Document MGX6OgpEr5rGb7x3DpkQb92wL
S e r ia l Humber 18071
f
Dr. X. Cube Imamu
Dr. H. A. Lubs ' {l)
Dr. E. K. Bolton (1)
Dr. Win. Kirk
(1)
Mr. J * S. Groves
for I.C.I. J, L. Files
(5) (8)
E. I. DuPont de Nemours & Company Jackson Laboratory September 29. 1942
' jO*J o
|4I -' # i
Azo Lakes and Pigments
N40787
JLR-4J-L, No. 24
mwji-
FEB 111943 &H.Cl
aa
Serial Number 18071
E. I. DuPont de Nemours & Company Jackson Laboratory Azo Colors Division S> S. Rossander
Progress Report
September 29, 1942
Azo Lakes and Pigments
Group Leader - D. E. Kvalnes Work Done By - H. E. Woodward
Reported By - H. E. Woodward
Work Started - March 1, 1942 Completed - July JO, 1942
J. M. TINKER, ASST. DIRECTOR
W. S. CALCOTT, DIRECTOR.
DUP050059099
JLR-43-L, No. 24
Azo Lakes and Pigments (Project Number 422)
H. E. Woodward
Serial Number 18071
Object of the Investigation:
.
The discovery of new azo compounds with superior properties, which might be desirable additions to our line of pigments and lake colors.
Period Covered by this Report: March 1 to July 30, 1942.
Historical Background:
In the previous report on this project the following interesting products were reported.
A preliminary sample was requested of the red pigment 2-amino-6-chi ortoluene ** Naphthanil AS.
A preliminary sample was requested of the yellow pigment 2-nitro-4-chloraniline - 2-methyl-3-chloracetoacetanilide,
Dichlorbenzidine (2-methyl-3-chlor-acetoacetanilide)2 is a possible outlet for 2-nitro-6-chlort oluene, being close in shade, strength and fastness properties to Lithosol Yellow G Cone.
Dichlorbenzidine -> (aceto-acetyl~o-amino-diphenyl)2 and dichlorbenzidine * (aceto-acetyl-pseudocumidine)2 are slightly
superior to Lithosol Yellow G Cone, in light fastness.
Yellow pigments from 2,5-2'51-tetrachlorbenzidine have very good light fastness but are weak tinctorlally.
j
A preliminary sample was requested of the non-migrating reddish yellow pigment, 3>3t^diphenyl benzidine -> (aceto-acetanilide)2 for testing in rubber.
A preliminary sample was requested of the Bordeaux toner j 2-amino-4-chlortoluene 2-hydroxy-3-naphthoic acid, nickel ? salt, which has very good light fastness.
Preliminary samples were requested of the manganese, cobalt and nickel salts of Tobias acid -> R-salt, all of which are maroons in masstone and show very good fastness to light.
The manganese> nickel and cadmium toners of Lithosol Red 2B are slightly superior to the standard calcium toner in fastness to light.
DUP0500591OO
The manganese tones' of 2-sulf o-3-amino-6-chiort oluene - 2-hydroxy-3-naphthoic acid Is of some interest as an outlet for 2-nit ro-6-chlort oluene.
Several metal complex compounds of very good light fast ness were found, hut they are too dull to be of much interest*
Conclusions;
The strong, light-fast greenish-yellow pigment 2-nitro-4chloraniline * 2-methyl-3-chlor-acetoacetanilide, J-43-P-198,
is approved by Technical Laboratory as a color for commercial expl oitation, and our Sales Division has requested that we call it to their attention for manufacturing consideration after the Swar. . I'
The fast-to-light manganese, cobalt and nickel toners of $ Tobias acid E-salt, J-43-P-199,p.200,p.-201 are of some interest \ in lacquers and paints and .they are undergoing outdoor exposure } tests.
Cf, K ltyo 1
(<61% fto-d)
The red pigment 2-amino-6-chlortoluene -> Naphthanil AS, J-43-P-205 (alkaline coupling) and J-43-P-206 (acid coupling) is of interest as a substitute for Toluidine Toner. Pinal samples of both couplings were requested and a new project was t ake^ o t ^ fqr^t^s^wQrk.
f%4 Hurtt , \ The red lake color 2-sulfo-3-amino-6-chlortoluene 2-
hydroxy-3-naphthoic acid, J-43-P-209, was not considered of
K'lW
interest by Technical Laboratory as long as present standard colors are available.
fr-mt)
The red lake color 2-amino-6-chlortoluene -> R-acld. J-43-P-214, was not of interest to Technical Laboratory as a substitute for Lithosol Scarlet 2R, because of weakness.
Summary:
The following preliminary samples were made -
J-43-P-198 - 2-Nitro-.4-chloraniline -> 2 -methy1 -3 - chlor'acet o-
acetanilide, a strong greenish yellow,
J-43-P-199 - Tobias acid -> R-salt, manganese toner, a fast-to- .. . light red.
J-43-P-200 - Tobias acid > R-salt, cobalt toner, a fast-to-light
red
J-43-P-201 - Tobias acid -> R-salt, nickel toner, a " " " red.
J-43-P-205 - 2-Amino-6-chlortoluene Naphthanil AS, powder
J-43-P-205A-
"
"
."
" , paste
j..if3_P-206 - 2- '*
" -* i ti ^ a p0SSipie
substitute for Toluidine Toner,
J-43-P-209 - 2-Sulfo-3-amino-6-chlortoluene 2-hydroxy-3-
naphthoic acid, a red lake color derived from 2-nitro-
6-chlortoluene. -2-
DUP050059101
J-43-P-210 - 3> 3 *-Dlphenylbenzidlne -> (acetoacetanilide)2 a
reddish yellow rubber color which is a possible
replacement for two rubber yellows - Rubber Yellow
RD and Rubber Yellow CG (Chro e Yellow of Krebs)
now in our line,
J-43-P-214 - 2-Amino-6-Chlortoluene R-salt, a red lake color
found by Krebs to be a desirable substitute for
Llthosol Scarlet 2R.
LeUuU
Some further process work was done on two pigments
1 - 3> 31-Dichlorbenzidine (2-methyl-3-chloraeetoacetanilide)2 a derivative of 2-nitro-6-chlortoluene which is somewhat like Llthosol Yellow G Cone*
2 ~ 2-Amino-4-chlortoluene -> 2-hydroxy-3-naphthoic acid, nickel toner, which is a fast-to-light bordeaux or maroon*
New pigments of the following types were made and tested,
1 - Monazo pigments
2 - Disazo and polyazo pigments
3 - Metallized pigments with no metallizing group on the diazo
component.
\
4 - Metallized pigments with metallizing group on the diazo
component.
Patent Status:
A patent memorandum OR-1507 was prepared on decorative and protective coating compositions colored with the pigment 2-amino-6-chlor-toluene -> Naphthanil AS.
The patentability of other pigments mentioned in this re port has not been investigated.
'
Plans for Future Work;
1 - Make a preliminary sample of the fast-to-light bordeaux 2-amino-4-chlortoluene -> 2-hydroxy-3-naphthOic acid, nickel toner.
2 - Evaluate available intermediate when they offer a possibility of lowering costs or improving properties or using by-products.
3 - Continue the investigation of Naphthanil pigments to improve fastness properties.
4 - Continue the investigation of co-valent metal azo pigments, looking for colors of unusual light fastness.
5 - Evaluate lakes of other hydroxy-naphthoic acids than 2hydroxy-3-naphthoic acid.
-3-
DUP050059102
Experimental Results;
I. Further Work on Colors Previously Reported
A. J-43-P-198 - 2-Nitro-4-chloraniline - 2-methyl-3chloracetoacetdnilide. This greenish yellow pigment, which is similar to Lithosol Fast Yellow 10G (2-nitro-4-chloraniline o-chloracetoacetanilide) hut twice as strong, was discussed at the Azo Lakes and Pigments Conference of February 19 and a preliminary sample was requested. It was reported oil Technical Laboratory Memo. 368-J as follows -
Krebs
Lithosol
Lithosol
YT454D Fast Yellow Y Fast Yellow HL
Masstone Tint
Strength Oil and Alcohol Bleed
Overstripe Light Fastness, Tint
Darker Darker
Greener
Redder, Greener,Bright
" ,Brighter
Duller er
46:100 125:100
155:100
v.Sli. sii.Sup,
Sli.Sup.
Inf.
Sli.Sup. Much Sup.
Equal
M II
Sli.Sup, Much "
The report stated'"This color is a strong greenish yellow of such interest that we recommend its addition to our line," The coupling component is a derivative of 2-nitro-6-chlor1! toluene, and the Intermediate Processes Division has developed
if an economical process for making it.
Bj. J-45-P-I99, -P-200, -P-201 - Tobias acid $ B-salft
manganese, cobalt and nickel toners. The original samples of - . these toners, although showing excellent light fastness, were ,// rather weak and dull. It was found that they could be improved
considerably in brightness and strength by precipitating at 60 or higher in the presence of about 160 parts of para soap per mole and holding at 900 for 1/2 hour or longer before filter ing. These preliminary samples were made and reported as fol lows against a barium lake of Lithosol Scarlet 3BI (anthranilic acid -* R-salt.)
P-199 (Mn)
P-200 (Co)
P-201 (Wi)
Masstone Tint Strength
Water Bleed
Alcohol Oil Soap
Fadeometer Masstone (100 hrs
Undertone " " Tint (75 hrs.)
Dark Brown Sli.Darker
Yellow,v.Dull Yellow,v.Dull
100:44
100:60
Inf.
Equal
SI.Inferior V.Sli.Inf.
M.Superior M.Superior
Inferior
Sli.Sup.
)
Equal fl
Superior tt
Equal -4-
Sli.Darker Yellower,Duller 100:44 Inferior M, " Sli.Superior Sli. "
Superior
It
Equal
DUP050059103
These samples were also made, into water dispersible powders
by W&P milling a mixture of 40$ toner, 50$ dextrin arid 10$
leukanol, and tested In paper dyeing against Lithosol Red
CSP as follows -
.
Shade - Consid. Yellower, Somewhat Brighter Strength - 170:100 Light Pastness - Much inferior
One of the water dispersible samples (nickel toner) was also tested In wall paper coating against Sulfanthrene Pink SV Paste, with the following results -
Shade -Yellow, Slightly Dull Strength - Weaker - 120:100 (Equal Color Basis) Light Pastness - Heavy Tint - Sli.Superior
C. J-43-P-205 - 2-Amino-6-chlortoluene Naphthanil AS This sample was made by coupling in sodium hydroxide solution in the presence of 10 parts of rosin per' mole. It was tested against Krebs Toluidine Toner, RT 386D and reported as LM-528J.
Ink Tests
Masstone
Darker
Tint
V.Yellow and light 100:140
Water Bleed
Superior (v.v.Sli.Bleed)
Alcohol
Sli,Inf,(Medium' " )
Oil
V.Sli.Sup. ( "
")
Soap
Equal
("
")
Fadeometer, ii j
Masstone Inferior
Tint
Much "
at 135 hours at 80 hours
Lacquer Grind Masstone Lighter, slightly brighter
Tint
Sli.Yellower,brighter,slightly strong
Overstripe Equal
Dulux Grind
Masstone Tint
Very slightly flat Yellow and strong
For final sample of this color JLR-43-450, No. 1
D. J-43-P-205A - Paste sample of above. This sample was prepared in order to test the possibility of making use of the extra strength of this pigment. A 62.5$ rosinated lake and a 6?.5$ aluminum hydrate lake were prepared and tested against RT386D.
-5,
DUP050059104
Rosin Lake
Aluminum Latte
Ink Tests Masstone
Sli.
Darker
Tint
V.Yellow
Water Bleed Equal
Alcohol " Equal
Oil " "
Light
Fastness Close
Sli,Dark, Sli.Brown
V.Yellow Equal. Equal
tr
Close
Lacquer Orind
Masstone Lighter and Brighter Lighter and Brighter
Tint
Brighter
Brighter
Strength . Equal
Equal
Overstripe V.Sli.Inferior
V.Sli.Inferior
Outdoor exposure tests on lacquered panels are not completed ' so it can not he stated at present whether the extended product
is satisfactory.
B. J-42-P-206 - 2-Amino-6-Chlortoluene -> Kaphthanil AS. This sample was made by acid coupling with sodium acetate buffer at 60. Compared with J-43-P-205 it is much bluer and slightly Veaker, through the reported strength against toluidine toner is better. The comparison against ET386D, as reported on LM717J is as follows:
Ink Tests
Masstone Tint Water Bleed Alcohol " Oil " Fadeometer
Slightly lighter and brighter Bluer and brighter 50:100 Slightly superior Equal Slightly inferior V.Sli.inferior
Lacquer Grind
Masstone Tint Overstripe
Sli,yellower, slightly brighter Bluer and slightly stronger Equal
For final sample pf this color see JLR-*F5-^50,
F. J-42-P-209 - 2-Sulfo-5-amino-6-chlortoluene 2-hydroxy l-naphthoic acid. In the last report on this project it was stated that this color would be of interest in case of a shortage of derivatives of p-toluidine used in lake colors, Laking experiments showed that the quality of. the toners could be improved by the use of para-soap or rosin in the precipitation of the calcium or manganese salts. Accordingly a preliminary sample of the sodium salt in paste form was submitted to Technical
-6-
DUP050059105
Laboratory and reported on LM1001J. A rosinated calcium lake
compared with Krebs RT455D (a rosinated calcium lake of Lith-
osol Bed 2B).
,
Masstone - Slightly Barker - Slightly Superior at 74 Hrs.
Tint
*"
Bluer - Inferior at 50 Hours
Unless outdoor exposure tests on paint panels show some advantage
this lake color is not of interest as long as present standards are available*
G. J-43-P-210 - Dlphenylbenzidine (acetoacetanilide)2. The preliminary sample previously requested has been made, but the Rubber Laboratory has not yet reported on it.
H. J-45-P-214 - 2-Amino-6-Chlor-Toluene + R-Salt This lake color was found by Krebs to be of interest as a replacement for Lithosol Scarlet SR,(m-xylidine R-Salt), so a preliminary sample was made for examination by Technical Laboratory. The comparison against Lithosol Scarlet 2R was reported on LM1412J.
Masstone
Much Limiter
Tint
" Yellower 127:100
Water Bleed
Slightly Superior
Alcohol "
""
Oil "
""
Padeometer (7 Hrs.)
"
"
Since it is planned to offer 2-amlno-6-chlortoluene for sale.. Technical Laboratory is not interested in further work on this color.
I. 3.31-Dichlorbenzidine > (2-Methyl-3-Chloracetoacetanilide) 2. Some further work was done on this color in coopera tion with Dr. Cooper of Krebs. It was found that this pigment
is very sensitive to over-drying* When carefully dried it is darker in masstone than Lithosol Yellow G Cone, and close in tint, but on further heating after it is dried it becomes much lighter in masstone and redder and weaker in tint. We are not interested in this Color as it would cost a few cents more than 0* Lithosol, Yellow G Cone, allowing recovery cost for 2-nitr0-6- 9* chlortoiuene,
J* 2-Amino-4-chlortoluene BON, nickel toner. The bright ness of this pigment in inks has been improved ao that it is now about equal in this respect to Lithosol Bordeaux BL. This improvement results from the use of 80 partiF^J^ftiole of color
and heating the suspension of `the sodium salt to 90 before addition of the nickel chloride. Lacquered panels of this color are on the outdoor exposure rack and the preparation of a pre liminary sample is awaiting the results of this test.
DUP050059106
II. Hew Pigments A. Monazo
Page Diazo
StanCoupler, dard Masstone Tint
Tint Fade- Oil Ometer Bleed
106A 2,5-Dichlor- Haphthanil AS
anlline
>B ff
IOTA
ft
B If
C ft
D If
" ASD " MX " PC " RL " OL
53A 2-Amino-6- BOH-2-Amino-
Cl-Toluene Diphenyl B ft BOH-p-aminp-
phenylme thy1
ct4r
*
Lt. Red
Die. " 1! ff It ft
ii
Blue Red Fair
Yel. " Weak M" Yel. ,f
it
Orange
n
Poor Fair Poor Fair Poor
Good
it
Fair . il
II it
Poor
Dk. " Bluish" Poor Good
sulfone 79 if B0H-2-amino-
6-Cl-Toluene
80 2-Amino-4-
ft
C1-Toluene 8l 2,5-Dichlor-
1!
anlline 85 2-Amino-4-
If
Dull " Deep " Dull " Brown
Orange Poor
Red Poor
Orange
n
Dull Red ft
Good Good
it fi
Cl-Anisol 86 2-Ritro-4-
It
Bed
Red
Fair
ti
Cl-Aniline 87 3-Hitro-4-
"
Dk. Red Bordeaux ti ,
H
Amino-Toluene 90 2-Amino-4-
ft
Lt. "
Yel. Red it
fl
Hitro-Tol. 91 2-Amino-4-
ff
ii
MH
ft
Hitro-Anisol 84 alpha-Naphthl-
"
Black
Dull Maroon Poor
If
amine
18 3 -Hitr0-4- AAA
Yel. S.Redder Close M.Inf. Iinf.
aminocumene
TOO
119A 3-Hitro-4- AAA
F. Or M. Yellower Mellower S.Inf. Equal
aminoanisol
ange G
D 3-Hltro-4- AA-p-phen- " M. Redder M.Redder Sup. Equal
aminoanlsol etidine
139 3-Hitro-4- AA-p-amino- F.Yel- M.Greener Greener, Inf* Equal
arainotoluene phenylmethyl lowHL
Weaker
sulfone
64 PHA
5-Hydroxy-
henzo2,1,3thiodiazo
Lt.Brown Dull Or. Poor
-8-
DUP050059107
(Quuap^sfa*uA> f
None of the preceding pigments is of much interests The sample 3-nitro-4-aminoanisol -> acetoacetyl-p-phenetidine has. good light fastness, hut it Is dominated by U.S. Patent 1,595,269.
B. Disazo and Polyazo
Diazo *
Coupler
Stan-
-
dard Masstone Tint
Tint Pade- Oil Ometer Bleed
5C 2,7-DiaminO- beta-NaphtholRT252D Mellower M.Yellower Equal Equal
xanthone
*
3D 450
n Naphthanil AS RT399 Lighter
2,7-Diamino-
It
Blue
M. Bluer Blue
Inf, Poor
ti
fluorene
158B 2,5,2`5'tet- AA-p-phenet- Ye1.G Dark and Green and Equal M.Inf.
-
rachlorbenzi-- idine dine
Dull
Weak
44a 2,5,2'5'tet- AA-0 -1 pluldlne "
Duller M.Weaker SI.Sup.
raehlorbenzi-
dine
44C 44B
it rt
AA-p- "
"
" phenetidfcie "
11 Grn.,Weak II II Dk.,Dull M.Weaker II It Equal
69 Dianisidine AA-p-phenyl- QrangeF M.Darker M,Duller M.Inf. 11
methylsulfone
128A Bithioanisi- AAA
Lt.Brown Dull Yel. Poor V.Sli.
dine
60A Bi-cresidine AAA I29A Dlnitrodiam- "
Yel.G Lighter M.Weaker M.Inf. Equal
Yel.G Duller Dull,Wk, S. "
11
lnodiphenyl-
sulfone 5A 2,7-Diamino- "
Yel.G M.Lighter M.Weaker
ti 11
xanthone 45A 2,7-Dlamino- ti
' Brown Yel.Brwn. V.Poor
fluorene 128B Bi-thioanis- PMP
Lt.Brwn, Dull Or.
11 Slight
idine
6pB Bi-cresidine "
OrangeF M.Yellower M.'&Uower Inf. S.Inf.
129B Dlnitrodiam- "
Yel.G M.Redder Tan
Tr N.B.
inodiphenyl-
sulfone
59 2,2'Dichlor- " 4,41 diamino
QrangeF M, Darker Redder Equal S.Inf.
stilbene 2,7Dlamtooxanthone PMP
" 0T Darker M.Yellower 11
Inf.
45B 2,7 " fluorene M
Red Brwn. Red Brwn. Poor
102A Tetraamino CPC l,40xyAdd
22A t!
Schaeffer "
105A 21A
It tl
J-Acid 8 -Byiroxyiilnollne
Black
n
if
11
GITra/y,W1! k.
Pair II
"It
,Str. IT Poor
Ii
ii
ii
ii
!1 1
Ii II
. !1
Ii 1 !
1 1 1
* ii
VDI!t li i!
DUP050059108
None of the preceding pigments is pf interest. 0. Metallized,-No Metallizing Group on the Piazo Component
Page
Diazo
Coupler Metal Masstone
Tint '
Fadeometer Masstone Tint
65A 65B 64b
PNA
tt
II
Aniline
Ni
ft Cu
5-Hydroxyben-- Ni
640
ft
zothiodiazol Cu
12A m-Nitro-
3-Methyl-8- Ni
aniline
Hydroxyquin-
oline
12B Cu
71 Aniline
4-Hydroxyquinoline
Cu
52A p-Chloranilinef1, 3 -DihydroXy-jNi
Jpyrido
/
B tf ] (4,3b)quino- iCu
V^.inel0(5)one
10A Benzidine
10B 13A
It ii
8-Hydroxyquinoline
ft
5-Methyl-8Hydroxy-
Ni
Cu Ni
1?B
it
quinoline
II
Cu
45D 2,7-Diamino- 2,4-Dihydroxy Cu
fluorene
quinoline
23B Ifetraamino CPC beta-Naphthol Ni
D ft
n Cu
22B
If
Schaeffer
Ni
C 1! H Cu
1Q2B 1020
t)
1!
1,4-Oxy Acid Ni ii Cu
102B 1Q3C
tt
11
J-Acid
it
Ni Cu
20B tf PMP
Ni
20P
It
it
Cu
21B If 8-Hydroxy- Ni
quinoline
2 ID
tt
ii Cu
Dull Bed Orange * Red Brown Dull " Olive " Khaki
Poor
ii h
Poor ;
it
it
Black ft Fair Fair Dark Brwn. Red Brwn. Good Poor
tt It Tan
it V. "
tt Brown
Good Poor
Light " V.Weak
tf Fair
Dark " Khaki
, ft V.Poor
Black
It ft
Gray n
Dull Blue
II
tt
Poor
ii
it
it
It Red Brwn. Pair V.Poor
ft Viol.
ft ft
It Gray Strong Good Pair
It
It tt ti
If
It
ft
It * Fair
ti
tt ft n tt
ft ti Good it
VIIt tt
tt
It it f! it
It
Dark Grn. . 'it tt
Black
ft
it
Dull n
Gray
tt
Pair it
Green Good ii n *t Poor ti Pair s
Pair Poor
None of the above pigments is of interest. -10-
DUP050059109
D. Metallized - With Metallizing Group on the Diazo Component
Page
Diazo
Met Coupler al Masstone
Tint
FedecWester Masst,one Tint
140A Anthranllic Asia p-OBorfhenol
B ir
It
C ti
- II
i 4ia
tt
Resorcin
B tt !
It
C ft
II
14 2A D
If It
Naphth. MX It
l44A D
It ft
II B3 II
145B D
It ft
If If
RL
680 It
II oA
D :l4jA
X)
It It ft
ft SW It BO fl
14A 2-Amino-4-Cl-
ff AS
Co Ni Cu Co Ni Cu Ni Cu Ni Cu Ni Cu Cu Cu
ni
Cu Co
Benzoic Acid '
,.B C
II II
ft If
Ni Cu
l6A 2-Amino-5-Cl-
ti Co
B C 17A B
'G 15A
Benzoic Acid. it it ti it ti
2-Amino-6-Cl-
tt Ni ff Cu 1! Co if n i tt Cu ft Co
Benzoic Acid
B C
H ii
51A 2-Amino-5-Nitro-
If If ,H
Ni Cu Ni
Benzoic Acid
BH
11 Cu
1?4a Anthranllic
AA-p-Chlor- Co
Acid B D 135A B D 6i a B C
11 It If
ti
ft If It II
Aniline It II
Ni Cu
AAoToluidlne Co II Ni ft Cu
PMP Co n Ni tt Cu
Black
Dk. Brown Black
ft
Dk. Brown Black Dk.Maroon Black Dk.Maroon
it ii it ii
Maroon DIkf .Matrt oon
II It
Black
Gray
Good
Lt.Brown Maroon
Ptat ir
Gray Gray
It tt
Wk. Brwn. II
Wk. Mar. Poor
Maroon Pair
V. Weak Maroon Dull Vi. Marbon
Good
ii
ti n
Brown Bordeaux Dull Vi. Brown '
Pair it it n
Gray
Good
ii
Dk,Brown Black
Wk.Maroon Pair it n Fair
Gray
Good
Dk.Brown fl tt 11 ft
" Maroon M it
Black
Dull Vi. Dull Mar. Gray Maroon
Brown
1! It tt ff
ft
Gray
Good
Dk.Brown Red Viol. Black
Wk.Maroon it Red Viol. n
Gray
Pair
Dk.Maroon Maroon
Brown
Tan
it Fair
lit. "
Dull Yel. Good
Dull Grn. " Grn. It
Dk.Brown Olive Bm. It
Lt. "
V.Weak
t!
Dull Grn. Dull Grn. If
Olive Brn, Olive Brn, ft
Dull Yel. Dull Yel. tt
Olive
Olive
tt
Poor Fair Poor Fair Good Poor Poor Poor .n
It Good Poor Poor
ii
Gtot od tt
Fair Poor
ii
Fair Poor
it Good Poor Poor
Good Poor Fair
Poor n
Good Fair Ptot or
Fair Good
It tt
-11-
DUP050059110
D. /Metallized - With Metallizing Group on the Diaz6 Component (Cont.)
Rage Diazo
Coupler
Met' al Masstone
Tint
Fadeometer Masstone Tint
147A AnthrariLlic Add Barbituric Add Co
B ft
ft Ni
C tl
It cm
148a 2-Amino-4-
p-Chlorphenol Co
Nitrophenol
B C 149A B 0
If ff tf tf
ii
ff Ni If Cu
heta-Haphthol Co it Ni tt Cu
156A 2-Amino-5-*
PMP
Co
Naphthoic Acid
Bn
tr
Ni
0 157A
1!
tr
m-Nitro-PMP
Cu Co
B if C if
ii Ni ti Cu
56A Dlanthranyl- Naphth. AS Co
methane B ii C it
Ni ii Cu
8a ii B ti
p-Nitro-PMP
ii
Ni Cu
9A it
p-Methyl-
Ni
Sulfonyl-PMP
B ti
ft Cu
11A
t
8-Hydroxy- Ni
Quinoline
D tr
ft Cu
Brown
Lt. Brwn. Poor
Olive Brwn.V.Weak Good
Dull Grn. Wk.Olive ft
Black
V.Weak
It
ff ft ft tl ft
Black:
Brown
It
Blue Gray tl
Dull Blue tl
Red Brwn. tt
Dull Viol ,, ft
Olive Brn it
Brown ft
Dk. " Lt .Brwn. Dk.Brwn. Black
Yel.Brwn. Orange " Brown Or.Brwn. Wk.Brwn.
it it
it tt tt
Gray
Fair
n n
Brown Black Brown
Dull Viol.k ti
ii ii
it
Yel. Brwn. V. Weak V. Weak
1! Black
V. " Gray
Fair
ft ft t!
Poor Good Poor V."
it V." Poor
ii
it Poor
Fair Poor
ii
Good V.Poor Poor
ii
n
Fair
Poor
The following pigments in the above table seem to be of possible interest on account of good light fastness:
Anthranilic acid * Naphthanil RL, Nickel Complex 2-Amino-4-Chlorbenzoic Acid - Naphthanil AS, Cobalt Complex 2-Amino-5 -Chlorbenzoic Acid - Naphthanil ASE, Nickel " 2-Amino-6-Chlorbenzoic Acid -> Naphthanil AS, Nickel " Anthranilic Acid -> Phenylmethylpyraz done, Cobalt Complex
" " , Nickel " " " , Copper n 2-Amino-3-Naphthoic Acid m-Nitrophenylmethylpyrazdone, nickel complex.
DUP050059111
Some of these pigments were tested for heater dyeing of \
paper, as follows:
'
2-Amlno-6-chlorbenzoic acid - Raphthanil AS, nickel coAf plex (3795-15B), was compared with J-43-F-430D, (aniline 2-hydroxy-3-naphthoic acid, nickel complex) and found to he slightly yellower, equal strength and much inferior to light fastness,
2-Amino-5-Chlorbenzoic acid -> Naphthanil AS, copper com plex (3795-16D), was found to he fast-to-acid and alkali and only very slightly affected hy eradicator. It is slightly superior to Lithosol Red CSP in fastness-to-light. It Is redder than the direct violets and faster-to-llght.
Anthranilic acid -* phenyl-methyl-pyrazolone, copper complex (5795-61D) , compared with J.43-F-391 (PNA -> DHQ, nickel complex) is much duller, hut about equal in light fastness. It is of interest for camouflage papers and a larger sample was prepared for further tests (2795-1^6). The nickel complex (3795-61B) was inferior in light fastness to the copper complex.
Submitted for Typing - September 29, 19^2 Typed - December 1, 19^2 Jeanette Lillian Blocksom
-13-
DUP050059112