JP2006225392A - Cross-linked polymer of carbohydrate - Google Patents
Cross-linked polymer of carbohydrate Download PDFInfo
- Publication number
- JP2006225392A JP2006225392A JP2006041154A JP2006041154A JP2006225392A JP 2006225392 A JP2006225392 A JP 2006225392A JP 2006041154 A JP2006041154 A JP 2006041154A JP 2006041154 A JP2006041154 A JP 2006041154A JP 2006225392 A JP2006225392 A JP 2006225392A
- Authority
- JP
- Japan
- Prior art keywords
- crosslinked
- skin
- group
- acid dichloride
- derived
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- 150000001720 carbohydrates Chemical class 0.000 title claims abstract description 55
- 229920006037 cross link polymer Polymers 0.000 title claims abstract description 26
- 239000000203 mixture Substances 0.000 claims abstract description 53
- 229920000642 polymer Polymers 0.000 claims abstract description 13
- 235000014633 carbohydrates Nutrition 0.000 claims description 52
- 229920001282 polysaccharide Polymers 0.000 claims description 38
- PEDCQBHIVMGVHV-UHFFFAOYSA-N glycerol Substances OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims description 37
- 239000005017 polysaccharide Substances 0.000 claims description 36
- 150000004804 polysaccharides Chemical class 0.000 claims description 35
- 238000000034 method Methods 0.000 claims description 34
- 238000004132 cross linking Methods 0.000 claims description 27
- 239000002537 cosmetic Substances 0.000 claims description 25
- 229920001285 xanthan gum Polymers 0.000 claims description 24
- GJCOSYZMQJWQCA-UHFFFAOYSA-N 9H-xanthene Chemical compound C1=CC=C2CC3=CC=CC=C3OC2=C1 GJCOSYZMQJWQCA-UHFFFAOYSA-N 0.000 claims description 22
- 229920001525 carrageenan Polymers 0.000 claims description 22
- 229920001542 oligosaccharide Polymers 0.000 claims description 21
- 150000002482 oligosaccharides Chemical class 0.000 claims description 21
- 150000003138 primary alcohols Chemical group 0.000 claims description 21
- 239000003431 cross linking reagent Substances 0.000 claims description 20
- 229920005862 polyol Polymers 0.000 claims description 19
- 150000003077 polyols Chemical class 0.000 claims description 19
- 239000008346 aqueous phase Substances 0.000 claims description 17
- 235000010418 carrageenan Nutrition 0.000 claims description 16
- 239000000679 carrageenan Substances 0.000 claims description 15
- 229940113118 carrageenan Drugs 0.000 claims description 15
- 238000006243 chemical reaction Methods 0.000 claims description 14
- -1 polythioisocyanates Polymers 0.000 claims description 14
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- WMPOZLHMGVKUEJ-UHFFFAOYSA-N decanedioyl dichloride Chemical compound ClC(=O)CCCCCCCCC(Cl)=O WMPOZLHMGVKUEJ-UHFFFAOYSA-N 0.000 claims description 13
- 235000011187 glycerol Nutrition 0.000 claims description 13
- LXEJRKJRKIFVNY-UHFFFAOYSA-N terephthaloyl chloride Chemical compound ClC(=O)C1=CC=C(C(Cl)=O)C=C1 LXEJRKJRKIFVNY-UHFFFAOYSA-N 0.000 claims description 13
- 150000001875 compounds Chemical class 0.000 claims description 12
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Abstract
Description
本発明は、いろいろな蛋白質またはペプチドの物質が基になっているが、そのような物質を用いた時に直面するアレルギーの問題がなくて、引き締める効果(tensing efffect)を有する活性成分の製造に関する。本発明は、更に、炭水化物の架橋重合体を製造することにも関する。 The present invention relates to the production of active ingredients which are based on various protein or peptide substances, but without the problems of allergies encountered when such substances are used and which have a tensing effect. The invention further relates to producing a crosslinked polymer of carbohydrates.
化粧品調剤(cosmetic formulations)には、非常に頻繁に、特徴的な引き締める効果を誘発し得る物質が入っている。そのような効果は、特に、消費者が有意に気づく知覚効果による化粧品調剤の有効性の認識を向上させ得る。 Cosmetic formulations very often contain substances that can induce a characteristic tightening effect. Such an effect can improve recognition of the effectiveness of cosmetic preparations, especially due to the perceptual effect noticed significantly by consumers.
その上、そのような引き締める効果は、一方では、皮膚のしわを一時的ではあるが即座に減少させ、他方では、目の回り、首、襟足または手の種類の調剤で用いられた時、皮膚を引き締め得る。 Moreover, such a tightening effect, on the one hand, temporarily reduces skin wrinkles, but on the other hand, when used in preparations around the eyes, neck, neckline or hand type, Can tighten.
そのような特性を有することが最も良く知られている物質は、とりわけ、ウシ血清アルブミンまたはコラーゲンであり、それらが以前には最も頻繁に用いられていた分子である。より最近になって、そのような活性の目的で開発される物質は植物が源の物質の方向に転じており、特に植物蛋白質がそのような活性の目的で幅広く用いられるようになってきている。 The substances best known to have such properties are, inter alia, bovine serum albumin or collagen, which are the molecules most frequently used before. More recently, substances developed for the purpose of such activity have turned to plant source materials, and in particular, plant proteins have become widely used for such activity purposes. .
従って、例えば、穀物または豆科植物の植物アルブミン画分がウシ血清アルブミンの類似物として特に興味の持たれている特許の主題であった(特許文献1)。二官能作用剤を補助で用いて植物蛋白質を重合させることも同様にいろいろな化粧品用途の目的で記述された(特許文献2および3)。また、植物蛋白質に加水分解を受けさせた画分を重合させることで作られた物質も記述されかつ化粧品で引き締める効果の目的で用いられた(特許文献4)。 Thus, for example, the plant albumin fraction of cereals or legumes was the subject of a patent of particular interest as an analog of bovine serum albumin (Patent Document 1). Polymerization of plant proteins with the aid of bifunctional agents has also been described for various cosmetic purposes (Patent Documents 2 and 3). In addition, substances made by polymerizing fractions obtained by subjecting plant proteins to hydrolysis have been described and used for the purpose of tightening with cosmetics (Patent Document 4).
しかしながら、蛋白質は免疫反応を様々な強さで誘発する可能性があり、全く耐えられないアレルギーさえ誘発し得ることから、蛋白質を化粧品で用いることは問題になってきている。そのような免疫反応を引き起こすことが本分野の技術者に良く知られている蛋白質のいくつかの例は、小麦、木の実、ヘーゼルナッツ、落花生、牛乳に由来する蛋白質である。 However, the use of proteins in cosmetics has become a problem because proteins can induce immune responses with varying strengths and can even induce allergies that cannot be tolerated at all. Some examples of proteins well known to those skilled in the art to cause such immune responses are proteins derived from wheat, nuts, hazelnuts, peanuts, and milk.
皮膚を刺激する化合物、例えば蛋白質などを化粧品で用いることは将来法律で制限または禁止される可能性があることを考慮する必要がある。 It should be taken into account that the use of skin irritating compounds, such as proteins, in cosmetics may be restricted or prohibited by law in the future.
引き締める効果の目的で化粧品または薬剤に使用可能なある種の化合物もまたしばしば刺激の原因になり得ると言った問題を本分野の技術者が軽減することを可能にするであろう特別な解決法は従来技術に記述されていない。
本発明の主目的は、そのような新規な技術的問題を解決することにあり、これは、皮膚表面を引き締めそして/または整える効果を使用者が感知できる様式で得ることを可能にするが識別可能なアレルギー反応を全く誘発しない化合物を提供することから成る。 The main object of the present invention is to solve such a new technical problem, which allows the user to obtain the effect of tightening and / or trimming the skin surface in a perceptible manner. Providing compounds that do not induce any possible allergic reactions.
本発明の1つの目的は、調整用溶液(toning solution)[これは、好適には、優れた生体適合性を示し、完全な生分解性を示し、完全な同化作用を示し、完全に無害であり、再生可能な生物学的材料に由来し、動物界ばかりでなくまた植物界にも存在し得かつまた微生物による発酵でも生じ得る出発材料が基になっている]を提供することでそのような技術的問題を解決することにある。 One object of the present invention is a toning solution [which preferably exhibits excellent biocompatibility, complete biodegradability, complete anabolism, is completely harmless. And is based on starting materials that can be found not only in the animal kingdom but also in the plant kingdom and can also be produced by microbial fermentation]. Is to solve various technical problems.
本発明の1つの目的は、また、この上に挙げた技術的問題を解決することを可能にする化合物の新規な製造方法を提供することで技術問題を解決することにもある。 One object of the present invention is also to solve the technical problem by providing a novel process for the preparation of compounds which makes it possible to solve the technical problems listed above.
そのような技術的問題の全部を満足される様式で安価にかつ産業規模、注目すべきは化粧品規模で使用可能な様式で解決するのは初めてのことである。 It is the first time that all such technical problems are solved in a manner that can be used inexpensively and on an industrial scale, notably in a cosmetic scale, in a satisfactory manner.
本発明者らは、少なくとも1種の炭水化物もしくは炭水化物誘導体の架橋重合体を皮膚組織、例えば人の皮膚などに用いるとそれを引き締めそして/または整える効果を得ることができることを驚くべき様式で見いだした。 The inventors have found in a surprising manner that a cross-linked polymer of at least one carbohydrate or carbohydrate derivative can be used on skin tissue, such as human skin, to obtain an effect of tightening and / or conditioning it. .
従って、本発明は、1番目の面に従い、第一級アルコール官能基を少なくとも1個含有する少なくとも1種の炭水化物の架橋重合体に関し、特に、以下に定義する方法に従って得ることができる架橋重合体に関する。第一級アルコール官能基を少なくとも1個含有する少なくとも1種の炭水化物の重合体がカプセルまたは球の形態、特にマイクロカプセルまたは微小球の形態、またはナノカプセルまたはナノ球の形態の場合には、そのような重合体を本重合体から除外する。 Accordingly, the present invention relates to a crosslinked polymer of at least one carbohydrate containing at least one primary alcohol functional group according to the first aspect, and in particular, a crosslinked polymer obtainable according to the method defined below. About. If the polymer of at least one carbohydrate containing at least one primary alcohol functional group is in the form of a capsule or sphere, in particular in the form of a microcapsule or microsphere, or in the form of a nanocapsule or nanosphere, Such polymers are excluded from the present polymer.
本発明は、2番目の面に従い、この上で定義した如き架橋重合体を含んで成る化粧品および/または皮膚−薬剤および/または薬剤組成物に関する。 The present invention relates to a cosmetic and / or skin-drug and / or pharmaceutical composition comprising a cross-linked polymer as defined above according to a second aspect.
本発明は、また、3番目の面に従い、この上で定義した如き架橋重合体を被験体の皮膚組織に塗布して前記組織を引き締めそして/または整える効果を得ることを意図する組成物の製造で用いることにも関する。 The present invention also provides a composition according to the third aspect intended to obtain an effect of tightening and / or conditioning said tissue by applying a cross-linked polymer as defined above to the skin tissue of a subject. Also related to use in
本明細書で用いる如き用語「炭水化物」は、炭水化物ばかりでなく第一級アルコール官能基を少なくとも1個またはそれ以上含有する炭水化物誘導体も意味する。 The term “carbohydrate” as used herein means not only carbohydrates but also carbohydrate derivatives containing at least one or more primary alcohol functions.
本発明の文脈の範囲内で、引き締めそして/または整える効果は、主に、志願者の意見および/または皮膚の粗さの測定および/または架橋させた炭水化物の水溶液が示す粘度を架橋させていない炭水化物の水溶液と比較することで測定した効果である。 Within the context of the present invention, the effect of tightening and / or trimming mainly does not cross-link the viscosity of the applicant's opinion and / or skin roughness measurement and / or the aqueous solution of the cross-linked carbohydrate. It is the effect measured by comparing with an aqueous solution of carbohydrates.
本発明は、1つの変形に従い、本架橋重合体を被験体の皮膚組織に塗布して前記組織のしわおよび/または小さなしわの減少を得ることを意図した組成物の製造で用いることに関する。 The present invention, according to one variant, relates to the use of the crosslinked polymer in the manufacture of a composition intended to be applied to the skin tissue of a subject to obtain a reduction in said tissue wrinkles and / or small wrinkles.
本発明は、別の変形に従い、本架橋重合体を被験体の皮膚組織に塗布して前記組織の生体力学的特性を改善することを意図した組成物の製造で用いることに関する。 The present invention, according to another variant, relates to the use of the crosslinked polymer in the manufacture of a composition intended to apply to the skin tissue of a subject to improve the biomechanical properties of the tissue.
本組成物は、有利に、顔の少なくとも一部、特に目の回りおよび/または首および/または手および/または襟足および/または胸に塗布することを意図した化粧品、皮膚薬剤または薬剤組成物である。 The composition is advantageously a cosmetic, dermopharmaceutical or pharmaceutical composition intended to be applied to at least part of the face, in particular around the eyes and / or neck and / or hands and / or neckline and / or chest. is there.
本発明に由来する製品は、それを含有させた組成物を塗布すると皮膚を整える効果を示す。本発明に由来する製品は、そのような組成物を皮膚に塗布した時に識別できるほどのアレルギーをもたらすと言った影響を全く与えない。 The product derived from the present invention exhibits the effect of conditioning the skin when a composition containing it is applied. The product derived from the present invention does not have any effect that it causes any appreciable allergy when such a composition is applied to the skin.
本発明の生成物は、皮膚の表面に吸着されて滑らかで連続的な弾性膜を形成する。このように、炭水化物、注目すべきは多糖類および/またはオリゴ糖および/またはポリオールをそのように重合させた時にそれらが示す膜形成(filmogenic)、引き締めおよび可塑化する特性に特に興味が持たれる。 The product of the present invention is adsorbed on the surface of the skin to form a smooth and continuous elastic membrane. Thus, of particular interest are the filmogenic, tightening and plasticizing properties that carbohydrates, notably polysaccharides and / or oligosaccharides and / or polyols, exhibit when they are so polymerized. .
従って、本発明の生成物は、有利に、膜形成および/または可塑化特性を有する。 Accordingly, the product of the present invention advantageously has film-forming and / or plasticizing properties.
そのような炭水化物を好適には多糖類、オリゴ糖、ポリオールおよび/またはこれらの混合物のいずれか1つから選択する。 Such carbohydrate is preferably selected from any one of polysaccharides, oligosaccharides, polyols and / or mixtures thereof.
本発明は、4番目の面に従い、美容手入れ方法(method of cosmetic care)に関し、これは、この上で定義した如き組成物を局所的に塗布することを含んで成る。 The present invention, according to a fourth aspect, relates to a method of cosmetic care, which comprises topically applying a composition as defined above.
本出願者は多糖類もしくはオリゴ糖を重合させる方法を認識している(COLETICA FR 2,688,422、米国特許第5,562,924号)。しかしながら、そのような方法は、マイクロカプセルを生じさせそして微小球を生じさせるに適した乳化界面重合方法である。従って、そのような方法を用いたのでは、炭水化物の高分子量重合体を球および/またはカプセル形態以外の形態、特にマイクロカプセルの形態でも微小球の形態でもない形態で得ることはできない。 Applicants are aware of a method of polymerizing polysaccharides or oligosaccharides (COLETICA FR 2,688,422, US Pat. No. 5,562,924). However, such a process is an emulsion interfacial polymerization process suitable for producing microcapsules and producing microspheres. Thus, using such a method, high molecular weight polymers of carbohydrates cannot be obtained in forms other than sphere and / or capsule form, particularly in neither microcapsule nor microsphere form.
従って、本発明は、5番目の面に従い、架橋重合体の製造方法を記述し、この方法は、炭水化物が有する第一級アルコール官能基と架橋剤が有する反応性官能基の間の架橋反応を均一な水相中で起こさせて少なくとも1種の炭水化物の架橋重合体を得ることを含んで成る。 Therefore, according to the fifth aspect, the present invention describes a method for producing a crosslinked polymer, which comprises a crosslinking reaction between a primary alcohol functional group possessed by a carbohydrate and a reactive functional group possessed by a crosslinking agent. Causing in a homogeneous aqueous phase to obtain a crosslinked polymer of at least one carbohydrate.
そのような炭水化物を好適には多糖類、オリゴ糖、ポリオールおよびこれらの混合物のいずれか1つから選択する。 Such carbohydrates are preferably selected from any one of polysaccharides, oligosaccharides, polyols and mixtures thereof.
1番目の態様における炭水化物、特にポリオールおよび/またはオリゴ糖の分子量は1モル当たり150グラムに等しいか或はそれ以上(本文脈の残りの部分ではg/モルまたはダルトン、即ちDaとして示す)、好適には2,000Daに等しいか或はそれ以上である。 The molecular weight of the carbohydrates in the first embodiment, in particular polyols and / or oligosaccharides, is equal to or greater than 150 grams per mole (shown as g / mol or Dalton, ie Da in the rest of the context), preferred Is equal to or greater than 2,000 Da.
この1番目の態様では、有利に、架橋剤に対する炭水化物、特にポリオールおよび/またはオリゴ糖のモル比を0.1以上、好適には1に等しいか或はそれ以上にする。 In this first embodiment, the molar ratio of carbohydrates, in particular polyols and / or oligosaccharides to crosslinker is advantageously greater than or equal to 0.1, preferably equal to or greater than 1.
2番目の態様における炭水化物、特に多糖類の分子量は50,000Daに等しいか或はそれ以上、好適には100,000Daに等しいか或はそれ以上、より好適には300
,000Daに等しいか或はそれ以上である。この場合、重合反応で主に可溶な重合体が生じ得るように、架橋反応に先立って加水分解を実施してもよい。炭水化物に加水分解を受けさせる方法は本分野の技術者に公知である。
The molecular weight of the carbohydrate, in particular the polysaccharide, in the second embodiment is equal to or greater than 50,000 Da, preferably equal to or greater than 100,000 Da, more preferably 300.
Equal to or greater than 1,000 Da. In this case, hydrolysis may be carried out prior to the crosslinking reaction so that a mainly soluble polymer can be produced by the polymerization reaction. Methods for subjecting carbohydrates to hydrolysis are known to those skilled in the art.
この2番目の態様では、有利に、架橋剤に対する炭水化物、特に多糖類のモル比を0.1未満、好適には0.01未満にする。 In this second embodiment, advantageously, the molar ratio of carbohydrate, in particular polysaccharide, to crosslinking agent is less than 0.1, preferably less than 0.01.
そのような多糖類は有利に第一級アルコール官能基をジオシド部分(diosidic
moiety)1個当たり0.5から4個含有する。
Such polysaccharides preferably have a primary alcohol function as a diosidic moiety.
moiety) 0.5 to 4 per one.
有利には、そのような炭水化物を反応させる前に、それを局所的経路により受け入れられる賦形剤、特に化粧品または皮膚科学的に受け入れられる賦形剤と混合しておく。 Advantageously, before reacting such a carbohydrate, it is mixed with excipients that are acceptable by the topical route, in particular cosmetically or dermatologically acceptable excipients.
別の特別な態様変形に従い、第一級アルコール官能基を有する炭水化物、注目すべきは多糖類および/またはオリゴ糖および/またはポリオールの濃度を水相の0.001重量%から50重量%、より特別には0.1から10重量%の範囲内にする。 According to another special embodiment variant, the concentration of carbohydrates with primary alcohol functionality, notably polysaccharides and / or oligosaccharides and / or polyols, is from 0.001% to 50% by weight of the aqueous phase, more Specially within the range of 0.1 to 10% by weight.
前記架橋剤は有利に多官能架橋剤、即ち炭水化物が有する第一級アルコール官能基と主に反応し得る反応性官能基を少なくとも2個含有する架橋剤であり、それを有利にはポリカルボン酸クロライド、無水カルボン酸、ポリイソシアネート、ポリチオイソシアネート、ポリアルデヒドおよびこれらの混合物のいずれか1つから選択する。 Said cross-linking agent is preferably a polyfunctional cross-linking agent, i.e. a cross-linking agent containing at least two reactive functional groups which can mainly react with the primary alcohol functional groups of the carbohydrate, which is preferably polycarboxylic acid It is selected from any one of chloride, carboxylic anhydride, polyisocyanate, polythioisocyanate, polyaldehyde and mixtures thereof.
そのような炭水化物が高分子量の範囲内の場合、それを反応させるに先立って、それに加水分解を均一な水相中で受けさせた後、それを架橋剤と接触させるのが好適である。 If such a carbohydrate is in the high molecular weight range, it is preferred to subject it to hydrolysis in a homogeneous aqueous phase and then contact it with a crosslinker prior to reacting it.
本方法は、有利に、反応終了時に不溶な化合物が存在する場合、水相に不溶な化合物を架橋反応後に除去することを含んで成る。 The method advantageously comprises removing the compound insoluble in the aqueous phase after the crosslinking reaction if insoluble compounds are present at the end of the reaction.
特別な態様における本方法は、当該炭水化物を水相に溶解させた後、それを架橋剤(これはアルコール、例えばエタノールおよび/またはブチレングリコールなどに溶解または不溶であり得る)を含有する相に前記炭水化物の架橋が得られるに充分な時間接触させることで炭水化物の架橋重合体、注目すべきは高分子量の重合体が生じさせることを含んで成る。 In a particular embodiment, the method comprises dissolving the carbohydrate in an aqueous phase and then adding it to a phase containing a cross-linking agent, which can be dissolved or insoluble in alcohols such as ethanol and / or butylene glycol. It comprises the formation of a crosslinked polymer of carbohydrates, notably a high molecular weight polymer, in contact for a time sufficient to obtain carbohydrate crosslinking.
この上のパラグラフで説明したように、本発明者らは、炭水化物を均一な水相中で重合させることで高分子量重合体を得た。本方法は、反応段階の数が限られており、出発材料のコストが限られておりかつまた作業者の安全が保持されることから、産業的生産の観点で極めて有利である。 As explained in the above paragraph, the inventors obtained high molecular weight polymers by polymerizing carbohydrates in a homogeneous aqueous phase. This method is extremely advantageous from the viewpoint of industrial production because the number of reaction steps is limited, the cost of starting materials is limited and the safety of workers is maintained.
その得た重合体が「引き締め効果」特性として知られる特性を持つことは予想外であった。 It was unexpected that the resulting polymer had a property known as the “tightening effect” property.
本発明は、特に、架橋した炭水化物、例えば多糖類および/またはオリゴ糖および/またはポリオールを架橋、好適には本分野の技術者に公知の多官能作用剤を補助で用いて架橋、注目すべきはそれらの第一級アルコール官能基による架橋で架橋させた炭水化物を用いることに関する。 The invention is particularly notable for crosslinking crosslinked carbohydrates such as polysaccharides and / or oligosaccharides and / or polyols, preferably with the aid of multifunctional agents known to those skilled in the art. Relates to the use of carbohydrates crosslinked by crosslinking with their primary alcohol functionality.
本発明は、第一級アルコール官能基を含有する炭水化物、注目すべきは多糖類および/またはオリゴ糖および/またはポリオールの高分子量重合体(または架橋体)を製造する
方法に関し、この方法は、下記の逐次的段階:
1)炭水化物、注目すべきは多糖類および/またはオリゴ糖および/またはポリオールが豊富に存在する材料を水相に溶解させ、
2)この上に記述した如く選択した多官能作用剤(架橋剤)を添加して前記炭水化物を重合させ、
3)場合により、不溶になった(不溶な)反応生成物を反応媒体から除去する、
ことから成る段階を含んで成る。
The present invention relates to a process for producing high molecular weight polymers (or cross-linked products) of carbohydrates, notably polysaccharides and / or oligosaccharides and / or polyols containing primary alcohol functional groups, The following sequential steps:
1) dissolving a material rich in carbohydrates, notably polysaccharides and / or oligosaccharides and / or polyols, in an aqueous phase;
2) Add the multifunctional agent (crosslinking agent) selected as described above to polymerize the carbohydrate,
3) optionally removing insoluble (insoluble) reaction products from the reaction medium,
Comprising the steps of:
本発明の方法を用いると、興味の持たれる、注目すべきは化粧品で興味の持たれる炭水化物、注目すべきは多糖類および/またはオリゴ糖および/またはポリオールの重合体(架橋体)を製造することができる。そのようにして得た炭水化物重合体は高い分子量を有し、かつ驚くべきことに、完全な皮膚許容性を示す。 Using the process of the present invention, a carbohydrate of interest, notably a carbohydrate of interest in cosmetics, notably a polysaccharide and / or oligosaccharide and / or polyol polymer (crosslinked) is produced. be able to. The carbohydrate polymer thus obtained has a high molecular weight and surprisingly exhibits full skin tolerance.
本発明の方法の利点の1つは、炭水化物、即ち多糖類および/またはオリゴ糖および/またはポリオールが豊富に存在する材料から高モル質量の分子構造物(皮膚の生体力学的特性の改善を誘発し得る三次元網状組織を作り出し得る)を生じさせることができる点にある。 One of the advantages of the method of the present invention is that high molecular weight molecular structures (inducing improved biomechanical properties of the skin) from materials rich in carbohydrates, ie polysaccharides and / or oligosaccharides and / or polyols. Can create a three-dimensional network that can be generated).
本発明に従う架橋重合体を明確な様式で定義することは容易なことではない、と言うのは、架橋度合を識別するのは不可能であるからである。説明するように、本発明者らが用いる用語「高分子量の重合体」は、鎖が有意なパーセントで50,000ダルトンに等しいか或はそれ以上の分子量を有し、特に多糖類を架橋させた場合、好適には150,000ダルトンに等しいか或はそれ以上、より好適には300,000ダルトンに等しいか或はそれ以上の分子量を有する重合体を意味する。 It is not easy to define a cross-linked polymer according to the invention in a clear manner, because it is impossible to identify the degree of cross-linking. As will be explained, the term “high molecular weight polymer” as used by the inventors means that a significant percentage of the chain has a molecular weight equal to or greater than 50,000 daltons, especially to crosslink polysaccharides. Preferably means a polymer having a molecular weight equal to or greater than 150,000 daltons, more preferably equal to or greater than 300,000 daltons.
本発明の方法の他の追加的または代替特徴は下記である:
− 炭水化物、注目すべきは多糖類および/またはオリゴ糖および/またはポリオールが豊富に存在する材料を好適には植物源および/または動物源の天然物質および/またはバイオ技術源(例えば発酵)から選択する。
− 前記材料を水相中に20g/lから500g/lの割合で溶解させる。
Other additional or alternative features of the method of the invention are the following:
The material rich in carbohydrates, notably polysaccharides and / or oligosaccharides and / or polyols, is preferably selected from natural sources of plant and / or animal sources and / or biotechnological sources (eg fermentation) To do.
The material is dissolved in the water phase at a rate of 20 g / l to 500 g / l.
特別な態様に従い、この上に挙げた第一級アルコール官能基を有する多糖類および/またはオリゴ糖および/またはポリオールを下記から成る群から選択する:
下記の多糖類:
−ガラクトマンナン、例えばグアーに由来するガラクトマンナン、例えばViscogum(商標)(SANOFI)など、またはカロブ豆に由来するガラクトマンナン、例えばLygomme(商標)(SANOFI)またはMeyproFleur(商標)またはMeyprodyn(商標)(MEYHALL)の名称の下で商業的に入手可能なガラクトマンナン;
−カラギナン、例えば紅藻から抽出されたカラギナン、例えばSatiagel(商標)またはSatiagum(商標)(DEGUSSA)またはGenuvisco(商標)(HERCULES)の名称の下で商業的に入手可能なカラギナン;
−グルコマンナン、例えばコンニャクゴムに由来するグルコマンナン、例えばNutricol(商標)(FMC Corporation)またはPropol(商標)(FMC SCHIITZU)の名称の下で商業的に入手可能なグルコマンナン;
−発酵に由来する第一級アルコール官能基を有する多糖類、例えばキサンタン(KELKO)、Gallane(商標)(KELKO)、Curdlane(商標)(TAKEDA)またはヒアルロン酸;
−セルロース、例えばNatrosol(商標)250HHX(AQUALON)、Klucel EF(商標)(AQUALON)、Vivapur(商標)(Instel
Chimos);
−セルロース誘導体、例えばヒドロキシプロピルメチルセルロース(Aqualon)、メチルエチルセルロース(Aqualon)、メチルヒドロキシメチルセルロース(Aqualon)またはBlanose(商標)(Aqualon);
−ポリホロシド、例えばDextran(商標)、Dextran T70、T500またはT2000、硫酸デキストラン(Pharmacia Fine Chemicals);
−寒天、例えば食品品質の寒天(Sigma)、細菌学的寒天(Setexam)、Monogar M540 Agar(Setexam)またはAgar QSN5(Setexam);
−アルギネート、例えばアルギン酸のナトリウム塩A2158(Sigma)、Satialgine(商標)(Degussa)またはアルギン酸ナトリウムFD 125(Danisco);
−澱粉、例えばアミロペクチン(Fluka)、アミロース(Fluka)、Nastar(商標)(Cosucra)、Waxy Maize澱粉(Roquette)、Waxillis(商標)(Roquette)、小麦に由来する澱粉(Roquette)、米に由来する澱粉(Roquette)、ジャガイモに由来する澱粉(Roquette)またはトウモロコシに由来する澱粉(Roquette);
−キトサン、例えばKitamer(商標)(Unipex);
−カードラン、例えばPureglucan(商標)(Takeda);
−アドラガンテゴム(gum adragante)またはトラガカントゴム(Emiga);
−アラビアゴムまたはアカシアゴム(Colin)またはValgum(商標)(Valmar);
−キアゴム(Chia gum)(Sigma);
−エレミゴム(Emiga);
−ゲランゴム(Gellan gum)、例えばKelcogel(商標)(SPCI);
−ガッチゴム(Gum ghatti)またはインドゴム(Indian Gum)(Sigma);
−カラヤゴム(Sigma);
−シェラック(Sigma);
−マニラゴム(Sigma);
例として示す下記のオリゴ糖、単糖類または二糖類(特に明記しない限り、Sigma社が市販):
−シクロデキストリン(特にα、βまたはγシクロデキストリンまたはこれらの誘導体);
−デキストリン(Glucidex 40(商標)またはGlucidex 47(商標)、Roquette);
−ラフィノース、セロビオース、スクロース、マルトース、ラクトース、トレハロース、ジヒドロキシアセトン(DHA)、フラクトース、ソルボース、リボース、デオキシリボース、キシロース、アラビノース、グルコース、マンノース、ガラクトース、エリスロース、トレオース、アロース、アトロース、グロース、イドース、タロース、エリトルロース、キシルロース、プシコース、タガトース、セドヘプツロース、キシロビオース、キトビオース、ニゲロース、アミナリビオース(aminaribiose)、コジビオース(kojibiose)、ソフォロース(sophorose)、ゲンチアノース(gentianose)、ゲンチオビオース(gentiobiose)、メリビオース、メレジトース(melezitose)、ツラノース、スタキオース、ベルバスコース(verbascose);
−グルコン酸、グルコノラクトン、グルコサミン、ガラクトサミン、硫酸ガラクトサミン
、硫酸グルコサミン;
−サポニン、例えばキラヤ(quillaya)の樹皮に由来するサポニン;
−グアノシン、ウリジン;
−硫酸ストレプトマイシン;
−リボフラビン;および
例として示す下記のポリオール:(特に明記しない限り、Roquette社が市販):
−グリセロール、ソルビトール、エリスリトール(Sigma)、マルチトール(maltitol)、ソルビトール、マンニトール、ラクチトール(lactitol)(Sigma)、ガラクチトール(galactitol)(Sigma)、リビトール(Sigma)、グリセロール(Sigma)、キシリトール、ミオ−イノシトール、ポリエチレングリコール、またはある分子質量を有する、従っていろいろな重合度のPEGなど。
According to a particular embodiment, the polysaccharides and / or oligosaccharides and / or polyols having the primary alcohol functional groups listed above are selected from the group consisting of:
The following polysaccharides:
-Galactomannans, such as galactomannans derived from guar, such as Viscogum (TM) (SANOFI), or galactomannans derived from carob beans, such as Lygomme (TM) (SANOFI) or MeyproFlure (TM) or Meyprodyn (TM) ( Commercially available galactomannans under the name MEYHALL);
-Carrageenans, eg carrageenans extracted from red algae, eg carrageenans commercially available under the name Satiagel ™ or Satiagum ™ (DEGUSSA) or Genvisco ™ (HERCULES);
-Glucomannan, for example glucomannan derived from konjac gum, such as glucomannan commercially available under the name Nutricol (TM) (FMC Corporation) or Propol (TM) (FMC SCHIITZU);
A polysaccharide having primary alcohol functional groups derived from fermentation, such as xanthan (KELKO), Gallane ™ (KELKO), Curdlane ™ (TAKEDA) or hyaluronic acid;
-Cellulose, such as Natrosol ™ 250HHX (AQUALON), Klucel EF ™ (AQUALON), Vivapur ™ (Instel)
Chimos);
-Cellulose derivatives such as hydroxypropylmethylcellulose (Aqualon), methylethylcellulose (Aqualon), methylhydroxymethylcellulose (Aqualon) or Blanose (TM) (Aqualon);
-Polyholosides, such as Dextran (TM), Dextran T70, T500 or T2000, Dextran sulfate (Pharmacia Fine Chemicals);
-Agar, eg food quality agar (Sigma), bacteriological agar (Setexam), Monogar M540 Agar (Setexam) or Agar QSN5 (Setexam);
An alginate, for example the sodium salt of alginic acid A2158 (Sigma), Satialgine ™ (Degussa) or sodium alginate FD 125 (Danisco);
-Derived from starch, eg amylopectin (Fluka), amylose (Fluka), Nastar ™ (Coscula), Waxy Maize starch (Roquette), Waxillis ™ (Roquette), starch derived from wheat (Roquette), rice Starch (Roquette), potato-derived starch (Roquette) or corn-derived starch (Roquette);
-Chitosan, such as Kitamer (TM) (Unipex);
A curdlan, eg Pureglucan ™ (Takeda);
-Gum adragante or gum tragacanth (Emiga);
-Gum arabic or gum acacia (Colin) or Valgum (TM) (Valmar);
-Chia gum (Sigma);
-Elemi rubber (Emiga);
-Gellan gum, such as Kelcogel ™ (SPCI);
-Gum gati or Indian Gum (Sigma);
-Karaya gum (Sigma);
-Shellac (Sigma);
-Manila rubber (Sigma);
Examples of the following oligosaccharides, monosaccharides or disaccharides (commercially available from Sigma unless otherwise specified):
-Cyclodextrins (especially alpha, beta or gamma cyclodextrins or their derivatives);
Dextrin (Glucidex 40 ™ or Glucidex 47 ™, Roquette);
-Raffinose, cellobiose, sucrose, maltose, lactose, trehalose, dihydroxyacetone (DHA), fructose, sorbose, ribose, deoxyribose, xylose, arabinose, glucose, mannose, galactose, erythrose, threose, allose, atrose, gulose, idose , Talose, erythrulose, xylulose, psicose, tagatose, cedoheptulose, xylobiose, chitobiose, nigerose, aminaribiose, kojibiose, sophorose, gentianse (gentiose) se), turanose, stachyose, bell bus course (verbascose);
-Gluconic acid, gluconolactone, glucosamine, galactosamine, galactosamine sulfate, glucosamine sulfate;
-Saponins, for example saponins from the bark of quilla;
-Guanosine, uridine;
-Streptomycin sulfate;
-Riboflavin; and the following polyols shown as examples: (commercially available from Roquette unless otherwise specified):
Glycerol, sorbitol, erythritol (Sigma), maltitol, sorbitol, mannitol, lactitol (Sigma), galactitol (Sigma), ribitol (Sigma), glycerol (Sigma), xylitol, myo -Inositol, polyethylene glycol, or PEG with a certain molecular mass and thus with different degrees of polymerization.
特別な態様に従い、上述した第一級アルコール官能基を有する多糖類および/またはオリゴ糖および/またはポリオールを好適には多糖類であるキサンタン、セルロース、カロブ豆に由来するゴム、キシリトール、マルトース、カラギナン、ラフィノース、アカシアゴム、グリセロール(例えば10%、重量/重量)とキサンタン(例えば2%、重量/重量)の混合物、マンニトール(例えば10%、重量/重量)とイヌリン(例えば5%、重量/重量)の混合物、およびこれらの混合物のいずれか1つから成る群から選択し、これらを好適にはセバシン酸ジクロライドまたはテレフタル酸ジクロライドを用いて架橋させる。 According to a special embodiment, the polysaccharides and / or oligosaccharides and / or polyols having the primary alcohol functional groups described above are preferably polysaccharides derived from xanthan, cellulose, carob beans, xylitol, maltose, carrageenan , Raffinose, acacia gum, mixture of glycerol (eg 10% w / w) and xanthan (eg 2% w / w), mannitol (eg 10% w / w) and inulin (eg 5% w / w) ) And any one of these mixtures, which are preferably cross-linked using sebacic acid dichloride or terephthalic acid dichloride.
特別な態様に従い、上述した第一級アルコール官能基を有する多糖類および/またはオリゴ糖および/またはポリオールを好適にはセバシン酸ジクロライドを用いて架橋させるキサンタン、セバシン酸ジクロライドを用いて架橋させるセルロース、セバシン酸ジクロライドを用いて架橋させるカロブ豆に由来するゴム、セバシン酸ジクロライドを用いて架橋させるキシリトール、セバシン酸ジクロライドを用いて架橋させるマルトース、テレフタル酸ジクロライドを用いて架橋させるカラギナン、テレフタル酸ジクロライドを用いて架橋させるラフィノース、テレフタル酸ジクロライドを用いて架橋させるアカシアゴム、テレフタル酸ジクロライドを用いて架橋させるグリセロール(例えば10%、重量/重量)とキサンタン(例えば2%、重量/重量)の混合物、テレフタル酸ジクロライドを用いて架橋させるマンニトール(例えば10%、重量/重量)とイヌリン(例えば5%、重量/重量)の混合物、およびこれらの混合物のいずれか1つである多糖類から成る群から選択する。 According to a special embodiment, xanthan which crosslinks polysaccharides and / or oligosaccharides and / or polyols having primary alcohol functional groups as described above preferably with sebacic acid dichloride, cellulose which is crosslinked with sebacic acid dichloride, Rubber derived from carob beans cross-linked with sebacic acid dichloride, xylitol cross-linked with sebacic acid dichloride, maltose cross-linked with sebacic acid dichloride, carrageenan cross-linked with terephthalic acid dichloride, terephthalic acid dichloride used Cross-linked raffinose, acacia rubber cross-linked with terephthalic acid dichloride, glycerol cross-linked with terephthalic acid dichloride (eg 10%, weight / weight) and xanthan (eg 2%, A mixture of mannitol (eg, 10%, weight / weight) and inulin (eg, 5%, weight / weight) and any one of these mixtures that are crosslinked using terephthalic acid dichloride. Select from the group consisting of polysaccharides.
本製造方法は、有利な態様に従い、第一級アルコール官能基を有する炭水化物、注目すべきは多糖類および/またはオリゴ糖および/またはポリオールを水相に溶解させた後、その炭水化物が入っている水相を架橋剤(これは当該炭水化物が有する第一級アルコール官能基と優先的に反応し得る官能基を有していてアルコール、例えば注目すべきはエタノールおよび/またはブチレングリコールなどに溶解または不溶であり得る)を含有する相と接触させることで前記炭水化物が有する第一級アルコール官能基と前記架橋剤が有する反応性官能基の間の重合を高分子量の炭水化物重合体が得られるに充分な時間実施することを特徴とする。 According to an advantageous embodiment, the production method comprises a carbohydrate having a primary alcohol function, notably polysaccharides and / or oligosaccharides and / or polyols, which are dissolved in the aqueous phase and then contain the carbohydrates. The aqueous phase is cross-linking agent (which has a functional group that can react preferentially with the primary alcohol function of the carbohydrate and is soluble or insoluble in alcohols such as ethanol and / or butylene glycol, notably Is sufficient to provide a high molecular weight carbohydrate polymer by polymerizing between the primary alcohol functional group of the carbohydrate and the reactive functional group of the cross-linking agent. It is characterized by being conducted for hours.
本発明に従う方法の変形である1つの態様に従い、そのような架橋剤をポリ(酸クロライド)、ポリ(酸無水物)、ポリイソシアネート、ポリチオイソシアネート、ポリアルデヒドおよびこれらの混合物のいずれか1つから成る群から選択する。有利には、反応物を中和させた後に分離操作を実施しなくてもよいように皮膚が許容し得る非反応性部分を有する架橋剤を選択する。 According to one embodiment, which is a variant of the process according to the invention, such a crosslinking agent is any one of poly (acid chloride), poly (anhydride), polyisocyanate, polythioisocyanate, polyaldehyde and mixtures thereof. Select from the group consisting of Advantageously, a cross-linking agent is selected that has a non-reactive portion that the skin can tolerate so that the separation operation does not have to be performed after neutralizing the reactants.
例えば、そのようなポリ(酸クロライド)をこれがエステル結合を形成するように酸トリクロライドおよび酸ジクロライドから選択する。 For example, such poly (acid chloride) is selected from acid trichloride and acid dichloride so that it forms an ester bond.
有利には、そのような架橋剤が当該アルコールに溶解する重量比は一般に5から30%の範囲で多様であるが、好適には10から20%の範囲である。 Advantageously, the weight ratio at which such crosslinkers dissolve in the alcohol generally varies from 5 to 30%, but preferably from 10 to 20%.
好適な特徴に従い、そのような架橋剤をフタル酸トリクロライド、フタル酸ジクロライド、セバシン酸ジクロライド、アゼライン酸ジクロライド、こはく酸ジクロライド、トリカルボン酸、例えばクエン酸などのジクロライドもしくはトリクロライドなどから選択する。前記ポリ(酸無水物)は例えば酸二無水物、例えばこはく酸二無水物またはマレイン酸二無水物などである。 According to preferred features, such cross-linking agents are selected from phthalic acid trichloride, phthalic acid dichloride, sebacic acid dichloride, azelaic acid dichloride, succinic acid dichloride, tricarboxylic acids such as dichloride or trichloride such as citric acid. The poly (acid anhydride) is, for example, an acid dianhydride, such as succinic dianhydride or maleic dianhydride.
本発明に従う方法の特に有利な別の態様に従う水相は、アルカリ水溶液相、即ちpHがアルカリ性、従ってpHが7より大きい水相である。好適なpH範囲は約7.1から約10の範囲のpHである。より好適なpHは8から10、好適には8から9の範囲である。水相を塩基性pHにする塩基として強塩基、例えばKOHまたはNaOHなど、または弱塩基、例えばアンモニア溶液、ホウ酸塩、燐酸塩または炭酸塩などを用いてもよい。 The aqueous phase according to another particularly advantageous embodiment of the process according to the invention is an aqueous alkaline phase, ie an aqueous phase whose pH is alkaline and therefore has a pH greater than 7. A preferred pH range is a pH in the range of about 7.1 to about 10. A more preferred pH is in the range of 8 to 10, preferably 8 to 9. A strong base such as KOH or NaOH, or a weak base such as ammonia solution, borate, phosphate or carbonate may be used as the base that brings the aqueous phase to a basic pH.
本発明に従う炭水化物の架橋重合体を局所用組成物、注目すべきは化粧品、皮膚−薬剤または薬剤組成物の形態で調製する。このことから、そのような組成物用の賦形剤に、例えば防腐剤、軟化剤、乳化剤、界面活性剤、保湿剤、増粘剤、コンディショナー、マチファイングエイジェント(matifying agents)、安定剤、抗酸化剤、質感剤(texture agents)、増白剤、膜形成剤、可溶化剤、顔料、染料、香料およびソラーフィルター(solar filters)から成る群から選択した少なくとも1種の化合物を含有させる。そのような賦形剤を好適にはアミノ酸およびこれらの誘導体、ポリグリセロール、セルロースのエステル、重合体および誘導体、ラノリン誘導体、燐脂質、ラクトフェリン、ラクトペルオキシダーゼ、スクロースが基になった安定剤、ビタミンEおよびこれの誘導体、天然および合成蝋、植物油、トリグリセリド、不鹸化剤(insaponifiables)、植物ステロール、植物エステル、シリコンおよびこれの誘導体、蛋白質加水分解物、ジョジョバ油およびこれの誘導体、脂溶性/水溶性エステル、ベタイン、アミノキサイド(aminoxides)、植物抽出液、スクロースのエステル、二酸化チタン、グリシンおよびパラベンから成る群から選択し、より好適には、ブチレングリコール、ステアレス−2、ステアレス−21、グリコール−15ステアリルエーテル、セテアリルアルコール、フェノキシエタノール、メチルパラベン、エチルパラベン、プロピルパラベン、ブチルパラベン、ブチレングリコール、天然トコフェロール、グリセロール、ナトリウムジヒドロキシセチル、イソプロピルヒドロキシセチルエーテル、グリコールステアレート、トリイソノナオイン(triisononaoine)、オクチルココエート、ポリアクリルアミド、イソパラフィン、ラウレス−7、カルボマー、プロピレングリコール、グリセロール、ビサボロール、ジメチコン、水酸化ナトリウム、PEG 30−ジポリヒドロキシステアレート、カプリン酸/カプリル酸トリグリセリド、オクタン酸セテアリル、アジピン酸ジブチル、ブドウ種油、ジョジョバ油、硫酸マグネシウム、EDTA、シクロメチコン、キサンタンゴム、クエン酸、ラウリル硫酸ナトリウム、鉱蝋および油、イソステアリン酸イソステアリル、プロピレングリコールジペラルゴネート、プロピレングリコールイソステアレート、PEG 8蜜蝋、水添ヤシハートオイル(palm tree heart oil)グリセリド、水添ヤシ油グリセリド、ラノリン油、ゴマ油、乳酸セチル、ラノリンアルコール、ヒマシ油、二酸化チタン、ラクトース、スクロース、低密度ポリエチレンおよび等張食塩水から成る群から選択する。 The crosslinked polymers of carbohydrates according to the present invention are prepared in the form of topical compositions, notably cosmetics, skin-drugs or pharmaceutical compositions. From this, excipients for such compositions include, for example, preservatives, softeners, emulsifiers, surfactants, humectants, thickeners, conditioners, matifying agents, stabilizers, At least one compound selected from the group consisting of antioxidants, texture agents, whitening agents, film forming agents, solubilizers, pigments, dyes, fragrances and solar filters is included. Such excipients are preferably amino acids and their derivatives, polyglycerol, cellulose esters, polymers and derivatives, lanolin derivatives, phospholipids, lactoferrin, lactoperoxidase, sucrose-based stabilizers, vitamin E And derivatives thereof, natural and synthetic waxes, vegetable oils, triglycerides, insaponifiables, plant sterols, plant esters, silicon and derivatives thereof, protein hydrolysates, jojoba oil and derivatives thereof, fat-soluble / water-soluble Selected from the group consisting of esters, betaines, aminoxides, plant extracts, esters of sucrose, titanium dioxide, glycine and parabens, more preferably butylene glycol, steareth-2, steareth-21 Glycol-15 stearyl ether, cetearyl alcohol, phenoxyethanol, methyl paraben, ethyl paraben, propyl paraben, butyl paraben, butylene glycol, natural tocopherol, glycerol, sodium dihydroxycetyl, isopropyl hydroxycetyl ether, glycol stearate, triisononaoine ), Octyl cocoate, polyacrylamide, isoparaffin, laureth-7, carbomer, propylene glycol, glycerol, bisabolol, dimethicone, sodium hydroxide, PEG 30-dipolyhydroxystearate, capric acid / caprylic acid triglyceride, cetearyl octanoate, Dibutyl adipate, grape seed oil, jojoba oil, magnesium sulfate Cium, EDTA, cyclomethicone, xanthan gum, citric acid, sodium lauryl sulfate, mineral wax and oil, isostearyl isostearate, propylene glycol dipelargonate, propylene glycol isostearate, PEG 8 beeswax, hydrogenated coconut heart oil (palm tree heart oil) glycerides, hydrogenated coconut oil glycerides, lanolin oil, sesame oil, cetyl lactate, lanolin alcohol, castor oil, titanium dioxide, lactose, sucrose, low density polyethylene and isotonic saline.
上述した組成物を有利には溶液(これは水溶液または油溶液である)、クリームまたは水性ゲルもしくは油性ゲル、注目すべきはポットまたはチューブに入っている形態、注目
すべきシャワーゲル、シャンプー、ミルク、エマルジョン、ミクロエマルジョンまたはナノエマルジョン[これは注目すべきは水中油もしくは油中水またはマルチプル(multiple)またはシリコン含有]、ローション、注目すべきはガラス瓶、プラスチックボトル、測定用ボトルに入っているローション、エーロゾル、アンプル、液体石鹸、皮膚科学的バー、軟膏、発泡体および無水製品(好適には液状、ペースト状または固体状、例えばスティックの形態、注目すべきはリップスティックの形態)などから成る群から選択した形態に調合する。
The composition described above is preferably a solution (which is an aqueous or oil solution), cream or aqueous gel or oily gel, notably in a pot or tube form, notable shower gel, shampoo, milk , Emulsions, microemulsions or nanoemulsions (which are noteworthy oil-in-water or water-in-oil or multiple or silicon containing), lotions, noteworthy lotions in glass bottles, plastic bottles, measuring bottles , Aerosols, ampoules, liquid soaps, dermatological bars, ointments, foams and anhydrous products (preferably in liquid, pasty or solid form, eg stick form, noteworthy lipstick form) etc. Formulate into a form selected from
説明的記述を単に説明として示しかつ本発明の範囲を決して限定するものでない本実施例を参照して読むことで本発明の他の目的、特徴および利点が本分野の技術者に明らかに思い浮かぶであろう。 Other objects, features and advantages of the present invention will clearly occur to those skilled in the art when read with reference to the present examples, which are given by way of illustration only and are not intended to limit the scope of the invention in any way. Will.
本実施例は本発明の一体部分を構成しかつ本実施例を包含する説明全体を解釈することで如何なる最新技術と比較しても新規であると思われる如何なる特徴もこれの機能および一般性の点で本発明の一体部分を構成する。 This embodiment constitutes an integral part of the present invention and any feature that appears to be novel compared to any state-of-the-art by interpreting the entire description encompassing this embodiment is the function and generality of this embodiment. This constitutes an integral part of the present invention.
従って、全ての実施例が有する範囲は一般的範囲である。 Accordingly, the range of all the examples is a general range.
その上、本実施例では、特に明記しない限り、パーセントを全部重量で示し、特に明記しない限り、温度を摂氏度で表し、そして特に明記しない限り、圧力は大気圧である。
実施例
Moreover, in this example, all percentages are by weight unless otherwise specified, temperatures are expressed in degrees Celsius unless otherwise specified, and pressures are atmospheric unless otherwise specified.
Example
キサンタンの2%水溶液の架橋、ヒト皮膚に対して示す引き締める効果の立証
1. 多糖類であるキサンタン(5,000,000Da)の調合液を下記の如く調製する:93.1gの冷脱塩水にキサンタン(KELTROL、SPCI)を2.10g溶解させる。次に、この調合液に強力撹拌下でNaHCO3を4.8g加える。完全溶解後にpHを8から8.4の範囲の値に安定化させる。
2. 架橋剤の調製:4.25gのブチレングリコールにセバシン酸ジクロライドを0.75g溶解させる。
3. キサンタン水溶液の架橋:2.で調製した溶液を1.で調製した溶液に撹拌下で添加する。その全体を撹拌下に60分間置くことで、一方の活性化された二酸と他方の多糖類が有するアルコール官能基の間の重合を起こさせる。媒体を塩基性にすることで前記反応を促進させる。反応後、キサンタンの架橋体が入っている溶液をそのまま用いることも可能であるが、それには不溶な物質が入っている。濾過を例えばカットオフ閾値が0.22μmの装置を用いて実施して生成物を濾過することで、そのような不溶物を除去してもよい。
4. 引き締める効果を測定する原理:本発明で多糖類を重合させることで生じさせた生成物が皮膚の生体力学的特性に対して示す美容効果を特徴づける目的で主に「Video
Digitizer(商標)」(Courage et Khazaka)の商標下で販売されている装置を用いて引き締める効果を測定する。そのような装置を用いると、皮膚の粗さの変数を測定することができ、それは、皮膚起伏の画像が「尾根と谷」の形態で表されることで測定される。引き締める効果は粗さが減少すればするほど大きい。前腕上に2つの測定領域(2cmx2cm)を決定し、1番目の領域に3.で調製した溶液を50mg塗布する。2番目の領域に架橋させていないキサンタンの溶液を50mg塗布する。1分間放置して乾燥させた後、「Video Digitizer(商標)」を用いて体積の変数を測定する。この測定の均一性を良好にする目的で測定を10回繰り返す。引き締める効果によって、処置後に測定する粗さの低下が誘発される。その結果を以下の表に示す:
Video Digitizer(商標)で測定した粗さ
重合させていない溶液 重合させた溶液
塗布前 64.22±1.56 76.80±0.83
塗布してから5分後 64.20±1.56 61.20±1.24
粗さの低下、即ち 0% 20.3%
引き締め効果(%)
この試験によって、本発明の生成物を健康な志願者の皮膚に塗布すると有意な引き締め効果を得ることができることが分かる。
Cross-linking of a 2% aqueous solution of xanthan, demonstrating the tightening effect shown on human skin A preparation of the polysaccharide xanthan (5,000,000 Da) is prepared as follows: 2.10 g of xanthan (KELTROL, SPCI) is dissolved in 93.1 g of cold demineralized water. Next, 4.8 g of NaHCO 3 is added to the blend under vigorous stirring. After complete dissolution, the pH is stabilized to a value in the range of 8 to 8.4.
2. Preparation of crosslinking agent: 0.75 g of sebacic acid dichloride is dissolved in 4.25 g of butylene glycol.
3. Crosslinking of aqueous xanthan solution: 2. 1. Prepare the solution prepared in 1. Add under stirring to the solution prepared in. The whole is left under stirring for 60 minutes to cause polymerization between the alcohol function of one activated diacid and the other polysaccharide. The reaction is promoted by making the medium basic. After the reaction, a solution containing a crosslinked xanthan can be used as it is, but it contains an insoluble substance. Such insoluble matter may be removed by filtering the product, for example, using a device having a cutoff threshold of 0.22 μm.
4). Principle of measuring the tightening effect: “Video” is mainly used for the purpose of characterizing the cosmetic effect exhibited by the product produced by polymerizing the polysaccharide in the present invention on the biomechanical properties of the skin.
The effect of tightening is measured using a device sold under the trademark Digitizer ™ (Courage et Kazaka). With such a device, a skin roughness variable can be measured, which is measured by the appearance of skin relief images in the form of “ridges and valleys”. The tightening effect increases as the roughness decreases. Two measurement areas (2 cm × 2 cm) are determined on the forearm, and 3. 50 mg of the solution prepared in (1) is applied. Apply 50 mg of uncrosslinked xanthan solution to the second region. After leaving to dry for 1 minute, the volume variable is measured using a “Video Digitizer ™”. The measurement is repeated 10 times for the purpose of improving the uniformity of the measurement. The tightening effect induces a reduction in roughness as measured after treatment. The results are shown in the following table:
Roughness measured with Video Digitizer ™
Unpolymerized solution Before polymerized solution application 64.22 ± 1.56 76.80 ± 0.83
5 minutes after application 64.20 ± 1.56 61.20 ± 1.24
Roughness reduction, ie 0% 20.3%
Tightening effect (%)
This test shows that a significant tightening effect can be obtained when the product of the present invention is applied to the skin of a healthy volunteer.
キサンタンの2%水溶液の架橋
実施例1の段階1中に2%のキサンタン溶液にクエン酸トリナトリウムを1%添加する。他の段階は全部同じである。引き締め効果は実施例1で得た効果に近い。
Crosslinking of a 2% aqueous solution of xanthan 1% trisodium citrate is added to a 2% xanthan solution during stage 1 of Example 1. All other steps are the same. The tightening effect is close to the effect obtained in Example 1.
キサンタンの2%水溶液の架橋
実施例1の段階1中に2%のキサンタン溶液に(トリス[ヒドロキシメチル]アミノメタン)を0.4%添加する。他の段階は全部同じである。引き締め効果は実施例1で得た効果に近い。
Crosslinking of 2% aqueous solution of xanthan 0.4% of (tris [hydroxymethyl] aminomethane) is added to the 2% xanthan solution during stage 1 of Example 1. All other steps are the same. The tightening effect is close to the effect obtained in Example 1.
キサンタンの2%水溶液の架橋
実施例1の段階1中に2%のキサンタン溶液に燐酸ジナトリウムを0.5%添加する。他の段階は全部同じである。引き締め効果は実施例1で得た効果に近い。
Cross-linking of 2% aqueous solution of xanthan 0.5% of disodium phosphate is added to 2% xanthan solution during stage 1 of Example 1. All other steps are the same. The tightening effect is close to the effect obtained in Example 1.
セルロース水溶液の架橋および感覚評価
1. セルロース(1,000,000Da)の水溶液の調製を下記の如く行う:94.64gの冷脱塩水にNatrosol(商標)250HHXを0.56g溶解させる。次に、この調合液に強力撹拌下でNaHCO3を4.8g加える。完全溶解後にpHを8から8.4の範囲の値に安定化させる。
2. 架橋剤の調製:8.5gのブチレングリコールにセバシン酸ジクロライドを1.5g溶解させる。
3. セルロース水溶液の架橋:2.で調製した溶液を1.で調製した溶液に撹拌下で添加する。その全体を撹拌下に60分間置くことで、一方の活性化された二酸と他方の多糖類が有するアルコール官能基の間の重合を起こさせる。媒体を塩基性にすることで前記反応を促進させる。反応後、Natrosol(商標)250HHXの架橋体が入っている溶液をそのまま用いることができる。
4. 引き締める効果を測定する原理:前腕上に2つの測定領域(2cmx2cm)を決定し、1番目の領域にNatrosol(商標)250HHXの架橋体が入っている溶液を50mg塗布する。2番目の領域に架橋させていないNatrosol(商標)250HHXの溶液を50mg塗布する。
Crosslinking of cellulose aqueous solution and sensory evaluation An aqueous solution of cellulose (1,000,000 Da) is prepared as follows: 0.56 g of Natrosol ™ 250HHX is dissolved in 94.64 g of cold demineralized water. Next, 4.8 g of NaHCO 3 is added to the blend under vigorous stirring. After complete dissolution, the pH is stabilized to a value in the range of 8 to 8.4.
2. Preparation of crosslinking agent: 1.5 g of sebacic acid dichloride is dissolved in 8.5 g of butylene glycol.
3. Crosslinking of aqueous cellulose solution: 2. 1. Prepare the solution prepared in 1. Add under stirring to the solution prepared in. The whole is left under stirring for 60 minutes to cause polymerization between the alcohol function of one activated diacid and the other polysaccharide. The reaction is promoted by making the medium basic. After the reaction, a solution containing a cross-linked product of Natrosol ™ 250HHX can be used as it is.
4). Principle for measuring the tightening effect: Two measurement areas (2 cm × 2 cm) are determined on the forearm, and 50 mg of a solution containing a cross-linked Natrosol ™ 250HHX is applied to the first area. Apply 50 mg of uncrosslinked Natrosol ™ 250HHX solution to the second area.
1分間放置して乾燥させた後、整える感覚を志願者の一団による感覚評価で評価する。ヒトの皮膚に対する感覚評価
架橋させていないNatrosol 架橋させたNatrosol
(商標)250HHXの溶液 (商標)250HHXの溶液
+ +++
+:引き締める効果を有意には感じなかった
+++:引き締める効果を非常に有意に感じた
この試験によって、本発明の生成物を健康な志願者の皮膚に塗布すると有意な引き締め
効果を得ることができることが分かり、これは感覚評価で検出可能である。
After leaving to dry for 1 minute, the sense of preparation is evaluated by sensory evaluation by a group of volunteers. Sensory evaluation for human skin Uncrosslinked Natrosol Crosslinked Natrosol
(Trademark) 250HHX solution (trademark) 250HHX solution
+++++
+: The effect of tightening was not significantly felt. +++: The effect of tightening was felt very significantly. By this test, when the product of the present invention was applied to the skin of a healthy volunteer, a significant tightening effect could be obtained. This can be detected by sensory evaluation.
カロブ豆ゴム(300,000Da)の水溶液の架橋
実施例5の段階1中にカロブ豆の5%溶液、好適にはカロブ豆の2%溶液を調製する。他の段階は全部同じである。引き締め効果は実施例5で得た効果に近い。
Cross-linking of an aqueous solution of carob bean gum (300,000 Da) During step 1 of Example 5, a 5% solution of carob beans, preferably a 2% solution of carob beans, is prepared. All other steps are the same. The tightening effect is close to the effect obtained in Example 5.
キシリトール(152Da)水溶液の架橋
実施例5の段階1中にキシリトールの5%溶液を調製する。他の段階は全部同じである。引き締め効果は実施例5で得た効果に近い。
Crosslinking of aqueous xylitol (152 Da) A 5% solution of xylitol is prepared during step 1 of Example 5. All other steps are the same. The tightening effect is close to the effect obtained in Example 5.
マルトース(342Da)水溶液の架橋
実施例5の段階1中にマルトースの20%溶液を調製する。他の段階は全部同じである。引き締め効果は実施例5で得た効果に近い。
Crosslinking of aqueous maltose (342 Da) solution During stage 1 of Example 5, a 20% solution of maltose is prepared. All other steps are the same. The tightening effect is close to the effect obtained in Example 5.
(実施例9a)
カラギナン水溶液の架橋および流動性の修飾
1. カラギナン(500,000Da)(Genuvisco(商標)、HERCULES)の水溶液の調製を下記の如く行う:94.65gの冷脱塩水にGenuvisco(商標)(HERCULES)を0.55g入れる。次に、この調合液に強力撹拌下でNaHCO3を4.8g加える。完全溶解後にpHを8から8.4の範囲の値に安定化させる。
2. 架橋剤の調製:0.9gのエタノールにテレフタル酸ジクロライドを0.1g溶解させる。
3. カラギナン水溶液の架橋:2.で調製した溶液を1.で調製した水溶液に撹拌下で添加する。その全体を撹拌下に60分間置くことで、一方の活性化された二酸と他方の多糖類が有するアルコール官能基の間の重合を起こさせる。媒体を塩基性にすることで前記反応を促進させる。反応後、カラギナンの架橋体が入っている溶液をそのまま用いてもよいか、或は不溶な化合物を除去する目的でそれを濾過してもよい。
Example 9a
Cross-linking and fluidity modification of carrageenan aqueous solution An aqueous solution of carrageenan (500,000 Da) (Genuvisco ™, HERCULES) is prepared as follows: 0.55 g of Genuvisco ™ (HERCULES) is placed in 94.65 g of cold demineralized water. Next, 4.8 g of NaHCO 3 is added to the blend under vigorous stirring. After complete dissolution, the pH is stabilized to a value in the range of 8 to 8.4.
2. Preparation of crosslinking agent: 0.1 g of terephthalic acid dichloride is dissolved in 0.9 g of ethanol.
3. Cross-linking of carrageenan aqueous solution: 2. 1. Prepare the solution prepared in 1. Add to the aqueous solution prepared in. The whole is left under stirring for 60 minutes to cause polymerization between the alcohol function of one activated diacid and the other polysaccharide. The reaction is promoted by making the medium basic. After the reaction, the solution containing the carrageenan crosslinked product may be used as it is, or may be filtered for the purpose of removing insoluble compounds.
引き締める効果は実施例5で得た効果に近い。
粘度測定の原理:架橋させた多糖類の水溶液の粘度を架橋させていない多糖類の水溶液の粘度と対比させることで粘度測定を実施する。使用した粘度計はBrookfieldのRVTDV−II型の回転装置であり、それを速度50で用いかつニードル04を用いる。
The effect of tightening is close to the effect obtained in Example 5.
Principle of viscosity measurement: Viscosity measurement is carried out by comparing the viscosity of an aqueous solution of a crosslinked polysaccharide with the viscosity of an aqueous solution of an uncrosslinked polysaccharide. The viscometer used is a Brookfield RVTDV-II rotating device, which is used at speed 50 and needle 04.
その上、炭水化物を重合させると分子質量の増加が誘発され、それによって、それが溶解媒体中で示す粘度の上昇が誘発される。このような粘度上昇検定によって重合の度合を測定することができる。
粘度測定
架橋させていないカラギナンの溶液 架橋させたカラギナンの溶液
588cps 2632cps
(実施例9b)
前以て加水分解を受けさせておいたカラギナン水溶液の架橋
1. カラギナン(Genuvisco(商標)、HERCULES)の加水分解物の水溶液の調製を下記の如く行う:90gの0.1M HCl溶液にGenuvisco(商標)(HERCULES)を10g入れる(0.1モル/リットル)。加水分解を穏やか
な撹拌下60℃で5時間実施した後、1MのNaOHを用いてpHを8から9の範囲にすることによる中和で加水分解を停止させる。
2. 架橋剤の調製:0.9gのエタノールにテレフタル酸ジクロライドを0.1g溶解させる。
3. カラギナン水溶液の架橋:2.で調製した溶液を1.で調製した水溶液に撹拌下で添加する。その全体を撹拌下に60分間置くことで、一方の活性化された二酸と他方の多糖類が有するアルコール官能基の間の重合を起こさせる。媒体を塩基性にすることで前記反応を促進させる。反応後、カラギナンの架橋体が入っている溶液に透析濾過を受けさせることで塩を除去した後、不溶な化合物を除去する目的で濾過してもよいか、或はそのまま用いてもよい。
Moreover, polymerizing carbohydrates induces an increase in molecular mass, thereby inducing an increase in viscosity that it exhibits in the dissolution medium. The degree of polymerization can be measured by such a viscosity increase test.
Viscosity measurement Uncrosslinked carrageenan solution Crosslinked carrageenan solution 588 cps 2632 cps
(Example 9b)
Crosslinking of an aqueous carrageenan solution that has been previously hydrolyzed 1. Preparation of an aqueous solution of carrageenan (Genuvisco ™, HERCULES) hydrolyzate is carried out as follows: 10 g of Genuvisco ™ (HERCULES) is placed in 90 g of 0.1 M HCl solution (0.1 mol / l). The hydrolysis is carried out for 5 hours at 60 ° C. with gentle stirring and then stopped by neutralization by using 1 M NaOH to bring the pH to the range 8-9.
2. Preparation of crosslinking agent: 0.1 g of terephthalic acid dichloride is dissolved in 0.9 g of ethanol.
3. Cross-linking of carrageenan aqueous solution: 2. 1. Prepare the solution prepared in 1. Add to the aqueous solution prepared in. The whole is left under stirring for 60 minutes to cause polymerization between the alcohol function of one activated diacid and the other polysaccharide. The reaction is promoted by making the medium basic. After the reaction, the solution containing the cross-linked carrageenan is subjected to diafiltration to remove salts, and then filtered for the purpose of removing insoluble compounds, or may be used as it is.
引き締める効果はこの上に示した実施例で観察した効果よりも大きい(特に実施例5の生成物を用いた時に得た効果よりも大きい)。 The effect of tightening is greater than the effect observed in the example shown above (particularly greater than the effect obtained when using the product of Example 5).
ラフィノース五水化物(594Da)の水溶液の架橋
実施例9の段階1中にラフィノースの10%溶液を調製する。他の段階は全部同じである。引き締め効果は実施例5で得た効果に近いが、パネリストは非常に明瞭な軟化効果を検出した。
Crosslinking of an aqueous solution of raffinose pentahydrate (594 Da) A 10% solution of raffinose is prepared during stage 1 of Example 9. All other steps are the same. Although the tightening effect is close to that obtained in Example 5, the panelists detected a very clear softening effect.
アカシアゴム水溶液の架橋
実施例9の段階1中にアカシアゴム(250,000Da)の5%溶液を調製する。他の段階は全部同じである。引き締め効果は実施例5で得た効果よりも大きい。
Crosslinking of Acacia Gum Aqueous Solution During step 1 of Example 9, a 5% solution of acacia gum (250,000 Da) is prepared. All other steps are the same. The tightening effect is greater than the effect obtained in Example 5.
多糖類/ポリオール混合物の水溶液の架橋
実施例9の段階1中にグリセロール(92Da)(10%、重量/重量)とキサンタン(2%、重量/重量)の溶液を調製する。他の段階は全部同じである。引き締め効果は実施例5で得た効果に近いが、パネリストは非常に明瞭な軟化効果を検出した。
Crosslinking of an aqueous solution of polysaccharide / polyol mixture A solution of glycerol (92 Da) (10%, weight / weight) and xanthan (2%, weight / weight) is prepared during Stage 1 of Example 9. All other steps are the same. Although the tightening effect is close to that obtained in Example 5, the panelists detected a very clear softening effect.
オリゴ糖/ポリオール混合物の水溶液の架橋
実施例9の段階1中にマンニトール(182Da)(10%、重量/重量)とイヌリン(約5000Da)(5%、重量/重量)の溶液を調製する。他の段階は全部同じである。引き締め効果は実施例5で得た効果に近いが、パネリストは非常に明瞭な軟化効果を検出した。
Crosslinking of an aqueous solution of an oligosaccharide / polyol mixture During Step 1 of Example 9, a solution of mannitol (182 Da) (10%, weight / weight) and inulin (about 5000 Da) (5%, weight / weight) is prepared. All other steps are the same. Although the tightening effect is close to that obtained in Example 5, the panelists detected a very clear softening effect.
本発明の生成物を水中油エマルジョン型の化粧品または薬製剤で使用
配合14a:
A 水 100になる量(Qsp)
ブチレングリコール 2
グリセリン 3
ジヒドロキシセチル燐酸ナトリウム 2
イソプロピルヒドロキシセチルエーテル
B グリコールステアレートSE 14
トリイソノナオイン 5
オクチルココエート 6
C ブチレングリコール、 2
メチルパラベン、
エチルパラベン、プロピルパラベン
pHを5.5に調整
D 本発明の生成物 0.01−10%
配合14b:
A 水 100になる量
ブチレングリコール 2
グリセリン 3
ポリアクリルアミド、イソパラフィン、 2.8
ラウレス−7
B ブチレングリコール、 2
メチルパラベン、
エチルパラベン、プロピルパラベン
フェノキシエタノール、 2
メチルパラベン、
プロピルパラベン、ブチルパラベン
エチルパラベン
ブチレングリコール 0.5
D 本発明の生成物 0.01−10%
配合14c:
A カルボマー 0.50
プロピレングリコール 3
グリセロール 5
水 100になる量
B オクチルココエート 5
ビサボロール 0.30
ジメチコン 0.30
C 水酸化ナトリウム 1.60
D フェノキシエタノール、 0.50
メチルパラベン、
プロピルパラベン、ブチルパラベン
エチルパラベン
E 香料 0.30
F 本発明の生成物 0.01−10%
Use of the product of the invention in an oil-in-water emulsion type cosmetic or pharmaceutical formulation 14a:
A Water 100 (Qsp)
Butylene glycol 2
Glycerin 3
Sodium dihydroxycetyl phosphate 2
Isopropyl hydroxycetyl ether
B Glycol stearate SE 14
Triisononaoin 5
Octyl cocoate 6
C butylene glycol, 2
Methylparaben,
Ethylparaben, propylparaben pH adjusted to 5.5 D Product of the invention 0.01-10%
Formula 14b:
A Water Amount to be 100 Butylene glycol 2
Glycerin 3
Polyacrylamide, isoparaffin, 2.8
Laureth-7
B Butylene glycol, 2
Methylparaben,
Ethylparaben, propylparaben, phenoxyethanol, 2
Methylparaben,
Propylparaben, Butylparaben Ethylparaben Butylene glycol 0.5
D Product of the invention 0.01-10%
Formula 14c:
A Carbomer 0.50
Propylene glycol 3
Glycerol 5
Amount of water to be 100 B Octyl cocoate 5
Bisabolol 0.30
Dimethicone 0.30
C Sodium hydroxide 1.60
D Phenoxyethanol, 0.50
Methylparaben,
Propylparaben, Butylparaben Ethylparaben E Fragrance 0.30
F Product of the invention 0.01-10%
本発明の実施例
本発明の生成物を油中水エマルジョン型の調合物で使用
A PEG 30ジポリヒドロキシステアレート 3
カプリン酸トリグリセリド 3
オクタン酸セテアリル 4
アジピン酸ジブチル 3
ブドウ種油 1.5
ジョジョバ油 1.5
フェノキシエタノール、 0.5
メチルパラベン、
プロピルパラベン、ブチルパラベン
エチルパラベン
B グリセリン 3
ブチレングリコール 3
硫酸マグネシウム 0.5
EDTA 0.05
水 100になる量
C シクロメチコン 1
ジメチコン 1
D 香料 0.3
E 本発明の生成物 0.01−10%
Examples of the Invention The product of the invention is used in a water-in-oil emulsion formulation A PEG 30 Dipolyhydroxystearate 3
Capric acid triglyceride 3
Cetearyl octoate 4
Dibutyl adipate 3
Grape seed oil 1.5
Jojoba oil 1.5
Phenoxyethanol, 0.5
Methylparaben,
Propylparaben, Butylparaben Ethylparaben B Glycerin 3
Butylene glycol 3
Magnesium sulfate 0.5
EDTA 0.05
Amount of water to be 100 C Cyclomethicone 1
Dimethicone 1
D Fragrance 0.3
E Product of the invention 0.01-10%
本発明の実施例
本発明の生成物をシャンプーまたはシャワーゲル型の調合物で使用
A キサンタンゴム 0.8
水 100になる量
B ブチレングリコール、 0.5
メチルパラベン、
メチルパラベン、
エチルパラベン、プロピルパラベン、
フェノキシエタノール、 0.5
メチルパラベン、
プロピルパラベン、ブチルパラベン
エチルパラベン
C クエン酸 0.8
D ラウレス硫酸ナトリウム 40.0
E 本発明の生成物 0.01−10%
Examples of the invention The products of the invention are used in shampoo or shower gel type formulations. A Xanthan gum 0.8
Amount of water to be 100 B Butylene glycol, 0.5
Methylparaben,
Methylparaben,
Ethyl paraben, propyl paraben,
Phenoxyethanol, 0.5
Methylparaben,
Propylparaben, Butylparaben Ethylparaben C Citric acid 0.8
D Sodium laureth sulfate 40.0
E Product of the invention 0.01-10%
本発明の実施例
本発明の生成物をリップスティック型の調合物および他の無水製品で使用
A 鉱蝋 17.0
イソステアリン酸イソステアリル 31.5
プロピレングリコールジペラルゴネート 2.6
プロピレングリコールイソステアレート 1.7
PEG 8蜜蝋 3.0
水添パーム核油グリセリド、 3.4
水添パームグリセリド
ラノリン油 3.4
ゴマ油 1.7
乳酸セチル 1.7
鉱油、ラノリンアルコール 3.0
B ヒマシ油 100になる量
二酸化チタン 3.9
CI 15850:1 0.616
CI 45410:1 0.256
CI 19140:1 0.048
CI 77491 2.048
C 本発明の生成物 0.01−5%
Examples of the invention The products of the invention are used in lipstick-type formulations and other anhydrous products A mineral wax 17.0
Isostearyl isostearate 31.5
Propylene glycol dipelargonate 2.6
Propylene glycol isostearate 1.7
PEG 8 beeswax 3.0
Hydrogenated palm kernel oil glycerides, 3.4
Hydrogenated palm glyceride lanolin oil 3.4
Sesame oil 1.7
Cetyl lactate 1.7
Mineral oil, lanolin alcohol 3.0
B Castor oil Amount to be 100 Titanium dioxide 3.9
CI 15850: 1 0.616
CI 45410: 1 0.256
CI 19140: 1 0.048
CI 77491 2.048
C Product of the invention 0.01-5%
本発明の実施例
本発明の生成物を水性ゲル(目の回り、スリマーなど)の調合物で使用
A 水 100になる量
カルボマー 0.5
ブチレングリコール 15
フェノキシエタノール、メチルパラベン、 0.5
プロピルパラベン、ブチルパラベン、
エチルパラベン
B 本発明の生成物 0.01−10%
Examples of the invention The product of the invention is used in a formulation of an aqueous gel (around eyes, slimer, etc.) A Amount of water to 100 Carbomers 0.5
Butylene glycol 15
Phenoxyethanol, methylparaben, 0.5
Propylparaben, butylparaben,
Ethylparaben B Product of the invention 0.01-10%
本発明の主題を含有させた調合物が化粧品で受け入れられることの評価
実施例2に従って得た化合物を0.5%のキサンタンゲルに10%混合し、それにウサギの眼を用いた評価、ラットに1回経口投与して異常な毒性が存在しないことを示す検定およびモルモットを用いた感作力の検定を受けさせることで、毒性試験を実施した。
ウサギ皮膚の一次刺激の評価
「皮膚に対する急性刺激/腐食の影響」の研究に関してOECDのDirctiveが推奨する方法に従って、この上に記述した調合物を希釈しないで3匹のウサギの皮膚に0.5mlの用量で塗布する。
Evaluation of cosmetic acceptance of the formulation containing the subject matter of the invention The compound obtained according to Example 2 was mixed with 10% in 0.5% xanthan gel and evaluated using the rabbit eye, in rats Toxicity studies were performed by taking a single oral dose test that showed no abnormal toxicity and a test of sensitization using guinea pigs.
Assessment of primary irritation of rabbit skin According to the method recommended by OECD Directive for the "Acute Irritation / Corrosion Effect on Skin" study, 0.5 ml was applied to the skin of 3 rabbits without diluting the formulation described above. Apply at a dose of
21/02/82のOfficial Journal of the French
Republic(「JORF」)に公開された1/2/1982のDecisionに定義されている判断基準に従って生成物の分類分けを行う。
21/02/82 Official Journal of the French
The products are classified according to the criteria defined in 1/2/1982 Decision published in Republic ("JORF").
この試験の結果によって、実施例2に従って得た化合物を含有させた調合物は皮膚に刺激を与えないと分類分けされると結論付けることができた。
ウサギ眼の刺激の評価
「眼に対する急性刺激/腐食の影響」の研究に関して1987年2月24日付けのOECD No.405のDirectiveが推奨する方法に従って、この上に記述した調合物をそのままの状態で3匹のウサギの眼に0.1mlの率で1回染み込ませた。
From the results of this test it was possible to conclude that the formulation containing the compound obtained according to Example 2 was classified as non-irritating to the skin.
Evaluation of Rabbit Eye Irritation OECD No. dated February 24, 1987 for the study of “Effects of Acute Irritation / Corrosion on the Eye”. In accordance with the method recommended by 405 Direct, the formulation described above was instilled once into the eyes of three rabbits at a rate of 0.1 ml.
この試験の結果によって、前記調合物はそのままの状態、即ち希釈なしに用いた時にDirctive 91/326 EECの意味で眼に刺激を与えないと見なすことができると結論付けることができた。
ラットに1回経口投与した時に異常な毒性が存在しないことに関する試験
1987年2月24日付けのOECD No.401のDirectiveが推奨しかつ化粧品に適合するプロトコルに従って、この上に記述した調合物を5匹のオスラットと5匹のメスラットに体重1kg当たり5gの用量で1回経口投与した。
From the results of this test, it was concluded that the formulation can be considered as non-irritating to the eye in the sense of Direct 91/326 EEC when used as is, ie without dilution.
Study on Absence of Abnormal Toxicity when Orally Administered to Rats Once OECD No. 24, Feb. 24, 1987 According to 401 Directive recommended and cosmetically compatible protocol, the formulation described above was administered orally once to 5 male rats and 5 female rats at a dose of 5 g / kg body weight.
測定LD0およびLD50は5,000mg/Kg以上である。従って、試験を受けさせた調合物は摂取が危険な調合物の中には入らないと分類分けされる。
モルモットにおける皮膚感作可能性の評価
この上に記述した調合物にMagnussonおよびKligmannが記述した極大化試験、即ちOECDのDirective line No.406に一致するプロトコルを受けさせた。
The measured LD0 and LD50 are 5,000 mg / Kg or more. Therefore, the tested formulations are classified as not being in danger of consumption.
Assessment of skin sensitization in guinea pigs A maximization test described by Magnusson and Kligmann in the formulation described above, ie Direct Line No. OECD. Received protocol matching 406.
この上に示した実施例に記述した調合物は、皮膚との接触で皮膚を感作しないと分類分けされる。 The formulations described in the examples given above are classified as not sensitizing the skin on contact with the skin.
比較として、実施例1の方法に従う架橋を受けさせた市販の小麦蛋白質は、前記試験プロトコルに従って試験を受けさせた動物の40%に感作を誘発した。 By way of comparison, commercial wheat protein that had been cross-linked according to the method of Example 1 induced sensitization in 40% of animals that were tested according to the test protocol.
Claims (17)
a)−ガラクトマンナン、グアーもしくはカロブ豆に由来するガラクトマンナン、
−カラギナン、紅藻に由来するカラギナン、
−グルコマンナン、コンニャクゴムに由来するグルコマンナン、
−発酵に由来する第一級アルコール官能基を有する多糖類、キサンタン、ヒアルロン酸、
−セルロース、
−ヒドロキシプロピルメチルセルロースおよびメチルエチルセルロース、メチルヒドロキシメチルセルロースから成る群から選択されるセルロース成分、
−ポリホロシド、
−寒天、
−アルギネート、アルギン酸のナトリウム塩、アルギン酸ナトリウム、
−澱粉、アミロペクチン、アミロース、小麦に由来する澱粉、米に由来する澱粉、ジャガイモに由来する澱粉、トウモロコシに由来する澱粉、
−キトサン、
−カードラン、
−アドラガンテゴムまたはトラガカントゴム、
−アラビアゴムまたはアカシアゴム、
−キアゴム、
−エレミゴム、
−ゲランゴム、
−ガッチゴムまたはインドゴム、
−カラヤゴム、
−シェラック、および
−マニラゴム、
から成る群から選択される多糖類、
b)−シクロデキストリン、αシクロデキストリン、βシクロデキストリンまたはγシクロデキストリンおよびこれらの任意混合物、
−デキストリン、
−ラフィノース、セロビオース、スクロース、マルトース、ラクトース、トレハロース、ジヒドロキシアセトン(DHA)、フラクトース、ソルボース、リボース、デオキシリボース、キシロース、アラビノース、グルコース、マンノース、ガラクトース、エリスロース、トレオース、アロース、アトロース、グロース、イドース、タロース、エリトルロース、キシルロース、プシコース、タガトース、セドヘプツロース、キシロビオース、キトビオース、ニゲロース、アミナリビオース、コジビオース、ソフォロース、ゲンチアノース、ゲンチオビオース、メリビオース、メレジトース、ツラノース、スタキオース、ベルバスコース、
−グルコン酸、グルコノラクトン、グルコサミン、ガラクトサミン、硫酸ガラクトサミン、硫酸グルコサミン、
−サポニン、キラヤの樹皮に由来するサポニン、
−グアノシン、ウリジン、
−硫酸ストレプトマイシン、および
−リボフラビン、
から成る群から選択されるオリゴ糖、単糖類および二糖類から選択される糖成分、およびc)−グリセロール、ソルビトール、エリスリトール、マルチトール、ソルビトール、マンニトール、ラクチトール、ガラクチトール、リビトール、グリセロール、キシリトール、ミオ−イノシトールおよびポリエチレングリコール、
から成る群から選択されるポリオール、
から成る群から選択される請求項7記載の架橋重合体。 The carbohydrate component is a) -galactomannan derived from galactomannan, guar or carob beans,
-Carrageenan, a carrageenan derived from red algae,
-Glucomannan, glucomannan derived from konjac gum,
-Polysaccharides with primary alcohol functional groups derived from fermentation, xanthan, hyaluronic acid,
-Cellulose,
A cellulose component selected from the group consisting of hydroxypropylmethylcellulose and methylethylcellulose, methylhydroxymethylcellulose;
-Polyholoside,
-Agar,
Alginate, sodium salt of alginic acid, sodium alginate,
-Starch, amylopectin, amylose, starch derived from wheat, starch derived from rice, starch derived from potato, starch derived from corn,
-Chitosan,
-Card run,
-Adragante rubber or tragacanth rubber,
-Gum arabic or gum acacia,
-Kia rubber,
-Elemi rubber,
-Gellan gum,
-Gatch rubber or Indian rubber,
-Karaya gum,
-Shellac, and-manila rubber,
A polysaccharide selected from the group consisting of:
b)-cyclodextrin, alpha cyclodextrin, beta cyclodextrin or gamma cyclodextrin and any mixtures thereof,
-Dextrin,
-Raffinose, cellobiose, sucrose, maltose, lactose, trehalose, dihydroxyacetone (DHA), fructose, sorbose, ribose, deoxyribose, xylose, arabinose, glucose, mannose, galactose, erythrose, threose, allose, atrose, gulose, idose , Talose, erythrulose, xylulose, psicose, tagatose, cedoheptulose, xylobiose, chitobiose, nigerose, aminaribiose, cojibiose, sofolose, gentianose, gentiobiose, melibiose, melezitose, turanose, stachyose, bell bass course
-Gluconic acid, gluconolactone, glucosamine, galactosamine, galactosamine sulfate, glucosamine sulfate,
-Saponins, saponins derived from quilla bark,
-Guanosine, uridine,
-Streptomycin sulfate, and-riboflavin,
Oligosaccharides selected from the group consisting of monosaccharides and disaccharides, and c) -glycerol, sorbitol, erythritol, maltitol, sorbitol, mannitol, lactitol, galactitol, ribitol, glycerol, xylitol, Myo-inositol and polyethylene glycol,
A polyol selected from the group consisting of:
The crosslinked polymer of claim 7 selected from the group consisting of:
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Application Number | Priority Date | Filing Date | Title |
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FRFR0501674 | 2005-02-18 | ||
FR0501674A FR2882366B1 (en) | 2005-02-18 | 2005-02-18 | RETICULATED CARBOHYDRATE POLYMER, IN PARTICULAR BASED ON POLYSACCHARIDES AND / OR POLYOLS |
US11/174414 | 2005-07-01 | ||
US11/174,414 US9133279B2 (en) | 2005-02-18 | 2005-07-01 | Cross-linked polymer of carbohydrate, notably based on polysaccharides, and/or on oligosaccharides and/or on polyols |
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JP2006225392A true JP2006225392A (en) | 2006-08-31 |
JP5291863B2 JP5291863B2 (en) | 2013-09-18 |
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JP (1) | JP5291863B2 (en) |
KR (1) | KR101372646B1 (en) |
DE (1) | DE102006007831C5 (en) |
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GB (1) | GB2423252B (en) |
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JP2009095792A (en) * | 2007-10-18 | 2009-05-07 | Neos Co Ltd | Selective sticking agent for halogenated aromatic compound contained in medium and selectively sticking method |
JP2010537959A (en) * | 2007-08-31 | 2010-12-09 | グリーンテク | Cosmetic composition containing one or more compounds of the type β- (1,3) -glucuronan or β- (1,3) -glucoglucuronan |
JP2015535307A (en) * | 2012-10-25 | 2015-12-10 | ビーエーエスエフ ビューティ ケア ソリューションズ フランス エスエーエスBASF Beauty Care Solutions France S.A.S. | Hyaluronate and glucomannan polymers |
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US8912304B2 (en) | 2007-05-17 | 2014-12-16 | Massachusetts Institute Of Technology | Polyol-based polymers |
WO2012022478A2 (en) * | 2010-08-19 | 2012-02-23 | Merz Pharma Gmbh & Co. Kgaa | Filler composition comprising beta-glucans |
CN114409929B (en) * | 2022-02-07 | 2024-07-05 | 南京易亨制药有限公司 | Polymer hydrogel, preparation method and application thereof |
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GB2423252A (en) | 2006-08-23 |
KR20060093072A (en) | 2006-08-23 |
KR101372646B1 (en) | 2014-03-10 |
DE102006007831C5 (en) | 2018-05-24 |
GB0602683D0 (en) | 2006-03-22 |
JP5291863B2 (en) | 2013-09-18 |
GB2423252B (en) | 2007-10-17 |
DE102006007831B4 (en) | 2009-08-20 |
ES2293816B2 (en) | 2010-03-11 |
ES2293816A1 (en) | 2008-03-16 |
DE102006007831A1 (en) | 2006-10-12 |
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