US2130242A - Vulcanization of rubber - Google Patents

Vulcanization of rubber Download PDF

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Publication number
US2130242A
US2130242A US6807A US680735A US2130242A US 2130242 A US2130242 A US 2130242A US 6807 A US6807 A US 6807A US 680735 A US680735 A US 680735A US 2130242 A US2130242 A US 2130242A
Authority
US
United States
Prior art keywords
rubber
vulcanization
diphenyl
sulphide
disulphide
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Expired - Lifetime
Application number
US6807A
Inventor
William E Messer
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Uniroyal Inc
Original Assignee
Us Rubber Prod Inc
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Us Rubber Prod Inc filed Critical Us Rubber Prod Inc
Priority to US6807A priority Critical patent/US2130242A/en
Priority to GB4778/36A priority patent/GB448237A/en
Application granted granted Critical
Publication of US2130242A publication Critical patent/US2130242A/en
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/0008—Organic ingredients according to more than one of the "one dot" groups of C08K5/01 - C08K5/59
    • C08K5/0025—Crosslinking or vulcanising agents; including accelerators

Definitions

  • This invention relates to the use of new and improved accelerator combinations, useful in the production of vulcanized rubber goods.
  • An object of this invention is to provide a new 5 activator for organic accelerators and more particularly for thiazyl sulphide vulcanization accelerators such as the arylene thiazyl sulphides and disulphides which when used in conjunction therewith will tend to produce less scorching and better calendering as well as better ageing rubber stocks.
  • activators are characterized in being broadly amino thiophenols characterized by the grouping 20 wherein R, is hydrogen or a substituted element or group.
  • R is hydrogen or a substituted element or group. Examples are o-amino thiophenol, o-o' diamino-diphenyl disulphide, o-o diaminodiphenyl monosulphide, p-amino thiophenol, p-p diamino-diphenyl monosulphide, m-amino thio- 25 phenol, m.m-diamino-diphenyl disulphide,
  • salts 30 and acyl derivatives of the amino thiophenols may also be used, as where the hydrogen of the sulfhydryl group is replaced by metal or an acyl group.
  • the following example is given to illustrate 35 preferred aspects of the invention and is not to be construed as limiting thereof.
  • the parts given are parts by Weight. T stands for tensile in pounds per square inch at break, and E stands for percent elongation at break. The stock that Scorch test (5 pounds per sq. in. steam pressure) Cure in minutes Unaged Cure in ruins. at 30 lbs. sq. in. steam pressure 168 hrs. in oxygen bomb (300 oxygen maintained at 60 C.)
  • mercaptobenzothiazole its disulphide, mercapto-benzo-thiazole-disulphide benzothiazyl disulphide
  • thiazole accelerators which are derivatives, substitution products or salts of mercaptobenzothiazole illustrated by dinitro phenyl ester of mercaptobenzothiazole, benzoyl benzothiazyl sulphide, etc.
  • the amount of activator usable may vary from that specifically shown. Generally it is usable in the same proportions as prior art activators of organic accelerators.
  • the term rubber is to be construed broadly as including caoutchouc, balata, gutta percha, rubber isomers, synthetic rub-- her, and is applicable to latex whether naturally occurring or artificially preferred.
  • the activators may be used with different types of stock than that illustrated, with other compounding ingredients and other proportions of ingredients.
  • the activator is substantially non-discoloring which is another attribute of this invention.
  • a process of producing vulcanized rubber goods which comprises accelerating the vulcanization of a vulcanizable rubber stock with an arylene thiazyl sulphide accelerator and an added amount of an activator therefor having the general formula which the proportion of the diphenyl sulphide preponderates over the proportion of the sulphide accelerator.

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  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Organic Chemistry (AREA)
  • Compositions Of Macromolecular Compounds (AREA)
  • Processes Of Treating Macromolecular Substances (AREA)

Description

Patented Sept. 13, 1938 UNITED STATES? PATENT." OFEtl-CEZ VULOANIZATION OF- RUBBER William-E.:Messer,- Cheshire, Conn assignor to.-.
United States Rubber Products,- Inc., New 1 York, N.. Y.; a corporation of.Delaware No- Drawingr Application February: 16,; 1935;-
Serial .No. (k807i 2 Claims.
This invention relates to the use of new and improved accelerator combinations, useful in the production of vulcanized rubber goods.
An object of this invention is to provide a new 5 activator for organic accelerators and more particularly for thiazyl sulphide vulcanization accelerators such as the arylene thiazyl sulphides and disulphides which when used in conjunction therewith will tend to produce less scorching and better calendering as well as better ageing rubber stocks.
These activators are characterized in being broadly amino thiophenols characterized by the grouping 20 wherein R, is hydrogen or a substituted element or group. Examples are o-amino thiophenol, o-o' diamino-diphenyl disulphide, o-o diaminodiphenyl monosulphide, p-amino thiophenol, p-p diamino-diphenyl monosulphide, m-amino thio- 25 phenol, m.m-diamino-diphenyl disulphide,
m.m'-diamino diphenyl monosulphide, o-p-diamino diphenyl disulphide, o-p-diamino diphenyl sulphide and halogen and or alkyl nuclear-substituted derivatives thereof. The salts 30 and acyl derivatives of the amino thiophenols may also be used, as where the hydrogen of the sulfhydryl group is replaced by metal or an acyl group.
The following example is given to illustrate 35 preferred aspects of the invention and is not to be construed as limiting thereof. The parts given are parts by Weight. T stands for tensile in pounds per square inch at break, and E stands for percent elongation at break. The stock that Scorch test (5 pounds per sq. in. steam pressure) Cure in minutes Unaged Cure in ruins. at 30 lbs. sq. in. steam pressure 168 hrs. in oxygen bomb (300 oxygen maintained at 60 C.)
It will be observed that the initial cure, shown by the scorch test, is retarded by use the combination in B. Also that the optimum cure is reached at about the same time as with the full amount of mercaptobenzothiazole (stock A) which shows that an economy in use of the thiazole accelerator may be obtained by the present invention and further with an improvement in ageing properties.
Instead of mercaptobenzothiazole, its disulphide, mercapto-benzo-thiazole-disulphide benzothiazyl disulphide) may be used, as well as other well known thiazole accelerators which are derivatives, substitution products or salts of mercaptobenzothiazole illustrated by dinitro phenyl ester of mercaptobenzothiazole, benzoyl benzothiazyl sulphide, etc.
The amount of activator usable may vary from that specifically shown. Generally it is usable in the same proportions as prior art activators of organic accelerators. The term rubber is to be construed broadly as including caoutchouc, balata, gutta percha, rubber isomers, synthetic rub-- her, and is applicable to latex whether naturally occurring or artificially preferred.
The activators may be used with different types of stock than that illustrated, with other compounding ingredients and other proportions of ingredients. In the case of white stocks the activator is substantially non-discoloring which is another attribute of this invention.
Having thus described my invention, what I claim and desire to protect by Letters Patent is:
l. A process of producing vulcanized rubber goods which comprises accelerating the vulcanization of a vulcanizable rubber stock with an arylene thiazyl sulphide accelerator and an added amount of an activator therefor having the general formula which the proportion of the diphenyl sulphide preponderates over the proportion of the sulphide accelerator.
WILLIAM E. MESSER.
US6807A 1935-02-16 1935-02-16 Vulcanization of rubber Expired - Lifetime US2130242A (en)

Priority Applications (2)

Application Number Priority Date Filing Date Title
US6807A US2130242A (en) 1935-02-16 1935-02-16 Vulcanization of rubber
GB4778/36A GB448237A (en) 1935-02-16 1936-02-17 Improvements in the vulcanization of rubber

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US6807A US2130242A (en) 1935-02-16 1935-02-16 Vulcanization of rubber

Publications (1)

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US2130242A true US2130242A (en) 1938-09-13

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Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2454260A (en) * 1946-02-12 1948-11-16 Hoffmann La Roche Preparation of metal mercaptides of amino-aryl mercaptans
US2490717A (en) * 1946-02-12 1949-12-06 Hoffmann La Roche Metal mercaptides of 2-amino-benzenethiol
US2683166A (en) * 1948-11-06 1954-07-06 American Cyanamid Co O, o'-di-(carbalkoxyamino)-diphenyldisulfides
DE1086427B (en) * 1953-10-22 1960-08-04 American Cyanamid Co Process for increasing the plasticization rate of unvulcanized natural or synthetic rubber
US4026963A (en) * 1975-08-21 1977-05-31 Uniroyal Inc. N-(o or p-thiophenyl) substituted polyhalo-5-norbornene-2,3,-dicarboximide flame retardants and polymers containing said imides
US5321067A (en) * 1990-10-24 1994-06-14 Ciba-Geigy Corporation Stabilizers derived from 3,5-dialkyl-4-aminobenzenethiol

Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2454260A (en) * 1946-02-12 1948-11-16 Hoffmann La Roche Preparation of metal mercaptides of amino-aryl mercaptans
US2490717A (en) * 1946-02-12 1949-12-06 Hoffmann La Roche Metal mercaptides of 2-amino-benzenethiol
US2683166A (en) * 1948-11-06 1954-07-06 American Cyanamid Co O, o'-di-(carbalkoxyamino)-diphenyldisulfides
DE1086427B (en) * 1953-10-22 1960-08-04 American Cyanamid Co Process for increasing the plasticization rate of unvulcanized natural or synthetic rubber
US4026963A (en) * 1975-08-21 1977-05-31 Uniroyal Inc. N-(o or p-thiophenyl) substituted polyhalo-5-norbornene-2,3,-dicarboximide flame retardants and polymers containing said imides
US5321067A (en) * 1990-10-24 1994-06-14 Ciba-Geigy Corporation Stabilizers derived from 3,5-dialkyl-4-aminobenzenethiol

Also Published As

Publication number Publication date
GB448237A (en) 1936-06-04

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