Organic compounds -- part of the class 532-570 series – Organic compounds – Amino nitrogen containing
Reexamination Certificate
2000-07-06
2002-03-19
Geist, Gary (Department: 1623)
Organic compounds -- part of the class 532-570 series
Organic compounds
Amino nitrogen containing
C560S129000
Reexamination Certificate
active
06359176
ABSTRACT:
TECHNICAL FIELD
The present invention relates to cationic surfactants, process for producing the same and utilization thereof. Specifically novel cationic surfactants of high biodegradability derived from hexose, process for producing the same and utilization thereof.
PRIOR ART
Cationic surfactants have been used as a softener for textiles, rinse for shampoo and hair treatment, or a bactericide. Those cationic surfactants contain quaternary ammonium salt and thus their poor biodegradability has been a serious disadvantage. Among those, alkyl trimethyl ammonium chlorides and dialkyl dimethyl ammonium chlorides that have been popular surfactants are being regulated in Europe, especially in Netherlands, because of their low biodegradability. The regulation in Europe has been advancing toward the use of the compounds having at least one ester, a decomposable group, in their molecular structure. Under such social condition, developing more biodegradable cationic surfactants is an utmost need not only from the viewpoint of safety (non-toxic to skin etc.) but also from the viewpoint of environmental protection.
Although the conventional development trend of cationic surfactants has been concentrated on the surfactants having a molecular structure in which esters are introduced into alkyl chains, it is more advantageous to develop compounds derived from natural sugars for meeting the current trend toward surfactants of higher biodegradability. The inventors of the present invention investigated on deriving cationic surfactants from the amine derivatives of reducing sugar of glucose or the amine derivatives of hexose alcohols that are reducing alcohol of hexose. As the result, the inventors found the cationic compound of superior biodegradability produced by esterifying a quaternary salt, which is a derivative of 1-amino-hexose alcohol produced by the reaction (reductive amination) of glucose or other hexose (a reducing sugar) with ammonia or primary amines, with a fatty acid.
DISCLOSURE OF INVENTION
The object of the present invention is to provide highly biodegradable new cationic surfactants produced from natural raw materials.
Another object of the present invention is to provide a profitable industrial process for producing the above cationic surfactants of the present invention.
Further object of the present invention is to provide fiber being treated with the above cationic surfactant of the present invention and having superior water absorptiveness and antistaticity and low friction.
Yet further object and advantage of the present invention are illustrated in the following description.
The above object and advantage of the present invention are, first, achieved by a cationic surfactant represented by the following formula (1),
R
1
—CH
2
—(CHR
1
)
4
—CH
2
—N
+
(R
2
)
3
X
−
(1)
wherein five R
1
s are hydroxyls or their esters independently to each other, three R
2
s are hydrocarbons having 1 to 6 carbon atoms and can contain hydroxyls or esters independently to each other, X
−
is an anion of halogen atoms, hydrogen sulfate or organic acid, and at least one of the five R
1
s is an ester.
The above object and advantage of the present invention are, secondly, achieved by a process for producing cationic surfactant (hereinafter referred to as the first production process of the present invention), wherein a cationic surfactant represented by the above-mentioned formula (1) is produced through the following steps,
(A) reacting 1-amino hexose alcohol represented by the following formula (2)
HO—CH
2
—(CH.OH)
4
—CH
2
—NH
2
(2)
with a halide represented by the following formula (3)
R
2
—X (3)
wherein R
2
and X are the same as defined in the above formula (1) to produce an ammonium salt of N-hydrocarbon-1-amino hexose alcohol represented by the following formula (4)
HO—CH
2
—(CH.OH)
4
—CH
2
—N
+
(R
2
)
3
X
−
(4)
wherein R
2
and X are the same as defined in the above formula (1); and
(B) reacting the above ammonium salt of N-hydrocarbon-1-amino hexose alcohol with an acid halide.
And the above object and advantage of the present invention are, thirdly, achieved by a process for producing cationic surfactant (hereinafter referred to as the second production process of the present invention), wherein a cationic surfactant represented by the above-mentioned formula (1) is produced through the following steps,
(A) reacting 1-amino hexose alcohol represented by the above formula (2) with a halide represented by the above formula (3) to produce an ammonium salt of N-hydrocarbon-1-amino hexose alcohol represented by the above formula (4); and
(B′) reacting the above ammonium salt of N-hydrocarbon-1-amino hexose alcohol with an organic acid in dehydration condensation.
Further the above object and advantage of the present invention are, fourthly, achieved by a process for producing cationic surfactant (hereinafter referred to as the third production process of the present invention), wherein a cationic surfactant represented by the above-mentioned formula (1) of which one of the three R
2
s is a methyl and other two are hydrocarbons that can contain hydroxyls or esters is produced through the following steps,
(A′) reacting N-methyl glucamine represented by the following formula (5)
HO—CH
2
—(CH.OH)
4
—CH
2
—NH.CH
3
(5)
with a halide represented by the above formula (3) to produce an ammonium salt of N-hydrocarbon-1-amino hexose alcohol represented by the above formula (4) of which one of the three R
2
s is a methyl and other two are hydrocarbons that can contain hydroxyls or esters; and
(B″) reacting the above ammonium salt of N-hydrocarbon-1-amino hexose alcohol with an acid halide.
Finally the above object and advantage of the present invention are achieved with the textile treated with the above cationic surfactants of the present invention.
PREFERRED EMBODIMENT OF INVENTION
The cationic surfactants of the present invention are represented by the above formula (1), wherein each of five R
1
s is a hydroxyl (—OH) or its ester independently to each other. The ester is represented by the formula, RCOO—; in which R is preferably a straight or branched chain and saturated or unsaturated hydrocarbon having 5 to 28 carbon atoms and may contain aromatics. The examples of such hydrocarbon are alkyls, such as pentyl, hexyl, heptyl, octyl, nonyl, decyl, lauryl, myristyl, cetyl, stearyl, eicosanyl and hexacosanyl; and their correspondent alkenyls, such as pentenyl and hexenyl.
Each of the three R
2
s in formula (1) is a hydrocarbon having 1 to 6 carbon atoms and may contain hydroxyls or esters independently. The hydrocarbon having 1 to 6 carbon atoms may be straight or branched chain and saturated or unsaturated. The examples of such hydrocarbon are alkyls, such as methyl, ethyl, propyl, butyl, pentyl and hexyl, and correspondent alkenyl or alkynyls having 2 to 6 carbon atoms.
The X
−
is an anion of halogen atoms, hydrogen sulfate (HSO
4
−
) or organic acids (RCOO
−
). The examples of preferable halogen anions are fluorine anion, chlorine anion, bromine anion and iodine anion. The examples of preferable anions of organic acids are those having 2 to 12 carbon atoms, i.e., monobasic acid anions, such as acetic acid an ion and propionic acid anion; dibasic acid anions, such as oxalic acid and malonic acid; and anions of oxyacid, such as citric acid and malic acid.
At least one of the five R
1
s of the cationic surfactant represented by the above formula (1) must be an ester, such as monoesters, di-esters, trimesters, tetra-esters and penta-esters.
Among the compounds represented by the above formula (1), the compound of which all of three R
2
s in formula (1) are methyls as represented by the following formula (6),
R
1
—CH
2
—(CHR
1
)
4
—CH
2
—N
+
(CH
3
)
3
.X
−
(6)
wherein R
1
and X
−
are the same as defined in the above formula (1), is preferable because of its superior biodegradability to that of others.
The cationic surfactants
Munekiyo Takeshi
Nakamura Masaki
Qian Jia-he
Seike Hiromitsu
Calve John N.
Geist Gary
Matsumoto Yushi-Seiyaku Co. Ltd.
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