hurrah stares rarest" orrieu

Patented Sept. 13, 1934
$73,860
hurrah stares rarest" orrieu
1,973,360
All!!!) E S OF N - BETA - HYDROXYALKYL
. AIVHNO CABBOXYLIC ’ AEIDS AN'D ?BOC—
ESS 0F PREPARING SAW
Heinrich Ulrich and Karl Saurwein, Ludwlgs
hafen-on-the-Rhine, Germany, assienors to
l’. G. Farbenindustrie Akiiengesellschait, Frank
iort-on-the-Main, Germany
No Drawing. Application February 6, 1932, Serial
No. 591,451. in Germany February M3, 1931
13 Claims. (Cl. 259-112)
The present invention relates to the production the presence of a quantity of alkali sumcient to
of assistants for the textile and related indus neutralize the halogen hydride formed, the alkali,
tries.
We have found that valuable assistants for the
5 textile and related industries, such as wetting,
washing, dispersing, softening and like agents,
can be obtained by causing N-?-hydroxyalkyl
amino carboxylic acids containing a hydrogen
atom connected to the nitrogen atom to react
10 with halides of aliphatic carboxylic acids con
taining at least a carbon atoms. The said fatty
acid halides may be chosen from the halides of
such as sodium or potassium hydroxides or car
bonates or calcium hydroxide, being usually em
ployed in the form of their aqueous solutions. 00
The reaction is preferably carried out at tem
peratures between 0° and 80° C., the temperature
varying ‘with the activity of the. initial materials
and being raised, if the reaction is to be ac-‘
celerated. For attaining a most uniform reaction
the acid- halide is preferably introduced, while
stirring, into an‘ aqueous solution of the alkali
open chain or cycle-aliphatic carboxylic acids metal salts of the amino carboxylic acids. The
especially of those of natural fatty acids and products obtained. according to the present in
15 particularly of those of vegetal, i. e. animal and vention are apparently amides ‘oi’ the amino
m
vegetable, origin, such as butyric, lauric, palmitic, carboxylic acids and fatty acids and correspond
stearic, oleic, montanic, myristic and like acids to the general formula
v
as well as of halides from mixtures of such
acids, as for example those of the acids of coco
20 not or peanut oils, train oils and like natural
acids. Halides of the acids from the oxidation
of paraffin ‘wax- and naphthenic .acids may be
also employed as well as halides of halogenated
acids of the said nature as for example of di
25 chlor stearic or mono-chlor palmitic acids. In
most cases the chlorides of the acids will be em
ployed, since they are easily available in com
30
oin-omomx
R—C 0-N
’
75
o (x) (x)_c cor
7
in which R denotes an aliphatic radicle contain
ing atleast 3 carbon atoms, X denotes either 80
hydrogen or an aliphatic radicle and Y denotes
hydrogen or a radicle of a base such as Na or K;
parison to bromides. The said N-p-hydroxy thus R-CO may be the radicle of butyric,
alkyl amino carbonylic acids correspond to the capryllc, lauric, oleic, stearic, di-chlorstearic,
general formula ’
palmitic, mono-chlorpalmitic, montanic or like 85
acids as described above, especially of those which
CHg-CH(OH)X
EN
contain from 4 to 20 carbon atoms, while X corre
sponds to the corresponding radicles of the
original hydroxy-alkyl amino carboxylic acids.
in which X denotes hydrogen or an alkyl radicle,
such as methyl, ethyl, propyl, butyl, amyl or
higher alkyl radicles. These carboxylic acids can
he obtained for example by saponifying nitriles
obtainable according to the present inventors’
application for U. S. Patent Ser. No. 591,450 ?led
February 6th, 1932 by condensing hydrocyanic
By the addition of alkili and the formation of 30
halogen hydride, alkali halides are formed as
by-products which may be left in the reaction
products without impairing their properties or
may be removed in any usual and convenient
manner.
95
‘ By the process according to this invention
products are frequently obtained ‘which are solu
ble in water and which are eminently suitable as
acid with oxazolidines corresponding to the
wetting, washing, dispersing and softening agents
45 general formula
in the textile industry; they may be employed 100
in acid, neutral and alkaline treatment baths
CHE-OHX
without any deposits of dimcultly soluble salts
HN
.
even when usingr water containing lime. The
said condensation products may be employed
with special advantage in the parchmentizing or 105
x \x
mercerizing h'eatment, of cotton fabrics or of
in which X denotes hydrogen or an alkyl radicle, paper with concentrated sulphuric acid; most
such as methyl, ethyl, propyl,‘ butyl, amvl or of them, especially those prepared from acid
higher alkyl radicles.
.
halides with'from 8 to about 14 carbon atoms,
The condensation is preferably carried out in easily dissolveior example in sulphuric acid of' 110
/G_
2
1,973,860
Example 2
5° Bé. as is usually employed for the parch
mentizing of paper. By adding-from 0.5 to 10 per
The a- (n-propyl) -a (N-péhydroxyethyl amino) cent by weight of the substances to the sulphuric acetonltrile
acid, the goods to be treated are wetted very
cnrcmon
rapidly and uniformly so that a previous wetting
is unnecessary. From 1 to 5 grams of the said
substances may be added to each litre of a bath
CH
for rendering arti?cial silk smooth and soft.
C 9111
The said products are also suitable as dispersi
ing agents for dyestuffs, resins, waxes, paraf?n obtainable according to the aforesaid applica
oils or waxes, mineral or vegetable oils or fats tion for patent Ser. No. 591,450 from equimolec
and organic solvents in liquids in which the said ular proportions of mono-ethanol amine, butyl
aldehyde and hydrocyanic acid, is saponi?ed as
materials are more or less insoluble.
The condensation products may be used as such described in Example 1. 1 molecular propor
or together with other substances, such as soaps, tion of the product obtained is caused to react
Turkey red oils or dispersive sulphuric esters of with 1 molecular proportion of n-butyric chloride.
other aliphatic compounds or 'sulphonic acids of The reaction product is a water-soluble oil which
aromatic compounds, or with salts, such as per has a very good wetting power in neutral and al
borates, Glauber’s salt or tartaric acid salts or kaline baths, as for example in caustic mercer
with glue, gum arabic or dextrine, a highly e?i izing lyes, as well as in sulphuric acid of from 95
cient composition consisting for example of N 40 to 70 per cent strength; the free acid‘may be
hydroxyethyl glycocoll stearic amide mixed with obtained by acidifying the aforesaid product
the sulphuric ester of mono-ethanol amine coco for example with hydrochloric or sulphuric acids.
fatty acid amide. The employment of the said
Example 3
100
condensation products in conjunction with or
The carboxylic acid
ganic solvents, such as cyclohexanol, tetrahydro
naphthalene, water-insoluble liquid or solid al
HN-CHr-CHaOH
cohols or ketones, is also advantageous.
coon
The following examples will further illustrate
—-C;H1
105
the nature of this invention but the invention is
not restricted to these examples.
H,
HN\ /CN
10
15
20
30
Example 1
obtainable by saponifying the nitrile obtainable
according to the aforesaid application ‘Ser. No.
from mono-ethanol amine, methyl-iso- no
One molecular proportion of the 'hydroxy ethyl 591,450
35
propyl ketone and hydrocyanic acid is condensed
amino acetonitrile
with the equimolecular amount of stearic chloride.
The paste obtained is dried on the water~bath,
a water-soluble powder is thus obtained which -
is an excellent washing agent.
40
“5
What we claim is:
obtainablev according to the aforesaid applica
tion Ser. No. 591,450 from molecular propor
tions each of mono-ethanol amine, formaldehyde
and hydrocyanic acid'is saponi?ed by boiling
45
with 2 molecular proportions of caustic soda in
the form of a 20 per cent aqueous-solution until
the whole ammonia formed by the saponi?cation
1. The process for the production of amides
suitable as assistants for the textile and related
industries which comprises reacting a N-s-hy-'
droxyalkyl amino carboxylic acid containing a
hydrogen atom connected to the nitrogen atom 120
with a halide of an aliphatic carboxylic acid con
taining at least 4 carbon- atoms.
' '
2. The process for the production of amides
is driven 011. 1 molecular proportion of co suitable as assistants for the textile and related
conut oil acid chloride is dropped at from 20° industries which comprises reacting a N-s-hy
to 30° C. into the alkaline solution obtained. A droxyalkyl amino carboxylic acid containing a
water-soluble oily, neutral solution of the sodium hydrogen atom connected to the nitrogen atom‘
salt of the amide and sodium chloride is formed with a halide of an aliphatic carboxylic acid con
which is readily soluble in alkalies of any con taining at least 4 carbon atoms in the presence
centration and which has a very good wetting of a quantity of aqueous alkali equivalent to that 130
55
power. The product is also soluble in strong
'
mineral acids; for example 0.5 to 1 per cent of the said halide.
3.
The
process
for
the production of amides
thereof may be introduced into sulphuric acid of suitable as assistants for‘7
the textile and related
about 54° Bé., its good wetting action not being industries which comprises
a N-?-hy
impaired thereby. The coconut oil acid chlo droxyalkyl amino carboxylic‘reacting
acid containing a 135
60 ride may also be replaced by stearic chloride, a
hydrogen atom connected to the nitrogen atom
water-soluble paste being thus obtained, the with a halide of an aliphatic carboxylic acid con
product consisting then mainly of
taining at least 4 carbon atoms at a temperature
between 0° and 80° C. in the presence of a quan
tity of aqueous alkali equivalent to that of the 140
65
CryHarCO-N
'
said halide.
orb-000m
4. The process for the production of amides
If from 1 to 5 grams of a mixture of 2 parts of suitable as assistants for the textile and related
oleyl mono-ethanol amide sulphuric ester or of industries which comprises reacting a N-p-hy
70 the amide obtainable by condensing coconut oil droxyalkyl amino carboxylic acid containing a hy 145
fatty acid chloride with amino-ethanol sulphuric drogen atom connected to the nitrogen atom with
' ester with 1 part of the aforesaid product be add a halide of a fatty acid containing from 4 to 20
ed to each litre of an aqueous bath for the treat carbon atoms at a temperature between 0°. and
ment of arti?cial silk a very smooth and soft 80° C. in the presence of a quantity of aqueous
CHg-CHIOH
75 silk is obtained.
alkali equivalent to that of the said halide.
3
1,973,860
-5. The process for the production of amides’ ing from 3 to 19 carbon atoms, X denotes either.
suitable as assistants for the textile and related hydrogen or an aliphatic radicle and Y denotes
industries which comprises reacting a N-?-hyc hydrogen or an alkali metal. I
droxyalkyl amino carboxylic acid containing a p 10. Condensation products suitable as assist
hydrogen atom connected to the nitrogen atom ants Ior the textile and related industries com
with a halide of a fatty acid mixture obtain prising amides corresponding to the vformula
able from vegetal material, at a temperature be
UHF-CHICK
tween 0° and 80° C. in the presence of a quantity
of aqueous alkali equivalent to that of the said
10 halide.
a-o 0-N
85
era-co OY
6. Condensation products suitable as assistants
for the textile and related industries comprising in which R denotes an aliphatic radicle contain
amides corresponding to the formula
ing from 3 to 19 carbon atoms and Y denotes hy
15
om-cmomx ."
drogen or an alkali metal.
11. Amides, suitable as assistants for the tex
n-o O-—N
c(x)(x)-0ooY
in which R denotes an aliphatic radicle contain
oHr-cmomx
ing at least 3 carbon atoms, X denotes either hy
20 drogen or an aliphatic radicle and Y denotes hy
drogen or an alkali metal.
90
tile and related industries, corresponding to the
formula
95
n-o O-N
'
-
'7. Condensation products suitable as assistants
o(x) (x)-coor
for the textile and related industries comprising in'which R—-CO denotes‘the radicles of a fatty
amides corresponding to the formula
acid mixture obtainable from vegetal materials,
25
X denotes either hydrogen or an aliphatic radicle 100
clan-onion
and Y denotes hydrogen or an alkali metal.
n-c 0—N
12. A condensation product suitable as assist
ant tor the textile and related, industries com
o (x) (X)—(; 0 OY
in which R denotes an aliphatic radicle contain
30 ing at least 3 carbon atoms, X denotes either
hydrogen or an aliphatic radicle and Y denotes
hydrogen or an alkali metal.
8. Condensation products suitable as assistants
for the textile and related industries comprising
prising the amide ot N-hydroxyethyl glycocoll
and stearic acid which corresponds to the for 105
mula,
11-0 0-
40
'
45
'
110
era-coon
13. A condensation product, suitable as assist- ‘I ‘
ant for the textile and related industries, com
'
v
in which R denotes an aliphatic radicle contain
ing from 3 to 19 carbon atoms, X denotes either
hydrogen or an aliphatic radicle and Y denotes
prising the amide oi' lN-hydroxy-ethyl glycocoll
and acids 01' coconut oil which corresponds to the 115
formula
cm-oraoir '
'
11-0 0-
9. Condensation products suitable ‘as assist
ants lor the textile and related industries com
prising amides corresponding to the formula v '
era-onion .
om-omon
cum-c041
1
c(x)(x‘)—o0oY
hydrogen or an alkali metal.
c
‘
35 amides corresponding to the formula
CHr-CH(OH)X
.
~
CHI-000E‘
120
in which n-co denotes the radicle oi.’ the acids
of- coconut' oil.
-
B-00—N ‘
011-0001!
,
HEINRICH
ULRICH. -'
KARL SAURWEIN.
125
in which n denotes an aliphatic radicle contain- _ v.
140'
70
76
145'

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