Kao Corporation

Akira Matsunaga

Tomihiro Kurosaki

Junya Wakatsuki

Takashi Imamura

Nobutaka Horinishi

Masayuki Ueda

Toshio Nozaki

Akira Fujiu

Shinji Tsuyutani

Tohru Katoh

Masaki Tsumadori

Akio Kimura

Akira Sakaguchi

Shigetoshi Suzue

Takeshi Shirasawa

Satoru Kijima

Yasuo Amishige

Kaoru Ohmae

Kaoru Omae

Kozo Ohira

Masami Itoh

Noboru Nomura

Jun Kurii

The present invention provides a method for producing polyoxyalkylene alkyl ether carboxylic acid and a salt thereof, including supplying polyoxyalkylene alkyl ether, oxygen, and water to a continuous stirred tank reactor containing a noble metal catalyst to oxidize the polyoxyalkylene alkyl ether with oxygen, in which the molar ratio of the salt of polyoxyalkylene alkyl ether carboxylic acid to the polyoxyalkylene alkyl ether in the continuous stirred tank reactor is controlled to 0.33 to 49.

Method for producing polyoxyalkylene alkyl ether carboxylic acid and salt thereof

The present invention relates to a process for producing an ether carboxylate which includes the steps of (1) reacting an aliphatic monohydric alcohol with an alkylene oxide in the presence of an alkali catalyst; (2) neutralizing a reaction solution obtained in the step (1) with an acid such as hydroxycarboxylic acids to obtain an ether alcohol; and (3-1) reacting the obtained ether alcohol with a monohalogenofatty acid or a salt thereof and an alkali metal hydroxide, or (3-2) subjecting the obtained ether alcohol to catalytic oxidation reaction in the presence of a catalyst. The obtained ether carboxylate has a less odor and a high quality and is therefore suitably used in the applications such as cosmetics and toiletries.

Process for production of ether carboxylates

Provided are a process for producing a phosphate and a process for stabilizing a phosphate, the phosphate being an acid-form phosphate wherein an organic hydroxy compound is an alkylene oxide adduct. A production process of a phosphate and a stabilization process of a phosphate, including the step 1 of reacting an organic hydroxy compound represented by the following general formula (I) with a phosphorylating agent:R&#x2014;O&#x2014;(AO)&#x2014;H&#x2003;&#x2003;(I)wherein Rrepresents a straight or branched alkyl group or alkenyl group having 6 to 36 carbon atoms, AO represents an oxyalkylene group having 2 to 4 carbon atoms, and n is a number of 0.1 to 100 on the average; the step 2 of purifying the reaction product obtained in the step 1 until the content of the organic hydroxy compound that has not yet reacted becomes 2% or less by weight; and the step 3 of adding water to the purified product obtained in the step 2 at such a ratio that the content of water in the final product is from 0.5 to 10% by weight.

Process for producing phosphate

An organic hydroxyl compound is reacted with a phosphorylating agent comprising phosphorus pentaoxide and at least one compound selected from the group consisting of water, phosphoric acid and polyphosphoric acid and having a value represented by formula (I) of from 0.5 to 1.0, under such a condition that the ratio as defined by formula (II) has a value in the range of from 2.8 to 3.2; or alternatively, an organic hydroxyl compound is reacted with the above phosphorylating agent under such a condition that the ratio as defined by formula (II) has a value in the range of from exceeding 3.2 up to 6.4 and then phosphorus pentaoxide is added to the reaction product in such an amount that the ratio as defined by formula (II) has a value in the range of from 2.8 to 3.2 with respect to the total feeds of the starting materials to conduct further reaction. Said process enables the preparation of a phosphoric ester mixture which is excellent in hue and odor, is reduced in the amount of orthophosphoric acid formed as a by-product and contains a phosphoric monoester useful as the component of detergent in an increased amount.

Process for the preparation of phosphoric monoester

An organic hydroxyl compound is reacted with a phosphorylating agent comprising phosphorus pentaoxide and at least one compound selected from the group consisting of water, phosphoric acid and polyphosphoric acid and having a value represented by formula (I) of from 0.5 to 1.0, under such a condition that the ratio as defined by formula (II) has a value in the range of from 2.8 to 3.2; or alternatively, an organic hydroxyl compound is reacted with the above phosphorylating agent under such a condition that the ratio as defined by formula (II) has a value in the range of from exceeding 3.2 up to 6.4 and then phosphorus pentaoxide is added to the reaction product in such an amount that the ratio as defined by formula (II) has a value in the range of from 2.8 to 3.2 with respect to the total feeds of the starting materials to conduct further reaction: ##EQU1## The above process produces a phosphoric ester mixture that is excellent in hue and odor, is reduced in the amount of orthophosphoric acid and contains a phosphoric monoester useful as a component of a detergent.

Bleaching composition

Phosphoric acid esters represented by the following formulae (I) and (IX) as well as processes for preparing them are disclosed. ##STR1## wherein R.sub.1 represents a linear or branched, alkyl or alkenyl group having a C.sub.1-36 carbon atom content, with or without the hydrogen atom(s) being substituted with fluorine atom(s), or a phenyl group with substituted linear or branched alkyl group(s) having a C.sub.1-15 carbon atom content, R.sub.2 represents an alkylene group having a C.sub.2-3 carbon atom content, R.sub.3 and R.sub.4 independently denote a hydrogen atom or an alkyl group having a C.sub.1-3 carbon atom content, R.sub.5 and R.sub.6 independently denote a hydrogen atom, or an alkyl, alkenyl, or phenyl group with or without the hydrogen atom(s) being substituted with group(s) containing hetero atom(s), excepting for a mercapto group, R.sub.7 and R.sub.8 independently denote a hydrogen atom, or an alkyl, or alkenyl group, m is an integer of 0-30, n is an integer of 0-5, l is an integer of 0-3, M is a hydrogen atom, an alkali metal, an alkali earth metal, an ammonium group, an alkyl amine group, or an alkanol amine group. The phosphoric acid esters have outstanding surface activity and good foaming capability, and imparts only extremely low irritation to the skin. The detergent composition into which they are formulated is particularly useful as, shampoo, baby shampoo, body shampoo.

Phosphoric acid ester, process for preparing the same, and detergent

A peptide or protein is modified by reacting a phosphoric acid ester represented by the following general formula (I) with a peptide or protein: ##STR1## wherein R.sub.1 means a linear or branched, C.sub.1-36 alkyl or C.sub.2-36 alkenyl group whose hydrogen atom or atoms may be substituted by the corresponding number of fluorine atom(s) or a phenyl group substituted by at least one linear or branched C.sub.1-15 alkyl group, R.sub.2 denotes a C.sub.2-3 alkylene group, m stands for a number of 0-30, and M is a hydrogen atom, an alkali metal ion, an alkaline earth metal ion, an ammonium ion, an alkylamine residue or an alkanolamine residue.

Modification method for peptides and proteins by reacting with a

Phosphoric acid esters represented by the following formulae (I) and (IX) as well as processes for preparing them are disclosed. ##STR1## wherein R.sub.1 represents a linear or branched, alkyl or alkenyl group having a C.sub.1-36 carbon atom content, with or without the hydrogen atom(s) being substituted with fluorine atom(s), or a phenyl group with substituted linear or branched alkyl group(s) having a C.sub.1-15 carbon atom content, R.sub.2 represents an alkylene group having a C.sub.2-3 carbon atom content, R.sub.3 and R.sub.4 independently denote a hydrogen atom or an alkyl group having a C.sub.1-3 carbon atom content, R.sub.5 and R.sub.6 independently denote a hydrogen atom, or an alkyl, alkenyl, or phenyl group with or without the hydrogen atom(s) being substituted with group(s) containing hetero atom(s), excepting for a mercapto group, R.sub.7 and R.sub.8 independently denote a hydrogen atom, or an alkyl, or alkenyl group, m is an integer of 0-30, n is an integer of 0-5, l is an integer of 0-3, M is a hydrogen atom, an alkali metal, an alkali earth metal, on ammonium group, an alkyl amine group, or an alkanol amine group. The phosphoric acid ester have outstanding surface activity and good foaming capability, and imparts only extremely low irritation to the skin. The detergent composition into which they are formulated is particularly useful as, shampoo, baby shampoo, body shampoo.

A novel phosphoric ester of the following formula (I) ##STR1## is prepared by reacting a phosphoric ester of the following formula (II) ##STR2## with a basic compound. By reacting the phosphoric ester (I) with various types of amine compounds or other acidic hydrogen-bearing compounds, various phospholipid analogue compounds or phosphoric esters can be derived.

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Wakayama, Japan

Akira Matsunaga