JPH0753690B2 - Cosmetic containing 1,3-diol ester - Google Patents
Cosmetic containing 1,3-diol esterInfo
- Publication number
- JPH0753690B2 JPH0753690B2 JP61023090A JP2309086A JPH0753690B2 JP H0753690 B2 JPH0753690 B2 JP H0753690B2 JP 61023090 A JP61023090 A JP 61023090A JP 2309086 A JP2309086 A JP 2309086A JP H0753690 B2 JPH0753690 B2 JP H0753690B2
- Authority
- JP
- Japan
- Prior art keywords
- present
- skin
- propanediol
- ester
- cosmetics
- 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 - Fee Related
Links
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q19/00—Preparations for care of the skin
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
- A61K8/37—Esters of carboxylic acids
- A61K8/375—Esters of carboxylic acids the alcohol moiety containing more than one hydroxy group
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
- A61K2800/74—Biological properties of particular ingredients
- A61K2800/75—Anti-irritant
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q1/00—Make-up preparations; Body powders; Preparations for removing make-up
- A61Q1/02—Preparations containing skin colorants, e.g. pigments
- A61Q1/04—Preparations containing skin colorants, e.g. pigments for lips
- A61Q1/06—Lipsticks
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q5/00—Preparations for care of the hair
Landscapes
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Dermatology (AREA)
- Emergency Medicine (AREA)
- Birds (AREA)
- Epidemiology (AREA)
- Cosmetics (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
【発明の詳細な説明】 （ａ）産業上の利用分野 本発明は、側鎖をもつ特定の1,3−ジオールエステルを
配合してなる皮膚用または頭髪用化粧料に関するもので
ある。DETAILED DESCRIPTION OF THE INVENTION (a) Field of Industrial Application The present invention relates to a skin or hair cosmetic composition containing a specific 1,3-diol ester having a side chain.
（ｂ）従来の技術 一般に化粧料の使用対象は人体の皮膚および頭髪である
ため、その主要な原料である油性基剤としては人体の皮
脂にできるだけ類似した成分及び性状のものを使用する
ことが望ましく、皮膚に対して刺激のないことが最も重
要である。(B) Conventional Technology Generally, cosmetics are used for human skin and hair. Therefore, as an oily base which is a main raw material of the cosmetics, it is preferable to use components and properties similar to human sebum as much as possible. Desirable, and non-irritating to the skin is of paramount importance.
人体皮脂に近づける手段のひとつとして、不飽和結合を
有する化合物を導入することが考えられるが、不飽和結
合は光、空気などに対して非常に不安定で、容易に酸化
する。そして酸化した化合物は皮膚に強い刺激および毒
性を及ぼすため好ましくない。As one of the means for bringing human skin oil closer, it is possible to introduce a compound having an unsaturated bond, but the unsaturated bond is very unstable to light and air and easily oxidizes. Oxidized compounds are not preferable because they have strong irritation and toxicity to the skin.
（ｃ）発明が解決しようとする問題点 本発明は、人体皮脂に類似した性状をもち、皮膚に対し
無刺激で、かつ優れた感触を有し、酸化および加水分解
に対して安定な、常温で液状の油性基剤を配合してなる
化粧料を提供することを目的とする。(C) Problems to be Solved by the Invention The present invention has properties similar to human sebum, has no irritation to the skin, has an excellent feel, and is stable to oxidation and hydrolysis at room temperature. An object of the present invention is to provide a cosmetic composition containing a liquid oily base.
（ｄ）問題点を解決するための手段 本発明者らは、種々研究を重ねた結果、下記の一般式
（Ｉ）のエステルが、この目的に合致することを見出し
本発明を完成した。(D) Means for Solving the Problems As a result of various studies, the present inventors have found that the ester of the following general formula (I) meets this purpose, and completed the present invention.
即ち、本発明は、一般式 （式中、Ｒは2,2−ジエチル−1,3−プロパンジオールま
たは２−ｎ−ブチル−２−エチル−1,3−プロパンジオ
ールの各アルキル残基、Ｒ′はｎ−デカン酸または２−
エチルヘキサン酸の各アルキル残基を表す）で示される
側鎖をもつ1,3−ジオールエステルの１種または２種以
上を配合してなる皮膚用または頭髪用化粧料である。That is, the present invention has the general formula (In the formula, R is each alkyl residue of 2,2-diethyl-1,3-propanediol or 2-n-butyl-2-ethyl-1,3-propanediol, and R'is n-decanoic acid or 2 −
A cosmetic for skin or hair comprising one or more kinds of 1,3-diol ester having a side chain represented by (representing each alkyl residue of ethylhexanoic acid).
一般式（Ｉ）のエステルは側鎖をもつ1,3−ジオールと
ｎ−デカン酸、２−エチルヘキサン酸の１種またはその
混合物とをエステル化反応して得ることができる。The ester of the general formula (I) can be obtained by esterifying a 1,3-diol having a side chain and one or a mixture of n-decanoic acid and 2-ethylhexanoic acid.
上記の側鎖をもつ1,3−ジオールとしては2,2−ジエチル
−1,3−プロパンジオール、２−ｎ−ブチル−２−エチ
ル−1,3−プロパンジオールの１種または２種のアルコ
ールを使用する。The 1,3-diol having the above side chain is one or two alcohols of 2,2-diethyl-1,3-propanediol and 2-n-butyl-2-ethyl-1,3-propanediol. To use.
エステル化反応は公知の方法が採用でき、触媒は使用し
ても、しなくてもよい。A known method can be adopted for the esterification reaction, and the catalyst may or may not be used.
エステル化反応終了後、必要に応じて常法に従い反応混
合物をアルカリ洗浄により脱酸、脱色剤により脱色、水
蒸気蒸留により脱臭精製するか真空蒸留による精製を行
う。After completion of the esterification reaction, if necessary, the reaction mixture is deoxidized by alkali washing, decolorized by a decoloring agent, deodorized by steam distillation, or purified by vacuum distillation.
得られた本発明のエステルは、いずれも無色無臭であ
り、常温で液状を呈し、酸化安定性および耐アルカリ加
水分解性に優れ、刺激性を有さない。All of the obtained esters of the present invention are colorless and odorless, exhibit a liquid state at room temperature, have excellent oxidation stability and alkali hydrolysis resistance, and have no irritation.
このエステルは種々の化粧料、例えば栄養クリーム、乳
液、バスオイル、口紅等の皮膚用化粧品、ヘアオイル、
ヘアリンス等の頭髪用化粧品に配合して用いることがで
きる。すなわち、常法による化粧料の製造に於いて、従
来の油性基剤の一部を本発明のエステルに代えて使用す
る。This ester is used in various cosmetics such as nutrition cream, emulsion, bath oil, skin cosmetics such as lipstick, hair oil,
It can be used by blending with hair cosmetics such as hair rinse. That is, in the production of cosmetics by a conventional method, a part of the conventional oily base is used in place of the ester of the present invention.
このようにして得られた化粧料は皮膚ないし頭髪に対す
る特性が極めて優れている。第１表に本発明に係る各種
エステルの酸化安定性をAOM（Active Oxygen Method）
試験によって調べた結果を示す。同表から明らかなよう
に、本発明に係るエステルはオリーブ油等の従来の化粧
料用油性基剤に比べ酸化安定性が非常に良好である。な
お、AOM試験はAOM測定用吹込管に試料20mlを入れ、97.8
±0.2℃の油浴中で空気を2.3ml/秒の割合で吹き込み、
一定時間毎に試料を採取し、その過酸化物価（POV）を
測定するものである。The cosmetic thus obtained has extremely excellent properties for skin and hair. Table 1 shows the oxidative stability of various esters according to the present invention by AOM (Active Oxygen Method).
The result investigated by the test is shown. As is clear from the table, the ester according to the present invention has very good oxidative stability as compared with conventional oily bases for cosmetics such as olive oil. For the AOM test, put 20 ml of the sample into the AOM measurement blow tube, and
Blow air at a rate of 2.3 ml / sec in an oil bath at ± 0.2 ° C,
A sample is taken at regular intervals and the peroxide value (POV) is measured.
また、第２表に本発明に係る各種エステルの耐アルカリ
加水分解性の試験結果を示す。同表から明らかなよう
に、本発明に係るエステルはオリーブ油等の従来の化粧
料用油性基剤に比べ耐アルカリ加水分解性に優れてい
る。なお、耐アルカリ加水分解性は試料約2gとN/3エタ
ノールカリ25mlをケン化価測定用フラスコに採り、冷却
管をつけ85℃に加熱し、一定時間毎に試料のケン化価を
測定し、その値を別に1Nエタノールカリにより85℃で３
時間反応させた時のケン化価で除して分解率を求めるも
のである。Further, Table 2 shows the test results of alkali hydrolysis resistance of various esters according to the present invention. As is clear from the table, the ester according to the present invention is more excellent in alkali hydrolysis resistance than conventional oily bases for cosmetics such as olive oil. For alkali hydrolysis resistance, sample about 2 g and 25 ml of N / 3 ethanol potassium in a saponification value measuring flask, attach a cooling tube and heat to 85 ° C, and measure the saponification value of the sample at regular intervals. , The value is separately 3 at 85 ℃ with 1N ethanol potassium.
The decomposition rate is obtained by dividing by the saponification value when reacted for a time.
第３表に本発明に係る各種エステルの皮膚１次刺激テス
トおよび眼粘膜刺激テストの試験結果を示す。同表から
明らかなように、本発明に係るエステルは刺激性がな
く、化粧品用油性基剤としてきわめて優れたものであ
る。Table 3 shows the test results of the primary skin irritation test and the eye mucous membrane irritation test of various esters according to the present invention. As is clear from the table, the ester according to the present invention is not irritating and is extremely excellent as an oily base for cosmetics.
なお、皮膚刺激試験は体重約3kgの雄ウサギ３羽を用
い、背面の体毛をバリカンで除去し、試料0.1mlずつ塗
布し、３時間、24時間および48時間後に塗布部位の発赤
（紅斑）、浮腫等の程度をDraizeの判定表により判定す
るもので、０は刺激が全くないことを表す。また、眼粘
膜試験は体重約2kgの雌ウサギ３羽を用い、試料を0.05m
lずつ点眼投与し、３時間、24時間および48時間後に観
察しDraizeの判定表を参考にして判定するもので、０は
刺激が全くないことを表す。In the skin irritation test, three male rabbits weighing about 3 kg were used, the back hair was removed with hair clippers, and 0.1 ml of each sample was applied, and after 3 hours, 24 hours, and 48 hours, redness (erythema) at the application site, The degree of edema or the like is judged by the Draize judgment table, and 0 means that there is no irritation. In the ocular mucosa test, 3 female rabbits weighing about 2 kg were used and the sample was 0.05 m.
It is administered by instillation of 1 each and observed after 3 hours, 24 hours, and 48 hours, and is determined by referring to the determination table of Draize, and 0 indicates that there is no irritation.
（ｅ）発明の効果 上記したように本発明のエステルは、従来の化粧料用油
性基剤に比べ、酸化安定性、耐加水分解性が高く、無色
・無臭で皮膚刺激、眼粘膜刺激も認められない。また、
人体皮脂に類似した性状と、良好な感触を持ち、これを
用いた化粧料も配合した本発明の油性基剤の特長にみあ
った優れた品質を有するものである。(E) Effects of the Invention As described above, the ester of the present invention has higher oxidation stability and higher hydrolysis resistance than conventional oily bases for cosmetics, is colorless and odorless, and is irritating to skin and eye mucous membranes. I can't. Also,
It has properties similar to human sebum and a good feel, and has excellent quality matching the features of the oil-based base of the present invention, which also contains a cosmetic using the same.
（ｆ）実施例 以下の合成例１〜４において本発明に係る各種エステル
の製造例および生成物の分析値を示す。(F) Example In the following Synthesis Examples 1 to 4, production examples of various esters according to the present invention and analytical values of products are shown.
合成例１ 2,2−ジエチル−1,3−プロパン−ジ−ｎ−デ
カノエートの合成 攪拌機、温度計、窒素ガス吹込管、水分離器を備えた１
の４ツ口フラスコに2,2−ジエチル−1,3−プロパンジ
オール1.0モル、ｎ−デカン酸2.06モル、キシロールを
全仕込量に対して５重量％加え、160〜260℃にて計算量
の水が水分離器にたまるまで反応した。反応時間は５時
間を要した。反応終了後、常法により脱酸を行い、次い
で脱色剤を用いて脱色後、水蒸気を吹き込み減圧下に脱
臭を行って無色無臭の目的物を得た。Synthesis Example 1 Synthesis of 2,2-diethyl-1,3-propane-di-n-decanoate 1 equipped with a stirrer, thermometer, nitrogen gas blowing pipe, water separator 1
Into a 4-necked flask, 1.0 mol of 2,2-diethyl-1,3-propanediol, 2.06 mol of n-decanoic acid and 5% by weight of xylol were added to the total charged amount, and the calculated amount was calculated at 160 to 260 ° C. The water reacted until it accumulated in the water separator. The reaction time required 5 hours. After completion of the reaction, deoxidation was carried out by a conventional method, followed by decolorization using a decolorizing agent, and then deodorization under reduced pressure by blowing steam to obtain a colorless and odorless target product.
合成例２ ２−ｎ−ブチル−２−エチル−1,3−プロパ
ン−ジ−ｎ−デカノエートの合成 合成例１と同様にして２−ｎ−ブチル−２−エチル−1,
3−プロパンジオール1.0モル、ｎ−デカン酸2.06モルを
反応させて無色無臭の目的物を得た。Synthesis Example 2 Synthesis of 2-n-butyl-2-ethyl-1,3-propane-di-n-decanoate 2-n-butyl-2-ethyl-1, in the same manner as in Synthesis Example 1.
1.0 mol of 3-propanediol and 2.06 mol of n-decanoic acid were reacted to obtain a colorless and odorless target product.
合成例３ 2,2−ジエチル−1,3−プロパン−ジ−２−エ
チルヘキサナートの合成 攪拌機、温度計、窒素ガス吹込管、水分離器を備えた１
の４ツ口フラスコに2,2−ジエチル−1,3−プロパンジ
オール1.0モル、２−エチルヘキサン酸2.06モル、エス
テル化触媒としてパラトルエンスルホン酸を全仕込量に
対して0.3重量％およびキシロールを全仕込量に対して
５重量％加え、160〜260℃にて計算量の水が水分離器に
たまるまで反応した。反応時間は10時間を要した。反応
終了後、常法により脱酸を行い、次いで脱色剤を用いて
脱色後、水蒸気を吹き込み減圧下に脱臭を行って無色無
臭の目的物を得た。Synthesis Example 3 Synthesis of 2,2-diethyl-1,3-propane-di-2-ethylhexanate 1 equipped with a stirrer, thermometer, nitrogen gas blowing pipe, water separator
In a 4-necked flask, 1.0 mol of 2,2-diethyl-1,3-propanediol, 2.06 mol of 2-ethylhexanoic acid, 0.3 wt% of paratoluenesulfonic acid as an esterification catalyst based on the total charged amount, and xylol were added. 5 wt% was added to the total amount charged, and the mixture was reacted at 160 to 260 ° C until the calculated amount of water was accumulated in the water separator. The reaction time required 10 hours. After completion of the reaction, deoxidation was carried out by a conventional method, followed by decolorization using a decolorizing agent, and then deodorization under reduced pressure by blowing steam to obtain a colorless and odorless target product.
合成例４ ２−ｎ−ブチル−２−エチル−1,3−プロパ
ン−ジ−２−エチルヘキサナートの合成 合成例３と同様にして２−ｎ−ブチル−２−エチル−1,
3−プロパンジオール1.0モル、２−エチルヘキサン酸2.
06モルを反応させて無色無臭の目的物を得た。Synthesis Example 4 Synthesis of 2-n-butyl-2-ethyl-1,3-propane-di-2-ethylhexanate In the same manner as in Synthesis Example 3, 2-n-butyl-2-ethyl-1,
1.0 mol of 3-propanediol, 2-ethylhexanoic acid 2.
06 mol was reacted to obtain a colorless and odorless target product.
以上の各種エステルの分析値を第４表に示す。以下の実
施例１〜４に於いて本発明に係る化粧料の例を示す。い
ずれも本発明のエステルを配合したことにみあう優れた
品質を有するものであった。Table 4 shows the analytical values of the above various esters. Examples of the cosmetics according to the present invention will be shown in Examples 1 to 4 below. All had excellent qualities that matched the incorporation of the ester of the present invention.
実施例１ W/O型栄養クリーム 2,2−ジエチル−1,3−プロパン−ジ−30重量％（以
下同様） ｎ−デカノエート スクアラン 15 ラノリン 15 ソルビタンモノオレート 6 ポリオキシエチレンソルビタンモノオレート 3
イオン交換水 30 香料・防腐剤 適量 上記のの各成分を50〜60℃に加熱し、攪拌混合して溶
解後、これにの成分を加え混合し、さらにの成分を
添加した。Example 1 W / O type nutritional cream 2,2-diethyl-1,3-propane-di-30 wt% (same below) n-decanoate squalane 15 lanolin 15 sorbitan monooleate 6 polyoxyethylene sorbitan monooleate 3
Ion-exchanged water 30 Perfume / preservative Appropriate amount Each of the above components was heated to 50 to 60 ° C., stirred and mixed to dissolve, then the components were added and mixed, and further components were added.
実施例２ 乳液 2,2−ジエチル−1,3−プロパン−ジ−20
２−エチルヘキサナート ラノリン 1 ミツロウ 2 ポリキシエチレンソルビタンモノオレート 1
ソルビタンモノステアレート 2 防腐剤 適量 抗酸化剤 適量 グリセリン 3 水 70 香料 適量 の各成分を60〜80℃で加熱溶解したのち、の成分を
加えて混合後、冷却しながら香料を加えて分散させた。Example 2 Emulsion 2,2-diethyl-1,3-propane-di-20
2-ethylhexanate lanolin 1 beeswax 2 polyoxyethylene sorbitan monooleate 1
Sorbitan monostearate 2 Preservative proper amount Antioxidant proper amount Glycerin 3 Water 70 Fragrance Appropriate amount of each component was heated and dissolved at 60-80 ° C, then after adding and mixing components, disperse by adding perfume while cooling. .
実施例３ 口紅 ２−ｎ−ブチル−２−エチル−1,3− 70
プロパン−ジ−ｎ−デカノエート ミツロウ 15 カルナバワックス 4 ラノリン 3 染料、顔料 7 香料、抗酸化剤 適量 の成分を加熱融解・混合したのち、の成分を加えて
良く分散したものに、の成分を加えて成型器で成型し
た。Example 3 Lipstick 2-n-butyl-2-ethyl-1,3-70
Propane-di-n-decanoate Beeswax 15 Carnauba wax 4 Lanolin 3 Dyes, pigments 7 Fragrances, antioxidants After heating and mixing a suitable amount of the ingredients, add the ingredients and add the ingredients to a well-dispersed mixture. It was molded with a molding machine.
実施例４ 透明オイルリンス ２−ｎ−ブチル−２−エチル−1,3− 5
プロパン−ジ−２−エチルヘキサナート カチオン界面活性剤 1.5 レシチン 1.5 グリセリン 10 ポリオキシエチレンソルビタンモノオレート 8
エタノール 7 防腐剤 適量 抗酸化剤 適量 水 66 香料 適量 の各成分を60℃で加熱混合したものを60℃の水の中に
加え、混合しながら冷却し、香料を加えた。Example 4 Clear oil rinse 2-n-butyl-2-ethyl-1,3-5
Propane-di-2-ethylhexanate Cationic surfactant 1.5 Lecithin 1.5 Glycerin 10 Polyoxyethylene sorbitan monooleate 8
Ethanol 7 Preservative: proper amount Antioxidant: proper amount Water 66: Fragrance A proper amount of each component was heated and mixed at 60 ° C, added to water at 60 ° C, cooled while mixing, and the flavor was added.
Claims (1)
たは２−ｎ−ブチル−２−エチル−1,3−プロパンジオ
ールの各アルキル残基、Ｒ′はｎ−デカン酸または２−
エチルヘキサン酸の各アルキル残基を表す）で示される
側鎖をもつ1,3−ジオールエステルの１種または２種以
上を配合してなる皮膚用または頭髪用化粧料。1. A general formula (I) (In the formula, R is each alkyl residue of 2,2-diethyl-1,3-propanediol or 2-n-butyl-2-ethyl-1,3-propanediol, and R'is n-decanoic acid or 2 −
A cosmetic for skin or hair comprising one or more kinds of 1,3-diol ester having a side chain represented by (each alkyl residue of ethylhexanoic acid).
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP61023090A JPH0753690B2 (en) | 1986-02-04 | 1986-02-04 | Cosmetic containing 1,3-diol ester |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP61023090A JPH0753690B2 (en) | 1986-02-04 | 1986-02-04 | Cosmetic containing 1,3-diol ester |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP26313894A Division JP2506062B2 (en) | 1994-10-03 | 1994-10-03 | Novel ester and cosmetics containing the same |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS62181236A JPS62181236A (en) | 1987-08-08 |
| JPH0753690B2 true JPH0753690B2 (en) | 1995-06-07 |
Family
ID=12100727
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP61023090A Expired - Fee Related JPH0753690B2 (en) | 1986-02-04 | 1986-02-04 | Cosmetic containing 1,3-diol ester |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH0753690B2 (en) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE102009048773A1 (en) * | 2009-10-08 | 2011-04-21 | Oxea Deutschland Gmbh | Process for the color lightening of polyol esters |
| DE102009048774A1 (en) * | 2009-10-08 | 2011-04-28 | Oxea Deutschland Gmbh | Process for the color lightening of polyol esters |
| DE102010027458A1 (en) * | 2010-07-17 | 2012-01-19 | Oxea Gmbh | Process for the post-treatment of polyol esters |
| CN110818560A (en) * | 2019-12-02 | 2020-02-21 | 怀化金鑫新材料有限公司 | Preparation method of 4-benzyloxy phenyl ethyl n-decanoate |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5529079B2 (en) * | 1972-09-06 | 1980-07-31 | ||
| JPS5581735A (en) * | 1978-12-14 | 1980-06-20 | Kao Corp | Emulsifier composition |
| EP0163806B1 (en) * | 1984-05-07 | 1990-08-29 | Miranol Inc. | Mixtures of oligomers of partially esterified pentaerythritol, their preparation and use |
-
1986
- 1986-02-04 JP JP61023090A patent/JPH0753690B2/en not_active Expired - Fee Related
Non-Patent Citations (1)
| Title |
|---|
| Ｊ．ＩｎｄｉａｎＣｈｅｍ．Ｓｏｃ．，５８〔６〕（１９８１），５９４−５９６ |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS62181236A (en) | 1987-08-08 |
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