Betaine compound and process for production thereof

Details Betaine compound and process for production thereof Betaine compound and process for production thereof

2000-11-17

2002-09-17

Rotman, Alan L. (Department: 1623)

Organic compounds -- part of the class 532-570 series

Organic compounds

Fatty compounds having an acid moiety which contains the...

C560S155000, C562S553000, C564S292000

Reexamination Certificate

active

06452030

ABSTRACT:

FIELD OF THE INVENTION
The present invention relates to a hydroxyl group-containing betaine compound, a long-chain alkyl group-containing betaine compound, and processes for producing said compounds.
PRIOR ART
The betaine compound has both a cationic group and an anionic group within its molecule and, because of this structural feature, has been attracting attention as an. amphoteric surfactant in recent years. Amphoteric surfactants have many beneficial properties such as exceptionally high resistance to hard water and low toxicity, and are used with advantage in various applications such as surfactants, bactericides, antistatic agents, softening agents, rust inhibitors and so on.
Japanese Kokai Publication Hei-5-32600 discloses a process for producing a betaine compound which comprises reacting an aliphatic primary amine with a quaternary ammonium compound having a defined structure at 6≦pH<8 and further reacting the reaction product with a defined halogenated lower carboxylic acid at 6≦pH<8. The betaine compound produced by this process has foaming and detergent properties so that it can be used as a surfactant for hair and body cleansing. However, in order that a variety of properties other than foaming and detergent properties may be imparted to such a betaine compound to thereby expand its scope of application, a further investigation into related compounds was needed.
Japanese Kokai Publication Hei-5-294905 discloses a carbobetaine compound and a process for its production. This process for producing a carbobetaine compound comprises reacting a defined amino compound with a defined halogen-containing salt. The carbobetaine compound obtainable by this process has an emolient action on the hairs and skin so that it finds application as an emolient in hair care and skin care products. However, with regard to such carbobetaine compound, too, further investigations are needed into related compounds in order to impart a variety of properties other than emolient activity for an expanded scope of application.
SUMMARY OF THE INVENTION
The present invention, developed in light of the above state of the art, has for its object to provide a hydroxyl group-containing betaine compound and a long-chain alkyl group-containing betaine compound, both of which are highly biodegradable and useful as surfactants, bactericides, antistatic agents, softening agents, rust inhibitors, resin-modifying agents, and synthetic intermediates, as well as processes for producing said compounds.
The present invention relates to a hydroxyl group-containing betaine compound of the following general formula (1):
wherein R
1
and R
2
may be the same or different and each represents a hydrogen atom, a C
1-8
hydrocarbon group or a C
1-8
hydrocarbon group having a hydroxyl group, exclusive of the case in which both of R
1
and R
2
respectively represent a hydrogen atom; in case neither R
1
nor R
2
represents a hydrogen atom, R
1
and R
2
may be joined to each other through a single bond or through at least one kind of element selected from the group consisting of O, S and N; R
3
represents a hydrogen atom, a methyl group or a hydroxymethyl group; A represents a C
2-25
hydrocarbon group.
In a further aspect, the present invention relates to a process for producing a hydroxyl group-containing betaine compound of the following general formula (1):
wherein R
1
, R
2
, R
3
and A are respectively as defined above,
which comprises a step of reacting a &bgr;-alanine derivative of the following general formula (2):
wherein R
1
, R
2
and R
3
are respectively as defined above, with a monooxirane compound.
In a further aspect, the present invention relates to a long-chain alkyl group-containing betaine compound of the following general formula (3):
wherein R
6
and R
7
maybe the same or different and each represents a hydrogen atom or a C
1-8
hydrocarbon group, exclusive of the case in which both of R
6
and R
7
respectively represent a hydrogen atom; in case neither R
6
nor R
7
represents a hydrogen atom, R
6
and R
7
may be joined to each other through a single bond or through at least one kind of element selected from the group consisting of O, S and N; R
3
and A are as defined above; R
4
and R
5
are such that whichever one of them represents a hydrogen atom and the other represents a C
5-30
hydrocarbon group; X represents a hydrogen atom or —COOM, where M represents a hydrogen atom, a metal atom or an ammonium group.
In a still further aspect, the present invention relates to a process for producing a long-chain alkyl group-containing betaine compound of the following general formula (3):
wherein R
6
, R
7
, R
3
, A, R
4
, R
5
and X are respectively as defined above,
which comprises a step of reacting a hydroxyl group-containing betaine compound of the following general formula (6):
wherein R
6
, R
7
, R
3
and A are respectively as defined above, with either a long-chain alkyl group-containing carboxylic acid of the following general formula (4):
wherein R
4
, R
5
and X are respectively as defined above, or a long-chain alkyl group-containing carboxylic anhydride of the following general formula (5):
wherein R
1
and R
5
are respectively as defined above.


REFERENCES:
patent: 3265719 (1966-08-01), Cowen et al.
patent: 3706562 (1972-12-01), Herz et al.
patent: 3838075 (1974-09-01), Dietrich et al.
patent: 4426445 (1984-01-01), Minamizono et al.
patent: 4470918 (1984-09-01), Mosier
patent: 4883917 (1989-11-01), Smith et al.
patent: 1 419 202 (1975-12-01), None
patent: 2 076 983 (1981-12-01), None
patent: 5032600 (1993-02-01), None
patent: 5294905 (1993-11-01), None
patent: WO 99/13197 (1999-03-01), None

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