to the polymer to be used in many cases, but polymers containing cyclodextrin groups have been reported. For example, a cyclodextrin condensation polymer obtained by reacting a cyclodextrin compound with a diisocyanate compound is used as a selective fixing agent for halogenated aromatic compounds contained in an organic medium (patent document 1). In addition, cyclodextrin derivatives bonded via amide groups can improve the water solubility of poorly water-soluble compounds, and their use in medicines and cosmetics has been reported (patent documents 2 and 3). Acrylic hydrogels having cyclodextrin in the side chain have the ability to introduce drugs, active substances, or protective agents, and are used for contact lenses and cosmetics (patent document 4). In addition, a plurality of guest molecules are included with a cyclodextrin conjugate including a polyoxyethylene group as a linker (patent document 5). However, these are all aimed at inclusion of various materials. Prior art literature Patent literature Patent document 1 Japanese patent application laid-open No. 2013-233673 Patent document 2 Japanese patent laid-open No. 2007-106789 Patent document 3 Japanese patent laid-open No. 2009-024094 Patent document 4 Japanese patent application laid-open No. 2011-529998 Patent document 5 Japanese patent laid-open No. 2007-023280 Disclosure of Invention Problems to be solved by the invention The invention aims to provide an organopolysiloxane-modified cyclodextrin compound and a cosmetic containing the same. The above compound can improve the blending stability (stability with time) of an oil agent such as silicone oil to a cosmetic. The cosmetic containing the above compound is excellent in spreading, is free from greasiness, stickiness and the like, has a fresh and soft touch which is characteristic of silicone oil, and is excellent in adhesion to skin, and therefore can improve the makeup retention (makeup sustainability). The purpose of the present invention is to provide a cosmetic material that can be stably blended with a cosmetic material that also contains a pharmaceutically active ingredient, a fragrance, or the like. Means for solving the problems As a result of intensive studies to achieve the above object, the present inventors have found that the above object can be achieved by setting the ratio of substitution of hydrogen atoms of 3 hydroxyl groups in saccharide units constituting an organopolysiloxane-modified cyclodextrin compound, that is, the ratio of the number of moles of hydrogen atoms N H, the number of moles of specific triorganosilyl-modified amide groups N S, and the number of moles of specific linking groups having a 2-valent urethane bond N L in a specific range, and have completed the present invention. Accordingly, the present invention provides the following organopolysiloxane-modified cyclodextrin compounds and cosmetics. 1. An organopolysiloxane-modified cyclodextrin compound composed of a saccharide unit represented by the following formula (1), [ Chemical 1] Wherein R is independently a hydrogen atom, a group represented by the following formula (2), or a group represented by the following formula (3), [ Chemical 2] Wherein R 1 is independently a group selected from the group consisting of an alkyl group having 1 to 8 carbon atoms, a fluorine-substituted alkyl group having 1 to 8 carbon atoms, an aryl group having 6 to 12 carbon atoms, and an aralkyl group having 7 to 12 carbon atoms, n is an integer of 1 to 10, a is an integer of 0 to 3, [ Chemical 3] Wherein X is a 2-valent organic group, is a bonding end bonded to a hydroxyl group of another sugar unit, The ratio of the number of moles of hydrogen atoms N H, the number of moles of groups represented by the formula (2) N S, and the number of moles of groups represented by the formula (3) N L in 1 mole of the organopolysiloxane-modified cyclodextrin compound is N H：NS：NL＝0.5～2.5：0.3～2.0：0.1～0.5,NH+NS+NL =3.0. 2. The organopolysiloxane-modified cyclodextrin compound according to claim 1, wherein X is a group selected from the group consisting of a 2-valent aliphatic hydrocarbon group having 1 to 10 carbon atoms, a 2-valent aromatic hydrocarbon group having 6 to 20 carbon atoms, and a 2-valent organic group in the following formula (4), [ Chemical 4] Wher