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96-91-3

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96-91-3 Usage

Uses

manufacture of azo dyes; rarely as indicator (yellow with acids, red with alkalies); reagent for albumin.

General Description

Dark red needles or prisms. Red crystals. Water insoluble. Explosive in the dry state but desensitized by wetting. Easily ignited and once ignited burn readily.

Air & Water Reactions

Highly flammable. Insoluble in water.

Reactivity Profile

Picramic acid should not be subjected to strong shock or heat, and is a dangerous fire risk. Picramic acid reacts with strong oxidizing agents. . Explodes if dried and exposed to heat, flame, friction or shock. Wetting greatly reduces this tendency. Treat as an explosive. Mixing with reducing agents, including hydrides, sulfides, nitrides, and alkali metals may lead to a vigorous reaction that culminates in a detonation. May explode in the presence of a base such as sodium hydroxide or potassium hydroxide, even in the presence of water or organic solvents. May be incompatible with isocyanates, halogenated organics, peroxides, phenols (acidic), epoxides, anhydrides, and acid halides. An amino acid (reacts as an acid with bases and as a base with acids).

Fire Hazard

Picramic acid ignites rapidly and burns relatively fast.

Flammability and Explosibility

Nonflammable

Check Digit Verification of cas no

The CAS Registry Mumber 96-91-3 includes 5 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 2 digits, 9 and 6 respectively; the second part has 2 digits, 9 and 1 respectively.
Calculate Digit Verification of CAS Registry Number 96-91:
(4*9)+(3*6)+(2*9)+(1*1)=73
73 % 10 = 3
So 96-91-3 is a valid CAS Registry Number.
InChI:InChI=1/C6H5N3O5/c7-4-1-3(8(11)12)2-5(6(4)10)9(13)14/h1-2,10H,7H2

96-91-3SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 17, 2017

Revision Date: Aug 17, 2017

1.Identification

1.1 GHS Product identifier

Product name 2-amino-4,6-dinitrophenol

1.2 Other means of identification

Product number -
Other names 4,6-dinitro-2-aminophenol

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:96-91-3 SDS

96-91-3Synthetic route

2,4,6-Trinitrophenol
88-89-1

2,4,6-Trinitrophenol

picramic acid
96-91-3

picramic acid

Conditions
ConditionsYield
With sulfur; sodium hydroxide In methanol; water at 80℃; for 8h; Green chemistry;87%
With ethanol; hydrogen sulfide; ammonia
With sodium hydrogensulfide in der Waerme;
ammonium 2-amino-4,6-dinitrophenolate

ammonium 2-amino-4,6-dinitrophenolate

picramic acid
96-91-3

picramic acid

Conditions
ConditionsYield
With acetic acid In water at 60℃; Inert atmosphere;79%
2-amino-6-nitrophenol
603-87-2

2-amino-6-nitrophenol

picramic acid
96-91-3

picramic acid

Conditions
ConditionsYield
With sulfuric acid; nitric acid at 0 - 5℃;40%
dopamine picrate
75802-61-8

dopamine picrate

picramic acid
96-91-3

picramic acid

Conditions
ConditionsYield
at 250℃; for 5h;8%
benzoic acid-(2-hydroxy-3,5-dinitro-anilide)
13316-89-7

benzoic acid-(2-hydroxy-3,5-dinitro-anilide)

picramic acid
96-91-3

picramic acid

Conditions
ConditionsYield
With hydrogenchloride at 140℃;
With hydrogenchloride at 130℃;
acetic acid-(2-hydroxy-3,5-dinitro-anilide)
5422-72-0

acetic acid-(2-hydroxy-3,5-dinitro-anilide)

furan-2,3,5(4H)-trione pyridine (1:1)

furan-2,3,5(4H)-trione pyridine (1:1)

picramic acid
96-91-3

picramic acid

sodium picrate
3324-58-1

sodium picrate

picramic acid
96-91-3

picramic acid

Conditions
ConditionsYield
With methanol; sodium hydrogensulfide
With water; sodium disulfide
ethanol
64-17-5

ethanol

hydrogen sulfide
7783-06-4

hydrogen sulfide

ammonia
7664-41-7

ammonia

2,4,6-Trinitrophenol
88-89-1

2,4,6-Trinitrophenol

picramic acid
96-91-3

picramic acid

ammonium chloride

ammonium chloride

water
7732-18-5

water

2,4,6-Trinitrophenol
88-89-1

2,4,6-Trinitrophenol

picramic acid
96-91-3

picramic acid

Conditions
ConditionsYield
und im Wasserstoff-Strom erhitztes Aluminium (in Kaeltemischung);
2,4,6-Trinitrophenol
88-89-1

2,4,6-Trinitrophenol

iron(II) sulfate

iron(II) sulfate

alkali

alkali

picramic acid
96-91-3

picramic acid

water
7732-18-5

water

2,4,6-Trinitrophenol
88-89-1

2,4,6-Trinitrophenol

D-(+)-lactose
63-42-3

D-(+)-lactose

alkali

alkali

picramic acid
96-91-3

picramic acid

ammonia
7664-41-7

ammonia

2,4,6-Trinitrophenol
88-89-1

2,4,6-Trinitrophenol

CuCl

CuCl

picramic acid
96-91-3

picramic acid

2,4,6-Trinitrophenol
88-89-1

2,4,6-Trinitrophenol

hydrosulfite sodium

hydrosulfite sodium

picramic acid
96-91-3

picramic acid

water
7732-18-5

water

2,4,6-Trinitrophenol
88-89-1

2,4,6-Trinitrophenol

iron-turnings

iron-turnings

picramic acid
96-91-3

picramic acid

Conditions
ConditionsYield
at 100℃;
water
7732-18-5

water

iron(III) chloride
7705-08-0

iron(III) chloride

2,4,6-Trinitrophenol
88-89-1

2,4,6-Trinitrophenol

iron-turnings

iron-turnings

picramic acid
96-91-3

picramic acid

Conditions
ConditionsYield
at 100℃;
water
7732-18-5

water

2,4,6-Trinitrophenol
88-89-1

2,4,6-Trinitrophenol

iron-turnings

iron-turnings

NaCl

NaCl

picramic acid
96-91-3

picramic acid

Conditions
ConditionsYield
at 100℃;
methanol
67-56-1

methanol

water
7732-18-5

water

2,4,6-Trinitrophenol
88-89-1

2,4,6-Trinitrophenol

Na2S

Na2S

NaHCO3

NaHCO3

picramic acid
96-91-3

picramic acid

Conditions
ConditionsYield
at 60℃;
ethanol
64-17-5

ethanol

water
7732-18-5

water

2,4,6-Trinitrophenol
88-89-1

2,4,6-Trinitrophenol

Na2S

Na2S

NaHCO3

NaHCO3

picramic acid
96-91-3

picramic acid

Conditions
ConditionsYield
at 80℃;
ammonia
7664-41-7

ammonia

2,4,6-Trinitrophenol
88-89-1

2,4,6-Trinitrophenol

SnCl2

SnCl2

picramic acid
96-91-3

picramic acid

2,4,6-Trinitrophenol
88-89-1

2,4,6-Trinitrophenol

sodium ferropyrophosphate

sodium ferropyrophosphate

picramic acid
96-91-3

picramic acid

water
7732-18-5

water

2,4,6-Trinitrophenol
88-89-1

2,4,6-Trinitrophenol

sodium hydrogensulfide

sodium hydrogensulfide

picramic acid
96-91-3

picramic acid

ethanol
64-17-5

ethanol

sulfuric acid
7664-93-9

sulfuric acid

2,4,6-Trinitrophenol
88-89-1

2,4,6-Trinitrophenol

vanadyl sulfate

vanadyl sulfate

picramic acid
96-91-3

picramic acid

Conditions
ConditionsYield
Electrolysis;
ammonia
7664-41-7

ammonia

2,4,6-Trinitrophenol
88-89-1

2,4,6-Trinitrophenol

zinc-dust

zinc-dust

picramic acid
96-91-3

picramic acid

ethanol
64-17-5

ethanol

ammonium chloride

ammonium chloride

2,4,6-Trinitrophenol
88-89-1

2,4,6-Trinitrophenol

cerium-powder

cerium-powder

A

2,4,6-triaminophenol
609-24-5

2,4,6-triaminophenol

B

picramic acid
96-91-3

picramic acid

hydrogenchloride
7647-01-0

hydrogenchloride

benzoic acid-(2-hydroxy-3,5-dinitro-anilide)
13316-89-7

benzoic acid-(2-hydroxy-3,5-dinitro-anilide)

A

benzoic acid
65-85-0

benzoic acid

B

picramic acid
96-91-3

picramic acid

Conditions
ConditionsYield
at 130℃;
3.5-dinitro-2-oxy-phenyl isocyanate

3.5-dinitro-2-oxy-phenyl isocyanate

water
7732-18-5

water

picramic acid
96-91-3

picramic acid

Conditions
ConditionsYield
beim Kochen;
acetic acid-(2-amino-4,6-dinitro-phenyl ester)

acetic acid-(2-amino-4,6-dinitro-phenyl ester)

aqueous NaOH-solution

aqueous NaOH-solution

picramic acid
96-91-3

picramic acid

C24H26N4O5

C24H26N4O5

picramic acid
96-91-3

picramic acid

C23H15N5O7

C23H15N5O7

Conditions
ConditionsYield
Stage #1: picramic acid With hydrogenchloride; acetic acid; sodium nitrite In methanol; water at 0℃; for 2h;
Stage #2: C24H26N4O5 With sodium hydroxide In methanol; 2-ethoxy-ethanol; water at 0℃; for 2h; pH=11;
98.3%
3-Hydroxy-naphthalene-2-carboxylic acid butylamide
3665-54-1

3-Hydroxy-naphthalene-2-carboxylic acid butylamide

picramic acid
96-91-3

picramic acid

C21H19N5O7

C21H19N5O7

Conditions
ConditionsYield
Stage #1: picramic acid With hydrogenchloride; acetic acid; sodium nitrite In methanol; water at 0℃; for 2h;
Stage #2: 3-Hydroxy-naphthalene-2-carboxylic acid butylamide With sodium hydroxide In methanol; 2-ethoxy-ethanol; water at 0℃; for 2h; pH=11;
95.1%
2,2-dimethyl-3-(N-methyl-N-phenylamino)-2H-azirine
75755-40-7

2,2-dimethyl-3-(N-methyl-N-phenylamino)-2H-azirine

picramic acid
96-91-3

picramic acid

2-(1-Amino-1-methylethyl)-5,7-dinitro-1,3-benzoxazole
130138-19-1

2-(1-Amino-1-methylethyl)-5,7-dinitro-1,3-benzoxazole

Conditions
ConditionsYield
In acetonitrile for 24h; Ambient temperature;83%
N-methyl-N-phenyl-1-azaspiro[2.4]hept-1-en-2-amine
116139-91-4

N-methyl-N-phenyl-1-azaspiro[2.4]hept-1-en-2-amine

picramic acid
96-91-3

picramic acid

2-(1-Aminocyclopentyl)-5,7-dinitro-1,3-benzoxazole
130138-32-8

2-(1-Aminocyclopentyl)-5,7-dinitro-1,3-benzoxazole

Conditions
ConditionsYield
In acetonitrile for 24h; 0 deg C to room temp.;81%
3,3-bis(3,4,5-trimethoxyphenyl)acrylaldehyde

3,3-bis(3,4,5-trimethoxyphenyl)acrylaldehyde

picramic acid
96-91-3

picramic acid

2-(2,2-bis(3,4,5-trimethoxyphenyl)vinyl)-5,7-dinitrobenzoxazole

2-(2,2-bis(3,4,5-trimethoxyphenyl)vinyl)-5,7-dinitrobenzoxazole

Conditions
ConditionsYield
Stage #1: 3,3-bis(3,4,5-trimethoxyphenyl)acrylaldehyde; picramic acid In ethanol for 3h; Reflux;
Stage #2: With lead(IV) tetraacetate; acetic acid at 20℃; for 1h;
78%
4-(9H-pyrido[3,4-b]indol-1-yl)thiazole-2-carbaldehyde

4-(9H-pyrido[3,4-b]indol-1-yl)thiazole-2-carbaldehyde

picramic acid
96-91-3

picramic acid

1-(2-(5,7-dinitrobenzo[d]oxazol-2-yl)thiazol-4-yl)−9H-pyrido[3,4-b]indole

1-(2-(5,7-dinitrobenzo[d]oxazol-2-yl)thiazol-4-yl)−9H-pyrido[3,4-b]indole

Conditions
ConditionsYield
With [bis(acetoxy)iodo]benzene In 1,4-dioxane at 20℃; for 0.25h;77%
chloroacetyl chloride
79-04-9

chloroacetyl chloride

picramic acid
96-91-3

picramic acid

6,8-dinitro-(2H)-1,4-benzoxazin-3(4H)-one
96753-74-1

6,8-dinitro-(2H)-1,4-benzoxazin-3(4H)-one

Conditions
ConditionsYield
With sodium hydrogencarbonate In water for 4h; Heating;75%
3-(Dimethylamino)spiro<2H-azirin-2,1'-cyclohexan>
56912-87-9

3-(Dimethylamino)spiro<2H-azirin-2,1'-cyclohexan>

picramic acid
96-91-3

picramic acid

A

2-(1-Aminocyclohexyl)-5,7-dinitro-1,3-benzoxazole
130138-33-9

2-(1-Aminocyclohexyl)-5,7-dinitro-1,3-benzoxazole

B

1',2',3',4'-Tetrahydro-5',7'-dinitrospiro-2'-one
130138-29-3

1',2',3',4'-Tetrahydro-5',7'-dinitrospiro-2'-one

C

2'-(Dimethylamino)-3',4'-dihydro-5',7'-dinitrospiro
130138-31-7

2'-(Dimethylamino)-3',4'-dihydro-5',7'-dinitrospiro

D

1-Amino-N-<2-(dimethylamino)-3,5-dinitrophenyl>cyclohexanecarboxamide
130138-35-1

1-Amino-N-<2-(dimethylamino)-3,5-dinitrophenyl>cyclohexanecarboxamide

Conditions
ConditionsYield
In acetonitrile for 24h; 0 deg C to room temp.;A 54%
B 3%
C 8%
D 27%
picramic acid
96-91-3

picramic acid

A

3'-(Dimethylamino)spiroazirin>
108805-12-5

3'-(Dimethylamino)spiroazirin>

B

2'-(Dimethylamino)-3',4'-dihydro-5',7'-dinitrospiro
130138-30-6

2'-(Dimethylamino)-3',4'-dihydro-5',7'-dinitrospiro

C

1-Amino-N-<2-(dimethylamino)-3,5-dinitrophenyl>cyclopentanecarboxamide
130138-34-0

1-Amino-N-<2-(dimethylamino)-3,5-dinitrophenyl>cyclopentanecarboxamide

D

1',2',3',4'-Tetrahydro-5',7'-dinitrospiro-2'-one
130138-28-2

1',2',3',4'-Tetrahydro-5',7'-dinitrospiro-2'-one

Conditions
ConditionsYield
In acetonitrile for 24h; 0 deg C to room temp.;A 40%
B 32%
C 16%
D 4%
3'-(Dimethylamino)spiroazirin>
108805-12-5

3'-(Dimethylamino)spiroazirin>

picramic acid
96-91-3

picramic acid

A

2'-(Dimethylamino)-3',4'-dihydro-5',7'-dinitrospiro
130138-30-6

2'-(Dimethylamino)-3',4'-dihydro-5',7'-dinitrospiro

B

1-Amino-N-<2-(dimethylamino)-3,5-dinitrophenyl>cyclopentanecarboxamide
130138-34-0

1-Amino-N-<2-(dimethylamino)-3,5-dinitrophenyl>cyclopentanecarboxamide

C

2-(1-Aminocyclopentyl)-5,7-dinitro-1,3-benzoxazole
130138-32-8

2-(1-Aminocyclopentyl)-5,7-dinitro-1,3-benzoxazole

D

1',2',3',4'-Tetrahydro-5',7'-dinitrospiro-2'-one
130138-28-2

1',2',3',4'-Tetrahydro-5',7'-dinitrospiro-2'-one

Conditions
ConditionsYield
In acetonitrile for 24h; 0 deg C to room temp.;A 32%
B 16%
C 40%
D 4%
2-phenylamino-5-hydroxynaphthalene-7-sulphonic acid
119-40-4

2-phenylamino-5-hydroxynaphthalene-7-sulphonic acid

picramic acid
96-91-3

picramic acid

C22H15N5O9S

C22H15N5O9S

Conditions
ConditionsYield
Stage #1: picramic acid With hydrogenchloride; sodium nitrite In water at 0 - 5℃; for 1h;
Stage #2: With aminosulfonic acid In water for 0.05h;
Stage #3: 2-phenylamino-5-hydroxynaphthalene-7-sulphonic acid In water at 10℃; for 2h;
3.4%
pyridine
110-86-1

pyridine

p-toluenesulfonyl chloride
98-59-9

p-toluenesulfonyl chloride

picramic acid
96-91-3

picramic acid

1-[2,4-dinitro-6-(toluene-4-sulfonylamino)-phenyl]-pyridinium betaine

1-[2,4-dinitro-6-(toluene-4-sulfonylamino)-phenyl]-pyridinium betaine

phthalic anhydride
85-44-9

phthalic anhydride

picramic acid
96-91-3

picramic acid

N-(2-hydroxy-3,5-dinitro-phenyl)-phthalimide

N-(2-hydroxy-3,5-dinitro-phenyl)-phthalimide

Conditions
ConditionsYield
With acetic acid
O4,O6-((R)-ethylidene)-O2,O3-((1Ξ,3Ξ)-1,3-dimethyl-2-oxa-propanediyl)-D-glucose

O4,O6-((R)-ethylidene)-O2,O3-((1Ξ,3Ξ)-1,3-dimethyl-2-oxa-propanediyl)-D-glucose

picramic acid
96-91-3

picramic acid

O4,O6-((R)-ethylidene)-O2,O3-((1Ξ,3Ξ)-1,3-dimethyl-2-oxa-propanediyl)-D-glucose-(2-hydroxy-3,5-dinitro-phenylimine)

O4,O6-((R)-ethylidene)-O2,O3-((1Ξ,3Ξ)-1,3-dimethyl-2-oxa-propanediyl)-D-glucose-(2-hydroxy-3,5-dinitro-phenylimine)

Conditions
ConditionsYield
With methanol
chloroformic acid ethyl ester
541-41-3

chloroformic acid ethyl ester

picramic acid
96-91-3

picramic acid

(2-hydroxy-3,5-dinitro-phenyl)-carbamic acid ethyl ester

(2-hydroxy-3,5-dinitro-phenyl)-carbamic acid ethyl ester

acetic anhydride
108-24-7

acetic anhydride

picramic acid
96-91-3

picramic acid

2-methyl-5,7-dinitro-benzooxazole
98434-14-1

2-methyl-5,7-dinitro-benzooxazole

Conditions
ConditionsYield
With sulfuric acid
acetic anhydride
108-24-7

acetic anhydride

picramic acid
96-91-3

picramic acid

A

acetic acid-(2-amino-4,6-dinitro-phenyl ester)

acetic acid-(2-amino-4,6-dinitro-phenyl ester)

B

acetic acid-(2-hydroxy-3,5-dinitro-anilide)
5422-72-0

acetic acid-(2-hydroxy-3,5-dinitro-anilide)

Conditions
ConditionsYield
With sulfuric acid
acetic anhydride
108-24-7

acetic anhydride

picramic acid
96-91-3

picramic acid

acetic acid-(2-hydroxy-3,5-dinitro-anilide)
5422-72-0

acetic acid-(2-hydroxy-3,5-dinitro-anilide)

acetic anhydride
108-24-7

acetic anhydride

picramic acid
96-91-3

picramic acid

2-acetoxy-1-acetylamino-3,5-dinitro-benzene
99057-38-2

2-acetoxy-1-acetylamino-3,5-dinitro-benzene

Conditions
ConditionsYield
With pyridine
4-nitrobenzaldehdye
555-16-8

4-nitrobenzaldehdye

picramic acid
96-91-3

picramic acid

2,4-dinitro-6-(4-nitro-benzylidenamino)-phenol

2,4-dinitro-6-(4-nitro-benzylidenamino)-phenol

1-methoxy-2,4,6-trinitrobenzene
606-35-9

1-methoxy-2,4,6-trinitrobenzene

picramic acid
96-91-3

picramic acid

1,3,6,8-tetranitro-phenoxazine

1,3,6,8-tetranitro-phenoxazine

Conditions
ConditionsYield
With ethanol; sodium acetate at 130℃; im Rohr;
benzyl chloride
100-44-7

benzyl chloride

picramic acid
96-91-3

picramic acid

2-benzylamino-4,6-dinitro-phenol

2-benzylamino-4,6-dinitro-phenol

Conditions
ConditionsYield
With water
salicylaldehyde
90-02-8

salicylaldehyde

picramic acid
96-91-3

picramic acid

salicylaldehyde-(3.5-dinitro-2-hydroxy-phenylimine)

salicylaldehyde-(3.5-dinitro-2-hydroxy-phenylimine)

Conditions
ConditionsYield
With potassium hydroxide

96-91-3Relevant articles and documents

A Common, Facile and Eco-Friendly Method for the Reduction of Nitroarenes, Selective Reduction of Poly-Nitroarenes and Deoxygenation of N-Oxide Containing Heteroarenes Using Elemental Sulfur

Cerecetto, Hugo,Romero, Angel H.

supporting information, (2020/03/23)

A transition metal-free, environment-friendly and practical protocol was developed either for the reduction of nitroarenes or for the deoxygenation of N-oxide containing heteroarenes. The reaction proceeded with the use of a non-toxic and cheap feedstock as elemental sulfur in aqueous methanol under relatively mild conditions. Green chemistry credentials were widely favorable compared to traditional and industrial protocols with good E-factors and a low production of waste. The strategy allowed the efficient reduction of a large variety of substituted-nitroarenes including various o-nitroanilines as well as selective reduction of various poly-nitroarenes in excellent yields with a broad substrate scope. The protocol was successfully extended to the deoxygenation of some N-oxide containing heteroarenes, like benzofuroxans, phenazine N,N'-dioxides, pyridine N-oxides, 2H-indazole N1-oxides, quinoxaline N1,N4-dioxides and benzo[d]imidazole N1,N3-dioxides. A gram-scale example for the synthesis of luminol, in green conditions, was reported. A solid mechanism of reaction was proposed from experimental evidences.

Exothermic thermal reaction of dopamine with 3,5-dinitrobenzoic acid

Ito, Yoshikatsu,Arimoto, Satoru

, p. 849 - 857 (2007/10/03)

Pyrolysis of the crystalline 1:1 molecular complex DA·dnba, which was prepared from cocrystallization of dopamine (DA) and 3,5-dinitrobenzoic acid (dnba), was studied. This cocrystal decomposed violently at the melting-point, leading to the formation of a black solid along with a tiny amount of 3-amino-5-nitrobenzoic acid (1). The pyrolysis reaction was followed by differential scanning calorimetry (DSC) and one large exothermic peak was observed at the decomposition temperature. In view of the DSC patterns for cocrystal DA·dnba and other compounds, it seems that both a catechol moiety and an amino group of DA in addition to a strong electron acceptor such as dnba are required for the appearance of the exothermic peak. On the basis of (a) elemental analysis of the black solid and (b) other pyrolysis experiments for cocrystals PA·dnba (PA: β-phenylethylamine), BA·dnba (BA: benzylamine), DMDA·dnba (DMDA: O,O′-dimethyldopamine) and DHBA·dnba (DHBA: 3,4-dihydroxybenzylamine), it is assumed that the black solid was formed mainly through elimination of more than one molecule of water from one molecule of DA·dnba. Copyright

Unsymmetrical 1:2-chromium complexes containing an azo compound and an azomethine compound

-

, (2008/06/13)

Compounds of the formula: STR1 WHICH ARE EMINENTLY SUITABLE FOR DYEING NATURAL AND SYNTHETIC POLYAMIDES AND FOR COLORING SURFACE COATINGS. Dyeings on textile material are distinguished by very good lightfastness and very good fastness to wet treatments, for example fastness to water, perspiration, sea water and washing.

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