DE573570C - Vulcanization accelerator - Google Patents

Description

GERMAN EMPIRE

Bibliotheek
Bur. Ind. Self-dom

17 MEI 1933

ISSUE ON APRIL 3, 1933

REICH PATENT OFFICE

PATENT LETTERING

CLASS 39b 'GROUP

■ '■' 140938 IVaJ ₃₉ V

I. G. Farbenindustrie Akt.-Ges. in Frankfurt a. M. *)

Vulcanization accelerator Patented in the German Empire on March 12, 1931

Some nitrogenous bases that are used as vulcanization accelerators can work so vigorously under certain processing conditions that scorch can occur. However, if you replace in nitrogenous bases, which have accelerator effect, at least one hydrogen atom bonded to nitrogen without ring formation by the remainder - S · R one in free form not accelerating acting mercapto compound R · S H, where R means substituted phenyl ^ so In general, accelerators with a very good critical temperature are obtained, but they do are vigorously effective during vulcanization. You own the grouping

\ _N —S —C ^

in which the sulfur is not bound in a ring.

By adding a suitable second accelerator, the effectiveness of the new accelerator while maintaining the

■ "good critical temperature usually increase.

Compounds of the type mentioned are obtained, for. B. by the action of the N-halogen compounds nitrogen-containing accelerator for non-accelerating mercaptans or their salts according to the general Scheme

Γ — HIg + Me —S-Ci ^ -> MeHIg -j-NN-S-C ^ -.

In this way, p-cresylsulfenic acid piperidide is obtained from N-chloropiperidine and sodium thiocresol ·

H,

Na-S

GH, -VNaClH-C ₅ H ₁₀ NS

C ₀ H ₄

CH ₃

H,

On the one hand, all nitrogen-containing accelerators are suitable for this implementation, which give chlorine compounds, on the other hand all mercaptans of the formula R-S H, in which R

*) The patent seeker indicated the following as the inventors:

Dr. Ewald Zaucker in Cologne-Mülheim, Dr. Ludwig Orthner in Leverkusen-I. G, plant and Dr. Max Bagemamn in Cologne-Mülheim.

Substituted phenyl means which in free form have no “accelerating properties” own.

Another way of displaying the accelerators mentioned is based on the

HIg-S

Effect of organic sulfur halides on nitrogen-containing accelerators of a basic character with at least one directly on nitrogen bonded hydrogen atom according to the general scheme

- S-C ^ + HHIg.

For example, dibutylamine and p-nitrophenylsulfur chloride are obtained after 65 10 equation *. "'.-.-

(C, H ₉ ) ₂ = NH + Cl-SC ₆ H ₄ -NH, _v HCl + (C ₄ H ₀ ), Z = NSC ₆ H ₄ -NO ₂

the p-nitrophenylsulfendibutylaniid.

For this "reaction those organic sulfur halides come into consideration, whose underlying mercaptan is not an accelerator. As a second component leaves use any nitrogen-containing basic accelerator, which at least one has a substitutable hydrogen atom bonded directly to nitrogen.

Example ι

The reaction products of p-nitrophenylsulfur chloride and dibutylamine were tested (I), piperidine (II), s-diphenylguanidine (III) and o-tolylbiguanide (IV), namely in the mixture ΐοο, ο parts by weight lighter Crepe, 3.5 parts by weight of sulfur, 5.0 parts by weight of zinc oxide, 0.5 part by weight of stearic acid, r, o part by weight accelerator at 3.5 atm. Furthermore, the reaction product from Chlorpiperidine with p-thiocresol (V) in the mixture 100.0 parts by weight of light crepe, 3.0 parts by weight of sulfur, 5.0 parts by weight of zinc oxide, 1.0 part by weight of accelerator 3.0 atm. .

The following strengths in kg / cm ^{2 were} obtained:

Heating time
in minutes I. ¹¹ III 1062 IV ι
V. 916 IO "3 16- 95 825 3 20th 99 161 170 792 109 59 45 ιδο 203 213 173 161 60 I ₇ p 195 207 177 182 Elongation in ⁵ rozeni 10 657 949 433. -. 20th ₉ Sg 933 978 ("above
\ 1000 55 45 873 810 861 905 60 833 764 822 858

'

During a heating period of 60 minutes at ¹ Z ₂ atm, none of the specified substances caused scorch.

If you replace the natural rubber in the above example with synthetic, z. B, derived from butadiene hydrocarbons rubber-like compositions, good results are also obtained.

Example 2

In a mixture of 100.0 parts by weight of light crepe, 5.0 parts by weight of zinc oxide, 3.0 parts by weight of sulfur, 0.3 part by weight of p-tolylsulfene piperidide and 0.2 part by weight Mercaptobenzothiazole (A) or 0.2 part by weight dibenzothiazyl-2 · 2'-disulfide (B) the following values were obtained:

heater atü Tear resistance
kg / cm ² B. strain
0 /
/ 0 Min. 0.5 A. - A t B 30th 0.5 ■ _ ■■ - ^l 60 3.0 ! 95 136 945! - IO 3, o 198 222 850 870 20th 3.0 219 '183 785! 805 60 • 198 775 i 765

Claims (2)

Patent claims: i. Vulcanization accelerator,. existing from products that are obtainable by in 'nitrogenous Accelerate at least one nitrogen-bonded hydrogen atom without ring formation by the radical 'RS-one in free form non-accelerating mercapto compound R — S H replaced, in which R is substituted phenyl. 2. Vulcanization accelerator according to claim ι mixed with other vulcanization accelerators.