N-CYCLOHEXYL-2-BENZOTHIAZOLESULFENAMIDE

PRODUCT IDENTIFICATION
CAS NO. 95-33-0; 51540-81-9; 108251-59-8; 156014-54-9

N-CYCLOHEXYL-2-BENZOTHIAZOLESULFENAMIDE
EINECS NO. 202-411-2
FORMULA C13H16N2S2
MOL WT. 264.40

H.S. CODE

 2934.20

TOXICITY

 Rat LD50 (Oral): 5300mg/kg
SYNONYMS CBS; N-Cyclohexylbenzothiazole-2-sulphenamide;
Benzothiazyl-2-cyclohexylsulfenamide; SULFENAX; N-Cyclohexyl-2-benzothiazosulfenamide; N-Cyclohexyl-2-benzothiazolesulfenamide; Vulkacite CZ; Sulfenax CB; Soxinol CZ; Sulfenamide TS; Cyclohexyl benzothiazolesulfenamide;
SMILES c12c(sc(n1)SNC1CCCCC1)cccc2

CLASSIFICATION

 Rubber cure accelerator, Sulfenamide

PHYSICAL AND CHEMICAL PROPERTIES
PHYSICAL STATE white to gray powder

MELTING POINT

97 - 105 C
BOILING POINT  
SPECIFIC GRAVITY 1.3

SOLUBILITY IN WATER

Insoluble

SOLVENT SOLUBILITY

Soluble in toluene. acetone, ether, ethanol
pH  
VAPOR DENSITY  
AUTOIGNITION

 

REFRACTIVE INDEX

 
NFPA RATINGS Health: 2; Flammability: 1; Reactivity: 0
FLASH POINT

 
STABILITY Stable under ordinary conditions

GENERAL DESCRIPTION & EXTERNAL LINKS
This compound is the most common sulfenamide accelerator in EDPM. It is a primarily amine-based accelerator providing medium-fast cure with good scorch safety and excellent modulus development.It is also used as a secondary accelerators in combination with such as TMTD to adjust curing characteristics.

Wikipedia Linking: http://en.wikipedia.org/wiki/Accelerant

http://www.springerlink.com/
Rubber accelerators are now being fabricated in finely dispersed powder form, which improves the distribution of the compounds in rubber mixes. But the dispersion of the accelerators causes lumping and caking, and this hinders process mechanization and automatic control in the preparation and processing of rubber mixes. Granulation of rubber cure accelerators results in material which flows freely and is easily transported, but the accelerator should retain its finely dispersed structure. Granules satisfying this requirements can be produced on extruders by taking advantage of the tendency of aqueous pastes of rubber vulcanizing accelerators to plasticize when subjected to intense mixing and grinding.

http://doc.utwente.nl/
The effects of N-cyclopentamethylene thiocarbamyl-N-(cyclohexyl,thiocyclohexyl)sulfenamide (CPCTS) and N-oxydiethylene thiocarbamyl-N-(cyclohexyl,thiocyclohexyl)sulfenamide (ODCTS) as cure modifiers on the vulcanization of natural rubber (NR) containing benzothiazole accelerators were studied. CPCTS and ODCTS were used separately with 2-mercaptobenzothiazole and N-oxydiethylene benzothiazole sulfenamide to determine their effects on these accelerators. CPCTS and ODCTS retarded the accelerators. Enhanced activity was found with respect to the torque, scorch, modulus, and tensile strength and was believed to be due to the formation of different intermediate components during the early stage of the vulcanization of NR. Reactions likely responsible for acceleration and retardation were explored. CPCTS and ODCTS provided better cure retardation than N-cyclohexyl thiophthalimide. The chemical characterization of the NR vulcanizates correlated with the physical properties obtained at 140°C. Stocks containing CPCTS or ODCTS produced mostly monosulfide linkages, which were affected when N-cyclohexyl thiophthalimide was used. This provided information concerning the heat-resistance properties of the vulcanizates
SALES SPECIFICATION

APPEARANCE

 white to gray powder

ASSAY (TITRATION)

94.0% min

MELTING POINT

96 C (Initial) , 100 - 105 C (Final)

SIEVE ANALYSIS

0.5% max (+ 63 µm), 0.1% max (+ 150 µm)

INSOLUBLE

0.5% max ( in methanol)

ASH

0.3% max

OIL CONTENT

2.0% max (According to Buyer's request)

MOISTURE

0.5% max
TRANSPORTATION
PACKING III
HAZARD CLASS 9
UN NO. 3077
SAFETY INFORMATION

Hazard Symbols: XI N, Risk Phrases: 31-43-50/53, Safety Phrases: 36/37-60-61
GENERAL DESCRIPTION OF ACCELERATOR
Sulfur combines with nearly all elements. Sulfur forms ring and chain structures as it is the second only to carbon in exhibiting catenation. The 8-membered ring and shorter chain structure of sulfur molecule is important in vulcanization process which individual polymers are linked to other polymer molecules by atomic bridges. This process produces thermoset materials which are cross-linked and irreversible substances. The term thermoplastic is for high molecular weight polymers which can undergo melting-freezing cycle. Thermosets are not melted and re-molded on heating after cured. The split of sulfur 8-membered ring structure into shorter chains provides rubber vulcanization process. The split are liked with cure sites (some of the solid bonds in the molecule) on rubber molecules, resulting in forming sulfur bridges typically between 2 and 10 atoms long. Vulcanization makes rubber harder, more durable and more resistant to heating, aging and chemical attacks. The number of sulfur atoms in the sulfur bridges varies physical properties of the end products. Short bridges containing one or two sulfur atoms offer heat resistance and long bridges offer flexible property. Vulcanization can also be accomplished with certain peroxides, gamma radiation, and several other organic compounds. The principal classes of peroxide cross-linking agents are dialkyl and diaralkyl peroxides, peroxyketals and peroxyesters. Other vulcanizing agents include amine compounds for the cross-linking of fluorocarbon rubbers, metal oxides for chlorine-containing rubbers (notably zinc oxide for chloroprene rubber) and phenol-formaldehyde resins for the production of heat-resistant butyl rubber vulcanizates. Accelerator, in the rubber industry, is added with a curing agent to speed the vulcanization. Accelerators contain sulfur and nitrogen like derivatives of benzothiazole and thiocarbanilides. The popular accelerators are sulfenamides (as a delayed-action accelerators), thiazoles, thiuram sulfides, dithocarbamates and guanidines.

There are some types of rubber accelerators. They are used in combination with each other in accordance with vulcanizing and/or acid-base conditions. Some examples classified by chemical structure are as below;

  • Thiazole
    • 2-Mercaptobenzothiazole (CAS #: 149-30-4)
    • Dibenzothiazole disulfide (CAS #: 120-78-5)
    • 2-Mercaptobenzothiazole Zinc salt (CAS #: 155-04-4)
  • Sulphenamide
    • N-Cyclohexyl-2-benzothiazole sulfenamide (CAS #: 95-33-0)
    • N-Oxydienthylene-2-benzothiazole sulfenamide (CAS #: 102-77-2)
    • N-tert-butyl-2-benzothiazyl sulfenamide (CAS #: 95-31-8)
  • Guanidine
    • Diphenyl guanidine (CAS #: 102-06-7)
    • Di-o-tolylguanidine (CAS #: 97-39-2)
  • Thiuram
    • Tetramethyl thiuram disulfide (CAS #: 137-26-8)
    • Tetraethyl thiuram disulfide (CAS #: 97-77-8)
    • Tetramethyl thiuram monosulfide (CAS #: 97-74-5)
    • Isobutyl thiuram disulfide (CAS #: 3064-73-1)
    • Tetrabenzylthiuram disulfide (CAS #: 10591-85-2)
    • Dipentamethylene thiuramtetrasulfide (CAS #: 120-54-7)
  • Dithiocarbamate
    • Zinc dimethyl dithiocarbamate (CAS #: 137-30-4)
    • Zinc diethyl dithiocarbamate (CAS #: 14324-55-1)
    • Zinc dibutyl dithiocarbamate (CAS #: 136-23-2)
    • Zinc N-ethyl-dithiocarbamate (CAS #: 14634-93-6)
    • Zinc dibenzyl dithiocarbamate (CAS #: 14726-36-4)
    • Copper dimethyl dithiocarbamate (CAS #: 137-29-1)
  • Thiourea
    • Ethylene thiourea (CAS #: 96-45-7)
    • N,N'-Diethylthiourea (CAS #: 105-55-5)
    • N-N'-Diphenylthiourea (CAS #: 102-08-9)

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