Note: Descriptions are shown in the official language in which they were submitted.
D 9347 ~ ~ Z 21 ~ 8 2 8 7
04.04.1991
Th~a u~e o~ e~t~r~ as ~abria; ~so~te~l~g ~ge~t~
Textiles which comes into contact with the human ski~
are often treated with abric-softening agents to give them
a pleasant soft feel. There are ~any known fabric-soft~n-
ing agents of which ~uaternary ammonium compounds contain-
ing two or three long-chain groups are used very frequently
and on a wide scale by virtue o~ their high effectiven~ss.
Despite their excellent ef~ect a~ fabric soften~r~,
quaternary ammonium compounds, of which the long-chain
groups are fatty alkyl groups, are not a per~ect solution
to a problem on account of their unsatisfactory biological
degradability. Accordingly, there has been no shortage of
attempt~ to Pind compounds which combine better biode~
gradability with a good fabric-softening effect. Ecologi-
cally improved ~abric-softening agents are, for example,
quaternary mmonium compounds of which the long-chain
groups are ~atty acyloxyal~yl groups. Quaternary ammonium
compounds such as th~se have long been known, for example
from German patent applicatio~s DE-A-16 19 058, DE-A 17 94
068, DE-A-19 35 499 or from US-PS 3,915,867. Their biode-
gradability i~ better than that of co mentional quaternary
ammoniu~ compound~ containing fatty alkyl groups. Never-
~heless, so~e o~ these more readily biodegradable quater-
nary ammonium compounds do not ~eet all the re~uirements
that an ideal compound would satisfy becauss their degrad-
ation ocasionally takes place via intermediate stages
which, ecologically, are no~ co~pletely safe. They can be
produced by various methods although it is generally dif-
ficult to obtain light-color~d products acceptable to the
consumer~ Accordingly, additional steps are often neces-
sary ~or separating dark-colored from light-colored prod-
ucts which increases the production costs of light-colored
2~g2~
D 9347 ~CT 2
products. In addition, the quaternization reaction re-
quires reagents of which the handling often entails addi-
tional safety measures. Accordingly, there is ~till a need
for fabric-softening agents which are readily biodegradable
and of which the degradation does not involve the formation
of ecologically unsafe intermediates and which can be
easily produced from starting ~aterials that are convenient
to handl0.
It has now ~urprisingly been found that certain esters
of alkanolamines ~an be used as fabric-softening agents.
These esters are derived from fatty acids which may be of
natural or synthetic origin and, hence, may be linear or
branched, saturated or unsaturated and may contain 6 to 24
carbon atoms per fatty acid unit. Preferred esters for ~he
use according to the invention are derived from C~2~ fatty
acids which are obtained easily and inexpensively from
natural fats. The natural fats source may be selected from
vegetable and animal fats, for example coconut oilJ palm
kernel oil, sunflower oil, rapeseed oil, beef tallow, fish
oil, sperm oil and the narrower or broader fatty acid cuts
produced therefrom. However, esters of alkan~lamines
derived fro~ pure or technical fatty acids, for example
from lauric acid, myristic acid, palmitic acid, stearic
acid, oleic acid, elaidic acid, behenic acid, acid derived
from Guerbet alcohols and substituted acids, ~or example
hydroxycarboxylic acids, are also suitable.
~ he alkanolamine esters are based on alkanolamines
containing 1, 2 or 3 alkanol groups. Esters particularly
suitable ~or the use according to the invention are derived
from alkanola~ines of which the alkanol groups contain 2 to
4 and, more particularly, 2 or 3 carbon atoms, i.e. for
exampl~ ethanolamines, propanol~mines and butanola~ines, of
which the ethanola~ines and the propanolamines are partic-
ularly preferred. Alkanolamines containing 3 carbon atoms
are derived fro~ n-propanolamine or i-propanolamine. Es-
~ 93~7 p~ 3 2~28~
ters derived from alkanolamines containing 2 or 3 alkanolgroups are preferred for the use according to the inven-
tion. Typical alkanolamines of which the esters are suit-
able for the u5e according to the invention are, for
5 example, dimethyl ethanola~ine, methyl diethanolamine,
triethanolamine, diethyl ethanolamine, ethyl diethanol-
amine, dimethyl-n-propanolamine, methyl di-n-propanolamine,
dimethyl-i-propanolamine, methyl-i-propanola~ine and the
higher n-propyl and i-propyl homologs of the oompounds
mentioned. Also suitable are esters derived from alkanol-
amines of which the alkyl or alkanol groups in the molecule
- where the molecule contains several alkyl or alkanol
~roup~ - are different. Examples of such compounds are
methylethyl ethanola~ine, methyl-i-propyl ethanolamine,
methylethyl-i-propanolamine or methylethyl-n-butanolamine.
The above-mentioned esters of alkanolamines are known
compounds which are used as precursors of the quaternary
ammonium compounds described in the literature references
cited above. They may be prepared by esterification of the
alkanolamines with fatty acids, fatty acid halides and
fatty acid esters, for example fatty acid methyl ester, or
even with fatty acid triylycerildes, the so-called trigly-
cerides. These precursors oP the guaternary ammo~ium
compounds known as fabric softeners are completely biode-
gradable without forming quaternary intermediates and,unlike the quater~ary ammonium compounds, do not have to be
subjected to a quaternization reaction so that their
production involves one less step which, i~ addition, would
normally hav~ to be carried out with reagents that are
diffioult to handle.
Esters paxticularly suitable for the use according to
the invention are derived from alkanola~ines which are
present in salt form. The salts of the alkanolamine esters
are obtained by simple neutralization o~ the alkanolamine
esters. Salts o~ the est~rified alkanola~ines which have
- : '
. . , ,.:
- . . . .
.
, . . .
D 93~ PC~ 4 2 1 ~ ~ 2 ,~ ~
been obtained by neutralization with short-chain organic or
inorganic acidq are pre~erably u~ed. Short-chain organic
acids are understood to be mono- or polybasic acids, for
example formic acid, acetic acid, sxalic acid, suceinic
acid, malonic acid, fumaric acid, and also substituted
acids, such as for example citric acid; tartaric acid,
glycolic acid, lactic acid, tartronic acid or gluconic
acid. Inorganic acids suitable for salt ~ormation are, for
example, hydrochloric acid, sul~uric acid, pho~phoric acid
or phosphorous acid. In general, 100 mol-% of the esters
are present in salt form. Occasionally, however, it is of
advantage if only 30 to 90 mol-% of the alkanolamine esters
are present in salt form. Alkanolamine esters having
particularly valuable performance propertie~ are present as
salt~ of lactic acid or phosphorous acid.
In one preferred embodiment of the use according to
the invention, the alkanolamine esters are used in water-
based treatment preparations which contain 0.5 to 20~ by
weiyht of the compounds mentioned as fa~ric-softening
agents. The esters mentioned are ~resent in dissolved or
dispersed form in the water-based treatment preparations.
Treatment preparations o~ the type in question are used for
: the treatment of freshly washed laundry. Another po~ential
use for the alkanola~ine esters mentioned is as an additive
to detergents or wash liquors. The laundry to be washed
collects the alkanolamin~ esters on its surface during the
washing process so that i~ is laft with an improved feel
after rinsing and drying. However, the alkanolamine esters
may also be used as fabric-softening agents in tumble-
drying auxiliarie~ in which the fabric softener is applied
to a substrate that transf~rs the active substances to the
laundry ~uring drying in an automatic dryer.
The water-ba~ed treatment preparations preferably have
a pH value of 2 to 7.
The treatment preparations contain more or less dif-
~;,.
.~. . .
,
.
` 2~2~
D 93~7 PCT 5
ferent additives, depending on the nature o~ the use
according to the invention. For example, water-based
treatment preparations contain preservatives, opaci~iers,
viscosity regulators, fragrances, dyes, emulsifiers or
dispersants. If necessary, the alkanolamine esters may
also be used in combination with other fabric-softening
agents. In some cases, it can be useful to add surfac-
tants, optical brighteners or solubilizers.
~ x a ~ p 1 ~ ~
Examples 1 to 6 below describe the production of
alkanolamine esters to be used in aceordance with th~
. inventlon.
E~a~plo 1
540 g (2 mol) molt~n tallow fatty acid (acid value
208, iodine value 52) were introdu~ed into a stirred
reactor equipped with a ther~ometer, gas inlet pipe and
Liebig condenser and then mixed at 90-C with 149 g (1 mol)
triethanolamine. The mixture wa~s then heated under nitro-
gen as inert gas until, at 150-C, the eli~ination of water
began. The temperature was then increased to 200 C over a
period of 1.5 hours and maintained until the acid value had
fallen t¢ below 5. A total o~ 37 g distillate wa~ col-
lected.
650 g o~ a solid mass tallow-like in consistency were
obtained after cooling. The titratable nitrogen content
was 2.17%.
61 g of the reaction product was mixed with 5.6 g
isoprcpanol at 60-C and neutralized with 10.6 g 80% lactic
acid. The ~elt was then stirred into 422.8 g water at
80-C, followed by rapid cooling to 30-C. A fine-particle
dispersion containing 20% by weight active substance was
obtained.
,
D 9347 PCT 6 210~2~7
Exa~pl~s 2 to 2.3
540 g (2 mol) hydrogenated tallow fatty acid (acid
value 208, iodine value 1) were reacted with 149 g ll mol~
trietha~olamine as in Example 1.
s The end product contained 2.12% titratabl~ nitrogen.
2.1
100 g of the reaction product of Example 2 were
neutralized with 17 ~ 80% lactic acid and the melt (temper-
ature 80'C) was stirred into S54.4 g water at 85-C. The
fine-particle dispersion obtained after cooling contained
20% by weight active substanc~.
2.2
~00 g of the reaction product of Example 2, 6.2 g
phosphorous acid and 424.8 g water were heated together to
85-C and homogeneously stirred. The fine-particle disper-
sion obtained a~ter cooling contained 20~ by weight active
substance.
2.3
: lOo g o~ the reaction product of Example 2 were
neutralized with 9~2 g acetic acid and th~ melt (tempex-
ature 80C) wa~ stirred into 436.8 g water at ~5-C. The
: 25 fine-particle dispersio~ obtained after cooling contained
: ~ 20% by wQight active substance.
Exa~ple 3
550 g (2 mol) hydrogenated fish oil ~atty acid ~acid
value 204~ were reacted with 149 g (1 mol~ triethanola~ine
as in Example 1.
The end product contained 2.14% titratable nitrogen.
100 g o~ the reaction product were neutralized with 17
g 80% lactic acid and ~he ~elt (temperature 80-C) was
: 35 stirred into 554.4 g wat~r at R5-C~ The fine-particle
..
,: '" . ~ , . :
: : ,
2 ~
D 93~7 PCT 7
dispersion obtained a~ter cooling contained 20% by weight
active substance.
Ex~mple ~
677 g (2 ~ol) of a technical behenic acid containing
80% C22 (acid value 165.7) were reacted with 149 g (l mol)
triethanolamine as in Example 1.
The end product contain~d 1.7% titratable nitrogenO
As in Example 3, 67.6 g of th~ end product were made
up with 10.2 g 80% lactic acid and 422.2 g water into a
viscous, fina-particle dispersion containing 15~ by weight
active substanc~.
~x~plo 5
677 g (2 mol) of the behenic acid used in Example 4
were reacted with 118.9 g (1 mol) methyl diethanolamine as
in Example 1.
The end product contained 1.79% titratable nitrogen.
As in Example 3, 67.2 g o~ the end product, 10.7 g 80%
lac~ic acid and 421.1 g water were made up into a viscous,
~ine-par~icle dispersion containing 15% by weight ac~ive
substance.
Exa~pl~ 6
677 g (2 ~ol~ behenic acid were reacted with 147 g (1
mol) methyl diisopropanolamine as in Example 1.
The end product contained 1.66% titratable nitrogen.
As in Exa~ple 3, 67.6 g of the end product, 10.2 g B0
lactic acid and 422.2 g water were made up into a viscou~,
fine-particle dispersion containing 15% by weight active
substance.
. ;, ~
. .
2 ~ 8 7
D 9347 PC~
~mple~ 7~1 to 6
A use according to the invention of the alkanolamine
esters pr~pared in accordance with Examples 1 to 6 is
~escribed in ~he following.
Cotton terry was treated by the absorption method with
liquors containing the products of Examples 1 to 6. The
liquors ~tere applied under the following conditions:
Liquor ratio: 1:20
Product input: 0.6~ by weight active substance,
based on the weight of the fabric
pH value: 5.5 (adjusted with acetic acid)
Temperature: 50~C
Treatment time: 20 minutes
After the treatment, the pieces of fabric were dried
at 120-C on a tenter frame and, after adaptation to a stan-
dard conditioning at~osphere (25-C/60% relative humidity),
were tested by 5 people experienced in assessing feel.
Feel marks were awarded on a scale of 1 to 6 (1 = rough, no
softness, 6 = full soft feel~. The softness evaluation
thus completed is reproduced in Table 1 below in the for~
of mean values of the particula~ sub~ective i~pression.
~b~o 1
. ._..... _ __ _
Product o~ 1 2.1 2.2 2.3 3 4 5 6
~xample . _ ._
Softness 5 5.5 i 5.5 5 5 5 4 5
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