CN108219063A - A kind of novel antifog resin of UV photocurings and its preparation method and application - Google Patents
A kind of novel antifog resin of UV photocurings and its preparation method and application Download PDFInfo
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- CN108219063A CN108219063A CN201711477012.3A CN201711477012A CN108219063A CN 108219063 A CN108219063 A CN 108219063A CN 201711477012 A CN201711477012 A CN 201711477012A CN 108219063 A CN108219063 A CN 108219063A
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- China
- Prior art keywords
- photocurings
- mixed solution
- resin
- antifog resin
- antifog
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- 239000011347 resin Substances 0.000 title claims abstract description 74
- 229920005989 resin Polymers 0.000 title claims abstract description 74
- 238000000016 photochemical curing Methods 0.000 title claims abstract description 73
- 238000002360 preparation method Methods 0.000 title claims abstract description 18
- 238000000576 coating method Methods 0.000 claims abstract description 28
- 239000011248 coating agent Substances 0.000 claims abstract description 21
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 3
- 239000011259 mixed solution Substances 0.000 claims description 64
- 239000002253 acid Substances 0.000 claims description 14
- ARXJGSRGQADJSQ-UHFFFAOYSA-N 1-methoxypropan-2-ol Chemical compound COCC(C)O ARXJGSRGQADJSQ-UHFFFAOYSA-N 0.000 claims description 13
- 238000010792 warming Methods 0.000 claims description 13
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims description 12
- -1 acrylic ester Chemical class 0.000 claims description 12
- 238000000034 method Methods 0.000 claims description 12
- 239000000178 monomer Substances 0.000 claims description 12
- 238000004321 preservation Methods 0.000 claims description 11
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 claims description 8
- 239000003054 catalyst Substances 0.000 claims description 7
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 claims description 6
- 238000006243 chemical reaction Methods 0.000 claims description 5
- SOGAXMICEFXMKE-UHFFFAOYSA-N Butylmethacrylate Chemical compound CCCCOC(=O)C(C)=C SOGAXMICEFXMKE-UHFFFAOYSA-N 0.000 claims description 4
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 claims description 4
- OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical group N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 claims description 2
- 239000004342 Benzoyl peroxide Substances 0.000 claims description 2
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 claims description 2
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 claims description 2
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 claims description 2
- 235000019400 benzoyl peroxide Nutrition 0.000 claims description 2
- 238000009413 insulation Methods 0.000 claims description 2
- 150000004702 methyl esters Chemical class 0.000 claims description 2
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 claims 1
- GMSCBRSQMRDRCD-UHFFFAOYSA-N dodecyl 2-methylprop-2-enoate Chemical compound CCCCCCCCCCCCOC(=O)C(C)=C GMSCBRSQMRDRCD-UHFFFAOYSA-N 0.000 claims 1
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 claims 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 claims 1
- 239000000853 adhesive Substances 0.000 abstract description 9
- 230000001070 adhesive effect Effects 0.000 abstract description 9
- 239000012752 auxiliary agent Substances 0.000 abstract description 4
- 239000012528 membrane Substances 0.000 abstract description 3
- 239000002994 raw material Substances 0.000 abstract description 2
- 239000000243 solution Substances 0.000 description 19
- 239000003973 paint Substances 0.000 description 7
- 238000010998 test method Methods 0.000 description 7
- 239000011521 glass Substances 0.000 description 6
- 239000000463 material Substances 0.000 description 6
- 238000003848 UV Light-Curing Methods 0.000 description 5
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 5
- 230000000694 effects Effects 0.000 description 5
- 238000002791 soaking Methods 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 4
- 230000000052 comparative effect Effects 0.000 description 4
- 239000003595 mist Substances 0.000 description 4
- 238000012544 monitoring process Methods 0.000 description 4
- 229920000642 polymer Polymers 0.000 description 4
- 239000000758 substrate Substances 0.000 description 4
- 238000012360 testing method Methods 0.000 description 4
- XOSRONVMJSCDAA-UHFFFAOYSA-N COCC(C)O.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1 Chemical compound COCC(C)O.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1 XOSRONVMJSCDAA-UHFFFAOYSA-N 0.000 description 3
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 description 2
- 239000003153 chemical reaction reagent Substances 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 239000012634 fragment Substances 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- HJOVHMDZYOCNQW-UHFFFAOYSA-N isophorone Chemical compound CC1=CC(=O)CC(C)(C)C1 HJOVHMDZYOCNQW-UHFFFAOYSA-N 0.000 description 2
- 238000011056 performance test Methods 0.000 description 2
- 239000002966 varnish Substances 0.000 description 2
- QNODIIQQMGDSEF-UHFFFAOYSA-N (1-hydroxycyclohexyl)-phenylmethanone Chemical group C=1C=CC=CC=1C(=O)C1(O)CCCCC1 QNODIIQQMGDSEF-UHFFFAOYSA-N 0.000 description 1
- LJRSZGKUUZPHEB-UHFFFAOYSA-N 2-[2-(2-prop-2-enoyloxypropoxy)propoxy]propyl prop-2-enoate Chemical compound C=CC(=O)OC(C)COC(C)COC(C)COC(=O)C=C LJRSZGKUUZPHEB-UHFFFAOYSA-N 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 1
- 239000004925 Acrylic resin Substances 0.000 description 1
- 229920000178 Acrylic resin Polymers 0.000 description 1
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 1
- 239000004425 Makrolon Substances 0.000 description 1
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical group COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 1
- 235000019082 Osmanthus Nutrition 0.000 description 1
- 241000333181 Osmanthus Species 0.000 description 1
- 239000002202 Polyethylene glycol Substances 0.000 description 1
- 150000001336 alkenes Chemical class 0.000 description 1
- 238000005452 bending Methods 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 230000002113 chemopreventative effect Effects 0.000 description 1
- 238000010276 construction Methods 0.000 description 1
- 238000001723 curing Methods 0.000 description 1
- 230000007812 deficiency Effects 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 239000008157 edible vegetable oil Substances 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 125000003700 epoxy group Chemical group 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- UHESRSKEBRADOO-UHFFFAOYSA-N ethyl carbamate;prop-2-enoic acid Chemical compound OC(=O)C=C.CCOC(N)=O UHESRSKEBRADOO-UHFFFAOYSA-N 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 125000003827 glycol group Chemical group 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000011159 matrix 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
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000002985 plastic film Substances 0.000 description 1
- 229920006255 plastic film Polymers 0.000 description 1
- 229920000515 polycarbonate Polymers 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 229920000139 polyethylene terephthalate Polymers 0.000 description 1
- 239000005020 polyethylene terephthalate Substances 0.000 description 1
- 239000002861 polymer material Substances 0.000 description 1
- 229920002635 polyurethane Polymers 0.000 description 1
- 239000004814 polyurethane Substances 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 238000003672 processing method Methods 0.000 description 1
- 238000007711 solidification Methods 0.000 description 1
- 230000008023 solidification Effects 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 239000005028 tinplate Substances 0.000 description 1
- 239000012780 transparent material Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
- C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
- C08F220/52—Amides or imides
- C08F220/54—Amides, e.g. N,N-dimethylacrylamide or N-isopropylacrylamide
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F8/00—Chemical modification by after-treatment
- C08F8/14—Esterification
-
- 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
- C09D133/00—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 only one carboxyl radical, or of salts, anhydrides, esters, amides, imides, or nitriles thereof; Coating compositions based on derivatives of such polymers
- C09D133/04—Homopolymers or copolymers of esters
- C09D133/14—Homopolymers or copolymers of esters of esters containing halogen, nitrogen, sulfur or oxygen atoms in addition to the carboxy oxygen
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- General Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Wood Science & Technology (AREA)
- Paints Or Removers (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Polymerisation Methods In General (AREA)
Abstract
The present invention relates to a kind of novel antifog resins of UV photocurings and its preparation method and application, and the structural formula of the antifog resin of UV photocurings is as follows：；Wherein, the value range that the value range that the value range of x is 1~6, y is 2~8, z is 9~16；R1For C1~C13One or more of alkyl group；The molecular weight of the antifog resin of UV photocurings is 1500~3200.There is preferable anti-fog performance, hardness and adhesive force using the photocureable coating that the novel antifog resin of UV photocurings provided by the invention is prepared as raw material.The antifog resin of UV photocurings provided by the invention and photoinitiator, auxiliary agent etc. dissolve each other, manufactured UV photocurings anti-fog coating under the irradiation of UV lamp can film-forming, membrane body has the characteristics that transparency height, good film-forming property, compatibility be good, good toughness.
Description
Technical field
The present invention relates to technical field of polymer materials, and in particular, to a kind of antifog resin of novel UV photocurings and its
Preparation method and application.
Background technology
Water vapour in air condenses into subtle water droplet in glass or transparent plastic surface, and water droplet constantly gathers on surface
It is opaque that collection makes these transparent materials thicken, and the production and life of people is influenced, so preventing the generation of fog from producing
With become particularly important in life.Antifog processing method mainly has electrothermal way and uses anti-fog coating method.Electrothermic fog prevention method is
Mix electric heater unit on antifog equipment is needed, increase equipment surface temperature by heating, fog rapid evaporation without
Mist layer can be formed, the method good antifogging effect antifog so as to achieve the purpose that, but construction is complicated of high cost, and cannot be in glasses
It is used in the small type mobile devices such as piece；The use of anti-fog coating method is to coat one layer of anti-fog coating in substrate surface, the method is convenient
Fast, it is at low cost, it is one of following antifog Main way.
UV photocureable coating products are various, different properties, but have relative to other traditional coatings that curing rate is fast, film
The features such as quality is high, and energy expenditure is low, excellent combination property.Zoromba etc. is prepared for a kind of polyurethane acrylate paint, uses
Isophorone is reacted again with HEA with the urethane acrylate anti-fog coating of poly ethyldiol modified preparation, can be applied to organic glass
The substrate surfaces such as glass, polyethylene terephthalate, makrolon, anti-fog performance is excellent, since polyethylene glycol structures therein make it
It is flexible good but bad to the adhesive force of ground.Zhao Ziqian gathers using photosensitive acrylic ester oligomer as matrix and HEA, AM, TPGDA
It closes, adds in photoinitiator auxiliary agent etc., be prepared for a kind of photocuring anti-fog coating, the study found that its film anti-fog performance is excellent,
In TPGDA（Tri (propylene glycol) diacrylate）Make its have to ground good adhesive force but cure after paint film hardness not
Height, not damage resistant and friction.Fumio Tanabiki in 9084982 B2 of foreign patent US have invented one kind with metering system
Sour methyl esters is copolymerized to obtain solvent type acrylic resin, anti-fog coating anti-fog performance prepared by the method with N,N-DMAA
It is good, glossiness is high, film forming is uniform, but antifog service life it is shorter, with the poor adhesive force of ground, compatibility is bad, easily goes out
Existing cut is also possible to will appear phenomena such as coming off, and it is clean and tidy with appearance to influence anti-fog effect.
Therefore, there is an urgent need for researching and developing, a kind of strong adhesive force, anti-fog performance be good, the antifog resin of UV photocurings with high hardness.
Invention content
It is an object of the invention to overcome the deficiencies of the prior art and provide a kind of novel antifog resin of UV photocurings, with this
The photocureable coating that the novel antifog resin of UV photocurings that invention provides is prepared for raw material has preferable anti-fog performance, hard
Degree and adhesive force.
Another object of the present invention is to provide the preparation method of the above-mentioned novel antifog resin of UV photocurings.
Another object of the present invention is to provide the above-mentioned novel antifog resin of UV photocurings in UV photocuring anti-fog coatings
Application.
Another object of the present invention is to provide a kind of UV photocurings anti-fog coating.
To achieve the above object, the present invention adopts the following technical scheme that：
A kind of novel antifog resin of UV photocurings, the structural formula of the antifog resin of UV photocurings are as follows：
；
Wherein, the value range that the value range that the value range of x is 1~6, y is 2~8, z is 9~16；R1For C1~C13Alkane
One or more of base group；The molecular weight of the antifog resin of UV photocurings is 1500~3200.
The present invention introduces epoxy group and double using acrylic monomer and N,N-DMAA as the main chain of polymer
Key can form antifog film under ultraviolet light in substrate surface, and other than with anti-fog performance, this film and base material are also preferable
Compatibility and mechanical performance.Contain double bond in UV light-cured resins provided by the invention, under the irradiation of UV lamp, can draw with light
Hair agent reaction and then film-forming, glass or other polymer surfaces are attached to, achieved the effect that antifog.What is formed is anti-
Mist film has the characteristics that transparency height, good toughness, good with the compatibility of material.In addition, UV photocurings provided by the invention are antifog
Resin also has many advantages, such as that solidification rate is fast, good film-forming property, good toughness, can be applied to anti-fog coating.
Preferably, the value range that the value range that the value range of x is 2~5, y is 3~7, z is 10~15.
Preferably, R1 C1~C12One or more of alkyl.
Preferably, the molecular weight of the antifog resin of UV photocurings is 1800~3000.
The present invention protects the preparation method of the above-mentioned novel antifog resin of UV photocurings simultaneously, and the method is as follows：
S1：Catalyst and propylene glycol monomethyl ether are hybridly prepared into mixed solution 1, triphenylphosphine and propylene glycol monomethyl ether are mixed
Mixed solution 2 is configured to, by glyceral methacrylate, N,N-DMAA, acrylic ester monomer, propylene glycol list
Methyl ether is hybridly prepared into mixed solution 3, and acrylic monomer and propylene glycol monomethyl ether are mixedly configured into mixed solution 4, spare；
S2：The mixed solution 1 of part and mixed solution 3 are mixed, are warming up to 88~92 DEG C and is flowed after keeping the temperature 25~35min plus is surplus
Remaining mixed solution then in 88~92 DEG C of 2~3h of insulation reaction, obtains ternary prepolymer；
S3：Mixed solution 2 and mixed solution 4 are added in ternary prepolymer obtained by S2, is warming up to 101~105 DEG C of 5~6h of heat preservation
Afterwards, acid value is monitored, when acid value ＜ 0.5mgKOH/g, is discharged up to the novel antifog resin of UV photocurings；
Wherein, the catalyst is azodiisobutyronitrile and/or benzoyl peroxide.
Reaction process is as follows：
The ternary high polymer copolymer that preparation method provided by the invention is prepared has good hydrophilic property, good toughness, stability
The advantages that good, using the ternary prepolymer as base-material, the UV light that superperformance can be prepared with acrylic monomer, catalyst reaction is consolidated
Chemoprevention mist resin.
Preferably, in S1, the acrylic ester monomer is methyl methacrylate, butyl methacrylate or methyl-prop
One or more of olefin(e) acid lauryl etc.；In S3, the acrylic monomer is acrylic acid.
Preferably, in S1, the mass ratio of the catalyst and propylene glycol monomethyl ether is 1：10~1:3.
Preferably, in S1, the glyceral methacrylate, N,N-DMAA, acrylic ester monomer
Molar ratio is 2~5：3~7：10~15.
Preferably, in S3, the temperature after heating is 105 DEG C, keeps the temperature 4h.
The present invention protects application of the above-mentioned novel antifog resin of UV photocurings in UV photocuring anti-fog coatings simultaneously.
The present invention also protects a kind of UV photocurings anti-fog coating, and the above-mentioned novel antifog tree of UV photocurings is included in the coating
Fat and photoinitiator.
The antifog resin of UV photocurings provided by the invention and photoinitiator, auxiliary agent etc. dissolve each other, and manufactured UV photocurings are antifog
Coating under the irradiation of UV lamp can film-forming, membrane body has the spies such as transparency height, good film-forming property, the good, good toughness of compatibility
Point.
Compared with prior art, the present invention has the advantages that：
Contain double bond in UV light-cured resins provided by the invention, under the irradiation of UV lamp, can be reacted with photoinitiator and then
Film-forming is attached to glass or other polymer surfaces, achievees the effect that antifog.The antifog film of formation has transparency
The features such as compatibility of height, good toughness and material is good.The antifog resin of UV photocurings provided by the invention and photoinitiator, auxiliary agent
Etc. dissolving each other, manufactured UV photocurings anti-fog coating under the irradiation of UV lamp can film-forming, membrane body has that transparency is high, film forming
The features such as property is good, compatibility is good, good toughness.
Description of the drawings
Fig. 1 is the preparation flow figure of UV photocurings anti-fog coating provided by the invention.
Specific embodiment
Further illustrated the present invention below in conjunction with specific embodiments and the drawings, but embodiment the present invention is not done it is any
The restriction of form.Unless stated otherwise, the reagent of the invention used, method and apparatus is the art conventional reagent, methods
And equipment.
Unless stated otherwise, agents useful for same and material of the present invention are purchased in market.
A kind of 1 antifog resin 1 of UV photocurings of embodiment
A kind of novel antifog resin of UV photocurings, the molecular weight of the antifog resin is about 1800, the antifog tree of UV photocurings
The structural formula of fat is as follows：
The preparation method of the above-mentioned antifog resin of UV photocurings is as follows：
S1：It is in right amount mixed solution 1 to prepare 8.92%wt benzoyl peroxides-propylene glycol monomethyl ether solution respectively, 5.66%wt's
Triphenylphosphine-propylene glycol monomethyl ether solution is in right amount mixed solution 2, and molar ratio is glyceral methacrylate：Methacrylic acid
Methyl esters:N, N- dimethacrylamide=3:2:12 16.0%wt propylene glycol monomethyl ethers solution is in right amount mixed solution 3,15.6%
The acrylic acid of wt-propylene glycol monomethyl ether solution is in right amount mixed solution 4, spare.
S2：The mixed solution 1 of part and mixed solution 3 are mixed, are warming up to 90 DEG C and keeps the temperature 30min, while flows plus remains
Remaining mixed solution 1 and mixed solution 3, time for adding 80min, after stream adds, 90 DEG C of heat preservations, soaking time 3h obtains ternary
Prepolymer；
S3：Mixed solution 2, mixed solution 4 are added in ternary prepolymer obtained by S2, after being warming up to 102 DEG C of heat preservation 6h, monitoring acid
Value when acid value ＜ 0.5mgKOH/g, discharges up to the novel antifog resin of UV photocurings.
A kind of 2 antifog resin 2 of UV photocurings of embodiment
A kind of novel antifog resin of UV photocurings, the molecular weight of the antifog resin is about 2500, the antifog tree of UV photocurings
The structural formula of fat is as follows：
The preparation method of the above-mentioned antifog resin of UV photocurings is as follows:
S1：It is in right amount mixed solution 1 to prepare 8.95%wt benzoyl peroxides-propylene glycol monomethyl ether solution respectively, 5.47%wt's
Triphenylphosphine-propylene glycol monomethyl ether solution is in right amount mixed solution 2, and molar ratio is glyceral methacrylate:Methacrylic acid
Methyl esters:N, N- dimethacrylamide=5:5:11 15.98%wt propylene glycol monomethyl ethers solution is in right amount mixed solution 3,16.4%
The acrylic acid of wt-propylene glycol monomethyl ether solution is in right amount mixed solution 4, spare.
S2：The mixed solution 1 of part and mixed solution 3 are mixed, are warming up to 90 DEG C and keeps the temperature 30min, while flows plus remains
Remaining mixed solution 1 and mixed solution 3, time for adding 80min, after stream adds, 90 DEG C of heat preservations, soaking time 3h obtains ternary
Prepolymer；
S3：Mixed solution 2, mixed solution 4 are added in ternary prepolymer obtained by S2, after being warming up to 102 DEG C of heat preservation 6h, monitoring acid
Value when acid value ＜ 0.5mgKOH/g, discharges up to the novel antifog resin of UV photocurings.
A kind of 3 antifog resin 3 of UV photocurings of embodiment
A kind of novel antifog resin of UV photocurings, the molecular weight of the antifog resin is about 3000, the antifog tree of UV photocurings
The structural formula of fat is as follows：
The preparation method of the above-mentioned antifog resin of UV photocurings is as follows:
S1：It is in right amount mixed solution 1 to prepare 9.05%wt benzoyl peroxides-propylene glycol monomethyl ether solution respectively, 5.39%wt's
Triphenylphosphine-propylene glycol monomethyl ether solution is in right amount mixed solution 2, and molar ratio is glyceral methacrylate:Methacrylic acid
Methyl esters：N, N- dimethacrylamide:=7:2:15 15.2%wt propylene glycol monomethyl ethers solution is in right amount mixed solution 3,16.4%
The acrylic acid of wt-propylene glycol monomethyl ether solution is in right amount mixed solution 4, spare.
S2：The mixed solution 1 of part and mixed solution 3 are mixed, are warming up to 90 DEG C and keeps the temperature 30min, while flows plus remains
Remaining mixed solution 1 and mixed solution 3, time for adding 80min, after stream adds, 90 DEG C of heat preservations, soaking time 3h obtains ternary
Prepolymer；
S3：Mixed solution 2, mixed solution 4 are added in ternary prepolymer obtained by S2, after being warming up to 102 DEG C of heat preservation 6h, monitoring acid
Value when acid value ＜ 0.5mgKOH/g, discharges up to the novel antifog resin of UV photocurings.
A kind of 4 antifog resin 4 of UV photocurings of embodiment
A kind of novel antifog resin of UV photocurings, the molecular weight of the antifog resin is about 2700, the antifog tree of UV photocurings
The structural formula of fat is as follows：
The preparation method of the above-mentioned antifog resin of UV photocurings is as follows:
S1：It is in right amount mixed solution 1 to prepare 10.3%wt benzoyl peroxides-propylene glycol monomethyl ether solution respectively, the three of 6.3%wt
Phenylphosphine-propylene glycol monomethyl ether solution is in right amount mixed solution 2, and molar ratio is glyceral methacrylate:The methacrylic acid moon
Osmanthus ester:N, N- dimethacrylamide=7:3:10 82.34%wt propylene glycol monomethyl ethers solution is in right amount mixed solution 3,23.0%
The acrylic acid of wt-propylene glycol monomethyl ether solution is in right amount mixed solution 4, spare.
S2：The mixed solution 1 of part and mixed solution 3 are mixed, are warming up to 90 DEG C and keeps the temperature 30min, while flows plus remains
Remaining mixed solution 1 and mixed solution 3, time for adding 80min, after stream adds, 90 DEG C of heat preservations, soaking time 3h obtains ternary
Prepolymer；
S3：Mixed solution 2, mixed solution 4 are added in ternary prepolymer obtained by S2, after being warming up to 102 DEG C of heat preservation 6h, monitoring acid
Value when acid value ＜ 0.5mgKOH/g, discharges up to the novel antifog resin of UV photocurings.
A kind of non-UV curing anti foggings resin 5 of comparative example 1
The non-antifog resins of UV are different in the film-forming mechanism of substrate surface from the antifog resin of UV photocurings, anti-fog performance, hard
Degree, adhesive force, transparency, flexibility etc. can all have differences, this comparative example compares itself and UV using the antifog resins of non-UV as control
The performance difference of the antifog resin of photocuring.
A kind of non-UV curing anti foggings resin, the molecular weight of the antifog resin is about 2000.The antifog resins of non-UV
Structural formula is as follows：
The preparation method of above-mentioned non-UV curing anti foggings resin is as follows:
S1：It is in right amount mixed solution 1 to prepare 8.29%wt benzoyl peroxides-propylene glycol monomethyl ether solution respectively, and molar ratio is first
Base methyl acrylate:N, N- dimethacrylamide=1:1 16.0%wt propylene glycol monomethyl ethers solution is mixed solution 3 in right amount；
S2：The mixed solution 1 of part and mixed solution 3 are mixed, are warming up to 90 DEG C and keeps the temperature 30min, at the same flow plus it is remaining
Mixed solution 1 and mixed solution 3, time for adding 80min, after stream adds, 90 DEG C of heat preservations, soaking time 3h discharges up to non-
UV curing anti fogging resins.
Performance test
The antifog resin of UV photocurings that Examples 1 to 4 is prepared is mixed with UV photocuring anti-fog coatings with photoinitiator.
The mass ratio of the UV light-cured resins and photoinitiator is 100:4, the photoinitiator is 1- hydroxycyclohexyl phenyl ketones
（184）.The photocuring anti-fog coating being prepared is tested for the property, the non-UV curing anti foggings being prepared with comparative example 1
Resin 5 is as control.Test method is as follows, and test result see the table below 1.
（1）Anti-fog performance
Test method refers to the hot mist method of water-bath in the anti-fog properties test method of GB/T 31726-2015 plastic films.
Anti-fog performance：D grades-film surface has part water droplet；The preferable transparencies of D/E-, film surface have a small amount of water droplet.
（2）Hardness
Test method refers to standard GB/T/T 6739-1996《Hardness of film pencil measuring method》：It is measured using testing machine method.
（3）Compatibility（Adhesive force）
Test method refers to standard GB/T/T9286-1998《The cross cut test of paint and varnish paint film》.0 grade：Cut edge
It completes smoothly, none lattice comes off；1 grade：Have a little coating shedding in notch infall, but cross-cut area is impacted cannot be bright
It is aobvious to be more than 5%；2 grades：There is coating shedding in notch infall/or along notching edge, impacted cross-cut area is significantly greater than
5%, but 15% cannot be significantly greater than；3 grades：Coating is partly or entirely come off with big fragment along cut edge and/or in grid difference
It is partly or entirely peeled off on position, impacted cross-cut area is significantly greater than 15%, but cannot be significantly greater than 35%；4%：It applies
Layer is peeled off along the big fragment in cut edge, and impacted cross-cut area is significantly greater than 35%, but cannot be significantly greater than 65%；5 grades：
Peeling degree is more than 4 grades.The rank of adhesive force is higher, better to the attachment of ground, and higher with the compatibility of ground, paint film is more not
It easily peels off, service life is longer.
（4）Transparency
Test method refers to standard GB/T/T1721-2008《Varnish, edible vegetable oil and diluent appearance and diapha nometry》.Make
Transparency value is measured with transparency meter, the transparency levels of sample are judged according to numerical value.It is transparent：Measured value 82~
100；It is micro- muddy：Measured value 52~81；It is muddy：Below measured value 51.
（5）Flexibility
Test method refers to standard GB/T/T1731-1993《Paint film flexibility measuring method》Regulation uses mandrel rod analyzer, survey
It is to be bent the tinplate of japanning on the mandrel rod of different-diameter during examination, with the minimum axis that paint film is not caused to destroy after its bending
The diameter of stick（mm）To represent；The diameter of axis be respectively 2mm, 3mm, 4mm, 5mm, 6mm, 8mm, 10mm, 12mm, 16mm, 20mm,
25mm and 32mm, measured diameter is smaller, and toughness is better.
The performance test of resin that 1 Examples 1 to 4 of table and comparative example 1 are prepared
Test result：The antifog resin of UV photocurings is compared with non-UV solidified resins, the antifog resin hardness higher of UV photocurings, to base
More preferably, flexibility is more preferable for the compatibility of material.
Above-described specific embodiment has carried out the purpose of the present invention, technical solution and advantageous effect further
It is described in detail, it should be understood that the foregoing is merely the specific embodiment of the present invention, is not intended to limit the present invention
Protection domain, all within the spirits and principles of the present invention, any modification, equivalent substitution, improvement and etc. done should all include
Within protection scope of the present invention.
Claims (10)
1. a kind of novel antifog resin of UV photocurings, which is characterized in that the structural formula of the antifog resin of UV photocurings is as follows：
；
Wherein, the value range that the value range that the value range of x is 1~6, y is 2~8, z is 9~16；R1For C1~C13Alkyl
One or more of group；The molecular weight of the antifog resin of UV photocurings is 1500~3200.
2. the novel antifog resin of UV photocurings according to claim 1, which is characterized in that the value range of x is 2~5, y's
The value range that value range is 3~7, z is 10~15.
3. the novel antifog resin of UV photocurings according to claim 1, which is characterized in that R1For C1~C12In alkyl group
It is one or more of.
4. the novel antifog resin of UV photocurings according to claim 1, which is characterized in that the antifog resin of UV photocurings
Molecular weight is 1800~3000.
5. the preparation method of any novel antifog resin of UV photocurings of Claims 1 to 4, which is characterized in that the method
It is as follows：
S1：Catalyst and propylene glycol monomethyl ether are hybridly prepared into mixed solution 1, triphenylphosphine and propylene glycol monomethyl ether are mixed
Mixed solution 2 is configured to, by glyceral methacrylate, N,N-DMAA, acrylic ester monomer, propylene glycol list
Methyl ether is hybridly prepared into mixed solution 3, and acrylic monomer and propylene glycol monomethyl ether are mixedly configured into mixed solution 4, spare；
S2：The mixed solution 1 of part and mixed solution 3 are mixed, are warming up to 88~92 DEG C and is flowed after keeping the temperature 25~35min plus is surplus
Remaining mixed solution then in 88~92 DEG C of 2~3h of insulation reaction, obtains ternary prepolymer；
S3：Mixed solution 2 and mixed solution 4 are added in ternary prepolymer obtained by S2, is warming up to 101~105 DEG C of 5~6h of heat preservation
Afterwards, acid value is monitored, when acid value ＜ 0.5mgKOH/g, is discharged up to the novel antifog resin of UV photocurings；
Wherein, the catalyst is azodiisobutyronitrile and/or benzoyl peroxide.
6. preparation method according to claim 5, which is characterized in that in S1, the acrylic ester monomer is metering system
One or more of sour methyl esters, butyl methacrylate or lauryl methacrylate；The acrylic monomer is propylene
Acid and/or methacrylic acid.
7. preparation method according to claim 5, which is characterized in that in S1, the matter of the catalyst and propylene glycol monomethyl ether
Amount is than being 1：10~1:3.
8. preparation method according to claim 5, which is characterized in that in S1, the glyceral methacrylate, N, N- diformazans
Base acrylamide, acrylic ester monomer molar ratio be 2~5：3~7：10~15.
9. application of any novel antifog resin of UV photocurings of Claims 1 to 4 in UV photocuring anti-fog coatings.
10. a kind of UV photocurings anti-fog coating, which is characterized in that any described novel comprising Claims 1 to 4 in the coating
The antifog resin of UV photocurings and photoinitiator.
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