CN103881031A - Special organic silicon resin for photocureable coating and preparation process of organic silicon resin - Google Patents
Special organic silicon resin for photocureable coating and preparation process of organic silicon resin Download PDFInfo
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- CN103881031A CN103881031A CN201410058584.8A CN201410058584A CN103881031A CN 103881031 A CN103881031 A CN 103881031A CN 201410058584 A CN201410058584 A CN 201410058584A CN 103881031 A CN103881031 A CN 103881031A
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Abstract
The invention relates to the field of a photocureable coating, and in particular relates to an organic silicon photocureable coating and a preparation method thereof. Specifically, the preparation method comprises the following steps: adding a basic organic silicon monomer, a special organic silicon monomer and a silane coupling agent to an organic solvent according to certain proportions and completely mixing, dropping mixture in water containing ethers, ketone or esters and co-hydrolyzing, and preparing an organic silicon resin prepolymer through controlling hydrolysis temperature and hydrolysis time; adding a special organic matter monomer, pressurizing and heating with presence of a catalyst, and implementing a blocking reaction and a grafting reaction; under a negative pressure condition, removing low molecules and solvent to the end of reaction in which no low molecule is removed, cooling, adding an active solvent and completely dissolving.
Description
Technical field
The present invention relates to a kind of resin and preparation field thereof, particularly a kind of photo-cured coating special-purpose organic silicon resin and preparation technology thereof.
Background technology
The excellent properties of silicone resin is generally familiar with by people, along with the change of synthetic resins composition of raw materials, can synthesize the silicone resin of many special performances, such as, what have can be high temperature resistant, low temperature resistant, what have can be by force and firmly, what have is all right strong and tough, and what have can radiation hardness, and what have can also high insulation etc.Although the performance of silicone resin is different, it is as coating resin, and its paint solidification method is more single, is all conventionally to adopt the thermofixation of solvent-borne type high temperature.
This paint solidification method is traditional, easy and simple to handle, can spray, and can brush, and can flood.But last curing molding is all wanted the high temperature of 160～200 DEG C.Therefore, some occasion, for example super-huge parts, the base materials of non-refractory etc., cannot implement, and its application will be restricted, moreover this class coating generally has solvent conventionally, brings adverse influence to environment.
The developing direction of coatings industry, except invention and introducing performance resins, also will reduce the toxicity in construction process, and solvent-free photo-cured coating is also the direction of a development.
Solvent-free being not equal to do not have solvent, but in Light Curing, the common film forming of solvent and resin, no longer includes solvent evaporates, and therefore this kind solvent is called strong solvent.
Photo-cured coating comes out now, but resin used is generally universal, and as previously mentioned, these paint solidification methods, are all to adopt the thermofixation of solvent-borne type high temperature conventionally.And the property of silicone resin, be incorporated in solvent-free photo-cured coating, be very significant as special performance resins, be also an important technological breakthrough of photo-cured coating aspect.
Therefore, require synthetic one or a series of silicone resin, they must realize photocuring, at room temperature, in ultraviolet ray several seconds to tens of second irradiation time, silicone resin is realized rapidly crosslinked, becomes insoluble macromolecule membrane, and this silicone resin, there is good consistency with selected strong solvent.
Summary of the invention
Technical problem to be solved by this invention is: the synthetic silicone resin of existing processing method is applied on coatings industry, needs heating to solidify.
For solving this technical problem, the invention provides under a kind of room temperature, the silicone resin that photo-cured coating is special and preparation technology thereof, with the synthetic photo-cured coating special-purpose organic silicon resin of the method, both there is advantage and the characteristic of silicone resin, can meet again the requirement that realizes photocuring completely, and good with strong solvent consistency.
The concrete technical scheme adopting of the present invention is:
The invention provides a kind of can carrying out at normal temperatures in the coating of photocuring, the silicone resin that adopts.
The preparation method of above-mentioned photo-cured coating special-purpose organic silicon resin is that concrete technology is as follows:
A, preparation starting monomer
Starting monomer comprises organosilane monomer (wherein, organosilane monomer comprises basic organosilane monomer and extraordinary organosilane monomer) and extraordinary organism monomer,
Basic organosilane monomer is two or more the organosilane monomer material blends in dimethyldichlorosilane(DMCS), diphenyl dichlorosilane, monomethyl trichlorosilane and a phenyl-trichloro-silicane,
Wherein, dimethyldichlorosilane(DMCS), this is the substantially linear skeleton of polysiloxane,
Diphenyl dichlorosilane, this is the linear material of polysiloxane, is again high temperature resistant, the main contributions person of shielding property and raising and solvent and polymer-polymer miscibility,
Monomethyl trichlorosilane, this is the main component of silicone resin crosslinking structure,
One phenyl-trichloro-silicane, this is the main component of silicone resin crosslinking structure,
For above-mentioned 4 kinds of basic organosilane monomers, monomethyl trichlorosilane and a phenyl-trichloro-silicane, in formula of the present invention, be must have, and all the other two kinds of monomers, can add as required or not add,
Extraordinary organosilane monomer is (as the triethoxyl silane containing epoxy group(ing) containing the organosilane monomer (methyl ethylene dichlorosilane) of two key groups, the organosilane monomer (methyl hydrogen dichlorosilane) that contains reactive hydrogen and silane coupling agent; containing the triethoxyl silane of ester group; and the triethoxyl silane of amino-contained, acryl etc.) in more than a kind organosilane monomer material
As preferably: in total organosilane monomer, the organic group R number on Siliciumatom and the ratio of Siliciumatom number, R/Si is between 1.0～1.6, and phenyl number accounts for 15～60% of total R number, and extraordinary organosilane monomer quality accounts for 10～40% of organosilane monomer total mass,
Further: in total organosilane monomer, the organic group R number on Siliciumatom and the ratio of Siliciumatom number, R/Si is between 1.1～1.4, and phenyl number accounts for 20～40% of total R number, and extraordinary organosilane monomer quality accounts for 10～25% of organosilane monomer total mass,
Extraordinary organism monomer is the polyfunctional group organic compound that contains two keys, as the mixture of one or more monomers in methacrylic acid, vinylformic acid, methyl acrylate, methyl methacrylate, Propylene glycol monoacrylate, Hydroxyethyl acrylate, two hydroxy acrylate, vinylformic acid ethylene glycol, MALEIC ANHYDRIDE and fumaric acid anhydride;
B, by ready basic organosilane monomer and extraordinary organosilane monomer in steps A, join in organic solvent and fully after mixing, obtain organosilane monomer mixed solution, the organosilane monomer mixed solution obtaining is added drop-wise in the water that contains ether, ketone or ester, carry out cohydrolysis, make silicone resin prepolymer system
Wherein, organic solvent is boiling point lower than the water-fast organic solvent of 120 DEG C, and organic solvent quality equals monomer mass (0.8-1.2 times that organic solvent quality is monomer mass) substantially,
Ketone, ether or ester are respectively butanone, pimelinketone; Butyl ether; Ethyl acetate, this kind solvent has good consistency with monomer, reacts mitigation, prevents into ring and crosslinked,
In this step, organosilane monomer mixed solution is added drop-wise in the water that contains ether, ketone or ester, carries out cohydrolysis, be specially, hydrolysis temperature is controlled at below 25 DEG C, preferably 5-10 DEG C, and time for adding is controlled at 3-5 hours.In order to make reaction more abundant, after dropwising, can also continue to react 15-30 minutes,
The quality of water is the more than 1.5 times of organosilane monomer total mass, and preferably 2-3 times, the quality of ketone, ether or ester is quality 1/3-1/2;
C, in the silicone resin prepolymer system obtaining in step B, add extraordinary organism monomer, under catalyst action, heating, compressive reaction (block reaction and graft reaction), then under condition of negative pressure, remove low molecule, desolvation, until while deviating from without low molecule, represent to have prepared, obtain photo-cured coating special-purpose organic silicon resin
In step C, specifically, add after extraordinary organism monomer, catalyzer, heating, compressive reaction for some time, stop heating, compressive reaction, be adjusted into condition of negative pressure (vacuumizing), remove after low molecule, solvent, reheat again, compressive reaction for some time, carry out negative pressure again and remove low molecule, solvent, so cyclical operation, until when deviate from without low molecule, be enough to represent to have prepared
The catalyzer of block and graft reaction is the salt of transition metal, mainly contains PtCl
6, lithium acetate, zinc acetate, zinc octoate, cobalt naphthenate etc., object is that the functional group reactions on organosilane monomer and Siliciumatom is completed,
The consumption of catalyzer is 0.1%-1% of total overall reaction monomer (organosilane monomer and extraordinary organism monomer) total mass,
In step C, the quality of the extraordinary organism monomer adding, is 15～35% of organosilane monomer total mass.
By the silicone resin of preparing by above-mentioned steps, be made into photo-cured coating, concrete operations are: under normal temperature, in above-mentioned silicone resin, add strong solvent, fully dissolve,
Strong solvent is vinyl toluene, Vinyl toluene, allyl acrylate or vinylbenzene, and in the photo-cured coating being made into, solid content is 45-55%(massfraction).
The invention has the beneficial effects as follows:
The present invention, by regulating the formula of organosilane monomer, has designed and has had organosilicon special property, and had the silicone resin prepolymer of good consistency.By extraordinary organosilane monomer cohydrolysis with it, make to there is active group on the main chain of silicone resin prepolymer, can carry out grafting and the block polymerization effect of next stage.
Under the effect of extraordinary catalyzer, there is the organic monomer of two keys, a part is with the functional group grafting on Siliciumatom in silicone resin prepolymer, and a part is reacted with the end group of silicone resin prepolymer, forms the segmented copolymer with two keys.
Synthetic like this silicone resin polymkeric substance all has a considerable amount of pairs of key groups on main chain and side chain, be beneficial under ultraviolet radiation with strong solvent in two keys form radical copolymerizations or ionic copolymerization, thereby reach the object of photocuring.
Synthesizing of this photocuring special-purpose organic silicon resin; the market and the market requirement that meets photo-cured coating of photo-cured coating are not only greatly opened up; make to have increased in photo-cured coating the silicone resin of high performance heat resistant; and make the market of silicone resin to nontoxic solvent-free direction exploitation; for photo-cured coating industry has been made contribution; photo-cured coating adapts to the requirement that low-carbon (LC) is nontoxic, energy-saving and cost-reducing solvent-free volatilization and waste, protection of the environment, for chemistry painting industry industry is made significant contribution.
Embodiment
Embodiment 1
A, starting material are by mass:
B, above-mentioned raw materials is joined in 180g toluene, fully mix, mixed solution is dropped in 400g water and 200g pimelinketone mixed solution and is hydrolyzed, hydrolysis temperature is controlled at 5-7 DEG C, within 5 hours, is added dropwise to complete, and obtains silicone resin prepolymer system;
C, in the silicone resin prepolymer system obtaining in step B, be added dropwise to the mixture of 15g methyl methacrylate and 15g Hydroxyethyl acrylate, set reaction pressure 0.15MPa, then add 1g PtCl
6catalyzer, 180 DEG C of reactions,
Vacuum removal solvent and low-boiling-point substance, until while deviating from without low molecule, represent prepare, lower the temperature, and obtains photo-cured coating special-purpose organic silicon resin,
The silicone resin of preparing by above-mentioned steps is cooled to 100 DEG C, adds Vinyl toluene, being made into solid content is 50%(massfraction) photo-cured coating.
The photo-cured coating making in the present embodiment, the key technical indexes is as follows:
Outward appearance: light yellow transparent liquid
Solid content: 50%
Period of storage: half a year above (25 DEG C of preservations)
Ultraviolet curing process:
Utilize the photo-cured coating in the present embodiment, add 0.5%(initiator to account for the mass percent of photo-cured coating) st-yrax be initiator, ultraviolet ray (wavelength is 300nm) is irradiated 20 seconds, rapidly crosslinked film forming, and without unnecessary dissolvent residual, functional (film forming thickness is set according to the requirement of following each performance test standard respectively) of film.
Adhesion property meets GB/T1720-79(89) 1 grade
Heat resistance meets GB/T1735-89 " paint film Heat-tolerance Determination method "
Chemical resistance meets GB/T1763-89 " paint film chemical reagent resistance assay method "
Wet-hot aging performance meets 1 grade of GB/T1740-91 " paint film wet-heat resisting assay method "
Petrol-resistance can meet GB/T1734-93 " paint film petrol-resistance assay method "
Embodiment 2
A, starting material are by mass:
B, above-mentioned raw materials is joined in 160g toluene, fully mix, mixed solution is dropped in 400g water and 200g butyl ether mixed solution and is hydrolyzed, hydrolysis temperature is controlled at 9-10 DEG C, within 3 hours, be added dropwise to complete, in order to make reaction more abundant, after dropwising, continue reaction 15 minutes, obtain silicone resin prepolymer system;
C, in the silicone resin prepolymer system obtaining in step B, be added dropwise to the mixture of 15g methyl methacrylate and 15g fumaric acid anhydride, set reaction pressure 0.05MPa, then add 0.7g zinc acetate catalyst, 170 DEG C of reactions,
Vacuum removal solvent and low molecule, until while deviating from without low molecule, represent prepare, lower the temperature, and obtains photo-cured coating special-purpose organic silicon resin,
The silicone resin of preparing by above-mentioned steps is cooled to 100 DEG C, adds vinylbenzene, being made into solid content is 45%(massfraction) photo-cured coating.
The photo-cured coating making in the present embodiment, the key technical indexes is as follows:
Outward appearance: light yellow transparent liquid
Solid content: 45%
Period of storage: half a year above (25 DEG C of preservations)
Ultraviolet curing process:
Utilize the photo-cured coating in the present embodiment, add 0.8%(initiator to account for the mass percent of photo-cured coating) benzophenone be initiator, ultraviolet ray (wavelength is 240nm) is irradiated 20 seconds, rapidly crosslinked film forming, and without unnecessary dissolvent residual, functional (film forming thickness is set according to the requirement of following each performance test standard respectively) of film.
Adhesion property meets GB/T1720-79(89) 1 grade
Heat resistance meets GB/T1735-89 " paint film Heat-tolerance Determination method "
Chemical resistance meets GB/T1763-89 " paint film chemical reagent resistance assay method "
Wet-hot aging performance meets 1 grade of GB/T1740-91 " paint film wet-heat resisting assay method "
Petrol-resistance can meet GB/T1734-93 " paint film petrol-resistance assay method "
Embodiment 3
A, starting material are by mass:
B, above-mentioned raw materials is joined in 200g toluene, fully mix, mixed solution is dropped in 400g water and 200g ethyl acetate mixed solution and is hydrolyzed, hydrolysis temperature is controlled at 7-9 DEG C, within 4 hours, be added dropwise to complete, in order to make reaction more abundant, after dropwising, continue reaction 30 minutes, obtain silicone resin prepolymer system;
C, in the silicone resin prepolymer system obtaining in step B, be added dropwise to the mixture of 5g methyl methacrylate, 15g fumaric acid anhydride and 10g methacrylic acid, set reaction pressure 0.05MPa, then add 0.6g cobalt naphthenate catalyzer, 180 DEG C of reactions,
Vacuum removal solvent and low molecule, until while deviating from without low molecule, represent prepare, lower the temperature, and obtains photo-cured coating special-purpose organic silicon resin,
The silicone resin of preparing by above-mentioned steps is cooled to 100 DEG C, adds vinylbenzene and ethyl propenoate mixture (both mass ratioes are 1:1), being made into solid content is 55%(massfraction) photo-cured coating.
The photo-cured coating making in the present embodiment, the key technical indexes is as follows:
Outward appearance: yellow transparent liquid
Solid content: 55%
Period of storage: half a year above (25 DEG C of preservations)
Ultraviolet curing process:
Utilize the photo-cured coating in the present embodiment, add 1%(initiator to account for the mass percent of photo-cured coating) benzoin isopropyl ether be initiator, ultraviolet ray (wavelength is 200nm) is irradiated 25 seconds, rapidly crosslinked film forming, and without unnecessary dissolvent residual, functional (film forming thickness is set according to the requirement of following each performance test standard respectively) of film.
Adhesion property meets GB/T1720-79(89) 1 grade
Heat resistance meets GB/T1735-89 " paint film Heat-tolerance Determination method "
Chemical resistance meets GB/T1763-89 " paint film chemical reagent resistance assay method "
Wet-hot aging performance meets 1 grade of GB/T1740-91 " paint film wet-heat resisting assay method "
Petrol-resistance can meet GB/T1734-93 " paint film petrol-resistance assay method ".
Claims (8)
1. a photo-cured coating special-purpose organic silicon resin, is characterized in that: described photo-cured coating can carry out photocuring at normal temperatures.
2. the preparation method of photo-cured coating special-purpose organic silicon resin as claimed in claim 1, is characterized in that: concrete technology is as follows:
A, preparation starting monomer
Starting monomer comprises organosilane monomer and extraordinary organism monomer, and wherein, organosilane monomer comprises basic organosilane monomer and extraordinary organosilane monomer,
Basic organosilane monomer is two or more the organosilane monomer material blends in dimethyldichlorosilane(DMCS), diphenyl dichlorosilane, monomethyl trichlorosilane and a phenyl-trichloro-silicane,
Extraordinary organosilane monomer is containing the organosilane monomer of two key groups, containing the more than a kind organosilane monomer material in organosilane monomer and the silane coupling agent organosilane monomer of reactive hydrogen,
Organosilane monomer containing two key groups is methyl ethylene dichlorosilane,
Organosilane monomer containing reactive hydrogen is methyl hydrogen dichlorosilane,
Extraordinary organism monomer is the mixture of one or more monomers in methacrylic acid, vinylformic acid, methyl acrylate, methyl methacrylate, Propylene glycol monoacrylate, Hydroxyethyl acrylate, two hydroxy acrylate, vinylformic acid ethylene glycol, MALEIC ANHYDRIDE and fumaric acid anhydride;
B, by ready basic organosilane monomer and extraordinary organosilane monomer in steps A, join in organic solvent and fully after mixing, obtain organosilane monomer mixed solution, the organosilane monomer mixed solution obtaining is added drop-wise in the water that contains ether, ketone or ester, carry out cohydrolysis, make silicone resin prepolymer system;
C, in the silicone resin prepolymer system obtaining in step B, add extraordinary organism monomer, under catalyst action, heating, compressive reaction, under condition of negative pressure, remove low molecule, desolvation again, until while deviating from without low molecule, represent to have prepared, obtain photo-cured coating special-purpose organic silicon resin.
3. the preparation method of photo-cured coating special-purpose organic silicon resin as claimed in claim 2, it is characterized in that: in steps A, in described organosilane monomer, organic group R number on Siliciumatom and the ratio of Siliciumatom number, R/Si is between 1.0～1.6, and phenyl number accounts for 15～60% of total R number, extraordinary organosilane monomer quality accounts for 10～40% of organosilane monomer total mass.
4. the preparation method of photo-cured coating special-purpose organic silicon resin as claimed in claim 2, is characterized in that: in step B, the quality of water is the more than 1.5 times of organosilane monomer total mass, and the quality of ketone, ether or ester is quality 1/3-1/2.
5. the preparation method of photo-cured coating special-purpose organic silicon resin as claimed in claim 3, it is characterized in that: in steps A, in described organosilane monomer, organic group R number on Siliciumatom and the ratio of Siliciumatom number, R/Si is between 1.1～1.4, and phenyl number accounts for 20～40% of total R number, extraordinary organosilane monomer quality accounts for 10～25% of organosilane monomer total mass.
6. the preparation method of photo-cured coating special-purpose organic silicon resin as claimed in claim 2, is characterized in that: in step C, the quality of the extraordinary organism monomer adding, is 15～35% of organosilane monomer total mass.
7. the preparation method of photo-cured coating special-purpose organic silicon resin as claimed in claim 2, is characterized in that: in step B, described organic solvent is boiling point lower than the water-fast organic solvent of 120 DEG C.
8. the preparation method of photo-cured coating special-purpose organic silicon resin as claimed in claim 2, it is characterized in that: in step B, described is added drop-wise to organosilane monomer mixed solution in the water that contains ether, ketone or ester, carry out cohydrolysis, be specially, hydrolysis temperature is controlled at 5-10 DEG C, and time for adding is controlled at 3-5 hours.
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Cited By (5)
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| CN106432736A (en) * | 2016-10-21 | 2017-02-22 | 湖南师范大学 | Preparation method of novel UV (Ultraviolet) curable polyfunctionality functional organosilicane monomer and application of novel UV curable polyfunctionality functional organosilicane monomer in stain resisting coating |
| CN107236449A (en) * | 2016-03-29 | 2017-10-10 | 沙河市湡久新材料有限公司 | UV curing types hard coating and it is coated with weatherability hard coat film obtained by the hard coating |
| CN108676125A (en) * | 2018-06-05 | 2018-10-19 | 南雄市瑞晟化学工业有限公司 | Organosilicon grafted and modified glass UV-cured resin |
| CN110183670A (en) * | 2019-06-04 | 2019-08-30 | 无锡博强高分子材料科技有限公司 | A kind of bipolarity dissaving polymer UV matt process for preparing resins and the resin |
| CN110734547A (en) * | 2019-10-25 | 2020-01-31 | 常州市嘉诺有机硅有限公司 | method for preparing organic silicon resin by stepwise hydrolysis |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| CN107236449A (en) * | 2016-03-29 | 2017-10-10 | 沙河市湡久新材料有限公司 | UV curing types hard coating and it is coated with weatherability hard coat film obtained by the hard coating |
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| CN108676125B (en) * | 2018-06-05 | 2020-04-28 | 南雄市瑞晟化学工业有限公司 | Organic silicon graft modified glass ultraviolet curing resin |
| CN110183670A (en) * | 2019-06-04 | 2019-08-30 | 无锡博强高分子材料科技有限公司 | A kind of bipolarity dissaving polymer UV matt process for preparing resins and the resin |
| CN110734547A (en) * | 2019-10-25 | 2020-01-31 | 常州市嘉诺有机硅有限公司 | method for preparing organic silicon resin by stepwise hydrolysis |
| CN110734547B (en) * | 2019-10-25 | 2022-04-08 | 常州市嘉诺有机硅有限公司 | Method for preparing organic silicon resin through stepwise hydrolysis |
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