JPH0254061B2 - - Google Patents
Info
- Publication number
- JPH0254061B2 JPH0254061B2 JP57038579A JP3857982A JPH0254061B2 JP H0254061 B2 JPH0254061 B2 JP H0254061B2 JP 57038579 A JP57038579 A JP 57038579A JP 3857982 A JP3857982 A JP 3857982A JP H0254061 B2 JPH0254061 B2 JP H0254061B2
- Authority
- JP
- Japan
- Prior art keywords
- egg white
- hydrolyzate
- acidic
- solution
- aqueous solution
- 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.)
- Expired - Lifetime
Links
- 102000002322 Egg Proteins Human genes 0.000 claims description 44
- 108010000912 Egg Proteins Proteins 0.000 claims description 44
- QCVGEOXPDFCNHA-UHFFFAOYSA-N 5,5-dimethyl-2,4-dioxo-1,3-oxazolidine-3-carboxamide Chemical compound CC1(C)OC(=O)N(C(N)=O)C1=O QCVGEOXPDFCNHA-UHFFFAOYSA-N 0.000 claims description 43
- 235000014103 egg white Nutrition 0.000 claims description 42
- 210000000969 egg white Anatomy 0.000 claims description 42
- 230000002378 acidificating effect Effects 0.000 claims description 14
- 108091005804 Peptidases Proteins 0.000 claims description 12
- 102000035195 Peptidases Human genes 0.000 claims description 12
- 102000004169 proteins and genes Human genes 0.000 claims description 9
- 108090000623 proteins and genes Proteins 0.000 claims description 9
- 238000004519 manufacturing process Methods 0.000 claims description 4
- 241000228212 Aspergillus Species 0.000 claims description 3
- 239000007864 aqueous solution Substances 0.000 description 10
- 239000000243 solution Substances 0.000 description 10
- 102000004190 Enzymes Human genes 0.000 description 8
- 108090000790 Enzymes Proteins 0.000 description 8
- 229940088598 enzyme Drugs 0.000 description 8
- 235000018102 proteins Nutrition 0.000 description 8
- 229940024999 proteolytic enzymes for treatment of wounds and ulcers Drugs 0.000 description 5
- 102000057297 Pepsin A Human genes 0.000 description 4
- 108090000284 Pepsin A Proteins 0.000 description 4
- 239000000796 flavoring agent Substances 0.000 description 4
- 235000019634 flavors Nutrition 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- 239000002994 raw material Substances 0.000 description 4
- CKLJMWTZIZZHCS-REOHCLBHSA-N L-aspartic acid Chemical compound OC(=O)[C@@H](N)CC(O)=O CKLJMWTZIZZHCS-REOHCLBHSA-N 0.000 description 3
- 239000004365 Protease Substances 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 238000000354 decomposition reaction Methods 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 238000006460 hydrolysis reaction Methods 0.000 description 3
- 238000000034 method Methods 0.000 description 3
- 229940111202 pepsin Drugs 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 235000001014 amino acid Nutrition 0.000 description 2
- 150000001413 amino acids Chemical class 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 230000015271 coagulation Effects 0.000 description 2
- 238000005345 coagulation Methods 0.000 description 2
- 238000007796 conventional method Methods 0.000 description 2
- 230000002255 enzymatic effect Effects 0.000 description 2
- 235000011389 fruit/vegetable juice Nutrition 0.000 description 2
- 230000007062 hydrolysis Effects 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 230000007935 neutral effect Effects 0.000 description 2
- 235000016709 nutrition Nutrition 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 230000001954 sterilising effect Effects 0.000 description 2
- 238000004659 sterilization and disinfection Methods 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 108091005658 Basic proteases Proteins 0.000 description 1
- 244000248349 Citrus limon Species 0.000 description 1
- 235000005979 Citrus limon Nutrition 0.000 description 1
- AFCARXCZXQIEQB-UHFFFAOYSA-N N-[3-oxo-3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)propyl]-2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidine-5-carboxamide Chemical compound O=C(CCNC(=O)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F)N1CC2=C(CC1)NN=N2 AFCARXCZXQIEQB-UHFFFAOYSA-N 0.000 description 1
- 108091005507 Neutral proteases Proteins 0.000 description 1
- 102000035092 Neutral proteases Human genes 0.000 description 1
- 235000003704 aspartic acid Nutrition 0.000 description 1
- OQFSQFPPLPISGP-UHFFFAOYSA-N beta-carboxyaspartic acid Natural products OC(=O)C(N)C(C(O)=O)C(O)=O OQFSQFPPLPISGP-UHFFFAOYSA-N 0.000 description 1
- 235000013361 beverage Nutrition 0.000 description 1
- 235000019658 bitter taste Nutrition 0.000 description 1
- 238000005119 centrifugation Methods 0.000 description 1
- 230000035622 drinking Effects 0.000 description 1
- 238000006911 enzymatic reaction Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- 238000004108 freeze drying Methods 0.000 description 1
- 238000007710 freezing Methods 0.000 description 1
- 230000008014 freezing Effects 0.000 description 1
- 235000012907 honey Nutrition 0.000 description 1
- 230000003301 hydrolyzing effect Effects 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 230000005923 long-lasting effect Effects 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 235000008935 nutritious Nutrition 0.000 description 1
- 210000000056 organ Anatomy 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 238000007665 sagging Methods 0.000 description 1
- 239000006228 supernatant Substances 0.000 description 1
- 230000003313 weakening effect Effects 0.000 description 1
Landscapes
- Meat, Egg Or Seafood Products (AREA)
Description
本発明は卵白加水分解物の製造法に関し、更に
詳しくは加熱殺菌時に凝固を起さず、しかも風味
が良好で、種々の飲料、栄養組成物の原料として
利用し得る卵白加水分解物の製造法に関する。
従来卵白飲料の開発が試みられているが、加熱
殺菌時に卵白蛋白質が凝固するため、蛋白質濃度
が低い場合は液状部と沈殿部に分離し、また、そ
の濃度が高い場合は全体がゲル状に固まるという
大きな問題があり、未だ商品化の段階に到つてい
ないのが現状である。このため従来酵素により蛋
白質を分解する方法や、多量の砂糖を添加して凝
固点を上げる方法、あるいは両者の併用法などの
手段が講じられている。しかしながら従来の上記
酵素処理法においては中性プロテアーゼ、アルカ
リプロテアーゼを用いると臭みを生じるという欠
点があり、また酸性プロテアーゼの中でもペプシ
ンの如き臓器由来の酵素もまた臭みを生じるとい
う欠点をもつていた。更に酵素反応を行なう卵白
溶液の濃度に関しても、高濃度液では酵素分解が
十分に行なわれないという欠点があつた。
更にまた、砂糖添加法においては飲用する際の
卵白含有量が少なくなり卵白飲料としての特質が
薄れ、更に、両者の併用法においてはいずれの問
題も解決されていないなど未だ不満足なものであ
る。
そこで、本発明者は、卵白飲料の原料として使
用できる卵白誘導体を得べく種々研究した結果、
一定の蛋白質濃度の卵白水溶液に特定の酸性蛋白
質分解酵素を作用させた後、該溶液を加熱変性さ
せ、生じた凝固物を除去すれば清澄な卵白加水分
解物水溶液が得られること、及びこの水溶液は再
度の加熱によつても凝固を起さず、水溶液として
長時間保存した場合通常生じる「オリ」が生じな
いこと並びに斯くして得られた卵白加水分解物は
風味が良好で、卵白飲料あるいは栄養組成物の原
料として有用であることを見出し、本発明を完成
した。
従つて本発明は、約１〜６％の蛋白質濃度の原
料卵白溶液にアスペルギルス（Aspergillus）属
の生産する酸性蛋白質分解酵素をPH３〜４の条件
下で作用させたのち、約80〜100℃に加熱し、凝
固物を除去することを特徴とする卵白加水分解物
の製造法を提供するものである。
本発明に用いる卵白は、生卵白、冷凍卵白、粉
末卵白のいずれもが使用できる。この卵白は、適
宜水で希釈するか、水戻しすることにより蛋白質
濃度として約１〜６％、好ましくは２〜５％の卵
白水溶液とされる。水溶液の蛋白質濃度が約１％
以下であると得られる製品に卵白加水分解物とし
ての特徴が表われがたく、また約６％以上である
と酵素分解がすみやかに行なわれにくくなり、苦
味等を生じてくる。次いで得られた卵白水溶液
に、有機酸あるいは無機酸を加えてPHを弱酸性、
好ましくは3.0〜4.0に調節する。
この卵白水溶液は更に酸性蛋白質分解酵素の作
用により加水分解反応に付される。酸性蛋白質分
解酵素とは至適PHが酸性にあるものの総称であ
る。本発明の加水分解に用いる酸性蛋白質分解酵
素は、アスペルギルス（Aspergillus）属の生産
するプロテアーゼで、たとえばオリエンターゼ
5A（阪急共栄物産）、ニユーラーゼ（天野製薬）、
プロチンFA（大和化成）、デナプシン2P（ナガセ
生化学工業）等が特に、適当である。使用量は反
応液に対して0.01〜0.4％が好ましいが、酵素の
力価によつてはこの限りではない。反応温度は酵
素の至適温度よりやや高い50〜60℃が好ましく、
反応時間は２〜24時間、好ましくは３〜５時間が
良い。
斯くして得られた加水分解物溶液を、更に約80
〜100℃で５〜30分間、好ましくは10〜20分間加
熱し、生じた凝固物を遠心分離または過により
除去することにより清澄な溶液として卵白加水分
解物が得られる。
この卵白加水分解物の特性の一部を示せば次の
通りである。
(1) 平均分子量：
分子量3000以下のものが大部分（酵素、分解
条件により異なるが、通常３〜６種の平均分子
量をもつものが得られる）であり、遊離アアミ
ノ酸は、10％前後である。
(2) アミノ酸組成：
それぞれの試料を12N HCl、減圧下、
16hrs，106℃で加水分解して測定した〔アスパ
ラギン酸（Asp）を1.00とした比〕。 卵白加水分解物 卵 白
Lys 0.69 0.64
HiS 0.22 0.20
Arg 0.40 0.43
Asp 1.00 1.00
Thr 0.48 0.48
Ser 0.61 0.70
Glu 1.20 1.20
Pro 0.64 0.54
Gly 0.65 0.63
Ala 1.14 1.21
Val 0.78 0.78
Met 0.42 0.43
Ileu 0.50 0.51
Leu 0.88 0.84
Tyr 0.16 0.22
Phe 0.62 0.59
叙上の如くして得られた卵白加水分解物は所望
により更に常法に従い、濃縮とされたり、冷凍乾
燥法により粉末とすることもでき、いずれの卵白
加水分解物水溶液と同様、卵白飲料、卵白含有食
品の原料とすることができる。
次に実施例、参考例及び試験例を挙げ本発明を
更に詳細に説明する。
実施例 １
乾燥卵白２Kgを清水48Kgに完全に溶解し、硫酸
を用いPHを3.0に調整した。次いでゆるやかな撹
拌下で、液温を50℃に維持しながら、プロチン
FA2ｇを添加し、４時間酵素処理を行なつた。そ
の後100℃で20分間加熱し、遠心分離して、その
上澄液42Kgを得た。
実施例 ２
上記卵白加水分解物を減圧濃縮後、凍結乾燥し
たもの10ｇに、レモン果汁15ｇ、梅果汁７ｇ、砂
糖140ｇ、蜂密30ｇ、クエン酸4.5ｇ、ドリンクフ
レーバー4.5ｇを加えてミネラルウオーター789ｇ
といつしよに撹拌したのち、95℃で５秒間加熱殺
菌を行なつたところ、卵白蛋白質の凝固は全く見
られず、美味かつ栄養豊富で保存性のある卵白飲
料が得られた。
試験例 １
乾燥卵白の４％水溶液を酸性、中性、アルカリ
性蛋白質分解酵素を用い加水分解した。この結果
を第１表に示す。
The present invention relates to a method for producing an egg white hydrolyzate, and more specifically, a method for producing an egg white hydrolyzate that does not cause coagulation during heat sterilization, has a good flavor, and can be used as a raw material for various beverages and nutritional compositions. Regarding. Previous efforts have been made to develop an egg white drink, but since the egg white protein coagulates during heat sterilization, if the protein concentration is low, it will separate into a liquid part and a precipitate part, and if the protein concentration is high, the whole will become gel-like. Currently, it has not yet reached the stage of commercialization due to the major problem of hardening. To this end, conventional methods have been used, such as decomposing proteins with enzymes, adding a large amount of sugar to raise the freezing point, or a combination of both. However, in the conventional enzyme treatment method described above, the use of neutral proteases and alkaline proteases has the disadvantage of producing odor, and among acidic proteases, organ-derived enzymes such as pepsin also have the disadvantage of producing odor. Furthermore, regarding the concentration of the egg white solution in which the enzymatic reaction is carried out, there is a drawback in that enzymatic decomposition cannot be carried out sufficiently with a highly concentrated solution. Furthermore, the sugar addition method reduces the egg white content when drinking, weakening its characteristics as an egg white drink, and the combined method of both is still unsatisfactory, as none of the problems has been solved. Therefore, as a result of various researches to obtain an egg white derivative that can be used as a raw material for egg white drinks, the present inventor found that
A clear egg white hydrolyzate aqueous solution can be obtained by treating an aqueous egg white solution with a certain protein concentration with a specific acidic proteolytic enzyme, denaturing the solution by heating, and removing the resulting coagulum; and this aqueous solution. The egg white hydrolyzate does not coagulate even when heated again, does not cause the "staleness" that normally occurs when stored as an aqueous solution for a long time, and the egg white hydrolyzate thus obtained has a good flavor and can be used as an egg white drink or They discovered that it is useful as a raw material for nutritional compositions, and completed the present invention. Therefore, in the present invention, an acidic proteolytic enzyme produced by Aspergillus is applied to a raw egg white solution having a protein concentration of about 1 to 6% under a pH of 3 to 4, and then heated to about 80 to 100°C. The present invention provides a method for producing an egg white hydrolyzate, which is characterized by heating and removing coagulum. As the egg white used in the present invention, any of fresh egg white, frozen egg white, and powdered egg white can be used. This egg white is appropriately diluted with water or reconstituted to form an aqueous egg white solution with a protein concentration of about 1 to 6%, preferably 2 to 5%. Protein concentration in aqueous solution is approximately 1%
If it is less than 6%, the characteristics of an egg white hydrolyzate will not be apparent in the product obtained, and if it is more than about 6%, enzymatic decomposition will not be carried out quickly, resulting in a bitter taste. Next, add an organic or inorganic acid to the resulting egg white aqueous solution to make the pH slightly acidic.
Preferably it is adjusted to 3.0 to 4.0. This egg white aqueous solution is further subjected to a hydrolysis reaction by the action of an acidic proteolytic enzyme. Acidic proteolytic enzymes are a general term for enzymes whose optimal pH is acidic. The acidic protease used in the hydrolysis of the present invention is a protease produced by the genus Aspergillus, such as orientase.
5A (Hankyu Kyoei Bussan), Neurase (Amano Pharmaceutical),
Particularly suitable are Protin FA (Daiwa Kasei), Denapsin 2P (Nagase Seikagaku Kogyo), and the like. The amount used is preferably 0.01 to 0.4% based on the reaction solution, but this may not be the case depending on the titer of the enzyme. The reaction temperature is preferably 50 to 60°C, which is slightly higher than the optimum temperature of the enzyme.
The reaction time is 2 to 24 hours, preferably 3 to 5 hours. The hydrolyzate solution thus obtained was further diluted with about 80%
The egg white hydrolyzate is obtained as a clear solution by heating at ~100° C. for 5 to 30 minutes, preferably 10 to 20 minutes, and removing the formed coagulum by centrifugation or filtration. Some of the characteristics of this egg white hydrolyzate are as follows. (1) Average molecular weight: The majority have a molecular weight of 3000 or less (depending on the enzyme and decomposition conditions, but usually 3 to 6 types of average molecular weight can be obtained), and free amino acids account for around 10%. be. (2) Amino acid composition: Each sample was dissolved in 12N HCl under reduced pressure.
Measured by hydrolysis at 106°C for 16 hours [ratio with aspartic acid (Asp) as 1.00]. Egg white hydrolyzate Egg white Lys 0.69 0.64 HiS 0.22 0.20 Arg 0.40 0.43 Asp 1.00 1.00 Thr 0.48 0.48 Ser 0.61 0.70 Glu 1.20 1.20 Pro 0.64 0.54 Gly 0.65 0.63 Ala 1.14 1.21 Val 0.78 0.78 Met 0.42 0.43 Ileu 0.50 0.51 Leu 0.88 0.84 Tyr 0.16 0.22 Phe 0.62 0.59 If desired, the egg white hydrolyzate obtained as described above can be further concentrated by a conventional method or powdered by freeze-drying, and can be made into a powder in the same manner as any aqueous solution of egg white hydrolyzate. It can be used as a raw material for egg white drinks, egg white-containing foods, etc. Next, the present invention will be explained in more detail with reference to Examples, Reference Examples, and Test Examples. Example 1 2 kg of dried egg white was completely dissolved in 48 kg of clear water, and the pH was adjusted to 3.0 using sulfuric acid. Next, add protein while maintaining the liquid temperature at 50℃ under gentle stirring.
2 g of FA was added and enzyme treatment was performed for 4 hours. Thereafter, it was heated at 100°C for 20 minutes and centrifuged to obtain 42 kg of supernatant. Example 2 To 10 g of the above egg white hydrolyzate concentrated under reduced pressure and freeze-dried, 15 g of lemon juice, 7 g of plum juice, 140 g of sugar, 30 g of honey, 4.5 g of citric acid, and 4.5 g of drink flavor were added to make 789 g of mineral water.
After stirring thoroughly, the mixture was heat sterilized at 95°C for 5 seconds, and no coagulation of the egg white protein was observed, resulting in a delicious, nutritious, and long-lasting egg white drink. Test Example 1 A 4% aqueous solution of dried egg white was hydrolyzed using acidic, neutral, and alkaline proteolytic enzymes. The results are shown in Table 1.
【表】
第１表から本発明の卵白溶液の加水分解には酸
性蛋白質分解酵素が適当であることがわかる。
また中性、アルカリ性蛋白質分解酵素による卵
白加水分解物は臭みがあつたが、酸性蛋白質分解
酵素によるものは臭みはなく心地よい風味があつ
た。
試験例 ２
乾燥卵白の４％水溶液を酸性蛋白質分解酵素で
あるペプシン及びオリエンターゼ5Aを用い加水
分解した。この結果を第２表に示す。Table 1 shows that acidic proteolytic enzymes are suitable for hydrolyzing the egg white solution of the present invention. Furthermore, the egg white hydrolyzate produced by neutral or alkaline proteolytic enzymes had a strong odor, but the product produced by acidic proteolytic enzymes had no odor and a pleasant flavor. Test Example 2 A 4% aqueous solution of dried egg white was hydrolyzed using acidic proteolytic enzymes pepsin and orientase 5A. The results are shown in Table 2.
【表】
なお、ペプシンにより調製した卵白加水分解物
は、その５％水溶液を５℃に保存した場合に２日
目に「オリ」を生じたが、アスペルギルス
（Aspergillus）属の生産する酵素により調製した
ものは同条件下で10日目でも「オリ」を生じなか
つた。
この結果からペプシンの至適PHは強酸性である
が、その卵白加水分解物は臭みを生じ、本発明に
は不適当であることがわかる。[Table] In addition, when the 5% aqueous solution of the egg white hydrolyzate prepared with pepsin was stored at 5°C, a "melt" formed on the second day. However, under the same conditions, no "sagging" occurred even on the 10th day. This result shows that although the optimal pH of pepsin is strongly acidic, its egg white hydrolyzate produces an odor and is unsuitable for the present invention.
Claims (1)
スペルギルス（Aspergillus）属の生産する酸性
蛋白質分解酵素をPH３〜４の条件下で作用させた
のち、約80〜100℃に加熱し、凝固物を除去する
ことを特徴とする卵白加水分解物の製造法。1. A raw egg white solution with a protein concentration of about 1 to 6% is treated with an acidic proteolytic enzyme produced by the genus Aspergillus under PH3 to 4 conditions, and then heated to about 80 to 100°C to form a coagulated product. A method for producing an egg white hydrolyzate, which comprises removing.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP57038579A JPS58155048A (en) | 1982-03-11 | 1982-03-11 | Preparation of hydrolyzed albumen |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP57038579A JPS58155048A (en) | 1982-03-11 | 1982-03-11 | Preparation of hydrolyzed albumen |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS58155048A JPS58155048A (en) | 1983-09-14 |
| JPH0254061B2 true JPH0254061B2 (en) | 1990-11-20 |
Family
ID=12529197
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP57038579A Granted JPS58155048A (en) | 1982-03-11 | 1982-03-11 | Preparation of hydrolyzed albumen |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS58155048A (en) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP4553859B2 (en) * | 2005-04-22 | 2010-09-29 | キユーピー株式会社 | Acid oil-in-water emulsified food |
| JP2007167041A (en) * | 2005-12-26 | 2007-07-05 | Taiyo Kagaku Co Ltd | Method for producing albumen decompose product |
| ES2539735B1 (en) | 2013-12-20 | 2016-02-02 | Consejo Superior De Investigaciones Científicas (Csic) | Healthy food compositions that have gel or foam textures and that comprise hydrolyzed egg products |
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|---|---|---|---|---|
| JPS5126496A (en) * | 1974-08-29 | 1976-03-04 | Matsushita Electric Ind Co Ltd | |
| JPS5128705A (en) * | 1974-09-05 | 1976-03-11 | Oki Electric Ind Co Ltd | Kokanmoniokeru fusetsukyoku fusetsugenin oyobi setsuzokukeiroshikibetsuhoshiki |
| JPS5436235A (en) * | 1977-08-24 | 1979-03-16 | Dainippon Ink & Chem Inc | 4-n-alkyl-delta'-cyclohexene-1-carboxylic acids |
| JPS5745560A (en) * | 1980-09-01 | 1982-03-15 | Ricoh Co Ltd | Method for synthesized recording of images |
-
1982
- 1982-03-11 JP JP57038579A patent/JPS58155048A/en active Granted
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5126496A (en) * | 1974-08-29 | 1976-03-04 | Matsushita Electric Ind Co Ltd | |
| JPS5128705A (en) * | 1974-09-05 | 1976-03-11 | Oki Electric Ind Co Ltd | Kokanmoniokeru fusetsukyoku fusetsugenin oyobi setsuzokukeiroshikibetsuhoshiki |
| JPS5436235A (en) * | 1977-08-24 | 1979-03-16 | Dainippon Ink & Chem Inc | 4-n-alkyl-delta'-cyclohexene-1-carboxylic acids |
| JPS5745560A (en) * | 1980-09-01 | 1982-03-15 | Ricoh Co Ltd | Method for synthesized recording of images |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS58155048A (en) | 1983-09-14 |
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