High-activity and stable-storage polyisocyanate composition

Abstract

The invention discloses a high-activity and stable-storage polyisocyanate composition. The high-activity and stable-storage polyisocyanate composition comprises polyisocyanate which is obtained by reacting aliphatic diisocyanate and has an isocyanuric acid group, and a structural substance as shown in a formula I, according to the invention, the polyisocyanate composition is controlled to contain a certain amount of sulfonamide-containing isocyanate compounds, especially a certain amount of structural substances shown in the formula I, so that the viscosity of the polyisocyanate composition is stable, and meanwhile, relatively high application activity is kept. # imgabs0 #

Description

Technical Field

[0001] The invention relates to a polyisocyanate composition, in particular to a highly active and storage-stable polyisocyanate composition. Background Art

[0002] Isocyanurate-containing polyisocyanate compositions, especially aliphatic polyisocyanate compositions, are widely used in coatings, adhesives, sealants, elastomers and other industries, and have excellent properties such as weather resistance, wear resistance, and chemical corrosion resistance.

[0003] Patent documents US6730628B2, US6800714B2, and US7001973B2 report methods for synthesizing such polyisocyanate compositions. However, in order to ensure that the catalyst is completely poisoned during the synthesis process, the amount of catalyst poison added is often excessive, thereby reducing its activity during application. At the same time, a large amount of residual additives will also affect the storage stability of the polyisocyanate, causing its viscosity to increase.

[0004] To solve some of the above problems, CN113265037B adds ionic liquids or introduces hydrogen chloride or phosgene to control the pH of the aqueous extract, which can effectively improve the long-term storage stability of polyisocyanates. However, the introduction of the above substances often leads to poor compatibility of the product or toxic residues, and therefore, further solutions and improvements are urgently needed.

[0005] Patent CN117700689A adds an appropriate amount of 4-methoxybenzenesulfonamide during the amination reaction of isocyanate and alcohol, which can keep the viscosity of the product stable for a long time for more than 2 years. Although the addition of sulfonamide can improve the stability of the product, research has found that it will also reduce the reactivity of the polyisocyanate composition with the downstream hydroxy resin. Summary of the invention

[0006] In order to solve the above technical problems, the present invention proposes a highly active and storage-stable polyisocyanate composition. The inventors have conducted in-depth research and found that by controlling the polyisocyanate composition to contain a certain amount of isocyanate compounds containing sulfonamide groups, especially a certain amount of substances with structure of formula I, the viscosity of the polyisocyanate composition can be stabilized while maintaining a high application activity. Compared with the previous scheme, the sulfonamide-containing isocyanate compound has low toxicity and the presence of isocyanate groups makes the system more compatible.

[0007] To achieve the above purpose, the technical solution adopted by the present invention is as follows:

[0008] A highly active and storage-stable polyisocyanate composition, comprising a polyisocyanate having an isocyanuric acid group obtained by reacting an aliphatic diisocyanate and a substance having a structure of formula I;

[0009]

[0010] In formula I, R1 is selected from C5-C18 aryl, substituted aryl, preferably phenyl, p-benzyl; R2 is selected from C4-C13 straight chain alkane, branched alkane, cycloalkyl alkane, preferably hexamethylene, pentamethylene diisocyanate, isophorone, methylene dicyclohexyl.

[0011] In some preferred examples, the content of the substance of formula I is 0.5-200 ppm, preferably 50-200 ppm, such as 0.6, 1.0, 5.0, 10.0, 100, 150, 150, 180, 200 ppm, etc., relative to the total mass of the polyisocyanate composition.

[0012] In some preferred examples, the polyisocyanate composition further comprises a substance having a structure of formula II;

[0013]

[0014] In formula II, R3 is selected from C5-C18 aryl, substituted aryl, preferably phenyl, p-phenylmethyl; R4 and R5 are each independently selected from C4-C13 straight chain alkane, branched alkane, cycloalkyl alkane, preferably hexamethylene, pentamethylene diisocyanate, isophorone, methylene dicyclohexyl;

[0015] Preferably, the content of the substance of formula II is 0.3-50 ppm, preferably 1-30 ppm, such as 0.4, 0.5, 0.8, 1.0, 5.0, 10, 20, 30, 40, 50 ppm, etc., relative to the total mass of the polyisocyanate composition.

[0016] The polyisocyanate composition of the present invention, after further comprising the substance of formula II, can further improve the storage stability and downstream reaction activity of the product.

[0017] In the present invention, as the content of the structural substances of formula I and formula II increases, the storage stability and reactivity of the polyisocyanate composition are correspondingly improved, but when the content exceeds the upper limit disclosed in the present invention, the solvent resistance of the composition will be affected.

[0018] In some preferred examples, the functionality of the polyisocyanate composition is 3.1-3.9, such as 3.2, 3.3, 3.4, 3.5, 3.6, 3.7, 3.8, etc. The functionality of the polyisocyanate composition is calculated by the isocyanate group concentration and the number average molecular weight of the polyisocyanate composition, functionality = NCO% * 100 / (42 * Mn), wherein Mn is the number average molecular weight of the polyisocyanate composition, and the number average molecular weight of the polyisocyanate composition is obtained by molecular gel chromatography test. The functionality of the polyisocyanate composition of the present invention is in the range of 3.1-3.9, the composition has a lower viscosity, a high crosslinking density of the film-forming film, and good weather resistance. When the functionality of the composition is less than 3.1, the crosslinking density of the paint film formed by the composition is low, and the weather resistance of the paint film is poor; and when the functionality of the composition is greater than 3.9, the viscosity of the composition is relatively large, and the viscosity of the formulation system formed with it as a raw material also increases accordingly, affecting downstream applications.

[0019] In some preferred examples, the aliphatic diisocyanate is selected from at least one aliphatic diisocyanate that does not contain an ester group and contains 4 to 20 carbon atoms in addition to the NCO group, preferably at least one of hexamethylene diisocyanate, pentamethylene diisocyanate, isophorone diisocyanate, cyclohexyl dimethylene diisocyanate, dicyclohexylmethane diisocyanate, norbornane dimethylene diisocyanate, cyclohexyl diisocyanate, 2,4,4-trimethylhexamethylene diisocyanate, and methylcyclohexyl diisocyanate, and more preferably at least one of hexamethylene diisocyanate (HDI) and pentamethylene diisocyanate (PDI).

[0020] In some preferred examples, the molar concentration of allophanate groups in the polyisocyanate composition is less than 20%, preferably less than 5%. The molar concentration of allophanate groups can be detected by nuclear magnetic carbon spectrum, expressed as the ratio of the carbonyl absorption peak area of ​​allophanate groups to the total carbonyl absorption peak area in the polyisocyanate composition. When the ratio exceeds 20%, the viscosity stability of the polyisocyanate composition in long-term storage becomes poor.

[0021] In some preferred examples, the residual monomer content in the polyisocyanate composition is less than 0.5wt%, preferably less than 0.1wt%, such as 0.1wt%, 0.2wt%, 0.3wt%, 0.4wt%, etc. When the residual monomer content is controlled to be less than 0.5wt%, occupational hazards in downstream applications can be significantly reduced, and the cross-linking performance of the polyisocyanate composition is further improved. The residual monomer content in the polyisocyanate composition can be tested by gas chromatography.

[0022] The polyisocyanate composition of the present invention has a viscosity growth rate of less than 15% when treated at 100° C. / 24 h.

[0023] The highly active and storage-stable polyisocyanate composition of the present invention can be introduced into the sulfonamide group-containing isocyanate compound shown in Formula I by conventional methods, and the present invention has no special requirements.

[0024] The highly active and storage-stable polyisocyanate composition of the present invention can be introduced into the isocyanate compound represented by Formula II by conventional methods, and the present invention has no special requirements.

[0025] In the above method, the polyisocyanate composition based on aliphatic dicyanate is a polyisocyanate composition obtained by any method disclosed in the prior art using aliphatic diisocyanate as a polymerization monomer. During the preparation process, conventional means such as controlling the reaction conversion rate, modifying the auxiliary agent, optimizing the catalyst type, etc. can be used to control the allophanate content within the scope of the present invention, and to control the residual monomers, functionality and other indicators. The present invention does not make special requirements for the specific operation process.

[0026] Regarding the manufacture of the polyisocyanate composition based on aliphatic diisocyanate, it can be prepared by a method that has been disclosed in the field, and the present invention has no special requirements. It should be understood by those skilled in the art that the following preparation method is only an exemplary description of the source of the polyisocyanate composition product of the present invention, but does not constitute any limitation. For example, it is preferably carried out by using a catalyst to carry out a self-polymerization reaction of the diisocyanate monomer, stopping the reaction when the target conversion rate is reached, and removing the diisocyanate monomer.

[0027] As the isocyanurate reaction catalyst used at this time, a basic catalyst is generally preferred. Specifically, the following can be cited: (1) hydroxides of tetraalkylammonium such as tetramethylammonium and tetraethylammonium, organic weak acid salts of acetic acid and capric acid, etc.; (2) hydroxides of hydroxyalkylammonium such as trimethylhydroxypropylammonium, trimethylhydroxyethylammonium, triethylhydroxypropylammonium, triethylhydroxyethylammonium, organic weak acid salts of acetic acid and capric acid, etc.; (3) metal salts of tin, zinc, lead, etc. of alkylcarboxylic acids such as acetic acid, hexanoic acid, octanoic acid, myristic acid, etc.; (4) metal alcoholates such as sodium and potassium; (5) aminosilyl-containing compounds such as hexamethyldisilazane, etc.; (6) Mannich bases; (7) combined use of tertiary amines and epoxy compounds; (8) phosphorus compounds such as tributylphosphine, etc. The amount of these catalysts used can be selected from the range of 10 ppm to 10000 ppm, for example, 10, 50, 100, 1000, 3000, 5000, 7000, 9000, 10000 ppm relative to the amount of diisocyanate as a raw material. These catalysts can be deactivated by, for example, adding an acidic substance such as phosphoric acid or an acidic phosphate ester to neutralize the catalyst, thermal decomposition, chemical decomposition, etc., in order to terminate the reaction.

[0028] In the present invention, the catalyst is added in the form of an alcohol solution; preferably, the mass concentration of the catalyst in the alcohol is 0.25-50%, for example 0.25, 1, 5, 10, 20, 30, 40, 50%.

[0029] In one embodiment, the diluent used as the catalyst may be, but is not limited to, a monohydric alcohol and / or a dihydric alcohol; preferably, the alcohol is selected from one or more of C1-C10 aliphatic alcohols, aromatic aliphatic alcohols, aromatic alcohols, aliphatic phenols, aromatic aliphatic phenols and aromatic phenols. The monohydric alcohol is preferably present in the form of a straight-chain, branched or cyclic alcohol or phenol; the dihydric alcohol is not limited to the following, for example, ethylene glycol, 1,3-propylene glycol, 1,2-propylene glycol, 1,3-butylene glycol, 1,4-butylene glycol, 2,3-butylene glycol, 1,5-pentanediol, 1,2-pentanediol, 1,3-pentanediol, 1,4-pentanediol, neopentyl glycol, 1,6-hexanediol, 1,7-heptanediol, 1,8-octanediol, 1,9-nonanediol, 1,10-decanediol, diethylene glycol, polyethylene glycol, polypropylene glycol, polytetramethylene glycol, 2-methyl-1,3-propanediol, 3-methyl-1,5-pentanediol, 2-ethyl-1,3-hexanediol, 2-methyl-1,8-octanediol and one or more of 2,2-diethyl-1,3-propanediol.

[0030] In the present invention, it is preferred to remove the diisocyanate monomer by thin film evaporation after the reaction is stopped.

[0031] The pressures involved in the present invention are all absolute pressures.

[0032] Compared with the prior art, the technical solution of the present invention has the following beneficial effects:

[0033] (1) By controlling the weight of the sulfonamide group-containing isocyanate compound represented by Formula I in the polyisocyanate composition to be 0.5-200 ppm, the obtained polyisocyanate composition has higher activity and storage stability.

[0034] (2) By further adding the isocyanate compound represented by formula II, the implementation effect of the present invention can be further improved.

[0035] (3) The preparation process is simple, has broad spectrum, and is easy to industrialize. DETAILED DESCRIPTION

[0036] The present invention is further described below by means of specific examples. The examples described in the present invention are only used to illustrate the present invention and do not limit the scope of the present invention.

[0037] The main raw material information in the following examples of the present invention is as follows:

[0038] 1,6-Hexamethylene diisocyanate, HDI, Wanhua Chemical;

[0039] Isophorone diisocyanate, IPDI, Wanhua Chemical;

[0040] 1-Butanol, purity ≥99%, Sigma-Aldrich;

[0041] Tetraethylammonium hydroxide solution (25%, methanol solution), Sigma-Aldrich;

[0042] p-Toluenesulfonic acid, purity ≥99%, Sigma-Aldrich;

[0043] Benzoic acid, purity ≥99%, Sigma-Aldrich;

[0044] Cerium oxide, purity ≥99%, Sigma-Aldrich;

[0045] Bismuth isooctanoate, purity ≥99%, MacLean;

[0046] 4-Methylbenzenesulfonamide, purity ≥99, Aladdin;

[0047] High hydroxyl resin, Tongde ACR6780;

[0048] Other materials, unless otherwise specified, are common commercially available raw materials.

[0049] The main detection methods involved in the following embodiments of the present invention are:

[0050] The content of each group in the polyisocyanate composition: the molar ratio of isocyanurate group can be quantified by the composition 13 C-NMR test. The specific test conditions are as follows:

[0051] 13 C-NMR equipment: AVANCE600 (Bruker)

[0052] BBO probe (Bruker)

[0053] Sample concentration: 30wt%

[0054] Resonance frequency: 150MHz

[0055] Displacement standard: 77.0ppm (CDCl3)

[0056] Pulse program: zgig30

[0057] Spectral width: 240ppm

[0058] Spectrum center: 100ppm

[0059] Isocyanurate group: integral value around 148.5ppm, uretdione group: integral value around 157.3ppm, allophanate group: sum of integral values ​​around 154ppm and 153ppm, carbamate group: integral value around 156.3ppm, uretonimine group: integral value around 149.8ppm;

[0060] Allophanate content: (integral value near 154ppm + integral value near 153ppm) / (integral value near 148.5ppm + integral value near 157.3ppm + integral value near 154ppm + integral value near 153ppm + integral value near 156.3ppm + integral value near 149.8ppm)

[0061] The present invention is based on the method of GB / T18583-2008, and uses an Agilent GC-7890B gas chromatograph manufactured by Agilent to determine the residual monomer content in the reaction system;

[0062] Functionality: functionality of the polyisocyanate composition = NCO%*100 / (42*Mn), where Mn is the number average molecular weight of the polyisocyanate composition;

[0063] Number average molecular weight Mn: The number average molecular weight Mn of the polyisocyanate composition of the present invention can be determined by GPC (gel chromatography) testing. The specific test conditions are as follows:

[0064] GPC equipment: Agilent1260

[0065] GPC columns: Pl1113-6520 and Pl113-6325 (Agilent)

[0066] Sample concentration: 3wt%

[0067] Mobile phase: tetrahydrofuran

[0068] Detection method: differential detector

[0069] Flow rate: 1ml / min

[0070] Column temperature: 35°C

[0071] The standard curve used polystyrene with a molecular weight range of 162-17900.

[0072] Drying (surface drying) test: GB / T 1728;

[0073] Solvent resistance wiping: GB / T 23989-2009 Coating solvent resistance test wiping method

[0074] Viscosity growth rate of the polyisocyanate composition: Under a nitrogen environment, the polyisocyanate was placed in an oven at 100°C for 24 hours, and its viscosity before and after placement was tested; Viscosity growth rate: (viscosity of the polyisocyanate placed in an oven at 100°C for 24 hours - initial viscosity of the polyisocyanate) / initial viscosity of the polyisocyanate.

[0075] The main equipment used in the following embodiments of the present invention are:

[0076] Two-stage thin film evaporator, first-stage evaporator area 0.1m 2 , secondary evaporator area 0.05m 2 ;

[0077] Reactor, volume 5L, anchor type stirring paddle, rotating diameter 100mm.

[0078] Synthesis example 1

[0079] Preparation of sulfonamide-containing isocyanate compound a shown in formula I:

[0080] Under a nitrogen atmosphere, 3000 g of the starting diisocyanate IPDI was added to a 5 L reaction container for mixing. The system temperature was raised to 140 ° C while stirring. 255 g of p-toluenesulfonic acid was added to the system at one time, and 5 g of cerium oxide was added. After reacting for 3 hours, the reaction temperature was further raised to 180 ° C and the reaction was continued for 3 hours. After the reaction was completed, the reaction temperature was lowered to room temperature, filtered, and purified using a thin film evaporator. The feed temperature was 50 ° C, the feed amount was 0.5 Kg / h, the primary separation temperature and pressure was 100 ° C, the primary absolute pressure was 80 Pa, the secondary separation temperature and pressure was 100 ° C, the secondary absolute pressure was 10 Pa, and the remaining IPDI monomer was removed to obtain a sulfonamide-containing isocyanate compound a shown in the following formula.

[0081]

[0082] 1 H NMR (400MHz, CDCl3): δ7.84(bs,1H,),7.74(d,2H,),7.40(d,2H,),3.36(s,2H),2.99(m,1H), 2.34(s,3H,),1.71(m,2H),1.46(m,2H),1.41(m,1H,),1.16(m,1H,),1.04(s,3H),0.99(s,6H)

[0083] Synthesis example 2

[0084] Preparation of isocyanate compound b shown in formula II:

[0085] Under a nitrogen atmosphere, 2000 g of the starting diisocyanate IPDI and 500 g of the sulfonamide-containing isocyanate compound a shown in formula I were added to a 5 L reaction container for mixing, the system temperature was raised to 140 ° C. under stirring, 0.5 g of bismuth isooctanoate was added dropwise to the system for reaction for 3 hours, and after the reaction was completed, the reaction temperature was lowered to room temperature and purified using a thin film evaporator, the feed temperature was 50 ° C., the feed amount was 0.5 Kg / h, the primary separation temperature and pressure was 130 ° C., the primary absolute pressure was 80 Pa, the secondary separation temperature and pressure was 130 ° C., the secondary absolute pressure was 10 Pa, and the remaining IPDI monomer was removed to obtain the isocyanate compound b shown in the following formula.

[0086]

[0087] 1 H NMR (400MHz, CDCl3): δ7.74(d,2H,),7.40(d,2H,),6.0(bs,1H,),3.36(s,2H),3.22(m,1H),3.21(m,2H),2.99(m,1H),2.34(s,3H,),1.71( m,2H),1.50(m,2H),1.46(m,2H),1.41(m,1H,),1.39(m,2H),1.21(m, 2H),1.16(m,1H,),1.04(s,3H),1.02(s,3H),0.99(s,6H),0.97(s,6H)

[0088] Synthesis example 3

[0089] Under nitrogen atmosphere, 3000g of starting diisocyanate HDI was preheated to 70°C, 4.5g of 10wt% tetraethylammonium hydroxide (25% tetraethylammonium hydroxide and 1-butanol) was added, and the NCO% of the reaction solution was tracked and measured. When the NCO% value dropped to 43.8%, 1.5g of diisooctyl phosphate was added to terminate the reaction. A thin film evaporator was used with a feed temperature of 80°C, a feed rate of 1Kg / h, a primary separation temperature and pressure of 160°C, a primary absolute pressure of 80Pa, a secondary separation temperature and pressure of 160°C, and a secondary absolute pressure of 10Pa to remove unreacted HDI monomers to obtain a polyisocyanate composition c.

[0090] Free hexamethylene diisocyanate content: 0.07%;

[0091] Allophanate content: 1.2%;

[0092] Functionality: 3.4.

[0093] Example 1

[0094] Preparation of a highly active and storage-stable polyisocyanate composition A based on HDI:

[0095] Under nitrogen conditions, 0.001 g of compound a (provided in Synthesis Example 1) and 1000 g of polyisocyanate composition c (provided in Synthesis Example 3) were mixed to obtain polyisocyanate composition A.

[0096] Compound a content: 1ppm

[0097] Free hexamethylene diisocyanate content: 0.07%;

[0098] Allophanate content: 1.2%.

[0099] Example 2

[0100] Preparation of a highly active and storage-stable polyisocyanate composition B based on HDI:

[0101] Under nitrogen conditions, 0.05 g of compound a (provided in Synthesis Example 1) and 1000 g of polyisocyanate composition c (provided in Synthesis Example 3) were mixed to obtain polyisocyanate composition B.

[0102] Compound a content: 50ppm

[0103] Free hexamethylene diisocyanate content: 0.07%;

[0104] Allophanate content: 1.2%.

[0105] Example 3

[0106] Preparation of a highly active and storage-stable polyisocyanate composition C based on HDI:

[0107] Under nitrogen conditions, 0.2 g of compound a (provided in Synthesis Example 1) and 1000 g of polyisocyanate composition c (provided in Synthesis Example 3) were mixed to obtain polyisocyanate composition C.

[0108] Compound a content: 200ppm

[0109] Free hexamethylene diisocyanate content: 0.07%;

[0110] Allophanate content: 1.2%.

[0111] Example 4

[0112] Preparation of a highly active and storage-stable polyisocyanate composition D based on HDI:

[0113] Under nitrogen conditions, 0.2 g of compound a (provided in Synthesis Example 1), 0.005 g of compound b (provided in Synthesis Example 2) and 1000 g of polyisocyanate composition c (provided in Synthesis Example 3) were mixed to obtain polyisocyanate composition D.

[0114] Compound a content: 200ppm

[0115] Compound b content: 5ppm

[0116] Free hexamethylene diisocyanate content: 0.07%;

[0117] Allophanate content: 1.2%.

[0118] Example 5

[0119] Preparation of highly active and storage-stable polyisocyanate composition E based on HDI:

[0120] Under nitrogen conditions, 0.2 g of compound a (provided in Synthesis Example 1), 0.02 g of compound b (provided in Synthesis Example 2) and 1000 g of polyisocyanate composition c (provided in Synthesis Example 3) were mixed to obtain polyisocyanate composition E.

[0121] Compound a content: 200ppm

[0122] Compound b content: 20ppm

[0123] Free hexamethylene diisocyanate content: 0.07%;

[0124] Allophanate content: 1.2%.

[0125] Comparative Example 1

[0126] Polyisocyanate composition c obtained in Synthesis Example 3.

[0127] Comparative Example 2

[0128] Under nitrogen conditions, 0.5 g of compound a (provided in Synthesis Example 1) and 1000 g of polyisocyanate composition c were mixed to obtain polyisocyanate composition B'.

[0129] Compound a content: 500ppm

[0130] Free hexamethylene diisocyanate content: 0.07%;

[0131] Allophanate content: 1.2%.

[0132] Comparative Example 3

[0133] Under nitrogen conditions, 0.05 g of compound b (provided in Synthesis Example 2) and 1000 g of polyisocyanate composition c (provided in Synthesis Example 3) were mixed to obtain polyisocyanate composition C'.

[0134] Compound b content: 50ppm

[0135] Free hexamethylene diisocyanate content: 0.07%;

[0136] Allophanate content: 1.2%.

[0137] Comparative Example 4

[0138] Under nitrogen conditions, 1.8 g of 4-methylbenzenesulfonamide and 1000 g of polyisocyanate composition c were mixed to obtain polyisocyanate composition D'.

[0139] 4-Methylbenzenesulfonamide content: 1800ppm

[0140] Free hexamethylene diisocyanate content: 0.07%;

[0141] Allophanate content: 1.2%.

[0142] Application Examples

[0143] The polyisocyanate compositions in Examples 1-5 and Comparative Examples 1-4 were used as raw materials, respectively, and mixed with a high hydroxyl resin (Tongde ACR6780) at an NCO / OH molar ratio of 1:1, and then a mixed solvent of ethyl acetate / xylene was added for dilution, wherein the content of the polyisocyanate composition in the solution formed by the polyisocyanate composition (curing agent) and ethyl acetate / xylene was 40wt%, and finally a paint was prepared.

[0144] The drying time, solvent resistance and viscosity growth rate of each paint were tested. The results are shown in Table 1.

[0145] Table 1. Performance test results

[0146] Polyisocyanate composition A B C D E c B’ C’ D’ Drying time / min 43 47 45 48 50 60 50 55 70 Solvent resistance / times ＞400 ＞400 ＞400 ＞400 ＞400 ＞400 250 ≥400 350 Viscosity growth rate / % 14.5％ 10％ 4％ 2％ 1.5％ 30％ 5％ 20％ 20％

[0147] The above is only a preferred embodiment of the present invention. It should be pointed out that ordinary technicians in this field can make several improvements and supplements without departing from the method of the present invention. These improvements and supplements should also be regarded as the scope of protection of the present invention.

Claims

1. A highly active and storage-stable polyisocyanate composition, characterized in that: Including polyisocyanates having isocyanuric groups obtained by reacting aliphatic diisocyanates and substances having a structure of formula I; In formula I, R1 is selected from C5-C18 aryl, substituted aryl, preferably phenyl, p-benzyl; R2 is selected from C4-C13 straight chain alkane, branched alkane, cycloalkyl alkane, preferably hexamethylene, pentamethylene diisocyanate, isophorone, methylene dicyclohexyl.

2. The highly active and storage-stable polyisocyanate composition according to claim 1, characterized in that: The content of the substance of formula I is 0.5-200 ppm, preferably 50-200 ppm, relative to the total mass of the polyisocyanate composition.

3. The highly active and storage-stable polyisocyanate composition according to claim 1 or 2, characterized in that: The polyisocyanate composition further comprises a substance of formula II; In formula II, R3 is selected from C5-C18 aryl, substituted aryl, R4 and R5 are each independently selected from C4-C13 straight chain alkane, branched alkane, cycloalkyl-containing alkane; Preferably, the content of the substance of formula II is 0.3-50 ppm, preferably 1-30 ppm, relative to the total mass of the polyisocyanate composition.

4. The highly active and storage-stable polyisocyanate composition according to any one of claims 1 to 3, characterized in that: The functionality of the polyisocyanate composition is 3.1-3.

9.

5. The highly active and storage-stable polyisocyanate composition according to any one of claims 1 to 4, characterized in that: The aliphatic diisocyanate is selected from at least one aliphatic diisocyanate that does not contain an ester group and contains 4 to 20 carbon atoms in addition to the NCO group, preferably at least one of hexamethylene diisocyanate, pentamethylene diisocyanate, isophorone diisocyanate, cyclohexyl dimethylene diisocyanate, dicyclohexylmethane diisocyanate, norbornane dimethylene diisocyanate, cyclohexyl diisocyanate, 2,4,4-trimethylhexamethylene diisocyanate, and methylcyclohexyl diisocyanate.

6. The highly active and storage-stable polyisocyanate composition according to any one of claims 1 to 5, characterized in that: The molar concentration of allophanate groups in the polyisocyanate composition is less than 20%, preferably less than 5%.

7. The highly active and storage-stable polyisocyanate composition according to any one of claims 1 to 6, characterized in that: The residual monomer content in the polyisocyanate composition is less than 0.5 wt %, preferably less than 0.1 wt %.

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