CN102660170B - Application of acrylic acid ester modified epoxy soybean oil in preparation of paper printing ink - Google Patents
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Abstract
The invention discloses an application of acrylic acid ester modified epoxy soybean oil in the preparation of paper printing ink. The application is as follows: epoxy soybean oil modified acrylic acid ester is used as a main component of the printing ink and is mixed with an active diluent, a pigment and a photoinitiator to prepare the paper printing ink; and an acrylate monomer bearing a hydroxyl group reacts with acid anhydrides to obtain a half-ester intermediate and the half-ester intermediate reacts with epoxy soybean oil to obtain the epoxy soybean oil modified acrylic acid ester. The product modified epoxy soybean oil obtained by the reaction between the acrylate monomer bearing a hydroxyl group and acid anhydrides can be applied to paper printing ink so as to significantly minimize the occurrence of misting.
Description
Technical field
The invention belongs to ink modification field, be specifically related to Acrylate Modified Epoxy soybean oil in the application of preparing in paper printing ink.
Background technology
Macromolecular material has excellent performance, is widely used in fields such as sophisticated technology, national defense construction and national economy, and they become modern science and technology and the indispensable irreplaceable important materials of life.What current most of synthesized polymer material adopted is that non-renewable petroleum resources are raw material, brings serious problem to environment.In addition, according to estimates the mankind at present just with a kind of " non-standing " speed than fast 100,000 times of natural output speed resource that consumes petroleum.Enter after 21 century; economize on resources and the energy; development low-carbon economy; the balance of preserving the ecological environment is that main green industry revolution is surging forward; the high speed consumption of petroleum resources; strengthened gradually global environment consciousness and the degree of social concern, sustainable development view has triggered the upsurge of the friendly product innovation of research environment and novel process jointly considering new environmental legislation.
The main component of bio-based product derives from plant, belongs to renewable resources, uses bio-based product, and the mankind can reduce the dependence to petroleum resources.It is widely distributed as biodegradable vegetables oil for soybean oil, aboundresources.Fatty acid chain in natural soybean oil contains higher degree of unsaturation, becomes the desirable monomer of multiple polyreaction.Utilize carbon carbon unsaturated link(age) in soybean oil, researchist carries out modification to it, obtains epoxy soybean oil.At present, epoxy soybean oil is widely used as plastic plasticizer.
About the method for modifying of epoxy soybean oil, comprise and adopt acrylic monomer modification, polyurethane-modified and Biodegradable polyester modification.About acrylic monomer modified epoxy soybean oil, at present morely concentrate on direct employing vinylformic acid and carry out modification.But the aspect such as tack, snappiness of acrylic acid modified epoxy soybean oil is all not very good, need to further improve.Xie Yijun etc. (" Synthesis of Epoxy Acrylate Type Photosensitive Coatings by Semi-ester Method ", Hebei University of Technology's journal, 2002,31 (2): 67-73) studied the reaction between Hydroxyethyl acrylate and epoxy soybean oil, the photosensitivity of product and film performance are all better than vinylformic acid and directly synthetic product of epoxy soybean oil.
At present also fewer about the research of this Acrylate Modified Epoxy soybean oil, be necessary it to carry out more deep research, to enrich the application of Acrylate Modified Epoxy soybean oil.
Summary of the invention
The object of the invention is to overcome prior art deficiency, provide Acrylate Modified Epoxy soybean oil in the application of preparing in paper printing ink, acrylate monomer and anhydride reaction that the epoxy soybean oil modified acrylic ester that the present invention adopts contains hydroxyl by employing obtain after half-ester intermediate, then react and obtain with epoxy soybean oil.It can improve the wettability of pigment and fly black situation as the main ingredient in ink formulations, has further enriched the Application Areas of Acrylate Modified Epoxy soybean oil.
Above-mentioned purpose of the present invention is achieved by following technical solution:
Acrylate Modified Epoxy soybean oil is in the application of preparing in paper printing ink, the main ingredient take epoxy soybean oil modified acrylic ester as ink, then be mixed with paper printing ink with reactive thinner, pigment and light trigger;
Acrylate monomer and anhydride reaction that described epoxy soybean oil modified acrylic ester contains hydroxyl by employing obtain after half-ester intermediate, then react and obtain with epoxy soybean oil.
Contriver finds through great many of experiments, in the time adopting this Acrylate Modified Epoxy soybean oil of having introduced anhydride group as ink main ingredient, utilize a small amount of carboxyl residual in resin, or the fatty segment containing in resin structure, can improve the wettability of pigment; Utilize acid anhydrides to epoxy resin chain extension, and then reduce residual micromolecular ratio in resin, can obviously improve resin and be applied to the black situation that flies in ink formulations.In addition the polar group containing in acid anhydrides, can improve the sticking power of resin to polar substrates.
The content of each component in formula, can carry out with reference to the ink of conventional modified soybean oil preparation.As a kind of preferred version, described paper printing ink is made up of the component counting by weight percentage as follows:
Epoxy soybean oil modified acrylic ester 25 ~ 60%;
Reactive thinner 20 ~ 60%;
Pigment 8 ~ 15%;
Light trigger 5 ~ 15%.
Acrylate monomer and anhydride reaction that described epoxy soybean oil modified acrylic ester contains hydroxyl by employing obtain after half-ester intermediate, then react and obtain with epoxy soybean oil.
As a kind of preferred version, described in contain hydroxyl acrylate monomer be preferably Hydroxyethyl acrylate, methacrylic ester hydroxyl ethyl ester, pentaerythritol triacrylate, Propylene glycol monoacrylate, Rocryl 410, trimethylolpropane diacrylate or TriMethylolPropane(TMP) dimethacrylate.
As a kind of preferred version, described acid anhydrides is preferably phthalic anhydride (PTD), Succinic anhydried (SCA), methyl hexahydrophthalic anhydride (MHHPA), MALEIC ANHYDRIDE, HHPA or tetrahydrophthalic anhydride.
Described reactive thinner can be the conventional reactive thinner in this area, as a kind of preferred version, described reactive thinner is preferably one or more the combination in tri methylol triacrylate, tri (propylene glycol) diacrylate, ethoxyquin tri methylol triacrylate or hexanediyl ester.
Described light trigger can be the conventional light trigger in this area, and as a kind of preferred version, described light trigger is preferably 2,4,6-Three methyl Benzene formyl diphenyl phosphine oxide and/or isopropyl thioxanthone.
Described pigment can be the conventional pigment in this area, and as a kind of preferred version, described pigment optimization is permanent bordeaux or phthalocyanine blue.
The preparation method of described paper printing ink obtains after each component being ground on three-roller evenly.
Compared with prior art, the present invention has following beneficial effect:
When the special Acrylate Modified Epoxy soybean oil that the present invention adopts is applied to paper printing ink, compared with only adopting acrylic acid modified epoxy soybean oil, can reduce significantly the wettability that flies black situation generation and improve pigment, simultaneously to the sticking power of the cured film effect that also has some improvement, the application of having widened modified epoxy soybean oil.
Embodiment
Further explain the present invention below in conjunction with specific embodiment, but embodiment does not do any type of restriction to the present invention.
In embodiment, agents useful for same source is as follows:
Epoxy soybean oil: technical grade, yellow transparent liquid (acid number 0.6 mg KOH/g, oxirane value 0.65 %), Guangzhou Hai Erma vegetables oil company limited;
Tetra hydro Phthalic anhydride (PTD): analytical pure, colourless crystallization powder, Guangzhou Chemical Reagent Factory;
Senecioate-hydroxyl ethyl ester (HEA): 97 %, colourless transparent liquid, Shanghai Aladdin reagent company limited;
Pentaerythritol triacrylate (PETA): hydroxyl value 114 mgKOH/g, water white transparency viscous fluid, Guangzhou Boxing Chemical Industry Science Co., Ltd;
Triphenylphosphine (TPP): 97%, white crystal, Shanghai Aladdin reagent company limited;
P methoxy phenol (MEHQ): analytical pure, white plates crystallization, Shanghai Aladdin reagent company limited;
N, N-dimethyl benzylamine (DMBA): analytical pure, colourless liquid, Shanghai Aladdin reagent company limited;
Four butyl bromation amine (TBAB): analytical pure, white crystal, Shanghai Aladdin reagent company limited;
Ink flies China ink test: it is to observe ink in the time of printing that ink flies China ink, and ink departs from the discrete case of ink roller; Its detection method is to utilize when measuring ink stickiness, the glutinous black situation of observing blank sheet of paper on ink stickiness instrument crossbeam judges, concrete grammar is to measure by the ink stickiness method of inspection, when ink stickiness instrument is opened after 1min, on crossbeam, put a blank sheet of paper, after being rotated further 1min, take off blank sheet of paper, observe on blank sheet of paper whether have China ink, how much judge according to the ink sticking on blank sheet of paper the black degree that flies.In embodiment, fly the number of black degree all by estimating more relative judgement with comparative example 1.
embodiment 1 HEAPTD-ESO preparation
(1) mixed in molar ratio with 1.05:1 by HEA and PTD, add again p methoxy phenol (MEHQ) with respect to mixture total mass 0.15 % as stopper, and with respect to the triphenylphosphine (TPP) (or other catalyzer) of mixture total mass 1.4 %, slowly be heated to 100 ℃, mixture slowly becomes the liquid of clarification;
(2) in the time that the reaction system acid number reduction of step (1) no longer changes, add epoxy soybean oil, carboxyl mole number after the add-on of epoxy soybean oil converts in oxirane value and actual acid number calculates with the ratio of 1.1:1, add respectively again triphenylphosphine and MEHQ, guarantee that its massfraction is that 1.4 % and 0.15 % are constant, temperature rise to 120 ℃, continuous sampling and testing acid number in reaction process, in the time that acid number drops to 5 mg/g, stopped reaction.Final product is shallow khaki color thick liquid, i.e. HEAPTD-ESO.
embodiment 2 PETAPTD-ESO preparations
(1) mixed in molar ratio with 1.08:1 by PETA and PTD, add again p methoxy phenol (MEHQ) with respect to mixture total mass 0.15% as stopper, and with respect to the triphenylphosphine (TPP) of mixture total mass 1.4 %, slowly be heated to 110 ℃, mixture slowly becomes the liquid of clarification;
(2) in the time that the reaction system acid number reduction of step (1) no longer changes, add epoxy soybean oil, carboxyl mole number after the add-on of epoxy soybean oil converts in oxirane value and actual acid number calculates with the ratio of 1.1:1, add respectively again triphenylphosphine and MEHQ, guarantee that its massfraction is that 1.4 % and 0.15 % are constant, 100 ℃ of temperature controls, continuous sampling and testing acid number in reaction process, in the time that acid number drops to 5 mg/g, stopped reaction.Final product is shallow khaki color thick liquid, i.e. PETAPTD-ESO.
embodiment 3 HEASCA-ESO preparations
(1) mixed in molar ratio with 1.08:1 by HEA and SCA, add again p methoxy phenol (MEHQ) with respect to mixture total mass 0.15 % as stopper, and with respect to the triphenylphosphine (TPP) of mixture total mass 1.4 %, slowly be heated to 110 ℃, mixture slowly becomes the liquid of clarification;
(2) in the time that the reaction system acid number reduction of step (1) no longer changes, add epoxy soybean oil, carboxyl mole number after the add-on of epoxy soybean oil converts in oxirane value and actual acid number calculates with the ratio of 1.1:1, add respectively again triphenylphosphine and MEHQ, guarantee that its massfraction is that 1.4 % and 0.15 % are constant, 100 ℃ of temperature controls, continuous sampling and testing acid number in reaction process, in the time that acid number drops to 5 mg/g, stopped reaction.Final product is shallow khaki color thick liquid, i.e. HEASCA-ESO.
embodiment 4 HEAMHHPA-ESO preparations
(1) mixed in molar ratio with 1.08:1 by HEA and MHHPA, add again p methoxy phenol (MEHQ) with respect to mixture total mass 0.15 % as stopper, and with respect to the triphenylphosphine (TPP) of mixture total mass 1.4%, slowly be heated to 110 ℃, mixture slowly becomes the liquid of clarification;
(2) in the time that the reaction system acid number reduction of step (1) no longer changes, add epoxy soybean oil, carboxyl mole number after the add-on of epoxy soybean oil converts in oxirane value and actual acid number calculates with the ratio of 1.1:1, add respectively again triphenylphosphine and MEHQ, guarantee its massfraction be 1.4% and 0.15 % constant, 100 ℃ of temperature controls, continuous sampling and testing acid number in reaction process, in the time that acid number drops to 5 mg/g, stopped reaction.Final product is shallow khaki color thick liquid, i.e. HEAMHHPA-ESO.
embodiment 5the preparation of HEAMAH-ESO
(1) mixed in molar ratio with 1.08:1 by HEA and MAH, add again p methoxy phenol (MEHQ) with respect to mixture total mass 0.15% as stopper, and with respect to the triphenylphosphine (TPP) of mixture total mass 1.4 %, slowly be heated to 110 ℃, mixture slowly becomes the liquid of clarification;
(2) in the time that the reaction system acid number reduction of step (1) no longer changes, add epoxy soybean oil, carboxyl mole number after the add-on of epoxy soybean oil converts in oxirane value and actual acid number calculates with the ratio of 1.1:1, add respectively again triphenylphosphine and MEHQ, guarantee that its massfraction is that 1.4 % and 0.15 % are constant, 100 ℃ of temperature controls, continuous sampling and testing acid number in reaction process, in the time that acid number drops to 5 mg/g, stopped reaction.Final product is shallow khaki color thick liquid, i.e. HEAMAH-ESO.
embodiment 6 prepares the application of paper printing ink
Formulated paper printing ink according to counting by weight percentage as follows:
Epoxy soybean oil modified acrylic ester: 45%
Tri methylol triacrylate (TMPTA): 13%
Tri (propylene glycol) diacrylate (TPGDA): 20%
Permanent bordeaux F4R:12%
Light trigger TPO(2,4,6-Three methyl Benzene formyl diphenyl phosphine oxide): 5%
Light trigger ITX(isopropyl thioxanthone): 5%
After above-mentioned component being ground on three-roller evenly, test ink performance; Another roller coat is on carton paper, and thickness 30um, solidifies 6s in lamp source power under the uv cure machine that is 3.6kW, take out; Test curing membrane performance, test result is as shown in table 1 below:
Table 1
Test result shows: with hydroxy acryl acid ester monomer and anhydride reaction after product modified epoxy soybean oil, compared with the epoxy soybean oil of the direct modification of vinylformic acid, can improve significantly the black situation that flies of ink, and improve the wettability of pigment, to the sticking power of the cured film effect that also has some improvement, can be used in paper printing ink formulations simultaneously.
embodiment 7 prepares the application of paper printing ink
According to the formula preparation preparation paper printing ink of table 2, in table 2, the content of each material is weight percentage: reactive thinner still adopts this area conventional ethoxyquin tri methylol triacrylate, tri (propylene glycol) diacrylate and hexanediyl ester, light trigger also adopts conventional TPO and ITX, and changing other also has similar effect.
Table 2
| ? | Epoxy soybean oil modified acrylic ester | Ethoxyquin tri methylol triacrylate | Tri (propylene glycol) diacrylate | Hexanediyl ester | Permanent bordeaux F4R | Phthalocyanine Blue BGS | Light trigger TPO | Light trigger ITX |
| Formula 2 | 50 | 10 | 20 | 0 | 10 | 0 | 5 | 5 |
| Formula 3 | 50 | 10 | 20 | 0 | 0 | 10 | 3 | 7 |
| Formula 4 | 30 | 25 | 25 | 0 | 10 | 0 | 5 | 5 |
| Formula 5 | 55 | 10 | 0 | 15 | 10 | 0 | 6 | 4 |
| Formula 6 | 40 | 10 | 15 | 15 | 0 | 10 | 5 | 5 |
Press described in table 2 after component grinds evenly on three-roller test ink performance; Another roller coat is on carton paper, and thickness 30um, solidifies 6s in lamp source power under the uv cure machine that is 3.6kW, take out; Test curing membrane performance, test result is as shown in table 3 below:
Table 3
Test result shows:
In described paper ink formula, described Acrylate Modified Epoxy soybean oil all can be improved significantly ink and fly black situation, and can improve the wettability of pigment, to the sticking power of the cured film ability that also has some improvement.
Claims (6)
1. Acrylate Modified Epoxy soybean oil, in the application of preparing in paper printing ink, is characterized in that, the main ingredient take epoxy soybean oil modified acrylic ester as ink, then be mixed with paper printing ink with reactive thinner, pigment and light trigger;
Described epoxy soybean oil modified acrylic ester is by adopting Hydroxyethyl acrylate to react and obtain after half-ester intermediate with phthalic anhydride, Succinic anhydried or methyl hexahydrophthalic anhydride, then reacts and obtain with epoxy soybean oil;
The preparation method of described epoxy soybean oil modified acrylic ester comprises the following steps:
(1) mixed in molar ratio with 1.05:1 by Hydroxyethyl acrylate and phthalic anhydride, add again p methoxy phenol with respect to mixture total mass 0.15 % as stopper, and with respect to the triphenylphosphine of mixture total mass 1.4 %, slowly be heated to 100 ℃, mixture slowly becomes the liquid of clarification;
(2) in the time that the reaction system acid number reduction of step (1) no longer changes, add epoxy soybean oil, carboxyl mole number after the add-on of epoxy soybean oil converts in oxirane value and actual acid number calculates with the ratio of 1.1:1, add respectively again triphenylphosphine and p methoxy phenol, guarantee that its massfraction is that 1.4 % and 0.15 % are constant, temperature rise to 120 ℃, continuous sampling and testing acid number in reaction process, in the time that acid number drops to 5 mg/g, stopped reaction; Final product is shallow khaki color thick liquid;
Or the preparation method of described epoxy soybean oil modified acrylic ester comprises the following steps:
(1) mixed in molar ratio with 1.08:1 by Hydroxyethyl acrylate and Succinic anhydried or methyl hexahydrophthalic anhydride, add again p methoxy phenol with respect to mixture total mass 0.15 % as stopper, and with respect to the triphenylphosphine of mixture total mass 1.4 %, slowly be heated to 110 ℃, mixture slowly becomes the liquid of clarification;
(2) in the time that the reaction system acid number reduction of step (1) no longer changes, add epoxy soybean oil, carboxyl mole number after the add-on of epoxy soybean oil converts in oxirane value and actual acid number calculates with the ratio of 1.1:1, add respectively again triphenylphosphine and p methoxy phenol, guarantee that its massfraction is that 1.4 % and 0.15 % are constant, 100 ℃ of temperature controls, continuous sampling and testing acid number in reaction process, in the time that acid number drops to 5 mg/g, stopped reaction; Final product is shallow khaki color thick liquid.
2. Acrylate Modified Epoxy soybean oil, in the application of preparing in paper printing ink, is characterized in that as claimed in claim 1, and described paper printing ink is made up of the component counting by weight percentage as follows:
Epoxy soybean oil modified acrylic ester 25 ~ 60%;
Reactive thinner 20 ~ 60%;
Pigment 8 ~ 15%;
Light trigger 5 ~ 15%.
3. Acrylate Modified Epoxy soybean oil, in the application of preparing in paper printing ink, is characterized in that as claimed in claim 2, and described reactive thinner is tri methylol triacrylate and/or tri (propylene glycol) diacrylate.
4. Acrylate Modified Epoxy soybean oil, in the application of preparing in paper printing ink, is characterized in that as claimed in claim 2, and described light trigger is 2,4,6-Three methyl Benzene formyl diphenyl phosphine oxide and/or isopropyl thioxanthone.
5. Acrylate Modified Epoxy soybean oil, in the application of preparing in paper printing ink, is characterized in that as claimed in claim 2, and described pigment is permanent bordeaux or phthalocyanine blue.
6. Acrylate Modified Epoxy soybean oil, in the application of preparing in paper printing ink, is characterized in that as claimed in claim 1, and the preparation method of described paper printing ink obtains after each component being ground on three-roller evenly.
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