CN111978784B - Preparation method of biomass-based environment-friendly UV (ultraviolet) photocuring ink - Google Patents
Preparation method of biomass-based environment-friendly UV (ultraviolet) photocuring ink Download PDFInfo
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- CN111978784B CN111978784B CN202010978026.9A CN202010978026A CN111978784B CN 111978784 B CN111978784 B CN 111978784B CN 202010978026 A CN202010978026 A CN 202010978026A CN 111978784 B CN111978784 B CN 111978784B
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- 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
- C09D11/00—Inks
- C09D11/02—Printing inks
- C09D11/10—Printing inks based on artificial resins
- C09D11/101—Inks specially adapted for printing processes involving curing by wave energy or particle radiation, e.g. with UV-curing following the printing
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- 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
- C09D11/00—Inks
- C09D11/02—Printing inks
- C09D11/03—Printing inks characterised by features other than the chemical nature of the binder
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- 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
- C09D11/00—Inks
- C09D11/02—Printing inks
- C09D11/08—Printing inks based on natural resins
Abstract
The invention discloses a preparation method of biomass-based environment-friendly UV (ultraviolet) photocuring ink, which comprises the following raw materials in parts by weight: 50-60 parts of acrylate maleic ester modified rosin, 8-16 parts of reactive diluent, 5-10 parts of photoinitiator, 1-2 parts of dispersant, 0.1-0.5 part of stabilizer, 15-30 parts of pigment, 2-5 parts of filler and 1-3 parts of functional assistant; the method specifically comprises the following steps: step 1, modifying rosin by adopting acrylate maleic acid ester; and 2, preparing the shape-preserving UV photocuring ink according to the product obtained in the step 1. The UV photocuring ink prepared by the invention avoids using acrylic acid modified rosin resin, reduces the smell of the ink, and does not cause secondary pollution to the environment.
Description
Technical Field
The invention belongs to the technical field of printing materials, and relates to a preparation method of biomass-based environment-friendly UV (ultraviolet) photocuring ink.
Background
Under the excitation of UV light, the ultraviolet light-activated photoinitiator in the UV light-cured ink absorbs the excitation of the ultraviolet light to generate active free radicals, and the crosslinking polymerization of oligomers in ink binder is initiated to form a film and dry the ink. Compared with ink of other curing modes, the ink has the advantages of excellent coating performance, quick curing, zero VOC (volatile organic compounds) emission and the like, and is widely applied to offset printing, screen printing, gravure printing and the like.
The binder, which is the main component of the UV light curable ink, constitutes the basic skeleton of the film layer and determines the physical and chemical properties of the film layer. In the existing UV light curing ink system, a connecting material mainly comprises olefine acid ester, epoxy resin and other petroleum-based polymers, and the long-term sustainable development is difficult to maintain. In order to further reduce the pollution of printing chemicals to the environment, the biomass material is adopted as a matrix, and the UV light-curable resin is prepared by modifying the functions of the biomass material, can be naturally degraded, cannot generate secondary pollution to the environment, and has a better development prospect. Therefore, a preparation method of the biomass-based environment-friendly UV photocuring ink is provided.
Disclosure of Invention
The invention aims to provide a preparation method of biomass-based environment-friendly UV (ultraviolet) photocuring ink, which avoids using acrylic acid modified rosin resin, reduces the smell of the ink and does not cause secondary pollution to the environment.
The invention adopts the technical scheme that a preparation method of biomass-based environment-friendly UV (ultraviolet) photocuring ink comprises the following raw materials in parts by weight: 50-60 parts of acrylate maleic ester modified rosin, 8-16 parts of reactive diluent, 5-10 parts of photoinitiator, 1-2 parts of dispersant, 0.1-0.5 part of stabilizer, 15-30 parts of pigment, 2-5 parts of filler and 1-3 parts of functional assistant;
the method specifically comprises the following steps:
step 1, modifying rosin by adopting acrylate maleic acid ester;
and 2, adding acrylate maleic acid ester modified rosin, an active diluent, a photoinitiator, a dispersant and a stabilizer into a reaction kettle according to parts by weight, stirring at the speed of 500r/min for 10 minutes for pre-dispersion, then adding a pigment, a filler and a functional assistant according to parts by weight while stirring, stirring at the speed of 1000r/min for 15 minutes to obtain a primarily dispersed ink material, taking the primarily dispersed ink material out of the reaction kettle, adding the primarily dispersed ink material into a three-roll grinder, and repeatedly rolling for 3-5 times to obtain the biomass-based environment-friendly UV photocuring ink.
The present invention is also technically characterized in that,
the specific process of the step 1 is as follows:
under the nitrogen atmosphere, adding rosin, hydroxyethyl acrylate and a polymerization inhibitor into a reaction kettle, heating to 120 ℃ until the rosin is molten, heating to 180-230 ℃, and reacting for 3-5 hours to obtain acrylate modified rosin; and after the temperature is reduced to 90-120 ℃, adding maleic anhydride into the reaction kettle, and continuously reacting for 4-6h to obtain the acrylate maleic ester modified rosin.
In the step 1, the mass ratio of rosin, hydroxyethyl acrylate and maleic anhydride is 1: (2-3): (1.5-2.7).
In the step 1, the polymerization inhibitor is hydroquinone, and the mass of the polymerization inhibitor is 0.5-1% of that of the hydroxyethyl acrylate.
The functional assistant is adhesion promoter acrylate phosphate.
In the three-roll grinder in the step 2, the speed ratio of the front roll, the middle roll and the rear roll is set to be 9:3: 1.
The invention has the following beneficial effects:
(1) the method takes biomass-based rosin as a raw material, and the biomass-based rosin is reacted with hydroxyethyl (methyl) acrylate through a Diels-Alder reaction, and then hydroxyl in a generated intermediate is utilized to react with maleic anhydride, so that a high-activity double bond is introduced. Meanwhile, the problem of large smell of the ink caused by residual acrylic acid in the traditional UV curing system of acrylic acid modified rosin is avoided, and the application of the UV light curing ink in the fields of food, medicines and the like is widened.
(2) The biomass-based environment-friendly UV photocuring ink prepared by the invention has the advantages of stable system, high curing speed, good adhesion property, high color concentration and good printability, is suitable for high-speed printing, and has good economic and social benefits.
Detailed Description
The present invention will be described in detail with reference to the following embodiments.
The invention relates to a preparation method of biomass-based environment-friendly UV (ultraviolet) photocuring ink, which comprises the following raw materials in parts by weight: 50-60 parts of acrylate maleic ester modified rosin, 8-16 parts of reactive diluent, 5-10 parts of photoinitiator, 1-2 parts of dispersant, 0.1-0.5 part of stabilizer, 15-30 parts of pigment, 2-5 parts of filler and 1-3 parts of functional assistant;
the method specifically comprises the following steps:
step 1, modifying rosin by adopting acrylate maleic acid ester;
the specific process of the step 1 is as follows:
under the nitrogen atmosphere, adding rosin, hydroxyethyl acrylate and a polymerization inhibitor into a reaction kettle, heating to 120 ℃ until the rosin is molten, heating to 180-230 ℃, and reacting for 3-5 hours to obtain acrylate modified rosin; and after the temperature is reduced to 90-120 ℃, adding maleic anhydride into the reaction kettle, and continuously reacting for 4-6h to obtain the acrylate maleic ester modified rosin.
In the step 1, the mass ratio of rosin, hydroxyethyl acrylate and maleic anhydride is 1: (2-3): (1.5-2.7).
In the step 1, the polymerization inhibitor is hydroquinone, and the mass of the polymerization inhibitor is 0.5-1% of that of the hydroxyethyl acrylate.
The synthetic route of the acrylate maleic ester modified rosin is as follows:
and 2, adding acrylate maleic acid ester modified rosin, an active diluent, a photoinitiator, a dispersant and a stabilizer into a reaction kettle according to parts by weight, stirring at the speed of 500r/min for 10 minutes for pre-dispersion, then adding a pigment, a filler and a functional assistant according to parts by weight while stirring, stirring at the speed of 1000r/min for 15 minutes to obtain a primarily dispersed ink material, taking the primarily dispersed ink material out of the reaction kettle, adding the primarily dispersed ink material into a three-roll grinder, and repeatedly rolling for 3-5 times to obtain the biomass-based environment-friendly UV photocuring ink. The rotating speed of the front roller is adjusted to be 400r/min, and the speed ratio of the front roller to the middle roller to the rear roller is set to be 9:3: 1.
The reactive diluent is prepared by mixing bifunctional UV monomers and trifunctional UV monomers in any proportion. The difunctional UV monomer is one of tripropylene glycol diacrylate, hexanediol diacrylate, dipropylene glycol diacrylate and neopentyl glycol diacrylate or a mixture of several monomers in any proportion.
The tri-functionality UV monomer is one of trimethylolpropane triacrylate, pentaerythritol triacrylate and propoxylated trimethylolpropane triacrylate or a mixture of several of the trimethylolpropane triacrylate in any proportion.
The photoinitiator is one or a mixture of irgacure 369 and ITX in any proportion.
The dispersant was lubrizol 24000. The stabilizer is tris (N-nitroso-N-phenylhydroxylamine) aluminum salt (510).
The filler is talcum powder and calcium powder. The mesh number of the stone powder is 3000 meshes, and the mesh number of the calcium powder is 1250 meshes.
The mass ratio of the talcum powder to the calcium powder is 3: 1;
in the pigment, the yellow color paste is one or two of a mixture of disazo pigment yellow and zinc sulfate in any proportion; the blue color paste is one or two of triarylmethane pigment blue and phthalocyanine pigment blue in any proportion; the red color paste is one or two of monoazo pigment red and iron oxide red in any proportion.
The functional assistant is adhesion promoter acrylate phosphate; the high light additive is polyethylene wax and printing ink light slurry. The mass ratio of the adhesion promoter to the high light additive is 2:1-1: 2.
Example 1
A preparation method of biomass-based environment-friendly UV (ultraviolet) photocuring ink specifically comprises the following steps:
step 1, preparation of acrylate maleic ester modified rosin:
adding 20g of rosin, 40g of hydroxyethyl acrylate HEA and 0.4g of hydroquinone into a reaction kettle, bubbling nitrogen for 30min, heating to 120 ℃, continuing to heat to 180 ℃ after the rosin is molten, and reacting for 3h to obtain acrylate modified rosin; and (3) stopping heating the reaction kettle, after the temperature is reduced to 90 ℃, adding 30g of maleic anhydride into the reaction kettle in the nitrogen atmosphere, and continuously reacting for 4 hours to obtain the acrylate maleic ester modified rosin.
Step 2, preparing the environment-friendly UV photocuring ink:
adding 60 parts of acrylate maleic acid ester modified rosin, 2 parts of tripropylene glycol diacrylate, 2 parts of hexanediol diacrylate, 6 parts of trimethylolpropane triacrylate, irgacure 3695 parts, 240001 parts of Lubrizol and 0.1 part of tri (N-nitroso-N-phenylhydroxylamine) aluminum salt into a reaction kettle according to the parts by weight, stirring at the speed of 500r/min for 10 minutes for pre-dispersion, then adding 1.5 parts of 3000-mesh talcum powder, 0.5 part of 1250-mesh calcium powder, 20 parts of red color paste and 2.9 parts of acrylate phosphate according to the weight parts while stirring, stirring for 15 minutes at the speed of 1000r/min to obtain primarily dispersed ink, taking the primarily dispersed ink out of the reaction kettle, adding the primarily dispersed ink into a three-roll grinder, and regulating the rotation speed of the front roller to be 400r/min, setting the speed ratio of the front roller to the middle roller to the rear roller to be 9:3:1, and repeatedly rolling for 3 times to obtain the biomass environment-friendly UV photocuring ink.
Example 2
A preparation method of biomass-based environment-friendly UV (ultraviolet) photocuring ink specifically comprises the following steps:
step 1, preparation of acrylate maleic ester modified rosin:
adding 20g of rosin, 60g of hydroxyethyl acrylate HEA and 0.3g of hydroquinone into a reaction kettle, bubbling nitrogen for 30min, heating to 120 ℃, continuing to heat to 230 ℃ after the rosin is molten, and reacting for 5h to obtain acrylate modified rosin; and stopping heating the reaction kettle, cooling to 120 ℃, adding 54g of maleic anhydride into the reaction kettle in the nitrogen atmosphere, and continuously reacting for 6 hours to obtain the acrylate maleic ester modified rosin.
Step 2, preparing the environment-friendly UV photocuring ink:
adding 50 parts of acrylate maleate modified rosin, 4.5 parts of neopentyl glycol diacrylate, 4 parts of pentaerythritol triacrylate, 3695.5 parts of irgacure, 240001.5 parts of lubrizol and 0.5 part of tris (N-nitroso-N-phenylhydroxylamine) aluminum salt into a reaction kettle according to the parts by weight, stirring at the speed of 500r/min for 10 minutes for pre-dispersion, then 2.25 parts of 3000-mesh talcum powder, 0.75 part of 1250-mesh calcium powder, 30 parts of yellow color paste and 1 part of acrylate phosphate are added according to the weight part while stirring, stirring for 15 minutes at the speed of 1000r/min to obtain primarily dispersed ink, taking the primarily dispersed ink out of the reaction kettle, adding the primarily dispersed ink into a three-roll grinder, regulating the rotation speed of the front roller to be 400r/min, setting the speed ratio of the front roller to the middle roller to the rear roller to be 9:3:1, and repeatedly rolling for 4 times to obtain the biomass environment-friendly UV photocuring ink.
Example 3
A preparation method of biomass-based environment-friendly UV (ultraviolet) photocuring ink specifically comprises the following steps:
step 1, preparation of acrylate maleic ester modified rosin:
adding 20g of rosin, 50g of hydroxyethyl acrylate HEA and 0.4g of hydroquinone into a reaction kettle, bubbling nitrogen for 30min, heating to 120 ℃, continuing to heat to 200 ℃ after the rosin is molten, and reacting for 4h to obtain acrylate modified rosin; and (3) stopping heating the reaction kettle, after the temperature is reduced to 100 ℃, adding 40g of maleic anhydride into the reaction kettle in the nitrogen atmosphere, and continuously reacting for 5 hours to obtain the acrylate maleic ester modified rosin.
Step 2, preparing the environment-friendly UV photocuring ink:
50.85 parts of acrylate maleate modified rosin, 10 parts of neopentyl glycol diacrylate, 6 parts of pentaerythritol triacrylate, 3697.3 parts of irgacure, 240002 parts of lubrizol and 0.15 part of tris (N-nitroso-N-phenylhydroxylamine) aluminum salt are added into a reaction kettle according to the parts by weight, stirred at the speed of 500r/min for 10 minutes for pre-dispersion, then adding 3.75 parts of 3000-mesh talcum powder, 1.25 parts of 1250-mesh calcium powder, 15.7 parts of yellow color paste and 3 parts of acrylate phosphate according to the weight parts while stirring, stirring for 15 minutes at the speed of 1000r/min to obtain primarily dispersed ink, taking the primarily dispersed ink out of the reaction kettle, adding the primarily dispersed ink into a three-roll grinder, regulating the rotation speed of the front roller to be 400r/min, setting the speed ratio of the front roller to the middle roller to the rear roller to be 9:3:1, and repeatedly rolling for 5 times to obtain the biomass environment-friendly UV photocuring ink.
Example 4
A preparation method of biomass-based environment-friendly UV (ultraviolet) photocuring ink specifically comprises the following steps:
step 1, preparation of acrylate maleic ester modified rosin:
adding 20g of rosin, 50g of hydroxyethyl acrylate HEA and 0.4g of hydroquinone into a reaction kettle, bubbling nitrogen for 30min, heating to 120 ℃, continuing to heat to 200 ℃ after the rosin is molten, and reacting for 4h to obtain acrylate modified rosin; and (3) stopping heating the reaction kettle, after the temperature is reduced to 100 ℃, adding 40g of maleic anhydride into the reaction kettle in the nitrogen atmosphere, and continuously reacting for 5 hours to obtain the acrylate maleic ester modified rosin.
Step 2, preparing the environment-friendly UV photocuring ink:
50.85 parts of acrylate maleate modified rosin, 10 parts of neopentyl glycol diacrylate, 3.3 parts of pentaerythritol triacrylate, irgacure 36910 parts, 240002 parts of lubrizol and 0.15 part of tris (N-nitroso-N-phenylhydroxylamine) aluminum salt are added into a reaction kettle according to the parts by weight, stirred at the speed of 500r/min for 10 minutes for pre-dispersion, then adding 3.75 parts of 3000-mesh talcum powder, 1.25 parts of 1250-mesh calcium powder, 15.7 parts of yellow color paste and 3 parts of acrylate phosphate according to the weight parts while stirring, stirring for 15 minutes at the speed of 1000r/min to obtain primarily dispersed ink, taking the primarily dispersed ink out of the reaction kettle, adding the primarily dispersed ink into a three-roll grinder, regulating the rotation speed of the front roller to be 400r/min, setting the speed ratio of the front roller to the middle roller to the rear roller to be 9:3:1, and repeatedly rolling for 4 times to obtain the biomass environment-friendly UV photocuring ink.
The preparation method of the biomass-based environment-friendly UV photocuring ink is characterized by comprising the following steps: firstly, carrying out Diels-Alder reaction on a conjugated diene structure in a rosin structure and hydroxyethyl acrylate to synthesize an intermediate
Hydroxyl in the intermediate reacts with maleic anhydride to introduce high-activity double bonds to obtain acrylate maleic acid ester modified rosin
The biomass-based environment-friendly UV photocuring ink is prepared by using the resin as film-forming resin and selecting reactive diluents, photoinitiators, pigments, fillers, dispersing agents, stabilizing agents and functional auxiliaries with different functionalities. The bio-based environment-friendly UV photocuring ink prepared by the invention avoids using acrylic acid modified rosin resin, reduces the smell of the ink, has high curing speed, good adhesion, high color concentration and good printability, is suitable for high-speed printing, and has good economic and social benefits.
Claims (4)
1. A preparation method of biomass-based environment-friendly UV (ultraviolet) photocuring ink is characterized by comprising the following steps: the feed comprises the following raw materials in parts by weight: 50-60 parts of acrylate maleic ester modified rosin, 8-16 parts of reactive diluent, 5-10 parts of photoinitiator, 1-2 parts of dispersant, 0.1-0.5 part of stabilizer, 15-30 parts of pigment, 2-5 parts of filler and 1-3 parts of functional assistant;
the method specifically comprises the following steps:
step 1, modifying rosin by adopting acrylate maleic acid ester;
the specific process of the step 1 is as follows:
under the nitrogen atmosphere, adding rosin, hydroxyethyl acrylate and a polymerization inhibitor into a reaction kettle, heating to 120 ℃ until the rosin is molten, heating to 180-230 ℃, and reacting for 3-5 hours to obtain acrylate modified rosin; after the temperature is reduced to 90-120 ℃, adding maleic anhydride into the reaction kettle, and continuing to react for 4-6h to obtain acrylate maleic ester modified rosin;
in the step 1, the mass ratio of rosin, hydroxyethyl acrylate and maleic anhydride is 1: 2-3: 1.5-2.7;
and 2, adding acrylate maleic acid ester modified rosin, an active diluent, a photoinitiator, a dispersant and a stabilizer into a reaction kettle according to parts by weight, stirring at the speed of 500r/min for 10 minutes for pre-dispersion, then adding a pigment, a filler and a functional assistant according to parts by weight while stirring, stirring at the speed of 1000r/min for 15 minutes to obtain a primarily dispersed ink material, taking the primarily dispersed ink material out of the reaction kettle, adding the primarily dispersed ink material into a three-roll grinder, and repeatedly rolling for 3-5 times to obtain the biomass-based environment-friendly UV photocuring ink.
2. The preparation method of the biomass-based environment-friendly UV photocuring ink as claimed in claim 1, characterized by comprising the following steps: in the step 1, the polymerization inhibitor is hydroquinone, and the mass of the polymerization inhibitor is 0.5-1% of that of the hydroxyethyl acrylate.
3. The preparation method of the biomass-based environment-friendly UV photocuring ink as claimed in claim 1, characterized by comprising the following steps: the functional assistant is adhesion promoter acrylate phosphate.
4. The preparation method of the biomass-based environment-friendly UV photocuring ink as claimed in claim 1, characterized by comprising the following steps: in the three-roller grinder in the step 2, the speed ratio of the front roller, the middle roller and the rear roller is set to be 9:3: 1.
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| CN115304757B (en) * | 2022-07-20 | 2023-08-11 | 成都托展新材料股份有限公司 | Block type ink resin and preparation method thereof |
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| US7001981B2 (en) * | 2003-04-25 | 2006-02-21 | Sun Chemical Corporation | Acrylated natural resins |
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