Classifications

• • 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
  • C08G18/00—Polymeric products of isocyanates or isothiocyanates
  • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
  • C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
  • C08G18/40—High-molecular-weight compounds
  • C08G18/42—Polycondensates having carboxylic or carbonic ester groups in the main chain
• • 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
  • C08G18/00—Polymeric products of isocyanates or isothiocyanates
  • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
  • C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
  • C08G18/40—High-molecular-weight compounds
  • C08G18/42—Polycondensates having carboxylic or carbonic ester groups in the main chain
  • C08G18/44—Polycarbonates
• • 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
  • C08G63/64—Polyesters containing both carboxylic ester groups and carbonate groups
• • 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
  • C08G63/91—Polymers modified by chemical after-treatment
• • 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
• • 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
• • 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
  • C08G64/42—Chemical after-treatment
• • C—CHEMISTRY; METALLURGY
  • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
  • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
  • C08L69/00—Compositions of polycarbonates; Compositions of derivatives of polycarbonates
• • C—CHEMISTRY; METALLURGY
  • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
  • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
  • C09D175/00—Coating compositions based on polyureas or polyurethanes; Coating compositions based on derivatives of such polymers
  • C09D175/04—Polyurethanes
• • C—CHEMISTRY; METALLURGY
  • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
  • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
  • C09D175/00—Coating compositions based on polyureas or polyurethanes; Coating compositions based on derivatives of such polymers
  • C09D175/04—Polyurethanes
  • C09D175/06—Polyurethanes from polyesters
• • C—CHEMISTRY; METALLURGY
  • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
  • C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
  • C09J175/00—Adhesives based on polyureas or polyurethanes; Adhesives based on derivatives of such polymers
  • C09J175/04—Polyurethanes
• • C—CHEMISTRY; METALLURGY
  • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
  • C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
  • C09J175/00—Adhesives based on polyureas or polyurethanes; Adhesives based on derivatives of such polymers
  • C09J175/04—Polyurethanes
  • C09J175/06—Polyurethanes from polyesters

Definitions

• the present invention relates to a polycarbonate polyol and a method for producing the same.
• Polycarbonate polyol like polyester polyol and polyether polyol, is useful as a raw material for producing a polyurethane resin by reacting with a polyisocyanate compound, a raw material for adhesives, paints, and the like. Since polyester polyols have ester bonds, polyurethane resins obtained from them have the drawback of being inferior in hydrolysis resistance, and polyether polyols have the disadvantages of being inferior in weather resistance and heat resistance because they have ether bonds. On the other hand, from polycarbonate polyol, a polyurethane resin having excellent durability such as heat resistance, weather resistance, hydrolysis resistance and chemical resistance can be obtained.
• Such a polycarbonate polyol is usually produced by transesterifying a carbonic acid ester and a diol in the presence of a catalyst.
• a polycarbonate polyol obtained by transesterifying an aryl carbonate, a primary aliphatic triol such as trimethylolpropane and an aliphatic or alicyclic diol is It has been proposed (Patent Document 1). Further, a polycarbonate polyol obtained by transesterification of a polycarbonate diol with a triol compound and/or a tetraol compound has also been proposed (Patent Documents 2 and 3).
• the present invention has been made in view of the above background art, and provides a polycarbonate polyol which is liquid at room temperature, has a reduced number of colors and turbidity, and has an average number of hydroxyl functional groups of more than 2, and a method for producing the same.
• the task is to do.
• the present inventors have found that by using a specific inorganic metal compound or organometallic compound, it is liquid at room temperature and the average number of hydroxyl functional groups is reduced in color number and turbidity. It was found that a polycarbonate polyol having a value of 2 or more can be obtained, and the present invention has been completed.
• the present invention includes the embodiments described below.
• Polycarbonate diol (A), polyol (B) containing polyester polyol (b1) having 3 or more hydroxyl functional groups (hereinafter, simply referred to as polyol (B)), and metal of Group 1 of the periodic table.
• polyol (B) polyester polyol having 3 or more hydroxyl functional groups
• polyol (C) inorganic metal compound or organometallic compound (C) containing at least one selected from the group consisting of metals of Group 2 of the periodic table, and a turbidity suppressor (D), and having an average number of hydroxyl functional groups of 2 Polycarbonate polyol characterized by exceeding.
• the polyol (B) contains a polyester polyol (b1) having a hydroxyl functional group number of 3 or more and a polyester polyol (b2) having a hydroxyl functional group number of 2 or more and less than 3; 1] Polycarbonate polyol.
• APHA No. based on JIS-K1557 A polycarbonate polyol having a color number of 100 or less, a kaolin turbidity based on JIS-K0101 of 5 or less, a liquid at 5° C. under normal pressure, and an average number of hydroxyl functional groups of more than 2.
• [5] Contains an inorganic metal compound or organometallic compound (C) containing at least one selected from the group consisting of metals of Group 1 of the periodic table and metals of Group 2 of the periodic table, and a turbidity suppressor (D)
• C inorganic metal compound or organometallic compound
• D turbidity suppressor
• the normal temperature in the present invention means 5°C or higher and 35°C or lower at normal pressure. Further, the liquid state in the present invention means a state in which even a slight fluidity is obtained at room temperature.
• a polycarbonate polyol which is liquid at normal temperature and has a reduced number of colors and turbidity and an average number of hydroxyl functional groups of more than 2.
• Examples of the polycarbonate diol (A) in the present invention include dialkyl carbonates such as dimethyl carbonate and diethyl carbonate, alkylene carbonates such as ethylene carbonate and propylene carbonate, diphenyl carbonate, dinaphthyl carbonate, dianthryl carbonate and diphenanthryl carbonate. , Diindanyl carbonate, tetrahydronaphthyl carbonate, and other carbonates such as diaryl carbonates, and those obtainable by the reaction with glycol.
• glycol examples include ethylene glycol, 1,2-propanediol, 1,3-propanediol, 1,2-butanediol, 1,3-butanediol, 1,4-butanediol, 1,5-pentanediol, 1,6-hexanediol, 1,8-octanediol, 1,9-nonanediol, 3-methyl-1,5-pentanediol, 3,3-dimethylolheptane, diethylene glycol, dipropylene glycol, neopentyl glycol, Cyclohexane-1,4-diol, cyclohexane-1,4-dimethanol, dimer acid diol, ethylene oxide or propylene oxide adduct of bisphenol A, bis( ⁇ -hydroxyethyl)benzene, xylylene glycol, and other diols are listed. be able to. These may be
• polyester polyol (b1) having 3 or more hydroxyl functional groups of the present invention examples include polyester polyols obtained from a dicarboxylic acid and a polyol containing a polyhydric alcohol having 3 or more hydroxyl functional groups, and 3 or more hydroxyl functional groups.
• polyester polyols obtained from a dicarboxylic acid and a polyol containing a polyhydric alcohol having 3 or more hydroxyl functional groups, and 3 or more hydroxyl functional groups examples thereof include polyols obtained by ring-opening addition polymerization of cyclic ester compounds such as lactones using the polyhydric alcohol as an initiator.
• polyhydric alcohol having 3 or more hydroxyl functional groups examples include trimethylolpropane, glycerin, pentaerythritol and sorbitol.
• a bifunctional alcohol such as ethylene glycol, diethylene glycol, propylene glycol, butanediol, neopentyl glycol, hexamethylene glycol, dipropylene glycol or trimethylene glycol may be used in combination as long as the performance is not deteriorated.
• dicarboxylic acid examples include polybasic acids such as oxalic acid, malonic acid, maleic acid, adipic acid, tartaric acid, pimelic acid, sebacic acid, phthalic acid and terephthalic acid, and one or two selected from these.
• polybasic acids such as oxalic acid, malonic acid, maleic acid, adipic acid, tartaric acid, pimelic acid, sebacic acid, phthalic acid and terephthalic acid, and one or two selected from these.
• One or more species can be used in combination.
• Preferred lactones include, for example, ⁇ -propiolactone, ⁇ -butyrolactone, ⁇ -butyrolactone, ⁇ -valerolactone, ⁇ -valerolactone, ⁇ -valerolactone, ⁇ -caprolactone, ⁇ -caprolactone, ⁇ -caprolactone, ⁇ -caprolactone, ⁇ -caprolactone, ⁇ -Caprolactone, ⁇ -caprolactone, ⁇ -methyl- ⁇ -caprolactone, ⁇ -methyl- ⁇ -caprolactone, 4-methylcaprolactone, ⁇ -caprylolactone, ⁇ -caprylolactone, ⁇ -palmitolactone and the like can be mentioned.
• One kind or two or more kinds selected from the above can be mixed and used. Of these, a ring-opening addition polymer of ⁇ -caprolactone using trimethylolpropane as an initiator is preferable in terms of stability during polymerization and economical efficiency.
• a polyester polyol (b2) having a hydroxyl functional group number of 2 or more and less than 3 may be used in combination.
• Particularly preferred are polyester polyols obtained from glycol and dicarboxylic acid, and polyols obtained by ring-opening addition polymerization of cyclic ester compounds such as lactones using glycol as an initiator.
• glycol examples include ethylene glycol, 1,2-propanediol, 1,3-propanediol, 1,2-butanediol, 1,3-butanediol, 1,4-butanediol, 1,5-pentanediol.
• dicarboxylic acid examples include polybasic acids such as oxalic acid, malonic acid, maleic acid, adipic acid, tartaric acid, pimelic acid, sebacic acid, phthalic acid and terephthalic acid, and one selected from these Alternatively, two or more kinds can be used in combination.
• lactones examples include ⁇ -propiolactone, ⁇ -butyrolactone, ⁇ -butyrolactone, ⁇ -valerolactone, ⁇ -valerolactone, ⁇ -valerolactone, ⁇ -caprolactone, ⁇ -caprolactone, ⁇ -caprolactone, ⁇ -caprolactone, ⁇ -methyl- ⁇ -caprolactone, ⁇ -methyl- ⁇ -caprolactone, 4-methylcaprolactone, ⁇ -caprylolactone, ⁇ -caprylolactone, ⁇ -palmitolactone and the like can be mentioned. One or two or more selected from these can be used in combination. Of these, a ring-opening addition polymer of ⁇ -caprolactone using ethylene glycol as an initiator is preferable from the viewpoint of stability during polymerization and economical efficiency.
• the average number of hydroxyl functional groups of the polycarbonate polyol of the present invention is more than 2, preferably 2.3 to 3.5, more preferably 2.5 to 3.0.
• the average hydroxyl value of the polycarbonate polyol is preferably 75 to 285 mgKOH/g, more preferably 90 to 180 mgKOH/g.
• the number average molecular weight of the polycarbonate polyol is preferably 400 to 5,000, more preferably 500 to 2,000, in consideration of easiness of synthesis and handling.
• the number average molecular weight can be determined by GPC (gel permeation chromatography) measurement using standard polystyrene as a calibration curve.
• This component (C) has the effect of promoting the transesterification reaction.
• the metal of Group 1 of the periodic table include lithium, sodium, potassium, rubidium and cesium
• examples of the metal of Group 2 of the periodic table include magnesium, calcium, strontium, barium and the like.
• inorganic metal compounds or organic metal compounds of these metals are mentioned, and one kind selected from these or two or more kinds can be used in combination.
• inorganic metal compounds of metals of Group 1 of the periodic table are preferable, and lithium acetate, potassium carbonate, and potassium hydrogen carbonate are particularly preferable in consideration of the ease of transesterification reaction and the ease of handling.
• the amount of the component (C) used is preferably 0.0001 to 1% by mass, and more preferably 0.001 to 0.1% by mass of the total mass of the polycarbonate diol (A) and the polyol (B).
• the amount of the component (C) is less than the lower limit, the reaction time becomes long and the resulting polycarbonate polyol is likely to be colored. If the upper limit is exceeded, the turbidity tends to increase.
• the reaction temperature of the transesterification reaction is preferably 70 to 250°C, more preferably 80 to 220°C.
• Polycarbonate polyol in which the transesterification reaction has not proceeded sufficiently is solid at room temperature due to the unreacted highly crystalline raw material.
• Examples of the turbidity suppressing agent (D) of the present invention include inorganic acids such as phosphoric acid and hydrochloric acid, organic acids having a sulfonic acid group, a sulfamic acid group, and the like, and their esters and acyl halides.
• inorganic acids such as phosphoric acid and hydrochloric acid
• organic acids having a sulfonic acid group, a sulfamic acid group, and the like and their esters and acyl halides.
• phosphorus compounds such as phosphoric acid, phosphoric acid ester, phosphorous acid, and phosphorous acid ester are preferable from the viewpoint of easy handling.
• the addition timing is preferably 140° C. or lower after completion of the transesterification reaction.
• the amount of the turbidity suppressor (D) added is preferably 0.0001 to 1% by mass, more preferably 0.001 to 0.1% by mass, based on the total mass of the polycarbonate diol (A) and the polyol (B). ..
• the amount added is less than the lower limit, the turbidity and the number of colors of the obtained polycarbonate polyol tend to increase, and when it exceeds the upper limit, the reactivity of the polycarbonate polyol may be slowed.
• the addition of the turbidity suppressor improves the compatibility between the obtained polycarbonate polyol and the component (C) and suppresses the turbidity.
• a polyurethane resin can be obtained by reacting the above-described polycarbonate polyol of the present invention with polyisocyanate by a known method.
• the polyisocyanate is not particularly limited and can be appropriately selected and used from various conventionally known polyisocyanates.
• polyisocyanates For example, hexamethylene diisocyanate, 1,4-tetramethylene diisocyanate, 2-methylpentane-1,5-diisocyanate, lysine diisocyanate and other aliphatic isocyanates; isophorone diisocyanate, norbornane diisocyanate, hydrogenated tolylene diisocyanate, hydrogenated xylene Alicyclic diisocyanates such as diisocyanate, hydrogenated diphenylmethane diisocyanate and hydrogenated tetramethylxylene diisocyanate; 2,4-tolylene diisocyanate, 2,6-tolylene diisocyanate, 4,4'-diphenylmethane diisocyanate, 2,4' -Diphenylmethane diisocyanate, 2,2'-diphenylmethan
• organic polyisocyanates and, if necessary, using alcohol or the like, urethane-modified polyisocyanates, urea-modified polyisocyanates, allophanate-modified polyisocyanates, burette-modified polyisocyanates, carbodiimide-modified polyisocyanates, and uretonimines that can be produced by conventionally known methods.
• the modified polyisocyanate, uretdione modified polyisocyanate, and isocyanurate modified polyisocyanate may be used alone or in combination of two or more.
• the polyurethane resin thus obtained can be suitably used for a coating composition, an adhesive composition and the like.
• a reactor equipped with a stirrer, a thermometer, a heating device, and a distillation column has a molar ratio of 1,6-hexanediol (hereinafter abbreviated as 1,6-HG) and diethyl carbonate (hereinafter abbreviated as DEC) of 1. 830 g of 1,6-HG and 771 g of DEC were charged so that the ratio was 08:1, and 0.05 g of tetrabutyl titanate (hereinafter, abbreviated as TBT) was further charged as a reaction catalyst, and gradually under a nitrogen stream. The temperature was raised to 190°C.
• 1,6-HG 1,6-hexanediol
• DEC diethyl carbonate
• Polyol-2 [Production of polycarbonate diol 2] Using the same apparatus as in the production of polycarbonate diol 1, except that 826 g of 1,6-HG and 787 g of DEC were charged so that the molar ratio of 1,6-HG and DEC was 1.05:1 Synthesis was carried out in the same manner as in Production 1 to obtain a polycarbonate diol (Polyol-2).
• the obtained Polyol-2 had an average number of hydroxyl functional groups of 2.0 and a hydroxyl value of 37.2 (mgKOH/g).
• Example 1 Production 1 of polycarbonate polyol
• a reactor equipped with a stirrer, a thermometer, and a heating device 600 g of Polyol-1 obtained in Production 1 of polycarbonate diol, 400 g of polycaprolactone triol (Plaxel 303), and 0.1 g of lithium acetate were charged and heated at 190°C.
• the transesterification reaction was carried out for 5 hours. Thereafter, the mixture was cooled to 120° C., 0.5 g of JP-508 (manufactured by Johoku Chemical Co., Ltd.) was added, and the mixture was stirred and mixed for 30 minutes to obtain a polycarbonate polyol (PCP-1).
• the average number of hydroxyl functional groups of the obtained PCP-1 was 2.81, and the hydroxyl value was 250.4 (mgKOH/g).
• Example 2 Production 2 of polycarbonate polyol
• a reactor equipped with a stirrer, a thermometer, and a heating device 500 g of Polyol-2 obtained in the production 2 of polycarbonate diol, 500 g of polycaprolactone triol (Plaxel 305) and 0.1 g of potassium carbonate were charged, and the mixture was heated at 190° C. The transesterification reaction was carried out for 5 hours. Then, the mixture was cooled to 120° C., 0.5 g of JP-508 was added, and the mixture was stirred and mixed for 30 minutes to obtain a polycarbonate polyol (PCP-2).
• the average number of hydroxyl functional groups of the obtained PCP-2 was 2.85, and the hydroxyl value was 171.7 (mgKOH/g).
• Example 3 Production 3 of polycarbonate polyol
• a reactor equipped with a stirrer, a thermometer, and a heating device 550 g of Polyol-2 obtained in Production 2 of polycarbonate diol, 400 g of polycaprolactone triol (Plaxel 305), and 50 g of polycaprolactone diol (Plaxel 210) were charged, 0.1 g of potassium hydrogen carbonate was charged, and transesterification reaction was carried out at 190° C. for 5 hours. Then, the mixture was cooled to 120° C., 0.5 g of JP-508 was added, and the mixture was stirred and mixed for 30 minutes to obtain a polycarbonate polyol (PCP-3). The average number of hydroxyl functional groups of the obtained PCP-3 was 2.76, and the hydroxyl value was 148.6 (mgKOH/g).
• Example 4 Production 4 of polycarbonate polyol
• 600 g of Polyol-2 obtained in the production 2 of polycarbonate diol 600 g of polycaprolactone tetraol (Plaxel 410), and 0.1 g of potassium hydrogen carbonate were charged, and 190 The transesterification reaction was carried out at 0°C for 5 hours. Thereafter, the mixture was cooled to 120° C., 0.5 g of JP-508 was added, and the mixture was stirred and mixed for 30 minutes to obtain a polycarbonate polyol (PCP-4).
• the obtained PCP-4 had an average hydroxyl functional group number of 3.32 and a hydroxyl value of 108.6 (mgKOH/g).
• Example 5 Production 5 of polycarbonate polyol
• 600 g of Polyol-2 obtained in the production 2 of polycarbonate diol, 400 g of polycaprolactone triol (Plaxel 305), and 0.1 g of barium acetate were charged and heated at 190°C.
• the transesterification reaction was carried out for 5 hours.
• the mixture was cooled to 120° C., 0.5 g of JP-508 was added, and the mixture was stirred and mixed for 30 minutes to obtain a polycarbonate polyol (PCP-5).
• the obtained PCP-5 had an average number of hydroxyl functional groups of 2.78 and a hydroxyl value of 144.9 (mgKOH/g).
• the color number of the obtained polycarbonate polyol was measured according to JIS-K1557, and if the color number is 100 or less, it can be said to be good.
• the kaolin turbidity (visual method) was measured according to JIS-K0101, and it can be said that the turbidity is 5 or less.

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