DE3516068A1 - USE OF 1,1,1-TRICHLORMETHYL COMPOUNDS AS A LUBRICANT ADDITION AND LUBRICANT CONTAINING SUCH ADDITIVES - Google Patents

Description

BASF Aktiengesellschaft '"*" ο.Ζ. 0050/37709

Use of 1,1 .1-trichloromethyl compounds as a lubricant additive and lubricant. containing such additives

The present invention relates to the use of 1,1,1-trichloro-.5 methyl compounds as lubricant additive, as well as mineral "or synthetic lubricants containing such additives.

The lubrication of moving machine parts, especially those that are extreme Exposure to stress plays a crucial role in containing friction and frictional wear.

It is known from many publications that the addition of high-pressure additives to lubricants their lubricating properties, especially im Area of boundary lubrication, can be improved.

Phosphorus, sulfur or chlorine compounds are often used for this purpose. In the case of chlorine compounds, the chlorinated paraffins are of great importance to (J.Falbe, U.Hasserodt "Catalysts, Surfactants and Mineral Oil Additives", Pp. 247f., G. Thieme Verlag, Stuttgart (1978) and literature cited there).

Polychlorinated carboxylic acids have also been suggested as extreme pressure additives been. For example, DE-B-952 925 and DE-B-1 041 624 are particular 10,12,12,12-tetrachloro-lauric acid derivatives mentioned.

According to the proposal of DE-A-1 033 355 and FR-A-1 242 382, 2,2,4,4-tetrachlorobutyric acid can be used or their lower alkyl esters are used as additives for lubricants.

Derivatives that differ from butyric acids with a terminal trichloromethyl group are described in EP-A-4 957 for this purpose.

In US-A-4 207 272, US-A-4 247 489 and US-A-4 289 712 2,4,4,4-tetrachlorobutyl- and 1,4,4,4-tetrachlorobutylphosphite described, wherein their use as a lubricant additive is also mentioned.

Finally, in DE-A-3 317 355, the use of special 4,4,4-tri- and 2, 4, 4, 4-tetrachlorobutanol derivatives as lubricant additives described.

It has now been found that 1,1,1-trichloromethyl compounds of the formula I

Cl ₃ C - CH ₂ - CH ₂ - R (I).

DASr Aktiengesellschaft "^" p '° · ^Ζ · 0050/37709

in which R is a straight-chain or branched alkyl radical with 3 to 21 carbon atoms means, which can optionally be further substituted, can advantageously be used as a lubricant additive.

As the alkyl radical R; which can be straight-chain or branched and 3 to 21, preferably has 5 to 15 carbon atoms, for example Propyl, butyl, isobutyl, perityl, isopentyl, hexyl, heptyl, octyl, 2-ethylhexyl, isooctyl, nonyl, isononyl, decyl, isodecyl, undecyl, Dodecyl, 1,3,5,7-tetramethyloctyl, tridecyl, isotridecyl, tetradecyl, Pentadecyl, hexadecyl, heptadecyl, octadecyl, nonadecyl, eicosyl or heneicosyl radicals.

The terms "isooctyl", "isononyl", "isodecyl" and "isotridecyl" represent trivial names that differ from after the oxo synthesis f5 derived alcohols (cf. Ullmarm, "Enzyklopadie der Technischen Chemie ", 4th edition, Volume 7, pages 216 and 217 and Volume 11, pages 435 and 436).

Preference is given to using 1,1,1-trichloro compounds with an unsubstituted alkyl radical R. However, products in which the alkyl radical R is further substituted can also be used. Possible substituents here are hydroxyl groups and / or chlorine atoms, in which case the alkyl radical R can then generally have 1 or 2 hydroxyl groups and / or chlorine atoms.
25th

The preparation of the 1,1,1-trichloromethyl compounds to be used according to the invention is known. These products are obtained by reacting chloroform with the corresponding olefins. A suitable method is in in EP-A-75 201.

The 1,1,1-trichloromethyl compounds of the formula I can be both mineral as well as synthetic lubricants (e.g. polyether oils, ester oils, Phosphoric acid esters, silicon or halogen-containing oils) can be added.

Even small concentrations of these substances in the lubricant, for example, 0.05 to 10 Gew.Ü, preferably 0.1 to 5 Gew.Z ₁ based on the total mixture, sufficient lubricating properties, particularly under boundary lubrication conditions, a decisive improvement.

In addition, the lubricants can be combined with other additives that are included in find modern lubrication technology use, be equipped. These are auxiliaries known per se, for example oxide

BAD ORIG'NAL

BASF Aktiengesellschaft U "Y -> ^ - ^: Y '' - 'OZ 0050/37709

tion inhibitors, viscosity index improvers, pour point improvers, Detergents, dispersants, antifoam agents, demulsifiers or Corrosion inhibitors (cf. J. Falbe, U. Hasserodt "Catalysts, Tenside und Mineralöladditive", pp. 235 f., G. Thieme Verlag, Stuttgart (1978) or Ulimann "Encyclopedia of Technical Chemistry", 2J) .. 540 f., 4th edition, Verlag Chemie, Weinheim (1981)).

The following examples are intended to illustrate the invention, with part A the manufacture of the products (according to the process of EP-A-75 201) and their application is described in Part B.

A) Manufacturing

Additive 1

In an enamel kettle B.500 parts by volume of chloroform and 100 parts of anhydrous sodium acetate were heated with stirring to 130 ⁰ C. A mixture of 1,190 parts of 1-octene and 120 parts of tert-butyl perbenzoate was pumped in over the course of 5 hours and the mixture was then kept at 130 ^° C. for a further 4 hours. After cooling, 2,000 parts by volume of water were added and the aqueous phase was separated off and the excess chloroform is distilled off. The subsequent vacuum distillation of the residue gave 2,081 parts of distillate with a content of 85% by weight 1,1-trichlorononane at 78 to 86 ° C./0.4 mbar. Yield: 72 '/ d.Th.

Additive 2 to 6 were also produced in the same way as additive 1.

The starting product for additive 2 was 1-nonene. One received 1,1,1-trichlorodecane.

The starting product for additives 3 to 5 was a CiaHaif / Ci ^ Hae olefin mixture. The following Ci2H25-CCl3 / Ci ^ H2g-CCl3 mixtures were obtained (Specification in area 7. - GC analysis)

Additive 3: C13: C ₁₅ = 51: 16.8 Additive 4: C13: Cis = 53.4: 24.9 Additive 5: C ₁₃ : C15 = 53: 23

The starting product for additive 6 was a Ci6H ₃ 2 / Ci8H ₃ 6-01efin mixture. This gave the following as an additive Ci6H33 6-CCl ₃ / CieH37-CCl ₃ mixture: ₁ C 9 = 58: 32 (Z-surfaces - GC analysis)

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BASF Aktiengesellschaft -Jf- - - O, Z. 0050/37709

B) The application tests were carried out in the Shell four-ball apparatus., in the Almen-Wieland machine, in the FZG gear tension testing machine and carried out according to the Brugger test.

1) Test in the Stiell four-ball apparatus (DIN 51350, parts 2 and 3) The welding force (test force at which welding of the four-ball system enters the test device) and the dome diameter (mean dome diameter created under the test conditions of the three steel balls).

The test oil was a solvent raffinate with a viscosity of 41.3 mm ² / s at 40 ⁰ C and 6.25 mm ² / s at 100 ⁰ C and a viscosity index of 97th The additive concentration was in each case 3% by weight, based on the mixture used.

Additive no. Welding force spherical diameter [mm] (1 hour at 1000 N)

without additive 1500 5

1 2600 1

2 2400 0.9 3 2200 1 5 2300 0.9 Ej 2100 1

2) Testing in the Almen-Wieland machine

The applied maximum normal force was measured, as well as the thereby adjusting frictional force. The coefficient of friction / ic> is the quotient of frictional force and normal force.

1. The test oil, based a solvent raffinate with a viscosity of 88.94 served mm ² / s at 40 mm ⁰ C and 10.24 ² / s at 100 ⁰ C and a viscosity index of 95. The additive concentration in each case was 3 wt. on the mixture used,

Additive no. Normal force [N] Friction force [N] ^ R without additive 3000 1200 0.4 1 18500 3500 0.19 2 19000 3500 0.18 3 10,000 2000 0.2 4th 23000 3500 0.15 6th 10,000 2150 0.22

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BASF Aktiengesellschaft II - - ^ I : _: __: OZ 0050/37709

3) Testing in the FZG gear tension testing machine (DIN 51354, Part 2); The damage power level was measured

As a lubricant having a viscosity of Getriebeölvormischung was 15Ϊ mm ² / s at 40 ⁰ C and 15.0 mm ² / s at TOO ⁰ C and a Vis kositätsindex of 95th The premix did not contain any other additives.

Additive no. Damage force level

f0 without additive 7

1 11

2 11

3 10

4 12

5 ok

6 10

4) Testing according to the Brugger test (petroleum and coal-natural gas-petrochemical 81 (1984))

The surface pressure (load capacity) was measured by a rotating friction roller is applied to a test roller.

The test oil is a solvent raffinate with a viscosity of 88.94 mm ² served / s at 40 ⁰ C and 10.24 mm ² / s at 100 ⁰ C and a viscosity index of 95. The additive concentration in each case was 3 wt. I, based on the mixture used.

Additive no. Resilience

without additive 17.4 1 39.8 2 41 3 45 6th 38.1

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Claims (2)

BASF Aktiengesellschaft - O.Z. 0050/37709 claims 1. Use of 1,1,1-trichloromethyl compounds of the general Formula I. Cl ₃ C - CH ₂ - CH ₂ - R (I), in which R denotes a straight-chain or branched alkyl radical having 3 to 21 carbon atoms, which is optionally further substituted 70 can be used as a lubricant additive. 2. Lubricating oil with lubricating viscosity from the class of mineral or synthetic lubricant, contained as an additive in amounts of 0.05 up to 10% by weight, based on the total mixture, a compound of 15 formula I according to claim 547/84 Kg / HB O ^ .O5 HB0038 Vk BAD ORiG'NAl