Alkylated diaminobenzene sulfonic acids

Details Alkylated diaminobenzene sulfonic acids Alkylated diaminobenzene sulfonic acids

2000-02-08

2001-04-24

Geist, Gary (Department: 1623)

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

Organic compounds

Sulfonic acids or salts thereof

Reexamination Certificate

active

06222067

ABSTRACT:

FIELD OF THE INVENTION
The present invention relates to a novel dyestuff intermediates.
BACKGROUND OF THE INVENTION
Synthetic dyestuffs have a history of more than a hundred years. In recent years few novel dyestuff intermediates have been developed. In fact the study of novel dyestuff intermediates is very important. For example, a novel dyestuff intermediate can be used to improve a manufacturing process or to synthesize a novel dyestuff.
SUMMARY OF THE INVENTION
The present invention relates to novel alkylated diaminobenzene sulfonic acid compounds of the following formula (I):
wherein R
1
is hydrogen or C
1-7
acyl; R
2
is C
1-3
alkylene, such as methylene (—CH
2
—), ethylene (—CH
2
CH
2
—) or methylethylene (—CH
2
CH(CH
3
)—); n is 0 or 1.
The alkylated diaminobenzene sulfonic acid compounds of the formula (I) of the present invention are a novel dyestuff intermediates. They can be used to synthesize fiber reactive dyestuffs. The fiber reactive dyestuffs can be widely applied to dyeing a great range of spun and woven products that contain a hydroxyl group or amide group, etc., such as wool, silk, polyamide, and natural or synthetic fiber; and also cellulose fiber like cotton, linen, artificial cotton, and artificial linen, etc.
The present invention also relates to a process for the preparation of compounds of formula (I). The operating procedures are easy and have the advantages of high production rates and high purity.
DESCRIPTION OF THE PREFERRED EMBODIMENTS
The preparation of compounds of formula (I) compound of the present invention is described below:
A diaminobenzene sulfonic acid compound of formula (II) is acylated to obtain a monoacyl compound of formula (III)
wherein n is 0 or 1; R
3
is C
1-7
acyl.
Regarding the acylation reaction of diaminobenzene sulfonic acids of formula (II), it can be carried out processed in aqueous solution or in organic solvent. The acylating reagent used in the reaction is a carboxylic acid derivative, such as an acid anhydride, acid chloride, or a mixture thereof. Preferred examples of acylating agents are acetic anhydride, propionic anhydride, formic anhydride, benzoic anhydride, maleic anhydride, succinic anhydride, chloroacetic anhydride, chloropropionyl chloride or benzoyl chloride; among them acetate anhydride is the most popular acylation reagent.
In the above acylation reaction of diaminobenzene sulfonic acid compound of formula (II), each mole of compound of formula (II) compound requires more than one mole of acylation reagent. More preferably 1.0-1.5 mole of acylation reagent, and most preferably 1.05-1.15 mole of acylation reagent is used. The reaction temperature of the above acylation reaction is controlled between 10° C. and 45° C., and more preferably is between 20° C. and 40° C. The pH value of the above acylation reaction is controlled between 1-10, and more preferably is between 4-6. The monoacyl compound of formula (III) can be isolated from the reaction or it is possible to proceed directly to the alkylation reaction in the next step.
The monoacyl compound of formula (III) is then reacted with an alkylation reagent that contains a carboxylic acid group to yield a compound of formula (IV) which is the compound of formula (I) of the present invention,
wherein n is 0 or 1; R
2
is C
1-3
alkylene and R
3
is C
1-7
acyl.
The alkylation reaction is carried out by reacting a monoacyl compound of formula (III) with an alkylating agent. The alkylating agent contains a carboxylic acid group and 2-4 carbon atoms. Examples include chloroacetic acid or 2-chloropropionic acid. Unsaturated carboxylic acids such as acrylic acid or methacrylic acid can also be used as alkylating agents. For each mole of monoacyl compound of formula (III) it is necessary to use more than one mole of alkylation reagent, preferably, 1-10 mol, and more preferably, 1.1-2.5. The reaction temperature of the alkylation reaction is controlled between 70° C. and 110° C., and, more preferably between 80° C. and 100° C. The pH value is generally controlled between 3-7, preferably between 4-6. Reaction is best carried out in presence of a catalyst such as acid, alkali or potassium iodide; the compound of formula (IV) described previously can thus be obtained.
The compound of formula (IV) can be deacylated to yield a compound of formula (V) (i.e. formula (I) of this invention, in which R
1
is hydrogen).
wherein n and R
2
are defined as stated previously.
The acylation of compound (IV) is carried out in aqueous medium. The reaction temperature is controlled between 70° C. and 110° C., and, more preferably, between 80° C. and 100° C. The pH value is controlled either above 10 or below 2. After the reaction is complete, the product is precipitated by acidifying the resultant solution, by salting out or by a combination of both to obtain the component of formula (V).


REFERENCES:
patent: 0113941 (1900-09-01), None
patent: 0712906 (1996-05-01), None

Affiliated with

Also associated with

Rating

Alkylated diaminobenzene sulfonic acids does not yet have a rating. At this time, there are no reviews or comments for this patent.

If you have personal experience with Alkylated diaminobenzene sulfonic acids, we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Alkylated diaminobenzene sulfonic acids will most certainly appreciate the feedback.

Rate now

Comments { 0 }

Profile ID: LFUS-PAI-O-2549512