WO2014178150A1 - Composition d'anhydride d'alcool de sucre, procédé pour la produire et résine - Google Patents

Composition d'anhydride d'alcool de sucre, procédé pour la produire et résine Download PDF

Info

Publication number
WO2014178150A1
WO2014178150A1 PCT/JP2013/075696 JP2013075696W WO2014178150A1 WO 2014178150 A1 WO2014178150 A1 WO 2014178150A1 JP 2013075696 W JP2013075696 W JP 2013075696W WO 2014178150 A1 WO2014178150 A1 WO 2014178150A1
Authority
WO
WIPO (PCT)
Prior art keywords
carbon atoms
hydrocarbon group
group
sugar alcohol
formula
Prior art date
Application number
PCT/JP2013/075696
Other languages
English (en)
Japanese (ja)
Inventor
大西　英明
倉橋　宏幸
Original Assignee
第一工業製薬株式会社
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by 第一工業製薬株式会社 filed Critical 第一工業製薬株式会社
Priority to TW103107516A priority Critical patent/TW201443119A/zh
Publication of WO2014178150A1 publication Critical patent/WO2014178150A1/fr

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D493/00—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system
    • C07D493/02—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system in which the condensed system contains two hetero rings
    • C07D493/04—Ortho-condensed systems
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
    • C08G63/66—Polyesters containing oxygen in the form of ether groups
    • C08G63/668—Polyesters containing oxygen in the form of ether groups derived from polycarboxylic acids and polyhydroxy compounds
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G64/00—Macromolecular compounds obtained by reactions forming a carbonic ester link in the main chain of the macromolecule
    • C08G64/02—Aliphatic polycarbonates
    • C08G64/0208—Aliphatic polycarbonates saturated
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G64/00—Macromolecular compounds obtained by reactions forming a carbonic ester link in the main chain of the macromolecule
    • C08G64/20—General preparatory processes
    • C08G64/30—General preparatory processes using carbonates
    • C08G64/305—General preparatory processes using carbonates and alcohols

Definitions

  • 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.
  • isosorbide is known to be produced by an intramolecular dehydration reaction of sorbitol.
  • isosorbide since isosorbide has a relatively low stability, there is a problem that decomposition or the like tends to occur over time.
  • Patent Document 1 discloses that the stability of the composition can be improved by adding sodium borohydride or disodium hydrogen phosphate to purified isosorbide.
  • Patent Document 2 discloses that the stability of the composition can be improved by adding a cyclic phosphite and a hindered amine to an anhydrous sugar alcohol.
  • the present invention provides an anhydrous sugar alcohol composition that is excellent in storage stability and can suppress coloring of a resin obtained using the same, a method for producing the same, and a resin produced using the anhydrous sugar alcohol composition The task is to do.
  • the anhydrous sugar alcohol composition according to the present invention contains an anhydrous sugar alcohol (A) and a hindered amine compound (B) and does not contain a cyclic phosphite.
  • the resin according to the present invention is produced using the above-mentioned 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 a hindered amine compound (B And without mixing the cyclic phosphite.
  • the anhydrous sugar alcohol composition of the present invention contains an anhydrous sugar alcohol (A).
  • anhydrous sugar alcohol (A) examples 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.
  • the anhydrous sugar alcohol (A) for example, one produced by heating a mixture of sugar and concentrated sulfuric acid to 100 to 180 ° C. and further neutralizing with an alkali component such as sodium hydroxide can be used.
  • anhydrous sugar alcohol obtained by using hydrochloric acid, phosphoric acid, sulfonated polystyrene, p-toluenesulfonic acid, methanesulfonic acid, etc. in place of concentrated sulfuric acid, in the presence of water and / or organic such as xylene, toluene, etc.
  • Anhydrosugar alcohol produced in the presence of a solvent can also be used.
  • the anhydrous sugar alcohol it is preferable to use an alcohol refined by distillation under reduced pressure, activated carbon, ion exchange, recrystallization or the like.
  • the anhydrous sugar alcohol composition of the present invention contains a hindered amine compound (B).
  • the hindered amine compound (B) is a compound having a structure in which nitrogen atoms are bonded to at least two carbon atoms, these carbon atoms are quaternary carbon atoms, and further substituted with at least two alkyl groups.
  • Examples of such compounds include 2,2,6,6-tetraalkyl-4-piperidine derivatives and 3,3,5,5-tetraalkylpiperazinone derivatives.
  • Examples of 2,2,6,6-tetraalkyl-4-piperidine derivatives include compounds represented by the following general formula (1).
  • A is a hydrogen atom, a hydrocarbon group having 1 to 18 carbon atoms, an alkoxy group having 1 to 18 carbon atoms, a hydroxyalkyl group having 1 to 18 carbon atoms, or an acyl group having 1 to 18 carbon atoms.
  • X is a group composed of at least one selected from a hydrogen atom, a carbon atom, an oxygen atom and a nitrogen atom, and R 1 to R 4 are each independently an alkyl group having 1 to 10 carbon atoms.
  • N is an integer from 1 to 40.
  • A is a hydrogen atom, an alkyl group having 1 to 12 carbon atoms, an alkoxy group having 1 to 12 carbon atoms, Alternatively, an acyl group having 1 to 12 carbon atoms is preferable.
  • R 1 to R 4 are preferably each independently an alkyl group having 1 to 4 carbon atoms, and more preferably a methyl group.
  • n is preferably 1 to 20, and more preferably 1 to 10.
  • any of the compounds represented by the general formulas (2) to (7) A compound is preferred.
  • A is a hydrogen atom, a hydrocarbon group having 1 to 18 carbon atoms, an alkoxy group having 1 to 18 carbon atoms, a hydroxyalkyl group having 1 to 18 carbon atoms, or 1 to 18 carbon atoms.
  • R 1 to R 4 are each independently an alkyl group having 1 to 10 carbon atoms.
  • A is preferably a hydrogen atom, an alkyl group having 1 to 12 carbon atoms, an alkoxy group having 1 to 12 carbon atoms, or an acyl group having 1 to 12 carbon atoms.
  • R 1 to R 4 are preferably alkyl groups having 1 to 4 carbon atoms, and more preferably methyl groups.
  • Z 1 is a hydrogen atom, a hydroxyl group, an amino group, or a substituent represented by the following general formula (8).
  • R 10 and R 11 are each independently a hydrogen atom or a hydrocarbon group having 1 to 18 carbon atoms.
  • R 5 is a hydrocarbon group having 1 to 24 carbon atoms
  • R 6 is a hydrocarbon group having 1 to 18 carbon atoms
  • a is an integer of 0 to 30
  • b is 1 to 30 Is an integer.
  • R 5 is preferably a hydrocarbon group having 1 to 10 carbon atoms
  • R 6 is preferably a hydrocarbon group having 1 to 14 carbon atoms.
  • a is preferably an integer of 0 to 20, and more preferably an integer of 0 to 10.
  • b is preferably an integer of 1 to 20, more preferably an integer of 1 to 10.
  • R 7 is a hydrocarbon group having 1 to 18 carbon atoms, and c is an integer of 1 to 20. Of these, R 7 is preferably a phenylene group, and c is preferably 2. 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.
  • R 8 is a hydrocarbon group having 1 to 18 carbon atoms
  • Z 2 is a hydrogen atom or a substituent represented by the following general formula (9)
  • d is an integer of 1 to 20
  • R 8 is preferably an alkylene group having 1 to 8 carbon atoms
  • d is preferably 2.
  • A is a hydrogen atom, a hydrocarbon group having 1 to 18 carbon atoms, an alkoxy group having 1 to 18 carbon atoms, a hydroxyalkyl group having 1 to 18 carbon atoms, or an acyl group having 1 to 18 carbon atoms.
  • R 1 to R 4 is independently an alkyl group having 1 to 10 carbon atoms
  • R 12 is a hydrocarbon group having 1 to 18 carbon atoms.
  • A is preferably a hydrogen atom, an alkyl group having 1 to 12 carbon atoms, an alkoxy group having 1 to 12 carbon atoms, or an acyl group having 1 to 12 carbon atoms.
  • R 1 to R 4 are preferably each independently an alkyl group having 1 to 4 carbon atoms, and more preferably a methyl group.
  • R 12 is preferably an alkyl group having 1 to 6 carbon atoms.
  • R 9 is a hydrocarbon group having 1 to 18 carbon atoms, and is preferably an alkyl group having 1 to 14 carbon atoms.
  • any of the compounds represented by the following general formulas (10) to (15) can be used.
  • R 1 to R 4 are each independently an alkyl group having 1 to 10 carbon atoms
  • R 13 and R 14 are each independently a hydrocarbon group having 1 to 18 carbon atoms
  • R 15 is a hydrogen atom or a hydrocarbon group having 1 to 18 carbon atoms
  • e is an integer of 1 to 40.
  • R 1 to R 4 are preferably each independently an alkyl group having 1 to 4 carbon atoms, and more preferably a methyl group.
  • R 13 and R 14 are preferably each independently an alkylene group having 2 to 8 carbon atoms, and R 15 is preferably a hydrogen atom or an alkyl group having 1 to 3 carbon atoms. Further, e is preferably from 1 to 30, and more preferably from 1 to 20. 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.
  • R 16 is a hydrocarbon group having 1 to 30 carbon atoms
  • Y 1 is a substituent represented by the following general formula (16)
  • f is an integer of 1 to 30.
  • R 16 is preferably an alkylene group having 1 to 26 carbon atoms
  • f is preferably 1 to 20 and more preferably 1 to 10.
  • R 17 is a hydrocarbon group having 1 to 10 carbon atoms
  • Y 1 is a substituent represented by the following general formula (16)
  • Z 3 is represented by the following formula (17).
  • G is an integer of 1 to 20, and R 17 and Y 1 may be the same or different. Of these, g is preferably from 1 to 10, and more preferably from 1 to 5.
  • R 18 is a hydrocarbon group having 1 to 18 carbon atoms
  • R 19 is a hydrogen atom or a hydrocarbon group having 1 to 18 carbon atoms
  • Y 1 is represented by the following general formula (16).
  • Z 4 is a hydrogen atom, a hydrocarbon group having 1 to 18 carbon atoms or a substituent represented by the following general formula (16)
  • h is an integer of 1 to 20, 1 may be the same or different, and when a plurality of R 18 , R 19 and Z 4 are contained, they may be the same or different.
  • R 18 is preferably an alkylene group having 1 to 8 carbon atoms
  • R 19 is preferably a hydrogen atom or an alkyl group having 1 to 6 carbon atoms
  • Z 4 is an alkyl group having 1 to 10 carbon atoms. It is preferably a hydrocarbon group or a substituent represented by the general formula (16), and h is preferably 1 to 10.
  • R 20 and R 21 are each independently a hydrocarbon group having 1 to 18 carbon atoms
  • R 22 is a hydrogen atom or a hydrocarbon group having 1 to 18 carbon atoms
  • Y 1 is A substituent represented by the following general formula (16)
  • Y 2 is a substituent represented by the following general formula (18) or (19)
  • i is an integer of 1 to 20
  • Y 1 and Y 2 may be the same or different, and when a plurality of R 20 and R 22 are contained, they may be the same or different.
  • R 20 and R 21 are preferably each independently an alkylene group having 1 to 8 carbon atoms
  • R 22 is preferably an alkyl group having 1 to 6 carbon atoms
  • i is 1 to 10 preferable.
  • R 23 and R 24 are each a hydrocarbon group having 1 to 18 carbon atoms, and Y 3 is a substituent represented by the following general formula (19). Of these, R 23 and R 24 are preferably each independently an alkylene group having 1 to 5 carbon atoms. 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.
  • A is a hydrogen atom, a hydrocarbon group having 1 to 18 carbon atoms, an alkoxy group having 1 to 18 carbon atoms, a hydroxyalkyl group having 1 to 18 carbon atoms, or an acyl group having 1 to 18 carbon atoms.
  • R 1 to R 4 are each independently an alkyl group having 1 to 10 carbon atoms, preferably an alkyl group having 1 to 4 carbon atoms, and more preferably a methyl group.
  • R 25 and R 26 are each independently a hydrogen atom or a hydrocarbon group having 1 to 18 carbon atoms, preferably an alkyl group having 1 to 6 carbon atoms.
  • R 27 is a hydrogen atom or a hydrocarbon group having 1 to 18 carbon atoms, preferably an alkyl group having 1 to 6 carbon atoms.
  • Y 1 is a substituent represented by the general formula (16).
  • 3,3,5,5-tetraalkylpiperazinone derivatives include compounds represented by general formulas (20) and (21).
  • A is a hydrogen atom, a hydrocarbon group having 1 to 18 carbon atoms, an alkoxy group having 1 to 18 carbon atoms, a hydroxyalkyl group having 1 to 18 carbon atoms, or an acyl group having 1 to 18 carbon atoms.
  • R 1 to R 4 is independently an alkyl group having 1 to 10 carbon atoms
  • R 28 is a hydrocarbon group having 1 to 18 carbon atoms
  • j is an integer of 1 to 20
  • R 1 to R 4 are preferably alkyl groups having 1 to 4 carbon atoms, and more preferably methyl groups.
  • R 28 is preferably an alkylene group having 1 to 8 carbon atoms, and j is preferably 2.
  • R 29 is a hydrogen atom or a hydrocarbon group having 1 to 18 carbon atoms
  • Y 4 is a substituent represented by the following general formula (22).
  • R 29 is preferably a cyclic hydrocarbon group having 1 to 10 carbon atoms.
  • A is a hydrogen atom, a hydrocarbon group having 1 to 18 carbon atoms, an alkoxy group having 1 to 18 carbon atoms, a hydroxyalkyl group having 1 to 18 carbon atoms, or an acyl group having 1 to 18 carbon atoms.
  • R 1 to R 4 is independently an alkyl group having 1 to 10 carbon atoms
  • R 30 is a hydrocarbon group having 1 to 18 carbon atoms.
  • R 1 to R 4 are preferably each independently an alkyl group having 1 to 4 carbon atoms, and more preferably a methyl group.
  • R 30 is preferably an alkylene group having 1 to 4 carbon atoms.
  • hindered amine compounds particularly preferred compounds are bis (2,2,6,6-tetramethyl-4-piperidyl) sebacate, bis (1,2,2,6,6-pentamethyl-4-piperidyl) sebacate, Bis (1-octyloxy-2,2,6,6-tetramethyl-4-piperidyl) sebacate, 2,2,6,6-tetramethylpiperidine, 1,2,2,6,6-pentamethylpiperidine, N-acetyl-3-dodecyl-1- (2,2,6,6-tetramethyl-4-piperidinyl) pyrrolidine-2,5-dione, tetrakis (2,2,6,6-tetramethyl-4-piperidyl ) 1,2,3,4-Butanetetracarboxylate, tetrakis (1,2,2,6,6-pentamethyl-4-piperidyl) 1,2,3,4-butanetetracar Xylates, N, N′-bis (2,2,6,6-tetramethyl
  • the anhydrous sugar alcohol composition of the present invention does not contain a cyclic phosphite.
  • “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.
  • the storage stability is excellent, and coloring of the resulting resin can be suppressed even when the anhydrous sugar alcohol composition is stored for a long period of time.
  • the anhydrous sugar alcohol composition of the present invention preferably contains 0.00005 to 1 part by mass, more preferably 0.00005 to 0.5 parts by mass of the hindered amine compound with respect to 100 parts by mass of the anhydrous sugar alcohol. More preferably, the content is 0.0001 to 0.2 parts by mass.
  • the anhydrous sugar alcohol composition of the present invention preferably contains no alkali metal hydroxide, alkali metal carbonate, alkali metal borate or alkali metal phosphate.
  • “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.
  • 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.
  • 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), a purified anhydrous sugar alcohol (A) and a hindered amine compound (B), and a cyclic phosphite. And a step of mixing without adding (step 2).
  • the hindered amine compound (B) in an inert gas stream in a state where the purified anhydrous sugar alcohol (A) is melted. It is preferable to mix for 0.1 to 5 hours.
  • the anhydrous sugar alcohol (A) and the hindered amine compound (B) are mixed in the step 2 without adding an alkali metal salt.
  • 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.
  • polycarbonate resins examples include polycarbonate resins and polyester resins.
  • Polycarbonate resin is produced, for example, by subjecting an anhydrous sugar alcohol composition and a carbonic acid diester to a transesterification 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, undergoes 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 out by-products such as methanol. Manufactured by.
  • the hindered amine compound (B) used is as follows, and each structure is represented by the following formulas [Chemical 9] and [Chemical 10].
  • X 1 to X 7 are as shown in the following formula [Chem. 11]
  • Z 3 is as shown in the formula (17).
  • Example 1 Production of anhydrous sugar alcohol composition Production method 1
  • 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.
  • 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.
  • Example 2 Production of anhydrous sugar alcohol composition, production method 2
  • 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.
  • 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.
  • Example 3 Production of anhydrous sugar alcohol composition Production method 3
  • 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.
  • 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.
  • Example 4 Production of Anhydrous Sugar Alcohol Composition Production Method 4
  • 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.
  • 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.
  • Examples 5 to 36 As an hindered amine compound (B), the same operation as Example 1 was performed except having used the compound and compounding quantity of Table 1, and the anhydrous sugar alcohol composition was obtained.
  • Example 37 The same operation as in Example 1 was performed to obtain 733 g of isosorbide (A-1). Subsequently, by mixing 0.02 g of the hindered amine compound (B-1) and 0.0003 g of the cyclic phosphite (B′-5) with 100 g of the obtained isosorbide (A-1), an anhydrous sugar alcohol A composition was obtained.
  • Example 38 The same operation as in Example 1 was performed to obtain 733 g of isosorbide (A-1). Subsequently, by mixing 0.02 g of the hindered amine compound (B-1) and 0.0001 g of the cyclic phosphite (B′-5) with 100 g of the obtained isosorbide (A-1), an anhydrous sugar alcohol A composition was obtained.
  • Example 39 The same operation as in Example 1 was performed to obtain 733 g of isosorbide (A-1). Subsequently, 0.02 g of the hindered amine compound (B-1) and 0.0001 g of the alkali metal phosphate (B′-2) are mixed with 100 g of the obtained isosorbide (A-1) to thereby obtain an anhydrous sugar alcohol. A composition was obtained.
  • Example 40 The same operation as in Example 1 was performed to obtain 733 g of isosorbide (A-1). Subsequently, 0.02 g of the hindered amine compound (B-1) and 0.00005 g of the alkali metal phosphate (B′-2) are mixed with 100 g of the obtained isosorbide (A-1) to thereby obtain an anhydrous sugar alcohol. A composition was obtained.
  • Example 41 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.
  • Example 42 As an hindered amine compound (B), the same operation as Example 41 was performed except having used the compound and compounding quantity of Table 1, and the anhydrous sugar alcohol composition was obtained.
  • 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 obtained reactant was pelletized to obtain a polycarbonate resin homopolymer (resin 1). Using the obtained resin 1, the hue was measured by the following method.
  • the polycarbonate resin (homopolymer) was used 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 operation as in the production was performed to obtain a polycarbonate resin copolymer (resin 2). Using the obtained resin 2, the hue was measured by the following method.
  • the anhydrous sugar alcohol compositions of Examples 1 to 42 are excellent in stability and can suppress the coloring of the resin even when stored for a long period of time.
  • the anhydrous sugar alcohol compositions of Comparative Examples 1 to 7 show resin coloring when stored for a long period of time.
  • 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.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Compositions Of Macromolecular Compounds (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
  • Polyesters Or Polycarbonates (AREA)

Abstract

La présente invention concerne : une composition d'anhydride d'alcool de sucre qui comprend un anhydride (A) d'alcool de sucre et un composé amine (B) encombré, mais ne comprend pas de phosphite cyclique ; un procédé pour produire ladite composition d'anhydride d'alcool de sucre qui comprend une étape de purification de l'anhydride (A) d'alcool de sucre (étape 1) et une étape de mélange de l'anhydride (A) d'alcool de sucre purifié et du composé amine (B) encombré, sans ajout de phosphite cyclique (étape 2) ; et une résine produite en utilisant ladite composition d'anhydride d'alcool de sucre.
PCT/JP2013/075696 2013-04-30 2013-09-24 Composition d'anhydride d'alcool de sucre, procédé pour la produire et résine WO2014178150A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
TW103107516A TW201443119A (zh) 2013-04-30 2014-03-05 無水糖醇組合物、其製造方法及樹脂

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
JP2013095126A JP2016121200A (ja) 2013-04-30 2013-04-30 無水糖アルコール組成物
JP2013-095126 2013-04-30

Publications (1)

Publication Number Publication Date
WO2014178150A1 true WO2014178150A1 (fr) 2014-11-06

Family

ID=51843299

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/JP2013/075696 WO2014178150A1 (fr) 2013-04-30 2013-09-24 Composition d'anhydride d'alcool de sucre, procédé pour la produire et résine

Country Status (3)

Country Link
JP (1) JP2016121200A (fr)
TW (1) TW201443119A (fr)
WO (1) WO2014178150A1 (fr)

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN104817430A (zh) * 2014-02-04 2015-08-05 第一工业制药株式会社 无水糖醇的精制方法、无水糖醇和树脂
JP2018535274A (ja) * 2015-11-30 2018-11-29 サムヤン コーポレイション 安定性を高めた濃縮無水糖アルコール製造用組成物及び無水糖アルコールの濃縮方法
JP2019501960A (ja) * 2015-11-30 2019-01-24 サムヤン コーポレイション 保存安定性を高めた無水糖アルコール組成物及び無水糖アルコールの保存方法
FR3116533A1 (fr) * 2020-11-26 2022-05-27 Roquette Freres Produit de déshydratation interne du sorbitol de haute pureté

Citations (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2010089223A1 (fr) * 2009-02-06 2010-08-12 Evonik Degussa Gmbh Procédé pour préparer de la 2,6-dioxabicyclo-(3.3.0)-octan-4,8-dione
WO2010089213A1 (fr) * 2009-02-06 2010-08-12 Evonik Degussa Gmbh Procédé pour préparer des aldéhydes et des cétones à partir d'alcools primaires et secondaires
WO2011118768A1 (fr) * 2010-03-26 2011-09-29 三菱化学株式会社 Formule de résine polycarbonate et article moulé
WO2011162386A1 (fr) * 2010-06-25 2011-12-29 三菱化学株式会社 Composition de résine de polycarbonate et article moulé
WO2012098513A1 (fr) * 2011-01-19 2012-07-26 Sabic Innovative Plastics Ip B.V. Stabilisation aux uv de polycarbonates d'isosorbide
JP2012197371A (ja) * 2011-03-22 2012-10-18 Mitsubishi Chemicals Corp Ｌｅｄ信号用部材
JP2012214793A (ja) * 2011-03-30 2012-11-08 Mitsubishi Chemicals Corp ポリカーボネート樹脂の製造方法
JP2013049846A (ja) * 2011-08-03 2013-03-14 Mitsubishi Chemicals Corp 遮音部材
JP2013049847A (ja) * 2011-08-03 2013-03-14 Mitsubishi Chemicals Corp 自動車内装品

Patent Citations (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2010089223A1 (fr) * 2009-02-06 2010-08-12 Evonik Degussa Gmbh Procédé pour préparer de la 2,6-dioxabicyclo-(3.3.0)-octan-4,8-dione
WO2010089213A1 (fr) * 2009-02-06 2010-08-12 Evonik Degussa Gmbh Procédé pour préparer des aldéhydes et des cétones à partir d'alcools primaires et secondaires
WO2011118768A1 (fr) * 2010-03-26 2011-09-29 三菱化学株式会社 Formule de résine polycarbonate et article moulé
WO2011162386A1 (fr) * 2010-06-25 2011-12-29 三菱化学株式会社 Composition de résine de polycarbonate et article moulé
WO2012098513A1 (fr) * 2011-01-19 2012-07-26 Sabic Innovative Plastics Ip B.V. Stabilisation aux uv de polycarbonates d'isosorbide
JP2012197371A (ja) * 2011-03-22 2012-10-18 Mitsubishi Chemicals Corp Ｌｅｄ信号用部材
JP2012214793A (ja) * 2011-03-30 2012-11-08 Mitsubishi Chemicals Corp ポリカーボネート樹脂の製造方法
JP2013049846A (ja) * 2011-08-03 2013-03-14 Mitsubishi Chemicals Corp 遮音部材
JP2013049847A (ja) * 2011-08-03 2013-03-14 Mitsubishi Chemicals Corp 自動車内装品

Cited By (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN104817430A (zh) * 2014-02-04 2015-08-05 第一工业制药株式会社 无水糖醇的精制方法、无水糖醇和树脂
JP2018535274A (ja) * 2015-11-30 2018-11-29 サムヤン コーポレイション 安定性を高めた濃縮無水糖アルコール製造用組成物及び無水糖アルコールの濃縮方法
JP2019501960A (ja) * 2015-11-30 2019-01-24 サムヤン コーポレイション 保存安定性を高めた無水糖アルコール組成物及び無水糖アルコールの保存方法
EP3384933A4 (fr) * 2015-11-30 2019-07-10 Samyang Corporation Composition d'alcool de sucre anhydre ayant une stabilité au stockage accrue et procédé de stockage d'alcool de sucre anhydre
EP3384932A4 (fr) * 2015-11-30 2019-07-24 Samyang Corporation Composition pour la production de polyol anhydre concentré ayant une stabilité accrue et procédé de concentration de polyol anhydre
FR3116533A1 (fr) * 2020-11-26 2022-05-27 Roquette Freres Produit de déshydratation interne du sorbitol de haute pureté
WO2022111849A1 (fr) * 2020-11-26 2022-06-02 Roquette Freres Produit de deshydratation interne du sorbitol de haute purete

Also Published As

Publication number Publication date
TW201443119A (zh) 2014-11-16
JP2016121200A (ja) 2016-07-07

Similar Documents

Publication Publication Date Title
ES2685836T3 (es) Agente antiestático, composición de agente antiestático, composición de resina antiestática y cuerpo moldeado
TWI613286B (zh) 抗靜電劑、抗靜電劑組成物、抗靜電性樹脂組成物及成形體
KR20170038009A (ko) 대전 방지제, 대전 방지제 조성물, 대전 방지성 수지 조성물 및 성형체
US20090111699A1 (en) Weakly Basic Hindered Amines Having Carbonate Skeletons, Synthetic Resin Compositions, And Coating Compositions
WO2014178150A1 (fr) Composition d'anhydride d'alcool de sucre, procédé pour la produire et résine
KR20170060051A (ko) 대전 방지제, 대전 방지제 조성물, 대전 방지성 수지 조성물 및 성형체
WO2009044907A1 (fr) Polycarbonate ayant un composant dérivé de plante et procédé pour produire celui-ci
CN113631622B (zh) 抗静电剂、包含其的抗静电剂组合物、包含这些的抗静电性树脂组合物及其成型体
KR20170045283A (ko) 대전 방지제, 대전 방지제 조성물, 대전 방지성 수지 조성물 및 성형체
JP4370000B2 (ja) ポリアルキル−１−オキサジアザスピロデカン化合物をベースとする化合物
JP2015145353A (ja) 無水糖アルコールの精製方法、無水糖アルコール及び樹脂
JP2017128679A (ja) 帯電防止性熱可塑性樹脂組成物およびそれを成形してなる成形体
US10308852B2 (en) Antistatic resin composition and polyolefin antistatic fiber for container and pipe for organic solvent
WO2019021944A1 (fr) Composé macromoléculaire, composition contenant celui-ci, composition de résine contenant ceux-ci ainsi que corps moulé associé
JP2022165548A (ja) 帯電防止剤、これを含む帯電防止剤組成物、これらを含む帯電防止性樹脂組成物、および、その成形体
JP2021102684A (ja) 帯電防止性樹脂組成物、ならびにこれを用いた容器および包装材
WO2021065727A1 (fr) Agent antistatique, composition antistatique contenant celui-ci, composition de resine antistatique contenant ledit agent et ladite composition et corps moule de ladite composition de resine
JP2022021149A (ja) 組成物、これを含有する合成樹脂組成物およびその成形体
JP7497180B2 (ja) 流動性向上剤、これを含む流動性向上剤組成物、これらを含む熱可塑性樹脂組成物、およびその成形体
JP7497179B2 (ja) 耐衝撃性改良剤、これを含む耐衝撃性改良剤組成物、これらを含む合成樹脂組成物、およびその成形体
JPH01193362A (ja) 安定化された合成樹脂組成物
JP2022089622A (ja) 組成物、これを含有する合成樹脂組成物およびその成形体
JP2017128676A (ja) 帯電防止性熱可塑性樹脂組成物およびそれを成形してなる成形体
JP2022044863A (ja) 帯電防止剤、帯電防止剤組成物、帯電防止性樹脂組成物およびその成形体
JP2016188312A (ja) 有機溶剤の容器および管用帯電防止性樹脂組成物、並びに、これを用いた容器および管

Legal Events

Date Code Title Description
121 Ep: the epo has been informed by wipo that ep was designated in this application

Ref document number: 13883663

Country of ref document: EP

Kind code of ref document: A1

NENP Non-entry into the national phase

Ref country code: DE

122 Ep: pct application non-entry in european phase

Ref document number: 13883663

Country of ref document: EP

Kind code of ref document: A1

NENP Non-entry into the national phase

Ref country code: JP