KR102446371B1 - Lipid composition and uses thereof - Google Patents

Abstract

The present invention relates to a mixed fat and oil composition prepared from vegetable oil and uses thereof, and more particularly, to a mixed fat and oil composition with improved feeling of use by optimizing each triglyceride content by transesterification reaction, and to a use thereof.
The mixed oil composition of the present invention improves the viscosity, thereby enhancing the skin absorption power during skin application, thereby improving the disadvantages of skin oiliness and shine, as well as improving the feeling of use by spreading softly and smoothly on the skin, such as cosmetics, external preparations for skin, etc. can be widely used as

Description

Oil composition and uses thereof

The present invention relates to a mixed fat and oil composition prepared from vegetable oil and uses thereof, and more particularly, to a mixed fat and oil composition with improved feeling of use by optimizing each triglyceride content by transesterification reaction, and to a use thereof.

Vegetable oils are composed of mixtures of esters, and in general, about 90-98% of vegetable oils and fats consist of triglycerides and less than 10% of mono and/or diglycerides.

These vegetable oils and fats are widely used as cosmetic and pharmaceutical compositions, but when applied to the skin, triglycerides, which are the main components of the oil, penetrate slowly into the skin, so there is a disadvantage that it is oily and shows a feeling of intense shine.

In order to solve this problem, research on various esters is in progress, and Korean Patent Publication No. 10-2002-0063909 discloses esters of fatty alcohols and fatty acids derived from transesterification of triglycerides of vegetable origin with fatty alcohols; And formulations containing residual triglycerides, diglycerides, and monoglycerides derived from the transesterification are known. A deodorant prepared from woolwax acid and partial glycerides for

In general, the transesterification reaction of triglycerides is produced by the synthesis between triglycerides or the chemical synthesis of fatty acids and glycerin. . In addition, various reaction catalysts such as metal catalysts are used as catalysts for chemical reactions, and it is known that these catalysts can cause safety problems due to residual problems in the final product. In addition, the thermal stability and functional value of the final product are disadvantageous due to the rancidity of the unsaturated fatty acids constituting the oil and fat due to the high temperature treatment of edible oils and fats. There are non-economic disadvantages.

As mentioned above, vegetable oils are also widely used in cosmetics and pharmaceutical compositions, but user satisfaction is not yet sufficient. Therefore, there is a demand for economical process development capable of preventing environmental pollution while improving user satisfaction such as skin penetration rate and skin glossiness when applying to the skin.

Korean Patent Publication No. 10-2002-0063909 Korean Patent No. 10-0337969

The present invention is to solve the above problems, and an object of the present invention is to provide an oil-fat composition with an improved feeling of use by optimizing the content of individual triglycerides through an ester conversion reaction of an eco-friendly vegetable oil.

Another object of the present invention is to provide a cosmetic composition, an anti-inflammatory composition, a composition for external application for skin, and a food containing the oil composition.

the present invention

5 to 30 wt% of a first triglyceride compound represented by the following formula (1);

10 to 70 wt% of a second triglyceride compound represented by the following formula (2) and

It provides a mixed fat and oil composition comprising 10 to 70% by weight of the third triglyceride compound represented by the following formula (3).

[Formula 1]

In Formula 1, RL ₁ to RL ₃ are each independently a linear or branched saturated or unsaturated C ₁₀ to C ₂₂ alkyl group, and may be the same as or different from each other.

[Formula 2]

In Formula 2, any one selected from Ra ₁ to Ra ₃ is hydrogen, a linear or branched saturated or unsaturated C ₁ to C ₉ alkyl group,

The other two of Ra ₁ to Ra ₃ are each independently a linear or branched saturated or unsaturated C ₁₀ to C ₂₂ alkyl group, and may be the same as or different from each other.

[Formula 3]

In Formula 3, any one selected from Rb ₁ to Rb ₃ is a linear or branched saturated or unsaturated C ₁₀ ~ C ₂₂ alkyl group,

The other two of Rb ₁ to Rb ₃ are each independently hydrogen or a linear or branched saturated or unsaturated C ₁ to C ₉ alkyl group, and may be the same as or different from each other.

In the present invention, the mixed oil composition may be prepared by transesterification of vegetable oil and carboxylic acid or a derivative thereof.

The vegetable oil is one or two selected from citron seed oil, camellia seed oil, green tea seed oil, coconut oil, palm oil, palm kernel oil, castor oil, olive oil, grape seed oil, canola oil, safflower oil, rice bran oil, sunflower oil and soybean oil It may be a mixture of the above.

The transesterification reaction may be performed by a lipase enzyme.

In addition, the present invention provides a cosmetic composition, an anti-inflammatory composition, a composition for external application to the skin, or a food comprising the mixed oil composition.

The oil-fat composition of the present invention uses an esterification reaction through a biological conversion reaction of vegetable oil, and is environmentally friendly and has high economic efficiency.

In particular, the mixed oil composition of the present invention improves the viscosity by improving the skin absorption power when applied to the skin, thereby improving the disadvantages of skin oiliness and shine, as well as improving the feeling of use by spreading it on the skin softly and smoothly. It can be widely used as an external preparation and the like.

1 is a photograph confirming the stability of an oil-fat composition according to the present invention.

Hereinafter, the present invention will be described in detail. Prior to this, the terms or words used in the present specification and claims should not be construed as being limited to conventional or dictionary meanings, and the inventor should properly understand the concept of the term in order to best describe his invention. Based on the principle that it can be defined, it should be interpreted as meaning and concept consistent with the technical idea of the present invention. Therefore, the configuration described in the embodiment described in this specification is only the most preferred embodiment of the present invention and does not represent all of the technical idea of the present invention, so various equivalents and It should be understood that there may be variations.

In describing the present invention, terms such as first, second, A, B, (a), (b), etc. may be used. These terms are only for distinguishing the elements from other elements, and the essence, order, or order of the elements are not limited by the terms.

In describing the present invention, the terms 'about', 'substantially', 'degree', etc. of degree are used in or close to the numerical value when manufacturing and material tolerances inherent to the stated meaning are presented. , in order to help the understanding of the present invention, precise or absolute figures are used to prevent an unconscionable infringer from using the disclosed disclosure unfairly.

The mixed fat and oil composition of the present invention is

5 to 30 wt% of a first triglyceride compound represented by the following formula (1);

10 to 70 wt% of a second triglyceride compound represented by the following formula (2) and

10 to 70% by weight of the third triglyceride compound represented by the following formula (3).

[Formula 1]

In Formula 1, RL ₁ to RL ₃ are each independently a linear or branched saturated or unsaturated C ₁₀ to C ₂₂ alkyl group, and may be the same as or different from each other.

[Formula 2]

In Formula 2, any one selected from Ra ₁ to Ra ₃ is hydrogen, a linear or branched saturated or unsaturated C ₁ to C ₉ alkyl group,

The other two of Ra ₁ to Ra ₃ are each independently a linear or branched saturated or unsaturated C ₁₀ to C ₂₂ alkyl group, and may be the same as or different from each other.

[Formula 3]

In Formula 3, any one selected from Rb ₁ to Rb ₃ is a linear or branched saturated or unsaturated C ₁₀ ~ C ₂₂ alkyl group,

The other two of Rb ₁ to Rb ₃ are each independently hydrogen or a linear or branched saturated or unsaturated C ₁ to C ₉ alkyl group, and may be the same as or different from each other.

In general, glyceride consists of an ester bond between fatty acid and glycerol, and is affected by physical/chemical properties such as melting point, hardness, and freezing point depending on the type of fatty acid having a straight or branched carbon chain.

For example, the more saturated fatty acids are bound, the higher the melting point, the solid phase, and the stability against oxidation increase, but in the case of unsaturated fatty acids, the liquid phase is displayed. However, even if it is a saturated fatty acid, if the chain of the fatty acid is shortened, it may be liquid.

In addition, even when applied to the skin, the type of fatty acid affects the skin penetration rate and stability. Unsaturated fatty acids are known to have low oxidation stability due to the increased degree of oxidation due to the dissociation of the double bond, whereas polyunsaturated fatty acids such as linoleic acid and linolenic acid It is known that unsaturated fatty acids can be transformed into other polyunsaturated fatty acids by enzymes contained in the epidermis, particularly to prevent transepidermal water loss. In addition, as the fatty acid chain length increases, it forms a protective film on the skin, thereby exhibiting the effect of preventing moisture loss and skin softness, but there is also a problem such as inducing oiliness and shine due to the low penetration rate into the epidermis.

Mixed oil composition of the present invention to improve the viscosity of the composition,

5 to 30% by weight of a first triglyceride compound in which three long chain fatty acid groups are bonded;

10 to 70 wt% of a second triglyceride compound in which two long-chain fatty acid groups and one short-chain fatty acid group are bonded;

10 to 70% by weight of the third triglyceride compound in which one long-chain fatty acid group and two short-chain fatty acid groups are bonded may be included.

More preferably, 10 to 20% by weight of the first triglyceride compound, 20 to 50% by weight of the second triglyceride compound, and 30 to 65% by weight of the third triglyceride may be included.

When the first triglyceride is present in less than the above range, the viscosity of the oil is too low and the feeling of use is light.

In addition, when the second triglyceride is present below the above range, the degree of improvement in spreadability and smoothness is not sufficient, and when the second triglyceride is present in excess of the above range, the degree of improvement in spreadability is not sufficient.

In addition, when the third triglyceride is present in less than the above range, the smooth feel is low, and when the third triglyceride is present in excess of the above range, the viscosity is low and the feeling of use is too light.

The mixed oil composition may be prepared by transesterification of vegetable oil and carboxylic acid or a derivative thereof.

The vegetable oil is one or two selected from citron seed oil, camellia seed oil, green tea seed oil, coconut oil, palm oil, palm kernel oil, castor oil, olive oil, grape seed oil, canola oil, safflower oil, rice bran oil, sunflower oil and soybean oil A mixture of the above may be used, but is not limited thereto.

As the carboxylic acid, formic acid or a compound containing an alkyl group of C ₁ to C ₉ may be used, and specifically, metanoic acid, etanoic acid, propanoic acid, butanoic acid, pentanoic acid, hexanoic acid, Heptanoic acid, octanoic acid, nonanoic acid or decanoic acid may be used, but is not limited thereto.

In addition, the derivative of the carboxylic acid may include an ester obtained by the reaction of the carboxylic acid with a polyhydric alcohol.

The carboxylic acid or its derivative compound may be used in an amount of 10 to 100 parts by weight, preferably 20 to 80 parts by weight, based on 100 parts by weight of the vegetable oil.

When the carboxylic acid or its derivative compound is used in less than the above range, the transesterification reaction does not proceed sufficiently, and when used in excess of the above range, the transesterification reaction proceeds excessively, so that a desired feeling of use is not obtained.

The transesterification reaction may be performed by a lipase enzyme.

The lipase enzyme may use a microorganism-derived enzyme or a commercially available enzyme, specifically selected from the group consisting of Novozyme 435 (Novozym 435), Lipozyme RM IM (Lipozyme RM IM), and Lipozyme TL IM (Lipozyme TL IM). One or more may be used, preferably lipozyme TL IM (Lipozyme TL IM), but is not limited thereto.

The transesterification reaction may be carried out by appropriately controlling the reaction time, temperature, and stirring speed.

The reaction time may be made for 3 to 50 hours, preferably 30 to 40 hours.

If the reaction time is too short, the transesterification reaction does not proceed sufficiently, so that the yield of the final product is reduced.

On the other hand, the reaction temperature may be 10 ~ 70 ℃, preferably 20 ~ 60 ℃.

If the reaction temperature is too low, the reaction does not proceed sufficiently, and the yield of the final product is reduced.

The composition on which the transesterification reaction is completed may be purified into a mixed oil and fat composition containing triglycerides through a distillation process, and the distillation process is not particularly limited.

As described above, the mixed oil composition according to the present invention is a triglyceride reconstituted by transesterification reaction, and not only is eco-friendly and economical in which various problems appearing in chemical transesterification reactions are solved, but also when applied to the skin. As a result, the tactile sensation such as spreadability and smoothness is improved, and the skin penetration rate is increased by improving the stickiness of the oil, that is, the viscosity, and the efficacy of the skin greasiness is significantly improved.

Therefore, the mixed fat and oil composition of the present invention can be usefully used as a cosmetic composition and a composition for external application for skin.

In addition, the mixed fat and oil composition according to the present invention is excellent in anti-inflammatory effect, moisturizing, heat and temperature stability, etc., it can be used as a composition for external application for skin or food.

Hereinafter, the present invention will be described in detail by way of Examples and Experimental Examples.

However, the following Examples and Experimental Examples only illustrate the present invention, and the present invention is not limited by the following Examples and Experimental Examples.

[Example 1] Preparation of mixed fat and oil composition 1

After mixing purified citron seed oil and ethanoic acid in a weight ratio of 1: 0.3 to a total of 1 kg, lipozyme TL IM (manufactured by Novozyme) 0.1 kg was used for transesterification at 50 ° C. for 30 hours. An oil-fat composition was obtained. The oil composition was subjected to molecular distillation at 150° C. under 0.1 Torr conditions to prepare a final mixed oil composition.

[Example 2] Preparation of mixed fat and oil composition 2

After mixing purified camellia seed oil and tricaprylin in a weight ratio of 1:0.7 each to a total of 1 kg, lipozyme TL IM (manufactured by Novozyme) 0.1 kg was used for transesterification at 50° C. for 30 hours and maintained. A composition was obtained.

The oil composition was subjected to molecular distillation at 170° C. under 0.1 Torr conditions to prepare a final mixed oil composition.

[Analysis Conditions]

Glyceride composition of mixed fat and oil composition (HPLC analysis)

The column uses Supelcosil LC-Si 5 μm, 25 cm (Supelco, USA), and the mobile phase solvent is solvent A (benzene 70: chloroform 30: acetic acid 2, volume ratio) and solvent B (ethyl acetate). , and the sample injection concentration was 1 mg/ml (chloroform solvent) and analyzed at a flow rate of 2.3 ml/min using an evaporative scattered light detector (ELSD). Through this, the content ratio of triglyceride in each composition was confirmed, and it is shown in Table 1 below as weight %.

division citron oil Example 1 Example 2 tertiary triglyceride 0.9 54.3 39.1 Second triglyceride
(1,3-position C10~22 alkyl group) 8.4 24.4 32.1 Second triglyceride
(1,2-position C10-22 alkyl group) 10.4 13.8 first triglyceride 87.3 10.9 15.0

Fatty Acid Analysis of Mixed Oil and Fat Composition (GC analysis)

The mixed oils and fats compositions of Examples 1 and 2 were methylated, and 50ul of the obtained methylated sample was dissolved in 1ml of hexane to analyze column conditions (SP ^TM -2560 Capillary, L 100m, ID 0.25 mm, dF 0.2 um), inlet conditions (250°C, Split Ratio 50:1), oven conditions (Flow 1.5ml/min, and initial temperature 140°C, 5min, 4°C/min, 210°C (10 min), 240°C (5 min) ), 250°C (5min)), FID detector conditions (250°C, H2 Flow 35 ml/min, Air Flow 300 ml/min, Makeup Flow (He) 20 ml/min) were analyzed by injecting 1 ul of sample.

Through the above analysis, the content ratio of carboxylic acid in each composition was measured, and it is shown in Table 2 below as weight %.

division citron oil Camellia Seed Oil Example 1 Example 2 Ethanoic acid 0.0 0.0 47.8 0.0 Octanoic acid 0.0 0.0 0.0 41.4 Hexadecanoic acid 18.09 18.8 11.2 11.1 Octadecanoic acid 3.26 8.5 2.0 5.0 Octadecenoic acid 34.44 71.2 19.6 41.7 Octadecadienoic acid 31.54 1.2 18.6 0.7 Octadecatrienoic acid 0.0 0.2 0.1 0.1

[Experimental Example 1] Test evaluation of the feeling of use of the oil-fat composition (Sensory test)

To evaluate the feeling of using natural oil, 11 male and female testers in their 20s and 50s were selected, applied 2 drops of each sample, and then applied to the skin using the index and middle fingers, and then evaluated for distribution, absorption and smoothness. , Stickiness and Gloss were evaluated for five tactile sensations. The degree of feeling of use was evaluated in 7 steps (-3 to +3) by comparing it with argan oil distributed in the market, and the results are shown in Table 3 below.

Evaluation items argan oil citron oil Example 1 Gloss 0 0.50 1.50 Stickiness 0 0.25 1.20 smoothness 0 0.60 -0.60 Distribution 0 0.00 -0.60 Absorption 0 0.60 -0.30

As shown in Table 3, the mixed oils and fats A of the present invention have significantly improved functions of distribution, absorption, and smoothness.

Spreadability means that it spreads smoothly and evenly over the entire area without biasing to one side when applied to the skin. Absorption means how quickly it is absorbed into the skin when applied to the skin. It is about how well it slides without a hitch, stickiness is how much parchment paper sticks when applied to the skin, and gloss is how shiny it is when applied to the skin.

In the case of citron seed oil, it is superior to argan oil in glossiness and spreadability, but its stickiness and smoothness are similar to argan oil. On the other hand, the mixed fat and oil composition of Example 1 had lower stickiness and gloss than citron seed oil, while remarkably improved dispersibility, absorbency, and smoothness. Predicting the reason, it seems that the viscosity of the oil is lowered due to the decrease in the chain length of the fatty acid, and the spreadability and smoothness are improved due to the improvement of the degree of stickiness. is reduced, and the feeling of use such as skin stickiness and skin greasiness is significantly improved compared to commonly used oils, and it may be usefully used as cosmetics and external preparations for skin.

[Experimental Example 2] Spreading test evaluation

After selecting 10 male and female testers in their 20s and 50s, applying 4 ul of the sample amount to the skin and leaving it for 10 minutes, lightly covering the application surface with oil paper, and measuring the area spread on the oil paper, the results are shown in Table 4 .

argan oil Example 1 196 mm2 310 mm2

The spreading test evaluation is for the degree of spreadability of the oil on the skin, and is closely related to the viscosity.

When compared with argan oil, it was confirmed that the spread area of the mixed oil composition of Example 1 was measured to be 1.5 times higher than that of argan oil, which means that the mixed oil composition of the present invention has remarkably good spreadability on the skin.

Combining the above Experimental Examples 1 and 2, the mixed fat and oil composition of the present invention has improved spreadability, stickiness, smoothness, absorbency, and shine (glossy). expected to increase

[Experimental Example 3] Anti-inflammatory evaluation of oil-fat composition

In the cytotoxicity evaluation, living cells convert MTT (3-[4,5-dimethylthiazol-2-yl]-2,5-diphenyltetrazolium bromide) into a blue formazon product by the reduction action of dehydrogenase present in mitochondria. After conversion, the resulting blue product was eluted with a solvent, and absorbance was measured at 540 nm using ELISA to measure the relative growth of living cells. RAW 264.7 cells or HaCaT cells were adjusted to a certain concentration using DMEM medium, inoculated in a 48 well plate, and pre-cultured for 18 hours. After treatment with a new medium containing the test substance and incubated for 24 hours, 100 μl of MTT solution (2 mg/ml) was added and reacted at 37° C. for 2-4 hours. After the reaction, remove the medium, dissolve the crystals formed in about 300 ~ 500 μl of DMSO, and measure the absorbance at 540 nm.

Nitric Oxide (NO) production inhibition evaluation One of the reactive oxygen species and the production amount of NO, which plays an important role in inducing inflammation, was measured in the form of NO ₂ ^- present in the cell culture medium using Griess Reagent. That is, RAW264.7 cells were adjusted to 1.0 × 10 ⁵ cells/ml using DMEM medium, inoculated in a 48 well plate, and pre-cultured for 18 hours. Therefore, 100 μl of cell culture supernatant and 100 μl of Griess reagent were mixed with 100 μl of cell culture supernatant that was simultaneously treated with a new medium containing the test substance and LPS (1 μg/ml), and reacted for 10 minutes in 96-well plates, followed by an ELISA reader. The absorbance was measured at 540 nm using the The amount of NO generated was measured in the form of NO ₂ ^- present in the cell culture medium using Griess reagent and compared with the positive control 2-Amino-4-methylpyridine (10 μM) treatment group, and the results are shown in Table 5 below. .

control argan oil citron oil Example 1 NO 100.0 111.0 111.6 81.2 cell viability 100.0 116.81 108.92 114.34

As shown in Table 5, it can be seen that the mixed fat and oil composition according to the present invention has an anti-inflammatory effect due to inhibition of NO production.

As in argan oil or citron seed oil, in general, vegetable oil has no anti-inflammatory effect, but the mixed oil composition according to the present invention has an anti-inflammatory or anti-inflammatory effect, so it will be usefully applicable to cosmetics, external preparations for skin and food.

[Experimental Example 4] Moisturizing evaluation of oil-fat composition

In order to confirm the excellent water-containing ability of the oil-fat composition of the present invention, Hyaluronic acid (HA), which is known to be involved in improving the skin barrier restoration ability when the content in the stratum corneum is increased, is added to the keratinocytes to maintain the water balance with its excellent water-containing ability. Measured in culture.

HaCaT cells were adjusted to 1.0 X 10 ⁵ cells/mL using DMEM medium, inoculated in a 24 well plate, and cultured for 18 hours. This was treated with a new medium containing the test substance, cultured for 24 hours, and the cell culture supernatant was taken and the HA content in the cell culture medium was measured using a Hyaluronic Acid (HA) ELISA kit. As a positive control group, a group added with retinoic acid (1.0 μM) was compared. The measurement results are shown in Table 6 below.

control argan oil Hexyl Laurate Example 1 HA production 100.0 74.4 82.2 111.5

As shown in Table 6 above, the hyaluronic acid producing ability of the mixed oil and fat composition of the present invention was increased by about 30 to 40% compared to commonly used argan oil or hexyl laurate, confirming that the moisturizing effect was excellent.

Therefore, the mixed fat and oil composition according to the present invention has improved moisturizing effect than vegetable oils, and thus can be usefully used as cosmetics and external preparations for skin.

[Experimental Example 5] Stability evaluation with respect to temperature and light

In order to confirm the stability according to the temperature of the oil composition of Example 1, the temperature according to the change of temperature (-20 ℃, 4 ℃, 25-30 ℃, 50 ℃) and stored under sunlight exposure conditions and aged for 28 days Enemy changes were observed. The results are shown in FIG. 1 .

As shown in Figure 1, it was confirmed that the mixed fat and oil composition according to the present invention is stable under conditions of room temperature, refrigeration, freezing and high temperature.

However, in sunlight, a change in color appeared after 2 weeks, which is thought to have occurred over time as unsaturated fatty acids were oxidized by light.

Therefore, it is seen that it is preferable to store the product containing the composition of the present invention, avoiding direct sunlight.

Claims (8)

5 to 30 wt% of a first triglyceride compound represented by the following formula (1);
10 to 70 wt% of a second triglyceride compound represented by the following formula (2) and
Mixed fat and oil composition comprising 10 to 70 wt% of a third triglyceride compound represented by the following formula (3):
[Formula 1]

In Formula 1, RL ₁ to RL ₃ are each independently a linear or branched saturated or unsaturated C ₁₀ to C ₂₂ alkyl group, and may be the same as or different from each other.
[Formula 2]

In Formula 2, any one selected from Ra ₁ to Ra ₃ is hydrogen, a linear or branched saturated or unsaturated C ₁ to C ₅ alkyl group,
The other two of Ra ₁ to Ra ₃ are each independently a linear or branched saturated or unsaturated C ₁₀ to C ₂₂ alkyl group, and may be the same as or different from each other.
[Formula 3]

In Formula 3, any one selected from Rb ₁ to Rb ₃ is a linear or branched saturated or unsaturated C ₁₀ ~ C ₂₂ alkyl group,
The other two of Rb ₁ to Rb ₃ are each independently hydrogen or a linear or branched saturated or unsaturated C ₁ to C ₅ alkyl group, and may be the same as or different from each other.
The method of claim 1,
The composition is prepared by transesterification of a vegetable oil and a carboxylic acid or a derivative thereof,
The carboxylic acid is a mixed oil composition, characterized in that formic acid, metanoic acid, etanoic acid, propanoic acid, butanoic acid or pentanoic acid.
3. The method of claim 2,
The vegetable oil is one or two selected from citron seed oil, camellia seed oil, green tea seed oil, coconut oil, palm oil, palm kernel oil, castor oil, olive oil, grape seed oil, canola oil, safflower oil, rice bran oil, sunflower oil and soybean oil A mixed fat and oil composition, characterized in that it is a mixture of the above.
3. The method of claim 2,
The transesterification reaction is a mixed fat and oil composition, characterized in that made by a lipase enzyme.
A cosmetic composition comprising the composition of any one of claims 1 to 4.
An anti-inflammatory composition comprising the composition of any one of claims 1 to 4.
A composition for external application for skin comprising the composition of any one of claims 1 to 4.
A food comprising the composition of any one of claims 1 to 4.

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