Compound, treatment agent, and use thereof

Abstract

A compound, a treatment agent, and a use thereof. Raw materials for preparing the compound comprise an isocyanate group-containing compound and an isocyanate reactive compound as shown in formula I. The compound can be used for the treatment of fiber fabrics, leather, non-woven fabrics, asbestos, fur, concrete, stones, paper products, plastics, or coatings, wherein the treatment can make the surfaces of articles have a water-repellent and oil-repellent function or an antifouling function.

Description

Compounds, treatment agents and their applications

[0001] CROSS-REFERENCE TO RELATED APPLICATIONS

[0002] This application claims priority to the Chinese patent application with application number 202310989101.5 filed on August 7, 2023, and invention name “Compounds, Treatment Agents and Their Applications”. The entire contents of the above patent application are incorporated into this application in their entirety. Technical Field

[0003] The present application relates to a compound, a treatment agent, and applications thereof. The compound of the present application can be used to treat fiber fabrics, leather, non-woven fabrics, asbestos, fur, concrete, stone, paper products, plastics, or coatings, and the treatment can impart water- and oil-repellent or antifouling properties to the surface of the article. Technical Background

[0004] In the past, fluoropolymers have been used to treat the surfaces of various items such as fiber fabrics for water and oil repellency or antifouling. Due to their low surface tension, fluoropolymers can change the surface properties of fiber fabrics without affecting their appearance, so they have been widely used.

[0005] However, in recent years, due to the increasing international attention on polyfluoroalkyl substances (PFAS), in March 2023, the European Chemicals Agency (ECHA) launched a public consultation on the proposal submitted by Denmark, Germany, the Netherlands, Norway and Sweden to ECHA to add restrictions on the manufacture, placing on the market and use of PFAS in the REACH restriction chapter (REACH Annex XIVII). The purpose is to give relevant parties the opportunity to express their opinions on the inclusion of PFAS in the REACH restriction chapter for control. After the public consultation, ECHA's Risk Assessment Committee (RAC) and Socio-Economic Analysis Committee (SEAC) will evaluate the proposed restrictions and form opinions based on the consultation opinions. Ultimately, the European Commission will decide whether to include PFAS in the restriction chapter for control.

[0006] In view of the above situation, some new non-fluorinated polymers have been proposed to replace the existing fluorinated finishing agents.

[0007] CN107548406A proposes a reaction between polyurethane and long-chain alcohol, and the resulting polymer is used to finish textiles and has a good water-repellent effect.

[0008] CN105980427A proposes a modified polyurethane, the resulting polymer is used to finish textiles and also has a good water-repellent effect.

[0009] The above polymers only have water-repellent effect but no oil-repellent effect, so the treated surfaces of items such as fiber fabrics have no barrier effect on oily stains.

[0010] Therefore, it is necessary to invent a new type of surface treatment agent that does not contain fluorine elements, can reduce the burden on the environment, and also has excellent water-repellent and oil-repellent effects, which can effectively resist various water-based and oil-based stains.

[0011] Summary of the Invention

[0012] The purpose of this application is to provide a novel compound. A treatment agent prepared based on the compound can be used to treat a variety of articles, thereby giving the surface of the articles excellent water-repellent, oil-repellent and anti-fouling properties, thereby effectively combating water-based and oil-based stains.

[0013] In the first aspect, the compound of the present application is prepared from raw materials including a compound containing an isocyanate group and an isocyanate-reactive compound shown in Formula I.

[0014] MZ or ZMZ

[0015] Formula I

[0016] Wherein, M is reactive with isocyanate;

[0017] Z is selected from the following structures,

[0018] In Z, R3 are each independently selected from C1-C 20 Alkyl, C6-C 20 Aryl, C7-C 12 Aralkyl, C7-C 12 Alkaryl, C1-C 20 Alkoxy or R4-O-R5- group, R4 is C1-C 20 Alkyl, C6-C 20 Aryl, C7-C 12 Arylalkyl or C7-C 12 Alkaryl, R5 is C1-C 20 Alkylene, 1≤a≤200;

[0019] Y1 and Y2 are the same or different and are independently selected from C1-C 20 Alkyl, C6-C 20 Aryl, C7-C 12 Aralkyl, C7-C 12 Alkyl or the following structure (1):

[0020] R7 are each independently selected from C1-C 20 Alkyl, C6-C 20 Aryl, C7-C 12 Arylalkyl or C7-C12 R8 are each independently selected from C1-C 20 Alkyl, C6-C 20 Aryl, C7-C 12 Aralkyl, C7-C 12 Alkaryl, C1-C 20 Alkoxy or R9-OR 10 - group, wherein R9 is C1-C 20 Alkyl, C6-C 20 Aryl, C7-C 12 Arylalkyl or C7-C 12 The alkylaryl group, R 10 C1-C 20 Alkylene, 0≤b≤200.

[0021] In some embodiments, the isocyanate group-containing compound is selected from one or more of hexamethylene diisocyanate homopolymer, 3-isocyanatomethyl-3,4,4-trimethylcyclohexyl isocyanate, bis-(4-isocyanatocyclohexyl)methane, diisocyanate trimers shown in formulas II a to II e, polymeric diphenylmethane diisocyanate shown in formula II f, and isophorone diisocyanate prepolymer shown in formula II g.

[0022] In formula II f, n is 0-10, for example, 1, 2, 3, 4, 5, 6, 7, 8 or 9; in formula II g, n is 0-10, for example, 1, 2, 3, 4, 5, 6, 7, 8 or 9.

[0023] The inventors of the present application unexpectedly discovered that when the surface of articles such as fiber fabrics is treated with the above-mentioned compound obtained by the reaction of isocyanate with a linear or branched silicon-containing compound, the articles have excellent water-repellent and oil-repellent effects, thereby making the surface of the treated articles have excellent resistance to various pollutants.

[0024] In particular, isocyanate-containing compounds used as reaction substrates can enhance the branching properties of the compound if they contain two or more isocyanate groups, particularly if they contain multiple isocyanate groups. When reacted with compounds of Formula I containing isocyanate-reactive groups, such as Zerewitinoff hydrogen atoms, the resulting compound can exhibit a branched structure and exhibit superior performance.

[0025] In some embodiments, compounds containing isocyanate groups are commonly available from chemical manufacturers, such as Wanhua Chemical. TT, PM, HT, HB, IT, IPP, etc.

[0026] In some embodiments, the compound containing an isocyanate group is selected from aliphatic and aromatic polyisocyanates having a biuret structure, preferably a compound of the trade name Wanhua Chemical. HT (trimer of hexamethylene diisocyanate) and HB (hexamethylene diisocyanate biuret polyisocyanate).

[0027] In some embodiments, the M group of Formula I contains one or more Zerewitinoff hydrogen atoms.

[0028] In some embodiments, M is represented by Formula I-1:

[0029] HXB-

[0030] Formula I-1

[0031] In formula I-1, B is selected from C1-C 20 Alkylene, C6-C 20 Aryl and combinations thereof; X is -O-, -S-, -N(R1)-, -O-(CH2) k -N(R2)-, -OC(O)-, R1 is selected from hydrogen atom or C1-C 20 Alkyl, R2 is selected from hydrogen atom or C1-C 20 Alkyl, 1≤k≤6.

[0032] In some embodiments, in Formula I-1, B is C1-C 10 Alkylene, for example, C1-C3 alkylene, C4-C6 alkylene or C8-C 10 of alkylene.

[0033] In some embodiments, in Formula I-1, B is C6-C 15 arylene, such as C6-C9 arylene, C 10 -C 12 Arylene or C 13 -C 15 arylene group.

[0034] In some embodiments, in formula I-1, X is -N(R1)-, and R1 is selected from hydrogen atom or C1-C 10 Alkyl, for example, C1-C3 alkyl, C4-C6 alkyl or C8-C 10 In some embodiments, in Formula I-1, R1 is selected from a hydrogen atom or a methyl group.

[0035] In some embodiments, in Formula I-1, X is -O-(CH2) k -N(R2)-, R2 is selected from hydrogen atom or C1-C 10 Alkyl, for example, C1-C3 alkyl, C4-C6 alkyl or C8-C 10 wherein R2 is an alkyl group, k is 1, 2, 3, 4, 5 or 6. In some embodiments, in Formula I-1, R2 is selected from a hydrogen atom or a methyl group.

[0036] In some embodiments, M is represented by Formula I-2:

[0037] In formula I-2, B is selected from C1-C 20 Alkylene, C6-C 20 arylene groups and combinations thereof.

[0038] In some embodiments, in Formula I-2, B is C1-C 10 Alkylene, for example, C1-C3 alkylene, C4-C6 alkylene or C8-C 10 of alkylene.

[0039] In some embodiments, in Formula I-2, B is C6-C 15 arylene, such as C6-C9 arylene, C 10 -C 12 Arylene or C 13 -C 15 arylene group.

[0040] In some embodiments, in Z, R3 are each independently C1-C 10 Alkyl, C6-C 10 Aryl, C7-C 12 Aralkyl, C7-C 12 Alkaryl, C1-C 10 Alkoxy or R4-O-R5- group, R4 is C1-C 10 Alkyl, C6-C 10 Aryl, C7-C 12 Arylalkyl or C7-C 12 Alkaryl, R5 is C1-C 10 alkylene, 1≤a≤100; R7 are each independently C1-C 10 Alkyl, C6-C 10 Aryl, C7-C 12 Arylalkyl or C7-C 12 R8 are each independently C1-C 10 Alkyl, C6-C 10Aryl, C7-C 12 Aralkyl, C7-C 12 Alkaryl, C1-C 10 Alkoxy or R9-OR 10 - group, wherein R9 is C1-C 10 Alkyl, C6-C 10 Aryl, C7-C 12 Arylalkyl or C7-C 12 The alkylaryl group, R 10 C1-C 10 Alkylene, 0≤b≤100.

[0041] In some embodiments, in Z, R3 are each independently C1-C6 alkyl, C6-C 10 Aryl, C7-C 10 Aralkyl, C7-C 10 Alkaryl, C1-C6 alkoxy or R4-O-R5- group, R4 is C1-C6 alkyl, C6-C 10 Aryl, C7-C 10 Arylalkyl or C7-C 10 R5 is a C1-C6 alkylene group, 1≤a≤30; R7 are each independently a C1-C6 alkyl group, a C6-C 10 Aryl, C7-C 10 Arylalkyl or C7-C 10 R8 are each independently C1-C6 alkyl, C6-C 10 Aryl, C7-C 10 Aralkyl, C7-C 10 Alkaryl, C1-C6 alkoxy or R9-OR 10 - group, wherein R9 is C1-C6 alkyl, C6-C 10 Aryl, C7-C 10 Arylalkyl or C7-C 10 The alkylaryl group, R 10 C1-C 16 Alkylene, 0≤b≤30.

[0042] In some embodiments, a is an integer from 1-80, an integer from 1-30, an integer from 1-20, or an integer from 1-10.

[0043] In some embodiments, b is 0. In some embodiments, b is an integer from 1-30, an integer from 1-20, an integer from 1-10, or an integer from 1-5.

[0044] In some embodiments, Z is independently selected from one or more of the following structures i-1 to i-6:

[0045] R is independently selected from C1-C 10 Alkyl, C6-C 10 Aryl, C7-C 12 Arylalkyl or C7-C 12 Alkaryl;

[0046] 1≤m+1≤60, preferably 1≤m+1≤30; 0≤p≤60, preferably 0≤p≤30; 0≤q≤60, preferably 0≤q≤30; 1≤x≤9, preferably 1≤x≤7, and each x may be the same or different.

[0047] In some embodiments, R is a C1-C3 alkyl group, such as a methyl group.

[0048] In some embodiments, Z is selected from

[0049] One or more of;

[0050] R is independently selected from C1-C 10 Alkyl, C6-C 10 Aryl, C7-C 12 Arylalkyl or C7-C 12 Alkaryl;

[0051] Me represents a methyl group, ph represents a phenyl group; 1≤m+1≤60, preferably 1≤m+1≤30; 0≤p≤60, preferably 0≤p≤30; 0≤q≤60, preferably 0≤q≤30; 1≤x≤9, preferably 1≤x≤7, and each x may be the same or different.

[0052] In some embodiments, m is 0, 1, 2, 3, 4, 5, 6, 7, 8, or 9.

[0053] In some embodiments, x is 1, 2, 3, 4, 5, 6, or 7.

[0054] In some embodiments, the isocyanate-reactive compound is selected from

[0055] HO-(CH2)3Si(OSi(CH3)3)3;

[0056] HS-(CH2)3Si(OSi(CH3)3)3;

[0057] HO-(CH2)3Si(CH3)(OSi(CH3)3)2;

[0058] NH2-(CH2)3Si(OSi(CH3)3)3;

[0059] NH(CH3)-(CH2)3Si(OSi(CH3)3)3;

[0060] NH2-(CH2)3Si(CH3)(OSi(CH3)3)2;

[0061] NH(CH3)-(CH2)3Si(CH3)(OSi(CH3)3)2;

[0062] HO-(CH2)3Si(OSi(CH2CH3)3)3;

[0063] HO-CH2-Si(OSi(CH3)3)3;

[0064] HO-(CH2)3Si(CH3)[O-[Si(CH3)2O]n-Si(CH3)2C4H9]2, 0 ≤ n ≤ 25;

[0065] HO-(CH2)3[Si(CH3)2O]n-Si(CH3)2C4H9, 1 ≤ n ≤ 25;

[0066] HO-(CH2)3[Si(CH3)2O]n-Si(CH3)2C8H 17 , 1 ≤ n ≤ 25;

[0067] HO-(CH2)3[Si(CH3)2O]n-Si(CH3)3, 1 ≤ n ≤ 25;

[0068] NH2-(CH2)3-[Si(CH3)2O]n-Si(CH3)2C4H9 (C4H9 represents butyl), 1 ≤ n ≤ 25;

[0069] HO-(CH2)2-NH-(CH2)3Si(OSi(CH3)3)3;

[0070] HO-(CH2)2-NH-(CH2)3[Si(CH3)2O]n-Si(CH3)2C{4H9} (C4H9 represents butyl), 1 ≤ n ≤ 25;

[0071] NH[-(CH2)3-Si(OSi(CH3)3)3]2;

[0072] NH[-(CH2)3-Si(CH3)(OSi(CH3)3)2]2;

[0073] NH[-(CH2)3-(Si(CH3)2O) n -Si(CH3)2C4H9]2 (C4H9 represents butyl), 1 ≤ n ≤ 25.

[0074] In some embodiments, the isocyanate-reactive compound includes isocyanate-reactive compound IA and / or isocyanate-reactive compound IB;

[0075] The general formula of compound IA is the same as formula I, and further satisfies the following conditions: when a is 1, Y1 and / or Y2 are structures of formula (1); when a is greater than 1 and ≤ 200, at least one Y1 is a structure of formula (1) and / or at least one Y2 is a structure of formula (1);

[0076] The general formula of compound IB is the same as that of formula I, and furthermore, Y1 and Y2 are the same or different and are independently selected from C1-C 20 Alkyl, C6-C 20 Aryl, C7-C 12 Arylalkyl and C7-C 12 of alkylaryl.

[0077] In some embodiments, the general formula of Compound IA is as shown in Formula IA:

[0078] M-Z1 or Z1-M-Z1

[0079] Formula IA

[0080] Wherein, M is reactive with isocyanate;

[0081] Z1 is selected from the following structures,

[0082] In Z1, R3 are each independently selected from C1-C 20 Alkyl, C6-C 20 Aryl, C7-C 12 Aralkyl, C7-C 12 Alkaryl, C1-C 20 Alkoxy or R4-O-R5- group, R4 is C1-C 20 Alkyl, C6-C 20 Aryl, C7-C 12 Arylalkyl or C7-C 12 Alkaryl, R5 is C1-C 20 Alkylene, 1≤a≤200;

[0083] Y1 and Y2 are the same or different and are independently selected from C1-C 20 Alkyl, C6-C 20 Aryl, C7-C 12 Aralkyl, C7-C 12and an alkylaryl group and a structure of the following formula (1), provided that when a is 1, Y1 and / or Y2 are structures of formula (1), and when a is greater than 1 and ≤ 200, at least one Y1 is a structure of formula (1) and / or at least one Y2 is a structure of formula (1):

[0084] R7 are each independently selected from C1-C 20 Alkyl, C6-C 20 Aryl, C7-C 12 Arylalkyl or C7-C 12 R8 are each independently selected from C1-C 20 Alkyl, C6-C 20 Aryl, C7-C 12 Aralkyl, C7-C 12 Alkaryl, C1-C 20 Alkoxy or R9-OR 10 - group, wherein R9 is C1-C 20 Alkyl, C6-C 20 Aryl, C7-C 12 Arylalkyl or C7-C 12 The alkylaryl group, R 10 C1-C 20 Alkylene, 0≤b≤200.

[0085] In this application, the definition of M in Formula IA is the same as that of M in Formula I.

[0086] In some embodiments, in Z1, R3 are each independently C1-C 10 Alkyl, C6-C 10 Aryl, C7-C 12 Aralkyl, C7-C 12 Alkaryl, C1-C 10 Alkoxy or R4-O-R5- group, R4 is C1-C 10 Alkyl, C6-C 10 Aryl, C7-C 12 Arylalkyl or C7-C 12 Alkaryl, R5 is C1-C 10 alkylene, 1≤a≤100; R7 are each independently C1-C 10 Alkyl, C6-C 10 Aryl, C7-C 12 Arylalkyl or C7-C 12 R8 are each independently C1-C 10 Alkyl, C6-C 10 Aryl, C7-C 12 Aralkyl, C7-C12 Alkaryl, C1-C 10 Alkoxy or R9-OR 10 - group, wherein R9 is C1-C 10 Alkyl, C6-C 10 Aryl, C7-C 12 Arylalkyl or C7-C 12 The alkylaryl group, R 10 C1-C 10 alkylene, and / or 0≤b≤80.

[0087] According to some embodiments of the present invention, in Z1, R3 are each independently C1-C6 alkyl, C6-C 10 Aryl, C7-C 10 Aralkyl, C7-C 10 Alkaryl, C1-C6 alkoxy or R4-O-R5- group, R4 is C1-C6 alkyl, C6-C 10 Aryl, C7-C 10 Arylalkyl or C7-C 10 R5 is a C1-C6 alkylene group, 1≤a≤30; R7 are each independently a C1-C6 alkyl group, a C6-C 10 Aryl, C7-C 10 Arylalkyl or C7-C 10 R8 are each independently C1-C6 alkyl, C6-C 10 Aryl, C7-C 10 Aralkyl, C7-C 10 Alkaryl, C1-C6 alkoxy or R9-OR 10 - group, wherein R9 is C1-C6 alkyl, C6-C 10 Aryl, C7-C 10 Arylalkyl or C7-C 10 The alkylaryl group, R 10 C1-C 16 Alkylene, 0≤b≤30.

[0088] In some embodiments, in Formula IA, a is an integer from 1-80, an integer from 1-30, an integer from 1-20, or an integer from 1-10.

[0089] In some embodiments, in Formula IA, b is 0. In some embodiments, in Formula IA, b is an integer from 1 to 30, an integer from 1 to 20, an integer from 1 to 10, or an integer from 1 to 5.

[0090] In particular, R3 and R8 represent C1-C 20 Alkyl, C1-C20 Alkoxy, C6-C 20 The aryl groups are particularly commonly used, such as C1-C8 alkyl and C1-C4 alkoxy. For example, methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, methoxy, ethoxy, propoxy and butoxy. Aryl groups include phenyl, tolyl and naphthyl. R3 and R8 can also be of the structure (R5-O-R6)-, where R5 is C1-C 10 Alkyl, R6 is C1-C 10 Alkylene, more common such as CH3O(CH2) x - etc. R6 is a 20 Alkyl groups and C6-C 20 The aryl groups are selected from, for example, alkyl groups are methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, undecyl, dodecyl, hexadecyl, etc., and aromatic groups are phenyl, tolyl and naphthyl, etc.

[0091] In some embodiments, Z1 is selected from one or more of the following structures i-3 to i-6:

[0092] R is independently selected from C1-C 10 Alkyl, C6-C 10 Aryl, C7-C 12 Arylalkyl or C7-C 12 Alkaryl;

[0093] 1≤m+1≤60, preferably 1≤m+1≤30; 0≤p≤60, preferably 0≤p≤30; 0≤q≤60, preferably 0≤q≤30; 1≤x≤9, preferably 1≤x≤7, and each x may be the same or different.

[0094] In some embodiments, R is a C1-C3 alkyl group, such as a methyl group.

[0095] In some preferred embodiments, Z1 is selected from the following structures:

[0096] One or more of;

[0097] Me represents a methyl group, 1≤m+1≤60, preferably 1≤m+1≤30; 0≤p≤60, preferably 0≤p≤30; 0≤q≤60, preferably 0≤q≤30; 1≤x≤9, preferably 1≤x≤7, and each x may be the same or different.

[0098] In some embodiments, the isocyanate-reactive compound IA is selected from

[0099] HO-(CH2)3Si(OSi(CH3)3)3;

[0100] HS-(CH2)3Si(OSi(CH3)3)3;

[0101] HO-(CH2)3Si(CH3)(OSi(CH3)3)2;

[0102] NH2-(CH2)3Si(OSi(CH3)3)3;

[0103] NH(CH3)-(CH2)3Si(OSi(CH3)3)3;

[0104] NH2-(CH2)3Si(CH3)(OSi(CH3)3)2;

[0105] NH(CH3)-(CH2)3Si(CH3)(OSi(CH3)3)2;

[0106] HO-(CH2)3Si(OSi(CH2CH3)3)3;

[0107] HO-CH2-Si(OSi(CH3)3)3;

[0108] HO-(CH2)3Si(CH3)[O-[Si(CH3)2O]n-Si(CH3)2C4H9]2,0≤n≤25

[0109] HO-(CH2)2-NH-(CH2)3Si(OSi(CH3)3)3;

[0110] NH[-(CH2)3-Si(OSi(CH3)3)3]2;

[0111] NH[-(CH2)3-Si(CH3)(OSi(CH3)3)2]2.

[0112] In some embodiments, the general formula of Compound IB is as shown in Formula IB:

[0113] M-Z2 or Z2-M-Z2

[0114] Formula IB

[0115] Wherein, M is reactive with isocyanate;

[0116] Z2 is selected from the following structures,

[0117] In Z2, Y1 and Y2 are the same or different and are independently selected from C1-C 20 Alkyl, C6-C 20 Aryl, C7-C 12Arylalkyl and C7-C 12 R3 are each independently selected from C1-C 20 Alkyl, C6-C 20 Aryl, C7-C 12 Aralkyl, C7-C 12 Alkaryl, C1-C 20 Alkoxy or R4-O-R5- group, R4 is C1-C 20 Alkyl, C6-C 20 Aryl, C7-C 12 Arylalkyl or C7-C 12 Alkaryl, R5 is C1-C 20 Alkylene, 1≤a≤200.

[0118] In this application, the definition of M in Formula IB is the same as that of M in Formula I.

[0119] In some embodiments, in Z2, Y1 and Y2 are the same or different and are independently selected from C1-C 10 Alkyl, C6-C 10 Aryl, C7-C 12 Arylalkyl and C7-C 12 R3 are each independently selected from C1-C 10 Alkyl, C6-C 12 Aryl, C7-C 12 Aralkyl, C7-C 12 Alkaryl, C1-C 10 Alkoxy or R4-O-R5- group, R4 is C1-C 10 Alkyl, C6-C 12 Aryl, C7-C 12 Arylalkyl or C7-C 12 Alkaryl, R5 is C1-C 10 of alkylene.

[0120] According to some embodiments of the present invention, in Z2, 1≤a≤80. According to some embodiments of the present invention, in Z2, 1≤a≤30. According to some embodiments of the present invention, in Z2, 1≤a≤20. According to some embodiments of the present invention, in Z2, 1≤a≤10.

[0121] In some embodiments, in Z2, Y1 and Y2 are the same or different and are independently selected from C1-C6 alkyl, C6-C 10 Aryl, C7-C 10 Arylalkyl and C7-C 10 R3 are each independently selected from C1-C6 alkyl, C6-C 10Aryl, C7-C 10 Aralkyl, C7-C 10 Alkaryl, C1-C6 alkoxy or R4-O-R5- group, R4 is C1-C6 alkyl, C6-C 10 Aryl, C7-C 10 Arylalkyl or C7-C 10 R5 is an alkylene group of C1-C6.

[0122] In some embodiments, Z2 is selected from one or more of the following structures i-1 to i-2:

[0123] R is independently selected from C1-C 10 Alkyl, C6-C 10 Aryl, C7-C 12 Arylalkyl or C7-C 12 Alkaryl;

[0124] 1≤m+1≤60, preferably 1≤m+1≤30; 1≤x≤9, preferably 1≤x≤7.

[0125] Z2 is preferably selected from the following structures:

[0126] One or more of;

[0127] Me represents a methyl group, ph represents a phenyl group; 1≤m+1≤60, preferably 1≤m+1≤30; 1≤x≤9, preferably 1≤x≤7.

[0128] In some embodiments, the isocyanate-reactive compound IB is selected from

[0129] HO-(CH2)3[Si(CH3)2O]n-Si(CH3)2C4H9, 1≤n≤25;

[0130] HO-(CH2)3[Si(CH3)2O]n-Si(CH3)2C8H 17 , 1≤n≤25;

[0131] HO-(CH2)3[Si(CH3)2O]n-Si(CH3)3, 1≤n≤25;

[0132] NH2-(CH2)3-[Si(CH3)2O]n-Si(CH3)2C4H9 (C4H9 represents butyl), 1≤n≤25;

[0133] HO-(CH2)2-NH-(CH2)3[Si(CH3)2O]n-Si(CH3)2C4H9 (C4H9 represents butyl), 1≤n≤25;

[0134] NH[-(CH2)3-(Si(CH3)2O) n -Si(CH3)2C4H9]2 (C4H9 represents butyl group), 1≤n≤25.

[0135] In some embodiments, the compound of the present application is formed by reacting a compound containing an isocyanate group with an organosilicon compound containing Zerewitinoff hydrogen atoms, and the molar ratio of isocyanate groups to active hydrogen atoms is 0.5:1 to 1.5:1, preferably 0.8:1 to 1.2:1.

[0136] In some embodiments, the synthesis of the compounds of the present application is carried out in a suitable dry organic solvent that is free of groups reactive with isocyanate groups. Ketones are preferred solvents, with methyl isobutyl ketone (MIBK) being particularly preferred. In some embodiments, the compounds of the present application can be dispersed and emulsified with an emulsifier, a cosolvent, water, etc. using a high-speed homogenizer to produce a uniform and stable emulsion.

[0137] In a second aspect, the present application provides a treating agent comprising the compound described in the first aspect, an emulsifier and an aqueous medium.

[0138] In some embodiments, the emulsifier is selected from one or more of nonionic surfactants, anionic surfactants, cationic surfactants, N-oxides, and amphoteric surfactants.

[0139] In some embodiments, the nonionic surfactant is selected from one or more of ethers, esters, ester ethers, alkanolamides, polyols, and amine oxides. In some embodiments, the nonionic surfactant is a nonionic surfactant having an oxyalkylene group.

[0140] In some embodiments, the nonionic surfactant can be one or more of linear and / or branched aliphatic oxyalkylene adducts, linear and / or branched fatty acid polyalkylene glycol esters, polyethylene oxide (POE) / polypropylene oxide (POP) copolymers (random copolymers or block copolymers), and oxyalkylene adducts of acetylene glycol.

[0141] In some embodiments, the nonionic surfactant includes addition products of ethylene oxide with hexylphenol, isooctylphenol, hexadecanol, oleic acid, alkane (C12-C16) mercaptan, sorbitan monofatty acid (C7-C9) or (C12-C18) amine, etc.

[0142] In some embodiments, the cationic surfactant is selected from one or more of amine, amine salt, amine salt, imidazoline and imidazolinium salt surfactants.

[0143] In some embodiments, examples of cationic surfactants are R1-N + (R2R3R4)X - Wherein, R1, R2, R3 and R4 are independently the same or different hydrogen atoms or hydrocarbon groups with 1 to 50 carbon atoms (e.g., C1-C6 alkyl, C7-C 10 Alkyl, C 11 -C 15 Alkyl or C 16 -C 20 alkyl), an aryl group having 6 to 50 carbon atoms, an aralkyl group having 7 to 50 carbon atoms, or an alkaryl group having 7 to 50 carbon atoms, and X is a halogen (e.g., chlorine or bromine), an acid (e.g., an inorganic acid such as hydrochloric acid or an organic acid such as acetic acid (particularly a fatty acid)).

[0144] In some embodiments, the cationic surfactant includes one or more of lauryltrimethylammonium acetate, tetradecyltrimethylammonium chloride, hexadecyltrimethylammonium bromide, trimethyloctadecylammonium chloride, and stearamidopropyldimethylamine.

[0145] In some embodiments, the emulsifier is a nonionic surfactant and a cationic surfactant.

[0146] In some embodiments, the amount of the emulsifier is 0.1-20 parts by weight relative to 100 parts by weight of the compound.

[0147] In some embodiments, the aqueous medium includes water and an optional organic solvent. In some embodiments, the aqueous medium is preferably water. The aqueous medium can also be mixed with water and an organic solvent as needed. As the organic solvent here, as long as it is an organic solvent miscible with water, there is no particular limitation, and examples include acetone, methyl ethyl ketone, ethyl acetate, ethanol, isopropyl alcohol, butyl diglycol, propylene glycol, dipropylene glycol, tripropylene glycol, dipropylene glycol monomethyl ether, tripropylene glycol monomethyl ether, dipropylene glycol monobutyl ether, dipropylene glycol dimethyl ether, propylene glycol monomethyl ether acetate, etc. It should be noted that the ratio of water to organic solvent is not particularly limited.

[0148] In a third aspect, the present application provides a method for preparing the treating agent of the second aspect, comprising mixing a solution comprising the compound of the first aspect with a solution comprising an emulsifier and water.

[0149] In some embodiments, the method for preparing the treatment agent comprises the following steps:

[0150] (1) reacting an isocyanate group-containing compound with an isocyanate-reactive compound in the presence of a solvent and a catalyst to obtain a reaction product;

[0151] (2) The reaction product of (1) is mixed with a solution containing an emulsifier and water, and then the solvent is removed to obtain the treating agent.

[0152] In some embodiments, the method of treating an agent comprises the following steps:

[0153] (1) adding a solvent, a compound containing an isocyanate group, an isocyanate-reactive compound, and a catalyst into a reaction kettle, heating the reaction kettle to a certain temperature, and reacting the reaction kettle for a period of time until the isocyanate functional groups are substantially reacted;

[0154] (2) The emulsifier and water are mixed evenly to form an emulsifier solution, which is then slowly added to the compound obtained above. The solution is homogenized in a high-pressure homogenizer to obtain a stable emulsion. The solvent is removed by reduced pressure distillation to obtain the treating agent.

[0155] In some embodiments, the solvent is selected from one or more of acetone, methyl ethyl ketone, ethyl acetate, ethanol, isopropyl alcohol, butyl diglycol, propylene glycol, dipropylene glycol, tripropylene glycol, dipropylene glycol monomethyl ether, tripropylene glycol monomethyl ether, dipropylene glycol monobutyl ether, dipropylene glycol dimethyl ether and propylene glycol monomethyl ether acetate.

[0156] In some embodiments, the catalyst is selected from one or more of ferric chloride, dibutyltin dilaurate, and sodium carbonate.

[0157] In a fourth aspect, the present application provides the use of the compound described in the first aspect, the treating agent described in the second aspect, or the treating agent prepared by the method described in the third aspect in fiber fabrics, leather, non-woven fabrics, asbestos, fur, concrete, stone, paper products, plastics or coatings.

[0158] In a fifth aspect, the present application provides a water-repellent, oil-repellent or anti-fouling product, which includes a product and the compound described in the first aspect or the treatment agent described in the second aspect or the treatment agent prepared by the method described in the third aspect, and the product is a fiber fabric, leather, non-woven fabric, asbestos, fur, concrete, stone, paper products, plastic or coating.

[0159] In some embodiments, the compound described in the first aspect, the treatment agent described in the second aspect, or the treatment agent prepared by the method described in the third aspect is attached to the surface and / or interior of the product.

[0160] In a sixth aspect, the present application provides a method for treating a product, which comprises contacting the product with the compound described in the first aspect or the treating agent described in the second aspect or the treating agent prepared by the method described in the third aspect, wherein the product is a fiber fabric, leather, non-woven fabric, asbestos, fur, concrete, stone, paper products, plastic or paint.

[0161] In some embodiments, the contacting is achieved by a surface sizing process, a surface coating process, a wet-end addition process, or an immersion treatment process.

[0162] The treatment agent of the present application can be applied to the treated object using existing known methods. Usually, the treatment agent is dispersed in an organic solvent or water for dilution, and is attached to the surface of the treated article by known methods such as dip coating, spray coating, and foaming cloth, and then dried. In addition, when necessary, it can be applied together with an appropriate cross-linking agent (such as blocked isocyanate) for vulcanization. Insect repellents, softeners, antibacterial agents, flame retardants, antistatic agents, wrinkle-resistant agents, etc. can also be added to the treatment agent of the present application for use together. The concentration of the compound in the treatment solution in contact with the substrate can be 0.01-10 weight % (especially when dip coating), for example, 0.05-10 weight %.

[0163] In the present application, fiber fabrics include natural fibers of animal or plant origin such as cotton, linen, wool, and silk, synthetic fibers such as polyamide, polyester, polyvinyl alcohol, polyacrylonitrile, polyvinyl chloride, polypropylene, and acrylic fibers, semi-synthetic fibers such as rayon and acetate fibers, inorganic fibers such as glass fibers, carbon fibers, and asbestos fibers, or mixed fiber fabrics thereof.

[0164] Effects of the Invention

[0165] The compounds of the present application and the resulting treatment agents can be applied under acidic, alkaline, and neutral conditions to treat the surfaces of a variety of articles, such as fabrics, leather, non-woven fabrics, asbestos, fur, concrete, natural stone, paper, plastics, and coatings. Treatment methods include immersion, surface coating, surface sizing, and internal addition (wet-end addition). After treatment, the treated articles can be endowed with excellent water- and oil-repellent properties or antifouling properties. DETAILED DESCRIPTION

[0166] To make the purpose, technical solutions, and advantages of this application more clearly understood, the present application is further described in detail below with reference to the following examples. These examples are intended only to illustrate this application and are not intended to constitute any limitation to this application. The actual scope of protection of this application is set forth in the claims.

[0167] In this application, unless otherwise specified, the terms used have the general meanings known to those skilled in the art.

[0168] In the present application, the term "alkyl" refers to a straight-chain alkyl or a branched-chain alkyl, non-limiting examples of which include: methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, n-pentyl, 1-ethylpropyl, 2-methylbutyl, 3-methylbutyl, 2,2-dimethylpropyl, n-hexyl, 2-methylpentyl, 3-methylpentyl, etc.

[0169] In the present application, the term "alkylene" refers to a straight chain alkylene or a branched chain alkylene, non-limiting examples of which include: methylene, ethylene, n-propylene, n-butylene, n-pentylene, -CHCH3CH2-, -CHCH3CH2CH2-, CH2CH3CHCH2-, etc.

[0170] In this application, unless otherwise specified, “%” refers to mass percentage.

[0171] 1. Synthesis Method

[0172] (1) adding a solvent, a compound containing an isocyanate group, an isocyanate-reactive compound, and a catalyst into a reaction kettle, heating the reaction kettle to a certain temperature, and reacting the reaction kettle for a period of time until the isocyanate functional groups are substantially reacted;

[0173] (2) The emulsifier and water are mixed evenly to form an emulsifier solution, which is then slowly added to the compound obtained above. The solution is homogenized in a high-pressure homogenizer to obtain a stable emulsion. The solvent is removed by reduced pressure distillation to obtain the treating agent.

[0174] 2. Test Method

[0175] Fiber fabric processing

[0176] The fabrics treated in this application can be dyed 100% polyester and 100% khaki cotton twill. The treatment method involves padding a sample of fabric in an aqueous solution containing a predetermined concentration of the treatment agent described herein (with a 70% absorption rate), followed by drying at 110°C for 90 seconds and baking at 170°C for 60 seconds. The resulting fabric samples are then evaluated for their water repellency, hydrophobicity, and oil resistance.

[0177] Evaluation Method

[0178] Test methods for fiber fabrics-Water resistance

[0179] According to Teflon global specifications and quality control testing methods, the sample fabric is tested using liquids containing different volumes of isopropyl alcohol to observe and determine the degree of surface wetting. This test provides a rough index of water stain resistance. The higher the repellency rating, the better the final substrate's resistance to water-based substances. The composition of the standard test liquid is shown in Table 1 below.

[0180] Table 1 Water resistance test grade composition

[0181] Fiber fabric test method - spray water repellency test

[0182] The dynamic water repellency of the treated substrate was measured according to the American Association of Textile Chemical and Tonerists (AATCC) TM-22, referring to published standards. A glass funnel with a volume of at least 250 ml and a nozzle capable of spraying 250 ml of water in 20-30 seconds was used. The test piece frame was a metal frame with a diameter of 15 cm. Three test pieces measuring approximately 20 cm x 20 cm were prepared and secured to the test piece holder frame, ensuring that the sheets were wrinkle-free. With the center of the spray positioned at the center of the sheet, 250 ml of room temperature water was added to the glass funnel and sprayed onto the test piece for 25-30 seconds. The holding frame was removed from the stand. Grasp one end of the frame, with the front surface facing downward, and gently tap the opposite end with a hard object. Rotate the frame 180° and repeat the same procedure, allowing any excess water to drip off. The wet test pieces were rated 0, 50, 70, 80, 90, and 100, starting with poor water repellency and ending with excellent (as shown in Table 2 below). Comparison was made with a wet comparison standard. Results were obtained based on the average of three determinations.

[0183] Table 2 Water repellency rating table

[0184] Test methods for fiber fabrics-Oil resistance

[0185] Oil repellency is evaluated according to the AATCC-TM118 test method. The basic principle is to drop test oils of different surface tensions onto the test cloth. The higher the level, the better the oil repellency. The composition of the standard test liquid is shown in Table 3 below.

[0186] Table 3 Fabric oil resistance test grade composition

[0187] Three Examples and Comparative Examples

[0188] See Table 4 for chemical abbreviations:

[0189] Table 4 Codes and chemical formulas of the compounds

[0190] Example 1

[0191] Step (1) Add 65 g (340 mmol NCO) into a four-necked flask equipped with a reflux condenser, a nitrogen inlet tube, a thermometer and a stirrer. HB-100 (hexamethylene diisocyanate-based biuret polyisocyanate) was dissolved in 100 g of methyl isobutyl ketone (MIBK) under nitrogen, followed by the addition of 121 g (340 mmol) of Si-B3-OH. The mixture was heated to 55°C, followed by the addition of a solution of 0.025 g of dibutyltin dilaurate dissolved in 2 ml of MIBK. The mixture was further heated to 95°C and allowed to react for 6 hours.

[0192] Step (2) 450 g of water, 7.8 g of stearamidopropyl dimethylamine, 4 g of fatty alcohol polyoxyethylene ether (EO number 9), 42 g of dipropylene glycol and 4.7 g of acetic acid were added to a beaker and stirred to form a uniform surfactant solution. The solution was heated to 65° C., the reaction mixture in step (1) was cooled to 65° C. and the surfactant solution was slowly added to produce an emulsion. The mixture was blended (2 minutes) and homogenized at 6000 psi using an immersion mixer, and then MIBK was removed by evaporation under reduced pressure to obtain a dispersion. The solid content of the dispersion was adjusted to 25% by adding water.

[0193] Example 2-Example 6

[0194] The same method as Example 1 was used, except that Si-B3-OH was replaced by equimolar amounts of the following isocyanate-reactive compounds of different structures, namely Si-B3-SH (Example 2), Si-B3-NHM (Example 3), Si-B2-OH (Example 4), Si-N2-B2-NH (Example 5), and Si-5-OH (Example 6). The solid content of the dispersion was adjusted to about 25% by the amount of water added in the final step.

[0195] Example 7

[0196] Step (1) Add 65 g (340 mmol NCO) into a four-necked flask equipped with a reflux condenser, a nitrogen inlet tube, a thermometer and a stirrer. HT-100 (HDI trimer) was dissolved in 100 g of methyl isobutyl ketone (MIBK) under nitrogen, followed by the addition of 121 g (340 mmol) of Si-B3-OH. The mixture was heated to 55°C, followed by the addition of a solution of 0.025 g of dibutyltin dilaurate dissolved in 2 ml of MIBK. The mixture was further heated to 95°C and allowed to react for 6 hours.

[0197] Step (2) 450 g of water, 7.8 g of stearamidopropyl dimethylamine, 4 g of fatty alcohol polyoxyethylene ether (EO number 9), 42 g of dipropylene glycol and 4.7 g of acetic acid were added to a beaker and stirred to form a uniform surfactant solution. The solution was heated to 65° C., the reaction mixture in step (1) was cooled to 65° C. and the surfactant solution was slowly added to produce an emulsion. The mixture was blended (2 minutes) and homogenized at 6000 psi using an immersion mixer, and then MIBK was removed by evaporation under reduced pressure to obtain a dispersion. The solid content of the dispersion was adjusted to 25% by adding water.

[0198] Example 8

[0199] Step (1) Add 84 g (340 mmol NCO) into a four-necked flask equipped with a reflux condenser, a nitrogen inlet tube, a thermometer and a stirrer. IT-100 (IPDI trimer) was dissolved in 100 g of methyl isobutyl ketone (MIBK) under nitrogen, followed by the addition of 121 g (340 mmol) of Si-B3-OH. The mixture was heated to 55°C, followed by the addition of a solution of 0.025 g of dibutyltin dilaurate dissolved in 2 ml of MIBK. The mixture was further heated to 95°C and allowed to react for 6 hours.

[0200] Step (2) 450 g of water, 7.8 g of stearamidopropyl dimethylamine, 4 g of fatty alcohol polyoxyethylene ether (EO number 9), 42 g of dipropylene glycol and 4.7 g of acetic acid were added to a beaker and stirred to form a uniform surfactant solution. The solution was heated to 65° C., the reaction mixture in step (1) was cooled to 65° C. and the surfactant solution was slowly added to produce an emulsion. The mixture was blended (2 minutes) and homogenized at 6000 psi using an immersion mixer, and then MIBK was removed by evaporation under reduced pressure to obtain a dispersion. The solid content of the dispersion was adjusted to 25% by adding water.

[0201] Example 9

[0202] Step (1) Add 53 g (340 mmol NCO) into a four-necked flask equipped with a reflux condenser, a nitrogen inlet tube, a thermometer and a stirrer. IPP (IPDI prepolymer) was dissolved in 100 g of methyl isobutyl ketone (MIBK) under nitrogen, followed by the addition of 121 g (340 mmol) of Si-B3-OH. The mixture was heated to 55°C, followed by the addition of a solution of 0.025 g of dibutyltin dilaurate dissolved in 2 ml of MIBK. The mixture was further heated to 95°C and allowed to react for 6 hours.

[0203] Step (2) 450 g of water, 7.8 g of stearamidopropyl dimethylamine, 4 g of fatty alcohol polyoxyethylene ether (EO number 9), 42 g of dipropylene glycol and 4.7 g of acetic acid were added to a beaker and stirred to form a uniform surfactant solution. The solution was heated to 65° C., the reaction mixture in step (1) was cooled to 65° C. and the surfactant solution was slowly added to produce an emulsion. The mixture was blended (2 minutes) and homogenized at 6000 psi using an immersion mixer, and then MIBK was removed by evaporation under reduced pressure to obtain a dispersion. The solid content of the dispersion was adjusted to 25% by adding water.

[0204] The dispersion was tested on textiles: 100% polyester and 100% cotton fabrics were diluted with tap water to 5%, 3%, and 2% (dispersion content), respectively. The fabrics were then padded (with a 70% pick-up rate), dried at 110°C for 90 seconds, and baked at 170°C for 60 seconds. The water repellency, water repellency, and oil repellency of the resulting fabrics were evaluated. The results are shown in Table 5.

[0205] Table 5 Performance test table

[0206] As can be seen from Table 5, the dispersions obtained in Examples 1-9 of the present application can all impart good oil and water repellency to polyester or cotton fabrics. In particular, the dispersion comprising compound IA (i.e., the treating agent) has better oil and water repellency than the treating agent comprising compound IB.

[0207] Comparative Example 1

[0208] Step (1) Add 65 g (340 mmol NCO) into a four-necked flask equipped with a reflux condenser, a nitrogen inlet tube, a thermometer and a stirrer. HB-100 (hexamethylene diisocyanate-based biuret polyisocyanate) was dissolved in 100 g of methyl isobutyl ketone (MIBK) under nitrogen, followed by the addition of 92 g (340 mmol) of StA-OH. The mixture was heated to 55°C, followed by the addition of a solution of 0.025 g of dibutyltin dilaurate dissolved in 2 ml of MIBK. The mixture was further heated to 95°C and allowed to react for 6 hours.

[0209] Step (2) 450 g of water, 7.8 g of stearamidopropyl dimethylamine, 4 g of fatty alcohol polyoxyethylene ether (EO number 9), 42 g of dipropylene glycol and 4.7 g of acetic acid were added to a beaker and stirred to form a uniform surfactant solution. The solution was heated to 65° C., the reaction mixture in step (1) was cooled to 65° C. and the surfactant solution was slowly added to produce an emulsion. The mixture was blended (2 minutes) and homogenized at 6000 psi using an immersion mixer, and then MIBK was removed by evaporation under reduced pressure to obtain a dispersion. The solid content of the dispersion was adjusted to 25% by adding water.

[0210] Comparative Example 2

[0211] Polyester polyol (Qingdao Xinyu Chemical Company, brand 7112T, 1.5g), isocyanate IPDI (11.1g) and di-OH-terminated polysiloxane SF8427 (Dow Chemical, 31g) were charged into a three-necked flask and mixed at 80°C for 1 hour, and then 0.2g of catalyst dibutyltin dilaurate was added to the flask to start the reaction. The reaction continued for two hours to produce a first prepolymer intermediate. Dimethylol propionic acid (1.68g) was added to the flask and reacted for 2 hours. The first prepolymer intermediate was cooled to 40°C and neutralized with triethanolamine (1.26g) for 30 minutes. A small amount of acetone was added to the flask during the above process to keep the viscosity of the reaction system at about 500cps. The flask was cooled to room temperature, and 135g of an aqueous solution of ethylenediamine (0.83g) was added to the flask under vigorous stirring to form a dispersion. Finally, acetone was removed from the dispersion by distillation under reduced pressure, and the solids content of the dispersion was adjusted to 25% by adding water.

[0212] The performance test was carried out according to the test method of Examples 1-9. The results are shown in Table 6.

[0213] Table 6 Performance test table

[0214] Based on the performance test results in Table 5 and Table 6, the dispersions obtained in Examples 1-9 of the present application can impart good oil and water repellency to fiber fabrics. In particular, the treatment agent containing compound IA has better oil and water repellency than the treatment agent containing compound IB.

[0215] The treating agent obtained by reacting a long carbon chain with isocyanate in Comparative Example 1 has good water repellency but no oil repellency.

[0216] Comparative Example 2 uses dihydroxy-terminated polysiloxane as the main reactant. The results show that the treating agent has a certain water repellency in the fiber fabric but does not have oil repellency.

[0217] The technical solution of the present application is not limited to the above-mentioned specific embodiments. Any technical variations made according to the technical solution of the present application fall within the protection scope of the present application.

Claims

1. A compound, the raw materials for its preparation include a compound containing an isocyanate group and an isocyanate-reactive compound of formula I, MZ or ZMZ Formula I in, M is reactive with isocyanate; Z is selected from the following structures, In Z, R3 is independently selected from C1-C 20 Alkyl, C6-C 20 Aryl, C7-C 12 Aralkyl, C7-C 12 Alkyl, C1-C 20 an alkoxy group or an R4-O-R5- group, R4 is C1-C 20 Alkyl, C6-C 20 Aryl, C7-C 12 Arylalkyl or C7-C 12 Alkaryl, R5 is C1-C 20 Alkylene, 1≤a≤200; Y1 and Y2 are the same or different and are independently selected from C1-C 20 Alkyl, C6-C 20 Aryl, C7-C 12 Aralkyl, C7-C 12 An alkylaryl group or a structure of the following formula (1): R7 are each independently selected from C1-C 20 Alkyl, C6-C 20 Aryl, C7-C 12 Arylalkyl or C7-C 12 R8 are each independently selected from C1-C 20 Alkyl, C6-C 20 Aryl, C7-C 12 Aralkyl, C7-C 12 Alkyl, C1-C 20 Alkoxy or R9-OR 10 - group, wherein R9 is C1-C 20 Alkyl, C6-C 20 Aryl, C7-C 12 Arylalkyl or C7-C 12 The alkylaryl group, R 10 C1-C 20 Alkylene, 0≤b≤200.

2. The compound according to claim 1, characterized in that The isocyanate group-containing compound is selected from one or more of hexamethylene diisocyanate homopolymer, 3-isocyanatomethyl-3,4,4-trimethylcyclohexyl isocyanate, bis-(4-isocyanatocyclohexyl)methane, diisocyanate trimers shown in formula II a to II e, polymeric diphenylmethane diisocyanate shown in formula II f, and isophorone diisocyanate prepolymer shown in formula II g, In formula II f, n is 0-10, and in formula II g, n is 0-10.

3. The compound according to claim 1 or 2, characterized in that The M group of formula I contains one or more Zerewitinoff hydrogen atoms.

4. The compound according to any one of claims 1 to 3, characterized in that M is shown in formula I-1: HXB- Formula I-1 In formula I-1, B is selected from C1-C 20 Alkylene, C6-C 20 Arylene and combinations thereof; X is -O-, -S-, -N(R1)-, -O-(CH2) k -N(R2)-, -OC(O)-, R1 is selected from hydrogen atom or C1-C 20 Alkyl, R2 is selected from hydrogen atom or C1-C 20 Alkyl, 1≤k≤6; and / or M is shown in formula I-2: In formula I-2, B is selected from C1-C 20 Alkylene, C6-C 20 arylene groups and combinations thereof.

5. The compound according to any one of claims 1 to 4, characterized in that: The isocyanate-reactive compound includes isocyanate-reactive compound IA and / or isocyanate-reactive compound IB; The general formula of compound IA is the same as formula I, and also satisfies that when a is 1, Y1 and / or Y2 are structures of formula (1); when a is greater than 1 and ≤ 200, at least one Y1 is a structure of formula (1) and / or at least one Y2 is a structure of formula (1); The general formula of compound IB is the same as that of formula I, and furthermore, Y1 and Y2 are the same or different and are independently selected from C1-C 20 Alkyl, C6-C 20 Aryl, C7-C 12 Arylalkyl and C7-C 12 of alkylaryl.

6. The compound according to any one of claims 1 to 5, characterized in that In formula I-1, B is C1-C 10 alkylene, preferably B is a C1-C6 alkylene; in X, R1 is selected from a hydrogen atom or a C1-C 10 Alkyl, preferably R1 is selected from a hydrogen atom or a methyl group; In formula I-2, B is C1-C 10 alkylene, preferably B is a C1-C6 alkylene; In Z, R3 is independently C1-C 10 Alkyl, C6-C 10 Aryl, C7-C 12 Aralkyl, C7-C 12 Alkyl, C1-C 10 Alkoxy or R4-O-R5- group, R4 is C1-C 10 Alkyl, C6-C 10 Aryl, C7-C 12 Arylalkyl or C7-C 12 Alkaryl, R5 is C1-C 10 alkylene, 1≤a≤100; R7 are each independently C1-C 10 Alkyl, C6-C 10 Aryl, C7-C 12 Arylalkyl or C7-C 12 R8 is independently C1-C 10 Alkyl, C6-C 10 Aryl, C7-C 12 Aralkyl, C7-C 12 Alkyl, C1-C 10 Alkoxy or R9-OR 10 - group, wherein R9 is C1-C 10 Alkyl, C6-C 10 Aryl, C7-C 12 Arylalkyl or C7-C 12 The alkylaryl group, R 10 C1-C 10 Alkylene, 0≤b≤100.

7. The compound according to any one of claims 1 to 6, characterized in that Z is independently selected from one or more of the following structures i-1 to i-6: Z is preferred from One or more of; R is independently selected from C1-C 10 Alkyl, C6-C 10 Aryl, C7-C 12 Arylalkyl or C7-C 12 Alkaryl; Me represents methyl, ph represents phenyl; 1≤m+1≤60, preferably 1≤m+1≤30; 0≤p≤60, preferably 0≤p≤30; 0≤q≤60, preferably 0≤q≤30; 1≤x≤9, preferably 1≤x≤7, and each x may be the same or different.

8. The compound according to any one of claims 1 to 7, characterized in that The isocyanate-reactive compound IA is selected from HO-(CH2)3Si(OSi(CH3)3)3; HS-(CH2)3Si(OSi(CH3)3)3; HO-(CH2)3Si(CH3)(OSi(CH3)3)2; NH2-(CH2)3Si(OSi(CH3)3)3; NH(CH3)-(CH2)3Si(OSi(CH3)3)3; NH2-(CH2)3Si(CH3)(OSi(CH3)3)2; NH(CH3)-(CH2)3Si(CH3)(OSi(CH3)3)2; HO-(CH2)3Si(OSi(CH2CH3)3)3; HO-CH2-Si(OSi(CH3)3)3; HO-(CH2)3Si(CH3)[O-[Si(CH3)2O]n-Si(CH3)2C4H9]2, 0≤n≤25; HO-(CH2)2-NH-(CH2)3Si(OSi(CH3)3)3; NH[-(CH2)3-Si(OSi(CH3)3)3]2; NH[-(CH2)3-Si(CH3)(OSi(CH3)3)2]2; and / or The isocyanate-reactive compound IB is selected from HO-(CH2)3[Si(CH3)2O]n-Si(CH3)2C4H9, 1≤n≤25; <h2 style=";text-align:left;direction:ltr">HO-(CH2)3[Si(CH3)2O]n-Si(CH3)2C8H<h2 style=";text-align:left;direction:ltr"> 17 <h2 style=";text-align:left;direction:ltr"> 1≤n≤25 HO-(CH2)3[Si(CH3)2O]n-Si(CH3)3, 1≤n≤25; NH2-(CH2)3-[Si(CH3)2O]n-Si(CH3)2C4H9 (C4H9 represents butyl), 1≤n≤25; HO-(CH2)2-NH-(CH2)3[Si(CH3)2O]n-Si(CH3)2C4H9 (C4H9 represents butyl), 1≤n≤25; NH[-(CH2)3-(Si(CH3)2O) n -Si(CH3)2C4H9]2 (C4H9 represents butyl), 1≤n≤25.

9. A treating agent comprising the compound according to any one of claims 1 to 8, an emulsifier and an aqueous medium, preferably, the aqueous medium comprises water and an optional organic solvent.

10. A method for preparing the treatment agent according to claim 9, comprising mixing a solution comprising the compound according to any one of claims 1 to 8 with a solution comprising an emulsifier and water, preferably comprising the following steps: (1) reacting an isocyanate group-containing compound and an isocyanate-reactive compound in the presence of a solvent and a catalyst to obtain a reaction product; (2) The reaction product in (1) is mixed with a solution containing an emulsifier and water, and then homogenized, and the solvent is removed to obtain the treating agent.

11. Use of the compound according to any one of claims 1 to 8, the treating agent according to claim 9, or the treating agent prepared by the method according to claim 10 in fiber fabrics, leather, non-woven fabrics, asbestos, fur, concrete, stone, paper products, plastics or coatings.

12. A water-repellent, oil-repellent or antifouling product, comprising a product and a compound according to any one of claims 1 to 8 or a treating agent according to claim 9 or a treating agent prepared by the method according to claim 10, wherein the product is a fiber fabric, leather, non-woven fabric, asbestos, fur, concrete, stone, paper product, plastic or coating, Preferably, the compound according to any one of claims 1 to 8, the treating agent according to claim 9, or the treating agent prepared by the method according to claim 10 is attached to the surface and / or interior of the product.

13. A method for treating a product, comprising contacting the product with a compound according to any one of claims 1 to 8, or a treating agent according to claim 9, or a treating agent prepared by the method according to claim 10, wherein the product is a fiber fabric, leather, non-woven fabric, asbestos, fur, concrete, stone, paper product, plastic or coating. Preferably, the contact is achieved by a surface sizing process, a surface coating process, a wet-end addition process or an immersion treatment process.

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