JPS61252219A - Catalyst for producing polyurethane - Google Patents

Abstract

PURPOSE:A catalyst for producing polyurethane which is odorless and has a moderate activity and excellent skin formability, comprising a dimethylethanolamine/ethylene oxide adduct. CONSTITUTION:The compound of the formula (wherein n is 3-4) is used as a catalyst for producing polyurethane. The amount of the catalyst used is preferably in the range of about 0.01-4pts.wt. per 100pts.wt. polyol used in the production of polyurethane. This catalyst may be used in combination with triethylenediamine or an organotin compound which is usually used in the production of polyurethane. The compound of the formula can be easily produced by an addition reaction between 1mol of dimethylethanolamine and 2-3mol of ethylene oxide.

Description

DETAILED DESCRIPTION OF THE INVENTION [Industrial Field of Application] The present invention relates to a catalyst used in the production of polyurethanes such as soft, hard, or nidistomer polyurethanes.

More specifically, it has a hydroxyl group. The present invention relates to a novel catalyst for producing polyurethane that is odorless and has excellent skin-forming ability.

[Conventional technology]

Conventionally, metal-based catalysts such as tin-based, iron-based, manganese-based, etc., and amine-based catalysts have been used as catalysts for polyurethane production, but tertiary amines are preferably used as catalysts for polyurethane production. Iriko is already widely known.

Examples, t, N-methylmorpholine, N-ethylmorpholine, N, N, N', N'-tetramethyl-1,5-
Butanediamine, lI4-diazabicyclo(2,2,2
) Octane (1''), N,M-dimethylcyclohexylamine, N,N-dimethylethanolamine, and other compounds are used as catalysts for polyurethane production.

Furthermore, dimethylbenzylamine is known as an amine catalyst having almost the same activity as a morpholine catalyst, but since it is insoluble in water, it is difficult to use in the work.

In addition, recently, 3-dimethylamino-M, H-dimethylglopionamide, 3-dimethylaminopropionitrile, etc. have been used as catalysts for polyurethane production (tlrl, I' 3821131, U, B, P
, 5925268) 0More recently, 2-(
2-dimethylaminoethoxy)ethanol, 1-(2-
dimethylaminoethoxy)-2-glopanol, 1-(
Dimethylaminomono- typified by compounds such as 1-dimethylamino>-2-propoxy)-2-globanol and 2-(1-dimethylamino-2-propoxy)ethanol.
Ether mono-ol compounds are used as catalysts for polyurethane production (Japanese Patent Publication No. 56-9168)
.

Among these polyurethane production catalysts, relatively weakly active catalysts (weak catalysts) include N-methylmorpholine,
Mention may be made of N-ethylmorpholine, dimethylamino mono-ether mono-ol compounds.

This weak catalyst plays an extremely important role in delicately controlling the polyurethane manufacturing process.

[Problem that the invention seeks to solve]

However, the weak catalysts for producing polyurethane that have been developed so far have various problems. That is, N-methylmorpholine and N-ethylmorpholine are
They have an extremely strong pungent odor, and when polyurethane is produced using these compounds, they have the disadvantage of poor skin formation rate.

In addition, the dimethylamino mono-ether mono-ol compound disclosed in Japanese Patent Publication No. 56-9168 has a strong pungent odor, and when producing polyurethane using this compound, it takes a long time to reach foaming ( Since the cream time (cream time) is short, the polyurethane resin has the disadvantage that the polyurethane resin may not reach every detail of the mold during polyurethane molding. Furthermore, when a dimethylamino mono-ether mono-ol compound is used, there is a drawback that the polyurethane skin formation rate is poor.

[Means for solving problems]

As a result of intensive studies to solve the above-mentioned problems, the present inventors found that dimethylethanolamine added with ethylene oxide (10) k2 to 3-v is odorless and has excellent skin-forming ability. It was discovered that the present invention can be suitably used in manufacturing, and the present invention was completed.

That is, the present invention provides a polyurethane creation catalyst comprising a compound represented by the following formula (%).

The catalyst for producing polyurethane of the present invention is as described above.
= 5 to 4, but when n is 2 or less, the odor is strong and the skin forming ability is poor. Also,
When n is 5 or more, the proportion of N atoms per molecular weight is small and the catalytic activity is low. Therefore, when n is 5 or more, a large amount must be used. However, if a large amount of a polyurethane with n of 5 or more is used, it acts as a plasticizer for the urethane resin and has an unfavorable effect on the physical properties of the polyurethane, particularly hardness, elongation, etc.

The novel catalyst of the present invention can be easily produced by known methods. That is, it can be produced by adding 2 to 3 moles of ethylene oxide to dimethylethanolamine.

The amount of the novel catalyst of the present invention used is preferably in the range of 0.01 to 4 parts, particularly preferably in the range of 0.1 to 2 parts, based on 100 parts of polyol used for the production of polyurethane. It is also possible to use it outside this range for the purpose of optimizing the polyurethane manufacturing process by controlling the amount. In addition, the novel catalyst of the present invention can be used in combination with triethylene diamine and organotin compounds that are normally used as cocatalysts in the production of polyurethane. As the polyisocyanate that can be used, any commonly known polyisocyanate may be used, such as 2゜4-tolylene diisocyanate, 2.6-)lylene diisocyanate, 4,4'-diphenylmethane diincyanate, and hexyl diisocyanate. methylene diisocyanate, lysine diisocyanate, inphorone diisocyanate, xylene diisocyanate, 7 chlorohexane diisocyanate, toluidine isocyanate, P-7 diisocyanate), m-phenyl diisocyanate)% 1,5-naphthylene diisocyanate, 4.4'-biphenyl diisocyanate, 3.3'-dimethylbiphenyl-4
, 4'-diisocyanate, s,s'-dimethoxybiphenyl-4,47-diisocyanate, and the like.

As polyols that can be used when producing polyurethane using the novel catalyst of the present invention, generally known polyester polyols, polyether polyols, etc. can be used. For example, ordinary dibasic acids and polyhydric Polyester polyols manufactured from alcohol,
Examples include polyether polyols obtained by adding ethylene oxide or propylene oxide to polyhydric alcohols such as glycol, glycerin, pentaerythritol, trimethylolpropane, and sucrose, and amine polyols.

When producing polyurethane using the novel catalyst of the present invention, C! F'07. Ya 0H
A foaming agent such as 2CA, a surfactant such as organopolysiloxane, a flame retardant such as a halogenated alkyl compound, a halogenated phosphorus compound, and other additives can be used. The types and amounts of these additives can be sufficiently used within the types and ranges commonly used.

[Effect]

The present invention provides a catalyst for polyurethane production comprising a compound represented by the following formula (n = 3 to 4). Below, how the novel catalyst of the present invention works and the effects of the present invention are explained. Describe how it brings about this.

The novel catalyst for polyurethane production of the present invention is odorless due to its relatively larger molecular weight and higher boiling point than those previously known.

In addition, the catalyst of the present invention has (OH,)rN- groups in the molecule and has appropriate activity as a catalyst for polyurethane production, and furthermore, the number of nitrogen atoms per molecular weight is low. It is assumed that the polyurethane manufacturing process can be easily controlled because it is less than known.

EXAMPLES The present invention will be specifically described below with reference to Examples and Comparative Examples, but the present invention is not limited to these Examples.

In Examples and Comparative Examples, the mixing ratios of raw materials for producing polyurethane were as shown in Table 1, and urethane foaming was carried out according to the usual procedure. That is, polyol, water, surfactant, catalyst, and polyisocyanate were mixed and stirred and poured into a 15 (~) square wooden mold lined with a polyethylene sheet kept at 20°C to form a 7-ohm urethane (
The top of the wooden mold is open). Next, a part of Four 4 was cut out, and its physical properties were measured based on various physical property measurement methods defined by Japanese Industrial Standards (JRS). Among the measured physical properties, cream time means the time from the start of mixing and stirring of raw materials until just before foaming begins, and rise time is:
It refers to the time it takes for the polyurethane foam to reach its maximum apparent height. Moreover, the set time means the time until the conversion of polyurethane into a resin is completed.

Table 1 α (1) Polyether polyol (average molecular weight 5oon) manufactured by Mitsui Nichi Urethane Co., Ltd. (2) Surfactant manufactured by Union Carbide ° Co., Ltd. (3) Trirange manufactured by Mitsui Nichi Urethane Co., Ltd. Isocyanate (
2,4 monomer, 2.6 monomer mixture, mixing ratio 80/2G) Examples 1 to 4 BO-2 mole adduct of dimethylethanolamine (OH
Table 2 shows the results when 5+rN-fOH20H209T-H was used as a catalyst. In this case there was no catalyst odor at all.

Table 2 Examples 5-8 10-3 molar adduct of dimethylethanol (a
Table 3 shows the results when m,+-N(-cH2c!2O-)-H was used as a catalyst. In this case there was no catalyst odor at all.

Table 3 Comparative Examples 1 to 8 Table 4 shows the results when N-methylmorpholine or N-ethylmorpholine was used as a catalyst. In these cases, the strong irritating odor of the catalyst is present.Comparative Examples 9-12 Dimethylethanolamine]! to-1 mole adduct (
Table 5 shows the results when OH,)2N+CTl20H20-1rH was used as a catalyst. In this case there was a pungent smell of catalyst.

Table 5 [Effects of the Invention] As specifically shown in the examples, the novel catalyst for producing polyurethane of the present invention has excellent skin-forming ability and is odorless. Furthermore, various physical properties of polyurethane produced using the catalyst of the present invention are equivalent to or better than those of polyurethane produced using hitherto known catalysts for producing polyurethane as shown in the comparative examples. It is.

More specifically regarding the skin-forming ability, when using catalysts known so far, such as N-ethylmorpholine, the phenomenon of skin peeling, which significantly impairs the appearance of polyurethane foam, has often been a problem. This problem is solved by using the polyurethane catalyst of the present invention.

The catalyst for producing polyurethane of the present invention has a relatively large molecular weight and a high boiling point, so it has extremely low volatility and is odorless, which can significantly improve the working environment in polyurethane production. . In addition, since the catalyst for producing polyurethane of the present invention has a hydroxyl group at the end of the molecule, when polyurethane is produced using this catalyst, the hydroxyl group reacts with the incyanate group in the raw material, resulting in the formation of hydroxyl groups in the polyurethane. Another advantage is that the catalyst does not bleed out from the polyurethane foam produced.

Furthermore, although not specifically shown in the examples, it has been confirmed through experiments by the present inventors that polyurethane produced using the catalyst of the present invention is resistant to moisture-heat deterioration.

Claims (1)

[Claims] Primary formula ▲Contains mathematical formulas, chemical formulas, tables, etc.▼ (n=3 to 4) A catalyst for producing polyurethane consisting of a compound represented by: