A coating additive, its preparation method and application

Abstract

This invention relates to the field of polymer technology, specifically to a coating additive, its preparation method, and its application. The coating additive comprises a polyether derivative backbone and at least one compound derived from general formula A; wherein, R... a Selected from hydrogen, -alkyl, -alkylene, -OH, -O-R b alkylene-O-R b The coating additives of the present invention can effectively change the wetting properties of coatings, have high-efficiency anti-aging properties, and the preparation method is simpler, low-carbon and environmentally friendly. These additives include alkyl groups spaced by one or more heteroatoms, alkyl groups spaced by one or more first spacer groups alone or in combination, alkyl groups substituted with one or more first substituents, and heteroalkyl groups substituted with one or more first substituents.

Description

Technical Field

[0001] This invention relates to the field of polymer technology, specifically to a coating additive, its preparation method, and its application. Background Technology

[0002] Paint is a continuous thin film that can be applied to the surface of an object to protect or decorate it. It is usually based on resin, oil, or emulsion. During the preparation process, pigments, fillers, and additives are usually added, and it needs to be dissolved in organic solvents or water to form a viscous liquid.

[0003] The lifespan of paint varies depending on the product. Liquid marble-textured products use modified silicone resin emulsion as a base material and employ a special coating technology to encapsulate various colored paints into colloidal water-based colored particles, ensuring their uniform and stable dispersion in a water-based solvent. The lifespan of this type of paint is approximately 15 years.

[0004] The film-forming mechanism of coatings can be divided into two types: physical film-forming and chemical film-forming. Physical film-forming relies on the evaporation or thermal melting of the solvent in the coating to obtain a dried film; this is generally the film-forming form for plastic coatings. To obtain a smooth and even coating film, the choice of solvent is particularly important. If the solvent evaporates too quickly, the concentration rises rapidly, reducing the fluidity of the coating surface and causing unevenness. Furthermore, different solvents can affect the molecular morphology of the polymer, thus influencing the microstructure of the coating film.

[0005] Chemical film formation involves first applying a soluble, low-molecular-weight polymer to the surface of a substrate. After a series of conditions or heating, the low-molecular-weight coating undergoes cross-linking or molecular weight increase to form a tough film. This method is primarily used for film formation in thermosetting plastics. For example, drying oils and alkyd resins form films through the reaction with oxygen; amino resins and hydroxyl-containing alkyd resins, polyesters and acrylic resins form films through ether exchange reactions; and epoxy resins and polyamines cross-link to form films—all utilizing chemical reactions. Because early coatings mostly used vegetable oils as their main raw material, they were also called paints. Now, synthetic resins have replaced vegetable oils, hence the term "coatings." Coatings are not liquid; powder coatings are a major category of coatings. Coatings belong to organic chemical polymer materials, and the resulting film is a type of polymer compound. According to modern classification of chemical products, coatings belong to fine chemical products. Modern coatings are gradually becoming a type of multifunctional engineering material and an important industry in the chemical industry. Their main functions are fourfold: protection, decoration, concealing product defects, and other special functions to enhance product value. Paints can be classified according to their application on buildings: interior wall paints, exterior wall paints, floor paints, door and window paints, and ceiling paints. They can also be classified according to their function: general-purpose paints and special-function building paints, such as fire-retardant paints, waterproof paints, mildew-resistant paints, and road marking paints. Finally, they can be classified according to their color effect, such as metallic paints, solid color paints (also called natural color paints), and clear varnishes.

[0006] Currently available coatings are prone to embrittlement after long-term use. When applied to the surface of a product, they may crack, yellow, or experience reduced strength. Furthermore, various surface defects such as cracks, pinholes, bubbles, and scratches can easily occur during the coating process, thus affecting the coating's usability. Summary of the Invention

[0007] To overcome the shortcomings of existing technologies, this invention provides a coating additive, its preparation method, and its application. The coating additive of this invention can effectively modify the wetting properties of coatings, has highly efficient anti-aging properties, and its preparation method is simpler, low-carbon, and environmentally friendly.

[0008] The first aspect of the present invention provides a coating additive, which is prepared by polymerization of a polyether derivative backbone and at least one compound having the general formula A;

[0009] The general formula A has the following structure:

[0010]

[0011] General formula A;

[0012] Among them, R a Selected from hydrogen, -alkyl, -alkylene, -OH, -OR b alkylene-ORb Alkyl groups separated by one or more heteroatoms, alkyl groups separated by one or more first spacer groups alone or in combination, alkyl groups substituted by one or more first substituents, and heteroalkyl groups substituted by one or more first substituents.

[0013] The first spacer group is selected from one or more combinations of the following groups: -C(=O)O-, amino, -OC(=O)O-, alkenyl, alkynyl, -C(=S)O-, amide group, urea group, arylene, heteroalkylene, heteroarylene;

[0014] The first substituent is selected from one or more combinations of the following groups: hydrogen, hydroxyl, halogen, aryl, cycloalkyl, hydroxyalkyl, alkoxy, thioalkoxy, nitro, cyano, amino, heteroaryl, heterocycloalkyl, alkoxycarbonyl, aryloxycarbonyl, heteroaryloxycarbonyl, alkoxycarbonyl, heteroalkoxycarbonyl, alkoxythiocarbonyl, acyloxy, alkanoyloxy, aromatic acyloxy, heteroaryloxy, cycloalkanoyloxy, heteroalkanoyloxy, alkanoyl, aminoacyl, alkylaminoacyl, alkylsulfonyl, aromatic acyl, alkyl separated by one or more heteroatoms, or separated by one or more -C groups. Alkyl groups separated by (=O)O-, alkyl groups separated by one or more -OC(=O)O-, alkyl groups separated by one or more -C(=O)-, alkyl groups separated by one or more -C(=S)O-, alkyl groups separated by one or more amide groups, alkyl groups separated by one or more urea groups, alkyl groups separated by one or more arylene groups, alkyl groups separated by one or more alkenyl groups, alkyl groups separated by one or more alkynyl groups, alkyl groups separated by one or more amino groups, alkyl groups separated by one or more heteroalkyl groups, and alkyl groups separated by one or more heteroaryl groups.

[0015] p is The degree of aggregation of the repeating unit, where p is 0 or 1; when p is 0, the repeating unit... It is a single bond;

[0016] The o is The degree of aggregation of the repeating unit, where o is an integer from 1 to 15 (e.g., o is 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14 or 15);

[0017] In one instance, the R b Selected from one or more of the following groups: alkyl, cycloalkyl, -C(=O)R c Heterocyclic alkyl, alkyl spaced by one or more heteroatoms, alkyl spaced by one or more first spacer groups alone or in combination, alkyl substituted by one or more first substituents, heteroalkyl substituted by one or more first substituents, cycloalkyl substituted by one or more first substituents, -phenyl.

[0018] In one instance, the R c The group is selected from one or more of the following groups: alkyl, cycloalkyl, phenyl, heterocycloalkyl, alkyl spaced by one or more heteroatoms, alkyl spaced by one or more first spacer groups alone or in combination, alkyl substituted by one or more first substituents, heteroalkyl substituted by one or more first substituents, and cycloalkyl substituted by one or more first substituents.

[0019] In one instance, o is The degree of aggregation of repeating units, where o is an integer from 1 to 11, including but not limited to 1, 2, 3, 4, 5, 6, 7, 8, 9, 10 or 11;

[0020] Specifically, the general formula A includes the following structure:

[0021]

[0022] Where i is an integer from 1 to 18 (for example, it can be 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17 or 18).

[0023] In one example, the polyether derivative skeleton is a compound comprising general formula B;

[0024] The general formula B has the following structure:

[0025]

[0026] General formula B;

[0027] in,

[0028] n1, n2, ..., n m The degree of aggregation of each repeating unit is an integer from 0 to 200 (e.g., it can be 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 50, 100, 150 or 200).

[0029] The n1+n2+……+n m ≥1;

[0030] When n1, n2...n m When one or more of the values ​​are 0, the repeating unit is a single bond;

[0031] m is an integer from 1 to 20 (for example, it can be 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19 or 20);

[0032] R1, R2, R3...R m The same or different substituents;

[0033] Rt1 and Rt2 are the same or different end-capping groups.

[0034] The R1, R2, R3...R m The independent group is selected from one or more combinations of the following groups: hydrogen, alkyl, cycloalkyl, heterocycloalkyl, phenyl, alkyl separated by one or more heteroatoms, alkyl separated by one or more -C(=O)O-, alkyl separated by one or more amino groups, alkyl separated by one or more -OC(=O)O-, alkyl separated by one or more alkenyl groups, alkyl separated by one or more alkynyl groups, alkyl separated by one or more -C(=S)O-, alkyl separated by one or more amide groups, alkyl separated by one or more urea groups, alkyl separated by one or more arylene groups, alkyl separated by one or more heteroalkylene groups, alkyl separated by one or more heteroarylene groups, alkyl separated by a combination of the above spacer groups, alkyl substituted with one or more second substituents, heteroalkyl substituted with one or more second substituents, cycloalkyl or -benzene ring substituted with one or more second substituents;

[0035] The second substituent is selected from one or more combinations of the following groups: hydroxyl, halogen, aryl, cycloalkyl, hydroxyalkyl, alkoxy, thioalkoxy, nitro, cyano, amino, heteroaryl, heterocycloalkyl, alkoxycarbonyl, aryloxycarbonyl, heteroaryloxycarbonyl, heteroalkoxycarbonyl, alkoxythiocarbonyl, acyloxy, alkanoyloxy, aromatic acyloxy, heteroaryloxy, cycloalkanoyloxy, heteroalkanoyloxy, alkanoyl, aminoacyl, alkylaminoacyl, alkylsulfonyl, aromatic acyl, alkyl separated by one or more heteroatoms, alkyl separated by one or more -C(=O)O- groups. Alkyl groups separated by one or more -OC(=O)O- groups, alkyl groups separated by one or more -C(=O)- groups, alkyl groups separated by one or more -C(=S)O- groups, alkyl groups separated by one or more amide groups, alkyl groups separated by one or more urea groups, alkyl groups separated by one or more arylene groups, alkyl groups separated by one or more alkenyl groups, alkyl groups separated by one or more alkynyl groups, alkyl groups separated by one or more amino groups, alkyl groups separated by one or more heteroalkyl groups, alkyl groups separated by one or more heteroarylene groups, and alkyl groups separated by a combination of the above spacer groups.

[0036] Preferably, the second substituent is selected from one or more combinations of the following groups: hydroxyl, cycloalkyl, hydroxyalkyl, alkoxy, thioalkoxy, nitro, cyano, amino, heterocycloalkyl, alkoxycarbonyl, heteroalkoxycarbonyl, alkoxythiocarbonyl, acyloxy, alkanoyloxy, cycloalkanoyloxy, heteroalkanoyloxy, alkanoyl, aminoacyl, alkylaminoacyl, alkylsulfonyl, aromatic acyl, alkyl separated by one or more heteroatoms, alkyl separated by one or more -C(=O)O-, alkyl separated by one or more -OC(=O)O-, alkyl separated by one or more -C(=O)-, alkyl separated by one or more -C(=S)O-, alkyl separated by one or more amide groups, alkyl separated by one or more urea groups, alkyl separated by one or more alkenyl groups, alkyl separated by one or more alkynyl groups, alkyl separated by one or more amino groups, alkyl separated by one or more heteroalkylene groups, and alkyl separated by a combination of the above spacer groups.

[0037] Rt1 and Rt2 are independently selected from one or more combinations of: hydrogen, alkyl, cycloalkyl, heterocycloalkyl, phenyl, alkyl separated by one or more heteroatoms, alkyl separated by one or more -C(=O)O-, alkyl separated by one or more amino groups, alkyl separated by one or more -OC(=O)O-, alkyl separated by one or more alkenyl groups, alkyl separated by one or more alkynyl groups, alkyl separated by one or more -C(=S)O-, alkyl separated by one or more amide groups, alkyl separated by one or more urea groups, alkyl separated by one or more arylene groups, alkyl separated by one or more heteroalkylene groups, alkyl separated by one or more heteroalkylene groups, alkyl separated by one or more heteroalkylene groups, alkyl separated by a combination of the above spacer groups, alkyl substituted with one or more third substituents, heteroalkyl substituted with one or more third substituents, and cycloalkyl substituted with one or more third substituents.

[0038] The third substituent is selected from one or more combinations of the following groups: hydroxyl, halogen, aryl, cycloalkyl, hydroxyalkyl, alkoxy, thioalkoxy, nitro, cyano, amino, heteroaryl, heterocycloalkyl, alkoxycarbonyl, aryloxycarbonyl, heteroaryloxycarbonyl, heteroalkoxycarbonyl, alkoxythiocarbonyl, acyloxy, alkanoyloxy, aromatic acyloxy, heteroaryloxy, cycloalkanoyloxy, heteroalkanoyloxy, alkanoyl, aminoacyl, alkylaminoacyl, alkylsulfonyl, aromatic acyl, alkyl separated by one or more heteroatoms, alkyl separated by one or more -C(=O)O-. Alkyl groups separated by one or more -OC(=O)O- groups, alkyl groups separated by one or more -C(=O)- groups, alkyl groups separated by one or more -C(=S)O- groups, alkyl groups separated by one or more amide groups, alkyl groups separated by one or more urea groups, alkyl groups separated by one or more arylene groups, alkyl groups separated by one or more alkenyl groups, alkyl groups separated by one or more alkynyl groups, alkyl groups separated by one or more amino groups, alkyl groups separated by one or more heteroalkyl groups, alkyl groups separated by one or more heteroarylene groups, and alkyl groups separated by a combination of the above spacer groups.

[0039] In one instance, in the general formula B, ------ represents one or more identical or different ones. And / or, ------ represents a single key.

[0040] Furthermore, the general formula B is selected from the following structures:

[0041]

[0042]

[0043]

[0044]

[0045]

[0046]

[0047]

[0048]

[0049]

[0050]

[0051]

[0052]

[0053]

[0054]

[0055]

[0056]

[0057] A second aspect of the present invention provides a method for preparing the coating additive described in the first aspect of the present invention, the method comprising a polymerization reaction of a compound of general formula A and a compound of general formula B; optionally, the polymerization reaction is carried out under conditions in the presence of a catalyst. Further, the polymerization reaction is carried out in a solvent selected from one or more of the following: tetrahydrofuran, 2-methyltetrahydrofuran, halogenated hydrocarbons, acetonitrile, propionitrile, butyronitrile, aromatic hydrocarbons, aliphatic hydrocarbons, alcohols, dimethyl sulfoxide, N,N-dimethylamide and diphenyl ether, and water;

[0058] Preferably, the halogenated hydrocarbons include one or more of dichloromethane, dichloroethane, or carbon tetrachloride;

[0059] Preferably, the aromatic hydrocarbons include one or more of benzene, toluene, xylene, chlorobenzene, or dichlorotoluene;

[0060] Preferably, the aliphatic hydrocarbons include one or more of petroleum ether, n-hexane, n-heptane, cyclohexane, and n-octane;

[0061] Preferably, the alcohols include one or more of methanol, ethanol, propanol, ethylene glycol, diethylene glycol, and ethylene glycol methyl ether.

[0062] More preferably, the solvent is selected from one or more of water, toluene, benzene, chlorobenzene, xylene, cyclohexane, n-heptane, or dichloromethane.

[0063] Particularly preferred is that the solvent is selected from one or more combinations of water, benzene, xylene or chlorobenzene.

[0064] Furthermore, the catalyst is an alkaline catalyst;

[0065] Preferably, the alkaline catalyst is selected from one or more combinations of the following: K2CO3, KOH, NaH, NaOMe, KO T Bu, rhodium complexes, ruthenium complexes, clay-supported nickel bromide, or ionic liquids;

[0066] More preferably, the molar ratio of the catalyst to the compound of general formula A is (1:0.5) to (1:2), (for example, the molar ratio can be 2:1, 1:1 or 1:2);

[0067] Particularly preferred is the polymerization reaction, which is a Michael addition reaction;

[0068] Particularly preferred is that the polymerization reaction temperature is 0-150℃ (including but not limited to 10℃, 20℃, 30℃, 40℃, 50℃, 60℃, 70℃, 80℃, 90℃, 100℃, 110℃, 120℃, 130℃, 140℃ or 150℃), preferably 0-80℃, and more preferably 0-40℃.

[0069] A third aspect of the present invention provides a composition comprising the coating additives described in the first aspect of the present invention and one or more organic substances sensitive to light, heat or oxidation; or, the coating additives prepared by the method described in the second aspect of the present invention and one or more organic substances sensitive to light, heat or oxidation.

[0070] In one example, the amount of the coating additive may be 0.01-5 wt% of the standard formulation weight, which is the total weight of the composition.

[0071] The fourth aspect of the present invention provides the application of the coating additive described in the first aspect of the present invention or the composition described in the third aspect of the present invention in the preparation of light stabilizers, the preparation of wetting agents, and on the surface of articles.

[0072] Specifically, the product is an industrial product or a non-industrial product that requires coating;

[0073] Preferably, the industrial product is a polymer material product.

[0074] By employing the above technical solution, the present invention has at least the following advantages compared with the prior art:

[0075] (1) The hardness, gloss, impact test and solvent resistance test of the coating film with the coating additive of the present invention are not weaker than those of the coating film with commercial additives. At the same time, the weather resistance of the coating film with the coating additive of the present invention is significantly stronger than that of commercial additives. The coating additive of the present invention can significantly improve the anti-aging performance of the coating.

[0076] (2) The coating additives of the present invention can be prepared with low alkalinity by selecting specific raw materials containing NOR amine ether structures;

[0077] (3) The preparation method of the coating additive of the present invention is simpler and more environmentally friendly.

[0078] The endpoints and any values ​​of the ranges disclosed herein are not limited to the precise ranges or values, and these ranges or values ​​should be understood to include values ​​close to these ranges or values. For numerical ranges, the endpoint values ​​of the various ranges, the endpoint values ​​of the various ranges and individual point values, and individual point values ​​can be combined with each other to obtain one or more new numerical ranges, which should be considered as specifically disclosed herein. Detailed Implementation

[0079] The following provides a detailed description of specific embodiments of the present invention. It should be understood that the specific embodiments described herein are for illustrative and explanatory purposes only and are not intended to limit the scope of the invention.

[0080] The inventors of this invention discovered that by containing With The raw materials are reacted to produce a high molecular weight coating additive. This new type of coating additive contains both hydrophilic ether-O- groups and lipophilic ester-C(=O)-O groups. When added to coatings, it can effectively change the wetting properties of the coatings.

[0081] The inventors of this invention also introduced a piperidine group with anti-photoaging properties, which makes the coating additives have high-efficiency anti-aging properties; by selecting specific raw materials containing NOR amine ether structures, coating additives with low alkalinity can be prepared.

[0082] The first aspect of the present invention provides a coating additive, which is prepared by polymerization of a polyether derivative backbone and at least one compound having the general formula A;

[0083] The general formula A has the following structure:

[0084]

[0085] General formula A;

[0086] Among them, R a Selected from hydrogen, -alkyl, -alkylene, -OH, -OR b alkylene-OR b Alkyl groups separated by one or more heteroatoms, alkyl groups separated by one or more first spacer groups alone or in combination, alkyl groups substituted by one or more first substituents, and heteroalkyl groups substituted by one or more first substituents.

[0087] In one example, the first spacer group is selected from one or more combinations of the following groups: -C(=O)O-, amino, -OC(=O)O-, alkenyl, alkynyl, -C(=S)O-, amide group, urea group, aryl, heteroalkyl, heteroaryl.

[0088] In one example, the first substituent is selected from hydrogen, hydroxyl, halogen, aryl, cycloalkyl, hydroxyalkyl, alkoxy, thioalkoxy, nitro, cyano, amino, heteroaryl, heterocycloalkyl, alkoxycarbonyl, aryloxycarbonyl, heteroaryloxycarbonyl, alkoxycarbonyl, heteroalkoxycarbonyl, alkoxythiocarbonyl, acyloxy, alkanoyloxy, aromatic acyloxy, heteroaryloxy, cycloalkanoyloxy, heteroalkanoyloxy, alkanoyl, aminoacyl, alkylaminoacyl, alkylsulfonyl, aromatic acyl, alkyl separated by one or more heteroatoms, alkyl separated by one or more -C(=O)O-, Alkyl groups separated by one or more -OC(=O)O-, alkyl groups separated by one or more -C(=O)-, alkyl groups separated by one or more -C(=S)O-, alkyl groups separated by one or more amide groups, alkyl groups separated by one or more urea groups, alkyl groups separated by one or more arylene groups, alkyl groups separated by one or more alkenyl groups, alkyl groups separated by one or more alkynyl groups, alkyl groups separated by one or more amino groups, alkyl groups separated by one or more heteroalkyl groups, alkyl groups separated by one or more heteroarylene groups, and alkyl groups separated by a combination of the above spacer groups.

[0089] In one instance, p is The degree of aggregation of the repeating unit, where p is 0 or 1;

[0090] The o is The degree of aggregation of repeating units, where o is an integer from 1 to 15;

[0091] In one instance, the R b Selected from one or more of the following groups: alkyl, cycloalkyl, -C(=O)R c Heterocyclic alkyl, alkyl spaced by one or more heteroatoms, alkyl spaced by one or more first spacer groups alone or in combination, alkyl substituted by one or more first substituents, heteroalkyl substituted by one or more first substituents, cycloalkyl substituted by one or more first substituents, -phenyl.

[0092] In one instance, the R c The group is selected from alkyl, cycloalkyl, phenyl, heterocycloalkyl, alkyl spaced by one or more heteroatoms, alkyl spaced by one or more first spacer groups alone or in combination, alkyl substituted by one or more first substituents, heteroalkyl substituted by one or more first substituents, and cycloalkyl substituted by one or more first substituents.

[0093] In one instance, o is The degree of aggregation of the repeating unit, where o is an integer from 1 to 15, preferably an integer from 1 to 11 (e.g., 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11).

[0094] In one instance, the general formula A includes the following structure:

[0095]

[0096]

[0097] Where i is an integer from 1 to 18 (e.g., 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18).

[0098] In one instance, the polyether derivative skeleton comprises a compound of general formula B;

[0099] The general formula B has the following structure:

[0100]

[0101] General formula B.

[0102] In one instance, n1, n2...n m The degree of aggregation of each repeating unit is an integer from 0 to 200 (e.g., 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 50, 100, 150 or 200).

[0103] In one instance, n1+n2+……+n m ≥1.

[0104] In one instance, when n1, n2... or n... m When any one of them is 0, the repeating unit is a single bond.

[0105] In one instance, m is an integer from 1 to 20 (e.g., 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20).

[0106] In one instance, R1, R2, R3...R m The same or different substituents;

[0107] In one instance, Rt1 and Rt2 are the same or different end-capping groups.

[0108] In one instance, R1, R2, R3...R m They are the same substituents.

[0109] In one instance, R1, R2, R3...R m For different substituents.

[0110] In one example, Rt1 and Rt2 are the same end-capping groups.

[0111] In one example, Rt1 and Rt2 are different end-capping groups.

[0112] In one instance, Rt1 and Rt2 can be any suitable end-capping groups.

[0113] In one instance, Rt1 and Rt2 may have potentially reactive groups or be inert end-capping groups.

[0114] In one example, Rt1 and Rt2 are independently selected from one or more combinations of the following groups: hydrogen, alkyl, cycloalkyl, heterocycloalkyl, phenyl, alkyl separated by one or more heteroatoms, alkyl separated by one or more -C(=O)O-, alkyl separated by one or more amino groups, alkyl separated by one or more -OC(=O)O-, alkyl separated by one or more alkenyl groups, alkyl separated by one or more alkynyl groups, alkyl separated by one or more -C(=S)O-, alkyl separated by one or more amide groups, alkyl separated by one or more urea groups, alkyl separated by one or more arylene groups, alkyl separated by one or more heteroalkylene groups, alkyl separated by one or more heteroalkylene groups, alkyl separated by one or more heteroalkylene groups, alkyl separated by a combination of the above spacer groups, alkyl substituted with one or more third substituents, heteroalkyl substituted with one or more third substituents, and cycloalkyl substituted with one or more third substituents.

[0115] The third substituent is selected from one or more combinations of the following groups: hydroxyl, halogen, aryl, cycloalkyl, hydroxyalkyl, alkoxy, thioalkoxy, nitro, cyano, amino, heteroaryl, heterocycloalkyl, alkoxycarbonyl, aryloxycarbonyl, heteroaryloxycarbonyl, heteroalkoxycarbonyl, alkoxythiocarbonyl, acyloxy, alkanoyloxy, aromatic acyloxy, heteroaryloxy, cycloalkanoyloxy, heteroalkanoyloxy, alkanoyl, aminoacyl, alkylaminoacyl, alkylsulfonyl, aromatic acyl, alkyl separated by one or more heteroatoms, alkyl separated by one or more -C(=O)O-. Alkyl groups separated by one or more -OC(=O)O- groups, alkyl groups separated by one or more -C(=O)- groups, alkyl groups separated by one or more -C(=S)O- groups, alkyl groups separated by one or more amide groups, alkyl groups separated by one or more urea groups, alkyl groups separated by one or more arylene groups, alkyl groups separated by one or more alkenyl groups, alkyl groups separated by one or more alkynyl groups, alkyl groups separated by one or more amino groups, alkyl groups separated by one or more heteroalkyl groups, alkyl groups separated by one or more heteroarylene groups, and alkyl groups separated by a combination of the above spacer groups.

[0116] In one example, the substituents selected from Rt1 and Rt2 are chosen from the group consisting of the following groups: hydroxyl, cycloalkyl, hydroxyalkyl, alkoxy, thioalkoxy, nitro, cyano, amino, heterocycloalkyl, alkoxycarbonyl, heteroalkoxycarbonyl, alkoxythiocarbonyl, acyloxy, alkanoyloxy, cycloalkanoyloxy, heteroalkanoyloxy, alkanoyl, aminoacyl, alkylaminoacyl, alkylsulfonyl, aromatic acyl, alkyl separated by one or more heteroatoms, alkyl separated by one or more -C(=O)O-, alkyl separated by one or more -OC(=O)O-, alkyl separated by one or more -C(=O)-, alkyl separated by one or more -C(=S)O-, alkyl separated by one or more amide groups, alkyl separated by one or more urea groups, alkyl separated by one or more alkenyl groups, alkyl separated by one or more alkynyl groups, alkyl separated by one or more amino groups, alkyl separated by one or more heteroalkylene groups, and alkyl separated by a combination of the above spacer groups.

[0117] In one instance, Rt1 and Rt2 are independently selected from hydrogen and C1-C4 alkyl groups.

[0118] In one instance, R1, R2, R3...R m The independent group is selected from one or more combinations of the following groups: hydrogen, alkyl, cycloalkyl, heterocycloalkyl, phenyl, alkyl separated by one or more heteroatoms, alkyl separated by one or more -C(=O)O-, alkyl separated by one or more amino groups, alkyl separated by one or more -OC(=O)O-, alkyl separated by one or more alkenyl groups, alkyl separated by one or more alkynyl groups, alkyl separated by one or more -C(=S)O-, alkyl separated by one or more amide groups, alkyl separated by one or more urea groups, alkyl separated by one or more arylene groups, alkyl separated by one or more heteroalkylene groups, alkyl separated by one or more heteroarylene groups, alkyl separated by a combination of the above spacer groups, alkyl substituted with one or more second substituents, heteroalkyl substituted with one or more second substituents, cycloalkyl or -benzene ring substituted with one or more second substituents;

[0119] The second substituent is selected from one or more of the following groups: hydroxyl, halogen, aryl, cycloalkyl, hydroxyalkyl, alkoxy, thioalkoxy, nitro, cyano, amino, heteroaryl, heterocycloalkyl, alkoxycarbonyl, aryloxycarbonyl, heteroaryloxycarbonyl, heteroalkoxycarbonyl, alkoxythiocarbonyl, acyloxy, alkanoyloxy, aromatic acyloxy, heteroaryloxy, cycloalkanoyloxy, heteroalkanoyloxy, alkanoyl, aminoacyl, alkylaminoacyl, alkylsulfonyl, aromatic acyl, alkyl separated by one or more heteroatoms, alkyl separated by one or more -C(=O)O-, etc. One or more -OC(=O)O- spaced alkyl groups, one or more -C(=O)- spaced alkyl groups, one or more -C(=S)O- spaced alkyl groups, one or more amide groups spaced alkyl groups, one or more urea groups spaced alkyl groups, one or more arylene groups spaced alkyl groups, one or more alkenyl groups spaced alkyl groups, one or more alkynyl groups spaced alkyl groups, one or more amino groups spaced alkyl groups, one or more heteroalkyl groups spaced alkyl groups, one or more heteroarylene groups spaced alkyl groups, or a combination of the above spacer groups.

[0120] More specifically, the second substituent is selected from one or more combinations of the following groups: hydroxyl, cycloalkyl, hydroxyalkyl, alkoxy, thioalkoxy, nitro, cyano, amino, heterocycloalkyl, alkoxycarbonyl, heteroalkoxycarbonyl, alkoxythiocarbonyl, acyloxy, alkanoyloxy, cycloalkanoyloxy, heteroalkanoyloxy, alkanoyl, aminoacyl, alkylaminoacyl, alkylsulfonyl, aromatic acyl, alkyl separated by one or more heteroatoms, alkyl separated by one or more -C(=O)O-, alkyl separated by one or more -OC(=O)O-, alkyl separated by one or more -C(=O)-, alkyl separated by one or more -C(=S)O-, alkyl separated by one or more amide groups, alkyl separated by one or more urea groups, alkyl separated by one or more alkenyl groups, alkyl separated by one or more alkynyl groups, alkyl separated by one or more amino groups, alkyl separated by one or more heteroalkylene groups, and alkyl separated by a combination of the above spacer groups.

[0121] In one instance, in general formula B, ------ represents one or more identical or different ones.

[0122] In one instance, ------ represents a single key.

[0123] In one instance, when m = 4, ------ represents

[0124] In one instance, when m = 5, ------ represents

[0125] In one embodiment, m is 1, and the general formula B has the following structure:

[0126]

[0127] B-1.

[0128] In one embodiment, m is 2, and the general formula B has the following structure:

[0129]

[0130] B-2.

[0131] In one instance, compounds derived from general formula B are selected from the following structures:

[0132]

[0133]

[0134]

[0135]

[0136]

[0137]

[0138]

[0139]

[0140]

[0141]

[0142]

[0143]

[0144]

[0145]

[0146]

[0147]

[0148] The inventors of this invention have discovered that the coating additives of this invention have wetting and light-stabilizing effects in coatings.

[0149] A second aspect of the present invention provides a method for preparing the coating additives described in the first aspect of the present invention, comprising a polymerization reaction of a compound of general formula A and a compound of general formula B.

[0150] Optionally, the polymerization reaction is carried out in the presence of a catalyst.

[0151] The polymerization reaction may or may not be carried out in a solvent. In one example, the polymerization reaction is carried out in a solvent.

[0152] In one example, the solvent may be selected from one or more of tetrahydrofuran, 2-methyltetrahydrofuran, halogenated hydrocarbons (such as dichloromethane, dichloroethane, carbon tetrachloride, etc.), acetonitrile, propionitrile, butyronitrile, aromatic hydrocarbons (such as benzene, toluene, xylene, chlorobenzene, dichlorotoluene, etc.), aliphatic hydrocarbons (such as petroleum ether, n-hexane, n-heptane, cyclohexane, n-octane, etc.), alcohols (such as methanol, ethanol, propanol, ethylene glycol, diethylene glycol, ethylene glycol methyl ether), dimethyl sulfoxide, N,N-dimethylamide and diphenyl ether, and water.

[0153] In one example, the solvent is selected from one or more of water, toluene, benzene, chlorobenzene, xylene, cyclohexane, n-heptane, and dichloromethane.

[0154] In one example, the solvent is an aromatic hydrocarbon solvent such as water, benzene, xylene, or chlorobenzene.

[0155] The polymerization reaction can be carried out with or without a catalyst.

[0156] In one instance, the polymerization reaction was carried out under catalyst-free conditions.

[0157] In one instance, the polymerization reaction was carried out in the presence of a catalyst.

[0158] In one example, the catalyst is a basic catalyst.

[0159] In one example, the alkaline catalyst is selected from K2CO3, KOH, NaH, NaOMe, and KO. T Bu, rhodium complexes, ruthenium complexes, clay-supported nickel bromide, ionic liquids, etc.

[0160] Specifically, the molar ratio of catalyst to raw material A is (1:0.5)-(1:2) (e.g., 1:0.5, 1:1, 1:1.5, 1:2).

[0161] In one instance, the polymerization reaction is a Michael addition reaction.

[0162] Specifically, the reaction temperature of the polymerization reaction is 0-150℃ (e.g., 10℃, 20℃, 40℃, 60℃, 80℃, 100℃, 120℃ or 150℃), preferably 0-80℃, and more preferably 0-40℃.

[0163] In one instance, the polymerization reaction is an atmospheric pressure reaction.

[0164] In one example, the polymerization reaction is carried out in a protective gas, which can be a chemically inert gas such as argon or nitrogen.

[0165] The above-mentioned raw materials can be commercially available products or prepared according to methods known in the art.

[0166] A third aspect of the present invention provides a composition comprising the coating additives described in the first aspect of the present invention and one or more organic substances sensitive to light, heat or oxidation; or the coating additives prepared by the method described in the second aspect of the present invention and one or more organic substances sensitive to light, heat or oxidation.

[0167] In the composition, the amount of coating additives is determined by the properties of the organic substances, their end use, and the additives used; coating additives can be used in various proportions.

[0168] In one example, the amount of the coating additive in the composition may be 0.01-5 wt% (e.g., 0.01%, 0.05%, 0.1%, 0.15%, 0.2%, 0.25%, 0.3%, 0.35%, 0.4%, 0.45%, 0.5%, 1%, 2%, 3%, 4%, 5%) of the standard formulation weight. The standard formulation weight is the total weight of the composition.

[0169] Preferably, the amount of the coating additive is 0.05%-2% of the standard formulation weight.

[0170] More preferably, the amount of the coating additive is 0.05%-1% of the standard formulation weight.

[0171] In one example, the organic substance in the composition may be selected from one or more combinations of polyurethane, polyamide-imide, polyamide, polyimide, polyphenylene sulfide, polyethersulfone, polyetheretherketone, siloxane, polytetrafluoroethylene, hexafluoropropylene, 1,1-difluoroethylene, polytetrafluoroethylene, fluorinated ethylene propylene, or perfluorocarbon.

[0172] In one example, the composition may further include one or more of the following: antioxidants, UV absorbers, hindered amine light stabilizers, reinforcing agents, fillers, flame retardants, plasticizers, lubricants, emulsifiers, pigments, rheology modifiers, catalysts, flow control agents, optical brighteners, refractories, antistatic agents, or foaming agents.

[0173] In one example, the antioxidant may be selected from: phenolic and / or amine antioxidants, phosphites, thioesters, etc., preferably, the antioxidant is selected from one or more of antioxidant 1010, antioxidant 1076, antioxidant 1098 or antioxidant 168.

[0174] In one example, the UV absorber may be selected from one or more of salicylates, benzoates, benzotriazoles, or triazines.

[0175] In one example, the filler and reinforcing agent may be selected from one or more of the following: zinc oxide, aluminum oxide, titanium dioxide, iron oxide, chromium dioxide, silicon oxide, aluminum silicate, magnesium aluminum silicate, silicon carbide, titanium carbide, silicon oxide, titanium nitride, or boron nitride.

[0176] In one example, the filler and reinforcing agent are selected from one or more of the following: calcium carbonate, silicate, glass fiber, glass beads, asbestos, talc, kaolin, mica, barium sulfate, metal oxides and hydroxides, carbon black, graphite, wood flour and flour or other natural product fibers or synthetic fibers.

[0177] In one example, the pigment may be selected from: cyan zeolite, channel black, carbon black, etc.

[0178] The fourth aspect of the present invention provides the application of the coating additives described in the first aspect of the present invention, or the compositions described in the third aspect of the present invention, in the preparation of light stabilizers, the preparation of wetting agents, and on the surface of articles.

[0179] Specifically, the product is an industrial product or a non-industrial product that requires coating;

[0180] Preferably, the industrial product is a polymer material product.

[0181] In one instance, the light stabilizer is used in the production, processing, and use of coating products to delay or prevent the aging of the coating products and improve their performance and service life.

[0182] Furthermore, the application areas of the coating products include various fields such as road traffic, construction, furniture, and electrical appliances.

[0183] In one example, the polymer material product can be plastic, rubber, fiber, coating, adhesive, composite material, etc., and can be used in automotive interior or exterior decoration materials, floating devices, road traffic devices, agricultural products, electrical appliances, furniture, footwear, hygiene products, health care products, construction and other fields.

[0184] This invention tests the paint film according to the following standards: the cross-cut test is based on GB / T9286-1998 Scratch test for paint and varnish films; the pencil hardness test method for paint film is based on GB / T 6739-2006 Pencil test for paint and varnish films; the gloss test method for gloss is based on GB / T 9754 Determination of 20°, 60° and 85° specular gloss of paint films without metallic pigments; the impact test is based on GB / T48939-2013 Test method for impact resistance of paint films on furniture surfaces; and the solvent resistance test is based on GB / T 23989-2009 Determination method for solvent resistance of coatings.

[0185] The term "alkyl" as used in this invention can be a straight-chain or branched alkyl group, typically containing 1 to 22 (e.g., 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22) carbon atoms, i.e., C1-22 alkyl, such as C1-8 alkyl, C1-6 alkyl, C1-3 alkyl, and examples of alkyl groups include methyl, ethyl, propyl, isopropyl, n-butyl, isobutyl, tert-butyl, n-pentyl, isopentyl, n-hexyl, n-dodecyl, and n-octadecyl. The same applies to alkoxy groups, which typically contain 1 to 22 (e.g., 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22) carbon atoms, i.e., C1-22 alkoxy groups, such as C1-8 alkoxy, C1-6 alkoxy, C1-3 alkoxy. Examples of alkoxy groups include methoxy, ethoxy, isopropoxy, propoxy, butoxy, hexoxy, octoxy, n-dodecyloxy, and n-octadecyloxy. Preferred substituents are halogens, aryl, hydroxyl, cyano, nitro, alkoxy, and alkylamino groups; preferred spacer groups are oxygen, nitrogen, sulfur, arylene, heteroalkyl, -C(=O)-, or -C(=O)O-.

[0186] The term "alkylene" as used in this invention can refer to a straight-chain or branched alkyl group. A typical alkylene group contains 1 to 22 (e.g., 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22) carbon atoms, i.e., C1-22 alkylene groups, such as C1-18 alkylene groups, C1-12 alkylene groups, C1-8 alkylene groups, C1-6 alkylene groups, C1-3 alkylene groups, and examples of alkylene groups include methylene, ethylene, propylene, butylene, etc.

[0187] The term "cycloalkyl" as used in this invention includes substituted cycloalkyl and unsaturated cycloalkyl. Typical cycloalkyl contains 1 to 10 (e.g., 1, 2, 3, 4, 5, 6, 7, 8, 9, 10) carbon atoms, i.e., C1-10 cycloalkyl, such as C3-6 cycloalkyl. Examples of cycloalkyl are cyclopentyl, cyclopropyl, and cyclohexyl.

[0188] The term "aryl" as used in this invention refers to, for example, benzene ring and naphthyl ring aryl groups, particularly benzene ring aryl groups. Aryl groups include unsubstituted and substituted aryl groups, wherein the substituents can be alkyl, cyano, nitro, alkoxy, hydroxy, halogen, amino, alkylamino, arylyl, alkanoyl, arylsulfonyloxy, alkamido, or alkanosulfonylamino.

[0189] The term "heterocyclic group" as used in this invention includes heteroaryl and heteroalicyclic groups containing 1 to 3 monocyclic and / or fused rings, and 3 to 18 ring atoms. Examples of "heterocyclic alkyl" include pyrrolidine, piperidine, morpholine, tetrahydrofuran, piperidinone, piperazine, imidazoline, imidazolinone, 1,3,5-triazine alkylone, or piperazine. Heterocyclic alkyl groups include unsubstituted and substituted forms of the above-mentioned groups, and the substituents can be alkyl, hydroxyalkyl, halogen, hydroxyl, alkoxy, aryl, alkylacyl, nitro, cyano, amino, or alkylamino. Examples of heteroaryl groups include benzotriazole and 1,3,5-triazine. Heteroaryl groups include unsubstituted and substituted forms of the above-mentioned groups, and the substituents can be aryl, alkyl, arylamino, hydroxyl, halogen, amino, alkenyl, nitro, cyano, or alkoxy. The heterocyclic group contains one, two or three heteroatoms, which can be selected from nitrogen, sulfur, oxygen, phosphorus, and silicon, especially oxygen and nitrogen.

[0190] The term "halogen" as used in this invention refers to bromine, chlorine, iodine, or fluorine.

[0191] The term "heteroatom" as used in this invention refers to N, O, or S.

[0192] All publications, patents, and published patent specifications cited in this article are incorporated herein in their entirety through citation.

[0193] The polymerizable raw materials shown above are known in the art, some of which are commercially available or can be synthesized using methods known in the art.

[0194] The technical solutions of the present invention will be clearly and completely described below with reference to the embodiments of the present invention. Obviously, the described embodiments are only some embodiments of the present invention, and not all embodiments. Based on the embodiments of the present invention, all other embodiments obtained by those of ordinary skill in the art without creative effort are within the scope of protection of the present invention.

[0195] Example 1

[0196] Ingredient 1-1:

[0197] Raw materials 1-2:

[0198] In a 2000mL round-bottom flask, 67.6g of raw material 1-1 was dissolved in 400mL of xylene, 300mL of KOH solution (1mol / L) was added, the mixture was heated to 40℃, and then 202g of raw material 1-2 was slowly added dropwise. The mixture was stirred continuously for 4h, and after the reaction was complete, 236.4g of the target product P1-EX1 was obtained.

[0199] The molecular weight of the target product P1-EX1 is 1081.

[0200] Viscosity (100℃) of target product P1-EX1: 461 cps.

[0201] Example 2

[0202] Raw material 2-1:

[0203] Raw material 2-2:

[0204] In a 2L round-bottom flask, 42.6g of raw material 2-1 was dissolved in 400mL of xylene, and 200mL of KOH solution (2mol / L) was added. The temperature was controlled at 20℃, and then 267g of raw material 2-2 was slowly added dropwise. The mixture was stirred continuously for 3h. After the reaction was complete, 276.41g of the target product P1-EX2 was obtained.

[0205] The molecular weight of the target product P1-EX2 is 1238.5.

[0206] The viscosity (100℃) of the target product P1-EX2 is 745 cps.

[0207] Example 3

[0208] Ingredient 3-1:

[0209] Raw material 3-2:

[0210] In a 2L round-bottom flask, 227.3g of raw material 3-1 was dissolved in 500mL of xylene, 0.6mol of NaOMe was added, the temperature was controlled at 30℃, and then 332.35g of raw material 3-2 was slowly added dropwise. The mixture was stirred continuously for 3h. After the reaction was complete, 521.3g of the target product P1-EX3 was obtained.

[0211] The molecular weight of the target product P1-EX3 is 2238.7.

[0212] Viscosity of target product P1-EX3 (100℃): 1045 cps

[0213] Example 4

[0214] Raw material 4-1:

[0215] Raw material 4-2:

[0216] In a 2L round-bottom flask, 220.32g of raw material 4-1 was dissolved in 600mL of xylene, 0.5mol of NaOMe was added, the temperature was controlled at 25℃, and then 385.8g of raw material 4-2 was slowly added dropwise. The mixture was stirred continuously for 1.5h. After the reaction was complete, 573.59g of the target product P1-EX4 was obtained.

[0217] The molecular weight of the target product P1-EX4 is 1859.

[0218] The viscosity (100℃) of the target product P1-EX4 is 1047 cps.

[0219] Example 5

[0220] Raw material 5-1:

[0221] Raw material 5-2:

[0222] In a 2L round-bottom flask, 154.7g of raw material 5-1 was dissolved in 600mL of xylene, 0.5mol of NaOMe was added, the temperature was controlled at 25℃, and then 103.5g of raw material 5-2 was slowly added dropwise. The mixture was stirred continuously for 2h. After the reaction was complete, 203g of the target product P1-EX5 was obtained.

[0223] The molecular weight of the target product P1-EX5 is 2065.

[0224] Viscosity of target product P1-EX5: 1683 cps (100℃).

[0225] Example 6

[0226] Raw material 6-1:

[0227] Raw material 6-2:

[0228] In a 2L round-bottom flask, 213g of raw material 6-1 was dissolved in 500mL of xylene, 0.5mol of NaOMe was added, the temperature was controlled at 30℃, and then 376g of raw material 6-2 was slowly added dropwise. The mixture was stirred continuously for 2h. After the reaction was complete, 541g of the target product P1-EX6 was obtained.

[0229] The molecular weight of the target product P1-EX6 is 2356.

[0230] Viscosity of target product P1-EX6: 1463 cps (100℃).

[0231] Example 7

[0232] Ingredient 7-1:

[0233] Raw material 7-2:

[0234] In a 2L round-bottom flask, 9.167g of raw material 7-1 was dissolved in 400mL of xylene, 0.04mol of NaOMe was added, the temperature was controlled at 30℃, and then 446g of raw material 7-2 was slowly added dropwise. The mixture was stirred continuously for 1h, and the reaction was completed to obtain 426g of the target product P1-EX7.

[0235] The molecular weight of the target product P1-EX7 is 18238.

[0236] Viscosity of target product P1-EX7: 1596 cps (100℃).

[0237] Example 8

[0238] Raw material 8-1:

[0239] Raw material 8-2:

[0240] In a 2L round-bottom flask, 113g of raw material 8-1 was dissolved in 300mL of benzene, 0.4mol of NaOMe was added, the temperature was controlled at 30℃, and then 486g of raw material 8-2 was slowly added dropwise. The mixture was stirred continuously for 1h, and the reaction was completed to obtain 516g of the target product P1-EX8.

[0241] The molecular weight of the target product P1-EX8 is 2402.

[0242] Viscosity of target product P1-EX8: 682 cps (100℃).

[0243] Example 9

[0244] Raw material 9-1

[0245] Raw material 9-2:

[0246] In a 2L round-bottom flask, 141.7g of raw material 9-1 was dissolved in 400mL of benzene, 0.5mol of NaOMe was added, the temperature was controlled at 30℃, and then 136g of raw material 9-2 was slowly added dropwise. The mixture was stirred continuously for 1h. After the reaction was complete, 246g of the target product P1-EX9 was obtained.

[0247] The molecular weight of the target product P1-EX9 is 1678.3.

[0248] Viscosity of target product P1-EX9: 1069 cps (100℃).

[0249] Example 10

[0250] Raw material 10-1:

[0251] Raw material 10-2:

[0252] In a 2L round-bottom flask, 197.5g of raw material 10-1 was dissolved in 400mL of benzene, 0.5mol of NaOMe was added, the temperature was controlled at 30℃, and then 319.5g of raw material 10-2 was slowly added dropwise. The mixture was stirred continuously for 1h. After the reaction was complete, 482g of the target product P1-EX10 was obtained.

[0253] The molecular weight of the target product P1-EX10 is 1033.

[0254] Viscosity of target product P1-EX10: 645 cps (100℃).

[0255] Example 11

[0256] Raw material 11-1:

[0257] Raw material 11-2:

[0258] In a 2L round-bottom flask, 85g of raw material 11-1 was dissolved in 400mL of water, and the temperature was controlled at 30℃. Then, 391g of raw material 11-2 was slowly added dropwise, and the mixture was stirred continuously for 2 hours. After the reaction was complete, 482g of the target product P1-EX11 was obtained.

[0259] The molecular weight of the target product P1-EX11 is 1702.

[0260] Viscosity of target product P1-EX11: 1036 cps (100℃).

[0261] Example 12

[0262] Raw material 12-1:

[0263] Raw material 12-2:

[0264] In a 2L round-bottom flask, 241g of raw material 12-1 was dissolved in 500mL of water and the temperature was controlled at 30℃. Then, 301g of raw material 12-2 was slowly added dropwise and stirred continuously for 3h. After the reaction was complete, 501g of the target product P1-EX12 was obtained.

[0265] The molecular weight of the target product P1-EX12 is 1033.

[0266] Viscosity of target product P1-EX12: 645 cps (100℃).

[0267] Test Example 1:

[0268] (1) Stable coating experiment (1-1) The basic formulation of the stable coating experiment is shown in Table 1.

[0269] Table 1 Standard Formulation

[0270]

[0271] The standard formula consists of the following:

[0272] Example 1 is the standard formulation in Table 1 with 99.7 wt% and 0.3 wt% coating additive P1-EX1; Example 2 is the standard formulation in Table 1 with 99.7 wt% and 0.3 wt% coating additive P1-EX2.

[0273] Example 3 is the standard formulation in Table 1, 99.7 wt%, with 0.3 wt% of coating additive P1-EX3;

[0274] Example 4 is the standard formulation in Table 1, 99.7 wt%, with 0.3 wt% of coating additive P1-EX4;

[0275] Example 5 is the standard formulation in Table 1, 99.7 wt%, with 0.3 wt% of coating additive P1-EX5;

[0276] Example 6 is the standard formulation in Table 1, 99.7 wt%, with 0.3 wt% of coating additive P1-EX6;

[0277] Example 7 is the standard formulation in Table 1, 99.7 wt%, with 0.3 wt% of coating additive P1-EX7;

[0278] Example 8 is the standard formulation in Table 1, 99.7 wt%, with 0.3 wt% of coating additive P1-EX8;

[0279] Example 9 is the standard formulation in Table 1, 99.7 wt%, with 0.3 wt% of coating additive P1-EX9;

[0280] Example 10 is the standard formulation in Table 1, 99.7 wt%, with 0.3 wt% of coating additive P1-EX10;

[0281] Example 11 is the standard formulation in Table 1, 99.7 wt%, with 0.3 wt% of coating additive P1-EX11;

[0282] Example 12 is the standard formulation in Table 1, 99.7 wt%, with 0.3 wt% of coating additive P1-EX12;

[0283] The comparative example is the standard formulation in Table 1, which is 99.7 wt% and contains 0.3 wt% of a commercial wetting agent (Dow Chemical wetting agent model: TERGITOL CA-90).

[0284] (1-2) Preparation of test samples:

[0285] Prepare the raw materials according to the basic formula in Table 1. Add the water-based dispersed polyurethane, dispersant, leveling agent, bactericide, film-forming aid, coating additive, auxiliary agent, water, and half of the defoamer to a container with high-speed stirring. While stirring, add the thickener. After the thickener is completely dispersed, add the nano-silicon carbide and stir it at high speed to disperse it. Quickly transfer the above dispersed liquid to a degassing device. After the bubbles are basically eliminated, transfer it to a low-speed stirring tank. After uniform dispersion, adjust the pH to 8 with a pH adjuster to obtain the coating slurry. The high-speed stirring speed is 1500 r / min, and the low-speed stirring speed is 450 r / min.

[0286] The cross-cut test is based on GB / T9286-1998 Scratch test for paint and varnish films; the pencil hardness test method for paint films is based on GB / T6739-2006 Pencil test for paint and varnish films; the gloss test method for gloss is based on GB / T9754 Determination of 20°, 60° and 85° specular gloss of paint films without metallic pigments; the impact test is based on GB / T48939-2013 Test method for impact resistance of paint films on furniture surfaces; and the solvent resistance test is based on GB / T 23989-2009 Determination of solvent resistance of coatings.

[0287] When applied to coating, the test results are shown in Table 2:

[0288] Table 2. Physical property test results of samples from Examples 1-12 and the comparative examples.

[0289]

[0290]

[0291] (2) Coating aging test

[0292] Based on the coating samples in the test samples in (1-2) of the stabilized coating experiment mentioned above, the samples were subjected to xenon lamp aging test according to standard GB / T 16422.2-2014. The test results of ΔE* (lower value required) of the samples after xenon lamp aging are shown in Table 3.

[0293] Table 3

[0294]

[0295] The experimental results in Tables 2 and 3 show that the hardness, gloss, impact resistance, and solvent resistance of the film surface with the coating additives of this invention are comparable to those with commercial additives. However, the coating additives of this invention have stronger weather resistance than commercial additives and possess good anti-aging properties.

[0296] The preferred embodiments of the present invention have been described in detail above; however, the present invention is not limited thereto. Within the scope of the inventive concept, various simple modifications can be made to the technical solutions of the present invention, including combinations of various technical features in any other suitable manner. These simple modifications and combinations should also be considered as the content disclosed in the present invention and are all within the protection scope of the present invention.

[0297] The foregoing embodiments and methods described in this invention may vary based on the capabilities, experience, and preferences of those skilled in the art.

[0298] Listing the steps of the method in a certain order in this invention does not constitute any restriction on the order of the method steps.

Claims

1. A coating additive, characterized in that, The coating additive is prepared by polymerization of a polyether derivative backbone and at least one compound having the general formula A; The general formula A has the following structure: General formula A; Among them, R a Selected from hydrogen, -alkyl, -alkylene, -OH, -OR b ,-alkylene-OR b Alkyl groups separated by one or more heteroatoms; alkyl groups separated by one or more first spacer groups alone or in combination; alkyl groups substituted with one or more first substituents; heteroalkyl groups substituted with one or more first substituents. The first spacer group is selected from one or more combinations of the following groups: -C(=O)O-, amino group, -OC(=O)O-, amide group, aryl group, heteroalkyl group, heteroaryl group; The first substituent is selected from hydroxyl, aryl, cycloalkyl, hydroxyalkyl, alkoxy, amino, heteroaryl, heterocycloalkyl, alkoxycarbonyl, aryloxycarbonyl, heteroaryloxycarbonyl, heteroalkoxycarbonyl, acyloxy, alkanoyloxy, aryloxy, heteroaryloxy, cycloalkanoyloxy, heteroalkanoyloxy, alkanoyl, aminoacyl, alkylaminoacyl, aryl, alkyl separated by one or more heteroatoms, alkyl separated by one or more -C(=O)O-, alkyl separated by one or more -OC(=O)O-, alkyl separated by one or more -C(=O)-, alkyl separated by one or more amide groups, alkyl separated by one or more arylene groups, alkyl separated by one or more amino groups, alkyl separated by one or more heteroalkyl groups, and alkyl separated by one or more heteroaryl groups. p is The degree of aggregation of the repeating unit, where p is 0 or 1; The o is The degree of aggregation of repeating units, where o is an integer from 1 to 15; The R b Selected from one or more of the following groups: alkyl, cycloalkyl, -C(=O)R c Heterocyclic alkyl, alkyl spaced by one or more heteroatoms, alkyl spaced by one or more first spacer groups alone or in combination, alkyl substituted by one or more first substituents, heteroalkyl substituted by one or more first substituents, cycloalkyl substituted by one or more first substituents, -phenyl; The R c The group is selected from one or more of the following groups: alkyl, cycloalkyl, phenyl, heterocycloalkyl, alkyl separated by one or more heteroatoms, alkyl separated by one or more first spacer groups alone or in combination, alkyl substituted by one or more first substituents, heteroalkyl substituted by one or more first substituents, and cycloalkyl substituted by one or more first substituents. The polyether derivative skeleton includes compounds of general formula B; The general formula B has the following structure: General formula B; in, n1, n2, ..., n m The degree of aggregation of each repeating unit is an integer between 0 and 200; The n1+n2+……+n m ≥1; m is an integer from 1 to 20; R1, R2, R3...R m The same or different substituents; Rt1 and Rt2 are the same or different end-capping groups; The R1, R2, R3...R m The independent group is selected from one or more combinations of the following groups: hydrogen, alkyl, cycloalkyl, heterocycloalkyl, phenyl, alkyl separated by one or more heteroatoms, alkyl separated by one or more alkenyl groups, alkyl separated by one or more alkynyl groups, alkyl separated by one or more arylene groups, alkyl separated by one or more heteroalkyl groups, alkyl separated by one or more heteroarylene groups, alkyl separated by a combination of the above spacer groups, alkyl substituted with one or more second substituents, heteroalkyl substituted with one or more second substituents, cycloalkyl substituted with one or more second substituents, or -benzene ring; The second substituent is selected from one or more of the following groups in combination: hydroxyl, aryl, cycloalkyl, hydroxyalkyl, alkoxy, heteroaryl, heterocycloalkyl, alkyl separated by one or more heteroatoms, alkyl separated by one or more arylene groups, alkyl separated by one or more alkenyl groups, alkyl separated by one or more alkynyl groups, alkyl separated by one or more heteroalkyl groups, alkyl separated by one or more heteroalkyl groups, alkyl separated by one or more heteroaryl groups, and alkyl separated by a combination of the above spacer groups. Rt1 and Rt2 are independently selected from one or more combinations of the following groups: hydrogen, alkyl, cycloalkyl, heterocycloalkyl, phenyl, alkyl separated by one or more heteroatoms, alkyl separated by one or more -C(=O)O-, alkyl separated by one or more -OC(=O)O-, alkyl separated by one or more alkenyl groups, alkyl separated by one or more alkynyl groups, alkyl separated by one or more amide groups, alkyl separated by one or more arylene groups, alkyl separated by one or more heteroalkylene groups, alkyl separated by one or more heteroalkylene groups, alkyl separated by one or more heteroarylene groups, alkyl separated by a combination of the above spacer groups, alkyl substituted with one or more third substituents, heteroalkyl substituted with one or more third substituents, and cycloalkyl substituted with one or more third substituents. The third substituent is selected from one or more combinations of the following groups: hydroxyl, aryl, cycloalkyl, hydroxyalkyl, alkoxy, amino, heteroaryl, heterocycloalkyl, alkoxycarbonyl, aryloxycarbonyl, heteroaryloxycarbonyl, heteroalkoxycarbonyl, acyloxy, alkanoyloxy, cycloalkanoyloxy, heteroalkanoyloxy, alkanoyl, alkyl separated by one or more heteroatoms, alkyl separated by one or more -C(=O)O-, alkyl separated by one or more -OC(=O)O-, alkyl separated by one or more -C(=O)-, alkyl separated by one or more amide groups, alkyl separated by one or more arylene groups, alkyl separated by one or more alkenyl groups, alkyl separated by one or more alkynyl groups, alkyl separated by one or more amino groups, alkyl separated by one or more heteroalkylene groups, alkyl separated by one or more heteroaryl groups, and alkyl separated by a combination of the above spacer groups.

2. The coating additive according to claim 1, wherein, The o is The degree of aggregation of repeating units, where o is an integer from 1 to 11.

3. The coating additive according to claim 1, wherein, The general formula A includes the following structure: Where i is an integer from 1 to 18.

4. The coating additive according to claim 1, wherein, In the general formula B, ------ represents one or more identical or different ones. And / or, ------ represents a single key.

5. The coating additive according to claim 1, wherein, The general formula B is selected from the following structures:

6. A method for preparing the coating additive according to any one of claims 1-5, characterized in that, The method involves a polymerization reaction between a compound of general formula A and a compound of general formula B; the polymerization reaction is carried out in the presence of a catalyst.

7. The method according to claim 6, wherein, The polymerization reaction is carried out in a solvent selected from one or more of the following: tetrahydrofuran, 2-methyltetrahydrofuran, halogenated hydrocarbons, acetonitrile, propionitrile, butyronitrile, aromatic hydrocarbons, aliphatic hydrocarbons, alcohols, dimethyl sulfoxide, N,N-dimethylamide and diphenyl ether, and water.

8. The method according to claim 7, wherein, The halogenated hydrocarbons include one or more of dichloromethane, dichloroethane, or carbon tetrachloride.

9. The method according to claim 7, wherein, The aromatic hydrocarbons include one or more of benzene, toluene, xylene, chlorobenzene, or dichlorotoluene.

10. The method according to claim 7, wherein, The aliphatic hydrocarbons include one or more of the following: petroleum ether, n-hexane, n-heptane, cyclohexane, and n-octane.

11. The method according to claim 7, wherein, The alcohols include one or more of methanol, ethanol, propanol, ethylene glycol, diethylene glycol, and ethylene glycol methyl ether.

12. The method according to claim 7, wherein, The solvent is selected from one or more of water, toluene, benzene, chlorobenzene, xylene, cyclohexane, n-heptane, or dichloromethane.

13. The method according to claim 7, wherein, The solvent is selected from one or more combinations of water, benzene, xylene, or chlorobenzene.

14. The method according to claim 6, wherein, The catalyst is an alkaline catalyst.

15. The method according to claim 14, wherein, The alkaline catalyst is selected from one or more combinations of the following: K2CO3, KOH, NaH, NaOMe, KO T Bu, rhodium complexes, ruthenium complexes, clay-supported nickel bromide, or ionic liquids.

16. The method according to claim 6, wherein, The molar ratio of the catalyst to the compound of general formula A is (1:0.5) to (1:2).

17. The method according to claim 6, wherein, The polymerization reaction is a Michael addition reaction.

18. The method according to claim 6, wherein, The polymerization reaction temperature is 0-150℃.

19. The method according to claim 18, wherein, The polymerization reaction is carried out at a temperature of 0-80℃.

20. The method according to claim 19, wherein, The polymerization reaction is carried out at a temperature of 0-40℃.

21. A composition, characterized in that, The composition comprises the coating additive as described in any one of claims 1-5, and one or more organic substances sensitive to light, heat or oxidation; or, the coating additive prepared by the method described in any one of claims 6-20, and one or more organic substances sensitive to light, heat or oxidation.

22. The composition according to claim 21, wherein, The amount of the coating additive is 0.01-5 wt% of the standard formulation weight, which is the total weight of the composition.

23. The application of a coating additive according to any one of claims 1-5 or the composition according to claim 21 or 22 in the preparation of light stabilizers, the preparation of wetting agents, and on the surface of articles.

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