JP5578061B2 - Chain extender for polyurea (urethane) system - Google Patents

Description

  The present invention relates to a chain extender for a reaction system for producing polyurea or polyureaurethane containing a specific amine compound, a reaction system for preparing polyurea or polyureaurethane using the same, and polyurea using the reaction system Or it relates to a method for producing polyureaurethane.

  Polyurethane is generally produced by reacting a polyol and a polyisocyanate in the presence of a catalyst and, if necessary, a foaming agent, a surfactant, a flame retardant, a crosslinking agent and the like. Polyurea is generally produced by reacting an amine with an isocyanate.

  Reaction system for producing polyurea or polyureaurethane [hereinafter sometimes referred to as a polyurea (urethane) system. ], The polyisocyanate composition and the isocyanate-reactive composition are usually held in separate containers. By contacting and reacting them in the presence of a chain extender, a polyurea elastomer or a polyurea urethane elastomer is formed.

  This polyurea (urethane) system is used as a coating material in surface protection where corrosion is a problem, for example, in bridges, steel tanks, pipes, metal structures and the like. Since this polyurea (urethane) system has a very high curing speed of about 2 to 3 seconds, the construction area can be returned to a usable state much faster than other coating systems. This is one of the major advantages of the polyurea (urethane) system as it allows time and cost savings for both builders and owners. In addition, since it has features such as high mechanical strength (for example, tensile strength, bending strength, hardness, etc.), durability, and chemical resistance, it has been used in various applications in recent years. It has increased.

  In polyurea (urethane) systems, diethylenetoluenediamine (DETDA), one of the commonly used aromatic chain extenders, can shorten the curing time due to its high reactivity, 1) Since the curing reaction is very fast, soaking into the substrate is not sufficient, and high adhesion to the substrate cannot be obtained. 2) The curing reaction is very fast and the viscosity rises so fast that the fluidity is high. It deteriorates and generates pinholes. 3) It has problems such as a change in the color tone of the coating due to ultraviolet deterioration.

  Therefore, various chain extenders have been proposed to solve the above problems. For example, acrylated amines have been introduced as low-reactivity chain extenders (see, for example, Patent Document 1), but there is a need for chain extenders that are not sufficient and have a slower reaction rate.

Special table 2010-521540

  The present invention has been made in view of the above-described background art, and an object of the present invention is to provide a chain extender having a slow reaction rate and good ultraviolet stability, and a polyurea (urethane) system using the chain extender. It is to provide.

  As a result of intensive studies to solve the above problems, the present inventors have shown that when a specific diamine is used as a chain extender, the gelation time is longer than that of the chain extender of the prior art, good processability, and The present inventors have found that the formed film exhibits good UV stability and have arrived at the present invention.

  That is, the present invention is a polyurea (urethane) system chain extender as shown below, a polyurea (urethane) system containing these chain extenders, and a method for producing polyurea or polyureaurethane using the reaction system It is.

  [1] The following formula (1)

［上記式（１）において、Ｒ_１及びＲ_２は各々独立して、水素原子、又は炭素数１〜２０のアルキル基を表す。またＲ_３及びＲ_４は各々独立して、炭素数１〜２０のアルキル基を表す。］
で示される化合物を含むポリウレア又はポリウレアウレタンを製造するための反応システム用鎖延長剤。

[In the above formula (1), R ₁ and R ₂ each independently represent a hydrogen atom or an alkyl group having 1 to 20 carbon atoms. R ₃ and R ₄ each independently represents an alkyl group having 1 to 20 carbon atoms. ]
A chain extender for a reaction system for producing a polyurea or polyureaurethane containing a compound represented by the formula:

[2] The chain extender according to the above [1], wherein in the formula (1), the substituents R ₁ and R ₂ are both hydrogen atoms.

[3] The chain extender according to the above [1], wherein in the formula (1), the substituents R ₁ and R ₂ are each independently an alkyl group having 1 to 6 carbon atoms.

[4] In the above formula (1), R ₃ and R ₄ are each independently an alkyl group having 1 to 6 carbon atoms, according to any one of the above [1] to [3] Chain extender.

  [5] A reaction system for preparing a polyurea or polyureaurethane comprising a polyisocyanate composition (A) and an isocyanate-reactive composition (B), wherein the isocyanate-reactive composition (B) is isocyanate-reactive. A reaction system comprising the compound (b1) and the chain extender (b2) according to any one of the above [1] to [4].

  [6] The reaction system according to [5], wherein the polyisocyanate composition (A) is an isocyanate monomer, a prepolymer, or a mixture thereof.

  [7] The reaction system as described in [5] or [6] above, wherein the isocyanate-reactive compound (b1) contains one or more compounds selected from the group consisting of polyhydric alcohols.

  [8] Any of the above [5] to [7], wherein the isocyanate-reactive compound (b1) includes one or more compounds selected from the group consisting of polyoxyalkylene polyamines. The described reaction system.

  [9] A process for producing polyurea or polyureaurethane, comprising reacting the polyisocyanate composition (A) according to any one of [5] to [8] above with an isocyanate-reactive composition (B).

  Since the polyurea (urethane) system containing the chain extender of the present invention has a slower curing speed and a longer pot life than the conventional polyurea (urethane) system containing a chain extender, the workability is excellent. In addition, the polyurea (urethane) system containing the chain extender of the present invention can provide a polyurea (urethane) elastomer having excellent UV stability.

  Hereinafter, the present invention will be described in detail.

  First, the chain extender for polyurea (urethane) system of the present invention will be described.

  The polyurea (urethane) system chain extender of the present invention contains a compound represented by the above formula (1).

In the above formula (1), R ₁ and R ₂ each independently represent a hydrogen atom or an alkyl group having 1 to 20 carbon atoms. When one or both of the substituents R ₁ and R ₂ is an alkyl group, it is preferably a linear or branched alkyl group, each having 1 to 20, preferably 2 to 6 carbon atoms. is there. Preferred alkyl groups include, for example, methyl group, ethyl group, propyl group, isopropyl group, butyl group, isobutyl group, secondary butyl group, tertiary butyl group, as well as various isomers of pentyl group and hexyl group. , Heptyl group, octyl group, nonyl group, decyl group and the like.

In the above formula (1), the substituents R ₃ and R ₄ each independently represent an alkyl group having 1 to 20 carbon atoms. The substituents R ₃ and R ₄ are preferably linear or branched alkyl groups, each having 1 to 20 carbon atoms, preferably 1 to 6 carbon atoms. Preferred alkyl groups include, for example, methyl group, ethyl group, propyl group, isopropyl group, butyl group, isobutyl group, secondary butyl group, tertiary butyl group, as well as various isomers of pentyl group and hexyl group. , Heptyl group, octyl group, nonyl group, decyl group and the like. While not wishing to be bound by any particular theory, it is believed that the chain extenders of the present invention exhibit good UV stability due to the substituents R ₃ and R ₄ being alkyl groups.

  In the compound represented by the above formula (1), for example, an aniline having an unsubstituted para position or an N-alkyl-substituted aniline derivative and an aliphatic ketone are condensed in the presence of a mineral acid or using a hydrochloride of the aniline derivative. It can be produced by a method (see, for example, JP-A-42-13099 and JP-A-59-27855).

  Further, the polyurea (urethane) system chain extender of the present invention can achieve the object of the present invention by containing only the compound represented by the above formula (1). Separately, a conventionally known chain extender for a urea (urethane) system may be contained within a range that does not impair the effects of the present invention.

  Examples of such chain extenders include aliphatic diamine chain extenders and alicyclic diamine chain extenders described in US Pat. No. 5,162,388 and US Pat. No. 5,480,955. Although an agent is mentioned, it is not necessarily limited to these. Also, an aromatic diamine chain extender described in US Pat. No. 5,317,076 can be suitably used. In the present invention, it is preferable to use an aromatic diamine chain extender in combination.

  Suitable chain extenders for use in combination include 1-methyl-3,5-diethyl-2,4-diaminobenzene and 1-methyl-3,5-diethyl-2,6-diaminobenzene. (These are also called diethyltoluenediamine or DETDA); 1,3,5-triethyl-2,6-diaminobenzene; 3,5,3 ′, 5′-tetraethyl-4,4′-diaminodiphenylmethane; Di (methylthio) -toluenediamine including di (methylthio) -2,4-toluenediamine and 3,5-di (methylthio) -2,6-toluenediamine; N, N′-bis (t-butyl) Ethylenediamine; 4,4′-methylenebis (2-isopropyl-6-methylaniline); 4,4′-methylenebis (2,6-diisopropylaniline); Diamines; guanamines described in WO 2004/090009, in particular 2,4-diamino-6-nonyl-1,3,5-triazine (commercially available from Degussa), Clearlink 1000 (commercially available from UOP) Polyclear 135 (commercially available from BASF); 4,4′-methylenebis (3-chloro-2,6-diethylaniline) [commercially available as LONZACURE M-CDEA]; acetamino-trimethylcyclohexanemethanamine [ And commercially available as JEFFLINK 754].

  Next, the polyurea (urethane) system of the present invention will be described.

  The polyurea (urethane) system of the present invention is a reaction system for preparing a polyurea or polyurethane comprising a polyisocyanate composition (A) and an isocyanate-reactive composition (B), wherein the isocyanate-reactive composition (B ) Contains the isocyanate-reactive compound (b1) and the chain extender (b2) of the present invention described above.

  Examples of the isocyanate used in the polyisocyanate composition (A) include conventionally known polyisocyanates. Specifically, hexamethylene diisocyanate (HDI), tetraalkylxylene diisocyanate, cyclohexane diisocyanate, 1,12- Dodecane diisocyanate, 1,4-tetramethylene diisocyanate, 1,3- or 1,4-cyclohexane diisocyanate, 1-isocyanate-3,3,5-trimethyl-5-isocyanatomethyl-cyclohexane (isophorone diisocyanate), 4,4 Aliphatic isocyanates such as' -dicyclohexyl-methane diisocyanate, 2,2'-dicyclohexyl-methane diisocyanate, 2,4'-dicyclohexyl-methane diisocyanate; m Phenylene diisocyanate, p-phenylene diisocyanate, 4,4'- or 2,4'- or 2,2'-diphenylmethane diisocyanate (MDI), polymethylene polyphenylene diisocyanate (MDI oligomers with isocyanate functionality greater than 2 and MDI Mixture), modified MDI obtained by uretonimine modification or carbodiimide modification, 2,4′- or 2,6′-toluene diisocyanate (TDI), dianisidine diisocyanate, vitorylene diisocyanate, naphthalene-1,4-diisocyanate, diphenylene-4 , 4′-diisocyanate, etc .; xylene-1,3-diisocyanate, bis (4-isocyanatophenyl) methane, bis (3-methyl-4-isocyanate) Phenyl) methane, and 4,4' although aliphatic or aromatic diisocyanates such as diphenyl propane diisocyanate, and the like, but is not necessarily limited thereto. In addition, the above-described isocyanates can be used alone or in combination.

  In the present invention, the preferred isocyanate is aromatic isocyanate, and liquid MDI obtained by uretonimine modification or carbodiimide modification of diphenylmethane diisocyanate is particularly preferred.

  In the present invention, in addition to the above-mentioned isocyanate monomer, a prepolymer formed by a reaction between an isocyanate and a polyhydric alcohol or polyamine can also be used.

  Examples of the polyhydric alcohol include polyether polyol, polyester polyol, polycarbonate polyol, polycaprolactone polyol, and the like. These polyhydric alcohols can be used alone or in combination of two or more.

  Examples of the polyether polyol include polyethylene glycol, polypropylene glycol, polypropylene glycol-ethylene glycol copolymer, polytetramethylene glycol, polyhexamethylene glycol, polyheptamethylene glycol, polydecamethylene glycol, or alkylene oxide (for example, ethylene oxide, propylene And polyether polyols obtained by ring-opening polymerization of an isocyanate-reactive initiator having a functionality of 2 to 8).

  As a polyester polyol, the polyester diol obtained by making a polyhydric alcohol and a polybasic acid react is mentioned, for example. Here, specific examples of the polyhydric alcohol include ethylene glycol, polyethylene glycol, tetramethylene glycol, polytetramethylene glycol, 1,6-hexanediol, 3-methyl-1,5-pentanediol, 1,9. -Nonanediol, 2-methyl-1,8-octanediol and the like are exemplified. Specific examples of the polybasic acid include phthalic acid, dimer acid, isophthalic acid, terephthalic acid, maleic acid, fumaric acid, adipic acid, and sebacic acid.

  Examples of the polycarbonate polyol include polytetrahydrofuran polycarbonate, poly (hexanediol carbonate), poly (nonanediol carbonate), and poly (3-methyl-1,5-pentamethylene carbonate).

  The polycaprolactone polyol preferably has a melting point of 0 ° C. or higher, and examples thereof include polycaprolactone diol obtained by reacting ε-caprolactone with a diol compound. Here, as the diol compound, for example, ethylene glycol, polyethylene glycol, polypropylene glycol, tetramethylene glycol, polytetramethylene glycol, 1,2-polybutylene glycol, 1,6-hexanediol, neopentyl glycol, 1,4 -Cyclohexanedimethanol, 1,4-butanediol and the like are exemplified.

  In the present invention, polyols other than those described above can be used as the polyhydric alcohol. Specific examples of such polyols include ethylene glycol, propanediol, 1,4-butanediol, 1,5-pentanediol, 1,6-hexanediol, cyclohexanedimethanol, polyoxyethylene bisphenol A ether, Examples include polyoxypropylene bisphenol A ether, polyoxyethylene bisphenol F ether, and polyoxypropylene bisphenol F ether.

  It is preferable that the isocyanate is stoichiometrically excessive with respect to the polyhydric alcohol or polyamine in the relative use amount of the isocyanate and the polyhydric alcohol or polyamine in producing the prepolymer. That is, the isocyanate is usually used in an amount of more than 1 mole, preferably 1.05 to 25 moles, more preferably 10 to 25 moles per mole of polyhydric alcohol or polyamine.

  Aromatic polyisocyanates preferred in the present invention usually have an isocyanate content of 5 to 35%, preferably 10 to 25%, more preferably 15 to 20%.

  In the present invention, particularly preferred isocyanate is usually 16 to 25%, preferably 16 to 20% obtained from MDI which may be modified with uretonimine and polypropylene glycol (which preferably has a molecular weight of about 2,000). Is a prepolymer having an NCO value in the range of

  In the present invention, the isocyanate-reactive composition (B) contains the isocyanate-reactive compound (b1) and the above-described chain extender (b2) of the present invention.

  The isocyanate-reactive compound (b1) preferably contains one or more compounds selected from the group consisting of polyhydric alcohols, and one or more compounds selected from the group consisting of polyoxyalkylene polyamines. More preferably, it comprises a compound.

  As the polyhydric alcohol, the polyhydric alcohol described above with respect to the prepolymer can be used. Preferred polyhydric alcohols used here are 1,4-butanediol, monoethylene glycol or both. The amount of the polyhydric alcohol used is not particularly limited, but is usually less than 50% by weight and preferably in the range of 5 to 15% by weight based on the whole isocyanate-reactive compound. Moreover, it is preferable that it is less than the usage-amount of polyoxyalkylene polyamine. Advantages of adding a polyhydric alcohol include, for example, a polyurea (urethane) urethane system containing some polyurethane groups, a controlled cure profile, and reliable mixing. And so on.

  In addition, as the polyoxyalkylene polyamine, for example, after adding lower alkylene oxide (specifically, ethylene oxide, propylene oxide, butylene oxide, or a mixture thereof) to an appropriate initiator, Mention is made of polyoxyalkylene polyamines produced by amination of the resulting hydroxyl-terminated polyols.

  In the present invention, for example, a high molecular weight polyoxyalkylene polyamine can be used as a single material. In addition, for example, a high molecular weight polyoxyalkylene polyamine can be used as a mixture of a bifunctional material and a trifunctional material, or a mixture of materials having different molecular weights or different chemical compositions. In the present invention, “high molecular weight” polyoxyalkylene polyamine means a polyoxyalkylene polyamine having a molecular weight of at least about 2,000.

  Furthermore, in the present invention, low molecular weight polyoxyalkylene polyamines other than high molecular weight polyoxyalkylene polyamines can also be used, and these can be used alone or in combination with the polyhydric alcohol described above.

  In the present invention, suitable polyoxyalkylene polyamines are the JEFFAMINE brand series of polyoxyalkylene polyamines available from Huntsman Specialty Chemicals, including JEFFAMINE D-2000, JEFFAMINE D-4000, JEFFAMINE T-3000, JEFFAMINE T-5000 etc. are included. These polyoxyalkylene polyamines are available from Huntsum Specialty Chemicals Corp., whose title is “The JEFFAMINE Polyoxyalkyleneamines”. It is described in detail in the product brochure.

  The polyurea (urethane) system of the present invention may further contain plasticizers, fillers, glass fibers, pigments, solvents and the like.

  In the polyurea (urethane) system of the present invention, a general blend composed of a polyisocyanate composition (A) and an isocyanate-reactive composition (B) is usually a polyisocyanate composition relative to the entire blend. (A) is included in the range of 30 to 70% by weight, and the isocyanate-reactive composition (B) is included in the range of 70 to 30% by weight. It is preferable that the polyisocyanate composition (A) is contained in the range of 40 to 60% by weight and the isocyanate-reactive composition (B) is contained in the range of 60 to 40% by weight with respect to the entire blend.

  In the present invention, the polyisocyanate composition (A) and the isocyanate-reactive composition (B) are mixed under any effective conditions in order to react with other optional components. The temperature during the reaction is usually in the range of 0 to 90 ° C, preferably 40 to 90 ° C, more preferably 60 to 80 ° C. These components are usually mixed at a pressure ranging from ambient pressure up to 3000 psig, but preferably at a pressure ranging from about 1500 psig to 3000 psig.

  When the polyurea (urethane) system of the present invention is used in spray applications, these components can be directly impact mixed using a high pressure spray device. Examples of the high pressure spray device include a GUSMER VR-H-3000 blending device equipped with a GUSMER Model GX-7 spray gun. In this apparatus, the pressurized streams of polyisocyanate composition (A) and isocyanate-reactive composition (B) are fed from two separate chambers and collided with each other at a high speed so that the coating composition is It is formed. The resulting coating composition is delivered onto or into the desired substrate using a spray gun.

  Other suitable coating devices include, for example, a ratio pack HSS system (supplied by PLAS PAK Industries). In this apparatus, the polyisocyanate composition (A) and the isocyanate-reactive composition (B) are stored in separate chambers, and when pressure is applied, the respective components are fed into the static mixer at a volume ratio of 1: 1. The Each component is mixed by a serpentine or helical passage in a static mixer and fed from the outlet end onto or into the substrate.

  The polyurea (urethane) system of the present invention can be applied to a wide variety of substrates. For example, metal, natural stone, synthetic stone, ceramic, glass, brick, cement, concrete, lightweight concrete block, wood, composite materials and laminates thereof; artificial wall board, dry wall, gypsum board, cement board, plastic, paper, Examples include PVC, expanded styrene, plastic composite, acrylic composite, ballistic composite, asphalt, glass fiber, soil, gravel, and the like. Although it does not specifically limit as a metal, For example, aluminum, a cold-rolled steel plate, electrogalvanized steel, hot dip galvanized steel, titanium, an alloy is mentioned. Although it does not specifically limit as a plastic, For example, TPO, SMC, TPU, a polypropylene, a polycarbonate, polyethylene, polyamide (Nylon) etc. are mentioned.

  EXAMPLES Hereinafter, although this invention is demonstrated further in detail based on an Example, this invention is limited to these and is not interpreted.

Synthesis Example 1
In a 1 L autoclave, 250 g of aniline hydrochloride, 199 g of water, and 40 g of acetone were added, and the mixture was heated to 130 ° C. with stirring and reacted for 18 hours. After allowing to cool, the solution was transferred to a 3 L separatory funnel, and diluted by adding 600 g of ethyl acetate and 100 g of water. Next, 178 g of a 48% by weight aqueous sodium hydroxide solution was added for alkali treatment, and the organic layer obtained by liquid separation was washed with 372 g of water. Subsequently, ethyl acetate and aniline in the organic layer were distilled off under reduced pressure, and 2,2-bis (4-aminophenyl) propane was distilled under reduced pressure at 186 to 190 ° C./3.5 mmHg. The obtained brown solid was recrystallized from toluene to obtain 70 g of the target product as white crystals (isolation yield 45%).

Synthesis Example 2
2,2-bis (4-aminophenyl) pentane was obtained as white crystals in the same manner as in Synthesis Example 1 except that 40 g of acetone in Synthesis Example 1 was changed to 60 g of 2-pentanone.

Synthesis Example 3
In a 2.5 L autoclave, 50 g of 2,2-bis (4-aminophenyl) propane of Synthesis Example 1, 290 g of an aqueous HBr solution (48% by weight), 143 g of pyridine, and 300 ml of dioxane were added, and 300 ml of isobutene was added. While stirring, the temperature was raised to 140 ° C. and reacted for 5 days. After allowing to cool, methyl tertiary butyl ether and aqueous NaOH solution were added, and the organic layer was separated. The obtained organic layer was removed by an evaporator, concentrated and purified by silica gel chromatography to obtain 53 g of N, N′-tert-butylated 2,2-bis (4-aminophenyl) propane.

Example 1.
The spray coating agent of the polyurea system containing 2,2-bis (4-aminophenyl) propane of Synthesis Example 1 was prepared by the following method. 29% by weight of 2,2-bis (4-aminophenyl) propane, 65% by weight of JEFFFAMINE D-2000 (manufactured by Huntsman Corporation), 6% by weight of JEFFFAMINE T-3000 (Huntsman) Component B was prepared by mixing with Corporation. Coronate 4554 (manufactured by Nippon Polyurethane Industry Co., Ltd.), which is an MDI prepolymer based on MDI and polypropylene glycol and having an isocyanate value of 16%, was used as Component A. Release agent containing sodium oleate at a pressure ratio of 0.7 MPa and a volume ratio of A component and B component of 1: 1 with both A component and B component adjusted to 80 ° C. filled in a ratio pack HSS system Was sprayed onto a metal panel coated with a film to form a coating. The coating was cured under ambient conditions for 2 days, followed by forced curing in an oven at 70 ° C. for 16 hours. The resulting coating had an effective gel time of 50 seconds. The obtained coating 6 cm × 6 cm was placed in a QUV cabinet (Q-Lab, Incorporated) and exposed to UVA light at 340 nm and an intensity of 0.89 W / m ² for 100 hours. When the change in color tone before and after UVA exposure was measured with a color difference meter CM-3500d (manufactured by Konica Minolta), the change in color tone (ΔE) was 6.5. These results are shown in Table 1.

実施例２．
実施例１の２９重量％の２，２−ビス（４−アミノフェニル）プロパンを、２０重量％の２，２−ビス（４−アミノフェニル）プロパンと１０重量％のＣｌｅａｒｌｉｎｋ（登録商標）１０００（Ｄｏｒｆ Ｋｅｔａｌ Ｃｈｅｍｉｃａｌｓ社製）とした以外は、実施例１と同様の方法で被膜を形成し、物性の評価を行った結果を表１に併せて示す。得られた被膜のゲル時間は８０秒であり、色調の変化は６．３であった。

Example 2
29% by weight of 2,2-bis (4-aminophenyl) propane of Example 1 was mixed with 20% by weight of 2,2-bis (4-aminophenyl) propane and 10% by weight of Clearlink® 1000 ( Table 1 also shows the results of forming a coating film by the same method as in Example 1 and evaluating the physical properties except that it was made by Dorf Chemical Chemicals). The gel time of the obtained film was 80 seconds, and the change in color tone was 6.3.

Example 3
A film was formed in the same manner as in Example 1 except that 2,2-bis (4-aminophenyl) propane in Example 1 was changed to 2,2-bis (4-aminophenyl) pentane (Synthesis Example 2). Table 1 also shows the results of the physical property evaluation. The gelation time of the obtained film was 60 seconds, and the color change was 6.4.

Example 4
2,2-bis (4-aminophenyl) propane of Example 1 was converted to N, N′-tert-butylated 2,2-bis (4-aminophenyl) propane 2,2-bis (4-aminophenyl) pentane ( Table 1 also shows the results of forming a film by the same method as in Example 1 except that the synthesis example 3) was changed and evaluating the physical properties. The gelation time of the obtained film was 100 seconds, and the change in color tone was 6.5.

Comparative Example 1
A film was formed in the same manner as in Example 1 except that 2,2-bis (4-aminophenyl) propane in Example 1 was changed to diethyltoluenediamine (DETDA, manufactured by ARBEMARLE), and physical properties were evaluated. The results are shown in Table 2. The gelation time of the obtained film was 5 seconds, and the change in color tone was 25.

比較例２．
実施例１の２，２−ビス（４−アミノフェニル）プロパンを４，４’−メチレンジアニリン（ＭＤＡ、和光純薬工業社製）と変更した以外は、実施例１と同様の方法で被膜を形成し、物性の評価を行った結果を表２に併せて示す。得られた被膜のゲル化時間は３秒、色調の変化は３２であった。

Comparative Example 2
The coating was made in the same manner as in Example 1 except that 2,2-bis (4-aminophenyl) propane in Example 1 was changed to 4,4′-methylenedianiline (MDA, manufactured by Wako Pure Chemical Industries, Ltd.). Table 2 also shows the results of the evaluation of physical properties. The resulting coating had a gel time of 3 seconds and a color tone change of 32.

Comparative Example 3
The same as Example 1 except that 2,2-bis (4-aminophenyl) propane of Example 1 was changed to 4,4′-methylenebis [N- (1-methylpropyl) aniline] (manufactured by UOP). Table 2 also shows the results of forming a film by the above method and evaluating the physical properties. The gelation time of the obtained film was 70 seconds, and the change in color tone was 30.

Claims (9)

Following formula (1)

[In the above formula (1), R ₁ and R ₂ each independently represent a hydrogen atom or an alkyl group having 1 to 20 carbon atoms. R ₃ and R ₄ each independently represents an alkyl group having 1 to 20 carbon atoms. ]
A chain extender for a reaction system for producing a polyurea or polyureaurethane containing a compound represented by the formula: The chain extender according to claim 1, wherein in the formula (1), the substituents R ₁ and R ₂ are both hydrogen atoms. In the formula (1), independently substituents R ₁ and R ₂ are each a chain extender according to claim 1, characterized in that an alkyl group having 1 to 6 carbon atoms. In formula (1), R < ₃ > and R < ₄ > are respectively independently a C1-C6 alkyl group, The chain extender in any one of the Claims 1 thru | or 3 characterized by the above-mentioned. A reaction system for preparing a polyurea or polyureaurethane comprising a polyisocyanate composition (A) and an isocyanate-reactive composition (B), wherein the isocyanate-reactive composition (B) comprises an isocyanate-reactive compound (b1 And a chain extender (b2) according to any one of claims 1 to 4. The reaction system according to claim 5, wherein the polyisocyanate composition (A) is an isocyanate monomer, a prepolymer, or a mixture thereof. The reaction system according to claim 5 or 6, wherein the isocyanate-reactive compound (b1) contains one or more compounds selected from the group consisting of polyhydric alcohols. The reaction system according to claim 5 or 6 , wherein the isocyanate-reactive compound (b1) contains one or more compounds selected from the group consisting of polyoxyalkylene polyamines. A method for producing polyurea or polyureaurethane, comprising reacting the polyisocyanate composition (A) according to any one of claims 5 to 8 with an isocyanate-reactive composition (B).