CN104961897B - A kind of preparation method of phenylalkyl silicone oil - Google Patents
A kind of preparation method of phenylalkyl silicone oil Download PDFInfo
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- CN104961897B CN104961897B CN201510287775.6A CN201510287775A CN104961897B CN 104961897 B CN104961897 B CN 104961897B CN 201510287775 A CN201510287775 A CN 201510287775A CN 104961897 B CN104961897 B CN 104961897B
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- 229920002545 silicone oil Polymers 0.000 title claims abstract description 60
- 125000003884 phenylalkyl group Chemical group 0.000 title claims abstract description 33
- 238000002360 preparation method Methods 0.000 title claims abstract description 19
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims abstract description 48
- -1 aminomethyl phenyl Chemical group 0.000 claims abstract description 48
- 239000001257 hydrogen Substances 0.000 claims abstract description 47
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 47
- 239000003921 oil Substances 0.000 claims abstract description 36
- 239000002253 acid Substances 0.000 claims abstract description 35
- 229910052710 silicon Inorganic materials 0.000 claims abstract description 27
- 239000010703 silicon Substances 0.000 claims abstract description 27
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 claims abstract description 26
- 238000006243 chemical reaction Methods 0.000 claims abstract description 24
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 22
- 150000002431 hydrogen Chemical class 0.000 claims abstract description 17
- 239000003960 organic solvent Substances 0.000 claims abstract description 13
- 239000002994 raw material Substances 0.000 claims abstract description 10
- 239000003153 chemical reaction reagent Substances 0.000 claims abstract description 8
- 239000011261 inert gas Substances 0.000 claims abstract description 6
- 238000000746 purification Methods 0.000 claims abstract description 6
- 239000000126 substance Substances 0.000 claims description 21
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 19
- 239000000463 material Substances 0.000 claims description 17
- 239000004711 α-olefin Substances 0.000 claims description 12
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 9
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 8
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 claims description 8
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims description 8
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 7
- VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 claims description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 4
- 229910052751 metal Inorganic materials 0.000 claims description 4
- 239000002184 metal Substances 0.000 claims description 4
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims description 4
- 239000003208 petroleum Substances 0.000 claims description 4
- 239000011347 resin Substances 0.000 claims description 4
- 229920005989 resin Polymers 0.000 claims description 4
- 239000007787 solid Substances 0.000 claims description 4
- 150000001768 cations Chemical class 0.000 claims description 3
- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 claims description 3
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 claims description 2
- YPTQLANVAZZAJF-UHFFFAOYSA-N CCO[SiH2]c1cc(C)cc(C)c1 Chemical compound CCO[SiH2]c1cc(C)cc(C)c1 YPTQLANVAZZAJF-UHFFFAOYSA-N 0.000 claims description 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 claims description 2
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 claims description 2
- 238000001514 detection method Methods 0.000 claims description 2
- OKONWUJRLPUUJT-UHFFFAOYSA-N dimethyl-phenyl-triphenylsilyloxysilane Chemical compound C=1C=CC=CC=1[Si](C)(C)O[Si](C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 OKONWUJRLPUUJT-UHFFFAOYSA-N 0.000 claims description 2
- KPUWHANPEXNPJT-UHFFFAOYSA-N disiloxane Chemical compound [SiH3]O[SiH3] KPUWHANPEXNPJT-UHFFFAOYSA-N 0.000 claims description 2
- ZVJXKUWNRVOUTI-UHFFFAOYSA-N ethoxy(triphenyl)silane Chemical compound C=1C=CC=CC=1[Si](C=1C=CC=CC=1)(OCC)C1=CC=CC=C1 ZVJXKUWNRVOUTI-UHFFFAOYSA-N 0.000 claims description 2
- POPACFLNWGUDSR-UHFFFAOYSA-N methoxy(trimethyl)silane Chemical compound CO[Si](C)(C)C POPACFLNWGUDSR-UHFFFAOYSA-N 0.000 claims description 2
- ALPYWOWTSPQXHR-UHFFFAOYSA-N methoxy-methyl-diphenylsilane Chemical compound C=1C=CC=CC=1[Si](C)(OC)C1=CC=CC=C1 ALPYWOWTSPQXHR-UHFFFAOYSA-N 0.000 claims description 2
- 239000011259 mixed solution Substances 0.000 claims description 2
- 229910017604 nitric acid Inorganic materials 0.000 claims description 2
- 230000000717 retained effect Effects 0.000 claims description 2
- 239000000243 solution Substances 0.000 claims description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 2
- ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical compound OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 0.000 claims description 2
- BMOGDWCLOBWOSC-UHFFFAOYSA-N trimethyl-[methyl(diphenyl)silyl]oxysilane Chemical compound C=1C=CC=CC=1[Si](C)(O[Si](C)(C)C)C1=CC=CC=C1 BMOGDWCLOBWOSC-UHFFFAOYSA-N 0.000 claims description 2
- IVZTVZJLMIHPEY-UHFFFAOYSA-N triphenyl(triphenylsilyloxy)silane Chemical compound C=1C=CC=CC=1[Si](C=1C=CC=CC=1)(C=1C=CC=CC=1)O[Si](C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 IVZTVZJLMIHPEY-UHFFFAOYSA-N 0.000 claims description 2
- LYKAQCCNZKZFRW-UHFFFAOYSA-N CO[SiH2]c1cc(C)cc(C)c1 Chemical compound CO[SiH2]c1cc(C)cc(C)c1 LYKAQCCNZKZFRW-UHFFFAOYSA-N 0.000 claims 1
- FJKCDSVHCNEOOS-UHFFFAOYSA-N ethoxy(diphenyl)silane Chemical compound C=1C=CC=CC=1[SiH](OCC)C1=CC=CC=C1 FJKCDSVHCNEOOS-UHFFFAOYSA-N 0.000 claims 1
- RSIHJDGMBDPTIM-UHFFFAOYSA-N ethoxy(trimethyl)silane Chemical compound CCO[Si](C)(C)C RSIHJDGMBDPTIM-UHFFFAOYSA-N 0.000 claims 1
- BKXVGDZNDSIUAI-UHFFFAOYSA-N methoxy(triphenyl)silane Chemical compound C=1C=CC=CC=1[Si](C=1C=CC=CC=1)(OC)C1=CC=CC=C1 BKXVGDZNDSIUAI-UHFFFAOYSA-N 0.000 claims 1
- 230000035935 pregnancy Effects 0.000 claims 1
- 239000002199 base oil Substances 0.000 abstract description 4
- 125000000962 organic group Chemical group 0.000 abstract description 4
- 150000001336 alkenes Chemical class 0.000 abstract description 3
- 238000013329 compounding Methods 0.000 abstract description 3
- 229910052500 inorganic mineral Inorganic materials 0.000 abstract description 3
- 239000000314 lubricant Substances 0.000 abstract description 3
- 239000011707 mineral Substances 0.000 abstract description 3
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 abstract 1
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 19
- 238000010992 reflux Methods 0.000 description 15
- 125000000217 alkyl group Chemical group 0.000 description 9
- UQEAIHBTYFGYIE-UHFFFAOYSA-N hexamethyldisiloxane Chemical group C[Si](C)(C)O[Si](C)(C)C UQEAIHBTYFGYIE-UHFFFAOYSA-N 0.000 description 9
- 230000015556 catabolic process Effects 0.000 description 8
- 238000006731 degradation reaction Methods 0.000 description 8
- 239000002480 mineral oil Substances 0.000 description 8
- 235000010446 mineral oil Nutrition 0.000 description 8
- 230000015572 biosynthetic process Effects 0.000 description 7
- 238000003786 synthesis reaction Methods 0.000 description 7
- 238000010792 warming Methods 0.000 description 7
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 6
- 238000010612 desalination reaction Methods 0.000 description 6
- 238000000703 high-speed centrifugation Methods 0.000 description 6
- 235000017557 sodium bicarbonate Nutrition 0.000 description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 5
- 230000000052 comparative effect Effects 0.000 description 4
- YCIVSJFIXXVSRH-UHFFFAOYSA-N amino-methyl-phenylsilicon Chemical compound C[Si](N)C1=CC=CC=C1 YCIVSJFIXXVSRH-UHFFFAOYSA-N 0.000 description 3
- 229910052799 carbon Inorganic materials 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 229920001296 polysiloxane Polymers 0.000 description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- 235000010290 biphenyl Nutrition 0.000 description 2
- 239000004305 biphenyl Substances 0.000 description 2
- 125000006267 biphenyl group Chemical group 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 239000012530 fluid Substances 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- 235000010755 mineral Nutrition 0.000 description 2
- 239000005416 organic matter 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 Substances [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
- 229920003216 poly(methylphenylsiloxane) Polymers 0.000 description 2
- 239000000376 reactant Substances 0.000 description 2
- 230000035484 reaction time Effects 0.000 description 2
- 238000007142 ring opening reaction Methods 0.000 description 2
- 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 description 1
- RMZNKGBPQWTSFN-UHFFFAOYSA-N 2,2-diphenylethoxy(methyl)silane Chemical compound C[SiH2]OCC(C1=CC=CC=C1)C1=CC=CC=C1 RMZNKGBPQWTSFN-UHFFFAOYSA-N 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- XAWZTWJVCCSMLF-UHFFFAOYSA-N O(C)[SiH3].CC1=C(C=CC=C1)C Chemical compound O(C)[SiH3].CC1=C(C=CC=C1)C XAWZTWJVCCSMLF-UHFFFAOYSA-N 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 239000005864 Sulphur Substances 0.000 description 1
- QYSYEILYXGRUOM-UHFFFAOYSA-N [Cl].[Pt] Chemical compound [Cl].[Pt] QYSYEILYXGRUOM-UHFFFAOYSA-N 0.000 description 1
- 238000007259 addition reaction Methods 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 150000001721 carbon Chemical group 0.000 description 1
- QABCGOSYZHCPGN-UHFFFAOYSA-N chloro(dimethyl)silicon Chemical compound C[Si](C)Cl QABCGOSYZHCPGN-UHFFFAOYSA-N 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 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 description 1
- 229940008099 dimethicone Drugs 0.000 description 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000004205 dimethyl polysiloxane Substances 0.000 description 1
- 235000013870 dimethyl polysiloxane Nutrition 0.000 description 1
- JZZIHCLFHIXETF-UHFFFAOYSA-N dimethylsilicon Chemical compound C[Si]C JZZIHCLFHIXETF-UHFFFAOYSA-N 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 238000006459 hydrosilylation reaction Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- NYMPGSQKHIOWIO-UHFFFAOYSA-N hydroxy(diphenyl)silicon Chemical group C=1C=CC=CC=1[Si](O)C1=CC=CC=C1 NYMPGSQKHIOWIO-UHFFFAOYSA-N 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- 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 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 229920000435 poly(dimethylsiloxane) Polymers 0.000 description 1
- 238000006068 polycondensation reaction Methods 0.000 description 1
- 238000012805 post-processing Methods 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 238000001179 sorption measurement Methods 0.000 description 1
- 230000003335 steric effect Effects 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- LFQCEHFDDXELDD-UHFFFAOYSA-N tetramethyl orthosilicate Chemical compound CO[Si](OC)(OC)OC LFQCEHFDDXELDD-UHFFFAOYSA-N 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
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- Silicon Polymers (AREA)
Abstract
The invention discloses a kind of preparation method of phenylalkyl silicone oil, and under inert gas shielding, high containing hydrogen silicone oil, aminomethyl phenyl mixed methylcyclosiloxane, end-capping reagent and strong acid are mixed, and 6~24h is reacted at 25~80 DEG C, post-treated to obtain methyl and phenyl hydrogen-containing silicon oil；Under inert gas shielding, alhpa olefin, organic solvent and chloroplatinic acid/aqueous isopropanol are mixed, are heated to 60~120 DEG C, and mixed with methyl and phenyl hydrogen-containing silicon oil, phenylalkyl silicone oil is obtained through purification process after reaction.The present invention provides a kind of preparation method of phenylalkyl silicone oil, raw material sources are wide, cost is low, reaction condition is gentle, it is easily controllable, be easy to industrialization；Organic group is more evenly distributed in synthetic product, transparency and heat resistance are more preferable, refractive index is high, the compounding oil especially suitable for mineral lubricant oil base oil.
Description
Technical field
The present invention relates to technical field prepared by organic silicone oil, more particularly to a kind of preparation method of phenylalkyl silicone oil.
Background technology
Silicone oil typically refers to have Viscosity Index height, viscosity-temperature characteristics energy for the linear polysiloxane of liquid condition at room temperature, resist
The advantages that oxidisability, low temperature flow be good, preferable heat endurance and anti-shear stability are good, various in style, application is very
Extensively.
The most common all methyl of silicone oil organic group, referred to as methyl-silicone oil.Phenylalkyl silicone oil can be regarded as first
Product after part methyl is substituted by phenyl and alkyl in base silicone oil, there is excellent high/low temperature mobility, lubricity, resistance to irradiation
Property, the compatibility to the adsorptivity of metal and with organic matter, are the wide products of development prospect.
Phenylalkyl silicone oil is a kind of lube base oil, and its molecular chain structure, molecular weight distribution directly influence its profit
Slip energy and operating temperature range.The preparation of existing phenylalkyl silicone oil is mainly using methylhydracyclosiloxane, dimethyl
Silicon oil of low hydrogen content is made with HMDO ring opening copolymer in cyclosiloxane；Silicon oil of low hydrogen content enters with alpha-olefin, styrene again
Row hydrosilylation and be made.But there are many shortcomings in this method：
First, the monomer purity used in silicon oil of low hydrogen content preparation process it is difficult to ensure that, if wherein retain a small amount of impurity,
Ring-opening reaction is difficult to control, and is easily crosslinked between Si-H, influences viscosity, translucency and structure distribution of product etc., in addition,
Second step Si―H addition reaction can also be made a big impact.
Second, the phenyl of introducing is in γ positions, and the fracture of silicone oil side base is occurred often on the carbon atom of β positions, causes benzene
Lifting unobvious of the base to silicone oil heat endurance.
In addition, at present some report in phenyl hydrogen-containing silicon oil preparation method there is also it is certain the defects of.For example, pass through
The Silicon Containing Hydrogen of the chain link of silica containing diphenyl is synthesized containing silicane hydroxide, dimethylchlorosilane and diphenyl dichlorosilane hydrolytie polycondensation
Oil.This synthetic method, the composition very different of products therefrom, the repeatability of product under different raw material proportionings and hydrolysising condition
And poor controllability.And because diphenyl siloxane chain link space steric effect is big, with methyl hydrogen silica chain link and dimethicone
The reactivity and compatibility of chain link differ greatly, it is difficult to obtain the diformazan that segment distribution is uniform, functional, molal weight is high
Base diphenyl containing hydrogen silicone oil.The resulting product transparency is poor, and cost of material is high, and low temperature properties and bin stability are poor, shadow
Ring its usability.
The content of the invention
The present invention provides a kind of preparation method of phenylalkyl silicone oil, raw material sources are wide, cost is low, reaction condition is gentle,
It is easily controllable, be easy to industrialization；Organic group is more evenly distributed in synthetic product, transparency and heat resistance are more preferable, refractive index is high,
Compounding oil especially suitable for mineral lubricant oil base oil.
A kind of preparation method of phenylalkyl silicone oil, comprises the following steps：
(1) under inert gas shielding, high containing hydrogen silicone oil, aminomethyl phenyl mixed methylcyclosiloxane, end-capping reagent and strong acid are mixed, 25
6~24h is reacted at~80 DEG C, it is post-treated to obtain methyl and phenyl hydrogen-containing silicon oil；
The high containing hydrogen silicone oil, aminomethyl phenyl mixed methylcyclosiloxane, the mass ratio of end-capping reagent and strong acid are 1: 5~50: 1~5: 1
~12；
(2) under inert gas shielding, alpha-olefin, organic solvent and chloroplatinic acid/aqueous isopropanol is mixed, are heated to 60
~120 DEG C, and mixed with methyl and phenyl hydrogen-containing silicon oil prepared by step (1), obtain phenylalkyl silicon through purification process after reaction
Oil；
Described alpha-olefin, organic solvent, the mass ratio of chloroplatinic acid/aqueous isopropanol and methyl and phenyl hydrogen-containing silicon oil are 1:
0.3~200: 0.001~1: 1~250.
Preferably, shown in the chemical structural formula such as formula (I) of the high containing hydrogen silicone oil：
Wherein, a is selected from natural number, and b is selected from not comprising 0 natural number, and a, b are separate, and a+b=1~50.
Preferably, shown in the chemical structural formula such as formula (II) of the aminomethyl phenyl mixed methylcyclosiloxane：
Wherein, x, y are independently selected from not comprising 0 natural number, and x+y=3~6.Further preferably, the aminomethyl phenyl
Phenyl content is 5~20mol.% in mixed methylcyclosiloxane.
Preferably, described end-capping reagent is HMDO, trimethylmethoxysilane, front three base oxethyl silicon
Alkane, tetramethyl diphenyl disiloxane, dimethyl benzene methoxylsilane, 3,5-dimethylphenyl Ethoxysilane, the benzene of dimethyl four
Base disiloxane, methyldiphenyl methoxylsilane, methyldiphenylethoxysilane, hexaphenyldisiloxane, triphenyl first
TMOS, triphenyl Ethoxysilane, in one or more；
Described strong acid is selected from the concentrated sulfuric acid, concentrated hydrochloric acid, concentrated nitric acid, perchloric acid, trifluoromethanesulfonic acid, Emathlite, solid and surpassed
One kind in strong acid, macropore strong acid cation exchanger resin.Its dosage is raw material gross mass (i.e. high containing hydrogen silicone oil, methylbenzene
The gross mass of base mixed methylcyclosiloxane, end-capping reagent and strong acid) 1~8%.Further preferably, described strong acid is 98% concentrated sulfuric acid,
Dosage is the 1~2% of raw material gross mass.
Preferably, in step (1), reaction temperature is 20~60 DEG C, and the reaction time is 16~24h.
Preferably, the preparation method of described chloroplatinic acid/aqueous isopropanol is：Chloroplatinic acid is dissolved in isopropanol, obtained
Isopropanol and chloroplatinic acid complex compound are obtained, chloroplatinic acid concentration is 0.1~2wt.%, and the dosage for participating in reaction is aminomethyl phenyl Silicon Containing Hydrogen
5~100ppm of oil quality (with the molar ratio computing of Si -- H bond contained in Pt and methyl and phenyl hydrogen-containing silicon oil).Preferably,
Described chloroplatinic acid concentration is 0.8~1wt.%, and the dosage for participating in reaction is 20~50ppm of addition raw material (with Pt and Si-H
The molar ratio computing of key).
Preferably, described alpha-olefin is the straight or branched type alkene that carbon number is selected from 2~20, aminomethyl phenyl Silicon Containing Hydrogen
C=C mol ratio is 1: 1.1~1.5 in contained Si -- H bond and alpha-olefin in oil；Further preferably, described alpha-olefin
Carbon number is 8~16 straight or branched alkene, and dosage is (Si-H): (C=C)=1: 1.2~1.3；Most preferably, described α-alkene
Hydrocarbon is 1- laurylenes.
Described organic solvent is in toluene, dimethylbenzene, tetrahydrofuran, isopropanol, n-butanol, n-hexane, petroleum ether
It is at least one.Its dosage is that (i.e. alpha-olefin, organic solvent, chloroplatinic acid/aqueous isopropanol and aminomethyl phenyl contain reactant gross mass
The gross mass of hydrogen silicone oil) 20~80%.Preferably, described organic solvent is toluene, dosage is reactant gross mass
30~50%.
Preferably, methyl and phenyl hydrogen-containing silicon oil prepared by step (1) is instilled by alpha-olefin, organic solvent and chlorine platinum
In the mixed solution of acid/aqueous isopropanol composition, temperature is no more than 90 DEG C in guarantee system during dropwise addition.
Preferably, the post processing described in step (1) is：
The reaction solution that step (1) obtains is cooled to room temperature, excessive nertralizer is added and is sufficiently stirred, neutralized, then pass through
High speed centrifugation removes solid therein, vacuum removal retained material and low-boiling-point substance；
Described nertralizer is at least one of carbonate, bicarbonate, oxidized metal；
Described vacuum removal condition is：Vacuum is -0.075~-0.096Mpa, and temperature is 150~210 DEG C, removing
Time is 1~4h.
Preferably, in step (2), reaction is extremely：In vSi-H=2158cm-1Place, it is without Si-H absworption peaks through infrared detection
Only, then purification process is carried out.Further preferably, in step (2), reaction temperature is 70~100 DEG C, and the reaction time is 8~12h.
Preferably, in step (2), described purification process is vacuum removal organic solvent, residual reaction raw materials and low
Boil thing；
Described vacuum removal condition is：Vacuum is -0.075~-0.096Mpa, and temperature is 150~210 DEG C, removing
Time is 1~4h.
The phenylalkyl silicone oil prepared according to the above method, its number-average molecular weight is 0.5 × 104~6 × 104Between, alkyl
Content is between 0.1~2.0mmol/g, and for phenyl content between 1~25mol.%, index of refraction can between 1.40~1.54
Adjust, there is radiation hardness, high temperature resistant, weather-proof, lubricity is good, to the excellent adsorption of metal, good with the compatibility of organic matter,
Compounding oil especially suitable for mineral lubricant oil base oil.
Compared with prior art, the invention has the advantages that：
1) raw material sources are wide, cost is low；
2) reaction condition is gentle, easily controllable；
3) organic group is more evenly distributed in synthetic product, transparency and heat resistance are more preferable, refractive index is high.
Embodiment
The present invention can be further illustrated by examples below, but embodiment is not the limit to the scope of the present invention
System.
Embodiment 1
In N2Under protection, four-hole bottle is dried to a 100mL equipped with reflux condensate device, thermometer, mechanical agitator
Middle addition aminomethyl phenyl mixed methylcyclosiloxane 47.48g (phenyl content 10mol.%), HMDO 1.5228g, height are hydrogeneous
Silicone oil (Jiaxing Joint Chemical Co., Ltd, UC202, similarly hereinafter) 0.9972g, 98% concentrated sulfuric acid 0.5g, 24h is reacted at 25 DEG C,
Then 2g anhydrous sodium bicarbonates are added fully to neutralize, through high speed centrifugation desalination, are pulled out not at vacuum -0.096Mpa, 205 DEG C
Reaction raw materials and low-boiling-point substance 2h, obtain methyl and phenyl hydrogen-containing silicon oil.
In N2Under protection, four-hole bottle is dried to a 100mL equipped with reflux condensate device, thermometer, mechanical agitator
Middle addition toluene 10g, 1- laurylene 1.89g, chloroplatinic acid/aqueous isopropanol (chloroplatinic acid concentration is 0.8wt.%) 1 drip, and are warming up to
75 DEG C, the methyl and phenyl hydrogen-containing silicon oil 25g of above-mentioned synthesis is slowly instilled in reaction system with constant pressure funnel, dripped in 2h
It is complete.Continue to react 6h.Toluene, unreacting material and low-boiling-point substance 2h are pulled out at vacuum -0.096Mpa, 205 DEG C, obtains phenyl
Alkyl-silicone oil.
Phenylalkyl silicone oil manufactured in the present embodiment, outward appearance clear, its molecular weight are 5500, PDI 1.67, wherein
Alkyl content is 0.296mmol/g, phenyl content 8.4mol.%, refractive index nD 25=1.4233；10% thermal degradation temperature is
398℃；It was layered with 3~4 days after mineral oil.Embody preparation method and property relationship
Embodiment 2
In N2Under protection, four-hole bottle is dried to a 100mL equipped with reflux condensate device, thermometer, mechanical agitator
Middle addition aminomethyl phenyl mixed methylcyclosiloxane 45.08g (phenyl content 10mol.%), HMDO 1.2636g, height are hydrogeneous
Silicone oil 3.6564g, 98% concentrated sulfuric acid 0.5g, react 24h at 25 DEG C, then add 2g anhydrous sodium bicarbonates and fully neutralize, pass through
High speed centrifugation desalination, unreacting material and low-boiling-point substance 2h are pulled out at vacuum -0.096Mpa, 205 DEG C, obtain aminomethyl phenyl and contain
Hydrogen silicone oil.
In N2Under protection, four-hole bottle is dried to a 100mL equipped with reflux condensate device, thermometer, mechanical agitator
Middle addition petroleum ether 10g, 1- laurylene 6.94g, chloroplatinic acid/aqueous isopropanol 3 drip, and are warming up to 75 DEG C, use constant pressure funnel
The methyl and phenyl hydrogen-containing silicon oil 25g of above-mentioned synthesis is slowly instilled in reaction system, dripped off in 2h.Continue to react 10h.In vacuum
Degree -0.096Mpa, petroleum ether, unreacting material and low-boiling-point substance 2h are pulled out at 205 DEG C, obtains phenylalkyl silicone oil.
Phenylalkyl silicone oil manufactured in the present embodiment, outward appearance clear, its molecular weight are 6900, PDI 1.69, wherein
Alkyl content is 0.998mmol/g, phenyl content 7.4mol.%, refractive index nD 25=1.4346；10% thermal degradation temperature is
407℃；It is not stratified after being dissolved each other with mineral oil.
Embodiment 3
In N2Under protection, four-hole bottle is dried to a 100mL equipped with reflux condensate device, thermometer, mechanical agitator
Middle addition aminomethyl phenyl mixed methylcyclosiloxane 47.69g (phenyl content 10mol.%), HMDO 0.648g, height are hydrogeneous
Silicone oil 1.662g, Emathlite (Anji County Zhong Xin atlapulgites Co., Ltd of Zhejiang Province, trade mark HT-1A) 2g are anti-at 60 DEG C
12h is answered, then filters and removes catalyst, unreacting material and low-boiling-point substance 2h are pulled out at vacuum -0.096Mpa, 205 DEG C, is obtained
To methyl and phenyl hydrogen-containing silicon oil.
In N2Under protection, four-hole bottle is dried to a 100mL equipped with reflux condensate device, thermometer, mechanical agitator
Middle addition isopropanol 10g, 1- laurylene 3.1558g, chloroplatinic acid/aqueous isopropanol 2 drip, and are warming up to 75 DEG C, are leaked with constant pressure addition
Bucket slowly instills the methyl and phenyl hydrogen-containing silicon oil 25g of above-mentioned synthesis in reaction system, is dripped off in 2h.Continue to react 8h.True
Reciprocal of duty cycle -0.096Mpa, isopropanol, unreacting material and low-boiling-point substance 2h are pulled out at 205 DEG C, obtains phenylalkyl silicone oil.
Phenylalkyl silicone oil manufactured in the present embodiment, outward appearance clear, its molecular weight are 9900, PDI 1.80, wherein
Alkyl content is 0.493mmol/g, phenyl content 8.1mol.%, refractive index nD 25=1.4319；10% thermal degradation temperature is
432℃；It is not stratified after being dissolved each other with mineral oil.
Embodiment 4
In N2Under protection, four-hole bottle is dried to a 100mL equipped with reflux condensate device, thermometer, mechanical agitator
Middle addition aminomethyl phenyl mixed methylcyclosiloxane 46.295g (phenyl content 10mol.%), HMDO 0.0486g, Gao Han
Hydrogen silicone oil 3.6564, macropore strong acid cation exchanger resin (day tunami letter resin Science and Technology Ltd., D001 types) 3g, 60
12h is reacted at DEG C, then filters and removes catalyst, unreacting material and low boiling are pulled out at vacuum -0.096Mpa, 205 DEG C
Thing 2h, obtains methyl and phenyl hydrogen-containing silicon oil.
In N2Under protection, four-hole bottle is dried to a 100mL equipped with reflux condensate device, thermometer, mechanical agitator
Middle addition dimethylbenzene 12g, 1- laurylene 6.94g, chloroplatinic acid/aqueous isopropanol 4 drip, and are warming up to 100 DEG C, use constant pressure funnel
The methyl and phenyl hydrogen-containing silicon oil 25g of above-mentioned synthesis is slowly instilled in reaction system, dripped off in 2h.Continue to react 8h.In vacuum
Degree -0.096Mpa, dimethylbenzene, unreacting material and low-boiling-point substance 2h are pulled out at 205 DEG C, obtains phenylalkyl silicone oil.
Phenylalkyl silicone oil manufactured in the present embodiment, outward appearance clear, its molecular weight are 20700, PDI 2.31, its
Middle alkyl content is 0.979mmol/g, phenyl content 7.8mol.%, refractive index nD 25=1.4377；10% thermal degradation temperature
For 469 DEG C；It is not stratified after being dissolved each other with mineral oil.
Embodiment 5
In N2Under protection, four-hole bottle is dried to a 100mL equipped with reflux condensate device, thermometer, mechanical agitator
Middle addition aminomethyl phenyl mixed methylcyclosiloxane 47.48g (phenyl content 5mol.%), HMDO 1.5228g, height are hydrogeneous
Silicone oil 0.9972, perchloric acid 0.5g, react 24h at 25 DEG C, then add 2g anhydrous sodium bicarbonates fully neutralize, through high speed from
Heart desalination, unreacting material and low-boiling-point substance 2h are pulled out at vacuum -0.096Mpa, 205 DEG C, obtain aminomethyl phenyl Silicon Containing Hydrogen
Oil.
In N2Under protection, four-hole bottle is dried to a 100mL equipped with reflux condensate device, thermometer, mechanical agitator
Middle addition isopropanol 12g, 1- laurylene 1.89g, chloroplatinic acid/aqueous isopropanol 1 drip, and are warming up to 75 DEG C, use constant pressure funnel
The methyl and phenyl hydrogen-containing silicon oil 25g of above-mentioned synthesis is slowly instilled in reaction system, dripped off in 2h.Continue to react 8h.In vacuum
Degree -0.096Mpa, isopropanol, unreacting material and low-boiling-point substance 2h are pulled out at 205 DEG C, obtains phenylalkyl silicone oil.
Phenylalkyl silicone oil manufactured in the present embodiment, outward appearance clear, its molecular weight are 5700, PDI 1.61, wherein
Alkyl content is 0.295mmol/g, phenyl content 3.6mol.%, refractive index nD 25=1.4174；10% thermal degradation temperature is
367℃；It was layered with 3~4 days after mineral oil.
Embodiment 6
In N2Under protection, four-hole bottle is dried to a 100mL equipped with reflux condensate device, thermometer, mechanical agitator
Middle addition aminomethyl phenyl mixed methylcyclosiloxane 47.48g (phenyl content 20mol.%), dimethyltetraphenyldisiloxane 3.9292g,
High containing hydrogen silicone oil 0.9972, concentrated sulfuric acid 0.5g, react 24h at 25 DEG C, then add 2g anhydrous sodium bicarbonates and fully neutralize, pass through
High speed centrifugation desalination, unreacting material and low-boiling-point substance 2h are pulled out at vacuum -0.096Mpa, 205 DEG C, obtain aminomethyl phenyl and contain
Hydrogen silicone oil.
In N2Under protection, four-hole bottle is dried to a 100mL equipped with reflux condensate device, thermometer, mechanical agitator
Middle addition n-butanol 12g, 1- laurylene 6.94g, chloroplatinic acid/aqueous isopropanol 4 drip, and are warming up to 90 DEG C, use constant pressure funnel
The methyl and phenyl hydrogen-containing silicon oil 25g of above-mentioned synthesis is slowly instilled in reaction system, dripped off in 2h.Continue to react 10h.In vacuum
Degree -0.096Mpa, n-butanol, unreacting material and low-boiling-point substance 2h are pulled out at 205 DEG C, obtains phenylalkyl silicone oil.
Phenylalkyl silicone oil manufactured in the present embodiment, outward appearance clear, its molecular weight are 4500, PDI 1.71, wherein
Alkyl content is 0.295mmol/g, phenyl content 14.6mol.%, refractive index nD 25=1.4529；10% thermal degradation temperature is
407℃；It is not stratified after being dissolved each other with mineral oil.
Comparative example 1
In N2Under protection, four-hole bottle is dried to a 100mL equipped with reflux condensate device, thermometer, mechanical agitator
Middle addition octamethylcy-clotetrasiloxane 47.48g, HMDO 1.5228g, high containing hydrogen silicone oil 0.9972g, 98% dense sulphur
Sour 0.5g, 24h is reacted at 25 DEG C, then add 2g anhydrous sodium bicarbonates and fully neutralize, through high speed centrifugation desalination, in vacuum
Degree -0.096Mpa, unreacting material and low-boiling-point substance 2h are pulled out at 205 DEG C, obtains Methyl Hydrogen Polysiloxane Fluid.
In N2Under protection, four-hole bottle is dried to a 100mL equipped with reflux condensate device, thermometer, mechanical agitator
Middle addition toluene 10g, 1- laurylene 1.89g, chloroplatinic acid/aqueous isopropanol 1 drip, and are warming up to 75 DEG C, will with constant pressure funnel
The Methyl Hydrogen Polysiloxane Fluid 25g of above-mentioned synthesis is slowly instilled in reaction system, is dripped off in 2h.Continue to react 6h.Vacuum-
0.096Mpa, toluene, unreacting material and low-boiling-point substance 2h are pulled out at 205 DEG C, obtains phenylalkyl silicone oil.
Phenylalkyl silicone oil prepared by this comparative example, outward appearance clear, its molecular weight is 5500, PDI 1.65, wherein
Alkyl content is 0.292mmol/g, refractive index nD 25=1.4104；10% thermal degradation temperature is 285 DEG C；With after mineral oil 3
It is layered within~4 days.
Comparative example 2
In N2Under protection, four-hole bottle is dried to a 100mL equipped with reflux condensate device, thermometer, mechanical agitator
Middle addition aminomethyl phenyl mixed methylcyclosiloxane 48.4772g (phenyl content 10mol.%), HMDO 1.5228g, 98%
Concentrated sulfuric acid 0.5g, 24h is reacted at 25 DEG C, then add 2g anhydrous sodium bicarbonates and fully neutralize, through high speed centrifugation desalination, true
Reciprocal of duty cycle -0.096Mpa, unreacting material and low-boiling-point substance 2h are pulled out at 205 DEG C, obtains methyl phenyl silicone oil.
Methyl phenyl silicone oil prepared by this comparative example, outward appearance clear, its molecular weight is 5300, PDI 1.62, wherein
Phenyl content is 7.9mol.%, refractive index nD 25=1.4262；10% thermal degradation temperature is 373 DEG C；It is immiscible with mineral oil, mix
It is layered at once after conjunction.
Claims (7)
1. a kind of preparation method of phenylalkyl silicone oil, it is characterised in that comprise the following steps：
(1) under inert gas shielding, high containing hydrogen silicone oil, aminomethyl phenyl mixed methylcyclosiloxane, end-capping reagent and strong acid are mixed, 25~80
6~24h is reacted at DEG C, it is post-treated to obtain methyl and phenyl hydrogen-containing silicon oil；
The high containing hydrogen silicone oil, aminomethyl phenyl mixed methylcyclosiloxane, the mass ratio of end-capping reagent and strong acid are 1:5~50:1~5:1~12；
Shown in the chemical structural formula such as formula (I) of the high containing hydrogen silicone oil：
Wherein, a is selected from natural number, and b is selected from not comprising 0 natural number, and a, b are separate, and a+b=1~50；
Shown in the chemical structural formula such as formula (II) of the aminomethyl phenyl mixed methylcyclosiloxane：
Wherein, x, y are independently selected from not comprising 0 natural number, x+y=3~6, and phenyl in the aminomethyl phenyl mixed methylcyclosiloxane
Content is 10mol.%；
(2) under inert gas shielding, alpha-olefin, organic solvent and chloroplatinic acid/aqueous isopropanol are mixed, it is heated to 60~
120 DEG C, and mixed with methyl and phenyl hydrogen-containing silicon oil prepared by step (1), obtain phenylalkyl silicone oil through purification process after reaction；
Described alpha-olefin, organic solvent, the mass ratio of chloroplatinic acid/aqueous isopropanol and methyl and phenyl hydrogen-containing silicon oil are 1:0.3
~200:0.001~1:1~250；
C=C mol ratio is 1 in contained Si -- H bond and alpha-olefin in the methyl and phenyl hydrogen-containing silicon oil:1.2~1.3.
2. the preparation method of phenylalkyl silicone oil according to claim 1, it is characterised in that described end-capping reagent is pregnancy
Base disiloxane, trimethylmethoxysilane, trimethylethoxysilane, tetramethyl diphenyl disiloxane, 3,5-dimethylphenyl
Methoxy silane, 3,5-dimethylphenyl Ethoxysilane, dimethyltetraphenyldisiloxane, methyldiphenyl methoxylsilane, first
At least one in base diphenyl Ethoxysilane, hexaphenyldisiloxane, triphenylmethoxy silane, triphenyl Ethoxysilane
Kind；
Described strong acid be selected from the concentrated sulfuric acid, concentrated hydrochloric acid, concentrated nitric acid, perchloric acid, trifluoromethanesulfonic acid, Emathlite, solid super-strong acid,
One kind in macropore strong acid cation exchanger resin.
3. the preparation method of phenylalkyl silicone oil according to claim 1, it is characterised in that described organic solvent is first
At least one of benzene, dimethylbenzene, tetrahydrofuran, isopropanol, n-butanol, n-hexane, petroleum ether.
4. the preparation method of phenylalkyl silicone oil according to claim 1, it is characterised in that the first for preparing step (1)
Base phenyl hydrogen-containing silicon oil is instilled in the mixed solution being made up of alpha-olefin, organic solvent and chloroplatinic acid/aqueous isopropanol, is added dropwise
Temperature is no more than 90 DEG C in guarantee system in journey.
5. the preparation method of phenylalkyl silicone oil according to claim 1, it is characterised in that the rear place described in step (1)
Manage and be：
The reaction solution that step (1) obtains is cooled to room temperature, excessive nertralizer is added and is sufficiently stirred, neutralized, then through at a high speed
It is centrifuged off solid therein, vacuum removal retained material and low-boiling-point substance；
Described nertralizer is at least one of carbonate, bicarbonate, oxidized metal；
Described vacuum removal condition is：Vacuum is -0.075~-0.096Mpa, and temperature is 150~210 DEG C, removes the time
For 1~4h.
6. the preparation method of phenylalkyl silicone oil according to claim 1, it is characterised in that in step (2), reaction is extremely：
In νSi-H=2158cm-1Place, through infrared detection without Si-H absworption peaks untill, then carry out purification process.
7. the preparation method of phenylalkyl silicone oil according to claim 1, it is characterised in that in step (2), described is pure
Change processing as vacuum removal organic solvent, residual reaction raw materials and low-boiling-point substance；
Described vacuum removal condition is：Vacuum is -0.075~-0.096Mpa, and temperature is 150~210 DEG C, removes the time
For 1~4h.
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| CN107286347B (en) * | 2017-07-25 | 2023-03-17 | 广州硅芯材料科技有限公司 | Method for preparing phenyl hydrogen-containing silicone resin from methyl hydrogen-containing silicone oil |
| CN107233862A (en) * | 2017-08-02 | 2017-10-10 | 王艺霖 | A kind of preparation method of methyl phenyl silicone oil adsorbent |
| CN107814586B (en) * | 2017-10-26 | 2020-11-06 | 杭州瑞江新材料技术有限公司 | Organic silicon waterproof and oilproof emulsion and preparation method thereof |
| CN108441278A (en) * | 2018-03-30 | 2018-08-24 | 王建东 | A kind of preparation of greases method |
| CN110358089A (en) * | 2018-04-11 | 2019-10-22 | 苏州润特新材料科技有限公司 | A kind of preparation method of alkylaryl modified silicon oil |
| CN112574417A (en) * | 2020-11-27 | 2021-03-30 | 山东大易化工有限公司 | Preparation method of release agent suitable for medium-high temperature metal die casting |
| CN112778527B (en) * | 2021-01-05 | 2022-05-27 | 吉林大学 | Polyol fatty acid ester/phenyl/polyether co-modified silicone oil, preparation method and special low silicone oil agent for carbon fibers |
| CN114133567B (en) * | 2021-09-11 | 2022-11-22 | 唐山三友硅业有限责任公司 | Preparation method of polysiloxane cross-linking agent |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101184762A (en) * | 2005-04-20 | 2008-05-21 | 莫门蒂夫功能性材料公司 | Process for making Si-H functional siloxane oligomer |
| CN101289538A (en) * | 2008-05-30 | 2008-10-22 | 杭州师范大学 | Method for preparing methyl and phenyl hydrogen-containing silicon oil for packaging LED |
| CN101851333A (en) * | 2010-05-28 | 2010-10-06 | 杭州师范大学 | Method for preparing methyl phenyl hydrogen-containing silicone oil by rare earth super acid catalysis |
-
2015
- 2015-05-28 CN CN201510287775.6A patent/CN104961897B/en active Active
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101184762A (en) * | 2005-04-20 | 2008-05-21 | 莫门蒂夫功能性材料公司 | Process for making Si-H functional siloxane oligomer |
| CN101289538A (en) * | 2008-05-30 | 2008-10-22 | 杭州师范大学 | Method for preparing methyl and phenyl hydrogen-containing silicon oil for packaging LED |
| CN101851333A (en) * | 2010-05-28 | 2010-10-06 | 杭州师范大学 | Method for preparing methyl phenyl hydrogen-containing silicone oil by rare earth super acid catalysis |
Non-Patent Citations (1)
| Title |
|---|
| 长链烷基硅油的研究;林茵;《中国优秀硕士学位论文全文数据库》;20050131;第15-18页 * |
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