JP4353603B2 - Catalyst composition for polyurethane production - Google Patents

Description

【００５０】
【表２】

【００５１】
表１〜２に示された結果から、各実施例で得られた触媒組成物は、いずれも、粘性に優れ、また溶液状態も均一透明であることがわかる。
【００５２】
また、比較例で得られた触媒組成物は、粘性に劣るか、或いは溶液状態が不良であることがわかる。
【００５３】
実験例
ポリオール成分（平均水酸基価：３９７ｍｇＫＯＨ／ｇ）〔トリレンジアミン系ポリエーテルポリオール（水酸基価：４５０ｍｇＫＯＨ／ｇ、旭硝子（株）製、商品名：エクセノール４５５ＡＲ）４５重量％、蔗糖系ポリエーテルポリオール（水酸基価：３８０ｍｇＫＯＨ／ｇ、住友バイエルウレタン（株）製、商品名：ポリオール０４７５）４５重量％及びグリセリン系ポリエーテルポリオール（水酸基価：２３５ｍｇＫＯＨ／ｇ、三井化学（株）製、商品名：ポリオールＭＮ−７００）１０重量％〕１００重量部に対して、シリコーン系整泡剤〔日本ユニカー（株）製、商品名：Ｌ−５３４０〕１．５重量部、発泡剤としてシクロペンタン及び水（コア密度がほぼ一定となるように調整した量）、並びに実施例１〜１２で得られた触媒組成物（ゲルタイムが一定となるように調整した量）をラボミキサーで混合してポリオール混合物を得た。
【００５４】
次に、得られたポリオール混合物と、イソシアネート成分〔住友バイエルウレタン（株）製、商品名：スミジュール４４Ｖ２０〕とをポリイソシアヌレート化率を勘案して適したイソシアネートインデックスとなるように２０℃でラボミキサーで混合、攪拌し、得られた混合物を用いてポリウレタン−ポリイソシアヌレート複合フォームを成形し、各種物性を調べた。
【００５５】
得られたポリウレタン−ポリイソシアヌレート複合フォームは、いずれも、良好な特性を有するものであった。
【００５６】
【発明の効果】
本発明のポリウレタン製造用触媒組成物は、室温で取り扱いが容易な程度に流動性があり、また２０℃で均一透明な液状であるので、各種フォームを製造する際の触媒として好適に使用しうるものである。[0001]
BACKGROUND OF THE INVENTION
The present invention relates to a catalyst composition for producing polyurethane. More specifically, polyurethane production that can be used for producing polyurethane foam, polyisocyanurate foam, and composite foams that are suitably used as building materials, electric refrigerators, refrigerators, heat insulating materials for bathtubs, automobile interior materials, etc. The present invention relates to a catalyst composition.
[0002]
[Prior art]
As a catalyst for producing polyurethane foam, organometallic compounds such as tin and lead and tertiary amine compounds are used, and tertiary amine compounds are particularly preferred. In recent years, in order to improve the properties of polyurethane foam, catalysts that promote the trimerization reaction of isocyanate have attracted attention and are used together with tertiary amine compounds.
[0003]
For example, in applications such as a heat insulating material for an electric refrigerator, in addition to a commonly used catalyst made of a tertiary amine compound, in order to improve curability and shorten the demolding time, a triazine-based third It is known to use an amine compound or a quaternary ammonium salt in combination (Japanese Patent Laid-Open Nos. 60-240416 and 63-265910).
[0004]
In addition, when producing a polyisocyanurate foam and a polyurethane-polyisocyanurate composite foam for the purpose of imparting flame retardancy to a heat insulating material for building materials, a carboxylic acid is used as a catalyst for forming a polyisocyanurate structure. Metal salts such as potassium salts, triazine-based tertiary amine compounds, quaternary ammonium salts and the like are used as all or part of the catalyst.
[0005]
However, quaternary ammonium salts have the disadvantages of high viscosity, poor handleability and large loss of adhesion to containers, and are almost in phase with general-purpose tertiary amine compounds that are generally used as catalysts for polyurethane production. Therefore, when preparing and mixing a polyol premix at the polyurethane foaming site, at least two catalyst storage tanks are required according to the composition of the polyol. There are problems such as securing tank space.
[0006]
On the other hand, when preparing and mixing a polyol premix, a plurality of types of catalysts are generally handled to satisfy each required characteristic such as polyurethane foam. It is not preferable, and there is a disadvantage that the possibility of mixing errors, which is an artificial factor, is increased.
[0007]
[Problems to be solved by the invention]
The present invention reduces the number of storage tanks for polyurethane production at the polyurethane foaming site, eliminates the need for new installation, reduces the chances of workers being exposed to the catalyst for polyurethane production by handling multiple catalysts, It is an object of the present invention to provide a uniform and transparent catalyst composition for producing polyurethane, which can be reduced and has a low viscosity and is easy to handle.
[0008]
[Means for Solving the Problems]
The present invention
Tertiary amine compounds, quaternary ammonium salts and formula (I):
HO-R-OH (I)
[Wherein, R represents —CHR ¹ CHR ² — (OCHR ¹ CHR ² ) _n — (R ¹ and R ² each independently represents a hydrogen atom or a methyl group, n represents an integer of 0 to 2) or —XNR ³ Y— (R ³ is a linear or branched alkyl or alkenyl group having 1 to 18 carbon atoms, X and Y are each independently —CH ₂ CH ₂ —, —CH (CH ₃ ) CH ₂ — or -CH ₂ CH (CH ₃ )-)
It is related with the catalyst composition for polyurethane manufacture formed by containing the compound represented by these.
[0009]
DETAILED DESCRIPTION OF THE INVENTION
As the tertiary amine compound, N, N, N ′, N′-tetramethyl-1,6-hexanediamine, N, N, N ′, N′-tetramethyl-1,3-propanediamine, N, N , N ′, N′-tetramethylethylenediamine, N- (2-dimethylaminoethyl) -N′-methylpiperazine, N, N-dimethylcyclohexylamine, N, N, N ′, N ″, N ″ — Pentamethyldiethylenetriamine, bis (2-dimethylaminoethyl) ether, triethylamine, triethylenediamine, N-methylmorpholine, N-ethylmorpholine, N- (dimethylaminoethyl) morpholine, N, N-dimethylbenzylamine, 1,8- Diazabicyclo (5.4.0) undecene-7, N, N ′, N ″ -tris (3-dimethylaminopropyl) hexahydro-s-triazi N, N-dimethylethanolamine, N, N-dimethylaminoethoxyethanol, N, N-dimethylaminoethoxyethoxyethanol, 6-dimethylamino-1-hexanol, 1-methylimidazole, 1,2-dimethylimidazole, -Isobutyl-2-methylimidazole etc. are mentioned, These tertiary amine compounds can be used individually or in mixture of 2 or more types. Among these tertiary amine compounds, N, N, N ′, N′-tetramethyl-1,6-hexanediamine, N, N, N ′, N′-tetramethyl-1,3-propanediamine, N, N, N ′, N′-tetramethylethylenediamine, N- (2-dimethylaminoethyl) -N′-methylpiperazine, N, N-dimethylcyclohexylamine, N, N, N ′, N ″, N One or more selected from the group consisting of '' -pentamethyldiethylenetriamine and bis (2-dimethylaminoethyl) ether can be suitably used from the viewpoints of catalyst activity, foam fluidity and handleability.
[0010]
Representative examples of quaternary ammonium salts include those of formula (II):
^{[R 4 R 5 R 6 R 7} N ] ⁺ · [O (CO) R ^{8] -} (II)
(Wherein R ⁴ and R ⁵ are each a methyl group; R ⁶ and R ⁷ are each independently an alkyl group having 1 to 4 carbon atoms, —CH ₂ CH ₂ OH group or —CH ₂ CH (CH ₃ ) OH; R ⁸ represents a hydrogen atom or a linear or branched alkyl group having 1 to 11 carbon atoms).
[0011]
Specific examples of the quaternary ammonium salt include N- (2-hydroxyethyl) -N- (2-hydroxypropyl) -N, N-dimethylammonium formate, N- (2-hydroxyethyl) -N- ( 2-hydroxypropyl) -N, N-dimethylammonium acetate, N- (2-hydroxyethyl) -N- (2-hydroxypropyl) -N, N-dimethylammonium (2-ethylhexanoate), N- ( 2-hydroxypropyl) -N, N, N-trimethylammonium formate, N- (2-hydroxypropyl) -N, N, N-trimethylammonium acetate, N- (2-hydroxypropyl) -N, N, N -Trimethylammonium (2-ethylhexanoate) etc. are mentioned, These are independent or mixed 2 or more types It is possible to have. Among these quaternary ammonium salts, N- (2-hydroxyethyl) -N- (2-hydroxypropyl) -N, N-dimethylammonium (2-ethylhexanoate), N- (2-hydroxy One or more selected from the group consisting of (propyl) -N, N, N-trimethylammonium (2-ethylhexanoate) is represented by the formula (I) used for compatibilization with the tertiary amine compound. Can be preferably used from the viewpoint of reducing the amount of the compound used.
[0012]
The compound represented by the formula (I) is used as a compatibilizing agent for a tertiary amine compound and a quaternary ammonium salt.
[0013]
Since the compound represented by the formula (I) is a low molecular weight diol having two hydroxyl groups in the molecule, the polyurethane does not extend during the urethanization reaction like monool, and the polyurethane has a low molecular weight. Therefore, the physical properties such as strength do not decrease, and the resulting catalyst composition such as a polyhydric alcohol of triol or higher, or a polymer compound such as polypropylene glycol, has a high viscosity and does not cause inconvenience in handling. It has excellent properties.
[0014]
Specific examples of the compound represented by the formula (I) include ethylene glycol, diethylene glycol, propylene glycol, dipropylene glycol, N-methyldiethanolamine, N-ethyldiethanolamine, N-propyldiethanolamine, N-butyldiethanolamine, N-hexyl. Examples include diethanolamine, N-octyldiethanolamine, N-dodecyldiethanolamine, and the like. These can be used alone or in admixture of two or more.
[0015]
The amount of the tertiary amine compound, the quaternary ammonium salt and the compound represented by the formula (I) in the catalyst composition for producing polyurethane is polyurethane foam, polyisocyanurate foam, and composite foams thereof (hereinafter, various foams). Depending on the properties required), and the composition ratio of uniform transparency varies depending on the type of tertiary amine compound, quaternary ammonium salt and the compound represented by formula (I). Cannot be determined. Here, “uniformly transparent” as used in the present specification means that each component in the catalyst composition is completely compatible at 20 ° C. to form a single solution and is transparent. The period for maintaining uniform transparency is preferably 7 days, more preferably 30 days, and most preferably 90 days.
[0016]
Usually, from the viewpoint of balance control of urethanization reaction and isocyanuration reaction, and improvement of required properties of various foams obtained, the content of each component in the catalyst composition is 25 to 90% by weight of a tertiary amine compound, preferably 35 to 80% by weight, quaternary ammonium salt 5 to 60% by weight, preferably 10 to 50% by weight, and the compound represented by formula (I) 5 to 50% by weight, preferably 5 to 35% by weight. It is desirable.
[0017]
The catalyst composition of the present invention can be easily prepared by mixing a tertiary amine compound, a quaternary ammonium salt and a compound represented by the formula (I). The temperature at the time of mixing is preferably about 20 to 55 ° C. from the viewpoint of reducing the viscosity of each component and preventing phase separation.
[0018]
The catalyst composition of the present invention is advantageous in that there is no phase separation at 60 ° C., excellent high temperature stability, low viscosity at room temperature and easy handling.
[0019]
Therefore, the catalyst composition of the present invention can be suitably used as a catalyst for producing various foams.
[0020]
From the viewpoint of increasing the reactivity of the polyol component and the isocyanate component and the reactivity of the trimerization of the isocyanate with respect to 100 parts by weight of the polyol component that is the raw material of the various foams, 0.5 parts by weight or more, preferably 1 part by weight or more, and from the viewpoint of maintaining the strength of various foams, 10 parts by weight or less, preferably 8 parts by weight or less with respect to 100 parts by weight of the polyol component. Is desirable. Therefore, in consideration of these circumstances, the desirable amount of the catalyst composition for producing polyurethane is 0.5 to 10 parts by weight, preferably 1 to 8 parts by weight with respect to 100 parts by weight of the polyol component.
[0021]
Various foams can be produced by reacting a polyol component and an isocyanate component in the presence of the catalyst composition of the present invention, a foaming agent, and if necessary, a foam stabilizer.
[0022]
The polyol component is not particularly limited as long as it is conventionally used when producing a polyurethane foam. Typical examples of the polyol component include polyester-based polyols and polyether-based polyols having 2 to 8 functional groups and a hydroxyl value of 200 to 700.
[0023]
The polyester polyol can be produced by a condensation reaction of a dicarboxylic acid and a polyhydric alcohol.
[0024]
Examples of dicarboxylic acids used in polyester polyols include saturated aliphatic dicarboxylic acids such as glutaric acid, adipic acid, pimelic acid, suberic acid, azelaic acid, and sebacic acid; saturated aliphatic dicarboxylic acids such as cyclohexanedicarboxylic acid; phthalic acid, Aromatic dicarboxylic acids such as terephthalic acid and isophthalic acid; unsaturated aliphatic dicarboxylic acids such as maleic acid, fumaric acid and itaconic acid; halogen-containing dicarboxylic acids such as tetrabromophthalic acid; these ester-forming derivatives, these acids An anhydride etc. are mentioned, These can be used individually or in mixture of 2 or more types. The dicarboxylic acid may optionally contain a tribasic or higher polybasic acid such as trimellitic acid or pyromellitic acid.
[0025]
Examples of the polyhydric alcohol constituting the polyester polyol include ethylene glycol, diethylene glycol, propylene glycol, 1,4-butanediol, 1,5-pentanediol, methylpentanediol-1,6-hexanediol, trimethylolpropane, and glycerin. , Pentaerythritol, diglycerin, dextrose, sorbitol and the like, and these can be used alone or in admixture of two or more.
[0026]
Typical examples of polyether polyols include polyoxypropylene polyols, polyoxytetramethylene glycol, and mixtures thereof.
[0027]
A polyoxypropylene-based polyol is a compound having two or more active hydrogen-containing groups as a starting material, and is an alkylene oxide such as ethylene oxide, propylene oxide, 1,2-butylene oxide, 1,3-butylene oxide, and styrene oxide. It can be produced by a cycloaddition reaction.
[0028]
Examples of the compound having two or more active hydrogen-containing groups include divalent alcohols such as ethylene glycol, diethylene glycol, propylene glycol, dipropylene glycol, neopentyl glycol, 1,4-butanediol, and 1,6-hexanediol; Trihydric or higher polyhydric alcohols such as glycerin, trimethylolpropane, pentaerythritol, diglycerin, dextrose, sorbitol, sucrose; polyhydric phenols such as resorcinol, hydroquinone, bisphenol A; ethylenediamine, tolylenediamine, 1,3-propane Examples include polyamines such as diamine and isophoronediamine; alkanolamines such as diethanolamine and triethanolamine, and modified products thereof. These may be used alone or in combination of two or more. It can be used.
[0029]
Polyoxytetramethylene glycol can be produced by ring-opening polymerization of tetrahydrofuran.
[0030]
As a polyol component, the said polyester-type polyol and polyether-type polyol can be used individually or in mixture of 2 or more types.
[0031]
As the isocyanate component, 2,4-tolylene diisocyanate, 2,6-tolylene diisocyanate, 4,4'-diphenylmethane diisocyanate, 2,2'-diphenylmethane diisocyanate, 2,4'-diphenylmethane diisocyanate, polymethylene polyphenylene polyisocyanate Aromatic polyisocyanates such as xylylene diisocyanate and naphthylene diisocyanate; aliphatic polyisocyanates such as hexamethylene diisocyanate and lysine diisocyanate; alicyclic polyisocyanates such as hydrogenated diphenylmethane diisocyanate, hydrogenated tolylene diisocyanate and isophorone diisocyanate; urethane Bond, carbodiimide bond, uretoimine bond, allophanate bond, urea bond, burette bond, The polyisocyanate modified product, and the like containing cyanurate binding one or more, and these may be used alone or in admixture of two or more.
[0032]
The ratio of the polyol component and the isocyanate component is usually preferably adjusted so that the isocyanate index is 95 to 300.
[0033]
Examples of the blowing agent include water, low-boiling hydrocarbons such as isopentane, normal pentane, and cyclopentane, gases such as nitrogen gas, air, and carbon dioxide, HCFC-141b, HCFC-142b, HCFC-22, HFC-134a, HFC-152a, HFC-245fa, HFC-245ca, HFC-236ea, HFC-365mfc and the like can be mentioned, and these can be used alone or in admixture of two or more.
[0034]
Since the amount of the foaming agent used varies depending on the type and density of various target foams, it cannot be determined unconditionally. Therefore, it is desirable that the amount used is appropriately adjusted according to the type of the foaming agent.
[0035]
Although a foam stabilizer can be used as needed, what is necessary is just what is generally used when manufacturing a polyurethane foam. Representative examples of foam stabilizers include silicone surfactants such as dimethylpolysiloxane and polyoxyalkylene-modified dimethylpolysiloxane, anionic surfactants such as fatty acid salts, sulfate ester salts, phosphate ester salts, and sulfonates. Is mentioned.
[0036]
The amount of the foam stabilizer used varies depending on the type and the density of the various foams intended, and cannot be determined unconditionally. Therefore, it is desirable to appropriately adjust the foam stabilizer in accordance with the type of the foam stabilizer.
[0037]
Furthermore, other components other than those described above, for example, other auxiliaries such as a crosslinking agent, a flame retardant, and a filler can be used as long as the object of the present invention is not impaired.
[0038]
Examples of the crosslinking agent include a low molecular weight compound having two or more active hydrogen-containing groups capable of reacting with a hydroxyl group, a first amino group, a second amino group, and other isocyanate groups. Examples include ethylene glycol, diethylene glycol, propylene glycol, dipropylene glycol, 1,4-butanediol, 1,6-hexanediol, neopentyl glycol, glycerin, trimethylolpropane, triethanolamine, alkylene oxide of bisphenol A. Examples include polyhydric alcohols such as adducts, polyamines such as diethyltoluenediamine, chlorodiaminobenzene, ethylenediamine, and 1,6-hexanediamine. These can be used alone or in admixture of two or more.
[0039]
Examples of the flame retardant include tricresyl phosphate, tris (2-chloroethyl) phosphate, tris (2-chloropropyl) phosphate, tris (1,3-dichloropropyl) phosphate, tris (2,3-dibromopropyl) phosphate, etc. Halogen-based flame retardant is mentioned.
[0040]
Examples of the filler include inorganic compounds such as silica-based fine particles and alumina-based fine particles, and organic compounds such as melamine-based resins and phenol-based resins.
[0041]
When producing a polyurethane foam, for example, a polyol component, a foaming agent, a catalyst composition, a foam stabilizer and other auxiliary agents are mixed, and the resulting polyol mixture and an isocyanate component are mixed by a molding machine or the like. It can be molded by stirring, pouring into a mold and foaming. More specifically, for example, after the temperature of the polyol mixture is adjusted to about 20 ° C. using a tank or the like, the isocyanate component is mixed with an isocyanate component using a foaming machine such as an automatic mixing injection type foaming machine or an automatic mixing injection type foaming machine. By reacting, a polyurethane foam can be produced.
[0042]
As described above, the catalyst composition of the present invention has a low viscosity and is easy to handle despite being premixed with a quaternary ammonium salt that promotes the trimerization reaction of isocyanate. Moreover, it is uniformly transparent at 20 ° C. Furthermore, since it is not necessary to mix and use with other catalysts, a plurality of catalyst storage tanks and the like are not required for preparing and mixing the polyol premix, reducing the chances of exposure to the polyurethane production catalyst, and the working environment. Can be improved, and problems such as blending errors can be reduced.
[0043]
Therefore, the various foams produced using the catalyst composition of the present invention can be suitably used for heat insulating materials such as electric refrigerators and freezer warehouses, heat insulating materials such as panels and boards for building materials, and the like.
[0044]
【Example】
Examples 1-12 and Comparative Examples 1-4 (However, Example 12 is a reference example)
In a transparent glass bottle, the amount of the tertiary amine compound, quaternary ammonium salt, and the compound represented by formula (I) shown in Tables 1 and 2 are weighed and heated to 60 ° C., and then thoroughly mixed and stirred. A catalyst composition was obtained.
[0045]
As physical properties of the catalyst composition, the viscosity and the solution state were examined based on the following methods. The results are shown in Tables 1-2.
[0046]
A. The flow of the catalyst composition when the glass bottle containing the viscous catalyst composition is tilted at room temperature (about 20 ° C.) is visually observed and evaluated based on the following evaluation criteria.
〔Evaluation criteria〕
○: When the catalyst composition can be easily taken out of the glass bottle by tilting the glass bottle ×: Even when the glass bottle is tilted, it takes time to take out the catalyst composition from the glass bottle, and there are many catalyst compositions on the wall surface. When adhering [0047]
B. The appearance of the solution state catalyst composition is visually observed at 20 ° C. and evaluated based on the following evaluation criteria.
〔Evaluation criteria〕
○: When the catalyst composition is uniformly transparent ×: When the catalyst composition is phase-separated or clouded
In Tables 1 and 2, each abbreviation means the following.
PPG700: Polypropylene glycol with an average molecular weight of 700 PEG400: Polyethylene glycol with an average molecular weight of 400
[Table 1]

[0050]
[Table 2]

[0051]
From the results shown in Tables 1 and 2, it can be seen that all of the catalyst compositions obtained in each Example are excellent in viscosity and the solution state is uniformly transparent.
[0052]
Moreover, it turns out that the catalyst composition obtained in the comparative example is inferior in viscosity or in a poor solution state.
[0053]
Experimental example Polyol component (average hydroxyl value: 397 mg KOH / g) [tolylenediamine-based polyether polyol (hydroxyl value: 450 mg KOH / g, manufactured by Asahi Glass Co., Ltd., trade name: Exenol 455AR) 45% by weight, sucrose-based polyether polyol (Hydroxyl value: 380 mg KOH / g, manufactured by Sumitomo Bayer Urethane Co., Ltd., trade name: polyol 0475) 45% by weight and glycerin polyether polyol (Hydroxyl value: 235 mg KOH / g, manufactured by Mitsui Chemicals, Inc., trade name: polyol MN-700) 10 wt%] 100 parts by weight of silicone foam stabilizer [manufactured by Nippon Unicar Co., Ltd., trade name: L-5340] 1.5 parts by weight, cyclopentane and water (core) as blowing agents The amount adjusted so that the density is substantially constant), and obtained in Examples 1-12 Medium composition was obtained by mixing with the polyol mixture (gel time controlled amount to be constant) laboratory mixer.
[0054]
Next, the obtained polyol mixture and the isocyanate component [manufactured by Sumitomo Bayer Urethane Co., Ltd., trade name: Sumidur 44V20] at 20 ° C. so as to have a suitable isocyanate index in consideration of the polyisocyanurate conversion rate. Mixing and stirring with a laboratory mixer, a polyurethane-polyisocyanurate composite foam was molded using the resulting mixture, and various physical properties were examined.
[0055]
All of the obtained polyurethane-polyisocyanurate composite foams had good characteristics.
[0056]
【The invention's effect】
The catalyst composition for polyurethane production according to the present invention is fluid to such an extent that it can be easily handled at room temperature, and is a uniform transparent liquid at 20 ° C., so that it can be suitably used as a catalyst for producing various foams. Is.

Claims (3)

25 to 80% by weight of tertiary amine compound, 5 to 60% by weight of quaternary ammonium salt and formula (I):
HO-R-OH (I)
[Wherein, R represents —CHR ¹ CHR ² — (OCHR ¹ CHR ² ) _n — (R ¹ and R ² each independently represents a hydrogen atom or a methyl group, n represents an integer of 0 to 2) or —XNR ³ Y— (R ³ is a linear or branched alkyl or alkenyl group having 1 to 18 carbon atoms, X and Y are each independently —CH ₂ CH ₂ —, —CH (CH ₃ ) CH ₂ — or -CH ₂ CH (CH ₃ )-)
A catalyst composition for polyurethane production comprising 5 to 50% by weight of a compound represented by the formula: wherein the quaternary ammonium salt is N- (2-hydroxyethyl) -N- (2-hydroxypropyl). A catalyst composition for producing polyurethane, which is N, N-dimethylammonium (2-ethylhexanoate) .   The tertiary amine compound is N, N, N ′, N′-tetramethyl-1,6-hexanediamine, N, N, N ′, N′-tetramethyl-1,3-propanediamine, N, N, N ′, N′-tetramethylethylenediamine, N- (2-dimethylaminoethyl) -N′-methylpiperazine, N, N-dimethylcyclohexylamine, N, N, N ′, N ″, N ″ -penta The catalyst composition according to claim 1, wherein the catalyst composition is at least one selected from the group consisting of methyldiethylenetriamine and bis (2-dimethylaminoethyl) ether. The compound represented by the formula (I) is ethylene glycol, diethylene glycol, propylene glycol, dipropylene glycol, N-methyldiethanolamine, N-ethyldiethanolamine, N-propyldiethanolamine, N-butyldiethanolamine, N-hexyldiethanolamine, N- The catalyst composition according to claim 1 or 2 , wherein the catalyst composition is one or more selected from the group consisting of octyl diethanolamine and N-dodecyl diethanolamine.