Isophorone diamine composition and isophorone diisocyanate composition

Abstract

The invention relates to an isophorone diamine composition and an isophorone diisocyanate composition. The content of the hydroxy nitrile compound in the isophorone diamine composition is 0.0001 to 0.0500 weight percent, preferably 0.0001 to 0.0300 weight percent, and more preferably 0.0005 to 0.0300 weight percent. The reaction activity of the isophorone diisocyanate composition prepared from the isophorone diamine composition and polyhydric alcohols is moderate, the color number and turbidity of obtained reaction liquid are lower, and fewer residual monomers exist.

Description

Technical Field

[0001] The invention provides an isophorone diamine composition and an isophorone diisocyanate composition. Background Art

[0002] Isophorone diamine (IPDA) is mainly used as a curing agent for epoxy resins. It is mainly used in epoxy formulations that require low color, low odor, high flexural strength and excellent chemical resistance. It is suitable for floor coatings, paving fillers and mixtures. Another use is as a raw material for isophorone diisocyanate (IPDI).

[0003] IPDI is a colorless or light yellow liquid at room temperature. It is an aliphatic isocyanate and an alicyclic isocyanate. It has lower reactivity and vapor pressure than aromatic isocyanates, and is less toxic than isocyanates. Since there is no benzene ring in its structure, it has excellent weather resistance and can be used to prepare high-end polyurethane materials with light stability, weather resistance and excellent mechanical properties, such as elastomers, water-based polyurethane dispersions, UV resins, etc. IPDI can also self-polymerize to form multifunctional polyisocyanates. The surface of the coating prepared with it dries quickly, and it has excellent application in automotive repair paint. In the above applications, the various components and impurity contents in the IPDI monomer are strictly required.

[0004] As the concept of environmental protection gradually takes root in people's minds, the market is paying more and more attention to the VOC volatilization problem during the use of isocyanate monomers. In order to reduce the volatilization of solvents during its use, the method adopted by CN94108263.6 is to react isocyanate monomers with polyols to form prepolymers. Since the molecular weight of the prepolymer is relatively large, the VOC volatilization amount during use is relatively small, so this solution is becoming more and more popular in the market.

[0005] As for IPDI, due to the difference in activity between its two NCOs, the NCO with higher activity participates in the reaction with the polyol in the early stage, while the NCO with lower activity participates in the reaction in the later stage. However, in the later stage of the reaction, the viscosity of the system will gradually increase, and the dispersion and mixing effect between IPDI and the polyol is poor, so the required reaction time is relatively long. On the other hand, the local aggregation of molecules and energy caused by the increase in viscosity will lead to excessive polymerization reaction, resulting in turbidity of the reaction liquid.

[0006] To solve this problem, the solution provided by DD151466A1 is to carry out the reaction in a solvent, but there is a subsequent desolventizing operation, and part of the solvent will remain in the prepolymer, which will volatilize VOC during subsequent use. The solution adopted by CN94108263.6 is to control 2% of the IPDI monomer residue to reduce the viscosity of the reaction system, thereby promoting the reaction of NCO and polyols, but the residual IPDI also has a certain amount of VOC volatilization, so it is not the optimal solution from an environmental perspective. In addition, increasing the temperature is also a way to reduce the viscosity, but long-term high temperature retention will cause the color number of IPDI monomer and prepolymer to increase, thereby affecting its performance in high-end applications. The same problem will also exist through high-temperature separation and other means.

[0007] Therefore, it is of great significance to develop an IPDI monomer with moderate activity, less residual monomer in the prepolymer after reaction with the polyol, and lower turbidity and color number of the prepolymer. Summary of the invention

[0008] In view of the above problems existing in the prior art, the present invention aims to provide an isophorone diamine composition and an isophorone diisocyanate composition. The isophorone diisocyanate composition has moderate reactivity with alcohols, less residual monomers in the prepolymer after reacting with polyols, and lower turbidity and color number of the prepolymer.

[0009] To achieve the above object, the present invention adopts the following technical solution:

[0010] An isophorone diamine (IPDA) composition, characterized in that the content of the hydroxy nitrile compound in the isophorone diamine composition is 0.0001-0.0500wt%, preferably 0.0001-0.0300wt%, and more preferably 0.0005-0.0300wt%.

[0011] The isophorone diamine composition is used to carry out a phosgenation reaction with a phosgene raw material to obtain the isophorone diisocyanate composition.

[0012] The hydroxynitrile compound in the isophorone diamine composition is 3-nitrile-3,5,5-trimethylcyclohexanol, and the structural formula is:

[0013]

[0014] There is no specific requirement for the preparation method of the isophorone diamine composition of the present invention, and the isophorone diamine composition of the composition can be obtained by any achievable method in the prior art.

[0015] In some embodiments of the present invention, the isophorone composition is prepared by adding a hydroxynitrile compound to IPDA, or by blending an IPDA composition having a high concentration of hydroxynitrile with conventional IPDA.

[0016] According to the preparation process of the entire industry chain of isophorone diisocyanate provided by patent CN109761855A, the conventional preparation method of isophorone diamine is to obtain it by amination and hydrogenation of isophorone nitrile, wherein the amination process is to amination the carbonyl group in isophorone nitrile to obtain an amine group, and the hydrogenation process is to hydrogenate the nitrile group in isophorone nitrile to obtain an amine group. In the conventional preparation process, it is difficult to obtain an IPDA composition containing a hydroxynitrile compound.

[0017] To this end, the present invention adopts the method of directly hydrogenating isophoronenitrile to prepare the hydroxynitrile compound, and the specific synthesis method is as follows:

[0018] a) mixing hydrogen and isophoronenitrile in a 1-5 wt % KOH ethanol solution in the presence of a hydrogenation catalyst to obtain a reaction product containing 3-nitrile-3,5,5-trimethylcyclohexanol (hydroxynitrile compound);

[0019] b) separating and purifying the reaction product obtained in step a) to obtain the hydroxynitrile compound required by the present invention.

[0020] The reaction temperature of the hydrogenation reaction in step a) is 50-200°C, more preferably 50-150°C, for example, 60°C, 70°C, 80°C, 100°C, 120°C, 140°C; the pressure is 0.3-2MPa, more preferably 0.5-1.5MPa, for example, 0.6MPa, 0.8MPa, 1.0MPa, 1.2MPa, 1.4MPa; the catalyst selected is Raney copper and / or Raney nickel.

[0021] In the step a), the mass ratio of the hydrogenation catalyst to the reaction raw material isophoronenitrile is 1:100-1000, more preferably 1:200-750, for example, 1:500, 1:250.

[0022] In the step b), the separation and purification process of the reaction product is carried out by distillation, and the distillation process is carried out by a distillation tower with a plate number of 10-20 to obtain a hydroxynitrile compound with a purity of >99%. A certain amount of hydroxynitrile compound can be added to conventional IPDA to obtain an IPDA composition with a hydroxynitrile compound content of 0.0001-0.0500wt%, preferably 0.0001-0.0300wt%, and more preferably 0.0005-0.0300wt%.

[0023] There may be other methods for controlling the hydroxynitrile compound in the IPDA composition, which are not listed one by one in the present invention. The above methods can be used in combination or alone, and the present invention does not limit the method for obtaining the IPDA composition.

[0024] The content of the hydroxynitrile compound in the isophoronediamine composition of the present invention can be analyzed by gas chromatography. The present invention has no specific requirements. For example, the method used in some specific examples is: the sample is dissolved in a solvent (preferably dichloromethane) and then analyzed by gas chromatography, detected by a hydrogen ion flame detector (FID), and quantitatively calculated by area normalization method.

[0025] The present invention also provides a method for preparing an isophorone diisocyanate composition (IPDI), wherein the isophorone diamine composition is subjected to a phosgenation reaction with a phosgene raw material to obtain the isophorone diisocyanate composition.

[0026] The phosgenation reaction can be any one of a gas phase phosgenation reaction, a cold or hot phosgenation reaction, and a salt-forming phosgenation reaction. The phosgenation reaction is carried out by reacting isophorone diamine with one or more of phosgene, diphosgene, triphosgene, fluorophosgene or bromophosgene.

[0027] The above-mentioned phosgenation reaction can be carried out in the gas phase. For the specific method, refer to Chinese patent CN105214568A, which is incorporated into the present application by reference. Specifically, 1) amine is gasified to form an amine gas stream, and the amine gas stream contains amine droplets; 2) the amine droplets contained in the amine gas stream are removed to obtain an amine gas stream substantially free of amine droplets; 3) the amine gas stream substantially free of amine droplets is subjected to a gas phase phosgenation reaction with phosgene to obtain isocyanate; at the same time, a heater is used to remove the amine droplets contained in the amine gas stream. The specific structure of the above-mentioned heater can be referred to patent document CN105214568A.

[0028] The reaction temperature of the gas phase phosgenation is 200-550°C, preferably 250-400°C, for example, 300°C, 320°C; the reaction pressure is 0.01-1MPa, preferably 0.03-0.3MPa, for example, 0.08MPa, 0.2MPa. In some specific embodiments, the mixed gas after the reaction of phosgene and isophoronediamine (IPDA for short) needs to be absorbed and cooled with a liquid inert medium or / and a mixture of an inert medium and isocyanate. The inert gas is preferably nitrogen or argon or the vapor of toluene, xylene, chlorobenzene, ortho-dichlorobenzene; the liquid inert medium is selected from all inert liquids suitable for the preparation of isocyanates, preferably chlorobenzene, dichlorobenzene, ortho-dichlorobenzene, toluene, chlorotoluene, xylene and / or a mixture thereof.

[0029] The above-mentioned phosgenation reaction can be carried out in the liquid phase. For specific methods, see Chinese patent CN103319372B, which is incorporated into the present application by reference. Specifically, a') cold reaction, the temperature is 0-130°C, preferably 40-70°C; the pressure is 0.1-1MPa absolute pressure; toluene, chlorobenzene, benzene, dichlorobenzene, cyclohexane, xylene or a mixture thereof is used as a solvent, chlorobenzene and dichlorobenzene are particularly preferred as solvents; react with superstoichiometric phosgene, and the reaction residence time is 2-120min, preferably 5-45min; b') is a hot reaction, the temperature is 60-190°C, preferably 110-165°C; the pressure is 0.1-1MPa absolute pressure; toluene, chlorobenzene, benzene, dichlorobenzene, cyclohexane, xylene or a mixture thereof is used as a solvent, chlorobenzene and dichlorobenzene are particularly preferred as solvents, and react with superstoichiometric phosgene, and the reaction residence time is 0.5-5h, preferably 1-4h. The above-mentioned phosgenation reaction can be a phosgenation reaction of hydrogen chloride and / or carbon dioxide salt formation. For specific methods, please refer to Chinese patents CN105218422B and CN107337615A, which are incorporated into the present application by reference. Specifically, 1') hydrogen chloride or / and carbon dioxide reacts with an amine in an inert solvent to form a salt, the molar equivalent ratio of the hydrogen chloride to the amino group of the amine is 1-2.5:1, preferably 1.2-2:1, the molar equivalent ratio of the carbon dioxide to the amino group of the amine is 0.5-5:1, preferably 0.6-3:1, and the mass ratio of the solvent to the amine is 25-5:1, preferably 20-5:1; the temperature of the salt-forming reaction is 0-50°C, preferably 5-30°C, and the pressure is an absolute pressure of 0.1-1MPa, preferably 0.2-0.5MPa; the reaction residence time is 1-15min, preferably 5-10min; the reaction pressure is an absolute pressure of 0.1-1MPa, preferably 0.2-0.5MPa. The hydrochloride or carbonate reaction liquid obtained after the salt formation reaction in step a) enters step 2') for phosgenation reaction at a temperature of 100-170°C, preferably 110-165°C; the pressure is an absolute pressure of 0.1-1MPa, preferably 0.2-0.5MPa; and reacts with superstoichiometric phosgene for a reaction residence time of 1-5h, preferably 1.5-4h. The inert solvent is toluene, chlorobenzene, benzene, dichlorobenzene, cyclohexane, xylene or a mixture thereof, more preferably chlorobenzene or dichlorobenzene.

[0030] In some specific embodiments, in the reaction processes of the above-mentioned gas-phase phosgenation, liquid-phase phosgenation and salt-forming phosgenation methods, phosgene is excessive in the phosgenation reaction, and the excess phosgene after the phosgenation reaction is preferably removed at about 50-180° C. and an absolute pressure of 0.05-0.1 MPa.

[0031] The IPDI composition obtained by phosgenation of the IPDA composition containing the hydroxynitrile compound provided by the present invention has a relatively moderate reactivity with polyols. A slow reaction affects production efficiency, while a fast reaction may lead to an aggravation of the reaction or even out of control, thereby causing the viscosity of the alcohol-modified product to be too high, even turbidity, and even a high color number of the reaction liquid.

[0032] The hydroxynitrile compound of the present invention undergoes the following reaction during the phosgenation process:

[0033]

[0034] The hydroxyl group in the hydroxynitrile compounds first reacts with phosgene during the phosgenation process to form acyl chlorides, which are then further heated and decomposed to obtain chloronitrile compounds.

[0035] It is further speculated that in the initial stage of the reaction between IPDI and polyols, the nitrile compounds in the chloronitrile compounds contained in the IPDI composition are easily hydrolyzed to form carboxylic acid structures in the presence of catalysts and polyols, thereby further promoting the reaction between polyols and IPDI, so that the reaction efficiency of the IPDI composition and polyols is improved, and excessive monomer residues caused by the low efficiency of the reaction process are avoided; when the reaction of the IPDI composition and polyols proceeds to a certain extent, the reaction temperature becomes higher and higher, and the rate becomes faster and faster, the chlorine of the chloronitrile compounds will decompose, resulting in a decrease in the catalytic activity of the reaction catalyst, thereby inhibiting the reaction of IPDI and polyols.

[0036] When the content of chloronitrile compounds in the IPDI composition is too high, the content of carboxylic acids obtained by hydrolysis of nitriles in the initial stage is too high, which may cause the reaction to intensify or even get out of control, thereby causing the viscosity of the alcohol-modified product to be too high, even turbidity, and even a high color number of the reaction liquid.

[0037] Therefore, the present invention limits the content of the hydroxynitrile compound in the raw material IPDA composition used to prepare the IPDI composition to 0.0001-0.0500wt%, preferably 0.0001-0.0300wt%, and more preferably 0.0005-0.0300wt%.

[0038] Compared with the prior art, the isophorone diamine composition provided by the present invention has the following beneficial effects:

[0039] 1. The IPDI composition obtained by phosgenation of the IPDA composition provided by the present invention has moderate reactivity with polyols;

[0040] 2. The prepolymer obtained after the IPDI composition reacts with the polyol has a lower color number and less residual monomers. DETAILED DESCRIPTION

[0041] The technical scheme of the present invention is further described below by specific implementation methods. Those skilled in the art should understand that the embodiments are only to help understand the present invention and should not be regarded as specific limitations of the present invention. The polypropylene glycol used in the embodiments is produced by Wanhua Chemical Group Co., Ltd. and the specification is PPG-2000.

[0042] The quantitative analysis of the hydroxynitrile compounds in the isophoronediamine composition was carried out on a gas chromatograph, and the gas chromatographic analysis conditions were as follows:

[0043] Chromatographic column: Agilent HP-5 (specifications: 30m*0.32mm*0.25mm); inlet temperature: 280℃; split ratio: 30:1; column flow rate: 1.5ml / min; column temperature: 100℃, retain for 0.5min, then increase to 260℃ at 15℃ / min, maintain for 8min; detector temperature: 280℃; H2 flow rate: 35ml / min.

[0044] Example 1 Preparation of IPDA compositions with different hydroxynitrile compound contents

[0045] (1) Synthesis of isophoronenitrile (IPN)

[0046] By the method provided in patent CN109761855A, isophorone is sent to a preheater at a speed of 200 kg / h and preheated to a reaction temperature of 120°C, and then, HCN and a basic catalyst sodium methoxide are respectively sent to the reactor disclosed in Example 1 of CN103301799B in a molar ratio of 2:1:0.003 and reacted under the operating conditions, the reaction pressure is an absolute pressure of 1 MPa, and after reacting for 25 minutes, isophorone nitrile (3-cyano-3,5,5-trimethylcyclohexanone, referred to as IPN) is obtained;

[0047] (2) Hydroxynitrile compounds

[0048] The isophorone nitrile (IPN) obtained above and hydrogen are reacted in the presence of a catalyst, specifically as follows: in the presence of a hydrogenation catalyst Raney copper, the space velocity of the catalyst is 1.5 g 3-cyano-3,5,5-trimethylcyclohexanone / (ml catalyst·hour), hydrogen and IPN are mixed in a 3% KOH-ethanol solution for reaction, and the reaction is carried out at a temperature of 120° C. and an absolute pressure of 1 MPa to obtain a reaction product containing 3-nitrile-3,5,5-trimethylcyclohexanol (hydroxynitrile compound);

[0049] The method provided by Chinese patent CN107304168A is used to purify the reaction product containing 3-nitrile-3,5,5-trimethylcyclohexanol (hydroxynitrile compound) to obtain a hydroxynitrile compound with a purity of more than 99%.

[0050] (3) Preparation of conventional IPDA compositions

[0051] The isophoronenitrile obtained in step (1), ammonia and hydrogen are reacted in the presence of a catalyst, specifically as follows: a) the isophoronenitrile obtained in step (1) is reacted with ammonia in a tubular reactor, the reaction is carried out at a temperature of 60° C. and an absolute pressure of 15 MPa, the molar ratio of ammonia to isophoronenitrile is 50:1, to obtain 3-cyano-3,5,5-trimethylcyclohexylimine;

[0052] b) in the presence of a hydrogenation catalyst Raney cobalt, the space velocity of the catalyst is 1.5 g 3-cyano-3,5,5-trimethylcyclohexanone / (ml catalyst hour), hydrogen, NH3 and the 3-cyano-3,5,5-trimethylcyclohexyl imine obtained in step a) are mixed and reacted in a 3% KOH-ethanol solution, and the reaction is carried out at a temperature of 80° C. and an absolute pressure of 18 MPa to obtain a product containing 3-aminomethyl-3,5,5-trimethylcyclohexylamine (abbreviated as IPDA) and 3-cyano-3,5,5-trimethylcyclohexylamine;

[0053] In step b), the mass ratio of KOH-ethanol solution to the added isophoronenitrile is 1:600, the molar ratio of NH3 to isophoronenitrile is 50:1, and the molar ratio of hydrogen to isophoronenitrile is 80:1;

[0054] c) In the presence of a hydrogenation catalyst Raney cobalt, the space velocity of the catalyst is 1.8 g 3-cyano-3,5,5-trimethylcyclohexanone / (ml catalyst·hour), hydrogen, NH3 and the product containing 3-aminomethyl-3,5,5-trimethylcyclohexylamine and 3-cyano-3,5,5-trimethylcyclohexylamine obtained in step b) are mixed and reacted in a 3% acetic acid-ethanol solution, and the reaction is carried out at a temperature of 120° C. and an absolute pressure of 18 MPa to convert 3-cyano-3,5,5-trimethylcyclohexylamine into 3-aminomethyl-3,5,5-trimethylcyclohexylamine. In step c), the mass ratio of the acetic acid-ethanol solution to the IPN obtained in step 1) is 1:500, the molar ratio of hydrogen to the IPN obtained in step 1) is 30:1, and the molar ratio of ammonia to the IPN obtained in step (1) is 50:1.

[0055] The method provided by Chinese patent CN107304168A was used to purify isophorone diamine to obtain a conventional IPDA composition, wherein the content of hydroxy nitrile compound was 0.00005 wt %.

[0056] (4) Preparation of IPDA compositions with different hydroxynitrile compound contents

[0057] The hydroxynitrile compound obtained in step (2) is blended into the conventional IPDA prepared in step (3) to obtain IPDA compositions with hydroxynitrile compound contents of 0.0003wt%, 0.001wt%, 0.005wt%, 0.01wt%, 0.02wt%, 0.04wt% and 0.1wt%, respectively.

[0058] Example 2 Preparation of IPDI compositions with different contents of chloronitrile compounds

[0059] The conventional IPDA composition (hydroxynitrile compound content of 0.00005 wt%) obtained in Example (1), and IPDA compositions having hydroxynitrile compound contents of 0.0003 wt%, 0.001 wt%, 0.005 wt%, 0.01 wt%, 0.02 wt%, 0.04 wt% and 0.1 wt%, respectively, were reacted with phosgene to obtain corresponding IPDI composition samples, which were named Sample 1, Sample 2, Sample 3, Sample 4, Sample 5, Sample 6, Sample 7 and Sample 8, respectively.

[0060] The specific method is: using the heater mentioned in Example 1 of Chinese patent CN105214568A, the obtained IPDA is gasified and heated to 355°C, and under the protection of nitrogen, the gaseous phosgene heated to 355°C is continuously added to the reactor through respective feed pipes for reaction, and the reaction pressure is 0.05MPa absolute pressure and the temperature is 360°C; wherein, the feed amount of IPDA is 800Kg / h, and the feed amount of phosgene is 3000Kg / h; the mixed gas after the reaction is rapidly cooled to 100°C with o-dichlorobenzene solution through a gas jet absorption device to obtain a photochemical liquid containing the product IPDI; excess phosgene is removed at 180°C and an absolute pressure of 0.1MPa to obtain a crude IPDI product without phosgene; and then the crude product is distilled by a distillation tower to obtain an IPDI composite product at 0.5KPa and a distillation range of 150-160°C.

[0061] Example 3 Evaluation of the reaction between IPDI composition and polyol

[0062] a) diluting the catalyst dibutyltin dilaurate (T12) with toluene to a concentration of 1% for standby use;

[0063] b) Add 67.5 g of PPG-2000 with a water content of 300 ppm to a 500 ml reactor, place the reactor in an 82° C. oil bath, and start stirring for preheating at a stirring speed of 180 r / min;

[0064] c) after the temperature in the reactor reaches 80° C., 0.3 g of the catalyst T12 prepared in step a) and 7.6 g of the IPDI composition are added to the reactor respectively, and reacted;

[0065] d) During the reaction process, samples were taken every 5 minutes to monitor the NCO content. When the NCO content no longer decreased, the reaction was judged to have stopped, heating was stopped, and the reaction time was recorded;

[0066] e) After the temperature of the reactor is lowered to room temperature, a sample is taken and the reaction solution is analyzed by area normalization through GPC to obtain the residual monomer content, and the chromaticity value thereof is measured by the method of GB / T605-2006.

[0067] In the example, six batches of IPDI compositions, namely samples 2, 3, 4, 5, 6 and 7, were tested respectively to obtain different batches of reaction solutions.

[0068] Comparative Example 1

[0069] The same method as in Example 3 was adopted, but the IPDI compositions used were samples 1 and 8, respectively, to obtain different batches of reaction solutions.

[0070]

[0071] The results in the table above show that the six batches of isophorone diisocyanate compositions tested in Example 3 have moderate reactivity with polyols, and the obtained reaction liquids have low color and turbidity, and the residual monomer content is below 0.01%, which is significantly superior to the comparative example.

[0072] The present invention illustrates the detailed method of the present invention through the above-mentioned embodiments, but the present invention is not limited to the above-mentioned detailed method, that is, it does not mean that the present invention must rely on the above-mentioned detailed method to be implemented. Those skilled in the art should understand that any improvement of the present invention, equivalent replacement of various raw materials of the product of the present invention, addition of auxiliary components, selection of specific methods, etc., all fall within the protection scope and disclosure scope of the present invention.

Claims

1. An isophorone diamine composition, characterized in that The content of the hydroxynitrile compound in the isophoronediamine composition is 0.0001-0.0500 wt %.

2. The composition according to claim 1, characterized in that The content of the hydroxynitrile compound in the isophoronediamine composition is 0.0001-0.0300 wt %.

3. The composition according to claim 1, characterized in that The content of the hydroxynitrile compound in the isophoronediamine composition is 0.0005-0.0300 wt %.

4. The composition according to any one of claims 1 to 3, characterized in that The hydroxynitrile compound is 3-nitrile-3,5,5-trimethylcyclohexanol.

5. The composition according to claim 1, characterized in that The preparation method of the hydroxynitrile compound comprises the following steps: a) in the presence of a hydrogenation catalyst, mixing hydrogen and isophoronenitrile in a 1-5wt% KOH ethanol solution to react to obtain 3-nitrile-3,5,5-trimethylcyclohexanol; b) separating and purifying the reaction product obtained in step a).

6. The composition according to claim 5, characterized in that The reaction temperature of the hydrogenation reaction in step a) is 50-200° C., preferably 50-150° C.; the pressure is 0.3-2 MPa, preferably 0.5-1.5 MPa; and the selected catalyst is Raney copper and / or Raney nickel.

7. The composition according to claim 5, characterized in that In the step a), the mass ratio of the hydrogenation catalyst to the reaction raw material isophoronenitrile is 1:100-1000, preferably 1:200-750.

8. An isophorone diisocyanate composition, characterized in that: The isophorone diamine composition according to any one of claims 1 to 7 is used as a raw material to carry out a phosgenation reaction.

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