CN115717034A - Water-resistant adhesive based on hydrogen bond condensate and hydrophobic group and preparation method and application thereof - Google Patents

Abstract

The application provides a water-resistant adhesive based on hydrogen bond condensates and hydrophobic groups, its preparation method and application, and relates to the field of materials. A water-resistant adhesive based on hydrogen bond condensates and hydrophobic groups, whose raw materials include polyvinylpyrrolidone, acrylic monomers, benzyl methacrylate monomers and initiators. The preparation method of the water-resistant adhesive based on the hydrogen bond condensate and the hydrophobic group comprises: mixing the raw materials to obtain a polymeric precursor, and then subjecting the polymeric precursor to ultraviolet radiation in-situ curing or heating reaction. Application of water-resistant adhesives based on hydrogen-bonded condensates and hydrophobic groups for underwater bonding. The water-resistant adhesive based on hydrogen bond condensates and hydrophobic groups provided by the application has excellent water resistance, salt water resistance, acid resistance and high humidity resistance.

Description

Water-resistant adhesive based on hydrogen bond condensate and hydrophobic group and its preparation method and application

technical field

The present application relates to the field of materials, in particular to a water-resistant adhesive based on hydrogen bond condensates and hydrophobic groups and its preparation method and application.

Background technique

Underwater adhesives play an important role in daily life and industrial scenarios, including wound dressings, underwater robots, aquatic energy devices, underwater repair, and marine industry, etc. A variety of high-strength adhesives have been developed for different substrates. However, most traditional adhesives cannot be used directly underwater, or have poor water resistance. This is because the surface of the underwater substrate will form a hydration layer, thereby preventing the adhesive and the interface from forming a high-strength effect, making it easy to cause problems such as debonding and weakening of the strength after bonding. In addition, direct use of adhesives in water environments, especially underwater, also requires adhesives to have certain stability, while most traditional adhesives have low viscosity, are easy to spread, and are easy to dissolve. If they cannot achieve the bonding effect, they will be lost. The traditional method is usually to use compounds with hydrophobic groups to achieve the effect of draining the hydration layer and water resistance. However, these adhesives are generally difficult to achieve high-strength adhesive properties on various substrates such as glass and metal.

In recent years, inspired by the adhesion in organisms, a series of underwater adhesives based on catechol groups have been developed. Through the synergistic effect of phenolic hydroxyl groups and benzene rings, this series of adhesives exhibit excellent bonding performance and water resistance on different substrates. However, these adhesives require complex precursor synthesis steps, greatly increasing the cost and difficulty of commercialization. At the same time, this kind of adhesive has low hardness after swelling under water, so it is not suitable for use as a structural adhesive. On the other hand, coacervates are also widely used for underwater bonding. Through the electrostatic interaction between groups, the condensate can also maintain stability and achieve good bonding strength under water. However, most coagulation processes have different requirements for external conditions, such as pH, ionic bond strength, ion concentration, etc., which limit the application scenarios of condensates.

Contents of the invention

The purpose of this application is to provide a water-resistant adhesive based on hydrogen bond condensate and hydrophobic groups, its preparation method and application, so as to solve the above problems.

To achieve the above object, the application adopts the following technical solutions:

A water-resistant adhesive based on hydrogen bond condensates and hydrophobic groups, the raw materials of which include polyvinylpyrrolidone, acrylic monomers, benzyl methacrylate monomers and initiators.

Preferably, the acrylic monomer comprises acrylic acid and/or methacrylic acid.

Preferably, the benzyl methacrylate monomer includes benzyl methacrylate and/or benzyl acrylate.

Preferably, the mass ratio of the benzyl methacrylate monomer to the acrylic monomer is (0.7-2.5):1.

Preferably, the initiator includes a photoinitiator and a thermal initiator;

The photoinitiator includes 2,2-diethoxyacetophenone and/or 1-hydroxycyclohexyl phenyl ketone;

The thermal initiator includes azobisisobutyronitrile and/or benzoyl peroxide.

Preferably, the mass of the photoinitiator or the thermal initiator is independently 0.7-2% of the total mass of the acrylic monomer and the benzyl methacrylate monomer.

Preferably, the molar ratio of the vinylpyrrolidone monomer in the polyvinylpyrrolidone to the acrylic monomer is 1:1.

The present application also provides a method for preparing the water-resistant adhesive based on hydrogen bond condensates and hydrophobic groups, including:

The raw materials are mixed to obtain a polymeric precursor, and then the polymeric precursor is subjected to in-situ curing by ultraviolet radiation or heating reaction.

Preferably, the power density of the ultraviolet light source used in the ultraviolet radiation in-situ curing is 30-50mW/cm ² , the time of the ultraviolet radiation in-situ curing is 5-60min, and the temperature of the heating reaction is 65-80°C , the time is 8-24h.

The present application also provides an application of the water-resistant adhesive based on hydrogen bond condensates and hydrophobic groups for underwater bonding.

Compared with the prior art, the beneficial effects of the present application include:

The water-resistant adhesive based on hydrogen bond condensates and hydrophobic groups provided by this application uses polyvinylpyrrolidone, acrylic monomers, benzyl methacrylate monomers and initiators as raw materials, and utilizes polyvinylpyrrolidone, acrylic monomers The coagulation effect can be obtained by the hydrogen bond between the bodies, and the benzyl methacrylate monomer is used as the hydrophobic monomer to copolymerize with polyvinylpyrrolidone and acrylic monomer to obtain the hydrophilic-hydrophobic synergy in the system; thus making the Adhesives can simultaneously absorb and drain the hydration layer on the substrate during underwater bonding, and on the other hand, can ensure water resistance while achieving high-strength bonding.

The water-resistant adhesive has a long-term water-resistant effect after curing, which can meet the needs of long-term use; and is not limited by the conditions of use and the environment, and the bonding process can be completely carried out underwater, including the application of precursors and photopolymerization, enriched Application scenarios. It has excellent water resistance, salt water resistance, acid resistance and high humidity resistance. Taking water resistance as an example, the adhesive strength of 7MPa can still be maintained after the sample is soaked in water for 30 days.

The water-resistant adhesive based on hydrogen bond condensate and hydrophobic groups provided by this application has super high bonding strength for different substrate surfaces, including glass, ceramics, metal, polyvinyl chloride, organic glass, etc.

Description of drawings

In order to more clearly illustrate the technical solutions of the embodiments of the present application, the following will briefly introduce the accompanying drawings used in the embodiments. It should be understood that the following drawings only show some embodiments of the present application, so should be considered as limiting the scope of the application.

Figure 1 is a schematic diagram of the in-situ condensation and photocuring of the precursors of acrylic acid, polyvinylpyrrolidone, and benzyl methacrylate, as well as the internal forces of the adhesive body and the possible forces formed between the adhesive and different substrates;

Fig. 2 is the comparison of the infrared spectra of the obtained adhesive in Example 1, polyvinylpyrrolidone, and acrylic acid-benzyl methacrylate copolymer;

Fig. 3 is the adhesive obtained in embodiment 1 and its infrared spectrogram after being processed in different environments for 30 days;

Figure 4 shows the pictures of Examples 4 and 5 hanging heavy objects for a long time in water and salt water environment respectively.

Detailed ways

As used herein:

"Prepared from" is synonymous with "comprising". As used herein, the terms "comprises," "including," "has," "containing," or any other variation thereof, are intended to cover a non-exclusive inclusion. For example, a composition, step, method, article, or device comprising listed elements is not necessarily limited to those elements, but may include other elements not explicitly listed or inherent to such composition, step, method, article, or device. elements.

The conjunction "consisting of" excludes any unspecified elements, steps or components. If used in a claim, this phrase will make the claim closed so that it does not contain material other than those described except for the customary impurities associated therewith. When the phrase "consisting of" appears in a clause of the subject of a claim rather than immediately following the subject matter, it only defines the elements described in that clause; other elements are not excluded from the claims as a whole. beyond the claims.

When amounts, concentrations, or other values or parameters are expressed in terms of ranges, preferred ranges, or ranges bounded by a series of upper preferred values and lower preferred values, it is to be understood that any range upper or preferred value combined with any lower range limit is specifically disclosed. All ranges formed by any pairing of values or preferred values, whether or not such ranges are individually disclosed. For example, when the range "1-5" is disclosed, the described range should be construed to include the ranges "1-4", "1-3", "1-2", "1-2 and 4-5" , "1 ~ 3 and 5" and so on. When a numerical range is described herein, unless otherwise stated, that range is intended to include its endpoints and all integers and fractions within the range.

In these examples, unless otherwise specified, the stated parts and percentages are by mass.

"Parts by mass" refers to the basic measurement unit that expresses the mass ratio relationship of multiple components, and 1 part can represent any unit mass, such as 1g or 2.689g. If we say that the mass part of A component is a part, and the mass part of B component is b part, it means that the mass ratio of A component to B component is a:b. Alternatively, it means that the mass of component A is aK, and the mass of component B is bK (K is an arbitrary number, representing a multiple factor). It should not be misunderstood that, unlike the parts by mass, the sum of parts by mass of all components is not limited to 100 parts.

"And/or" is used to indicate that one or both of the stated situations may occur, for example, A and/or B includes (A and B) and (A or B).

A water-resistant adhesive based on hydrogen bond condensate and hydrophobic groups, its raw materials include polyvinylpyrrolidone, acrylic monomers, benzyl methacrylate monomers and photoinitiators.

Agglomeration can also occur between stronger hydrogen bond donors (such as acrylic acid, methacrylic acid, etc.) and stronger hydrogen bond acceptors (such as polyvinylpyrrolidone, etc.). Compared with the electrostatic condensation process, condensation based on hydrogen bonding has significant advantages, such as low requirements on the external environment, simple operation, low cost, and suitable for large-scale production. Taking polyacrylic acid and polyvinylpyrrolidone as an example, the strengths of their hydrogen bonds with water molecules in aqueous solution are about -22.28kJ/mol and -24.59kJ/mol respectively, and the hydrogen bonds between them are about - 35.86kJ/mol, so that the coagulation effect can be achieved simply by mixing its aqueous solution. At the same time, the in-situ coagulation during the underwater polymerization can make it achieve high bonding strength on the interface. In addition, it can be copolymerized with hydrophobic monomers (such as benzyl methacrylate, benzyl acrylate, etc.) during the in-situ coagulation process, so that the hydrophilic and hydrophobic synergies in the system can be achieved. In underwater bonding, on the one hand, it can simultaneously absorb and drain the hydration layer on the substrate, and on the other hand, it can ensure water resistance while achieving high-strength bonding. This application provides the principle and method for the preparation of adhesives based on the synergistic effect of hydrogen bond condensates and hydrophobic groups, and provides a suitable solution for scenarios that require high-strength bonding and long-term water and acid resistance under water. The raw materials are simple, cheap and Easy to commercialize.

In Figure 1, a) represents the in-situ condensation and photocuring of the precursors of acrylic acid (AA), polyvinylpyrrolidone (PVP), and benzyl methacrylate (BzMA); b) represents the possible interfacial forces between the adhesive and different substrates And the non-covalent interaction formed inside the adhesive.

In an optional embodiment, the acrylic monomer includes acrylic acid and/or methacrylic acid.

In an optional embodiment, the benzyl methacrylate monomer includes benzyl methacrylate and/or benzyl acrylate.

In an optional embodiment, the mass ratio of the benzyl methacrylate monomer to the acrylic monomer is (0.7-2.5):1.

By adjusting this mass ratio, the viscosity of the polymerization precursor can be changed so that the precursor remains stable under water for a short time to complete photopolymerization.

Optionally, the mass ratio of the benzyl methacrylate monomer to the acrylic monomer may be 0.7:1, 1:1, 1.5:1, 2:1, 2.5:1 or (0.7- 2.5): Any value between 1.

In an optional embodiment, the initiator includes a photoinitiator and a thermal initiator;

The photoinitiator includes 2,2-diethoxyacetophenone and/or 1-hydroxycyclohexyl phenyl ketone;

The thermal initiator includes azobisisobutyronitrile and/or benzoyl peroxide.

In an optional embodiment, the mass of the photoinitiator is 0.7-2% of the total mass of the acrylic monomer and the benzyl methacrylate monomer.

In an optional embodiment, the molar ratio of the vinylpyrrolidone monomer in the polyvinylpyrrolidone to the acrylic monomer is 1:1.

The present application also provides a method for preparing the water-resistant adhesive based on hydrogen bond condensates and hydrophobic groups, including:

The raw materials are mixed to obtain a polymeric precursor, and then the polymeric precursor is subjected to in-situ curing by ultraviolet radiation or heating reaction.

In an optional embodiment, the power density of the ultraviolet light source used in the ultraviolet radiation in-situ curing is 30-50mW/cm ² , the time for the ultraviolet radiation in-situ curing is 5-60min, and the heating reaction The temperature is 65-80°C, and the time is 8-24h.

Optionally, the power density of the ultraviolet light source used in the in-situ curing of ultraviolet radiation can be 30mW/cm ² , 40mW/cm ² , 50mW/cm ² or any value between 30-50mW/cm ² , the The time of in-situ curing by ultraviolet radiation can be any value between 5min, 10min, 15min, 20min, 25min, 30min, 35min, 40min, 45min, 50min, 55min, 60min or 5-60min, and the temperature of the heating reaction can be It can be any value between 65°C, 70°C, 75°C, 80°C or 65-80°C, and the time can be any value between 8h, 12h, 16h, 20h, 24h or 8-24h.

The present application also provides an application of the water-resistant adhesive based on hydrogen bond condensates and hydrophobic groups for underwater bonding.

The implementation of the present application will be described in detail below in conjunction with specific examples, but those skilled in the art will understand that the following examples are only used to illustrate the present application, and should not be considered as limiting the scope of the present application. Those who do not indicate the specific conditions in the examples are carried out according to the conventional conditions or the conditions suggested by the manufacturer. The reagents or instruments used were not indicated by the manufacturer, and they were all conventional products that could be purchased from the market.

Example 1

This embodiment provides a water-resistant adhesive based on hydrogen bond condensates and hydrophobic groups, and its preparation method is as follows:

Mix 1g of acrylic acid, 1.54g of polyvinylpyrrolidone, 1.5g of benzyl methacrylate and 25mg of photoinitiator 2,2-diethoxyacetophenone, and evenly coat the precursor on the substrate in the air , irradiating with a UV light source with a power density of 50mW/cm ² for 30min to complete the curing.

Fig. 2 is the comparison of the infrared spectra of the adhesive obtained in Example 1, polyvinylpyrrolidone, and acrylic acid-benzyl methacrylate copolymer. In the examples, the characteristic peak of polyacrylic acid moves from 1703cm ^-1 to 1720cm ^-1 , and the characteristic peak of polyvinylpyrrolidone moves from 1645cm ^-1 to 1630cm ^-1 , indicating the strong hydrogen bond between the two.

Figure 3 is a comparison of the infrared spectrum of the adhesive obtained in Example 1 and its treatment in different environments for 30 days. The results of Example 1 that the infrared characteristic peaks of PAA and PVP before and after treatment remained similar, indicating that the hydrogen bond between PAA and PVP in the treated sample was not affected.

Example 2

This embodiment provides a water-resistant adhesive based on hydrogen bond condensates and hydrophobic groups, and its preparation method is as follows:

Mix 1.2g of methacrylic acid, 1.54g of polyvinylpyrrolidone, 1.8g of benzyl methacrylate and 30mg of photoinitiator 2,2-diethoxyacetophenone, and evenly coat the precursor in the air On the substrate, irradiate with an ultraviolet light source with a power density of 50mW/cm ² for 30min to complete the curing.

Example 3

This embodiment provides a water-resistant adhesive based on hydrogen bond condensates and hydrophobic groups, and its preparation method is as follows:

Mix 1g of acrylic acid, 1.54g of polyvinylpyrrolidone, 1.5g of benzyl acrylate and 25mg of photoinitiator 2,2-diethoxyacetophenone, and evenly coat the precursor on the substrate in the air to 50mW/cm ² power density of ultraviolet light source irradiation for 30min to complete the curing.

Example 4

This embodiment provides a water-resistant adhesive based on hydrogen bond condensates and hydrophobic groups, and its preparation method is as follows:

Mix 1g of acrylic acid, 1.54g of polyvinylpyrrolidone, 1.5g of benzyl methacrylate and 25mg of photoinitiator 2,2-diethoxyacetophenone, and evenly coat the precursor on the substrate in the air , irradiating with a UV light source with a power density of 50mW/cm ² for 30min to complete the curing. The obtained samples were soaked in water for 30 days.

Example 5

This embodiment provides a water-resistant adhesive based on hydrogen bond condensates and hydrophobic groups, and its preparation method is as follows:

Mix 1g of acrylic acid, 1.54g of polyvinylpyrrolidone, 1.5g of benzyl methacrylate and 25mg of photoinitiator 2,2-diethoxyacetophenone, and evenly coat the precursor on the substrate in the air , irradiating with a UV light source with a power density of 50mW/cm ² for 30min to complete the curing. Soak the obtained sample in 1mol/L sodium chloride aqueous solution for 30 days.

Fig. 4 is the photograph that embodiment 4 and embodiment 5 hang 5kg weight in water and 1M saline respectively and keep for two months. It shows good water resistance and salt water resistance bonding performance (the bonding area is about 4 cm ² ).

Example 6

This embodiment provides a water-resistant adhesive based on hydrogen bond condensates and hydrophobic groups, and its preparation method is as follows:

Mix 1g of acrylic acid, 1.54g of polyvinylpyrrolidone, 1.5g of benzyl methacrylate and 25mg of photoinitiator 2,2-diethoxyacetophenone, and evenly coat the precursor on the substrate in the air , irradiating with a UV light source with a power density of 50mW/cm ² for 30min to complete the curing. The obtained sample was soaked in an aqueous hydrogen chloride solution with pH=1 for 30 days.

Example 7

This embodiment provides a water-resistant adhesive based on hydrogen bond condensates and hydrophobic groups, and its preparation method is as follows:

Mix 1g of acrylic acid, 1.54g of polyvinylpyrrolidone, 1.5g of benzyl methacrylate and 25mg of photoinitiator 2,2-diethoxyacetophenone, and evenly coat the precursor on the substrate in the air , irradiating with a UV light source with a power density of 50mW/cm ² for 30min to complete the curing. The obtained samples were kept in a humidity chamber at 90% relative humidity for 30 days.

By adjusting the content of benzyl methacrylate in the adhesive component, the viscosity of the precursor can be changed, so that the precursor can remain stable under water for a short time, so that the adhesive can be directly coated on the surface of the substrate under water and complete polymerization ,Specifically:

Example 8

This embodiment provides a water-resistant adhesive based on hydrogen bond condensates and hydrophobic groups, and its preparation method is as follows:

Mix 1g of acrylic acid, 1.54g of polyvinylpyrrolidone, 0.7g of benzyl methacrylate and 17mg of photoinitiator 2,2-diethoxyacetophenone, and evenly coat the precursor directly on the substrate under water On the surface, irradiate with a UV light source with a power density of 50mW/cm ² for 30min in a water environment to complete the curing.

Comparative example 1

The glass substrates were bonded using commercial 3M quick-drying adhesive (model CA40H) and their lap shear strength was measured.

Comparative example 2

2g of acrylic acid, 1.54g of polyvinylpyrrolidone, ^and 25mg of photoinitiator 2,2-diethoxyacetophenone were mixed evenly, and the precursor was evenly coated on the substrate in the air, with a power density of 50mW/cm The UV light source was irradiated for 30 minutes to complete the curing.

Test the adhesive performance data of its initial state, and then soak the obtained samples in water for 7 days to test their adhesive performance.

Comparative example 3

Mix and shake the same mass of 10wt% polyacrylic acid aqueous solution and 15wt% polyvinylpyrrolidone aqueous solution, centrifuge at a speed of 7000rpm for 10min, obtain a white condensate, apply it evenly on the substrate in the air, and dry it in the air for 3 days until condensed The object becomes transparent, and its adhesive performance is tested.

Comparative example 4

Mix 1g of acrylic acid, 1.5g of benzyl methacrylate and 25mg of photoinitiator 2,2-diethoxyacetophenone evenly, and evenly coat the precursor on the substrate in the air at 50mW/cm ² The UV light source of power density was irradiated for 30 minutes to complete the curing. The obtained samples were soaked in water for 30 days.

Unless otherwise specified, the substrates used in the tests of the examples and comparative examples are all glass.

Table 1 compares the adhesive properties of different formulations of Examples 1-3 and Comparative Example 1.

Table 1 Example 1-3 and Comparative Example 1 glass substrate lap shear test performance comparison (not soaked in water)

sample Shear strength (MPa) Example 1 8.73±0.37 Example 2 8.60±2.07 Example 3 9.49±0.39 Comparative example 1 2.00±0.40

Table 2 compares the adhesive properties of different formulations of Examples 4-7 and Comparative Examples 2-3.

Table 2 Example 4-7 and Comparative Example 2-3 Comparison of lap shear performance of glass substrates

sample processing conditions Shear strength (MPa) Example 4 water (30 days) 7.00±0.12 Example 5 1mol/L sodium chloride aqueous solution (30 days) 8.04±0.85 Example 6 pH=1 hydrogen chloride aqueous solution (30 days) 7.31±0.45 Example 7 90% relative humidity (30 days) 9.18±0.46 Example 8 Precursor applied directly underwater and cured underwater 9.29±1.03 Comparative example 2 water (7 days) 1.55±0.26 Comparative example 4 water (30 days) 3.01±0.20

Table 3 compares the adhesive properties of Comparative Example 2 and Comparative Example 4 without soaking in water.

Table 3 Comparative Example 2 and Comparative Example 4 Comparison of Lap Shear Performance of Glass Substrates

sample processing conditions Shear strength (MPa) Comparative example 2 unsoaked water 11.75±0.40 Comparative example 4 unsoaked water 8.53±1.00

From the comparison of Table 3 and Table 2, it can be seen that when the lack of polyvinylpyrrolidone or benzyl methacrylate, although the initial shear strength is very high, the shear strength after soaking in water is greatly reduced, and it is not suitable for underwater use. .

More importantly, the aggregation brought about by the super-strong hydrogen bond between polyacrylic acid and polyvinylpyrrolidone can cooperate with the hydrophobic group, and the protection of the internal hydrogen bond keeps it low in water for a long time, ensuring a long-term Resistant to water use. However, in Comparative Examples 2 and 3, when the components lacked hydrophobic groups or hydrogen bonds condensed, the water resistance decreased significantly.

In addition, since the adhesive can form non-covalent interactions with the surfaces of different substrates, the adhesive exhibits good bonding strength on different substrates.

Table 4 compares the adhesive properties of Example 1 and Example 8 on different substrates.

Table 4 embodiment 1 and embodiment 8 in the lap shear performance of different substrates

It should be noted that the polymerization methods in the above-mentioned implementation methods are all ultraviolet light polymerization, which requires ultraviolet rays to pass through the substrate to initiate polymerization. For the bonding of opaque substrates, the above methods are limited. The formulation of the present application can solve this problem by generating adhesive strength through thermally induced polymerization.

Specifically: keep the other components of the adhesive unchanged, use a thermal initiator instead of a photoinitiator, and polymerize the precursor by heating to a certain temperature. The thermal initiator can be azobisisobutyronitrile, benzoyl peroxide, etc., and the thermal curing time varies.

The specific plan is:

Example 9

Mix 1g of acrylic acid, 1.54g of polyvinylpyrrolidone, 1.5g of benzyl methacrylate and 50mg of azobisisobutyronitrile evenly, put in a round-bottom bottle to remove oxygen for 20min, and gradually heat to 60°C in the bottle Keep it for 30min, then evenly coat the precursor on the substrate and heat it to 70°C for 10h.

After the above embodiments are cured on the glass substrate, the bonding strength measured by the lap shear test is 8.03±1.14 MPa, which is close to the bonding effect of light curing.

Finally, it should be noted that: the above embodiments are only used to illustrate the technical solutions of the present application, and are not intended to limit it; although the application has been described in detail with reference to the foregoing embodiments, those of ordinary skill in the art should understand that: It is still possible to modify the technical solutions described in the foregoing embodiments, or perform equivalent replacements for some or all of the technical features; and these modifications or replacements do not make the essence of the corresponding technical solutions deviate from the technical solutions of the various embodiments of the present application. scope.

In addition, those skilled in the art will appreciate that although some embodiments herein include some features included in other embodiments but not others, combinations of features from different embodiments are meant to be within the scope of the present application. And form different embodiments. For example, in the following claims, any one of the claimed embodiments may be used in any combination. The information disclosed in the background technology section is only intended to deepen the understanding of the general background technology of the application, and should not be regarded as an acknowledgment or any form of suggestion that the information constitutes the prior art known to those skilled in the art.

Claims (10)

1. The water-resistant adhesive is characterized in that raw materials comprise polyvinylpyrrolidone, acrylic monomers, benzyl methacrylate monomers and an initiator.

2. A water resistant adhesive based on hydrogen bond condensates and hydrophobic groups as claimed in claim 1 characterised in that said acrylic monomer includes acrylic acid and/or methacrylic acid.

3. The water resistant adhesive based on hydrogen bond agglomerates and hydrophobic groups of claim 1 wherein said benzyl methacrylate monomers comprise benzyl methacrylate and/or benzyl acrylate.

4. The water-resistant adhesive based on hydrogen bond condensates and hydrophobic groups as claimed in claim 1, characterized in that the mass ratio of the benzyl methacrylate monomer to the acrylic monomer is (0.7-2.5): 1.

5. the water-resistant adhesive based on hydrogen bond condensates and hydrophobic groups of claim 1, characterized in that said initiator comprises a photoinitiator and a thermal initiator;

the photoinitiator comprises 2, 2-diethoxyacetophenone and/or 1-hydroxycyclohexyl phenyl ketone;

the thermal initiator comprises azobisisobutyronitrile and/or benzoyl peroxide.

6. A water-resistant adhesive based on hydrogen bond condensates and hydrophobic groups as claimed in claim 5, characterized in that the mass of said photoinitiator or said thermal initiator is each independently 0.7-2% of the total mass of said acrylic monomer and said benzyl methacrylate monomer.

7. The water-resistant adhesive based on hydrogen bond condensates and hydrophobic groups of any one of claims 1 to 6, characterized in that the molar ratio of vinylpyrrolidone monomer to acrylic monomer in the polyvinylpyrrolidone is 1:1.

8. a method of preparing a water-resistant adhesive based on hydrogen bond condensates and hydrophobic groups as claimed in any one of claims 1 to 7, which comprises:

mixing the raw materials to obtain a polymerization precursor, and then carrying out ultraviolet radiation in-situ curing or heating reaction on the polymerization precursor.

9. The method of claim 8, wherein the UV radiation cures in situ using a UV light source having workThe specific density is 30-50mW/cm ² The time of the ultraviolet radiation in-situ curing is 5-60min, the temperature of the heating reaction is 65-80 ℃, and the time is 8-24h.

10. Use of a water-resistant adhesive based on hydrogen bond condensates and hydrophobic groups as defined in any one of claims 1 to 7 for underwater bonding.

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