JPH02202581A - Inhibitor of photo-deterioration - Google Patents
Inhibitor of photo-deteriorationInfo
- Publication number
- JPH02202581A JPH02202581A JP1022112A JP2211289A JPH02202581A JP H02202581 A JPH02202581 A JP H02202581A JP 1022112 A JP1022112 A JP 1022112A JP 2211289 A JP2211289 A JP 2211289A JP H02202581 A JPH02202581 A JP H02202581A
- Authority
- JP
- Japan
- Prior art keywords
- acid
- gallate
- catechins
- catechin
- appropriate amount
- 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.)
- Pending
Links
- 239000003112 inhibitor Substances 0.000 title claims abstract description 14
- ADRVNXBAWSRFAJ-UHFFFAOYSA-N catechin Natural products OC1Cc2cc(O)cc(O)c2OC1c3ccc(O)c(O)c3 ADRVNXBAWSRFAJ-UHFFFAOYSA-N 0.000 claims abstract description 41
- 235000005487 catechin Nutrition 0.000 claims abstract description 41
- PFTAWBLQPZVEMU-DZGCQCFKSA-N (+)-catechin Chemical compound C1([C@H]2OC3=CC(O)=CC(O)=C3C[C@@H]2O)=CC=C(O)C(O)=C1 PFTAWBLQPZVEMU-DZGCQCFKSA-N 0.000 claims abstract description 21
- 150000001765 catechin Chemical class 0.000 claims abstract description 21
- 229950001002 cianidanol Drugs 0.000 claims abstract description 20
- XMOCLSLCDHWDHP-IUODEOHRSA-N epi-Gallocatechin Chemical compound C1([C@H]2OC3=CC(O)=CC(O)=C3C[C@H]2O)=CC(O)=C(O)C(O)=C1 XMOCLSLCDHWDHP-IUODEOHRSA-N 0.000 claims abstract description 16
- WMBWREPUVVBILR-UHFFFAOYSA-N GCG Natural products C=1C(O)=C(O)C(O)=CC=1C1OC2=CC(O)=CC(O)=C2CC1OC(=O)C1=CC(O)=C(O)C(O)=C1 WMBWREPUVVBILR-UHFFFAOYSA-N 0.000 claims abstract description 11
- XMOCLSLCDHWDHP-UHFFFAOYSA-N L-Epigallocatechin Natural products OC1CC2=C(O)C=C(O)C=C2OC1C1=CC(O)=C(O)C(O)=C1 XMOCLSLCDHWDHP-UHFFFAOYSA-N 0.000 claims abstract description 10
- 244000269722 Thea sinensis Species 0.000 claims abstract description 10
- DZYNKLUGCOSVKS-UHFFFAOYSA-N epigallocatechin Natural products OC1Cc2cc(O)cc(O)c2OC1c3cc(O)c(O)c(O)c3 DZYNKLUGCOSVKS-UHFFFAOYSA-N 0.000 claims abstract description 10
- 239000000284 extract Substances 0.000 claims abstract description 10
- LSHVYAFMTMFKBA-TZIWHRDSSA-N (-)-epicatechin-3-O-gallate Chemical compound O([C@@H]1CC2=C(O)C=C(C=C2O[C@@H]1C=1C=C(O)C(O)=CC=1)O)C(=O)C1=CC(O)=C(O)C(O)=C1 LSHVYAFMTMFKBA-TZIWHRDSSA-N 0.000 claims abstract description 9
- WMBWREPUVVBILR-WIYYLYMNSA-N (-)-Epigallocatechin-3-o-gallate Chemical compound O([C@@H]1CC2=C(O)C=C(C=C2O[C@@H]1C=1C=C(O)C(O)=C(O)C=1)O)C(=O)C1=CC(O)=C(O)C(O)=C1 WMBWREPUVVBILR-WIYYLYMNSA-N 0.000 claims abstract description 8
- 235000009411 Rheum rhabarbarum Nutrition 0.000 claims abstract description 8
- LVJJFMLUMNSUFN-UHFFFAOYSA-N gallocatechin gallate Natural products C1=C(O)C=C2OC(C=3C=C(O)C(O)=CC=3)C(O)CC2=C1OC(=O)C1=CC(O)=C(O)C(O)=C1 LVJJFMLUMNSUFN-UHFFFAOYSA-N 0.000 claims abstract description 8
- LSHVYAFMTMFKBA-UHFFFAOYSA-N ECG Natural products C=1C=C(O)C(O)=CC=1C1OC2=CC(O)=CC(O)=C2CC1OC(=O)C1=CC(O)=C(O)C(O)=C1 LSHVYAFMTMFKBA-UHFFFAOYSA-N 0.000 claims abstract description 7
- 229940030275 epigallocatechin gallate Drugs 0.000 claims abstract description 7
- PFTAWBLQPZVEMU-ZFWWWQNUSA-N (+)-epicatechin Natural products C1([C@@H]2OC3=CC(O)=CC(O)=C3C[C@@H]2O)=CC=C(O)C(O)=C1 PFTAWBLQPZVEMU-ZFWWWQNUSA-N 0.000 claims abstract description 5
- PFTAWBLQPZVEMU-UKRRQHHQSA-N (-)-epicatechin Chemical compound C1([C@H]2OC3=CC(O)=CC(O)=C3C[C@H]2O)=CC=C(O)C(O)=C1 PFTAWBLQPZVEMU-UKRRQHHQSA-N 0.000 claims abstract description 5
- 239000004480 active ingredient Substances 0.000 claims abstract description 5
- LPTRNLNOHUVQMS-UHFFFAOYSA-N epicatechin Natural products Cc1cc(O)cc2OC(C(O)Cc12)c1ccc(O)c(O)c1 LPTRNLNOHUVQMS-UHFFFAOYSA-N 0.000 claims abstract description 5
- 235000012734 epicatechin Nutrition 0.000 claims abstract description 5
- XMOCLSLCDHWDHP-SWLSCSKDSA-N (+)-Epigallocatechin Natural products C1([C@H]2OC3=CC(O)=CC(O)=C3C[C@@H]2O)=CC(O)=C(O)C(O)=C1 XMOCLSLCDHWDHP-SWLSCSKDSA-N 0.000 claims abstract description 4
- LSHVYAFMTMFKBA-PZJWPPBQSA-N (+)-catechin-3-O-gallate Chemical compound O([C@H]1CC2=C(O)C=C(C=C2O[C@@H]1C=1C=C(O)C(O)=CC=1)O)C(=O)C1=CC(O)=C(O)C(O)=C1 LSHVYAFMTMFKBA-PZJWPPBQSA-N 0.000 claims abstract description 4
- WMBWREPUVVBILR-GHTZIAJQSA-N (+)-gallocatechin gallate Chemical compound O([C@H]1CC2=C(O)C=C(C=C2O[C@@H]1C=1C=C(O)C(O)=C(O)C=1)O)C(=O)C1=CC(O)=C(O)C(O)=C1 WMBWREPUVVBILR-GHTZIAJQSA-N 0.000 claims abstract description 4
- 235000011468 Albizia julibrissin Nutrition 0.000 claims abstract description 4
- 240000005852 Mimosa quadrivalvis Species 0.000 claims abstract description 4
- 244000299790 Rheum rhabarbarum Species 0.000 claims abstract 2
- 238000001782 photodegradation Methods 0.000 claims description 16
- 239000002738 chelating agent Substances 0.000 claims description 9
- 244000062793 Sorghum vulgare Species 0.000 claims description 4
- 235000019713 millet Nutrition 0.000 claims description 4
- 239000003795 chemical substances by application Substances 0.000 claims description 3
- 239000002537 cosmetic Substances 0.000 abstract description 12
- 235000013305 food Nutrition 0.000 abstract description 9
- 235000013616 tea Nutrition 0.000 abstract description 4
- 230000006866 deterioration Effects 0.000 abstract description 3
- 230000002401 inhibitory effect Effects 0.000 abstract description 3
- 244000235603 Acacia catechu Species 0.000 abstract 1
- 235000006226 Areca catechu Nutrition 0.000 abstract 1
- 244000209117 Castanea crenata Species 0.000 abstract 1
- 235000003801 Castanea crenata Nutrition 0.000 abstract 1
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- 238000004519 manufacturing process Methods 0.000 description 30
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- 239000000203 mixture Substances 0.000 description 25
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 20
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 15
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 15
- 239000003205 fragrance Substances 0.000 description 15
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- 239000008213 purified water Substances 0.000 description 13
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 12
- 239000002253 acid Substances 0.000 description 11
- 239000003755 preservative agent Substances 0.000 description 10
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 8
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 8
- 230000000694 effects Effects 0.000 description 8
- BXWNKGSJHAJOGX-UHFFFAOYSA-N hexadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCO BXWNKGSJHAJOGX-UHFFFAOYSA-N 0.000 description 8
- 235000019645 odor Nutrition 0.000 description 8
- 238000003756 stirring Methods 0.000 description 8
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- 150000003839 salts Chemical class 0.000 description 7
- ALYNCZNDIQEVRV-UHFFFAOYSA-N 4-aminobenzoic acid Chemical compound NC1=CC=C(C(O)=O)C=C1 ALYNCZNDIQEVRV-UHFFFAOYSA-N 0.000 description 6
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- KCXVZYZYPLLWCC-UHFFFAOYSA-N EDTA Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(O)=O)CC(O)=O KCXVZYZYPLLWCC-UHFFFAOYSA-N 0.000 description 5
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- 239000002202 Polyethylene glycol Substances 0.000 description 4
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 4
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 4
- 235000010323 ascorbic acid Nutrition 0.000 description 4
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- ALSTYHKOOCGGFT-KTKRTIGZSA-N (9Z)-octadecen-1-ol Chemical compound CCCCCCCC\C=C/CCCCCCCCO ALSTYHKOOCGGFT-KTKRTIGZSA-N 0.000 description 3
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 3
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- 239000011721 thiamine Substances 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- 239000004408 titanium dioxide Substances 0.000 description 1
- 229940042585 tocopherol acetate Drugs 0.000 description 1
- 235000019149 tocopherols Nutrition 0.000 description 1
- 229960000716 tonics Drugs 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- UNXRWKVEANCORM-UHFFFAOYSA-N triphosphoric acid Chemical compound OP(O)(=O)OP(O)(=O)OP(O)(O)=O UNXRWKVEANCORM-UHFFFAOYSA-N 0.000 description 1
- 229960005066 trisodium edetate Drugs 0.000 description 1
- DCXXMTOCNZCJGO-UHFFFAOYSA-N tristearoylglycerol Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCC(OC(=O)CCCCCCCCCCCCCCCCC)COC(=O)CCCCCCCCCCCCCCCCC DCXXMTOCNZCJGO-UHFFFAOYSA-N 0.000 description 1
- 229960004418 trolamine Drugs 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000003871 white petrolatum Substances 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
- 235000014692 zinc oxide Nutrition 0.000 description 1
- 229930007845 β-thujaplicin Natural products 0.000 description 1
- QUEDXNHFTDJVIY-UHFFFAOYSA-N γ-tocopherol Chemical class OC1=C(C)C(C)=C2OC(CCCC(C)CCCC(C)CCCC(C)C)(C)CCC2=C1 QUEDXNHFTDJVIY-UHFFFAOYSA-N 0.000 description 1
Landscapes
- Food Preservation Except Freezing, Refrigeration, And Drying (AREA)
- Medicinal Preparation (AREA)
- Cosmetics (AREA)
- Anti-Oxidant Or Stabilizer Compositions (AREA)
Abstract
Description
【発明の詳細な説明】
［産業上の利用分野］
本発明は、新規にして、かつ安全なる光劣化防止剤、さ
らに詳しくは、カテキン類またはその縮合物とキレ−１
・剤とを有効成分とする食品、化粧品、医薬品等用の光
劣化防止剤に関する。DETAILED DESCRIPTION OF THE INVENTION [Industrial Application Field] The present invention provides a novel and safe photodegradation inhibitor, more specifically, a novel and safe photodegradation inhibitor.
・Related to photodegradation inhibitors for foods, cosmetics, pharmaceuticals, etc. that have this as an active ingredient.
［従来の技術］
食品、化粧品、医薬品等は、直射日光下やショーケース
の光の下で陳列される場合が多く、また特に化粧品や医
薬品の場合、皮Ｉｆ！Ｉや毛髪等に塗擦して使用する物
は、人体上で光にさらされることになる。その際、これ
らの光によって、配合成分である油脂や活性剤等の基剤
が劣化したり、薬剤や色素が変質して、風味の悪化、異
臭の発生、変色等が起き、さらには効果の低下、毒性や
刺激性を有する物質の発生等が生じる場合がある。これ
らを防ぐために、３ａ常は紫外線吸収剤や酸化防止剤を
配合したり、遮光容器に入れたりしていた。[Prior Art] Foods, cosmetics, pharmaceuticals, etc. are often displayed under direct sunlight or under the light of showcases, and especially in the case of cosmetics and pharmaceuticals, skin If! Products that are used by rubbing on skin or hair are exposed to light on the human body. At that time, these lights deteriorate the base ingredients such as oils and fats and active agents, which are compounded ingredients, and change the quality of drugs and pigments, causing deterioration of flavor, generation of strange odors, discoloration, etc., and even reducing effectiveness. This may result in the production of toxic or irritating substances. To prevent these, 3a products are usually mixed with ultraviolet absorbers and antioxidants, or placed in light-shielding containers.
［発明が解決しようとする課題］
従来技術の問題点
しかしながら処方上やデザイン上の制約を受けるねりに
は、光劣化を防止する効果が十分ではなかった。[Problems to be Solved by the Invention] Problems with the Prior Art However, the effect of preventing photodeterioration was not sufficient for bends that are subject to prescription and design constraints.
従って、各種の剤型に容易に配合でき、光劣化に対して
これを有効に防止する、安全性の高い光劣化防止剤の出
現が望まれていた。Therefore, there has been a desire for a highly safe photodegradation inhibitor that can be easily incorporated into various dosage forms and effectively prevents photodegradation.
発明の目的
本発明者らは、上記事情に鑑み、鋭意検討した結果、カ
テキン類およびその縮合物に、強い光劣化防止効果があ
ること発見し、その上、キレート剤のと組合せにより、
さらに効果が強まることを見出し、本発明を完成するに
至った。Purpose of the Invention In view of the above circumstances, the present inventors have made extensive studies and discovered that catechins and their condensates have a strong photodegradation prevention effect, and in addition, by combining them with a chelating agent,
They discovered that the effect was even stronger and completed the present invention.
［課題を解決するための手段］
すなわち本発明は、カテキン類やその縮合物、またはこ
れらとキレート剤とを有効成分とする光劣化防止剤であ
る。[Means for Solving the Problems] That is, the present invention is a photodegradation inhibitor containing catechins, condensates thereof, or these and a chelating agent as active ingredients.
以下、本発明の構成について詳述する。Hereinafter, the configuration of the present invention will be explained in detail.
カテキン類は、植物に含まれる縮合型タンニンの単量体
であり、フラバン−３−オールを基本骨格として有する
物質群で、カテキンやガロカテキンの他、没食子酸のエ
ステルであるカテキンガレート、ガロカテキンガレート
、これらの立体異性体であるエピカテキン、エピガロカ
テキン、エピカテキンガレート、エピガロカテキンガレ
ートなどを含んでいる。これらのカテキン類は、合成に
よって得ることもできるが、植物９例えば大黄、何首烏
、地楡、ミモザ、粟、阿仙薬、茶などから溶媒抽出等で
、容易に得ることができる。その抽出方法は特に限定さ
れるものではないが、例えば、以下のようにして抽出を
行なう。Catechins are monomers of condensed tannins contained in plants, and are a group of substances that have flavan-3-ol as a basic skeleton.In addition to catechin and gallocatechin, catechin gallate, which is an ester of gallic acid, and gallocatechin gallate , these stereoisomers include epicatechin, epigallocatechin, epicatechin gallate, epigallocatechin gallate, etc. Although these catechins can be obtained by synthesis, they can also be easily obtained by solvent extraction from plants such as rhubarb, heshuwuru, jiyue, mimosa, millet, Asianyaku, and tea. Although the extraction method is not particularly limited, for example, extraction is performed as follows.
すなわち、乾燥した各植物を、メタノール、エタノール
などのアルコール、１，３−ブチＩノングリコール等の
多価アルコール、アセトン、エーテル、酢酸エチルなど
の極性有機溶媒、水などの単独または混合溶媒に浸漬し
、室温または加熱抽出する。That is, each dried plant is immersed in a single or mixed solvent such as an alcohol such as methanol or ethanol, a polyhydric alcohol such as 1,3-buty-I non-glycol, a polar organic solvent such as acetone, ether, or ethyl acetate, or water. and extract at room temperature or with heat.
その抽出液から溶媒を留去して、各種カテキン含有抽出
物を得る。これを、高速液体クロマトグラフィーなどに
よって各種カテキンの単品を得ることができるが、抽出
物のまま、または抽出液の形で配合してもよい。The solvent is distilled off from the extract to obtain various catechin-containing extracts. Various catechins can be obtained individually by high-performance liquid chromatography or the like, but they may also be blended as an extract or in the form of an extract.
溶媒抽出を行なう前に、粉砕した葉をクロロホルムなど
に浸漬しておくと、不要な色素などが除去され、後処理
が行ないやすい場合がある。If the crushed leaves are immersed in chloroform or the like before solvent extraction, unnecessary pigments may be removed and post-processing may be easier.
かくして本発明のカテキン類が得られる。このものは、
水、アルコール、多価アルコールまたはアルコール水溶
液に溶解することによって、水中にも油中にも自由に溶
解させることが可能であり、従来用いられていた紫外線
吸収剤や酸化防止剤などに比較して応用範囲が広い。In this way, the catechins of the present invention are obtained. This thing is
By dissolving in water, alcohol, polyhydric alcohol, or aqueous alcohol solution, it can be freely dissolved in both water and oil, and is more effective than conventionally used ultraviolet absorbers and antioxidants. Wide range of applications.
本発明で用いられる縮合物とは縮合型タンニンであり、
これらはカテキン類の酸化重合物である。The condensate used in the present invention is a condensed tannin,
These are oxidized polymers of catechins.
これらの縮合物は合成によって得ることもできるが、大
黄、何首烏、地楡、ミモザ、粟、阿仙薬、茶など植物か
ら溶媒抽出等で、容易に得ることができる。Although these condensates can be obtained by synthesis, they can also be easily obtained by solvent extraction from plants such as rhubarb, heshuwura, jiyue, mimosa, millet, asianyaku, and tea.
本発明で用いられるキレート剤としては、ビロリン酸、
トリポリリン酸、メタリン酸、ヘキサメタリン酸、１−
ヒドロキシエタン−１，１−シフオスホン酸、フィチン
酸等のリン酸およびその塩、イミノニ酢酸、エチレンジ
アミン四酢酸、ジエチレントリアミン五酢酸、グリコー
ルエーテルジアミン四酢酸、トノエチレンテトラミン六
酢酸等のアミノポリ酢酸およびその塩、グリコール酸、
リンゴ酸、酒石酸、クエン酸、乳酸、グルコン酸、グル
クロン酸等のヒドロキシカルボン酸およびその塩、コハ
ク酸、マロン酸、マレイン酸、フマール酸、フタル酸等
の有機酸およびその塩、アスパラギン酸、グルタミン酸
、グリシン等のアミノ酸およびその塩等が挙げられる。Chelating agents used in the present invention include birophosphoric acid,
Tripolyphosphoric acid, metaphosphoric acid, hexametaphosphoric acid, 1-
Phosphoric acids and their salts such as hydroxyethane-1,1-cyphosphonic acid and phytic acid, aminopolyacetic acids and their salts such as iminodiacetic acid, ethylenediaminetetraacetic acid, diethylenetriaminepentaacetic acid, glycol etherdiaminetetraacetic acid, tonoethylenetetraminehexaacetic acid, glycolic acid,
Hydroxycarboxylic acids and their salts such as malic acid, tartaric acid, citric acid, lactic acid, gluconic acid, and glucuronic acid, organic acids and their salts such as succinic acid, malonic acid, maleic acid, fumaric acid, and phthalic acid, aspartic acid, and glutamic acid. , amino acids such as glycine, and salts thereof.
上記成分のうち、特に好ましいものとしてはリン酸およ
びその塩が挙げられる。Among the above components, particularly preferred are phosphoric acid and its salts.
本発明のカテキン類またはその縮合物の化粧品、医薬品
、食品またはその原料への配合量は、乾燥残分として０
．００１〜２重量％であり、好ましくはｏ、ｏｏｓ〜０
．２重量％である。０．００１重量％未満では本発明の
光劣化防止効果が得られず、２重量％を超えると系への
着色が著しいなど製剤上不都合である。またキレート剤
に関しては、０．００１〜５重量％、好ましくは０．０
１〜１重量％である。０．００１重量％未満では本発明
において、キレート剤を添加することによる、さらなる
効果は得られず、５型皿％を超えると、系のｐＨが下が
ったり、溶解性の問題など製剤上不都合である。The amount of the catechins or their condensates of the present invention incorporated into cosmetics, pharmaceuticals, foods, or their raw materials is 0 as a dry residue.
．． 001 to 2% by weight, preferably o, oos to 0
．． It is 2% by weight. If it is less than 0.001% by weight, the photodegradation prevention effect of the present invention cannot be obtained, and if it exceeds 2% by weight, there are problems in terms of formulation, such as significant coloring of the system. Regarding the chelating agent, 0.001 to 5% by weight, preferably 0.0%
It is 1 to 1% by weight. If it is less than 0.001% by weight, no further effect can be obtained by adding the chelating agent in the present invention, and if it exceeds 5% by weight, the pH of the system may drop and there may be problems with the formulation, such as solubility problems. be.
本発明の光劣化防止剤は、基剤、例えば油脂類やグリセ
リン、グリセリン誘導体、ポリグリセリン、ポリグリセ
リン脂肪酸エステル、ポリグリセリンアルキルエーテル
等、あるいはポリエチレングリコール、ポリエチレング
リコール脂肪酸エステル、ポリオキシエチレンアルキル
エーテル、ポリオキシエチレンボリオキシプロビレンア
ルキルエーテル等のオキシアルキレン鎖を有する物質お
よびこれらと無機酸との縮合物またはその塩等、さらに
は色素や各種薬剤等に対して、あるいはこれらが水系ま
たは油系を問わず配合されている各種の化粧品、医薬品
、食品等に対して効果を発揮する。またバラアミノ安息
香酸およびその誘導体、ジベンゾイルメタンおよびその
誘導体、桂皮酸およびその誘導体等の紫外線吸収剤や、
トコフェロール、有機酸。The photodegradation inhibitor of the present invention is a base material such as oils and fats, glycerin, glycerin derivatives, polyglycerin, polyglycerin fatty acid ester, polyglycerin alkyl ether, or polyethylene glycol, polyethylene glycol fatty acid ester, polyoxyethylene alkyl ether, etc. Substances with oxyalkylene chains such as polyoxyethylene polyoxypropylene alkyl ether, condensates of these with inorganic acids, or their salts, as well as pigments and various chemicals, or when they are water-based or oil-based. It is effective in a variety of cosmetics, pharmaceuticals, foods, etc., regardless of the product. In addition, ultraviolet absorbers such as paraaminobenzoic acid and its derivatives, dibenzoylmethane and its derivatives, cinnamic acid and its derivatives,
Tocopherol, organic acid.
あるいはＢＨＴ、ＢＨＡ等の酸化防止剤と併用すること
により一届の効果を期待出来る。Alternatively, a great effect can be expected by using it in combination with an antioxidant such as BHT or BHA.
本発明においては、前記必須成分としてのカテキン類ま
たはその縮合物、それらとキレート剤との組合せに加え
て、目的に応じ通常の化粧品、医薬品、食品の含有成分
が利用できる。そのような成分としでは、油分、界面活
性剤、増粘剤、中和剤、防腐剤、酸化防止剤、粉体成分
、色素、香料、紫外線吸収剤、薬効剤などが挙げられ、
必要に応じて適宜組合せて用いられるものである。In the present invention, in addition to catechins or their condensates as the above-mentioned essential components, and their combination with a chelating agent, common ingredients contained in cosmetics, pharmaceuticals, and foods can be used depending on the purpose. Such ingredients include oils, surfactants, thickeners, neutralizers, preservatives, antioxidants, powder ingredients, pigments, fragrances, ultraviolet absorbers, medicinal agents, etc.
They may be used in appropriate combinations as necessary.
本発明に係る化粧品、医薬品、食品の剤型は任意であり
、例えば、水溶液系、可溶化系、乳化系、粉末分散系、
水−油２層系、水−油一粉末３層系など、どのような基
剤でもよく、用途も化粧水、乳液、クリーム、パックな
どの基礎化粧料、口紅、ファンデーションなどのメーキ
ャップ化粧料、シャンプー、リンス、ヘアトニックなど
の頭髪化粧料などの化粧料あるいは医薬品、医薬部外品
など、乳製品、即席麺、粉末または液体スープ、フライ
食品、果汁飲料、炭酸飲料、漬物、菓子など多岐にわた
る。さらに、これらの原料、例えば、動植物油、活性剤
、色素、香料、薬剤または動物肉、魚肉などに直接添加
することもできる。The dosage form of the cosmetics, pharmaceuticals, and foods according to the present invention is arbitrary, and includes, for example, an aqueous solution system, a solubilized system, an emulsion system, a powder dispersion system,
Any base may be used, such as a two-layer water-oil system or a three-layer water-oil/powder system, and can be used for basic cosmetics such as lotions, emulsions, creams, and packs, makeup cosmetics such as lipsticks, foundations, etc. A wide variety of products, including cosmetics such as hair cosmetics such as shampoos, conditioners, and hair tonics, pharmaceuticals, quasi-drugs, dairy products, instant noodles, powdered or liquid soups, fried foods, fruit juice drinks, carbonated drinks, pickles, and sweets. . Furthermore, it can also be directly added to these raw materials, such as animal and vegetable oils, active agents, pigments, fragrances, drugs, animal meat, fish meat, and the like.
［発明の効果］
本発明の光劣化防止剤は、次のような利点を持っている
。[Effects of the Invention] The photodegradation inhibitor of the present invention has the following advantages.
（１）製品のｐＨが下がるのを抑える。(1) Prevent the pH of the product from decreasing.
（２）製品からの酸化生成物−例えば過酸化物等の発生
を抑える。(2) Suppress the generation of oxidation products such as peroxides from the product.
（３）製品の変色を抑える。(3) Suppress product discoloration.
（４）製品のにおい悪化を抑える。(4) Suppress product odor deterioration.
（５）製品中の各種薬剤の減少を抑える。(5) Suppress the reduction of various drugs in products.
［実施例］
次に、実施例によって、本発明をさらに詳細に説明する
。本発明は、これによって限定されるものではない。[Example] Next, the present invention will be explained in more detail with reference to Examples. The present invention is not limited thereby.
製造例１
本例は、本発明による茶からのカテキンの抽出方法を説
明する。Preparation Example 1 This example illustrates a method for extracting catechins from tea according to the present invention.
乾燥した緑茶１ｋｇにクロロホルム１０ｋｇを加えて還
流洗浄した後、クロロホルムを除去する。残渣９５０８
に水３ｋｇを加えて撹拌し、浸潤させる。ここに、酢酸
エチル１０に８を加える。液相と残渣を分離し、液相か
ら酢酸エチルを留去する。残った水相を粉霧乾燥して緑
茶タンニン９７８を得る。これのカテキン純度は、７０
％以上であり、エピカテキン、エピガロカテキン、エピ
カテキンガレート、エピガロカテキンガレートなどが含
まれる。After adding 10 kg of chloroform to 1 kg of dried green tea and washing under reflux, the chloroform is removed. Residue 9508
Add 3 kg of water and stir to infiltrate. To this, add 8 parts to 10 parts of ethyl acetate. The liquid phase and the residue are separated and ethyl acetate is distilled off from the liquid phase. The remaining aqueous phase is powder-dried to obtain green tea tannin 978. The catechin purity of this is 70
% or more, and includes epicatechin, epigallocatechin, epicatechin gallate, epigallocatechin gallate, etc.
製造例２
本例は、製造例１で得られた緑茶カテキン混合物から各
種カテキンを単離する方法を説明する。Production Example 2 This example describes a method for isolating various catechins from the green tea catechin mixture obtained in Production Example 1.
製造例１で得られた緑茶タンニン１２ｇを、逆相分配カ
ラムを用い、アセトン：テトラヒドロフラン：水＝１２
： １０ ： ７８（容量％）なる展開溶媒で高速液
体クロマトグラフィーにて分離すれば、エピガロカテキ
ン（１，４ｇ）、エピカテキン（０，９ｇ）、カテキン
（０，７８）、エピガロカテキンガレート（４，９ｇＬ
エピカテキンガレート（１，２ｇ）の順で溶出し、各カ
テキンを単離することができる。Using a reverse phase distribution column, 12 g of green tea tannin obtained in Production Example 1 was mixed with acetone:tetrahydrofuran:water=12
When separated by high performance liquid chromatography using a developing solvent of : 10 : 78 (volume %), epigallocatechin (1.4 g), epicatechin (0.9 g), catechin (0.78), epigallocatechin gallate (4.9gL
Each catechin can be isolated by elution in the order of epicatechin gallate (1.2 g).
製造例３ 本例では、大黄からタンニンを得る方法を説明する。Manufacturing example 3 This example describes a method for obtaining tannins from rhubarb.
乾燥した大黄の根２ｋｇを、水５ｋｇに浸漬した後口過
して水層を得る。これにエーテル３ｋｇを加えてよく振
盪し、エーテル層を除去する。さらに、水層に酢酸エチ
ル３ｋｇを加えて抽出する。酢酸工チル層から溶媒を留
去して屹燥し、大黄タンニン６０８を得る。この抽出物
には、分子量１０００〜３０００の縮合型タンニン（カ
テキン類の酸化重合物）が含まれており、タンニン含量
は７０％程度である。2 kg of dried rhubarb root is soaked in 5 kg of water and passed through the mouth to obtain a water layer. Add 3 kg of ether to this and shake well to remove the ether layer. Furthermore, 3 kg of ethyl acetate is added to the aqueous layer for extraction. The solvent is distilled off from the ethyl acetate layer and dried to obtain Rhubarb Tannin 608. This extract contains condensed tannins (oxidized polymers of catechins) with a molecular weight of 1000 to 3000, and the tannin content is about 70%.
実験例１ 本発明例として、以下の試験を行なった。Experimental example 1 As an example of the present invention, the following tests were conducted.
リノール酸エチル（日本油脂■製）５ｇ中に、製造例１
で得た緑茶由来のカテキン混合物を添加して、Ｘｅフェ
ードメーター（中心にＸｅランプがあり、その周りを試
料が回転しながら光照射を受ける機械）に入れ、２５℃
で保存して経時の光劣化の度合を、過酸化物価を指標と
して評価した。また、比較として、バラアミノ安息香酸
（ＰＡＢＡ）を添加した試験も行なった。In 5 g of ethyl linoleate (manufactured by NOF ■), Production Example 1
Add the green tea-derived catechin mixture obtained above, place it in a Xe fade meter (a machine with a Xe lamp in the center, around which the sample rotates and receives light irradiation), and heat at 25°C.
The degree of photodeterioration over time after storage was evaluated using peroxide value as an index. For comparison, a test was also conducted in which paraaminobenzoic acid (PABA) was added.
なお、用いたＸｅランプは、そのスペクトルが太陽光の
スペクトルに類似しており、また、紫外部の照射エネル
ギー量は太陽光のそれにほぼ等しいことから採用した。The Xe lamp used was chosen because its spectrum is similar to that of sunlight, and the amount of irradiation energy in the ultraviolet region is approximately equal to that of sunlight.
結果を表−１に示す。The results are shown in Table-1.
また、１６時間後の油のにおいを、専門パネラ−３名に
判定させたところ、Ｎｔ１２〜４では変臭が認められな
かったが、磁５では明らかな異臭が認められた。Furthermore, when three expert panelists judged the odor of the oil after 16 hours, no off-odor was observed for Nt12-4, but a clear off-odor was observed for Magnet 5.
表−１およびにおい判定から明らかなように、カテキン
混合物は光劣化を強く抑制した。As is clear from Table 1 and the odor evaluation, the catechin mixture strongly suppressed photodeterioration.
実験例２
製造例２で得られたカテキンを用いて、実験例１と同様
の試験を行なった。なお、比較として、ＢＨＴ、ＢＨＡ
、トコフェロールを用いた試験も行なった。結果を表−
２に示す。Experimental Example 2 Using the catechin obtained in Production Example 2, a test similar to Experimental Example 1 was conducted. For comparison, BHT, BHA
, tests were also conducted using tocopherols. Display the results -
Shown in 2.
のの、いずれも既存の酸化防止剤より強い抑制効果を示
した。All of NONO's antioxidants showed stronger inhibitory effects than existing antioxidants.
実験例３
製造例１で得られたカテキン混合物とキレート剤とを組
合せて、実験例１と同様の試験を行なった。結果を表−
３に示す。Experimental Example 3 A test similar to Experimental Example 1 was conducted using a combination of the catechin mixture obtained in Production Example 1 and a chelating agent. Display the results -
Shown in 3.
また、１６時間後の油のにおいを、専門パネラ−３名に
判定させたところ、Ｎｎ２〜６では変臭が認められなか
ったが、慮７〜９では明らかな異臭が認められた。Moreover, when three expert panelists judged the odor of the oil after 16 hours, no off-odor was observed in Nn2-6, but clear off-odor was observed in Nn7-9.
また、１６時間後の油のにおいを、専門パネラ−３名に
判定させたところ、Ｎα２〜６では変臭が認められなか
ったが、階７〜９では明らかな異臭が認められた。Furthermore, when three expert panelists judged the smell of the oil after 16 hours, no off-odor was observed on Nα2-6, but a clear off-odor was observed on floors 7-9.
表−２およびにおい判定かられかるように、カテキンの
種類によって光劣化防止力の差はあるも＊ 表中Ｎ０２
〜５には製造例１で得られたカテキン混合物が２階６・
７にはＢＨＴが、ＮＱ８・９にはトコフェロールが、い
ずれも１１００ｐｐずつ添加されている。As can be seen from Table 2 and odor evaluation, there are differences in the ability to prevent photodegradation depending on the type of catechin. *N02 in the table
~ 5 contains the catechin mixture obtained in Production Example 1 on the second floor 6.
BHT is added to No. 7, and tocopherol is added to No. 8 and No. 9, each of which has an amount of 1,100 pp.
＊ キレート剤の添加量は、黒２・３が２００ｐｐｍ
。*The amount of chelating agent added is 200 ppm for Black 2 and 3.
.
他は１１０００ｐｐである。Others are 11000pp.
＊表中数値は過酸化物（ｌＩ（ｍｅｑ／ｋｇ）実験例４
基剤油分を、実験例１・２のリノール酸エチルからトリ
エチレングリコール（牛丼化学製）の５０％水溶液５ｇ
に変えて試験を行なった。比較としてアスコルビン酸、
トコフェロール、４−ｔ−ブチル−４°−メトキシ−ジ
ベンゾイルメタン（ＢＭＤＭ）を添加したトリエチレン
グリコールで同様の試験を行なった。ただし、評価は１
週間後のにおい判定で行なった。判定は専門パネラ−３
名による。*The values in the table are peroxide (lI (meq/kg)) Experimental Example 4 The base oil was changed from ethyl linoleate of Experimental Examples 1 and 2 to 5 g of a 50% aqueous solution of triethylene glycol (Gyudon Kagaku).
I changed it and tested it. Ascorbic acid for comparison,
Similar tests were conducted with triethylene glycol spiked with tocopherol, 4-tert-butyl-4°-methoxy-dibenzoylmethane (BMDM). However, the rating is 1
The odor was evaluated after a week. Judgment by expert panel 3
By name.
結果を表−４に示す。The results are shown in Table 4.
例２で得たカテキン類を加えて、Ｘｅフェードメーター
中で２５℃で保存し、１週間後の変色、変臭の程度を調
べた。比較として、バラジメチルアミノ安息香酸２−エ
チルヘキシル（ＰＤＡＢＡ）を添加したものについても
評価した。なお、ギシギシ抽出物は、ギシギシの乾燥根
をへ午サンで抽出したものの乾燥残分である。このもの
は、黄色の色剤または肌あれ防止剤等として使用される
。The catechins obtained in Example 2 were added and stored at 25°C in a Xe fade meter, and the degree of discoloration and odor was examined after one week. For comparison, a sample to which 2-ethylhexyl valadimethylaminobenzoate (PDABA) was added was also evaluated. Incidentally, the Kishigishi extract is the dry residue obtained by extracting the dried roots of the Kishigishi with hegosan. This product is used as a yellow coloring agent or a skin roughness preventive agent.
結果を表−５に示す。The results are shown in Table-5.
表−４から明らがなごとく、カテキン類は、アスコルビ
ン酸、トコフェロール、４−ｔ−ブチル−４−メトキシ
−ジベンゾイルメタン単独の場合に比較して、顕著な光
劣化防止効果を有している。As is clear from Table 4, catechins have a remarkable photodegradation prevention effect compared to ascorbic acid, tocopherol, and 4-t-butyl-4-methoxy-dibenzoylmethane alone. There is.
実験例５
ギシギシ抽出物のトリオクタン酸グリセリル溶液をオリ
ーブ油に１％添加したもの５ｇに、製造数に、
本発明の光劣化防止剤を用いた化粧品、食品、医薬品の
製剤例を示す。当然のことながら、本発明は、これらに
限定されるものではない。Experimental Example 5 Examples of formulations of cosmetics, foods, and pharmaceuticals using the photodegradation inhibitor of the present invention are shown below. Naturally, the present invention is not limited to these.
実施例１ 乳液
ステアリン酸 ２．５セチル
アルコール １・５ワセリン
５．０流動パラフイン
１０．０ＰＯＥ （１０モル）モノ
オレイン酸エステル ２．０ポリエチレングリコール１
５００３．０トリエタノールアミン
１．０アスコルビン酸 ５．０
力テキン混合物（製造例１ ） ０．ＩＥ
Ｄ Ｔ Ａ Ｏ，０
１イオン交換水 残余香′１
ｌ１４３Ｉｌｌ量
（製法）
イオン交換水にポリエチレングリコール１５００とトリ
エタノールアミンおよびアスコルビン酸・カテキン混合
物・ＥＤＴＡを加え、加熱溶解して７０℃に保つ（水相
）。他の成分を混合し、加熱融解して７０℃に保つ（油
相）。水相に油相を加え予備乳化を行ない、ホモミキサ
ーで均一に乳化し、乳化後よくかきまぜながら３０℃ま
で冷却する。Example 1 Emulsion stearic acid 2.5 cetyl alcohol 1.5 vaseline
5.0 liquid paraffin
10.0 POE (10 mol) Monooleic acid ester 2.0 Polyethylene glycol 1
5003.0 Triethanolamine
1.0 Ascorbic acid 5.0
Chiritekin mixture (Production example 1) 0. IE
D T A O, 0
1 ion exchange water residual fragrance'1
Amount of 1143Ill (manufacturing method) Add polyethylene glycol 1500, triethanolamine, ascorbic acid/catechin mixture/EDTA to ion-exchanged water, dissolve by heating, and keep at 70°C (water phase). Mix other ingredients, heat and melt and keep at 70°C (oil phase). The oil phase is added to the water phase for preliminary emulsification, and the mixture is uniformly emulsified using a homomixer. After emulsification, the mixture is cooled to 30°C while stirring well.
実施例２ 化粧水
（アルコール相）
９５％エチルアルコール ２５・Ｏシ
コンエキス ０．５ＰＯＥ
（６０モル）硬化ヒマシ油エーテル ２．０酸化防止
剤・防腐剤 適量香料
適量（水相）
カテキン混合物（製造例１ ） ０．０５
グリセリン ５．０へキサメ
タリン酸ナトリウム ０．０５紫外線吸収剤
適量イオン交換水
残余（製法）
水相・アルコール相を調整後可溶化する。Example 2 Lotion (alcohol phase) 95% ethyl alcohol 25.Osicon extract 0.5POE
(60 mol) Hydrogenated castor oil ether 2.0 Antioxidant/preservative Appropriate amount Fragrance
Appropriate amount (aqueous phase) Catechin mixture (Production example 1) 0.05
Glycerin 5.0 Sodium hexametaphosphate 0.05 Ultraviolet absorber Appropriate amount of ion exchange water
Residue (manufacturing method) Solubilize after adjusting the aqueous and alcohol phases.
実施例３ クレンジングクリーム
（Ａ）セタノール ２．０ピー
スワツクス １．０固形パラフイン
１・０オレイン酸
２．０ワセリン １
０．０オリーブ油 ３５．０Ｐ
ＯＥ （２０）ソルビタンオレート２．４ジグリセリン
ジオレート２．６
プロビルバラベン ０．３（Ｂ）大黄
タンニン ０．１ポリエチレング
リコール ５．０水酸化カリウム
０．０８１−ヒドロキシエタン−１，１−シ
フオスホン酸水溶液 ０．８精製水
残余（製法）
（Ａ）の油相部と（Ｂ）の水相部を別々に加熱撹拌溶解
する。油相部を水相部中に添加し、乳化、冷却してクリ
ームを得た。Example 3 Cleansing cream (A) Setanol 2.0 piece wax 1.0 solid paraffin 1.0 oleic acid
2.0 Vaseline 1
0.0olive oil 35.0P
OE (20) Sorbitan oleate 2.4 Diglycerin diolate 2.6 Probylbaraben 0.3 (B) Rhubarb tannin 0.1 Polyethylene glycol 5.0 Potassium hydroxide
0.08 1-Hydroxyethane-1,1-cyphosphonic acid aqueous solution 0.8 Purified water
Residue (manufacturing method) The oil phase part of (A) and the aqueous phase part of (B) are separately heated and stirred to dissolve. The oil phase was added to the water phase, emulsified, and cooled to obtain a cream.
実施例４ 栄養乳液 （Ａ）ピースワックス ワセリン 脱臭ラノリン 月見草油 セチルイソオクタノエート ＰＯＥ （２）オレイルエーテル エチルバラベン ブチルパラベン 香料 （Ｂ）カルボキシビニルポリマー エビガロカテキンガレート ジエチレントリアミン−五酢酸水溶液 ジプロピレングリコール し−アルギニン 精製水 （製法） 実施例３に準じる。Example 4 Nutritional emulsion (A) Peace wax Vaseline deodorizing lanolin evening primrose oil Cetyl isooctanoate POE (2) Oleyl ether Ethylbaraben butylparaben fragrance (B) Carboxyvinyl polymer shrimp gallocatechin gallate Diethylenetriamine-pentaacetic acid aqueous solution dipropylene glycol Shi-Arginine purified water (Manufacturing method) Same as Example 3.
１．０
２．０
１．５
６．０
４．０
２．０
０．２
０．１
０．３
０．２
０．０１
０．１
２．０
０．２
残余
実施例５ ファンデーション
（Ａ）ステアリン酸 ２．０セチル
アルコール ０．３流動パラフイン
２０．０ポリオキシエチレン（１０モル
）オレイン酸エステル １．０ソルビタ
ントリオレイン酸エステル１．０香料
適量防腐剤 適
量（Ｂ）二酸化チタン ６．０タル
ク ６．０カオリン
３．０顔料
適量（Ｃ）カテキン混合物（ｒＭ、造例１ ）０
．００５１−ヒドロキシエタン−１，１−シフオスホン
酸ナトリウム ０．００５プロピレングリコー
ル ５．０ポリエチレングリコール４０００
５．０トリエタノールアミン ｉ、
。1.0 2.0 1.5 6.0 4.0 2.0 0.2 0.1 0.3 0.2 0.01 0.1 2.0 0.2 Remaining Example 5 Foundation (A) Stearic acid 2.0 Cetyl alcohol 0.3 Liquid paraffin
20.0 Polyoxyethylene (10 mol) Oleic acid ester 1.0 Sorbitan trioleic acid ester 1.0 Fragrance
Appropriate amount of preservative Appropriate amount (B) Titanium dioxide 6.0 Talc 6.0 Kaolin
3.0 pigment
Appropriate amount (C) Catechin mixture (rM, Example 1) 0
．． 0051-Hydroxyethane-1,1-sodium cyphosphonate 0.005 Propylene glycol 5.0 Polyethylene glycol 4000
5.0 triethanolamine i,
.
ビーガム ０．５精製水
残余（製法）
加熱溶解した（Ｃ）に、粉砕混合した（Ｂ）を加え、ホ
モミキサーで均一に分散させ７０℃に保つ。（Ａ）を混
合し加熱溶解して７０℃に保つ。前者を後者に加え乳化
を行い、乳化後冷却しながら撹拌してファンデーション
を得た。Veegum 0.5 purified water
Residue (manufacturing method) Add pulverized and mixed (B) to heated and dissolved (C), uniformly disperse with a homomixer, and maintain at 70°C. (A) is mixed, heated and dissolved, and kept at 70°C. The former was added to the latter to perform emulsification, and after emulsification, the mixture was stirred while cooling to obtain a foundation.
実施例６ アイライナー
（Ａ）軽質流動パラフィン
（Ｂ）ピースワックス
キャンデリラロウ
防腐剤
香料
（Ｃ）ジメチルジアルキルアンｔ−ラムヘクトライト（
Ｄ）エチルアルコール
ＨＥＣ
エピカテキンガレート
シクロヘキサンジアミン四酢酸ナトリウム（Ｅ）タルク
黒色酸化鉄
（製法）
（Ａ）の一部および（Ｂ）を加熱溶解後、６８．４７
３．０
３．０
０．１
０．１
４．５
２．８
３．０
０．０２
０．０１
５．０
１０．０
（Ｃ）を加
えて撹拌混合する。次に、（Ａ）の残部および（Ｄ）を
加温溶解し、前記混合物に添加し混合する。さらに、（
Ｅ）をホモミキサーにて分散し、冷却後容器に充填する
。Example 6 Eyeliner (A) Light liquid paraffin (B) Peace wax Candelilla wax Preservative Fragrance (C) Dimethyl dialkyl ant-ram hectorite (
D) Ethyl alcohol HEC epicatechin gallate cyclohexane diamine sodium tetraacetate (E) Talc black iron oxide (manufacturing method) After heating and dissolving a part of (A) and (B), 68.47 3.0 3.0 0.1 0.1 4.5 2.8 3.0 0.02 0.01 5.0 10.0 Add (C) and mix with stirring. Next, the remainder of (A) and (D) are dissolved by heating, and added to the mixture and mixed. moreover,(
Disperse E) using a homomixer, cool it, and then fill it into a container.
実施例７ 口紅
（Ａ）カルナバロウ ３゜０ミツロ
ウ ５．０（Ｂ）ヒマシ油
残余ラノリン
１１．０ミリスチン酸イソプロピル １０
．０（Ｃ）カテキン混合物（製造例１ ） ０．
０４エタノール ２．０（Ｄ）酸
化チタン ２．０ベンガラ
１．０赤色２０２号
３，０（Ｅ）香料
０．１（製法）
（Ａ）を加熱融解後、（Ｃ）を加えた（Ｂ）をこれに加
えて混合し、そこへ（Ｄ）ｆ！：加えて熱時ミキサーに
て分散する。残りの（Ｅ）を熱時添加して分散し、脱気
後成型して製品とする。Example 7 Lipstick (A) Carnauba wax 3°0 beeswax 5.0 (B) Castor oil
residual lanolin
11.0 Isopropyl myristate 10
．． 0(C) Catechin mixture (Production example 1) 0.
04 Ethanol 2.0 (D) Titanium oxide 2.0 Red iron
1.0 Red No. 202
3,0 (E) Fragrance
0.1 (Production method) After heating and melting (A), (B) with (C) added thereto is added and mixed, and (D) f! :Additionally, disperse with a mixer when hot. The remaining (E) is added and dispersed while hot, and after degassing, the product is molded.
実施例８ 口紅
（Ａ）流動パラフィン
グリセリントリステアレート
ヒマシ油
キャンデリラロウ
ポリエチレンワックス
ポリオキシエチレン（２０モル）ポリオキシプロピレン
（２０モル）２テトラデシルオクタデシルエーテル（Ｂ
）赤色２０２号
赤色２０４号
青色１号
黒色酸化鉄
雲母チタン
（Ｃ）エピカテキンガレート
１−ヒドロキシエタン−１，１−シフオスホン酸ナトリ
ウムポリビニルアルコール
ラポナイトＸ Ｌ Ｇ ”’
２０．０
２０、Ｏ
残余
８．０
１０．０
４．０
０．５
０．５
１．０
０．５
５．０
０．０Ｑ１
０．００１
０．５
１．０
イオン交換水 １０．０＊ 英国ラ
ボルテ社製の合成ベントナイトの商品名
（製法）
（Ａ）を８０℃にて溶解後、（Ｂ）を混合溶解し、同じ
く混合溶解した（Ｃ）を撹拌添加して乳化する。Example 8 Lipstick (A) Liquid paraffin Glycerin Tristearate Castor oil Candelilla wax Polyethylene wax Polyoxyethylene (20 mol) Polyoxypropylene (20 mol) 2 Tetradecyl octadecyl ether (B
) Red No. 202 Red No. 204 Blue No. 1 Black iron mica titanium oxide (C) Epicatechin gallate 1-hydroxyethane-1,1-sodium cyphosphonate Polyvinyl alcohol Laponite X L G ''' 20.0 20, O Remaining 8 .0 10.0 4.0 0.5 0.5 1.0 0.5 5.0 0.0Q1 0.001 0.5 1.0 Ion exchange water 10.0* Synthetic bentonite manufactured by Laborte, UK Product name (manufacturing method) After dissolving (A) at 80°C, (B) is mixed and dissolved, and (C), which has also been mixed and dissolved, is added with stirring to emulsify.
その後、室温まで冷却して口紅を得た。Thereafter, it was cooled to room temperature to obtain a lipstick.
実施例９ 白粉
（Ａ）亜鉛華 １２．０タルク
３．０顔料
適量
（Ｂ）グリセリン ５．０カテキン
０．００１精製水
８０．０（Ｃ）香料
適量（製法）
（Ａ）をブレンダーで撹拌しながら（Ｃ）を均一に噴霧
し、これに均一に溶解した（Ｂ）を徐々に加えて練り合
わせ水白粉を得た。Example 9 White powder (A) Zinc white 12.0 Talc 3.0 Pigment
Appropriate amount (B) Glycerin 5.0 Catechin 0.001 Purified water
80.0 (C) Fragrance
Appropriate amount (manufacturing method) While (A) was stirred with a blender, (C) was uniformly sprayed, and (B) uniformly dissolved therein was gradually added and kneaded to obtain a white powder.
実施例１０ ネールトリートメント
（Ａ）プロピレングリコール ５．０トリエ
タノールアミン １．０阿仙薬カテキン
０．１精製水
残余
（Ｂ）ビーガム ０．３（］ス
テアリン酸 ２．０マイクロクリス
タリンワツクス ３．０ワセリン
７．０水添ラノリン ２．０
流動パラフイン ２２．０ポリオキシ
エチレン（５七ル）オレイン酸エステル
２．０防腐剤 適量
香料 適量
（製法）
（Ａ）を溶解した後（Ｂ）を加えて均一に分散させ加熱
して７０℃に保つ。（Ｃ）を混合して加熱溶解して７０
℃に保つ。水相に油相を加え予備乳化を行ない、ホモミ
キサーで均一に乳化する。乳化後撹拌しながら３０℃ま
で冷却してネールトリートメントを得る。Example 10 Nail treatment (A) Propylene glycol 5.0 Triethanolamine 1.0 Asenyaku catechin
0.1 purified water
Remaining (B) Veegum 0.3 (] Stearic acid 2.0 Microcrystalline wax 3.0 Vaseline
7.0 Hydrogenated lanolin 2.0
Liquid paraffin 22.0 polyoxyethylene (57) oleate ester
2.0 Preservatives Appropriate amount Fragrance Appropriate amount (Production method) After dissolving (A), add (B), disperse uniformly, heat, and keep at 70°C. Mix (C) and heat to dissolve
Keep at ℃. Pre-emulsify by adding the oil phase to the water phase, and homogeneously emulsify using a homomixer. After emulsification, the mixture is cooled to 30° C. while stirring to obtain a nail treatment.
実施例１１ シャンプー
ラウリルポリオキシエチレン（３モル）Ｍ 酸Ｉステル
トリエタノールアミン塩（４０％水溶液）
３２．０ラウ’Ｊ Ｉｕ ；ｆｉミリオキシエチ
レン３ｆル）（ｉ４酸Ｉズテルナトリウム塩（３０％水
溶液） ２１．０ラウロイル
ジエタノールアミド ４．０ポリオキシエチレン
グリコール４００ １．０何鋳烏タンニン
０．１へキサメタリン酸ナトリウム
０．１エデト酸３．５ナトリウム
０．２防腐剤 適量紫外線
吸収剤 適量染料
適量精製水
４１・７香料 適
量（製法）
精製水を７０℃に加熱し、他の成分を加え均一に溶解し
た後、冷却しシャンプーを得る。Example 11 Shampoo lauryl polyoxyethylene (3 mol) M acid I ster triethanolamine salt (40% aqueous solution)
32.0 Lau'J Iu; fi myrioxyethylene 3f) (i4 acid I duter sodium salt (30% aqueous solution) 21.0 Lauroyl diethanolamide 4.0 Polyoxyethylene glycol 400 1.0 He Jingwu tannin
0.1 Sodium hexametaphosphate
0.1 edetate 3.5 sodium
0.2 Preservatives Appropriate amount UV absorber Appropriate amount dye
Appropriate amount of purified water
41.7 Fragrance Appropriate amount (manufacturing method) Heat purified water to 70°C, add other ingredients and dissolve uniformly, then cool to obtain shampoo.
実施例１２ リンス
（Ａ）グリセリン ５．０蛋白質誘
導体 ２．０ガロカテキン
ｏ、ｏｏｉｌ−ヒドロキシエタン−１，１
−ジフォズホン酸ナトリウム ０．１染料
適量
精製水 残余
（Ｂ） ステアリルトリメチルアンモニウムクロライド
２．０セチルアルコール
２．０シリコン油 ３
．０ポリオキシエチレン（１０モル）オレイルアルコー
ルエーテル １．０防腐剤
適量紫外線吸収剤 適量
（製法）
（Ａ）を加熱溶解して７０゛Ｃに保つ。（Ｂ）を加熱融
解して７０℃に保つ。油相に水相を加え撹拌する。Example 12 Rinse (A) Glycerin 5.0 Protein derivative 2.0 Gallocatechin
o,ooil-hydroxyethane-1,1
- Sodium diphosphonate 0.1 dye
Appropriate amount of purified water Remainder (B) Stearyltrimethylammonium chloride 2.0 Cetyl alcohol
2.0 silicone oil 3
．． 0 polyoxyethylene (10 mol) oleyl alcohol ether 1.0 preservative
Appropriate amount of UV absorber Appropriate amount (Production method) Heat and dissolve (A) and maintain at 70°C. (B) is melted by heating and kept at 70°C. Add the water phase to the oil phase and stir.
その後冷却しながらさらに撹拌してリンスを得る。Thereafter, the mixture is further stirred while being cooled to obtain a rinse.
実施例１３ ヘアトニック
（Ａ）エタノール
５５．０
ポリオキシエチレン（８ｔル）オレイルアルコールエー
テル ２．０ビタミンＥアセテート０．２
ヒノキチオール ０．０２エチニルエ
ストラジオール ０．０００４紫外線吸収剤
０．２（Ｂ）ミモザタンニン
０．０５エデト酸２ナトリウム
０．１５精製水 残余（Ｃ）
染料 適量（製法）
（Ａ）を溶解した後、（Ｂ）を加えて可溶化を行う。Example 13 Hair tonic (A) Ethanol 55.0 Polyoxyethylene (8 t) Oleyl alcohol ether 2.0 Vitamin E acetate 0.2 Hinokitiol 0.02 Ethinyl estradiol 0.0004 Ultraviolet absorber
0.2(B) Mimosa tannin
0.05 edetate disodium
0.15 Purified water remainder (C)
Appropriate amount of dye (manufacturing method) After dissolving (A), add (B) to solubilize.
（Ｃ）で着色した後口過してトニックを得る。After coloring with (C), pass through the mouth to obtain tonic.
実施例１４ ヘアリキッド
（Ａ）ポリオキシプロピレン（４０モル）フチルエーテ
ルラノリン誘導体
エタノール
防腐剤
紫外線吸収剤
香料
２０．０
１．０
５５．０
適量
適量
１．０
（Ｂ）カテキンガレート
エデト酸
ジエブレントリアミンー五酢酸水溶液
精製水
（Ｃ）染料
（製法）
実施例１３に準じる。Example 14 Hair liquid (A) Polyoxypropylene (40 mol) Phthyl ether Lanolin derivative Ethanol Preservative Ultraviolet absorber Fragrance 20.0 1.0 55.0 Appropriate amount Appropriate amount 1.0 (B) Catechin gallate Edetate acid Diebrentria Mine-pentaacetic acid aqueous solution purified water (C) Dye (manufacturing method) According to Example 13.
０．０２
０．００５
０．０３５
残余
適量
実施例１５ ヘアクリーム
（Ａ）ミツロウ
ワセリン
流動パラフィン
ポリオキシエチレン（５モル）ステアリン酸エステルポ
リオキシエチレン（６ｔル）オレイルアルコールエーテ
ルポリオキシエチレン（６モル）セチルアルコールエー
テル防腐剤
香料
（Ｂ）カテキン混合物
（製造例１で得られた
ヘキサメタリン酸ナトリウム
３．０
１５．０
４２．０
３．０
２．０
１．０
適量
適量
）０．００５
０．００１
精製水 残余
（製法）
（Ａ）を加熱溶解して７０℃に保つ。これに、７０℃に
加熱した（Ｂ）を徐々に加え乳化する。乳化後撹拌しな
がら３０℃まで冷却してヘアクリームを得る。0.02 0.005 0.035 Remaining appropriate amount Example 15 Hair cream (A) Beeswax Vaseline Liquid paraffin Polyoxyethylene (5 moles) Stearate polyoxyethylene (6 tons) Oleyl alcohol ether polyoxyethylene (6 moles) Cetyl alcohol ether preservative fragrance (B) catechin mixture (sodium hexametaphosphate obtained in Production Example 1 3.0 15.0 42.0 3.0 2.0 1.0 appropriate amount) 0.005 0.001 Purification Water Residual (manufacturing method) Heat and dissolve (A) and keep at 70°C. To this, (B) heated to 70° C. is gradually added and emulsified. After emulsification, the mixture is cooled to 30° C. while stirring to obtain a hair cream.
実施例１６ セットローション
（Ａ）プロピレングリコール ２．０ポリ
オキシエチレン（２０モル）ステア１几アルコールエー
テル １．５防腐剤
適量紫外線吸収剤 適量香料
Ｊ量エタノール
１０．０（Ｂ）ポリビニルピロリドン
３．０（Ｃ）粟タンニン
０．０８エデト酸３ナトリウム ０
．０２精製水 残余（Ｄ）
染料 適量（！１２法）
（Ａ）を溶解し、これに（Ｂ）を加えて湿潤させ、撹拌
しながら（Ｃ）を徐々に加え（Ｄ）で着色してセットロ
ーションとする。Example 16 Set lotion (A) Propylene glycol 2.0 Polyoxyethylene (20 mol) Stair 1 liter Alcohol ether 1.5 Preservative
Appropriate amount of UV absorber Appropriate amount of fragrance
J amount ethanol
10.0(B) Polyvinylpyrrolidone
3.0(C) Millet tannin
0.08 Trisodium edetate 0
．． 02 Purified water remainder (D)
Dye Appropriate amount (!12 method) Dissolve (A), add (B) to it and moisten it, gradually add (C) while stirring and color with (D) to make a setting lotion.
実施例１６ 健康ドリンク
果糖ぶどう糖液
蜂蜜
クエン酸
ＤＬ−リンゴ酸
Ｌ−アスパラギン酸
Ｌ−アルギニン
ニコチン酸アミド
グルタミン酸ナトリウム
チアミンＮＤＳ
リボフラビン
ピリドキシン塩酸塩
Ｌ−アスコルビン酸
エピガロカテキン
精製水
香料
１７．９
０．１
８２ｍ８％
４１ｍ８％
２０ｍ８％
２０ｍｇ％
１０ｍｇ％
１ｍｇ％
０．１７ｍｇ％
０．２５ｍｇ％
０．５ｉＢχ
５０ｍｇ％
０．０３
残余
適量
実施例１７ 軟膏剤
γ−オリザノール １．０エピガロカ
テキンガレート０．１
親水性軟膏 残余（製法）
γ−オリザノールと製造例２で得たエピガロカテキンガ
レートを、少量の親水性軟膏と十分に混ぜ合わせた後、
残余の親水性軟膏を徐々に加えて全１（１００％）とし
、全質均等として製する。Example 16 Health drink Fructose glucose liquid Honey Citric acid DL - Malic acid L - Aspartic acid L - Arginine Nicotinic acid amide Glutamate Sodium Thiamine NDS Riboflavin Pyridoxine Hydrochloride L - Ascorbic acid Epigallocatechin Purified water Fragrance 17.9 0.1 82m8 % 41m8% 20m8% 20mg% 10mg% 1mg% 0.17mg% 0.25mg% 0.5iBχ 50mg% 0.03 Remaining appropriate amount Example 17 Ointment γ-oryzanol 1.0 Epigallocatechin gallate 0.1 Hydrophilic ointment Residue (Production method) After thoroughly mixing γ-oryzanol and epigallocatechin gallate obtained in Production Example 2 with a small amount of hydrophilic ointment,
The remaining hydrophilic ointment is gradually added to make a total of 1 (100%), and the whole product is made uniform.
ただし、親水性軟膏基剤の処方は次に示すとおりである
。However, the formulation of the hydrophilic ointment base is as follows.
一親水性軟膏基剤一
セタノール ６．０ポリオキシエチ
レン（３０モル）
セチルエーテル ２．０
グリセリルモノステアレート
（自己乳化型） １０．０
流動パラフイン １０・０白色ワセリン
５．０メチルパラベン
０．１プチルバラベン
プロピレングリコール
精製水- Hydrophilic ointment base - Cetyl 6.0 Polyoxyethylene (30 mol) Cetyl ether 2.0 Glyceryl monostearate (self-emulsifying type) 10.0 Liquid paraffin 10.0 White petrolatum 5.0 Methyl paraben
0.1 butylbaraben propylene glycol purified water
Claims (1)
化防止剤。 ２）カテキン類が、カテキン、エピカテキン、ガロカテ
キン、エピガロカテキン、カテキンガレート、エピカテ
キンガレート・ガロカテキンガレート、エピガロカテキ
ンガレートの群から選ばれる一種または二種以上である
請求項１記載の光劣化防止剤。 ３）カテキン類の縮合物が、大黄、何首烏、地楡、ミモ
ザ、粟、阿仙薬、茶の抽出物である請求項１記載の光劣
化防止剤。 ４）カテキン類またはその縮合物と、キレート剤とを組
合せてなる光劣化防止剤。[Scope of Claims] 1) A photodegradation inhibitor containing catechins or condensates thereof as an active ingredient. 2) The light according to claim 1, wherein the catechins are one or more selected from the group of catechin, epicatechin, gallocatechin, epigallocatechin, catechin gallate, epicatechin gallate/gallocatechin gallate, and epigallocatechin gallate. Anti-deterioration agent. 3) The photodegradation inhibitor according to claim 1, wherein the condensate of catechins is an extract of rhubarb, heshuwura, jiyue, mimosa, millet, asianyaku, or tea. 4) A photodegradation inhibitor comprising a combination of catechins or condensates thereof and a chelating agent.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP1022112A JPH02202581A (en) | 1989-01-31 | 1989-01-31 | Inhibitor of photo-deterioration |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP1022112A JPH02202581A (en) | 1989-01-31 | 1989-01-31 | Inhibitor of photo-deterioration |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPH02202581A true JPH02202581A (en) | 1990-08-10 |
Family
ID=12073805
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP1022112A Pending JPH02202581A (en) | 1989-01-31 | 1989-01-31 | Inhibitor of photo-deterioration |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH02202581A (en) |
Cited By (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH06172122A (en) * | 1992-08-31 | 1994-06-21 | Uenoya Honpo:Kk | Production of cosmetic |
| WO1996026705A1 (en) * | 1995-02-28 | 1996-09-06 | Handelman, Joseph, H. | Reduction of hair growth |
| JPH11169148A (en) * | 1997-12-18 | 1999-06-29 | Ogawa Koryo Co Ltd | Suppressant for flavor deterioration |
| EP0995427A3 (en) * | 1998-09-07 | 2000-05-03 | Dragoco Gerberding & Co Aktiengesellschaft | O/W emulsions containing green tea extract |
| JP2002537862A (en) * | 1999-03-08 | 2002-11-12 | ザ プロクター アンド ギャンブル カンパニー | Beverage products with excellent vitamin stability |
| KR100398628B1 (en) * | 2000-08-21 | 2003-09-19 | 손석민 | Polyphenol oxidase activity inhibition composite containing rhubarb juice and antibrowsing method |
| JP2006169144A (en) * | 2004-12-14 | 2006-06-29 | Nippon Menaade Keshohin Kk | Cosmetic |
| JP2007044053A (en) * | 2006-11-13 | 2007-02-22 | Ogawa & Co Ltd | Flavor deterioration inhibitor |
| JP2007082555A (en) * | 2006-11-13 | 2007-04-05 | Ogawa & Co Ltd | Flavor deterioration inhibitor |
| JP2007097594A (en) * | 2006-11-13 | 2007-04-19 | Ogawa & Co Ltd | Inhibitor of flavor deterioration |
| JP2009510003A (en) * | 2005-09-30 | 2009-03-12 | ディーエスエム アイピー アセッツ ビー．ブイ． | NOVEL COMPOSITION CONTAINING POLYPHENOL |
| JP2009091293A (en) * | 2007-10-09 | 2009-04-30 | Kao Corp | Antimicrobial agent composition |
| JP2009213369A (en) * | 2008-03-07 | 2009-09-24 | Taiyo Kagaku Co Ltd | Packaged drink |
| JP2011529041A (en) * | 2008-07-23 | 2011-12-01 | ケイミュン ユニバーシティ インダストリー アカデミック コーオペレイション ファンデーション | Composition for controlling blood sugar increase |
| JP2016041666A (en) * | 2014-08-19 | 2016-03-31 | 株式会社山田養蜂場本社 | Skin whitening composition |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS59216810A (en) * | 1983-05-24 | 1984-12-06 | Osaka Chem Lab | Cosmetic composition containing catechin compound |
| JPS6115732A (en) * | 1984-06-29 | 1986-01-23 | Pola Chem Ind Inc | Emulsified composition |
-
1989
- 1989-01-31 JP JP1022112A patent/JPH02202581A/en active Pending
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS59216810A (en) * | 1983-05-24 | 1984-12-06 | Osaka Chem Lab | Cosmetic composition containing catechin compound |
| JPS6115732A (en) * | 1984-06-29 | 1986-01-23 | Pola Chem Ind Inc | Emulsified composition |
Cited By (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH06172122A (en) * | 1992-08-31 | 1994-06-21 | Uenoya Honpo:Kk | Production of cosmetic |
| WO1996026705A1 (en) * | 1995-02-28 | 1996-09-06 | Handelman, Joseph, H. | Reduction of hair growth |
| JPH11169148A (en) * | 1997-12-18 | 1999-06-29 | Ogawa Koryo Co Ltd | Suppressant for flavor deterioration |
| EP0995427A3 (en) * | 1998-09-07 | 2000-05-03 | Dragoco Gerberding & Co Aktiengesellschaft | O/W emulsions containing green tea extract |
| JP2002537862A (en) * | 1999-03-08 | 2002-11-12 | ザ プロクター アンド ギャンブル カンパニー | Beverage products with excellent vitamin stability |
| KR100398628B1 (en) * | 2000-08-21 | 2003-09-19 | 손석민 | Polyphenol oxidase activity inhibition composite containing rhubarb juice and antibrowsing method |
| JP2006169144A (en) * | 2004-12-14 | 2006-06-29 | Nippon Menaade Keshohin Kk | Cosmetic |
| JP4600922B2 (en) * | 2004-12-14 | 2010-12-22 | 日本メナード化粧品株式会社 | Cosmetics |
| JP2009510003A (en) * | 2005-09-30 | 2009-03-12 | ディーエスエム アイピー アセッツ ビー．ブイ． | NOVEL COMPOSITION CONTAINING POLYPHENOL |
| JP2007082555A (en) * | 2006-11-13 | 2007-04-05 | Ogawa & Co Ltd | Flavor deterioration inhibitor |
| JP2007097594A (en) * | 2006-11-13 | 2007-04-19 | Ogawa & Co Ltd | Inhibitor of flavor deterioration |
| JP2007044053A (en) * | 2006-11-13 | 2007-02-22 | Ogawa & Co Ltd | Flavor deterioration inhibitor |
| JP2009091293A (en) * | 2007-10-09 | 2009-04-30 | Kao Corp | Antimicrobial agent composition |
| JP2009213369A (en) * | 2008-03-07 | 2009-09-24 | Taiyo Kagaku Co Ltd | Packaged drink |
| JP2011529041A (en) * | 2008-07-23 | 2011-12-01 | ケイミュン ユニバーシティ インダストリー アカデミック コーオペレイション ファンデーション | Composition for controlling blood sugar increase |
| JP2016041666A (en) * | 2014-08-19 | 2016-03-31 | 株式会社山田養蜂場本社 | Skin whitening composition |
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