JP2015212238A - Anhydrosugar alcohol composition, method for producing the same and resin - Google Patents

Abstract

PROBLEM TO BE SOLVED: To provide an anhydrosugar alcohol composition excellent in storage stability and further capable of suppressing the coloring of a resin obtained using the same and the reduction of glass transition temperature, a method for producing the same, and a resin.SOLUTION: Provided is an anhydrosugar alcohol composition comprising anhydrosugar alcohol (A) and amino alcohol (B) having two active hydrogen groups and not comprising cyclic phosphite, also provided is a method for producing an anhydrosugar alcohol composition including (step 1) of refining the anhydrosugar alcohol (A) without refining the same and (step 2) of mixing the anhydrosugar alcohol (A) refined by the (step 2) and amino alcohol (B) without being added with cyclic phosphite, and also provided is a resin produced using the anhydrosugar alcohol composition.

Description

  The present invention relates to an anhydrous sugar alcohol composition, a method for producing the same, and a resin produced using the anhydrous sugar alcohol composition.

  In recent years, there is concern about the depletion of petroleum resources and global warming, and as a countermeasure, materials using renewable biomass materials are attracting attention. In particular, anhydrous sugar alcohol is easy to obtain because it is obtained from sugar or starch, and its use as a raw material for polycarbonate resin and the like is widespread.

  Among such anhydrous sugar alcohols, it is known that isosorbide can be produced by an intramolecular dehydration reaction of sorbitol. However, since isosorbide has a relatively low stability, there is a problem that decomposition or the like tends to occur over time.

  As a method for solving this problem, for example, Patent Document 1 discloses that the stability of the composition can be improved by adding sodium borohydride or disodium hydrogen phosphate to purified isosorbide.

  For example, Patent Document 2 discloses that the stability of the composition can be improved by adding a cyclic phosphite and an amino alcohol to an anhydrous sugar alcohol.

JP 2005-509667 A International Publication No. WO2009 / 057609

  However, when a resin is produced using anhydrous sugar alcohol to which sodium borohydride or disodium hydrogen phosphate is added, the resulting resin is colored, and in some cases, a purification step such as distillation is required before use. It has been found.

  It has also been found that when a resin is produced using an anhydrous sugar alcohol to which a cyclic phosphite is added, the resulting resin may be colored or the glass transition temperature may be lowered.

  Thus, the present invention uses an anhydrous sugar alcohol composition that is excellent in storage stability and can also suppress the coloring of the resin and the decrease in glass transition temperature obtained using the same, its production method, and the anhydrous sugar alcohol composition. It is an object of the present invention to provide a resin to be manufactured.

  In order to solve the above problems, the anhydrous sugar alcohol composition according to the present invention contains an anhydrous sugar alcohol (A) and an amino alcohol (B) having two active hydrogen groups, and does not contain a cyclic phosphite.

  Moreover, in the anhydrous sugar alcohol composition of the said structure, it is preferable to contain 0.00005-1 mass part of said amino alcohol (B) with respect to 100 mass parts of said anhydrous sugar alcohol (A).

  Moreover, in the anhydrous sugar alcohol composition of the said structure, it is preferable that the said amino alcohol (B) has a tertiary amino group.

  Moreover, in the anhydrous sugar alcohol composition of the said structure, it is preferable that the said amino alcohol (B) has two hydroxyl groups.

  Moreover, it is preferable that the anhydrous sugar alcohol composition of the said structure does not contain an alkali metal hydroxide, an alkali metal carbonate, an alkali metal borate, and an alkali metal phosphate.

  Moreover, resin which concerns on this invention is manufactured using the said anhydrous sugar alcohol composition.

  The method for producing an anhydrous sugar alcohol composition according to the present invention includes (Step 1) a step of purifying the anhydrous sugar alcohol (A), and (Step 2) a purified anhydrous sugar alcohol (A) and an active hydrogen group. A step of mixing two amino alcohol compounds (B) without adding cyclic phosphite is included.

  ADVANTAGE OF THE INVENTION According to this invention, while using the anhydrous sugar alcohol composition which is excellent in storage stability, and can also suppress the coloring of the resin obtained using this, and the fall of a glass transition temperature, its manufacturing method, and this anhydrous sugar alcohol composition are used. A resin produced is provided.

  Hereinafter, preferred embodiments of the present invention will be described.

  The anhydrous sugar alcohol composition of the present invention contains an anhydrous sugar alcohol (A).

  Examples of the anhydrous sugar alcohol (A) include anhydrous sugar alcohols in which sugars such as sorbitol, mannitol and iditol are dehydrated and condensed in the molecule. Specifically, one molecule is dehydrated in the molecule such as sorbitan and mannitan. Examples include condensed anhydrous sugar alcohols; anhydrous sugar alcohols in which two molecules are dehydrated and condensed in molecules such as isosorbide, isomannide, and isoidide. Of these, anhydrous sugar alcohols in which two molecules are dehydrated and condensed in the molecule are preferred.

  The method for producing the anhydrous sugar alcohol (A) is not particularly limited. As anhydrous sugar alcohol (A), what was manufactured by heating the mixture of saccharide | sugar and concentrated sulfuric acid to 100-180 degreeC, and also neutralizing with alkali components, such as sodium hydroxide, can be used, for example. . In addition, anhydrous sugar alcohol obtained by using hydrochloric acid, phosphoric acid, sulfonated polystyrene, p-toluenesulfonic acid, methanesulfonic acid or the like instead of concentrated sulfuric acid, and / or organic such as xylene, toluene, etc. Anhydrosugar alcohol produced in the presence of a solvent can also be used. As the anhydrous sugar alcohol, it is preferable to use a product purified by distillation under reduced pressure, activated carbon, ion exchange, recrystallization or the like.

  The anhydrous sugar alcohol composition of this embodiment contains an amino alcohol (B) having two active hydrogen groups. Examples of the active hydrogen group include a hydroxyl group, a primary amino group, and a secondary amino group.

  The amino alcohol (B) having two active hydrogen groups is a compound having at least one hydroxyl group and at least one amino group, and active hydrogen groups such as a hydroxyl group, a primary amino group, and a secondary amino group. Is a compound having two in total. Examples of such compounds include amino alcohols having one tertiary amino group and two hydroxyl groups, amino alcohols having one secondary amino group and one hydroxyl group, one primary amino group and one amino group. Examples include amino alcohols having a hydroxyl group.

  Examples of the amino alcohol having one tertiary amino group and two hydroxyl groups include N-methyldiethanolamine, N-ethyldiethanolamine, N-propyldiethanolamine, N-methyldipropanolamine, N-ethyldipropanolamine, An alkyl group is formed on a nitrogen atom such as N-propyldipropanolamine, 3- (dimethylamino) -1,2-propanediol, and 2-[(dimethylamino) methyl] -2-ethyl-1,3-propanediol. And the like.

  Examples of the amino alcohol having one secondary amino group and one hydroxyl group include 2- (methylamino) ethanol, 2- (ethylamino) ethanol, 2- (propylamino) ethanol, and 2- (methylamino). ) Propanol and 2- (methylamino) butanol.

  Examples of the amino alcohol having one primary amino group and one hydroxyl group include monoethanolamine, 3-amino-1-propanol, 1-amino-2-propanol, and 2- (2-aminoethoxy) ethanol. Etc.

  The two active hydrogen groups are superior in that they are excellent in storage stability and can further suppress coloring of the resulting resin and a decrease in glass transition temperature even when the anhydrous sugar alcohol composition is stored for a long period of time. The amino alcohol (B) having is preferably an amino alcohol having a tertiary amino group.

  In addition, the amino group contained in the amino alcohol (B) having two active hydrogen groups has 2 hydroxyl groups from the viewpoint that the storage stability, the coloration of the resin, and the glass transition temperature can be further suppressed. One amino alcohol is preferred.

  The anhydrous sugar alcohol composition of this embodiment does not contain a cyclic phosphite. Here, “does not contain cyclic phosphite” means that it does not substantially contain this, and here, it is less than 0.0005 parts by mass, preferably 100 parts by mass of anhydrous sugar alcohol (A), preferably It contains 0.0003 parts by mass or less, more preferably 0.0001 parts by mass or less of cyclic phosphite.

  According to the anhydrous sugar alcohol composition of the present invention, it has excellent storage stability, and even when the anhydrous sugar alcohol composition is stored for a long period of time, it suppresses coloring of the resin obtained and reduction in the glass transition temperature. it can.

  The anhydrous sugar alcohol composition of the present invention preferably contains 0.00005 to 1 part by weight, more preferably 0.00005 to 0 parts by weight of amino alcohol having two active hydrogen groups per 100 parts by weight of anhydrous sugar alcohol. 0.5 parts by mass, and more preferably 0.0001-0.2 parts by mass. By making it within the above range, the storage stability of the anhydrous sugar alcohol composition and the hue of the resin using the same will be more excellent. Moreover, the fall of the glass transition temperature of resin using this can be suppressed.

It is preferable that the anhydrous sugar alcohol composition of this embodiment does not contain an alkali metal hydroxide, an alkali metal carbonate, an alkali metal borate and an alkali metal phosphate. Here, “not containing alkali metal hydroxide, alkali metal carbonate, alkali metal borate and alkali metal phosphate” means substantially free of these, and here, anhydrous sugar Contains less than 0.0001 parts by weight, preferably 0.00005 parts by weight or less of alkali metal hydroxide, alkali metal carbonate, alkali metal borate or alkali metal phosphate with respect to 100 parts by weight of alcohol (A) To include.
Examples of the alkali metal hydroxide include sodium hydroxide and potassium hydroxide.
Examples of the alkali metal carbonate include sodium carbonate.
Examples of the alkali metal borate include sodium borohydride and sodium metaborate.
Examples of the alkali metal phosphate include disodium hydrogen phosphate.
By not containing the alkali metal hydroxide, alkali metal carbonate, alkali metal borate and alkali metal phosphate, the storage stability of the anhydrous sugar alcohol composition and the color of the resin using the same are further improved. It will be a thing. In addition, a purification step such as distillation may be unnecessary before the production of the resin using the anhydrous sugar alcohol. That is, it is possible to suppress a change in the hue of the obtained resin and a decrease in the glass transition temperature while eliminating such a purification step.

  The method for producing an anhydrous sugar alcohol composition of the present invention comprises a step of purifying an anhydrous sugar alcohol (A) (Step 1), an amino alcohol (B) having two purified hydrogenated alcohol alcohols (A) and active hydrogen groups. Are mixed without adding cyclic phosphite (step 2). In particular, since the storage stability of the anhydrous sugar alcohol composition and the hue of the resin using the composition are superior, and the glass transition temperature of the resin using the composition can be further suppressed, the purified anhydrous sugar alcohol ( In a state where A) is melted, it is preferable to add amino alcohol (B) under an inert gas stream and mix for 0.1 to 5 hours.

  In the method for producing the anhydrous sugar alcohol composition, in step 2, the anhydrous sugar alcohol (A) and the amino alcohol (B) having two active hydrogen groups are mixed without adding an alkali metal salt. It is preferable to do.

The resin of the present invention is produced using the above-mentioned anhydrous sugar alcohol composition.
Furthermore, the resin of the present invention is produced using the anhydrous sugar alcohol composition obtained by the production method described above.

  Examples of such a resin include a polycarbonate resin and a polyester resin. The polycarbonate resin is produced, for example, by subjecting an anhydrous sugar alcohol composition and a carbonic acid diester to an ester exchange reaction while distilling off by-products such as alcohol and phenol under the conditions of 0.01 to 100 kPa and 150 to 270 ° C. Is done. The polyester resin, for example, performs an ester exchange reaction between an anhydrous sugar alcohol composition and dicarboxylic acid dimethyl ester under the conditions of 0.01 to 100 kPa and 130 to 270 ° C. while distilling off by-products such as methanol. Manufactured by.

  The present invention will be described more specifically based on examples and comparative examples, but the present invention is not limited to this. Those skilled in the art can make various changes, modifications, and alterations without departing from the scope of the present invention.

  The amino alcohol (B) having two active hydrogen groups used is as follows.

(B-1)
N-methyldiethanolamine (B-2)
N-ethyldiethanolamine (B-3)
Nt-butyldiethanolamine (B-4)
N-methyldiisopropanolamine (B-5)
3- (Dimethylamino) -1,2-propanediol (B-6)
2-[(Dimethylamino) methyl] -2-ethyl-1,3-propanediol

(Raw material for comparative example)
(B'-1)
Morpholine (B'-2)
Hydroxylamine (B'-3)
2-Aminopyridine (B'-4)
Imidazole (B'-5)
Diethanolamine (B'-6)
6- [3- (3-t-Butyl-4-hydroxy-5-methylphenyl) propoxy] -2,4,8,10-tetra-t-butyldibenz [d, f] [1,3,2] di Oxaphosphepine, trade name: SUMILIZER GP (manufactured by Sumitomo Chemical Co., Ltd.)
(B'-7)
Disodium hydrogen phosphate

[Example 1: Production of anhydrous sugar alcohol composition Production method 1]
In a vacuum reactor equipped with a stirrer, 1930 g of a 70% by mass aqueous solution of sorbitol was charged, and water was distilled off under conditions of 5 kPa and 120 ° C. Next, 15 g of 98% concentrated sulfuric acid was added to the obtained residue, and these were reacted under the conditions of 5 kPa and 120 ° C. for 5 hours. The obtained product was cooled to 90 ° C., neutralized by adding 24 g of a 50% by mass aqueous sodium hydroxide solution, water was distilled off under conditions of 5 kPa and 120 ° C., and further at 1 kPa and 200 ° C. By distillation for 10 hours, 788 g of crude isosorbide was obtained. Subsequently, 760 g of pure water was added to the obtained crude isosorbide to obtain a homogeneous solution. 146 g of powdered activated carbon was added to this solution and stirred for 3 hours, followed by filtration to remove the activated carbon. Furthermore, 733 g of isosorbide (A-1) was obtained by distilling water off from the obtained filtrate under conditions of 5 kPa and 120 ° C. Subsequently, 0.02 g of amino alcohol (B-1) having two active hydrogen groups was mixed with 100 g of the obtained isosorbide (A-1) to obtain an anhydrous sugar alcohol composition.

[Example 2: Production of anhydrous sugar alcohol composition, production method 2]
In a vacuum reactor equipped with a stirrer, 1930 g of a 70% by mass aqueous solution of sorbitol was charged, and water was distilled off under conditions of 5 kPa and 120 ° C. Subsequently, 57 g of p-toluenesulfonic acid monohydrate was added to the obtained residue, and these were reacted at 5 kPa and 150 ° C. for 20 hours. The obtained product was cooled to 90 ° C., neutralized by adding 24 g of a 50% by mass aqueous sodium hydroxide solution, water was distilled off under conditions of 5 kPa and 120 ° C., and further at 1 kPa and 200 ° C. By distillation for 10 hours, 780 g of crude isosorbide was obtained. Subsequently, 760 g of pure water was added to the obtained crude isosorbide to obtain a homogeneous solution. 146 g of powdered activated carbon was added to this solution and stirred for 3 hours, followed by filtration to remove the activated carbon. Furthermore, after the obtained filtrate was treated with a cation exchange resin and an anion exchange resin, water was distilled off from the obtained treatment liquid under conditions of 5 kPa and 120 ° C., and then a fraction at 190 ° C. under a reduced pressure of 1 kPa. 720 g of isosorbide (A-1) was obtained. Subsequently, 0.02 g of amino alcohol (B-1) having two active hydrogen groups was mixed with 100 g of the obtained isosorbide (A-1) to obtain an anhydrous sugar alcohol composition.

[Example 3 Production of anhydrous sugar alcohol composition Production method 3]
In a vacuum reactor equipped with a stirrer, 1930 g of a 70% by mass aqueous solution of sorbitol was charged, and water was distilled off under conditions of 5 kPa and 120 ° C. Subsequently, 28 g of methanesulfonic acid was added to the obtained residue, and these were reacted under conditions of 5 kPa and 150 ° C. for 20 hours. The obtained product was cooled to 90 ° C., neutralized by adding 24 g of a 50% by mass aqueous sodium hydroxide solution, water was distilled off under conditions of 5 kPa and 120 ° C., and further at 1 kPa and 200 ° C. By distillation for 10 hours, 782 g of crude isosorbide was obtained. Subsequently, 760 g of pure water was added to the obtained crude isosorbide to obtain a homogeneous solution. 146 g of powdered activated carbon was added to this solution and stirred for 3 hours, followed by filtration to remove the activated carbon. Furthermore, water was distilled off from the obtained filtrate under conditions of 5 kPa and 120 ° C., and then a fraction at 190 ° C. was fractioned under reduced pressure of 1 kPa to obtain 727 g of isosorbide (A-1). Subsequently, 0.02 g of amino alcohol (B-1) having two active hydrogen groups was mixed with 100 g of the obtained isosorbide (A-1) to obtain an anhydrous sugar alcohol composition.

[Example 4 Production of Anhydrous Sugar Alcohol Composition Production Method 4]
In a vacuum reactor equipped with a stirrer, 1930 g of a 70% by mass aqueous solution of sorbitol was charged, and water was distilled off under conditions of 5 kPa and 120 ° C. Next, 11 g of 85% by mass phosphoric acid was added to the obtained residue, and these were reacted for 10 hours under conditions of 5 kPa and 180 ° C. The obtained product was cooled to 90 ° C., neutralized by adding 24 g of a 50% by mass aqueous sodium hydroxide solution, water was distilled off under conditions of 5 kPa and 120 ° C., and further 1 kPa, 200 ° C. To obtain 780 g of crude isosorbide. Subsequently, 760 g of pure water was added to the obtained crude isosorbide to obtain a homogeneous solution. 146 g of powdered activated carbon was added to this solution and stirred for 3 hours, followed by filtration to remove the activated carbon. Furthermore, water was distilled off from the obtained filtrate under conditions of 5 kPa and 120 ° C., and then recrystallization from ethanol gave 718 g of isosorbide (A-1). 0.5 g of an acetone solution containing 0.02 g of amino alcohol (B-1) having two active hydrogen groups is mixed with 100 g of the obtained isosorbide (A-1), and the conditions are 5 kPa and 80 ° C. By removing the solvent, an anhydrous sugar alcohol composition was obtained.

[Examples 5 to 16]
As the amino alcohol (B) having two active hydrogen groups, the same operation as in Example 1 was carried out except that the compounds and blending amounts shown in Table 1 were used to obtain an anhydrous sugar alcohol composition.

[Example 17]
A reduced pressure reactor equipped with a stirrer was charged with 1350 g of crystalline mannitol and heated at 170 ° C. to melt. Next, 15 g of 98% concentrated sulfuric acid was added to the obtained melt, and these were reacted at 5 kPa and 170 ° C. for 20 hours. The obtained product was cooled to 90 ° C., neutralized by adding 24 g of a 50% by mass aqueous sodium hydroxide solution, water was distilled off under conditions of 5 kPa and 120 ° C., and further at 1 kPa and 200 ° C. Distilling for 10 hours gave 546 g of crude isomannide. Subsequently, 760 g of pure water was added to the obtained crude isomannide to obtain a homogeneous solution. 146 g of powdered activated carbon was added to this solution and stirred for 3 hours, followed by filtration to remove the activated carbon. Of the obtained filtrate, 0.5 g of an acetone solution containing 0.02 g of amino alcohol (B-1) having two active hydrogen groups was mixed with a solution corresponding to 100 g of isomannide (A-2). Then, water and acetone were distilled off under conditions of 5 kPa and 120 ° C. to obtain 524 g of an anhydrous sugar alcohol composition.

[Example 18]
The same operation as in Example 1 was performed to obtain 733 g of isosorbide (A-1). Subsequently, 0.02 g of amino alcohol (B-1) having two active hydrogen groups and 0.0001 g of cyclic phosphite (B′-6) were mixed with 100 g of the obtained isosorbide (A-1). By doing so, an anhydrous sugar alcohol composition was obtained.

[Example 19]
The same operation as in Example 1 was performed to obtain 733 g of isosorbide (A-1). Subsequently, 0.02 g of amino alcohol (B-1) having two active hydrogen groups and 0.0001 g of alkali metal phosphate (B′-7) were mixed with 100 g of the obtained isosorbide (A-1). By doing so, an anhydrous sugar alcohol composition was obtained.

[Example 20]
The same operation as in Example 1 was performed to obtain 733 g of isosorbide (A-1). Subsequently, 0.02 g of amino alcohol (B-1) having two active hydrogen groups and 0.00005 g of alkali metal phosphate (B′-7) were mixed with 100 g of the obtained isosorbide (A-1). By doing so, an anhydrous sugar alcohol composition was obtained.

[Comparative Example 1]
Except not using amino alcohol (B) which has two active hydrogen groups, operation similar to Example 1 was performed and the anhydrous sugar alcohol composition (containing only anhydrous sugar alcohol) was obtained.

[Comparative Examples 2 to 6]
An anhydrous sugar alcohol composition was obtained in the same manner as in Example 1 except that the compounds and blending amounts shown in Table 1 were used in place of the amino alcohol (B) having two active hydrogen groups.

[Comparative Example 7]
An anhydrous sugar alcohol composition was obtained in the same manner as in Example 18 except that the amount of cyclic phosphite (B′-6) was changed to 0.0005 g.

  The following evaluation was performed using the obtained anhydrous sugar alcohol composition. The obtained results are shown in Table 1.

(1) Stability of anhydrous sugar alcohol composition (Stability test)
In a 100 ml container, 30 g of the anhydrous sugar alcohol composition obtained in Examples 1 to 20 and Comparative Examples 1 to 7 was charged and sealed in a nitrogen atmosphere. This was left in a 50 ° C. environment for 1000 hours or 2000 hours, and the hue (ΔYI value) was measured by the following method. Moreover, in order to confirm the hue of the anhydrous sugar alcohol composition immediately after manufacture, in Reference Example 1, the hue was similarly measured using the anhydrous sugar alcohol composition immediately after manufactured by the method of Comparative Example 1. The results are shown in Table 1.

(Measurement of hue (ΔYI value))
In accordance with JIS K 2580, the YI value of a 40 mass% aqueous solution of the anhydrous sugar alcohol composition was measured, and the difference from the YI value of water measured in advance was calculated as a ΔYI value. Note that the ΔYI value is closer to colorless as the numerical value is lower.

(2) Color of resin Resins 1 to 3 were prepared by the following method using raw sugar alcohol compositions obtained in Examples 1 to 20 or Comparative Examples 1 to 7 in a 50 ° C. environment for 1000 hours as raw materials. And the hue of the resin was evaluated. Moreover, in order to confirm coloring with the anhydrous sugar alcohol composition immediately after manufacture, in Reference Example 1, resin 1-3 is similarly used using the anhydrous sugar alcohol composition immediately after manufactured by the method of Comparative Example 1. Manufactured and evaluated the hue of the resin. The results are shown in Table 1.

(Evaluation with resin 1 (a homopolymer of polycarbonate resin))
A reactor equipped with a stirrer and an effluent condenser was charged with 73 g of anhydrous sugar alcohol composition, 107 g of diphenyl carbonate, and 8 × 10 ⁻⁵ g of sodium hydroxide as a polymerization catalyst, and heated to 165 ° C. in a nitrogen atmosphere. It melted by mixing. Subsequently, the pressure was gradually reduced to remove by-produced phenol, and the reaction was further continued for 15 minutes after the pressure in the reactor reached 13.3 kPa. Subsequently, after the temperature was raised to 190 ° C., the pressure was gradually reduced and the reaction was further continued for 15 minutes after the pressure in the reactor reached 5 kPa, followed by further reaction at 230 ° C. for 30 minutes and then at 250 ° C. for 30 minutes. I let you. Further, the pressure was reduced until reaching 0.1 kPa, and the reaction was further performed at 250 ° C. for 30 minutes. Thereafter, the resultant reaction product was pelletized to obtain a homopolymer (resin 1) of a polycarbonate resin. Using the obtained resin 1, the hue was measured by the following method.

(Evaluation with resin 2 (polycarbonate resin copolymer))
Polycarbonate resin (homopolymer) except that the raw materials used were 55 g of anhydrous sugar alcohol composition, 26 g of 1,4-cyclohexanedimethanol, 118 g of diphenyl carbonate, and 13 × 10 ⁻⁵ g of sodium hydroxide as a polymerization catalyst. The same operations as in the production of were carried out to obtain a polycarbonate resin copolymer (resin 2). Using the obtained resin 2, the hue was measured by the following method.

(Evaluation with resin 3 (polyester resin))
To a reactor equipped with a stirrer and an effluent condenser, 761 g of dimethyl terephthalate, 48 g of anhydrous sugar alcohol composition, 553 g of ethylene glycol, and 0.8 g of titanium (IV) butoxide were added, and the temperature was raised to 135 ° C. in a nitrogen atmosphere. After warming and reacting for 30 minutes, the temperature was raised to 200 ° C. and reacted for another 30 minutes. Subsequently, the temperature was raised to 220 ° C., the pressure was reduced to 13.3 kPa, and the reaction was further performed for 30 minutes. The reaction was further performed at 270 ° C. and 6.7 kPa for 30 minutes, and then the pressure was reduced to 0.02 kPa. By further reacting for a time, a polyester resin (resin 3) was obtained. Using the obtained resin 3, the hue was measured by the following method.

(Measurement of hue (ΔYI value))
According to JIS K 2580, YI values of 10% methylene chloride solutions of resins 1 to 3 were measured and measured in advance using a petroleum product measuring device (trade name: OME-2000, manufactured by Nippon Denshoku Industries Co., Ltd.). The difference from the YI value of methylene chloride was calculated as the ΔYI value.

(3) Glass transition temperature of resin According to JIS K7121 (1987), using TG-DTA / DSC (trade name: Thermo plus EVO, manufactured by Rigaku), a temperature increase rate of 10 ° C./min in a nitrogen gas atmosphere The glass transition temperature was measured at a measurement temperature of 25 ° C to 200 ° C.

  As is clear from Table 1, it can be seen that the anhydrous sugar alcohol compositions of Examples 1 to 20 are excellent in stability and can suppress resin coloring even when stored for a long period of time. On the other hand, when the anhydrous sugar alcohol compositions of Comparative Examples 1 to 7 are stored for a long period of time, the resin is colored or the glass transition temperature of the resin is decreased.

  The anhydrous sugar alcohol composition of the present invention can be used as a raw material for various resins such as polycarbonate resins and polyester resins.

Claims (8)

  An anhydrous sugar alcohol composition containing an anhydrous sugar alcohol (A) and an amino alcohol (B) having two active hydrogen groups, and no cyclic phosphite.   The anhydrous sugar alcohol composition of Claim 1 which contains 0.00005-1 mass part of said amino alcohol (B) with respect to 100 mass parts of said anhydrous sugar alcohol (A).   The anhydrous sugar alcohol composition according to claim 1 or 2, wherein the amino alcohol (B) has a tertiary amino group.   The anhydrous sugar alcohol composition according to any one of claims 1 to 3, wherein the amino alcohol (B) has two hydroxyl groups.   The anhydrous sugar-alcohol composition of any one of Claims 1-4 which does not contain an alkali metal hydroxide, an alkali metal carbonate, an alkali metal borate, and an alkali metal phosphate.   Resin manufactured using the anhydrous sugar-alcohol composition of any one of Claims 1-5. (Step 1) a step of purifying the anhydrous sugar alcohol (A), and
(Step 2) A method for producing an anhydrous sugar alcohol composition comprising a step of mixing a purified anhydrous sugar alcohol (A) and an amino alcohol (B) having two active hydrogen groups so as not to contain a cyclic phosphite.   Resin manufactured using the anhydrous sugar-alcohol composition obtained by the manufacturing method of Claim 7.