JPS63117069A - Method of purifying carthamin - Google Patents
Method of purifying carthaminInfo
- Publication number
- JPS63117069A JPS63117069A JP26177486A JP26177486A JPS63117069A JP S63117069 A JPS63117069 A JP S63117069A JP 26177486 A JP26177486 A JP 26177486A JP 26177486 A JP26177486 A JP 26177486A JP S63117069 A JPS63117069 A JP S63117069A
- Authority
- JP
- Japan
- Prior art keywords
- carthamin
- calsamine
- extract
- chitosan
- cellulose
- 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
- 238000000034 method Methods 0.000 title claims description 9
- WLYGSPLCNKYESI-RSUQVHIMSA-N Carthamin Chemical compound O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@H]1[C@@]1(O)C(O)=C(C(=O)\C=C\C=2C=CC(O)=CC=2)C(=O)C(\C=C\2C([C@](O)([C@H]3[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O3)O)C(O)=C(C(=O)\C=C\C=3C=CC(O)=CC=3)C/2=O)=O)=C1O WLYGSPLCNKYESI-RSUQVHIMSA-N 0.000 title abstract 7
- DYQVDISPPLTLLR-HJQYTNQXSA-N Carthamin Natural products CC[C@H]1O[C@H]([C@H](O)[C@@H](O)[C@@H]1O)[C@]2(O)C(=C(C=C/3C(=O)C(=C(O)[C@](O)([C@@H]4O[C@H](CO)[C@@H](O)[C@H](O)[C@H]4O)C3=O)C(=O)C=Cc5ccc(O)cc5)C(=O)C(=C2O)C(=O)C=Cc6ccc(O)cc6)O DYQVDISPPLTLLR-HJQYTNQXSA-N 0.000 title abstract 7
- 229920001661 Chitosan Polymers 0.000 claims abstract description 16
- 239000000049 pigment Substances 0.000 claims abstract description 16
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 16
- 239000001913 cellulose Substances 0.000 claims abstract description 12
- 229920002678 cellulose Polymers 0.000 claims abstract description 12
- 239000012670 alkaline solution Substances 0.000 claims description 10
- 239000002994 raw material Substances 0.000 claims description 6
- 239000003960 organic solvent Substances 0.000 claims description 4
- 235000003255 Carthamus tinctorius Nutrition 0.000 abstract description 15
- 244000020518 Carthamus tinctorius Species 0.000 abstract description 15
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 abstract description 10
- 238000005406 washing Methods 0.000 abstract description 5
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 abstract description 4
- 229910000029 sodium carbonate Inorganic materials 0.000 abstract description 2
- 239000000463 material Substances 0.000 abstract 2
- MCSXGCZMEPXKIW-UHFFFAOYSA-N 3-hydroxy-4-[(4-methyl-2-nitrophenyl)diazenyl]-N-(3-nitrophenyl)naphthalene-2-carboxamide Chemical compound Cc1ccc(N=Nc2c(O)c(cc3ccccc23)C(=O)Nc2cccc(c2)[N+]([O-])=O)c(c1)[N+]([O-])=O MCSXGCZMEPXKIW-UHFFFAOYSA-N 0.000 abstract 1
- 230000001747 exhibiting effect Effects 0.000 abstract 1
- 239000002904 solvent Substances 0.000 abstract 1
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 12
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 10
- KINGXFAMZNIVNL-SXQDSXCISA-N safflor yellow A Natural products OC[C@@H]1O[C@H]2[C@H](OC3=C2C(=O)C(=C(O)C=Cc4ccc(O)cc4)C(=O)[C@]3(O)[C@@H]5O[C@H](CO)[C@@H](O)[C@H](O)[C@H]5O)[C@@H](O)[C@H]1O KINGXFAMZNIVNL-SXQDSXCISA-N 0.000 description 10
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 8
- 239000007864 aqueous solution Substances 0.000 description 8
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 6
- 239000000975 dye Substances 0.000 description 6
- 239000000243 solution Substances 0.000 description 6
- 229910000027 potassium carbonate Inorganic materials 0.000 description 5
- 238000011109 contamination Methods 0.000 description 4
- 239000000843 powder Substances 0.000 description 4
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 239000003513 alkali Substances 0.000 description 3
- 239000001052 yellow pigment Substances 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- 239000000356 contaminant Substances 0.000 description 2
- 150000007522 mineralic acids Chemical class 0.000 description 2
- 150000007524 organic acids Chemical class 0.000 description 2
- BJEPYKJPYRNKOW-REOHCLBHSA-N (S)-malic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O BJEPYKJPYRNKOW-REOHCLBHSA-N 0.000 description 1
- HMUNWXXNJPVALC-UHFFFAOYSA-N 1-[4-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]piperazin-1-yl]-2-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)ethanone Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)N1CCN(CC1)C(CN1CC2=C(CC1)NN=N2)=O HMUNWXXNJPVALC-UHFFFAOYSA-N 0.000 description 1
- VZSRBBMJRBPUNF-UHFFFAOYSA-N 2-(2,3-dihydro-1H-inden-2-ylamino)-N-[3-oxo-3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)propyl]pyrimidine-5-carboxamide Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C(=O)NCCC(N1CC2=C(CC1)NN=N2)=O VZSRBBMJRBPUNF-UHFFFAOYSA-N 0.000 description 1
- WZFUQSJFWNHZHM-UHFFFAOYSA-N 2-[4-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]piperazin-1-yl]-1-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)ethanone Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)N1CCN(CC1)CC(=O)N1CC2=C(CC1)NN=N2 WZFUQSJFWNHZHM-UHFFFAOYSA-N 0.000 description 1
- 102000004190 Enzymes Human genes 0.000 description 1
- 108090000790 Enzymes Proteins 0.000 description 1
- 241000519695 Ilex integra Species 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- BJEPYKJPYRNKOW-UHFFFAOYSA-N alpha-hydroxysuccinic acid Natural products OC(=O)C(O)CC(O)=O BJEPYKJPYRNKOW-UHFFFAOYSA-N 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 1
- 239000001630 malic acid Substances 0.000 description 1
- 235000011090 malic acid Nutrition 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 239000001054 red pigment Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
Landscapes
- Saccharide Compounds (AREA)
Abstract
Description
【発明の詳細な説明】
本発明は、カルサミン（紅花紅色色素）の精製方法に関
するものである。DETAILED DESCRIPTION OF THE INVENTION The present invention relates to a method for purifying calsamine (safflower pink pigment).
更に詳細には、本発明は、カルサミン含有原料の色素成
分からカルサミンを単離精製する方法に関するものであ
る。More specifically, the present invention relates to a method for isolating and purifying calsamine from a pigment component of a calsamine-containing raw material.
一般に、カルサミン色素を精製するためには、乾燥紅花
を充分水洗し、アルカリで抽出し、酸を添加して色素安
定化を行っている。この方法によれば初めの水洗で乾燥
紅花中に含まれるサフラワーイエロー（紅花黄色色素）
を除去し、残ったカルサミンをアルカリで抽出すること
になる。しかしながら、水洗により黄色色素を完全に除
去するのはきわめて困難であり、アルカリ抽出されたカ
ルサミンを化学分析するとかなりの黄色色素が混入して
いることがわかる。Generally, in order to purify calsamine pigments, dried safflower is thoroughly washed with water, extracted with alkali, and acid is added to stabilize the pigments. According to this method, the safflower yellow (safflower yellow pigment) contained in dried safflower is obtained by washing with water for the first time.
is removed, and the remaining calsamine is extracted with alkali. However, it is extremely difficult to completely remove the yellow pigment by washing with water, and chemical analysis of calsamine extracted with alkali reveals that a considerable amount of yellow pigment is mixed in.
また、従来、紅花から含水アセトンで抽出した粗カルサ
ミン水溶液に無機酸、有機酸などを添加し沈澱法により
カルサミンを精製する方法も提案されている。（特公昭
５３−２２６）
また、酵素等を作用させて紅花紅色色素を製造する方法
も示されている。（特公昭４９−２６３２８）しかし、
これらの方法によっても、カルサミンからサフラワーイ
エローを十分に除去することはできていない。Furthermore, a method has been proposed in which calsamine is purified by a precipitation method by adding an inorganic acid, an organic acid, etc. to a crude calsamine aqueous solution extracted from safflower with aqueous acetone. (Japanese Patent Publication No. 53-226) Furthermore, a method for producing a safflower red pigment by the action of an enzyme or the like is also disclosed. (Special Publication No. 49-26328) However,
Even with these methods, safflower yellow cannot be sufficiently removed from calsamine.
本発明者らは１色調があざやかな純粋のカルサミンを得
るために鋭意研究した結果、本発明においてほとんど純
粋のカルサミンを得ることに成功したのである。The present inventors conducted intensive research to obtain pure calsamine with a bright color tone, and as a result of the present invention, they succeeded in obtaining almost pure calsamine in the present invention.
本発明は、カルサミン含有原料をアルカリ溶液で処理し
、得られた抽出液を酸性に調整した後、キトサン及び／
又はセルロースと接触させて色素を吸着させ、水洗し、
アルカリ溶液又は有機溶媒で処理してカルサミンを分離
することを特徴とするカルサミンの精製方法である。In the present invention, calsamine-containing raw materials are treated with an alkaline solution, the resulting extract is adjusted to acidity, and then chitosan and/or
Or, contact with cellulose to adsorb the pigment, wash with water,
This is a method for purifying calsamine, which is characterized by separating calsamine by treatment with an alkaline solution or an organic solvent.
本発明において精製されたカルサミンは、サフラワーイ
エローやその他の夾雑色素等がほぼ完全に除去されてい
るために、カルサミンの赤色色調はきわめてすぐれ、深
く澄んだ赤色を呈している。Since the calsamine purified in the present invention has almost completely removed safflower yellow and other contaminant pigments, the calsamine has an extremely excellent red tone and exhibits a deep, clear red color.
本発明の原料としてはカルサミンを含有する紅花、乾燥
紅花、紅もちが使用できる。As raw materials for the present invention, safflower, dried safflower, and beni mochi containing calsamine can be used.
本発明においては、まず紅花又は乾燥紅花、紅もちをア
ルカリ溶液で処理して色素を抽出する。In the present invention, first, safflower or dried safflower or safflower is treated with an alkaline solution to extract the pigment.
アルカリ溶液としては微アルカリ水溶液でよく、例えば
０．１〜１％程度の炭酸カリウム水溶液、炭酸ソーダ水
溶液などでよい。The alkaline solution may be a slightly alkaline aqueous solution, such as a 0.1 to 1% potassium carbonate aqueous solution or a sodium carbonate aqueous solution.
処理としては、アルカリ溶液にカルサミン含有原料を投
入して十分攪拌したり、また、カルサミン含有原料を一
定容器に入れておいて、これにアルカリ溶液を循環させ
て色素を抽出したりすることができる。For processing, the calsamine-containing raw material can be added to an alkaline solution and thoroughly stirred, or the calsamine-containing raw material can be placed in a container and the alkaline solution can be circulated through it to extract the pigment. .
色素抽出液には酸を添加して酸性に調整される。An acid is added to the pigment extract to make it acidic.
酸としては燐酸、塩酸、炭酸等の無機酸、クエン酸、リ
ンゴ酸等の有機酸などが使用されるが、調整されるＰ）
１としてはｐ）１２．０〜６．０程度が好ましい。As the acid, inorganic acids such as phosphoric acid, hydrochloric acid, and carbonic acid, and organic acids such as citric acid and malic acid are used, but P) may be adjusted.
1 is preferably about p) 12.0 to 6.0.
酸性に調整された色素抽出液はキトサン及び／又はセル
ロースと接触させて、色素をキトサン及び／又はセルロ
ースに吸着させる６キトサン及び／又はセルロースはそ
のまま色素抽出液と混合してもよいし、また、カラムに
つめて、これに色素抽出液を通してもよい。The acidified pigment extract is brought into contact with chitosan and/or cellulose to adsorb the pigment onto the chitosan and/or cellulose.6 Chitosan and/or cellulose may be mixed with the pigment extract as is, or It may be packed in a column and the dye extract may be passed through it.
キトサン及び／又はセルロースはいかなるものでもよい
が、市販の粉末状のキトサン又はセルロースが一般的で
ある。Although any chitosan and/or cellulose may be used, commercially available powdered chitosan or cellulose is generally used.
次に１色素を吸着したキトサン及び／又はセルロースは
水でよく洗滌される。Next, the chitosan and/or cellulose adsorbed with one dye are thoroughly washed with water.
水による洗滌によって、サフラワーイエローやその他の
夾雑物が流去され、純粋なカルサミンだけが残ることに
なる。Rinsing with water washes away the safflower yellow and other contaminants, leaving only pure calsamine.
カルサミンが残ったキトサン及び／又はセルロースはＰ
Ｈ９，０〜１１．０のアルカリ溶液または含水アセトン
、ピリジン等の有機溶媒で処理することによってカルサ
ミンが抽出されてくる。Chitosan and/or cellulose with remaining calsamine are P
Calsamine is extracted by treatment with an alkaline solution of H9.0 to H11.0 or an organic solvent such as hydrous acetone or pyridine.
使用するアルカリ溶液としては２〜５％の炭酸カリが好
ましい、また使用する有機溶媒としては含水率２０〜８
０％のアセトン、ピリジンが好ましい。The alkaline solution used is preferably 2-5% potassium carbonate, and the organic solvent used is preferably a water content of 20-8.
0% acetone, pyridine is preferred.
ここに得られるカルサミンの抽出液はＴ、Ｌ、Ｃで単一
のスポットを示し、Ｒｆ値も純水のカルサミンのものと
一致し、サフラワーイエローの混入は全く認められない
ものである。The calsamine extract obtained here shows a single spot in T, L, and C, and the Rf value matches that of pure water calsamine, and no safflower yellow is observed at all.
次に、本発明の実施例を示す。Next, examples of the present invention will be shown.
実施例１
乾燥紅花１ｋｇを０．３％炭酸カリウム水溶液１０Ωに
浸し３０分間十分に攪拌し、色素を抽出し、抽出液を分
離する。得られた抽出液９Ｑを１％クエン酸溶液により
ｐＨ４，０に調整し、これにセルロースパウダー５００
ｇ添加し攪゛拌する。色素を吸着したセルロースパウダ
ーを取り出し、十分水洗した後。Example 1 1 kg of dried safflower is immersed in a 0.3% potassium carbonate aqueous solution of 10 Ω and thoroughly stirred for 30 minutes to extract the pigment and separate the extract. The obtained extract 9Q was adjusted to pH 4.0 with a 1% citric acid solution, and 500 g of cellulose powder was added to this.
g and stir. After taking out the cellulose powder that has absorbed the dye and washing it thoroughly with water.
３％炭酸カリウム溶液３Ｑでカルサミンを抽出した。Calsamine was extracted with 3% potassium carbonate solution 3Q.
抽出物は、Ｔ、Ｌ、Ｃで単一スポットであり、Ｒｆ値は
純粋のカルサミンのものと一致し、サフラワーイエロー
の混入はなかった。The extract was a single spot in T, L, and C, and the Rf value matched that of pure calsamine, with no safflower yellow contamination.
実施例２
生の紅花１ｋｇを０．０５％水酸化ナトリウム水溶液５
１２に浸し３０分間十分に攪拌し１色素を抽出し、抽出
液を分離する。得られた抽出液４．５Ｑを１％クエン酸
溶液によりｐＨ３，５に調整し、これにセルロースパウ
ダー１５０ｇを添加し攪拌する６色素を吸着したセルロ
ースパウダーを取り出し、十分水洗した後、８０％アセ
トン水ＩＱでカルサミンを抽出した。Example 2 1 kg of fresh safflower was added to 0.05% sodium hydroxide aqueous solution 5
12 and thoroughly stirred for 30 minutes to extract 1 pigment and separate the extract. The obtained extract 4.5Q was adjusted to pH 3.5 with a 1% citric acid solution, and 150 g of cellulose powder was added thereto and stirred. The cellulose powder adsorbed with 6 dyes was taken out, thoroughly washed with water, and then added with 80% acetone. Calsamine was extracted with water IQ.
抽出物は、Ｔ、Ｌ、Ｃで単一スポットであり、Ｒｆ値は
純粋のカルサミンのものと一致し、サフラワーイエロー
の混入はなかった。The extract was a single spot in T, L, and C, and the Rf value matched that of pure calsamine, with no safflower yellow contamination.
実施例３
乾燥紅花１ｋｇを０．３％炭酸カリウム水溶液１０１２
に浸し３０分間十分に攪拌し、抽出液を分離する。Example 3 1 kg of dried safflower was added to 0.3% potassium carbonate aqueous solution 1012
Stir thoroughly for 30 minutes and separate the extract.
得られた抽出液９Ｑを１０％酢酸溶液によりｐＨ４，０
に調整し、これにキトサンパウダー５００ｇを添加し攪
拌する１色素を吸着したキトサンパウダーを取り出し、
十分に水洗した後、８０％ピリジン溶液ＩＱでカルサミ
ンを抽出した。The obtained extract 9Q was adjusted to pH 4.0 with 10% acetic acid solution.
Add 500g of chitosan powder to this and stir.Take out the chitosan powder that has absorbed the dye,
After thorough washing with water, calsamine was extracted with 80% pyridine solution IQ.
抽出物はＴ、Ｌ、Ｃで単一スポットであり、 Ｒｆ値は
純粋のカルサミンのものと一致し、サフラワーイエロー
の混入はなかった。The extract was a single spot at T, L, and C, and the Rf value matched that of pure calsamine, with no safflower yellow contamination.
実施例４
乾燥紅花１ｋｇを０．３％炭酸カリウム水溶液ｉｌｌに
浸し３０分間十分に攪拌し、抽出液を分離する。Example 4 1 kg of dried safflower is soaked in 0.3% potassium carbonate aqueous solution ill, thoroughly stirred for 30 minutes, and the extract is separated.
得られた抽出液９ρを１％クエン酸溶液によりｐＨ４，
０に調整し、これにセルロースパウダー３００ｇとキト
サンパウダーＺｏｏ ｇを添加し攪拌する０色素を吸着
したセルロースパウダーとキトサンパウダーを取り出し
、十分に水洗した後、８０％ピリジン溶液１ａでカルサ
ミンを抽出した。The obtained extract 9ρ was adjusted to pH 4 with 1% citric acid solution.
0, add 300 g of cellulose powder and Zoo g of chitosan powder, and stir. The cellulose powder and chitosan powder adsorbed with the dye were taken out, thoroughly washed with water, and then calsamine was extracted with 80% pyridine solution 1a.
抽出物はＴ、Ｌ、Ｃで単一スポットであり、Ｒｆ値は純
粋のカルサミンのものと一致し、サフラワーイエローの
混入はなかった。The extract was a single spot at T, L, and C, and the Rf value matched that of pure calsamine, with no safflower yellow contamination.
Claims (1)
抽出液を酸性に調整した後、キトサン及び／又はセルロ
ースと接触させて色素を吸着させ、水洗し、アルカリ溶
液又は有機溶媒で処理してカルサミンを分離することを
特徴とするカルサミンの精製方法。The calsamine-containing raw material is treated with an alkaline solution, the resulting extract is adjusted to acidity, and then brought into contact with chitosan and/or cellulose to adsorb the pigment, washed with water, and treated with an alkaline solution or an organic solvent to release calsamine. A method for purifying calsamine, which comprises separating it.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP26177486A JPS63117069A (en) | 1986-11-05 | 1986-11-05 | Method of purifying carthamin |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP26177486A JPS63117069A (en) | 1986-11-05 | 1986-11-05 | Method of purifying carthamin |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPS63117069A true JPS63117069A (en) | 1988-05-21 |
Family
ID=17366511
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP26177486A Pending JPS63117069A (en) | 1986-11-05 | 1986-11-05 | Method of purifying carthamin |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS63117069A (en) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7645172B2 (en) | 2007-01-24 | 2010-01-12 | Sumitomo Wiring Systems, Ltd. | Connector and assembling method therefor |
| CN105906596A (en) * | 2016-05-04 | 2016-08-31 | 浙江大学 | Carthamin yellow refining process |
| CN112521769A (en) * | 2020-11-25 | 2021-03-19 | 清华大学 | Safflower red pigment and preparation method and dyeing method thereof |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5641667A (en) * | 1979-09-13 | 1981-04-18 | Mitsubishi Electric Corp | Electrode for discharge lamp |
| JPS5725576A (en) * | 1980-07-22 | 1982-02-10 | Matsushita Electric Ind Co Ltd | Small type electro-magnetic valve |
-
1986
- 1986-11-05 JP JP26177486A patent/JPS63117069A/en active Pending
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5641667A (en) * | 1979-09-13 | 1981-04-18 | Mitsubishi Electric Corp | Electrode for discharge lamp |
| JPS5725576A (en) * | 1980-07-22 | 1982-02-10 | Matsushita Electric Ind Co Ltd | Small type electro-magnetic valve |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7645172B2 (en) | 2007-01-24 | 2010-01-12 | Sumitomo Wiring Systems, Ltd. | Connector and assembling method therefor |
| CN105906596A (en) * | 2016-05-04 | 2016-08-31 | 浙江大学 | Carthamin yellow refining process |
| CN112521769A (en) * | 2020-11-25 | 2021-03-19 | 清华大学 | Safflower red pigment and preparation method and dyeing method thereof |
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