KR20180094097A - Fatty acid methyl ester composition having a low pour point - Google Patents

Abstract

The present invention relates to a composition comprising:
- a mixture of 95% or more castor oil fatty acid methyl esters;
- additive to lower the pour point;
The maximum pour point of the composition is 0 ° C.
The present invention also relates to the use of the composition as a lubricant, a formwork remover for concrete, a degreasing agent or a detergent.

Description

Fatty acid methyl ester composition having a low pour point

The present invention relates to a composition based on a fatty acid methyl ester derived from a castor oil channel having a low pour point. Such compositions are used, inter alia, as lubricants or to facilitate the release of concrete.

For example, it is known to transesterify vegetable or animal oils, which are mixtures of different fatty acids, to produce the products used for lubrication.

The composition of the fatty acid is highly variable from one vegetable or animal oil to another to the extent that each ester-exchanged oil has different properties.

Particularly useful products, especially those used as lubricants or concrete release agents, are mixtures of fatty acid methyl esters derived from castor oil. These products mainly contain C11-C22 fatty acid methyl esters, the main examples of which are methyl linoleate and methyl oleate. These products also contain two specific compounds, 10-undecylenic acid and methyl ricinoleate, which are not commonly found in products derived from other vegetable oils.

Such products are in particular sold under the trade name Oleris® Esterol A by Arkema. However, one drawback of this product is that it has a relatively high pour point, about + 6 ° C (according to standard ASTM D97). For this reason, the use of this product is difficult in cold weather.

It is known to use a pour point depressant additive to lower the pour point of various products from vegetable or animal oils.

Accordingly, various compositions are described in which the pour point depressant additives are used in the documents EP 0543356, EP 0626442, US 6,409,778, US 6,051,538 and US 2011/296743.

Generally speaking, however, the possibility of lowering the pour point of a product derived from vegetable or animal oils to enable their use in cold weather is dependent on the nature and properties of such products. As a result, it is necessary to be able to improve the mixture of fatty acid methyl esters derived from castor oil to enable their use in cold weather.

The present invention is primarily directed to compositions comprising:

A mixture of at least 95% by weight castor oil fatty acid methyl ester;

- Pour point depressant additives;

The pour point of the composition is 0 DEG C or less.

According to one embodiment, the pour point of the composition is -5 DEG C or less, preferably -9 DEG C or less.

According to one embodiment, the mixture of castor oil fatty acid methyl esters has an iodine value of 100 to 120 g / 100 g, and in a weight ratio comprises:

- 5 to 20%, preferably 8 to 12% methyl stearate;

- 20 to 40%, preferably 25 to 35% methyl oleate;

- 30 to 50%, preferably 35 to 45% of methyl linoleate;

- less than 10%, preferably less than 8.5% methyl palmitate;

- 1.5 to 4%, preferably 2 to 3% of methyl ricinoleate;

- 0.4 to 1.5%, preferably 0.6 to 1% 10-undecylenic acid.

According to one embodiment, the composition comprises, by weight, 1 to 2%, preferably 1.2 to 1.8%, of a pour point depressant additive.

According to one embodiment, the pour point depressant additive is an acrylic polymer (preferably according to the general formula given below) that is soluble in the oil and the ratio is preferably from 15 to 40 parts of 60 to 100 parts of acrylic polymer per oil.

According to one embodiment, the oil is a paraffinic distillate.

According to one embodiment, the additive has:

A viscosity of from 200 to 500 mm ² / s, preferably from 300 to 400 mm ² / s at 100 캜 according to standard ASTM D445;

A pour point of not more than -30 占 폚, preferably not more than -36 占 폚 according to standard ASTM D97;

An acid number of not more than 0.6 mg KOH / g, preferably not more than 0.5 mg KOH / g according to standard ASTM D974.

The invention also relates to the use of said composition as a lubricant, a concrete release agent, a degreasing agent or a detergent.

The present invention makes it possible to overcome the disadvantages of the state of the art. It more particularly provides a mixture of fatty acid methyl esters derived from castor oil which can be used in cold weather.

 This is achieved by the use of additives which can lower the pour point of the mixture below 0 ° C, preferably below -5 ° C or below -9 ° C.

1 , (Y-axis, in mm) of the layer of crystals formed by the temperature (x-axis, in degrees Celsius). Details are included in the following Example 1.

The present invention will now be described in more detail and in a non-limiting manner in the following detailed description.

The composition according to the invention is obtained by mixing a mixture of fatty acid methyl esters derived from castor oil and a pour point depressant additive.

Mixtures of fatty acid methyl esters derived from castor oil are obtained by transesterification of methanol and castor oil. The degree of transesterification of the mixture need not necessarily be 100%, which means that the mixture of methyl esters being discussed may contain a certain proportion of non-esterified fatty acids.

Mixtures of fatty acid methyl esters derived from castor oil preferably have a pour point of from 5 to 8 DEG C according to standard ASTM D97; And / or from 100 to 120 g / 100 g of iodine. The iodine value can be measured according to standard ISO 3961.

The mixture of fatty acid methyl esters being discussed preferably includes:

- 5 to 20%, preferably 8 to 12% methyl stearate (C18: 0);

- 20 to 40%, preferably 25 to 35% methyl oleate (C18: 1);

- 30 to 50%, preferably 35 to 45% of methyl linoleate (C18: 2);

- less than 10%, preferably less than 8.5% methyl palmitate (C16: 0);

- 1.5 to 4%, preferably 2 to 3%, of methylisinolate (C18: 1 (OH));

- 0.4 to 1.5%, preferably 0.6 to 1% 10-undecylic acid (C11: 1).

The pour point depressant additive is selected so that the pour point of the composition according to the invention is less than 0 ° C (preferably less than -1 ° C, or less than -2 ° C, or less than -3 ° C, or less than -4 ° C, Less than 6 ° C, or less than -7 ° C, or less than -8 ° C, or less than -9 ° C, according to standard ASTM D97).

This may in particular be an acrylic polymer (which includes an acrylic copolymer) that is soluble in the oil. The relative proportions are preferably from 15 to 40 parts of 60 to 100 parts of acrylic polymer per oil.

The acrylic polymer is preferably a polyalkyl methacrylate of the general formula:

Wherein n is an integer of preferably 200 to 2000, and each R independently represents a C1 to C22 alkyl group.

The oil may be obtained, for example, by catalytic hydrogenation of petroleum fractions and may predominantly contain predominantly saturated C 15 to C 30 hydrocarbons and may have a viscosity of less than 19 cSt at 40 ° C. This may in particular be an oil having the reference number CAS 64742-55-8.

The oil may also be obtained by catalytic hydrogenation of petroleum fractions and may predominantly contain predominantly saturated C20 to C30 hydrocarbons and may have a viscosity of greater than 19 cSt at 40 占 폚. This may in particular be an oil having the reference CAS 64742-54-7.

The oil may also be obtained from petroleum fractions by removing paraffins by crystallization in a solvent, and may comprise mainly C20 to C30 hydrocarbons and may have a viscosity of greater than 19 cSt at 40 占 폚. This may in particular be an oil having the reference number CAS 64742-65-0.

It is also possible to use a mixture of the above oils.

The additive preferably has the following:

A viscosity of from 200 to 500 mm ² / s, preferably from 300 to 400 mm ² / s at 100 캜 according to standard ASTM D445; And / or

A pour point of not more than -30 占 폚, preferably not more than -36 占 폚 according to standard ASTM D97; And / or

- an acid value of not more than 0.6 mg KOH / g, preferably not more than 0.5 mg KOH / g according to standard ASTM D974.

Particularly suitable additives are those sold by Evonik under the reference VISCOPLEX® 1-211.

The additives may be present in the composition in a weight ratio of from 0.1 to 5% and preferably from 1 to 2%. A preferred content range is as follows: 1.0 to 1.1%; 1.1 to 1.2%; 1.2 to 1.3%; 1.3 to 1.4%; 1.4 to 1.5%; 1.5 to 1.6%; 1.6 to 1.7%; 1.7 to 1.8%; 1.8 to 1.9% and 1.9 to 2.0%. A weight content of about 1.5% is particularly suitable.

The content of acrylic copolymer or polymer in the composition of the present invention is preferably 0.5 to 2%, more particularly preferably 0.8 to 1.4% (especially 0.8 to 0.9%, or 0.9 to 1.0%, or 1.0 to 1.1% Or 1.1 to 1.2%, or 1.2 to 1.3%, or 1.3 to 1.4%).

According to one embodiment, the composition consists essentially of a mixture of fatty acid methyl esters derived from castor oil and a pour point depressant additive. According to another embodiment, the composition comprises a mixture of fatty acid methyl esters derived from castor oil and a pour point depressant additive.

Example

The following examples illustrate the invention without limiting it.

Example 1

A variety of pour point depressant additives are added to the mixture of fatty acid methyl esters derived from castor oil sold by Arkema under the trade name Oleris® Esterol A (pour point: + 6 ° C) in an amount of 1 to 2.5%.

The additives used are:

VISCOPLEX® 10-310 (Evonik): an acrylic copolymer in an amount of at least 60%, combined with rapeseed oil having a viscosity of 1800 mm ² / s at 100 ° C;

- VISCOPLEX® 1-211 (Evonik): an acrylic polymer in an amount of at least 60%, in combination with a neutral oil, having a viscosity of 400 mm ² / s at 100 ° C;

- VISCOPLEX® 1-180 (Evonik): an acrylic copolymer in an amount of 40 to 70%, in combination with a neutral oil, having a viscosity of 300 mm ² / s at 100 ° C;

- VISCOPLEX® 1-255 (Evonik): An acrylic copolymer in an amount of 15 to 40% in combination with a neutral oil having a viscosity of 45 mm ² / s at 100 ° C.

The pour points of the compositions obtained in this way are summarized in the following table:

Pour Point (ASTM D97)

It is observed that the additive VISCOPLEX® 1-211 is particularly beneficial because it can drop the pour point to -9 ° C at a concentration of only 1.5%.

Furthermore, the measurement of the crystallization rate was carried out at 5 to -3 DEG C by measuring the thickness of the layer of crystals formed in the sample (packing height 55 mm) stored in the test tube. This measurement relates to four compositions prepared using 1.5% of the above four additives and also to the control sample Oleris (R) Esterol A. The results are shown in Fig. They demonstrate that the additive VISCOPLEX® 1-211 provides the slowest crystallization rate.

 Curve 1 represents the control composition without additive, Curve 2 represents the composition prepared using VISCOPLEX® 1-255, Curve 3 represents the composition prepared using VISCOPLEX® 1-180, Curve 4 represents the composition prepared using VISCOPLEX® 1-155 10-310, and curve 5 represents the composition prepared using VISCOPLEX® 1-211.

Example 2

The consistency of the various compositions made with the same products as in Example 1 was evaluated after storage under fixed conditions at -7 C for 7 days.

The results are shown in the following table:

Homogeneity and fluidity of the product

The composition obtained using VISCOPLEX (R) 1-211 is most advantageous in terms of homogeneity and fluidity with respect to the moderate amount of additive remaining (1.5%).

Claims (9)

Claims 1. A composition comprising:
A mixture of at least 95% by weight castor oil fatty acid methyl ester;
- Pour point depressant additives;
RTI ID = 0.0 > 0 C < / RTI > The composition of claim 1, wherein the pour point is -5 占 폚 or lower, preferably -9 占 폚 or lower. The composition of claim 1 or 2, wherein the mixture of castor oil fatty acid methyl esters has an iodine number of 100 to 120 g / 100 g,
- 5 to 20%, preferably 8 to 12% methyl stearate;
- 20 to 40%, preferably 25 to 35% methyl oleate;
- 30 to 50%, preferably 35 to 45% of methyl linoleate;
- less than 10%, preferably less than 8.5% methyl palmitate;
- 1.5 to 4%, preferably 2 to 3% of methyl ricinoleate;
- 0.4 to 1.5%, preferably 0.6 to 1% 10-undecylenic acid. 4. The composition of any one of claims 1 to 3, wherein the pour point depressant additive comprises 1 to 2% by weight, preferably 1.2 to 1.8% by weight. 5. The composition according to any one of claims 1 to 4, wherein the pour point depressant additive is an acrylic polymer dissolved in an oil and the ratio is preferably from 15 to 40 parts of 60 to 100 parts of acrylic polymer per oil. 6. The composition of claim 5, wherein the acrylic polymer is a polymer of the formula:

Wherein n is an integer of preferably 200 to 2000, and each R represents a C1 to C22 alkyl group. The composition according to claim 5 or 6, wherein the oil is a paraffinic distillate. 8. The composition according to any one of claims 1 to 7, wherein the additive is:
A viscosity of from 200 to 500 mm ² / s, preferably from 300 to 400 mm ² / s at 100 캜 according to standard ASTM D445;
A pour point of not more than -30 占 폚, preferably not more than -36 占 폚 according to standard ASTM D97;
An acid number of not more than 0.6 mg KOH / g, preferably not more than 0.5 mg KOH / g according to standard ASTM D974. Use of a composition according to any one of claims 1 to 8 as a lubricant, a concrete release agent, a degreasing agent or a detergent.

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