KR20060097587A - Dipropyleneglycol ester plasticizer composition and process for preparing the same - Google Patents

Abstract

The present invention relates to a plasticizer composition composed of three different dipropyleneglycol esters and a method for preparing the same, and the plasticizer composition according to the present invention has a tensile strength, elongation, and inner ear without having a structure of an environmental hormone-inducing substance. The planet, hardness, transparency and tackiness are imparted to the resin, and excellent compatibility with the resin can be usefully used to prepare polyvinyl chloride resin for wrap film.

Dipropylene glycol, ester, polyvinyl chloride, benzoic acid, 2-ethylhexanoic acid, plasticizer, initial viscosity, viscosity stability.

Description

Dipropylene glycol ester plasticizer composition and preparation method thereof {Dipropyleneglycol ester plasticizer composition and process for preparing the same}

1 is a gas chromatography analysis result of the dipropylene glycol ester plasticizer composition obtained in Example 1. FIG.

The present invention relates to a dipropyleneglycol ester plasticizer composition, and more particularly, to a dipropyleneglycol ester plasticizer composition which can be used as a plasticizer of polyvinyl chloride resin (PVC).

Wrap film used as a food packaging material has excellent tensile strength, hardness, resistance to migration, transparency to directly observe the food, elongation to pack the product well, and adhesion to prevent falling after packaging. shall. In order to satisfy such physical properties, a plasticizer may be added to the resin that is the basis of the wrap film. Examples of conventional plasticizers include phthalates, adipates, and the like. The most widely used plasticizers are phthalate-based di-2-ethylhexylphthalate (DEHP) and adipate-based di-2-ethylhexyladipate (DEHA). These plasticizers serve as standard plasticizers for evaluating the performance of other plasticizers.

However, the US Environmental Protection Agency and the National Institute of Pharmaceutical Food Hygiene have classified phthalates and adipate compounds as environmental hormone substances. Therefore, development of a plasticizer which does not contain a phthalate type or an adipate type structure is calculated | required.

Meanwhile, polyvinyl chloride resin is prepared by polymerizing a vinyl chloride monomer or copolymerizing a vinyl chloride monomer and a copolymerizable monomer, and various additives such as plasticizers, stabilizers, fillers, and pigments. It is a general purpose resin that can impart various processing properties by appropriately mixing. By using such various processing properties, polyvinyl chloride resins are used for various purposes in many fields such as pipes, electric wires, artificial leather, wallpaper, gloves, toys, and food packaging materials.

As an example of a plasticizer that does not contain a phthalate- or adipate-based structure, 2-ethylhexanoic acid synthesized by reacting triethylene glycol with 2-ethylhexanoic acid [2- {2- (2-ethylhexa) 2-ethylhexanoic acid [2- {2- (2-ethylhexanoyloxy) -ethoxy} ethoxy] -ethyl ester) has excellent workability in the production of polymer resin, Physical properties such as elongation, adhesiveness and transparency of resin are poor.

In addition, there is a report that a single component ester synthesized by reacting neopentyl glycol with aliphatic butyric acid and 2-ethylhexanoic acid may be used as a plasticizer (Romanian Patent No. 6255), but compared to phthalate plasticizers. There is a drop in the compatibility with the polyvinyl chloride resin still, the polyvinyl chloride resin prepared by using the high hardness, low transparency and elongation has a problem that is not suitable as a wrap film.

Therefore, the technical problem to be achieved by the present invention does not have a phthalate- or adipate-based structure, which is an environmental hormone-inducing substance, and has excellent compatibility with polymer resins, and has excellent tensile strength, elongation, hardness, resistance, transparency, and adhesion. It is to provide a plasticizer composition capable of providing a resin and a method for producing the same.

In order to achieve the above object, in the first aspect of the present invention

(A) 5 to 80% by weight of the dipropylene glycol ester compound of Formula 1;

(b) 10 to 80% by weight of the dipropylene glycol ester compound of Formula 2; And

(c) 5 to 80% by weight of the dipropylene glycol ester compound of the formula

There is provided a dipropylene glycol ester plasticizer composition consisting of:

[Formula 1]

R ₁ OCO-C ₃ H ₆ -OC ₃ H ₆ -OCOR ₁

[Formula 2]

R ₂ OCO-C ₃ H _6- OC ₃ H _6- OCOR ₃

[Formula 3]

R ₄ OCO-C ₃ H ₆ -OC ₃ H ₆ -OCOR ₄

In the above formulas,

R ₁ is an alkyl group having 3 to 12 carbon atoms,

R ₂ is an alkyl group having 3 to 12 carbon atoms, R ₃ is an aryl group having 6 to 10 carbon atoms,

R ₄ is an aryl group having 6 to 10 carbon atoms.

According to one embodiment of the present invention, the dipropylene glycol ester plasticizer composition comprises 10 to 70% by weight of the dipropylene glycol ester compound of Chemical Formula 1; 20 to 70% by weight of the dipropylene glycol ester compound of Formula 2; And it may be made of 1 to 70% by weight of the dipropylene glycol ester compound of Formula 3.

According to another embodiment of the present invention, the compound of Formula 1 is 2-2 (2- (2-ethylhexanoyloxy) propoxy) isopropyl 2-ethylhexanoate [2-2 (2- (2-ethylhexanoyloxy ) propoxy) isopropyl 2-ethylhexanoate], and the compound of Formula 2 is 1-methyl-2- (2-phenylcarbonyloxypropoxy) ethyl 2-ethylhexanoate [1-Methyl-2- (2-phenylcarbonyloxypropoxy ) ethyl 2-ethylhexanoate, and the compound of Formula 3 is 1-methyl-2- (2-phenylcarbonyloxypropoxy) ethyl benzoate [1-Methyl-2- (2-phenylcarbonyloxypropoxy) ethyl benzoate] yl Can be.

In a second aspect of the present invention, the step of reacting 10 to 40% by weight of dipropylene glycol, 1 to 70% by weight of fatty acids having 3 to 12 carbon atoms and 1 to 70% by weight of aromatic acids having 6 to 10 carbon atoms is carried out. Provided is a method for producing the dipropylene glycol ester plasticizer composition comprising.

According to an embodiment of the present invention, the fatty acid may be 2-ethylhexanoic acid, and the aromatic acid may be benzoic acid.

According to another embodiment of the present invention, the dipropylene glycol ester composition may be prepared by reacting at a temperature of 100 to 220 ° C. for 4 to 10 hours.

According to another embodiment of the present invention, 1 to 20 parts by weight of xylene and 0.0001 to 1 part by weight of tetraisopropyl titanate may be added to 100 parts by weight of the total reactant.

In a third aspect of the present invention, there is provided a polyvinyl chloride resin comprising the dipropylene glycol ester plasticizer composition.

In a fourth aspect of the present invention, there is provided a dipropylene glycol compound of Formula 1 or Formula 2.

The dipropylene glycol ester plasticizer composition according to the present invention can be used as a plasticizer in the production of polyvinyl chloride resin, and in particular, can provide a polyvinyl chloride resin for a wrap film excellent in tensile strength, elongation, hardness, migration resistance, transparency, and adhesion. .

EMBODIMENT OF THE INVENTION Hereinafter, this invention is demonstrated in detail.

The present invention does not have a structure of phthalates and adipates, which are known as environmental hormone-inducing substances, and specifically, is suitable for tensile strength, elongation, hardness, migration resistance, A plasticizer composition which can be applied to a polyvinyl chloride resin having excellent physical properties such as transparency and adhesiveness, comprising: (a) 5 to 80% by weight of a dipropylene glycol ester compound represented by Formula 1 below; (b) 10 to 80% by weight of the dipropylene glycol ester compound of Formula 2; And (c) 5 to 80% by weight of a dipropylene glycol ester compound of formula (3) is provided:

[Formula 1]

R ₁ OCO-C ₃ H ₆ -OC ₃ H ₆ -OCOR ₁

[Formula 2]

R ₂ OCO-C ₃ H ₆ -OC ₃ H ₆ -OCOR ₃

[Formula 3]

R ₄ OCO-C ₃ H ₆ -OC ₃ H ₆ -OCOR ₄

In the above formulas,

R ₁ is an alkyl group having 3 to 12 carbon atoms,

R ₂ is an alkyl group having 3 to 12 carbon atoms, R ₃ is an aryl group having 6 to 10 carbon atoms,

R ₄ is an aryl group having 6 to 10 carbon atoms.

In the dipropylene glycol ester compound of Formula 1, R ₁ is an alkyl group having 3 to 12 carbon atoms, preferably an alkyl group having 6 to 10 carbon atoms, and most preferably 2-ethylhexyl.

Dipropylene glycol ester compound of Formula 1 is included in an amount of 5 to 80% by weight, preferably 10 to 70% by weight. When the dipropylene glycol ester compound of Formula 1 is less than 5% by weight, when used as a plasticizer of polyvinyl chloride resin, the tensile strength is low, the hardness is high, and thus the physical properties and plasticization efficiency of the product are lowered, than 80% by weight. When there are many, when it manufactures with a wrap film, adhesiveness becomes high too much.

In the dipropylene glycol ester compound of Formula 2, R ₂ is an alkyl group having 3 to 12 carbon atoms, preferably an alkyl group having 6 to 10 carbon atoms, most preferably 2-ethylhexyl, and R ₃ is an aryl having 6 to 10 carbon atoms. Group, Preferably they are a C6-C8 aryl group, Most preferably, they are a phenyl group.

The dipropylene glycol ester compound of Formula 2 is included in an amount of 10 to 80% by weight, preferably 20 to 70% by weight. When the dipropylene glycol ester compound of Formula 2 is less than 10% by weight, it is not compatible with polyvinyl chloride, which is the basic physical property of the plasticizer, and thus does not satisfy the basic physical properties. When more than 80% by weight, the tensile strength and adhesiveness of the resulting resin are increased. And physical properties such as elongation deteriorate.

In the dipropylene glycol ester compound of Formula 3, R ₄ is an aryl group having 6 to 10 carbon atoms, preferably an aryl group having 6 to 8 carbon atoms, and most preferably a phenyl group.

Dipropylene glycol ester compound of Formula 3 is included in an amount of 5 to 80% by weight, preferably 5 to 70% by weight. When the dipropylene glycol ester compound of Formula 3 is less than 5% by weight, the adhesiveness of the wrap film is increased, and a phenomenon in which the film is entangled in a roll may occur during the processing, and when the dipropylene glycol ester compound is greater than 80% by weight, the tensile strength of the wrap film Low and high hardness lowers the physical properties and plasticization efficiency of the product.

In Formulas 1 to 3, the propylene group (-C ₃ H _6- ) includes an isopropylene group.

Particularly preferred among the dipropylene glycol ester plasticizer compositions according to the invention is that the compound of formula 1 is 2-2 (2- (2-ethylhexanoyloxy) propoxy) isopropyl 2-ethylhexanoate, the compound of formula 2 Is 1-methyl-2- (2-phenylcarbonyloxypropoxy) ethyl 2-ethylhexanoate, and the compound of formula 3 is 1-methyl-2- (2-phenylcarbonyloxypropoxy) ethyl benzoate If

Dipropylene glycol ester plasticizer composition according to the invention comprises the step of reacting 10 to 40% by weight of dipropylene glycol, 1 to 70% by weight of fatty acids having 3 to 12 carbon atoms and 1 to 70% by weight of aromatic acids having 6 to 10 carbon atoms It can be prepared by the method.

When reacting with the reactant and the composition ratio, it is possible to obtain a dipropylene glycol ester plasticizer composition having the composition and components according to the present invention.

The reaction can be carried out for 4 to 10 hours at a temperature of 100 to 220 ℃.

Fatty acids in the reactants have 3 to 12 carbon atoms, preferably 6 to 10 carbon atoms, most preferably 2-ethylhexanoic acid.

The aromatic acid in the reactants has 6 to 10 carbon atoms, preferably 6 to 8 carbon atoms, most preferred is benzoic acid.

Dipropylene glycol in the reactants means that their isomers can also be used.

After obtaining a composition consisting of the compounds of Formula 1 to Formula 3, each compound is separated by a method known in the art to obtain a compound of Formula 1 or Formula 2, and the separation method is not particularly limited.

As one embodiment of the separation method, there is a method using column chromatography. As the adsorbent used as the stationary phase, materials known in the art such as alumina (Al ₂ O ₃ ), silica (SiO ₂ ), charcoal, or magnesium silicate (MgSiO ₂ ) may be used, and silica gel is preferable. It is not limited to this. As the mobile phase, materials known in the art, such as n-hexane, ethyl acetate, chloroform, or an organic solvent such as toluene, may be used. Particularly, n-hexane or ethyl acetate is preferable, but is not limited thereto. In general, the solvent varies depending on the polarity of the mixture and the stationary phase to be separated, but usually the solvent having a high polarity and a solvent having a low polarity is adjusted to have an appropriate polarity.

In the compounds of the above formulas, R ₁ and R ₂ are 1-ethyl pentyl groups, and R ₃ and R ₄ are preferably phenyl groups, but are not limited thereto.

In addition, the production method may further include a catalyst, an entrainer, and the like, in addition to the above-described reactants, tetraisopropyl titanate is preferred as the catalyst, and xylene is preferred as the entrainment material. Tetraisopropyl titanate is preferably used in an amount of 0.0001 to 1 part by weight based on 100 parts by weight of the total reactant, and xylene is preferably used in an amount of 1 to 20 parts by weight based on 100 parts by weight of the total reactant.

Looking at the production method of one embodiment of the dipropylene glycol ester plasticizer composition according to the present invention in more detail as follows.

1 to 70% by weight of dipropylene glycol, 1 to 70% by weight of 2-ethylhexanoic acid, 1 to 70% by weight of benzoic acid, and 100 parts by weight of the reaction mixture, xylene 1 to 1 in a flask equipped with a stirrer and a condenser. 20 parts by weight and 0.0001 to 1 part by weight of tetraisopropyltitanate, which is a catalyst, are added thereto, and then the temperature is raised to 220 ° C. for 4 to 10 hours. After the esterification reaction, the unreacted acid is removed by a vacuum pump, and the remaining acid is neutralized by adding sodium hydroxide in an amount of 5 to 50 parts by weight based on 100 parts by weight of the total reactants, followed by washing with water, dehydration and filtration. 10 to 80% by weight of final 2-2 (2- (2-ethylhexanoyloxy) propoxy) isopropyl 2-ethylhexanoate by removing, 1-methyl-2- (2-phenylcarbonyloxypropoxy A dipropylene glycol ester plasticizer composition comprising 10 to 80% by weight of ethyl 2-ethylhexanoate and 1 to 80% by weight of 1-methyl-2- (2-phenylcarbonyloxypropoxy) ethyl benzoate is obtained. .

Polyvinyl chloride resin may be prepared using the dipropylene glycol ester plasticizer composition according to the present invention. The polyvinyl chloride resin thus prepared is excellent in tensile strength, elongation, hardness, migration resistance, transparency, and adhesion. The polyvinyl chloride resin may be prepared by a conventional resin production method using raw materials commonly used in preparing a resin in addition to the dipropylene glycol ester plasticizer composition according to the present invention.

In addition, the dipropylene glycol ester plasticizer composition according to the present invention can be applied not only as a plasticizer of polyvinyl chloride resin, but also to other resins for improving tensile strength, elongation, migration resistance, hardness, transparency, and adhesion. In particular, it is suitable for polyvinyl chloride resin for wrap film used as a food packaging material, and is applicable to polyethylene foam sheets.

Hereinafter, the present invention will be described in more detail with reference to Examples, but the scope of the present invention is not limited to the following Examples.

Example

In the following Examples and Comparative Examples, the tensile strength, elongation, hardness, migration resistance, transparency and adhesion of the polyvinyl chloride resin specimens were evaluated in the following manner, and the results are shown in Table 1 below.

The tensile strength

Tensile strength (kgf / mm2) = load by measuring the point where the specimen is cut after pulling the crosshead speed to 500 mm / min using the test device UTM by the ASTM D638 method It calculated by the value (kgf) / {thickness (mm) x width (mm)}.

Elongation

According to the ASTM D638 method, the cross head speed was pulled to 500 mm / min using the test instrument UTM, and then the point where the specimen was cut was measured, and then the elongation (%) = {extension / Initial length} × 100.

Hardness

Hardness Tester (C type) After completely lowering the needle, the hardness value was read after 10 seconds, and after testing five places for each specimen, the average value was calculated.

Implosion

Measure the initial weight (Wi) to 4 decimal places for the specimen, place the sheet (3cm ㅧ 3cm) between polystyrene (PS) plates in an oven at 80 ° C, and leave it for 48 hours under a load of 1 kg. After taking out and storing in a thermostat for at least 4 hours, after measuring the weight (Wo) of the specimen was calculated by the amount of transfer (%) = {(Wi-Wo) / Wi} x 100.

transparency

Observed visually, the degree of transparency was superior to that of the standard plasticizer, di-2-ethylhexyladipate (DEHA), and was evaluated as superior. The case of transparency similar to DEHA was evaluated as equivalent, and opaque compared to DEHA. One case was evaluated as inferior.

Sticky

It was evaluated that the degree of adhesion was good compared to DEHA by direct contact with the hand, and the case similar to DEHA was evaluated as equivalent, and the case of poor adhesion compared to DEHA was evaluated as inferior.

Example 1

(1) Preparation of Dipropylene Glycol Ester Plasticizer Composition

3 mol dipropylene glycol (CAS No. 25265-71-8) 3 mol, 3.3 mol 2-ethylhexanoic acid, 3.3 mol benzoic acid, 60 g of xylene as an entrained material and tetraiso catalyst as catalyst After injecting 1.9 g of propyl titanate, the temperature was raised to 220 ° C. and the esterification reaction was carried out for 10 hours.

After the esterification reaction, the unreacted acid was removed under reduced pressure up to 2 mmHg with a vacuum pump at 220 ° C., and the non-removed acid was neutralized with 10 wt% sodium hydroxide, followed by washing with water and dehydration. After washing and dehydrating, an adsorbent was added and filtered to prepare a dipropylene glycol ester composition. The composition ratio of the prepared dipropylene glycol ester composition was 2-2 (2- (2-ethylhexanoyloxy) propoxy) isopropyl 2 20% by weight ethylhexanoate, 1-methyl-2- (2-phenylcarbonyloxypropoxy) 48% by weight ethyl 2-ethylhexanoate, 1-methyl-2- (2-phenylcarbonyloxyprop Foxy) ethyl benzoate 32% by weight, the components and contents were confirmed by gas chromatography and shown in FIG.

(2) Preparation of Polyvinyl Chloride Resin Using Dipropylene Glycol Ester Plasticizer Composition

36 parts by weight of a dipropylene glycol ester plasticizer composition prepared in (1) above as a plasticizer with respect to 100 parts by weight of a polyvinyl chloride resin (LG Chemical, product name LS100S), calcium-zinc stabilizer (KOLON, product name KCZ) -08) After blending 1.3 parts by weight and 12 parts by weight of epoxy soybean oil (Xindongbang Co., Ltd.), a roll mill was used for 3 minutes at a temperature of 165 ° C. to prepare a sheet having a thickness of 5 mm. The 5 mm thick sheet was pressed into a 1 mm thick sheet, and the press working conditions were preheated 3 minutes, heated 3 minutes, and cooled 3 minutes at a temperature of 185 ° C. The prepared 1 mm sheet was made into a plurality of dumbbell-shaped specimens of type C (type C) and tested.

Example 2

A dipropylene glycol ester plasticizer composition was prepared in the same manner as in Example 1 except for using the components and contents shown in Table 1 below, and the composition ratio of the prepared dipropylene glycol ester composition was 2-2 (2- (2). -Ethylhexanoyloxy) propoxy) isopropyl 2-ethylhexanoate 5% by weight, 1-methyl-2- (2-phenylcarbonyloxypropoxy) ethyl 2-ethylhexanoate 27% by weight and 1- Methyl-2- (2-phenylcarbonyloxypropoxy) ethyl benzoate was 68% by weight, and the ingredients and contents were confirmed by a gas chromatography mass spectrometer.

The polyvinyl chloride resin was obtained using the dipropylene glycol ester composition obtained above as a plasticizer. As in Example 1, a plurality of dumbbell-shaped specimens of type C were manufactured and tested.

Example 3

A dipropylene glycol ester plasticizer composition was prepared in the same manner as in Example 1 except for using the components and contents shown in Table 1 below, and the composition ratio of the prepared dipropylene glycol ester composition was 2-2 (2- (2). -Ethylhexanoyloxy) propoxy) isopropyl 2-ethylhexanoate 1% by weight, 1-methyl-2- (2-phenylcarbonyloxypropoxy) ethyl 2-ethylhexanoate, and 1 -Methyl-2- (2-phenylcarbonyloxypropoxy) ethyl benzoate was 87% by weight, and the components and contents were confirmed by a gas chromatography mass spectrometer.

The polyvinyl chloride resin was obtained using the dipropylene glycol ester composition obtained above as a plasticizer. As in Example 1, a plurality of dumbbell-shaped specimens of type C were manufactured and tested.

Comparative Example 1

In the same manner as in Example 1 except that di 2-ethylhexyl adipate (di-ethylhexyladipate, Co., Ltd. LG Chemical, trade name: DOA) was used instead of the dipropylene glycol ester plasticizer composition according to the present invention as a plasticizer. A polyvinyl chloride resin was prepared, from which a plurality of dumbbell-shaped specimens of type C were prepared and tested.

Comparative Example 2

Instead of the dipropylene glycol ester plasticizer composition according to the present invention as a plasticizer, except for using the ester plasticizer obtained by reacting neopentyl glycol and 2-ethylhexanoic acid as shown in Table 1 below and Polyvinyl chloride resin was prepared in the same manner, from which a plurality of dumbbell-shaped specimens of type C were prepared and tested.

Comparative Example 3

Instead of the dipropylene glycol ester plasticizer composition according to the present invention as a plasticizer, except that the ester plasticizer obtained by reacting triethylene glycol and 2-ethylhexanoic acid as shown in Table 1 below was used and Polyvinyl chloride resin was prepared in the same manner, from which a plurality of dumbbell-shaped specimens of type C were prepared and tested.

Comparative Example 4

Polyvinyl chloride resin as in Example 1, except that diisononladipate (diisonoyladipate, LG Chemical, trade name: DINA) was used instead of the dipropylene glycol ester plasticizer composition according to the present invention as a plasticizer. Was prepared, from which a plurality of dumbbell-type specimens of type C were prepared and tested.

division Example Comparative example One 2 3 One 2 3 4     Raw material of plasticizer     Ester Dipropylene glycol mol (g)  3 (402)  3 (402)  3 (402)  -  -  -  - 2-ethylhexanoic acid mol (g)  3.3 (476)  1.5 (216)  0.6 (86.5)  -  3.1 (744)  2.2 (528)  - Benzoic acid mol (g)  3.3 (403)  5.1 (623)  6.0 (733)  -  -  -  - Neopentylglycol mol (g)  -  -  -  -  1.2 (124.8)  -  - Triethylene glycol mol (g)  -  -  -  -  -  1 (150) - Xylene (g)  60  60  60  -  60  60  - Tetraisopropyl titanate (g)  1.9  1.9  1.9  -  1.5  2  - Tensile strength (kgf / ㎡) 1.94 1.88 1.85 1.81 1.87 1.84 1.73 % Elongation 389 390 388 380 385 348 371 Migratory resistance (%) 1.95 1.99 2.25 0.2 0.2 0.3 0.1 Hardness (R-scale) 78 78 79 78 76 78 76 transparency Great Great Great standard equal Inferior equal Sticky Great Great equal standard Inferior Inferior Inferior

As shown in Table 1, the polyvinyl chloride resin prepared by using the dipropylene glycol ester plasticizer composition of Example 1 as a plasticizer is the DOA of Comparative Example 1, which is the plasticizer most widely used for wrap film, is a standard plasticizer Comparison of the single component ester of Comparative Example 2 synthesized by reacting 2-ethylhexanoic acid with DNA and neopentyl glycol of Comparative Example 4 having a structure similar to DEHA, and 2-ethylhexanoic acid with triethylene glycol Tensile strength, elongation, transparency, and adhesion were superior to those of the polyvinyl chloride resin prepared using the single component ester of Example 3 as a plasticizer, and showed similar hardness. These properties indicate that the plasticizer of Example 1 can be suitably used as a plasticizer for resins for wrap films. The polyvinyl chloride resins according to Examples 1 to 3 exhibit somewhat higher values in the deviability, but in the case of wrap film processing, it is preferable that the polyvinyl chloride resin has appropriate delamination resistance rather than too low or too high. Polyvinyl chloride resin is particularly suitable for resins for wrap films.

In addition, the polyvinyl chloride resin prepared using the dipropylene glycol ester composition of Example 2 as a plasticizer and the polyvinyl chloride resin prepared using the dipropylene glycol ester composition of Example 3 as a plasticizer were polyvinyl chloride resins of the comparative example. Compared to or somewhat superior to the physical properties, these properties are also good values to apply to the resin for the wrap film.

As described above, the dipropylene glycol ester plasticizer composition according to the present invention does not have an adipate-based or phthalate-based structure, which is an environmental hormone-inducing substance, and when used as a plasticizer of polyvinyl chloride resin, tensile strength, elongation, and inner ear There is an effect of providing a polyvinyl chloride resin for wrap film having excellent compatibility with planets, hardness, transparency, adhesion, and resin.

While the present invention has been described in detail with reference to the described embodiments, it will be apparent to those skilled in the art that various modifications and variations are possible within the scope and spirit of the present invention, and such modifications and modifications fall within the scope of the appended claims. It is also natural.

Claims (12)

Dipropylene glycol ester compound of Formula 1 [Formula 1] R ₁ OCO-C ₃ H ₆ -OC ₃ H ₆ -OCOR ₁ In the above formula, R ₁ is an alkyl group having 3 to 12 carbon atoms. Dipropylene glycol ester compound of Formula 2  [Formula 2] R ₂ OCO-C ₃ H ₆ -OC ₃ H ₆ -OCOR ₃ In the above formula, R ₂ is an alkyl group having 3 to 12 carbon atoms, R ₃ is an aryl group having 6 to 10 carbon atoms. The dipropylene glycol ester compound according to claim 1, wherein R ₁ is 1-ethylpentyl. The dipropylene glycol ester compound according to claim 2, wherein R ₂ is 1-ethylpentyl and R ₃ is phenyl. (A) 5 to 80% by weight of the dipropylene glycol ester compound of Formula 1; (b) 10 to 80% by weight of the dipropylene glycol ester compound of Formula 2; And (c) 5 to 80% by weight of the dipropylene glycol ester compound of the formula Dipropylene glycol ester plasticizer composition consisting of: [Formula 1] R ₁ OCO-C ₃ H ₆ -OC ₃ H ₆ -OCOR ₁ [Formula 2] R ₂ OCO-C ₃ H ₆ -OC ₃ H ₆ -OCOR ₃ [Formula 3] R ₄ OCO-C ₃ H ₆ -OC ₃ H ₆ -OCOR ₄ In the above formulas, R ₁ is an alkyl group having 3 to 12 carbon atoms, R ₂ is an alkyl group having 3 to 12 carbon atoms, R ₃ is an aryl group having 6 to 10 carbon atoms, R ₄ is an aryl group having 6 to 10 carbon atoms. According to claim 5, Dipropylene glycol ester compound of Formula 1 10 to 70% by weight; 20 to 70% by weight of the dipropylene glycol ester compound of Formula 2; And 1 to 70% by weight of the dipropylene glycol ester compound of Chemical Formula 3. A compound according to claim 5, wherein the compound of formula 1 is 2-2 (2- (2-ethylhexanoyloxy) propoxy) isopropyl 2-ethylhexanoate [2-2- (2- (2-ethylhexanoyloxy) propoxy) isopropyl 2-ethylhexanoate], and the compound of Formula 2 is 1-methyl-2- (2-phenylcarbonyloxypropoxy) ethyl 2-ethylhexanoate [1-methyl-2- (2-phenylcarbonyloxypropoxy) ethyl 2-ethylhexanoate], and the compound of Formula 3 is 1-methyl-2- (2-phenylcarbonyloxypropoxy) ethyl benzoate [1-methyl-2- (2-phenylcarbonyloxypropoxy) ethyl benzoate] Dipropylene glycol ester plasticizer composition A dipropylene glycol according to claim 5 comprising reacting 10 to 40% by weight of dipropylene glycol, 1 to 70% by weight of fatty acids having 3 to 12 carbon atoms and 1 to 70% by weight of aromatic acids having 6 to 10 carbon atoms. Process for producing propylene glycol ester plasticizer composition. The production method according to claim 8, wherein the fatty acid is 2-ethylhexanoic acid and the aromatic acid is benzoic acid. The method according to claim 8, wherein the reaction is carried out at a temperature of 100 to 220 캜 for 4 to 10 hours. The method according to claim 8, wherein 1 to 20 parts by weight of xylene and 0.0001 to 1 part by weight of tetraisopropyl titanate are added to the total 100 parts by weight of the reactant. Polyvinyl chloride resin containing the dipropylene glycol ester plasticizer composition of any one of Claims 5-7.

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