Kao Corporation

Junya Wakatsuki

Tomihiro Kurosaki

Takashi Imamura

Akira Matsunaga

Nobutaka Horinishi

Tohru Katoh

Toshio Nozaki

Tomohiko Sano

Hisakazu Furugaki

Kiyoshi Aimono

Katsutoshi Kojima

Toru Kato

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.

Phosphoric esters and process for preparing the same

A detergent composition contains as an essential component a compound represented by the following general formula (I): ##STR1## wherein R means ##STR2## R.sup.1 denotes a straight-chain or branched alkyl or alkenyl group or a substituted phenyl group. R.sup.2 is an alkylene group having 2-3 carbon atoms, m is 0-30, and n stands for 0 or 1. M means a hydrogen atom or denotes an alkali metal, alkaline earth metal, zinc or aluminum atom, an ammonium ion, or an alkylamine or alkanolamine residuum thereby to indicate the formation of a salt of the compound of the general formula (I).

Detergent composition

Novel phosphoric esters represented by the following general formula (I) ##STR1## wherein R.sub.1 represents a linear or branched alkyl or alkenyl group having 1 to 36 carbon atoms, or a phenyl group substituted with a linear or branched alkyl group having 1 to 15 carbon atoms, R.sub.2 represents an alkylene group having 2 to 3 carbon atoms, R.sub.3, R.sub.4 and R.sub.5 individually represent a hydrogen atom or a linear or branched alkyl group having 1 to 36 carbon atoms providing that any one of R.sub.3, R.sub.4 and R.sub.5 has 5 or more carbon atoms, and n is a number from 0 to 30 are obtained by reacting phosphoric esters of the following formula ##STR2## with amines at a high purity and in a high yield. The phosphoric esters (I) are excellent in the surface tension and foaming property, and give extremely low stimulus to the skin, so that they can be utilized in detergent compositions, cosmetic compositions, emulsifiers, dispersants, anti-static agents and the like.

Phosphoric ester

A phosphoric ester salt of high purity is produced by converting a phosphoric ester in a mixture containing the phosphoric ester and one or more nonionic compounds into a phosphoric ester salt by using a basic compound, and extracting nonionic compounds from the above mixture by using a mixed solvent of aliphatic hydrocarbons or cycloaliphatic hydrocarbons, a lower alcohol and water. The above method is applicable to a non-crystalline phosphoric ester from which nonionic compounds cannot be removed by recystallization. The above obtained phosphoric ester salt of high purity can be used as it is or after condensation.

Process for producing phosphoric ester salt of high purity

A process for preparing an alkali metal salt of a phosphoric ester represented by the following general formula (III): ##STR1## wherein R.sup.1 means an organic group, R.sup.2, R.sup.3, R.sup.4 and R.sup.5 denote individually a hydrogen atom or organic group, R.sup.2 and R.sup.4 may optionally be coupled together into a ring, and M stands for an alkali metal, which comprises reacting a monoalkali metal salt of an organophosphoric monoester, represented by the following general formula (I): ##STR2## wherein R.sup.1 and M have the same meaning as defined above, with an epoxy compound represented by the following general formula (II): ##STR3## wherein R.sup.2, R.sup.3, R.sup.4 and R.sup.5 have the same meaning as defined above.

Process for the preparation of an alkali metal salt of a diester

A novel process for producing a phosphoric monoester which comprises reacting per 1 mole of a linear or branched, saturated or non-saturated aliphatic alcohol having from 8 to 36 carbon atoms, from 2 to 10 moles of a polyphosphoric acid at 100 to 116% concetration converted as orthophosphoric acid in (a) one or more solvents selected from the group consisting of linear or branched saturated aliphatic hydrocarbons having from 4 to 8 carbon atoms and saturated cycloaliphatic hydrocarbons having from 5 to 7 carbon atoms, then adding (b) a lower alcohol having from 1 to 4 carbon atoms and water to the reaction mixture, transferring the orthophosphoric acid to the lower alcohol-aqueous phase to separate it from the phosphoric monoester, and concentrating the thus recovered orthophosphoric acid for reuse. The process reaction proceeds smoothly, separation and purification can be carried out readily and very effectively and the recovered phosphoric acid can be re-used.

Growing community of inventors

Wakayama, Japan

Junya Wakatsuki