Fatty acid derivatives and their use as surfactants in...

Details Fatty acid derivatives and their use as surfactants in... Fatty acid derivatives and their use as surfactants in...

1999-10-25

2002-04-30

Carr, Deborah D. (Department: 1621)

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

Organic compounds

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

C510S470000, C510S488000, C510S490000, C510S499000

Reexamination Certificate

active

06380410

ABSTRACT:

The present invention relates to the use of fatty acid derivatives of the general formula I:
A
1
—CO—R
1
  I
as surfactants for cleaner systems for cleaning grease-soiled nontextile material, where the substituents have the following meanings:
A
1
an aliphatic C
8
-C
24
radical with unbranched carbon chain, which contains in the chain one or more groups of the formula II:
R
1
an —N(R
2
)R
3
radical, a hydroxyl radical and its alkali metal or ammonium salts, a C
1
-C
4
-alkoxy radical or a radical of a mono-, di- or triglyceride, it being possible for the two latter to be radicals of natural saturated or unsaturated fatty acids or identical or different radicals A
1
;
R
2
a hydrophilic radical having 2-40 carbon atoms;
R
3
hydrogen, a C
1
-C
4
-alkyl radical or one of the R
2
radicals.
The invention additionally relates to the novel fatty acids of the formula Ia;
A
1
—COOR
4
  Ia
where R
4
is hydrogen or an alkali metal or ammonium cation of the corresponding fatty acid salt, and A
1
has the meaning stated at the outset, and to their use as surfactants. The invention further relates to surfactant formulations comprising compounds I or Ia. DE-A 27 34 596 discloses fatty acid derivatives of type I as detersive substances for washing textiles.
For cleaning nontextile surfaces, surfactants must have additional properties such as good fat-removal capacities. Cleaning processes of this type take place mainly in the metal industry, in the food industry, in the catering trade and in the household. Thus, for example, it is often necessary to remove drawing and rolling greases from metal articles after processing thereof. The primary object in the other sectors mentioned is also in particular to remove fats of varying origin from equipment and containers, because fats prevent the wetting of other soiled particles.
It is an object of the invention to use surfactants for aqueous cleaner systems for cleaning nontextile material with an improved fat-removal capacity.
We have found that this object is achieved by using the amino hydroxy fatty acid derivatives I defined at the outset for cleaning nontextile grease-soiled materials, the compounds Ia as novel substances, and formulations containing I.
Compounds I can be obtained in a manner known per se by epoxidizing fatty acid esters III:
and further reaction of the epoxidized products IV with an amine V:
with opening of the epoxide ring. A
2
in this case is an unsaturated radical which corresponds to the saturated or partially saturated radical A
1
in I, and B
1
is the radical of a 1- to 3-hydric aliphatic C
1
-C
6
-alcohol. In the case of a polyhydric alcohol, its other hydroxyl groups may also be esterified, preferably with fatty acids.
Depending on the chosen ratio of III to V there is mainly reaction of the epoxide groups with the amine V. If there is an excess of amine, B
1
is replaced by the radical —N(R
2
)R
3
.
The esters obtained where appropriate in the reaction can be used, for example, to prepare the novel fatty acids or their alkali metal salts by known reactions such as alkaline hydrolysis and, if required, acidification.
The ammonium salts, which are likewise novel, can be obtained preferably directly from the epoxidized fatty acids by reaction with V. This results in the preferred ammonium salts with
⊕
NH
2
R
2
R
3
as cation, where R
2
and R
3
have the same meanings as in the amino group of the fatty acid ester. Any desired ammonium salts can be prepared by subsequent reaction of a fatty acid Ia′ with an amine.
Among unsaturated unbranched aliphatic fatty acids from which the esters III are derived, the unsaturated hydroxy fatty acid ricinoleic acid is suitable, but preference is given to:
monounsaturated C
9
-C
25
-fatty acids such as petroselinic acid, undecenoic acid, &Dgr;
9
-decylenic acid, &Dgr;
9
-dodecylenic acid, vaccenic acid, palmitoleic acid, erucic acid and, in particular, oleic acid
diunsaturated C
9
-C
25
-fatty acids such as stillingic acid, preferably linoleic acid
triunsaturated fatty acids such as eleostearic and, preferably, linolenic acid.
Unsaturated C
18
-fatty acids are particularly suitable because they are readily available. The acids obtainable by isomerization of the double bond are also suitable.
It is likewise possible to use mixtures of fatty acids or fatty acid esters like those obtainable, for example, by transesterification or hydrolysis of natural fats with C
1
-C
4
-alcohols.
The preparation of compounds I preferably starts from natural fats, ie. the glycerol esters comprising at least one unsaturated radical A
2
. Examples of such natural fats are olive oil, cotton-seed oil, linseed oil, tallow, fish oils, tall oils, castor oil, coconut oil, dodder oil, sunflower oil, peanut oil, palm oil, euphorbia oil and, in particular, soybean oil and rapeseed oil.
The epoxidation is carried out in a manner known per se by reacting compound III with peracids such as performic acid and peracetic acid. However, some epoxidized fatty acid esters IV are also commercially available.
The amines V are primary or secondary amines having at least one hydrophilic aliphatic C
2
-C
40
radical. The amines may be branched and have several hydroxyl or amino groups, such as tris(hydroxyethyl)methylamine, but preferably have at least one unbranched (&ohgr;-hydroxyalkyl radical or an &ohgr;-aminoalkyl radical having 2 to 6 carbon atoms, it being possible for the alkyl radical to be interrupted by nonadjacent oxygen atoms, —NH groups, N—C
1
-C
4
-alkyl groups or N—C
1
-C
4
-hydroxyalkyl groups. Also suitable are N—C
1
-C
4
-alkyl-substituted derivatives if they also contain at least one reactive amino or imino group. Suitable and preferred in this connection are:
hydroxyalkylamines such as mono- and diethanolamine, mono- and diisopropanolamine, 2-(2-aminoethoxy)ethanol, 2-(2-aminoethylamino)ethanol, 3-aminopropanol and N-alkyl-substituted hydroxyalkylamines such as methylethanolamine, n-propylethanolamine, butylethanolamine, 2-amino-1-butanol and, particularly preferably, aminopropyldiethanolamine.
aminoalkylamines such as ethylenediamine, trimethylenediamine, 1,2-propylenediamine, 3-amino-1-methylaminopropane, diethylenetriamine, dipropylenetriamine, N,N′-bis(3-aminopropyl)ethylenediamine, 3-(2-aminoethoxy)propylamine, 2-(2-aminoethoxy)ethylamine, 3-(3-aminopropoxy)propylamine and their symmetrically and asymmetrically N-substituted mono- and dialkyl derivates such as N,N-dimethylaminopropylamine, diethylaminoethylamine, diethylaminopropylamine, 1-diethylamino-4-aminopentane, neopentanediamine, hexamethylenediamine, 4,9-dioxadodecane-1,12-diamine, 4,7,10-trioxatridecane-1,13-diamine, 3-(2-aminoethyl)-aminopropylamine.
Amines which are likewise preferred and result in products with beneficial properties are polyalkylene glycol amines of the general formula VI:
R
4
—(O—C
n
H
2n
)
y
—(O—C
2
H
4
)
x
—(O—C
n
H
2n
)
z
—NH
2
  VI
where
n is 2, 3 or 4
x is from 1 to 10
y and z are from 0 to 10
R
4
is hydrogen or a C
1
-C
4
-alkyl radical,
having a total of 3 to 40, in particular 3 to 20 carbon atoms. These known amines are normally obtained by alkoxylating aliphatic C
1
-C
4
-alcohols or ethylene glycol and subsequently aminating. This alkoxylation can take place either with ethylene oxide, propylene oxide and/or butylene oxide or mixtures thereof.
Examples of suitable amines are methylglycolamine and methyltetraglycolamine.
The reaction of the epoxidized fatty acid esters, acids or their salts with the amines normally takes place at from 30 to 170° C., preferably in the presence of an alkaline catalyst such as alkali metal hydroxides, carbonates or alcoholates, for example sodium methoxide. The reaction is complete when epoxy groups are no longer detectable. The reaction is complete after about 2 to 4 hours at 100° C.
The reaction can be carried out in the presence of a solvent, but this is usually unnecessary, so that a solvent is preferably omitted.
The amine is generally employed in an amount which is from stoichiometric to 10 molar, preferably stoichiome

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