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Патент USA US2118713

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Patented May 24, 1938
UNITED STATES
PATENT orrice ‘
2,118,713
MANUFACTURE OF NITROGEN CONTAIN
ING DERIVATIVES 0F POLYMERIZED
VINYL ESTERS OF HALOGEN FATTY ACIDS
Herbert Rein, Leipzig, Germany, assignor to I. G.
Aktiengesellschaft,
fort-on-the-Main, Germany
Farbenindustrie
Frank
No Drawing. Application August 1, 1935, Serial
No. 34,298. In Germany August 7, 1934
12 Claims. '
My present invention relates to the manufac
- ture of nitrogen containing derivatives of poly
merized vinyl esters of halogen fatty acids.
,
One of its objects is a process of producing
5 nitrogen containing derivatives of polymerized
vinyl esters of halogen fatty acids.
Another ob
ject are the nitrogen containing derivatives of
polymerized vinyl esters of halogen fatty acids.
Further objects will be seen from the detailed
10 speci?cation following hereafter.
I have found that nitrogen containing poly
vinyl derivatives are obtainable by treating a
polymerized vinyl ester of a halogen fatty acid
r with an organic base in the warmth.
As or
ganic bases which enter into consideration I
enumerate primary and secondary aliphatic
aromatic and hydroaromatic amines; further
more, tertiary aliphatic aromatic and hydro
aromatic amines preferably those which contain
at least 1 methyl group; futhermore, pyridine,
piperidine and cyclohexylamine. Such amines
are for instance, methyl amine, tetramethyl
ethylenediamine, n-dimethyl-Z-aminobutane, di
methyldodecylamine and methylbenzylamine.
The condensation is performed while using the
(01. 260-2)
The following examples illustrate the inven
tion:
.
Example 1.—12 grams of polymeric vinyl
chloracetate are dissolved with aid of heat in
30 to 50 cc. of pyridine. After heating for about‘
15 minutes at 100° 0., the reaction begins and
the solution solidi?es to a yellowish-white, solid,
radiated mass, which is easily soluble inv water.
By pulverization and subsequent extraction with
carbon tetrachloride or another suitable ‘solvent 10
the mass can be thoroughly freed from excess of
pyridine. There is ?nally produced a white,
nearly odourless powder which dissolves gradual
ly' when heated with water, while swelling.
Instead of pyridine a homologue of pyridine 15.
may be used either alone or together with
pyridine.
'
Example 2.—120 grams of polymeric vinyl
chloracetate dissolved in 500 cc. of acetone are
slowly mixed with 85' grams of piperidine, if 20
necessary while cooling. The solution solidi?es
to a ?brous mass. After washing with'methyl
alcohol the reaction product has a content of
nitrogen of 4.34%.
-
'
Example 3.—120 grams of polymerized vinyl 25
base alone or with the addition of diluents and/or ' chloroacetate dissolved in 500 cc. of acetone are
‘solvents, for instance, water or acetone. ‘The
condensation takes place already at room tem
perature, however, it is preferably carried out at
30 a temperature of 80 to 120° C.
In some cases
there may be used a temperature higher than
, 120° (2., however, in general thereoccurs more
or less strong degradation. The products ob
tained contain about 2 to 7% of nitrogen. The
35 content of nitrogen depends on the magnitude
of the molecule of the_.._polymerized vinyl com
pound and of the organic base. Generally two
molecular proportions of polymerized vinyl
reacted upon with 84 grams of piperidine in the
manner described in. Example 2. The reac
tion product is washed with carbon tetrachlo
30
ride and dried at 60° p.
Example 4.—120 grams of polymerid vinyl
chloroacetate dissolved in 500 cc. of acetone are
reacted upon with 100 grams of cyclohexylamine.
The reaction product is washed with carbon
tetrachloride and has a content of 8.3 of ni 35
trogen.
The yield is 215 grams. .
Example 5.—120 grams of polymerized vinyl‘
chloroacetate dissolved in 500 cc. of acetone
halogen fatty acid ester (calculated on the un
after interaction with 45 grams of dimethyla
til polymerized product) react with one molecular mine yield a product containing 6.6% 01’ ni 40
proportion of base. This proportion is obtained ‘ trogen.
when using a su?iciently high temperature and
Example 6.-—In a solution of 120 grams of
when continuing the reaction ,sumciently long.
The products obtained are water soluble, or swell
45 able in water, or insoluble in water. The solu
bility in water depends on the kind of base in
troduced in the molecule of the polymerized
vinyl compound, and on eventually occurring
partial saponification. In the latter case al
50 cohol groups are introduced in the molecule of
the polymerized vinyl compound.
The products according to this invention may
be used as protective colloids, emulsifying agents,
thickening agents, adhesives, textile assistants
55 and the like.
vinyl chloroacetate there are introduced 120 '
grams of trimethylamine, whereby the solution
becomes-‘turbid and soon a crystalline precipi 45
tate separates.
'
Example 7.-.-120 grams of polymeric vinyl
chloroacetate dissolved in 500 cc. of acetone are
mixed with 120 grams of tetramethylethylene
diamine and allowed to stand- for 48 hours. 50
There are obtained 222 grams of a white powder
containing 6.75% of nitrogen.
‘
Example 8.—120 grams of polymeric vinyl
chloroacetate dissolved in 500 cc. of acetone yield
when heated with 205 grams of dimethyl 55
2
9,118,718
dodecylamine on the steam-bath to 60° on cool
ing 290 grams 01' a wax-like powder containing
3.23 per cent of nitrogen.
Example 9.-—400' grams of polymeric . vinyl-.
100° C. for about 15' minutes and carrying on the
reaction until separation of a solid mass.
,
5. A process 01' introducing nitrogen in a poly
merized vinyl ester of a- chloroaliphatic acid
chloroacetate of which half of its ,chloroacetyl which ‘comprises dissolving polymeric vinyl
groups have been split oil by saponi?cation with chloracetate in acetone, and interacting this so- a methyl alcoholic solution of caustic soda, are _ lution with dimethylamine.
boiled with 1000 cc. of water and 200 grams oi
6. A process of introducing nitrogen in a poly
trimethylamine for 12 hours under‘re?ux and merized vinyl ester vof a chloroaliphatic acid
10 precipitated by means of acetone. "I'here re
which comprises saponiiying 'vinylchloracetate
sults a white powder with a content of nitrogen until half of its chloracetyl groups have'been split
of 2.3 per cent. 1
.
.
off, boiling the resulting product with 1000 cc. of
In the examples polymerized vinyl chloroac
water and 200 grams of trimethylamine for 12’
etate hasbeen used as a starting material in
hours under re?ux, and precipitating the reaction
asmuch as this compound is the'practically most product with aceton.‘ - I
\
important. However, the invention is not lim
7. A polyvinylester of a chloroaliphatic acid
ited to the use of this compound, but other containing‘ about 2 to 7 per cent 01' nitrogen
polymerized vinylesters oi chloro-i'atty acids bound in amine residues.
with a straight or branched‘ chain of carbon '
20 atoms may be used, for instance, lower members
such as chloropropionate or higher members such
as chlorolaurateor chlorostearate.
3
What I claim is:
.
,
_
1. A process of introducing nitrogen in a poly
25 merized vinyl ester: of a chloroaliphatic acid
which comprises treating said polymerized vinyl
which comprises treating said polymerized vinyl
ester or a chloro-aliphaitic acid with a tertiary
‘ amine containing in its molecule at least one
methyl group.
9. A process of introducing nitrogen in a poly
merized vinylester o! a chloro-aliphatic acid
ester of a chloroaliphatic acid with an amine
which comprises heating said polymerized vinyl
selected from the group consisting oi primary
ester or a chloro-aliphatic acid with an amine
secondary andptertiary amines.
30
8. A process of introducing nitrogen in a poly- '
merized vinylester of a chloro-aliphatic acid 20
selected from the group consisting of primary,
2. A process of introducing nitrogen in a poly
secondary and tertiary amines.
merized vinyl ester 0”! a chloroaliphatic acid
10. A process of introducing nitrogen in a poly
which comprises treating said polymerized vinyl fmerized vinylester of a chloro-aliphatic acid
ester of a chloroaliphatic acid with an amine which comprises heating said polymerized vinyl
selected from the group consisting of primary ester of a chloro-allphatic acid with an amine
35 secondary and tertiary amines; in the presence of selected from the group consisting of primary,,
a diluent.
;nerized vinyl‘ ester of a chloroaliphatic acid
which comprises treating said polymerized vinyl
40 ester 01' a chloroaliphatic acid with an amine
selected from the group consisting of primary
secondary and tertiary amines in the‘ presence of
'
30
' secondary and tertiary amines in the presence of
’
- 3. A process of introducing nitrogen in a poly
a solvent.
25
.
4. A processor introducing nitrogen in a poly
merized vinyl ester 01' a chloroaliphatic acid
which comprises dissolving polymeric vinyl
chlcracetate in pyridine, heating the mixture to
'a diluent.
-
-
11. A process of introducing nitrogen in a poly
merized vinylester of a chloro-aliphatic acid
which comprises heating said polymerized vinyl 40
ester 01a chloro-aliphatic acid with an‘ amine
selected from the group consisting oi! primary,
secondary and tertiary amines in the presence of
a solvent.
'
_
.
‘12. A polymerized vinyl-chloracetate contain
ing. about 2 to 7% 01' nitrogen bound in an amine 45
v residue.
:m- = w-
REIN.
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