CN109021005A - A kind of preparation method of water solubility 2- hydroxyl benzophenone derivant base silane - Google Patents
A kind of preparation method of water solubility 2- hydroxyl benzophenone derivant base silane Download PDFInfo
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- CN109021005A CN109021005A CN201810960160.9A CN201810960160A CN109021005A CN 109021005 A CN109021005 A CN 109021005A CN 201810960160 A CN201810960160 A CN 201810960160A CN 109021005 A CN109021005 A CN 109021005A
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- hydroxyl
- base silane
- water solubility
- preparation
- benzophenone derivant
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- 241001597008 Nomeidae Species 0.000 title claims abstract description 32
- HJIAMFHSAAEUKR-UHFFFAOYSA-N (2-hydroxyphenyl)-phenylmethanone Chemical compound OC1=CC=CC=C1C(=O)C1=CC=CC=C1 HJIAMFHSAAEUKR-UHFFFAOYSA-N 0.000 title claims abstract description 31
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 title claims abstract description 26
- 238000002360 preparation method Methods 0.000 title claims abstract description 25
- 229910000077 silane Inorganic materials 0.000 title claims abstract description 25
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 title claims abstract description 23
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims abstract description 32
- 238000006243 chemical reaction Methods 0.000 claims abstract description 22
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims abstract description 18
- 229920001296 polysiloxane Polymers 0.000 claims abstract description 14
- UKRDPEFKFJNXQM-UHFFFAOYSA-N vinylsilane Chemical class [SiH3]C=C UKRDPEFKFJNXQM-UHFFFAOYSA-N 0.000 claims abstract description 11
- 238000003756 stirring Methods 0.000 claims abstract description 8
- 239000003054 catalyst Substances 0.000 claims abstract description 6
- 239000003112 inhibitor Substances 0.000 claims abstract description 5
- 238000006116 polymerization reaction Methods 0.000 claims abstract description 5
- 238000010792 warming Methods 0.000 claims abstract description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 14
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 claims description 11
- -1 propoxyl group Chemical group 0.000 claims description 10
- 239000002253 acid Substances 0.000 claims description 9
- XCJXQCUJXDUNDN-UHFFFAOYSA-N chlordene Chemical compound C12C=CCC2C2(Cl)C(Cl)=C(Cl)C1(Cl)C2(Cl)Cl XCJXQCUJXDUNDN-UHFFFAOYSA-N 0.000 claims description 9
- 239000000126 substance Substances 0.000 claims description 9
- 239000012965 benzophenone Substances 0.000 claims description 8
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N 1,4-Benzenediol Natural products OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 claims description 7
- 238000010992 reflux Methods 0.000 claims description 7
- NWVVVBRKAWDGAB-UHFFFAOYSA-N p-methoxyphenol Chemical compound COC1=CC=C(O)C=C1 NWVVVBRKAWDGAB-UHFFFAOYSA-N 0.000 claims description 5
- OOPYUNNXQSWBQE-UHFFFAOYSA-N OC(C(=O)OC1=C(C(=O)C2=CC=CC=C2)C=CC(=C1)C)=C Chemical compound OC(C(=O)OC1=C(C(=O)C2=CC=CC=C2)C=CC(=C1)C)=C OOPYUNNXQSWBQE-UHFFFAOYSA-N 0.000 claims description 4
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 claims description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
- 229910052760 oxygen Inorganic materials 0.000 claims description 4
- 239000001301 oxygen Substances 0.000 claims description 4
- CNHDIAIOKMXOLK-UHFFFAOYSA-N toluquinol Chemical compound CC1=CC(O)=CC=C1O CNHDIAIOKMXOLK-UHFFFAOYSA-N 0.000 claims description 4
- LJWQJECMFUGUDV-UHFFFAOYSA-N (4-benzoyl-3-hydroxyphenyl) prop-2-enoate Chemical compound OC1=CC(OC(=O)C=C)=CC=C1C(=O)C1=CC=CC=C1 LJWQJECMFUGUDV-UHFFFAOYSA-N 0.000 claims description 3
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims description 2
- 239000005977 Ethylene Substances 0.000 claims description 2
- 150000001336 alkenes Chemical class 0.000 claims description 2
- 229940106691 bisphenol a Drugs 0.000 claims description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 2
- 239000000203 mixture Substances 0.000 claims description 2
- 229940051841 polyoxyethylene ether Drugs 0.000 claims description 2
- 229920000056 polyoxyethylene ether Polymers 0.000 claims description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- JIGUICYYOYEXFS-UHFFFAOYSA-N 3-tert-butylbenzene-1,2-diol Chemical compound CC(C)(C)C1=CC=CC(O)=C1O JIGUICYYOYEXFS-UHFFFAOYSA-N 0.000 claims 1
- 238000006555 catalytic reaction Methods 0.000 claims 1
- 239000003795 chemical substances by application Substances 0.000 claims 1
- 125000000687 hydroquinonyl group Chemical group C1(O)=C(C=C(O)C=C1)* 0.000 claims 1
- 238000010521 absorption reaction Methods 0.000 abstract description 7
- 239000000463 material Substances 0.000 abstract description 7
- 239000007788 liquid Substances 0.000 abstract description 6
- 239000004575 stone Substances 0.000 abstract description 6
- 239000004753 textile Substances 0.000 abstract description 4
- 230000007613 environmental effect Effects 0.000 abstract description 3
- 238000000016 photochemical curing Methods 0.000 abstract description 3
- 230000009257 reactivity Effects 0.000 abstract description 3
- 239000011248 coating agent Substances 0.000 abstract description 2
- 238000000576 coating method Methods 0.000 abstract description 2
- 238000001816 cooling Methods 0.000 abstract description 2
- 238000007599 discharging Methods 0.000 abstract description 2
- 239000010985 leather Substances 0.000 abstract description 2
- 239000006096 absorbing agent Substances 0.000 description 5
- 230000032683 aging Effects 0.000 description 5
- 238000009833 condensation Methods 0.000 description 5
- 230000005494 condensation Effects 0.000 description 5
- 238000000034 method Methods 0.000 description 4
- GPMCZKILFBRNNY-UHFFFAOYSA-N 2,3-bis(2-methylbutan-2-yl)benzene-1,4-diol Chemical compound CCC(C)(C)C1=C(O)C=CC(O)=C1C(C)(C)CC GPMCZKILFBRNNY-UHFFFAOYSA-N 0.000 description 3
- 239000000835 fiber Substances 0.000 description 3
- 0 C*C([I+]C1*)=CC(C)=C1C=O Chemical compound C*C([I+]C1*)=CC(C)=C1C=O 0.000 description 2
- QYKIQEUNHZKYBP-UHFFFAOYSA-N Vinyl ether Chemical compound C=COC=C QYKIQEUNHZKYBP-UHFFFAOYSA-N 0.000 description 2
- 230000001680 brushing effect Effects 0.000 description 2
- YCIMNLLNPGFGHC-UHFFFAOYSA-N catechol Chemical compound OC1=CC=CC=C1O YCIMNLLNPGFGHC-UHFFFAOYSA-N 0.000 description 2
- FWDBOZPQNFPOLF-UHFFFAOYSA-N ethenyl(triethoxy)silane Chemical compound CCO[Si](OCC)(OCC)C=C FWDBOZPQNFPOLF-UHFFFAOYSA-N 0.000 description 2
- NKSJNEHGWDZZQF-UHFFFAOYSA-N ethenyl(trimethoxy)silane Chemical compound CO[Si](OC)(OC)C=C NKSJNEHGWDZZQF-UHFFFAOYSA-N 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 150000002576 ketones Chemical class 0.000 description 2
- 230000005855 radiation Effects 0.000 description 2
- OTEKOJQFKOIXMU-UHFFFAOYSA-N 1,4-bis(trichloromethyl)benzene Chemical compound ClC(Cl)(Cl)C1=CC=C(C(Cl)(Cl)Cl)C=C1 OTEKOJQFKOIXMU-UHFFFAOYSA-N 0.000 description 1
- STMDPCBYJCIZOD-UHFFFAOYSA-N 2-(2,4-dinitroanilino)-4-methylpentanoic acid Chemical compound CC(C)CC(C(O)=O)NC1=CC=C([N+]([O-])=O)C=C1[N+]([O-])=O STMDPCBYJCIZOD-UHFFFAOYSA-N 0.000 description 1
- 201000009030 Carcinoma Diseases 0.000 description 1
- BPQQTUXANYXVAA-UHFFFAOYSA-N Orthosilicate Chemical compound [O-][Si]([O-])([O-])[O-] BPQQTUXANYXVAA-UHFFFAOYSA-N 0.000 description 1
- 239000004952 Polyamide Substances 0.000 description 1
- 239000004743 Polypropylene Substances 0.000 description 1
- 208000027418 Wounds and injury Diseases 0.000 description 1
- 230000002745 absorbent Effects 0.000 description 1
- 239000002250 absorbent Substances 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 150000001335 aliphatic alkanes Chemical class 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000004566 building material Substances 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000000919 ceramic Substances 0.000 description 1
- 239000002537 cosmetic Substances 0.000 description 1
- 230000006378 damage Effects 0.000 description 1
- KPUWHANPEXNPJT-UHFFFAOYSA-N disiloxane Chemical class [SiH3]O[SiH3] KPUWHANPEXNPJT-UHFFFAOYSA-N 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 125000003700 epoxy group Chemical group 0.000 description 1
- NUFVQEIPPHHQCK-UHFFFAOYSA-N ethenyl-methoxy-dimethylsilane Chemical compound CO[Si](C)(C)C=C NUFVQEIPPHHQCK-UHFFFAOYSA-N 0.000 description 1
- 231100000040 eye damage Toxicity 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 238000007654 immersion Methods 0.000 description 1
- 208000026278 immune system disease Diseases 0.000 description 1
- 208000014674 injury Diseases 0.000 description 1
- 238000002386 leaching Methods 0.000 description 1
- 230000007774 longterm Effects 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- WSFSSNUMVMOOMR-BJUDXGSMSA-N methanone Chemical class O=[11CH2] WSFSSNUMVMOOMR-BJUDXGSMSA-N 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 238000010422 painting Methods 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 229920001155 polypropylene Polymers 0.000 description 1
- 238000004611 spectroscopical analysis Methods 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 239000000516 sunscreening agent Substances 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/18—Compounds having one or more C—Si linkages as well as one or more C—O—Si linkages
- C07F7/1804—Compounds having Si-O-C linkages
- C07F7/1872—Preparation; Treatments not provided for in C07F7/20
- C07F7/1892—Preparation; Treatments not provided for in C07F7/20 by reactions not provided for in C07F7/1876 - C07F7/1888
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
- C08G65/02—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
- C08G65/32—Polymers modified by chemical after-treatment
- C08G65/329—Polymers modified by chemical after-treatment with organic compounds
- C08G65/331—Polymers modified by chemical after-treatment with organic compounds containing oxygen
- C08G65/3311—Polymers modified by chemical after-treatment with organic compounds containing oxygen containing a hydroxy group
- C08G65/3314—Polymers modified by chemical after-treatment with organic compounds containing oxygen containing a hydroxy group cyclic
- C08G65/3315—Polymers modified by chemical after-treatment with organic compounds containing oxygen containing a hydroxy group cyclic aromatic
- C08G65/3317—Polymers modified by chemical after-treatment with organic compounds containing oxygen containing a hydroxy group cyclic aromatic phenolic
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
- C08G65/02—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
- C08G65/32—Polymers modified by chemical after-treatment
- C08G65/329—Polymers modified by chemical after-treatment with organic compounds
- C08G65/336—Polymers modified by chemical after-treatment with organic compounds containing silicon
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
Abstract
The present invention relates to a kind of preparation methods of water solubility 2- hydroxyl benzophenone derivant base silane, the following steps are included: 2- hydroxyl benzophenone derivant, allyl polyethenoxy ether, vinyl silanes, methylhydrogen silicone ring body and polymerization inhibitor to be added in reaction kettle and stir, it is warming up to 60~100 DEG C, then Pt catalyst is added, keep the temperature 80~120 DEG C of 1~6h of reaction, cooling, discharging, obtains the i.e. water-soluble 2- hydroxyl benzophenone derivant base silane of faint yellow to amber thick liquid.The 2- hydroxyl benzophenone derivant base silane that the present invention synthesizes has good absorption to the ultraviolet light of 280nm~400nm, reactivity and film forming under temperate condition, the preparation that can be used for the antiultraviolet processing and photocuring function film of textile, leather, stone material etc., has the characteristics that safety and environmental protection, using simple, Coating Durability is good.
Description
Technical field
The invention belongs to the preparation technical fields of chemical products, are related to a kind of preparation method of organosilicon material, specially
One kind having the function of that water solubility, ultraviolet radiation absorption, photocuring receive function and reactive water solubility 2- dihydroxy benaophenonel is derivative
The preparation method of object base silane.
Background technique
Ultraviolet light irradiation can cause human eye's damage, skin tanning, burn, and even result in the generation of cutaneum carcinoma, or
It is to cause immune system disorder.Meanwhile ultraviolet light the main reason for being also light aging.Long-term sunlight irradiation accelerates ancient architecture
It builds, stone inscription, woodcarving, the aging of the historical relics and historical place such as calligraphy and painting.Anti-ultraviolet finishing is carried out to clothing, can effectively be mitigated ultraviolet
Injury of the line to human body, and in one layer of the brushing of the cultural artifact surfaces such as ancient building material with ultraviolet radiation absorption function, can effectively it press down
The light aging of the historical relics such as ancient building processed, extend historical place there are the times.
Benzophenone and its derivative are one of most widely used ultraviolet absorbers of current industrial circle, can be used for fiber
In the formula such as the processes such as element, polyester, polyamide, polypropylene fibre and its plastic processing and cosmetics, sun-screening agent, effectively absorb
Wave-length coverage is 280~400nm.Currently, common benzophenone product exists in the market: (1) cannot by, brush, leaching
The modes such as bubble are in the surfaces such as fiber, building, stone material direct formation of film at surface, to play the role of anti-ultraviolet；(2) with oil product
Based on, lack the aqueous product of environmental protection；(3) the blending type product used in the form of additive is in the majority, and response type product is then less.
However, textile anti-ultraviolet finishing, stone material processing and in terms of, then require ultraviolet absorbing agent to have both
Reactivity, water-soluble and film forming.
An Qiufeng, Wang Yan et al. are by 4- (beta-hydroxy-gamma-allyl oxygen) propoxyl group -2- dihydroxy benaophenonel, allyl polyoxy
Vinethene and allyl glycidyl ether are introduced into simultaneously in methylhydrogen silicone ring body, and having obtained one kind can be directly dilute with water
The reactive diphenyl ketone ultraviolet absorbing agent released, and be used in textile anti-ultraviolet finishing.However, the ultraviolet light
The reactive group of absorbent is epoxy group, has certain requirement to the material and reaction condition of processing, and be not suitable for
The processing of the materials such as stone material, timber, glass, metal in natural environment.
Summary of the invention
It is an object of the invention to solve to problem of the existing technology, a kind of water solubility 2- hydroxyl hexichol is provided
The preparation method of ketone derivatives base silane.
The technical solution used for achieving the above object is such that provided water solubility 2- hydroxyl two
The preparation method of methanone derivatives base alkane is comprising the following specific steps by 2- hydroxyl benzophenone derivant, allyl polyoxy
Vinethene, vinyl silanes, methylhydrogen silicone ring body and polymerization inhibitor are added in the reaction kettle equipped with reflux unit, 100~
500r/min stirring, is warming up to 60~100 DEG C, and Pt catalyst is then added, and then keeps the temperature 80~120 DEG C of 1~6h of reaction, finally
Cooling, discharging, obtains light yellow to amber product i.e. water solubility 2- hydroxyl benzophenone derivant base silane.
In above-mentioned preparation step, the chemical structure of the 2- hydroxyl benzophenone derivant is
(2- hydroxy-4-methyl acryloxybenzophenone),
(2- hydroxyl -4- propenyloxy group benzophenone),
(2- hydroxyl -4- acryloxybenzophenone),
(2- hydroxyl -4- (2- acryloyl-oxy) oxethyl-diphenyl-ketone)
(2- hydroxyl -4- (2- hydroxyl -3- allyl oxygen) propoxyl group hexichol first
One of ketone).
In above-mentioned preparation step, the chemical structure of the allyl polyethenoxy ether is H2C=CHCH2O(CH2CH2O)nH, wherein n=3~12.
In above-mentioned preparation step, the chemical structure of the vinyl silanes isWherein R1、R2、R3It can
Respectively-OCH3、-OCH2CH3、-CH3, but be not simultaneously-CH3。
In above-mentioned preparation step, the chemical structure of the methylhydrogen silicone ring body isWherein n
=3~6, and the ratio of n=4 is not less than 75%.
In above-mentioned preparation step, the polymerization inhibitor be hydroquinone, p-hydroxyanisole, methyl hydroquinone, to uncle
Butyl faces the mixture of one or more of benzenediol, 2,5-, bis- tertiary pentyl hydroquinone, bisphenol-A, phenthazine, and additional amount is
2- hydroxyl benzophenone derivant, allyl polyethenoxy ether, vinyl silanes quality sum 0.005wt%~0.1wt%.
In above-mentioned preparation step, the Pt catalyst is the aqueous isopropanol that chlordene closes platinic acid, and chlordene closes the dense of platinic acid
Degree is 0.3wt%~5.0wt%, and Pt catalyst amount is 2- hydroxyl benzophenone derivant, allyl polyethenoxy ether, ethylene
0.0001wt%~0.01wt% of base silane and methylhydrogen silicone ring body quality sum.
In above-mentioned preparation step, 2- hydroxyl benzophenone derivant, allyl polyethenoxy ether, vinyl silanes mole
The ratio between the sum of number and the molal quantity of Si-H in methylhydrogen silicone ring body are 1:1~1:1.5；2- dihydroxy benaophenonel is derivative
Object, allyl polyethenoxy ether, vinyl silanes molar fraction be the 22.22%~55.56% of the sum of three's molal quantity.
Compared with prior art, the present invention is by 2- hydroxyl benzophenone derivant, allyl polyethenoxy ether, vinyl silicon
Alkane introduces methylhydrogen silicone ring body simultaneously, has synthesized one kind and has had both water solubility, film forming, reactive diphenyl ketone purple
Ultraviolet absorbers.The 2- hydroxyl benzophenone derivant base silane that the present invention synthesizes has the ultraviolet light of 280nm~400nm good
Good absorption, due to the introducing of silane group, also make the ultraviolet absorbing agent have the reactivity under temperate condition at
Film property, application range are extended to leather, ancient building, ruins, stone inscription, woodcarving and ceramics in addition to textile, silicate etc.
Anti-light aging protection.It can directly be diluted with water, be handled using spraying, immersion or brushing technique when in use, it can be in substrate
Surface forms one layer of siloxane film containing high density benzophenone group, plays antiultraviolet, anti-light aging or photocuring
Function has the characteristics that safety and environmental protection, using simple, Coating Durability is good.
Specific embodiment
The present invention will be further described with reference to the examples below.
Embodiment 1:
2- hydroxy-4-methyl acryloxybenzophenone is added in the reaction kettle for being equipped with condensation reflux unit
98.8Kg, allyl polyethenoxy ether (n=8) 143.5Kg, vinyltriethoxysilane 66.6Kg, methylhydrogen silicone
Ring body 60Kg, hydroquinone 30.9g, 150r/min stirring, increase system temperature to 70~80 DEG C, the chlordene for putting into 2wt% closes
The aqueous isopropanol 92.2g of platinic acid, then keeps the temperature 95~105 DEG C of reaction 2h, and product confirms 2160cm with infra-red sepectrometry-1It inhales at place
It receives peak and disappears substantially and reach reaction end, discharge, obtain yellow viscous liquid i.e. water solubility 2- hydroxyl benzophenone derivant
Base silane.
Embodiment 2:
2- hydroxyl -4- propenyloxy group benzophenone 101.7Kg, alkene are added in the reaction kettle for being equipped with condensation reflux unit
Propyl polyoxyethylene ether (n=8) 164.0Kg, vinyltrimethoxysilane 59.3Kg, methylhydrogen silicone ring body 60Kg,
Benzenediol 65.0g is faced to tert-butyl, 200r/min stirring increases system temperature to 60~70 DEG C, and the chlordene for putting into 5.0wt% closes
The aqueous isopropanol 77.0g of platinic acid, then keeps the temperature 80~90 DEG C of reaction 3h, and product confirms 2160cm with infra-red sepectrometry-1It inhales at place
It receives peak and disappears substantially and reach reaction end, discharge, it is derivative to obtain pale yellow viscous liquid i.e. water solubility 2- dihydroxy benaophenonel
Object base silane.
Embodiment 3:
2- hydroxy-4-methyl acryloxybenzophenone is added in the reaction kettle for being equipped with condensation reflux unit
211.7Kg, allyl polyethenoxy ether (n=12) 219.8Kg, vinyltriethoxysilane 71.4Kg, methyl hydrogen silicon oxygen
Alkane ring body 60Kg, 2,5-, bis- tertiary pentyl hydroquinone 150.8g, 235r/min stirring, increase system temperature to 70~80 DEG C, throw
The chlordene for entering 0.5wt% closes the aqueous isopropanol 1688.7g of platinic acid, then keeps the temperature 110~120 DEG C of reaction 5h, product is with infrared
Spectroscopic methodology confirms 2160cm-1Place's absorption peak disappears substantially reaches reaction end, discharges, it is i.e. water-soluble to obtain amber thick liquid
Property 2- hydroxyl benzophenone derivant base silane.
Embodiment 4:
2- hydroxyl -4- (2- hydroxyl -3- allyl oxygen) propoxyl group two is added in the reaction kettle for being equipped with condensation reflux unit
Benzophenone 246.1Kg, allyl polyethenoxy ether (n=10) 186.8Kg, vinyltrimethoxysilane 55.5Kg, methyl contain
Hydrogen siloxane ring body 60Kg, p-hydroxyanisole 54.9g, 250r/min stirring, increase system temperature to 80~90 DEG C, put into
The chlordene of 5wt% closes the aqueous isopropanol 109.68g of platinic acid, then keeps the temperature 110~120 DEG C of reaction 2.5h, product infrared light
Spectrometry confirms 2160cm-1Place's absorption peak disappears substantially reaches reaction end, discharges, it is i.e. water-soluble to obtain amber thick liquid
2- hydroxyl benzophenone derivant base silane.
Embodiment 5:
In the reaction kettle for being equipped with condensation reflux unit be added 2- hydroxyl -4- acryloxybenzophenone 69.8Kg,
Allyl polyethenoxy ether (n=6) 213.2Kg, vinyl-dimethyl methoxylsilane 26.3Kg, methylhydrogen silicone ring body
60Kg, 2,5-, bis- tertiary pentyl hydroquinone 154.7g, 225r/min stirring, increase system temperature to 75~85 DEG C, put into
The chlordene of 2.0wt% closes the aqueous isopropanol 184.7g of platinic acid, then keeps the temperature 80~95 DEG C of reaction 6h, product infra-red sepectrometry
Confirm 2160cm-1Place's absorption peak disappears substantially reaches reaction end, discharges, obtains amber thick liquid i.e. water solubility 2- hydroxyl
Base benzophenone derivates base silane.
Claims (8)
1. a kind of preparation method of water solubility 2- hydroxyl benzophenone derivant base silane, it is characterised in that preparation step includes:
By 2- hydroxyl benzophenone derivant, allyl polyethenoxy ether, vinyl silanes, methylhydrogen silicone ring body and polymerization inhibitor
It is added in the reaction kettle equipped with reflux unit, 100~500r/min stirring is warming up to 60~100 DEG C, and Pt catalysis is then added
Agent then keeps the temperature 80~120 DEG C of 1~6h of reaction, finally cools down, and discharges, obtains light yellow to amber product i.e. water solubility 2-
Hydroxyl benzophenone derivant base silane.
2. the preparation method of water solubility 2- hydroxyl benzophenone derivant base silane as described in claim 1, it is characterised in that:
The chemical structure of the 2- hydroxyl benzophenone derivant is
(2- hydroxy-4-methyl acryloxybenzophenone),
(2- hydroxyl -4- propenyloxy group benzophenone),
(2- hydroxyl -4- acryloxybenzophenone),
(2- hydroxyl -4- (2- acryloyl-oxy) oxethyl-diphenyl-ketone)
In (2- hydroxyl -4- (2- hydroxyl -3- allyl oxygen) propoxyl group benzophenone)
One kind.
3. the preparation method of water solubility 2- hydroxyl benzophenone derivant base silane as described in claim 1, it is characterised in that:
The chemical structure of the allyl polyethenoxy ether is H2C=CHCH2O(CH2CH2O)nH, wherein n=3~12.
4. the preparation method of water solubility 2- hydroxyl benzophenone derivant base silane as described in claim 1, it is characterised in that:
The chemical structure of the vinyl silanes isWherein R1、R2、R3It may respectively be-OCH3、-OCH2CH3、-
CH3, but be not simultaneously-CH3。
5. the preparation method of water solubility 2- hydroxyl benzophenone derivant base silane as described in claim 1, it is characterised in that:
The chemical structure of the methylhydrogen silicone ring body isWherein n=3~6, and the ratio of n=4 is not small
In 75%.
6. the preparation method of water solubility 2- hydroxyl benzophenone derivant base silane as described in claim 1, it is characterised in that:
The polymerization inhibitor is hydroquinone, p-hydroxyanisole, methyl hydroquinone, faces tert-butyl benzenediol, bis- uncle penta of 2,5-
The mixture of one or more of base hydroquinone, bisphenol-A, phenthazine, additional amount are 2- hydroxyl benzophenone derivant, alkene
0.005wt%~0.1wt% of propyl polyoxyethylene ether, vinyl silanes quality sum.
7. the preparation method of water solubility 2- hydroxyl benzophenone derivant base silane as described in claim 1, it is characterised in that:
The Pt catalyst is the aqueous isopropanol that chlordene closes platinic acid, and the concentration that chlordene closes platinic acid is 0.3wt%~5.0wt%, Pt
Catalyst amount is 2- hydroxyl benzophenone derivant, allyl polyethenoxy ether, vinyl silanes and methylhydrogen silicone
0.0001wt%~0.01wt% of ring body quality sum.
8. the preparation method of water solubility 2- hydroxyl benzophenone derivant base silane as described in claim 1, it is characterised in that:
2- hydroxyl benzophenone derivant, allyl polyethenoxy ether, vinyl silanes the sum of molal quantity and methylhydrogen silicone
The ratio between molal quantity of Si-H is 1:1~1:1.5 in ring body；2- hydroxyl benzophenone derivant, allyl polyethenoxy ether, ethylene
The molar fraction of base silane is the 22.22%~55.56% of the sum of three's molal quantity.
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| CN110117357A (en) * | 2019-04-12 | 2019-08-13 | 浙江新安化工集团股份有限公司 | A kind of silane modified polyether and preparation method thereof |
| CN114277579A (en) * | 2021-12-28 | 2022-04-05 | 浙江东进新材料有限公司 | Processing method of sun-proof polyester cotton-like fabric |
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| JP2013190542A (en) * | 2012-03-13 | 2013-09-26 | Shin Etsu Chem Co Ltd | Composition for coating and plastic lens |
| CN105272988A (en) * | 2015-11-09 | 2016-01-27 | 上海天伟纺织质量技术服务有限公司 | Overall extraction method of effective components of mulberry leaves |
| CN105294753A (en) * | 2015-11-19 | 2016-02-03 | 陕西省石油化工研究设计院 | Preparation method of 2-hydroxybenzophenone derivative-based silane |
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| JP2013190542A (en) * | 2012-03-13 | 2013-09-26 | Shin Etsu Chem Co Ltd | Composition for coating and plastic lens |
| CN105272988A (en) * | 2015-11-09 | 2016-01-27 | 上海天伟纺织质量技术服务有限公司 | Overall extraction method of effective components of mulberry leaves |
| CN105294753A (en) * | 2015-11-19 | 2016-02-03 | 陕西省石油化工研究设计院 | Preparation method of 2-hydroxybenzophenone derivative-based silane |
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| CN110117357A (en) * | 2019-04-12 | 2019-08-13 | 浙江新安化工集团股份有限公司 | A kind of silane modified polyether and preparation method thereof |
| CN114277579A (en) * | 2021-12-28 | 2022-04-05 | 浙江东进新材料有限公司 | Processing method of sun-proof polyester cotton-like fabric |
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