Process for producing polyether polyol and / or polyether monoalcohol
The method of ring-opening addition polymerization using a composite metal cyanide complex catalyst addresses the high viscosity issue in polyether poly(mono)ol production, resulting in low viscosity products that are easier to handle.
Patent Information
- Application Number
- JP2021113605
- Authority / Receiving Office
- JP · JP
- Patent Type
- Patents
- Current Assignee / Owner
- Filing Date
- 2021-07-08
- Publication Date
- 2025-06-17
- Estimated Expiration
- 2041-07-08
AI Technical Summary
Existing methods for producing polyether poly(mono)alcohols result in high viscosity products, which are difficult to handle.
A method involving ring-opening addition polymerization of alkylene oxide in the presence of a composite metal cyanide complex catalyst, with specific reaction conditions and catalyst ratios to achieve a polyether poly(mono)ol with low viscosity.
The method effectively produces polyether poly(mono)ols with low viscosity, even at high molecular weights, thereby improving handleability.
Smart Images

Figure 0007693423000002 
Figure 0007693423000003 
Figure 0007693423000004
Abstract
Description
Technical Field
[0001] The present invention relates to a method for producing polyether polyol and / or polyether monoalcohol.
Background Art
[0002] Conventionally, polyether poly(mono)alcohol is widely known as a polyurethane raw material for reacting with polyisocyanate to obtain a polyurethane resin.
[0003] Such polyether poly(mono)alcohol can be produced, for example, by subjecting an initiator having an active hydrogen group to ring-opening addition polymerization of an alkylene oxide.
[0004] As such a production method, for example, a method for producing a polyether polyol having an equivalent molecular weight of 8,000 to 20,000 g / mol from one or more H-functional starter compounds and one or more alkylene oxides in the presence of a double metal cyanide (DMC) catalyst has been proposed (see, for example, Patent Document 1). Further, in this method, alkylene oxide is supplied to the reactor over 15 to 23 hours.
Prior Art Documents
Patent Documents
[0005]
Patent Document 1
Summary of the Invention
Problems to be Solved by the Invention
[0006] On the other hand, from the viewpoint of handleability, it is required to lower the viscosity of polyether poly(mono)alcohol.
[0007] The present invention provides a method for producing polyether poly(mono)alcohol that produces polyether poly(mono)alcohol having a low viscosity.
Means for Solving the Problem
[0008] The present invention [1] is a method for producing a polyether poly(mono)ol by subjecting an initiator having an active hydrogen group to ring-opening addition polymerization of an alkylene oxide in the presence of a composite metal cyanide complex catalyst, wherein the equivalent molecular weight of the polyether poly(mono)ol is 2000 g / mol or more, and the method satisfies the following formulas (1) to (3). Reaction ratio = Equivalent molecular weight of polyether poly(mono)ol / Equivalent molecular weight of initiator (1) X = Supply time of alkylene oxide / Reaction ratio (2) X ≧ Equivalent molecular weight of polyether poly(mono)ol / 3000 (3)
[0009] The present invention [2] includes the method for producing a polyether poly(mono)ol according to [1] above, wherein the equivalent molecular weight of the polyether poly(mono)ol is 5000 g / mol or more and 12500 g / mol or less.
Advantages of the Invention
[0010] In the method for producing a polyether poly(mono)ol of the present invention, the reaction ratio, the supply time of the alkylene oxide, and the equivalent molecular weight of the polyether poly(mono)ol satisfy a predetermined relationship. Therefore, a polyether poly(mono)ol having a low viscosity can be produced.
Brief Description of the Drawings
[0011]
Figure 1
Figure 2
Figure 3
Mode for Carrying Out the Invention
[0012] The method for producing a polyether poly(mono)ol of the present invention is a method for producing a polyether poly(mono)ol having a predetermined equivalent molecular weight by subjecting an initiator having an active hydrogen group to ring-opening addition polymerization of an alkylene oxide under predetermined reaction conditions in the presence of a double metal cyanide complex catalyst.
[0013] <Double metal cyanide complex catalyst> As the double metal cyanide complex catalyst (hereinafter sometimes referred to as a DMC catalyst), a known one can be used. Specific examples and production methods of the double metal cyanide complex catalyst are described in the specification of International Publication Pamphlet WO2013 / 157486.
[0014] <Initiator> The initiator has one or more active hydrogen groups. Examples of the active hydrogen group include a hydroxyl group, a thiol group, and an amino group, and preferably a hydroxyl group. That is, the initiator is preferably an initiator having one or more hydroxyl groups.
[0015] Examples of the initiator having one or more hydroxyl groups include low molecular weight hydroxyl group-containing compounds and high molecular weight hydroxyl group-containing compounds.
[0016] The low molecular weight hydroxyl group-containing compound is a compound having an equivalent molecular weight of 20 g / mol or more and less than 200 g / mol, preferably less than 150 g / mol. Examples of the low molecular weight hydroxyl group-containing compound include monohydric alcohols, dihydric alcohols, trihydric alcohols, tetrahydric alcohols, pentahydric alcohols, hexahydric alcohols, heptahydric alcohols, and octahydric alcohols.
[0017] Examples of the monohydric alcohol include methanol, ethanol, 1-propanol, 2-propanol, 1-butanol, 2-methyl-2-propanol, 2-ethylhexanol, and phenol. Examples of the dihydric alcohol include ethylene glycol, propylene glycol (1,2-propylene glycol), dipropylene glycol, tripropylene glycol, butylene glycol, pentamethylene glycol, hexamethylene glycol, heptamethylene glycol, and octamethylene glycol. Examples of the trihydric alcohol include glycerin, trimethylolpropane, and triisopropanolamine. Examples of the tetrahydric alcohol include tetramethylolmethane (pentaerythritol) and diglycerin. Examples of the pentahydric alcohol include xylitol. Examples of the hexahydric alcohol include sorbitol, mannitol, allitol, iditol, dulcitol, altitol, inositol, and dipentaerythritol. Examples of the heptahydric alcohol include perseitol. Examples of the octahydric alcohol include sucrose.
[0018] The high molecular weight hydroxyl group-containing compound is a compound having an equivalent molecular weight of 200 g / mol or more, preferably 500 g / mol or more and 5000 g / mol or less. Examples of the high molecular weight hydroxyl group-containing compound include polyether poly(mono)ol (polyether polyol and / or polyether mono-ol), polyester poly(mono)ol (polyester polyol and / or polyester mono-ol), and polycarbonate poly(mono)ol (polycarbonate polyol and / or polycarbonate mono-ol), and preferably polyether poly(mono)ol.
[0019] Examples of the polyether poly(mono)ol include polyoxyalkylene (C2-C3) monoalcohol, polyoxyalkylene (C2-C3) polyalcohol, polytetramethylene ether monoalcohol, and polytetramethylene ether polyalcohol. Preferably, polyoxyalkylene (C2-C3) monoalcohol and polyoxyalkylene (C2-C3) polyalcohol are mentioned. The polyoxyalkylene (C2-C3) monoalcohol and polyoxyalkylene (C2-C3) polyalcohol are polyoxyalkylene monoalcohol and polyoxyalkylene polyalcohol in which the alkylene has 2 or more and 3 or less carbon atoms. Examples of the polyoxyalkylene (C2-C3) monoalcohol include polyoxyethylene monoalcohol and polyoxypropylene monoalcohol. Examples of the polyoxyalkylene (C2-C3) polyalcohol include polyoxyethylene glycol (polyethylene glycol) and polyoxypropylene glycol (polypropylene glycol). Preferably, polyoxypropylene glycol is mentioned.
[0020] In addition, the polyether poly(mono)ol as an initiator is produced by a known method.
[0021] Examples of the initiator having one or more hydroxyl groups preferably include high molecular weight hydroxyl group-containing compounds, and more preferably polyether poly(mono)ols.
[0022] The hydroxyl value of the initiator having one or more hydroxyl groups is, for example, 11 mgKOH / g or more and, for example, 2800 mgKOH / g or less. As described above, since a high molecular weight hydroxyl group-containing compound is preferably selected as the initiator having one or more hydroxyl groups, the hydroxyl value of the initiator having one or more hydroxyl groups is preferably 11 mgKOH / g or more, more preferably 18 mgKOH / g or more, and, for example, preferably 280 mgKOH / g or less, more preferably 112 mgKOH / g or less.
[0023] The hydroxyl value of the initiator having one or more hydroxyl groups can be determined by an acetylation method or a phthalation method conforming to Method A or Method B of JIS K 1557-1 (2007) (the same shall apply hereinafter).
[0024] The functional group number of the initiator is, for example, 1 or more, preferably 2 or more, and, for example, 8 or less, preferably 3 or less.
[0025] The equivalent molecular weight of the initiator is, for example, 20 g / mol or more, and, for example, 5000 g / mol or less. As described above, since a high molecular weight hydroxyl group-containing compound is preferably selected as the initiator, the equivalent molecular weight of the initiator is preferably 200 g / mol or more, more preferably 500 g / mol or more, and preferably 5000 g / mol or less, more preferably 3000 g / mol or less.
[0026] In addition, the equivalent molecular weight of the initiator can be determined by the following formula (4).
[0027] Equivalent molecular weight of initiator = 56100 / hydroxyl value of initiator (4)
[0028] In addition, the equivalent molecular weight of the initiator, although it will be described in detail later, satisfies the following formula (1).
[0029] The initiator can be used alone or in combination of two or more kinds.
[0030] <Alkylene oxide> Examples of the alkylene oxide include alkylene oxides having 2 to 20 carbon atoms. Examples of the alkylene oxide having 2 to 20 carbon atoms include ethylene oxide, propylene oxide (1,2-propylene oxide), butylene oxide, pentylene oxide, hexylene oxide, heptylene oxide, octylene oxide, nonylene oxide, styrene oxide, and decylene oxide.
[0031] As the alkylene oxide, preferably, an alkylene oxide having 2 to 6 carbon atoms, more preferably, ethylene oxide and propylene oxide (1,2-propylene oxide) are mentioned.
[0032] The alkylene oxide can be used alone or in combination of two or more, and preferably, the single use of propylene oxide and the combined use of ethylene oxide and propylene oxide are mentioned. <Polyether poly(mono)ol> The polyether poly(mono)ol is a reaction product obtained by this production method. The polyether poly(mono)ol is defined as a polyether polyol and / or a polyether monoalcohol, and preferably, it is a polyether polyol.
[0033] The hydroxyl value of the polyether poly(mono)ol is, for example, 1 mgKOH / g or more, preferably, 5 mgKOH / g or more, and, for example, 50 mgKOH / g or less, preferably, 30 mgKOH / g or less.
[0034] The functional group number of the polyether poly(mono)ol is the functional group number corresponding to the functional group number of the initiator. Specifically, when an initiator having a functional group number of 1 is used, a polyether monoalcohol having a functional group number of 1 is obtained, when an initiator having a functional group number of 2 is used, a polyether diol having a functional group number of 2 is obtained, and when an initiator having a functional group number of 3 is used, a polyether triol having a functional group number of 3 is obtained. Specifically, the functional group number of the polyether poly(mono)ol is, for example, 1 or more, preferably, 2 or more, and, for example, 8 or less, preferably, 3 or less.
[0035] The equivalent molecular weight of the polyether poly(mono)ol is 2000 g / mol or more.
[0036] In the method for producing a polyether poly(mono)ol of the present invention, a relatively high molecular weight polyether poly(mono)ol having a molecular weight of 2000 g / mol or more is produced. Although a relatively high molecular weight polyether poly(mono)ol tends to have a high viscosity, in the method for producing a polyether poly(mono)ol of the present invention, a low viscosity polyether poly(mono)ol can be produced even if it has a relatively high molecular weight.
[0037] Further, the equivalent molecular weight of the polyether poly(mono)ol is preferably 5000 g / mol or more, and for example, 12500 g / mol or less, from the viewpoint of increasing the molecular weight of the polyether poly(mono)ol.
[0038] The equivalent molecular weight of the polyether poly(mono)ol satisfies the following formula (1) and the following formula (3), which will be described in detail later.
[0039] Further, the equivalent molecular weight of the polyether poly(mono)ol can be determined by the following formula (5).
[0040] Equivalent molecular weight of polyether poly(mono)ol = 56100 / Hydroxyl value of polyether poly(mono)ol (5)
[0041] <Production method and reaction conditions> The method for producing a polyether poly(mono)ol includes a first step of charging a part of an alkylene oxide into a reaction solution containing a double metal cyanide complex catalyst and an initiator, and a second step of supplying the remainder of the alkylene oxide to a reaction solution containing an initiator and a double metal cyanide complex catalyst.
[0042] [First step] In the first step, first, a double metal cyanide complex catalyst and an initiator are blended in a reactor to prepare a reaction solution containing the double metal cyanide complex catalyst and the initiator. Then, the reaction solution is heated while stirring under a nitrogen atmosphere.
[0043] The blending ratio of the composite metal cyanide complex catalyst is appropriately set according to the equivalent molecular weight of the polyether poly(mono)ol.
[0044] Specifically, after the reaction is completed, the composite metal cyanide complex catalyst is blended so that, for example, it is 1 ppm or more, preferably 30 ppm or more, and for example, 500 ppm or less, preferably 200 ppm or less, based on 100 g of the polyether poly(mono)ol.
[0045] As heating conditions, the heating temperature is, for example, 70 °C or more, preferably 90 °C or more, and for example, 150 °C or less, preferably 120 °C or less. The heating time is, for example, 10 minutes or more, preferably 20 minutes or more, and for example, 120 minutes or less, preferably 60 minutes or less.
[0046] Next, a part of the alkylene oxide is charged into the reaction solution. Specifically, the alkylene oxide is charged at a ratio of, for example, 1 part by mass or more, preferably 5 parts by mass or more, and for example, 80 parts by mass or less, preferably 20 parts by mass or less, based on 100 parts by mass of the initiator.
[0047] Thereby, the composite metal cyanide complex catalyst is activated. The activation of the composite metal cyanide complex catalyst can be confirmed by the heat generation of the reaction solution and the decrease in the pressure inside the reactor.
[0048] [Second Step] In the second step, after the first step (after the activation of the composite metal cyanide complex catalyst), the remainder of the alkylene oxide is supplied to the reaction solution. Specifically, the alkylene oxide is supplied at a ratio of, for example, 50 parts by mass or more, preferably 100 parts by mass or more, and for example, 2000 parts by mass or less, preferably 1000 parts by mass or less, based on 100 parts by mass of the initiator.
[0049] Also, the supply time is, for example, 2 hours or more, preferably 6 hours or more, more preferably 9 hours or more, and for example, 80 hours or less, preferably 50 hours or less, more preferably 25 hours or less.
[0050] The reaction temperature is, for example, 100°C or higher, and, for example, 150°C or lower, preferably 130°C or lower.
[0051] As described above, the alkylene oxide can be subjected to ring-opening addition polymerization with the initiator. Thereby, a polyether poly(mono)ol can be obtained.
[0052] After the reaction is completed, unreacted alkylene oxide can also be removed by a known method such as distillation or extraction.
[0053] In the above reaction, the reaction ratio, the supply time of the alkylene oxide, and the equivalent molecular weight of the polyether poly(mono)ol satisfy a predetermined relationship.
[0054] The reaction ratio is the ratio of the equivalent molecular weight of the reaction product (polyether poly(mono)ol) to the initiator, and is represented by the following formula (1). Reaction ratio = Equivalent molecular weight of polyether poly(mono)ol / Equivalent molecular weight of initiator (1)
[0055] The supply time of the alkylene oxide is the supply time in the second step described above. Specifically, the supply time of the alkylene oxide is the supply time starting from the point when the double metal cyanide complex catalyst is activated.
[0056] The equivalent molecular weight of the polyether poly(mono)ol is the equivalent molecular weight of the polyether poly(mono)ol (reaction product) described above.
[0057] And the reaction ratio, the supply time of the alkylene oxide, and the equivalent molecular weight of the polyether poly(mono)ol satisfy the following formula (2) and the following formula (3). X = Supply time of alkylene oxide / Reaction ratio (2) X ≥ Equivalent molecular weight of polyether poly(mono)ol / 3000 (3)
[0058] In the above formula (2), X is a parameter for estimating the relationship between the supply time of alkylene oxide and the reaction magnification. Specifically, as the reaction magnification increases, it is necessary to increase the supply time of alkylene oxide.
[0059] If the reaction magnification, the supply time of alkylene oxide, and the equivalent molecular weight of the polyether poly(mono)ol satisfy the above formulas (1) to (3), a polyether poly(mono)ol with a low viscosity can be produced.
[0060] <Function and Effect> In the method for producing a polyether poly(mono)ol, the reaction magnification, the supply time of alkylene oxide, and the equivalent molecular weight of the polyether poly(mono)ol satisfy a predetermined relationship (the above formulas (1) to (3)). Therefore, a polyether poly(mono)ol with a low viscosity can be produced.
[0061] The relationship between X and the viscosity of the polyether poly(mono)ol will be described with reference to FIG. 1.
[0062] FIG. 1 is a graph showing the relationship between X and viscosity for three polyether poly(mono)ols (Polyether poly(mono)ol A to Polyether poly(mono)ol C) having different equivalent molecular weights from each other.
[0063] In FIG. 1, the equivalent molecular weights of Polyether poly(mono)ol A to Polyether poly(mono)ol C increase in the order of Polyether poly(mono)ol A, Polyether poly(mono)ol B, and Polyether poly(mono)ol C.
[0064] In each polyether poly(mono)ol, the viscosity of the polyether poly(mono)ol tends to decrease exponentially with an increase in X up to a predetermined X value (X A , X B and X C reference). Then, at a predetermined X value (X A , X B and XC ) exceeds, the viscosity tends to gradually decrease or become constant.
[0065] Also, as the equivalent molecular weight of the polyether poly(mono)ol increases, the predetermined X value tends to increase.
[0066] And the above formulas (1) to (3) show the above-mentioned tendency. Specifically, as shown in FIG. 2, the above formula (3) (X ≥ equivalent molecular weight of polyether poly(mono)ol / 3000) shows the change amount of the equivalent molecular weight of the polyether poly(mono)ol with respect to the change amount of the above-mentioned predetermined X value. If the X value and the equivalent molecular weight of the polyether poly(mono)ol are in the hatched region of FIG. 2, a polyether poly(mono)ol with a low viscosity can be produced. On the other hand, if the X value and the equivalent molecular weight of the polyether poly(mono)ol are outside the above region (for example, point a in FIG. 2), since the X value is small with respect to the equivalent molecular weight of the polyether poly(mono)ol, the viscosity of the polyether poly(mono)ol cannot be lowered (specifically, point a in FIG. 1).
[0067] As described above, the viscosity of the polyether poly(mono)ol decreases with an increase in X and finally reaches a constant value. And the point where the merit of the viscosity reduction rate (viscosity reduction) exceeds the demerit of the increase in X (reduction in production efficiency) is defined as the optimum viscosity. Specifically, as shown in FIG. 1, the optimum viscosity of the polyether poly(mono)ol is the viscosity (P A , P B and P C ) at the predetermined X values (X A , P B and P C ).
[0068] Also, the optimum viscosity of the polyether poly(mono)ol can be estimated as the viscosity at the point when the decrease amount of the viscosity with respect to the increase amount of X becomes 10% or less. For example, when the increase amount of X is 0.3 or more, the viscosity at the point when the decrease amount of the viscosity becomes 10% or less can be estimated as the optimum viscosity.
[0069] The optimum viscosity of the polyether poly(mono)ol is determined according to the type of alkylene oxide, the equivalent molecular weight of the polyether poly(mono)ol, and the functional group number of the polyether poly(mono)ol. Specifically, as the equivalent molecular weight of the polyether poly(mono)ol increases, the optimum viscosity of the polyether poly(mono)ol increases. Also, as the functional group number of the polyether poly(mono)ol increases, the optimum viscosity of the polyether poly(mono)ol increases.
[0070] Note that the method for measuring viscosity will be described in detail in the examples below.
[0071] <Modification Example> In the modification example, for the members and steps similar to those in one embodiment, the same reference numerals are given, and the detailed description thereof is omitted. Also, the modification example can exhibit the same effects as those of one embodiment unless otherwise specified. Furthermore, one embodiment and these modification examples can be appropriately combined.
[0072] In the above description, a part of the alkylene oxide is charged into the reaction solution containing the initiator and the double metal cyanide complex catalyst, and after activating the double metal cyanide complex catalyst (the first step), the remaining part of the alkylene oxide is supplied (the second step). On the other hand, it is also possible to carry out only the second step without carrying out the first step. That is, in the second step, all of the alkylene oxide can also be supplied to the reaction solution. The supply time of the alkylene oxide in such a case is the supply time starting from the point when the double metal cyanide complex catalyst is activated.
[0073] In the first step and the second step, if necessary, a known solvent can also be blended into the reaction solution. That is, this production method can be carried out without a solvent or under a solvent. Preferably, this production method is carried out without a solvent.
[0074] In addition, in the method for producing a polyether poly(mono)ol of the present invention, the equivalent molecular weight of the polyether poly(mono)ol is 2000 g / mol or more. However, even if the equivalent molecular weight of the polyether poly(mono)ol is less than 2000 g / mol, a polyether poly(mono)ol with low viscosity can be produced as long as the above formulas (1) to (3) are satisfied.
Examples
[0075] Next, the present invention will be described based on examples and comparative examples, but the present invention is not limited by the following examples. Note that "parts" and "%" are based on mass unless otherwise specified. In addition, specific numerical values such as the blending ratio (content ratio), physical property values, and parameters used in the following description can be replaced with the upper limit values (numerical values defined as "below" and "less than") or lower limit values (numerical values defined as "above" and "exceeding") of the corresponding blending ratio (content ratio), physical property values, parameters, etc. described in the above "Mode for Carrying Out the Invention".
[0076] 1. Details of Components The trade names and abbreviations of the components used in each example and each comparative example will be described in detail. PH-DMC: Composite metal cyanide complex catalyst (DMC catalyst), manufactured by Pharmicell Co., Ltd. PO: Propylene oxide (1,2-propylene oxide) EO: Ethylene oxide D-400: Trade name "Actocol D-400", polyoxypropylene glycol, hydroxyl value 280 mgKOH / g, equivalent molecular weight 200 g / mol, manufactured by Mitsui Chemicals SKC Polyurethane Co., Ltd. D-2000: Trade name "Actocol D-2000", polyoxypropylene glycol, hydroxyl value 56.1 mgKOH / g, equivalent molecular weight 1000 g / mol, manufactured by Mitsui Chemicals SKC Polyurethane Co., Ltd. T-3000: Trade name "Actocol T-3000", polyoxypropylene triol, hydroxyl value 56.1 mg KOH / g, equivalent molecular weight 1000 g / mol, manufactured by Mitsui Chemicals SKC Polyurethane Co., Ltd. ML-3000: Trade name "Actocol ML-3000", polyoxypropylene monoalcohol, hydroxyl value 18.7 mg KOH / g, equivalent molecular weight 3000 g / mol, manufactured by Mitsui Chemicals SKC Polyurethane Co., Ltd. DL-6000: Trade name "Actocol DL-6000", polyoxypropylene glycol, hydroxyl value 18.7 mg KOH / g, equivalent molecular weight 3000 g / mol, manufactured by Mitsui Chemicals SKC Polyurethane Co., Ltd.
[0077] 2. Production of polyether poly(mono)ol Example 1 <First step> 500 g of D-2000 as an initiator and 135 mg of PH-DMC were blended in a reactor to prepare a reaction solution containing the initiator and PH-DMC. Next, degassing under reduced pressure and nitrogen substitution were carried out to remove oxygen in the reactor.
[0078] Next, while stirring the reaction solution at a speed of 300 rpm with a stirring blade, it was heated to raise the temperature of the reaction solution to 100°C.
[0079] Next, 50 g of PO was charged into the reaction solution over 10 minutes. While maintaining the temperature of the reaction solution at 100°C, the reaction solution was stirred, and after 30 minutes, a rapid heat generation and pressure drop of the reaction solution occurred. Thereby, the activation of PH-DMC was confirmed. The temperature of the reaction solution at that time was 120°C.
[0080] <Second step> While maintaining the temperature of the reaction solution at 120 °C, 2450 g of PO was continuously supplied over 12 hours (supply time). After the supply, while maintaining the temperature of the reaction solution at 120 °C, the reaction solution was continuously stirred and aged. Subsequently, a small amount of unreacted PO was removed by vacuum treatment. Thereby, polyether poly(mono)ol (specifically, polyether diol) was produced. The production amount of polyether poly(mono)ol was 3000 g.
[0081] Examples 2 to 18 and Comparative Examples 1 to 7 Polyether poly(mono)ol was produced in the same procedure as in Example 1. However, based on Table 1, the alkylene oxide, initiator, reaction conditions, and the amount of PH-DMC were changed.
[0082] In Examples 14 to 16 and Comparative Example 6, 1610 g of PO and 790 g of EO were used as the alkylene oxide.
[0083] 3. Evaluation <Hydroxyl value> The hydroxyl value of the polyether poly(mono)ol (reaction product) of each example and each comparative example was determined by the phthalation method in accordance with Method B of JIS K 1557-1 (2007). Further, the equivalent molecular weight of the polyether poly(mono)ol (reaction product) was calculated from the obtained hydroxyl value. The results are shown in Table 1.
[0084] <Viscosity> The viscosity of the polyether poly(mono)ol (reaction product) of each example and each comparative example was determined by a method using a cone and plate rotational viscometer in accordance with JIS K 1557-5 (2007). The results are shown in Table 1. Also, when the decrease in viscosity with respect to the increase in X was 10% or less, it was determined that the viscosity reached the optimum viscosity. The results are shown in Table 1.
[0085] 4. Discussion The relationship between X and the equivalent molecular weight of the polyether poly(mono)ol in each example and each comparative example is shown in Figure 3.
[0086] At this time, it was found that the range (the shaded portion in FIG. 3) of X, which can sufficiently reduce the viscosity of the polyether poly(mono)ol, and the equivalent molecular weight of the polyether poly(mono)ol is determined by the relational expression in FIG. 3 (X ≧ equivalent molecular weight of the polyether poly(mono)ol / 3000).
[0087] [Table 1]
Claims
1. In the presence of a composite metal cyanide complex catalyst, A method for producing a polyether poly(mono)ol by subjecting an initiator having an active hydrogen group to ring-opening addition polymerization of an alkylene oxide to produce a polyether poly(mono)ol, wherein the equivalent molecular weight of the polyether poly(mono)ol is 5000 g / mol or more, A method for producing a polyether poly(mono)ol that satisfies the following formula (1) to the following formula (3). Reaction ratio = Equivalent molecular weight of polyether poly(mono)ol / Equivalent molecular weight of initiator (1) X = Supply time of alkylene oxide (hours) / Reaction ratio (2) X ≥ Equivalent molecular weight of polyether poly(mono)ol / 3000 (3)
2. The method for producing a polyether poly(mono)ol according to claim 1, wherein the equivalent molecular weight of the polyether poly(mono)ol is 12500 g / mol or less.
Citation Information
Patent Citations
Method of producing polyether polyol
JP2005179567A
Method for producing high molecular weight polyether polyols
JP2014518302A
Soft polyurethane foam, method for producing the same, and seat cushion for automobile
WO2011043345A1
Polyethers and method for producing the same
WO2011043349A1