CN109880511B - Photocuring-thermal crosslinking self-repairing coating and preparation method and application thereof - Google Patents
Photocuring-thermal crosslinking self-repairing coating and preparation method and application thereof Download PDFInfo
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Abstract
The invention discloses a photocuring-thermal crosslinking self-repairable coating, which relates to the field of preparation of functional coatings and is provided based on the problems that a complete crosslinking network is difficult to form and a formed coating is easy to damage due to the limitation of motion diffusion in most photocuring crosslinking reaction processes, and the photocuring-thermal crosslinking self-repairable coating is mainly prepared from the following raw materials in parts by weight: 20-50 parts of bismaleimide crosslinking agent, 20-30 parts of furfuryl alcohol acrylate monomer, 50-60 parts of compound light-cured resin and 0.5-3 parts of light-cured initiator, and the invention also provides a preparation method of the coating, wherein the raw materials are mixed to prepare the coating, and the invention also provides application of the coating in preparing a coating, wherein the coating is prepared by performing film coating, light curing and heat treatment on the prepared self-repairable coating composition, and the beneficial effects of the invention are as follows: the photocuring coating prepared by the invention forms a thermal cross-linking network in a curing grid structure; and has self-repairing performance.
Description
Technical Field
The invention relates to the field of preparation of functional coatings, in particular to a photocuring-thermal crosslinking self-repairing coating and a preparation method and application thereof.
Background
The viscosity of the resin system of the photocureable coating is adjusted by adopting the polymerizable reactive diluent, and a solvent is not required to be used, so that the organic solvent is prevented from being released into the environment. In the coating industry where environmental problems are increasingly emphasized, photocureable coatings have a tendency to develop rapidly. The photopolymerization system composition usually comprises photosensitive resin, reactive diluent and photoinitiator, and corresponding auxiliary agents and pigments and fillers are added according to the application. The reaction involved in the curing process is mainly that the photosensitive resin and the reactive diluent initiate polymerization and curing under the action of a photoinitiator to form a film. The photocuring system is prepared by compounding photosensitive resin with two or more functional groups and reactive diluent, and the curing process is fast and usually can be completed within seconds. Therefore, most photocuring crosslinking reaction processes are limited by the movement diffusion, and a perfect crosslinking network is difficult to form. The rapid curing reaction and the volume shrinkage during curing tend to create internal stresses in the coating, thereby degrading the properties of the coating.
Disclosure of Invention
The invention aims to solve the problems that the cross-linking reaction process of most photocuring is limited by motion diffusion, so that a complete cross-linking network is difficult to form, and a formed coating is easy to damage.
The invention adopts the following technical scheme to solve the technical problems:
the invention provides a photocuring-thermal crosslinking self-repairing coating which is mainly prepared from the following raw materials in parts by weight: 20-50 parts of bismaleimide crosslinking agent, 20-30 parts of furfuryl alcohol acrylate monomer, 50-60 parts of compound light-cured resin and 0.5-3 parts of light-cured initiator.
Preferably, the bismaleimide crosslinker has the following general structural formula:
wherein n is 3-12.
Preferably, the preparation method of the bismaleimide cross-linking agent is as follows: adding maleic anhydride into a reaction system, heating, dropwise adding an amine compound, continuing heating for reaction, and dehydrating after the reaction is finished to obtain the bismaleimide crosslinking agent.
Preferably, the feeding ratio of the maleic anhydride to the amine compound is 2.05-2.10: 1.
Preferably, the reaction temperature after the first temperature rise is 60-70 ℃, the reaction temperature after the second temperature rise is 120-160 ℃, and the reaction time is 7-8 h.
Preferably, the dropping rate of the amine compound is 0.1-0.5g/10 min.
Preferably, the amine compound is a primary diamine having 3 to 12 carbon atoms, and the molar ratio of the added maleic anhydride to the added amine compound is 2.05 to 2.10: 1.
Preferably, the furfuryl alcohol acrylate monomer has the general structural formula:
preferably, the preparation method of the acrylate monomer comprises the following steps: taking furfuryl alcohol, adding p-toluenesulfonic acid and p-hydroxyanisole, adding cyclohexane, dropwise adding acrylic acid, and stopping reaction when the acid value of a system is less than 10mg KOH/g.
Preferably, the feeding molar ratio of the furfuryl alcohol to the acrylic acid is 1.05-1.1:1, the addition amount of the p-toluenesulfonic acid is 1-3 wt% of the total mass of the furfuryl alcohol and the acrylic acid, the addition amount of the p-hydroxyanisole is 0.5-1 wt% of the total mass of the furfuryl alcohol and the acrylic acid, and the addition amount of the cyclohexane is 8 wt% of the total mass of the furfuryl alcohol and the acrylic acid.
Preferably, the composite light-curable resin consists of 40-60 parts of photosensitive resin and 40-50 parts of reactive diluent.
Preferably, the photosensitive resin is one or more of urethane acrylate resin, epoxy acrylate resin and polyester acrylate resin; the active diluent is one or more of trimethylolpropane triacrylate, diethylene glycol diacrylate and 1, 6-hexanediol diacrylate.
Preferably, the photo-curing initiator is one of 2-hydroxy-2-methyl-1-phenyl acetone, 1-hydroxycyclohexyl phenyl ketone, 2-methyl-2- (4-morpholinyl) -1- [4- (methylthio) phenyl ] -1-propanone, 2,4, 6-trimethylbenzoyl-diphenyl phosphine oxide, phenyl bis (2,4, 6-trimethylbenzoyl) phosphine oxide, 2-hydroxy-4- (2-hydroxyethoxy) -2-methyl propiophenone (2959), and 2-phenylbenzyl-2-dimethylamino-1- (4-morpholine benzyl) butanone.
The invention also provides a preparation method of the photocuring-thermal crosslinking self-repairable coating, which comprises the following steps:
(1) adding maleic anhydride and an amine compound into a reaction system, heating, then dropwise adding the amine compound, continuing heating for reaction, and dehydrating after the reaction is finished to obtain a bismaleimide crosslinking agent;
(2) taking furfuryl alcohol, adding p-toluenesulfonic acid and p-hydroxyanisole, adding cyclohexane, dropwise adding acrylic acid, stopping reaction when the acid value of a system is less than 10mg KOH/g, and obtaining a furfuryl alcohol acrylate monomer;
(3) mixing photosensitive resin and reactive diluent, adding photoinitiator, and blending to prepare compound photosensitive resin;
(4) and (3) mixing the products obtained in the steps (1), (2), (3) and (4), and stirring to obtain the self-repairing coating.
The invention also provides a self-repairing coating of photo-curing-thermal crosslinking, which is prepared by coating, photo-curing and heat treatment of the self-repairing coating composition prepared by the method.
Preferably, the curing energy in the photocuring is 150mJ/cm2。
Preferably, the temperature of the heat treatment is 120-160 ℃, and the heat treatment time is 10-15 min.
The invention has the beneficial effects that:
(1) the photocuring coating prepared by the invention forms a thermal cross-linking network in a curing grid structure by heat treatment and Diels-Alder reaction, so that the mechanical property and the temperature resistance of the coating can be improved;
(2) when the photocuring coating prepared by the invention is damaged, the crosslinking network is subjected to Diels-Alder reaction reverse reaction through heat treatment, the high molecular chain segment is rearranged, the double rings formed by heat crosslinking are depolymerized, and then the thermal crosslinking network is formed again through cooling, so that the self-repairing of the coating is completed.
Detailed Description
The present invention will be described in further detail with reference to examples.
Test materials, reagents and the like used in the following examples are commercially available unless otherwise specified.
Example 1
The chemical reaction of the curing process of the photocuring-thermal crosslinking self-repairable dual-curing coating is as follows:
example 2
Preparation of the photocured coating:
(1) weighing 51.0g of maleic anhydride in a three-neck flask, and heating to 60 ℃; weighing 22.0g of butanediamine in a constant-pressure dropping funnel, dropwise adding into a three-neck flask at a rate of 0.5g/10min, heating to 120 ℃ after dropwise adding, carrying out heat preservation reaction for 8h, and carrying out vacuum dehydration for 2h to obtain a bismaleimide crosslinking agent with a binary structure;
(2) weighing 53.0g of furfuryl alcohol in a three-neck flask, adding 2.4g of p-toluenesulfonic acid and 0.4g of p-hydroxyanisole, adding 6.4g of cyclohexane, weighing 36.0g of acrylic acid in a constant-pressure dropping funnel, slowly dropping the acrylic acid into a reaction system, after dropping for 30min, heating to 90 ℃ for reaction, after reacting for 2h, dividing water through a water separator, and stopping the reaction when the acid value of the system is less than 10mg KOH/g to obtain furfuryl alcohol acrylate;
(3) weighing 6.0g of urethane acrylate photosensitive resin (Sadoma resin CN9001), adding 4.0g of trimethylolpropane triacrylate, adding 0.05g of photoinitiator 2-hydroxy-2-methyl-1-phenyl acetone (1173), and blending to prepare compound photosensitive resin;
(4) taking 3.0g of the bismaleimide crosslinking agent prepared in the step (1), 2.0g of furfuryl alcohol acrylate prepared in the step (2) and 5.0g of the compound photosensitive resin prepared in the step (3), uniformly stirring, and carrying out vacuum defoaming;
(5) preparing a coating on the tinplate sample by using the resin prepared in the step (4), wherein the wet film thickness is 80 microns, and performing photocuring by using a crawler-type photocuring machine until the light intensity is 150mJ/cm2Then, after photocuring, the coating is placed in an oven at 150 ℃ for baking for 10min to obtain a photocured coating;
(6) if the prepared photocuring coating is damaged, the photocuring coating can be subjected to heat treatment again at the temperature of 120-160 ℃, so that the crosslinking network has a Diels-Alder reaction reverse reaction, the macromolecular chain segments are rearranged at the temperature higher than the glass transition temperature, and the thermal crosslinking network is newly formed by cooling to room temperature.
Example 3
Preparation of the photocured coating:
(1) weighing 50.0g of maleic anhydride in a three-neck flask, and heating to 60 ℃; weighing 28.5g of hexamethylenediamine in a constant-pressure dropping funnel, dropwise adding the hexamethylenediamine into a three-neck flask at a rate of 0.5g/10min, heating to 130 ℃ after the dropwise adding is finished, carrying out heat preservation reaction for 8 hours, and carrying out vacuum dehydration for 2 hours to obtain a bismaleimide cross-linking agent;
(2) weighing 53.0g of furfuryl alcohol in a three-neck flask, adding 2.4g of p-toluenesulfonic acid and 0.4g of p-hydroxyanisole, adding 6.4g of cyclohexane, weighing 36.0g of acrylic acid in a constant-pressure dropping funnel, slowly dropping the acrylic acid into a reaction system, after dropping for 30min, heating to 90 ℃ for reaction, after reflux reaction for 2h, dividing water by a water separator, and stopping the reaction when the acid value of the system is less than 10mg KOH/g to obtain furfuryl alcohol acrylate;
(3) weighing 5.0g of urethane acrylate photosensitive resin (sartomer resin CN9010), adding 5.0g of trimethylolpropane triacrylate and 0.1g of photoinitiator 1-hydroxycyclohexyl phenyl ketone (184), and blending to prepare compound photosensitive resin;
(4) taking 3.0g of the bismaleimide crosslinking agent prepared in the step (1), 2.0g of furfuryl alcohol acrylate prepared in the step (2) and 5.0g of the compound photosensitive resin prepared in the step (3), uniformly stirring, and carrying out vacuum defoaming;
(5) preparing a coating on the tinplate sample by using the resin prepared in the step (4), wherein the wet film thickness is 80 microns, and the light intensity is 150mJ/cm by using a crawler-type light curing machine2Is carried out byAfter photocuring, baking in an oven at 120 ℃ for 10min to obtain a photocured coating;
(6) if the prepared photocuring coating is damaged, the photocuring coating can be subjected to heat treatment again at the temperature of 120-160 ℃, so that the crosslinking network has a Diels-Alder reaction reverse reaction, the macromolecular chain segments are rearranged at the temperature higher than the glass transition temperature, and the thermal crosslinking network is newly formed by cooling to room temperature.
Example 4
Preparation of the photocured coating:
(1) weighing 52.0g of maleic anhydride in a three-neck flask, and heating to 60 ℃; weighing 44.0g of decamethylenediamine in a constant-pressure dropping funnel, dropwise adding into a three-neck flask at a rate of 0.5g/10min, heating to 120 ℃ after dropwise adding, carrying out heat preservation reaction for 8h, and carrying out vacuum dehydration for 2h to obtain a bismaleimide cross-linking agent;
(2) weighing 52.0g of furfuryl alcohol in a three-neck flask, adding 2.4g of p-toluenesulfonic acid and 0.4g of p-hydroxyanisole, adding 6.4g of cyclohexane, weighing 36.0g of acrylic acid in a constant-pressure dropping funnel, slowly dropping the acrylic acid into a reaction system, after dropping for 30min, heating to 90 ℃ for reaction, after reacting for 2h, dividing water through a water separator, and stopping the reaction when the acid value of the system is less than 10mg KOH/g to obtain furfuryl alcohol acrylate;
(3) weighing 5.0g of urethane acrylate photosensitive resin (sartomer resin CN104), adding 5.0g of trimethylolpropane triacrylate, adding 0.15g of photoinitiator 2-methyl-2- (4-morpholinyl) -1- [4- (methylthio) phenyl ] -1-acetone (907), and blending to prepare compound photosensitive resin;
(4) taking 2.0g of the bismaleimide crosslinking agent prepared in the step (1), 2.0g of the furfuryl alcohol acrylate prepared in the step (2) and 6.0g of the compound photosensitive resin prepared in the step (3), uniformly stirring, and carrying out vacuum defoaming;
(5) preparing a coating on the tinplate sample by using the resin prepared in the step (4), wherein the wet film thickness is 80 microns, and performing photocuring by using a crawler-type photocuring machine until the light intensity is 150mJ/cm2Then, after photocuring, the coating is placed in an oven at 150 ℃ for baking for 10min to obtain a photocured coating;
(6) if the prepared photocuring coating is damaged, the photocuring coating can be subjected to heat treatment again at the temperature of 120-160 ℃, so that the crosslinking network has a Diels-Alder reaction reverse reaction, the macromolecular chain segments are rearranged at the temperature higher than the glass transition temperature, and the thermal crosslinking network is newly formed by cooling to room temperature.
Example 5
Preparation of the photocured coating:
(1) weighing 50.5g of maleic anhydride in a three-neck flask, and heating to 60 ℃; weighing 22.0g of butanediamine in a constant-pressure dropping funnel, dropwise adding into a three-neck flask at a rate of 0.3g/10min, heating to 120 ℃ after dropwise adding, carrying out heat preservation reaction for 8 hours, and carrying out vacuum dehydration for 2 hours to obtain a bismaleimide cross-linking agent;
(2) weighing 51.5g of furfuryl alcohol in a three-neck flask, adding 2.4g of p-toluenesulfonic acid and 0.4g of p-hydroxyanisole, adding 6.4g of cyclohexane, weighing 36.0g of acrylic acid in a constant-pressure dropping funnel, slowly dropping the acrylic acid into a reaction system, after dropping for 30min, heating to 90 ℃ for reaction, after reacting for 2h, dividing water through a water separator, and stopping the reaction when the acid value of the system is less than 10mg KOH/g to obtain furfuryl alcohol acrylate;
(3) weighing 6.0g of urethane acrylate photosensitive resin (sartomer resin CNUVE151), adding 4.0g of trimethylolpropane triacrylate, adding 0.2g of photoinitiator phenyl bis (2,4, 6-trimethylbenzoyl) phosphine oxide (819), and blending to prepare compound photosensitive resin;
(4) taking 2.0g of the bismaleimide crosslinking agent prepared in the step (1), 2.0g of the furfuryl alcohol acrylate prepared in the step (2) and 6.0g of the compound photosensitive resin prepared in the step (3), uniformly stirring, and carrying out vacuum defoaming;
(5) preparing a coating on the tinplate sample by using the resin prepared in the step (4), wherein the wet film thickness is 80 microns, and performing photocuring by using a crawler-type photocuring machine until the light intensity is 150mJ/cm2Then, after photocuring, the coating is placed in an oven at 150 ℃ for baking for 10min to obtain a photocured coating;
(6) if the prepared photocuring coating is damaged, the photocuring coating can be subjected to heat treatment again at the temperature of 120-160 ℃, so that the crosslinking network has a Diels-Alder reaction reverse reaction, the macromolecular chain segments are rearranged at the temperature higher than the glass transition temperature, and the thermal crosslinking network is newly formed by cooling to room temperature.
Example 6
Preparation of the photocured coating:
(1) weighing 51.2g of maleic anhydride in a three-neck flask, and heating to 60 ℃; weighing 22.0g of butanediamine in a constant-pressure dropping funnel, dropwise adding into a three-neck flask at a rate of 0.5g/10min, heating to 120 ℃ after dropwise adding, carrying out heat preservation reaction for 8 hours, and carrying out vacuum dehydration for 2 hours to obtain a bismaleimide cross-linking agent;
(2) weighing 53.5g of furfuryl alcohol in a three-neck flask, adding 2.4g of p-toluenesulfonic acid and 0.4g of p-hydroxyanisole, adding 6.4g of cyclohexane, weighing 36.0g of acrylic acid in a constant-pressure dropping funnel, slowly dropping the acrylic acid into a reaction system, after dropping for 30min, heating to 90 ℃ for reaction, after reacting for 2h, dividing water through a water separator, and stopping the reaction when the acid value of the system is less than 10mg KOH/g to obtain furfuryl alcohol acrylate;
(3) weighing 6.0g of urethane acrylate photosensitive resin (sartomer resin CN2264), adding 4.0g of trimethylolpropane triacrylate, adding 0.15g of photoinitiator 2-hydroxy-4- (2-hydroxyethoxy) -2-methyl propiophenone (2959), and blending to prepare compound photosensitive resin;
(4) taking 2.0g of the bismaleimide crosslinking agent prepared in the step (1), 2.0g of the furfuryl alcohol acrylate prepared in the step (2) and 6.0g of the compound photosensitive resin prepared in the step (3), uniformly stirring, and carrying out vacuum defoaming;
(5) preparing a coating on the tinplate sample by using the resin prepared in the step (4), wherein the wet film thickness is 80 microns, and performing photocuring by using a crawler-type photocuring machine until the light intensity is 150mJ/cm2Then, after photocuring, the coating is placed in an oven at 150 ℃ for baking for 10min to obtain a photocured coating;
(6) if the prepared photocuring coating is damaged, the photocuring coating can be subjected to heat treatment again at the temperature of 120-160 ℃, so that the crosslinking network has a Diels-Alder reaction reverse reaction, the macromolecular chain segments are rearranged at the temperature higher than the glass transition temperature, and the thermal crosslinking network is newly formed by cooling to room temperature.
Example 7
Preparation of the photocured coating:
(1) weighing 51.4g of maleic anhydride in a three-neck flask, and heating to 60 ℃; weighing 22.0g of butanediamine in a constant-pressure dropping funnel, dropwise adding into a three-neck flask at a rate of 0.5g/10min, heating to 120 ℃ after dropwise adding, carrying out heat preservation reaction for 8 hours, and carrying out vacuum dehydration for 2 hours to obtain a bismaleimide cross-linking agent;
(2) weighing 53.0g of furfuryl alcohol in a three-neck flask, adding 2.4g of p-toluenesulfonic acid and 0.4g of p-hydroxyanisole, adding 6.4g of cyclohexane, weighing 36.0g of acrylic acid in a constant-pressure dropping funnel, slowly dropping the acrylic acid into a reaction system, after dropping for 30min, heating to 90 ℃ for reaction, after reacting for 2h, dividing water through a water separator, and stopping the reaction when the acid value of the system is less than 10mg KOH/g to obtain furfuryl alcohol acrylate;
(3) weighing 6.0g of urethane acrylate photosensitive resin (sartomer resin CN2264), adding 4.0g of trimethylolpropane triacrylate, adding 0.05g of 2-phenylbenzyl-2-dimethylamino-1- (4-morpholinylbenzyl) butanone (369) serving as a photoinitiator, and blending to prepare compound photosensitive resin;
(4) taking 2.0g of the bismaleimide crosslinking agent prepared in the step (1), 2.0g of the furfuryl alcohol acrylate prepared in the step (2) and 6.0g of the compound photosensitive resin prepared in the step (3), uniformly stirring, and carrying out vacuum defoaming;
(5) preparing a coating on the tinplate sample by using the resin prepared in the step (4), wherein the wet film thickness is 80 microns, and performing photocuring by using a crawler-type photocuring machine until the light intensity is 150mJ/cm2Then, after photocuring, the coating is placed in an oven at 150 ℃ for baking for 10min to obtain a photocured coating;
(6) if the prepared photocuring coating is damaged, the photocuring coating can be subjected to heat treatment again at the temperature of 120-160 ℃, so that the crosslinking network has a Diels-Alder reaction reverse reaction, the macromolecular chain segments are rearranged at the temperature higher than the glass transition temperature, and the thermal crosslinking network is newly formed by cooling to room temperature.
The above is only a preferred embodiment of the present invention, and the protection scope of the present invention is not limited to the above examples, and various process schemes having no substantial difference from the concept of the present invention are within the protection scope of the present invention.
Claims (4)
1. A preparation method of a photocuring-thermal crosslinking self-repairable coating is characterized by comprising the following steps: the method comprises the following steps:
(1) adding maleic anhydride into a reaction system, heating, dropwise adding an amine compound, continuing heating reaction, and dehydrating after the reaction is finished to obtain a bismaleimide crosslinking agent;
(2) taking furfuryl alcohol, adding p-toluenesulfonic acid and p-hydroxyanisole, adding cyclohexane, dropwise adding acrylic acid, stopping reaction when the acid value of a system is less than 10mg KOH/g, and obtaining a furfuryl alcohol acrylate monomer;
(3) mixing photosensitive resin and reactive diluent to prepare compound light-cured resin, adding a photoinitiator, and blending to prepare compound photosensitive resin;
(4) mixing the products obtained in the steps (1), (2) and (3), and stirring to obtain the self-repairing coating;
the photocuring-thermal crosslinking self-repairing coating is mainly prepared from the following raw materials in parts by weight: 20-50 parts of bismaleimide crosslinking agent, 20-30 parts of furfuryl alcohol acrylate monomer, 50-60 parts of compound light-cured resin and 0.5-3 parts of photoinitiator;
the bismaleimide crosslinker has the following general structural formula:
wherein n is 3-12;
the furfuryl alcohol acrylate monomer has the following general structural formula:
2. the method for preparing a photocuring-thermal crosslinking self-repairable coating according to claim 1, characterized in that: the photosensitive resin is one or more of polyurethane acrylate resin, epoxy acrylate resin and polyester acrylate resin; the active diluent is one or more of trimethylolpropane triacrylate, diethylene glycol diacrylate and 1, 6-hexanediol diacrylate.
3. The method for preparing a photocuring-thermal crosslinking self-repairable coating according to claim 1, characterized in that: the photoinitiator is one of 2-hydroxy-2-methyl-1-phenyl acetone, 1-hydroxycyclohexyl phenyl ketone, 2-methyl-2- (4-morpholinyl) -1- [4- (methylthio) phenyl ] -1-acetone, 2,4, 6-trimethylbenzoyl-diphenyl phosphine oxide, phenyl bis (2,4, 6-trimethylbenzoyl) phosphine oxide and 2-hydroxy-4- (2-hydroxyethoxy) -2-methyl phenylpropyl ketone.
4. Use of a photocuring-thermal crosslinking self-healing coating prepared by the preparation process according to any one of claims 1 to 3 for the preparation of self-healing coatings, characterized in that: the self-repairing coating is prepared by mixing, coating, photocuring and heat treatment of a self-repairing coating.
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