KR101476378B1 - Modified polylactide resin with cadanol and preparation method thererof - Google Patents

Abstract

The present invention relates to a modified polylactide resin which is excellent in various physical properties such as mechanical properties, transparency and processability, is excellent in coating properties, is free from problems such as contamination or toxicity, . The polylactide resin is provided through copolymerization of an epoxidized cardanol derivative, which is a biomass, with a lactide monomer.

Description

MODIFIED POLYLACTIDE RESIN WITH CADANOL AND PREPARATION METHOD THEREROF [0002]

The present invention relates to a modified polylactide resin and a method for producing the same.

The polylactide (or polylactic acid or polylactic acid) resin is a kind of resin containing a repeating unit represented by the following formula. Because these polylactide resins are biomass-based, unlike conventional crude oil-based resins, it is possible to utilize recycled resources and produce less CO _{2, which} is a global warming gas, than conventional resins. , Biodegradable by moisture and microorganisms at the time of landfilling, and has appropriate mechanical strength similar to that of conventional crude oil-based resins.

[General formula]

As a method for producing a polylactide resin, there is known a method of directly condensing lactic acid or ring opening polymerization of an lactide monomer under an organometallic catalyst. Among them, in the direct condensation polymerization method, the viscosity increases sharply as the condensation polymerization progresses, and it becomes very difficult to effectively remove moisture as a reaction by-product. Therefore, it is difficult to obtain a polymer having a high molecular weight of 100,000 or more as a weight average molecular weight, and therefore it is difficult to sufficiently secure the physical and mechanical properties of the polylactide resin. On the other hand, the ring-opening polymerization method of lactide monomers requires a lactide monomer to be prepared first in lactic acid. Therefore, the production process is complicated and requires a high unit cost compared to the polycondensation, but lactide ring- Can be relatively easily obtained and the polymerization rate can be controlled in a favorable manner.

Such polylactide resins have been mainly used for disposable packaging / containers, coatings, foams, films / sheets and fibers. In recent years, polylactide resins have been used in the production of conventional resins such as acrylonitrile butadiene styrene (ABS), polycarbonate or polypropylene To enhance the physical properties thereof, and thereafter, efforts are being made to use them for semi-permanent use such as a cellular phone exterior material or automobile interior material.

However, the polylactide resin has its own weak physical properties such as hydrolysis by the catalyst used in the production and factors such as moisture in the air. Also, when the polylactide resin or the copolymer containing the polylactide resin is processed into a film form and used as a disposable packaging material, it may be vulnerable to impact, and mechanical properties such as coating and flexibility may be deteriorated. In order to improve such physical properties, it is necessary to have a functional group having a high molecular weight and to form an additional bond between the polymer chains and to crosslink the polymer, or the functional group having a desired characteristic is exposed on the surface of the film, I need a plan.

Therefore, in recent years, studies have been made to develop a modified polylactide resin which is produced by using various monomers in the production of polylactide resin.

For example, Korean Patent Laid-Open Publication No. 2008-0053219 discloses a polyether polyol prepared by alkoxylation of a cashew nutshell liquid (CNSL) which is a renewable material, and a process for producing these novel polyether polyols have. However, this method is limited to the flexible polyurethane foam, and since the Tm of the polymer formed is high, a large amount of energy is required at the time of processing, molecular weight control is difficult, and it is difficult to uniformly modify the chemical characteristics.

Accordingly, the present invention provides a modified polyphenylene sulfide resin composition which is excellent in all of mechanical properties such as coating properties, processability, and heat resistance, has a narrow molecular weight distribution and is easy to control molecular weight and has no problems such as contamination or toxicity, Lactide resin and a process for producing the same.

The present invention relates to an epoxidized cardanol compound represented by the following formula (1); And

A copolymer of a poly (lactic acid) having a repeating unit represented by the following formula (2)

Modified polylactide resin.

[Chemical Formula 1]

(2)

(Wherein R 'is an unsaturated hydrocarbon having 15 or more carbon atoms and having at least one double bond,

and n is an integer of 1 to 6000)

In the above formula (1), R 'may be any one selected from the following formulas.

The present invention also relates to a process for producing an epoxidized cardanol compound of the above formula (1) under catalytic conditions; And copolymerizing the lactide monomer

And a method for producing the modified polylactide resin.

Hereinafter, a modified polylactide resin according to a specific embodiment of the invention and a method for producing the modified polylactide resin will be described in detail.

According to one embodiment of the invention, an epoxidized cardanol compound of formula 1: And a polylactic acid having a repeating unit represented by the following formula (2).

[Chemical Formula 1]

(2)

(Wherein R 'is an unsaturated hydrocarbon having 15 or more carbon atoms having at least one double bond, and n is an integer of 1 to 6000, more preferably an integer of 100 to 3000)

In the above formula (1), R 'may be any one selected from the following structural formulas, and preferably a structure having 2 to 3 double bonds is used.

According to another embodiment of the present invention, there is provided an epoxidized cardanol compound of Formula 1, And a step of copolymerizing the lactide monomer with the lactide monomer.

The modified polylactide resin referred to in the present invention is obtained using cashew nutshell (cardanol) derivatives and lactide. That is, the polylactide resin of the present invention has a structure derived from a cadanol-based compound of the formula (1), which is a biomass, and a lactide that satisfies predetermined structural characteristics including a biodegradable polymer, ≪ / RTI >

The modified polylactide resin of the present invention can improve various properties such as mechanical properties, transparency and processability by improving the coating property upon processing, and is also excellent in heat resistance and can be obtained by using a biopolymer, There is no problem. Further, the present invention can variously control the molecular weight range of the modified polylactide resin by controlling the content of the compound of formula (1), and also can narrow the molecular weight distribution to the existing range.

Hereinafter, the modified polylactide resin of the present invention and the production method thereof will be described in more detail. The modified polylactide resin may be prepared by following the procedure of Reaction Scheme 1 below.

[Reaction Scheme 1]

(Wherein R ' and n are as defined above)

Referring to Scheme 1, in the present invention epichlorohydrin represented by Chemical Formula 3 and Chemical Formula 4 is subjected to a nucleophilic substitution reaction in the presence of a base such as sodium hydroxide to prepare an epoxidized cardanol compound represented by Chemical Formula 1 as a cardanol derivative. Since the compound of Formula 1 contains an epoxy group and three unsaturated hydrocarbons in a long chain hydrocarbon having 15 carbon atoms, it can provide a multifunctional group.

Accordingly, in the present invention, it is possible to provide a modified polylactide resin (formula (A)) which is a PLA biodegradable polymer having a polylactic acid repeat unit of formula (2) by copolymerizing a lactide monomer represented by formula (1). The modified polylactide resin has excellent coating properties and mechanical properties.

In addition, in the present invention, all bio-based materials as natural materials can be used in PLA to improve functionalities such as workability and coating properties. Here, the functional groups including the epoxy group of Formula 1 may be bonded to the ether functional group of poly (lactic acid). That is, the ring-opening polymerization of lactide is induced in the epoxy group of the formula (1), and binding of cardanol to PLA occurs. Further, since a substance in which a functional group (ex., Unsaturated bond) of an alkyl group is retained even after polymerization is used, an additional reaction process can be performed, and at the same time, an improvement in coating property and solubility is expected.

Furthermore, the present invention can control the molecular weight and conversion of the final polylactide resin through controlling the addition amount of the cardanol derivative of the formula (1), thereby controlling the mechanical properties.

Since the polylactic acid repeating unit of formula (2) exhibits hydrophilicity, in the present invention, by introducing the cardanol derivative of formula (1) having hydrophobicity in the production of modified polylactide resin, The hydrophilicity of the polylactic acid of formula (2) can be controlled.

In addition, since the present invention provides a multifunctional group using one to three double bonds contained in the cardanol derivative, multifunctional groups including an unsaturated bond after reacting with the lactide monomer can impart crosslinkability to the modified PLA resin . The molecular weight of the modified polylactide resin can be controlled depending on the amount of the cardanol derivative added.

The modified polylactide resin preferably has a weight average molecular weight of 10,000 to 500,000, a PDI of 1.01 to 2.5, a glass transition temperature (Tg) of 40 to 80 占 폚, a crystallization temperature (Tc) of 80 to 130 占 폚, (Tm) may be from 150 캜 to 200 캜. Also, according to the present invention, the conversion of the polylactide may be from 60% to 98%, more preferably from 75% to 98%. More preferably, the modified polylactide resin has a weight average molecular weight of 20,000 to 500,000, a PDI of 1.1 to 2.5, a glass transition temperature (Tg) of 40 to 80 ° C, a crystallization temperature (Tc) of 90 to 120 ° C , And the melting temperature (Tm) may be from 150 캜 to 190 캜.

On the other hand, in the production of the modified polylactide resin, the epoxidized cardanol compound: lactide monomer of Formula 1 is used at a ratio of 1:10 to 1:15 (mmole / mmole ratio), more preferably 1: 5 to 1 : 100 (mmole / mmole ratio). If the ratio is less than 1:10 (mole / mole ratio), there is a problem of adversely affecting the molecular weight of the obtained polylactide polymer. If the ratio is more than 1: 150 (mole / mole ratio), the content of the cardanol derivative is too small There is a problem that the lactide is not uniformly dispersed in the melt.

Further, throughout the present specification, "lactide monomer" can be defined as follows. Generally, lactide can be divided into L-lactide composed of L-lactic acid, D-lactide composed of D-lactic acid, and meso-lactide composed of one L-form and one D-form. Also, a mixture of L-lactide and D-lactide at 50:50 is referred to as D, L-lactide or rac-lactide. In the present invention, any of the above compounds among these lactides can be used, but it is more preferable to use L-lactide or D-lactide having high optical purity. It is known that when L-lactide or D-lactide having high optical purity is used, L- or D-polylactide (PLLA or PDLA) having very high stereoregularity is obtained, and such polylactide has optical purity It is known that the crystallization speed is higher than that of low polylactide and the crystallinity is also high. However, the term "lactide monomer" is defined herein to include all types of lactide, regardless of the difference in properties of the lactide according to each type and the characteristic difference of the formed polylactide therefrom.

In the present invention, ring-opening polymerization may be carried out under the organometallic catalyst when the above-mentioned formula (1) and the lactide monomer are polymerized.

That is, in order to produce the finally obtained modified polylactide resin, the reaction can be carried out in the presence of a catalyst such as an organotin compound in the same manner as in the production of a general polylactide resin.

The catalyst may be used at a ratio of 1: 10000 to 1: 100,000 (mmole / mmole ratio), more preferably from 1: 10000 to 1: 60000 (mmole / mmole ratio), based on the lactide monomer. On the contrary, when the addition ratio of the catalyst is too large, the amount of the residual catalyst of the produced modified polylactide resin becomes large, so that the decomposition or molecular weight reduction of the copolymer, And the like.

It is also preferred that the catalyst comprises a mixture of organometallic complexes of the following general formula (4) or of the following general formulas (5) and (6).

[Chemical Formula 4]

[Chemical Formula 5]

[Chemical Formula 6]

MX _p Y _{2 -p}

(Wherein, n is an integer of 0 to 15, p is an integer of 0 to 2, M is Sn or Zn, R ¹ and R ³ may be the same or different from each other, Substituted or unsubstituted C 3 -C 10 alkyl, substituted or unsubstituted C 3 -C 10 cycloalkyl, substituted or unsubstituted C 6 -C 10 aryl, and R ² is a substituted or unsubstituted C 3 -C 10 A substituted or unsubstituted alkylene, a substituted or unsubstituted cycloalkylene having 3 to 10 carbon atoms, a substituted or unsubstituted arylene having 6 to 10 carbon atoms, and each of X and Y is independently an alkoxy or carboxyl group)

More preferably, the catalyst comprises Sn (Oct) ₂ and N, N'-carbonyldiimidazole.

In addition, as described above, the copolymerization reaction between the lactone monomer and the lactone monomer of the present invention may be carried out by a ring-opening polymerization. Preferably, the ring-opening polymerization proceeds substantially to a bulk polymerization not using a solvent. At this time, substantially no solvent is used to include a small amount of solvent for dissolving the catalyst, for example, up to about 1 ml of solvent per kg of the polylactic acid of formula 2 used for polymerization .

As the ring-opening polymerization proceeds to bulk polymerization, the step for removing the solvent after polymerization can be omitted, and the decomposition or loss of the copolymer in the solvent removal step can be suppressed. In addition, the lactide copolymer can be obtained at a high conversion rate and yield by the bulk polymerization.

The copolymerization may be carried out at a temperature of 170 to 190 DEG C for 30 minutes to 6 hours. More preferably, the copolymerizing step can be carried out at a temperature of 170 to 180 DEG C for 30 minutes to 4 hours.

According to the above-mentioned production method, the present invention provides a process for producing a polyolefin resin composition, which is capable of securing excellent mechanical properties, flexibility and processability by improving the coating property by exhibiting a predetermined structural characteristic, a high molecular weight and an appropriate melt viscosity The modified polylactide resin can be produced at a high conversion rate.

On the other hand, as described above, the epoxidized cardanol compound of Formula 1 is a derivative of cardanol, which is prepared by a nucleophilic substitution reaction of a compound of Formula 3, which is extracted from cardanol with a base catalyst, and epichlorohydrin .

(3)

(Wherein R 'is any one selected from the following structural formulas)

Generally, cadanol is obtained by extraction of cashew netshell liquid, its derivatives being mainly used as epoxy curing agent, phenolic resin, surfactant and emulsion breaker. The cashew nut shell liquid is a natural vegetable oil extracted from the fruit skin of cashew belonging to the lacquer tree in the rainforest, and the cardanol extracted therefrom can be represented by the following Formula 3-1.

[Formula 3-1]

(Wherein R " includes the following structural formula)

As can be seen from the above formula, the cardanol is a mixture of phenol derivatives having four kinds of alkyl groups at the meta position, and the compounds having each alkyl group are mixed at a ratio of 3%, 34%, 22% and 41%, respectively .

However, there is a problem in that the cardanol itself is not stable enough. The phenol group present in cardanol corrodes the mucous membrane of the skin, denatures the protein and the cell prototype, damages the cell membrane of red blood cells, . Since the polymerization reactivity is very low, only a polymer substance having a number average molecular weight of several thousands or less can be obtained even if polymerization and curing are carried out by maintaining an appropriate temperature and humidity. Therefore, it has recently been widely used as a derivative.

In the present invention, the above-described epichlorohydrin is reacted with the above-described cardanol to allow the oxygen of the phenol group to spontaneously bond with the hydrocarbon compound having one epoxy functional group through the nucleophilic substitution, ) Can be provided. At this time, in the present invention, it is preferable to extract and use only the substance having an unsaturated hydrocarbon in cardanol. Accordingly, in the present invention, a compound having the definition of the compound of the above-mentioned formula (3) can be used to react with epichlorohydrin. In addition, since the coating property can be improved by introducing a long alkyl group at the terminal thereof even if it does not have an unsaturated bond, the present invention can use a structure that does not contain an unsaturated bond, if necessary . However, as described above, it is preferable to use a substance having an unsaturated bond for imparting multiple functional groups.

Since the nucleophilic substitution reaction can be carried out within a short time, a cardanol derivative of the formula (1) can be synthesized by a simple method. Preferably, the nucleophilic substitution reaction can be carried out at a reaction temperature of 10 ° C to 70 ° C for 1 hour to 20 hours.

The base catalyst may be at least one selected from the group consisting of potassium hydroxide, barium hydroxide, cesium hydroxide, sodium hydroxide, strontium hydroxide, calcium hydroxide, lithium hydroxide and rubidium hydroxide.

Also, the reaction may be carried out in bulk during the reaction, or a conventional organic solvent may be used. For example, the organic solvent includes chloroform, toluene, xylene, and the like.

In the epoxidized cardanol-based compound obtained by this method, R 'is preferably any one selected from the following structural formulas including a double bond, more preferably a structure having two or three double bonds .

In the case of containing at least one double bond, the functional group for copolymerization may be imparted as described above to improve the crosslinking property.

On the other hand, according to another embodiment of the present invention, there is provided a resin composition comprising the above-mentioned modified polylactide resin.

Such a resin composition exhibits excellent physical and mechanical properties due to the inclusion of a lactide copolymer exhibiting excellent mechanical properties, flexibility, hydrolysis resistance and heat resistance, and exhibits excellent physical and mechanical properties and is useful as a food packaging film, sheet, flooring material, electronic product packaging, And can be preferably used for semi-permanent use.

The resin composition may be a liquid or solid resin composition before molding the final product, or may be a plastic or a fabric in the final product state. The final plastic or fabric product may be manufactured by a conventional method .

Particularly, the above-mentioned resin composition has excellent transparency when forming a film, and has low toxicity due to low residual metal content and greatly improved flexibility, and thus can be usefully used in food packaging films. Therefore, such packaging films can be suitably applied as packaging materials in various fields. For example, sanitary films, lamination films, shrinkable labels, and matte films for snack packaging, such as consumer packaged goods or grocery packages, envelopes, refrigerated / frozen food packaging, shrinkable over-wrapping films, Bundle bundle films, sanitary napkins or baby products In addition, it can be widely used as packing materials for industrial materials such as agricultural mulching films, automobile paint film protective sheets, garbage bags or compost pouches.

The modified polylactide resin of the present invention is a copolymer comprising recurring units of an epoxidized cardanol derivative as a biomass and polylactic acid as a biodegradable polymer and is capable of exhibiting excellent mechanical properties and maintaining excellent flexibility and heat resistance And workability, and there is little fear of contamination or toxicity by the residual catalyst and the monomer. Particularly, the present invention can control the hydrophilicity of the poly (lactic acid) in the resin by controlling the content of the cardanol derivative, and the molecular weight can be controlled by the double bond in the cardanol derivative. Thus, a polylactide resin having an appropriate molecular weight .

Therefore, the modified polylactide resin of the present invention can be suitably applied as various packaging materials such as food packaging materials.

FIG. 1 is a graph showing the conversion rates of the modified polylactide resin of Examples 1 to 3 and the polylactide resin of Comparative Example 1 in accordance with the reaction time and the content of the cardanol derivative.
2 is a graph comparing the weight average molecular weights of the modified polylactide resins of Examples 1 to 3 and the polylactide resins of Comparative Example 1 with respect to the reaction time and the content of cardanol derivatives.
3 is a graph showing the weight average molecular weights of the modified polylactide resin of Examples 1 to 3 and the polylactide resin of Comparative Example 1 in comparison.
4 is a graph comparing the contact angles of Examples 1 to 3 and Comparative Example 1 with respect to water.
5 is a graph showing the heat resistance of the modified polylactide resin of Examples 2 to 3 and the polylactide resin of Comparative Example 1 in comparison.
6 is a ¹ H NMR spectrum of the modified polylactide resin of Example 3.

Best Mode for Carrying Out the Invention Hereinafter, the function and effect of the present invention will be described in more detail through specific examples of the present invention. It is to be understood, however, that these embodiments are merely illustrative of the invention and are not intended to limit the scope of the invention.

[Experimental Method]

In the following Examples and Comparative Examples, all work to treat air- or water-sensitive compounds was carried out using the standard Schlenk technique or the dry box technique.

In the following examples, definitions and measurement methods of physical properties are as summarized below.

[Synthesis Example 1]

120 g of cardanol (3 - ((8E, 11E) -pentadeca-8,11,14-trienyl) phenol of Formula 3-1 and 38 ml of epichlorohydrin extracted from the cashew nut shell liquid were put into a 500 ml reactor. Then, 19.3 g of NaOH was added. Then, the mixture was reacted with stirring at 100 DEG C for 4 hours. The solvent was then removed under vacuum and purified to give the epoxidized cardanol derivative of Formula 1-1.

[Formula 1-1]

[Formula 3-1]

[Examples 1 to 3]

Lactide monomer (2 g, 13.8 mmol) and Sn (Oct) ₂ (toluene solution, 0.1 mL) were added to each 30 mL vial and left under vacuum for 2 hours.

The epoxidized cardanol derivative of formula (1-1) was added to the vial (reactor) with the contents shown in Table 1 below. Then, a ring-opening polymerization reaction was carried out at a temperature of 180 ° C for 1 hour to prepare a modified polylactide resin.

At this time, the polylactic acid repeating unit contained in the modified polylactide resin was obtained after the polymerization was carried out by adding the cardanol derivative and the lactide monomer together in the polymerization step.

[Comparative Example 1]

A commercially available NatureWorks 4032D polylactide resin was used.

[Experimental Example 1]

A part of the polymer resins of the above Examples and Comparative Examples was sampled and the weight average molecular weight was measured using GPC (Gel Permeation Chromatography). From the above results, the number average molecular weight was measured and the catalytic activity, PDI, glass transition temperature (Tg), crystallization temperature (Tc) and melting temperature (TM) of the polylactide resin were measured and the results are shown in Table 1 .

Further, the polymerization reaction time was increased to 2 hours, and the change of the weight average molecular weight and conversion rate with time was observed.

1 and 2 show the conversion ratio and the weight average molecular weight of the modified polylactide resin of Examples 1 to 3 and the polylactide resin of Comparative Example 1, respectively, according to the reaction time and the content of the cardanol derivative. 3 is a graph showing the weight average molecular weights of the modified polylactide resin of Examples 1 to 3 and the polylactide resin of Comparative Example 1 in comparison.

Example 1 Example 2 Example 3 Comparative Example 1 Cardanol: Lactide
(mmol / mmol) 1: 140 1:70 1:15 - Reaction time (hr) One 2 One 2 One 2 One 2 Conversion Rate (%) 90 89 88 87 81 79 85 86 activation
(Kg-pol /
h.mol.cat) 4480 2219 4480 2214 4652 2286 4911 2479 Mn (* 10 ³ Da) 180 134 101 80 19.8 18.5 243 204 Mw (* 10 ³ Da) 309 242 173 132 33 31 457 425 PDI 1.72 1.8 1.71 1.65 1.68 1.67 1.88 2.08 Tg (占 폚) 61 61 53 63 Tc (占 폚) 109 105 100 110 Tm (占 폚) 175 175 164 178 * Codanol content: Represents molar ratio value to lactide content
* PDI: Represents the polydispersity index (PDI).

Referring to the above Table 1, it was confirmed that the modified polylactide resins of Examples 1 to 3 can produce a resin having a wider range of molecular weight than that of Comparative Example 1. In particular, the embodiment of the present invention can provide a modified polylactide resin having a narrow molecular weight distribution because the PDI is low as compared with the comparative example.

It is also possible to provide a polylactide resin having a high molecular weight and an excellent conversion rate even when a small amount of a cardanol derivative is used. In addition, the glass transition temperature, the crystallization temperature, and the melting temperature of the examples of the present invention were the same as those of the comparative examples.

1 and 2, when the polymerization time is increased from 1 hour to 2 hours, it can be seen that conversion rate and molecular weight are decreased overall. In the case of FIG. 3, the molecular weight of the modified polylactide resin is decreased with an increase in the content of the cardanol derivative as a result of the reaction for 1 hour. From these results, it was confirmed that the molecular weight range according to the present invention can be variously controlled.

In addition, the modified polylactide resin of Example 2-3 and the polylactide resin of Comparative Example 1 were measured for heat resistance, and the results are shown in FIG. 4 (a) and 4 (b) illustrate thermal-mechanical properties of polylactide resins using a differential scanning calorimeter (DSC) and a thermogravimetric analyzer (TGA).

In addition, in the case of Fig. 4, Examples 1 to 3 of the present invention improved the surface properties, and thus the contact angles to water were better than those of Comparative Example 1.

It can be seen from FIG. 5 that the thermal stability of the present invention is better than that of the comparative example and general cardanol.

The ¹ H NMR spectrum of the modified polylactide resin of Example 3 is as shown in FIG. From Fig. 6, it was confirmed that double bonds of the chain of the cardanol derivatives remained after the polymerization. From this, improvement of properties such as multi-functional group addition and coating property improvement was expected.

As described above, the present invention uses a modified polymer obtained by introducing a functional group into a PLA polymer chain, and therefore, when a further process is carried out (for example, a process of forming a film or further crosslinking to increase the strength of the coating surface is performed , It is possible to impart functional groups to PLA of all biobased materials and to improve physical properties such as workability and coating properties.

Claims (13)

An epoxidized cardanol compound of Formula 1; And
A copolymer of a poly (lactic acid) having a repeating unit represented by the following formula (2)
Modified polylactide resin.
[Chemical Formula 1]

(2)

(Wherein R 'is an unsaturated hydrocarbon having 15 or more carbon atoms and having at least one double bond,
and n is an integer of 1 to 6000)
The modified polylactide resin according to claim 1, wherein R 'in the formula (1) comprises any one selected from the following formulas.

The method according to claim 1,
A glass transition temperature (Tg) of 40 to 80 占 폚, a crystallization temperature (Tc) of 80 to 130 占 폚, a melting temperature (Tm) of 150 to 500 占 폚, a weight average molecular weight of 10,000 to 500,000, a PDI of 1.01 to 2.5, 200 <
Modified polylactide resin.
The modified polylactide resin according to claim 1, wherein the conversion is 60% to 98%.
Under catalytic conditions,
An epoxidized cardanol compound of Formula 1; And copolymerizing the lactide monomer
Wherein the modified polylactide resin is a polylactide resin.
[Chemical Formula 1]

(Wherein R 'is an unsaturated hydrocarbon having 15 or more carbon atoms having at least one double bond)
The process for producing a modified polylactide resin according to claim 5, wherein R 'in the formula (1) is any one selected from the following formulas.

6. The process for producing a modified polylactide resin according to claim 5, wherein the cardanol compound: lactide monomer of Formula 1 is used in a molar ratio of 1:10 to 1: 150 (mmole / mmole ratio).
6. The process according to claim 5,
Wherein the modified polylactide resin is used in a ratio of 1: 10000 to 1: 100000 (mmole / mmole ratio) to the lactide monomer.
6. The process according to claim 5,
A method for producing a modified polylactide resin comprising an organometallic complex represented by the following general formula (4), or a mixture of the following general formulas (5) and (6).
[Chemical Formula 4]

[Chemical Formula 5]

[Chemical Formula 6]
MX _p Y _{2 -p}
(Wherein, n is an integer of 0 to 15, p is an integer of 0 to 2, M is Sn or Zn, R ¹ and R ³ may be the same or different from each other, Substituted or unsubstituted C 3 -C 10 alkyl, substituted or unsubstituted C 3 -C 10 cycloalkyl, substituted or unsubstituted C 6 -C 10 aryl, and R ² is a substituted or unsubstituted C 3 -C 10 A substituted or unsubstituted alkylene, a substituted or unsubstituted cycloalkylene having 3 to 10 carbon atoms, a substituted or unsubstituted arylene having 6 to 10 carbon atoms, and each of X and Y is independently an alkoxy or carboxyl group)
6. The method of producing a modified polylactide resin according to claim 5, wherein the catalyst comprises Sn (Oct) ₂ and N, N'-carbonyldiimidazole.
6. The method of claim 5, wherein the epoxidized cardanol compound of formula (1)
Wherein the nucleophilic substitution reaction is carried out by a nucleophilic substitution reaction of a compound represented by the following formula (3) extracted from cardanol with a base catalyst and epichlorohydrin.
(3)

(Wherein R 'is any one selected from the following structural formulas)

6. The method of claim 5,
At a temperature of 170 to 190 캜 for 30 minutes to 6 hours.
A polylactide resin composition comprising the modified polylactide resin according to claim 1.

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