CN101343365A - Preparation method for methyl phenyl vinyl polysiloxane for packaging LED - Google Patents
Preparation method for methyl phenyl vinyl polysiloxane for packaging LED Download PDFInfo
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- CN101343365A CN101343365A CNA200810120378XA CN200810120378A CN101343365A CN 101343365 A CN101343365 A CN 101343365A CN A200810120378X A CNA200810120378X A CN A200810120378XA CN 200810120378 A CN200810120378 A CN 200810120378A CN 101343365 A CN101343365 A CN 101343365A
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- toluene
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- water
- sicl
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- -1 methyl phenyl vinyl Chemical group 0.000 title claims abstract description 46
- 238000002360 preparation method Methods 0.000 title claims abstract description 27
- 238000004806 packaging method and process Methods 0.000 title claims abstract description 7
- 229920001296 polysiloxane Polymers 0.000 title claims description 22
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims abstract description 279
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 67
- 238000006068 polycondensation reaction Methods 0.000 claims abstract description 22
- 239000002904 solvent Substances 0.000 claims abstract description 10
- 239000005046 Chlorosilane Substances 0.000 claims abstract description 9
- 239000003153 chemical reaction reagent Substances 0.000 claims abstract description 9
- KOPOQZFJUQMUML-UHFFFAOYSA-N chlorosilane Chemical compound Cl[SiH3] KOPOQZFJUQMUML-UHFFFAOYSA-N 0.000 claims abstract description 9
- 238000006460 hydrolysis reaction Methods 0.000 claims abstract description 6
- 239000000203 mixture Substances 0.000 claims abstract description 5
- 238000006243 chemical reaction Methods 0.000 claims abstract description 4
- 238000003756 stirring Methods 0.000 claims description 39
- 230000007935 neutral effect Effects 0.000 claims description 26
- SCPYDCQAZCOKTP-UHFFFAOYSA-N silanol Chemical compound [SiH3]O SCPYDCQAZCOKTP-UHFFFAOYSA-N 0.000 claims description 25
- 239000008367 deionised water Substances 0.000 claims description 24
- 229910021641 deionized water Inorganic materials 0.000 claims description 24
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 18
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims description 16
- 229920002554 vinyl polymer Polymers 0.000 claims description 16
- 239000000047 product Substances 0.000 claims description 15
- 239000012141 concentrate Substances 0.000 claims description 14
- 239000000178 monomer Substances 0.000 claims description 14
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical group [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 12
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 8
- IJOOHPMOJXWVHK-UHFFFAOYSA-N chlorotrimethylsilane Chemical group C[Si](C)(C)Cl IJOOHPMOJXWVHK-UHFFFAOYSA-N 0.000 claims description 8
- 229920000642 polymer Polymers 0.000 claims description 8
- 239000003054 catalyst Substances 0.000 claims description 7
- WGTYBPLFGIVFAS-UHFFFAOYSA-M tetramethylammonium hydroxide Chemical compound [OH-].C[N+](C)(C)C WGTYBPLFGIVFAS-UHFFFAOYSA-M 0.000 claims description 6
- UQEAIHBTYFGYIE-UHFFFAOYSA-N hexamethyldisiloxane Chemical compound C[Si](C)(C)O[Si](C)(C)C UQEAIHBTYFGYIE-UHFFFAOYSA-N 0.000 claims description 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 5
- CRXNJSWBRJXDTE-UHFFFAOYSA-N Cl[SiH2]Cl.CC=C Chemical compound Cl[SiH2]Cl.CC=C CRXNJSWBRJXDTE-UHFFFAOYSA-N 0.000 claims description 4
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims description 4
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 claims description 4
- DKPFZGUDAPQIHT-UHFFFAOYSA-N butyl acetate Chemical compound CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 claims description 4
- QABCGOSYZHCPGN-UHFFFAOYSA-N chloro(dimethyl)silicon Chemical compound C[Si](C)Cl QABCGOSYZHCPGN-UHFFFAOYSA-N 0.000 claims description 4
- GNEPOXWQWFSSOU-UHFFFAOYSA-N dichloro-methyl-phenylsilane Chemical compound C[Si](Cl)(Cl)C1=CC=CC=C1 GNEPOXWQWFSSOU-UHFFFAOYSA-N 0.000 claims description 4
- LIKFHECYJZWXFJ-UHFFFAOYSA-N dimethyldichlorosilane Chemical compound C[Si](C)(Cl)Cl LIKFHECYJZWXFJ-UHFFFAOYSA-N 0.000 claims description 4
- 239000007788 liquid Substances 0.000 claims description 4
- 239000006228 supernatant Substances 0.000 claims description 4
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 4
- 239000005051 trimethylchlorosilane Substances 0.000 claims description 4
- 239000003643 water by type Substances 0.000 claims description 4
- 239000000413 hydrolysate Substances 0.000 claims description 3
- 239000007787 solid Substances 0.000 claims description 3
- YJTKZCDBKVTVBY-UHFFFAOYSA-N 1,3-Diphenylbenzene Chemical group C1=CC=CC=C1C1=CC=CC(C=2C=CC=CC=2)=C1 YJTKZCDBKVTVBY-UHFFFAOYSA-N 0.000 claims description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- OSXYHAQZDCICNX-UHFFFAOYSA-N dichloro(diphenyl)silane Chemical compound C=1C=CC=CC=1[Si](Cl)(Cl)C1=CC=CC=C1 OSXYHAQZDCICNX-UHFFFAOYSA-N 0.000 claims description 2
- 239000012467 final product Substances 0.000 claims description 2
- 239000005055 methyl trichlorosilane Substances 0.000 claims description 2
- JLUFWMXJHAVVNN-UHFFFAOYSA-N methyltrichlorosilane Chemical compound C[Si](Cl)(Cl)Cl JLUFWMXJHAVVNN-UHFFFAOYSA-N 0.000 claims description 2
- 239000011734 sodium Substances 0.000 claims description 2
- 229910000029 sodium carbonate Inorganic materials 0.000 claims description 2
- 238000005406 washing Methods 0.000 claims description 2
- 239000000463 material Substances 0.000 abstract description 21
- 238000000034 method Methods 0.000 abstract description 10
- 230000005855 radiation Effects 0.000 abstract description 6
- 230000005540 biological transmission Effects 0.000 abstract description 5
- 229920002050 silicone resin Polymers 0.000 abstract description 5
- 239000003292 glue Substances 0.000 abstract description 4
- 239000000565 sealant Substances 0.000 abstract description 4
- 239000000853 adhesive Substances 0.000 abstract 1
- 230000001070 adhesive effect Effects 0.000 abstract 1
- 238000005352 clarification Methods 0.000 abstract 1
- 239000005022 packaging material Substances 0.000 abstract 1
- 239000002253 acid Substances 0.000 description 12
- 238000001816 cooling Methods 0.000 description 12
- 238000002156 mixing Methods 0.000 description 10
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 8
- 229910052739 hydrogen Inorganic materials 0.000 description 5
- 239000001257 hydrogen Substances 0.000 description 5
- 238000002834 transmittance Methods 0.000 description 5
- 230000000903 blocking effect Effects 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 238000005538 encapsulation Methods 0.000 description 3
- 150000002431 hydrogen Chemical class 0.000 description 3
- 238000000465 moulding Methods 0.000 description 3
- 229920005989 resin Polymers 0.000 description 3
- 239000011347 resin Substances 0.000 description 3
- 239000004065 semiconductor Substances 0.000 description 3
- 229920002545 silicone oil Polymers 0.000 description 3
- 229920002379 silicone rubber Polymers 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- 239000004593 Epoxy Substances 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 2
- 235000010290 biphenyl Nutrition 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 239000003822 epoxy resin Substances 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 230000003287 optical effect Effects 0.000 description 2
- 239000002245 particle Substances 0.000 description 2
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
- 229920000647 polyepoxide Polymers 0.000 description 2
- 229910052710 silicon Inorganic materials 0.000 description 2
- 239000010703 silicon Substances 0.000 description 2
- 238000005245 sintering Methods 0.000 description 2
- WUOACPNHFRMFPN-SECBINFHSA-N (S)-(-)-alpha-terpineol Chemical compound CC1=CC[C@@H](C(C)(C)O)CC1 WUOACPNHFRMFPN-SECBINFHSA-N 0.000 description 1
- 229920001342 Bakelite® Polymers 0.000 description 1
- 241000237502 Ostreidae Species 0.000 description 1
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 230000032683 aging Effects 0.000 description 1
- OVKDFILSBMEKLT-UHFFFAOYSA-N alpha-Terpineol Natural products CC(=C)C1(O)CCC(C)=CC1 OVKDFILSBMEKLT-UHFFFAOYSA-N 0.000 description 1
- 229940088601 alpha-terpineol Drugs 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000002131 composite material Substances 0.000 description 1
- 230000001351 cycling effect Effects 0.000 description 1
- 230000007812 deficiency Effects 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 230000018109 developmental process Effects 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 235000021323 fish oil Nutrition 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000005286 illumination Methods 0.000 description 1
- 239000004973 liquid crystal related substance Substances 0.000 description 1
- 238000012423 maintenance Methods 0.000 description 1
- 239000011159 matrix material Substances 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 235000019198 oils Nutrition 0.000 description 1
- 125000001181 organosilyl group Chemical group [SiH3]* 0.000 description 1
- 235000020636 oyster Nutrition 0.000 description 1
- 238000012856 packing Methods 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 239000004945 silicone rubber Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 125000002769 thiazolinyl group Chemical group 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- 238000004073 vulcanization Methods 0.000 description 1
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- Silicon Polymers (AREA)
Abstract
The invention discloses a preparation method for organosilicon, in particular relates to a preparation method of methyl-phenyl-vinyl silicone resin with high refractive index and high light transmission rate for packaging LED. The preparation method adopts the steps that the mixture of chlorosilane and toluene is added into the solvent which is composed of water and the toluene, the hydrolysis reaction is performed, then an amount of catalyzer is added into the silanol-toluene solution as hysrolysis product, the polycondensation reaction is performed, end capping reagent is finally added to perform the reaction, thus the objective product is obtained. The methyl-phenyl-vinyl silicone resin prepared by utilizing the method has the advantages of high refractive index, transparent clarification, radiation resistance, and high and low temperature resistance and weather resistance, thereby being especially suitable for the high modular basic glue in the packaging material for LED and expected to be applied in organosilicon material such as elastomeric sealant, pouring sealant, elastomoric adhesive and the like.
Description
Technical field
The present invention relates to a kind of organosilyl preparation method, refer in particular to the preparation method of a kind of LED encapsulation with high refractive index, high transmission rate methyl phenyl vinyl polysiloxane.
Technical background
Power type light-emitting diode (Light Emitting Diode, LED) through the development of decades, be widely used in the big area picture and text and show that full-color screen, state indication, sign illumination, signal show, Backlight For Liquid Crystal Display Panels, aspects such as automobile combined tail lamp and room light.LED has energy-saving and environmental protection, safety, life-span length, low consumption, low-heat, shockproof, waterproof, miniature, high brightness, easily light modulation, light beam is concentrated and reduce advantage such as maintenance, be expected to become after incandescent light, luminescent lamp, high-intensity gas discharge lamp the 4th generation light source.
Traditional LED packaged material is a Resins, epoxy.Because the specific refractory power between semi-conductor and the epoxy resin encapsulating material differs bigger, finally influences the optical efficiency of getting of semiconductor material.On the other hand, Resins, epoxy thermal resistance height, flavescence easily, not UV resistant radiation.Organosilicon material has advantages such as high-low temperature resistant, ageing-resistant, UV resistant, radiation hardness, is ideal LED packaged material.WO2004107458 has reported under the platinum catalyst effect, the crosslinked method for preparing the LED packaged material of ethenyl blocking silicone resin and containing hydrogen silicone oil, and behind the packaged material sulfidization molding, shrinking percentage is low, and fast light Good Heat-resistance does not ftracture and transmittance reaches 95%.U.S. Pat 20050212008 (its equating patent EP1424363) has been reported employing silicon hydrogen addition vulcanization technology, with ethenyl blocking silicon rubber and the crosslinked preparation power-type LED of containing hydrogen silicone oil packaged material, the refractive index of packaged material reaches 1.51 behind the sulfidization molding, behind 400nm light source irradiation 100h, transmittance drops to 92% from initial 95%, behind the irradiation 500h still is 92%, obviously is better than epoxy resin encapsulating material.U.S. Pat 20050006794 has been reported employing silicon hydrogen additive process, organo-silicone rubber and the crosslinked method for preparing the LED packaged material of containing hydrogen silicone oil with ethenyl blocking, packaged material behind the sulfidization molding has excellent mechanical property and non-viscosity energy, can stand the cold cycling impact between 1000 times-50 ℃ to 150 ℃ and does not ftracture.
External semiconductor lighting company and main organosilicon material manufacturing enterprise have all carried out research and have applied for patent the optical grade organosilicon encapsulating material, and that domestic correlative study is still owed is active.Have only the report of three pieces of Chinese patents at present relevant for LED, they are respectively one piece of patent " a kind of white light LEDs and method for packing thereof " (Chinese invention patents of Zhongshan University's application, CN1838440A), reported the method that adopts silicon rubber encapsulation white light LEDs, and organosilicon material itself has not been made reports; One piece of patent " with the method for nano mattisolda low temp sintering, packaging and connecting high power LED " (Chinese invention patent of University Of Tianjin's application, CN1870310), method in this invention is to adopt particle diameter less than the 100nm nano silver particles, prepare the nano mattisolda of gained, low temp sintering, packaging and connecting high power LED with dispersion agent fish oil, binding agent alpha-terpineol and solvent acetone uniform mixing under ultrasonic water bath is assisted; One piece of patent (Chinese invention patent that is entitled as " transparent composite composition " of SUMITOMO CHEMICAL bakelite Co., Ltd. application, CN1649966), this patent report a kind ofly use general glass filler, the matrix material that has high transmitance in very wide wavelength region, this material can be used for the LED encapsulation.These two patents do not relate to organosilicon encapsulating material.
Want the basic glue as the LED packaged material, the necessary even structure of silicone resin, purity height, highly transparent and refractive index contain two active vinyl at least greater than 1.5 in the molecule, have the suitable viscosity and the degree of branching simultaneously.Above-mentioned foreign patent thiazolinyl silicone resin all is to use Ph
2SiCl
2With Me
2SiCl
2, MeViSiCl
2Deng cohydrolysis-polycondensation and get.Because Ph
2SiCl
2With Me
2SiCl
2And MeViSiCl
2Hydrolytic activity differs greatly, it is complicated to make product form, wherein both there had been the organic block polymkeric substance that contains phenylbenzene silica chain link and dimethyl silica chain link simultaneously, also there is the polymkeric substance of only forming by dimethyl silica chain link or phenylbenzene silica chain link, each component refractive index difference is bigger, finally causes the product transmittance lower.
Summary of the invention
The present invention is directed to deficiency of the prior art, propose a kind of effective process for preparing resins that improves refractive index, transmittance.
The present invention is achieved by following technical proposals:
A kind of preparation method of LED methyl phenyl vinyl polysiloxane for packaging is characterized in that being undertaken by following step:
(1) mixture of chlorosilane and toluene is joined in 0 ℃ ~ 60 ℃ the solvent of forming by water and toluene, react the hydrolysis reaction of 0.5h ~ 10h;
(2) after reaction finishes, leave standstill, layering, get supernatant liquid, with 30 ℃ ~ 60 ℃ deionized waters the supernatant liquid washing to neutrality, obtain hydrolysate silanol toluene solution; What obtained this moment is about solid content 50% hydrolysate silanol toluene solution;
(3) the silanol toluene solution being made into solid content is 20 ~ 30% silanol toluene solution, adds proper catalyst, carries out polycondensation, and backflow 0.5h ~ 12h adds an amount of end-capping reagent after being cooled to room temperature, stirs behind 0.5h ~ 5h with deionized water wash to neutral;
(4) with the product that obtains in the step (3), under 0.8MPa ~ 0.96MPa, concentrate, and remove the water of toluene and polycondensation generation, get final product product.
Polyreaction general formula among the present invention is as follows:
As preferably, the chlorosilane as polymer monomer described in the above-mentioned preparation method is phenyl-trichloro-silicane (PhSiCl
3), methyl ethylene dichlorosilane (MeViSiCl
2), dimethyldichlorosilane(DMCS) (Me
2SiCl
2), dichloromethyl phenylsilane (MePhSiCl
2), METHYL TRICHLORO SILANE (MeSiCl
3), diphenyl dichlorosilane (Ph
2SiCl
2) in one or more;
In the solvent that described toluene and water are formed, the toluene consumption is 0.5 ~ 5 times of monomer consumption (quality), and the consumption of water is 1 ~ 20 times of monomer consumption (quality);
Described hydrolysis reaction is to be to carry out under 20 ℃ ~ 50 ℃ conditions in temperature, and return time is 2 ~ 6h;
Described end-capping reagent is trimethylchlorosilane (Me
3SiCl), tri-phenyl chloride (Ph
3SiCl), one or more in the hexamethyldisiloxane (MM);
Described catalyzer is sodium hydroxide (NaOH), potassium hydroxide (KOH), sodium carbonate solution (Na
2CO
3), in the Tetramethylammonium hydroxide one or more;
The used solvent of preparation silanol toluene solution described in the step (3) is one or more in toluene, dimethylbenzene, di-toluene, tetrahydrofuran (THF), N-BUTYL ACETATE, Virahol, propyl carbinol, sherwood oil and the water;
As preferably, described polycondensation is to carry out under temperature is 40 ℃ ~ 120 ℃ condition.As more preferably selecting, the temperature of described polycondensation is 60 ℃ ~ 100 ℃.
As better selection, the chlorosilane as polymer monomer described in the above-mentioned preparation method is dichloromethyl phenylsilane (MePhSiCl
2), phenyl-trichloro-silicane (PhSiCl
3), methyl ethylene dichlorosilane (MeViSiCl
2) and dimethyldichlorosilane(DMCS) (Me
2SiCl
2), its consumption is 0.2 ~ 0.9 (mol ratio) according to Ph/R, and Vi/R is 0.01 ~ 0.4 (mol ratio), and wherein: Ph is a phenyl,
R is alkyl (Me), phenyl (Ph), vinyl (Vi).
The consumption of described chlorosilane as polymer monomer is 0.3 ~ 0.6 (mol ratio) according to Ph/R, better effects if when Vi/R is 0.10 ~ 0.35 (mol ratio).
As preferably, in the solvent that toluene described in the above-mentioned preparation method and water are formed, the toluene consumption is 1 ~ 2 times of monomer consumption (quality), and the consumption of water is 5 ~ 10 times of monomer consumption (quality).
As preferably, the catalyzer described in the above-mentioned preparation method is potassium hydroxide (KOH), and catalyst levels (mass concentration) is 0.1 ‰ ~ 100 ‰.As better selection, described catalyzer is potassium hydroxide (KOH), and catalyst levels (mass concentration) is 0.1 ‰ ~ 5 ‰.
As preferably, the end-capping reagent described in the above-mentioned preparation method is trimethylchlorosilane (Me
3SiCl) and/or hexamethyldisiloxane (MM), its consumption by 0.5% ~ 10% (mass percent) of adding silanol toluene solution.As better selection, described end-capping reagent be consumption by 1.0% ~ 5% (mass percent) of adding silanol toluene solution.
This patent adopts and Me
2SiCl and MeViSiCl
2The equimolecular structure is close, the MePhSiCl that hydrolysis rate is comparatively approaching
2Replace Ph
2SiCl
2, it is more even to make product form, and improves the transmittance of product effectively; In addition, use MePhSiCl
2Replace Ph
2SiCl
2, it is more even to make in the product that phenyl disperses, and can improve the resistance to ultraviolet(ray) radiation energy of product.The present invention optimizes synthesis techniques such as temperature of reaction and polymerization time by the control proportioning raw materials, has obtained a series of high refractive index, high transmission rate, has contained the methyl phenyl vinyl polysiloxane of aminomethyl phenyl silica chain link.
Beneficial effect: the methyl phenyl vinyl polysiloxane with method preparation of the present invention contains aminomethyl phenyl silica chain link, the methyl phenyl vinyl polysiloxane of high refractive index, high transmission rate.Prepared methyl phenyl vinyl polysiloxane refractive index is 1.48 ~ 1.54,0.10 ~ 0.35 (mol ratio), R/Si is 1.20 ~ 1.70 (mol ratios), toluene viscosity is 1.4 ~ 6.8 relatively, have high refractive index, high transmission rate, radiation hardness, high-low temperature resistant, advantage such as weather-proof are especially suitable for use as polymer basis glue in the LED packaged material, also are expected to be used for other seal gum, joint sealant and tackiness agent.Methyl phenyl vinyl polysiloxane of the present invention has good performance, as high refractive index, clear, radiation hardness, high-low temperature resistant, weather-proof, be particularly suitable for polymer basis glue in the LED packaged material, also be expected to be used for other seal gum, joint sealant and tackiness agent.
Embodiment
The present invention can further specify by following embodiment, but embodiment is not a limiting the scope of the invention.
Embodiment 1
In the 1L there-necked flask that 46ml toluene and 360ml water are housed, under 45 ℃ of stirrings, with 50ml PhSiCl
3, 39.2mlMeViSiCl
2, 45.1ml Me
2SiCl
2, the about 1h of 95ml toluene dropwises, and continues to stir 1h.Leave standstill, layering, separating funnel removes the sub-cloud acid solution.Extremely neutral with 40 ℃ ~ 50 ℃ deionized waters.Get gained silanol toluene solution 50g, add 50g toluene, 0.05gKOH, 70 ~ 80 ℃ of following backflow 5h in the 250ml there-necked flask, cooling adds 1.5g MeSiCl
3, stirring 1h, deionized water wash is to neutral.Concentrate under 0.8MPa ~ 0.96MPa, and remove the water of residual toluene and polycondensation generation, gained clear methyl phenyl vinyl polysiloxane, the molar content of its vinyl are 0.304, R/Si=1.38, refractive index 1.490.
Embodiment 2
In the 1L there-necked flask that 46ml toluene and 360ml water are housed, under 40 ℃ of stirrings, Dropwise 5 0ml PhSiCl in the 2h
3, 22ml MeViSiCl
2, 26ml Me
2SiCl
2, 35ml MePhSiCl
2, 88ml toluene mixing solutions, continue to stir 1h.Leave standstill, layering, separating funnel removes the sub-cloud acid solution.To neutral, the silanol toluene solution 50g that obtains adds 50g toluene with 40 ℃ ~ 50 ℃ deionized water wash 7-8 time, 0.05gKOH, and 70 ~ 80 ℃ of following backflow 2h in the 250ml there-necked flask, cooling adds 1.5g MeSiCl
3, stirring 1h, deionized water wash is to neutral.Concentrate under 0.8MPa ~ 0.96MPa, and remove the water of residual toluene and polycondensation generation, obtain the clear methyl phenyl vinyl polysiloxane, the molar content of its vinyl is 0.185, R/Si=1.47, refractive index n
D 25=1.5465.
Embodiment 3
In the 1L there-necked flask that 46ml toluene and 360ml water are housed, under 50 ℃ of stirrings, Dropwise 5 0ml PhSiCl in the 2h
3, 22ml MeViSiCl
2, 13ml Me
2SiCl
2, 17.5ml MePhSiCl
2, 88ml toluene mixing solutions, continue to stir 1h.Leave standstill, layering, separating funnel removes the sub-cloud acid solution.To neutral, the silanol toluene solution 50g that obtains adds 50g toluene with 40 ℃ ~ 50 ℃ deionized water wash 7-8 time, 0.15g KOH, and 70 ~ 80 ℃ of following backflow 2h in the 250ml there-necked flask, cooling adds 4.5g MeSiCl
3, stirring 1h, deionized water wash is to neutral.Under 0.8MPa ~ 0.96MPa, concentrate, and remove the water that residual toluene and polycondensation generate, obtain containing the product of part white filament, after activated carbon decolorizing, filtration, be the water white transparency methyl phenyl vinyl polysiloxane, the molar content of its vinyl is 0.242, R/Si=1.31, refractive index n
D 25=1.5250.
Embodiment 4
In the 1L there-necked flask that 46ml toluene and 360ml water are housed, under 40 ℃ of stirrings, Dropwise 5 0ml PhSiCl in the 2h
3, 22ml MeViSiCl
2, 18ml Me
2SiCl
2, 9ml MePhSiCl
2, 88ml toluene mixing solutions, continue to stir 1h.Leave standstill, layering, separating funnel removes the sub-cloud acid solution.To neutral, the silanol toluene solution 50g that obtains adds 50g toluene with 40 ℃ ~ 50 ℃ deionized water wash 7-8 time, 0.05gKOH, and 70 ~ 80 ℃ of following backflow 5h in the 250ml there-necked flask, cooling adds 1.5g MeSiCl
3, stirring 1h, deionized water wash is to neutral.Under 0.8MPa ~ 0.96MPa, concentrate, and remove the water that residual toluene and polycondensation generate, obtain containing the product of part white filament, after activated carbon decolorizing, filtration, be the water white transparency methyl phenyl vinyl polysiloxane, the molar content of its vinyl is 0.242, R/Si=1.31, refractive index n
D 25=1.5250.
Embodiment 5
In the 1L there-necked flask that 46ml toluene and 360ml water are housed, 40 ℃, stir under Dropwise 5 0ml PhSiCl in the 2h
3, 22ml MeViSiCl
2, 26ml Me
2SiCl
2, 26ml MePhSiCl
2, 88ml toluene continues to stir 1h.Leave standstill, layering, separating funnel removes the sub-cloud acid solution.With 40 ℃ ~ 50 ℃ deionized water wash 7-8 time to neutral.The silanol toluene solution 50g that obtains adds 50g toluene, 0.05g KOH, and 70 ~ 80 ℃ of following backflow 5h in the 250ml there-necked flask, cooling adds 1.5gMeSiCl
3, stirring 1h, deionized water wash is to neutral.Concentrate under 0.8MPa ~ 0.96MPa, and remove the water of residual toluene and polycondensation generation, the molar content of the methyl phenyl vinyl polysiloxane vinyl that obtains is 0.197, R/Si=1.44, refractive index n
D 25=1.5281.
Embodiment 6
In the 1L there-necked flask that 46ml toluene and 360ml water are housed, under 20 ℃ of stirrings, Dropwise 5 0ml PhSiCl in the 2h
3, 22ml MeViSiCl
2, 18ml Me
2SiCl
2, 9ml MePhSiCl
2, 88ml toluene mixing solutions, continue to stir 1h.Leave standstill, layering, separating funnel removes the sub-cloud acid solution.To neutral, the silanol toluene solution 50g that obtains adds 50g toluene with 40 ℃ ~ 50 ℃ deionized water wash 7-8 time, 0.05gKOH, and 100 ℃ of following backflow 5h in the 250ml there-necked flask, cooling adds 1.5g MeSiCl
3, stirring 1h, deionized water wash is to neutral.Concentrate under 0.8MPa ~ 0.96MPa, and remove the water of residual toluene and polycondensation generation, obtain water white transparency, flowability methyl phenyl vinyl polysiloxane preferably, its vinyl molar content is 0.242, R/Si=1.31, refractive index n
D 25=1.5184.
Embodiment 7
In the 1L there-necked flask that 46ml toluene and 360ml water are housed, under 30 ℃ of stirrings, Dropwise 5 0ml PhSiCl in the 2h
3, 22ml MeViSiCl
2, 18ml Me
2SiCl
2, 9ml MePhSiCl
2, 88ml toluene mixing solutions, continue to stir 1h.Leave standstill, layering, separating funnel removes the sub-cloud acid solution.To neutral, the silanol toluene solution 50g that obtains adds 50g toluene with 40 ℃ ~ 50 ℃ deionized water wash 7-8 time, 0.05gKOH, and 100 ℃ of following backflow 5h in the 250ml there-necked flask, cooling adds 1.5g MeSiCl
3, stirring 1h, deionized water wash is to neutral.Under 0.8MPa ~ 0.96MPa, concentrate, and remove the water of residual toluene and polycondensation generation, obtain containing oyster white filament product, after stirring, decolour, gac obtains transparent methyl phenyl vinyl polysiloxane, its vinyl molar content is 0.242, R/Si=1.31, refractive index n
D 25=1.5255.
Embodiment 8
In the 1L there-necked flask that 46ml toluene and 360ml water are housed, under 50 ℃ of stirrings, Dropwise 5 0ml PhSiCl in the 2h
3, 22ml MeViSiCl
2, 18ml Me
2SiCl
2, 9ml MePhSiCl
2, 88ml toluene mixing solutions, continue to stir 1h.Leave standstill, layering, separating funnel removes the sub-cloud acid solution.To neutral, the silanol toluene solution 50g that obtains adds 50g toluene with 40 ℃ ~ 50 ℃ deionized water wash 7-8 time, 0.05gKOH, and 100 ℃ of following backflow 5h in the 250ml there-necked flask, cooling adds 1.5g MeSiCl
3, stirring 1h, deionized water wash is to neutral.Concentrate under 0.8MPa ~ 0.96MPa, and remove the water of residual toluene and polycondensation generation, obtain muddy thickness methyl phenyl vinyl polysiloxane, its vinyl molar content is 0.242, R/Si=1.31, refractive index n
D 25=1.5250.
Embodiment 9
In the 1L there-necked flask that 46ml toluene and 360ml water are housed, under 20 ℃ of stirrings, Dropwise 5 0ml PhSiCl in the 2h
3, 22ml MeViSiCl
2, 18ml Me
2SiCl
2, 9ml MePhSiCl
2, 88ml toluene mixing solutions, continue to stir 1h.Leave standstill, layering, separating funnel removes the sub-cloud acid solution.To neutral, the silanol toluene solution 50g that obtains adds 50g toluene with 40 ℃ ~ 50 ℃ deionized water wash 7-8 time, 0.005gKOH, and 100 ℃ of following backflow 5h in the 250ml there-necked flask, cooling adds 1.5g MeSiCl
3, stirring 1h, deionized water wash is to neutral.Concentrate under 0.8MPa ~ 0.96MPa, and remove the water of residual toluene and polycondensation generation, obtain the clear methyl phenyl vinyl polysiloxane, its vinyl molar content is 0.242, R/Si=1.31, refractive index n
D 25=1.5165.
Embodiment 10
In the 1L there-necked flask that 46ml toluene and 360ml water are housed, under 20 ℃ of stirrings, Dropwise 5 0ml PhSiCl in the 2h
3, 22ml MeViSiCl
2, 18ml Me
2SiCl
2, 9ml MePhSiCl
2, 88ml toluene mixing solutions, continue to stir 1h.Leave standstill, layering, separating funnel removes the sub-cloud acid solution.To neutral, the silanol toluene solution 50g that obtains adds 50g toluene with 40 ℃ ~ 50 ℃ deionized water wash 7-8 time, 0.15gKOH, and 100 ℃ of following backflow 5h in the 250ml there-necked flask, cooling adds 1.5g MeSiCl
3, stirring 1h, deionized water wash is to neutral.Under 0.8MPa ~ 0.96MPa, concentrate, and remove the water of residual toluene and polycondensation generation, obtain adularescent crystal in the product, filter acquisition clear methyl phenyl vinyl polysiloxane through activated carbon decolorizing, its vinyl molar content is 0.242, R/Si=1.31, refractive index n
D 25=1.5270.
Embodiment 11
In the 1L there-necked flask that 46ml toluene and 360ml water are housed, under 45 ℃ of stirrings, with 50ml PhSiCl
3, 39.2mlMeViSiCl
2, 45.1ml Me
2SiCl
2, the about 1h of 95ml toluene dropwises, and continues to stir 1h.Leave standstill, layering, separating funnel removes the sub-cloud acid solution.Extremely neutral with 40 ℃ ~ 50 ℃ deionized waters.Get gained silanol toluene solution 50g, add 50g toluene, 0.05gNaOH, 90 ℃ of following backflow 5h in the 250ml there-necked flask, cooling adds 2.1g PhSiCl
3, stirring 1h, deionized water wash is to neutral.Concentrate under 0.85MPa ~ 0.90MPa, and remove the water of residual toluene and polycondensation generation, gained clear methyl phenyl vinyl polysiloxane, the molar content of its vinyl are 0.304, R/Si=1.38, refractive index 1.500.
Embodiment 12
In the 1L there-necked flask that 46ml toluene and 360ml water are housed, under 30 ℃ of stirrings, Dropwise 5 0mlPhSiCl in the 2h
3, 22ml MeViSiCl
2, 18ml Me
2SiCl
2, 9ml MePhSiCl
2, 88ml toluene mixing solutions, continue to stir 1h.Leave standstill, layering, separating funnel removes the sub-cloud acid solution.With 40 ℃ ~ 50 ℃ deionized water wash 7-8 time to neutral, the silanol toluene solution 50g that obtains, add 50g toluene, 0.10g Tetramethylammonium hydroxide, 100 ℃ of following backflow 5h in the 250ml there-necked flask, cooling adds 1.6g hexamethyldisiloxane (MM), stir 1h, deionized water wash is to neutral.Under 0.8MPa ~ 0.96MPa, concentrate, and remove the water of residual toluene and polycondensation generation, obtain adularescent crystal in the product, filter acquisition clear methyl phenyl vinyl polysiloxane through activated carbon decolorizing, its vinyl molar content is 0.241, R/Si=1.30, refractive index n
D 25=1.5170.
Claims (10)
1, a kind of preparation method of LED methyl phenyl vinyl polysiloxane for packaging is characterized in that being undertaken by following step:
(1) mixture of chlorosilane and toluene is joined in 0 ℃ ~ 60 ℃ the solvent of forming by water and toluene, react the hydrolysis reaction of 0.5h ~ 10h;
(2) after reaction finishes, leave standstill, layering, get supernatant liquid, with 30 ℃ ~ 60 ℃ deionized waters the supernatant liquid washing to neutrality, obtain hydrolysate silanol toluene solution;
(3) the silanol toluene solution being made into solid content is 20 ~ 30% silanol toluene solution, adds proper catalyst, carries out polycondensation, and backflow 0.5h ~ 12h adds an amount of end-capping reagent after being cooled to room temperature, stirs behind 0.5h ~ 5h with deionized water wash to neutral;
(4) with the product that obtains in the step (3), under 0.8MPa ~ 0.96MPa, concentrate, and remove the water of toluene and polycondensation generation, get final product product.
2, preparation method according to claim 1 is characterized in that:
Described chlorosilane as polymer monomer is phenyl-trichloro-silicane (PhSiCl
3), methyl ethylene dichlorosilane (MeViSiCl
2), dimethyldichlorosilane(DMCS) (Me
2SiCl
2), dichloromethyl phenylsilane (MePhSiCl
2), METHYL TRICHLORO SILANE (MeSiCl
3), diphenyl dichlorosilane (Ph
2SiCl
2) in one or more;
In the solvent that described toluene and water are formed, the toluene consumption is 0.5 ~ 5 times of monomer consumption (quality), and the consumption of water is 1 ~ 20 times of monomer consumption (quality);
Described hydrolysis reaction is to be to carry out under 20 ℃ ~ 50 ℃ conditions in temperature, and return time is 2 ~ 6h;
Described end-capping reagent is trimethylchlorosilane (Me
3SiCl), tri-phenyl chloride (Ph
3SiCl), one or more in the hexamethyldisiloxane (MM);
Described catalyzer is sodium hydroxide (NaOH), potassium hydroxide (KOH), sodium carbonate solution (Na
2CO
3), in the Tetramethylammonium hydroxide one or more;
The used solvent of preparation silanol toluene solution described in the step (3) is one or more in toluene, dimethylbenzene, di-toluene, tetrahydrofuran (THF), N-BUTYL ACETATE, Virahol, propyl carbinol, sherwood oil and the water;
Described polycondensation is to carry out under temperature is 40 ℃ ~ 120 ℃ condition.
3, preparation method according to claim 2 is characterized in that described chlorosilane as polymer monomer is dichloromethyl phenylsilane (MePhSiCl
2), phenyl-trichloro-silicane (PhSiCl
3), methyl ethylene dichlorosilane (MeViSiCl
2) and dimethyldichlorosilane(DMCS) (Me
2SiCl
2), its consumption is 0.2 ~ 0.9 (mol ratio) according to Ph/R, Vi/R is 0.01 ~ 0.4 (mol ratio),
Wherein: Ph is a phenyl,
R is alkyl (Me), phenyl (Ph), vinyl (Vi).
4, preparation method according to claim 3 is characterized in that the consumption of described chlorosilane as polymer monomer is 0.3 ~ 0.6 (mol ratio) according to Ph/R, and Vi/R is 0.10 ~ 0.35 (mol ratio).
5, preparation method according to claim 2 is characterized in that the toluene consumption is 1 ~ 2 times of monomer consumption (quality) in the solvent of described toluene and water composition, and the consumption of water is 5 ~ 10 times of monomer consumption (quality).
6, preparation method according to claim 2 it is characterized in that described catalyzer is KOH, and catalyst levels (mass concentration) is 0.1 ‰ ~ 100 ‰.
7, preparation method according to claim 6 it is characterized in that described catalyzer is KOH, and catalyst levels (mass concentration) is 0.1 ‰ ~ 5 ‰.
8, preparation method according to claim 2 is characterized in that described end-capping reagent is trimethylchlorosilane (Me
3SiCl) and/or hexamethyldisiloxane (MM), its consumption by 0.5% ~ 10% (mass percent) of adding silanol toluene solution.
9, preparation method according to claim 8, it is characterized in that described end-capping reagent be consumption by 1.0% ~ 5% (mass percent) of adding silanol toluene solution.
10, preparation method according to claim 2, the temperature that it is characterized in that described polycondensation are 60 ℃～100 ℃.
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|---|---|---|---|
| CNA200810120378XA CN101343365A (en) | 2008-08-28 | 2008-08-28 | Preparation method for methyl phenyl vinyl polysiloxane for packaging LED |
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CNA200810120378XA CN101343365A (en) | 2008-08-28 | 2008-08-28 | Preparation method for methyl phenyl vinyl polysiloxane for packaging LED |
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|---|---|
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ID=40245487
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|---|---|---|---|
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