CN110938392B - Silicone adhesive anti-yellowing agent and preparation method thereof - Google Patents

Silicone adhesive anti-yellowing agent and preparation method thereof Download PDF

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CN110938392B
CN110938392B CN201911276643.8A CN201911276643A CN110938392B CN 110938392 B CN110938392 B CN 110938392B CN 201911276643 A CN201911276643 A CN 201911276643A CN 110938392 B CN110938392 B CN 110938392B
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silicone adhesive
yellowing
agent
aqueous solution
yellowing agent
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CN110938392A (en
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刘正辉
王长杰
杨丽芳
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Guangzhou Xinyue New Material Technology Co ltd
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    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • C09J11/00—Features of adhesives not provided for in group C09J9/00, e.g. additives
    • C09J11/02—Non-macromolecular additives
    • C09J11/04—Non-macromolecular additives inorganic
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09C—TREATMENT OF INORGANIC MATERIALS, OTHER THAN FIBROUS FILLERS, TO ENHANCE THEIR PIGMENTING OR FILLING PROPERTIES ; PREPARATION OF CARBON BLACK  ; PREPARATION OF INORGANIC MATERIALS WHICH ARE NO SINGLE CHEMICAL COMPOUNDS AND WHICH ARE MAINLY USED AS PIGMENTS OR FILLERS
    • C09C1/00—Treatment of specific inorganic materials other than fibrous fillers; Preparation of carbon black
    • C09C1/28—Compounds of silicon
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09C—TREATMENT OF INORGANIC MATERIALS, OTHER THAN FIBROUS FILLERS, TO ENHANCE THEIR PIGMENTING OR FILLING PROPERTIES ; PREPARATION OF CARBON BLACK  ; PREPARATION OF INORGANIC MATERIALS WHICH ARE NO SINGLE CHEMICAL COMPOUNDS AND WHICH ARE MAINLY USED AS PIGMENTS OR FILLERS
    • C09C3/00—Treatment in general of inorganic materials, other than fibrous fillers, to enhance their pigmenting or filling properties
    • C09C3/08—Treatment with low-molecular-weight non-polymer organic compounds
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • C09J11/00—Features of adhesives not provided for in group C09J9/00, e.g. additives
    • C09J11/02—Non-macromolecular additives
    • C09J11/06—Non-macromolecular additives organic
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • C09J183/00—Adhesives based on macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon, with or without sulfur, nitrogen, oxygen, or carbon only; Adhesives based on derivatives of such polymers
    • C09J183/04—Polysiloxanes
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L2201/00—Properties
    • C08L2201/08—Stabilised against heat, light or radiation or oxydation

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  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Inorganic Chemistry (AREA)
  • Adhesives Or Adhesive Processes (AREA)

Abstract

The invention belongs to the field of organic silicon additives, and discloses a silicone adhesive anti-yellowing agent and a preparation method thereof. The silicone adhesive anti-yellowing agent has a chemical structure shown in a formula (I). The silicon white carbon black can be prepared in an organic solvent or a water phase, a fluorescent whitening structure is chemically grafted to the silicon white by adopting a silane coupling agent, and the silicon white carbon black is used as a silicon-based material, so that the silicon white carbon black has excellent compatibility in a silicone product, and the dispersion performance of an anti-yellowing agent in the silicone adhesive product can be remarkably improved. The white carbon black can be used as a filler component of the silicone adhesive, and the silicone adhesive anti-yellowing agent can play a role in reinforcing and anti-yellowing agents at the same time.
Figure DDA0002315734760000011

Description

Silicone adhesive anti-yellowing agent and preparation method thereof
Technical Field
The invention relates to the field of organic silicon additives, and particularly relates to a silicone adhesive anti-yellowing agent and a preparation method thereof.
Background
The silicone adhesive has the characteristics of strong bonding force, high tensile strength, weather resistance, vibration resistance, moisture resistance, odor resistance and large adaptability to cold and heat changes. In addition, the wide applicability of the adhesive can realize the adhesion among most building material products, so the application value is very high. However, after the silicone adhesive is used for a long time, for example, after long-time sunlight irradiation or when the silicone adhesive is mildewed, the silicone adhesive is easy to have a yellowing phenomenon, and particularly when the silicone adhesive is used in hot and humid coastal areas, the yellowing phenomenon is more serious, and the attractiveness is greatly influenced. Therefore, how to improve the yellowing resistance of silicone adhesive is a technical problem to be solved by those skilled in the art.
Patent 201410510343.2 discloses an acidic transparent silicone weather-resistant sealant for construction, which is composed of hydroxy-terminated polydimethylsiloxane, methyl-terminated polydimethylsiloxane, fumed silica, a cross-linking agent, a catalyst and a composite anti-yellowing agent. The patent utilizes the synergistic effect of a compound anti-yellowing agent of 2, 3-dihydroxy-4-n-decyloxy benzophenone and tris (1,2,2,6, 6-pentamethylpiperidinyl) phosphite to widen the wavelength of the absorbed light of the benzophenone ultraviolet absorbent, improve the conversion efficiency from amido to nitryl free radical and further integrally improve the weather resistance (anti-yellowing) of the sealant.
Patent 200910066244.9 discloses a neutral transparent silicone sealant, which is composed of hydroxyl-terminated polydimethylsiloxane, plasticizer, cross-linking agent, coupling agent, catalyst, silicon dioxide and anti-yellowing agent. The anti-yellowing agent is at least one of an ultraviolet absorbent, an antioxidant or a light stabilizer. Patent 201010557084.0 also discloses a technical solution of adding an anti-yellowing agent such as an ultraviolet absorber and a light stabilizer to control the yellowing of silicone adhesive.
Patent 201510946060.7 discloses an anti-fatigue, anti-ultraviolet single-component dealcoholized silicone sealant and its preparation method, which comprises hydroxyl-terminated polydimethylsiloxane, reinforcing filler, plasticizer, bimetallic aluminum-zirconium coupling agent, catalyst and deep curing agent. The principle is still to achieve the purpose of anti-yellowing by improving the anti-fatigue and anti-ultraviolet performance of the material.
Patent 201410029398.1 discloses a single-component mildew-proof transparent dealcoholized silicone sealant and a preparation method thereof, which is prepared by adding an organic arsenic compound mildew preventive taking polyether polyol as a carrier on the basis of the transparent dealcoholized silicone sealant, and has the advantages of excellent mildew-proof effect, low smell, yellowing resistance and rapid deep curing while not influencing the transparency, manufacturability and storage stability of the transparent dealcoholized silicone sealant.
In the prior art, the purpose of yellowing resistance is achieved by adding additives with ultraviolet resistance, oxidation resistance and fatigue resistance or adding light stabilizers and mildewproof agents. However, the additives have poor compatibility with the silicone gum base and poor dispersibility.
The fluorescent whitening agent (fluorescent brightener) is a fluorescent dye, has high light quantum yield, and can effectively whiten and brighten a treated substrate. Fluorescent whitening agent molecules have a large conjugated system, can absorb ultraviolet light with the wavelength range of about 300-400 nm and emit blue fluorescent light with the wavelength range of about 420-450 nm, so that visual yellowing caused by blue light deficiency in a matrix is compensated. People feel brighter and brighter substrates treated by compensating blue light. Fluorescent whitening agents are widely used in many fields such as paper making, textiles, detergents, plastics, inks, leather, ultraviolet absorbers, developers and the like, and the market demand is huge. But currently, there are few reports of application to silicone adhesives.
Patent 201610987718.3 discloses a process for the preparation of a matte silicone gel comprising a polydiorganosiloxane containing active segments, a plasticizer, a filler, a pigment, a fluorescent whitening agent and a matte agent. The fluorescent whitening agent is one or a mixture of OB, KWN and KSN. However, the purpose of the fluorescent whitening agent incorporated in this patent is to make the silicone sealant fluorescent, and the problem of dispersion of the fluorescent whitening agent in the silicone adhesive matrix is not solved either.
Disclosure of Invention
The invention aims to provide a silicone adhesive anti-yellowing agent, which solves the yellowing problem of silicone adhesive by using the optical principle of a conjugated system in a fluorescent brightener for the first time; and simultaneously solves the problem of dispersibility in silicone adhesive.
In order to achieve the purpose, the invention provides the following technical scheme:
a silicone adhesive anti-yellowing agent has a chemical structure as shown in the following:
Figure BDA0002315734740000031
wherein X is Na or K, L is a silane coupling agent connecting group,
Figure BDA0002315734740000032
refers to white carbon black.
Further, L refers to an aminosilane coupling agent linking group.
The preparation method of the silicone adhesive anti-yellowing agent comprises the following steps:
(1) dissolving or dispersing 4,4 '-diaminostilbene-2, 2' -disulfonic acid (DSD acid) in an organic solvent, then adding cyanuric chloride, stirring and dissolving uniformly, adding a sodium ethoxide or potassium ethoxide solution for neutralization, and stirring and reacting at the temperature of 10-30 ℃;
(2) adding an aminosilane coupling agent into the reaction mixture obtained in the step (1), heating to 30-80 ℃, and continuing stirring for reaction;
(3) and (3) adding white carbon black into the reaction mixture obtained in the step (2), stirring and mixing uniformly, then dropwise adding a sodium carbonate or potassium carbonate aqueous solution for coupling reaction, and drying the product to remove the solvent to obtain the silicone adhesive anti-yellowing agent.
Further, the organic solvent in the step (1) refers to ethanol or diethyl ether.
The preparation method of the silicone adhesive anti-yellowing agent comprises the following steps:
(1) dissolving 4,4 '-diaminostilbene-2, 2' -disulfonic acid (DSD acid) in Na2CO3Or K2CO3Adding cyanuric chloride into the aqueous solution, and adding Na2CO3Or K2CO3Maintaining the pH value of the system to be 3-4 by using an aqueous solution, and stirring and reacting at the temperature of 0-5 ℃;
(2) adding the white carbon black into an isopropanol aqueous solution for uniform dispersion, then adding an aminosilane coupling agent for modification reaction, and separating and drying a solid product to obtain surface modified white carbon black;
(3) adding the surface modified white carbon black obtained in the step (2) into the reaction system in the step (1), and adding Na2CO3Or K2CO3And (3) maintaining the pH value of the system to be 6-7 by using an aqueous solution, stirring and reacting at the temperature of 30-50 ℃, and separating and drying a solid product to obtain the silicone adhesive anti-yellowing agent.
Further, in the two preparation methods, the molar ratio of the DSD acid to the cyanuric chloride is 1: 1.8-2.2.
Further, in the above two preparation methods, the aminosilane coupling agent is selected from at least one of 3-aminopropyltriethoxysilane, 3-aminopropyltrimethoxysilane and N- (beta-aminoethyl) -gamma-aminopropyltriethoxysilane.
Furthermore, in the two preparation methods, the addition amount of the aminosilane coupling agent is 0.1-10% of the mass of the DSD acid.
Further, in the two preparation methods, the addition amount of the DSD acid is 1-10% of the mass of the white carbon black.
Further, in the two preparation methods, the white carbon black refers to fumed silica.
Compared with the prior art, the invention has the beneficial effects that:
(1) the silicone adhesive anti-yellowing agent disclosed by the invention contains a fluorescent whitening conjugated structure, can absorb ultraviolet light with the wavelength range of about 300-400 nm and emit blue fluorescence with the wavelength range of about 420-450 nm, so that the visual yellowing caused by blue light deficiency in a matrix is compensated, and the anti-yellowing performance of a base material is improved on the optical principle.
(2) According to the invention, the silane coupling agent is adopted to chemically graft the fluorescent whitening structure on the white carbon black, and the white carbon black is used as a silicon-based material, so that the silicon-based material has excellent compatibility in a silicone product, and the dispersion performance of the anti-yellowing agent in the silicone adhesive product can be obviously improved.
(3) The white carbon black can be used as a filler component of the silicone adhesive, and the silicone adhesive anti-yellowing agent can play a role in reinforcing and anti-yellowing agents at the same time.
(4) The preparation method is simple, can be carried out in aqueous solution or organic solvent, and has good industrial application prospect.
Drawings
FIG. 1 is a synthetic scheme of the anti-yellowing agent for silicone adhesive of example 5 of the present invention;
FIG. 2 is a fluorescence spectrum of the anti-yellowing agent for silicone adhesive obtained in examples 1 and 5 of the present invention.
Detailed Description
Specific embodiments of the present invention will be described in further detail below with reference to examples and drawings, but the present invention is not limited thereto. All other embodiments, which can be derived by a person skilled in the art from the embodiments given herein without making any creative effort, shall fall within the protection scope of the present invention.
Example 1
The preparation method of the silicone adhesive anti-yellowing agent of the embodiment includes the following steps:
(1) dissolving 4,4 '-diaminostilbene-2, 2' -disulfonic acid (DSD acid) in 300ml of ethanol, then adding 36.9g of cyanuric chloride, stirring and dissolving uniformly, adding sodium ethoxide solution for neutralization, and stirring and reacting at the temperature of 10 ℃ for 2 hours;
(2) adding 0.37g of aminosilane coupling agent 3-aminopropyltriethoxysilane (KH-550) into the reaction mixture obtained in the step (1), heating to 30 ℃, and continuously stirring for reaction for 6 hours;
(3) 740g of fumed silica is added into the reaction mixture obtained in the step (2) and is stirred and mixed uniformly, then a sodium carbonate aqueous solution is dripped to carry out coupling reaction, and the product is dried to remove the solvent, so that the silicone adhesive anti-yellowing agent is obtained.
Example 2
(1) Dissolving 4,4 '-diaminostilbene-2, 2' -disulfonic acid (DSD acid) in 200ml of ethanol, adding 36.9g of cyanuric chloride, stirring and dissolving uniformly, adding sodium ethoxide solution for neutralization, and stirring and reacting at the temperature of 20 ℃ for 2 hours;
(2) adding 0.37g of aminosilane coupling agent N- (beta-aminoethyl) -gamma-aminopropyl triethoxysilane (KH-792) into the reaction mixture in the step (1), heating to 40 ℃, and continuously stirring for reaction for 6 hours;
(3) and (3) adding 370g of fumed silica into the reaction mixture obtained in the step (2), uniformly stirring and mixing, then dropwise adding a sodium carbonate aqueous solution for coupling reaction, and drying the product to remove the solvent to obtain the silicone adhesive anti-yellowing agent.
Example 3
(1) Dissolving 4,4 '-diaminostilbene-2, 2' -disulfonic acid (DSD acid) in 200ml of diethyl ether, adding 36.9g of cyanuric chloride, stirring and dissolving uniformly, adding a potassium ethylate solution for neutralization, and stirring and reacting at the temperature of 30 ℃ for 2 hours;
(2) adding 0.74g of aminosilane coupling agent 3-aminopropyltrimethoxysilane (KH-540) into the reaction mixture obtained in the step (1), heating to 50 ℃, and continuously stirring for reacting for 6 hours;
(3) and (3) adding 1110g of fumed silica into the reaction mixture obtained in the step (2), uniformly stirring and mixing, then dropwise adding a potassium carbonate aqueous solution for coupling reaction, and drying the product to remove the solvent to obtain the silicone adhesive anti-yellowing agent.
Example 4
(1) Dissolving 4,4 '-diaminostilbene-2, 2' -disulfonic acid (DSD acid) in 500ml of ethanol, then adding 40g of cyanuric chloride, stirring and dissolving uniformly, adding sodium ethoxide solution for neutralization, and stirring and reacting at the temperature of 20 ℃ for 2 hours;
(2) adding 1.85g of aminosilane coupling agent 3-aminopropyltriethoxysilane (KH-550) into the reaction mixture obtained in the step (1), heating to 60 ℃, and continuously stirring for reaction for 6 hours;
(3) and (3) adding 1000g of fumed silica into the reaction mixture obtained in the step (2), uniformly stirring and mixing, then dropwise adding a potassium carbonate aqueous solution for coupling reaction, and drying the product to remove the solvent to obtain the silicone adhesive anti-yellowing agent.
Example 5
(1) 37g of 4,4 '-diaminostilbene-2, 2' -disulfonic acid (DSD acid) were dissolved in 500ml of Na2CO3To the aqueous solution, 36.9g of cyanuric chloride are then added, over Na2CO3The pH value of the water solution maintaining system is 3, and the stirring reaction is carried out for 2h under the ice-water bath condition;
(2) 370g of fumed silica is added into 1000ml of isopropanol aqueous solution for uniform dispersion, then 1.85g of aminosilane coupling agent 3-aminopropyltriethoxysilane (KH-550) is added for modification reaction, and the solid product is separated and dried to obtain surface modified silica;
(3) adding the surface modified white carbon black obtained in the step (2) into the reaction system in the step (1), and adding Na2CO3And (3) maintaining the pH value of the system to be 6 by using the aqueous solution, stirring and reacting at the temperature of 50 ℃, and performing suction filtration, separation and drying on the solid product to obtain the silicone adhesive anti-yellowing agent.
The synthetic route of the silicone adhesive anti-yellowing agent of the embodiment is shown in fig. 1.
Example 6
(1) 37g of 4,4 '-diaminostilbene-2, 2' -disulfonic acid (DSD acid) were dissolved in 500ml of Na2CO3To the aqueous solution, 33.5g of cyanuric chloride are then added, over Na2CO3The pH value of the water solution maintaining system is 4, and the stirring reaction is carried out for 2h under the ice-water bath condition;
(2) 740g of fumed silica is added into 2000ml of isopropanol water solution for uniform dispersion, then 1g of aminosilane coupling agent 3-aminopropyltrimethoxysilane (KH-540) is added for modification reaction, and the solid product is separated and dried to obtain surface modified silica;
(3) adding the surface modified white carbon black obtained in the step (2) into the reaction system in the step (1), and adding Na2CO3And (3) maintaining the pH value of the system to be 7 by using the aqueous solution, stirring and reacting at the temperature of 40 ℃, and performing suction filtration, separation and drying on the solid product to obtain the silicone adhesive anti-yellowing agent.
Example 7
(1) 37g of 4,4 '-diaminostilbene-2, 2' -disulfonic acid (DSD acid) were dissolved in 1000ml of Na2CO3To the aqueous solution, 37g of cyanuric chloride are then added, over Na2CO3The pH value of the system is maintained to be 4 by the aqueous solution, and the stirring reaction is carried out for 2 hours at the temperature of 4 ℃;
(2) 740g of fumed silica is added into 2000ml of isopropanol water solution for uniform dispersion, then 2g of aminosilane coupling agent N- (beta-aminoethyl) -gamma-aminopropyltriethoxysilane (KH-792) is added for modification reaction, and the solid product is separated and dried to obtain surface modified silica;
(3) adding the surface modified white carbon black obtained in the step (2) into the reaction system in the step (1), and adding Na2CO3And (3) maintaining the pH value of the system to be 7 by using the aqueous solution, stirring and reacting at the temperature of 40 ℃, and performing suction filtration, separation and drying on the solid product to obtain the silicone adhesive anti-yellowing agent.
Example 8
(1) 37g of 4,4 '-diaminostilbene-2, 2' -disulfonic acid (DSD acid) were dissolved in 1000ml of Na2CO3To the aqueous solution, 40g of cyanuric chloride are then added, using K2CO3The pH value of the water solution maintaining system is 3, and the stirring reaction is carried out for 2h at the temperature of 4 ℃;
(2) adding 800g of fumed silica into 1500ml of isopropanol aqueous solution for uniform dispersion, then adding 1.5g of aminosilane coupling agent 3-aminopropyltriethoxysilane (KH-550) for modification reaction, and separating and drying a solid product to obtain surface modified silica;
(3) adding the surface modified white carbon black obtained in the step (2) into the reaction system in the step (1), and using K2CO3And (3) maintaining the pH value of the system to be 7 by using the aqueous solution, stirring and reacting at the temperature of 40 ℃, and performing suction filtration, separation and drying on the solid product to obtain the silicone adhesive anti-yellowing agent.
The fluorescence spectra of the anti-yellowing agents for silicone adhesive obtained in examples 1 and 5 are shown in FIG. 2. As can be seen from the results of FIG. 2, the silicone adhesive anti-yellowing agents prepared by the two methods of the present invention can emit blue fluorescence with a wavelength range of about 440 nm.

Claims (1)

1. The application of the silicone adhesive anti-yellowing agent in the silicone adhesive is characterized in that the silicone adhesive anti-yellowing agent has a chemical structure as shown in the following:
Figure DEST_PATH_IMAGE001
wherein X is Na or K, L is an aminosilane coupling agent linking group,
Figure 940609DEST_PATH_IMAGE002
refers to fumed silica;
the silicone adhesive anti-yellowing agent is prepared by the following steps:
(1) dissolving DSD acid in Na2CO3Or K2CO3Adding cyanuric chloride into the aqueous solution, and adding Na2CO3Or K2CO3Maintaining the pH value of the system to be 3-4 by using an aqueous solution, and stirring and reacting at the temperature of 0-5 ℃;
(2) adding the fumed silica into an isopropanol aqueous solution for uniform dispersion, then adding an aminosilane coupling agent for modification reaction, and separating and drying a solid product to obtain surface modified silica;
(3) adding the surface modified white carbon black obtained in the step (2) into the reaction system in the step (1), and adding Na2CO3Or K2CO3Maintaining the pH value of the system to be 6-7 by using an aqueous solution, stirring and reacting at the temperature of 30-50 ℃, and separating and drying a solid product to obtain the silicone adhesive anti-yellowing agent;
the mol ratio of the DSD acid to the cyanuric chloride is 1: 1.8-2.2;
the aminosilane coupling agent is selected from at least one of 3-aminopropyltriethoxysilane, 3-aminopropyltrimethoxysilane and N- (beta-aminoethyl) -gamma-aminopropyltriethoxysilane; the addition amount of the aminosilane coupling agent is 0.1-10% of the mass of the DSD acid;
the addition amount of the DSD acid is 1-10% of the mass of the fumed silica.
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