KR101406909B1 - Method of manufacturing biodegradable polyester resin - Google Patents

Abstract

The present invention relates to a method for producing a biodegradable polyester resin, and more particularly to a method for producing a polyester resin having practical biodegradability and excellent mechanical properties such as tensile strength, elongation, and tensile elastic modulus.
As a means for solving the above-mentioned object, the present invention relates to a process for producing a dicarboxylic acid, which comprises the steps of: S1) mixing 10 to 60% by weight of an aliphatic dicarboxylic acid or a cycloaliphatic dicarboxylic acid or an ester-forming derivative thereof with an aromatic dicarboxylic acid or an ester- A mixture of 20 to 70% by weight of a forming derivative; And 20 to 60% by weight of a mixture of any one of aliphatic diols and mixtures thereof is subjected to an esterification reaction at 180 to 230 ° C in a stream of nitrogen in the presence of dehydration; S2) After dehydration, 0.6 to 1.0 part by weight of a titanium catalyst is added to 100 parts by weight of the oligomer obtained in the step S1) to carry out the deglycolysis at 230 to 250 ° C .; And S3) 1 to 15 parts by weight of magnesium oxide or zinc oxide and 5 to 10 parts by weight of 1,3,5-triglycidyl isocyanurate as a coupling agent are added to 100 parts by weight of the polyester after the step S2) And then reacting the mixture at a reduced pressure at 250 to 270 ° C to react the biodegradable polyester resin.
According to the present invention, in the production of the conventional biodegradable polyester, the problem that the biodegradability is remarkably reduced as the molecular weight of the homopolymer is increased can be solved. In the case of the biodegradable polyester according to the present invention, As the polymer having a molecular weight of 80,000 or more, a dicarboxylic acid and an aromatic dicarboxylic acid and 1,3,5 triglycidyl isocyanurate are used in combination, which is suitable for production of a molded article and excellent mechanical strength can be obtained.

Description

METHOD OF MANUFACTURING BIODEGRADABLE POLYESTER RESIN BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to a biodegradable polyester resin,

The present invention relates to a process for producing a biodegradable polyester resin, and more particularly to a process for producing a biodegradable polyester resin having practical biodegradability and having excellent thermal properties in vacuum forming and blow molding.

In general, polyester has excellent mechanical properties, chemical resistance and durability, and is widely used in daily life as a substitute for natural fibers. However, polyester has a disadvantage that it can not be reduced to nature when it is disposed of after use. Disposable packaging materials, which have a constant demand, are often consumed, but they are often left untreated because they are not recovered smoothly. Agricultural films are difficult to recover completely, so they are buried in the soil and cause a great deal of obstacles to cultivation of crops. Is becoming a reality.

As environmental pollution caused by such plastic wastes has become a social problem, the development of decomposable resins which are automatically decomposed at the time of disposal after a certain period of use has been actively promoted in order to protect the environment.

Therefore, studies using lignin are underway to develop cheap and biodegradable resins. This lignin is a natural polymer that can be easily decomposed by microorganisms in the ground. Since it is a polymer material that can be easily and mass-produced from wood, various application methods are proposed.

Conventional methods for producing biodegradable resins using such lignin include a copolymer of acrylamide and lignin, a copolymer of acrylic acid and lignin, a copolymer of substituted acrylamide and lignin, a copolymer of substituted acrylic acid and lignin, a polyethylene glycol Copolymers of acrylate and lignin, copolymers of styrene and lignin, and methods of making copolymers of acrylonitrile and lignin. This method grafts lignin to the side chains of the non-degradable thermoplastic resin to make the resin biodegradable. Resin made by this method has many differences in the degree of decomposition depending on the content of lignin and the molecular weight of non-degradable thermoplastic resin.

In order to make a high-degradable resin, it is necessary to considerably increase the content of lignin. This is because, when landfilled, microorganisms for decomposing lignin are easily contacted and decomposition is facilitated. However, resins having an increased content of lignin exhibit characteristics of lignin itself, resulting in poor processability and loss of physical properties of desired resins, which limits their use.

On the other hand, when the thermoplastic resin in the copolymer is a resin having a high molecular weight, phase transformation occurs from the phase of lignin to the phase of the thermoplastic resin, so that desired processing characteristics and the like can be obtained. However, It is disadvantageous that decomposition is not easily performed because it interferes with the contact of microorganisms for decomposing lignin upon embedding due to resin.

Therefore, the mechanical properties of the thermoplastic resin can be maintained while containing a large amount of the lignin, so that the mechanical properties are maintained at the time of using the thermoplastic resin. However, biodegradation can be easily performed after the thermoplastic resin is used, The development of cast polyesters is required.

Disclosure of the Invention The present invention has been made to solve the above-mentioned problems, and provides a process for producing a biodegradable polyester resin which is excellent in practicality and biodegradability, has excellent thermal stability and mechanical strength, and is excellent in blow moldability. .

The thermal stability and the mechanical strength were characterized by chain extension using a mixture of? -Triglycidyl isocyanurate and? -Triglycidyl isocyanurate to improve mechanical properties, while the main chain was biodegradable The polyolefin has an ester, and the lignin is grafted to the side chain, and the contact surface is formed widely to decompose the lignin after use of the polyester, thereby improving the efficiency of the degradability.

As a means for solving the above-mentioned object, the present invention relates to a process for producing a dicarboxylic acid, which comprises: S1) 10 to 60% by weight of an aliphatic dicarboxylic acid or a cycloaliphatic dicarboxylic acid or an ester-forming derivative thereof, -Forming derivative of 20 to 70% by weight; And an aliphatic diol or a mixture thereof in an amount of 30 to 60% by weight, the mixture being subjected to an esterification reaction at 180 to 230 ° C in a stream of nitrogen in the course of dehydration;

S2) After dewatering, 0.6 to 1.0 part by weight of tetrabutyl titanate as a catalyst is added to 100 parts by weight of the oligomer obtained in the step S1), and the deglycol reaction is carried out at 230 to 250 ° C .; And

S3) 1 to 3 parts by weight of magnesium oxide or zinc oxide, 1 to 3 parts by weight of 1,3,5-triglycidyl isocyanurate, 50 to 60 parts by weight of lean green to 100 parts by weight of the polyester after step S2) And the mixture is reacted by stirring at a speed of 150 to 250 rpm for 2 to 4 hours under a reduced pressure at 250 to 270 ° C to prepare a biodegradable polyester resin.

The 1,3,5-triglycidyl isocyanurate is a mixture of α-triglycidyl isocyanurate and β-triglycidyl isocyanurate in a ratio of 70 to 80% by weight: 20 to 30% by weight .

The aliphatic dicarboxylic acid or the cycloaliphatic dicarboxylic acid or an ester-forming derivative thereof is preferably adipic acid and sebacic acid, and the mixing ratio thereof is preferably adipic acid: sebacic acid = 1: 0.5 to 1.5.

The aromatic dicarboxylic acid or an ester-forming derivative thereof is preferably any one of terephthalic acid, isophthalic acid, 2,6 naphthalic acid and 1,5-naphthalic acid, or a mixture thereof.

The aliphatic diol may be selected from the group consisting of 1,3-butanediol, 2-methyl-1,2-propanediol, 2-methyl-1,3-propanediol, Pentanediol, 2-methyl-2,4-pentanediol, 1,2-hexanediol, 1,3-hexanediol, 1,5-hexanediol, 2,3- , 4-hexanediol, 2,5-hexanediol, 3,4-hexanediol, 1,2-heptanediol, 1,3-heptanediol, 1,4-heptanediol, 3-heptanediol, 2,5-heptanediol, 2,6-heptanediol, 3,4-heptanediol and 3,5-heptanediol, or a mixture of two or more thereof.

According to the present invention, in the production of the conventional biodegradable polyester, the problem that the biodegradability is remarkably reduced as the molecular weight of the homopolymer is increased can be solved. In the case of the biodegradable polyester according to the present invention, As the polymer having a molecular weight of 80,000 or more, a dicarboxylic acid and an aromatic dicarboxylic acid and 1,3,5 triglycidyl isocyanurate are used in combination, which is suitable for production of a molded article and excellent mechanical strength can be obtained.

Further, biodegradable polyester grafted with lignin as a side chain has a high number-average molecular weight and is excellent in mechanical strength, and has good biodegradability due to smooth contact with microorganisms during its decomposition.

Hereinafter, embodiments of the present invention will be described in detail so that those skilled in the art can easily carry out the present invention.

The present invention relates to a process for the preparation of a mixture comprising: S1) 10 to 60% by weight of an aliphatic dicarboxylic acid or a cycloaliphatic dicarboxylic acid or an ester-forming derivative thereof, 20 to 70% by weight of an aromatic dicarboxylic acid or an ester-forming derivative thereof; And an aliphatic diol or a mixture thereof in an amount of 30 to 60% by weight, the mixture being subjected to an esterification reaction at 180 to 230 ° C in a stream of nitrogen in the course of dehydration; S2) After dewatering, 0.6 to 1.0 part by weight of tetrabutyl titanate as a catalyst is added to 100 parts by weight of the oligomer obtained in the step S1), and the deglycol reaction is carried out at 230 to 250 ° C .; And S3) 1 to 3 parts by weight of magnesium oxide or zinc oxide, 1 to 3 parts by weight of 1,3,5-triglycidyl isocyanurate, 100 to 3 parts by weight of leucine 50 To 60 parts by weight of a polyester resin, and the mixture is reacted under reduced pressure at 250 to 270 ° C for 2 to 4 hours at a speed of 150 to 250 rpm to react.

The aliphatic dicarboxylic acid generally has 2 to 10 carbon atoms, preferably 4 to 6 carbon atoms. They may be linear and may be branched. Meanwhile, the cycloaliphatic dicarboxylic acid of the present invention generally has 7 to 10 carbon atoms, preferably 8 carbon atoms. However, it is also generally possible to use dicarboxylic acids having a larger number of carbon atoms, for example, up to 30 carbon atoms.

As an example, there may be mentioned, for example, malonic acid, succinic acid, glutaric acid, adipic acid, pimelic acid, azelaic acid, sebacic acid, fumaric acid, 2,2-dimethylglutaric acid, suberic acid, Cyclohexane dicarboxylic acid, diglycolic acid, itaconic acid, maleic acid, and 2,5-norbornanedicarboxylic acid, and among these, adipate Acid or sebacic acid is preferred.

The ester-forming derivatives of the above-mentioned aliphatic or cycloaliphatic dicarboxylic acids include di-C 1 -C 6 -alkyl esters such as dimethyl, diethyl, di-n-propyl, diisopropyl, di- Butyl, diisobutyl, di-t-butyl, di-n-pentyl, diisopentyl or di-n-hexyl esters. Similarly, it is also possible to use an anhydride of a dicarboxylic acid.

It is also possible to use dicarboxylic acids or their ester-forming derivatives alone or a mixture of two or more thereof.

Preferably, the adipic acid or its ester-forming derivative may be used singly or in combination with sebacic acid or an ester-forming derivative thereof or a mixture of adipic acid and sebacic acid or an ester-forming derivative thereof, Adipic acid or its ester-forming derivative can be used alone.

The aromatic dicarboxylic acids are those having 8 to 12, preferably 8, carbon atoms.

Examples thereof include terephthalic acid, isophthalic acid, 2,6-naphthalic acid and 1,5-naphthalic acid, and ester-forming derivatives thereof. Particularly, a di-C1-C6-alkyl ester such as dimethyl, diethyl, di-n-propyl, diisopropyl, di- Pentyl, diisopentyl or di-n-hexyl esters. Anhydrides of dicarboxylic acids may likewise be suitable ester-forming derivatives. In the present invention, terephthalic acid or an ester-forming derivative thereof, especially a dimethyl ester, or a mixture thereof is preferable.

In general, it is also possible to use a large number of aromatic dicarboxylic acids having 20 or fewer carbon atoms, for example.

In the case of the aliphatic alcohol, all aliphatic polyhydric alcohols capable of forming a dicarboxylic acid or ester can be generally used.

In general, branched or linear alkanediols having 2 to 12, preferably 4 to 6, carbon atoms, or cycloalkanediol having 5 to 10 carbon atoms, polyether diols, i.e., Dihydroxy compounds may be used.

Examples of suitable alkanediols are 1,3-butanediol, 2-methyl-1,2-propanediol, 2-methyl-1,3-propanediol, 1,2-pentanediol, Pentanediol, 2-methyl-2,4-pentanediol, 1,2-hexanediol, 1,3-hexanediol, 1,5-hexanediol, 2,3- , 2,4-hexanediol, 2,5-hexanediol, 3,4-hexanediol, 1,2-heptanediol, 1,3-heptanediol, 1,4-heptanediol, 2,3-heptanediol, 2,5-heptanediol, 2,6-heptanediol, 3,4-heptanediol and 3,5-heptanediol, or a mixture of two or more thereof.

 Examples of polyetherdiols are diethylene glycol, triethylene glycol, polyethylene glycol, polypropylene glycol, polytetrahydrofuran, especially diethylene glycol, triethylene glycol, polyethylene glycol, or mixtures thereof, or a different number of ether units For example, a polyethylene glycol obtained by polymerizing propylene oxide after first polymerizing ethylene oxide by a conventional method and having a propylene unit, for example. The molecular weight (Mn) of the polyethylene glycol which can be used is generally about 500 to about 9,000 g / mole, preferably about 1000 to 7,000 g / mole. Mixtures of different polyether diols may likewise be used.

The present invention relates to a composition comprising 10 to 60% by weight of said aliphatic dicarboxylic acid or cycloaliphatic dicarboxylic acid or ester-forming derivative thereof, 20 to 70% by weight of an aromatic dicarboxylic acid or ester-forming derivative thereof; And an aliphatic diol or a mixture thereof in an amount of 20 to 60% by weight is subjected to an esterification reaction at 180 to 230 ° C in a stream of nitrogen by a dehydration reaction. Thereafter, 0.6 to 1.0 part by weight of a titanium catalyst is added to 100 parts by weight of the oligomer obtained after the esterification reaction, and deglycolysis is carried out at 230 to 250 ° C. to obtain a polyester.

Tetrabutyl titanate or the like can be used as a titanium compound which is a reaction promoter added for promoting the deglycolysis which proceeds in the esterification reaction. The amount of the titanium compound to be used is 0.6 to 1.0 part by weight per 100 parts by weight of the oligomer, 0.7 to 0.85 parts by weight is appropriate. When the amount of the titanium catalyst is less than 0.6 parts by weight, the reaction rate is not greatly affected. When the amount is more than 1.0 part by weight, it does not contribute to the substantial reaction rate.

After the deglycolysis, 1 to 3 parts by weight of magnesium oxide or zinc oxide as a coupling agent is added to 100 parts by weight of the polyester obtained at 250 to 270 DEG C, and 1,3,5-triglycidyl And 1 to 3 parts by weight of diallyl isocyanurate. Then, 50 to 60 parts by weight of green is put into the autoclave, the pressure is reduced at 250 to 270 ° C., and the mixture is reacted at a speed of 150 to 250 rpm for 2 to 4 hours to react to prepare a biodegradable polyester.

The 1,3,5-triglycidyl isocyanurate (TGIC) is used as a curing agent for molding, adhesives, and powder paints, and is excellent in adhesion to metals, as well as high heat resistance, And has excellent properties such as weather resistance and is being applied to the field of compounds. It is also widely used in optical and electronic fields due to its excellent transparency and conductivity. In addition, triglycidyl isocyanurate is composed of a pair of stereoisomers, and there are α-type and β-type, one of the α-type is opposite to the other, and β-type is three epoxy groups It is facing the same direction. This is shown in the following chemical formula (1).

[Chemical Formula 1]

The triglycidyl isocyanurate may be prepared by reacting cyanuric acid and epichlorohydrin in the presence of a tetraalkylammonium chloride chloride catalyst at 85 to 120 ° C to produce triglycidyl isocyanurate have.

In the present invention, it is preferable to use 1,3,5-triglycidyl isocyanurate of the? -Type and? -Type, and the proportion of the? -Type triglycidyl isocyanurate and the? It is preferable that the syndiotissocyanurate has 70 to 80% by weight: 20 to 30% by weight. If the weight percentage of? -triglycidyl isocyanurate is less than 20%, the mechanical properties may deteriorate, and if it exceeds 30% by weight, the biodegradability may be deteriorated. On the other hand, in the above-mentioned numerical range, since it has an average melting point of 92 to 115 캜, blow molding can be easily performed, and mechanical properties are excellent at temperatures below that range.

As the coupling agent, magnesium oxide or zinc oxide is preferably used, and 1 to 15 parts by weight, preferably 5 to 10 parts by weight, based on 100 parts by weight of the obtained polyester after the deglycolysis is used proper. When the amount of the coupling agent is less than 1 part by weight, it is difficult to form a polymer having a high average molecular weight. When the amount is more than 15 parts by weight, gelation may occur.

When grafting is performed using lignin, the grafting rate may be lowered when the amount is less than 50 parts by weight based on 100 parts by weight of the polyester obtained after the deglycolysis, and when the amount is more than 60 parts by weight, There is significance of the numerical limitation in that it can be done.

A grafted peroxide radical initiator may be used as a reaction catalyst to introduce a reactive group, followed by grafting. At this time, there is significance of the numerical value limitation in that a time of about 2 to 4 hours and stirring of 150 to 250 rpm are required to have a number average molecular weight of about 100,000.

As a method for introducing a reactive group into lignin, it is preferable to dissolve lignin in an organic solvent such as dichloromethane or chloroform, and then introduce a reactive group so that the polymer chain can grow in the repeating unit of lignin. Examples of the compound that can be used as the reactive group include azo compounds such as hydrogen peroxide, azobis (2,4-dimethylpentanenitrile), azobis (cyclohexanecarbonitrile), azobis-isobutyronitrile (AIBN), alkyl peroxides (Tertiary butyl peroxide), acyl peroxide (acetyl peroxide, benzoyl peroxide), hydroperoxide (cumyl hydroperoxide, tertiary butyl hydroperoxide), tertiary butyl perbenzoate, acyl alkylsulfonyl peroxide , Dialkyl peroxydicarbonate, diperoxydiacetate, and ketone peroxide can be used.

Hereinafter, the constitution and effect of the present invention will be described in more detail with reference to examples and test examples. However, the embodiments are merely examples for explaining the constitution of the present invention, and the scope of the present invention is not limited to these embodiments.

≪ Example 1 >

To a 250 ml four-necked glass flask equipped with a stirrer, a gas introducing tube, a low-boiling compound outflow tube such as water and a classifying condenser equipped with a thermometer, 35 g of adipic acid, 35 g of terephthalic acid and 30 g of 1,3- After the addition, the temperature was adjusted to 200 ° C and the esterification reaction was carried out by dehydration reaction in a stream of nitrogen.

After the water outflow was completed, 0.7 g of tetrabutyl titanate as a deglycol catalyst was added to the resulting oligomer in a nitrogen atmosphere, and the temperature of the reactor was raised to 240 캜 and the pressure was reduced to carry out deglycolysis.

To the resulting polyester was added 2 g of? -Triglycidyl isocyanurate and? -Type triglycidyl isocyanurate in a ratio of 70% by weight to 30% by weight, and 1.5 g of zinc oxide was added thereto 50 g of lignin was dissolved in chloroform and reacted at 260 DEG C for about 4 hours at 200 rpm.

The polyester resin thus obtained had a number average molecular weight (Mn) of 105,000, a weight average molecular weight (Mw) of 325,000, a melting point of 75 占 폚 and a softening point of 67 占 폚.

≪ Example 2 >

A polyester resin was prepared in the same manner as in Example 1 except that 60 g of lignin was dissolved in chloroform and then charged. The obtained resin had a number average molecular weight (Mn) of 115,000, a weight average molecular weight (Mw) Was 335,000 and had a melting point of 78 캜 and a softening point of 68 캜.

≪ Comparative Example 1 &

A polyester resin was prepared in the same manner as in Example 1, except that 40 g of lignin was dissolved in chloroform in Example 1 and then added. The obtained resin had a number average molecular weight (Mn) of 92,000 and a weight average molecular weight (Mw) 225,000, a melting point of 60 占 폚, and a softening point of 52 占 폚.

≪ Comparative Example 2 &

A polyester resin was prepared in the same manner as in Example 1, except that 70 g of lignin was dissolved in chloroform in Example 1 and then added. The obtained resin had a number average molecular weight (Mn) of 135,000 and a weight average molecular weight (Mw) 355,000, a melting point of 80 占 폚, and a softening point of 69 占 폚.

≪ Test Example 1 > Property evaluation

The physical properties of the polyester resins obtained in Examples 1 and 2 and Comparative Examples 1 and 2 were measured at room temperature in accordance with KSM3006 specification, and the results are shown in Table 1.

Tensile Strength (MPa) Elongation (%) Tensile modulus (MPa) Example 1 54 750 783 Example 2 51 745 795 Comparative Example 1 42 530 761 Comparative Example 2 28 490 752

As can be seen in Table 1, the mechanical properties of triglycidyl isocyanurate were adjusted to 70 wt%: 30 wt% and 80 wt%: 20 wt% for α- and β-form, respectively, but after deglycolysis When the content of lignin was less than 50 parts by weight with respect to 100 parts by weight of the obtained polyester, the number average molecular weight was relatively low and the tensile strength was low. On the other hand, when the content of lignin exceeds 60 parts by weight, it can be confirmed that the mechanical properties such as tensile strength are low.

However, as an example of the present invention, it was confirmed that the mechanical properties such as tensile strength and elongation were very good in Examples 1 and 2.

The foregoing description is merely illustrative of the technical idea of the present invention and various changes and modifications may be made by those skilled in the art without departing from the essential characteristics of the present invention. Therefore, the embodiments disclosed in the present invention are intended to illustrate rather than limit the scope of the present invention, and the scope of the technical idea of the present invention is not limited by these embodiments. The scope of protection of the present invention should be construed according to the following claims, and all technical ideas falling within the scope of the same shall be construed as falling within the scope of the present invention.

Claims (5)

S1) a mixture of 10 to 60% by weight of an aliphatic dicarboxylic acid or a cycloaliphatic dicarboxylic acid or an ester-forming derivative thereof, and 20 to 60% by weight of an aromatic dicarboxylic acid or an ester-forming derivative thereof; And an aliphatic diol or a mixture thereof in an amount of 30 to 60% by weight, the mixture being subjected to an esterification reaction at 180 to 230 ° C in a stream of nitrogen in the course of dehydration;
S2) After dewatering, 0.6 to 1.0 part by weight of tetrabutyl titanate as a catalyst is added to 100 parts by weight of the oligomer obtained in the step S1), and the deglycol reaction is carried out at 230 to 250 ° C .; And
S3) 1 to 3 parts by weight of magnesium oxide or zinc oxide, 1 to 3 parts by weight of 1,3,5-triglycidyl isocyanurate as a coupling agent, 100 to 3 parts by weight of 1,3,5-triglycidyl isocyanurate with respect to 100 parts by weight of the polyester after the step S2) And 50 to 60 parts by weight of water are added to the reaction mixture at a reduced pressure at 250 to 270 ° C. and at a speed of 150 to 250 rpm for 2 to 4 hours to react,
The 1,3,5-triglycidyl isocyanurate is a mixture of α-triglycidyl isocyanurate and β-triglycidyl isocyanurate in a ratio of 70 to 80% by weight: 20 to 30% by weight Lt; / RTI >
Wherein the step S3) includes grafting using the lignin,
Wherein the grafting using the lignin comprises:
The lignin is dissolved in dichloromethane or chloroform,
The lignin may be mixed with an organic peroxide such as hydrogen peroxide, azobis (2,4-dimethylpentanenitrile), azobis (cyclohexanecarbonitrile), azobisisobutyronitrile (AIBN), alkylperoxide (cumylperoxide, tertiary butylperoxide ), Acyl peroxides (acetyl peroxide, benzoyl peroxide), hydroperoxides (cumyl hydroperoxide, tertiary butyl hydroperoxide), tertiary butyl perbenzoate, acyl alkyl sulfonyl peroxide, A method for producing a biodegradable polyester resin, which comprises introducing a reactive group using one or two or more selected from the group consisting of a carbonate, a difluoroacetal, and a ketone peroxide. delete The method according to claim 1,
Wherein the aliphatic dicarboxylic acid or the cycloaliphatic dicarboxylic acid or an ester-forming derivative thereof is adipic acid and sebacic acid, and the mixing ratio thereof is adipic acid: sebacic acid = 1: 0.5 to 1.5. A method for producing an ester resin. The method according to claim 1,
Wherein the aromatic dicarboxylic acid or its ester-forming derivative is any one of terephthalic acid, isophthalic acid, 2,6 naphthalic acid and 1,5-naphthalic acid, or a mixture thereof. . The method according to claim 1,
The aliphatic diol may be selected from the group consisting of 1,3-butanediol, 2-methyl-1,2-propanediol, 2-methyl-1,3-propanediol, Pentanediol, 2-methyl-2,4-pentanediol, 1,2-hexanediol, 1,3-hexanediol, 1,5-hexanediol, 2,3- , 4-hexanediol, 2,5-hexanediol, 3,4-hexanediol, 1,2-heptanediol, 1,3-heptanediol, 1,4-heptanediol, Heptanediol, 3,5-heptanediol, 2,5-heptanediol, 2,6-heptanediol, 3,4-heptanediol and 3,5-heptanediol, or a mixture of two or more thereof. A method for producing a resin.