N-페닐-N'-이소프로필-p-페닐렌디아민

Plastics & Rubber -> Rubber Additives

Nitrogen Compounds -> Amines, Polyaromatic

1.04 (NTP, 1992) - Denser than water; will sink

1.04 @ 25 °C

1.04 g/cm³

less than 1 mg/mL at 64 °F (NTP, 1992)

Soluble in benzene and gasoline; insoluble in water.

Insoluble water; soluble in aromatic solvents

Solubility in water: none

162 to 169 °F (NTP, 1992)

75 °C

72-76 °C

0.00343 mmHg at 194 °F (NTP, 1992)

0.0000711 [mmHg]

N-isopropyl-n'-phenyl-p-phenylenediamine appears as dark gray to black flakes or brown-black small chip-like solid with an aromatic odor. (NTP, 1992)

Large Crystals; Other Solid; Dry Powder

Dark grey to black solid; [Hawley] Brown, grey, or dark purple to black solid; [CHEMINFO]

DARK GREY-TO-BLACK FLAKES.

Warning

H302: Harmful if swallowed [Warning Acute toxicity, oral]

P261, P264, P270, P272, P273, P280, P301+P317, P302+P352, P321, P330, P333+P317, P362+P364, P391, and P501 (click each P-code to see the statement)

Warning

H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]

P261, P264, P270, P272, P273, P280, P301+P317, P302+P352, P321, P330, P333+P317, P362+P364, P391, and P501 (click each P-code to see the statement)

Chemical: 1,4-Benzenediamine, N-(1-methylethyl)-N'-phenyl-

1,4-Benzenediamine, N1-(1-methylethyl)-N4-phenyl- is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of 1,4-Benzenediamine, N1-(1-methylethyl)-N4-phenyl- are required to report information about their production and use of this chemical to the EPA under the Toxic Substances Control Act (TSCA). (40 eCFR Part 711)

REACH registered substance: N-isopropyl-N'-phenyl-p-phenylenediamine (EC: 202-969-7)

Isopropylphenyl p-phenylenediamine: Does not have an individual approval but may be used under an appropriate group standard

This chemical is combustible. (NTP, 1992)

Combustible. Gives off irritating or toxic fumes (or gases) in a fire. Finely dispersed particles form explosive mixtures in air.

N-lsopropyl-N'-phenyl Paraphenylenediamine (IPPD) CAS # 101-72-4;\\ N-Cyclohexyl-N'-phenyl-Paraphenylenediamine (CPPD);\\ N,N'-Diphenyl Paraphenylenediamine ((DPPD) CAS # 74-31-7;\\ These amines are added to rubber products (tires, tubes, pipes, gaskets, flanges, boots, shoes, etc.) during manufacturing to retard degradation by oxidants and ozone. [Marks, p. 68]

A skin and eye irritant; May cause skin sensitization; [ICSC] Emergency treatment: Paraphenylenediamine; Paraphenylenediamine can cause angioneurotic edema, the most common cause of death after an overdose; Other effects after ingestion are vomiting, acute tubular necrosis, liver injury, methemoglobinemia, and seizures; p-Phenylenediamine is a skin and respiratory tract sensitizer; [HSDB] A skin, eye, and respiratory tract irritant; May cause contact dermatitis; [CAMEO] Does not readily penetrate intact skin; Not an eye or skin irritant based on animal studies; May cause skin sensitization; No data available on inhalation toxicity, respiratory sensitization, or carcinogenicity; [OECD SIDS: N-Isopropyl-N'-phenyl-p-phenylenediamine (IPPD) - 2000] See p-Phenylenediamine.

N-ISOPROPYL-N'-PHENYL-P-PHENYLENEDIAMINE reacts with oxidizing agents (NTP, 1992). Neutralizes acids in exothermic reactions to form salts plus water. May be incompatible with isocyanates, halogenated organics, peroxides, phenols (acidic), epoxides, anhydrides, and acid halides. Flammable gaseous hydrogen may be generated in combination with strong reducing agents, such as hydrides.

Fires involving this material can be controlled with a dry chemical, carbon dioxide or Halon extinguisher. A water spray may also be used. (NTP, 1992)

Use water spray, powder.

Fresh air, rest.

Remove contaminated clothes. Rinse and then wash skin with water and soap. Refer for medical attention .

First rinse with plenty of water for several minutes (remove contact lenses if easily possible), then refer for medical attention.

Rinse mouth.

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. IMMEDIATELY transport the victim after flushing eyes to a hospital even if no symptoms (such as redness or irritation) develop.

SMALL SPILLS AND LEAKAGE: If a spill of this chemical occurs, FIRST REMOVE ALL SOURCES OF IGNITION, then you should dampen the solid spill material with acetone and transfer the dampened material to a suitable container. Use absorbent paper dampened with acetone to pick up any remaining material. Seal your contaminated clothing and the absorbent paper in a vapor-tight plastic bag for eventual disposal. Solvent wash all contaminated surfaces with acetone followed by washing 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.

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.

Personal protection: chemical protection suit. Do NOT let this chemical enter the environment. Sweep spilled substance into covered containers. If appropriate, moisten first to prevent dusting. Carefully collect remainder. Then store and dispose of according to local regulations.

TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 1.3X10+4(SRC), determined from a structure estimation method(2), indicates that 4-(iso-propylamino)diphenylamine is expected to be immobile in soil(SRC). Volatilization of 4-(iso-propylamino)diphenylamine from moist soil surfaces is not expected to be an important fate process(SRC) given an estimated Henry's Law constant of 1.4X10-9 atm-cu m/mole(SRC), using a fragment constant estimation method(3). The estimated pKa of 4-(iso-propylamino)diphenylamine is 5.1(5), indicating that this compound will exist only slightly in the cation form(SRC). Cations generally adsorb to organic carbon and clay more strongly than their neutral counterparts. 4-(Iso-propylamino)diphenylamine is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 3.5X10-5 mm Hg(SRC), determined from a fragment constant method(4).

AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 1.3X10+4(SRC), determined from an estimation method(2), indicates that the non-protonated form of 4-(iso-propylamino)diphenylamine is expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is not expected(3) based upon an estimated Henry's Law constant of 1.4X10-9 atm-cu m/mole(SRC), developed using a fragment constant estimation method(4). An estimated pKa of 5.1(8) indicates 4-(iso-propylamino)diphenylamine will exist only slightly in the cation form at pH values of 5 to 9(SRC). Cations generally adsorb to suspended solids and sediment more strongly thantheir neutral counterparts. According to a classification scheme(5), an estimated BCF of 67(SRC), from an estimated log Kow of 3.3(6), and a regression-derived equation(7), suggests the potential for bioconcentration in aquatic organisms is moderate.

ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), 4-(iso-propylamino)diphenylamine, which has an estimated vapor pressure of 3.5X10-5 mm Hg at 25 °C(SRC), determined from a fragment constant method(2), will exist in both the vapor and particulate phases in the ambient atmosphere. Vapor-phase 4-(iso-propylamino)diphenylamine is degraded in the atmosphere by reaction with photochemically-produced hydroxyl radicals(SRC); the half-life for this reaction in air is estimated to be 2 hours(SRC), calculated from its rate constant of 2.2X10-10 cu cm/molecule-sec at 25 °C(SRC) determined using a structure estimation method(3). Particulate-phase 4-(iso-propylamino)diphenylamine may be removed from the air by wet and dry deposition(SRC).

Skin Sensitizer - An agent that can induce an allergic reaction in the skin.

Occupational hepatotoxin - Secondary hepatotoxins: the potential for toxic effect in the occupational setting is based on cases of poisoning by human ingestion or animal experimentation.

Redness.

Redness. Pain.

Using a structure estimation method based on molecular connectivity indices(1), the Koc for 4-(iso-propylamino)diphenylamine can be estimated to be 1.3X10+4(SRC). According to a classification scheme(2), this estimated Koc value suggests that 4-(iso-propylamino)diphenylamine is expected to be immobile in soil(SRC). The estimated pKa of 4-(iso-propylamino)diphenylamine is 5.1(3), indicating that this compound will exist only slightly in the cation form and cations generally adsorb to organic carbon and clay more strongly than their neutral counterparts.

A study of the prevalence of HLA antigens in persons sensitized to N-isopropyl-N'-phenyl-p-phenylenediamine was conducted to determine if an association between N-isopropyl-N'-phenyl-p-phenylenediamine sensitivity and the gene product of theHLA complex exists. The cohort consisted of 32 Czech patients sensitized to N-isopropyl-N'-phenyl-p-phenylenediamine, as determined by patch tests. The comparisons consisted of 159 persons from the general Slovak population who were unrelated to the patients. Blood samples were collected and serological typing for HLA-A, HLA-B, HLA-C and the HLA-Dw antigens HLA-Dw1, HLA-Dw2, HLA-Dw3, HLA-Dw4, HLA-Dw5, HLA-Dw7, HLA-Dw8, hLA-Dw9, HLA-Dw10, and HLA-Dw11 was performed. The prevalence of HLA-Dw3 in thecohort was significantly elevated relative to the comparisons, 37.5 versus 8.7%.The increased HLA-Dw3 prevalence was associated with a relative risk of 6.3 of developing allergy to N-isopropyl-N'-phenyl-p-phenylenediamine. The prevalence of the HLA-Dw4 antigen was nonsignificantly elevated in the cohort. The prevalence of the other HLA antigens did not differ significantly between the two groups. The authors conclude that allergy to N-isopropyl-N'-phenyl-p-phenylenediamine has a polygenetic background and that genes of theHLA antigen complex are involved.

DERMATITIS WAS CAUSED BY N-ISOPROPYL-N-PHENYL-P-PHENYLENEDIAMINE (SANTOFLEX IP).

CONTACT ALLERGIC ECZEMA AT WRIST REGION IN 9 PROFESSIONALS & 36 HOUSEWIVES IN CONTACT WITH RUBBER PARTS OF ELECTRIC IRONS PRODUCED CHARACTERISTIC COLOR CAUSED BY PETECHIAE & HEMOSIDERIN PIGMENTATION. EXAM REVEALED CAPILLARITIS. IN 5 CASES PURPURA SPREAD TO WHOLE BODY.

51 PATIENTS ALLERGIC TO IPPD WERE REVIEWED & CLINICAL FEATURES & PROGNOSIS DISCUSSED. IN 38 OF 51 PATIENTS, THE DERMATITIS WAS CONSIDERED OCCUPATIONAL, MAJORITY BEING EMPLOYED IN TRANSPORT INDUSTRY.

For more Human Toxicity Excerpts (Complete) data for 4-(ISOPROPYLAMINO)DIPHENYLAMINE (10 total), please visit the HSDB record page.

An estimated BCF of 67 was calculated for 4-(iso-propylamino)diphenylamine(SRC), using an estimated log Kow of 3.3(1) and a regression-derived equation(2). According to a classification scheme(3), this BCF suggests the potential for bioconcentration in aquatic organisms is moderate.

The Henry's Law constant for 4-(iso-propylamino)diphenylamine is estimated as 1.4X10-9 atm-cu m/mole(SRC) using a fragment constant estimation method(1). This Henry's Law constant indicates that 4-(iso-propylamino)diphenylamine is expected to be essentially nonvolatile from water and moist soil surfaces(2). 4-(Iso-propylamino)diphenylamine is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 3.5X10-5 mm Hg(SRC), determined from a fragment constant method(3).

The rate constant for the vapor-phase reaction of 4-(iso-propylamino)diphenylamine with photochemically-produced hydroxyl radicals has been estimated as 2.2X10-10 cu cm/molecule-sec at 25 °C(SRC) using a structure estimation method(1). This corresponds to an atmospheric half-life of approximately 2 hours at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(1).

0M7PSL4100

N-ISOPROPYL-N'-PHENYL-1,4-PHENYLENEDIAMINE

Established Pharmacologic Class [EPC] - Standardized Chemical Allergen

Physiologic Effects [PE] - Increased Histamine Release

Physiologic Effects [PE] - Cell-mediated Immunity

Chemical Structure [CS] - Allergens

Urinary excretion of N-isopropyl-N'-phenyl-p-phenylenediamine (101724) (IPPD) was analyzed in 16 press operators exposed to this compound in a rubber curing workshop. A total of 22 urine samples were collected from each worker at the beginning and end of each work day over a 2 week period. ... Rapid excretion of IPPD occurred during the working day, with mean levels of IPPD in urine samples collected before and after shifts of 19.55 and 83.57 micrograms per liter (microg/l), respectively. A total of 4.4 percent of before and 28.7 percent of after shift samples showed no detectable IPPD. A second slow component of excretion was observed during the week, with mean concentrations in before shift samples rising from 10.8 to 25.8microg/l between the beginning and end of the week. In a skin absorption experiment, with one of the authors as subject, one hand was immersed in water containing IPPD for 90 minutes. IPPD levels in the urine were measured at 0, 3, 5, and 10.5 hours after exposure, and were found to be 0, 100, 350, and 570 ug/l, respectively. The excretion rate ceased 7 days after exposure. It was concluded that the kinetics of excretion of IPPD in workers exposed daily to this compound has two different components, an initially rapid one followed by a slow one, and that there are three different components of excretion kinetics after skin absorption with half times of 3, 7, and 24 hours.

Used to protect rubber against oxidation, ozone, and contamination by copper and manganese; [Hawley] Occupational exposures are mainly to rubber tires; [Kanerva, p. 1805]

Protection of rubbers against oxidation, ozone, flexcracking, and poisoning by copper and manganese.

(1979) 2.11X10+8 GRAMS (PRINCPL CUSTMS DISTS)

(1981) 2.40X10+7 GRAMS (PRINCPL CUSTMS DISTS)

2023: 250,000 - <400,000 lb

(1979) PROBABLY GREATER THAN 2.27X10+6 GRAMS

(1981) PROBABLY GREATER THAN 2.27X10+6 GRAMS

REACTION OF P-CHLORONITROBENZENE WITH ANILINE TO YIELD P-NITRODIPHENYLAMINE WHICH IS REDUCTIVELY ALKYLATED WITH ACETONE OVER A NICKEL/CHROMIUM CATALYST

Acetone + p-aminodiphenylamine (reductive amination)

"Flexzone" /is/ trademark for a series of antiozonants, antioxidants and stabilizers based on para-phenylenediamine. /Flexzone/

"Santoflex" /is/ trademark for a series of rubber antioxidants and antiozonants. /Santoflex/

Synthetic Rubber Manufacturing

1,4-Benzenediamine, N1-(1-methylethyl)-N4-phenyl-: ACTIVE

ELIMINATION OF ANTIOXIDANT 4010NA FROM RUBBER IS RECOMMENDED FOR ARTICLES WHICH CONTACT SKIN. A CHANGE IN DESIGN OF ELECTRIC IRONS IS SUGGESTED.