CN102634026B - Hydrogen-based silicone resin containing trifunctional group chain element and preparation method thereof - Google Patents
Hydrogen-based silicone resin containing trifunctional group chain element and preparation method thereof Download PDFInfo
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- CN102634026B CN102634026B CN201210096422.4A CN201210096422A CN102634026B CN 102634026 B CN102634026 B CN 102634026B CN 201210096422 A CN201210096422 A CN 201210096422A CN 102634026 B CN102634026 B CN 102634026B
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- 229910052739 hydrogen Inorganic materials 0.000 title claims abstract description 49
- 239000001257 hydrogen Substances 0.000 title claims abstract description 49
- 229920002050 silicone resin Polymers 0.000 title claims abstract description 43
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 title claims abstract description 42
- 238000002360 preparation method Methods 0.000 title abstract description 11
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 34
- 238000006243 chemical reaction Methods 0.000 claims abstract description 14
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 13
- 239000003960 organic solvent Substances 0.000 claims abstract description 13
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 12
- 239000003377 acid catalyst Substances 0.000 claims abstract description 9
- 230000007062 hydrolysis Effects 0.000 claims abstract description 6
- 238000006460 hydrolysis reaction Methods 0.000 claims abstract description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 27
- 238000000034 method Methods 0.000 claims description 25
- 239000002904 solvent Substances 0.000 claims description 24
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical group OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 20
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 16
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical group CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 claims description 15
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims description 13
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 12
- 229910052799 carbon Inorganic materials 0.000 claims description 11
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 10
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 10
- 230000002378 acidificating effect Effects 0.000 claims description 10
- BFXIKLCIZHOAAZ-UHFFFAOYSA-N methyltrimethoxysilane Chemical compound CO[Si](C)(OC)OC BFXIKLCIZHOAAZ-UHFFFAOYSA-N 0.000 claims description 10
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 9
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 9
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical group CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 9
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 claims description 9
- 239000003054 catalyst Substances 0.000 claims description 9
- 238000004821 distillation Methods 0.000 claims description 9
- VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 claims description 8
- 238000010992 reflux Methods 0.000 claims description 8
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 claims description 6
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims description 6
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 claims description 6
- 230000001476 alcoholic effect Effects 0.000 claims description 6
- 150000002148 esters Chemical class 0.000 claims description 6
- 150000002576 ketones Chemical class 0.000 claims description 6
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 claims description 6
- WGTYBPLFGIVFAS-UHFFFAOYSA-M tetramethylammonium hydroxide Chemical compound [OH-].C[N+](C)(C)C WGTYBPLFGIVFAS-UHFFFAOYSA-M 0.000 claims description 6
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 5
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 claims description 4
- 239000000706 filtrate Substances 0.000 claims description 4
- CPUDPFPXCZDNGI-UHFFFAOYSA-N triethoxy(methyl)silane Chemical compound CCO[Si](C)(OCC)OCC CPUDPFPXCZDNGI-UHFFFAOYSA-N 0.000 claims description 4
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 claims description 3
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 claims description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 3
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 claims description 3
- 235000011054 acetic acid Nutrition 0.000 claims description 3
- 229910000147 aluminium phosphate Inorganic materials 0.000 claims description 3
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims description 3
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 claims description 3
- SBRXLTRZCJVAPH-UHFFFAOYSA-N ethyl(trimethoxy)silane Chemical compound CC[Si](OC)(OC)OC SBRXLTRZCJVAPH-UHFFFAOYSA-N 0.000 claims description 3
- 235000019253 formic acid Nutrition 0.000 claims description 3
- 229910000042 hydrogen bromide Inorganic materials 0.000 claims description 3
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 claims description 3
- 229940071870 hydroiodic acid Drugs 0.000 claims description 3
- 229910017604 nitric acid Inorganic materials 0.000 claims description 3
- 235000006408 oxalic acid Nutrition 0.000 claims description 3
- 229940095064 tartrate Drugs 0.000 claims description 3
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical group CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 claims description 3
- DENFJSAFJTVPJR-UHFFFAOYSA-N triethoxy(ethyl)silane Chemical compound CCO[Si](CC)(OCC)OCC DENFJSAFJTVPJR-UHFFFAOYSA-N 0.000 claims description 3
- 239000006227 byproduct Substances 0.000 abstract description 11
- -1 alkoxy silane Chemical compound 0.000 abstract description 9
- 239000000047 product Substances 0.000 abstract description 9
- 229920001296 polysiloxane Polymers 0.000 abstract description 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract description 5
- 238000004132 cross linking Methods 0.000 abstract description 3
- 229910000077 silane Inorganic materials 0.000 abstract 2
- 238000001704 evaporation Methods 0.000 abstract 1
- 239000005022 packaging material Substances 0.000 abstract 1
- 239000003795 chemical substances by application Substances 0.000 description 20
- 239000000463 material Substances 0.000 description 10
- LIVNPJMFVYWSIS-UHFFFAOYSA-N silicon monoxide Inorganic materials [Si-]#[O+] LIVNPJMFVYWSIS-UHFFFAOYSA-N 0.000 description 10
- 239000008367 deionised water Substances 0.000 description 8
- 229910021641 deionized water Inorganic materials 0.000 description 8
- 238000005538 encapsulation Methods 0.000 description 7
- 150000002431 hydrogen Chemical class 0.000 description 7
- 229920002545 silicone oil Polymers 0.000 description 7
- 239000000126 substance Substances 0.000 description 7
- 230000004044 response Effects 0.000 description 6
- 238000013019 agitation Methods 0.000 description 5
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical group [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 5
- 229920002554 vinyl polymer Polymers 0.000 description 5
- 229910018557 Si O Inorganic materials 0.000 description 4
- 238000006482 condensation reaction Methods 0.000 description 4
- 229960004756 ethanol Drugs 0.000 description 4
- 238000001914 filtration Methods 0.000 description 4
- 239000002253 acid Substances 0.000 description 3
- 230000008901 benefit Effects 0.000 description 3
- 239000003822 epoxy resin Substances 0.000 description 3
- 125000000524 functional group Chemical group 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 229920000647 polyepoxide Polymers 0.000 description 3
- 229920005989 resin Polymers 0.000 description 3
- 239000011347 resin Substances 0.000 description 3
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- 230000032683 aging Effects 0.000 description 2
- 230000009286 beneficial effect Effects 0.000 description 2
- 238000001723 curing Methods 0.000 description 2
- 239000004205 dimethyl polysiloxane Substances 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000006459 hydrosilylation reaction Methods 0.000 description 2
- 238000005286 illumination Methods 0.000 description 2
- 239000003112 inhibitor Substances 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- HMMGMWAXVFQUOA-UHFFFAOYSA-N octamethylcyclotetrasiloxane Chemical compound C[Si]1(C)O[Si](C)(C)O[Si](C)(C)O[Si](C)(C)O1 HMMGMWAXVFQUOA-UHFFFAOYSA-N 0.000 description 2
- 230000003287 optical effect Effects 0.000 description 2
- 229920000435 poly(dimethylsiloxane) Polymers 0.000 description 2
- 230000008569 process Effects 0.000 description 2
- 230000005855 radiation Effects 0.000 description 2
- 229920000260 silastic Polymers 0.000 description 2
- 229920002379 silicone rubber Polymers 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- JCVQKRGIASEUKR-UHFFFAOYSA-N triethoxy(phenyl)silane Chemical compound CCO[Si](OCC)(OCC)C1=CC=CC=C1 JCVQKRGIASEUKR-UHFFFAOYSA-N 0.000 description 2
- ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical compound OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 0.000 description 2
- QYLFHLNFIHBCPR-UHFFFAOYSA-N 1-ethynylcyclohexan-1-ol Chemical group C#CC1(O)CCCCC1 QYLFHLNFIHBCPR-UHFFFAOYSA-N 0.000 description 1
- DHXVGJBLRPWPCS-UHFFFAOYSA-N Tetrahydropyran Chemical compound C1CCOCC1 DHXVGJBLRPWPCS-UHFFFAOYSA-N 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 238000013006 addition curing Methods 0.000 description 1
- 229920005601 base polymer Polymers 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000005336 cracking Methods 0.000 description 1
- 230000006837 decompression Effects 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 229960000935 dehydrated alcohol Drugs 0.000 description 1
- 229920001971 elastomer Polymers 0.000 description 1
- 239000000806 elastomer Substances 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 244000037666 field crops Species 0.000 description 1
- 238000001879 gelation Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 125000001183 hydrocarbyl group Chemical group 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 231100000567 intoxicating Toxicity 0.000 description 1
- 230000002673 intoxicating effect Effects 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000001225 nuclear magnetic resonance method Methods 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 238000004806 packaging method and process 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
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
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- Silicon Polymers (AREA)
Abstract
The invention relates to hydrogen-based silicone resin containing a trifunctional group chain element and a preparation method thereof. The hydrogen-based silicone resin containing the trifunctional group chain element has the following structural general formula: (R12HSiO1/2) a (R2SiO3/2) b, wherein a is not less than 3 and is of an integer, b is not less than 1 and is of an integer, the relation between a and b meets the condition that b/a is not less than 0.33 and not more than 4, R1 is of alkyl with 1-3 carbon atoms, and R2 is of phenyl or alkyl with 1-3 carbon atoms. The preparation method sequentially comprises the following steps of: 1) mixing trifunctional alkoxy silane, tetra-alkyl-dihydro-disiloxane, an organic solvent and an acid catalyst; 2) adding water to perform hydrolysis on the trifunctional alkoxy silane; and 3) evaporating out byproducts so as to get the hydrogen-based silicone resin disclosed by the invention. The hydrogen-based silicone resin disclosed by the invention can be used for cross-linking and curing reaction of LED (light-emitting diode) packaging materials and other addition type polysiloxane, and has the characteristics of high curing speed and smooth appearance of the obtained product.
Description
Technical field
The invention belongs to polymeric material field, be specifically related to a kind of based hydrogen-based silicone resin containing trifunctional chain link and preparation method thereof.
Background technology
Photodiode, is called for short LED (Light Emitting Diode), is the solid state device of a based electroluminescent, and its structure mainly consists of PN junction chip, electrode and optical system.LED has the good characteristics such as volume is little, safety low-voltage, the life-span is long, electro-optical efficiency is high, fast response time, energy-saving and environmental protection, and it is referred to as " green illumination light source ".LED Application Areas is now very extensive, and state shows, sign illumination, backlight of LCD, traffic sign, picture and text show full-color screen and need pointolite or the interior lighting of area source is all the application market of LED.
Structure and the complex process of LED encapsulation, the packaged material of its use directly has influence on use properties and life-span.Traditional epoxy resin encapsulating material quality under light wave radiation and high temperature action is crisp, easy cracking, and it exists the defects such as xanthochromia, luminous efficiency decay be fast.Compare with epoxy resin, organosilicon encapsulating material has excellent moisture resistance, insulativity and flexibility, and with its outstanding heat-proof aging and ultraviolet aging resistance performance, and the feature such as optical attenuation is extremely low, become the best materials of current LED encapsulation, it is replacing traditional epoxy resin, and is widely used.
LED organosilicon material for packaging, common main body is to consist of, the organopolysiloxane of take containing vinyl is base polymer, organopolysiloxane containing a plurality of Si-H keys is linking agent, under platinum group catalyst effect, under room temperature or heating condition, carry out hydrosilylation reaction, thereby obtain having silicon rubber and the silicone resin of cross-linked network structure.Wherein, containing the organopolysiloxane linking agent of a plurality of Si-H keys, be generally low viscous line style methylhydrogenpolysi,oxane, be commonly called as containing hydrogen silicone oil.
For example, disclose that a kind of to take octamethylcyclotetrasiloxane, tetramethyl-tetrahydrochysene cyclotetrasiloxane and closure agent be raw material in Chinese patent application CN201010239022.5, under an acidic catalyst, polymerization obtains the preparation method of line style containing hydrogen silicone oil.But synthetic linking agent in this way, thus carrying out hydrosilylation reaction preparation LED encapsulation with in the process of silastic material, its speed of response is slower, and finished surface is prone to fold and decorative pattern, affect production efficiency and luminous efficiency that LED encapsulates.
Chinese patent application 200910302074 discloses a kind of method of preparing phenyl resin, and the method is not used solvent in preparation process.Yet organic solvent is highly beneficial to preparation feedback.If solvent-free, between reaction process Raw, be very easy to occur cross-linked network, producing gelation even becomes solid, thereby can not get object product.In addition, in the embodiment of this application, all use two functionality organoalkoxysilanes, so in its product, contained two functional group's link configuration.And the reactive behavior of the product of this Han Er functional group link configuration in addition-crosslinked reaction is low, thereby cause speed of response slow, resulting addition-crosslinked reaction product fold has lines, can not reach the requirement of flat appearance light.
Summary of the invention
For solving existing problem in above-mentioned prior art, the invention provides a kind of based hydrogen-based silicone resin containing trifunctional chain link and preparation method thereof.
Particularly, the invention provides:
(1) containing a based hydrogen-based silicone resin for trifunctional chain link, it has following general structure:
(R
1 2HSiO
1/2)
a(R
2SiO
3/2)
b，
Wherein, (R
1 2hSiO
1/2)
afor simple function group chain link, (R
2siO
3/2)
bfor trifunctional chain link, a>=3 and be integer, b>=1 and be integer, the relation of a and b meets 0.33≤b/a≤4, R
1for thering is the alkyl of 1～3 carbon atom, R
2for phenyl or there is the alkyl of 1～3 carbon atom.
(2) according to the based hydrogen-based silicone resin (1) described, wherein, the relation of a and b meets 0.4≤b/a≤2.5.
(3) according to a method for the based hydrogen-based silicone resin (1) described, it comprises the step that next coming in order carry out:
1) three-functionality-degree organoalkoxysilane, tetraalkyl dihydro sily oxide, organic solvent and acid catalyst are mixed, wherein, alkyl in described tetraalkyl dihydro sily oxide comprises 1～3 carbon atom independently of one another, and the mol ratio of described three-functionality-degree organoalkoxysilane and described tetraalkyl dihydro sily oxide is (0.67～8): 1;
2) at 40 ℃～90 ℃, add water, under reflux conditions continue afterwards reaction 1～4 hour;
3) distillation at 85 ℃～110 ℃, adds alkaline neutraliser after gained residuum is cooled to 40 ℃～50 ℃, filters, and by the underpressure distillation at 70 ℃～140 ℃ of gained filtrate, thereby obtains described based hydrogen-based silicone resin.
(4) according to the method (3) described, wherein, in described step 1) in, the mol ratio of described three-functionality-degree organoalkoxysilane and described tetraalkyl dihydro sily oxide is (0.8～5): 1.
(5) according to the method (3) described, wherein, in described step 1) in, described three-functionality-degree organoalkoxysilane is one or more that are selected from methyltrimethoxy silane, Union carbide A-162, phenyltrimethoxysila,e, phenyl triethoxysilane, ethyl trimethoxy silane, ethyl triethoxysilane.
(6) according to the method (3) described, wherein, in described step 1) in, described organic solvent is one or more that are selected from varsol, ketones solvent, alcoholic solvent, esters solvent; And wherein, the consumption of described organic solvent be described three-functionality-degree organoalkoxysilane and described tetraalkyl dihydro sily oxide quality sum 10%～400%.
(7) according to the method (6) described, wherein, described varsol is selected from toluene, dimethylbenzene and/or industrial naptha; Described ketones solvent is selected from methylethylketone, acetone, butanone and/or pimelinketone; Described alcoholic solvent is selected from methyl alcohol, ethanol and/or Virahol; Described esters solvent is selected from ethyl acetate and/or methyl-formiate.
(8) according to the method (3) described, wherein, in described step 1) in, described acid catalyst is one or more that are selected from hydrochloric acid, sulfuric acid, nitric acid, phosphoric acid, perchloric acid, sulfonic acid, formic acid, acetic acid, oxalic acid, tartrate, phenylformic acid, tosic acid, Hydrogen bromide, hydroiodic acid HI, acidic white earth; And wherein, the consumption of described an acidic catalyst be described three-functionality-degree organoalkoxysilane and described tetraalkyl dihydro sily oxide quality sum 0.1%～3%.
(9) method according to (3), wherein, in described step 2) in, described water dropwise adds, and the consumption of described water be described in complete hydrolysis the required water total mass of three-functionality-degree organoalkoxysilane 50%～200%.
(10) according to the method (3) described, wherein, in described step 3) in, described alkaline neutraliser is one or more that are selected from sodium bicarbonate, Tetramethylammonium hydroxide, pyridine.
The present invention compared with prior art has the following advantages and positively effect:
1. the invention provides a kind of based hydrogen-based silicone resin containing trifunctional chain link, compare with line style containing hydrogen silicone oil of the prior art, it has the advantages such as reactive behavior is high, speed of response is fast, be particularly suitable for the linking agent as LED organosilicon encapsulating material, also can, in the cross-linking and curing reaction of the addition type polysiloxane of other purposes, as linking agent, use.
2. its transparency of based hydrogen-based silicone resin containing trifunctional chain link of the present invention is high, and specific refractory power is 1.41～1.53, and has radiation hardness, high-low temperature resistant, the advantage such as weather-proof.Use the LED product making containing the based hydrogen-based silicone resin of trifunctional chain link of the present invention to have the characteristic of flat appearance light, this can improve production efficiency and the luminous efficiency of LED encapsulation.
Embodiment
Below the invention will be further described for the description by embodiment, but this is not limitation of the present invention, those skilled in the art are according to basic thought of the present invention, can make various modifications or improvement, but only otherwise depart from basic thought of the present invention, all within the scope of the present invention.
The invention provides a kind of based hydrogen-based silicone resin containing trifunctional chain link, and a kind of method of preparing containing the based hydrogen-based silicone resin of trifunctional chain link.
Particularly, one aspect of the present invention provides a kind of based hydrogen-based silicone resin containing trifunctional chain link, and it has following general structure:
(R
1 2HSiO
1/2)
a(R
2SiO
3/2)
b，
(R
1 2hSiO
1/2)
afor simple function group chain link, (R
2siO
3/2)
bfor trifunctional chain link, a>=3 and be integer, b>=1 and be integer, the relation of a and b meets 0.33≤b/a≤4, R
1for thering is the alkyl of 1～3 carbon atom, R
2for phenyl or there is the alkyl of 1～3 carbon atom.
Preferably, in above-mentioned general formula, the relation of a and b preferably meets 0.4≤b/a≤2.5.
Based hydrogen-based silicone resin containing trifunctional chain link of the present invention is owing to having trifunctional link configuration, so reactive behavior is high, speed of response is fast, is particularly suitable for as the linking agent in the cross-linking and curing reaction of LED packaged material and other addition type polysiloxane.
In addition, the transparency of the based hydrogen-based silicone resin containing trifunctional chain link of the present invention is high, utilizes ultraviolet-visible pectrophotometer, and under 0.5cm thickness, between 500nm～860nm, its transmissivity is all greater than 99%.Therefore based hydrogen-based silicone resin of the present invention has optically transparent characteristic, and the product making during as linking agent has the characteristic of appearance transparent, light.
Another aspect of the present invention provides a kind of method of preparing containing the based hydrogen-based silicone resin of trifunctional chain link.The method comprises the step that next coming in order carry out: 1) three-functionality-degree organoalkoxysilane, tetraalkyl dihydro sily oxide, organic solvent and acid catalyst are mixed, wherein, alkyl in described tetraalkyl dihydro sily oxide comprises 1～3 carbon atom independently of one another, and the mol ratio of described three-functionality-degree organoalkoxysilane and described tetraalkyl dihydro sily oxide is (0.67～8): 1; 2) at 40 ℃～90 ℃, add water, under reflux conditions continue afterwards reaction 1～4 hour; 3) at 85 ℃～110 ℃, steam partial solvent and by product (for example water, alcohol), after being cooled to 40 ℃～50 ℃, add alkaline neutraliser, filter, by the underpressure distillation at 70 ℃～140 ℃ of gained filtrate, for example, to steam whole solvents and by product (water, alcohol).
Preferably, above-mentioned in step 1) in, the mol ratio of described three-functionality-degree organoalkoxysilane and described tetraalkyl dihydro sily oxide is (0.8～5): 1.
Simple function group chain link also claims M chain link, by tetraalkyl dihydro sily oxide, is provided, and trifunctional chain link also claims T chain link, by three-functionality-degree organoalkoxysilane, is provided.In the present invention, R
1 2hSiO
1/2be M chain link, R
2siO
3/2be T chain link, therefore, the based hydrogen-based silicone resin that contains trifunctional chain link also can be described as MT based hydrogen-based silicone resin.
In step 1) and 2) in, under acidic conditions, the Si-O key of the tetraalkyl dihydro sily oxide of 1mol disconnects, and can produce the R of 2mol
1 2hSiO
1/2, i.e. M chain link.And under acid and enough water exist, the reaction that can be hydrolyzed of three-functionality-degree organoalkoxysilane, generation R
2siO
3/2, i.e. T chain link.Three-functionality-degree organoalkoxysilane self carries out condensation reaction simultaneously, or carries out condensation reaction with M chain link, dewaters and generates by-product alcohol, forms new Si-O chain.
The methyltrimethoxy silane of take reacts as example with tetramethyl-dihydro sily oxide, and its reaction formula is:
Wherein, tetramethyl-dihydro sily oxide generates (CH under acidic conditions
3)
2hSiO
1/2, the reaction that is partly hydrolyzed of the methoxyl group in methyltrimethoxy silane, methoxyl group is substituted by hydroxyl, and generates by-product carbinol.Meanwhile, after methyltrimethoxy silane hydrolysis, carry out each other condensation reaction, or itself and (CH
3)
2hSiO
1/2carry out condensation reaction.
In step 3) in, the object that steams by product is unnecessary water and alcohol to shift out system, promotes reaction to carry out to condensation direction, thereby forms macromole product.In addition, can mole recently control product structure, the i.e. ratio of M chain link and T chain link by what control three-functionality-degree organoalkoxysilane and tetraalkyl dihydro sily oxide.The present invention controls the mol ratio of three-functionality-degree organoalkoxysilane and tetraalkyl dihydro sily oxide for (0.67～8): 1, be preferably (0.8～5): and 1, obtain thus the based hydrogen-based silicone resin containing trifunctional chain link.
In the present invention, preferably, three-functionality-degree organoalkoxysilane has general formula R
2si (OR
3), wherein, R
2for phenyl or there is the alkyl of 1～3 carbon atom, R
3for thering is the saturated hydrocarbyl of 1～2 carbon atom, comprise methyl, ethyl.In the present invention, operable three-functionality-degree organoalkoxysilane is one or more that are selected from methyltrimethoxy silane, Union carbide A-162, phenyltrimethoxysila,e, phenyl triethoxysilane, ethyl trimethoxy silane, ethyl triethoxysilane.
In the present invention, operable organic solvent is one or more that are selected from varsol, ketones solvent, alcoholic solvent, esters solvent.Described varsol is selected from toluene, dimethylbenzene and/or industrial naptha; Described ketones solvent is selected from methylethylketone, acetone, butanone and/or pimelinketone; Described alcoholic solvent is selected from methyl alcohol, ethanol and/or Virahol; Described esters solvent is selected from ethyl acetate and/or methyl-formiate.Preferably, organic solvent used in the present invention is varsol, for example one or more in toluene, dimethylbenzene, industrial naptha.
The amount of the organic solvent using preferably, step 1) be described three-functionality-degree organoalkoxysilane and described tetraalkyl dihydro sily oxide quality sum 10%～400%, be preferably 30%～200%.
In the present invention, operable acid catalyst is one or more that are selected from hydrochloric acid, sulfuric acid, nitric acid, phosphoric acid, perchloric acid, sulfonic acid, formic acid, acetic acid, oxalic acid, tartrate, phenylformic acid, tosic acid, Hydrogen bromide, hydroiodic acid HI, acidic white earth, is preferably one or more in hydrochloric acid, sulfuric acid, sulfonic acid, acidic white earth.
The amount of the catalyzer using preferably, step 1) be described three-functionality-degree organoalkoxysilane and described tetraalkyl dihydro sily oxide quality sum 0.1%～3%, be preferably 0.15%～2%.
In the present invention, the water using preferably, step 2) is deionized water.More preferably, water dropwise adds, and the amount adding be described in complete hydrolysis the required water total mass of three-functionality-degree organoalkoxysilane 50%～200%, be preferably 60%～150%.
In the present invention, operable alkaline neutraliser is one or more that are selected from sodium bicarbonate, Tetramethylammonium hydroxide, pyridine.
To step 3) in consumption concrete restriction not of the alkaline neutraliser that uses, as long as the acid adding before can be neutralized completely.For example, the consumption of this alkaline neutraliser is for to neutralize 100%～500% of required total mass completely by the acid adding before.
According to a kind of specific embodiments of the present invention, preparation comprises containing the method for the based hydrogen-based silicone resin of trifunctional chain link the step that next coming in order carry out: by three-functionality-degree organoalkoxysilane and tetramethyl-dihydro sily oxide, be 1) (0.67～5) in molar ratio: 1 mixes, join in the reaction flask with backflow and whipping appts, add organic solvent and acid catalyst simultaneously; 2) under constant agitation, dropwise add deionized water in 40 ℃～90 ℃, continue afterwards stir and reflux 1～4 hour, wherein, the consumption of deionized water is 50%～200% of the required deionized water total mass of complete hydrolysis three-functionality-degree organoalkoxysilane; 3) make water distilling apparatus into, be warmed up to 85 ℃～110 ℃ and steam by product.After cooling, add alkaline neutraliser, filter, filtrate is carried out to pump vacuum decompression, at 70 ℃～140 ℃, distill out low-boiling-point substance and discard, obtain thus the based hydrogen-based silicone resin containing trifunctional chain link.
Mode by example further explains and describes content of the present invention below, but these examples should not be understood to the restriction to protection scope of the present invention.
Embodiment
In following examples, methyltrimethoxy silane and Union carbide A-162 are purchased from Qufu morning twilight Chemical Co., Ltd., tetramethyl-dihydro sily oxide is purchased from ACROS company, the conventional reagent such as dimethylbenzene, toluene, sulfuric acid, hydrochloric acid, dehydrated alcohol, anhydrous methanol, pyridine, sodium bicarbonate are purchased from Beijing Chemical Plant, trifluoromethanesulfonic acid is purchased from Japanese great achievement KCC, vacuum pump is purchased from Gongyi City Ke Rui Instrument Ltd., and NDJ-79 type rotational viscosimeter is purchased from dynamo-electric factory of Tongji University.
Embodiment 1
136g methyltrimethoxy silane, 67g tetramethyl-dihydro sily oxide, 70g dimethylbenzene and the 0.35g vitriol oil are added in 500ml there-necked flask, under 55 ℃, constant agitation, dropwise add 35g deionized water, carry out about 50 minutes, reflux afterwards 1.5 hours.Make water distilling apparatus into, be warmed up to 105 ℃, distill out by product.Be cooled to after 45 ℃, add 0.8g pyridine, stir and make solution become neutrality in about 30 minutes.Utilize filter paper filtering, afterwards, at 130 ℃, utilize vacuum pump underpressure distillation to go out solvent xylene and lower-molecular substance, thereby obtain the water white based hydrogen-based silicone resin containing trifunctional chain link of 123g.Utilize NDJ-79 type rotational viscosimeter to record its viscosity for 15mPa.s, utilizing nuclear magnetic resonance method to record its active H massfraction is 0.7%.
Embodiment 2
267g Union carbide A-162,67g tetramethyl-dihydro sily oxide, 360g toluene and 3.3g concentrated hydrochloric acid are added in 1000ml there-necked flask, under 85 ℃, constant agitation, dropwise add 100g deionized water, carry out about 50 minutes, reflux afterwards 3.5 hours.Make water distilling apparatus into, be warmed up to 100 ℃, distill out by product.Be cooled to after 42 ℃, add 3.5g sodium bicarbonate, stir and make solution become neutrality in about 30 minutes.Utilize filter paper filtering, afterwards, at 120 ℃, utilize vacuum pump underpressure distillation to go out solvent toluene and lower-molecular substance, thereby obtain the water white based hydrogen-based silicone resin containing trifunctional chain link of 150g.Utilize the mode identical with embodiment 1, recording its viscosity is 21mPa.s, and active H massfraction is 0.58%.
Embodiment 3
102g methyltrimethoxy silane, 67g tetramethyl-dihydro sily oxide, 10g dehydrated alcohol and 140g toluene, 0.33g trifluoromethanesulfonic acid are added in 500ml there-necked flask, under 60 ℃ of constant agitation, dropwise add 40g deionized water, carry out about 35 minutes, reflux afterwards 2 hours.Make water distilling apparatus into, be warmed up to 105 ℃, distill out by product.Be cooled to after 48 ℃, add 1.5g sodium bicarbonate, stir and make solution become neutrality in about 30 minutes.Utilize filter paper filtering, afterwards, at 130 ℃, utilize vacuum pump underpressure distillation to go out solvent toluene, ethanol and lower-molecular substance, thereby obtain the water white based hydrogen-based silicone resin containing trifunctional chain link of 109g.Utilize the mode identical with embodiment 1, recording its viscosity is 12mPa.s, and active H massfraction is 0.79%.
Embodiment 4
The perchloric acid that is 70% by 31g methyltrimethoxy silane, 41g Union carbide A-162,67g tetramethyl-dihydro sily oxide, 15g anhydrous methanol and 150g industrial naptha, 1.8g concentration adds in 500ml there-necked flask, under 70 ℃ of constant agitation, dropwise add 35g deionized water, carry out about 40 minutes, reflux afterwards 2.5 hours.Make water distilling apparatus into, be warmed up to 90 ℃, distill out by product.Be cooled to after 44 ℃, add 4g sodium bicarbonate, stir and make solution become neutrality in about 30 minutes.Utilize filter paper filtering, afterwards, at 85 ℃, utilize vacuum pump underpressure distillation to go out industrial naptha, methyl alcohol, ethanol and lower-molecular substance, thereby obtain the water white based hydrogen-based silicone resin containing trifunctional chain link of 91g.Utilize the mode identical with embodiment 1, recording its viscosity is 9mPa.s, and active H massfraction is 0.95%.
Test example 1
By α, ω-divinyl polydimethylsiloxane, containing the MQ resin of vinyl (its silicone resin for being formed with four-functional group Si-O unit (Q unit) by simple function group Si-O unit (M unit)), inhibitor and platinum group catalyst, mix basis of formation pre-composition.Several different hydrogeneous linking agents (in Table 2) are mixed again with above-mentioned basic prepolymer respectively, and it is 1.1: 1 that the addition of several different hydrogeneous linking agents all makes the mol ratio of Si-H/Si-Vi.After vacuum defoamation, in the mould of 6 * 6cm, at 150 ℃, toast one hour the external appearance characteristic (in Table 1) of each silicon rubber print that observation post obtains afterwards.Respectively above-mentioned each sample preparing of 20g is put into beaker, at 25 ℃, observe their gel time, thereby contrast.Fill a prescription and the results are shown in Table 1.
Table 1
In above-mentioned formula forms, α, the viscosity of ω-divinyl polydimethylsiloxane is 5000mPa.s, vinyl massfraction is 0.12%; The M/Q value that contains the MQ resin of vinyl is 0.8, and the massfraction of vinyl is 5.4%; Inhibitor is 1-ethynylcyclohexanol; Platinum group catalyst is Karstedt platinum catalyst, and platiniferous massfraction is 1%; Linking agent 1 is the based hydrogen-based silicone resin containing trifunctional chain link of embodiment 1; Linking agent 2 is the based hydrogen-based silicone resin containing trifunctional chain link of embodiment 2; Linking agent 3 is the based hydrogen-based silicone resin containing trifunctional chain link of embodiment 3; Linking agent 4 is the based hydrogen-based silicone resin containing trifunctional chain link of embodiment 4; Linking agent 5 is respectively the different line style of hydrogen content (two functional group's chain links) containing hydrogen silicone oil 1 and line style containing hydrogen silicone oil 2 (purchased from land for growing field crops, Panshi City auxiliary chemicals institute) with linking agent 6.The parameter of these hydrogeneous linking agents is in Table 2.
Table 2
As shown in Table 1, in the reaction of silastic elastomer print, compare with line style containing hydrogen silicone oil linking agent, based hydrogen-based silicone resin linking agent containing trifunctional chain link of the present invention makes obtained product attractive in appearance, smooth corrugationless phenomenon, this is extremely beneficial in LED encapsulation field, and this can improve production efficiency and the luminous efficiency of LED encapsulation.
In addition, as shown in Table 1, compare with line style containing hydrogen silicone oil linking agent, the gel time of the based hydrogen-based silicone resin containing trifunctional chain link of the present invention significantly reduces, and this shows that its reactive behavior is high, and speed of response is fast, this is also favourable in LED encapsulation field, it can eliminate fluorescent material settlement issues, alleviates addition curing catalysts intoxicating phenomenon, and enhances productivity.
Claims (11)
1. containing a based hydrogen-based silicone resin for trifunctional chain link, it has following general structure:
(R
1 2HSiO
1/2)
a(R
2SiO
3/2)
b，
Wherein, (R
1 2hSiO
1/2)
afor simple function group chain link, (R
2siO
3/2)
bfor trifunctional chain link, a>=3 and be integer, b>=1 and be integer, the relation of a and b meets 0.33≤b/a≤4, R
1for thering is the alkyl of 1～3 carbon atom, R
2for thering is the alkyl of 1～3 carbon atom.
2. based hydrogen-based silicone resin according to claim 1, wherein, the relation of a and b meets 0.4≤b/a≤2.5.
3. a method of preparing based hydrogen-based silicone resin according to claim 1, it comprises the step that next coming in order carry out:
1) three-functionality-degree organoalkoxysilane, tetraalkyl dihydro sily oxide, organic solvent and acid catalyst are mixed, wherein, alkyl in described tetraalkyl dihydro sily oxide comprises 1～3 carbon atom independently of one another, and the mol ratio of described three-functionality-degree organoalkoxysilane and described tetraalkyl dihydro sily oxide is (0.67～8): 1;
2) at 40 ℃～90 ℃, add water, under reflux conditions continue afterwards reaction 1～4 hour;
3) distillation at 85 ℃～110 ℃, adds alkaline neutraliser after gained residuum is cooled to 40 ℃～50 ℃, filters, and by the underpressure distillation at 70 ℃～140 ℃ of gained filtrate, thereby obtains described based hydrogen-based silicone resin.
4. method according to claim 3, wherein, in described step 1), the mol ratio of described three-functionality-degree organoalkoxysilane and described tetraalkyl dihydro sily oxide is (0.8～5): 1.
5. method according to claim 3, wherein, in described step 1), described three-functionality-degree organoalkoxysilane is one or more that are selected from methyltrimethoxy silane, Union carbide A-162, ethyl trimethoxy silane, ethyl triethoxysilane.
6. method according to claim 3, wherein, in described step 1), described organic solvent is one or more that are selected from varsol, ketones solvent, alcoholic solvent, esters solvent; And wherein, the consumption of described organic solvent be described three-functionality-degree organoalkoxysilane and described tetraalkyl dihydro sily oxide quality sum 10%～400%.
7. method according to claim 6, wherein, described varsol is selected from toluene, dimethylbenzene and/or industrial naptha; Described ketones solvent is selected from methylethylketone, acetone, butanone and/or pimelinketone; Described alcoholic solvent is selected from methyl alcohol, ethanol and/or Virahol; Described esters solvent is selected from ethyl acetate and/or methyl-formiate.
8. method according to claim 3, wherein, in described step 1), described acid catalyst is one or more that are selected from hydrochloric acid, sulfuric acid, nitric acid, phosphoric acid, perchloric acid, sulfonic acid, formic acid, acetic acid, oxalic acid, tartrate, phenylformic acid, Hydrogen bromide, hydroiodic acid HI, acidic white earth; And wherein, the consumption of described an acidic catalyst be described three-functionality-degree organoalkoxysilane and described tetraalkyl dihydro sily oxide quality sum 0.1%～3%.
9. method according to claim 3, wherein, in described step 1), described acid catalyst is tosic acid; And wherein, the consumption of described an acidic catalyst be described three-functionality-degree organoalkoxysilane and described tetraalkyl dihydro sily oxide quality sum 0.1%～3%.
10. method according to claim 3, wherein, in described step 2) in, described water dropwise adds, and the consumption of described water be described in complete hydrolysis the required water total mass of three-functionality-degree organoalkoxysilane 50%～200%.
11. methods according to claim 3, wherein, in described step 3), described alkaline neutraliser is one or more that are selected from sodium bicarbonate, Tetramethylammonium hydroxide, pyridine.
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| CN103540289B (en) * | 2013-05-23 | 2015-05-13 | 杭州师范大学 | Preparation method and application of organic silicon resin adhesive |
| CN103762298A (en) * | 2014-02-02 | 2014-04-30 | 芜湖市神龙新能源科技有限公司 | LED wafer combination package material and technology |
| CN104086771A (en) * | 2014-07-15 | 2014-10-08 | 广东万木新材料科技有限公司 | Preparation method of low-water-absorptivity phenyl hydrogen-containing silicon resin |
| CN104513644B (en) * | 2014-12-10 | 2017-05-10 | 东莞兆舜有机硅科技股份有限公司 | Transparent pouring sealant and use thereof |
| CN105542167B (en) * | 2016-02-22 | 2018-01-09 | 山东省科学院新材料研究所 | A kind of phenyl-based hydrogen-based polysiloxanes and preparation method thereof |
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| CN101712800A (en) * | 2009-11-06 | 2010-05-26 | 陈俊光 | Organic silicon resin encapsulant of large power LED and preparing method thereof |
| CN101891893A (en) * | 2010-07-23 | 2010-11-24 | 深圳市安品有机硅材料有限公司 | Preparation method of phenyl-based hydrogen-based silicone resin for encapsulating LED |
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| US4615782A (en) * | 1984-06-11 | 1986-10-07 | Nippon Telegraph And Telephone Corporation | Intermediate layer material of three-layer resist system and method of forming resist pattern |
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