A highly reactive and storage-stable polyisocyanate composition

Abstract

The application discloses a high-activity and storage-stable polyisocyanate composition, which comprises a polyisocyanate with an isocyanuric acid group obtained by reacting an aliphatic diisocyanate and a substance with the structure of formula I; by controlling the polyisocyanate composition to contain a certain amount of an isocyanate compound containing a sulfonamide group, especially a certain amount of the substance with the structure of formula I, the viscosity of the polyisocyanate composition can be stabilized while the application activity is kept high.

Description

Technical Field

[0001] This invention relates to a polyisocyanate composition, and more particularly to a highly active and storage-stable polyisocyanate composition. Background Technology

[0002] Polyisocyanate compositions containing isocyanurates, especially aliphatic polyisocyanate compositions, are widely used in industries such as coatings, adhesives, sealants, and elastomers, 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 complete poisoning of the catalyst during the synthesis process, the amount of catalyst poison added is often excessive, which reduces its activity during application. At the same time, the residual amount of a large amount of additives can also affect the storage stability of polyisocyanates, causing their viscosity to increase.

[0004] To address some of the aforementioned issues, CN113265037B describes adding ionic liquids or introducing 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 these substances often leads to poor product compatibility or toxic residues; therefore, further solutions and improvements are urgently needed.

[0005] Patent CN117700689A describes a method to maintain product viscosity stability for over two years by adding an appropriate amount of 4-methoxybenzenesulfonamide during the urethane reaction of isocyanate and alcohol. While adding sulfonamide improves product stability, research has found that it also reduces the reactivity of the polyisocyanate composition with downstream hydroxyl resins. Summary of the Invention

[0006] To address the aforementioned technical problems, this invention proposes a highly active and storage-stable polyisocyanate composition. The inventors conducted in-depth research and discovered that by controlling the content of a certain amount of sulfonamide-containing isocyanate compounds in the polyisocyanate composition, especially a certain amount of substances with Formula I structure, it is possible to achieve viscosity stability while maintaining high application activity. Compared to previous methods, the sulfonamide-containing isocyanate compounds have lower toxicity, and the presence of isocyanate ions improves system compatibility.

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

[0008] A highly active and storage-stable polyisocyanate composition comprising a polyisocyanate having isocyanuric acid groups obtained by reacting aliphatic diisocyanates and a substance of formula I.

[0009]

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

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

[0012] In some preferred embodiments, the polyisocyanate composition further includes a substance of formula II;

[0013]

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

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

[0016] The polyisocyanate composition of the present invention, by further including a substance of formula II, can further improve the storage stability and downstream reactivity of the product.

[0017] In this invention, as the content of the substances of Formula I and Formula II increases, the storage stability and reactivity of the polyisocyanate composition are correspondingly improved. However, when the content exceeds the upper limit disclosed in this invention, it will affect the solvent resistance of the composition.

[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 using the isocyanate group concentration and the number-average molecular weight of the polyisocyanate composition: Functionality = NCO% * 100 / (42 * Mn), where Mn is the number-average molecular weight of the polyisocyanate composition, obtained by molecular gel chromatography. The polyisocyanate composition of this invention has a functionality in the range of 3.1-3.9, exhibiting low viscosity, high crosslinking density in the film-forming process, and good weather resistance. When the functionality of the composition is less than 3.1, the crosslinking density of the paint film is low, resulting in poor weather resistance; while when the functionality is greater than 3.9, the viscosity of the composition is high, and the viscosity of the formulation system formed using it as a raw material also increases accordingly, affecting downstream applications.

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

[0020] In some preferred examples, the molar concentration of urea-formate groups in the polyisocyanate composition is less than 20%, preferably less than 5%. The molar concentration of urea-formate groups can be detected by carbon NMR spectroscopy and is expressed as the ratio of the carbonyl absorption peak area of ​​urea-formate groups to the total carbonyl absorption peak area in the polyisocyanate composition. When this ratio exceeds 20%, the viscosity stability of the polyisocyanate composition deteriorates during long-term storage.

[0021] In some preferred embodiments, the monomer residue in the polyisocyanate composition is less than 0.5 wt%, preferably less than 0.1 wt%, for example, 0.1 wt%, 0.2 wt%, 0.3 wt%, 0.4 wt%, etc. Controlling the monomer residue to less than 0.5 wt% can significantly reduce occupational hazards in downstream applications, while further improving the crosslinking properties of the polyisocyanate composition. The monomer residue content in the polyisocyanate composition can be tested by gas chromatography.

[0022] The polyisocyanate composition described in this invention exhibits a viscosity increase rate of less than 15% when treated at 100°C for 24 hours.

[0023] The present invention provides a highly active and storage-stable polyisocyanate composition, which can introduce the sulfonamide-containing isocyanate compound of Formula I by conventional methods, without any particular requirement in the present invention.

[0024] The present invention provides a highly active and storage-stable polyisocyanate composition, which can be introduced by conventional methods containing an isocyanate compound represented by Formula II, without any particular requirement in the present invention.

[0025] In the above method, the polyisocyanate composition based on aliphatic diisocyanate is a polyisocyanate composition prepared by any method disclosed in the prior art using aliphatic diisocyanate as the polymerizing monomer. In this preparation process, conventional means such as controlling the reaction conversion rate, modifying the additives, and optimizing the type of catalyst can be used to control the urea carbamate content within the range of the present invention, as well as to control indicators such as residual monomer and functionality. The present invention does not make special requirements for the specific operation process.

[0026] Regarding the manufacture of polyisocyanate compositions based on aliphatic diisocyanates, methods already disclosed in the art can be used. This invention does not impose any particular requirements, and those skilled in the art should understand that the following preparation method is merely an illustrative description of the source of the polyisocyanate composition product of this invention, and does not constitute any limitation. For example, it is preferable to use a catalyst to carry out the self-polymerization reaction of the diisocyanate monomer, stop the reaction when the target conversion rate is reached, and remove the diisocyanate monomer.

[0027] As the catalyst for the isocyanurate esterification reaction used at this time, a basic catalyst is generally preferred. Specifically, examples include: (1) organic weak acid salts such as hydroxides of tetraalkylammonium such as tetramethylammonium and tetraethylammonium, acetic acid, and decanoic acid; (2) organic weak acid salts such as hydroxides of hydroxyalkylammonium such as trimethylhydroxypropylammonium, trimethylhydroxyethylammonium, triethylhydroxypropylammonium, and triethylhydroxyethylammonium, acetic acid, and decanoic acid; (3) metal salts such as tin, zinc, and lead of alkyl carboxylic acids such as acetic acid, hexanoic acid, octanoic acid, and myristic acid; (4) metal alkoxides such as sodium and potassium; (5) compounds containing aminosilyl groups such as hexamethyldisilazane; (6) Mannich bases; (7) combinations of tertiary amines and epoxy compounds; and (8) phosphorus compounds such as tributylphosphine. Regarding the amount of these catalysts used, relative to the amount of diisocyanate used as a raw material, they can be selected from a range of 10 ppm to 10,000 ppm, for example, 10, 50, 100, 1000, 3000, 5000, 7000, 9000, and 10000 ppm. To terminate the reaction, these catalysts can be deactivated, for example, by adding acidic substances such as neutralizing phosphoric acid or acidic phosphate esters, thermal decomposition, or chemical decomposition.

[0028] In this 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 a 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, aryl aliphatic alcohols, aromatic alcohols, aliphatic phenols, aryl 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, but may include, for example, one or more of ethylene glycol, 1,3-propanediol, 1,2-propanediol, 1,3-butanediol, 1,4-butanediol, 2,3-butanediol, 1,5-pentanediol, 1,2-pentanediol, 1,3-pentanediol, 1,4-pentanediol, neopentanediol, 1,6-hexanediol, 1,7-heptanediol, 1,8-octanediol, 1,9-nonanediol, 1,10-decanediol, diethylene glycol, polyethylene glycol, polypropylene glycol, polytetramethylenediol, 2-methyl-1,3-propanediol, 3-methyl-1,5-pentanediol, 2-ethyl-1,3-hexanediol, 2-methyl-1,8-octanediol, and 2,2-diethyl-1,3-propanediol.

[0030] In this invention, it is preferable to remove the diisocyanate monomer by film evaporation after the reaction has stopped.

[0031] All pressures involved in this invention are absolute pressures.

[0032] Compared with the prior art, the beneficial effects of the technical solution of the present invention are as follows:

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

[0034] (2) By further adding the isocyanate compound shown in Formula II, the implementation effect of the present invention can be further improved.

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

[0036] The present invention will be further illustrated below with specific embodiments. These embodiments are merely illustrative and do not limit the scope of the invention.

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

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

[0039] Isoflurone 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's;

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

[0047] High hydroxyl resin, Tongde ACR6780;

[0048] Unless otherwise specified, all other ingredients are ordinary 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 groups can be quantified by the composition. 13 The result is determined using C-NMR spectroscopy. The specific test conditions are as follows:

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

[0052] BBO probe (Bruker)

[0053] Sample concentration: 30 wt%

[0054] Resonant frequency: 150MHz

[0055] Displacement reference: 77.0 ppm (CDCl3)

[0056] Pulse program: zgig30

[0057] Spectral width: 240ppm

[0058] Spectral center: 100ppm

[0059] Isocyanurate group: integral value around 148.5 ppm, diuret group: integral value around 157.3 ppm, urethane group: sum of integral values ​​around 154 ppm and 153 ppm, carbamate: integral value around 156.3 ppm, urea ketimino group: integral value around 149.8 ppm;

[0060] Urea carbamate content: (integral value around 154ppm + integral value around 153ppm) / (integral value around 148.5ppm + integral value around 157.3ppm + integral value around 154ppm + integral value around 153ppm + integral value around 156.3ppm + integral value around 149.8ppm)

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

[0062] Functionality: The 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 in the polyisocyanate composition of this invention can be determined by GPC (molecular gel chromatography). The specific test conditions are as follows:

[0064] GPC equipment: Agilent 1260

[0065] GPC pillars: PL1113-6520 and PL113-6325 (Agilent)

[0066] Sample concentration: 3wt%

[0067] Mobile phase: Tetrahydrofuran

[0068] Detection method: Differential detector

[0069] Flow rate: 1 ml / min

[0070] Column temperature: 35℃

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

[0072] Dryness (surface dryness) test: GB / T 1728;

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

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

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

[0076] Two-stage thin-film evaporator, with the first-stage evaporator having an area of ​​0.1 m². 2 The secondary evaporator has an area of ​​0.05m². 2 ;

[0077] The reactor has a volume of 5L and an anchor-type agitator with a rotation diameter of 100mm.

[0078] Synthesis example 1

[0079] Preparation of isocyanate compound a containing sulfonamide group as shown in Formula I:

[0080] Under a nitrogen atmosphere, 3000g of starting diisocyanate IPDI was added to a 5L reaction vessel and mixed. The system temperature was raised to 140℃ with stirring. 255g of p-toluenesulfonic acid and 5g of cerium oxide were added to the system at once. After reacting for 3 hours, the reaction temperature was raised to 180℃ and the reaction was continued for another 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℃, the feed rate was 0.5Kg / h, the first-stage separation temperature and pressure were 100℃, the first-stage absolute pressure was 80Pa, the second-stage separation temperature and pressure were 100℃, and the second-stage absolute pressure was 10Pa. The remaining IPDI monomer was removed to obtain the isocyanate compound a containing sulfonamide groups as 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 as shown in Formula II:

[0085] Under a nitrogen atmosphere, 2000g of starting diisocyanate IPDI and 500g of isocyanate compound a containing sulfonamide groups (as shown in Formula I) were added to a 5L reaction vessel and mixed. The system temperature was raised to 140°C with stirring. 0.5g of bismuth isooctanoate was added dropwise to the system and reacted for 3 hours. After the reaction was completed, the reaction temperature was lowered to room temperature. Purification was carried out using a thin-film evaporator with a feed temperature of 50°C, a feed rate of 0.5 kg / h, a first-stage separation temperature and pressure of 130°C and a first-stage absolute pressure of 80 Pa, a second-stage separation temperature and pressure of 130°C and a second-stage absolute pressure of 10 Pa, and the remaining IPDI monomer was removed to obtain isocyanate compound b (as shown in Formula I).

[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 a nitrogen atmosphere, 3000g of starting diisocyanate (HDI) was preheated to 70°C. 4.5g of 10wt% tetraethylammonium hydroxide (prepared from 25% tetraethylammonium hydroxide and 1-butanol) was added, and the NCO% of the reaction solution was monitored. 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 first-stage separation temperature and pressure of 160°C, a first-stage absolute pressure of 80Pa, a second-stage separation temperature and pressure of 160°C, and a second-stage absolute pressure of 10Pa to remove unreacted HDI monomers, yielding polyisocyanate composition c.

[0090] Free hexamethylene diisocyanate content: 0.07%;

[0091] Urea carbamate content: 1.2%;

[0092] Functionality: 3.4.

[0093] Example 1

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

[0095] Under nitrogen atmosphere, 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: 1 ppm

[0097] Free hexamethylene diisocyanate content: 0.07%;

[0098] Urea carbamate content: 1.2%.

[0099] Example 2

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

[0101] Under nitrogen atmosphere, 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: 50 ppm

[0103] Free hexamethylene diisocyanate content: 0.07%;

[0104] Urea carbamate content: 1.2%.

[0105] Example 3

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

[0107] Under nitrogen atmosphere, 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: 200 ppm

[0109] Free hexamethylene diisocyanate content: 0.07%;

[0110] Urea carbamate content: 1.2%.

[0111] Example 4

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

[0113] Under nitrogen atmosphere, 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: 200 ppm

[0115] Compound b content: 5 ppm

[0116] Free hexamethylene diisocyanate content: 0.07%;

[0117] Urea carbamate content: 1.2%.

[0118] Example 5

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

[0120] Under nitrogen atmosphere, 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: 200 ppm

[0122] Compound b content: 20 ppm

[0123] Free hexamethylene diisocyanate content: 0.07%;

[0124] Urea carbamate content: 1.2%.

[0125] Comparative Example 1

[0126] Polyisocyanate composition c obtained by synthesis example 3.

[0127] Comparative Example 2

[0128] Under nitrogen atmosphere, 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: 500 ppm

[0130] Free hexamethylene diisocyanate content: 0.07%;

[0131] Urea carbamate content: 1.2%.

[0132] Comparative Example 3

[0133] Under nitrogen atmosphere, 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: 50 ppm

[0135] Free hexamethylene diisocyanate content: 0.07%;

[0136] Urea carbamate content: 1.2%.

[0137] Comparative Example 4

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

[0139] 4-Methylbenzenesulfonamide content: 1800 ppm

[0140] Free hexamethylene diisocyanate content: 0.07%;

[0141] Urea carbamate content: 1.2%.

[0142] Application examples

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

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

[0145] Table 1. Performance Test Results

[0146] Drying time / min 43 47 45 48 50 60 50 55 70 Solvent resistance / time ＞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 description is only a preferred embodiment of the present invention. It should be noted that those skilled in the art can make several improvements and additions without departing from the method of the present invention, and these improvements and additions should also be considered within the scope of protection of the present invention.

Claims

1. A highly active and storage-stable polyisocyanate composition, characterized in that, This includes polyisocyanates with isocyanuric acid groups obtained from the reaction of aliphatic diisocyanates, as well as formulas... Structural materials; Mode , Mode In this context, R1 is selected from C5-C18 aryl and substituted aryl groups; R2 is selected from C4-C13 straight-chain alkane groups, branched alkane groups, and cycloalkyl alkane groups. Mode The content of the structural substance relative to the total mass of the polyisocyanate composition is 0.5-200 ppm; The aliphatic diisocyanate is selected from at least one of aliphatic diisocyanates that do not contain an ester group and contain 4-20 carbon atoms in addition to an NCO group.

2. The highly active and storage-stable polyisocyanate composition according to claim 1, characterized in that, Mode In this context, R1 is selected from phenyl or p-phenylmethyl.

3. The highly active and storage-stable polyisocyanate composition according to claim 1, characterized in that, Mode In this context, R2 is selected from hexamethylene, pentamethylene, isophorone, and methylene dicyclohexyl.

4. The highly active and storage-stable polyisocyanate composition according to claim 1, characterized in that, Mode The content of the structural material relative to the total mass of the polyisocyanate composition is 50-200 ppm.

5. The highly active and storage-stable polyisocyanate composition according to any one of claims 1-4, characterized in that, The polyisocyanate composition also includes the formula Structural materials; Mode , Mode In this context, R3 is selected from C5-C18 aryl and substituted aryl groups, while R4 and R5 are each independently selected from C4-C13 straight-chain alkane groups, branched alkane groups, and cycloalkyl alkane groups.

6. The highly active and storage-stable polyisocyanate composition according to claim 5, characterized in that, Mode The content of the structural material relative to the total mass of the polyisocyanate composition is 0.3-50 ppm.

7. The highly active and storage-stable polyisocyanate composition according to claim 6, characterized in that, Mode The content of the structural material relative to the total mass of the polyisocyanate composition is 1-30 ppm.

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

9.

9. The highly active and storage-stable polyisocyanate composition according to claim 1, characterized in that, The aliphatic diisocyanate is selected from at least one of hexamethylene diisocyanate, pentamethylene diisocyanate, isophorone diisocyanate, cyclohexyldimethylene diisocyanate, dicyclohexylmethane diisocyanate, norbornene dimethylene diisocyanate, cyclohexyl diisocyanate, 2,4,4-trimethylhexane diisocyanate, and methylcyclohexyl diisocyanate.

10. The highly active and storage-stable polyisocyanate composition according to any one of claims 1-4, characterized in that, The molar concentration of urea-formate groups in the polyisocyanate composition is less than 20%.

11. The highly active and storage-stable polyisocyanate composition according to claim 10, characterized in that, The molar concentration of urea-formate groups in the polyisocyanate composition is less than 5%.

12. The highly active and storage-stable polyisocyanate composition according to any one of claims 1-4, characterized in that, The residual monomer content in the polyisocyanate composition is less than 0.5 wt%.

13. The highly active and storage-stable polyisocyanate composition according to claim 12, characterized in that, The residual monomer content in the polyisocyanate composition is less than 0.1 wt%.

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