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Home > Encyclopedia > Pigment Yellow 12

Pigment Yellow 12

Pigment Yellow 12 structure

Pigment Yellow 12 

structure
  • CAS No:

    6358-85-6

  • Formula:

    C32H26Cl2N6O4

  • Chemical Name:

    Pigment Yellow 12

  • Synonyms:

    Butanamide,2,2′-[(3,3′-dichloro[1,1′-biphenyl]-4,4′-diyl)bis(2,1-diazenediyl)]bis[3-oxo-N-phenyl-;C.I. Pigment Yellow 12;Butanamide,2,2′-[(3,3′-dichloro[1,1′-biphenyl]-4,4′-diyl)bis(azo)]bis[3-oxo-N-phenyl-;Acetoacetanilide,2,2′′-(3,3′-dichloro-4,4′-biphenylylenebisazo)bis-;2,2′-[(3,3′-Dichloro[1,1′-biphenyl]-4,4′-diyl)bis(2,1-diazenediyl)]bis[3-oxo-N-phenylbutanamide];C.I. 21090;Amazon Yellow X 2485;Benzidine Lacquer Yellow G;Benzidine Yellow E;Benzidine Yellow 45-2650;Benzidine Yellow 45-2685;Benzidine Yellow 45-2680;Benzidine Yellow GF;Benzidine Yellow GT;Benzidine Yellow GTR;Benzidine Yellow HG;Benzidine Yellow HG-Plv;Benzidine Yellow G;Benzidine Yellow Toner;Benzidine Yellow Toner YA 8081;Benzidine Yellow Toner YT 378;Bis(acetyl-N-phenylcarbamylmethyl)-4,4′-disazo-3,3′-dichlorobiphenyl;Brilliant Yellow Slurry;Carnelio Yellow GX;Dainichi Benzidine Yellow G;Dainichi Benzidine Yellow GRT;Dainichi Benzidine Yellow GT;Dainichi Benzidine Yellow GY;Dainichi Benzidine Yellow GYT;Daltolite Fast Yellow GT;Eljon Yellow BG;Hancock Yellow 10010;Helio Yellow GW;Helio Yellow GWN;Irgalite Yellow BO;Irgalite Yellow BST;Irgalite Yellow BTR;Isol Benzidine Yellow G;Isol Benzidine Yellow G Special;Kromon Yellow GXT Conc;Kromon Yellow MTB;Light Yellow JB;Light Yellow JBO;Light Yellow JBT;Lodestone Yellow YB 57;Monolite Yellow 2GRA;Monolite Yellow GRA;Monolite Yellow GT;Monolite Yellow GTA;82197-93-1;82249-35-2;97794-07-5;127546-11-6;142583-27-5;912849-92-4;1438404-83-1;2284459-75-0

  • Categories:

    Cosmetic Ingredient  >  Hair Dyeing

Description

Diarylanilide yellow is an odorless fine yellow powder. (NTP, 1992)|DryPowder; WetSolid


Diarylanilide yellow is an odorless fine yellow powder. (NTP, 1992)

Pigment Yellow 12 Basic Attributes

629.5

629.49

228-787-8

N52TUS5TRY

521237

DTXSID1021451

A yellow diazo pigment.

Characteristics

142

8.16640

Diarylanilide yellow is an odorless fine yellow powder. (NTP, 1992)

1.22 (NTP, 1992)

320 °C

805.4ºC at 760 mmHg

440.9ºC

1.65

H2O: <0.1 G/100 ML AT 22 ºC

5.64E-26mmHg at 25°C

CLAIMED TO BE LIGHT-FAST & ALKALI-RESISTANT /BENZIDINE DYES/

Azo dyes can be explosive when suspended in air at specific concentrations. Insoluble in water.

Amides and Imides

Explosive

DIARYLANILIDE YELLOW is incompatible with strong oxidizing agents. (NTP, 1992)

Safety Information

P273, P501

H412

SRP: At the time of review, criteria for land treatment or burial (sanitary landfill) disposal practices are subject to significant revision. Prior to implementing land disposal of waste residue (including waste sludge), consult with environmental regulatory agencies for guidance on acceptable disposal practices.

ITC/USEPA; Information Review #133A (Draft) Pigment Yellow 12 CI, 21090 (1/25/88).|Bioassay of Diarylanilide for Possible Carcinogenicity (1978) Technical Rpt Series No. 30 DHEW Pub No. (NIH) 78-830, U.S. Department of Health Education and Welfare, National Cancer Institute, Bethesda, MD 20014

Flash point data for this chemical are not available; however, it is probably combustible. (NTP, 1992)

Not Classified

Fires involving this material can be controlled with a dry chemical, carbon dioxide or Halon extinguisher. (NTP, 1992)

SMALL SPILLS AND LEAKAGE: If you spill this chemical, you should dampen the solid spill material with water, then transfer the dampened material to a suitable container. Use absorbent paper dampened with water to pick up any remaining material. Seal your contaminated clothing and the absorbent paper in a vapor-tight plastic bag for eventual disposal. Wash all contaminated surfaces with a soap and water solution. Do not reenter the contaminated area until the Safety Officer (or other responsible person) has verified that the area has been properly cleaned. STORAGE PRECAUTIONS: You should store this chemical at ambient temperatures, and keep it away from oxidizing materials. (NTP, 1992)

RECOMMENDED RESPIRATOR: Where the neat test chemical is weighed and diluted, wear a NIOSH-approved half face respirator equipped with an organic vapor/acid gas cartridge (specific for organic vapors, HCl, acid gas and SO2) with a dust/mist filter. (NTP, 1992)

Toxicity

A bioassay of technical grade diarylanilide yellow for possible carcinogenicity was conducted using Fischer 344 rats and B6C3F1 mice. Diarylanilide yellow was administered in the feed, at either of two concentrations, to groups of 50 male and 50 female animals of each species. The high and low dietary concentrations used in the chronic study for male and female rats and mice were 5.0 and 2.5%, respectively, of the chemical in the feed. After a 78 wk treatment period, observation of the rats continued for an additional 28 wk and observation of the mice continued for an additional 19 wk for high dose males and low and high dose females and 18 wk for low dose males. For each species, 50 animals of each sex were placed on test as controls, and fed only the basal diet. The dietary concn of diarylanilide yellow admin during the chronic bioassay had no significant effect on survival or body wt gain in either species. Except for yellow staining and some isolated neoplasms, the only adverse clinical sign or pathologic lesion observed in treated rats or mice was basophilic cytoplasm changes in hepatocytes of treated rats. In both species the survival in all groups was adequate for statistical analysis of late appearing tumors. No treatment related incr in the incidence of neoplasms or nonneoplastic lesions was evident in treated rats or mice. A few unusual findings was observed in both species, including single cases of metastatic chordoma and osteogenic sarcoma in rats, and single cases of squamous cell carcinoma of the ear, infiltrating duct carcinoma of the mammary gland, and subcutaneous mastocytoma in mice. The results of this study did not provide evidence for the carcinogenicity of diarylanilide yellow in Fischer 344 rats or B6C3F1 mice. Levels of Evidence of Carcinogenicity: Male Rats: Negative; Female Rats: Negative; Male Mice: Negative; Female Mice: Negative.

C.I. Pigment Yellow 12's production and use as a pigment for lacquers, printing inks, plastics, and rubber(1) may result in its release to the environment through various waste streams(SRC).

TERRESTRIAL FATE: Based on a recommended classification scheme(1), an estimated Koc value of 68(SRC), determined from an estimated log Kow(2) and a recommended regression-derived equation(3), indicates that C.I. Pigment Yellow 12 will have high mobility in soil(SRC). As C.I. Pigment Yellow 12 may act as an ionic compound in the environment, volatilization of this compound will not be important from moist soil surfaces(4,SRC). Based on limited data, C.I. Pigment Yellow 12 is expected to be resistant to aerobic biodegradation in soil(SRC); in the MITI test this compound is resistant to biodegradation; 0 biodegradation occurred after a period of two weeks(5).|AQUATIC FATE: Based on a recommended classification scheme(1), an estimated Koc value of 68(SRC), determined from an estimated log Kow(2) and a recommended regression-derived equation(1), indicates that C.I. Pigment Yellow 12 will not adsorb to suspended solids and sediment in water(SRC). As C.I. Pigment Yellow 12 may act as an ionic compound, volatilization from water surfaces is not expected(3,SRC). According to a classification scheme(4), experimental BCF values ranging from 0.38 to 5.4(5,SRC), suggests that bioconcentration in aquatic organisms is low(SRC). Based on limited data, C.I. Pigment Yellow 12 is expected to be resistant to aerobic biodegradation in water(SRC). Using the MITI test, this compound is resistant to biodegradation; 0 biodegradation occurred after a period of two weeks(5).|ATMOSPHERIC FATE: The ionic nature of C.I. pigment Yellow 12 in the environment makes this compound essentially non-volatile(1,SRC).

When carp were exposed to 0.1 mg/l C.I. Pigment Yellow 12, the experimental BCF ranged from 0.38 to 3.2 over a period of 6 weeks. When carp were exposed to 0.01 mg/l C.I. Pigment Yellow 12, the experimental BCF ranged from 2.4 to 5.4 over a 6 week period(1). According to a classification scheme(2), these BCF values suggest that bioconcentration in aquatic organisms is low.

The Koc of C.I. Pigment Yellow 12 is estimated as approximately 67(SRC), using an estimated log Kow(1) and a regression-derived equation(2,SRC). According to a recommended classification scheme(3), this estimated Koc value suggests that C.I. Pigment Yellow 12 has high mobility in soil(SRC). However, the ionic nature of the pigment may slow down or prevent leaching(SRC).

Since C.I. Pigment Yellow 12 is an ionic compound, volatilization from water and moist soil surfaces will not be important(1,SRC).

Processes in which dried dye is handled have the greatest potential for employee exposure during the manufacture or repackaging of benzidine-based dyes. ... During use of benzidine-based dyes, the greatest potential for exposure would be expected to be among dye-weighers who handle dry powders. /Benzidine-based dyes/|NIOSH (NOES Survey 1981-1983) has statistically estimated that 63,185 workers (4,180 of these are female) are potentially exposed to C.I. Pigment Yellow 12 in the US(1). Occupational exposure may be through inhalation and dermal contact with this compound at workplaces where C.I. Pigment Yellow 12 is produced or used(SRC). The general population will be exposed to C.I. Pigment Yellow 12 via dermal contact with products containing this compound(SRC).

Drug Information

PIGMENTS /INCLUDING PIGMENT YELLOW 12/ WERE NOT ABSORBED AFTER CHRONIC ORAL INGESTION & DID NOT UNDERGO METABOLIC SPLITTING TO 3,3-DICHLOROBENZIDINE OR 3,3-DIMETHYLBENZIDINE /IN MICE OR RATS/.|The average environmental exposure levels of four of the workers /in a dye manufacturing facility/ were 4.3, 5.2, 11.7, and 17.4 mg total particulate/cu m. The corresponding urinary concentrations of benzidine average 52, 11, 10, and 112 ppb, respectively /SRP: from the precursor during manufacturing/. /Benzidine-based dyes/|The oral and dermal absorption and distribution of water insoluble (WI) 3,3'-dichlorobenzidine (DCB) based pigments were evaluated in Fischer 344 rats. Chlorodiane blue (CDB) and pigment yellow 12 (PY-12) ... were synthesized from DCB and labeled with (14)C. Rats were given oral doses of ... 1.11 mg/kg labeled WI PY-12 for absorption studies or 0.99 mg/kg for a 24 hour balance study. ... In an 8 hour oral study of CDB, blood samples taken from 10 min to 8 hr showed radioactivity at background levels. Dermal application resulted in background levels, as well. After the oral dose, all of the administered dose was accounted for in feces. For PY-12, radioactivity in blood at background levels after oral or dermal application. The entire dose was accounted for in feces after the oral dose. ...

Various bacteria and yeast normally found in the small and large intestine can reduce the azo bond in /some/ benzidine-based dyes and release benzidine. /Benzidine-based dyes/|Humans as well as other mammals can change (metabolize) /some/ benzidine-based dyes back to benzidine. The major organ in which /some/ benzidine-based dyes are metabolized to benzidine is the liver, but other organs also can do this to a greater or lesser degree. /Benzidine-based dyes/

ACUTE/CHRONIC HAZARDS: When heated to decomposition this compound emits very toxic fumes of chlorine and nitrogen oxides. (NTP, 1992)

EYES: First check the victim for contact lenses and remove if present. Flush victim's eyes with water or normal saline solution for 20 to 30 minutes while simultaneously calling a hospital or poison control center. Do not put any ointments, oils, or medication in the victim's eyes without specific instructions from a physician. If symptoms (such as redness or irritation) develop, immediately transport the victim to a hospital. SKIN: IMMEDIATELY flood affected skin with water while removing and isolating all contaminated clothing. Gently wash all affected skin areas thoroughly with soap and water. If symptoms such as redness or irritation develop, IMMEDIATELY call a physician and be prepared to transport the victim to a hospital for treatment. INHALATION: IMMEDIATELY leave the contaminated area; take deep breaths of fresh air. If symptoms (such as wheezing, coughing, shortness of breath, or burning in the mouth, throat, or chest) develop, call a physician and be prepared to transport the victim to a hospital. Provide proper respiratory protection to rescuers entering an unknown atmosphere. Whenever possible, Self-Contained Breathing Apparatus (SCBA) should be used; if not available, use a level of protection greater than or equal to that advised under Protective Clothing. INGESTION: DO NOT INDUCE VOMITING. If the victim is conscious and not convulsing, give 1 or 2 glasses of water to dilute the chemical and IMMEDIATELY call a hospital or poison control center. Be prepared to transport the victim to a hospital if advised by a physician. If the victim is convulsing or unconscious, do not give anything by mouth, ensure that the victim's airway is open and lay the victim on his/her side with the head lower than the body. DO NOT INDUCE VOMITING. IMMEDIATELY transport the victim to a hospital. (NTP, 1992)

... An incr in color printed newspapers might be a new source of clinical allergy to azo dyes. Patch tests were performed in 32 patients with an established p-aminoazobenzene allergy using a series of important azo dyes used in offset printing ink (Pigment Yellow 12, Pigment Yellow 13, Pigment Red 53, Pigment Red 57), as well as with dye containing inks and specimens of color printed newspaper containing these azo dyes. In 25 out of the 32 patients (78%), positive patch tests were seen to textile azo dyes, in particular to Disperse Orange 3 (24 patients). In none of the 32 patients were reactions observed to the azo dyes used in printing ink, to the inks used or to the color printed paper specimens, indicating that these products were apparently not a cause of contact dermatitis in /this/ group of patients with azo dye sensitization.

benzidine yellow

Pigment Yellow 12 Use and Manufacturing

Methods of Manufacturing

3,3'-Dichlorobenzidene dihydrochloride + acetoactanilide (diazotisation/azo coupling).|Condensation of 3,3'-dichlorobenzidine di-diazotate with acetoacetanilide.

Uses

Paint additives and coating additives not described by other categories


Agricultural products (non-pesticidal)

Production

10,000,000 - 50,000,000 lb|(1972) 1.86X10+9 GRAMS|(1975) 1.77X10+9 GRAMS|(1984) 7.03X10+9 GRAMS|13,892X10+3 lb|1.066X10+7 kg (1993)

Paint and coating manufacturing|Butanamide, 2,2'-[(3,3'-dichloro[1,1'-biphenyl]-4,4'-diyl)bis(2,1-diazenediyl)]bis[3-oxo-N-phenyl-: ACTIVE

Cosmetics -> Hair dyeing

Computed Properties

Molecular Weight:629.5
XLogP3:8.1
Hydrogen Bond Donor Count:2
Hydrogen Bond Acceptor Count:8
Rotatable Bond Count:11
Exact Mass:628.1392587
Monoisotopic Mass:628.1392587
Topological Polar Surface Area:142
Heavy Atom Count:44
Complexity:979
Undefined Atom Stereocenter Count:2
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

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