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CN111040223B - Preparation method and application of light diffusant - Google Patents

Preparation method and application of light diffusant Download PDF

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CN111040223B
CN111040223B CN201911364818.0A CN201911364818A CN111040223B CN 111040223 B CN111040223 B CN 111040223B CN 201911364818 A CN201911364818 A CN 201911364818A CN 111040223 B CN111040223 B CN 111040223B
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diffusing agent
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CN111040223A (en
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陈志强
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Tangshan Coupling Silicon Industry Co ltd
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    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
    • C08J7/00—Chemical treatment or coating of shaped articles made of macromolecular substances
    • C08J7/12—Chemical modification
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L33/00—Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides or nitriles thereof; Compositions of derivatives of such polymers
    • C08L33/04—Homopolymers or copolymers of esters
    • C08L33/06—Homopolymers or copolymers of esters of esters containing only carbon, hydrogen and oxygen, which oxygen atoms are present only as part of the carboxyl radical
    • C08L33/10—Homopolymers or copolymers of methacrylic acid esters
    • C08L33/12—Homopolymers or copolymers of methyl methacrylate
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L69/00—Compositions of polycarbonates; Compositions of derivatives of polycarbonates
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
    • C08J2383/00—Characterised by the use of 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; Derivatives of such polymers
    • C08J2383/04—Polysiloxanes
    • C08J2383/07—Polysiloxanes containing silicon bound to unsaturated aliphatic groups
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
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    • 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
    • C08L2205/00—Polymer mixtures characterised by other features
    • C08L2205/14—Polymer mixtures characterised by other features containing polymeric additives characterised by shape
    • C08L2205/18—Spheres

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Abstract

The invention relates to the field of modification of high polymer materials, in particular to a preparation method and application of a lighting high polymer material modifier, and particularly relates to a preparation method and application of a light diffuser. The light diffusant can also be used as a flame retardant, a surface friction-resistant agent, a silky handfeel agent and the like, and is used in the industries of coatings, plastics, rubber, medicines, hair care products, textiles and the like.

Description

Preparation method and application of light diffusant
Technical Field
The invention relates to the field of modification of high polymer materials, and relates to a preparation method and application of a lighting high polymer material modifier, in particular to a preparation method and application of a light diffusant.
Background
The light diffusing agent is a microsphere product developed by means of crosslinking, grafting functional groups and the like by utilizing a high molecular polymerization technology. The light-emitting diode can be added into transparent resin such as PC, PVC, PS, PMMA, PET, epoxy resin and the like and an LED (light-emitting diode), so that the light scattering and transmission are increased, a light source and a glaring light source are shielded, the whole resin can emit softer, more attractive and more elegant light, and the comfortable effect of light transmission and opaqueness is achieved. The light diffusing agent is mainly classified into inorganic type light diffusing agents such as nano barium sulfate, calcium carbonate and silica, and organic type light diffusing agents such as acryl type and styrene type. Since light cannot pass through the inorganic type light diffusing agent, only a part of light passes through by refraction, and thus brightness is affected. The organic light diffusant is transparent or semitransparent, most of light can pass through the organic light diffusant, and by means of the difference between the refractive index of the material of the light diffusant and the refractive index of the base material, the light passing through the base material is bright and soft after being refracted for multiple times, and the influence on the light transmittance of the material is small.
The organic silicon resin light diffusant has the characteristics of both an inorganic light diffusant and an organic light diffusant, has the advantages of low specific gravity, good lubricity, low volatility, good heat resistance and the like, has excellent light diffusion performance in transparent resins such as Polycarbonate (PC), Polyphenylene Sulfide (PS), Polyacrylate (PMMA) and the like, and has good balance among impact strength, haze and light transmittance.
However, silicone resin diffusers have the disadvantage of not being well dispersed in the resin. Chinese patent CN105566579B discloses a method for preparing an organic silicon light diffusant, emulsifying and polymerizing an emulsifier, an initiator, organic silicon resin microspheres, 1-methoxy-3-trimethylsiloxy-1, 3-butadiene, divinyl polydimethylsiloxane and pentafluoro-1-propylene to obtain modified organic silicon resin microspheres, and adding the modified organic silicon resin microspheres into a PC board to improve light transmittance and have better dispersibility.
However, the method is essentially to polymerize an organic polymer on the surface of the organic silicon resin microsphere to improve the compatibility with the resin, and the method sacrifices the characteristics of high temperature resistance, low volatilization, lubricity and the like of the organic silicon resin.
Disclosure of Invention
The invention aims to overcome the defects of the prior art and provide a preparation method of a light diffusant, which solves the problem of dispersibility of the existing organic silicon resin light diffusant.
Another object of the present invention is to provide a light diffusing agent.
It is a further object of the present invention to provide a use of the light diffuser.
The invention adopts the following technical scheme:
a method for preparing light diffusion agent is prepared by grafting cage polysilsesquioxane on the surface of organic silicon resin microsphere, and specifically comprises the following steps of adding vinyl silicon resin microsphere into a first organic solvent for ultrasonic dispersion for 5-10 minutes, and adding the vinyl silicon resin microsphere with a chemical general formula of R 1 R 2 7 (SiO 1.5 ) 8 The single-functional cage-type octa-polysilsesquioxane is evenly stirred, and a photoinitiator is added, wherein the dominant wavelength is 365nm, and the light intensity is 0.5-10mW/cm 2 Irradiating for 0.2-20 minutes under ultraviolet light, centrifuging, removing filtrate, collecting solid powder, and cleaning the powder with a second organic solvent for three times to obtain a light diffusant; the R is 1 Selected from 2-mercaptoethyl or 3-mercaptopropyl, said R 2 One selected from isobutyl, phenyl, methyl, propyl and gamma-chloropropyl.
Preferably, the vinyl silicone resin microspheres have an average particle size of 0.5-20 μm and a vinyl content of 0.1-5% by mass. More preferably, the vinyl silicone resin microspheres have an average particle size of 1-15 microns; further preferably, the vinyl silicone resin microspheres have an average particle size of 2 μm, 3 μm, 5 μm, 8 μm, 10 μm or 12 μm.
More preferably, the vinyl content in the vinyl silicone resin microspheres is 0.5-3% by mass; more preferably, the vinyl content is 0.8%, 1.2%, 1.5%, 2%, 2.5% or 3% by mass.
Publication No. CN103214674B discloses a method for producing organic silicon resin microspheres, which comprises hydrolyzing silane with three or four hydrolyzable groups at high temperature and high pressure, condensing, balling to obtain aqueous suspension of organic silicon resin microspheres, neutralizing, filtering, and oven drying to obtain organic silicon resin microspheres.
In the article document, "spherical silicone resin micropowder" (journal, "silicone material", 2007, vol 21, No. 6, page 364-370), several methods for preparing vinyl silicone resin micropowder are reported, all of which are prepared by performing hydrolytic condensation on methyltrimethoxysilane and vinyl trialkoxysilane in an aqueous alkali solution.
Preferably, the first organic solvent is selected from one or a combination of acetone, ethyl acetate, butyl acetate, xylene, trimethylbenzene, toluene, methyl ethyl ketone, cyclohexanone and ethylene glycol dimethyl ether.
Preferably, the weight ratio of the vinyl silicone resin microspheres to the first organic solvent is 1: 2-10. More preferably, the weight ratio of the vinyl silicone resin microspheres to the first organic solvent is 1: 3-6; further preferably, the weight ratio is 1:3, 1:4, 1:5 or 1: 6.
Preferably, the ratio of the mole number of vinyl groups of the vinyl silicon resin microspheres to the mole number of the cage-type octasilsesquioxane is 1: 1.05-2. More preferably, the ratio of the mole number of vinyl groups of the vinyl silicon resin microspheres to the mole number of the cage-type octasilsesquioxane is 1: 1.1-1.7; further preferably, the molar ratio is 1:1.1, 1:1.2, 1:1.3, 1:1.4, 1: 1.5.
The most common method for preparing monofunctional cage polysilsesquioxanes is the "capping at the apex", i.e., trichlorosilane or trialkoxy silicon containing inert groups The alkane is hydrolyzed and condensed in acetone water solution or other organic solvent water solution under the alkaline or acidic condition to obtain semi-closed cage polysilsesquioxane trisilicol T 7 (OH) 3 Or cage polysilsesquioxane trisilicate, and then dehydrochlorination or chloride reaction is carried out on the cage polysilsesquioxane trisilicate and trichlorosilane containing functional groups under the alkaline condition to obtain the cage polysilsesquioxane with the single functional group.
The patent CN101906116B granted by the invention in China provides a method for synthesizing cage-type octa-polysilsesquioxane with the same or different functional groups and non-functional groups, which comprises the steps of dropwise adding a mixed solution of non-functional silane and functional silane into a mixed solution of a solvent, deionized water and a catalyst, refluxing, stirring, reacting, filtering and cleaning to obtain the cage-type octa-polysilsesquioxane with the single functional group, the double functional group and the multifunctional group.
Preferably, the photoinitiator is selected from one or a combination of benzoin dimethyl ether, benzoin ethyl ether and benzoin butyl ether, and the usage weight of the photoinitiator is 1-5% of the weight of the vinyl silicone resin microspheres. More preferably, the photoinitiator is used in an amount of 2 to 4.5% by weight based on the weight of the vinyl silicone resin microspheres.
Preferably, the second solvent is selected from one or a combination of absolute ethyl alcohol, isopropyl alcohol, acetone and butyl acetate.
A light diffusing agent prepared by the method of any one of the above embodiments.
The light diffusing agent of the above embodiment is applied to polycarbonate, polyacrylate, polyphenylene sulfide, polypropylene, polyethylene and polyester.
The light diffusant prepared by the method can also be used as a flame retardant, a surface friction-resistant agent, a silky handfeel agent and the like, and is used in the industries of coatings, plastics, rubber, medicines, hair care products, textiles and the like.
The cage-type polysilsesquioxane is grafted on the surface of the organic silicon resin microsphere of the light diffuser, because the size of the cage-type polysilsesquioxane is nano-scale, the surface roughness of the organic silicon resin microsphere is improved as the cage-type polysilsesquioxane is grafted on the surface of the organic silicon resin microsphere, and the refractive index of the cage-type polysilsesquioxane is different from that of the organic silicon resin microsphere, when the light diffuser is added into a polymer material, light rays can be refracted on the light diffuser for multiple times when entering the material, so that the refraction times of the light rays are improved, and even if the refractive indexes of the light diffuser and the polymer resin material are close, the refraction times of the light rays can be increased, and the haze of the material is improved. Meanwhile, the cage-type polysilsesquioxane is grafted on the surface of the organic silicon resin microsphere, so that the dispersibility of the organic silicon resin microsphere in a polymer material is improved, and the light transmittance is improved.
The beneficial effects of the invention are:
(1) the obtained light diffusant is added into a polymer resin material, so that light rays entering the material are refracted for more times, the haze of the material can be improved, and compared with organic silicon resin microspheres, the light diffusant has better haze and has no influence on light transmittance; even if the haze of the light diffusing agent of the present invention is closer to that of the polymer resin material, the haze is better.
(2) The obtained light diffusant is added into the polymer resin material, so that the mechanical strength and the heat resistance of the material can be effectively improved, the aging of the resin material caused by long-term heating of a light source is slowed down, and the service life of the resin material is prolonged;
(3) the method for preparing the light diffusant has the advantages of convenient raw material source, simple preparation steps and convenient post-treatment, and is suitable for batch production;
(4) according to the R in the raw material cage type octa-polysilsesquioxane 2 The light diffusant with different properties can be obtained by the difference of the groups, and can be applied to other fields.
Drawings
Fig. 1 is a schematic view of the diffusion principle of the prior silicone resin microsphere as a light diffuser.
In the figure, 1 is a silicone resin microsphere, and 2 is a light propagation path;
FIG. 2 is a schematic view showing the diffusion principle of the light diffusing agent of the present invention.
In the figure, 1-organic silicon resin microsphere, 2-grafted cage polysilsesquioxane and 3-ray propagation path;
Detailed Description
The technical solution of the present invention is further illustrated and described by the following detailed description.
Unless otherwise specified, parts in the following embodiments are parts by weight.
Description of the preferred embodiment
Preparation of monofunctional cage type octapolysilsesquioxane
Reference journal literature synthesis and characterization of monofunctional silsesquioxane (organosilicon materials 2011, 25(5), 300-305 pages) preparation of heptaisobutyl (3-mercaptopropyl) cage octapolysilsesquioxane
Adding 5 parts of heptaisobutyl trisilicon hydroxyl cage type polysilsesquioxane into a container, adding 110 parts of newly distilled tetrahydrofuran, uniformly stirring, adding 3 parts of triethylamine and 1 part of mercaptopropyl trichlorosilane into the container by using an injector, stirring the mixture at normal temperature for reaction for 15 hours, filtering the mixture, collecting filtrate, concentrating the filtrate to 15 parts, adding 15 parts of acetonitrile into the filtrate, filtering the mixture, collecting white solid, and drying the white solid to obtain the heptaisobutyl (3-mercaptopropyl) cage type octapolysilsesquioxane (HS-POSS 1 for short).
Preparation of heptaphenyl (3-mercaptopropyl) cage type octapolysilsesquioxane (HS-POSS 2 for short) by referring to patent granted on invention CN104262385B
Example 1
10 parts of vinyl silicone resin microspheres with the average particle size of 3 mu m and the vinyl content of 1.2 wt% are added into 30 parts of butyl acetate for ultrasonic dispersion for 8 minutes, 22.5 parts of HS-POSS1 are added, the mixture is stirred uniformly, 0.3 part of benzoin dimethyl ether is added, and the mixture is stirred uniformly under the conditions that the dominant wavelength is 365nm and the light intensity is 8mW/cm 2 Irradiating for 8 minutes under ultraviolet light, centrifuging, removing filtrate, collecting solid powder, and washing the powder with absolute ethanol for three times to obtain the light diffusant 1. The refractive index of the light diffusing agent 1 was measured to be 1.446(20 ℃ C.).
Example 2
Adding 10 parts of vinyl silicone resin microspheres with the average particle size of 5 mu m and the vinyl content of 1.5 wt% into 50 parts of butyl acetate for ultrasonic dispersion for 5 minutes, adding 30.4 parts of HS-POSS1, stirring uniformly, adding 0.4 part of benzoin dimethyl ether, and stirring at the dominant wavelength of 365nm and the light intensity of 5mW/cm 2 Ultraviolet ray of (2)Irradiating under light for 7 minutes, centrifuging, removing filtrate, collecting solid powder, and washing the powder with anhydrous ethanol for three times to obtain light diffusant 2. The refractive index of the light diffuser 2 was measured at 1.449(20 ℃ C.).
Example 3
Adding 10 parts of vinyl silicone resin microspheres with the average particle size of 8 mu m and the vinyl content of 2.1 wt% into 40 parts of ethyl acetate for ultrasonic dispersion for 5 minutes, adding 45.8 parts of HS-POSS1, stirring uniformly, adding 0.5 part of benzoin butyl ether, and stirring at the dominant wavelength of 365nm and the light intensity of 0.8mW/cm 2 Irradiating for 20 minutes under ultraviolet light, centrifuging, removing filtrate, collecting solid powder, and washing the powder with isopropanol three times to obtain the light diffusant 3. The refractive index of the light diffusing agent 3 was measured to be 1.455(20 ℃ C.).
Example 4
10 parts of vinyl silicone resin microspheres with the average particle size of 5 mu m and the vinyl content of 1.5 wt% are added into 40 parts of butyl acetate for ultrasonic dispersion for 8 minutes, 35.5 parts of HS-POSS2 are added, the mixture is stirred uniformly, 0.3 part of benzoin dimethyl ether is added, and the mixture is stirred uniformly under the conditions that the dominant wavelength is 365nm and the light intensity is 3mW/cm 2 Irradiating for 15 minutes under ultraviolet light, centrifuging, removing filtrate, collecting solid powder, and washing the powder with isopropanol three times to obtain the light diffusant 4. The refractive index of the light diffusing agent 4 was measured to be 1.491(20 ℃ C.).
Example 5
10 parts of vinyl silicone resin microspheres with the average particle size of 8 mu m and the vinyl content of 2.5 weight percent are added into 50 parts of butyl acetate for ultrasonic dispersion for 6 minutes, 64.1 parts of HS-POSS2 are added and stirred uniformly, 0.3 part of benzoin butyl ether is added, and the mixture is stirred uniformly under the conditions that the dominant wavelength is 365nm and the light intensity is 3mW/cm 2 Irradiating for 15 minutes under ultraviolet light, centrifuging, removing filtrate, collecting solid powder, and washing the powder with isopropanol three times to obtain the light diffusion agent 5. The refractive index of the light diffusing agent 5 was measured to be 1.502(20 ℃).
Applications of
Adding the light diffusant and the polymer resin material into PC and PMMA according to the weight ratio of 0.4:99.6, and extruding and pelletizing by a double screw. The specific formulation is shown in table 1.
TABLE 1
Figure BDA0002338125260000051
Figure BDA0002338125260000061
Test method
The composite material of the light diffusing agent and the resin material for each application was injection-molded into a sheet material of 10mm × 10mm × 2mm using a high-specular mold having a center line average roughness of 1.0 nm.
Haze and light transmittance: the plaques are tested according to ASTM D1003-61(97) using HR-100 haze transmittance reflectometry. The results are shown in Table 2.
Evaluation of light diffusibility: placing the plate at a position 1cm away from a 5W LED light source, observing the light diffusion effect at the position opposite to the light source, wherein the optical fiber is uniform and has no bright spot of grade 1; the optical fiber is uniform, and has slight bright spots of grade 2; the optical fiber is not uniform, and the obvious bright spot is grade 3. The results are shown in Table 2.
Mechanical strength: and testing the tensile strength and the bending strength of the plate by using an electronic tensile machine. The results are shown in Table 2.
Heat resistance: the initial decomposition temperature of the above composite material under nitrogen atmosphere was measured by DSC. The results are shown in Table 2.
TABLE 2
Figure BDA0002338125260000062
Figure BDA0002338125260000071
From the results in table 2, it can be seen that the light diffusing agent of the present invention, when added to the polymer resin materials PC and PMMA, can significantly improve the haze, light diffusivity, tensile strength, bending strength and heat resistance of the polymer resin materials, and has a small influence on the light transmittance, indicating that the light diffusing agent of the present invention has a good dispersibility in the polymer resin materials. The light diffusing agent of the present invention can make the polymer resin material have better haze even under the condition that the refractive index is close to that of the polymer resin material.
The foregoing has shown and described the fundamental principles, major features and advantages of the invention. It should be understood by those skilled in the art that the present invention is not limited by the foregoing examples, which are only preferred embodiments of the present invention, and the scope of the present invention should not be limited by these examples. The scope of the invention is defined by the appended claims and equivalents thereof.

Claims (9)

1. A preparation method of a light diffusion agent is characterized by comprising the following steps: the preparation method is characterized in that the preparation method comprises the following steps of adding vinyl silicone resin microspheres into a first organic solvent for ultrasonic dispersion for 5-10 minutes, and adding a compound with a chemical general formula of R 1 R 2 7 (SiO 1.5 ) 8 The single-functional cage-type octa-polysilsesquioxane is evenly stirred, and a photoinitiator is added, wherein the dominant wavelength is 365nm, and the light intensity is 0.5-10mW/cm 2 Irradiating for 0.2-20 minutes under ultraviolet light, centrifuging, removing filtrate, collecting solid powder, and cleaning the powder with a second organic solvent for three times to obtain a light diffusant; the R is 1 Selected from 2-mercaptoethyl or 3-mercaptopropyl, said R 2 One selected from isobutyl, phenyl, methyl, propyl and gamma-chloropropyl.
2. The method for producing a light diffusing agent according to claim 1, characterized in that: the average grain diameter of the vinyl silicone resin microspheres is 0.5-20 μm, and the mass percentage of vinyl is 0.1-5%.
3. The method for producing a light diffusing agent according to claim 1, characterized in that: the first organic solvent is selected from one or a combination of acetone, ethyl acetate, butyl acetate, xylene, trimethylbenzene, toluene, methyl ethyl ketone, cyclohexanone and ethylene glycol dimethyl ether.
4. The method for producing a light diffusing agent according to claim 1, characterized in that: the weight ratio of the vinyl silicone resin microspheres to the first organic solvent is 1: 2-10.
5. The method for producing a light diffusing agent according to claim 1, wherein: the ratio of the mole number of vinyl groups of the vinyl silicon resin microspheres to the mole number of the cage-type octasilsesquioxane is 1: 1.05-2.
6. The method for producing a light diffusing agent according to claim 1, wherein: the photoinitiator is selected from one or a composition of benzoin dimethyl ether, benzoin ethyl ether and benzoin butyl ether, and the usage weight of the photoinitiator is 1-5% of the weight of the vinyl silicone resin microspheres.
7. The method for producing a light diffusing agent according to claim 1, characterized in that: the second solvent is selected from one or a combination of absolute ethyl alcohol, isopropanol, acetone and butyl acetate.
8. A light diffusing agent produced by the method for producing a light diffusing agent according to any one of claims 1 to 7.
9. Use of the light diffuser of claim 8 in polycarbonate, polyacrylate, polyphenylene sulfide, polypropylene, polyethylene or polyester.
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Publication number Priority date Publication date Assignee Title
US5352747A (en) * 1992-12-24 1994-10-04 Ge Plastics, Japan, Ltd. Light-diffusing polycarbonate resin compositions containing polymethyl silsesquioxane
CN103122070A (en) * 2011-10-14 2013-05-29 信越化学工业株式会社 Silicone fine particles and production method thereof
CN103755901A (en) * 2014-01-21 2014-04-30 上海交通大学 Preparation method of octasulfydryl polyhedral oligomeric silsesquioxane modified elastomer material

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5352747A (en) * 1992-12-24 1994-10-04 Ge Plastics, Japan, Ltd. Light-diffusing polycarbonate resin compositions containing polymethyl silsesquioxane
CN103122070A (en) * 2011-10-14 2013-05-29 信越化学工业株式会社 Silicone fine particles and production method thereof
CN103755901A (en) * 2014-01-21 2014-04-30 上海交通大学 Preparation method of octasulfydryl polyhedral oligomeric silsesquioxane modified elastomer material

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