CN110760067A - Organic silicon oligomer and synthesis method and application thereof - Google Patents

Organic silicon oligomer and synthesis method and application thereof Download PDF

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CN110760067A
CN110760067A CN201911010477.7A CN201911010477A CN110760067A CN 110760067 A CN110760067 A CN 110760067A CN 201911010477 A CN201911010477 A CN 201911010477A CN 110760067 A CN110760067 A CN 110760067A
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epoxy resin
resin composition
oligomer
organic silicon
antioxidant
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CN110760067B (en
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袁有学
张宗勋
李劲辉
聂晓李
张文彬
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GUANGDONG WAMO NEW MATERIAL TECHNOLOGY Ltd
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    • C—CHEMISTRY; METALLURGY
    • 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
    • C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
    • C08G77/04—Polysiloxanes
    • C08G77/22—Polysiloxanes containing silicon bound to organic groups containing atoms other than carbon, hydrogen and oxygen
    • C08G77/26—Polysiloxanes containing silicon bound to organic groups containing atoms other than carbon, hydrogen and oxygen nitrogen-containing groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
    • C07F7/02—Silicon compounds
    • C07F7/08—Compounds having one or more C—Si linkages
    • C07F7/0834—Compounds having one or more O-Si linkage
    • C07F7/0838—Compounds with one or more Si-O-Si sequences
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
    • C07F7/02—Silicon compounds
    • C07F7/08—Compounds having one or more C—Si linkages
    • C07F7/0834—Compounds having one or more O-Si linkage
    • C07F7/0838—Compounds with one or more Si-O-Si sequences
    • C07F7/0872—Preparation and treatment thereof
    • C07F7/0876—Reactions involving the formation of bonds to a Si atom of a Si-O-Si sequence other than a bond of the Si-O-Si linkage
    • C07F7/0878—Si-C bond
    • C07F7/0879—Hydrosilylation reactions
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L63/00—Compositions of epoxy resins; Compositions of derivatives of epoxy resins
    • 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
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L2201/00—Properties
    • C08L2201/10—Transparent films; Clear coatings; Transparent materials
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • 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
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L2205/00—Polymer mixtures characterised by other features
    • C08L2205/02—Polymer mixtures characterised by other features containing two or more polymers of the same C08L -group
    • C08L2205/025—Polymer mixtures characterised by other features containing two or more polymers of the same C08L -group containing two or more polymers of the same hierarchy C08L, and differing only in parameters such as density, comonomer content, molecular weight, structure
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L2205/00—Polymer mixtures characterised by other features
    • C08L2205/03—Polymer mixtures characterised by other features containing three or more polymers in a blend
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L2205/00—Polymer mixtures characterised by other features
    • C08L2205/03—Polymer mixtures characterised by other features containing three or more polymers in a blend
    • C08L2205/035—Polymer mixtures characterised by other features containing three or more polymers in a blend containing four or more polymers in a blend

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Silicon Polymers (AREA)
  • Epoxy Resins (AREA)

Abstract

The invention discloses an organic silicon oligomer, which has a structural formula shown as a formula (I). The organic silicon oligomer is added into the basic epoxy resin, so that the cured epoxy resin has good adhesion with a silver coating, good thermal aging resistance and good thermal shock resistance. The invention also discloses a synthetic method of the organic silicon oligomer, an epoxy resin composition containing the organic silicon oligomer, and an epoxy resin formula for packaging an LED display screen, wherein the epoxy resin composition is especially suitable for packaging the LED display screen.

Description

Organic silicon oligomer and synthesis method and application thereof
Technical Field
The invention belongs to the technical field of high polymer materials, and particularly relates to an organic silicon oligomer and a synthesis method and application thereof.
Background
The epoxy resin for packaging the LED display screen is a high-performance epoxy resin composition which has high transparency, high thermal aging resistance and ultraviolet aging resistance, good bonding force to a silver coating and an LED chip bracket and cold and hot shock resistance.
The problem of bonding the epoxy resin and the silver coating can be solved by directly adding the tris (glycidyl isocyanurate) into the epoxy resin for packaging the LED display screen, but the requirement on cold and hot shock performance cannot be met. Therefore, a sufficient amount of toughening agent must be added simultaneously to satisfy both of the above requirements. However, the epoxy resin composition has a significantly reduced thermal aging resistance due to the excessive use of the toughening agent.
Disclosure of Invention
The invention aims to overcome the defects in the prior art and provide an organic silicon oligomer and a synthesis method and application thereof.
In order to achieve the purpose, the invention adopts the technical scheme that: an organosilicon oligomer having the formula (I):
Figure BDA0002242801330000021
wherein n is 0-8; m is 0 to 1.
The organic silicon oligomer adopts polysiloxane with a certain chain length to connect two or three mono-epoxypropyl isocyanurate molecules into a di-epoxy or tri-epoxy molecule, and the organic silicon oligomer is added into the basic epoxy resin, so that the epoxy resin composition can be well adhered to a silver coating, has good heat resistance and aging resistance and has good cold and heat shock resistance after being cured.
N may be an integer of 0 to 8 for a single molecule of the silicone oligomer, and the silicone oligomer may be composed of a plurality of silicone oligomers having different n for the entire finally prepared silicone oligomer, so that n is actually an average number between 0 and 8 for the silicone oligomer.
Another object of the present invention is also to provide a method for synthesizing the silicone oligomer, comprising the steps of:
Figure BDA0002242801330000022
(1) adding a catalyst Pt into a compound shown as a formula (II), and heating to 80-85 ℃;
(2) and (2) dropwise adding a compound shown as a formula (III) into the solution obtained in the step (1), maintaining the temperature of the solution obtained in the step (1) at 80-85 ℃, and then reacting at 83-87 ℃ for 8-12 hours to obtain the organic silicon oligomer.
The organosilicon oligomer prepared by adopting the synthesis conditions has stable properties.
As a preferred embodiment of the synthesis method of the organic silicon oligomer, the catalyst Pt is a Pt toluene solution, and the concentration of the catalyst Pt in the system is 15 ppm.
In the step (2), the compound represented by the formula (III) is dripped into the solution obtained in the step (1) at a dripping speed of 0.2-0.3 g/min, which is a preferable embodiment of the method for synthesizing the organic silicon oligomer.
Another object of the present invention is to provide an epoxy resin composition comprising the above silicone oligomer.
In a preferred embodiment of the epoxy resin composition of the present invention, the silicone oligomer is added in an amount of 2.5 to 10% to the epoxy resin composition. The silicone oligomer can achieve good thermal aging resistance, good thermal shock resistance and good adhesion performance by adding the content into the epoxy resin composition. An excessively high amount of addition results in a decrease in transparency.
As a preferred embodiment of the epoxy resin composition, the epoxy resin composition comprises the following components in parts by weight: 40-47.5 parts of epoxy resin, 2.5-10 parts of organic silicon oligomer, 42.5-47.5 parts of curing agent and 2.5-7.5 parts of toughening agent.
As a preferred embodiment of the epoxy resin composition of the present invention, the curing agent comprises methylhexahydrophthalic anhydride, a curing accelerator, an antioxidant and an ultraviolet absorber; the curing accelerator is at least one of 2-methylimidazole, 2-methyl-4-ethylimidazole, triphenylphosphine, tetrabutylphosphonium chloride, tetrabutylphosphonium bromide, benzyltriphenylphosphonium chloride and benzyltriphenylphosphonium bromide; the antioxidant is at least one of antioxidant 1098, antioxidant 1010, antioxidant 2246 and antioxidant 168; the ultraviolet absorbent is at least one of UV-P, UV-234, UV-326 and UV-327. The toughening agent is polyester diol.
As a preferred embodiment of the epoxy resin composition of the present invention, the curing agent comprises the following components in parts by weight: 41.9-46.8 parts of methyl hexahydrophthalic anhydride, 0.38-0.43 part of curing accelerator, 0.13-0.14 part of antioxidant and 0.085-0.095 part of ultraviolet absorber.
As a preferred embodiment of the epoxy resin composition of the present invention, the epoxy resin is a bisphenol a epoxy resin and/or a cycloaliphatic epoxy resin. More preferably, the epoxy resin is a mixture of bisphenol a epoxy resin and cycloaliphatic epoxy resin, and the weight ratio of the bisphenol a epoxy resin to the cycloaliphatic epoxy resin is: bisphenol a epoxy resin: 1-50% of alicyclic epoxy resin: 50 to 99 parts.
The invention also aims to provide an epoxy resin formula for encapsulating the LED display screen, which comprises the epoxy resin composition. The epoxy resin composition is particularly suitable for packaging LED display screens, and has the advantages of heat aging resistance, cold and heat shock resistance and good adhesion performance with a silver coating.
The invention has the beneficial effects that: the organic silicon oligomer is added into basic epoxy resin, so that the cured epoxy resin has good adhesion with a silver coating, good heat aging resistance and good cold and heat shock resistance. The invention also provides a synthetic method of the organic silicon oligomer, an epoxy resin composition containing the organic silicon oligomer, and an epoxy resin formula for packaging an LED display screen, wherein the epoxy resin composition is especially suitable for packaging the LED display screen.
Drawings
FIG. 1 is a structural formula of an organosilicon oligomer of formula (I);
FIG. 2 is a NMR spectrum of the silicone oligomer of example 1;
FIG. 3 is a NMR spectrum of the silicone oligomer of example 2;
FIG. 4 is a NMR spectrum of the silicone oligomer described in example 3.
Detailed Description
To better illustrate the objects, aspects and advantages of the present invention, the present invention will be further described with reference to specific examples.
Example 1
The structural formula of the silicone oligomer in the embodiment is shown as formula (i) in fig. 1, wherein n is 0, and m is 0-1.
The synthesis method of the organic silicon oligomer described in this example is: 15.91 g (0.060 mol) of diallyl-epoxypropane isocyanurate and 0.110 g of Pt catalyst toluene solution (Pt content 0.2%) were added to a 100 ml three-necked flask equipped with a constant pressure dropping funnel, condenser and thermometer, stirred and heated to 80 ℃ in an oil bath, and then 6.50 g of tetramethyldisiloxane was slowly (30 minutes) added dropwise to the three-necked flask through the constant pressure dropping funnel, and the temperature was maintained between 80 ℃ and 85 ℃. Then, the reaction was maintained at 85 ℃ for 8 hours to obtain 20.01 g of a colorless and transparent liquid product, which was the silicone oligomer of the present example.
The nmr hydrogen spectrum of the silicone oligomer described in this example is shown in figure 2.
Example 2
The structural formula of the silicone oligomer is shown in formula (i), wherein n is 4, and m is 0-1.
The synthesis method of the organic silicon oligomer described in this example is: 15.91 g (0.060 mol) of diallyl-epoxypropane isocyanurate and 0.330 g of Pt catalyst toluene solution (Pt content 0.2%) were added to a 100 ml three-neck flask equipped with a constant pressure dropping funnel, condenser and thermometer, stirred and heated to 80 ℃ in an oil bath, and then 13.00 g of four-chain hydrogen-containing silazane was slowly (60 minutes) dropped into the three-neck flask through the constant pressure dropping funnel, and the temperature was maintained between 80 ℃ and 85 ℃. Then the reaction was maintained at 85 ℃ for 12 hours to obtain 29.00 g of a colorless and transparent liquid product, which was the silicone oligomer of the present example.
The nmr hydrogen spectrum of the silicone oligomer described in this example is shown in figure 3.
Example 3
The structural formula of the silicone oligomer is shown in formula (i), wherein n is 8, and m is 0-1.
The synthesis method of the organic silicon oligomer described in this example is: 15.91 g (0.060 mol) of diallyl-epoxypropane isocyanurate and 0.330 g of Pt catalyst toluene solution (Pt content 0.2%) were added to a 100 ml three-neck flask equipped with a constant pressure dropping funnel, condenser and thermometer, stirred in an oil bath and heated to 80 ℃, and then 21.80 g of octamer hydrogen-containing silazane was slowly (60 minutes) dropped into the three-neck flask through the constant pressure dropping funnel, and the temperature was maintained between 80 ℃ and 85 ℃. Then the reaction was maintained at 85 ℃ for 12 hours to obtain 37.81 g of a colorless and transparent liquid product, which is the silicone oligomer of the present example.
The nmr spectrum of the silicone oligomer described in this example is shown in fig. 4.
Examples 4 to 6 and comparative examples 1 to 2
The formulations of the epoxy resins described in examples 4 to 6 and comparative examples 1 to 2 are shown in Table 1.
In examples 4 to 6 and comparative examples 1 to 2, the plasticizer was a polyester diol having a commercial model number of L3009, produced by great republic of chemical limited corporation in shanghai; the base epoxy resin is a mixture of bisphenol A epoxy resin and alicyclic epoxy resin, and the weight ratio of the bisphenol A epoxy resin to the alicyclic epoxy resin is as follows: bisphenol a epoxy/cycloaliphatic epoxy 50/50.
TABLE 1 formulation of epoxy resins described in examples 4-6 and comparative examples 1-2
Figure BDA0002242801330000061
Example 7
10 parallel samples of the epoxy resins described in examples 4 to 6 and comparative examples 1 to 2 were tested by the following methods:
the bonding performance with the silver coating is analyzed by ultrasonic scanning (using an ultrasonic microscope) to observe whether the layering phenomenon occurs;
the cold and hot impact number is tested by a high and low temperature cycle test machine, and the cold and hot impact conditions are as follows: and (3) standing at-40 ℃ for 15 minutes and then at 125 ℃ for 15 minutes, testing whether the sample fails or not every 50 times for one cycle, stopping a subsequent cold-heat impact test after more than one sample in 10 samples fails, and recording the number of cycles when the samples fail, namely the number of cold-heat impacts.
The aging resistance is tested by an aging resistant thermal aging oven, the yellowing degree of the product after 72 hours at the temperature of 150 ℃ is observed, and the test results are shown in table 2.
TABLE 2 Performance test results for epoxy resins described in examples 4-6 and comparative examples
Group of Adhesion to silver coating Number of cold and hot impacts Thermal aging resistance Cured transparency
Example 4 ★★★★ 50 ★★★★ Is transparent
Example 5 ★★★★★ 200 ★★★★ Is transparent
Example 6 ★★★★★ 300 ★★★★★ Semi-transparent
Comparative example 1 ★★ 300 ★★★ Is transparent
Comparative example 2 ★★★★ 50 ★★ Is transparent
In the table, ★ indicates the worst, and ★★★★★ indicates the best.
As can be seen from table 2, the epoxy resin of example 4, to which the silicone oligomer of example 1 was added, has better adhesive properties, thermal aging resistance and transparency, and although the thermal shock properties are similar to those of comparative example 2, which is very yellowing and greatly reduced in thermal aging resistance, is achieved only by adding a large amount of a toughening agent, whereas comparative example 2, which is poor in both adhesive properties and thermal aging resistance. The epoxy resin of example 6 to which the silicone oligomer of example 3 was added had high adhesive properties, cold and thermal shock properties, and aging resistance, and the epoxy resin of example 5 to which the silicone oligomer of example 2 was added had good adhesive properties, cold and thermal shock properties, thermal aging resistance, and transparency.
Finally, it should be noted that the above embodiments are only used for illustrating the technical solutions of the present invention and not for limiting the protection scope of the present invention, and although the present invention is described in detail with reference to the preferred embodiments, it should be understood by those skilled in the art that modifications or equivalent substitutions can be made on the technical solutions of the present invention without departing from the spirit and scope of the technical solutions of the present invention.

Claims (10)

1. An organosilicon oligomer having the formula (I):
Figure FDA0002242801320000011
wherein n is 0-8; m is 0 to 1.
2. The method of synthesizing the silicone oligomer of claim 1, comprising the steps of:
(1) adding a catalyst Pt into a compound shown as a formula (II), and heating to 80-85 ℃;
(2) and (2) dropwise adding a compound shown as a formula (III) into the solution obtained in the step (1), maintaining the temperature of the solution obtained in the step (1) at 80-85 ℃, and then reacting at 83-87 ℃ for 8-12 hours to obtain the organic silicon oligomer.
3. The method for synthesizing the organic silicon oligomer according to claim 2, wherein the catalyst Pt is a Pt complex toluene solution, and the concentration of the catalyst Pt in the system is 15 ppm; in the step (2), the compound shown in the formula (III) is dripped into the solution obtained in the step (1) at a dripping speed of 0.2-0.3 g/min.
4. An epoxy resin composition comprising the silicone oligomer according to claim 1.
5. The epoxy resin composition according to claim 4, wherein the silicone oligomer is present in the epoxy resin composition in an amount of 2.5 to 10% by weight.
6. The epoxy resin composition according to claim 4, comprising the following components in parts by weight: 40-47.5 parts of epoxy resin, 2.5-10 parts of organic silicon oligomer, 42.5-47.5 parts of curing agent and 2.5-7.5 parts of toughening agent.
7. The epoxy resin composition of claim 6, wherein the curing agent comprises methylhexahydrophthalic anhydride, a curing accelerator, an antioxidant, and an ultraviolet absorber; the curing accelerator is at least one of 2-methylimidazole, 2-methyl-4-ethylimidazole, triphenylphosphine, tetrabutylphosphonium chloride, tetrabutylphosphonium bromide, benzyltriphenylphosphonium chloride and benzyltriphenylphosphonium bromide; the antioxidant is at least one of antioxidant 1098, antioxidant 1010, antioxidant 2246 and antioxidant 168; the ultraviolet absorbent is at least one of UV-P, UV-234, UV-326 and UV-327.
8. The epoxy resin composition according to claim 6, wherein the curing agent comprises the following components in parts by weight: 41.9-46.8 parts of methyl hexahydrophthalic anhydride, 0.38-0.43 part of curing accelerator, 0.13-0.14 part of antioxidant and 0.085-0.095 part of ultraviolet absorber.
9. The epoxy resin composition according to claim 6, wherein the epoxy resin is a bisphenol A epoxy resin and/or a cycloaliphatic epoxy resin.
10. An epoxy resin for encapsulating an LED display screen, comprising the epoxy resin composition according to any one of claims 4 to 9.
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