Adhesion promoting compounds and uses thereof

Abstract

The present invention relates to novel compounds and their use as adhesion promoting additives. In particular, the present invention relates to additives for promoting adhesion between epoxy amines and polysiloxanes. In marine and protective coating applications, the additives are particularly useful for promoting adhesion between epoxy amine coatings and polysiloxane coatings. The present invention also relates to methods of promoting adhesion between epoxy amines and polysiloxanes.

Description

[0001] This invention relates to novel compounds and their use as adhesion-promoting additives. In particular, this invention relates to additives for promoting adhesion between epoxyamines and polysiloxanes. In marine and protective coating applications, the additives are particularly useful for promoting adhesion between epoxyamine coatings and polysiloxane coatings. This invention also relates to methods for promoting adhesion between epoxyamines and polysiloxanes.

[0002] Marine coatings are protective coatings applied to marine environments to protect primarily submerged materials from the effects of seawater. Therefore, marine coatings are applied to surfaces such as the hulls of ships and other maritime vessels, as well as to submerged static structures such as oil and gas pipes, water pipes, and oil and gas rigs. Typically, marine coating is a three-stage process. In the first stage, a primer or base coat is applied. Primers / base coats are generally used to impart corrosion-resistant properties to exposed surfaces. Amine-cured epoxy-functionalized polymers are commonly used in these primer coatings because of their ability to impart the necessary corrosion resistance while also bonding firmly to metallic surfaces such as ship hulls. For submerged surfaces, at least three such primer coatings are typically applied.

[0003] In addition to a primer / base coat, an antifouling top coat is required to prevent slime buildup and the adhesion of marine species (barnacles, algae, etc.) to the material surface. This prevents increased drag (leading to reduced fuel efficiency) and cross-contamination of marine species throughout the waterway. While biocides such as cuprous oxide were previously added to marine coatings to prevent scaling, their use is now regulated due to the leaching of these biocides into the waterway. Polysiloxanes (organosilicones) are now the preferred material for antifouling / topcoats due to their low surface energy, which prevents marine organisms from attaching to the surface.

[0004] A problem associated with using silicone topcoats is that their low surface energy properties (crucial for antifouling effectiveness) also prevent adhesion to the primer or base coat. Therefore, an intermediate coat, or "tie-coat," is needed, which exhibits good adhesion to both the primer and topcoat and serves to bond or join the two coats together. The primary purpose of the tie-coat is to prevent peeling between the primer and topcoat. However, considering formulation costs, application costs, and dry-dock time during vessel downtime, the application of tie-coats can typically account for up to 35% of the cost of vessel coating.

[0005] In summary, while known primer and topcoat formulations each impart the necessary functionality to marine and protective coatings, their lack of adhesion to each other poses problems from both a cost and efficiency perspective. Eliminating and / or mitigating one or more of these problems would be advantageous. In particular, it would be advantageous to eliminate the need to apply separate adhesive coatings to ensure adhesion between the primer and topcoat formulations. Providing methods to promote adhesion between epoxyamine and polysiloxane coatings would also be more generally useful. Invention Overview According to a first aspect of the invention, compounds of formula I(a)(i), I(a)(ii), I(b)(i), I(b)(ii), I(c)(i), or I(c)(ii) are provided: ; R can be the same or different 1 and R 2 Each is H or alkyl C 1-10 ; Or R 1 and R 2 Together with -OBO-, they form a 5-, 6-, or 7-membered ring optionally substituted with one or more C1-C4 alkyl groups; Each R 3 It is independently a C1-C8 alkyl or phenyl group; A 1 and A 2 Each is independently -CH2 or CHY; The Y group, which may or may not be present, consists of one or more substituents selected from the following: C1-C 20 Straight-chain or branched saturated or unsaturated aliphatic hydrocarbons; halogen-substituted C1-C 20 Straight-chain or branched saturated or unsaturated aliphatic hydrocarbons; halogens; -OR 4 ;-NR 4 2; -NO2; -SO3H; -C(=O)R 4 ;-C(=O)OR 4 ;-OC(=O)NR 4 2; -C≡N; -SR 4 ;-P(=O)R 4 2; -OC(=O)OR 5 ;-NC(=O)OR 5 ;-SO2R 5 ;-SOR 5 ;where R 4 It is H, C1-C 20 Straight-chain or branched aliphatic hydrocarbon groups or PhY; and R 5 It is C1-C20 A straight-chain or branched saturated or unsaturated hydrocarbon group or PhY; or Y is PhY; PhY is a phenyl group that is optionally substituted with Y; And m is an integer from 1 to 3; and its isomers; Where equation I is not: .

[0007] In the implementation scheme, the compound of formula I is not: .

[0008] As used herein, the term "alkyl" refers to a fully saturated, branched, unbranched, or cyclic hydrocarbon moiety, i.e., a primary alkyl, secondary alkyl, or tertiary alkyl, or, where appropriate, a cycloalkyl or an alkyl group substituted with a cycloalkyl group. Unless otherwise indicated, an alkyl group comprises 1 to 10 carbon atoms, preferably 1 to 6 carbon atoms, or more preferably 1 to 4 carbon atoms. Representative examples of alkyl groups include, but are not limited to: methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, n-pentyl, isopentyl, neopentyl, n-hexyl, 3-methylhexyl, 2,2-dimethylpentyl, 2,3-dimethylpentyl, n-heptyl, n-octyl, n-nonyl, and n-decyl.

[0009] Compounds of formula I(a)(i), I(a)(ii), I(b)(i), and I(b)(ii) include their isomers, and in particular, constitutional isomers. Thus, as those skilled in the art will understand, although 1,4-(para)-substituted isomers are shown, the formulas explicitly cover compounds with 1,2-(ortho) and 1,3-(meta) substitutions.

[0010] As those skilled in the art will understand, the compounds of formula I(a)(i) and I(a)(ii) are isomers. Any mixture or additive containing these compounds may contain a single isomer or a mixture of two isomers. Similarly, the compounds of formula I(b)(i) and I(b)(ii) are isomers, and mixtures or additives containing these compounds may contain a single isomer or a mixture of two isomers. Likewise, the compounds of formula I(c)(i) and I(c)(ii) are isomers, and mixtures or additives containing these compounds may contain a single isomer or a mixture of two isomers.

[0011] The compound can be used as a single isomer or as a mixture of isomers.

[0012] Advantageously, the inventors have discovered that compounds of formulas I(a)(i)-I(a)(ii), I(b)(i)-I(b)(ii), and I(c)(i)-I(c)(ii) can be used as adhesion promoters. In particular, the inventors have demonstrated that compounds of formulas I(a)(i)-I(a)(ii), I(b)(i)-I(b)(ii), and I(c)(i)-I(c)(ii) can be used to promote adhesion between epoxy amine coatings and silicone coatings, such as, but not limited to, those coatings used as primers / base coats and antifouling topcoats in marine and protective coating applications. These compounds can be used as additives to promote adhesion between these coatings, and in embodiments, the need for an intermediate bonding layer is eliminated.

[0013] The compounds of formula I(a)(i)-I(a)(ii), I(b)(i)-I(b)(ii) and I(c)(i)-I(c)(ii) can be monoalkoxysilanes, dialkoxysilanes or trialkoxysilanes.

[0014] In the implementation plan, m is 2 or 3.

[0015] In the implementation plan, m is 3.

[0016] Trialkoxysilanes are generally commercially available and can be a useful and cost-effective option, especially for large-scale applications.

[0017] In the implementation plan, each R 3 It is independently a C1-C8 alkyl group.

[0018] In the implementation plan, each R 3 It is independently a C1-C4 alkyl group.

[0019] In the implementation plan, each R 3 It is either methyl or ethyl.

[0020] In some implementations, each R 3 They can be the same.

[0021] In the implementation plan, each R 3 It is an ethyl group.

[0022] R can be the same or different 1 and R 2 Each is H or alkyl C 1-10 ; Or R 1 and R 2 Together with -OBO-, they form a 5-, 6-, or 7-membered ring optionally substituted with one or more C1-C4 alkyl groups.

[0023] In the implementation plan, when R 1 and R 2 Each is an alkyl C 1-10 At that time, R 1 and R 2 They can be the same. As a technician will understand, when R 1 and R 2 When they are the same, this may have an advantage in terms of ease of synthesis. However, R 1 and R 2 Sameness is not required, and R is... 1 and R 2 Different compounds will function as adhesion promoters required by this invention.

[0024] In the implementation plan, R 1 and R 2 Each is an alkyl C 1-6 .

[0025] In the implementation plan, R 1 and R 2 Each is an alkyl C 2-4 .

[0026] In the implementation plan, R 1 and R 2 Each is a DINK.

[0027] In the implementation plan, R 1 and R 2 Each is an butyl group.

[0028] Advantageously, when R 1 and R 2 When both compounds are butyl, hydrolysis during adhesion leads to the release of butanol, a common solvent in paints and coating formulations. Therefore, R... 1 and R 2 Compounds of formula I that are butyl may be advantageous as additives in some cases for use in such known formulations.

[0029] In the implementation scheme, when the compound is a compound of formula I(a), and R 1 and R 2 When each component is butyl, the compound is a compound of formula I(a)(i)(a) or formula I(a)(ii)(a): In this implementation scheme, Y may not exist.

[0030] When the compound is a compound of formula I(a)(i)(a) or formula I(a)(ii)(a), m is preferably 3.

[0031] Each R 3 It can preferably be ethyl.

[0032] In the implementation scheme, the compound is a compound of formula I(a)(i)(a)(i) or formula I(a)(ii)(a)(i): The compound of formula I(a)(i)(a)(i) or formula I(a)(ii)(a)(i) is referred to LE below. As previously stated, any additive may contain a mixture of these two isomers.

[0033] In the implementation scheme, when the compound is a compound of formula I(b), and R 1 and R 2 When each component is butyl, the compound is a compound of formula I(b)(i)(a) or formula I(b)(ii)(a): In this implementation scheme, Y may not exist.

[0034] When the compound is a compound of formula I(b)(i)(a) or formula I(b)(ii)(a), m is preferably 3.

[0035] Each R 3 It can preferably be ethyl.

[0036] In the implementation scheme, the compound is a compound of formula I(b)(i)(a)(i) or formula I(b)(ii)(a)(i): .

[0037] In the implementation scheme, when the compound is a compound of formula I(c), and R 1 and R 2 When each component is butyl, the compound is a compound of formula I(c)(i)(a) or formula I(c)(ii)(a): In equation I(c)(i)(a), A 1 and A 2 Each is independently -CH2 or CHY.

[0038] In the implementation plan, A 1 and A 2 Not all of them are Y.

[0039] In this implementation scheme, Y does not exist. In this implementation scheme, A 1 and A 2 Each is -CH2.

[0040] When the compound is a compound of formula I(c)(i)(a) or formula I(c)(ii)(a), m is preferably 3.

[0041] Each R 3 It can preferably be ethyl.

[0042] In the implementation scheme, the compound is a compound of formula I(c)(i)(a)(i) or formula I(c)(ii)(a)(i): .

[0043] The compound of formula I(c)(i)(a)(i) or formula I(c)(ii)(a)(i) is referred to ALBE below. As previously discussed, any additive may contain a mixture of these two isomers.

[0044] Alternatively, in compounds of formula I(a)(i)-I(a)(ii), formula I(b)(i)-I(b)(ii), or formula I(c)((i)-(ii), R 1 and R 2 It can form a 5-, 6-, or 7-membered ring with -OBO-, said 5-, 6-, or 7-membered ring which may optionally be substituted with one or more C1-C4 alkyl groups. Such compounds are shown below as formulas I(a)(i)(b)(i)-I(c)(ii)(b)(iii): Where R 6 To R 23 They can be H or Cl-C independently. 10 Alkyl, provided that in formula I(a)(i)(b)(i), when m=3 and R 3 When it is ethyl, then R 6 R 7 R 8 and R 9 Not all of them are methyl.

[0045] In the implementation plan, Y does not exist.

[0046] In the implementation plan, R 6 To R 23 Each can be an H or C1-C6 alkyl group independently.

[0047] In the implementation plan, R 6 To R 23 Each can be H.

[0048] In the implementation plan, the 5-membered, 6-membered, and 7-membered rings can be unreplaced.

[0049] Compounds with 5- or 6-membered rings are preferred because they are easy to synthesize.

[0050] In the implementation plan, R 1 and R 2 Together with -OBO-, a 5-membered ring is formed, wherein the 5-membered ring is optionally substituted with one or more C1-C4 alkyl groups. In this embodiment, the compound may have the following formula: The condition is in I(a)(i)(b)(i) when m is 3 and R 3 When it is ethyl, all R 6 To R 9 It cannot be methyl.

[0051] In this embodiment, the compound is a compound of formula I(a)(i)(b)(i) or formula I(a)(ii)(b)(i). In these compounds, R 6 R 7 R 8 and R 9 They can be the same.

[0052] In the implementation plan, m is 3.

[0053] In the implementation plan, R 3 It is a C1-C4 alkyl group.

[0054] In the implementation plan, R 3 It is a C1 alkyl or C2 alkyl.

[0055] In the implementation plan, R 3 It is an ethyl group.

[0056] In the implementation plan, Y does not exist.

[0057] In the implementation scheme, the 5-membered ring is not replaced, that is, R 6 R 7 R 8 and R 9 All are H and the compound is a compound of formula I(a)(i)(b)(i)(a) or formula I(a)(ii)(b)(i)(a): These compounds are referred to as CE in the following text.

[0058] As stated above, the inventors have advantageously determined that compounds of formulas I(a)(i)-I(a)(ii), I(b)(i)-I(b)(ii), and I(c)(i)-I(c)(ii) possess adhesion-promoting properties. In particular, the inventors have demonstrated that compounds of formulas I(a)(i)-I(a)(ii), I(b)(i)-I(b)(ii), and I(c)(i)-I(c)(ii) can be used to promote adhesion between epoxyamines and polysiloxanes, such as those commonly used in primer and topcoat coatings, for marine and protective coating applications. However, the invention is not limited to marine and protective coating applications, and the compounds can be used to promote adhesion between epoxyamines and silicones in any application area. Therefore, the present invention relates to these compounds for promoting adhesion, particularly adhesion between epoxyamines and silicones.

[0059] In this regard, the present invention relates to the use of compounds of formula II as adhesion promoters: In Equation II, R can be the same or different. 1 and R 2 Each is H or alkyl C 1-10 ; Or R 1 and R 2 Together with -OBO-, they form a 5-, 6-, or 7-membered ring optionally substituted with one or more C1-C4 alkyl groups; Each R 3 Independently, it is C1-C 10 Alkyl or phenyl; m is an integer from 1 to 3; And L is the formula X 1 nL 1 -X 2 The linker group of o, wherein: L 1 It is C1-C 20 Aliphatic groups or C5-C 14 Aromatic cyclic groups or C3-C8 cyclic hydrocarbon groups; and X 1 and X 2 Each of them is C1-C 20 Straight-chain or branched saturated or unsaturated aliphatic hydrocarbon groups; and wherein X 1 X 2 and L 1 Each of the terms in the equation is optionally replaced by Y, where Y is C1-C. 20Straight-chain or branched aliphatic hydrocarbons; halogen-substituted C1-C 20 Straight-chain or branched aliphatic hydrocarbons; halogens; -OR 4 ;-NR 4 2; -NO2; -SO3H; -C(=O)R 4 ;-C(=O)OR 4 ;-OC(=O)NR 4 2; -C≡N; -SR 4 ;-P(=O)R 4 2; -OC(=O)OR 5 ;-NC(=O)OR 5 ;-SO2R 5 ;-SOR 5 ;where R 4 It is H, C1-C which is optionally replaced by Y. 20 Branched or straight-chain alkyl groups or phenyl groups; and R 5 It is C1-C 20 Branched or straight-chain alkyl groups, and n and o are each independently 0 or 1.

[0060] In the implementation plan, each X 1 and X 2 In its presence, it is independently a C1-C8 straight-chain or branched saturated or unsaturated aliphatic hydrocarbon group.

[0061] In the implementation plan, L 1 It is a C1-C8 straight-chain or branched hydrocarbon group or a C5-C... 14 Aromatic cyclic groups.

[0062] In the implementation plan, L 1 It is a C1-C4 straight-chain or branched hydrocarbon group, or benzene or naphthalene.

[0063] In the implementation plan, L 1 It is a C2 alkyl group, or benzene or naphthalene.

[0064] In the implementation scheme, the use relates to compounds of formula II, where both n and o are 0.

[0065] In the implementation plan, L 1 It has not been replaced.

[0066] In aspects of the present invention, the use of compounds of formula II(a)(i)-II(a)(ii), II(b)(i)-II(b)(ii), or II(c)(i)-II(c)(ii) as adhesion promoters is provided. The compounds of formula II(a)(i)-II(a)(ii), II(b)(i)-II(b)(ii), or II(c)(i)-II(c)(ii) have the following structures: ; R can be the same or different 1 and R 2 Each is H or alkyl C 1-10 ; Or R 1 and R 2 Together with -OBO-, they form a 5-, 6-, or 7-membered ring optionally substituted with one or more C1-C4 alkyl groups; Each R 3 It is independently a C1-C8 alkyl or phenyl group; A 1 and A 2 Independently, it is -CH2 or CY; The Y group, which may or may not be present, consists of one or more substituents selected from the following: C1-C 20 Straight-chain or branched saturated or unsaturated aliphatic hydrocarbons; halogen-substituted C1-C 20 Straight-chain or branched saturated or unsaturated aliphatic hydrocarbons; halogens; -OR 4 ;-NR 4 2; -NO2; -SO3H; -C(=O)R 4 ;-C(=O)OR 4 ;-OC(=O)NR 4 2; -C≡N; -SR 4 ;-P(=O)R 4 2; -OC(=O)OR 5 ;-NC(=O)OR 5 ;-SO2R 5 ;-SOR 5 ;where R 4 It is H, C1-C 20 Straight-chain or branched aliphatic hydrocarbon groups or PhY; and R 5 It is C1-C 20 A straight-chain or branched saturated or unsaturated hydrocarbon group or PhY; or Y is PhY; PhY is a phenyl group that is optionally substituted with Y; And m is an integer from 1 to 3.

[0067] As previously stated, compounds of formula II(a)(i) and II(a)(ii) are isomers of each other, compounds of formula II(b)(i) and II(b)(ii) are isomers of each other, and compounds of formula II(c)(i) and II(c)(ii) are isomers of each other. Uses of the compounds include use in their single isomer form or as a mixture of isomers.

[0068] Compounds I(a), I(b), and I(c) have the same structure as compounds II(a), II(b), and II(c), respectively; however, compound I(a) specifically excludes R. 1 and R 2 The implementation scheme that forms a 5-membered ring with -OBO- (i.e., compound I(a)(i)(b)(i), where m is 3, R 3 It is an ethyl group, and it is in R 6 R 7 R 8 and R 9 (The part is replaced by -CH3), which is explicitly included in formula II(a). Therefore, the present invention relates to the compounds of formula I(a)(i)-I(a)(ii), I(b)(i)-I(b)(ii) and I(c)(i)-I(c)(ii) themselves, and to formula II, and in particular to the use of compounds of formula II(a)(i)-II(a)(ii), II(b)(i)-II(b)(ii) and II(c)(i)-II(c)(ii) as adhesion promoters.

[0069] In embodiments, the present invention relates to the use of compounds of formula II(a)(i)-II(a)(ii), formula II(b)(i)-II(b)(ii) or formula II(c)(i)-II(c)(ii) as adhesion promoters to promote adhesion between epoxides and polysiloxanes.

[0070] Throughout this specification, the terms polysiloxane and organosilicon are used interchangeably.

[0071] In embodiments, the compounds of formulas II(a)(i)-II(a)(ii) and / or II(b)(i)-II(b)(ii) and / or II(c)(i)-II(c)(ii) can be used as adhesion promoters for marine applications. For example, this use can be as an adhesion promoter between an epoxyamine primer (or base) coating and a polysiloxane topcoat. This use can eliminate the need for an adhesive coating between the primer and the topcoat, particularly in marine applications.

[0072] This offers significant advantages in reducing dry-dock time, lowering costs, and / or reducing labor. As those skilled in the art will understand, the uses are not limited to marine applications, and the compound can be used as an adhesion promoter between epoxides and polysiloxanes in non-marine applications, such as for buildings, bridges, etc.

[0073] However, the uses are not limited to applications where no adhesive coating is present, and as those skilled in the art will understand, the compound can be used to improve the adhesion between the adhesive coating and a primer or base coat, wherein the adhesive coating is based on similar chemicals.

[0074] The compounds of formulas II(a)(i)-II(a)(ii), II(b)(i)-II(b)(ii), or II(c)(i)-II(c)(ii) may be used as additives. The compounds may be used as a single isomer or as a mixture of isomers. In this embodiment, the additive may be added to a primer / basecoat formulation and / or a topcoat formulation. The additive may be added purely or as a solution in a solvent. Suitable solvents include, for example, xylene, toluene, ethyl acetate, propyl acetate, butyl acetate, methyl ethyl ketone, methyl isobutyl ketone, propylene glycol methyl ether acetate, mineral oil, naphtha, and turpentine, as will be apparent to those skilled in the art.

[0075] In the implementation scheme, the additive is added to the primer or topcoat formulation at a concentration of 0.001% to 15% (w / w) based on the total weight of the formulation.

[0076] In the implementation scheme, the additive is added to the primer or topcoat formulation at a concentration of 0.001% to 7% (w / w) based on the total weight of the formulation.

[0077] In the implementation scheme, the additive is added to the primer or topcoat formulation at a concentration of 0.001% to 4% (w / w) based on the total weight of the formulation.

[0078] In the implementation scheme, the additive is added to the primer or topcoat formulation at a concentration of 0.1% to 4% (w / w) based on the total weight of the formulation.

[0079] In the implementation scheme, the additive is added to the primer or topcoat formulation at a concentration of 0.8% to 2.1% (w / w) based on the total weight of the formulation.

[0080] In the implementation plan, the additive may be added to the formulation in place of a portion or all of the curing agent.

[0081] Such curing agents (sometimes referred to as curing catalysts) used for polysiloxane coatings are typically based on tetraethyl orthosilicate (TEOS) condensation curing chemistry (including oligomers, polymers, and adducts of TEOS), and commercially available silicone coatings are typically provided as two- or three-part condensation curing formulations consisting of silicone, a curing agent, and optional other performance additives. The inventors have advantageously determined that the additives of the present invention perform a dual function, wherein the siloxane functional groups of the additives of formula II(a) / II(b) / II(c) replace TEOS as curing agents. This means that part or all of the curing agent can be replaced by the additive, such that the properties of the resulting polysiloxane coating are minimally affected by the presence of the additive, while still effectively curing. Advantageously, this allows the compounds of the present invention to be easily incorporated into existing commercially available formulations.

[0082] In the implementation scheme, the additive may be added to the base coating formulation. When the additive is added to the base coating formulation, it may be added to the formulation at a concentration based on the total weight of the formulation, ranging from 0.001% to 15% (w / w), from 0.001% to 7% (w / w), from 0.001% to 4% (w / w), from 0.1% to 4% (w / w), or from 0.8% to 2.1% (w / w).

[0083] In the implementation scheme, the additive is added to both the topcoat and the basecoat formulations.

[0084] In the implementation scheme, additives are added to the adhesive coating.

[0085] According to an aspect of the invention, a method for promoting adhesion between an epoxyamine coating formulation and a polysiloxane coating formulation is provided, wherein the method comprises adding a compound of formula II (as defined above) to at least one of the coating formulations and bringing the coating formulations into contact.

[0086] According to an aspect of the invention, a method is provided for adhering an epoxyamine coating formulation and a polysiloxane coating formulation, wherein the method comprises adding a compound of formula II(a)(i)-II(a)(ii) or II(b)(i)-II(b)(ii) or II(c)(i)-II(c)(ii) to at least one of the coating formulations prior to contacting the formulations.

[0087] In an embodiment, the method includes adding a compound of formula II(a)(i)-II(a)(ii), or formula II(b)(i)-II(b)(ii), or formula II(c)(i)-II(c)(ii) to a polysiloxane coating formulation. In an embodiment, the polysiloxane coating formulation is a multi-part formulation comprising a polysiloxane and a curing agent, and the compound is added in place of a portion of the curing agent. The compound may be added at a concentration from 0.001% to 15% (w / w) based on the total weight of the formulation or in place of a curing agent from 0.001 mol% to 100 mol%.

[0088] As will be understood by those skilled in the art, the compounds of Formula I / II can provide the formulation with the same concentration of reactive Si-OR as the original TEOS curing agent. 3 The concentration of the functional groups is added to the silicone formulation. Alternatively, in addition to the TEOS curing agent, compounds of formula I / II may be added.

[0089] The invention will now be described with reference to the accompanying drawings, in which: Figure 1 This illustrates the coating of aluminum strip with an epoxy amine undercoat as described in Example 3; Figure 2 The construction of a sample for the overlap shear test, as described in Example 4, is shown.

[0090] experiment: All reagents were purchased from Sigma-Aldrich. TM Fisher Scientific TM and Fluorochem TM And it is used without further purification. Two-component room temperature curing silicone, silicone moisture-curing resin CS25 TM Purchased from easycomposites TM If necessary, the solvent is dried over a 3Å molecular sieve.

[0091] High-resolution mass spectrometry (HRMS) HRMS was performed at the Swansea National Mass Spectrometry Facility (NMSF). Samples were analyzed using an Atmospheric Solids Analysis Probe (ASAP) on the APcI source of a Waters Xevo G2-S QTOF MS. Conditions: Source temperature 80 °C. Samples were introduced into the source as solids or liquids held in an open glass capillary within the ASAP probe. The initial probe temperature (T) was ~40 °C; the T was then increased until the sample evaporated (Vap T depends on the sample), and ions were formed using a corona discharge current of 4 µA. Ms resolution: >32,500 FWHM. Mass range: m / z 50–2000. Mass accuracy: <3 ppm (using peptide leucine enkephalin in solution as the locked mass).

[0092] Nuclear magnetic resonance (NMR) Using a JOEL ECS400 Delta spectrometer at 25°C to target 1 399.78 MHz of H-NMR and targeting 13 NMR analysis was obtained at a frequency of 100.53 MHz using C-NMR. All chemical shifts are expressed relative to deuterated chloroform (CDCl3) or deuterated dimethyl sulfoxide (DMSO-d). 6 The parts per million (ppm) of tetramethylsilane (TMS, δ=0 ppm) used as an internal standard in the sample. 13 C -NMR attribution was confirmed by DEPT analysis. Spectroscopic data were recorded as chemical shifts (δ), relative integrals, multiplicity (s = singlet, br = broad peak, d = doublet, t = triplet, q = quartet, quintet, sext = sextet, dd = doublet of doublet, m = multiplet) and coupling constant (J = Hz).

[0093] Example 1: Synthesis of compounds of formula I 1.1. Preparation of vinyl esters Esterification of 1,4-vinylphenylboronic acid (BA) into the corresponding linear and cyclic (5-membered ring) esters is shown in Scheme 1 and is carried out as follows: Option 1: Esterification of vinylphenylboronic acid (BA) into vinyl cyclic esters (VCE) and vinyl linear esters (VLE).

[0094] 1.1.1 Preparation of Vinyl Cyclic Esters (VCEs) 1,4-vinylphenylboronic acid (100.0 g, 0.676 mol) was dissolved in dichloromethane (DCM) (1 L) in a 2 L round-bottom flask to form a turbid suspension. Ethylene glycol (42.2 g, 0.678 mol) was added to this suspension, followed by MgSO4 (~20 g). The reaction was stirred at room temperature (RT) for 24 hours using a magnetic stirrer, and then filtered to remove MgSO4. DCM was removed under reduced pressure to yield a solid product (116.71 g, 0.670 mol, 99%), which was used in subsequent reactions without further purification.

[0095] 1 H-NMR (400 MHz, chloroform-D) δ 7.78 (d, J = 8.2 Hz, 2H), 7.43 (d, J = 8.2Hz, 2H), 6.74 (dd, J = 17.6, 10.8 Hz, 1H), 5.83 (d, J = 17.4 Hz, 1H), 5.31 (d, J = 10.5 Hz, 1H), 4.38 (s, 4H).

[0096] carbon: 13 C-NMR (101 MHz, chloroform-D) δ 140.4, 136.8, 135.1, 125.7, 115.1, 66.0.

[0097] IR: 2980 w C=CH, 2915 w BO-CH2, 1608 m Ar, 1330 s BO.

[0098] 1.1.2 Preparation of vinyl linear esters (VLE) In a 1 L round-bottom flask, 1,4-vinylphenylboronic acid (40.00 g, 0.27 mol) was dissolved in butanol (371 mL, 300.51 g, 4.05 mol), heated to 30 °C, and stirred continuously for 4 hours using a magnetic stirrer. Then, a vacuum was applied to the distillation apparatus, and the temperature was raised to 70 °C and distillation continued until no more butanol or water distilled off. Complete conversion (as per [previous method]) was achieved. 1 The sample was characterized by H-NMR, and the resulting liquid was filtered through filter paper. The filtrate was then used for subsequent reactions without further purification. (69.55 g, 0.267 mol, 99%) 1H-NMR (400 MHz, chloroform-D) δ 7.57 (br.s, 2H), 7.40 (d, J = 5.5 Hz, 2H), 6.75-6.68 (m, 1H), 5.78 (d, J = 17.4 Hz, 1H), 5.26 (d, J = 10.1 Hz, 1H), 4.02(br.s, 4H), 1.51 (br.d, J = 74.2 Hz, 8H), 0.93 (br.s, 6H).

[0099] 13 C-NMR (101 MHz, chloroform-D) δ 138.5, 136.9, 134.8, 133.7, 125.5, 114.3, 64.3, 33.9, 19.0, 13.9.

[0100] IR: 2960 w OC-H2, 2930 w BO-CH2, 1610 w Ar, 1315 s BO.

[0101] 1.2 Preparation of Triethoxysilane Ester Additive After preparing the vinyl linear ester and vinyl cyclic ester in Example 1.1 above, the esters are subjected to hydrogenation and silanization to prepare the triethoxysilane ester additive according to the present invention, as shown in Scheme 2. Option 2: Hydrosilylation of vinyl cyclic esters (VCE) and vinyl linear esters (VLE) to form compound CE And LE.

[0102] 1.2.1 Preparation of Triethoxysilane Cyclic Esters (CE) The vinyl cyclic ester (VCE) (20.00 g, 0.115 mol) prepared in Example 1.1.1 above and a platinum(O)-1,3-divinyl-1,1,3,3-tetramethyldisiloxane complex solution (3%-3.5% platinum concentration, 0.219 g) were dissolved in 20 mL of dried xylene in a flame-dried 250 mL round-bottom flask that had been cooled under a drying tube (CaCl2 was used as a desiccant). The reaction was heated to 60 °C for 20 minutes under the drying tube, and then HSi(OEt)3 (24.5 g, 0.149 mol) was added. The reaction was stirred at 60 °C for another 24 hours, and then... 1 ¹H-NMR analysis indicated complete conversion by the absence of olefin peaks at 6.74 ppm and 5.83 ppm. The reaction mixture was then filtered through glass wool to remove any precipitates that had formed. The resulting solution of CE in xylene was used directly as an additive (see examples later).

[0103] High-resolution mass spectrometry (APCI) was used to calculate the C of the proposed product. 16 H 28 BO5Si + (MH + The actual value is 339.1794, and the measured value is 399.1790.

[0104] To facilitate solvent-free testing of the additive, xylene was removed by first replacing 20 ml of the xylene reaction solvent with an equal volume (20 ml) of lower-boiling toluene, and then removing the toluene and xylene under reduced pressure by vacuum distillation in a fume hood. Pure CE was used directly as the additive (see examples later).

[0105] 1.2.2 Preparation of Triethoxysilane Straight-Chain Ester (LE) The vinyl linear ester (VLE) (20.00 g, 0.077 mol) prepared in Example 1.1.2 above and a platinum(O)-1,3-divinyl-1,1,3,3-tetramethyldisiloxane complex solution (3%-3.5% platinum concentration, 0.146 g) were dissolved in 20 mL of dried xylene in a flame-dried 250 mL round-bottom flask that had been cooled under a drying tube (CaCl2 was used as a desiccant). The reaction was heated to 60 °C under the drying tube for 20 minutes, and then HSi(OEt)3 (16.440 g, 0.100 mol) was added. The reaction was stirred for 48 hours using a magnetic stirrer. 1 ¹H-NMR analysis revealed the absence of olefin peaks at 6.75 ppm–6.68 ppm and 5.78 ppm, indicating the completion of the reaction. The reaction mixture was then filtered through glass wool to remove any precipitate. The resulting LE, as a solution in xylene, was then used as an additive in organosilicon-based coatings (see examples later).

[0106] To facilitate solvent-free testing of LE additives, xylene was removed by first replacing 20 ml of xylene reaction solvent with an equal volume (20 ml) of lower boiling point toluene, and then removing toluene and xylene under reduced pressure by vacuum distillation in a fume hood.

[0107] High-resolution mass spectrometry (APCI) was used to calculate the C of the proposed product. 22 H 42 BO5Si + (MH + The actual value is 425.2889, and the measured value is 425.2885.

[0108] 1.2.3 Preparation of alkyl-linked butyl esters (ALBE) As shown in Scheme 3, ALBE is prepared from vinyl butyl borate (EBBE). Option 3: Preparation of alkyl-linked butyl ester (ALBE) .

[0109] Ethylene butyl borate (CAS: 6336-45-4, mass = 3 g, 0.0163 mol) and a platinum (O)-1,3-divinyl-1,1,3,3-tetramethyldisiloxane complex solution (3%-3.5% platinum concentration, 0.0310 g) were dissolved in xylene (3 g) and stirred at 60 °C for 20 minutes in a flame-dried round-bottom flask with a CaCl2 protective tube. Triethoxysilane (3.4855 g, 0.0212 mol) was added dropwise to the mixture and stirred at 60 °C for an additional 24 hours. 1 ¹H-NMR analysis revealed the absence of three olefin peaks between 5.84 ppm and 6.21 ppm, indicating the completion of the reaction. The reaction mixture was then filtered through glass wool to remove any precipitate. The resulting ALBE solution in xylene was then used as an additive in silicone-based coatings (see examples later).

[0110] Example 2: Preparation of organosilicon formulations with CE / LE additives 2.1: Preparation of Model Primer / Undercoat Formulation Two model primer coating systems were prepared. These model systems are intended to simulate commercially available epoxy amine coating formulations, such as those used as primers or base coats in marine and high-performance coating applications.

[0111] The first model primer coating system (BC1) is prepared by combining a commercial bisphenol A-based epoxy resin (DER331), a commercial amine curing agent (1,3-bis(aminomethyl)cyclohexane (also known as 1,3-BAC)) and a catalyst (2,4,6-tris-(dimethylaminomethyl)phenol (also known as DMP-30)) into a formulation that yields a 1:1 molar ratio of epoxide groups to NH (amine) groups.

[0112] The second model primer system (BC2) is prepared by combining a commercial bisphenol A-based epoxy resin (DER331), a commercial phenolic amine curing agent (Carolite NC 541 LV), and a catalyst (DMP-30) to give a molar ratio of epoxide groups to NH (amine) groups of 1:0.75 equivalent molecular weights of Carolite NC 541 LV and DER 331. Carolite NC 541 LV is a phenolic amine curing agent based on the reaction product of cashew nut shell phenol, formaldehyde, and 1,2-ethylenediamine, and therefore, this model primer system very closely represents commercial epoxy amine-based anti-corrosion coating systems, such as those used to protect marine vessels and offshore oil and gas assets.

[0113] The weight percentages of BC1 and BC2 are shown in Table 1: Table 1: Weight percentage of components used in the preparation of the model primer coating formulation Example 2.2: Preparation of Organosilicon Topcoat Formulation with Additives By using easycomposite TM Silicone rubber-based compounds and easycomposite TM The curing agent was combined with the CE, LE, or ALBE additives prepared in Examples 1.2.1 to 1.2.3 above to prepare the silicone topcoat formulation. The components were combined in 20 ml glass sample vials and manually homogenized using a spatula for 120 seconds, then applied to the top 30 mm of the cured epoxyamine layer using a 400 µm drawdown bar (details below). Samples were prepared as shown in Table 2. Adhesion-promoting additives (CE, LE, or ALBE) were added as solutions in xylene, where CE was a 68 / 32 (Ce / xylene) w / w xylene solution, LE was a 66 / 34 (LE / xylene) w / w xylene solution, and ALBE was a 66 / 34 (ALBE / xylene) w / w xylene solution. The weight percentage of additives in the silicone topcoat was calculated only based on the weight of CE / LE / ALBE (i.e., xylene was not calculated). Depending on the loading of the adhesion promoter, each formulation also contains trace amounts (0.25 wt% to 2.2 wt%) of xylene. The samples shown in Item 5 were prepared with pure CE additive, i.e., without added xylene, to evaluate the effect of the solvent on the resulting adhesion. Table 2: Weight % of components in organosilicon formulations Example 3: Coating Test Cut the aluminum strip into 100 mm × 25 mm pieces, roughen it with sandpaper, wash it with deionized water, and then wash it with industrial methylated alcohol (IMS). Then dry the strip for at least 30 minutes.

[0114] like Figure 1 As shown in the figure, the aluminum sample strip (1) is coated with an epoxy amine undercoat (2) (BC1 or BC2 - see Table 1), which is applied using a 400 µm coating rod. The epoxy amine coating is then cured at low temperature (LC) or high temperature (HC) conditions, as shown in Table 3 below. Table 3: Experimental curing conditions like Figure 2 As shown in the diagram, the silicone topcoat (3) (prepared as described above) is then applied to the top 30 mm of the cured epoxy amine layer with a wet film thickness of 400 µm using a coating rod. Figure 2 As shown, a second aluminum strip, cut to the same size and also coated with the same epoxy amine coating, is placed on top of a 30 mm silicone topcoat, giving a 30 mm overlap (O), and then cured at room temperature for 24 hours.

[0115] Example 4: Overlap Shear Test Overlap shear tests were performed using an Instron tensile tester equipped with a 3 kN load cell at an elongation rate of 1 mm / min, and the maximum tensile force (N) was measured in each case. Each coating system was tested five times. The failure method of the samples was recorded using the following code: Table 4: Failure Codes 4.1: Effect of CE concentration (BC1) The effect of CE concentration in the silicone topcoat was evaluated by preparing silicone topcoats 1 with CE additive concentrations ranging from 0.5% w / w to 2.5% w / w (see Table 2, entries 2-5). Sample 1 was a control sample without any CE additive. The sample was prepared as described in Example 2.2 above. The primer was model system BC1 (Table 1) prepared using high-temperature curing (HC) conditions. The results are shown in Table 5. Table 5: Effect of CE additive concentration in xylene on adhesion The lap shear test of Sample #1 (control) shows an average adhesion loss of 245 N and adhesion failure mechanism 'A' when the silicone topcoat does not contain additives. When CE is added, all silicone topcoats show improved adhesion to the undercoat, with the best results obtained at 1.5 wt% CE. At this concentration, adhesion loss does not occur until 1,351 N, indicating a 550% increase in adhesion strength compared to Control Sample #1 without CE additives.

[0116] Example 4.2: Effect of LE concentration (BC1) The experiment of Example 4.1 was repeated, but LE additive was used instead of CE (corresponding to samples 6, 7, 8 and 9 in Table 2, where sample 1 again represents the control). The results are shown in Table 6. Table 6: Effect of LE additive concentration on adhesion Sample #1 in Table 6 again shows the adhesion strength (245 N) of the control system without additives, used for comparison with coating formulations containing 0.6 wt.%, 1.3 wt.%, 1.9 wt.%, and 3.1 wt.% LE additives. The best-performing coating was sample #3 (1.3% LE, 1318 N), and the addition of all levels of LE from 0.6 wt% to 3.1 wt% had a significant positive effect on the adhesion between the silicone topcoat and the epoxy amine undercoat.

[0117] Example 4.3: Effect of CE concentration (BC2) The experiment of Example 4.1 was repeated under low temperature (LC) curing conditions using primer 2 (BC2, the formulation shown in Table 1). The results are shown in Table 7. Table 7: Effect of CE concentration on adhesion, BC2 Table 7 shows the results of introducing CE additive as a solution in xylene at 0.5 w / w and 2.5 w / w (68 / 32 CE / xylene w / w%) compared to the control unadulterated silicone topcoat (sample #1, 102 N). Both samples #2 and #3 showed significant improvements in adhesion compared to control sample #1. Sample #2 (0.5 wt% CE) showed an adhesion of 563 N, while sample #3 (2.5 wt% CE) showed an adhesion of 947 N. Both examples showed large and significant improvements in adhesion compared to the control sample which did not contain the CE additive.

[0118] 4.4: Effect of LE concentration (BC2) The experiments of Example 4.1 were repeated using primer coating 2 (BC2, formulation shown in Table 1) prepared under high (HC, 60°C) and low (LC, room temperature) curing conditions. The effect of LE concentration in the silicone topcoat was evaluated by preparing silicone topcoat 1 with LE additive concentrations ranging from 1.3% w / w to 3.1% w / w as described in Example 2.2 above. The results are shown in Table 8. Table 8: Effect of LE additive concentration on BC2 adhesion Sample #1 is a control sample without the adhesion promoter, while samples 2-5 show the effects of LE adhesion promoters introduced into xylene at different levels (66 / 34 LE / xylene w / w%). Sample #4, containing the highest concentration of LE adhesion promoter (3.1% w / w), was found to have the greatest adhesion performance (1026 N) compared to control sample #1 (adhesion at 102 N) without the LE additive. Samples containing 3.1 wt% LE were tested under high temperature (HC) and low temperature (LC) curing conditions to evaluate the effect of curing conditions on adhesion promotion. The results (samples 4 and 5) demonstrate that significant improvements in adhesion were observed regardless of the curing conditions of the base coat. When using LC curing conditions (i.e., room temperature, Table 3), a significant improvement in adhesion was observed at 856 N (compared to 102 N for the control). This indicates that the additive can be used to promote adhesion at ambient temperature.

[0119] 4.5: Effect of ALBE concentration (BC2) The experiments of Example 4.1 were repeated using primer coating 2 (BC2, formulation shown in Table 1) prepared under low (LC, room temperature) curing conditions. The effect of ALBE concentration in the silicone topcoat was evaluated by preparing silicone topcoat 3 with ALBE additive concentrations ranging from 0.6% w / w to 2.7% w / w (see Table 2, entries 10-11). Sample 1 was a control sample without any ALBE additive. The results are shown in Table 9. Table 9: Effect of ALBE additive concentration on BC2 adhesion The lap shear test of Sample #1 (control) shows the average adhesion loss and adhesion failure mechanism 'A' at 102 N when the silicone topcoat does not contain additives. When ALBE is added, all silicone topcoats show improved adhesion to the undercoat, with the best results obtained at 2.7 wt% ALBE. At this concentration, adhesion loss does not occur until 1025 N, indicating a 1005% increase in adhesion strength compared to Control Sample #1 without ALBE additives.

[0120] Further tests using commercially available primer and topcoat formulations confirmed that the improved adhesion between coatings resulting from the addition of the additive was sufficient to eliminate the need for adhesive coatings.

Claims

1. Compounds of formula I(a)(i), I(a)(ii), I(b)(i), I(b)(ii) or I(c)(i)-I(c)(ii): Among them, R can be the same or different 1 and R 2 Each is H or alkyl C 1-10 ; Or R 1 and R 2 Together with -OBO-, they form a 5-, 6-, or 7-membered ring optionally substituted with one or more C1-C4 alkyl groups; Each R 3 It is independently a C1-C8 alkyl or phenyl group; A 1 and A 2 Independently, it is -CH2 or CHY; The presence or absence of Y can be due to one or more substituents selected from the following: C1-C 20 Straight-chain or branched saturated or unsaturated aliphatic hydrocarbons; halogen-substituted C1-C hydrocarbons 20 Straight-chain or branched saturated or unsaturated aliphatic hydrocarbons; halogens; -OR 4 ;-NR 4 2; -NO2; -SO3H; -C(=O)R 4 ;-C(=O)OR 4 ;-OC(=O)NR 4 2; -C≡N; -SR 4 ;-P(=O)R 4 2; -OC(=O)OR 5 ;-NC(=O)OR 5 ;-SO2R 5 ;-SOR 5 ;where R 4 It is H, C1-C 20 Straight-chain or branched aliphatic hydrocarbon groups or PhY; and R 5 It is C1-C 20 A straight-chain or branched saturated or unsaturated hydrocarbon group or PhY; or Y is PhY; PhY is a phenyl group that is optionally substituted with Y; And m is an integer from 1 to 3; and its isomers; where equation I is not: 。 2. The compounds of formula I(a)(i)-I(a)(ii), I(b)(i)-I(b)(ii) or I(c)(i)-I(c)(ii) according to claim 1, wherein m is 2 or 3.

3. The compounds of formula I(a)(i)-I(a)(ii), I(b)(i)-I(b)(ii) or I(c)(i)-I(c)(ii) according to claim 2, wherein m is 3.

4. A compound of formula I(a)(i)-I(a)(ii), formula I(b)(i)-I(b)(ii) or formula I(c)(i)-I(c)(ii) according to any one of the preceding claims, wherein each R 3 It is independently a C1-C8 alkyl group.

5. The compounds of formula I(a)(i)-I(a)(ii), I(b)(i)-I(b)(ii) or I(c)(i)-I(c)(ii) according to claim 4, wherein each R 3 It is independently a C1-C4 alkyl group.

6. The compounds of formula I(a)(i)-I(a)(ii), I(b)(i)-I(b)(ii) or I(c)(i)-I(c)(ii) according to claim 5, wherein each R 3 It is methyl or ethyl.

7. The compounds of formula I(a)(i)-I(a)(ii), I(b)(i)-I(b)(ii) or I(c)(i)-I(c)(ii) according to claim 6, wherein each R 3 It is an ethyl group.

8. A compound of formula I(a)(i)-I(a)(ii), formula I(b)(i)-I(b)(ii) or formula I(c)(i)-I(c)(ii) according to any one of the preceding claims, wherein R 1 and R 2 Each is independently C1-C 10 alkyl.

9. The compounds of formula I(a)(i)-I(a)(ii), I(b)(i)-I(b)(ii) or I(c)(i)-I(c)(ii) according to claim 8, wherein R 1 and R 2 They are the same.

10. The compounds of formula I(a)(i)-I(a)(ii), I(b)(i)-I(b)(ii), or I(c)(i)-I(c)(ii) according to claim 8 or claim 9, wherein R 1 and R 2 It is a C1-C6 alkyl group.

11. A compound of formula I(a)(i)-I(a)(ii), formula I(b)(i)-I(b)(ii) or formula I(c)(i)-I(c)(ii) according to any one of claims 8 to 10, wherein R 1 and R 2 It is butyl.

12. A compound of formula I(a)(i)-I(a)(ii), formula I(b)(i)-I(b)(ii) or formula I(c)(i)-I(c)(ii) according to any one of claims 1 to 7, wherein R 1 and R 2 Together with -OBO-, they form a 5-, 6-, or 7-membered ring optionally substituted with one or more C1-C4 alkyl groups.

13. The compounds of formula I(a)(i)-I(a)(ii), I(b)(i)-I(b)(ii) or I(c)(i)-I(c)(ii) according to claim 12, wherein R 1 and R 2 Together with -OBO-, it forms a 5- or 6-membered ring optionally substituted with one or more C1-C4 alkyl groups.

14. The compounds of formula I(a)(i)-I(a)(ii), I(b)(i)-I(b)(ii), or I(c)(i)-I(c)(ii) according to claim 12 or 13, wherein R 1 and R 2 Together with -OBO-, they form unsubstituted 5-, 6-, or 7-membered rings.

15. A compound of formula I(a)(i)-I(a)(ii), formula I(b)(i)-I(b)(ii) or formula I(c)(i)-I(c)(ii) according to any one of the preceding claims, wherein Y is absent.

16. A compound of formula I(a)(i)-I(a)(ii), formula I(b)(i)-I(b)(ii) or formula I(c)(i)-I(c)(ii) according to any one of the preceding claims, wherein the compound is selected from: ， ， ， and 。 17. Uses of compounds of formula II as adhesion promoters: In Equation II, R can be the same or different. 1 and R 2 Each is H or alkyl C 1-10 ; Or R 1 and R 2 Together with -OBO-, they form a 5-, 6-, or 7-membered ring optionally substituted with one or more C1-C4 alkyl groups; Each R 3 Independently, it is C1-C 10 Alkyl or phenyl; m is an integer from 1 to 3; And L is the formula X 1 nL 1 -X 2 The linker group of o, wherein: L 1 It is C1-C 20 Aliphatic groups or C5-C 14 Aromatic cyclic groups or C3-C8 cyclic hydrocarbon groups; and X 1 and X 2 Each of them is C1-C 20 Straight-chain or branched saturated or unsaturated aliphatic hydrocarbon groups; and wherein X 1 X 2 and L 1 Each of the terms in the equation is optionally replaced by Y, where Y is C1-C. 20 Straight-chain or branched aliphatic hydrocarbons; halogen-substituted C1-C 20 Straight-chain or branched aliphatic hydrocarbons; halogens; -OR 4 ;-NR 4 2; -NO2; -SO3H; -C(=O)R 4 ;-C(=O)OR 4 ;-OC(=O)NR 4 2; -C≡N; -SR 4 ;-P(=O)R 4 2; -OC(=O)OR 5 ;-NC(=O)OR 5 ;-SO2R 5 ;-SOR 5 ;where R 4 It is H, C1-C which is optionally replaced by Y. 20 Branched or straight-chain alkyl groups or phenyl groups; and R 5 It is C1-C 20 Branched or straight-chain alkyl groups, and n and o are each independently 0 or 1.

18. Use of the compound of formula II according to claim 17, wherein X 1 and X 2 When present, each is independently a C1-C8 straight-chain or branched saturated or unsaturated aliphatic hydrocarbon group.

19. Use of the compound of formula II according to claim 17 or claim 18, wherein L 1 It is a C1-C8 straight-chain or branched hydrocarbon group or a C5-C... 14 Aromatic cyclic groups.

20. Use of the compound of formula II according to claim 19, wherein L 1 It is a C1-C4 straight-chain or branched hydrocarbon group, or benzene or naphthalene.

21. Use of the compound of formula II according to claim 19, wherein L 1 It is a C2 alkyl group, or benzene or naphthalene.

22. Use of the compound of formula II according to any one of claims 17 to 21, wherein both n and o are 0.

23. Use of the compound of formula II according to any one of claims 17 to 22, wherein L 1 It has not been replaced.

24. Use of the compound of formula II according to any one of claims 17 to 23, wherein the compound of formula II is selected from: ， ， ， and .

25. A method for promoting adhesion between an epoxyamine coating formulation and a polysiloxane coating formulation, wherein the method comprises adding a compound of formula II as defined in any one of claims 17 to 24 to at least one of the coating formulations and bringing the formulations into contact.

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