KR20210059240A - Dipropylene glycol composition and preparation method thereof - Google Patents

Abstract

An embodiment relates to a composition and a manufacturing method thereof. The composition comprises: 25-40 wt% of 1,1'-oxibis (2-propanol); 46-70 wt% of 2-(2-hydroxypropoxy)-1-propanol; and 3-15 wt% of 2,2-oxibis (1-propanol) based on the total weight of the composition. The composition according to the embodiment can be usefully applied to a use sensitive to smell by reducing the smell. Especially, when the dipropylene glycol composition is used for cosmetics or medicines, the dipropylene glycol composition provides excellent usability and applicability, is not sticky and oily, and can realize a natural appearance after use.

Description

Dipropylene glycol composition and its manufacturing method {DIPROPYLENE GLYCOL COMPOSITION AND PREPARATION METHOD THEREOF}

Embodiment relates to a dipropylene glycol composition and a method for preparing the same

The propylene glycol composition is a raw material for a wide range of applications, such as pharmaceuticals such as cosmetics and ointments, antifreeze, surfactants, and raw materials for high-end polar solvents.

Such a propylene glycol composition is generally prepared by reacting propylene oxide and water. In addition, monopropylene glycol, dipropylene glycol, and tripropylene glycol can be obtained by the classification of the propylene glycol.

The propylene glycol composition may contain impurities that may be introduced from propylene oxide and affect subsequent processes, and such impurities may adversely affect the properties or odor of the propylene glycol composition. In addition, depending on the degree of such odor, the feeling of use may vary when used for odor-sensitive applications, for example, pharmaceuticals such as cosmetics or ointments.

Therefore, in order to use the propylene glycol composition in odor sensitive applications, for example, cosmetics, foods, pharmaceuticals, and tobacco, it is most important to reduce the physical properties and odor of the composition, so research on this is continued. Has become.

U.S. Patent Publication No. 3,574,772

In embodiments, by adjusting the isomer content of dipropylene glycol to a specific range, it has excellent odor reduction effect, as well as excellent feeling and spreadability when used in cosmetics or pharmaceuticals, without stickiness and greasyness, and can implement a natural appearance after use, resulting in a high-quality product. It is intended to provide a composition and a method of manufacturing the same that can provide.

One embodiment to achieve the above object, based on the total weight of the composition, 1,1'-oxybis (2-propanol) 25% by weight to 40% by weight, 2-(2-hydroxypropoxy)-1- It provides a dipropylene glycol composition comprising 46% to 70% by weight of propanol, and 3% to 15% by weight of 2,2-oxybis (1-propanol).

In another embodiment, a first process of reacting propylene oxide and water; A second step of supplying the product obtained in the first step to a first distillation column and distilling it to separate monopropylene glycol; A third step of supplying the mixed solution remaining in the first distillation column to a second distillation column and distilling to separate dipropylene glycol to obtain a dipropylene glycol composition, based on the total weight of the composition, 1,1′- Oxybis(2-propanol) 25% to 40% by weight, 2-(2-hydroxypropoxy)-1-propanol 46% to 70% by weight, and 2,2-oxybis(1-propanol) 3 It provides a method for producing a dipropylene glycol composition comprising a weight% to 15% by weight.

Another embodiment provides a product using the dipropylene glycol composition.

The dipropylene glycol composition according to the embodiment is capable of producing a high-purity and high-quality composition with reduced odor by adjusting the isomer content of dipropylene glycol to a specific range. It can be applied in various ways such as medicine and tobacco. Particularly, when the dipropylene glycol composition is used in cosmetics or pharmaceuticals, it has excellent feeling and spreadability, has no stickiness and greasyness, and can implement a natural appearance after use.

Hereinafter, the invention will be described in detail through embodiments. The implementation is not limited to the content disclosed below, and may be modified in various forms unless the gist of the invention is changed.

In the present specification, when a part "includes" a certain component, it means that other components may be further included rather than excluding other components unless otherwise stated.

In addition, all numbers and expressions indicating amounts of constituents, reaction conditions, and the like described herein are to be understood as being modified by the term "about" in all cases unless otherwise specified.

<Composition>

Dipropylene glycol composition according to an embodiment of the present invention, based on the total weight of the composition, 1,1'-oxybis (2-propanol) 25% to 40% by weight, 2-(2-hydroxypropoxy)- 46% to 70% by weight of 1-propanol, and 3% to 15% by weight of 2,2-oxybis(1-propanol).

The 1,1′-oxybis(2-propanol), 2-(2-hydroxypropoxy)-1-propanol and 2,2-oxybis(1-propanol) are isomers of dipropylene glycol, Specifically, it is a structural isomer.

The isomers are 　molecules having the same molecular formula but different physical or chemical properties.Isomer molecules have the same type and number of elements, but their constituent groups or structures are completely different, or even if they have the same structure, they have different properties due to different relative arrangements. Will have. This is because the properties of molecules can be changed by changing various properties, including the structure and shape of molecules, interactions between molecules, and physical properties. Therefore, the composition of the dipropylene glycol is a very important factor because the characteristics or effects of the dipropylene glycol composition may be sensitively changed depending on the content of the isomer.

According to an embodiment of the present invention, by adjusting the content of the isomer of the dipropylene glycol, it is possible to prepare a composition of high purity and high quality with reduced odor. Therefore, the composition can be applied in various ways such as odor sensitive applications, for example, cosmetics, food, medicine, and tobacco. In addition, when the composition is applied to a cosmetic or medical product, there is an advantage in that it has excellent feeling of use and application, has no stickiness and greasyness, and can realize a natural appearance even after use.

1,1'-oxybis(2-propanol) contained in the composition according to an embodiment of the present invention (referred to herein as DPG 1) may be represented by the following formula (1).

[Formula 1]

The 1,1'-oxybis(2-propanol) may contain two secondary alcohols.

The 1,1'-oxybis (2-propanol) is 25% to 40% by weight, 28% to 40% by weight, 26% to 37% by weight, 27% to 38% by weight based on the total weight of the composition. Wt%, 28 wt% to 37 wt%, 28 wt% to 36 wt%, 28 wt% to 35 wt%, 30 wt% to 36 wt%, or 25 wt% to 29 wt%.

2-(2-hydroxypropoxy)-1-propanol (referred to herein as DPG 2) contained in the composition according to an embodiment of the present invention may be represented by Formula 2 below.

[Formula 2]

The 2-(2-hydroxypropoxy)-1-propanol may include one secondary alcohol and one primary alcohol.

The 2-(2-hydroxypropoxy)-1-propanol is 46 wt% to 70 wt%, 48 wt% to 68 wt%, 50 wt% to 66 wt%, 58 wt% based on the total weight of the composition To 66%, 58% to 63%, 58% to 62%, 58% to 61%, 50% to 60%, 60% to 65%, or 59% to It may be 63% by weight.

2,2-oxybis (1-propanol) contained in the composition according to an embodiment of the present invention (referred to herein as DPG 3) may be represented by the following formula (3).

[Formula 3]

The 2,2-oxybis (1-propanol) may contain two primary alcohols.

The 2,2-oxybis (1-propanol) is 3% to 15% by weight, 4% to 12% by weight, 6% to 12% by weight, 5% to 10% by weight based on the total weight of the composition %, 6% to 10%, 8% to 12%, or 5% to 9% by weight.

The 1,1′-oxybis(2-propanol, 2-(2-hydroxypropoxy)-1-propanol and 2,2-oxybis(1-propanol) are polar and Specifically, when the content of the isomer of dipropylene glycol exceeds or is less than the above-described content range, a change may occur in the appropriate hydrogen bonding force, and in this case, the isomer of dipropylene glycol is In addition, when the viscosity and polarity of the composition are changed, when the composition is applied to, for example, a cosmetic product, not only the feeling of use but also the degree of moisturizing power may be changed. Therefore, when the content of the isomer of the dipropylene glycol satisfies the above range, it is possible to implement the viscosity and polarity of an appropriate composition, whereby, when the composition is applied to cosmetics, a satisfactory feeling of use and moisturizing power can be realized.

According to an embodiment of the present invention, the mixing weight ratio of the 2-(2-hydroxypropoxy)-1-propanol and the 1,1'-oxybis(2-propanol) is 1:0.4 to 0.8, 1: It may be 0.4 to 0.7, 1: 0.4 to 0.65, or 1: 0.4 to 0.6. When the above content range is satisfied, the feeling and spreadability is excellent when used in cosmetics or pharmaceuticals, and there is no stickiness and greasyness, and a natural appearance can be realized after use.

In addition, the mixing weight ratio of the 2-(2-hydroxypropoxy)-1-propanol and the 2,2-oxybis(1-propanol) is 1:0.02 to 0.3, 1:0.05 to 0.2, or 1:0.08 To 0.19. When the above content range is satisfied, the feeling and spreadability is excellent when used in cosmetics or pharmaceuticals, and there is no stickiness and greasyness, and a natural appearance can be realized after use.

In addition, the mixing weight ratio of the 1,1'-oxybis (2-propanol) and the 2,2-oxybis (1-propanol) is 1: 0.1 to 0.5, 1: 0.15 to 0.48, or 1: 0.17 to 0.45 Can be When the above content range is satisfied, the feeling and spreadability is excellent when used in cosmetics or pharmaceuticals, and there is no stickiness and greasyness, and a natural appearance can be realized after use.

According to an embodiment of the present invention, the dipropylene glycol composition includes an enantiomer of 2-(2-hydroxypropoxy)-1-propanol, and the enantiomer is (R, R)-(±)- 2-(2-hydroxypropoxy)-1-propanol, (R, S)-2-(2-hydroxypropoxy)-1-propanol, and (S-(R, R)-2-(2 -Hydroxypropoxy)-1-propanol.

The (R, R)-(±)-2-(2-hydroxypropoxy)-1-propanol is 22% to 32% by weight, 22% to 30% by weight, 23% by weight based on the total weight of the composition % To 30% by weight, 24% to 30% by weight, or 24% to 28% by weight.

In addition, the (R, S)-2-(2-hydroxypropoxy)-1-propanol is from 19% to 28%, 20% to 28%, and 20% by weight based on the total weight of the composition. It may be included in an amount of 27% by weight, 21% by weight to 27% by weight, or 22% by weight to 26% by weight.

In addition, the (S-(R, R)-2-(2-hydroxypropoxy)-1-propanol is 4 wt% to 10 wt%, 4 wt% to 9 wt%, 5 It may be included in an amount of weight% to 9 weight %, 6 weight% to 10 weight %, 6 weight% to 9 weight %, or 7 weight% to 9 weight %.

In addition, the (R, R)-(±)-2-(2-hydroxypropoxy)-1-propanol and the (R, S)-2-(2-hydroxypropoxy)-1-propanol The mixing weight ratio may be 1: 0.7 to 1.2, 1: 0.8 to 1.1, or 1: 0.85 to 1.0. When the above content range is satisfied, the feeling and spreadability is excellent when used in cosmetics or pharmaceuticals, and there is no stickiness and greasyness, and a natural appearance can be realized after use.

In addition, the (R, R)-(±)-2-(2-hydroxypropoxy)-1-propanol and the (S-(R, R)-2-(2-hydroxypropoxy)-1 -The mixing weight ratio of propanol may be 1: 0.15 to 0.45, 1: 0.15 to 0.4, or 1: 0.15 to 0.38. If the above content range is satisfied, it is excellent in feeling and spreadability when used in cosmetics or pharmaceuticals, and stickiness and glossiness There is no, and a natural appearance can be realized after use.

The mixing weight ratio of the (R, S)-2-(2-hydroxypropoxy)-1-propanol and the (S-(R, R)-2-(2-hydroxypropoxy)-1-propanol is It may be 1: 0.15 to 0.5, 1: 0.17 to 0.4, 1: 0.2 to 0.4, or 0.25 to 0.38 If the above content range is satisfied, it has excellent feeling and spreadability when used in cosmetics or pharmaceuticals, and there is no stickiness or greasyness. , After use, natural appearance can be realized.

According to an embodiment of the present invention, the dipropylene glycol composition is based on the total weight of the composition, the (R, R)-(±)-2-(2-hydroxypropoxy)-1-propanol 22 Wt% to 30 wt%, 20 wt% to 28 wt% of the (R, S)-2-(2-hydroxypropoxy)-1-propanol, and the (S-(R, R)-2- (2-hydroxypropoxy)-1-propanol may be included in an amount of 4 to 9% by weight.

In addition, the dipropylene glycol composition, based on the total weight of the composition, the 1,1'-oxybis (2-propanol) 27% by weight to 38% by weight, the (R, R)-(±)-2 -(2-hydroxypropoxy)-1-propanol 23% to 30% by weight, the (R, S)-2-(2-hydroxypropoxy)-1-propanol 20% to 27% by weight %, the (S-(R, R)-2-(2-hydroxypropoxy)-1-propanol is 4 to 9% by weight, and the 2,2-oxybis(1-propanol) is 4% by weight It may be included in an amount of to 12% by weight.

In addition to the enantiomer of 2-(2-hydroxypropoxy)-1-propanol, the composition according to an embodiment of the present invention may include an enantiomer of 1,1′-oxybis(2-propanol). . In addition, the composition may contain an enantiomer of 2,2-oxybis(1-propanol). In addition, the composition may further include possible isomers in addition to the isomers described above.

Specifically, the enantiomer of 1,1'-oxybis(2-propanol) is (R, R)-(±)-1,1'-oxybis-2propanol, (R, S)-1,1 '-Oxybis-2-propanol, and (S-(R, R)-1,1'-oxybis-2-propanol.

The enantiomer of 2,2-oxybis(1-propanol) is (R, R)-(±)-2,2'-oxybis-1-propanol, (R, S)-2,2'-oxy Bis-1-propanol, and (S-(R, R)-2,2'-oxybis-1-propanol.

The composition according to an embodiment of the present invention is dipropylene glycol; And monopropylene glycol, tripropylene glycol, or a mixture thereof, wherein the dipropylene glycol is a structural isomer thereof, 1,1'-oxybis(2-propanol), 2-(2-hydroxypropoxy )-1-propanol and 2,2-oxybis(1-propanol).

The content of the dipropylene glycol, specifically, the total of 1,1'-oxybis (2-propanol), 2- (2-hydroxypropoxy) -1-propanol and 2,2-oxybis (1-propanol) The content may be 99.5% by weight or more based on the total weight of the composition.

The total content of 1,1'-oxybis(2-propanol), 2-(2-hydroxypropoxy)-1-propanol and 2,2-oxybis(1-propanol) according to an embodiment of the present invention By controlling to 99.5% by weight or more, it is possible to prepare a composition of high purity and high quality with controlled odor. Therefore, the composition can be applied in various ways, such as cosmetics, food, medicine, and tobacco, etc., for applications sensitive to odors. In particular, when the composition is applied to cosmetics, it is excellent in use and spreadability of cosmetics, and stickiness and shine. There is no advantage, and it has the advantage of realizing the appearance of a natural cosmetic film.

Specifically, the dipropylene glycol may be 99.5% by weight or more, 99.6% by weight or more, 99.7% by weight or more, 99.8% by weight or more, or 99.9% by weight or more based on the total weight of the composition.

Since the composition has a different odor depending on the content of each component, particularly the content of dipropylene glycol, the content of each component included in the composition may be a very important factor to achieve the effect of the composition.

If the dipropylene glycol is less than 99.5% by weight based on the total weight of the composition, a odor may occur, and as the content of dipropylene glycol is low, an unpleasant odor or a fishy odor that is perceived by everyone as well as skilled persons may occur. In addition, the feeling of use and application of cosmetics may be adversely affected or the degree of stickiness may be severe.

The odor may be generated from odor-causing substances generated from propylene oxide, a raw material used in manufacturing high-purity dipropylene glycol, or impurities generated in the process of classifying dipropylene glycol, and the higher the content of dipropylene glycol Odor can be reduced because of the reduction of impurities (odor-causing substances). In this case, the odor-causing substance may include an aldehyde compound, a ketone compound, or a mixture thereof, but is not limited thereto.

According to an embodiment of the present invention, the dipropylene glycol composition may further include monopropylene glycol, tripropylene glycol, or a mixture thereof, and the content of the monopropylene glycol, tripropylene glycol or a mixture thereof is the total composition It may be 0.001% by weight to 0.5% by weight based on the weight.

Specifically, the monopropylene glycol may be included in an amount of 0.5% by weight or less, 0.3% by weight or less, 0.2% by weight or less, or 0.1% by weight or less based on the total weight of the composition. In addition, the monopropylene glycol may be 0.05% by weight or less, 0.02% by weight or less, or 0.01% by weight or less based on the total weight of the composition.

In addition, the tripropylene glycol may be included in an amount of 0.5% by weight or less, 0.4% by weight or less, or 0.3% by weight or less based on the total weight of the composition. The tripropylene glycol may be 0.25% by weight or less, 0.1% by weight or less, 0.05% by weight or less, 0.02% by weight or less, or 0.01% by weight or less based on the total weight of the composition.

When the composition comprises a mixture of monopropylene glycol and tripropylene glycol, the mixture is 0.001% by weight to 0.5% by weight, 0.001% by weight to 0.45% by weight, 0.001% by weight to 0.4% by weight, based on the total weight of the composition, It may be included in an amount of 0.001% by weight to 0.3% by weight, 0.001% by weight to 0.2% by weight, or 0.001% by weight to 0.1% by weight.

In addition, according to an embodiment of the present invention, the content ratio of each component may be important in order to improve the effect of the present invention, for example, the content ratio of the dipropylene glycol and the monopropylene glycol, specifically the 1,1' The total content of -oxybis (2-propanol), the 2-(2-hydroxypropoxy)-1-propanol and the 2,2-oxybis (1-propanol) and the mixing weight ratio of the monopropylene glycol is 1 : 0.0001 to 0.005, 1: 0.0001 to 0.004 or 1: 0.0001 to 0.003. If the content of the monopropylene glycol is larger than the above range, the odor increases, and when the composition is applied to cosmetics, the feeling of use and application effect of the cosmetics may be poor, and stickiness may increase.

In addition, the mixing weight ratio of the dipropylene glycol and the tripropylene glycol, specifically, the 1,1'-oxybis (2-propanol), the 2- (2-hydroxypropoxy) -1-propanol and the 2, The total content of 2-oxybis (1-propanol) and the mixing weight ratio of the tripropylene glycol may be 1: 0.0001 to 0.005, 1: 0.0001 to 0.004, or 1: 0.0001 to 0.003. If the content of the tripropylene glycol is larger than the above range, the odor increases, and when the composition is applied to a cosmetic, the feeling of use and application of the cosmetic may be poor, and stickiness may increase.

In addition, the mixed weight ratio of the monopropylene glycol and the tripropylene glycol may be 1: 10 to 10: 1, 1: 8 to 8: 1, 1: 5 to 5: 1, 1: 3 to 3: 1. When the content range of the monopropylene glycol and the tripropylene glycol is satisfied, the odor removal effect may be further improved. In particular, when the mixing weight ratio of the monopropylene glycol and the tripropylene glycol satisfies 1:3 to 3:1, it is possible to further improve the feeling of use and application of cosmetics when the composition is applied to cosmetics as well as odor removal effects. .

In addition, the composition may further contain tetrapropylene glycol in an amount of 0.01% by weight or less, for example, 0.005% by weight or less, for example, 0.0005% by weight or less. In addition, the composition may further contain at least one selected from the group consisting of pentapropylene glycol and hexapropylene glycol in an amount of 0.01% by weight or less, for example, 0.005% by weight or less, for example, 0.0005% by weight or less. If the content of one or more selected from the group consisting of tetrapropylene glycol, pentapropylene glycol, and hexapropylene glycol is larger than the above range, the odor increases, the feeling of use and application of cosmetics are poor, and stickiness may increase. .

<Method of preparing the composition>

On the other hand, the present invention is a first process of reacting propylene oxide and water according to the embodiment; A second step of supplying the product obtained in the first step to a first distillation column and distilling it to separate monopropylene glycol; A third step of supplying the mixed solution remaining in the first distillation column to a second distillation column and distilling to separate dipropylene glycol to obtain a dipropylene glycol composition, based on the total weight of the composition, 1,1′- Oxybis(2-propanol) 25% to 40% by weight, 2-(2-hydroxypropoxy)-1-propanol 46% to 70% by weight, and 2,2-oxybis(1-propanol) 3 It can provide a method for producing a dipropylene glycol composition comprising a weight% to 15% by weight.

The dipropylene glycol composition includes an enantiomer of 2-(2-hydroxypropoxy)-1-propanol, and the enantiomer is (R, R)-(±)-2-(2-hydroxypropoxy )-1-propanol, (R, S)-2-(2-hydroxypropoxy)-1-propanol, and (S-(R, R)-2-(2-hydroxypropoxy)-1- It may contain propanol The content of the enantiomer of 2-(2-hydroxypropoxy)-1-propanol is as described above.

According to one embodiment of the present invention, the content of dipropylene glycol separated in the method for preparing the dipropylene glycol composition may be 99.5% by weight or more.

The composition may further include monopropylene glycol, tripropylene glycol, or a mixture thereof, and the content of the monopropylene glycol, tripropylene glycol, or a mixture thereof is as described above.

In the preparation method of the composition, the distillation may use a distillation method commonly used, for example, monodistillation or multistage distillation may be used.

In the method for preparing the composition according to an embodiment of the present invention, the first and second distillation columns include a top zone and a bottom zone, and each of the stages provided in the top zone and the bottom zone is in a distillation curve. It may be in the range of 80% to 200%, 100% to 170%, or 120% to 140% of the number of theoretical plates calculated by.

Since the number of 　 stages of the tower obtained here is the number of theoretical stages and is an ideal 　 number of stages, the actual number of stages in the tower is preferably 80 to 200% of the theoretical stage according to the general design criteria. If it is less than 80% of the calculated theoretical plates, the separation of the low-boiling and high-boiling components in the pre-separation area may be difficult, and if it exceeds 200%, the energy saving effect is not increased anymore, only the investment cost is increased because it is the minimum reflux area. It is not desirable. In the present invention, the theoretical number of stages was calculated using the Fenske-Underwood equation (the Fenske-Underwood equation is an equation widely known to those of ordinary skill in the art).

In addition, the top section may mean the uppermost end of the distillation column, and the bottom section may mean the lowermost end of the distillation column.

In the above manufacturing method, the first step includes a step of reacting propylene oxide and water.

The dipropylene glycol composition may be prepared by reacting a propylene oxide composition and water, as shown in Scheme 1 below.

[Scheme 1]

The mixing weight ratio of the propylene oxide and water may be 1: 1 to 5, 1: 2 to 5, 2 to 4, or 2.5 to 3.5.

The reaction is 10 kg/cm 2G to 30 kg/cm 2G, 13 to 25 kg/cm 2G, 10 kg/cm 2G to 20 kg/cm 2 G, 15 kg/cm 2G to 20 kg/cm 2 G, or 10 kg It can be performed at a pressure of /cm2G to 15 kg/cm2G. In addition, the reaction temperature may be carried out at a temperature of 100°C to 250°C, 100°C to 200°C, 110°C to 190°C, or 120°C to 180°C. In addition, the reaction time may be about 0.2 hours to 3 hours, 0.5 hours to 2.5 hours, or 1 hour to 2 hours.

In addition, before supplying the product obtained in the first process to the first distillation column (second process), the step of removing unreacted substances and other impurities may be further included.

Specifically, in order to remove unreacted propylene oxide, water and other impurities among the products obtained in the first process, the product obtained in the first process may be supplied to the distillation column A.

In the above manufacturing method, the second step includes a step of supplying the product obtained in the first step to a first distillation column and distilling it to separate monopropylene glycol.

At this time, when unreacted propylene oxide, water, and other impurities among the products obtained in the first process are removed in the distillation column A, the bottom liquid of the distillation column A may be supplied to the first distillation column.

In addition, in the second process, the separation of the monopropylene glycol may be performed at a pressure of 50 Torr to 200 Torr and a temperature of 100° C. to 200° C. in the top section of the first distillation column. In addition, the temperature of the bottom section of the first distillation column may be 100 ℃ to 300 ℃. High purity monopropylene glycol may be separated from the top of the first distillation column.

In the manufacturing method, the third step includes a step of supplying the mixed solution remaining in the first distillation column to the second distillation column and distilling it to separate dipropylene glycol.

In the third process, the mixed liquid remaining in the first distillation column, specifically, the bottom liquid of the first distillation column may be supplied to the second distillation column.

Separation of the dipropylene glycol may be performed at a pressure of 20 Torr to 100 Torr and a temperature of 130° C. to 180° C. in the top section of the second distillation column.

In the third process, the mixed solution may contain dipropylene glycol and tripropylene glycol, and may be operated under high vacuum to lower the boiling points of the dipropylene glycol and the tripropylene glycol in the bottom section of the second distillation column. , The temperature of the bottom zone may be 150 ℃ to 300 ℃. In addition, the boiling points of the dipropylene glycol and the tripropylene glycol may be 130 °C to 180 °C and 150 °C to 250 °C, respectively. Dipropylene glycol of high purity may be separated from the top of the second distillation column.

If necessary, the second distillation column may be composed of two in series so that the separated dipropylene glycol can be mixed.

A composition containing dipropylene glycol according to an embodiment of the present invention may include monopropylene glycol, tripropylene glycol, or a mixture thereof in addition to the separated dipropylene glycol.

In the composition according to an embodiment of the present invention, the content of dipropylene glycol may be 99.5% by weight or more based on the total weight of the composition, and the content of dipropylene glycol can be measured through gas chromatography (GC) analysis. have. Specifically, it can be quantitatively analyzed through gas chromatography based on the ASTM E (Standard Test Methods for Analysis of Ethylene Glycols and Propylene Glycols) test method.

<The properties of the composition>

According to an embodiment of the present invention, the odor index of the composition may be less than 3. In addition, the odor intensity index of the composition may be 1 or less. Specifically, the odor intensity index of the composition may be 0 to less than 3, 0 to 2, 0 to 1, or 0 to 0.5, but is not limited thereto. At this time, the odor index is 0 when odor is confirmed by mixing the composition with water at about 1: 1 weight ratio at 60° C., 1.0 when detected only by skilled workers, and is detected by anyone, 1.5 to 2.0 were not unpleasant to smell, and 2.5 to 3.0 were evaluated for the case of a fishy smell while being detected by anyone.

According to an embodiment of the present invention, a dipropylene glycol composition containing an isomer of dipropylene glycol in a specific content range can be usefully applied to odor sensitive applications due to reduced odor. In particular, the dipropylene glycol composition may be used in cosmetics or pharmaceuticals. When used on, it has excellent feeling of use and application, has no stickiness and greasyness, and can realize a natural appearance after use.

Accordingly, the present invention may provide a product using the composition according to embodiments, and the product may specifically include cosmetics, foods, medicines, or tobacco.

The above will be described in more detail by the following examples. However, the following examples are for illustrative purposes only, and the scope of the examples is not limited thereto.

Example

<Example 1>

1st process

0.5 kg of propylene oxide and 1.5 kg of water were reacted in an adiabatic reactor. The pressure of the reactor was 15 kg/cm 2 G, and the temperature was maintained at about 150°C. In the reactor effluent, unreacted propylene glycol, water and other impurities were removed.

2nd process

The product obtained in the first step was fed to a first distillation column, and distilled at a top temperature of 130° C. under vacuum to separate monopropylene glycol from the propylene glycol in the top section. At this time, the bottom temperature of the first distillation column was 200 °C.

3rd process

The mixed solution remaining in the bottom section of the first distillation column was supplied to the second distillation column and distilled to separate dipropylene glycol to obtain a dipropylene glycol composition. In the top section of the second distillation column, high-purity dipropylene glycol was separated by performing at a temperature of 160° C. under high vacuum at a pressure of 80 Torr to obtain a composition containing the same. At this time, the bottom temperature of the second distillation column was 200 °C.

The content of each component included in the composition was confirmed through gas chromatography ( GC).

<Examples 2 to 5>

Dipropylene glycol was carried out in the same manner as in Example 1, except that the contents of dipropylene glycol isomers (DPG 1, DPG 2, DPG 3), monopropylene glycol, and tripropylene glycol were adjusted as shown in Table 1 below. To obtain a composition containing.

<Comparative Examples 1 to 3>

Dipropylene glycol was carried out in the same manner as in Example 1, except that the contents of dipropylene glycol isomers (DPG 1, DPG 2, DPG 3), monopropylene glycol, and tripropylene glycol were adjusted as shown in Table 1 below. To obtain a composition containing.

Evaluation example

<Evaluation Example 1: Gas Chromatography ( GC ) Measurement>

Gas chromatography (GC ) of the compositions obtained in Examples and Comparative Examples based on ASTM E (Standard Test Methods for Analysis of Ethylene Glycols and Propylene Glycols) Quantitative analysis was performed by the method:

GC: HP 7890, column

CP WAX 52CB, 30m

Sample + water = 1:1 (0.5 μl)

Each component and content of dipropylene glycol prepared in Examples and Comparative Examples are summarized in Table 1 below.

<Evaluation Example 2: Measurement of odor index>

The compositions obtained in Examples and Comparative Examples were mixed with water at 60° C. at a ratio of 1:1, and the odor intensity index of each composition was measured according to the following criteria.

0: odorless

1.0: Detected only by skilled people.

1.5~2.0: It is detected by anyone, but it is not an unpleasant smell.

2.5~3.0: Detected by anyone, and smells fishy.

The odor test results in which the measured intensity index is expressed as O and X according to the following criteria are shown in Table 1 below:

O: Odor intensity index 1.0 or less

X: odor intensity index 1.5 to 3.0

As shown in Table 1, it was confirmed that the odor was significantly removed from the compositions obtained in Examples 1 to 5 compared to the compositions obtained in Comparative Examples 1 to 3.

Specifically, it was confirmed that the contents of the isomers of dipropylene glycol were all within the scope of the present invention in the compositions obtained in Examples 1 to 5, and the compositions obtained in Comparative Examples 1 to 3 in which the contents of the isomers were out of the scope of the present invention. Compared to, the odor intensity index was lower than 1.0.

Accordingly, the compositions obtained in Examples 1 to 5 of the present invention can be usefully applied to products such as cosmetics, foods, medicines, and tobacco, which are applications sensitive to odors.

Claims (19)

Based on the total weight of the composition,
1,1'-oxybis (2-propanol) 25% to 40% by weight,
2-(2-hydroxypropoxy)-1-propanol 46% to 70% by weight, and
2,2-oxybis (1-propanol) 3% to 15% by weight
Containing, dipropylene glycol composition.
The method of claim 1,
The weight ratio of the 2-(2-hydroxypropoxy)-1-propanol and the 1,1′-oxybis(2-propanol) is 1:0.4 to 0.8, a dipropylene glycol composition.
The method of claim 1,
The weight ratio of the 2-(2-hydroxypropoxy)-1-propanol and the 2,2-oxybis(1-propanol) is 1:0.02 to 0.3, dipropylene glycol composition.
The method of claim 1,
The weight ratio of the 1,1'-oxybis (2-propanol) and the 2,2-oxybis (1-propanol) is 1: 0.1 to 0.5, dipropylene glycol composition.
The method of claim 1,
The dipropylene glycol composition contains an enantiomer of 2-(2-hydroxypropoxy)-1-propanol,
The enantiomer is (R, R)-(±)-2-(2-hydroxypropoxy)-1-propanol, (R, S)-2-(2-hydroxypropoxy)-1-propanol, And (S-(R, R)-2-(2-hydroxypropoxy)-1-propanol.
The method of claim 5,
Based on the total weight of the dipropylene glycol composition,
22% to 32% by weight of the (R, R)-(±)-2-(2-hydroxypropoxy)-1-propanol,
19% to 28% by weight of the (R, S)-2-(2-hydroxypropoxy)-1-propanol,
Dipropylene glycol composition comprising the (S-(R, R)-2-(2-hydroxypropoxy)-1-propanol in an amount of 4% to 10% by weight.
The method of claim 5,
The weight ratio of the (R, R)-(±)-2-(2-hydroxypropoxy)-1-propanol and the (R, S)-2-(2-hydroxypropoxy)-1-propanol 1: 0.7 to 1.2, dipropylene glycol composition.
The method of claim 5,
The above (R, R)-(±)-2-(2-hydroxypropoxy)-1-propanol and the above (S-(R, R)-2-(2-hydroxypropoxy)-1-propanol The weight ratio of 1: 0.15 to 0.45, dipropylene glycol composition.
The method of claim 5,
The weight ratio of the (R, S)-2-(2-hydroxypropoxy)-1-propanol and the (S-(R, R)-2-(2-hydroxypropoxy)-1-propanol is 1 : 0.15 to 0.5, dipropylene glycol composition.
The method of claim 1,
Based on the total weight of the composition,
The total content of the 1,1'-oxybis (2-propanol), 2- (2-hydroxypropoxy) -1-propanol and 2,2-oxybis (1-propanol) is 99.5% by weight or more, di Propylene glycol composition.
A first step of reacting propylene oxide and water;
A second step of supplying the product obtained in the first step to a first distillation column and distilling it to separate monopropylene glycol;
And a third step of supplying the mixed solution remaining in the first distillation column to a second distillation column and distilling to separate dipropylene glycol to obtain a dipropylene glycol composition,
Based on the total weight of the composition,
1,1'-oxybis (2-propanol) 25% to 40% by weight,
2-(2-hydroxypropoxy)-1-propanol 46% to 70% by weight, and
2,2-oxybis (1-propanol) 3% to 15% by weight
Containing, a method for producing a dipropylene glycol composition.
The method of claim 11,
The first and second distillation columns include a top section and a bottom section,
Each of the number of stages provided in the top section and the bottom section is within a range of 80% to 200% of the number of theoretical plates calculated by a distillation curve.
The method of claim 11,
In the first process, the reaction is performed at a pressure of 10 kg/cm 2G to 30 kg/cm 2 G and a temperature of 100°C to 250°C, a method for producing a dipropylene glycol composition.
The method of claim 12,
In the second process, the separation of the monopropylene glycol is carried out at a pressure of 50 Torr to 200 Torr and a temperature of 100° C. to 200° C. in the top section of the first distillation column.
The method of claim 12,
In the third process, the separation of the dipropylene glycol is carried out at a pressure of 20 Torr to 100 Torr and a temperature of 130 °C to 180 °C in the top section of the second distillation column, a method for producing a dipropylene glycol composition.
The method of claim 11,
In the third step, the mixed solution comprises dipropylene glycol and tripropylene glycol, a method for producing a dipropylene glycol composition.
The method of claim 11,
Before supplying the product obtained in the first process to the first distillation column, the method further comprises removing unreacted substances and other impurities.
Based on the total weight of the composition,
1,1'-oxybis (2-propanol) 25% to 40% by weight,
2-(2-hydroxypropoxy)-1-propanol 46% to 70% by weight, and
2,2-oxybis (1-propanol) 3% to 15% by weight
A product using a dipropylene glycol composition comprising a.
The method of claim 18,
A product, wherein the product is a cosmetic, food, pharmaceutical, or tobacco product.