JPH11349981A - Natural oil and fat-based liquid composition - Google Patents

Abstract

PROBLEM TO BE SOLVED: To obtain a natural oil and fat-based liquid composition having good handleability through seasons, exhibiting sufficient viscosity even at high temperature, capable of ensuring stability to oxidation and sufficiently practicing even from the viewpoint of cost by using natural liquid oil and fat free from problem on environment as a base and improving the viscosity. SOLUTION: This liquid composition is obtained by compounding natural oil and fat component A with an ester component B comprising a polyhydric alcohol ester of an oxyfatty acid condensate as a viscosity adjusting agent. Average condensation degree of the oxyfatty acid condensate is >=2.5 and when the total amount of both of the natural oil and fat component A and the ester component B is 100 wt.%, the ratio of the natural oil and fat component A is 98-55 wt.% and the ratio of the ester component B is 2-45 wt.% and viscosity η40 at 40 deg.C of compositions of both components is 70-500 cps and viscosity η100 at 100 deg.C is 15-60 cps and ratio [log (η40 )/log (η100 )] of logarithm of viscosities at both temperatures is <=1.80.

Description

DETAILED DESCRIPTION OF THE INVENTION

[0001]

TECHNICAL FIELD The present invention relates to a natural fat and oil component,
The present invention relates to a natural oil / fat liquid composition having improved viscosity by blending a specific ester component as a viscosity modifier.

[0002]

2. Description of the Related Art <Viscosity of natural fats and oils> In recent years, natural fats and oils are being re-evaluated in a wide range of fields from the viewpoints of reproducibility, biodegradability and safety. Regarding the viscosity of typical natural fats and oils, the constituent fatty acids will be described briefly below, divided into those that are oxy fatty acids (fatty acids having OH groups) and those that are non-oxy fatty acids (fatty acids having no OH groups). I do.

Castor oil is a unique fat and oil among natural fats and oils in terms of chemical structure in that most of the constituent fatty acids (about 90%) are oxyfatty acids. Is found only in resquerella oil besides castor oil, but resquerella oil is difficult to obtain). Castor oil is a triglyceride of a fatty acid whose main component is ricinoleic acid (fatty acid having 18 carbon atoms having an OH group at the C atom at position 12 and a C = C double bond at the 9-10 position) which is an oxy fatty acid. It is the fat with the highest viscosity among the fats and oils.
Although it is as high as 00 cps, the viscosity at 40 ° C is about 280 cps
s, viscosity at 100 ° C is about 18 cps,
The viscosity decreases rapidly with increasing temperature. The drawback of castor oil is that the viscosity has a large temperature dependency, and there is a problem in handling in winter such as pumping becomes difficult at low temperatures due to high viscosity.
At a high temperature exceeding ℃, the viscosity is remarkably reduced, so that sufficient oiliness cannot be maintained, and it may be difficult to exhibit functions. The iodine value of castor oil is about 86 ± 3.

Most of the general natural liquid fats and oils have non-oxy fatty acids such as oleic acid, linoleic acid and linolenic acid as their main constituent fatty acids. The common viscosity property is that the viscosity has a temperature dependence. Although small, the viscosity tends to be low near normal temperature, lower by about an order of magnitude at 100 ° C., and lower throughout the entire temperature range. As an example, the viscosity of rapeseed oil is 38 at 40 ° C.
cps, 7 cps at 100 ° C.

[0005] In this kind of general natural liquid oils and fats,
Oxidation stability-there is a dilemma at the pour point. For example, many of such natural liquid fats (such as rapeseed oil, soybean oil, corn oil, safflower oil, sunflower oil, and cottonseed oil) lack heat and oxidation stability because their iodine values are 100 or more. Among them, rapeseed oil has an iodine value of 105 to 1
Although it is about 15 and has relatively stable oxidation, it becomes difficult to employ it when the conditions of use are a little harsh. Palm oil, on the other hand, has a pour point of 30 although the iodine value is as low as 50-60.
C. or higher, and even palm olein obtained by removing the high pour point portion from the palm oil has a melting point of about 20 ° C. and is solid from fall to spring for half a year, and cannot be said to be a stable oily oil.

Among the above-mentioned general natural liquid fats and oils, natural fats and oils having a high oleic acid content, such as olive oil and camellia oil, have the disadvantage of high cost, but have an iodine value of 80.
Keep liquid as low as ~ 95. In addition, high oleic oil such as rapeseed oil with high oleic acid content by genetic technology,
It is a liquid fat with a low iodine value (100 or less). These fats and oils avoid the dilemma of oxidative stability and pour point, but still have low viscosities over the entire temperature range.

<Improvement of viscosity of natural fats and oils> As described above, natural fats and oils each have a unique viscosity.
For applications that require liquids at low temperatures, maintain viscosity at high temperatures, and have oxidative stability, selection of natural fats and oils alone is not sufficient. Therefore, it is proposed to take various measures as described below.

[0008] (1) US Pat.
It has been shown that the reaction of castor oil OH groups with fatty acids or dibasic acids improves the temperature dependence of the viscosity of castor oil.

(2) US Pat. No. 4,522,250 and JP-A-61-95736 show that a composition containing 50% by weight or more of glycerin trioleate is used in continuous casting of aluminum and its alloys. I have. This specification also describes the case where castor oil, ethyl oleate, methyl oleate, butyl ricinoleate, methyl ricinoleate, methyl acetyl ricinoleate, butyl oleate, glycerin triacetyl ricinoleate, and butyl acetyl ricinoleate are used. There is.
It also shows examples of the combination of glycerin trioleate / castor oil and n-butylacetyl ricinoleate / castor oil.

(3) US Pat. No. 5,427,704 includes:
In triglyceride estolide, compositions are shown that have thickened animal fats, vegetable oils or synthetic triglyceride oils. Triglyceride estolide is obtained, for example, by reacting castor oil or resquerella oil with heptanoic acid, isostearic acid, oleic acid and the like.

(4) JP-A-63-168256 discloses that castor oil is 61.7%, graphite is 0.8 to 5%, and grease is 5 to 1%.
There is disclosed a lubricating oil for casting (particularly a lubricating oil for hot-top casting of non-ferrous metals such as aluminum) having a viscosity of 300 to 4000 cps at 25 ° C., comprising 3.3% and 8 to 20% of other fats and oils. Japanese Unexamined Patent Publication (Kokai) No. 4-153296 discloses a non-ferrous metal casting lubricant in which the content of boron nitride powder is 0.5 to 3% by weight and the balance is a vegetable oil-based liquid lubricant. The one specifically mentioned as a vegetable oil-based liquid lubricant is castor oil only.

(5) JP-A-7-228881 discloses an ester composition comprising an ester of a condensed fatty acid (estolide) and a hindered alcohol, and this composition has various properties which require lubricating performance. It can be used for applications. See also JP-A-8-274
No. 73 discloses a lubricant containing an ester of a condensed fatty acid (estolide) and a hindered alcohol as an essential component, and this lubricant has a lubricating performance either alone or in combination with another lubricant. Although it can be used for various required applications, there is no description about specific examples used in combination with other lubricants. JP-A-8-92581 discloses a lubricating composition containing an esterification reaction product of castor oil or hydrogenated castor oil with a condensed fatty acid as an essential component. Conventional lubricating compositions such as animal and vegetable oils, esterified oils and mineral oils are disclosed. There is also a statement that it is used by being mixed with a used lubricating oil at an appropriate ratio.

(6) JP-A-5-78673 discloses that
There is disclosure of using esters of condensed 12-hydroxystearic acid and polyhydric alcohols as flow improvers for fuel oils from petroleum middle distillates.

[0014]

The present invention is based on natural fats and oils having no environmental problems, and has a stable liquid state throughout the season, has a sufficient oily viscosity even at high temperatures, and has a viscosity such as transportation at low temperatures. It is required to maintain a viscosity that does not hinder the work and have a certain degree of oxidation stability.
However, as mentioned above, a product satisfying such a requirement cannot be obtained only by selecting a certain fat or oil from natural fats and oils, and a product satisfying such a requirement only by blending natural fats and oils together. Is difficult to obtain.

The above (1) has an effect of suppressing an increase in the viscosity of castor oil at a low temperature, but the effect of suppressing a decrease in the viscosity at a high temperature is rather deteriorated. Note that this method
Since this is a reaction in which a fatty acid or dibasic acid is condensed in a cap shape with the OH group of castor oil, it can be said to be a kind of estolide formation reaction. However, when focusing on the constituent fatty acids of castor oil, the degree of condensation is only 2 at most.

In the composition (2), the high viscosity at low temperatures can be solved by adding castor oil to glycerin trioleate, but the property of decreasing the viscosity at high temperatures cannot be solved.

The composition of the above (3) is, for example, as shown in Table 1
According to the composition of 90 parts by weight of vegetable oil and 10 parts by weight of triglyceride estolide, the viscosity at 40 ° C. is increased from 40 Cst in the case of vegetable oil alone to about 45 to 65 Cst, and the viscosity at 100 ° C. of vegetable oil alone. 8.3 ~ 8.6 Cs in case
t is increased only to about 9 to 13 Cst. Even in the case of a composition comprising 80 parts by weight of vegetable oil and 20 parts by weight of triglyceride estolide, the viscosity at 40 ° C. is increased from about 40 Cst to 50 to 99 Cst in the case of vegetable oil alone. Up to 100
The viscosity at ℃ is 10 from 8.3 ~ 8.6 Cst of vegetable oil alone.
It only increases the viscosity to about 18 Cst, and the effect of increasing the viscosity is limited. Since this method also condenses an acid to the OH group of castor oil in the form of a cap, the degree of condensation is only 2 at most when focusing on the constituent fatty acids of castor oil.

The viscosity of the casting lubricating oil or casting lubricant (4) is controlled by blending graphite or boron nitride. However, inorganic substances that do not dissolve in fats and oils have problems in terms of dispersion, sedimentation, environment and the like. Therefore, it is desirable to improve the viscosity of the base fat component itself.

The composition (5) is not directly intended to improve the viscosity of natural fats and oils, but merely discloses background technology.

The fluidity improver for fuel oil of the above (6) is also said to improve the fluidity of fuel oil from petroleum middle distillate, but is intended to improve the viscosity of natural fats and oils. Not.

The object of the present invention is to improve the viscosity of natural liquid oils and fats which have no environmental problems,
Natural oils and fats that are easy to handle throughout the season, exhibit sufficient viscosity even at high temperatures, can ensure oxidative stability, and can be implemented sufficiently in terms of cost. It is to provide a composition.

[0022]

The natural oil / fat liquid composition of the present invention comprises a natural oil / fat component (A) and an ester component (B) comprising a polyhydric alcohol ester of an oxy fatty acid condensate as a viscosity modifier. Composition comprising an ester component
When the average degree of condensation of the oxy fatty acid condensate in (B) is 2.5 or more, and the total amount of the natural oil and fat component (A) and the ester component (B) is 100% by weight, the natural oil and fat component ( (A) is 98 to 55% by weight, the proportion of the ester component (B) is 2 to 45% by weight, and the two components of the natural fat / oil component (A) and the ester component (B) are measured by a B-type viscometer. The viscosity η _{40 at} a temperature of 40 ° C. of the composition of the present invention is 70 to 500 cps,
The viscosity η _{100 at a} temperature of 100 ° C. is 15 to 60 cps,
And the logarithmic ratio of the viscosities at both temperatures log (η ₄₀ ) / lo
g (η ₁₀₀ ) is 1.80 or less, and the above object has been achieved by finding such a specific natural fat / oil-based liquid composition.

[0023]

BEST MODE FOR CARRYING OUT THE INVENTION The natural fat / oil composition of the present invention comprises a natural fat / oil component (A) and an ester component (B) as main components.

The natural fats and oils (A) include castor oil, rapeseed oil, palm olein, soybean oil, palm oil, palm kernel oil, olive oil, corn oil, safflower oil, rubber seed oil, tea seed oil, sunflower oil, Cottonseed oil, meadowfoam oil,
Vegetable oils such as camellia oil, vegetable oils having an increased oleic acid content by genetic manipulation, or animal oils such as lard and orange luffy are used. From the viewpoint of characteristic balance and cost, the weight ratio of castor oil to common natural fats and oils other than castor oil (such as rapeseed oil) is 95: 5 to 5: 9.
It is particularly desirable to use a mixture of 5 (especially 90:10 to 10:90).

As the ester component (B), a polyhydric alcohol ester of an oxy fatty acid condensate is used.

The oxyfatty acid condensate is obtained by converting C
It is synthesized by a condensation reaction between an OOH group and an OH group of an oxy fatty acid. Representative examples of oxy fatty acids are castor oil fatty acids whose main component is ricinoleic acid,
Hydrogenated castor oil fatty acid which is hydroxystearic acid.

The condensation reaction can be achieved by heating the above fatty acid or a mixture thereof under an inert gas atmosphere at a temperature of about 160 to 220 ° C. At this time, it is preferable to carry out the reaction under reflux conditions in the presence of an appropriate solvent, and to remove by-product water from the system by azeotropic distillation. A catalyst may not be used, but an acid catalyst may be used.

The average degree of condensation of the oxy fatty acid condensate must be at least 2.5 or more, particularly preferably 3 or more. When the average degree of condensation is smaller than this range, the effect of improving the viscosity of the natural fat / oil component (A) is insufficient.
The upper limit of the average degree of condensation is not limited, but is usually set to about 7 from the viewpoint of ease of reaction. A particularly preferred range of the average degree of condensation is 4 to 6.

The average degree of condensation of the condensate when the above-mentioned condensation reaction is carried out can be judged from the decrease in the acid value. That is, when the oxy fatty acid is a castor oil fatty acid having 18 carbon atoms or a hydrogenated castor oil fatty acid, the acid value is approximately 180. Therefore, if the acid value of the reaction product after the condensation reaction is 1 / n, the average is Thus, it can be said that an n-mer is generated. For example, if the acid value is 40, the average is about 4.5 mer, and if the acid value is 36, the average is about 5 mer.

As the polyhydric alcohol for obtaining the polyhydric alcohol ester of the oxy fatty acid condensate, those having an OH functionality of 2, such as polyethylene glycol and neopentyl glycol, can be used. The above, for example, trimethylolpropane, glycerin, diglycerin (OH functional number is 4), polyglycerin (glycerin is connected with 3 or more molecules and OH functional number is 5 or more), pentaerythritol, dipentaerythritol, Sorbitol and the like are preferred. Of these, di- or polyglycerin is particularly suitable for the purposes of the present invention. The _{polyglycerol, CH 2 (OH) -CH (} OH) -CH 2 -O- (CH 2 -CH (OH) -CH 2 -O) n -CH 2 -CH (O
H) -CH ₂ (OH) (n is 1 or more).

The polyhydric alcohol ester of the oxyfatty acid condensate is obtained by converting the oxyfatty acid condensate and the polyhydric alcohol to zinc chloride, stannous chloride, paratoluenesulfonic acid, sulfuric acid, hydrochloric acid, phosphoric acid, sodium methylate, etc. It is obtained by performing a heating reaction at a temperature of about 170 to 220 ° C. in the presence of a catalyst. Although the coloring is less likely to occur when the reaction is performed in an inert gas atmosphere, the reaction may be performed in an air atmosphere. It is preferable that the reaction is carried out under reflux in the presence of an appropriate solvent in the system, and that water produced as a by-product is removed from the system by azeotropic distillation.

The reaction ratio between the oxyfatty acid condensate and the polyhydric alcohol is set so as to be approximately equivalent or slightly higher for the polyhydric alcohol.
It is sufficient if at least 70%, preferably at least 80% of the groups are esterified.

The iodine value of the ester component (B) is desirably 40 or less, preferably 35 or less, and more preferably 30 or less. Setting the iodine value of the ester component (B) within this range can be easily achieved by selecting the oxy fatty acid in the oxy fatty acid condensate.

When the total amount of the natural fat / oil component (A) and the ester component (B) is 100% by weight, the ratio of the natural fat / oil component (A) is 98 to 55% by weight ( The proportion of the ester component (B) is set to 2 to 45% by weight (preferably 5 to 40% by weight). When the proportion of the ester component (B) is too small, the viscosity at a high temperature of the composition becomes too small and the effect of improving the viscosity is insufficient.On the other hand, when the proportion of the ester component (B) is too large, the viscosity of the natural fat or oil is improved. In addition to deviating from the purpose, the cost becomes high and practicality is lost.

In the present invention, the viscosity η _{40 at} a temperature of 40 ° C. of the two compositions of the natural fat / oil component (A) and the ester component (B) as measured by a B-type viscometer is 70 to 500.
cps (preferably 80-450 cps, more preferably 90-420 cps) and a viscosity η at a temperature of 100 ° C.
It is necessary that ₁₀₀ is 15 to 60 cps (preferably 17 to 50 cps, more preferably 18 to 45 cps). When the viscosity at each temperature is out of the above range, the fluidity at a low temperature is impaired, or the viscosity at a high temperature becomes insufficient.

Further, in the present invention, the logarithm of the viscosity η _{40 at} a temperature of 40 ° C. and the viscosity η _{100 at a} temperature of 100 ° C.
Log (η ₄₀ ) / log (η ₁₀₀ ) must be 1.80 or less. When this ratio exceeds 1.80, the tendency of viscosity increase at low temperature becomes large, and the tendency of viscosity decrease at high temperature becomes large. log (η ₄₀ ) / log (η ₁₀₀ ) is 1.77 or less,
Further, it is preferably 1.75 or less, particularly preferably 1.73 or less. Although the lower limit is preferably closer to 1, the influence of temperature on the viscosity is unavoidable due to the laws of nature. Therefore, in practice, the lower limit is about 1.40, and the usual lower limit is about 1.50.

The iodine value of the two compositions of the natural fat / oil component (A) and the ester component (B) cannot be determined unequivocally because the allowable range differs depending on the application, but is 90 or less, and even 85 or less. Preferably, there is. This is because the smaller the iodine value, the higher the oxidation stability. Therefore, the type and ratio of the natural fat / oil component (A) and steal component (B) should be set in consideration of the iodine value according to the use.

The natural oil / fat liquid composition of the present invention may contain, besides the above-mentioned natural oil / fat component (A) and ester component (B), other organic or An appropriate amount of an inorganic component can be contained.

The natural oil / fat composition of the present invention can be used as an electrorheological fluid, an ultrasonic medium, a lubricant for casting non-ferrous metals, a lubricating oil, etc. (various lubricating oils, engine oils, chainsaw oils,
It is also useful as a hydraulic oil, rolling oil, processing oil, refrigerating machine oil, air compressor oil, and the like.

<Action> In the natural oil / fat liquid composition of the present invention, the natural oil / fat component (A) plays a role of a base,
The ester component (B) acts as a viscosity modifier. The average degree of condensation of the oxyfatty acid condensate in the ester component (B), the ratio of the two components of the natural fat / oil component (A) and the ester component (B), and the viscosity η _{40 of} these two compositions at a temperature of 40 ° C. , viscosity eta ₁₀₀ at temperature 100 ° C., further the ratio of the logarithm of the viscosity at these two temperatures _{log (η 40) / log (} η 100)
In the natural oil-and-fat-based liquid composition of the present invention selected from the above-specified range, the increase in viscosity in a low-temperature region of 40 ° C. or less is suppressed, and the viscosity in a high-temperature region of 100 ° C. or more is reduced. The decrease is effectively suppressed, and as a result, handling properties throughout the season are improved, and sufficient oiliness can be obtained even at high temperatures, while leaving the goodness of natural liquid fats and oils having no environmental problems. It is also easy to ensure oxidation stability.

[0041]

EXAMPLES Next, examples of the synthesis of oxyfatty acid condensates, examples of the synthesis of esters using the oxyfatty acid condensates, examples of the natural fat / oil composition of the present invention, and comparative examples will be given.
The present invention will be further described.

<Synthesis of oxy fatty acid condensate> Synthesis Example 1 Castor oil fatty acid 20 was placed in a four-necked flask equipped with a stirrer, a thermometer, a nitrogen inlet tube and a reflux condenser equipped with a water sample tube.
0 g, hydrogenated castor oil fatty acid 400 g and xylene 12
0 ml was charged and heated to 180 to 210 ° C. under a nitrogen stream, and the reaction was carried out for 7 hours while removing generated water out of the system to recover xylene. The acid value of the obtained condensate was 39.

Synthesis Example 2 500 g of hydrogenated castor oil fatty acid and 100 ml of xylene were charged into a four-necked flask equipped with a stirrer, a thermometer, a nitrogen inlet tube and a reflux condenser equipped with a test tube, and heated to 180 to 210 ° C. under a nitrogen stream. The mixture was heated and reacted for 9 hours while removing generated water out of the system, and xylene was recovered. The acid value of the obtained condensate was 34.

Synthesis Example 3 Castor oil fatty acid 40 was placed in a four-necked flask equipped with a stirrer, a thermometer, a nitrogen inlet tube and a reflux condenser equipped with a test tube.
0 g and xylene 100 ml were charged, and the
The mixture was heated to ２１０210 ° C. and reacted for 6 hours while removing generated water out of the system to recover xylene. The acid value of the obtained condensate was 40.

Summary of Synthesis Examples 1 to 3 Table 1 summarizes the production conditions of the above Synthesis Examples 1 to 3, the acid value of the obtained oxyfatty acid condensate, and the average degree of condensation. In Table 1, COFA is castor oil fatty acid, and HCOFA is hydrogenated castor oil fatty acid. The average degree of condensation was determined by dividing 180 by the acid value of the condensate.

[0046]

[Table 1] Type and amount of oxy fatty acid Reaction Acid value Average time Condensation degree Synthesis example 1 COFA 200 g + HCOFA 400 g 7 hr 39 4.6 Synthesis example 2 HCOFA 400 g 9 hr 34 5.3 Synthesis example 3 COFA 400 g 6 hr 40 4.5

<Synthesis of Ester> Synthesis Example 4 In a four-necked flask, 400 g of the oxyfatty acid condensate having an acid value of 34 of Synthesis Example 2 described above and polyglycerin (“Polyglycerin # 310” manufactured by Sakamoto Yakuhin Kogyo Co., Ltd.) Hydroxyl value 1
050-1090, polyglycerin content 80-90%)
16 g, xylene 120 ml and stannous chloride (catalyst)
0.4 g was charged and reacted for 6 hours while removing generated water out of the system under xylene reflux conditions to recover xylene. The acid value of the obtained ester was 8.

Synthesis Example 5 A four-necked flask was charged with 400 g of the oxyfatty acid condensate having an acid value of 39 described in Synthesis Example 1, 12 g of diglycerin, 120 ml of xylene and 0.4 g of stannous chloride (catalyst).
The reaction was carried out for 6 hours while removing generated water out of the system under xylene reflux conditions, and xylene was recovered. The acid value of the obtained ester was 6.

Synthesis Example 6 In a four-necked flask, 400 g of the oxyfatty acid condensate having an acid value of 39 obtained in Synthesis Example 1 and trimethylolpropane 14 were added.
g, xylene 120 ml and stannous chloride (catalyst) 0.4
g of xylene and reacted for 6 hours while removing generated water out of the system under xylene reflux conditions to recover xylene. The acid value of the obtained ester was 9.

Synthesis Example 7 In a four-necked flask, 350 g of the oxyfatty acid condensate having an acid value of 34 of the above-mentioned Synthesis Example 2, 150 g of the oxyfatty acid condensate having an acid value of 40 of the above Synthesis Example 3, and polyethylene glycol having an average molecular weight of 200 33 g, 120 ml of xylene and 0.4 g of stannous chloride (catalyst) were charged and reacted for 6 hours while removing generated water out of the system under xylene reflux conditions to recover xylene. The acid value of the obtained ester was 2.

Synthesis Example 8 In a four-necked flask, 350 g of the oxyfatty acid condensate having an acid value of 34 obtained in Synthesis Example 2 above, 150 g of the oxyfatty acid condensate having an acid value of 40 obtained in Synthesis Example 3 described above, and diglycerin having an average molecular weight of 200 were prepared. 14 g, 120 ml of xylene and 0.4 g of stannous chloride (catalyst) were charged and reacted for 6 hours while removing generated water from the system under reflux conditions of xylene to recover xylene. The acid value of the obtained ester was 5.

Summary of Synthesis Examples 4 to 8 Table 2 summarizes the production conditions of the above Synthesis Examples 4 to 8 and the acid value, viscosity and iodine value of the obtained ester. The reaction ratio between the oxy fatty acid condensate and the polyhydric alcohol in the synthesis of the ester uses the latter approximately 1.1 times equivalent to the theoretical amount. In Table 2, polygly. Is polyglycerin, di
gly. is diglycerin, TMP is trimethylolpropane, and PEG is polyethylene glycol. In addition, since the iodine value of the esters obtained in Synthesis Examples 4 to 8 is considerably low, it can be seen that when they are blended with natural fats and oils, they are also advantageous in terms of oxidation stability. Incidentally, as disclosed in U.S. Pat. No. 5,427,704 described in the prior art, triglyceride estolide obtained by reacting a fatty acid with an OH group of castor oil in a cap form has an iodine value of only about 45 at a minimum.

[0053]

[Table 2] Oxy fatty acid condensate: Polyhydric alcohol: Acid value Iodine g number g number Synthesis example 4 Synthesis example 2: 400 polygly .: 16 8 2 Synthesis example 5 Synthesis example 1: 400 digly .: 12 6 25 Synthesis example 6 Synthesis example 1: 400 TMP: 14 9 24 Synthesis Example 7 Synthesis Example 1: 400 PEG: 33 222 Synthesis Example 8 Synthesis Example 2: 350 + Synthesis Example 3: 150 digly .: 14 5 28

<Natural fat / oil type liquid composition> Examples 1 to 13 Examples of synthesis as ester component (B) using one or a combination of castor oil, rapeseed oil and palm olein as natural fat / oil component (A) Using the esters obtained in 4 to 8, the iodine value and the temperature of 1
The viscosities at 0 ° C, 40 ° C, 100 ° C and 130 ° C (measured using a B-type viscometer) were measured. Tables 3 and 4 show the conditions and results. "%" Is% by weight.
"-" Indicates that no measurement was performed.

[0055]

[Table 3] Example 1 2 3 4 5 6 7 8 Natural fat component (A) (%) Castor oil 60 72 40 64 50 80 40 35 Rapeseed oil 30 40 10 40 35 Palm olein 18 16 30 Ester component (B) (%) Synthesis example 4 10 10 20 20 20 Synthesis example 5 10 20 30 Viscosity (cps) 10 ° C 738 1200 713 1650 1028 1260 675 994 40 ° C 176 240 185 330 240 246 180 260 100 ° C 21 24 24 32 28 24 24 34 130 ° C 12 13 14 18 16 13 14 19 log (η ₄₀ ) / log (η ₁₀₀ ) 1.70 1.72 1.64 1.67 1.64 1.73 1.63 1.58 Iodine value 83 72 75 64 60 81 81 74

[0056]

[Table 4] Example 9 10 11 12 13 Natural fat component (A) (%) Castor oil 30 80 80 80 Rapeseed oil 30 10 10 50 Palm olein 20 Ester component (B) (%) Synthesis example 5 40 Synthesis example 6 10 20 Synthesis example 7 10 Synthesis example 8 30 Viscosity (cps) 10 ° C 1448 1302 1250 450 1895 40 ° C 365 250 235 150 337 100 ° C 46 24 22 25 30 130 ° C 26 13 12 15 − log (η ₄₀ ) / log (η ₁₀₀ ) 1.54 1.74 1.77 1.56 1.71 Iodine value 67 81 81 72 73

Comparative Examples 1 to 3 Castor oil alone (Comparative Example 1) as a natural fat / oil component (A)
75:25, 50: 5 by weight ratio of castor oil and rapeseed oil
Table 5 shows iodine values and viscosities at various temperatures when a mixture of 0, 25:75 (Comparative Examples 2 to 4) and rapeseed oil alone (Comparative Example 5) were not used and the ester component (B) was not blended.

[0058]

[Table 5] Comparative Example 1 2 3 4 5 Natural fat component (A) Castor oil 100 75 50 25 0 Rapeseed oil 0 25 50 75 100 Viscosity (cps) 10 ° C 2062 1053 653 412 103 40 ° C 280 140 93 50 38 100 ° C 18 15 12 8 7 130 ° C 9 7 6 5 4 log (η ₄₀ ) / log (η ₁₀₀ ) 1.95 1.82 1.82 1.88 1.87 Iodine value 85 90 95 100 105

From Tables 3 and 4, it can be seen that in all of Examples 1 to 13, the viscosity at a low temperature is suppressed to a relatively low level and the viscosity at a high temperature is maintained at a relatively high level. In particular, as in Examples 1 to 5, polyglycerol ester of an oxy fatty acid condensate (Synthesis Example 4) as the ester component (B), and as in Examples 6 to 9 and Example 12, the oxy fatty acid as the ester component (B). Optimum results are obtained when diglycerin esters of condensates (Synthesis Examples 5 and 8) are used.

Example 12 is an example in which rapeseed oil and palm olein were used in combination as the natural fat / oil component (A) and castor oil was not used. However, good results were obtained by blending 30% of the ester component (B). Have been. Example 13
When only castor oil is used as the natural fat / oil component (A), when 20% of the ester component (B) is blended, the temperature is 40 ° C.
Although the viscosity is slightly high, the viscosity at 100 ° C. is high and the ratio of log (η ₄₀ ) / log (η ₁₀₀ ) is small, so that it can be used for a suitable application.

On the other hand, as shown in Table 5, in the case of castor oil alone (Comparative Example 1), the viscosity was significantly dependent on temperature, and
It shows the highest viscosity at 0 ° C. and at 130 ° C. Example 1
To 13 are lower in viscosity. In the case of rapeseed oil alone (Comparative Example 5), although the temperature dependence of the viscosity is small, the viscosity is too low regardless of the temperature. 75:25, 50:50, 25:75 by weight ratio of castor oil and rapeseed oil
In the case of the mixture (Comparative Examples 2 to 4), the mixture exhibits a viscosity behavior which is intermediate between Comparative Examples 1 and 5, but is relatively close to that of Comparative Example 5. The viscosity rankings of Comparative Examples 1 to 5 show the same tendency regardless of the temperature. In any case, the use of castor oil or rapeseed oil alone, or a mixed system of any ratio thereof, is too low in viscosity at a high temperature of 100 ° C., 130 ° C. or more, so that various applications are restricted.

[0062]

According to the natural oil / fat liquid composition of the present invention, the viscosity increases at a low temperature of 40 ° C. or less and the viscosity increases at 100 ° C.
Both of the above-mentioned lowering of the viscosity in the high temperature range are effectively suppressed, and as a result, the handling properties throughout the season are improved while leaving the goodness of the natural liquid oil and fat without environmental problems,
In addition, sufficient oiliness can be obtained even at high temperatures. It is also easy to ensure oxidation stability. In addition, the implementation is sufficiently possible in terms of cost.

Claims (5)

[Claims] 1. A composition comprising a natural oil component (A) and an ester component (B) comprising a polyhydric alcohol ester of an oxy fatty acid condensate as a viscosity modifier, wherein the oxy fatty acid in the ester component (B) is When the average degree of condensation of the condensate is 2.5 or more, and the total amount of the two components, the natural fat / oil component (A) and the ester component (B), is 100% by weight, the ratio of the natural fat / oil component (A) is 98%. 55% by weight and the proportion of the ester component (B) is 2 to 45%.
And the viscosity η at a temperature of 40 ° C. of the two compositions of the natural fat / oil component (A) and the ester component (B) as measured by a B-type viscometer.
₄₀ is 70-500 cps, viscosity η at a temperature of 100 ° C.
₁₀₀ is 15 to 60 cps, and the ratio of logarithm of viscosity at these two temperatures, log (η ₄₀ ) / log (η ₁₀₀ ), is 1.80 or less. 2. The natural oil / fat liquid composition according to claim 1, wherein log (η ₄₀ ) / log (η ₁₀₀ ) is 1.75 or less. 3. The natural fat component (A) is 95: 5 to 5: 9 by weight ratio of castor oil to general natural fats other than castor oil.
The natural oil-and-fat-based liquid composition according to claim 1, which is a mixture of No. 5 and No. 5. 4. The natural oil / fat liquid composition according to claim 1, wherein the polyhydric alcohol in the ester component (B) is di- or polyglycerin. 5. The natural oil-based liquid composition according to claim 1, wherein the iodine value of the ester component (B) is 40 or less.