Organic compounds -- part of the class 532-570 series – Organic compounds – Carboxylic acid esters
Reexamination Certificate
2000-05-01
2002-04-09
Gitomer, Ralph (Department: 1623)
Organic compounds -- part of the class 532-570 series
Organic compounds
Carboxylic acid esters
C560S344000, C560S129000, C562S566000, C564S511000
Reexamination Certificate
active
06369268
ABSTRACT:
The present invention relates to diester amine adducts, to a process for the preparation of these compounds and to their use.
The diester amine adducts of this invention correspond to formula
wherein
R
1
, R
2
, R
3
, R
4
are each independently of one another C
4
-C
22
alkyl; C
2
-C
22
alkenyl; or C
5
-C
7
-cycloalkyl;
X
1
and X
2
are each independently of the other hydrogen, C
1
-C
4
alkyl; C
2
-C
4
hydroxyalkyl or C
2
-C
4
hydroxyhaloalkyl;
Y is a radical of formula (1b)
A
1
is C
2-C
3
alkylene or 2-hydroxy-n-propylene;
X
3
is hydrogen; C
1
-C
4
alkyl, C
2
-C
4
hydroxyalkyl; or C
2-C
4
hydroxyhaloalkyl;
is an asymmetrical carbon atom in the R- or S-configuration, wherein, if
C
1
=R, C
2
=R;
C
1
=S, C
2
=S; and
C
1
=R; C
2
=S;
m
1
is 1 or 2; and
n is an integer from 1 to 4;
p is 0 or 1;
which adduct may be in the form of a free base, acid, acid salt or quatemary ammonium salt.
The diester amine adducts are stereochemically uniform compounds in the (SS)-, (RR)- or (RS)-configuration, i.e. compounds which can be represented by formulae
C
1
-C
22
Alkyl is a straight-chain or branched alkyl radical, for example methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, tert-butyl, amyl, isoamyl or tert-amyl, heptyl, octyl, isooctyl, nonyl, decyl, undecyl, dodecyl, tetradecyl, pentadecyl, hexadecyl, heptadecyl or octadecyl or eicosyl.
C
2
-C
22
Alkenyl is, for example, allyl, methallyl, isopropenyl, 2-butenyl, 3-butenyl, isobutenyl, n-penta-2,4-dienyl, 3-methyl-but-2-enyl, n-oct-2-enyl, n-dodec-2-enyl, iso-dodecenyl, n-dodec-2-enyl or n-octadec-4-enyl.
C
5
-C
7
Cycloalkyl is typically cyclopentyl, cycloheptyl or, preferably, cyclohexyl.
C
2
-C
4
Hydroxyalkyl is, for example, 2-hydroxyethyl or 4-hydroxy-n-butyl.
C
2
-C
4
Hydroxyhaloalkyl is typically 1-chloro-2-hydroxyethyl.
Preferred diester amine adducts of formula (1) are those, wherein
A
1
is C
2
-C
3
alkylene;
m is 2; and
p is 0.
Particularly preferred diester amine adducts of formula (1) are those, wherein X
1
and X
2
are hydrogen and very particularly preferably those, wherein R
1
, R
2
, R
3
and R
4
are C
4
-C
2
alkyl.
Examples of diester diamine adducts of this invention are the compounds of formulae
The novel diester amine adducts, which are stereochemically uniform with respect to the C
1
and C
2
atoms (see formula (1)), are prepared by methods known per se by reacting an aminodicarboxylic acid of formula
with an excess of the relevant alcohol under the action of gaseous HCl or thionyl chloride in a one-pot reaction. Such a process is disclosed, inter alia, in C.A. 62, 11911g (1965). The corresponding diester amine adducts can be converted to the corresponding diester amine adducts of formula (1) by reacting the resultant aminodicarboxylates of formula
with a dihalogen compound of formula
Hal—(A
1
)
m−1
Hal. (1f)
The entire course of the reaction can be represented as follows:
Tetraesters which are stereochemically uniform with respect to the amino carboxylic acid frameare also obtained by reacting, for example, the diaminotetracarboxylic acid of formula (1g) or the salts of this acidwith thionyl chloride and an alcohol to the corresponding ester compound of formula (1f):
The thionyl chloride is added dropwise usually in the temperature range from −70 to 80°, preferably from −10 to 30° C. In the further course of the reaction the temperature is raised up to 200° C., the preferred temperature range being from 40 to 80° C.
Thionyl chloride is usually used in excess. In principle, thionyl chloride can also be replaced with gaseous hydrogen chloride.
After the reaction is complete, the hydrochlorides of the tetraesters may, if required, be isolated in the form of crystalline compounds and then recrystallised.
The alcohol component is used as solvent for the reaction (high excess).
The starting compound can be a water-containing tetracarboxylic acid, e.g. EDDS having a water content of about 20%.
Monoesters of the aminodicarboxylic acid can be obtained in good yields by a commonly known process by reacting the carboxylic acid with the relevant alcohol.
Mixtures of the compounds of formulae (1a), (1b) and (1c) are obtained by first esterifying maleic anhydride with an alcohol to the corresponding diester and then reacting 2 mol of the respective diester with diamine.
For many applications it is also possible to replace the stereochemically uniform products with mixtures of the stereoisomers of formulae (1a), (1b) and (1c) which are also obtained in the above manner.
The stereochemically uniform compounds of formula (1) and the diester amine adducts of formula
are precursors of compounds having pronounced complex-forming properties. Under physio-logical conditions, the ester groups can be split by esterases. The chemical hydrolysis is carried out in aqueous medium in the presence of OH
−
or H
+
ions. Compounds are obtained wherein R
1
=R
2
=R
3
=R
4
=H, for example N,N′-ethylenediamine disuccinic acid (EDDS). Such compounds are thus able to effectively bind heavy metal ions such as iron, zinc, magnesium or copper ions and to prevent metal-initiated oxidations.
In contrast to the free acids or the salts of the acids (R
1
=R
2
=R
3
=R
4
=H), the compounds of formula (1) are readily soluble in organic solvents, fats and oils, new fields of application being thus obtained. Said compounds are therefore suitable as additives in food and beverages products which are susceptible to oxidation and which are inclined to spoil or to become rancid. The foods susceptible to oxidation are, in particular, compounds or compositions containing olefinic double bonds.
Owing to their complex-forming properties, the novel diester amine adducts can also be used for removing undesirable calcium depositions, boiler scale and rust. They are usually used to this purpose in alkaline derusting and decalcification baths.
The novel compounds are furthermore used as additives in liquids for cooling-water circuits for preventing and dissolving calcium depositions.
The novel adducts are also used in personal-care products, for example in creams, lotions, body-care products, such as deodorants, soaps or shampoos and ointments, for preventing oxidation, rancidness, turbidity and the like.
It is possible to achieve, in particular, a soft handle effect on hair.
Furthermore, the novel diamine adducts are used as bleaching stabilisers, e.g. for sodium perborate, in detergents or in textile or paper bleaching. Heavy metal traces, for example iron, copper or magnesium, are present in detergent formulations, in water and in textile and paper materials and catalyse the degradation of sodium perborate as well as of other bleaches present in the detergent. The novel compounds bind these metal ions and prevent the undesirable degradation of the bleaching system both during storage of the corresponding detergent as well as in the washing liquor. The effectivity of the bleaching system is thus improved and fibre damage is prevented. In addition, other sensitive detergent components, such as enzymes, fluorescent whitening agents and fragrances are advantageously protected against oxidative degradation.
The novel adducts can also be used in cleaning agents and detergents for removing metal ions and as preservatives. In liquid cleaning formulations, the novel compounds may advantageously be used in a concentration of 0.05 to 15% by weight, based on the entire weight of the formulation.
The novel diester amine adducts can also be advantageously used in the textile industry for removing traces of heavy metal during production and when dyeing natural and synthetic fibres. They prevent spotty and streaky dyeings on textile material, bad wettability and unlevelness.
The novel diester amine adducts of formula (1) are also very suitable as soft handle agents for organic fibre materials such as paper or, in particular, textile fibre materials. Particularly good soft handle effects are achieved in the case of loose fibres,
Ehlis Thomas
Frankhauser Peter
Hüglin Dietmar
Ciba Specialty Chemicals Corporation
Gitomer Ralph
Khare Devesh
Mansfield Kevin T.
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