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Patented Sept. 10, 1946
' 2,407,346
UNITED‘ vs'm'rII-ZYs
OFFICE
MANUFACTURE OF NEW-"COLORING
-
-
MATTERS
'
-
I Maurice Arthur-TThorold Rogers, Blackley, Man
chester,‘-England, ,assignor to Imperial Chemical
Industries Limited, a corporation’ 1of' ‘Great
Britain‘
.No Drawing’. Application July 9, 12943, 'S‘eriaLNo.
494,120. ‘In, Great BritainJuly 13,1942
3 Claims.
(Cl. 260-13139 -
1
2
The present‘ invention-‘relates to the manufac
ture of new coloring matters.
In British application No. 16,2'76/41, and in
copendin'g" application Serial No. 457,2'2‘8,*?led
,
2 :2 ' :4 1 4 ’ - tetraphenyl-meso -phenyl-dipyrromon
. omethine,
The metal complexes may be formed by ‘using
the metals themselves, for example in a ?nely
September 3, '1;942,,.:now' ‘U. 1S‘. ‘Patent 2,382,914, 5 divided form, or by "using salts, for example the
there' are ‘described vtetraaryleaza-dipyrrometh
acetates, sulphates, chlorides, phosphates or dou
inesofxformula:
ble salts such as dichromates.
.
'
,
'
_R1v
N
tate.
and in copending application No. 494,126, ?led
Ju1yf9, 1943, there are described tetraaryldipyr
romonomethines of ‘formula
I
Rm__.((;_._'-g_._Rn,Rv-Q=G_Rvi
RI-g
'(IL-—-CR=’CIZ
‘(ll-RIV
Good results have
been obtained with, for example, copper acetate,
copper sulphate, zinc acetate, chromimn ?uoride,
10 cobalt sulphate, cobaltacetate, and nickel ace
V
-
‘
'
I
r
"
The reaction may be carried out by heating the
reagents by' themselves or ‘in'the' presence of a
solventfor one or both.
Alternatively, when metal complexes ‘are to be
15
made ‘from water-soluble derivatives of tetra
aryl-azaedipyrromethines Tor tetraaryldipy-rro
monomethines, for example, their ‘sulphonic acid
derivatives'which are‘ described in 'copen'ding ap-;
wherev RI, R11, It,w and'R.V stand ‘for ,aryl radicals, 20 plication Serial No. 482,479, ?led April '9', 1943,
‘ N
‘
~N
now U. S. Patent~2;382,l91~7, or the‘ salts of their
for example of-the benzenelorinaphthalene series,
substituted or not, the same ordifferent, where
Rm and R“ each. stand for hydrogen or for a
amino-derivatives, they may be‘ made by treat
ing dyeings of these Water-soluble compounds,
R.‘ stands for hydrogen or an alkyl-, aralkyl or
The invention is illustrated'but not limited by
the following examples, inv which the parts are
for example on wool, with aqueous‘ solutions of
non-reactive substituent, the‘ same or di?’erent,“
for example, an'aryl-,,,alkyl-, alkylamino-, ben 25 the metal salts. In this way, the metal com
plexes are formed on the ?bre.
zylideneamino- or acylamino- radical, and where
aryl-radical, or forra heterocyclic residue.
The present invention is directed to the pro
duction of’, ; metal “complexes, from. “these com
pounds that is to say,,_from_:compounds of the
formula
'
'
'
expressed by Weight.
Example I,
1 part of 2:2’,:4:4"-tetraphenyl-aza-dipyrro
'
methine, 0.5 part‘ of copper acetate and 50 parts
of butanol:are'rboiledtogether for 1 hourrand the
coppery brown crystalline material which forms
N
If
35 is collected by ?ltration.
The product analyses
for C64H44N6Cu, and has the probable formula: :
where RI, Rn, Rm, RI", RV and RVI have the sig
ni?cance given above, and where A stands for
nitrogen or for the group CR, R being, as before,
hydrogen or an alkyl-, aralkyl- or aryl-radical,
or a heterocyclic residue.
According to the invention the metal com
plexes are manufactured by a process which com
prises bringing into reaction with each other a
compound of the general formula given above
and ametal of the group consisting of copper,
zinc, nickel, cobalt, chromium and cadmium.
Suitable compounds of the formula given above
include 2:2’ : 4 :4’ -tetraphenyl-aza-dipyrrometh- 50
inc, 2:2’:4:4'-tetraphenyl - aza - dipyrromethine
disulphonic acid, 2 :2’ -diphenyl-4 :4'-di- (p-meth
oxyphenyl) -aza-dipyrromethine, 2:2’ :4 : 4’-tetra
phenyldipyrromonomethine, 2: 2' :4-triphenyl-4' (p - methoxyphenyl) - dipyrromonomethine and
OH=C—Ph rh-cli—-~<lin
It is sparingly soluble in nitrobenzene, dioxan,
pyridine and dimethylformamide forming solu
tions which are blue in color.
I
_ In a similar manner, cobalt, nickel and zinc
55 acetates yield the corresponding complexes.
9,407,346
3
4
where R1, R11, R1", and Rv stand for aryl radi»
Example II
cals, RI11 and R" each are a member of the group
consisting of hydrogen, aryl-_ alkyl-, alkylamino-,
benzylideneamino-, and acylamino- radicals, A is
a member of the group consisting of nitrogen and
In place of the aza methine in Example I there
is used 1 part of 2:2":4:4’-tetraphenyldipyrro
monomethine. The copper complex forms cop-.
pery brown platelets, which are crystallised from
a mixture of pyridine and methyl alcohol in the
the group
.
‘
,:,.=
.
».
.
l
I‘
..
’
I
form of platelets. The product analyses forv
R
CcsHnsNeCu and is believed to have a structure .
similar to that assigned to the product of EXam-' 10 wherein R is a member of the group consisting of
ple I.
Example III
p
, hydrogen, alkyl-, aralkyl-, aryl-, and hetero
cyclic radicals; and B is a metal of the group
consisting of 'copper_ zinc, nickel, cobalt, chromi
The disulphonic acid derivative of 2122414’
tetraphenyl-aza-dipyrromethine is dyed on to
um, and cadmium.
2. Process for the manufacture of metal com
wool from an acid dyebath. The dyed Wool so
obtained is heated in a %% aqueous solution of
copper sulphate for 1 hour at 80-90° C. The
color of the dyeing changes from a reddish-blue
to a greener color as the copper complex is
formed.
plexes, which comprises bringing into reaction
with each other a, compound of the general for
mula:
20
Example IV
A compound of the formula
T
~
M03931
_
where RI, RH, RW, and RV stand for aryl radi
N(CHa)aI
25
cals, RIII and R“ each are a member. of the group
consisting of hydrogen, ary1-, alkyl-, alkylamino-,
benzylideneamino-, and acylaminoé radicals, Ais
a. member of the group consisting of nitrogen and
the group 1
'
_.G=
l
R
made’ by interacting -2:2’-diphenyl-4:4’-(p-di
wherein'R is a member of the group consisting of
methyl-aminophenyl)-aza-dipyrromethine with
hydrogen, alkyl-, aralkyl-, aryl-, and heterocyclic
methyl iodide is dyed on to wool from a neutral
dyebathp The greenish blue dyeing so obtained
radicals, with a member taken from the group
consisting of copper, zinc, nickel, cobalt, chromi
is heated in a 1% aqueous solution of copper ace
tate; I The color of the dyeing changes to a -red—,
um, and cadmium and their salts.
3. The compound of the formula:
dish blue as the copper complex is formed.
I claim:
1
_
> > 1.‘ Metal complexes of the formula:
(‘info-P11 Ph-C=GH
Ph--C
0-——N=o
\N/
45
v
C-Ph
/
7 \‘Cu
/ ,
50
55
ROGERS.
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