WO2012157690A1 - Photopolymerizable inkjet ink, ink cartridge, and printer - Google Patents
Photopolymerizable inkjet ink, ink cartridge, and printer Download PDFInfo
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- WO2012157690A1 WO2012157690A1 PCT/JP2012/062573 JP2012062573W WO2012157690A1 WO 2012157690 A1 WO2012157690 A1 WO 2012157690A1 JP 2012062573 W JP2012062573 W JP 2012062573W WO 2012157690 A1 WO2012157690 A1 WO 2012157690A1
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- Prior art keywords
- ink
- photopolymerizable
- inkjet ink
- inks
- photopolymerizable inkjet
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Classifications
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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
-
- 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
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B41—PRINTING; LINING MACHINES; TYPEWRITERS; STAMPS
- B41J—TYPEWRITERS; SELECTIVE PRINTING MECHANISMS, i.e. MECHANISMS PRINTING OTHERWISE THAN FROM A FORME; CORRECTION OF TYPOGRAPHICAL ERRORS
- B41J11/00—Devices or arrangements of selective printing mechanisms, e.g. ink-jet printers or thermal printers, for supporting or handling copy material in sheet or web form
- B41J11/0015—Devices or arrangements of selective printing mechanisms, e.g. ink-jet printers or thermal printers, for supporting or handling copy material in sheet or web form for treating before, during or after printing or for uniform coating or laminating the copy material before or after printing
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B41—PRINTING; LINING MACHINES; TYPEWRITERS; STAMPS
- B41J—TYPEWRITERS; SELECTIVE PRINTING MECHANISMS, i.e. MECHANISMS PRINTING OTHERWISE THAN FROM A FORME; CORRECTION OF TYPOGRAPHICAL ERRORS
- B41J2/00—Typewriters or selective printing mechanisms characterised by the printing or marking process for which they are designed
- B41J2/005—Typewriters or selective printing mechanisms characterised by the printing or marking process for which they are designed characterised by bringing liquid or particles selectively into contact with a printing material
- B41J2/01—Ink jet
- B41J2/17—Ink jet characterised by ink handling
- B41J2/175—Ink supply systems ; Circuit parts therefor
- B41J2/17503—Ink cartridges
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B41—PRINTING; LINING MACHINES; TYPEWRITERS; STAMPS
- B41J—TYPEWRITERS; SELECTIVE PRINTING MECHANISMS, i.e. MECHANISMS PRINTING OTHERWISE THAN FROM A FORME; CORRECTION OF TYPOGRAPHICAL ERRORS
- B41J2/00—Typewriters or selective printing mechanisms characterised by the printing or marking process for which they are designed
- B41J2/005—Typewriters or selective printing mechanisms characterised by the printing or marking process for which they are designed characterised by bringing liquid or particles selectively into contact with a printing material
- B41J2/01—Ink jet
- B41J2/21—Ink jet for multi-colour printing
- B41J2/2107—Ink jet for multi-colour printing characterised by the ink properties
-
- 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
Definitions
- the present invention relates to a photopolymerizable inkjet ink, an ink cartridge which houses the ink, and a printer to which the ink cartridge is mounted.
- Photopolymerizable monomers used in photopolymerizable inkjet inks are, for example, (meth)acrylic acid ester compounds, acryl amide compounds, cation polymerizable oxetane compounds and epoxy compounds.
- (meth)acrylic acid ester compounds and acryl amide compounds are available in large amounts, inexpensive, easily procurable, and capable of being used in combination with a radical polymerizable photopolymerization initiator that is inexpensive and commonly used among polymerization initiators.
- the present inventor previously found that there were some (meth)acrylic acid ester compounds and acryl amide compounds usable as photopolymerizable monomers and having a Stimulation Index (SI value) of less than 3 where the Stimulation Index indicates the extent of sensitization as measured by a skin sensitization test based on the LLNA (Local Lymph Node Assay).
- SI value Stimulation Index
- those compounds are formulated so as to attain practically usable curing property, the curing property of the resultant inks becomes inferior to those of commonly used photopolymerizable inkjet inks.
- a photoradical polymerization initiator has to be incorporated in a larger amount than usual. Such a large amount of the photoradical polymerization initiator incorporated was found to prevent the resultant inks from showing sufficient storage stability in high-temperature environments such as summer.
- the present inventor previously found a photopolymerizable inkjet ink which is negative for skin sensitization, improves the coated film in curing property, enables possible curing failures in the coated film to be visually confirmed, and facilitates quality control in the production process.
- the photopolymerizable inkjet ink contains: one or more types of photopolymerizable monomers each having a SI value of less than 3) ' a self-cleaving photopolymerization initiator; a
- photopolymerizable inkjet ink can be improved by the addition of a material called a polymerization inhibitor.
- a material called a polymerization inhibitor examples include phenol compounds and quinone compounds such as methoquinone and benzoquinone, and aromatic secondary amine compounds such as diphenyl amine and phenothiazine (see, for example, PTLs 1 and 2).
- JP-A Japanese Patent Application Laid-Open
- An object of the present invention is to provide a
- photopolymerizable inkjet ink that is safe in skin sensitization and good in storage stability at high temperatures.
- a photopolymerizable inkjet ink of the present invention contains : a photopolymerizable monomer having a Stimulation Index (SI value) of less than 3, where the Stimulation Index indicates the extent of sensitization as measured by a skin sensitization test (LLNA)," and a phenol aromatic compound having two hydroxyl groups in the molecule thereof.
- SI value Stimulation Index
- LLNA skin sensitization test
- the present invention can provide a photopolymerizable inkjet ink that is safe in skin sensitization and good in storage stability at high temperatures.
- Fig. 1 schematically illustrates one exemplary ink bag of an ink cartridge.
- Fig. 2 schematically illustrates an ink cartridge which houses an ink bag.
- Fig. 3 schematically illustrates one exemplary printer of the present invention.
- a photopolymerizable inkjet ink of the present invention contains ⁇ a photopolymerizable monomer having a Stimulation Index (SI value) of less than 3, where the Stimulation Index indicates the extent of sensitization as measured by a skin sensitization test (LLNA); and a phenol aromatic compound having two hydroxyl groups in the molecule thereof.
- the photopolymerizable inkjet ink preferably contains at least one selected from the group consisting of a photopolymerization initiator and an amine compound serving as a polymerization accelerator! and, if necessary, further contains other ingredients.
- the present inventor has found that by incorporating the phenol aromatic compound having two hydroxyl groups in the molecule thereof into a photopolymerizable inkjet ink (hereinafter may be referred to as "ink") containing a safe photopolymerizable monomer having a SI value of less than 3 where the SI value indicates the extent of sensitivity as measured by the skin sensitization test (LLNA), the resultant ink can show good storage stability even at high temperatures.
- a photopolymerizable inkjet ink hereinafter may be referred to as "ink”
- LLNA skin sensitization test
- the "LLNA” is the skin sensitization test defined as OECD test guideline 429.
- the compound having a Stimulation Index (SI value) of less than 3, where the Stimulation Index indicates the extent of skin sensitization is judged as being negative for skin sensitization.
- the compounds evaluated as "negative for skin sensitization” or “no skin sensitization” in their MSDS (Material Safety Data Sheet) and/or literatures for example, van der Walle HB.
- the lower SI value means lower skin sensitization.
- a monomer or an oligomer having lower SI value is preferably used.
- the SI value of the monomer or the oligomer used is preferably 2 or lower, more preferably 1.6 or lower.
- the phenol aromatic compound having two hydroxyl groups in the molecule thereof is not particularly limited and may be appropriately selected depending on the intended purpose. Examples thereof include hydroquinone, methylhydroquinone, tert-butylhydroquinone,
- hydroquinone hydroquinone
- methylhydroquinone hydroquinone
- tert-butylhydroquinone and 2,5-di-tert-butylhydroquinone are preferred since they are particularly excellent in storage stability at high
- a proper amount of the phenol aromatic compound having two hydroxyl groups in the molecule thereof varies with properties required for inks depending on their applications.
- the amount of the phenol aromatic compound having two hydroxyl groups in the molecule thereof is too small, satisfactory effects cannot be obtained in some cases, whereas when it is too large, the curing property of the resultant ink may be degraded.
- the amount of the phenol aromatic compound having two hydroxyl groups in the molecule thereof contained in the ink is preferably 0.001 parts by mass to 1 part by mass per 100 parts by mass of the photopolymerizable monomer.
- the amount of the phenol aromatic compound having two hydroxyl groups in the molecule thereof is necessarily limited to this range.
- the amount of the phenol aromatic compound having two hydroxyl groups in the molecule thereof is preferably larger for improving storage stability.
- a larger amount of the phenol aromatic compound having two hydroxyl groups in the molecule thereof is not preferred for obtaining sufficient curing property. Therefore, the amount of the phenol aromatic compound having two hydroxyl groups in the molecule thereof is not preferred for obtaining sufficient curing property. Therefore, the amount of the phenol aromatic compound having two hydroxyl groups in the molecule thereof is not preferred for obtaining sufficient curing property. Therefore, the amount of the phenol aromatic
- the photopolymerizable monomer involving no problems in skin sensitization, inexpensive and easily procurable is not particularly limited and may be appropriately selected depending on the intended purpose.
- Examples thereof include polyethylene glycol dimethacrylates represented by the following General Formula (l) where n is nearly equal to 2, 9 or 14, ⁇ -butyrolactone methacrylate, trimethylolpropane trimethacrylate, tricyclodecanedimethanol dimethacrylate, caprolactone-modified
- polyethylene glycol dimethacrylates represented by the following General Formula (l) where n is nearly equal to 2, 9 or 14, ⁇ -butyrolactone methacrylate, trimethylolpropane
- trimethacrylate tricyclodecanedimethanol dimethacrylate
- dimethacrylate steary acrylate, 1,4-butanediol dimethacrylate,
- C H 2 C C O - (C H 2 - C H 2 0) n - C C - C H 2
- n is nearly equal to 2, 9 or 14.
- polyethylene glycol dimethacrylates each represented by General Formula (l), the average of the numbers indicated by "n,” which are calculated through analysis such as measurement of their molecular weights, preferably falls within the range of 9 to 14.
- Examples thereof include ethylene glycol di(meth)acrylate, neopentylglycol hydroxypivalate di(meth)acrylate, ybutyrolactone acrylate, isobornyl acrylate, formalized trimethylolpropane
- hydroxypenta(meth)acrylate caprolactone-modified dipentaerythritol hydroxypenta(meth)acrylate, ditrimethylolpropane tetra(meth)acrylate, pentaerythritol tetra(meth)acrylate, trimethylolpropane triacrylate, ethylene oxide-modified trimethylolpropane triacrylate, propylene oxide-modified trimethylolpropane triacrylate, caprolactone-modified trimethylolpropane tri(meth)acrylate, pentaerythritol tri(meth)acrylate, tris(2-hydroxyethyl)isocyanurate tri(meth) aery late, neopentyl glycol diacrylate, ethoxylated neopentyl glycol di(meth)acrylate, propoxylated neopentyl glycol di(meth)acrylate, propoxylated neopent
- N-vinylformamide polyurethane di(meth)acrylate, polyurethane tri(meth)acrylate, polyurethane tetra(meth)acrylate, polyurethane penta(meth)acrylate, polyurethane poly(meth)acrylate,
- the amount of these photopolymerizable monomers contained in the ink is not particularly limited and may be appropriately selected depending on the intended purpose. It is preferably 50% by mass to 100% by mass, more preferably 80% by mass to 100% by mass. Although incorporating a colorant and other additives into the ink can provide the ink with various functions, the polymerization reaction of the monomers may be inhibited depending on the amount thereof. Thus, it is not preferred to incorporate an unnecessarily excessive amount of a colorant and other additives.
- the ink may further contain a photopolymerization initiator.
- the photopolymerization initiator is preferably a self-cleaving
- the photopolymerization initiator used is preferably negative for skin sensitization similar to the
- the self-cleaving photopolymerization initiator is not particularly limited and may be appropriately selected depending on the intended purpose. Examples thereof include
- the hydrogen-abstracting photopolymerization initiator is not particularly limited and may be appropriately selected depending on the intended purpose. Examples thereof include " - thioxanthone compounds such as 2,4-diethylthioxanthone, 2-chlorothioxanthone,
- benzophenone compounds such as benzophenone, methylbenzophenone, methyl-2-benzoylbenzoate, 4-benzoyl-4'-methyldiphenyl sulfide and phenylbenzophenone. These may be used alone or in combination.
- LED light sources As light sources for curing photopolymerizable inks since the LED light sources exhibit higher energy efficiency than conventional mercury lamps and metal halide lamps and realize energy saving.
- the wavelength of the LED light sources free from practical problems is 365 nm or greater.
- benzophenone compounds it is difficult to expect benzophenone compounds to satisfactorily serve as an initiator, judging from their specific absorption spectra. For this reason, thioxanthone compounds are more suitable. Among them, chlorine-free
- the polymerization accelerator is not particularly limited, so long as it is an amine compound, and may be appropriately selected depending on the intended purpose.
- examples thereof include benzoic acid ester compounds containing an ⁇ , ⁇ -dimethylamino group, such as ethyl p-dimethylaminobenzoate, 2-ethylhexyl p-dimethylaminobenzoate, methyl p-dimethylaminobenzoate, 2-dimethylaminoethyl benzoate and butoxyethyl p-dimethylaminobenzoate. These may be used alone or in combination.
- ethyl p-dimethylaminobenzoate is preferred since it is inexpensive, easily procurable and has the highest viscosity-reducing effect.
- the amine compound serves as a source for supplying hydrogen to the hydro gen -abstracting photopolymerization initiator.
- a benzoic acid ester compound having a ⁇ , ⁇ -dimethylamino group can more efficiently accelerate the curing reaction.
- the photopolymerization reaction hardly proceeds whereby sufficient curing cannot be attained in some cases.
- the polymerization reaction proceeds, but the polymerization degree does not increase so that the cured product may be brittle. ' or the photopolymerization initiator may excessively increase the viscosity of the ink to cause failures in inkjet ejection.
- the total amount of the photopolymerization initiators and the polymerization accelerator is preferably 1 part by mass to 50 parts by mass, particularly preferably 10 parts by mass to 35 parts by mass, per 100 parts by mass of the photopolymerizable monomer.
- the other ingredients are not particularly limited and may be appropriately selected depending on the intended purpose.
- examples thereof include colorants, ' higher-fatty-acid esters having, for example, a polyether, an amino group, a carboxyl group, and/or a hydroxyl group in the side chain or the end thereof; polydimethylsiloxane compounds having, for example, a polyether, an amino group, a carboxyl group, and/or a hydroxyl group in the side chain or the end thereof; surfactants such as fluoroalkyl compounds having, for example, a polyether, an amino group, a carboxyl group, and/or a hydroxyl group; and polar group-containing polymeric pigment dispersing agents. These may be used alone or in combination. «Colorant»
- the colorant of the ink is not particularly limited and may be appropriately selected from known inorganic pigments and organic pigments considering, for example, physical properties of the ink.
- black pigments those such as carbon black produced by the furnace method or the channel method can be used. These may be used alone or in combination.
- Pig. Yellow series pigments can be used: Pig. Yellow 1, Pig. Yellow 2, Pig. Yellow 3, Pig. Yellow 12, Pig. Yellow 13, Pig. Yellow 14, Pig. Yellow 16, Pig. Yellow 17, Pig. Yellow 73, Pig. Yellow 74, Pig. Yellow 75, Pig. Yellow 83, Pig. Yellow 93, Pig. Yellow 95, Pig. Yellow 97, Pig. Yellow 98, Pig. Yellow 114, Pig. Yellow 120, Pig. Yellow 128, Pig. Yellow 129, Pig. Yellow 138, Pig. Yellow 150, Pig. Yellow 151, Pig. Yellow 154, Pig. Yellow 155, and Pig. Yellow 180. These may be used alone or in combination.
- magenta pigments for example, the following Pig. Red series pigments can be used: Pig. Red 5, Pig. Red 7, Pig. Red 12, Pig. Red 48 (Ca), Pig. Red 48 (Mn), Pig. Red 57 (Ca), Pig. Red 57:1, Pig. Red 112, Pig. Red 122, Pig. Red 123, Pig. Red 168, Pig. Red 184, Pig. Red 202, and Pig. Violet 19. These may be used alone or in combination.
- Pig. Blue series pigments can be used: Pig. Blue 1, Pig. Blue 2, Pig. Blue 3, Pig. Blue 15, Pig. Blue 15:3, Pig. Blue 15:4, Pig. Blue 16, Pig. Blue 22, Pig. Blue 60, Vat Blue 4, and Vat Blue 60. These may be used alone or in combination.
- white pigments for example, sulfuric acid salts of alkaline earth metals such as barium sulfate, carbonic acid salts of alkaline earth metals such as calcium carbonate, silica such as fine silicic acid powder and synthetic silicic acid salts, calcium silicate, alumina, alumina hydrate, titanium oxide, zinc oxide, talc and clay. These may be used alone or in combination.
- An inkjet cartridge of the present invention includes at least the above -described photopolymerizable inkjet ink of the present invention.
- the ink of the present invention can suitably be used as an ink cartridge where the ink is housed in a container.
- users do not have to directly touch the ink during works such as exchange of the ink, and thus they are not concerned with staining of their fingers, hands or clothes.
- it is possible to prevent interfusion of foreign matter such as dust into the ink.
- the container is not particularly limited, and the shape, structure, size and material thereof may be appropriately selected depending on the intended purpose.
- the container is preferably selected from those having an ink bag formed of an aluminum laminate film, or a resin film.
- Fig. 1 schematically illustrates an example of an ink bag 241 of an ink cartridge.
- Fig. 2 schematically illustrates an ink cartridge 200
- the ink bag 241 is filled with the ink by injecting the ink from an ink inlet 242. After removal of air present inside the ink bag 241, the ink inlet 242 is sealed by fusion bonding. At the time of use, a needle attached to the main body of the device is inserted into an ink outlet 243 formed of a rubber member to supply the ink to the device therethrough.
- the ink bag 241 is formed of a wrapping member such as an air non-permeable aluminum laminate film.
- the ink bag 241 is typically housed in a plastic cartridge case 244, which is then detachably mounted in use to various inkjet recording devices as the ink cartridge 200.
- the ink cartridge of the present invention is preferably detachably mounted to inkjet recording devices (e.g., a printer).
- the ink cartridge can simplify the refill and exchange of the ink to improve workability. (Printer)
- a printer of the present invention includes at least the
- Fig. 3 schematically illustrates one exemplary printer.
- the printer illustrated in Fig. 3 forms a color image as follows. Specifically, printing units 3 (i.e., printing units 3a, 3b, 3c and 3d having ink cartridges 200a, 200b, 200c and 200d for respective colors (e.g., yellow, magenta, cyan and black)) eject color inks (yellow, magenta, cyan and black) on a base material to be printed 2 (which is conveyed from left to right in Fig. 3) fed from a base material feed roller 1, and light (UV rays) is applied from UV light sources (curing light sources) 4a, 4b, 4c and 4d to the corresponding color inks for curing.
- printing units 3 i.e., printing units 3a, 3b, 3c and 3d having ink cartridges 200a, 200b, 200c and 200d for respective colors (e.g., yellow, magenta, cyan and black)
- eject color inks yellow, magenta, cyan and
- the base material 2 used is, for example, paper, a film, a metal or a composite material thereof.
- the base material 2 illustrated in Fig. 3 is a roll but may be a sheet.
- the base material may be subjected to double-side printing as well as single-side printing.
- the UV light sources 4a, 4b and 4c may be lowered in output power or may be omitted, so that the UV light source 4d is made to apply a sufficient dose of UV rays to a composite printed image formed of a plurality of colors. By doing so, energy saving and cost reduction can also be realized.
- reference numeral 5 denotes a processing unit and reference numeral 6 denotes a wind-up roll for printed products.
- Preparation Examples 1 to 120 were prepared by mixing the following photopolymerizable monomers Al to A23 (i.e., (meth)acrylic acid ester compounds or acrylamide compounds each being negative for skin sensitization or having a SI value of less than 3) with at least one of the following self-cleaving photopolymerization initiators Bl-1 and Bl-2, the following hydrogen-abstracting photopolymerization initiator B2-1 and B2-2, and the following polymerization accelerator B3 in the compositions and the amounts (parts by mass) shown in Tables 1 to 12.
- photopolymerizable monomers Al to A23 i.e., (meth)acrylic acid ester compounds or acrylamide compounds each being negative for skin sensitization or having a SI value of less than 3
- the following self-cleaving photopolymerization initiators Bl-1 and Bl-2, the following hydrogen-abstracting photopolymerization initiator B2-1 and B2-2, and the following polymerization accelerator B3 in the compositions and the amounts
- the units of the amounts of the photopolymerizable monomers, the photopolymerization initiators, and the phenol aromatic compound having two hydroxyl groups in the molecule thereof shown in Tables 1 to 12 are "parts by mass.”
- Inks of Comparative Examples 1 to 240 were produced in the same manner as in each of Examples 1 to 480, except that 0.1 parts by mass of the phenol aromatic compound CI, C2, C3 or C4 having two hydroxyl groups in the molecule thereof was changed to 0.1 parts by mass of each of the following phenol aromatic compounds C5 and C6 having one hydroxyl group in the molecule thereof as shown in Tables 13-1 to 18-2.
- the units of the amounts of the photopolymerizable monomers, the photopolymerization initiators, and the phenol aromatic compound having one hydroxyl group in the molecule thereof shown in Tables 1 to 12 are "parts by mass.”
- NPG Neopentyl glycol dimethacrylate
- A2 Polyethylene glycol dimethacrylate represented by the following General Formula (l) (n is nearly equal to 9) (1.3) ("LIGHT ESTER 9EG,” product of KYOEISHA CHEMICAL CO., LTD.)
- C H 2 C C O - (C H 2 - C H 2 0) n - C C - C H 2
- General Formula (l) A3 Polyethylene glycol dimethacrylate represented by General Formula (l) (n is nearly equal to 14) (1.6) ("LIGHT ESTER 14EG,” product of KYOEISHA CHEMICAL CO., LTD.)
- A6 Tricyclodecanedimethanol dimethacrylate (1.3) ("DCP,” product of Shin-Nakamura Chemical Co., Ltd.)
- A12 Stearyl acrylate (2.7) ("STA,” product of OSAKA ORGANIC
- A23 Polyethylene glycol dimethacrylate represented by General Formula (l) (n is nearly equal to 2) (l.l) ("2G,” product of Shin-Nakamura Chemical Co., Ltd.)
- Bl-2 2-Dimethylamino-2"(4-methylbenzyl)-l-(4-morpholin-4-yl-phenyl)- butan-l-one ("Irgacure379,” product of BASF Co.)
- each of the inks of Examples 1 to 480 and Comparative Examples 1 to 240 was placed in a container, which was then hermetically sealed in the dark and left to stand at 70°C for 1 week.
- the ink was evaluated for "rate of change in viscosity at 60°C" and "inkjetting property.”
- the inks were subjected to the acceleration test at 70°C.
- each of the inks of Examples 1 to 480 and Comparative Examples 1 to 240 was measured for viscosity at 60°C (mPa-S) and the obtained value was used to calculate the rate of change (%) in viscosity at 60°C from the following equation.
- the viscosity at 60°C was measured with a cone -plate -type rotary viscometer (TV-22L, product of TOKI SANGYO CO., LTD.) with the temperature of circulating water being constantly set to 60°C.
- the temperature of 60°C is a temperature set considering the specification of a commercially available inkjet ejection head able to be heated, such as GEN4 (product of Ricoh Printing Systems, Ltd.).
- Rate of change (%) [l - (viscosity after the acceleration test / viscosity before the acceleration test)] ⁇ 100
- An aluminum pouch bag having a shape illustrated in Fig. 1 was charged with each of the inks of Examples 1 to 480 and Comparative Examples 1 to 240 before and after the acceleration test, and hermetically sealed so as to avoid inclusion of air bubbles.
- the hermetically sealed pouch bag containing the ink was housed in a plastic cartridge as illustrated in Fig. 2. This cartridge was mounted to a casing adapted for housing it. In the casing, an ink flow channel was provided from the cartridge to an inkjet head (GEN4, product of Ricoh Printing Systems, Ltd.).
- each of the inks of Examples 1 to 480 and Comparative Examples 1 to 240 before and after the acceleration test was ejected through the ink flow channel to form a solid coated film (i.e., a uniformly and entirely coated film) on a commercially available polyethylene terephthalate film (product name: COSMOSHINE A4300, product of TOYOBO CO., LTD.) so that the solid coated film had a thickness of about 10 ⁇ .
- a solid coated film i.e., a uniformly and entirely coated film
- a commercially available polyethylene terephthalate film product name: COSMOSHINE A4300, product of TOYOBO CO., LTD.
- the inks of Examples 1 to 480 could be ejected without any particular problems both before and after the acceleration test.
- the solid coated films formed of the inks of Example 1 to 480 both before and after the acceleration test were cured without any problems. Specifically, by applying a light dose twice or less times of that required for curing the initial solid coated films formed of the inks of Example 1 to 480 before the acceleration test, the solid coated films formed of the inks of Example 1 to 480 after the acceleration test were cured to be in a non-sticky state which was judged by touching them with a finger.
- hermetically sealed pouch bag containing the mixture was housed in a plastic cartridge as illustrated in Fig. 2.
- This cartridge was mounted to a casing adapted for housing it.
- an ink flow channel was provided from the cartridge to an inkjet head (GEN4, product of Ricoh Printing Systems, Ltd.).
- the mixture was ejected through the ink flow channel to form a solid coated film (i.e., a uniformly and entirely coated film) on a commercially available polyethylene terephthalate film (product name: COSMOSHINE A4300, product of TOYOBO CO., LTD.) so that the solid coated film had a thickness of about 10 ⁇ , whereby an uncured film was formed.
- the thus-formed uncured film was irradiated with light using a UV curing device (LH6, product of Fusion UV Systems Co.), with the light dose being changed stepwise to 1,000 mJ/cm 2 , 500 mJ/cm 2 , 300 mJ/cm 2 , 100 mJ/cm 2 , 50 mJ/cm 2 , 20 mJ/cm 2 , 10 mJ/cm 2 and 5 mJ/cm 2 .
- the state of the coated film was confirmed by touching it with a finger. The coated film that had lost tackiness was judged as being cured.
- the minimum light dose required that the coated film had been cured was used as a curing light dose required that the coated film had lost tackiness.
- the curing light dose required that the coated film had lost tackiness is shown as "curing light dose" in Tables 1 to 12.
- the uncured coated film was irradiated with the curing light dose required that the coated film would lose tackiness to prepare a cured coated film.
- the above -prepared uncured and cured coated films were observed for appearance. The results are shown in Tables 1 to 12.
- Comparative Examples 1 to 240 each containing each of the mixtures of Preparation Examples 1 to 120 together with the phenol aromatic compound having two hydroxyl groups in the molecule thereof (any one of CI to C4) or the phenol aromatic compound having one hydroxyl group in the molecule thereof (C5 or C6), were measured for curing light dose, and the appearance of cured and uncured coated films made of each ink was observed.
- the present inventor previously found a photopolymerizable inkjet ink which is negative for skin sensitization, improves the coated film in curing property, enables possible curing failures in the coated film to be visually confirmed, and facilitates quality control in the production process.
- the photopolymerizable inkjet ink contains: one or more types of photopolymerizable monomers each having a SI value of less than 3; a self-cleaving photopolymerization initiator; a hydrogen-abstracting polymerization initiator; and an amine compound serving as a polymerization accelerator.
- the self-cleaving photopolymerization initiator, the hydrogen-abstracting polymerization initiator, and the amine compound serving as a polymerization accelerator as photopolymerization initiators were mixed with the phenol aromatic compound having two hydroxyl groups in the molecule thereof (any one of CI to C4), the obtained inks were found to exhibit good storage stability similar to the mixtures of Preparation Examples 1 to 40 each containing the self-cleaving
- Example 481 An ink of Example 481 was produced in the same manner as in Example 60, except that the amount of the phenol aromatic compound having two hydroxyl groups in the molecule thereof C3 was changed from 0.1 parts by mass from 0.01 parts by mass per 100 parts by mass of the mixture of Preparation Example 20.
- the thus-produced ink was measured for rate of change in viscosity at 60°C in the same manner as described above.
- the rate of change of the ink was +2.2%, indicating good storage stability.
- Example 482 An ink of Example 482 was produced by adding 0.1 parts by mass of phenol aromatic compound having two hydroxyl groups in the molecule thereof C7 [2,2'-methylenebis(4-methyl-6-tert-butylphenol) (NONFLEX MBP, product of Seiko Chemical Co., Ltd.)] to 100 parts by mass of the mixture of Preparation Example 20.
- the thus-produced ink was measured for rate of change in viscosity at 60°C in the same manner as described above.
- the rate of change of the ink was +3.0%, indicating good storage stability.
- An ink of Example 483 was produced by adding 0.1 parts by mass of phenol aromatic compound having two hydroxyl groups in the molecule thereof C8 [2,2'-methylenebis(4-ethyl-6-tert-but lphenol) (NONFLEX MBP, product of Seiko Chemical Co., Ltd.)] to 100 parts by mass of the mixture of Preparation Example 20.
- the thus-produced ink was measured for rate of change in viscosity at 60°C in the same manner as described above.
- the rate of change of the ink was +3.2%, indicating good storage stability.
- An ink of Example 484 was produced by adding 0.1 parts by mass of phenol aromatic compound having two hydroxyl groups in the molecule thereof C9 [2,2'-methylenebis[6-(l-methylcyclohexyl-p-cresol) (NONFLEX MBP, product of Seiko Chemical Co., Ltd.)] to 100 parts by mass of the mixture of Preparation Example 20.
- the thus-produced ink was measured for rate of change in viscosity at 60°C in the same manner as described above.
- the rate of change of the ink was +2.9%, indicating good storage stability.
- a mixture of Preparation Example 121 was prepared in the same manner as in Preparation Example 20, except that 40 parts by mass of A20 and 10 parts by mass of A24 [diethyleneglycol diacrylate (SR230, product of Sartomer Co.)] were added instead of 50 parts by mass of A20. (Example 485)
- An ink of Example 485 was produced by adding 0.1 parts by mass of the phenol aromatic compound having two hydroxyl groups in the molecule thereof CI to 100 parts by mass of the mixture of Preparation Example 121.
- the thus-produced ink was measured for rate of change in viscosity at 60°C in the same manner as described above.
- the rate of change of the ink was +1.9%, indicating good storage stability.
- a mixture of Pre aration Example 122 was prepared in the same manner as in Preparation Example 20, except that 40 parts by mass of A20 and 10 parts by mass of A25 [trimethylolpropane triacrylate (M-309, product of Toagosei Chemical CO., LTD.)] instead of 50 parts by mass of A20.
- M-309 trimethylolpropane triacrylate
- An ink of Example 486 was produced by adding 0.1 parts by mass of the phenol aromatic compound having two hydroxyl groups in the molecule thereof Cl to 100 parts by mass of the mixture of Preparation Example 122.
- the thus-produced ink was measured for rate of change in viscosity at 60°C in the same manner as described above.
- the rate of change of the ink was +2.1%, indicating good storage stability.
- a photopolymerizable inkjet ink including:
- phenol aromatic compound having two hydroxyl groups in the molecule thereof is at least one selected from the group consisting of hydroquinone, methylhydroquinone, tert-butylhydroquinone and
- ⁇ 5> The photopolymerizable inkjet ink according to ⁇ 3> or ⁇ 4>, wherein the amine compound is a benzoic acid ester compound containing a ⁇ , ⁇ -dimethylamino group.
- ⁇ 6> The photopolymerizable inkjet ink according to any one of ⁇ 1> to ⁇ 5>, wherein the photopolymerizable monomer is at least one selected from the group consisting of polyethylene glycol dimethacrylates represented by the following General Formula (l), ⁇ -butyrolactone methacrylate, trimethylolpropane trimethacrylate,
- the photopolymerizable monomer is at least one selected from the group consisting of polyethylene glycol dimethacrylates represented by the following General Formula (l), ⁇ -butyrolactone methacrylate, trimethylolpropane trimethacrylate,
- C H 2 C C O - (C H 2 - C H 2 0) n - C C - C H 2
- n is nearly equal to 2, 9 or 14.
- An ink cartridge including:
- a container which houses the photopolymerizable inkjet ink.
- a printer including:
- the photopolymerizable inkjet ink according to any one of ⁇ 1> to ⁇ 6>, or the ink cartridge according to ⁇ 7>, or both thereof.
- the present invention can provide : a photopolymerizable inkjet ink safe in skin sensitization and good in storage stability at high temperatures; an ink cartridge housing the ink; and a printer containing the ink cartridge mounted thereto.
- curing failures can easily be determined visually, not requiring dangerous actions such as inserting fingers into printers in operation nor providing printers with expensive detectors.
- printed products obtained by using the ink of the present invention are safe in skin sensitization even if uncured monomers remain.
- the printed products do not sensitize the skin of, for example, fingers and hands which have been brought into contact therewith.
- the ink of the present invention can provide safe printed products.
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- 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)
- Ink Jet Recording Methods And Recording Media Thereof (AREA)
- Ink Jet (AREA)
Abstract
Description
Claims
Priority Applications (8)
Application Number | Priority Date | Filing Date | Title |
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EP12786152.4A EP2710081B1 (en) | 2011-05-18 | 2012-05-10 | Photopolymerizable inkjet ink, ink cartridge, and printer |
US14/118,405 US9068094B2 (en) | 2011-05-18 | 2012-05-10 | Photopolymerizable inkjet ink, ink cartridge, and printer |
CN201280024150.5A CN103547640B (en) | 2011-05-18 | 2012-05-10 | Photopolymerizable inkjet ink, ink, print cartridge and printer |
CA2835165A CA2835165C (en) | 2011-05-18 | 2012-05-10 | Photopolymerizable inkjet ink, ink cartridge, and printer |
RU2013156237/05A RU2570666C2 (en) | 2011-05-18 | 2012-05-10 | Photopolymerisable ink for jet printing, cartridge with ink and printer |
KR1020137033459A KR101580027B1 (en) | 2011-05-18 | 2012-05-10 | Photopolymerizable inkjet ink, ink cartridge, and printer |
BR112013029528-7A BR112013029528B1 (en) | 2011-05-18 | 2012-05-10 | light-curing inkjet ink |
US14/703,241 US9493663B2 (en) | 2011-05-18 | 2015-05-04 | Photopolymerizable inkjet ink, ink cartridge, and printer |
Applications Claiming Priority (2)
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JP2011111757 | 2011-05-18 | ||
JP2011-111757 | 2011-05-18 |
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US14/118,405 A-371-Of-International US9068094B2 (en) | 2011-05-18 | 2012-05-10 | Photopolymerizable inkjet ink, ink cartridge, and printer |
US14/703,241 Continuation US9493663B2 (en) | 2011-05-18 | 2015-05-04 | Photopolymerizable inkjet ink, ink cartridge, and printer |
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WO2012157690A1 true WO2012157690A1 (en) | 2012-11-22 |
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PCT/JP2012/062573 WO2012157690A1 (en) | 2011-05-18 | 2012-05-10 | Photopolymerizable inkjet ink, ink cartridge, and printer |
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US (2) | US9068094B2 (en) |
EP (1) | EP2710081B1 (en) |
JP (1) | JP5994357B2 (en) |
KR (1) | KR101580027B1 (en) |
CN (1) | CN103547640B (en) |
BR (1) | BR112013029528B1 (en) |
CA (1) | CA2835165C (en) |
RU (1) | RU2570666C2 (en) |
WO (1) | WO2012157690A1 (en) |
Cited By (1)
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EP2776520A4 (en) * | 2011-11-07 | 2015-06-03 | Ricoh Co Ltd | Photopolymerizable inkjet ink |
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EP2776520A4 (en) * | 2011-11-07 | 2015-06-03 | Ricoh Co Ltd | Photopolymerizable inkjet ink |
US9802413B2 (en) | 2011-11-07 | 2017-10-31 | Ricoh Company, Ltd. | Photopolymerizable inkjet ink |
US10259226B2 (en) | 2011-11-07 | 2019-04-16 | Ricoh Company, Ltd. | Photopolymerizable inkjet ink |
US10562311B2 (en) | 2011-11-07 | 2020-02-18 | Ricoh Company, Ltd. | Photopolymerizable inkjet ink |
Also Published As
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CN103547640B (en) | 2016-04-13 |
BR112013029528A2 (en) | 2017-01-24 |
JP2012255137A (en) | 2012-12-27 |
EP2710081A4 (en) | 2015-05-06 |
US9493663B2 (en) | 2016-11-15 |
JP5994357B2 (en) | 2016-09-21 |
RU2013156237A (en) | 2015-06-27 |
RU2570666C2 (en) | 2015-12-10 |
CA2835165C (en) | 2016-07-05 |
BR112013029528B1 (en) | 2021-01-19 |
US20150232677A1 (en) | 2015-08-20 |
EP2710081B1 (en) | 2024-09-18 |
KR20140016383A (en) | 2014-02-07 |
EP2710081A1 (en) | 2014-03-26 |
KR101580027B1 (en) | 2015-12-23 |
CA2835165A1 (en) | 2012-11-22 |
US9068094B2 (en) | 2015-06-30 |
CN103547640A (en) | 2014-01-29 |
US20140125744A1 (en) | 2014-05-08 |
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