CN106939143A - The preparation method of photocuring aqueous polyurethane silica silicon inierpeneirating network structure coating material - Google Patents
The preparation method of photocuring aqueous polyurethane silica silicon inierpeneirating network structure coating material Download PDFInfo
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- 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
- C09D183/00—Coating compositions based on macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon, with or without sulfur, nitrogen, oxygen, or carbon only; Coating compositions based on derivatives of such polymers
- C09D183/04—Polysiloxanes
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- C08G18/0819—Manufacture of polymers containing ionic or ionogenic groups containing anionic or anionogenic groups
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- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/08—Processes
- C08G18/10—Prepolymer processes involving reaction of isocyanates or isothiocyanates with compounds having active hydrogen in a first reaction step
- C08G18/12—Prepolymer processes involving reaction of isocyanates or isothiocyanates with compounds having active hydrogen in a first reaction step using two or more compounds having active hydrogen in the first polymerisation step
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- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/30—Low-molecular-weight compounds
- C08G18/34—Carboxylic acids; Esters thereof with monohydroxyl compounds
- C08G18/348—Hydroxycarboxylic acids
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- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/40—High-molecular-weight compounds
- C08G18/42—Polycondensates having carboxylic or carbonic ester groups in the main chain
- C08G18/4266—Polycondensates having carboxylic or carbonic ester groups in the main chain prepared from hydroxycarboxylic acids and/or lactones
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- C08G18/00—Polymeric products of isocyanates or isothiocyanates
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- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/65—Low-molecular-weight compounds having active hydrogen with high-molecular-weight compounds having active hydrogen
- C08G18/66—Compounds of groups C08G18/42, C08G18/48, or C08G18/52
- C08G18/6666—Compounds of group C08G18/48 or C08G18/52
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- C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
- C08G77/04—Polysiloxanes
- C08G77/14—Polysiloxanes containing silicon bound to oxygen-containing groups
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- C09D7/00—Features of coating compositions, not provided for in group C09D5/00; Processes for incorporating ingredients in coating compositions
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- C08L2205/04—Polymer mixtures characterised by other features containing interpenetrating networks
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Abstract
The preparation method of photocuring aqueous polyurethane silica silicon inierpeneirating network structure coating material, belongs to the preparing technical field of aqueous photo-curing organic-inorganic coating material.The method comprises the steps of firstly, preparing can be compatible with organic-silicon-modified tetraethyl orthosilicate pre-condensation presoma, and can UV photocuring aqueous polyurethane emulsion, then again can UV photocurings aqueous polyurethane emulsion and organic-silicon-modified tetraethyl orthosilicate pre-condensation presoma be mixed with and obtain photocuring aqueous polyurethane silica silicon inierpeneirating network structure coating material.The coating material that the present invention is obtained has excellent hardness, gloss, adhesive force, toughness and water resistance etc., the drawbacks of solving Water-resistance of Waterborne Polyurethane difference and low gloss.
Description
Technical field
The invention belongs to the preparing technical field of aqueous photo-curing organic and inorganic coating material.
Background technology
Attention with China to environmental protection, environmental protection legislation is increasingly perfect, people to the cry of environmental protection increasingly
Height, is strictly controlled VOC emission in coating.Aqueous polyurethane light solidifying coating material has efficient, energy-saving and environmental protection, peace
The advantages of full health, and it is widely used in the fields such as gloss oil for paper, woodenware lacquer, ink for screen printing, electro-deposition photoresist.
But mechanical property, water resistance, heat resistance and the surface hydrophobic of its coating do not reach traditional oiliness light-solidifying poly ammonia much also
Ester, so, how to improve the performance of photocuring aqueous polyurethane turns into the Main way of aqueous polyurethane coating Materials
One of, UV curable waterborne coatings technology is because its efficiency of construction is high and environment-friendly advantage is increasingly concerned.
Photocuring aqueous polyurethane is mainly made up of binder resin, light trigger and auxiliary agent.The performance of solidify coating is main
Determined by the design feature of binder resin.The binder resin of the aqueous polyurethane of photocuring, which is included, can carry out photocuring active group
Such as double bond and salifiable group.Therefore, photocuring activity group content and photolytic activity, flexible polyurethane hard segment structure are with comparing
Example, combination property of the content to photocuring water-base polyurethane material into hydrophilic radical after salt play important influence.However,
Photocuring activity group content is low in aqueous polyurethane, causes that coating crosslink density is low, and coating hardness is poor, and gloss is low, alcohol resistance
Difference；Simultaneously because a large amount of hydrophilic radicals inevitably bring the problem of water-resistant coating is poor, it is difficult to meet right in application process
The higher and higher performance requirement that coating is proposed.
The content of the invention
Have that hardness is low, gloss is not high for existing photocuring aqueous polyurethane coating material, alcohol resistance is poor and water-fast
Property difference shortcoming, propose a kind of preparation method of photocuring aqueous polyurethane-silicon-oxygen-silicon inierpeneirating network structure coating material.
Technical solution of the present invention comprises the following steps：
1）Diisocyanate, polyester diol, dihydromethyl propionic acid (DMPA) and dibutyl tin laurate are mixed, mixed
The temperature of zoarium system is the obtained performed polymer of reaction under conditions of 75~80 DEG C；
2）The acrylic resin of performed polymer and hydroxyl is mixed, reacts to after terminating, is cooled under conditions of 70~75 DEG C
After 40 DEG C, add triethylamine and carry out neutralization reaction, neutralization reaction adds deionized water emulsification again after terminating, and obtaining can UV photocuring water
Property polyaminoester emulsion；
3）Can UV photocurings aqueous polyurethane emulsion and the pre-condensation presoma mixing of organic-silicon-modified tetraethyl orthosilicate, warp by described in
UV photocurings and condensation polymerization, obtain photocuring aqueous polyurethane-silicon-oxygen-silicon inierpeneirating network structure coating material.
The method comprises the steps of firstly, preparing can with organic-silicon-modified tetraethyl orthosilicate pre-condensation presoma it is compatible, and can UV light consolidate
Change aqueous polyurethane emulsion, then again can UV photocurings aqueous polyurethane emulsion and the pre-condensation of organic-silicon-modified tetraethyl orthosilicate
Presoma, which is mixed with, obtains photocuring aqueous polyurethane-silicon-oxygen-silicon inierpeneirating network structure coating material.Can UV photocuring water
Property polyaminoester emulsion and organic-silicon-modified tetraethyl orthosilicate be pre-condensed the compatible feature of presoma, i.e., it is heavy not produced when both mix
The phenomenon such as shallow lake or viscosity increase, both are in mixing film forming procedure, and organosilicon can occur hydrophobic with aqueous polyurethane hydrophobic chain
Interaction, organic-silicon-modified tetraethyl orthosilicate pre-condensation presoma is sent out with the volatilization of decentralized medium in UV Light Curings
Raw condensation polymerization reaction, ultimately forms polymer and Si-O-Si inierpeneirating network structure organic-inorganic hybridized coatings.This hair
Bright obtained coating material has excellent hardness, gloss, adhesive force, toughness and water resistance etc., solves aqueous polyurethane
The drawbacks of poor water resistance and low gloss.
The key technology and beneficial effect of the present invention：（1）Replace traditional solvent as medium using water, reduce VOC row
Put, reduce the pollution to environment.（2）Organic and inorganic interpenetrating networks cross-linked structure is designed to improve the poly- ammonia of water-based ultraviolet (UV) curable
The crosslink density of ester coating, so that the hardness for solving existing aqueous polyurethane generally existing is low, the gloss not high, scrubbing character of resistance to alcohol
Poor, not water-fast the drawbacks of.
Further, the mol ratio of the total amount and diisocyanate of polyester diol of the present invention and dihydromethyl propionic acid
For 1: 1.4~1.75, and, dihydromethyl propionic acid accounts for diisocyanate, polyester diol, dihydromethyl propionic acid (DMPA) and two
The 4%~6% of the mixing gross mass of dibutyl tin laurate, dibutyl tin laurate accounts for diisocyanate, polyester diol, two
The 0.1~0.2% of the mixing gross mass of hydroxymethyl propionic acid (DMPA) and dibutyl tin laurate.Hydrophilic chain extender dihydroxymethyl
Propionic acid can make it that aqueous polyurethane emulsion is stable in this ratio, and catalyst dibutyltin dilaurylate can be such that reaction more puts down
Surely.
The step 1）In, the diisocyanate is in hexamethylene diisocyanate or IPDI
Any one.Hexamethylene diisocyanate and IPDI are aliphatic diisocyanates, with preferable
Yellowing resistance, the aqueous polyurethane of synthesis is difficult yellowing.
The polyester diol is polycaprolactone diols.The aqueous polyurethane synthesized using polycaprolactone diols it is resistance to
Gentle water resistance is all relatively good.
The acrylic resin of the hydroxyl is hydroxy-ethyl acrylate, hydroxypropyl acrylate or pentaerythritol triacrylate
In any one.The acrylic resin of hydroxyl can both react there is provided hydroxyl with isocyano, again can containing activity double key
Carry out UV photocurings.
The step 2）In, NCO mole feeds intake in the mole and performed polymer of the acrylic resin of the hydroxyl
Than for 0.1~0.6: 1, can completely be blocked with p- NCO, and there is provided preferable activity double key content.
The step 2）In, the mole for adding triethylamine is identical with the mole of dihydromethyl propionic acid.When triethylamine mistake
When amount or deficiency, it can make it that the storage stability of aqueous polyurethane declines.
It is described can UV photocurings aqueous polyurethane emulsion and organic-silicon-modified tetraethyl orthosilicate be pre-condensed the mixing of presoma
Mass ratio is 1: 1.5~3, under this ratio, the excellent combination property such as hardness, gloss of paint film, can UV photocuring aqueous polyurethanes
Emulsion is excessive so that the glossiness of paint film not enough, can UV photocuring aqueous polyurethane emulsions it is very few, the poor in flexibility of paint film.
Embodiment
Embodiment 1：
1st, the preparation of photocurable aqueous polyurethane emulsion：
By 40.0g (0.24mol) hexamethylene diisocyanate (HDI), 58.0g (0.11mol) PCL205u（Polycaprolactone two
First alcohol）, 4.0g (0.027mol) dihydromethyl propionic acid (DMPA), 0.2g dibutyl tin laurates, 75 DEG C react 4h, system
Standby performed polymer.Now PCL205u and DMPA total amount and HDI molar ratio are 1: 1.75, and dihydromethyl propionic acid is occupied
Prepare the 4% of the raw material gross mass of performed polymer, dibutyl tin laurate occupies the raw material gross mass for preparing performed polymer
0.2%。
16.6g (0.14mol) hydroxy-ethyl acrylate is added into performed polymer, 70 DEG C of reaction 2h enter to-the NCO of performed polymer
Row end-blocking.Now, the rate of charge of NCO mole is 0.6: 1 in the mole and performed polymer of hydroxy-ethyl acrylate.It is cooled to
40 DEG C, add 2.7g (0..027mol) triethylamine and carry out neutralization reaction 10min generation salt.Wherein the mole of triethylamine with
DMPA mole is identical.Add deionized water and carry out emulsification 15min, obtain photocurable aqueous polyurethane emulsion.
2nd, organic-silicon-modified tetraethyl orthosilicate is pre-condensed the preparation of presoma：
By 7.7g tetraethyl orthosilicates（TEOS）, 0.545g γ-methacryloxypropyl trimethoxy silane（KH570）、1g
After water, the mixing of 3.4g ethanol, the pH to 6 that mixed system is adjusted with hydrochloric acid, 6h is reacted in 60 DEG C, organic-silicon-modified positive silicic acid is obtained
Ethyl ester is pre-condensed presoma.
3rd, the preparation of coating material：
It is 1: 1.5 in mass ratio by photocurable aqueous polyurethane emulsion and organic-silicon-modified tetraethyl orthosilicate pre-condensation presoma
Ratio mixing, carry out after UV photocurings and further condensation polymerization, obtain coating material.
4th, properties of product are verified：
By the coating material of acquirement, glossiness test is carried out according to GB/T 1743-1979, coating gloss 92 is obtainedo；
Adhesive force detection, adhesion 1 grade are carried out according to GB 1720-1979.
Hardness determination is carried out according to GB/T 6739-1996, hardness is 2H.
Embodiment 2：
1st, the preparation of photocurable aqueous polyurethane emulsion：
By 52.0g (0.23mol) IPDI (IPDI), 58.0g (0.11mol) PCL205u（Polycaprolactone
Dihydric alcohol）, 7.0g (0.047mol) dihydromethyl propionic acid (DMPA), 0.16g dibutyl tin laurates, 75 DEG C reaction
4h, prepares performed polymer.Now PCL205u and DMPA total amount and IPDI molar ratio are 1: 1.465, dihydroxymethyl third
Acid occupies the 6% of the raw material gross mass for preparing performed polymer, and dibutyl tin laurate occupies the total matter of raw material for preparing performed polymer
The 0.14% of amount.
11.0g (0.082mol) hydroxypropyl acrylate, 70 DEG C of reaction 2h the, to-NCO of performed polymer are added into performed polymer
Blocked.Now, the rate of charge of NCO mole is 0.35 in the mole and performed polymer of hydroxypropyl acrylate：1.Cooling
To 40 DEG C, add 4.8g (0..047mol) triethylamine and carry out neutralization reaction 10min generation salt.Wherein the mole of triethylamine with
DMPA mole is identical.Add deionized water and carry out emulsification 15min, obtain photocurable aqueous polyurethane emulsion.
2nd, organic-silicon-modified tetraethyl orthosilicate is pre-condensed the preparation of presoma：
Ibid.
3rd, the preparation of coating material：
It is in mass ratio 1: 3 that photocurable aqueous polyurethane emulsion and organic-silicon-modified tetraethyl orthosilicate are pre-condensed into presoma
Ratio is mixed, and is carried out after UV photocurings and further condensation polymerization, is obtained coating material.
4th, properties of product are verified：
By the coating material of acquirement, glossiness test is carried out according to GB/T 1743-1979, coating gloss 93 is obtainedo；
Adhesive force detection, adhesion 1 grade are carried out according to GB 1720-1979.
Hardness determination is carried out according to GB/T 6739-1996, hardness is 3H.
Embodiment 3：
1st, the preparation of photocurable aqueous polyurethane emulsion：
By 45.5g (0.20mol) IPDI (IPDI), 58.0g (0.11mol) PCL205u（Polycaprolactone
Dihydric alcohol）, 5.5g (0.037mol) dihydromethyl propionic acid (DMPA), 0.11g dibutyl tin laurates, 75 DEG C reaction
4h, prepares performed polymer.Now PCL205u and DMPA total amount and IPDI molar ratio are 1: 1.36, dihydromethyl propionic acid
The 5% of the raw material gross mass for preparing performed polymer is occupied, dibutyl tin laurate occupies the raw material gross mass for preparing performed polymer
0.1%.
11.0g (0.072mol) pentaerythritol triacrylate, 70 DEG C of reaction 2h, to performed polymer are added into performed polymer
- NCO blocked.Now, in the mole and performed polymer of pentaerythritol triacrylate NCO mole rate of charge
For 0.1：1.40 DEG C are cooled to, 3.8g (0..037mol) triethylamine is added and carries out neutralization reaction 10min generation salt.Wherein three
The mole of ethamine is identical with DMPA mole.Add deionized water and carry out emulsification 15min, obtain photocurable aqueous
Polyaminoester emulsion.
2nd, organic-silicon-modified tetraethyl orthosilicate is pre-condensed the preparation of presoma：
Ibid.
3rd, the preparation of coating material：
It is in mass ratio 1: 2 that photocurable aqueous polyurethane emulsion and organic-silicon-modified tetraethyl orthosilicate are pre-condensed into presoma
Ratio is mixed, and is carried out after UV photocurings and further condensation polymerization, is obtained coating material.
4th, properties of product are verified：
By the coating material of acquirement, glossiness test is carried out according to GB/T 1743-1979, coating gloss 95 is obtainedo；
Adhesive force detection, adhesion 1 grade are carried out according to GB 1720-1979.
Hardness determination is carried out according to GB/T 6739-1996, hardness is 3H.
Claims (8)
1. the preparation method of photocuring aqueous polyurethane-silicon-oxygen-silicon inierpeneirating network structure coating material, it is characterised in that including
Following steps：
1）Diisocyanate, polyester diol, dihydromethyl propionic acid and dibutyl tin laurate are mixed, in mixed system
Temperature is the obtained performed polymer of reaction under conditions of 75~80 DEG C；
2）The acrylic resin of performed polymer and hydroxyl is mixed, reacts to after terminating, is cooled under conditions of 70~75 DEG C
After 40 DEG C, add triethylamine and carry out neutralization reaction, neutralization reaction adds deionized water emulsification again after terminating, and obtaining can UV photocuring water
Property polyaminoester emulsion；
3）Can UV photocurings aqueous polyurethane emulsion and the pre-condensation presoma mixing of organic-silicon-modified tetraethyl orthosilicate, warp by described in
UV photocurings and condensation polymerization, obtain photocuring aqueous polyurethane-silicon-oxygen-silicon inierpeneirating network structure coating material.
2. the preparation of photocuring aqueous polyurethane-silicon-oxygen-silicon inierpeneirating network structure coating material according to claim 1
Method, it is characterised in that the step 1）In, mole of the total amount and diisocyanate of polyester diol and dihydromethyl propionic acid
Than for 1: 1.4~1.75, and, dihydromethyl propionic acid accounts for diisocyanate, polyester diol, dihydromethyl propionic acid and tin dilaurate
The 4%~6% of the mixing gross mass of dibutyl tin, dibutyl tin laurate accounts for diisocyanate, polyester diol, dihydroxymethyl
The 0.1~0.2% of the mixing gross mass of propionic acid and dibutyl tin laurate.
3. the system of photocuring aqueous polyurethane-silicon-oxygen-silicon inierpeneirating network structure coating material according to claim 1 or 2
Preparation Method, it is characterised in that the diisocyanate is hexamethylene diisocyanate or IPDI.
4. the system of photocuring aqueous polyurethane-silicon-oxygen-silicon inierpeneirating network structure coating material according to claim 1 or 2
Preparation Method, it is characterised in that the polyester diol is polycaprolactone diols.
5. the system of photocuring aqueous polyurethane-silicon-oxygen-silicon inierpeneirating network structure coating material according to claim 1 or 2
Preparation Method, it is characterised in that the acrylic resin of the hydroxyl is hydroxy-ethyl acrylate, hydroxypropyl acrylate or pentaerythrite
Triacrylate.
6. the preparation of photocuring aqueous polyurethane-silicon-oxygen-silicon inierpeneirating network structure coating material according to claim 1
Method, it is characterised in that the step 2）In, NCO mole in the mole and performed polymer of the acrylic resin of the hydroxyl
The rate of charge of amount is 0.1~0.6: 1.
7. the preparation of photocuring aqueous polyurethane-silicon-oxygen-silicon inierpeneirating network structure coating material according to claim 1
Method, it is characterised in that the step 2）In, the mole for adding triethylamine is identical with the mole of dihydromethyl propionic acid.
8. the preparation of photocuring aqueous polyurethane-silicon-oxygen-silicon inierpeneirating network structure coating material according to claim 1
Method, it is characterised in that it is described can UV photocurings aqueous polyurethane emulsion and organic-silicon-modified tetraethyl orthosilicate pre-condensation presoma
Mixed volume ratio be 1: 1.5~3.
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Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN108148171A (en) * | 2017-12-11 | 2018-06-12 | 湖北大学 | A kind of hydrolysis-resistant waterborne polyurethane dispersion and preparation method thereof |
| CN111560204A (en) * | 2020-06-15 | 2020-08-21 | 李艳艳 | Self-repairable polycarbonate surface antifogging coating and preparation method thereof |
| CN112119353A (en) * | 2018-02-09 | 2020-12-22 | 联合富大有限公司 | Photosensitive binder |
| CN113416280A (en) * | 2021-05-28 | 2021-09-21 | 华南理工大学 | Ultraviolet-cured silicon-containing organic-inorganic hybrid resin and preparation method thereof |
| CN113637137A (en) * | 2021-07-22 | 2021-11-12 | 昆山优瑞森医疗科技有限公司 | Preparation method of synthetic siloxane polyurethane copolymer |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN101735599A (en) * | 2009-12-24 | 2010-06-16 | 华南理工大学 | Ultraviolet curing organic silicon modified polyurethane aqueous dispersoid and preparation method thereof |
| CN103709927A (en) * | 2013-12-04 | 2014-04-09 | 江南大学 | Preparation method for antifogging thin film coating with high light transmission |
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| CN101735599A (en) * | 2009-12-24 | 2010-06-16 | 华南理工大学 | Ultraviolet curing organic silicon modified polyurethane aqueous dispersoid and preparation method thereof |
| CN103709927A (en) * | 2013-12-04 | 2014-04-09 | 江南大学 | Preparation method for antifogging thin film coating with high light transmission |
Cited By (7)
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| CN108148171A (en) * | 2017-12-11 | 2018-06-12 | 湖北大学 | A kind of hydrolysis-resistant waterborne polyurethane dispersion and preparation method thereof |
| CN108148171B (en) * | 2017-12-11 | 2020-10-30 | 湖北大学 | Hydrolysis-resistant aqueous polyurethane dispersion and preparation method thereof |
| CN112119353A (en) * | 2018-02-09 | 2020-12-22 | 联合富大有限公司 | Photosensitive binder |
| CN111560204A (en) * | 2020-06-15 | 2020-08-21 | 李艳艳 | Self-repairable polycarbonate surface antifogging coating and preparation method thereof |
| CN113416280A (en) * | 2021-05-28 | 2021-09-21 | 华南理工大学 | Ultraviolet-cured silicon-containing organic-inorganic hybrid resin and preparation method thereof |
| CN113637137A (en) * | 2021-07-22 | 2021-11-12 | 昆山优瑞森医疗科技有限公司 | Preparation method of synthetic siloxane polyurethane copolymer |
| CN113637137B (en) * | 2021-07-22 | 2023-06-06 | 昆山优瑞森医疗科技有限公司 | Preparation method of synthetic siloxane polyurethane copolymer |
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| CN106939143B (en) | 2019-03-29 |
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