CN101386722A - Organosilicon coating levelling agent - Google Patents
Organosilicon coating levelling agent Download PDFInfo
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- CN101386722A CN101386722A CNA200710045840XA CN200710045840A CN101386722A CN 101386722 A CN101386722 A CN 101386722A CN A200710045840X A CNA200710045840X A CN A200710045840XA CN 200710045840 A CN200710045840 A CN 200710045840A CN 101386722 A CN101386722 A CN 101386722A
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Abstract
The invention discloses an organosilicon paint leveling agent with a general formula of a structure as shown in a formula (I) and a preparation method thereof. The method adopts two steps for reaction: (1) preparing a methyl part containing hydrogenous silicone oil by a mixed siloxane balancing method; and (2) preparing organic group modified polymethyl silica to obtain the organosilicon paint leveling agent. The organosilicon paint leveling agent has the performances of controlling surface flowing, improving leveling, increasing the lustrousness of a coating film, enhancing smoothness and resisting scratch.
Description
Technical field
The present invention relates to a kind of coating levelling agent, more specifically to polyethers, alkane modified polyorganosiloxane and in coating as the purposes of flow agent.
Background technology
In order to overcome coating bad disadvantage of levelling in the coating decoration process, coating is flowed and drying and forming-film after obtain smooth filming, need be controlled film coated surface.
In order to improve the levelling property of coating, can adopt the surface tension that reduces between coating and the base material, make coating and ground have good wettability; Adjust evaporation rate of solvent; Reduce viscosity; Improve the flowability of coating; Prolong flow time; In film coated surface formation unimolecular layer as thin as a wafer, so that uniform surface tension to be provided.By the adding of anti-shrinkage cavity, flow agent, just can all or part ofly satisfy above condition, thereby obtain better levelling effect, make film coated surface smooth smooth.
The past adopts in solvent based coating often with ketone, ester class, aromatic hydrocarbons or the main multi-functional fine solvent of being made up of the high boiling solvent mixture for improving the paint flow levelling, thereby adjusted the evaporation rate of solvent, made coating in drying process, have average evaporation rate and solvency power.In Air drying coating, because of solvent evaporation is fast, dope viscosity is excessive, flows and hinder.At this moment, it is effective using the solvent based flow agent.Only increasing solids constituent that solvent can make coating descends and causes disadvantage such as sagging; Perhaps keep solvent, only add high boiling solvent and adjust evaporation rate and improve levelling, consequently prolong time of drying.
Another kind of coating levelling agent is to be main constituent with the restricted long-chain resin of consistency, as cellaburate class, polyacrylate(s) etc.Can reduce the surface tension between coating and the ground and improve wettability.But its molecular weight is lower, and is not exclusively miscible with the resin of coating.Can form defectives such as depression, shrinkage cavity, orange peel on the cured coating film surface like this.
The third coating levelling agent is to be main constituent with the restricted long-chain polysiloxane of consistency, as phenylbenzene polysiloxane, methyl phenyl silicone and organic radical modified polyorganosiloxane etc.It has the mobile effect of control surface, plays and improves the levelling effect.And after solvent evaporates, polysiloxane forms unimolecular layer in film coated surface, be one deck as thin as a wafer and slick film, thereby improve the gloss of filming.Polysiloxane itself is a kind of tensio-active agent, can improve the wettability to ground again, thereby reaches the purpose of improving levelling.
Organosilicon is prevented the action effect of shrinkage cavity, flow agent, depends on the chemical structure and the usage quantity of polysiloxane.As polysiloxane molecule amount size, the type of organic group and position, the Siliciumatom type of attachment all will influence its action effect.How having experimental results show that its consumption has side effects on the contrary.
Because polydimethylsiloxane is poor to the coating resin consistency, can increase its consistency by the modification of phenyl.But can only provide limited effect to coating, tangible levelling effect is promptly arranged, not have and add lustre to, increase sliding effect, in formulation for coating material, use not general.
Have been found that organic radical modification polymethyl siloxane is as containing the organopolysiloxane of multiple organic group modifications such as polyethers, alkane, reactive organic radical, as long as select suitable big or small organic radical, on long-chain polysiloxane part chain belt Si atom, adopt the Si-C key mode of hydrolysis to connect organic group simultaneously, this class modification organopolysiloxane compound has good wettability, improve levelling property effectively, promote gloss, slippery and anti scuffing performance.
Summary of the invention
Purpose of the present invention is for providing a kind of organosilicon coating levelling agent, and its general formula is as follows:
Or
Wherein, x=10-100, y+z=2-15;
One or more;
R2 is-(CH
2)
3-O-(C
2H
4O)
a(C
3H
6O)
b-R '
A=0-25 wherein, b=0-25, R '=H, CH
3, C
2H
5, C
4H
9And COCH
3
Above-mentioned R2 can be identical, also can be different.
Another object of the present invention is the preparation method that this organosilicon coating levelling agent is provided.
The preparation method of organosilicon coating levelling agent of the present invention comprises the steps:
(1) the hybrid silicone null readings prepares the methyl moiety containing hydrogen silicone oil
Balanced reaction:
With methyl hydrogen cyclosiloxane, dimethyl cyclosiloxane and hexamethyldisiloxane, also can replace the methyl hydrogen cyclosiloxane with the full containing hydrogen silicone oil of methyl, in the presence of an acidic catalysts such as trifluoromethane sulfonic acid, sulfuric acid, atlapulgite and strongly acidic macroporous cation exchange resin, balanced reaction 3-24h makes the methyl moiety containing hydrogen silicone oil through aftertreatment more at a certain temperature.
Adopt trifluoromethane sulfonic acid or sulfuric acid to carry out to remove catalyzer after balanced reaction is finished, can adopt to leave standstill and tell acid, be washed to neutrality, perhaps with in yellow soda ash, the sodium bicarbonate and after-filtration remove sodium sulfate byproduct, also can wash with water to neutrality, steam low-boiling-point substance and water in the heating decompression again, obtain clear, colorless methyl moiety containing hydrogen silicone oil.If make catalyzer with acidic white earth or strongly-acid macropore cation resin, balanced reaction is after remove by filter catalyzer, and distills with above same method and to remove low-boiling-point substance, obtains clear, colorless methyl moiety containing hydrogen silicone oil equally.Temperature of reaction is low more, and it is long more to reach the balance required time, otherwise temperature is high more, and it is short more to reach the balance required time.And the balanced reaction time is too short, and the polysiloxane molar mass distribution is wide, may influence quality product; Balanced reaction temp is too high, though can shorten the reaction times, reaction may make silicon oil viscosity too high, also easily takes place crosslinked.Balanced reaction is preferably in 40-70 ℃, and the 5-8h. catalyst levels is controlled at the 1-10% of reactant total mass number, consumption<1%, and it is long that reaction reaches balance time; If though 10% can reduce temperature of reaction, shorten the reaction times, and may bring difficulty to aftertreatment, therefore, only catalyst levels is 2-6%, and selects the different sorts catalyzer for use, its consumption is different.
(2) preparation of organic radical modification methyl polysilicone
The present invention partly links at the long-chain polysiloxane to adopt the Si-C key mode of hydrolysis to connect organic group on the Si atom, rather than the Si-O-C key mode of connection of facile hydrolysis.Its reaction formula is as follows:
Y+z=y wherein
1X, y, z, a, b, R ' define the same;
R3 is H or CH
3
By the polydimethylsiloxane that contains the Si-H base, be methyl moiety containing hydrogen silicone oil and single-ended allyl polyether and other olefin(e) compound, in the presence of platinum catalyst, prepare in the organic radical modification polydisiloxane process through polyaddition reaction, because the methyl moiety containing hydrogen silicone oil is immiscible with the organic compound that contains unsaturated link(age), and addition polymerization begins to be thermopositive reaction, will add solvent such as toluene, Virahol or its mixture usually.Solvent load is the 5-120% of reactant total mass number, and<do not have ideal role at 5% o'clock, 120% pair of safety and some product aftertreatment make troubles, being fit to consumption is 30-70%.
In order to prevent that side reactions such as unsaturated reactant generation autohemagglutination, oxidation, isomerization from taking place, must be in the addition polymerization process at rare gas element such as N
2Carry out down Deng protection, and add an amount of stopper such as antioxidants such as phenols, phytic acid and prevent autohemagglutination and oxidation generation as single-ended alkylene polyethers; Add an amount of organic carboxylate such as sodium acetate, Trisodium Citrate is made buffer reagent, makes allyl group stable, suppress isomerization and take place.
The polyaddition reaction catalyzer can be used platinum, carrier platinum, platinic compound and platinum inner complex etc.Usually use the alcoholic solution or the toluene solution of platinic compound, platinum-vinylsiloxane inner complex, but side reaction can take place with the Si-H base in alcohol, preferably selects platinum-vinylsiloxane inner complex toluene solution etc. for use.
The addition reaction schedule of operation can take a unsaturated organic compound and solvent to be added in the reactor earlier, mix and intensification, adding platinum catalyst when temperature reaches 60-80 ℃ mixes, drip the methyl moiety containing hydrogen silicone oil in the time of 90-120 ℃, reactant becomes an even transparent single-phase body gradually by the heterogeneous body of muddiness, after tear drop finishes, continues reaction 2-8h at 90-110 ℃ again, survey Si-H base remaining quantity, the decision reaction end.Also can take the anti-method that drips, promptly unsaturated organic compound is added drop-wise to and carry out polyaddition reaction in the methyl moiety containing hydrogen silicone oil.Can also be added to unsaturated organic compound, methyl moiety containing hydrogen silicone oil and solvent in the reactor, mixing and heat temperature raising are to 60-80 ℃, add platinum catalyst, the reaction heating, and become an even transparent single-phase body by muddiness, continue reaction 2-8h at 90-120 ℃, survey the Si-H remaining quantity, the decision reaction end.
Beneficial effect of the present invention:
Organosilicon coating levelling agent of the present invention has control surface and flows, and improves levelling, improves the gloss of filming, and promotes slippery and anti scuffing performance.
Embodiment
The present invention is further elaborated below in conjunction with specific embodiment, but embodiment does not limit protection scope of the present invention.
Embodiment 1
Synthesizing of methyl moiety containing hydrogen silicone oil
In the 1000ml four-hole glass reaction bottle of electric mixer, loop condenser and thermometer is housed, add 431.4gD4 (prestox ring first siloxanes), 56.8gD4 respectively
H(1,3,5,7-tetrahydrochysene tetramethyl-ring tetrasiloxane), 11.8gMM and 25g acidic white earth, heat temperature raising is to 50-75 ℃, and at this thermotonus 8h, be cooled to then<50 ℃, and remove by filter catalyzer.Then reactor is made into water distilling apparatus, and under 100 ℃, 1.3KPa, distill, steam low-boiling-point substance, obtain water white transparency methyl moiety containing hydrogen silicone oil, warp
29SiNMR analyzes, and its structural formula is
Embodiment 2
Synthesizing of methyl moiety containing hydrogen silicone oil
Replace acidic white earth with sulfuric acid, reaction unit, reactant, feeding quantity and working method are with embodiment 1.Behind 50-75 ℃ of reaction 8h, 60 ℃ of control temperature of charges add 30gNa slowly equally
2CO
3,, after filtration, remove white solid Na to PH=7
2SO
4, make water distilling apparatus equally into, under 100 ℃, 1.3MPa, steam low-boiling-point substance, obtain the water white transparency methyl moiety containing hydrogen silicone oil identical with formula (II) structure.
Embodiment 3
Synthesizing of organically-modified silicone oil
Electric mixer, reflux exchanger, thermometer, tear drop equilibration tube are being housed, are leading N
2In the 1000mL four-hole glass reaction bottle of tracheae and electrically heated cover, adding formula (II) methyl moiety containing hydrogen silicone oil 300g, polyglycol allyl group methyl ether 173g, CH
3COOK15g (aqueous isopropanol of 1% massfraction), toluene 200g feed dry N
2Gas starts electric mixer, and heating, and when temperature reached 65 ℃, (the platinum feeding quantity was 15 * 10 of a reactant total mass to the toluene solution 1g of adding platinum-divinyl tetramethyl disiloxane inner complex
-6), when reaching 90 ℃, system temperature suspends heating, and reactant is by muddy bleach.At this moment, drip 1-dodecylene 79.2g and glycidyl allyl ether 6g by the tear drop equilibration tube, system becomes transparent by little muddiness again.Gob speed is limited to the reactive system temperature, preferably is controlled at 95-110 ℃, drip off material after, again at this thermotonus 4h.Warp
29It is qualified that SiNMR analyzes Si-H chain link content, but stopped reaction then, otherwise should suitably add catalyzer, prolong the reaction times until qualified.If need to repack distillation into, remove and desolvate.Cooling, stopped reaction.It is yellowish to brown transparent thick liquid getting product.Warp
29SiNMR assay products structural formula is suc as formula (III):
Embodiment 4
Device, identical feeding quantity and working method replace glycidyl allyl ether with alpha-methyl styrene 6.2g similarly to Example 3.Make product through 29SiNMR analytical structure formula suc as formula (IV):
Embodiment 5
Device, identical feeding quantity and working method similarly to Example 3 are with the poly-trimethylene list propenyl ether [CH of poly-ethylene ethylene glycol
2=CHCH
2-O-(C
2H
4O)
13-(C
3H
6O)
10-H] 190.4g replacement polyoxyethylene glycol allyl group methyl ether.Make the product warp
29SiNMR analytical structure formula such as formula V:
Embodiment 6
The preparation of organosilicon coating levelling agent
In three mouthfuls of vials of the 500ml that electric mixer is housed, add embodiment 3 prepared organic base modified dimethyl polysiloxane 40g, start and stir, and add dimethylbenzene 160g, continue to stir 20min, be made into transparent organosilicon coating levelling agent.
Embodiment 7
Organosilicon coating levelling agent is used
(1) organosilicon coating levelling agent and coating resin compatibility test
The organosilicon coating levelling agent 0.2% (based on various coating total mass numbers) that adds the embodiment of the invention 4 respectively in Synolac, polyester and acrylic resin stirs, and blade coating is on sheet glass, and 105 ℃ are toasted 1h.In kind do simultaneously blank test.The back is observed and to be added that not add the flow agent transparency of filming in organosilicon coating levelling agent of the present invention and the blank test all fine.
(2) organosilicon coating levelling property test
Select vibrin to join white paint (face/base=40/60), organosilicon coating levelling agent consumption of the present invention is 0.3% of a resin solid total mass number, joins lacquer spray plate, 140 ℃ of baking 20min.Similarity condition is done and is not added flow agent lacquer plate.Observation is filmed, and the result is that to have added organosilicon coating levelling agent smooth coating of the present invention good, good luster, and feel is smooth; The unfairness and blank is filmed has obvious corrugated defective and pin hole etc., and gloss is poor slightly, and feel is undesirable.
Claims (8)
1. organosilicon coating levelling agent, structural formula is as follows:
Wherein, x=10-100, y+z=2-15;
R2 is-(CH
2)
3-O-(C
2H
4O)
a(C
3H
6O)
b-R '
A=0-25 wherein, b=0-25, R '=H, CH
3, C
2H
5, C
4H
9And COCH
3
Above-mentioned R2 can be identical, also can be different.
2. the preparation method of organosilicon coating levelling agent as claimed in claim 1 comprises the steps:
1) the hybrid silicone null readings prepares the methyl moiety containing hydrogen silicone oil: with methyl hydrogen cyclosiloxane, dimethyl cyclosiloxane and hexamethyldisiloxane, perhaps replace the methyl hydrogen cyclosiloxane with the full containing hydrogen silicone oil of methyl, in the presence of an acidic catalyst, balanced reaction 3-24h makes the methyl moiety containing hydrogen silicone oil through aftertreatment again;
2) preparation of organic radical modification methyl polysilicone: under protection of inert gas, the methyl moiety containing hydrogen silicone oil and the olefin(e) compound of step 1) gained, in the presence of platinum catalyst, add stopper and add buffer reagent, in solvent, prepare organic radical modification polydisiloxane through polyaddition reaction;
Above-mentioned steps 1), 2) in,
Y+z=y
1X, y, z, a, b, R ' define with claim 1;
R3 is H or CH
3
3. the preparation method of organosilicon coating levelling agent according to claim 2 is characterized in that, an acidic catalyst described in the step 1) is trifluoromethane sulfonic acid, sulfuric acid, atlapulgite or strongly acidic macroporous cation exchange resin.
4. the preparation method of organosilicon coating levelling agent according to claim 2 is characterized in that step 2) described in stopper be phenols, phytic acid class antioxidant.
5. the preparation method of organosilicon coating levelling agent according to claim 2 is characterized in that step 2) described in buffer reagent be that organic carboxylate comprises sodium acetate, Trisodium Citrate.
6. the preparation method of organosilicon coating levelling agent according to claim 2 is characterized in that step 2) described in solvent be toluene, Virahol or its mixture, solvent load is the 5-120% of reactant total mass number.
7. the preparation method of organosilicon coating levelling agent according to claim 2 is characterized in that step 2) described in platinum catalyst be platinum, carrier platinum, platinic compound or platinum inner complex.
8. the preparation method of organosilicon coating levelling agent according to claim 7 is characterized in that, the platinum inner complex is the toluene solution of platinum-vinylsiloxane inner complex.
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