KR102424919B1 - Tertiary amine polyols, tertiary amine catalyst comprising same and manufacture method thereof - Google Patents

Abstract

The present invention relates to a tertiary amine-based polyol, a tertiary amine catalyst comprising the same, and a method for preparing the same, and more particularly, when a polyurethane is prepared using the tertiary amine-based polyol of the present invention, the tertiary amine Since the polyol-based polyol contains three or more hydroxyl groups, it acts as a reactant and at the same time serves as a catalyst, so that polyurethane can be prepared without a separate tertiary amine catalyst.

Description

Tertiary amine-based polyol, tertiary amine catalyst comprising same, and method for preparing the same

The present invention relates to a tertiary amine-based polyol, a tertiary amine catalyst comprising the same, and a method for preparing the same, and more particularly, when a polyurethane is prepared using the tertiary amine-based polyol of the present invention, the tertiary amine Since the polyol-based polyol contains three or more hydroxyl groups, it acts as a reactant and at the same time serves as a catalyst, so that polyurethane can be prepared without a separate tertiary amine catalyst.

Polyurethane (PU) has excellent mechanical properties, thermal insulation, shock absorption, sound absorption properties and excellent processability, and for this reason, polyurethane is used in an amount of 15 to 20% of the total amount of plastic used. In addition, the field of application is widely used in automobile interior and exterior parts such as chair cushions, instrument panels, soundproofing materials, awnings, doors, and ceiling cushions. Furthermore, as the international economy recovers, recovery/growth of the household furniture industry, which has been stagnant along with real estate, is expected, and the use and usage of PU materials is expected to increase.

On the other hand, the general method of synthesizing polyurethane is shown in Scheme 1 below.

[Scheme 1]

As shown in Scheme 1, an isocyanate group (-N=C=O) is easily combined with a hydroxyl group (-OH) to form a urethane bond. In more detail, when a compound having two hydroxyl groups is reacted with a diisocyanate compound, a linear polymer is obtained, and the linear polymer is polyurethane. Generally, toluene diisocyanate is used as diisocyanate, and polyether and polyester are used as a compound (polyol) which has two hydroxyl groups. When polyether is used, a softer polyurethane can be produced, and when polyester is used, a harder plastic can be produced. In addition, when a compound having three or more hydroxyl groups is used as the polyol, the prepared polyurethane has a three-dimensionally combined form.

In polyurethane synthesis, the reaction of polyol and polyisocyanate is carried out in the presence of a catalyst, a foaming agent, a surfactant, a flame retardant, a crosslinking agent, and the like, if necessary. In the manufacture of polyurethane, various metal-based compounds or tertiary amine compounds are used as catalysts alone or in combination (Korean Patent Publication No. 2001-0041368, Korean Patent Publication No. 2008-0112352, Korean Patent No. 10-1126960) and Korean Patent Registration No. 10-0729826).

Among the catalysts, a tertiary amine catalyst is widely used, and as the tertiary amine catalyst, for example, triethylene-diamine (TEDA), N,N,N',N'-tetramethyl- 1,6-Hexanediamine, bis(2-dimethylaminoethyl)ether, N,N,N',N",N"-pentamethyldiethylenetriamine, N-methylmorpholine, N-ethylmorpholine , N,N-dimethylethanolamine, and the like. Although organometallic compounds such as organotin compounds are frequently used as the metal-based compound, the productivity, moldability, and physical properties of the polyurethane deteriorate, and at the same time, heavy metals contained in the metal-based compound remain, causing toxicity. It is often used in combination with a catalyst and is rarely used alone.

However, the tertiary amine catalyst is slowly released as a volatile amine from the product after polyurethane or polyurethane foam production. Due to this, there is a problem of causing headache, nausea, vomiting, temporary blurring of vision, halo phenomenon, etc. caused by the odor of volatile amines, or causing discoloration of other materials (e.g., epidermal vinyl chloride).

Accordingly, as a method of solving the above problem of volatile tertiary amine catalysts, an amine catalyst having a hydroxyl group or primary and secondary amino groups capable of reacting with polyisocyanate in a molecule (generally referred to as a reactive catalyst) is used. It has been proposed to use or to use a bifunctional crosslinking agent having a tertiary amino group in the molecule.

The use of the reactive catalyst as described above is effective in reducing the odor of the final resin product because the reactive catalyst is immobilized in the polyurethane resin skeleton in a form reacted with polyisocyanate. However, these reactive catalysts have a problem in that the activity to the resination reaction (reaction of a polyol and an isocyanate) is low, and the curability of the polyurethane resin obtained is lowered.

In addition, the method of using the bifunctional crosslinking agent is an effective method for reducing the odor of the final polyurethane product and improving the working environment at the time of manufacturing the polyurethane resin. However, there is a problem in that physical properties such as hardness of the polyurethane produced through this is insufficient.

Accordingly, the present inventors have developed a novel tertiary amine compound capable of reducing the generation of volatile organic compounds, and applied it as a catalyst for polyurethane production.

Republic of Korea Patent Publication No. 2001-0041368 Republic of Korea Patent Publication No. 2008-0112352 Republic of Korea Patent No. 10-1126960 Republic of Korea Patent Registration No. 10-0729826

Accordingly, an object of the present invention is to provide a tertiary amine-based polyol with less generation of volatile organic compounds (VOC), a tertiary amine catalyst comprising the same, and a method for preparing the same, which can solve the problems of the conventional amine catalyst for preparing polyurethane will do

In order to achieve the above object, the present invention provides a tertiary amine-based polyol represented by the following formula (1):

In Formula 1,

또는

이고,L ₁ to L ₃ are each independently

or

ego,

L ₄ is C _1-6 alkylene,

R ₁ to R ₆ are each independently hydrogen or C _{1-6 alkyl} ,

n is each independently an integer from 1 to 6.

In addition, the present invention provides a tertiary amine catalyst for preparing a polyurethane comprising a tertiary amine-based polyol as described above.

Furthermore, the present invention provides a method for preparing a compound of Formula 10 by reacting a compound of Formula 8 with a compound of Formula 9 below; And (2) provides a method for preparing a tertiary amine-based polyol of the following formula (1), comprising the step of reacting a compound of formula (10) with a compound of formula (11):

[Formula 9]

R ₇ -NH-R ₈

[Formula 1]

In the above formula,

또는

이고, L ₁ to L ₃ are each independently

or

ego,

L ₄ is C _{1-6 alkylene} ,

R ₁ to R ₈ are each independently hydrogen or C _{1-6 alkyl} ,

n is each independently an integer from 1 to 6.

In addition, the present invention provides a polyol composition comprising a tertiary amine-based polyol as described above; And it provides a method for producing a polyurethane, comprising the step of reacting a polyisocyanate having two or more isocyanate groups.

In addition, the present invention provides a polyol composition comprising a tertiary amine-based polyol as described above; and a polyurethane formed through the reaction of a polyisocyanate having two or more isocyanate groups.

The tertiary amine-based polyol of the present invention is an autocatalytic polyol, and has a tertiary amine group and a polyol structure, so that it can act as a reactant and a catalyst during polyurethane production, so that polyurethane can be prepared without a separate amine catalyst. can In addition, the polyurethane prepared as described above generates less volatile organic compounds than conventional polyurethanes, and thus can minimize odor, visual flow, and discoloration of other materials.

1 is a ¹ H-NMR spectrum result graph of the tertiary amine-based polyol of Example 1.
2 is a graph showing the results of ESI-MS spectrum analysis of the tertiary amine-based polyol of Example 1.

Hereinafter, the present invention will be described in detail.

The present invention provides a tertiary amine-based polyol represented by the following formula (1):

[Formula 1]

In Formula 1, L ₁ to L ₄ , R ₁ to R ₆ and n are as defined above.

Specifically, in Formula ₁ , L ₄ is C _1-4 alkylene, and R ₁ and R ₂ , R ₃ and R ₄ , and R ₅ and R ₆ are C _{1-4 alkyl} and each other may be the same, and n may be each independently 1 or 2.

The tertiary amine-based polyol may have a weight average molecular weight of 800 to 8,000, specifically 890 to 5,000. Further, the tertiary amine-based polyol may have a hydroxyl number of 25 to 250 mg KOH/g, and an amine value of 25 to 280 mg KOH/g.

More specifically, in Formula 1, R ₁ to R ₆ may be the same as C _{1-4 alkyl} .

The tertiary amine-based polyol of the present invention is an autocatalytic polyol, and has a tertiary amine group and a polyol structure, so that it can act as a reactant during polyurethane production and also serve as a catalyst.

More specifically, the tertiary amine-based polyol may be any one of compounds of Formulas 2 to 7 below.

In addition, the present invention provides a tertiary amine catalyst for preparing a polyurethane comprising a tertiary amine-based polyol as described above.

Amine catalysts are classified into gel reaction catalysts, surface cure catalysts, blowing catalysts, or isocyanate reactive catalysts according to their structures. In the case of an autocatalyst, it has a functional group serving as an initiator for propylene oxide and ethylene oxide, and has a structure in which an amine catalyst is bonded to a polyol. Due to the structural features as described above, the autocatalyst can reduce the generation of volatile organic compounds during polyurethane production. In particular, the tertiary amine catalyst for preparing a polyurethane including the tertiary amine-based polyol of the present invention has excellent performance as an initiator and a catalyst due to the high content of N and OH when the molecular weight is similar compared to the conventional autocatalyst.

In addition, the present invention comprises the steps of (1) reacting a compound of the following formula (8) with a compound of the following formula (9) to prepare a compound of the following formula (10); And (2) provides a method for preparing a tertiary amine-based polyol of the following formula (1), comprising the step of reacting a compound of formula (10) with a compound of formula (11):

[Formula 8]

[Formula 9]

R ₇ -NH-R ₈

[Formula 10]

[Formula 11]

[Formula 1]

In the above formula, L ₁ to L ₄ , R ₁ to R ₈ and n are as defined above.

Hereinafter, the manufacturing method of the present invention will be described in detail for each step.

First, in step (1), as shown in Scheme 2 below, a compound of Formula 8 is reacted with a compound of Formula 9 to obtain a compound of Formula 10.

[Scheme 2]

In the above formula, n, R ₇ and R ₈ are as defined above.

In the above reaction, a preferred example of the compound of Formula 8 may include epichlorohydrin, and a preferred example of the compound of Formula 9 may include diethyl amine, and a preferred example of the compound of Formula 10 An example is glycidyl diethyl amine.

In the above reaction, the compound of Formula 9 may be used in an amount of 0.5 to 2.0 molar equivalents, or 0.8 to 1.5 molar equivalents based on 1 molar equivalent of the compound of Formula 8. At this time, the reaction may be carried out without a reaction solvent.

In addition, the reaction conditions may be carried out by stirring at 0 to 20 °C, or 0 to 5 °C, for 3 to 72 hours, or 12 to 48 hours.

Next, in step (2), as shown in Scheme 3 below, a compound of Formula 10 is reacted with a compound of Formula 11 to obtain a compound of Formula 1.

[Scheme 3]

In the above formula, n, L ₁ to L ₄ and R ₁ to R ₈ are as defined above.

In the above reaction, a preferred example of the compound of Formula 10 is glycidyl diethyl amine, and a preferred example of the compound of Formula 11 is 2-(piperazin-1-yl)ethane-1- amines (2-(piperazine-1-yl)ethane-1-amine).

In the above reaction, the compound of Formula 10 may be used in an amount of 2.0 to 4.0 molar equivalents, or 2.5 to 3.5 molar equivalents based on 1 molar equivalent of the compound of Formula 11. In this case, the reaction may be performed without using a solvent, and if necessary, methanol, ethanol, dimethylformamide (DMF), or a mixture thereof may be used.

In addition, the reaction conditions may be carried out by stirring at 30 to 120 °C, or 60 to 90 °C, for 3 to 72 hours, or 12 to 48 hours.

Furthermore, the present invention provides a polyol composition comprising a tertiary amine-based polyol as described above; And it provides a method for producing a polyurethane comprising the step of reacting a polyisocyanate having two or more isocyanate groups.

The tertiary amine-based polyol may serve as a catalyst when generating a urethane bond between the hydroxyl group of the polyol composition and the isocyanate group of the polyisocyanate, and therefore, the preparation method is a tertiary amine catalyst in addition to the tertiary amine-based polyol may not be used, but a catalyst typically used in the production of polyurethane, for example, a primary, secondary, tertiary, quaternary amine or organometallic catalyst, etc. may be further added.

The organometallic catalyst is, for example, stanas diacetate, stanas dioctoate, stanas dioleate, stanas dilaurate, dibutyl tin oxide, dibutyl tin diacetate, dibutyl tin dilaurate , dibutyl tin dichloride, dioctyl tin dilaurate, lead octanoate, lead naphthenate, nickel naphthenate, cobalt naphthenate, and the like.

The polyol composition may further include a polyol including at least one hydroxyl group in addition to the tertiary amine-based polyol of the present invention. The polyol including at least one hydroxyl group may be specifically, a polyether polyol, a polyester polyol, or the like.

The polyisocyanate produces a urethane bond by causing a gel reaction with the hydroxyl group (-OH) of the polyol, thereby forming polyurethane.

The polyisocyanate may be, specifically, an aliphatic, cycloaliphatic, arylaliphatic or aromatic polyisocyanate, and more specifically, an aromatic polyisocyanate.

The aromatic polyisocyanate is, for example, a 4,4'-, 2,4' or 2,2'-isomer of diphenylmethane diisocyanate (MDI); his blend; its polymer; mixtures of monomeric MDI with toluene-2,4- or 2,6-diisocyanate (TDI); m- or p-phenylenediisocyanate; chlorophenylene-2,4-diisocyanate; diphenylene-4,4'-diisocyanate;4,4'-diisocyanate-3,3'-dimethyldiphenyl;3-methyldiphenyl-methane-4,4'-diisocyanate; diphenyl ether diisocyanate; 2,4,6-triisocyanatotoluene; and 2,4,4'-triisocyanatodiphenyl ether.

The polyurethane manufacturing method may include the step of adding an additive according to the intended use of the prepared polyurethane. The additive may include a foaming agent, water, a crosslinking agent, a cell stabilizer, a flame retardant, a chain extender, an epoxy resin, a filler, a pigment, and the like.

The blowing agent, specifically, may be selected from the group consisting of water, methylene chloride, acetone, chlorofluorocarbons, hydrofluorocarbons, hydrochlorofluorocarbons, hydrocarbons, and combinations thereof. The hydrofluorocarbon (HFC) includes, for example, HFC-245fa, HFC-134a, and HFC-365. The hydrochlorofluorocarbons (HCFCs) include, for example, HCFC-141b, HCFC-22, HCFC-123, and the like. The hydrocarbon includes, for example, n-pentane, iso-pentane, cyclopentane, or a combination thereof.

The amount of the foaming agent added may vary depending on the purpose, use, foam rigidity and density of the foam of the polyurethane product to be prepared. Specifically, it may be added in an amount of 1 to 13.5, or 3 to 4.5 parts by weight based on 100 parts by weight of the polyol composition.

The amount of water that is not used as a foaming agent may be added in an amount of 0 to 20 parts by weight based on 100 parts by weight of the polyol composition.

The crosslinking agent may be, for example, diethanolamine, diisopropanolamine, triethanolamine, tripropanolamine, etc., and the amount of the crosslinking agent added may be 0.1 to 5.4, or 0.3 to 1.8 parts by weight based on 100 parts by weight of the polyol composition. .

The cell stabilizer may be, for example, a surfactant such as an organopolysiloxane. The amount of the cell stabilizer added may be 0.1 to 3.6 parts by weight, or 0.3 to 1.2 parts by weight based on 100 parts by weight of the polyol composition.

The flame retardant includes, for example, a halogenated compound and a non-halogenated compound. The halogenated compound is, for example, trichloropropylphosphate (TCPP). The non-halogenated compound is, for example, triethylphosphate ester (TEP) and

Dimethylphenylpiperazinium (DMMP; Dimethylphenylpiperazinium). The amount of the flame retardant added may be 0 to 50 parts by weight, 0 to 40 parts by weight, 0 to 30 parts by weight, or 0 to 20 parts by weight based on 100 parts by weight of the polyol composition.

The chain extender includes, for example, a chain extender of diols such as ethylene glycol and butane diol.

In one embodiment, in the method for producing the polyurethane of the present invention, the polyol composition and the polyisocyanate are dissolved in a solvent, stirred, and then injected into an appropriate container or mold to be foam-molded. A conventional stirrer may be used for the stirring, and a polyurethane foaming machine may be used for foam molding. The polyurethane foaming machine may be, for example, a high pressure, low pressure or spray type device.

In addition, the present invention provides a polyurethane prepared by the manufacturing method as described above. The polyurethane obtained by the production method of the present invention can be molded into, for example, an elastomer without using a foaming agent, a polyurethane foam using a foaming agent, or the like.

Furthermore, the polyurethane prepared by the manufacturing method of the present invention may be in the form of a foam. Examples of the polyurethane foam include a flexible polyurethane foam, a semi-rigid polyurethane foam, and a rigid polyurethane foam. Specifically, it may be a car seat of a flexible polyurethane foam that can be used as an automobile interior material, a dashboard or handle of a semi-rigid polyurethane foam, and an insulating material using a rigid polyurethane foam.

The flexible polyurethane foam has an open cell structure, exhibits high air permeability, and is capable of reversible deformation. As the physical properties of the flexible polyurethane foam, for example, a density of 10 to 100 kg/m2, a compressive strength (ILD25%) of 200 to 8000 kPa, and an elongation of 80 to 500% may be in the range.

In addition, the semi-rigid polyurethane foam has higher foam density and compressive strength than the flexible polyurethane foam, but has an open cell structure like the flexible polyurethane foam, and exhibits high air permeability to allow reversible deformation. Physical properties of the semi-rigid urethane foam may be, for example, a density of 40 to 800 kg/m 3 , a compressive strength (ILD25%) of 10 to 200 kPa, and a growth rate of 40 to 200%.

In addition, the rigid polyurethane foam is highly crosslinked and has a closed cell structure and is not capable of reversible deformation. The physical properties of the rigid urethane foam may be, for example, a density of 10 to 100 kg/m 3 and a compressive strength of 50 to 1000 kPa.

Hereinafter, the present invention will be described in more detail by way of Examples and Experimental Examples. However, the following examples and experimental examples are only for illustrating the present invention, and the scope of the present invention is not limited thereto.

[ Example ]

Example One: new polyol synthesis

1-1. glycidyl Synthesis of diethylamine

After mixing 39 g (0.42 mol, 32.96 ml) of epichlorohydrin and 29 g (0.4 mol, 41.018 ml) of diethyl amine, 50 wt. % NaOH aqueous solution was added 28 g (1.75 mol) to obtain a mixture. The mixture was stirred at 10 °C for 24 hours and then filtered to obtain a filtrate. Then, ethyl acetate was added to the filtrate, and the upper liquid layer was separated using a separatory funnel. The upper liquid was dried over Na ₂ SO ₄ , filtered and vacuum distilled to obtain glycidyl diethyl amine.

1-2. New catalyst synthesis

Glycidyl diethylamine (0.1548 mol, 20 g) obtained in 1-1 above was mixed with 2-(piperazin-1-yl)ethan-1-amine (2-(piperazine-1-yl)ethane-1- amine; 0.0503 mol, 6.5 g) was added dropwise at 80 °C and stirred for 24 hours to obtain a tertiary amine-based polyol.

Experimental example One.

The weight average molecular weight and molecular formula of the amine-based polyol of Example 1 were determined using LC/MS spectroscopy (manufacturer: Thermo finnigan LCQ decaplus), and nuclear magnetic resonance spectrum (NMR) (400 MHz FT-NMR Spectrometer (Varian, 400-) MR)) was used to obtain a ¹ H NMR spectrum of the amine-based polyol of Example 1. Specifically, the ¹ H NMR spectrum graph is In FIG. 1 , a graph of ESI-MS results is shown in FIG. 2 .

1) Weight average molecular weight: 895 g/mol

2) ¹ H NMR data (see Fig. 1)

3) ESI-MS data at m/z 517.48 [M+H] ⁺ (calcd. for C ₂₇ H ₆₀ N ₆ O ₃ : 516.47) (see FIG. 2)

For this reason, it was confirmed that the tertiary amine-based catalyst (tertiary amine-based polyol) prepared in Example 1 was a compound represented by the following Chemical Formulas 2 to 7.

[Formula 2]

[Formula 3]

[Formula 4]

[Formula 5]

[Formula 6]

[Formula 7]

Experimental example 2: Measurement of physicochemical properties

2-1. hydroxyl number (hydroxyl number)

The hydroxyl value of the tertiary amine-based polyol of Example 1 was measured.

Specifically, according to the acetic anhydride-pyridine method (JISK 8004-1961), 5 ml of the tertiary amine-based polyol of Example 1 and the acetic anhydride-pyridine mixture (8:2 volume ratio) was put into a 200 ml Erlenmeyer flask and heated to 30 ° C. Shaking for 30 minutes was performed once, and after shaking three times, a cooler was attached and reacted for 90 minutes in an oil bath. After that, 1 ml of distilled water was added, and after shaking 5 times as described above, it was left in an oil bath for 10 minutes. After that, it was taken out of the oil bath and left at room temperature for 10 minutes, then the inner wall of the cooler was washed with 10 ml of acetone and then shaken 5 times as described above. Then, 4 drops of phenolphthalein indicator were added and titrated with 0.5 N KOH standard solution. The hydroxyl value was calculated through Equation 1 below.

[Equation 1]

Hydroxyl number = [(B - A) × F × 28.05 / S] + acid number

In Equation 1, B is the 0.5N KOH content (ml) required for the blank,

A is the 0.5N KOH amount (ml) required in the above experiment,

F is the acid value of the sample used in the above experiment,

S is the amount (ml) of the tertiary amine-based polyol of Example 1 used in the above experiment.

As a result of calculation, the hydroxyl value of the tertiary amine-based polyol of Example 1 was found to be 198 mg KOH/g.

2-2. Determination of amine value

The amine value of the tertiary amine-based polyol of Example 1 was measured.

Specifically, after dissolving the tertiary amine-based polyol of Example 1 in methanol, bromocresol red was used as an indicator and titrated with a hydrochloric acid standard solution, and the amine value was measured in Eg/g unit in which the molecular weight of the polyol is expressed as 1 g equivalent. .

As a result of the measurement, the amine value of the tertiary amine-based polyol of Example 1 was 213 mg KOH/g.

Claims (14)

A tertiary amine-based polyol represented by the following formula (1):
[Formula 1]

In Formula 1,
L ₁ to L ₃ are each independently

or

ego,
L ₄ is C _{1-6 alkylene} ,
R ₁ to R ₆ are each independently hydrogen or C _{1-6 alkyl} ,
n is each independently an integer from 1 to 6.
According to claim 1,
The L ₄ is C _{1-4 alkylene} ,
The R ₁ and R ₂ , R ₃ and R ₄ , and R ₅ and R ₆ are the same as each other as C _{1-4 alkyl} ,
Wherein n is each independently 1 or 2, a tertiary amine-based polyol.
3. The method of claim 2,
said R ₁ to R ₆ are all the same as C _1-4 alkyl, tertiary amine _- based polyols.
According to claim 1,
The tertiary amine-based polyol is any one of the compounds of Formulas 2 to 7, tertiary amine-based polyol:
[Formula 2]

[Formula 3]

[Formula 4]

[Formula 5]

[Formula 6]

[Formula 7]

According to claim 1,
The tertiary amine-based polyol is a tertiary amine-based polyol having a weight average molecular weight of 800 to 8,000.
According to claim 1,
The tertiary amine-based polyol has a hydroxyl number of 25 to 250 mg KOH/g, a tertiary amine-based polyol.
According to claim 1,
The tertiary amine-based polyol has an amine value of 25 to 280 mg KOH/g, a tertiary amine-based polyol.
A tertiary amine catalyst for polyurethane production, comprising the tertiary amine-based polyol according to any one of claims 1 to 7.
(1) reacting a compound of Formula 8 with a compound of Formula 9 to prepare a compound of Formula 10; and
(2) A method for preparing a tertiary amine-based polyol of the following formula (1), comprising reacting a compound of formula (10) with a compound of formula (11):
[Formula 8]

[Formula 9]
R ₇ -NH-R ₈
[Formula 10]

[Formula 11]

[Formula 1]

In the above formula,
L ₁ to L ₃ are each independently

or

ego,
L ₄ is C _{1-6 alkylene} ,
R ₁ to R ₈ are each independently hydrogen or C _{1-6 alkyl} ,
n is each independently an integer from 1 to 6.
A polyol composition comprising a tertiary amine-based polyol according to any one of claims 1 to 7; and
reacting a polyisocyanate having two or more isocyanate groups;
Method for producing polyurethane.
11. The method of claim 10,
The tertiary amine-based polyol serves as a catalyst when generating a urethane bond between the hydroxyl group of the polyol composition and the isocyanate group of the polyisocyanate.
11. The method of claim 10,
The production method is a method for producing a polyurethane that does not use a tertiary amine catalyst other than the tertiary amine-based polyol,
A polyol composition comprising a tertiary amine-based polyol according to any one of claims 1 to 7; and a polyurethane formed through the reaction of a polyisocyanate having two or more isocyanate groups.
14. The method of claim 13,
The polyurethane is in the form of a foam, polyurethane.

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