CN112939775B - Oligomer suitable for photocuring inkjet ink - Google Patents
Oligomer suitable for photocuring inkjet ink Download PDFInfo
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- CN112939775B CN112939775B CN202110262691.2A CN202110262691A CN112939775B CN 112939775 B CN112939775 B CN 112939775B CN 202110262691 A CN202110262691 A CN 202110262691A CN 112939775 B CN112939775 B CN 112939775B
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/24—Preparation of carboxylic acid esters by reacting carboxylic acids or derivatives thereof with a carbon-to-oxygen ether bond, e.g. acetal, tetrahydrofuran
- C07C67/26—Preparation of carboxylic acid esters by reacting carboxylic acids or derivatives thereof with a carbon-to-oxygen ether bond, e.g. acetal, tetrahydrofuran with an oxirane ring
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/04—Preparation of carboxylic acid esters by reacting carboxylic acids or symmetrical anhydrides onto unsaturated carbon-to-carbon bonds
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/08—Preparation of carboxylic acid esters by reacting carboxylic acids or symmetrical anhydrides with the hydroxy or O-metal group of organic compounds
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/30—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group
- C07C67/313—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group by introduction of doubly bound oxygen containing functional groups, e.g. carboxyl groups
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/52—Esters of acyclic unsaturated carboxylic acids having the esterified carboxyl group bound to an acyclic carbon atom
- C07C69/533—Monocarboxylic acid esters having only one carbon-to-carbon double bond
- C07C69/54—Acrylic acid esters; Methacrylic acid esters
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/76—Esters of carboxylic acids having a carboxyl group bound to a carbon atom of a six-membered aromatic ring
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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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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2603/00—Systems containing at least three condensed rings
- C07C2603/56—Ring systems containing bridged rings
- C07C2603/58—Ring systems containing bridged rings containing three rings
- C07C2603/60—Ring systems containing bridged rings containing three rings containing at least one ring with less than six members
- C07C2603/66—Ring systems containing bridged rings containing three rings containing at least one ring with less than six members containing five-membered rings
Abstract
The invention discloses an oligomer suitable for photocuring inkjet ink and a preparation method thereof, and belongs to the technical field of photocuring resin materials. An oligomer suitable for photocuring inkjet ink is mainly prepared from the following raw materials: the synthetic material comprises triphenol methane triglycidyl ether, acrylic acid, 1, 8-naphthalic anhydride, dicyclopentadiene and synthetic auxiliary materials, wherein the synthetic auxiliary materials specifically comprise the following raw materials: hydroquinone, triphenyl phosphine, trifluoromethanesulfonic acid, p-hydroxyanisole and ACMO monomers; the invention can effectively solve the problems of unstable ink printing caused by insufficient cohesion of low molecular weight UV resin in formula application of UV ink and plug and unsmooth printing caused by poor compatibility and fluidity of high molecular weight UV resin.
Description
Technical Field
The invention relates to the technical field of light-cured resin materials, in particular to an oligomer suitable for light-cured ink-jet ink.
Background
UV ink-jet printing is a new technology developed at the end of the 20 th century, which combines the advantages of ink-jet printing technology and ultraviolet curing technology, and has the advantages of both the convenience of use and operation of ink-jet printing technology and the advantages of light curing technology in terms of efficiency and physical properties. As one of the fastest growing technologies in the field of UV technology, UV inkjet printing has achieved significant success in recent years with the value of production increasing from $ 39 billion in 2008 to $ 67 billion in 2012, and expected to increase to $ 159 billion in 2018.
The most applied field at present is large-format printing, and particularly outdoor advertisements and road flags are very suitable for using a UV platform type ink jet printing technology. In addition, UV inkjet technology is rapidly spreading in the fields of label packaging printing and decoration industry printing. Currently, many domestic inkjet ink production enterprises have mastered a large amount of data and experience on the aspects of formula matching, performance adjustment and the like in research and product development work in the field of UV inkjet ink.
However, because raw material manufacturers lack research and development of UV resins applied to UV inkjet inks, in the face of requirements of low viscosity (4-35cpa. S/25 ℃) of UV inks, printing fluency, no blockage of nozzles, ink dot stability and the like, developers usually can only select some UV resins with low molecular weight as main performance resins, which leads to that the printing stability is easily influenced due to the change of external printing conditions because the cohesive force of an ink system is insufficient; such as: the ink is easy to generate ink flying, broken lines, thick ink dots and the like when the ink is good, and the problem that the ink developers are most worried at present is that the ink is easy to block and print unsmooth due to the influence of the compatibility, the fluidity and the like of a system when the high-molecular-weight high-viscosity resin is added.
Disclosure of Invention
The invention aims to solve the problems of unstable ink printing caused by insufficient cohesive force of low-molecular-weight UV resin and poor plug and printing caused by poor compatibility and fluidity of high-molecular-weight UV resin in the formula application of UV ink in the prior art, and provides an oligomer suitable for photocuring inkjet ink.
In order to achieve the purpose, the invention adopts the following technical scheme:
an oligomer suitable for photo-curing ink-jet ink is mainly prepared from the following raw materials: the photo-curing ink-jet ink comprises trisphenol methane triglycidyl ether, acrylic acid, 1, 8-naphthalic anhydride, dicyclopentadiene and a synthetic auxiliary material, wherein each component of an oligomer of the photo-curing ink-jet ink consists of the following components in parts by mass:
20% -30% of triphenol methane triglycidyl ether;
4% -13% of acrylic acid;
10% -25% of 1, 8-naphthalic anhydride;
5 to 15 percent of dicyclopentadiene.
The synthesis auxiliary raw materials specifically comprise the following materials: hydroquinone, triphenyl phosphine, trifluoromethanesulfonic acid, p-hydroxyanisole and ACMO monomers.
The synthetic auxiliary raw materials comprise the following components in parts by mass:
0.01 to 0.05 percent of hydroquinone;
0.1 to 0.2 percent of triphenyl phosphine;
0.05 to 0.1 percent of trifluoromethanesulfonic acid;
0.05 to 0.1 percent of p-hydroxyanisole;
14% -25% of ACMO monomer.
A preparation method of photocuring inkjet ink oligomer comprises the following steps:
s1: firstly, adding a proper amount of triphenol methane triglycidyl ether, hydroquinone and a catalyst triphenylphosphine into a two-neck flask, then installing a stirrer and a heating device, stirring and heating to 85 ℃, slowly pouring acrylic acid while stirring after the resin is liquefied, heating to 105 ℃, keeping the temperature constant, introducing protective gas for protection, and reacting until the acid value is less than 3mgKOH;
s2: after the first step of reaction is finished, cooling to 80 ℃, pouring 1, 8-naphthalic anhydride while stirring, heating to 95 ℃, and reacting at constant temperature for 2 hours;
s3: and after the second step is finished, cooling to 60 ℃, adding dicyclopentadiene, trifluoromethanesulfonic acid and p-hydroxyanisole while stirring, heating to 80 ℃, reacting at constant temperature until the acid value is less than 2mgKOH, cooling to 60 ℃, adding an ACMO monomer, uniformly mixing, filtering by using a stainless steel filter screen, and discharging.
The heating device is a water bath heating device.
The protective gas is specifically nitrogen.
The stainless steel filter screen is 800 meshes.
Compared with the prior art, the invention provides an oligomer suitable for photocuring inkjet ink, which has the following beneficial effects:
1. according to the oligomer suitable for the photocuring inkjet ink, the photocuring resin is trifunctional, huge triphenylmethane is used as a main framework, a side chain comprises naphthyl and is terminated by dicyclopentadiene, so that the sufficient photocuring speed is ensured, and meanwhile, the oligomer has high hardness and extremely low curing shrinkage, and provides a great space for adjusting the performance of the photocuring inkjet ink; meanwhile, the ink has good cohesive force, and the stability of ink drops of an ink system is ensured.
2. The low polymer suitable for the photo-curing ink-jet ink has a huge side chain ring structure, is not easy to cause molecular chain winding, has excellent fluidity, compatibility and dilutability, and ensures the printing smoothness of the photo-curing ink.
3. The bulky aromatic ring of the resin of the oligomer suitable for the photocuring ink-jet ink has extremely high refractive index, so that the ink has high color-spreading power and glossiness, and meets the mainstream requirements of the application market.
The parts which are not related in the device are the same as or can be realized by adopting the prior art, and the invention solves the problems of unstable ink printing caused by insufficient cohesion of low molecular weight UV resin and unstable printing caused by poor compatibility and fluidity of high molecular weight UV resin in formula application of UV ink.
Drawings
FIG. 1 is a molecular structure of an oligomer suitable for use in a photo-curable inkjet ink according to the present invention;
FIG. 2 is a molecular structure of an oligomer suitable for use in a photo-curable inkjet ink, shown as R1 in FIG. 1;
FIG. 3 shows the molecular structure of R2 in FIG. 1 of an oligomer suitable for photo-curable inkjet ink according to the present invention;
FIGS. 4-6 are partial reaction diagrams of an oligomer suitable for use in a photocurable inkjet ink according to the present invention.
Detailed Description
The technical solutions in the embodiments of the present invention will be clearly and completely described below with reference to the drawings in the embodiments of the present invention, and it is obvious that the described embodiments are only a part of the embodiments of the present invention, and not all of the embodiments.
In the description of the present invention, it is to be understood that the terms "upper", "lower", "front", "rear", "left", "right", "top", "bottom", "inner", "outer", and the like, are used in the orientations and positional relationships indicated in the drawings, which are based on the orientations and positional relationships indicated in the drawings, and are used for convenience of description and simplicity of description, but do not indicate or imply that the devices or elements referred to must have a particular orientation, be constructed and operated in a particular orientation, and thus, are not to be construed as limiting the present invention.
Example 1:
referring to fig. 1-3, an oligomer suitable for photo-curable inkjet ink is prepared from the following raw materials: triphenol methane triglycidyl ether, acrylic acid, 1, 8-naphthalic anhydride, dicyclopentadiene and synthetic auxiliary materials.
The synthetic auxiliary raw materials specifically comprise the following materials: hydroquinone, triphenyl phosphine, trifluoromethanesulfonic acid, p-hydroxyanisole and ACMO monomers.
A preparation method of an oligomer suitable for photo-curing ink-jet ink comprises the following steps:
s1: firstly, 460g of triphenol methane triglycidyl ether, 0.6g of hydroquinone and 3g of catalyst triphenylphosphine are added into a two-neck flask, then a stirrer and a heating device are installed, the mixture is stirred and heated to 85 ℃, after the resin is liquefied, 216g of acrylic acid is slowly poured into the flask while stirring, the flask is heated to 105 ℃, the temperature is kept constant, protective gas is introduced for protection, and the reaction is carried out until the acid value is less than 3mgKOH;
s2: after the first step of reaction is finished, cooling to 80 ℃, pouring 396g of 1, 8-naphthalic anhydride while stirring, heating to 95 ℃, and reacting at constant temperature for 2 hours;
s3: and after the second step is finished, cooling to 60 ℃, adding 264g of dicyclopentadiene, 1g of trifluoromethanesulfonic acid and 1g of p-hydroxyanisole while stirring, heating to 80 ℃, reacting at a constant temperature until the acid value is less than 2mgKOH, cooling to 60 ℃, adding 445g of ACMO monomer, uniformly mixing, filtering by using a stainless steel filter screen, and discharging.
The heating device specifically adopts a water bath heating device.
The protective gas is nitrogen.
The stainless steel filter screen specifically adopts the stainless steel filter screen that mesh number is 800.
Example 2:
an oligomer suitable for photocuring inkjet ink is prepared from the following raw materials: the triphenolylmethane triglycidyl ether, the acrylic acid, the 1, 8-naphthalic anhydride, the dicyclopentadiene and the synthesis auxiliary raw materials specifically comprise the following materials: hydroquinone, triphenyl phosphine, trifluoromethanesulfonic acid, p-hydroxyanisole and ACMO monomers.
The synthetic auxiliary raw materials specifically comprise the following materials: hydroquinone, triphenyl phosphine, trifluoromethanesulfonic acid, p-hydroxyanisole and ACMO monomers.
A preparation method of an oligomer suitable for photocuring inkjet ink is prepared by the following steps:
s1: firstly, adding 460g of triphenol methane triglycidyl ether, 0.6g of hydroquinone and 3g of catalyst triphenylphosphine into a two-neck flask, then installing a stirrer and a heating device, stirring and heating to 85 ℃, slowly pouring 72g of acrylic acid while stirring after the resin is liquefied, heating to 105 ℃, keeping the temperature, introducing protective gas for protection, and reacting until the acid value is less than 3mgKOH;
s2: after the first-step reaction is finished, cooling to 80 ℃, pouring 198g1, 8-naphthalic anhydride while stirring, heating to 95 ℃ and reacting for 2 hours at constant temperature;
s3: and after the second step is finished, cooling to 60 ℃, adding 132g of dicyclopentadiene, 1g of trifluoromethanesulfonic acid and 1g of p-hydroxyanisole while stirring, heating to 80 ℃, reacting at constant temperature until the acid value is less than 2mgKOH, cooling to 60 ℃, adding 445g of ACMO monomer, mixing uniformly, filtering by using a stainless steel filter screen, and discharging.
The heating device is a water bath heating device.
The protective gas is specifically nitrogen.
The stainless steel filter screen is 800 meshes.
The molecular structures of the oligomers suitable for photo-curable inkjet inks prepared in the embodiments 1 and 2 are specifically shown in fig. 1, wherein the molecular structure of R1 is specifically shown in fig. 2, the molecular structure of R2 is specifically shown in fig. 3, the synthesis reaction diagrams thereof are shown in fig. 4-6, and the structural formula of the oligomers suitable for photo-curable inkjet inks prepared in the embodiments 6 is shown in fig. 6;
weighing the components of the examples 1-2 and the comparative examples according to the corresponding formula in the following table, mixing the prepared light-cured resin, the light-cured monomer, the photoinitiator and the color paste, and stirring the mixture until the mixture is fully and uniformly mixed; adding surface auxiliary agent, stirring uniformly, filtering with filter membrane with pore diameter of 1 μm under indoor UV-shielding condition, and finishing ink preparation.
In the table:
resin A: the light-cured resin prepared by the invention;
BASF LR 8996 (a low-viscosity resin commonly used for ink);
c, resin: japanese Synthesis of UV-3000B (typical high molecular weight UV resin);
HDDA the most commonly used difunctional UV monomers;
ACMO: the most commonly used monofunctional monomers;
THFA: monofunctional monomers most commonly used for viscosity reduction;
TPO is an acylphosphorus oxide photoinitiator;
ITX is a photoinitiator of thioxanthone;
BYK 333 Beck leveling agent.
And (3) carrying out performance detection on the photocuring inkjet ink prepared according to the proportion in the table:
firstly, the viscosity of the ink at normal temperature (25 ℃) is detected.
The viscosity of the ink at normal temperature (25 ℃ C.) was measured with a DV2T viscometer from BROOK FIELD, USA.
(II) ink jet printing fluency:
1) Inks of each example and comparative example were jet-printed on glass by an ink jet printer, and ink jet fluency was evaluated according to the following criteria:
a: after continuously spraying and printing color blocks of 20 square meters, testing meshes without line breakage;
b: after continuously spraying and printing the color block of 20 square meters, testing meshes, wherein 1 to 2 meshes have a line breakage phenomenon;
c: after the color block is continuously sprayed and printed by 20 square meters, the test meshes have more than 3 meshes and the phenomenon of line breakage occurs.
(III) ink flying property of jet printing:
the inks of the examples and comparative examples were jet-printed on glass with 10cm × 10cm color blocks by a UV inkjet printer, and the number of satellite dots at the edges of the pattern was observed with a magnifier. The printing ink flying was evaluated as follows:
a: no satellite points are arranged at the edge of the pattern;
b: pattern edge is less than or equal to 10 satellite points;
c: pattern edge >10 satellite spots.
(IV) dot shape and size performance:
the inks of the examples and the comparative examples are subjected to ink-jet printing on glass by a UV ink-jet printer to form a dot matrix diagram, observed by a magnifying glass and judged according to the following standards:
a: the ink dots are round and solid without diffusion;
b, ink dots are round but not practical and slightly diffuse;
c: the ink dots are not round in shape and spread obviously.
(V) force application performance:
and (3) spraying and printing a standard test pattern on the blank acrylic material by using the ink of each embodiment and the comparative example through a UV ink-jet printer, and judging the adhesion force by a check method:
a: level 0;
b: grade 5;
c: large area of falling off.
(VI) hardness:
the glass on which the coating film had been cured was tested by the pencil hardness test, and the result was represented by the corresponding H.
The results are shown in the following table:
as can be seen from the test results in the table, the UV resin applied to photo-curable ink prepared by the present invention fully satisfies the requirements in the application, and solves the problems of unstable ink printing caused by insufficient cohesion of low molecular weight UV resin and poor printing caused by poor compatibility and flowability of high molecular weight UV resin in formulation application of UV ink.
Claims (4)
1. The oligomer suitable for the photocuring ink-jet ink is characterized by being prepared from the following raw materials: the photo-curing ink-jet ink comprises trisphenol methane triglycidyl ether, acrylic acid, 1, 8-naphthalic anhydride, dicyclopentadiene and a synthetic auxiliary material, wherein each component of an oligomer of the photo-curing ink-jet ink consists of the following components in percentage by mass:
20% -30% of triphenol methane triglycidyl ether;
4% -13% of acrylic acid;
10% -25% of 1, 8-naphthalic anhydride;
5% -15% of dicyclopentadiene;
the synthetic auxiliary material specifically comprises the following materials: the synthetic auxiliary material comprises hydroquinone, triphenyl phosphine, trifluoromethanesulfonic acid, p-hydroxyanisole and ACMO monomers, wherein the synthetic auxiliary material comprises the following components in parts by mass:
0.01 to 0.05 percent of hydroquinone;
0.1 to 0.2 percent of triphenyl phosphine;
0.05 to 0.1 percent of trifluoromethanesulfonic acid;
0.05 to 0.1 percent of p-hydroxyanisole;
14% -25% of ACMO monomer;
the sum of the mass percentages of the components is 100%;
the preparation method of the oligomer suitable for the photocuring inkjet ink is prepared by the following steps:
s1: firstly, adding a proper amount of triphenol methane triglycidyl ether, hydroquinone and a catalyst triphenylphosphine into a two-neck flask, then installing a stirrer and a heating device, stirring and heating to 85 ℃, slowly pouring acrylic acid while stirring after the resin is liquefied, heating to 105 ℃, keeping the temperature constant, introducing protective gas for protection, and reacting until the acid value is less than 3mgKOH;
s2: after the first step of reaction is finished, cooling to 80 ℃, pouring 1, 8-naphthalic anhydride while stirring, heating to 95 ℃, and reacting at constant temperature for 2 hours;
s3: and after the second step is finished, cooling to 60 ℃, adding dicyclopentadiene, trifluoromethanesulfonic acid and p-hydroxyanisole while stirring, heating to 80 ℃, reacting at constant temperature until the acid value is less than 2mgKOH, cooling to 60 ℃, adding an ACMO monomer, uniformly mixing, filtering by using a stainless steel filter screen, and discharging.
2. The oligomer suitable for use in a photocurable inkjet ink according to claim 1, wherein the heating device is a water bath heating device.
3. The oligomer suitable for photo-curable inkjet ink according to claim 1, wherein the protective gas is nitrogen.
4. The oligomer suitable for use in a photocurable inkjet ink according to claim 1, wherein the stainless steel screen is a stainless steel screen with a mesh number of 800.
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| CN114316149A (en) * | 2021-12-22 | 2022-04-12 | 深圳锐沣科技有限公司 | Preparation method of thermoplastic 3D printing light-cured resin |
| CN114213252A (en) * | 2021-12-30 | 2022-03-22 | 广东希必达新材料科技有限公司 | Method for continuously preparing dicyclopentenyl acrylate |
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| JPH10237288A (en) * | 1997-02-24 | 1998-09-08 | Toyo Ink Mfg Co Ltd | Composition curable with active energy ray |
| CN1842742A (en) * | 2003-08-28 | 2006-10-04 | 日立化成工业株式会社 | Photosensitive resin composition, photosensitive element using same, method for forming resist pattern, method for producing printed wiring board, and method for removing photocured product |
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