CN112358765A - Low-odor UV ink-jet ink and preparation method thereof - Google Patents
Low-odor UV ink-jet ink and preparation method thereof Download PDFInfo
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- CN112358765A CN112358765A CN202011158709.6A CN202011158709A CN112358765A CN 112358765 A CN112358765 A CN 112358765A CN 202011158709 A CN202011158709 A CN 202011158709A CN 112358765 A CN112358765 A CN 112358765A
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- acrylate
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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
- C09D11/30—Inkjet printing inks
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B41—PRINTING; LINING MACHINES; TYPEWRITERS; STAMPS
- B41M—PRINTING, DUPLICATING, MARKING, OR COPYING PROCESSES; COLOUR PRINTING
- B41M5/00—Duplicating or marking methods; Sheet materials for use therein
- B41M5/0023—Digital printing methods characterised by the inks used
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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
- C09D11/30—Inkjet printing inks
- C09D11/38—Inkjet printing inks characterised by non-macromolecular additives other than solvents, pigments or dyes
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- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Wood Science & Technology (AREA)
- Organic Chemistry (AREA)
- Inks, Pencil-Leads, Or Crayons (AREA)
Abstract
The invention belongs to the technical field of printing consumables and discloses low-odor UV ink-jet ink and a preparation method thereof. The UV ink-jet ink is mainly prepared from a monomer, a photoinitiator, a dispersant and a pigment; the monomer comprises a functional monomer which is a monofunctional monomer containing ethoxy and/or a monofunctional monomer containing propoxy. The monomer used by the UV ink-jet ink contains low-irritation ethoxy and propoxy, and the ethoxy and propoxy increase the molecular weight of the monomer, so that the monomer has low odor and low irritation, and the UV ink-jet ink has low odor and low irritation; meanwhile, the ink has high flexibility, folding resistance, ductility and adhesiveness, and excellent comprehensive performance. The preparation method is simple and easy to operate.
Description
Technical Field
The invention belongs to the technical field of printing consumables, and particularly relates to low-odor UV ink-jet ink and a preparation method thereof.
Background
The UV ink-jet printing has digital editing capability, and can be applied to various substrates, such as flexible film substrates and hard materials such as plastics, metals, ceramics and the like, and has good adhesion performance and flexible and folding-resistant performance.
Meanwhile, UV ink-jet is more and more favored because of the advantages of no solvent volatilization, rapid photo-curing, energy saving, carbon reduction, green environment and the like. However, since the main raw material of the UV inkjet ink has a molecular structure of acrylate monomer, low molecular weight monomer has a sharp odor and skin irritation, which requires a good ventilation equipment in the UV inkjet printing shop. Especially high print throughput single pass printers, the accumulated odor, if not dealt with in time, can cause discomfort and even physical harm to the operator.
Most of the monomers with irritation and irritation are low molecular weight monofunctional monomers, which are essential materials for adjusting viscosity, improving adhesion and flexibility and folding resistance of UV ink. Such as benzyl acrylate (BZA), tetrahydrofurfuryl acrylate (THFA), Dimethylacrylamide (DMAA), 2-phenoxyethyl acrylate (PHEA), isobornyl acrylate (IBOA), and N-vinyl pyrrolidone (NVP) which are commonly used. The monomers have low viscosity, strong dilutability, good folding resistance and adhesion, and are excellent monomer materials. However, these monomers are not used in a large amount in ink because of their odor and irritation. With the popularity of high-speed single-channel wide format printers, there is an urgent need in the market for low odor, low irritation UV inkjet inks.
Therefore, it is desirable to provide a low odor, low irritation UV inkjet ink that solves the problem of the harsh and irritating nature of conventional acrylate monomers to accommodate high speed single channel printers.
Disclosure of Invention
The present invention is directed to solving at least one of the problems of the prior art described above. To this end, the present invention proposes a low-odor UV inkjet ink having low odor and low irritation.
The invention provides a low-odor UV ink-jet ink which is mainly prepared from a monomer, a photoinitiator, a dispersant and a pigment; the monomer comprises a functional monomer, and the functional monomer is a monofunctional monomer containing ethoxy and/or a monofunctional monomer containing propoxy.
Preferably, the monofunctional monomer having an ethoxy group is selected from the group consisting of 2- (p-cumyl-phenoxy) -ethyl acrylate (CPEA-EO), benzyl ethoxy acrylate (BZA-EO), o-phenylphenoxyethyl acrylate (OPPEA), diethoxyphenylphenoxyethyl acrylate (OPPEA-2EO), dicyclopentadienyl ethoxy acrylate, tetrahydrofurfuryl diethoxy acrylate (THFA-2EO), tetrahydrofurfuryl triethoxy acrylate (THFA-3PO), diethoxyphenol acrylate (PHEA-2EO), ethoxydimethylacrylamide (DMAA-EO), triethoxyphenol acrylate (PHEA-3EO), tetraethoxyphenol acrylate (PHEA-4EO), diethoxyphenol acrylate (NPA-2PO), At least one of tetraethoxynonylphenol acrylate (NPA-4EO) or octaethoxynonylphenol acrylate (NPA-8 EO). The ethoxyl EO with low irritation is introduced into a monomer structure, so that the molecular weight of the monomer is increased to meet the performance of the ink, and the ink has low odor and low irritation.
Preferably, the propoxy group containing monofunctional monomer is selected from tetrahydrofurfuryl tripropoxy acrylate (THFA-3PO) or/and dipropoxynonylphenol acrylate (NPA-2 PO). The propoxy PO with low irritation is introduced into the monomer structure, so that the molecular weight of the monomer is increased to meet the performance of the ink, and the ink has low odor and low irritation.
Preferably, the monomers further comprise a viscosity adjusting monomer; the viscosity adjusting monomer is a monomer containing a single functional group. The viscosity adjusting monomer is a monomer for adjusting the viscosity of the ink. The monomer containing the monofunctional group is convenient to adjust the viscosity of the ink, and can not cause excessive crosslinking to influence the performance of the ink. If the monomer containing multiple functional groups is selected, the mechanical strength and toughness of the coating can be improved, the odor is low, excessive crosslinking is easy to generate, the coating is brittle and hard to shrink, and the addition amount needs to be controlled during use.
Further preferably, the viscosity adjusting monomer is selected from the group consisting of 4-hydroxybutyl acrylate (HBA), dicyclopentadienyl acrylate (DCPA), phenoxybenzyl acrylate (PBA), cyclo-trimethylolpropane formal acrylate (CTFA), trimethylol cyclohexyl acrylate (TMCHA), 4-tert-butylcyclohexyl acrylate (TBCHA), Caprolactone Acrylate (CA), N-Acryloylmorpholine (ACMO), N-vinylcaprolactam (NVC), 2- (2-vinyloxyethoxy) ethyl acrylate (VEEA), N-hydroxyethyl acrylamide (HEAA), 1, 6-hexanediol diacrylate (HDDA), trimethylolpropane triacrylate (TMPTA), dipropylene glycol diacrylate (DPGDA), tripropylene glycol diacrylate (TPGDA), dipropylene glycol diacrylate (NPG (2PO) DA), neopentyl glycol, At least one of triethoxy trimethylolpropane triacrylate (TMP (3EO) TA) or nonaethoxy trimethylolpropane triacrylate (TMP (9EO) TA).
Preferably, the photoinitiator is selected from bis (2,4, 6-trimethylbenzoyl) phenylphosphine oxide, 2,4, 6-trimethylbenzoyldiphenylphosphine oxide, hydroxycyclohexyl benzophenone, 2-hydroxy-2-methyl-1-phenyl-1-propanone, 1' - (methylenebis-4, 1-phenylene) bis [ 2-hydroxy-2-methyl-1-propanone ], 2-benzyl-2-dimethylamino-1- (4-morpholinylphenyl) butanone, 2- (4-methylbenzyl) -2- (dimethylamino) -1- (4-morpholinylphenyl) -1-butanone, 2-methyl-1- (4-methylthiophenyl) -2-morpholinyl-1-propanone, and mixtures thereof, At least two of 2, 4-diethylthiazolone or 2-isopropylthioxanthone. The photoinitiator, upon absorption of ultraviolet light (UV), decomposes to form an initiating free radical, initiating polymerization of the monomer. Because the pigment can absorb part of ultraviolet light, the photo-curing reaction needs to be carried out by matching with photoinitiators with different absorption wave bands.
Preferably, the dispersant is selected from Dispers 710/685/655 from degussa, BYK Disper BYK-168/9130/9131/9132/9150/9151/9152/2100/2200/2205, Solsperse 24000/32000/32500/36000/39000 from lubrium, EFKA 4310/4330/4030/4701 from EFKA, and the like. Dispersants are used to disperse pigments.
Preferably, the pigments include blue pigments PB15:1, PB15:2, PB15:3, PB15: 4; yellow pigments PY138, PY150, PY151, PY155, PY168, PY180, PY183, PY185, PY 194; red pigments PV19, PR122, PR146, PR254, PR 269; black pigment carbon black; white pigment titanium dioxide, and the like. Can be purchased from basf, langen, clarien, japanese ink, mitsubishi chemical, winning, dupont or stone sources.
Preferably, the UV ink-jet ink is mainly prepared from the following components in percentage by weight:
further preferably, the UV inkjet ink is mainly prepared from the following components in percentage by weight:
preferably, the mass ratio of the functional monomer to the viscosity adjusting monomer is (50-80): (4-25); further preferably, the mass ratio of the functional monomer to the viscosity adjusting monomer is (58-80): (4-20).
Preferably, the UV inkjet ink further comprises an auxiliary agent, wherein the auxiliary agent comprises a wetting agent or/and a stabilizer. The wetting agent is used for wetting the substrate, so that the ink can be smoothly attached to the surface of the substrate and can be leveled to form a uniform coating. The stabilizer is used for stabilizing the ink so that the ink is not influenced by the light and heat in the environment to deteriorate in the storage process.
Preferably, the wetting agent comprises BYK-371/377/378/337/3500/3505/361; the stabilizer comprises 2, 6-di-tert-butyl-4-methylphenol (BHT), 4-Methoxyphenol (MEHQ), GENORAD 16/18/20/22/23 from RAHN, and Cyanote S100/110/210/130.
Preferably, the wetting agent is added in an amount of 0-5% of the total mass of the UV inkjet ink.
Preferably, the stabilizer is added in an amount of 0 to 5% of the total mass of the UV inkjet ink.
The preparation method of the UV ink-jet ink comprises the following steps: and mixing the monomer, the photoinitiator, the dispersant and the pigment, grinding and filtering to obtain a filtrate, namely the UV ink-jet ink.
Specifically, the preparation method of the UV ink-jet ink comprises the following steps: adding a photoinitiator and a dispersant into a monomer, and stirring until the photoinitiator and the dispersant are completely dissolved; then adding the pigment into the mixture and stirring the mixture evenly, introducing the mixture into a sand mill and using grinding beads with the particle size of 0.1-0.5mm to grind the mixture to the particle size of 100-200 nm; filtering with 1.0 μm glass fiber and 0.45 μm PP filter membrane, and collecting the filtrate to obtain ink.
A printed product comprises a substrate and a printing layer formed by the UV ink-jet ink.
Preferably, the substrate is selected from at least one of paper, plastic, metal, ceramic, or glass.
Preferably, the printed product is advertisement paper, wallpaper and the like.
The inventors have found that monomer odor is related to monomer volatility, and generally the higher the molecular weight, the less volatile and the lower the odor. The irritation is related to the molecular structure, and the monomer containing ethoxy or propoxy has low irritation, so that the ethoxy or propoxy structure is adopted to increase the molecular weight of the monomer, the odor and the irritation of the monomer can be effectively reduced, and the odor and the irritation of the UV ink-jet ink can be effectively reduced. The monofunctional monomer has small molecular weight, so that viscosity is low, dilution is good, but odor is large, and the monofunctional monomer needs to be reasonably matched with the monomer containing ethoxy or propoxy to prepare the UV ink-jet ink with low odor and low irritation.
Compared with the prior art, the invention has the following beneficial effects:
(1) the monomer used by the UV ink-jet ink contains ethoxy, propoxy and the ethoxy and propoxy increase the molecular weight of the monomer, so that the monomer has low odor and low irritation, and the UV ink-jet ink has low odor and low irritation; meanwhile, the ink has high flexibility, folding resistance, ductility and adhesiveness, is excellent in comprehensive performance, and can adapt to a high-speed single-channel printer.
(2) The preparation method is simple and easy to operate.
Detailed Description
In order to make the technical solutions of the present invention more apparent to those skilled in the art, the following examples are given for illustration. It should be noted that the following examples are not intended to limit the scope of the claimed invention.
In the following examples, monomers were purchased from Changxing chemical Co., Ltd, Korea Meiyuan specialization Co., China Dride chemical Co., Ltd, photoinitiators were purchased from Hubei Gurun science and technology Co., Ltd, auxiliary agents were purchased from German Yingchu, German Bike chemical Co., Ltd, dispersants were purchased from U.S. Loborun, German Yingchu, German Bike chemical Co., Ltd, and pigments were purchased from Japan ink chemical Co., Ltd. Other materials, reagents or equipment used may be obtained from conventional commercial sources or may be obtained by known methods in the art, unless otherwise specified.
Example 1
The ethoxylated or propoxylated monomer comprises 20.2 parts of diethoxyphenol acrylate PHEA-2EO, 25.0 parts of diethoxyphenol acrylate tetrahydrofurfuryl-THFA-2 EO, 20.0 parts of ethoxybenzyl acrylate BZA-EO, 5.0 parts of o-phenylphenoxyethyl acrylate OPPEA; the adjusting monomer comprises 8.0 parts of cyclotrimethylolpropane formal acrylate CTFA, 8.0 parts of N-acryloyl morpholine ACMO and 4.0 parts of nonaethoxylated trimethylolpropane triacrylate TMP (9EO) TA; the photoinitiator included 5.0 parts of 2,4, 6-trimethylbenzoyldiphenylphosphine oxide (TPO); the auxiliary agent comprises 1.0 part of BYK-337 wetting agent and 0.3 part of GENORAD16 stabilizer; and 1.5 parts of a dispersing agent Solsperse24000, stirring until the dispersing agent is completely dissolved, wherein the stirring speed is 1000rpm, and the stirring time is 4 hours, so as to obtain a pre-solution.
Mixing and stirring the pre-solution and 2.0 parts of yellow pigment PY-150 until the pigment is completely wetted, wherein the stirring speed is 1000rpm, and the stirring time is 8 hours, so as to obtain a pre-dispersion solution; and then introducing the pre-dispersion solution into a sand mill, grinding at the rotating speed of 2000rpm, grinding with 0.4mm yttrium zirconium grinding beads at the temperature of 20-40 ℃, grinding to the particle size of 100-200nm, and filtering with 1.0 mu m glass fiber and 0.45 mu m PP filter membrane to obtain the filtrate, namely the UV ink-jet ink.
Examples 2 to 8
The formulations of examples 2-8 are shown in Table 1, and the preparation is as in example 1.
Comparative examples 1 to 4
The formulations of comparative examples 1-4 are shown in Table 2, and the preparation is the same as in example 1.
TABLE 1 raw material compositions for examples 1-8
TABLE 2 feed compositions for comparative examples 1-4
Product effectiveness testing
A domestic UV wide-width printer of a test platform is used, an LED-UV curing lamp (with the wavelength of 395nm) is carried, and a light-regulating five-generation industrial spray head MH5420 is adopted. The printer test conditions were set to: the voltage of the nozzle is 18.5V +/-0.5V, the temperature of the nozzle is 45 +/-5 ℃, the temperature of the secondary ink box is 45 +/-5 ℃, the negative pressure is 4.5kPa +/-0.5 kPa, and 6Pass high-speed printing is carried out.
1. Ink odor and irritation testing
During the process of continuously printing the full ink quantity of yellow, red, blue and black for 3 m, 10 persons were asked to feel the smell and the irritation of the UV ink-jet ink on the operation site and judge according to the personal sense. Acceptable for more than 7 people (including 7 people) represents mild and low irritation; 4-6 people can accept the medicine, and the medicine has moderate smell and irritation; acceptable to 0-3 people represents a strong odor and strong irritation. Through the tests, the number of persons acceptable for the inks obtained in the examples is shown in Table 3, and the number of persons acceptable for the inks obtained in the comparative examples is shown in Table 4.
2. Ink adhesion test
The ink is printed on a domestic acrylic plate to carry out a check standard test by adopting the national standard GB9286 and the ISO2409 standard. The grade 0 represents that the cut of the hundred-grid cutter is smooth and has no spalling or crevasse; grade 1 represents 5% spalling or crevasse; grade 2 represents 5-15% of the cracks or breaks; grade 3 represents 15-35% of the cracks or breaks; grade 4 represents 35-65% of the cracks or breaks; grade 5 represents more than 65% of the cracks or tears. The adhesion property was acceptable when the grade was not more than 1 (including grade 1), and was not acceptable when the grade was not less than 2. The test results are shown in tables 3 and 4.
3. Flexibility and folding endurance test
And printing the ink on a PVC flexible film, folding twice (cross folding), pressurizing the cross center point by using fingers for 1min, spreading the cross center point by using the fingers, and observing whether the printed coating cracks. The cross crease does not crack, and the folding resistance is qualified; if the crease cracks, the folding resistance is not qualified. The test results are shown in tables 3 and 4.
Table 3 results of functional testing of examples 1-8
Table 4 comparative examples 1-4 functional test results
Comparative examples 1-4, which did not employ the low odor and low irritation monomer formulation of the present invention, had a large odor and strong irritation upon printing. Examples 1-8 using the monofunctional monomer having ethoxy group and/or the monofunctional monomer having propoxy group according to the present invention, inks were obtained which were less irritating, less smelling, and consistent with and even superior to conventional inks in terms of adhesion and folding endurance.
Claims (10)
1. A UV inkjet ink, characterized in that the UV inkjet ink is mainly made of monomers, photoinitiators, dispersants and pigments; the monomer comprises a functional monomer, and the functional monomer is a monofunctional monomer containing ethoxy and/or a monofunctional monomer containing propoxy.
2. The UV inkjet ink according to claim 1, wherein the mono-functional monomer containing an ethoxy group is selected from at least one of 2- (p-cumyl-phenoxy) -ethyl acrylate, benzyl ethoxy acrylate, o-phenylphenoxyethyl acrylate, diethoxyphenyl phenoxyethyl acrylate, dicyclopentadienyl ethoxy acrylate, tetrahydrofurfuryl diethoxy acrylate, tetrahydrofurfuryl triethoxy acrylate, diethoxy phenol acrylate, ethoxy dimethylacrylamide, triethoxy phenol acrylate, tetraethoxy phenol acrylate, diethoxy phenol acrylate, tetraethoxy nonyl phenol acrylate, or octaethoxy nonyl phenol acrylate.
3. The UV inkjet ink of claim 1, wherein the propoxy-containing monofunctional monomer is selected from tetrahydrofurfuryl tripropoxy acrylate or/and dipropoxynonylphenol acrylate.
4. The UV inkjet ink of claim 1, wherein the monomers further comprise a viscosity adjusting monomer; the viscosity adjusting monomer is selected from at least one of 4-hydroxybutyl acrylate, dicyclopentadienyl acrylate, phenoxybenzyl acrylate, cyclotrimethylolpropane formal acrylate, trimethylolpropane cyclohexyl acrylate, 4-tert-butylcyclohexyl acrylate, caprolactone acrylate, N-acryloylmorpholine, N-vinylcaprolactam, 2- (2-vinyloxyethoxy) ethyl acrylate, N-hydroxyethyl acrylamide, 1, 6-hexanediol diacrylate, trimethylolpropane triacrylate, dipropylene glycol diacrylate, tripropylene glycol diacrylate, dipropoxy neopentyl glycol diacrylate, triethoxy trimethylolpropane triacrylate or nonaethoxy trimethylolpropane triacrylate.
5. The UV inkjet ink according to any one of claims 1 to 4, characterized by being prepared from essentially the following components in weight percent:
6. the UV inkjet ink of claim 5, wherein the UV inkjet ink is prepared from the following components in percentage by weight:
7. the UV inkjet ink according to claim 4, wherein the mass ratio of the functional monomer to the viscosity adjusting monomer is (50-80): (4-25); preferably, the mass ratio of the functional monomer to the viscosity adjusting monomer is (58-80): (4-20).
8. The UV inkjet ink according to any one of claims 1 to 4, wherein the UV inkjet ink further comprises an auxiliary agent, wherein the auxiliary agent comprises a wetting agent or/and a stabilizer.
9. The method of making a UV inkjet ink according to any one of claims 1 to 7, comprising the steps of: and mixing the monomer, the photoinitiator, the dispersant and the pigment, grinding and filtering to obtain a filtrate, namely the UV ink-jet ink.
10. A printed article comprising a substrate and a printed layer of the UV inkjet ink of any one of claims 1 to 7.
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Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20180273782A1 (en) * | 2015-09-28 | 2018-09-27 | MGI Digital Technology | Varnish composition with low levels of migration for inkjet-printed substrate |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20180273782A1 (en) * | 2015-09-28 | 2018-09-27 | MGI Digital Technology | Varnish composition with low levels of migration for inkjet-printed substrate |
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Address after: 1st and 2nd Floor East Area and 3rd and 4th Floor, Phase II Logistics Center Plant, No. 3, Dingwan 7th Road, Sanzao Town, Jinwan District, Zhuhai City, Guangdong Province, 519000 Applicant after: Zhuhai Chuanmeixun New Materials Co.,Ltd. Address before: 519090 No.3, dingdingwan 7th Road, Sanzao, Jinwan District, Zhuhai City, Guangdong Province Applicant before: TrendVision Electronics Science Technology (Zhuhai) Co.,Ltd. |
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