CN111154091A - Vinyl polyether surfactant, preparation method and application thereof, and LED packaging material - Google Patents
Vinyl polyether surfactant, preparation method and application thereof, and LED packaging material Download PDFInfo
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- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
- C08G65/02—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
- C08G65/26—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers and other compounds
- C08G65/2639—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers and other compounds the other compounds containing elements other than oxygen, nitrogen or sulfur
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- 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
- C09J11/08—Macromolecular additives
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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
- 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
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- C08L2203/00—Applications
- C08L2203/20—Applications use in electrical or conductive gadgets
- C08L2203/206—Applications use in electrical or conductive gadgets use in coating or encapsulating of electronic parts
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Abstract
The invention relates to the field of LED packaging, and discloses a vinyl polyether surfactant, a preparation method and application thereof, and an LED packaging material. The invention takes vinyl silane as a main body, and introduces polyether chain segments into the side groups of the vinyl silane to obtain the vinyl polyether surfactant. When the vinyl polyether surfactant disclosed by the invention is used as a leveling agent and is matched with an LED packaging adhesive for use, the surface tension of the adhesive can be reduced, and the leveling performance is obviously improved.
Description
Technical Field
The invention relates to the field of LED packaging, in particular to a vinyl polyether surfactant, a preparation method and application thereof and an LED packaging material.
Background
A Light Emitting Diode (LED) is a solid state semiconductor device that can directly convert electrical energy into light energy. The LED illuminating lamp has the characteristics of low energy consumption, small volume, long service life and the like, and can replace traditional light sources such as incandescent lamps, fluorescent lamps and the like to become a fourth-generation illuminating light source. The heart of the LED illuminating lamp is a semiconductor wafer (lamp bead), one end of the semiconductor wafer is attached to the support and is a negative electrode, the other end of the semiconductor wafer is connected with a positive electrode of a power supply, and the whole semiconductor wafer is packaged by epoxy resin or silica gel. In recent years, the LED packaging industry develops rapidly, the epoxy resin is easy to yellow due to the weak ozone resistance of the epoxy resin, the light transmission effect is influenced, and the epoxy resin is replaced by the silica gel material in the application of high-end products due to the excellent performances of atmospheric aging resistance, ultraviolet aging resistance and the like of the silica gel material.
The addition type silica gel has the advantages of no by-product, low curing shrinkage rate, complete curing at high temperature and the like in the curing process, so that the addition type silica gel is widely applied to the field of Light Emitting Diode (LED) packaging. However, the silica gel has too high viscosity, and has the problem of difficult leveling in the packaging process. At present, most packaging plants adopt a preheating method to solve the leveling problem, but the preheating method can cause silica gel curing to a certain extent. In addition, for example, CN106867259A discloses a silicone composition applied to semiconductor encapsulation, which comprises: silicone-based rubbers, silicone resins containing vinyl functional groups, silicone resins containing Si-H functional groups, hydrosilylation catalysts, fluorescent materials, and solvents or diluents. When applied, the silicone composition is applied to a substrate to form a film; removing the solvent and/or the pre-cured composition from the film under heating and/or irradiation to form a pre-cured film that can be lifted and has no surface tack; attaching the pre-cured film to an article; and finally, completely curing the pre-cured film to realize the packaging of the article. The above silicone composition also has the drawback of excessive curing upon heating; therefore, another method is needed to solve the problem of normal-temperature leveling of the glue.
Disclosure of Invention
The invention aims to solve the problem of normal-temperature leveling of the existing LED packaging silica gel, and provides a vinyl polyether surfactant, a preparation method and application thereof, and an LED packaging material.
The invention takes vinyl silane as a main body, and introduces polyether chain segments into the side groups of the vinyl silane to obtain the vinyl polyether surfactant. Furthermore, products with different HLB values (hydrophilic-lipophilic balance values) can be synthesized by controlling the content of each group of the polyether; and the vinyl polyether surfactant can be connected into the LED sealant by a Pt catalyst and utilizing a hydrosilylation reaction, so that the surface tension of the glue and the PCT/PPA/Ag is reduced, and the spreadability of the glue is improved. Therefore, the vinyl polyether surfactant disclosed by the invention is used as a leveling agent to be matched with the LED packaging adhesive, the compatibility of the leveling agent and the LED packaging adhesive is good, and the normal-temperature leveling performance is obviously improved.
The invention provides a vinyl polyether surfactant, which contains at least one of a compound shown in a formula (1), a compound shown in a formula (2) and a compound shown in a formula (3),
wherein R is1Is vinyl or hydrogen, R2、R3Each independently is C1-C10M, n and p are each an integer of 0 to 100, and are not simultaneously 0.
The invention also provides a preparation method of the vinyl polyether surfactant, which comprises the following steps:
(1) subjecting a compound represented by the formula (4) to a hydrolysis reaction in the presence of an acidic catalyst, an organic solvent and water, so that R5、R6And R7At leastHydrolyzing one group to a hydroxyl group to obtain a hydrolysate;
(2) carrying out ring-opening polymerization reaction on the hydrolysate, ethylene oxide and propylene oxide;
wherein R is1Is vinyl or hydrogen, R5、R6、R7Each independently is C1-C10Alkyl or alkoxy groups of (a).
The invention also provides the vinyl polyether surfactant prepared by the method.
The invention also provides application of the vinyl polyether surfactant as a leveling agent.
In addition, the invention also provides an LED packaging material, which contains silica gel and a leveling agent, wherein the leveling agent is the vinyl polyether surfactant.
After intensive research, the inventors of the present invention have found that when a vinyl polyether surfactant having the above-mentioned composition is used as a leveling agent in combination with an LED encapsulating adhesive, the terminal group R in the molecule of the organosilicon compound1Can be connected with LED encapsulation glue molecule, the other end can reduce the surface tension of glue with support substrate effect, improves the levelling performance, and can reduce the surface tension of encapsulation glue half, glue when becoming 0S with T reduces to 68 from 110 with LED support substrate' S contact angle, and the levelling is showing and is improving.
Additional features and advantages of the invention will be set forth in the detailed description which follows.
Drawings
Fig. 1 is a graph showing the results of a surface tension test of LED encapsulating material G1 prepared in example 6;
fig. 2 is a graph of the contact angle test result of the LED encapsulating material G1 prepared in example 6;
FIG. 3 is a graph showing the results of a surface tension test of the LED encapsulating material G2 prepared in example 7;
fig. 4 is a graph of the contact angle test result of the LED encapsulating material G2 prepared in example 7;
fig. 5 is a graph showing the results of a surface tension test of the LED encapsulating material G3 prepared in example 8;
fig. 6 is a graph of the contact angle test result of the LED encapsulating material G3 prepared in example 8;
fig. 7 is a graph showing the results of a surface tension test of the LED encapsulating material G4 prepared in example 9;
fig. 8 is a graph showing the contact angle test result of the LED encapsulating material G4 prepared in example 9;
fig. 9 is a graph showing the results of a surface tension test of the LED encapsulating material G5 prepared in example 10;
fig. 10 is a graph of the contact angle test result of the LED encapsulating material G5 prepared in example 10;
fig. 11 is a graph showing the results of a surface tension test of the LED encapsulating material C1 prepared in comparative example 1;
fig. 12 is a graph showing the contact angle test result of the LED encapsulation material C1 prepared in comparative example 1.
Detailed Description
The following describes in detail specific embodiments of the present invention. It should be understood that the detailed description and specific examples, while indicating the present invention, are given by way of illustration and explanation only, not limitation.
The endpoints of the ranges and any values disclosed herein are not limited to the precise range or value, and such ranges or values should be understood to encompass values close to those ranges or values. For ranges of values, between the endpoints of each of the ranges and the individual points, and between the individual points may be combined with each other to give one or more new ranges of values, and these ranges of values should be considered as specifically disclosed herein.
The vinyl polyether surfactant provided by the invention contains at least one of a compound shown in a formula (1), a compound shown in a formula (2) and a compound shown in a formula (3),
wherein R is1Is vinyl or hydrogen, R2、R3Each independently is C1-C10M, n and p are each an integer of 0 to 100, and are not simultaneously 0. C1-C10The alkyl group of (a) may be a linear or branched alkyl group.
In the above formulae (1) to (3), R2、R3Specific examples of (a) include, but are not limited to; methyl, methoxy, ethyl, ethoxy, n-propyl, n-butyl, n-pentyl, n-hexyl, n-heptyl, n-octyl, isopropyl, isobutyl, sec-butyl, tert-butyl, isopentyl, neopentyl, tert-pentyl, isohexyl or cyclohexyl.
According to the present invention, R is preferably selected from the viewpoint of availability of raw materials2、R3Each independently is C1-C3Such as methyl, ethyl, n-propyl, methoxy or ethoxy.
The preparation method of the vinyl polyether surfactant provided by the invention comprises the following steps:
(1) subjecting a compound represented by the formula (4) to a hydrolysis reaction in the presence of an acidic catalyst, an organic solvent and water, so that R5、R6And R7At least one group in the (a) is hydrolyzed to a hydroxyl group to obtain a hydrolysate;
(2) carrying out ring-opening polymerization reaction on the hydrolysate, ethylene oxide and propylene oxide;
wherein R is1Is vinyl or hydrogen, R5、R6、R7Each independently is C1-C10Alkyl or alkoxy groups of (a).
In the above formula (4), R5、R6、R7Specific examples of (a) include, but are not limited to; methyl, methoxy, ethyl, ethoxy, n-propyl, n-butyl, n-pentyl, n-hexyl, n-heptyl, n-octyl, isopropylAn alkyl group, an isobutyl group, a sec-butyl group, a tert-butyl group, an isopentyl group, a neopentyl group, a tert-pentyl group, an isohexyl group or a cyclohexyl group.
According to the present invention, R is preferably selected from the viewpoint of availability of raw materials5、R6、R7Each independently is C1-C3Such as methyl, ethyl, n-propyl, methoxy or ethoxy.
The type of the acidic catalyst is not particularly limited in the present invention, and may be any of various conventional acidic catalysts capable of catalyzing hydrolysis reaction, for example: at least one of hydrochloric acid, sulfuric acid, trifluoroacetic acid, trifluoromethanesulfonic acid and nitric acid, preferably hydrochloric acid and/or sulfuric acid.
The kind of the organic solvent is not particularly limited in the present invention, and may be various liquid inert substances which are used to hydrolyze an alkoxy group into a hydroxyl group and can be used as a reaction medium, for example: at least one of dimethylacetamide, dimethylformamide, acetone, toluene, and xylene.
In the step (1), H is added to 1mol of the compound represented by the formula (4)+The amount of the acidic catalyst to be used may be 0.002 to 0.01mol, specifically, for example, 0.002mol, 0.003mol, 0.004mol, 0.005mol, 0.006mol, 0.007mol, 0.008mol, 0.009mol or 0.01 mol.
In the step (1), the amount of the water may be 1 to 3mol, specifically, for example, 1mol, 1.5mol, 2mol, 2.5mol, or 3mol, with respect to 1mol of the compound represented by the formula (4).
In the step (1), the molar ratio of the compound represented by the formula (4) to the amount of the organic solvent may be 1: 0.3 to 1, specifically, for example, may be 1: 0.3, 1: 0.4, 1: 0.5, 1: 0.6, 1: 0.7, 1: 0.8, 1: 0.9 or 1: 1.
in step (1), the conditions of the hydrolysis reaction may include: the temperature is 40-55 ℃ and the time is 2-3 h.
In the step (2), the ethylene oxide may be used in an amount of 1 to 200mol, preferably 20 to 200mol, relative to 1mol of the compound represented by the formula (4).
In the step (2), the propylene oxide may be used in an amount of 1mol relative to the compound represented by the formula (4); 1 to 100mol, preferably 10 to 100 mol.
In the step (2), the conditions of the ring-opening polymerization reaction may include: the temperature is 100-120 ℃; the time is 1-8 h.
In the present invention, the order of addition of the substances in step (1) is not particularly limited, and the reaction products may be mixed in various conventional orders. In the step (2), propylene oxide may be added to react after the product of the hydrolysis reaction is subjected to ring-opening polymerization with propylene oxide.
According to the present invention, preferably, the method for producing the organosilicon compound further comprises neutralizing the reaction product with an acid after completion of step (2), adding an alcohol to remove the neutralized salt in layers, and finally performing distillation under reduced pressure to remove the solvent to obtain the target product. Wherein, the acid can be at least one of formic acid, acetic acid, propionic acid, butyric acid, oxalic acid, malonic acid, succinic acid, benzoic acid and phenylacetic acid. The alcohol may be at least one of methanol, ethanol, ethylene glycol, isopropanol, and n-butanol.
The invention also provides the vinyl polyether surfactant prepared by the method.
The invention also provides application of the vinyl polyether surfactant as a leveling agent.
In addition, the invention also provides an LED packaging material, which contains silica gel and a leveling agent, wherein the leveling agent is the vinyl polyether surfactant.
In the LED packaging material, the content of the silica gel is 99-99.5 wt%, preferably 99.25-99.5 wt% based on the total weight of the LED packaging material; the content of the leveling agent is 0.5 to 1 wt%, preferably 0.5 to 0.75 wt%.
The main improvement of the present invention is that the vinyl polyether surfactant of the present invention is added to the existing silica gel for LED encapsulation to improve the adhesion performance, and the kind of the silica gel may be the same as the existing one, specifically, the silica gel may be various existing silica gels capable of being used as LED encapsulation materials, and it can be known by those skilled in the art, and is not described herein again.
The present invention will be described in detail below by way of examples.
In the following examples and comparative examples, the encapsulating silica gel was purchased from Beijing Kogyo New Material science and technology Co., Ltd under the designation SK 6180.
Example 1
(1) Adding 1mol of vinyltrimethoxysilane into 0.01mol of hydrochloric acid (the concentration is 36 weight percent) and 1mol of DMAC (dimethylacetamide) solution, dropwise adding 3mol of deionized water at 40 ℃, and heating to 50 ℃ to react for 3 hours after dropwise adding;
(2) putting the reaction product obtained in the step (1) and 20mol of Propylene Oxide (PO) into a reaction kettle, screwing a screw by using a wrench, replacing air in the reaction kettle with nitrogen for three times, and opening a heating switch to slowly heat to 120 ℃. And after the pressure in the kettle is reduced to 0, keeping the temperature and continuing to react for 60 min. Then opening cold water, cooling to room temperature, adding 10mol Ethylene Oxide (EO) and repeating the replacement and heating processes. The above-mentioned displacement and heating process was repeated by adding 10mol of Propylene Oxide (PO). After the reaction is finished, adding a small amount of acid for neutralization, and refining for later use to obtain the vinyl polyether surfactant S1.
Example 2
(1) Adding 1mol of methylvinyldimethoxysilane into 0.01mol of hydrochloric acid (the concentration is 36 weight percent) and 1mol of DMAC solution, dropwise adding 2mol of deionized water at 40 ℃, and heating to 55 ℃ to react for 3 hours after dropwise adding;
(2) putting the reaction product obtained in the step (1) and 20mol of Propylene Oxide (PO) into a reaction kettle, screwing a screw by using a wrench, replacing air in the reaction kettle with nitrogen for three times, and opening a heating switch to slowly heat to 120 ℃. And after the pressure in the kettle is reduced to 0, keeping the temperature and continuing to react for 60 min. Then opening cold water, cooling to room temperature, adding 10mol Ethylene Oxide (EO) and repeating the replacement and heating processes. The above-mentioned displacement and heating process was repeated by adding 10mol of Propylene Oxide (PO). After the reaction is finished, adding a small amount of acid for neutralization, and refining for later use to obtain the vinyl polyether surfactant S2.
Example 3
This preparation example is illustrative of the organosilicon compound provided by the present invention and the preparation method thereof
(1) Adding 1mol of dimethylvinylmethoxysilane into 0.01mol of hydrochloric acid (the concentration is 36 weight percent) and 1mol of DMAC solution, dropwise adding 2mol of deionized water at 40 ℃, and heating to 50 ℃ to react for 2 hours after the dropwise adding is finished;
(2) putting the reaction product obtained in the step (1) and 20mol of Propylene Oxide (PO) into a reaction kettle, screwing a screw by using a wrench, replacing air in the reaction kettle with nitrogen for three times, and opening a heating switch to slowly heat to 120 ℃. And after the pressure in the kettle is reduced to 0, keeping the temperature and continuing to react for 60 min. Then opening cold water, cooling to room temperature, adding 10mol Ethylene Oxide (EO) and repeating the replacement and heating processes. The above-mentioned displacement and heating process was repeated by adding 10mol of Propylene Oxide (PO). After the reaction is finished, adding a small amount of acid for neutralization, and refining for later use to obtain the vinyl polyether surfactant S3.
Example 4
This preparation example is illustrative of the organosilicon compound provided by the present invention and the preparation method thereof
(1) Adding 1mol of isobutyl vinyldimethoxysilane into 0.005mol of sulfuric acid (with the concentration of 98%) and 0.6mol of dimethylformamide solution, dripping 3mol of deionized water at 40 ℃, and heating to 40 ℃ to react for 3 hours after dripping is finished;
(2) putting the reaction product obtained in the step (1) and 200mol of Propylene Oxide (PO) into a reaction kettle, screwing a screw by using a wrench, replacing air in the reaction kettle with nitrogen for three times, and opening a heating switch to slowly heat to 120 ℃. And after the pressure in the kettle is reduced to 0, keeping the temperature and continuing to react for 60 min. Then opening cold water, cooling to room temperature, adding 100mol Ethylene Oxide (EO) and repeating the replacement and heating processes. The above-mentioned displacement and heating process was repeated by adding 100mol of Propylene Oxide (PO). After the reaction is finished, adding a small amount of acid for neutralization, and refining for later use to obtain the vinyl polyether surfactant S4.
Example 5
This preparation example is illustrative of the organosilicon compound provided by the present invention and the preparation method thereof
(1) 1mol of vinyltriethoxysilane is added to a mixed acid of hydrochloric acid and sulfuric acid (as H)+0.009mol) and 0.4mol of acetone solution, 2mol of deionized water is dripped at 40 ℃, and the temperature is raised to 45 ℃ after the dripping is finished to react for 3 hours;
(2) putting the reaction product obtained in the step (1) and 100mol of Propylene Oxide (PO) into a reaction kettle, screwing a screw by using a wrench, replacing air in the reaction kettle with nitrogen for three times, and opening a heating switch to slowly heat to 100 ℃. And after the pressure in the kettle is reduced to 0, keeping the temperature and continuing to react for 60 min. Then opening cold water, cooling to room temperature, adding 50mol Ethylene Oxide (EO) and repeating the replacement and heating processes. The above-mentioned displacement and heating process was repeated by adding 50mol of Propylene Oxide (PO). After the reaction is finished, adding a small amount of acid for neutralization, and refining for later use to obtain the vinyl polyether surfactant S5.
Example 6
0.75G of the vinyl polyether surfactant S1 prepared in example 1 was attached to 99.25G of LED encapsulating silica gel using hydrosilylation reaction over a Pt catalyst to give an LED encapsulating material designated G1.
Examples 7 to 10
0.5G of each of the vinyl polyether surfactants S2-S5 prepared in examples 2-5 was attached to 99.5G of an LED encapsulating silica gel by hydrosilylation reaction using a Pt catalyst to obtain LED encapsulating materials, which were respectively designated as G2-G5.
Comparative example 1
This comparative example serves to illustrate the preparation of a reference LED encapsulant.
A blank silica gel sample was used as a control sample, and no vinyl polyether surfactant was added to obtain a reference LED encapsulating material, which was designated C1.
Test example
(1) The surface tension of the LED encapsulating material was tested according to the pendant Drop method using a KRUSS interfacial tensiometer (model: Drop Shape Analyzer DSA-100);
(2) according to the GB/T6541 method, a PCT material is used as a substrate, and the contact angle between the LED packaging material and the substrate is tested.
The test results are shown in table 1 below. Wherein, the surface tension test result of the LED packaging material G1 prepared in example 6 is shown in fig. 1, and the contact angle test result of the LED packaging material G1 prepared in example 6 is shown in fig. 2; the surface tension test result of the LED encapsulating material G2 prepared in example 7 is shown in fig. 3, and the contact angle test result of the LED encapsulating material G2 prepared in example 7 is shown in fig. 4; the surface tension test result of the LED encapsulation material G3 prepared in example 8 is shown in fig. 5, and the contact angle test result of the LED encapsulation material G3 prepared in example 8 is shown in fig. 6; the surface tension test result of the LED encapsulating material G4 prepared in example 9 is shown in fig. 7, and the contact angle test result of the LED encapsulating material G4 prepared in example 9 is shown in fig. 8; the surface tension test result of the LED encapsulating material G5 prepared in example 10 is shown in fig. 9, and the contact angle test result of the LED encapsulating material G5 prepared in example 10 is shown in fig. 10; the surface tension test result of the LED encapsulating material C1 prepared in comparative example 1 is shown in fig. 11, and the contact angle test result of the LED encapsulating material C1 prepared in comparative example 1 is shown in fig. 12.
TABLE 1
| LED packaging material | Surface tension (mN/m) | Contact angle (°) |
| G1 | 47.12 | 77.1 |
| G2 | 40.62 | 69.8 |
| G3 | 42.80 | 79.0 |
| G4 | 39.76 | 81.5 |
| G5 | 47.90 | 85.5 |
| C1 | 72.12 | 110.3 |
Therefore, when the vinyl polyether surfactant disclosed by the invention is used as a leveling agent and is matched with an LED packaging adhesive for use, the surface tension of the adhesive can be reduced, and the leveling performance is obviously improved.
The preferred embodiments of the present invention have been described above in detail, but the present invention is not limited thereto. Within the scope of the technical idea of the invention, many simple modifications can be made to the technical solution of the invention, including combinations of various technical features in any other suitable way, and these simple modifications and combinations should also be regarded as the disclosure of the invention, and all fall within the scope of the invention.
Claims (10)
1. A vinyl polyether surfactant, characterized in that the vinyl polyether surfactant contains at least one of a compound represented by formula (1), a compound represented by formula (2) and a compound represented by formula (3),
wherein R is1Is vinyl or hydrogen, R2、R3Each independently is C1-C10M, n and p are each an integer of 0 to 100, and are not simultaneously 0.
2. The organosilicon compound of claim 1, wherein R is2、R3Each independently is methyl, methoxy, ethyl, ethoxy, n-propyl, n-butyl, n-pentyl, n-hexyl, n-heptyl, n-octyl, isopropyl, isobutyl, sec-butyl, tert-butyl, isopentyl, neopentyl, tert-pentyl, isohexyl or cyclohexyl.
3. A method for preparing a vinyl polyether surfactant, comprising:
(1) subjecting a compound represented by the formula (4) to a hydrolysis reaction in the presence of an acidic catalyst, an organic solvent and water, so that R5、R6And R7At least one group in the (a) is hydrolyzed to a hydroxyl group to obtain a hydrolysate;
(2) carrying out ring-opening polymerization reaction on the hydrolysate, ethylene oxide and propylene oxide;
wherein R is1Is vinyl or hydrogen, R5、R6、R7Each independently is C1-C10Alkyl or alkoxy groups of (a).
4. The method of claim 3, wherein R is5、R6、R7Each independently is methyl, methoxy, ethyl, ethoxy, n-propyl, n-butyl, n-pentyl, n-hexyl, n-heptyl, n-octyl, isopropyl, isobutyl, sec-butyl, tert-butyl, isopentyl, neopentyl, tert-pentyl, isohexyl or cyclohexyl.
5. The process according to claim 3 or 4, wherein in step (1), the acidic catalyst is at least one of hydrochloric acid, sulfuric acid, trifluoroacetic acid, trifluoromethanesulfonic acid and nitric acid, preferably hydrochloric acid and/or sulfuric acid;
preferably, the organic solvent is at least one of dimethylacetamide, dimethylformamide, acetone, toluene, and xylene.
6. The method according to claim 3 or 4, wherein, in step (1), H is used relative to 1mol of the compound represented by formula (4)+The dosage of the acid catalyst is 0.002-0.01 mol;
preferably, the amount of water used is 1 to 3mol with respect to 1mol of the compound represented by the formula (4);
preferably, the molar ratio of the compound represented by the formula (4) to the amount of the organic solvent is 1: 0.3 to 1;
preferably, the conditions of the hydrolysis reaction include: the temperature is 40-55 ℃ and the time is 2-3 h.
7. The method according to claim 3, wherein in step (2), the ethylene oxide is used in an amount of 1 to 200mol relative to 1mol of the compound represented by formula (4); the using amount of the propylene oxide is 1-100 mol;
preferably, the conditions of the ring-opening polymerization reaction include: the temperature is 100-120 ℃, and the time is 1-8 h.
8. A vinyl polyether surfactant prepared by the process of any one of claims 3-7.
9. Use of the vinyl polyether surfactant according to claim 1, 2 or 8 as a leveling agent.
10. An LED packaging material, which contains silica gel and a leveling agent, wherein the leveling agent is the vinyl polyether surfactant according to claim 1, 2 or 8;
preferably, the content of the silica gel is 99-99.5 wt% and the content of the leveling agent is 0.5-1 wt% based on the total weight of the LED packaging material.
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| Publication number | Priority date | Publication date | Assignee | Title |
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| CN112044353A (en) * | 2019-06-05 | 2020-12-08 | 新特能源股份有限公司 | Novel Gemini surfactant and preparation method thereof, novel comb-type surfactant and preparation method thereof |
| CN112044353B (en) * | 2019-06-05 | 2022-06-28 | 新特能源股份有限公司 | Novel Gemini surfactant and preparation method thereof, novel comb-type surfactant and preparation method thereof |
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| CN111154091B (en) | 2022-04-19 |
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