CN110903314B - Silane coupling agent and preparation method and application thereof - Google Patents
Silane coupling agent and preparation method and application thereof Download PDFInfo
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- CN110903314B CN110903314B CN201911227176.XA CN201911227176A CN110903314B CN 110903314 B CN110903314 B CN 110903314B CN 201911227176 A CN201911227176 A CN 201911227176A CN 110903314 B CN110903314 B CN 110903314B
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- 239000006087 Silane Coupling Agent Substances 0.000 title claims abstract description 26
- 238000002360 preparation method Methods 0.000 title abstract description 6
- 238000006243 chemical reaction Methods 0.000 claims abstract description 58
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 48
- 239000012043 crude product Substances 0.000 claims abstract description 41
- LZCLXQDLBQLTDK-UHFFFAOYSA-N ethyl 2-hydroxypropanoate Chemical compound CCOC(=O)C(C)O LZCLXQDLBQLTDK-UHFFFAOYSA-N 0.000 claims abstract description 38
- 239000000839 emulsion Substances 0.000 claims abstract description 36
- GQIUQDDJKHLHTB-UHFFFAOYSA-N trichloro(ethenyl)silane Chemical compound Cl[Si](Cl)(Cl)C=C GQIUQDDJKHLHTB-UHFFFAOYSA-N 0.000 claims abstract description 28
- 239000005050 vinyl trichlorosilane Substances 0.000 claims abstract description 28
- -1 vinyl ethoxy ethyl Chemical group 0.000 claims abstract description 22
- 229940116333 ethyl lactate Drugs 0.000 claims abstract description 20
- 238000010438 heat treatment Methods 0.000 claims abstract description 19
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims abstract description 13
- 229910000077 silane Inorganic materials 0.000 claims abstract description 13
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 claims abstract description 12
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 claims abstract description 9
- 230000007935 neutral effect Effects 0.000 claims abstract description 3
- 229910003946 H3Si Inorganic materials 0.000 claims description 16
- 229920001909 styrene-acrylic polymer Polymers 0.000 claims description 12
- 238000000034 method Methods 0.000 claims description 10
- 238000009835 boiling Methods 0.000 claims description 9
- KCWYOFZQRFCIIE-UHFFFAOYSA-N ethylsilane Chemical compound CC[SiH3] KCWYOFZQRFCIIE-UHFFFAOYSA-N 0.000 claims description 6
- 230000035484 reaction time Effects 0.000 claims description 2
- 238000003756 stirring Methods 0.000 claims description 2
- 239000000126 substance Substances 0.000 claims description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 abstract description 52
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 abstract description 19
- 235000011114 ammonium hydroxide Nutrition 0.000 abstract description 19
- 239000003973 paint Substances 0.000 abstract description 18
- 238000000354 decomposition reaction Methods 0.000 abstract 1
- 238000001179 sorption measurement Methods 0.000 description 18
- 239000007822 coupling agent Substances 0.000 description 15
- 239000000047 product Substances 0.000 description 12
- XDLMVUHYZWKMMD-UHFFFAOYSA-N 3-trimethoxysilylpropyl 2-methylprop-2-enoate Chemical compound CO[Si](OC)(OC)CCCOC(=O)C(C)=C XDLMVUHYZWKMMD-UHFFFAOYSA-N 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- 230000000694 effects Effects 0.000 description 6
- 239000000945 filler Substances 0.000 description 6
- 230000003472 neutralizing effect Effects 0.000 description 6
- 238000004321 preservation Methods 0.000 description 6
- 239000002893 slag Substances 0.000 description 6
- 230000015572 biosynthetic process Effects 0.000 description 5
- 238000003786 synthesis reaction Methods 0.000 description 5
- NKSJNEHGWDZZQF-UHFFFAOYSA-N ethenyl(trimethoxy)silane Chemical compound CO[Si](OC)(OC)C=C NKSJNEHGWDZZQF-UHFFFAOYSA-N 0.000 description 4
- 230000007062 hydrolysis Effects 0.000 description 4
- 238000006460 hydrolysis reaction Methods 0.000 description 4
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 238000007792 addition Methods 0.000 description 3
- 230000036541 health Effects 0.000 description 3
- 230000008569 process Effects 0.000 description 3
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- 230000006750 UV protection Effects 0.000 description 2
- 239000000853 adhesive Substances 0.000 description 2
- 230000001070 adhesive effect Effects 0.000 description 2
- 239000003995 emulsifying agent Substances 0.000 description 2
- 230000007613 environmental effect Effects 0.000 description 2
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 2
- 230000004224 protection Effects 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- 150000001299 aldehydes Chemical class 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 239000006172 buffering agent Substances 0.000 description 1
- CQEYYJKEWSMYFG-UHFFFAOYSA-N butyl acrylate Chemical compound CCCCOC(=O)C=C CQEYYJKEWSMYFG-UHFFFAOYSA-N 0.000 description 1
- 238000010276 construction Methods 0.000 description 1
- 239000008367 deionised water Substances 0.000 description 1
- 229910021641 deionized water Inorganic materials 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 235000013373 food additive Nutrition 0.000 description 1
- 239000002778 food additive Substances 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 239000003999 initiator Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012856 packing Methods 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 230000000630 rising effect Effects 0.000 description 1
- 238000010079 rubber tapping Methods 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 239000002699 waste material Substances 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
- C07F7/188—Preparation; Treatments not provided for in C07F7/20 by reactions involving the formation of Si-O linkages
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D125/00—Coating compositions based on homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by an aromatic carbocyclic ring; Coating compositions based on derivatives of such polymers
- C09D125/02—Homopolymers or copolymers of hydrocarbons
- C09D125/04—Homopolymers or copolymers of styrene
- C09D125/08—Copolymers of styrene
- C09D125/14—Copolymers of styrene with unsaturated esters
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D7/00—Features of coating compositions, not provided for in group C09D5/00; Processes for incorporating ingredients in coating compositions
- C09D7/40—Additives
- C09D7/60—Additives non-macromolecular
- C09D7/63—Additives non-macromolecular organic
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Wood Science & Technology (AREA)
- Chemical Kinetics & Catalysis (AREA)
Abstract
The invention discloses a silane coupling agent and a preparation method and application thereof, wherein the silane coupling agent is chemically named as vinyl ethoxy ethyl dilactate silane, and the preparation method comprises the following steps: vinyl trichlorosilane and ethanol with the molar ratio of 1:1.1-1.2 are stirred and reacted for 2-3 hours at the temperature of 100-110 ℃, and an intermediate is obtained; and (3) reacting the intermediate with ethyl lactate at the temperature of 150-160 ℃ for 4-6 hours to obtain a crude product, wherein the molar ratio of the vinyl trichlorosilane to the ethyl lactate is 1: 2-4; heating the crude product to 90-110 ℃, vacuumizing to-0.09 MPa to-0.095 MPa, keeping the temperature and the pressure constant for 2-3 hours, reducing the pressure, adding magnesium powder to neutralize the crude product to be neutral, and rectifying to obtain vinyl ethoxy ethyl dilactate silane, wherein hydrochloric acid generated in the reaction process is adsorbed by ammonia water with the concentration of 10 wt%, so that the environment pollution is prevented; the silane coupling agent is added into the acrylic emulsion, so that the paint film performance can be improved, the storage stability of the emulsion can be improved, and no pollution is caused after decomposition.
Description
Technical Field
The invention relates to the field of organic chemistry, in particular to a silane coupling agent and a preparation method and application thereof.
Background
Along with the improvement of the living standard of people, the health attention degree is enhanced, the requirement of environment-friendly materials is increased day by day, the traditional oil paint has large smell and pollutes the environment, VOC can be generated after the paint is used, and particularly ethers and aldehydes can cause great harm to the health of people. At present, the traditional oil paint can not meet the current requirements, and the water paint has a rapid development trend due to environmental protection and health. At present, the most widely used and continuously rising water-based paint is acrylic emulsion, and compared with oil-based paint, the high gloss and the environmental protection of the water-based paint have irreplaceable advantages and are widely applied to the fields of automobiles, machinery, papermaking, buildings and the like.
At present, a paint film of acrylic emulsion is poorer than that of the traditional oil paint in the aspects of adhesive force, ultraviolet resistance, water resistance, solvent resistance and the like, and in order to improve the performance of the paint film of the acrylic emulsion and enable the paint film to meet the application requirements of various fields, a main means is to add a silane coupling agent into the paint film to modify the paint film so as to improve the performances of the paint film such as adhesive force, ultraviolet resistance, water resistance, solvent resistance and the like. Silane coupling agents commonly used in acrylic emulsions are vinyltrimethoxysilane, methacryloxypropyltrimethoxysilane, and the like. However, the emulsion is unstable after the silane coupling agent is added, and the first aspect is that the alkoxy end of the silane coupling agent is a hydrolyzable group with higher activity, and the hydrolyzable group can be rapidly condensed into a net structure after being hydrolyzed too fast, so that the emulsion synthesis process has high slag yield and even breaks emulsion; the second aspect is represented by the poor storage stability of the emulsion, the fast hydrolysis of the silane alkoxy group leads to the fact that the emulsion must be prepared immediately, otherwise, the emulsion is inactivated after more than 24 hours, which is inconvenient for construction and has the problem of raw material waste.
Disclosure of Invention
Aiming at the problem of instability of acrylic emulsion caused by the addition of a silane coupling agent in the prior art, the invention provides the silane coupling agent to solve the problem of instability of the acrylic emulsion.
The technical scheme provided by the invention is as follows:
the silane coupling agent provided by the invention has a chemical name of vinyl ethoxy ethyl dilactate silane, and has a structural formula as follows:
the preparation method of the vinyl ethoxy ethyl dilactate silane provided by the invention comprises the following steps:
(1) vinyl trichlorosilane and ethanol with the molar ratio of 1:1.1-1.2 are stirred and reacted for 2-3 hours at the temperature of 100-110 ℃ to obtain an intermediate C2H3Si(OC2H5)Cl2；
(2) Reacting the intermediate C2H3Si(OC2H5)Cl2Stirring and reacting with ethyl lactate at 150-160 ℃ for 4-6 hours to obtain a crude product; wherein the vinyl trichlorosilane and the emulsionThe molar ratio of ethyl acetate is 1: 2-4;
(3) heating the crude product to 90-120 ℃, vacuumizing to-0.09 MPa to-0.095 MPa, maintaining constant temperature and constant pressure for 2-3 hours, reducing pressure, adding magnesium powder to neutralize the crude product to be neutral, and rectifying to obtain the vinyl ethoxy ethyl lactate silane.
On the basis of the technical scheme, in the step (1), firstly, heating the ethanol to slight boiling, and then dropwise adding the vinyltrichlorosilane into the ethanol.
On the basis of the technical scheme, in the step (1), the reaction temperature is 100 ℃, and the reaction time is 2 hours.
On the basis of the technical scheme, in the step (1), the dripping speed of the vinyl trichlorosilane is 3.8 g/min-5.8 g/min.
On the basis of the technical scheme, in the step (2), ethyl lactate is added into a reaction kettle firstly, the reaction kettle is heated to be slightly boiled, and then the intermediate C is dropwise added into the ethyl lactate2H3Si(OC2H5)Cl2。
On the basis of the technical scheme, in the step (2), the intermediate C2H3Si(OC2H5)Cl2The dropping speed of (A) is 5g/min-6.6 g/min.
On the basis of the technical scheme, in the step (3), the heating temperature of the crude product is 120 ℃, and the heating time is 2 hours.
The invention also provides an application of the silane coupling agent in acrylic emulsion, which specifically comprises the following steps:
the styrene-acrylic emulsion is added with the silane coupling agent, and the adding amount of the silane coupling agent is 1-12 wt% of the total weight of the styrene-acrylic emulsion.
The reaction mechanism for synthesizing the vinyl ethoxy ethyl dilactate silane is as follows:
C2H3SiCl3+C2H6O→C2H3Si(OC2H5)Cl2+HCl
C2H3Si(OC2H5)Cl2+C5H10O3→C14H26O7Si+HCl。
compared with the traditional coupling agent with three methoxyl groups and one ethoxyl group, the invention has the following advantages and beneficial effects:
(1) the ethylene ethoxy dilactate ethyl silane provided by the invention has two ethyl lactate groups and one ethoxy group, one ethoxy group retains the reaction activity, and meanwhile, the steric hindrance effect and the reaction activity of the ethyl lactate gene are relatively low, so that the hydrolysis is slow, the slag yield in the emulsion synthesis process is reduced, and demulsification caused by a net structure is avoided.
(2) The dosage of the traditional coupling agent in the acrylic emulsion is at most 3 wt%, and the dosage of the silane coupling agent in the emulsion provided by the invention can be increased to 10 wt%, so that the paint film performance can be improved, and the storage stability of the emulsion can be improved.
(3) The traditional silane coupling agent can release methanol after hydrolysis, and the ethyl lactate released after hydrolysis of the silane coupling agent provided by the invention can be used as a food additive, can cover up the smell of acrylic emulsion, and is more environment-friendly and healthy compared with the traditional silane coupling agent.
Detailed Description
The technical solution of the present invention is further illustrated by the following specific examples.
Example 1
(1) Feeding and reacting according to the molar ratio of the vinyl trichlorosilane to the ethanol of 1: 1.1: firstly adding ethanol into a reaction kettle, heating to 80 ℃ to enable the ethanol to be in a slightly boiling state, then slowly dropwise adding vinyl trichlorosilane from the top of a filler tower at a dropwise adding speed of 3.8g/min to enable the vinyl trichlorosilane and the filler to be in full contact reaction in the tower, keeping the temperature at 100 ℃ after dropwise adding is finished to react for 2 hours, guiding hydrochloric acid generated in the reaction period into ammonia water with the concentration of 10 wt% for adsorption to obtain an intermediate C2H3Si(OC2H5)Cl2；
(2) According to the molar ratio of 1: 2, carrying out feeding reaction: adding ethyl lactate into a reaction kettle, heating to slightly boil, then dripping the intermediate obtained in the step (1) into the reaction kettle from the top of the tower at a dripping speed of 6.6g/min, keeping the temperature at 160 ℃ for reacting for 4 hours after dripping is finished, and introducing hydrochloric acid generated in the reaction into ammonia water with the concentration of 10 wt% for adsorption during the reaction period to obtain a crude product;
(3) keeping the temperature of the crude product at 120 ℃ for 2 hours, vacuumizing to-0.09 MPa during the heat preservation period to remove hydrochloric acid, introducing the hydrochloric acid into ammonia water with the concentration of 10 wt% for adsorption to obtain the crude product with the pH value of 5, adding a proper amount of magnesium powder, and neutralizing the crude product to the pH value of about 7; and rectifying the crude product under reduced pressure to obtain a product of vinyl ethoxy ethyl dilactate silane, wherein the content of the product is 99.0 percent, and the yield is 80 percent.
Example 2
(1) Feeding and reacting according to the molar ratio of the vinyl trichlorosilane to the ethanol of 1: 1.2: firstly adding ethanol into a reaction kettle, heating to 80 ℃ to enable the ethanol to be in a slightly boiling state, then slowly dropwise adding vinyl trichlorosilane from the top of a filler tower at a dropwise adding speed of 3.8g/min to enable the vinyl trichlorosilane to be in full contact reaction in the tower, keeping the temperature at 100 ℃ after dropwise adding is finished to react for 2 hours, and introducing hydrochloric acid generated in the reaction period into ammonia water with the concentration of 10 wt% for adsorption to obtain an intermediate C2H3Si(OC2H5)Cl2；
(2) According to the molar ratio of 1: 2, feeding reaction: adding ethyl lactate into a reaction kettle, heating to slightly boil, then dripping the intermediate obtained in the step (1) into the reaction kettle from the top of the tower at the dripping speed of 6.6g/min, keeping the temperature at 150 ℃ for reacting for 5 hours after dripping is finished, and introducing hydrochloric acid generated in the reaction into ammonia water with the concentration of 10 wt% for adsorption during the reaction period to obtain a crude product;
(3) keeping the temperature of the crude product at 120 ℃ for 2 hours, vacuumizing to-0.09 MPa during the heat preservation period to remove hydrochloric acid, introducing the hydrochloric acid into ammonia water with the concentration of 10 wt% for adsorption to obtain the crude product with the pH value of 5, adding a proper amount of magnesium powder, and neutralizing the crude product to the pH value of about 7; and rectifying the crude product under reduced pressure to obtain a product of vinyl ethoxy ethyl dilactate silane, wherein the content of the product is 99.0 percent, and the yield is 82 percent.
Example 3
(1) Feeding and reacting according to the molar ratio of the vinyl trichlorosilane to the ethanol of 1: 1.2: ethanol is added firstlyHeating the reaction kettle to 80 ℃ to be in a slightly boiling state, then slowly dropwise adding vinyltrichlorosilane from the top of the packing tower at a dropwise adding speed of 3.8g/min to ensure that the vinyltrichlorosilane is fully contacted and reacted in the tower, keeping the temperature at 100 ℃ for 2 hours after dropwise adding, and introducing hydrochloric acid generated in the reaction period into ammonia water with the concentration of 10 wt% for adsorption to obtain an intermediate C2H3Si(OC2H5)Cl2；
(2) According to the molar ratio of 1: 2, feeding reaction: adding ethyl lactate into a reaction kettle, heating to slightly boil, then dripping the intermediate obtained in the step (1) into the reaction kettle from the top of the tower at the dripping speed of 6.6g/min, keeping the temperature at 160 ℃ for reacting for 4 hours after dripping is finished, and introducing hydrochloric acid generated in the reaction into ammonia water with the concentration of 10 wt% for adsorption during the reaction period to obtain a crude product;
(3) keeping the temperature of the crude product at 120 ℃ for 2 hours, vacuumizing to-0.09 MPa during the heat preservation period to remove hydrochloric acid, introducing the hydrochloric acid into ammonia water with the concentration of 10 wt% for adsorption to obtain the crude product with the pH value of 5, adding a proper amount of magnesium powder, and neutralizing the crude product to the pH value of about 7; and rectifying the crude product under reduced pressure to obtain a product of vinyl ethoxy ethyl dilactate silane, wherein the content of the product is 99.0 percent, and the yield is 82 percent.
Example 4
(1) Feeding and reacting according to the molar ratio of the vinyl trichlorosilane to the ethanol of 1: 1.2: firstly adding ethanol into a reaction kettle, heating to 80 ℃ to enable the ethanol to be in a slightly boiling state, then slowly dropwise adding vinyl trichlorosilane from the top of a filler tower at a dropwise adding speed of 5.8g/min to enable the vinyl trichlorosilane to be in full contact reaction in the tower, keeping the temperature at 100 ℃ after dropwise adding is finished to react for 2 hours, and introducing hydrochloric acid generated in the reaction period into ammonia water with the concentration of 10 wt% for adsorption to obtain an intermediate C2H3Si(OC2H5)Cl2；
(2) According to the molar ratio of 1: 2, feeding reaction: adding ethyl lactate into a reaction kettle, heating to slightly boil, then dripping the intermediate obtained in the step (1) into the reaction kettle from the top of the tower at the dripping speed of 6.6g/min, keeping the temperature at 160 ℃ for reacting for 4 hours after dripping is finished, and introducing hydrochloric acid generated in the reaction into ammonia water with the concentration of 10 wt% for adsorption during the reaction period to obtain a crude product;
(3) keeping the temperature of the crude product at 120 ℃ for 2 hours, vacuumizing to-0.09 MPa during the heat preservation period to remove hydrochloric acid, introducing the hydrochloric acid into ammonia water with the concentration of 10 wt% for adsorption to obtain the crude product with the pH value of 5, adding a proper amount of magnesium powder, and neutralizing the crude product to the pH value of about 7; and rectifying the crude product under reduced pressure to obtain a product of vinyl ethoxy ethyl dilactate silane, wherein the content of the product is 99.0 percent, and the yield is 78 percent.
Example 5
(1) Feeding and reacting according to the molar ratio of the vinyl trichlorosilane to the ethanol of 1: 1.2: firstly adding ethanol into a reaction kettle, heating to 80 ℃ to enable the ethanol to be in a slightly boiling state, then slowly dropwise adding vinyl trichlorosilane from the top of a filler tower at a dropwise adding speed of 3.8g/min to enable the vinyl trichlorosilane to be in full contact reaction in the tower, keeping the temperature at 100 ℃ after dropwise adding is finished to react for 2 hours, guiding hydrochloric acid generated in the reaction period into ammonia water with the concentration of 10 wt% for adsorption to obtain an intermediate C2H3Si(OC2H5)Cl2；
(2) According to the molar ratio of 1: 3, feeding reaction: adding ethyl lactate into a reaction kettle, heating to slightly boil, then dripping the intermediate obtained in the step (1) into the reaction kettle from the top of the tower at the dripping speed of 6.6g/min, keeping the temperature at 150 ℃ for reacting for 4 hours after dripping is finished, and introducing hydrochloric acid generated in the reaction into ammonia water with the concentration of 10 wt% for adsorption during the reaction period to obtain a crude product;
(3) keeping the temperature of the crude product at 120 ℃ for 2 hours, vacuumizing to-0.09 MPa during the heat preservation period to remove hydrochloric acid, introducing the hydrochloric acid into ammonia water with the concentration of 10 wt% for adsorption to obtain the crude product with the pH value of 5, adding a proper amount of magnesium powder, and neutralizing the crude product to the pH value of about 7; and rectifying the crude product under reduced pressure to obtain a product of vinyl ethoxy ethyl dilactate silane, wherein the content of the product is 99.0 percent, and the yield is 85 percent.
Example 6
(1) Feeding and reacting according to the molar ratio of the vinyl trichlorosilane to the ethanol of 1: 1.2: firstly adding ethanol into a reaction kettle, heating to 80 ℃ to ensure that the ethanol is in a slightly boiling state, and thenSlowly dropwise adding vinyltrichlorosilane from the top of the filler at a dropwise adding speed of 3.8g/min to ensure that the vinyltrichlorosilane is fully contacted and reacted in the tower, keeping the temperature at 100 ℃ for 2 hours after the dropwise adding is finished, introducing hydrochloric acid generated in the reaction period into ammonia water with the concentration of 10 wt% for adsorption to obtain an intermediate C2H3Si(OC2H5)Cl2；
(2) According to the molar ratio of 1: 4, feeding reaction: adding ethyl lactate into a reaction kettle, heating to slightly boil, then dripping the intermediate obtained in the step (1) into the reaction kettle from the top of the tower at the dripping speed of 6.6g/min, keeping the temperature at 150 ℃ for reacting for 6 hours after dripping is finished, and introducing hydrochloric acid generated in the reaction into ammonia water with the concentration of 10 wt% for adsorption during the reaction period to obtain a crude product;
(3) keeping the temperature of the crude product at 120 ℃ for 2 hours, vacuumizing to-0.09 MPa during the heat preservation period, removing hydrochloric acid, introducing the hydrochloric acid into ammonia water with the concentration of 10 wt% for adsorption to obtain the crude product with the pH value of 6, adding a proper amount of magnesium powder, and neutralizing the crude product to the pH value of about 7; and rectifying the crude product under reduced pressure to obtain a product of vinyl ethoxy ethyl dilactate silane, wherein the content of the product is 99.2 percent, and the yield is 88 percent.
Example 7
TABLE 1 styrene-acrylic emulsion formulation
| Components | Added amount (g) |
| Deionized water | 380 |
| Emulsifier SR-10 | 12 |
| Emulsifier ER-10 | 3 |
| Initiator | 1.2 |
| Buffering agent | 0.2 |
| Methacrylic acid methyl ester | 32 |
| Acrylic acid | 14 |
| Acrylic acid isooctyl ester | 40 |
| Acrylic acid butyl ester | 80 |
| Styrene (meth) acrylic acid ester | 130 |
| Silane coupling agent | -- |
Three different coupling agents, namely, conventional coupling agent vinyl trimethoxy silane (KH-171), methacryloxypropyl trimethoxy silane (KH-570) and vinyl ethoxy ethyl lactate silane (M1), are respectively used for preparing styrene-acrylic emulsion according to the formula shown in Table 1, the reaction activities of the different coupling agents are tested according to the slag yield after the synthesis of the styrene-acrylic emulsion, and the higher the slag yield in the synthesis process of the styrene-acrylic emulsion, the higher the reaction activity of the coupling agent is, and the results are shown in Table 2.
TABLE 2 slag tapping rate of styrene-acrylic emulsion to which different kinds of coupling agents were added
Three different coupling agents, namely, conventional coupling agent vinyl trimethoxy silane (KH-171), methacryloxypropyl trimethoxy silane (KH-570) and vinyl ethoxy ethyl lactate silane (M1), are respectively used for preparing the styrene-acrylic emulsion according to the formula shown in the table 1, the addition amount of the coupling agents is 1wt%, the adhesion and the water resistance of a paint film are tested, and the influence of different coupling agents on the performance of the paint film is compared, wherein the results are shown in the table 3:
TABLE 3 film testing of different coupling agent synthetic emulsions
Three different coupling agents, namely, conventional coupling agent vinyl trimethoxy silane (KH-171), methacryloxypropyl trimethoxy silane (KH-570) and vinyl ethoxy ethyl lactate silane (M1), are respectively used for preparing styrene-acrylic emulsion according to the formula shown in Table 1, the using amount of the coupling agent is increased to more than 3 wt% for experiment, the slag yield of the synthesized emulsion is detected, and compared with the influence of the increased adding amount of different silane coupling agents on emulsion synthesis, the result is shown in Table 4.
TABLE 4 influence of different silane coupling agent additions on the stability of styrene-acrylic emulsions
The above embodiments are merely for clearly illustrating the embodiments and are not intended to limit the embodiments. Other variants and modifications of the invention, which are obvious to those skilled in the art and can be made on the basis of the above description, are not necessary or exhaustive for all embodiments, and are therefore within the scope of the invention.
Claims (10)
1. A silane coupling agent characterized in that: the chemical name is vinyl ethoxy ethyl dilactate silane, and the structural formula is as follows:
2. a method for preparing the vinylethoxydiacetoxyethylsilane according to claim 1, comprising the steps of:
(1) vinyl trichlorosilane and ethanol with the molar ratio of 1:1.1-1.2 are stirred at 100-110 ℃ for reaction for 2-3 hours to obtain an intermediate C2H3Si(OC2H5)Cl2；
(2) Reacting the intermediate C2H3Si(OC2H5)Cl2Stirring and reacting with ethyl lactate at 150-160 ℃ for 4-6 hours to obtain a crude product; wherein the molar ratio of the vinyl trichlorosilane to the ethyl lactate is 1: 2-4;
(3) heating the crude product to 90-120 ℃, vacuumizing to-0.09 MPa to-0.095 MPa, maintaining constant temperature and constant pressure for 2-3 hours, reducing pressure, adding magnesium powder to neutralize the crude product to be neutral, and rectifying to obtain the vinyl ethoxy ethyl lactate silane.
3. The method for preparing vinylethoxydilactate ethylsilane according to claim 2, characterized in that: in the step (1), firstly, the ethanol is heated to slight boiling, and then the vinyl trichlorosilane is dropwise added into the ethanol.
4. The method of preparing vinylethoxydiacetoxyethylsilane according to claim 2, characterized in that: in the step (1), the reaction temperature is 100 ℃ and the reaction time is 2 hours.
5. The method for preparing vinylethoxydilactate ethylsilane according to claim 2, characterized in that: in the step (1), the dripping speed of the vinyl trichlorosilane is 3.8 g/min-5.8 g/min.
6. The method for preparing vinylethoxydilactate ethylsilane according to claim 2, characterized in that: in the step (2), ethyl lactate is added into a reaction kettle firstly, heated to slight boiling, and then the intermediate C is dropwise added into the ethyl lactate2H3Si(OC2H5)Cl2。
7. The method for preparing vinylethoxydilactate ethylsilane according to claim 2, characterized in that: in the step (2), the intermediate C2H3Si(OC2H5)Cl2The dropping speed of (A) is 5g/min-6.6 g/min.
8. The method for preparing vinylethoxydilactate ethylsilane according to claim 2, characterized in that: in the step (3), the heating temperature of the crude product is 120 ℃, and the heating time is 2 hours.
9. Use of the silane coupling agent according to claim 1 in acrylic emulsions.
10. The styrene-acrylic emulsion is characterized in that: the silane coupling agent as claimed in claim 1 is added in an amount of 1wt% to 12wt% based on the total weight of the styrene-acrylic emulsion.
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