JP3513370B2 - Method for preserving and stabilizing cinamic aldehydes - Google Patents
Method for preserving and stabilizing cinamic aldehydesInfo
- Publication number
- JP3513370B2 JP3513370B2 JP27612297A JP27612297A JP3513370B2 JP 3513370 B2 JP3513370 B2 JP 3513370B2 JP 27612297 A JP27612297 A JP 27612297A JP 27612297 A JP27612297 A JP 27612297A JP 3513370 B2 JP3513370 B2 JP 3513370B2
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- general formula
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/78—Separation; Purification; Stabilisation; Use of additives
- C07C45/86—Use of additives, e.g. for stabilisation
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
【０００１】[0001]
【発明の属する技術分野】本発明はシンナミックアルデ
ヒド類の保存安定化方法に関し、詳しくは、香料等とし
て有用なシンナミックアルデヒド類の保存中の色や匂い
の劣化を防止するためのシンナミックアルデヒド類の保
存安定化方法に関するものである。BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to a method for preserving and stabilizing cinnamic aldehydes, and more specifically, a cinnamic aldehyde for preventing deterioration of color and odor during storage of cinnamic aldehydes useful as perfumes. The present invention relates to a method for stabilizing and preserving various kinds of storage.
【０００２】[0002]
【従来の技術及び発明が解決しようとする課題】シンナ
ミックアルデヒド類は酸化されやすく、またその製造段
階や保存中に変色や匂いの変化といった品質劣化を生じ
やすいため、その対策としてジフェニルアミンを製造段
階及び／又は生成物中に添加することが行なわれてき
た。BACKGROUND OF THE INVENTION Since cinnamic aldehydes are easily oxidized and quality deterioration such as discoloration or change of odor during storage and storage thereof is likely to occur, diphenylamine is used as a countermeasure. And / or addition into the product has been carried out.
【０００３】しかしながら、前記ジフェニルアミンは、
その後、インターナショナル・フレグランス・アソシエ
ーシェン（ＩＦＲＡ）の規制リストに登録され、香料用
途としてはその使用が禁止された。そのため、シンナミ
ックアルデヒド類の保存中の品質劣化を防止するための
安全な添加剤の開発が望まれていた。However, the diphenylamine is
After that, it was registered on the regulation list of International Fragrance Associates (IFRA) and its use as a fragrance was prohibited. Therefore, development of a safe additive for preventing quality deterioration of cinnamic aldehydes during storage has been desired.
【０００４】従って、本発明の目的はジフェニルアミン
に代わる安全な添加剤を用いた、シンナミックアルデヒ
ド類の安全性に優れた保存安定化方法を提供することに
ある。Therefore, it is an object of the present invention to provide a storage stabilizing method which is excellent in safety of cinnamic aldehydes and which uses a safe additive in place of diphenylamine.
【０００５】[0005]
【課題を解決するための手段】本発明者らは、前記目的
を達成すべく鋭意研究を重ねた結果、ジフェニルアミン
に代えて特定の化合物をシンナミックアルデヒド類に添
加することにより、シンナミックアルデヒド類の保存中
の品質劣化を安全に防止できることを見出し、本発明を
完成するに到った。Means for Solving the Problems As a result of intensive studies to achieve the above object, the present inventors have found that by adding a specific compound to cinnamic aldehydes instead of diphenylamine, cinnamic aldehydes can be obtained. It was found that the deterioration of quality during storage can be safely prevented, and the present invention has been completed.
【０００６】即ち本発明は、一般式（Ｉ）That is, the present invention has the general formula (I)
【０００７】[0007]
【化１０】 [Chemical 10]
【０００８】（式中、R1は水素原子又は炭素数１〜８の
直鎖又は分岐鎖のアルキル基を示す。）で表されるシン
ナミックアルデヒド類に、一般式（II）(In the formula, R 1 represents a hydrogen atom or a linear or branched alkyl group having 1 to 8 carbon atoms), and the cinnamic aldehyde represented by the general formula (II)
【０００９】[0009]
【化１１】 [Chemical 11]
【００１０】〔式中、R2は水素原子、炭素数１〜５の直
鎖又は分岐鎖のアルキル基、置換基として水酸基もしく
は炭素数１〜５の直鎖又は分岐鎖のアルキル基を有して
もよいアリール基あるいはアリールアルキル基を示し、
R3及びR4は同一又は異なって、炭素数１〜５の直鎖又は
分岐鎖のアルキル基、水酸基、置換基として水酸基もし
くは炭素数１〜５の直鎖又は分岐鎖のアルキル基を有し
てもよいアリール基あるいはアリールアルキル基を示
し、ｍ及びｎは０〜５の数を示す。また、ｍ個のR3及び
ｎ個のR4は同一でも異なっていても良い。〕で表される
化合物を添加することを特徴とするシンナミックアルデ
ヒド類の保存安定化方法を提供するものである。[In the formula, R 2 has a hydrogen atom, a linear or branched alkyl group having 1 to 5 carbon atoms, a hydroxyl group or a linear or branched alkyl group having 1 to 5 carbon atoms as a substituent. Optionally represents an aryl group or an arylalkyl group,
R 3 and R 4 are the same or different and each have a linear or branched alkyl group having 1 to 5 carbon atoms, a hydroxyl group, or a hydroxyl group or a linear or branched alkyl group having 1 to 5 carbon atoms as a substituent. Optionally represents an aryl group or an arylalkyl group, and m and n are numbers from 0 to 5. Further, m R 3 and n R 4 may be the same or different. ] A method for preserving and stabilizing cinnamic aldehydes, which comprises adding a compound represented by the formula
【００１１】また本発明、上記一般式（Ｉ）で表される
シンナミックアルデヒド類に、上記一般式（II）で表さ
れる化合物と、下記一般式(III),（IV),（Ｖ）又は（V
I）で表される化合物あるいはトコフェロールからなる
群から選ばれる少なくとも１種の化合物とを添加するこ
とを特徴とするシンナミックアルデヒド類の保存安定化
方法を提供するものである。In the present invention, the cinnamic aldehydes represented by the above general formula (I), the compound represented by the above general formula (II) and the following general formulas (III), (IV) and (V) Or (V
A method for preserving and stabilizing cinnamic aldehydes, which comprises adding the compound represented by I) or at least one compound selected from the group consisting of tocopherols.
【００１２】[0012]
【化１２】 [Chemical 12]
【００１３】〔上記一連の式中、R5, R6, R7及びR9は同
一又は異なって、炭素数１〜５の直鎖又は分岐鎖のアル
キル基もしくはアルコキシ基、あるいは式-R13COOR
14（R13 は炭素数１〜５の直鎖又は分岐鎖のアルキレン
基、R14 は炭素数１〜５の直鎖又は分岐鎖のアルキル基
を示す）で表される基を示し、R8は炭素数１〜５の直鎖
又は分岐鎖のアルキレン基を示し、R10, R11及びR12 は
同一又は異なって、式[In the above series of formulas, R 5 , R 6 , R 7 and R 9 are the same or different and each represents a linear or branched alkyl group or alkoxy group having 1 to 5 carbon atoms, or a compound represented by formula -R 13 COOR
14 (R 13 represents a linear or branched alkylene group having 1 to 5 carbon atoms, R 14 represents a linear or branched alkyl group having 1 to 5 carbon atoms), R 8 Represents a linear or branched alkylene group having 1 to 5 carbon atoms, R 10 , R 11 and R 12 are the same or different,
【００１４】[0014]
【化１３】 [Chemical 13]
【００１５】で表される基を示し、ｐは１〜５の数、
ｑ，ｒ及びｓは１〜４の数を示す。また、ｐ個のR5、ｑ
個のR6、ｒ個のR7、ｓ個のR9は同一でも異なっていても
良い。〕Represents a group represented by, p is a number from 1 to 5,
q, r, and s show the number of 1-4. In addition, p R 5 , q
R 6's , r R 7's , and s R 9's may be the same or different. ]
【００１６】[0016]
【発明の実施の形態】以下、本発明の実施の形態を詳細
に説明する。BEST MODE FOR CARRYING OUT THE INVENTION Embodiments of the present invention will be described in detail below.
【００１７】本発明において、一般式（Ｉ）で表される
シンナミックアルデヒド類の具体例としては、シンナミ
ックアルデヒド、α−メチルシンナミックアルデヒド、
α−エチルシンナミックアルデヒド、α−プロピルシン
ナミックアルデヒド、α−ブチルシンナミックアルデヒ
ド、α−アミルシンナミックアルデヒド、α−ヘキシル
シンナミックアルデヒド、α−オクチルシンナミックア
ルデヒド等が挙げられ、香料として用いるためには、α
−アミルシンナミックアルデヒド、α−ヘキシルシンナ
ミックアルデヒドが好ましい。In the present invention, specific examples of the cinnamic aldehydes represented by the general formula (I) include cinnamic aldehyde, α-methylcinnamic aldehyde,
α-Ethyl cinnamic aldehyde, α-propyl cinnamic aldehyde, α-butyl cinnamic aldehyde, α-amyl cinnamic aldehyde, α-hexyl cinnamic aldehyde, α-octyl cinnamic aldehyde, and the like, for use as a fragrance. Is α
-Amylcinnamic aldehyde and α-hexylcinnamic aldehyde are preferred.
【００１８】本発明においては、前記一般式（II）で表
される化合物を一般式（Ｉ）で表されるシンナミックア
ルデヒド類に添加することによりシンナミックアルデヒ
ド類の保存中の品質劣化を防止することができるのであ
るが、一般式（II）において、R2、R3及びR4で示される
炭素数１〜５の直鎖又は分岐鎖のアルキル基としては、
メチル基、エチル基、プロピル基、ｔ−ブチル基、ペン
チル基等が挙げられる。また、置換基として水酸基もし
くは炭素数１〜５の直鎖又は分岐鎖のアルキル基を有し
てもよいアリール基あるいはアリールアルキル基として
は、置換基として水酸基、メチル基、エチル基、プロピ
ル基、ｔ−ブチル基、ペンチル基等を有してもよいフェ
ニル基、ベンジル基、フェニルエチル基、フェニルプロ
ピル基、フェニルブチル基等が挙げられる。In the present invention, the compound represented by the general formula (II) is added to the cinnamic aldehyde represented by the general formula (I) to prevent quality deterioration of the cinnamic aldehyde during storage. In general formula (II), the straight-chain or branched-chain alkyl group having 1 to 5 carbon atoms represented by R 2 , R 3 and R 4 is as follows.
Examples thereof include a methyl group, an ethyl group, a propyl group, a t-butyl group and a pentyl group. Further, as the aryl group or arylalkyl group which may have a hydroxyl group or a linear or branched alkyl group having 1 to 5 carbon atoms as a substituent, a hydroxyl group, a methyl group, an ethyl group, a propyl group as a substituent, Examples thereof include a phenyl group which may have a t-butyl group and a pentyl group, a benzyl group, a phenylethyl group, a phenylpropyl group and a phenylbutyl group.
【００１９】本発明において、一般式（II）で表される
化合物としては、下記化合物群から選ばれるものが好ま
しく、これらの中では、２, ２' −メチレンビス（４−
エチル−６−ｔ−ブチルフェノール）、４, ４' −ブチ
リデンビス（３−メチル−６−ｔ−ブチルフェノール）
が特に好ましい。In the present invention, the compound represented by the general formula (II) is preferably one selected from the following compound group, and among these, 2,2'-methylenebis (4-
Ethyl-6-t-butylphenol), 4,4'-butylidenebis (3-methyl-6-t-butylphenol)
Is particularly preferable.
【００２０】[0020]
【化１４】 [Chemical 14]
【００２１】（式中、t-Buはｔ−ブチル基を示す。）
本発明において、一般式（II）で表される化合物の添加
量は、一般式（Ｉ）で表されるシンナミックアルデヒド
類に対して、50〜10,000ppm が好ましく、100〜4,000pp
mが更に好ましい。(In the formula, t-Bu represents a t-butyl group.) In the present invention, the addition amount of the compound represented by the general formula (II) is the cinnamic aldehyde represented by the general formula (I). 50 to 10,000 ppm is preferable for 100 to 4,000 pp
m is more preferred.
【００２２】本発明においては、上記一般式（II）で表
される化合物とともに、更に上記一般式(III),（IV),
（Ｖ）又は（VI）で表される化合物あるいはトコフェロ
ールからなる群から選ばれる少なくとも１種の化合物を
添加すると更にシンナミックアルデヒド類の保存安定性
が向上し好ましい。In the present invention, in addition to the compound represented by the above general formula (II), the above general formula (III), (IV),
It is preferable to add the compound represented by (V) or (VI) or at least one compound selected from the group consisting of tocopherols because the storage stability of cinnamic aldehydes is further improved.
【００２３】上記一般式(III),（IV),（Ｖ）又は（VI）
において、R5, R6, R7, R9及びR14で示される炭素数１
〜５の直鎖又は分岐鎖のアルキル基としては、メチル
基、エチル基、プロピル基、ｔ−ブチル基、ペンチル基
等が挙げられ、R5, R6, R7及びR9で示される炭素数１〜
５のアルコキシ基としては、メトキシ基、エトキシ基、
プロポキシ基、ブトキシ基等が挙げられる。また、R8及
びR13 で示される炭素数１〜５の直鎖又は分岐鎖のアル
キレン基としては、メチレン基、エチレン基、プロピレ
ン基、ブチレン基、ペンチレン基等が挙げられる。The above general formula (III), (IV), (V) or (VI)
Has 1 carbon number represented by R 5 , R 6 , R 7 , R 9 and R 14.
Examples of the linear or branched alkyl group of to 5 include a methyl group, an ethyl group, a propyl group, a t-butyl group, a pentyl group, and the like, and carbons represented by R 5 , R 6 , R 7 and R 9 Number 1
As the alkoxy group of 5, a methoxy group, an ethoxy group,
Examples include propoxy group and butoxy group. Examples of the linear or branched alkylene group having 1 to 5 carbon atoms represented by R 8 and R 13 include methylene group, ethylene group, propylene group, butylene group, pentylene group and the like.
【００２４】これらの化合物の中で、一般式（III)で表
される化合物としては、Among these compounds, the compound represented by the general formula (III) is
【００２５】[0025]
【化１５】 [Chemical 15]
【００２６】（式中、t-Bu及びR14 は前記の意味を示
す。）が好ましく、一般式（IV）で表される化合物とし
ては、(Wherein, t-Bu and R 14 have the above-mentioned meanings), and the compound represented by the general formula (IV) is
【００２７】[0027]
【化１６】 [Chemical 16]
【００２８】（式中、t-Buは前記の意味を示す。）が好
ましく、一般式（Ｖ）で表される化合物としては、(Wherein t-Bu has the above-mentioned meaning), and the compound represented by the general formula (V) is
【００２９】[0029]
【化１７】 [Chemical 17]
【００３０】（式中、t-Buは前記の意味を示す。）が好
ましく、一般式（VI）で表される化合物としては、(Wherein t-Bu has the above-mentioned meaning), and the compound represented by the general formula (VI) is
【００３１】[0031]
【化１８】 [Chemical 18]
【００３２】（式中、t-Buは前記の意味を示す。）が好
ましい。更にこれらの化合物の中では、２, ６−ジ−ｔ
−ブチル−４−メチルフェノール（ブチル化ヒドロキシ
トルエン、以下ＢＨＴと略記する）、トコフェロールが
好ましく、特にＢＨＴが好ましい。(In the formula, t-Bu has the above-mentioned meaning.) Is preferred. Further, among these compounds, 2,6-di-t
-Butyl-4-methylphenol (butylated hydroxytoluene, hereinafter abbreviated as BHT) and tocopherol are preferable, and BHT is particularly preferable.
【００３３】上記一般式(III),（IV),（Ｖ）又は（VI）
で表される化合物あるいはトコフェロールからなる群か
ら選ばれる少なくとも１種の化合物の添加量は、一般式
（Ｉ）で表されるシンナミックアルデヒド類に対して、
50〜10,000ppm が好ましく、100 〜4,000ppmが更に好ま
しい。The above general formula (III), (IV), (V) or (VI)
The addition amount of at least one compound selected from the group consisting of the compound represented by: or tocopherol, relative to the cinnamic aldehyde represented by the general formula (I),
50 to 10,000 ppm is preferable, and 100 to 4,000 ppm is more preferable.
【００３４】本発明においては、安全性に優れた上記一
般式（II）で表される化合物、更に好ましくはこの一般
式（II）で表される化合物と、上記一般式(III),（IV),
（Ｖ）又は（VI）で表される化合物あるいはトコフェロ
ールからなる群から選ばれる少なくとも１種の化合物と
をシンナミックアルデヒド類に添加することにより、シ
ンナミックアルデヒド類の保存中の品質の劣化を安全に
防止することができる。In the present invention, the compound represented by the general formula (II) which is excellent in safety, more preferably the compound represented by the general formula (II) and the compounds represented by the general formula (III), (IV ),
The addition of the compound represented by (V) or (VI) or at least one compound selected from the group consisting of tocopherols to cinnamic aldehydes makes it possible to safely prevent deterioration of quality of the cinnamic aldehydes during storage. Can be prevented.
【００３５】[0035]
【実施例】以下、本発明を実施例により更に詳細に説明
するが、本発明はこれらの実施例に限定されるものでは
ない。EXAMPLES The present invention will now be described in more detail with reference to examples, but the present invention is not limited to these examples.
【００３６】実施例１〜２及び比較例１〜３
α−ヘキシルシンナミックアルデヒドに対して、表１に
示す抗酸化剤を1000ppm 添加し、その直後、並びに室温
で12時間及び24時間保存後の匂いを以下に示す方法で官
能評価した。結果を表１に示す。Examples 1 and 2 and Comparative Examples 1 to 3 To the α-hexylcinnamic aldehyde, 1000 ppm of the antioxidant shown in Table 1 was added, and immediately after that, and after storage at room temperature for 12 hours and 24 hours. The odor was sensory-evaluated by the following method. The results are shown in Table 1.
【００３７】＜匂いの評価方法＞匂い紙で匂いを下記の
基準で官能評価した。<Odor Evaluation Method> The odor was sensory-evaluated using odor paper according to the following criteria.
【００３８】 ○：異臭なし △：ほとんど異臭なし ×：異臭あり[0038] ○: No offensive odor △: Almost no offensive odor ×: There is an offensive odor
【００３９】[0039]
【表１】 [Table 1]
【００４０】注）
*1 アンテージW-500 ：川口化学（株）製商品名、２,
２' −メチレンビス（４−エチル−６−ｔ−ブチルフェ
ノール）
*2 アンテージW-300 ：川口化学（株）製商品名、４,
４' −ブチリデンビス（３−メチル−６−ｔ−ブチルフ
ェノール）
*3 トミノックスTT：吉富製薬（株）製商品名、テトラ
キス−〔メチレン−３−(3',5'−ジ−ｔ−ブチル−4'−
ヒドロキシフェニル）プロピオネート〕メタン
実施例３〜４及び比較例４〜５
α−ヘキシルシンナミックアルデヒドに対して、表２に
示す抗酸化剤を3000ppm 添加して室温で12時間、24時
間、２日間及び３日間保存後の匂いを、上記方法で官能
評価した。結果を表２に示す。Note) * 1 Antage W-500: Trade name of Kawaguchi Chemical Co., Ltd., 2,
2'-Methylenebis (4-ethyl-6-t-butylphenol) * 2 Antage W-300: trade name, Kawaguchi Kagaku KK, 4,
4'-butylidene bis (3-methyl-6-t-butylphenol) * 3 Tominox TT: trade name, tetrakis- [methylene-3- (3 ', 5'-di-t-butyl-, manufactured by Yoshitomi Pharmaceutical Co., Ltd.] 4'-
Hydroxyphenyl) propionate] methane Examples 3 to 4 and Comparative Examples 4 to 5 To the α-hexylcinnamic aldehyde, 3000 ppm of the antioxidant shown in Table 2 was added, and the mixture was added at room temperature for 12 hours, 24 hours, and 2 days. The odor after storage for 3 days was sensory-evaluated by the above method. The results are shown in Table 2.
【００４１】[0041]
【表２】 [Table 2]
【００４２】注）
*1：ビン口では酸臭あり
実施例５〜１４及び比較例６〜１０
30mlのスクリュー管に10ｇのα−ヘキシルシンナミック
アルデヒド及び表３に示す抗酸化剤を表３に示す量添加
し、振盪後、１日２回フタを取り、ビン口で匂いを観察
した。結果を表３に示す。Note) * 1: There is an acid odor at the bottle mouth. Examples 5 to 14 and Comparative Examples 6 to 10 10 g of α-hexylcinnamic aldehyde and the antioxidant shown in Table 3 are shown in Table 3 in a 30 ml screw tube. After adding the indicated amount and shaking, the lid was removed twice a day, and the odor was observed at the bottle mouth. The results are shown in Table 3.
【００４３】[0043]
【表３】 [Table 3]
【００４４】注） *1：α−ヘキシルシンナミックアルデヒドに対する量Note) * 1: Amount for α-hexylcinnamic aldehyde
───────────────────────────────────────────────────── フロントページの続き (56)参考文献 特開 平３−14535（ＪＰ，Ａ) 特開 平９−40538（ＪＰ，Ａ) 特開 平７−10728（ＪＰ，Ａ) 特開 平７−187976（ＪＰ，Ａ) 特開 平７−10791（ＪＰ，Ａ) ─────────────────────────────────────────────────── ─── Continued front page (56) References JP-A-3-14535 (JP, A) JP 9-40538 (JP, A) JP 7-10728 (JP, A) Japanese Patent Laid-Open No. 7-187976 (JP, A) JP-A-7-10791 (JP, A)
Claims (4)
鎖のアルキル基を示す。）で表されるシンナミックアル
デヒド類に、一般式（II） 【化２】 〔式中、R2は水素原子、炭素数１〜５の直鎖又は分岐鎖
のアルキル基、置換基として水酸基もしくは炭素数１〜
５の直鎖又は分岐鎖のアルキル基を有してもよいアリー
ル基あるいはアリールアルキル基を示し、R3及びR4は同
一又は異なって、炭素数１〜５の直鎖又は分岐鎖のアル
キル基、水酸基、置換基として水酸基もしくは炭素数１
〜５の直鎖又は分岐鎖のアルキル基を有してもよいアリ
ール基あるいはアリールアルキル基を示し、ｍ及びｎは
０〜５の数を示す。また、ｍ個のR3及びｎ個のR4は同一
でも異なっていても良い。〕で表される化合物を添加す
ることを特徴とするシンナミックアルデヒド類の保存安
定化方法。1. A compound represented by the general formula (I): (In the formula, R 1 represents a hydrogen atom or a linear or branched alkyl group having 1 to 8 carbon atoms.) The cinnamic aldehyde represented by the general formula (II) [In the formula, R 2 is a hydrogen atom, a linear or branched alkyl group having 1 to 5 carbon atoms, a hydroxyl group or 1 to 1 carbon atoms as a substituent.
5 represents an aryl group or an arylalkyl group which may have a linear or branched alkyl group, wherein R 3 and R 4 are the same or different, and are a linear or branched alkyl group having 1 to 5 carbon atoms. , Hydroxyl group, hydroxyl group as substituent or carbon number 1
~ 5 represents an aryl group or an arylalkyl group which may have a linear or branched alkyl group, and m and n represent a number of 0 to 5. Further, m R 3 and n R 4 may be the same or different. ] The storage stabilization method of the cinnamic aldehydes characterized by adding the compound represented by these.
は（VI）で表される化合物あるいはトコフェロールから
なる群から選ばれる少なくとも１種の化合物を添加する
ことを特徴とする請求項１記載の保存安定化方法。 【化３】 〔上記一連の式中、R5, R6, R7及びR9は同一又は異なっ
て、炭素数１〜５の直鎖又は分岐鎖のアルキル基もしく
はアルコキシ基、あるいは式-R13COOR14（R13 は炭素数
１〜５の直鎖又は分岐鎖のアルキレン基、R14 は炭素数
１〜５の直鎖又は分岐鎖のアルキル基を示す）で表され
る基を示し、R8は炭素数１〜５の直鎖又は分岐鎖のアル
キレン基を示し、R10, R11及びR12 は同一又は異なっ
て、式 【化４】 で表される基を示し、ｐは１〜５の数、ｑ，ｒ及びｓは
１〜４の数を示す。また、ｐ個のR5、ｑ個のR6、ｒ個の
R7及びｓ個のR9は同一でも異なっていても良い。〕2. A compound represented by the following general formula (III), (IV), (V) or (VI) or at least one compound selected from the group consisting of tocopherols is added. The storage stabilization method according to claim 1. [Chemical 3] [In the above series of formulas, R 5 , R 6 , R 7 and R 9 are the same or different and each represents a linear or branched alkyl group or alkoxy group having 1 to 5 carbon atoms, or a group represented by formula -R 13 COOR 14 ( R 13 represents a linear or branched alkylene group having 1 to 5 carbon atoms, R 14 represents a linear or branched alkyl group having 1 to 5 carbon atoms, and R 8 represents carbon. A linear or branched alkylene group of the formulas 1 to 5, wherein R 10 , R 11 and R 12 are the same or different and are represented by the formula: Is shown, p is a number of 1 to 5, q, r and s are numbers of 1 to 4. Also, p R 5 , q R 6 , and r R
R 7 and s R 9 may be the same or different. ]
合物群から選ばれるものである請求項１又は２記載の保
存安定化方法。 【化５】 （式中、t-Buはｔ−ブチル基を示す。）3. The storage stabilization method according to claim 1, wherein the compound represented by the general formula (II) is selected from the following compound group. [Chemical 5] (In the formula, t-Bu represents a t-butyl group.)
一般式（IV）で表される化合物が、 【化７】 （式中、t-Buは前記の意味を示す。）であり、一般式
（Ｖ）で表される化合物が、 【化８】 （式中、t-Buは前記の意味を示す。）であり、一般式
（VI）で表される化合物が、 【化９】 （式中、t-Buは前記の意味を示す。）である請求項２又
は３記載の保存安定化方法。4. A compound represented by the general formula (III) is: (In the formula, t-Bu and R 14 have the above-mentioned meanings.),
The compound represented by the general formula (IV) is (In the formula, t-Bu has the above-mentioned meaning.), And the compound represented by the general formula (V) is (In the formula, t-Bu has the above-mentioned meaning.), And the compound represented by the general formula (VI) is (In the formula, t-Bu has the above-mentioned meaning.) The storage stabilization method according to claim 2 or 3.
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP27612297A JP3513370B2 (en) | 1997-10-08 | 1997-10-08 | Method for preserving and stabilizing cinamic aldehydes |
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| Publication Number | Publication Date |
|---|---|
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| JP3513370B2 true JP3513370B2 (en) | 2004-03-31 |
Family
ID=17565106
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|---|---|---|---|
| JP27612297A Expired - Fee Related JP3513370B2 (en) | 1997-10-08 | 1997-10-08 | Method for preserving and stabilizing cinamic aldehydes |
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