WO2024122422A1 - Ink compositions - Google Patents
Ink compositions Download PDFInfo
- Publication number
- WO2024122422A1 WO2024122422A1 PCT/JP2023/042658 JP2023042658W WO2024122422A1 WO 2024122422 A1 WO2024122422 A1 WO 2024122422A1 JP 2023042658 W JP2023042658 W JP 2023042658W WO 2024122422 A1 WO2024122422 A1 WO 2024122422A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- copper phthalocyanine
- fatty acid
- hydrocarbon
- ink composition
- present
- Prior art date
Links
- 239000000203 mixture Substances 0.000 title claims abstract description 145
- RBTKNAXYKSUFRK-UHFFFAOYSA-N heliogen blue Chemical compound [Cu].[N-]1C2=C(C=CC=C3)C3=C1N=C([N-]1)C3=CC=CC=C3C1=NC([N-]1)=C(C=CC=C3)C3=C1N=C([N-]1)C3=CC=CC=C3C1=N2 RBTKNAXYKSUFRK-UHFFFAOYSA-N 0.000 claims abstract description 78
- 150000002430 hydrocarbons Chemical class 0.000 claims abstract description 75
- 229930195733 hydrocarbon Natural products 0.000 claims abstract description 74
- 235000014113 dietary fatty acids Nutrition 0.000 claims abstract description 66
- 239000000194 fatty acid Substances 0.000 claims abstract description 66
- 229930195729 fatty acid Natural products 0.000 claims abstract description 66
- -1 fatty acid amine salt Chemical class 0.000 claims abstract description 66
- 239000004215 Carbon black (E152) Substances 0.000 claims abstract description 62
- 150000004702 methyl esters Chemical class 0.000 claims abstract description 23
- 150000004665 fatty acids Chemical class 0.000 claims abstract description 21
- 238000000034 method Methods 0.000 claims abstract description 10
- 238000007639 printing Methods 0.000 claims abstract description 5
- 229920000180 alkyd Polymers 0.000 claims description 17
- 125000003118 aryl group Chemical group 0.000 claims description 13
- 150000001875 compounds Chemical class 0.000 claims description 12
- 239000000758 substrate Substances 0.000 claims description 8
- 239000000463 material Substances 0.000 claims description 6
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 239000000976 ink Substances 0.000 description 67
- 150000002148 esters Chemical class 0.000 description 37
- 239000002253 acid Substances 0.000 description 18
- 229910052757 nitrogen Inorganic materials 0.000 description 18
- 125000004433 nitrogen atom Chemical group N* 0.000 description 18
- 125000001453 quaternary ammonium group Chemical group 0.000 description 13
- 239000002270 dispersing agent Substances 0.000 description 11
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 10
- 229910052739 hydrogen Inorganic materials 0.000 description 10
- 239000001257 hydrogen Substances 0.000 description 10
- 235000021281 monounsaturated fatty acids Nutrition 0.000 description 10
- 125000001273 sulfonato group Chemical group [O-]S(*)(=O)=O 0.000 description 10
- 230000000052 comparative effect Effects 0.000 description 9
- 239000002245 particle Substances 0.000 description 8
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 7
- OYHQOLUKZRVURQ-IXWMQOLASA-N linoleic acid Natural products CCCCC\C=C/C\C=C\CCCCCCCC(O)=O OYHQOLUKZRVURQ-IXWMQOLASA-N 0.000 description 7
- 239000000049 pigment Substances 0.000 description 7
- 239000000126 substance Substances 0.000 description 7
- OYHQOLUKZRVURQ-HZJYTTRNSA-N Linoleic acid Chemical compound CCCCC\C=C/C\C=C/CCCCCCCC(O)=O OYHQOLUKZRVURQ-HZJYTTRNSA-N 0.000 description 6
- 125000000217 alkyl group Chemical group 0.000 description 6
- QYDYPVFESGNLHU-UHFFFAOYSA-N elaidic acid methyl ester Natural products CCCCCCCCC=CCCCCCCCC(=O)OC QYDYPVFESGNLHU-UHFFFAOYSA-N 0.000 description 6
- 235000020778 linoleic acid Nutrition 0.000 description 6
- 239000003921 oil Substances 0.000 description 6
- 235000019198 oils Nutrition 0.000 description 6
- 150000005846 sugar alcohols Polymers 0.000 description 6
- 125000004122 cyclic group Chemical group 0.000 description 5
- 230000007062 hydrolysis Effects 0.000 description 5
- 238000006460 hydrolysis reaction Methods 0.000 description 5
- QYDYPVFESGNLHU-KHPPLWFESA-N methyl oleate Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OC QYDYPVFESGNLHU-KHPPLWFESA-N 0.000 description 5
- 229940073769 methyl oleate Drugs 0.000 description 5
- XSXIVVZCUAHUJO-AVQMFFATSA-N (11e,14e)-icosa-11,14-dienoic acid Chemical compound CCCCC\C=C\C\C=C\CCCCCCCCCC(O)=O XSXIVVZCUAHUJO-AVQMFFATSA-N 0.000 description 4
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 4
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 description 4
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 description 4
- 235000021297 Eicosadienoic acid Nutrition 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 description 4
- 239000005642 Oleic acid Substances 0.000 description 4
- 229910052799 carbon Inorganic materials 0.000 description 4
- 230000002349 favourable effect Effects 0.000 description 4
- IPCSVZSSVZVIGE-UHFFFAOYSA-N hexadecanoic acid Chemical compound CCCCCCCCCCCCCCCC(O)=O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 description 4
- 125000000904 isoindolyl group Chemical group C=1(NC=C2C=CC=CC12)* 0.000 description 4
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 4
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 4
- 235000021313 oleic acid Nutrition 0.000 description 4
- HVGRZDASOHMCSK-UHFFFAOYSA-N (Z,Z)-13,16-docosadienoic acid Natural products CCCCCC=CCC=CCCCCCCCCCCCC(O)=O HVGRZDASOHMCSK-UHFFFAOYSA-N 0.000 description 3
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 150000007513 acids Chemical class 0.000 description 3
- 150000001721 carbon Chemical group 0.000 description 3
- XCJYREBRNVKWGJ-UHFFFAOYSA-N copper(II) phthalocyanine Chemical compound [Cu+2].C12=CC=CC=C2C(N=C2[N-]C(C3=CC=CC=C32)=N2)=NC1=NC([C]1C=CC=CC1=1)=NC=1N=C1[C]3C=CC=CC3=C2[N-]1 XCJYREBRNVKWGJ-UHFFFAOYSA-N 0.000 description 3
- 239000013078 crystal Substances 0.000 description 3
- CVCXSNONTRFSEH-UHFFFAOYSA-N docosa-2,4-dienoic acid Chemical compound CCCCCCCCCCCCCCCCCC=CC=CC(O)=O CVCXSNONTRFSEH-UHFFFAOYSA-N 0.000 description 3
- 239000012530 fluid Substances 0.000 description 3
- 125000003976 glyceryl group Chemical group [H]C([*])([H])C(O[H])([H])C(O[H])([H])[H] 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- 229920006395 saturated elastomer Polymers 0.000 description 3
- 235000021122 unsaturated fatty acids Nutrition 0.000 description 3
- 150000004670 unsaturated fatty acids Chemical group 0.000 description 3
- 235000015112 vegetable and seed oil Nutrition 0.000 description 3
- 239000008158 vegetable oil Substances 0.000 description 3
- OYHQOLUKZRVURQ-NTGFUMLPSA-N (9Z,12Z)-9,10,12,13-tetratritiooctadeca-9,12-dienoic acid Chemical group C(CCCCCCC\C(=C(/C\C(=C(/CCCCC)\[3H])\[3H])\[3H])\[3H])(=O)O OYHQOLUKZRVURQ-NTGFUMLPSA-N 0.000 description 2
- 235000021314 Palmitic acid Nutrition 0.000 description 2
- 235000021355 Stearic acid Nutrition 0.000 description 2
- DTOSIQBPPRVQHS-PDBXOOCHSA-N alpha-linolenic acid Chemical compound CC\C=C/C\C=C/C\C=C/CCCCCCCC(O)=O DTOSIQBPPRVQHS-PDBXOOCHSA-N 0.000 description 2
- 235000020661 alpha-linolenic acid Nutrition 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 239000003086 colorant Substances 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 125000005908 glyceryl ester group Chemical group 0.000 description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
- 238000007641 inkjet printing Methods 0.000 description 2
- 229960004488 linolenic acid Drugs 0.000 description 2
- KQQKGWQCNNTQJW-UHFFFAOYSA-N linolenic acid Natural products CC=CCCC=CCC=CCCCCCCCC(O)=O KQQKGWQCNNTQJW-UHFFFAOYSA-N 0.000 description 2
- WQEPLUUGTLDZJY-UHFFFAOYSA-N n-Pentadecanoic acid Natural products CCCCCCCCCCCCCCC(O)=O WQEPLUUGTLDZJY-UHFFFAOYSA-N 0.000 description 2
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 2
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 2
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 2
- IEQIEDJGQAUEQZ-UHFFFAOYSA-N phthalocyanine Chemical compound N1C(N=C2C3=CC=CC=C3C(N=C3C4=CC=CC=C4C(=N4)N3)=N2)=C(C=CC=C2)C2=C1N=C1C2=CC=CC=C2C4=N1 IEQIEDJGQAUEQZ-UHFFFAOYSA-N 0.000 description 2
- 229920005989 resin Polymers 0.000 description 2
- 239000011347 resin Substances 0.000 description 2
- 239000008117 stearic acid Substances 0.000 description 2
- 238000001132 ultrasonic dispersion Methods 0.000 description 2
- HBOQXIRUPVQLKX-BBWANDEASA-N 1,2,3-trilinoleoylglycerol Chemical compound CCCCC\C=C/C\C=C/CCCCCCCC(=O)OCC(OC(=O)CCCCCCC\C=C/C\C=C/CCCCC)COC(=O)CCCCCCC\C=C/C\C=C/CCCCC HBOQXIRUPVQLKX-BBWANDEASA-N 0.000 description 1
- CXJBZEHYQPVBRM-UHFFFAOYSA-N 2,3-dihydroxypropyl icosa-2,4-dienoate Chemical compound CCCCCCCCCCCCCCCC=CC=CC(=O)OCC(O)CO CXJBZEHYQPVBRM-UHFFFAOYSA-N 0.000 description 1
- SZINCBKGFWRJJE-UHFFFAOYSA-N C(C=CC=CCCCCCCCCCCCCCCC)(=O)OCCC(CO)(CO)CO Chemical compound C(C=CC=CCCCCCCCCCCCCCCC)(=O)OCCC(CO)(CO)CO SZINCBKGFWRJJE-UHFFFAOYSA-N 0.000 description 1
- WZKPCVBGFMZFQF-UHFFFAOYSA-N C(C=CC=CCCCCCCCCCCCCCCCCC)(=O)OCCC(CO)(CO)CO Chemical compound C(C=CC=CCCCCCCCCCCCCCCCCC)(=O)OCCC(CO)(CO)CO WZKPCVBGFMZFQF-UHFFFAOYSA-N 0.000 description 1
- CZXNAFSBPVCVQL-UHFFFAOYSA-N C(C=CC=CCCCCCCCCCCCCCCCCCC)(=O)OCC(O)CO Chemical compound C(C=CC=CCCCCCCCCCCCCCCCCCC)(=O)OCC(O)CO CZXNAFSBPVCVQL-UHFFFAOYSA-N 0.000 description 1
- XSPBGRGDUMNERV-UHFFFAOYSA-N C(C=CC=CCCCCCCCCCCCCCCCCCC)(=O)OCCC(CO)(CO)CO Chemical compound C(C=CC=CCCCCCCCCCCCCCCCCCC)(=O)OCCC(CO)(CO)CO XSPBGRGDUMNERV-UHFFFAOYSA-N 0.000 description 1
- UAMPDBBNZBZEOM-HZJYTTRNSA-N CCCCC\C=C/C\C=C/CCCCCCCC(=O)OCCC(CO)(CO)CO Chemical compound CCCCC\C=C/C\C=C/CCCCCCCC(=O)OCCC(CO)(CO)CO UAMPDBBNZBZEOM-HZJYTTRNSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- JPVYNHNXODAKFH-UHFFFAOYSA-N Cu2+ Chemical compound [Cu+2] JPVYNHNXODAKFH-UHFFFAOYSA-N 0.000 description 1
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 235000021588 free fatty acids Nutrition 0.000 description 1
- 239000003446 ligand Substances 0.000 description 1
- OYHQOLUKZRVURQ-AVQMFFATSA-N linoelaidic acid Chemical compound CCCCC\C=C\C\C=C\CCCCCCCC(O)=O OYHQOLUKZRVURQ-AVQMFFATSA-N 0.000 description 1
- HBOQXIRUPVQLKX-UHFFFAOYSA-N linoleic acid triglyceride Natural products CCCCCC=CCC=CCCCCCCCC(=O)OCC(OC(=O)CCCCCCCC=CCC=CCCCCC)COC(=O)CCCCCCCC=CCC=CCCCCC HBOQXIRUPVQLKX-UHFFFAOYSA-N 0.000 description 1
- ZMKDEQUXYDZSNN-UHFFFAOYSA-N linolelaidic acid Natural products CCCCCCCCC=CCC=CCCCCC(O)=O ZMKDEQUXYDZSNN-UHFFFAOYSA-N 0.000 description 1
- 238000003801 milling Methods 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 238000000634 powder X-ray diffraction Methods 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
Classifications
-
- 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
- C09D11/32—Inkjet printing inks characterised by colouring agents
- C09D11/322—Pigment 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
- C09D11/102—Printing inks based on artificial resins containing macromolecular compounds obtained by reactions other than those only involving unsaturated carbon-to-carbon bonds
- C09D11/104—Polyesters
- C09D11/105—Alkyd resins
-
- 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
- C09D11/32—Inkjet printing inks characterised by colouring agents
- C09D11/324—Inkjet printing inks characterised by colouring agents containing carbon black
- C09D11/326—Inkjet printing inks characterised by colouring agents containing carbon black characterised by the pigment dispersant
-
- 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
- C09D11/36—Inkjet printing inks based on non-aqueous solvents
-
- 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 ink compositions, methods for producing ink compositions, methods of printing and printed articles.
- the present invention provides a method of manufacturing an ink composition
- a method of manufacturing an ink composition comprising: - providing a methyl ester of a C 16 -C 18 fatty acid; - providing beta-form copper phthalocyanine having a bulk density of 0.40 kgL -1 or more; - providing a C 14 -C 18 hydrocarbon; and - providing a fatty acid amine salt of sulfonated copper phthalocyanine; wherein the weight ratio of the C 14 -C 18 hydrocarbon to the fatty acid amine salt of sulfonated copper phthalocyanine is from 6:1 to 45:1.
- ink composition of the present invention which will be apparent from the following detailed description of the invention, and include good particle size stability and good viscosity stability when using a plant-based carrier fluid and a high flashpoint dispersant
- the acid component of the first ester may be branched or unbranched, and may be linear or cyclic. Typically the acid component of the first ester is linear and unbranched.
- the acid component of the first ester may be saturated or unsaturated.
- Suitable acid components of the first ester include polyunsaturated acids (examples of which include linoleic acid and linolenic acid), monounsaturated acids (examples of which include oleic acid), saturated acids (examples of which include palmitic acid and stearic acid), and mixtures thereof.
- the acid component of the first ester is linoleic acid, oleic acid, palmitic acid, linolenic acid. stearic acid, or a mixture thereof.
- the acid component of the first ester is an unsaturated fatty acid.
- the acid component of the first ester is a mono-unsaturated fatty acid.
- Mono-unsaturated fatty acids may be obtained, for example, by hydrolysis of vegetable oils (e.g. soy oil).
- suitable mono-unsaturated fatty acids include C 18 monounsaturated fatty acids such as oleic acid.
- C 18 monounsaturated fatty acids such as oleic acid can be obtained by hydrolysis of soy oil.
- the amount of the methyl ester of a C 16 -C 18 fatty acid present in the ink composition of the present invention is not particularly limited.
- the amount of the methyl ester of a C 16 -C 18 fatty acid present in the ink composition of the present invention may be around 60 wt% or more, based on the total weight of the composition, for example 65 wt% or more, 70 wt% or more, or 75 wt% or more, based on the total weight of the composition.
- Copper phthalocyanine is generally crystalline, and may exist in different crystalline forms. Crystalline forms include the ⁇ , s, ⁇ , ⁇ , and ⁇ polymorphs.
- the copper phthalocyanine in the ink composition of the present invention is in the s crystal form, and is referred to as beta-form copper phthalocyanine.
- the s crystal form is well known in the art and is described for example by J. M. Robertson, J. Chem. Soc. (1935) 615.
- the C 14 -C 18 hydrocarbon is a mixture of compounds and comprises one or more C 14 -C 18 n-alkane, one or more C 14 -C 18 isoalkane, one or more non-aromatic cyclic C 14 -C 18 hydrocarbon, and one or more aromatic C 14 -C 18 hydrocarbon, wherein the one or more aromatic C 14 -C 18 hydrocarbon is present in an amount of 2 wt% to 30 wt%, based on the total weight of the C 14 -C 18 hydrocarbon.
- the absolute amount of the C 14 -C 18 hydrocarbon in the ink composition of the present invention is not particularly limited.
- the amount of the C 14 -C 18 hydrocarbon present in the ink composition of the present invention may be around 4 wt% or more, based on the total weight of the composition, for example 6 wt% or more, 8 wt% or more, or 10 wt% or more, based on the total weight of the composition.
- the amount of the C 14 - C 18 hydrocarbon present in the ink composition of the present invention may be around 18 wt% or less, based on the total weight of the composition, for example 16 wt% or less, 14 wt% or less, or 12 wt% or less, based on the total weight of the composition.
- the ink composition of the present invention comprises a fatty acid amine salt of sulfonated copper phthalocyanine.
- the fatty acid amine salt of sulfonated copper phthalocyanine may act as a dispersant synergist in the ink composition of the present invention.
- the presence of a fatty acid amine salt of sulfonated copper phthalocyanine in the ink composition of the present invention results in favourable properties such as particle size stability and viscosity stability.
- C 8 to C 22 hydrocarbon groups in the quaternary ammonium cation in the fatty acid amine salt may be the same or different and may each be, for example, a C 14 to C 22 hydrocarbon group, C 16 to C 20 hydrocarbon group, or C 18 hydrocarbon group, such as a C 14 to C 22 alkyl group, C 16 to C 20 alkyl group, or C 18 alkyl group.
- the 4-n other groups in the quaternary ammonium cation in the fatty acid amine salt may be the same or different and may each be, for example a hydrogen atom or a C 1 to C 2 alkyl group; such as for example a methyl group.
- the quaternary ammonium cation comprises 2 C 18 alkyl groups attached to the quaternary nitrogen atom, and 2 methyl groups attached to the quaternary nitrogen atom.
- the amount of the fatty acid amine salt of sulfonated copper phthalocyanine present in the ink composition of the present invention may be around 0.50 wt% or less, based on the total weight of the composition, for example 0.45 wt% or less, 0.40 wt% or less, or 0.35 wt% or less, based on the total weight of the composition.
- the ink composition comprises - 70 wt% to 80 wt%, based on the total weight of the composition, of a methyl ester of a C 18 monounsaturated fatty acid; - 6 wt% to 14 wt%, based on the total weight of the composition, of beta-form copper phthalocyanine having a bulk density of from 0.46 kgL -1 to 0.60 kgL -1 ; - 8 wt% to 14 wt%, based on the total weight of the composition, of a C 14 -C 18 hydrocarbon which is a mixture of one or more C 14 -C 18 n-alkane, one or more C 14 -C 18 isoalkane, one or more non-aromatic cyclic C 14 -C 18 hydrocarbon, and one or more aromatic C 14 -C 18 hydrocarbon, wherein the one or more aromatic C 14 -C 18 hydrocarbon is present in an amount of 2 wt% to 30wt%, based on the total weight
Landscapes
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Wood Science & Technology (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Inks, Pencil-Leads, Or Crayons (AREA)
Abstract
Disclosed is an ink composition comprising: - a methyl ester of a C16-C18 fatty acid; - beta-form copper phthalocyanine having a bulk density of 0.40 kgL-1 or more; - a C14-C18 hydrocarbon; and - a fatty acid amine salt of sulfonated copper phthalocyanine; wherein the weight ratio of the C14-C18 hydrocarbon to the fatty acid amine salt of sulfonated copper phthalocyanine is from 6:1 to 45:1. Methods for producing ink compositions, methods of printing and printed articles are also disclosed
Description
The present invention relates to ink compositions, methods for producing ink compositions, methods of printing and printed articles.
Growing interest in sustainability and environmentally-friendly technologies has led to increased demand for plant-based inks. In addition, concerns over the flammability of ink components has led to increased demand for inks with non-flammable components. Changes in particle size and viscosity over time will lead to inks being unsuitable for inkjet printing.
There is therefore a need for new ink compositions which solve the above problems.
In one aspect, the present invention provides an ink composition comprising:
- a methyl ester of a C16-C18 fatty acid;
- beta-form copper phthalocyanine having a bulk density of 0.40 kgL-1 or more;
- a C14-C18 hydrocarbon; and
- a fatty acid amine salt of sulfonated copper phthalocyanine; wherein the weight ratio of the C14-C18 hydrocarbon to the fatty acid amine salt of sulfonated copper phthalocyanine is from 6:1 to 45:1.
- a methyl ester of a C16-C18 fatty acid;
- beta-form copper phthalocyanine having a bulk density of 0.40 kgL-1 or more;
- a C14-C18 hydrocarbon; and
- a fatty acid amine salt of sulfonated copper phthalocyanine; wherein the weight ratio of the C14-C18 hydrocarbon to the fatty acid amine salt of sulfonated copper phthalocyanine is from 6:1 to 45:1.
In another aspect, the present invention provides a method of manufacturing an ink composition comprising:
- providing a methyl ester of a C16-C18 fatty acid;
- providing beta-form copper phthalocyanine having a bulk density of 0.40 kgL-1 or more;
- providing a C14-C18 hydrocarbon; and
- providing a fatty acid amine salt of sulfonated copper phthalocyanine; wherein the weight ratio of the C14-C18 hydrocarbon to the fatty acid amine salt of sulfonated copper phthalocyanine is from 6:1 to 45:1.
- providing a methyl ester of a C16-C18 fatty acid;
- providing beta-form copper phthalocyanine having a bulk density of 0.40 kgL-1 or more;
- providing a C14-C18 hydrocarbon; and
- providing a fatty acid amine salt of sulfonated copper phthalocyanine; wherein the weight ratio of the C14-C18 hydrocarbon to the fatty acid amine salt of sulfonated copper phthalocyanine is from 6:1 to 45:1.
In a further aspect, the present invention provides a method of printing comprising:
- providing an ink composition of the present invention; and
- using an inkjet printer to print the ink composition onto a substrate.
- providing an ink composition of the present invention; and
- using an inkjet printer to print the ink composition onto a substrate.
In a still further aspect, the present invention provides a printed article comprising a substrate and an ink composition of the present invention.
Advantages of the ink composition of the present invention which will be apparent from the following detailed description of the invention, and include good particle size stability and good viscosity stability when using a plant-based carrier fluid and a high flashpoint dispersant
In one aspect, the present invention provides an ink composition comprising:
- a methyl ester of a C16-C18 fatty acid;
- beta-form copper phthalocyanine having a bulk density of 0.40 kgL-1 or more;
- a C14-C18 hydrocarbon; and
- a fatty acid amine salt of sulfonated copper phthalocyanine; wherein the weight ratio of the C14-C18 hydrocarbon to the fatty acid amine salt of sulfonated copper phthalocyanine is from 6:1 to 45:1.
- a methyl ester of a C16-C18 fatty acid;
- beta-form copper phthalocyanine having a bulk density of 0.40 kgL-1 or more;
- a C14-C18 hydrocarbon; and
- a fatty acid amine salt of sulfonated copper phthalocyanine; wherein the weight ratio of the C14-C18 hydrocarbon to the fatty acid amine salt of sulfonated copper phthalocyanine is from 6:1 to 45:1.
The ink composition of the present invention comprises a methyl ester of a C16-C18 fatty acid (hereinafter referred to as a first ester). The first ester may act as a carrier fluid in the ink composition.
As used herein a methyl ester of a C16-C18 fatty acid is a fatty acid having 16 to 18 carbon atoms in which the -OH group of the acid moiety is replaced with an -O-CH3 group. The first ester may be a single compound or a mixture of compounds. The first ester is derived from a fatty acid or mixture of fatty acids (hereinafter the acid component of the first ester) and methanol. The first ester may be a plant-based material. As used herein, a plant-based material is a material obtainable by processing vegetable matter, e.g., by hydrolysis of vegetable oil such as soy oil. Plant-based materials suitable for the first ester include plant-based oils described for example in CRC Handbook of Chemistry and Physics, edited by Robert C. Weast and Melvin J. Astle, CRC Press, 1979.
The acid component of the first ester may be branched or unbranched, and may be linear or cyclic. Typically the acid component of the first ester is linear and unbranched. The acid component of the first ester may be saturated or unsaturated. Suitable acid components of the first ester include polyunsaturated acids (examples of which include linoleic acid and linolenic acid), monounsaturated acids (examples of which include oleic acid), saturated acids (examples of which include palmitic acid and stearic acid), and mixtures thereof. In some embodiments the acid component of the first ester is linoleic acid, oleic acid, palmitic acid, linolenic acid. stearic acid, or a mixture thereof.
In some embodiments, the acid component of the first ester is an unsaturated fatty acid. Preferably the acid component of the first ester is a mono-unsaturated fatty acid. Mono-unsaturated fatty acids may be obtained, for example, by hydrolysis of vegetable oils (e.g. soy oil). Preferred examples of suitable mono-unsaturated fatty acids include C18 monounsaturated fatty acids such as oleic acid. C18 monounsaturated fatty acids such as oleic acid can be obtained by hydrolysis of soy oil.
Thus, in preferred embodiments, the methyl ester of a C16-C18 fatty acid in the ink composition of the present invention is a methyl ester of a C18 monounsaturated fatty acid, such as methyl oleate, for example having the CAS number 67762-38-3.
Suitable methyl esters of C16-C18 fatty acids are available commercially, such as METHYL OLEATE P, available from Mosselman S.A. In some embodiments, the methyl esters of C16-C18 fatty acids is METHYL OLEATE P, available from Mosselman S.A.
The amount of the methyl ester of a C16-C18 fatty acid present in the ink composition of the present invention is not particularly limited. The amount of the methyl ester of a C16-C18 fatty acid present in the ink composition of the present invention may be around 60 wt％ or more, based on the total weight of the composition, for example 65 wt％ or more, 70 wt％ or more, or 75 wt％ or more, based on the total weight of the composition. The amount of the methyl ester of a C16-C18 fatty acid present in the ink composition of the present invention may be around 95 wt％ or less, based on the total weight of the composition, for example 90 wt％ or less, 85 wt％ or less, or 80 wt％ or less, based on the total weight of the composition. The amount of the methyl ester of a C16-C18 fatty acid present in the ink composition of the present invention may be from 60 wt％ to 90 wt％, from 65 wt％ to 85 wt％, or from 70 wt％ to 80 wt％, based on the total weight of the composition.
The ink composition of the present invention comprises beta-form copper phthalocyanine. The beta-form copper phthalocyanine may act as a cyan pigment in the ink composition. Thus, the ink composition of the present invention is typically a cyan ink.
Copper phthalocyanine, also known as CuPc or phthalocyanine blue, is a blue phthalocyanine pigment having CAS number 147-14-8 and the following chemical structure 1:
As can be seen from the structure above, copper phthalocyanine comprises a phthalocyanine macrocyclic ligand having four isoindole units and Cu(II).
Copper phthalocyanine is generally crystalline, and may exist in different crystalline forms. Crystalline forms include the α, s, γ, η, and χ polymorphs. The copper phthalocyanine in the ink composition of the present invention is in the s crystal form, and is referred to as beta-form copper phthalocyanine. The s crystal form is well known in the art and is described for example by J. M. Robertson, J. Chem. Soc. (1935) 615. The s crystal form of copper phthalocyanine may be characterised by an XRPD (CuKα) spectrum comprising peaks at 7.1±0.2 °2θ, 9.1±0.2 °2θ, 10.6±0.2 °2θ, 28.5±0.2 °2θ, and 31.9±0.2 °2θ. Beta-form copper phthalocyanine pigments are widely available from commercial sources, for example as Heliogen Blue L7101F (15:4) from Sun Chemical Colors & Effects GmbH and as Lionol Blue FG-7400-G (15:4) available from Toyocolor Co., Ltd.
The beta-form copper phthalocyanine in the ink composition of the present invention has a bulk density of 0.40 kgL-1 or more. As used herein, the bulk density of the beta-form copper phthalocyanine is typically as measured according to ASTM D1895-17.
In the ink composition of the present invention, the beta-form copper phthalocyanine has a bulk density of 0.40 kgL-1 or more. Preferably the beta-form copper phthalocyanine has a bulk density of 0.42 kgL-1 or more, more preferably 0.44 kgL-1 or more, still more preferably 0.46 kgL-1 or more, most preferably 0.48 kgL-1 or more. The beta-form copper phthalocyanine typically has a bulk density of 1.50 kgL-1 or less preferably has a bulk density of 1.00 kgL-1 or less, more preferably 0.80 kgL-1 or less, still more preferably 0.60 kgL-1 or less, most preferably 0.50 kgL-1 or less. Typically the beta- form copper phthalocyanine has a bulk density of from 0.40 kgL-1 to 1.50 kgL-1, preferably from 0.42 kgL-1 to 1.00 kgL-1, more preferably from 0.44 kgL-1 to 0.80 kgL-1, still more preferably from 0.46 kgL-1 to 0.60 kgL-1, most preferably from 0.48 kgL-1 to 0.50 kgL-1. When the beta-form copper phthalocyanine has a bulk density of 0.40 kgL-1 or more, and particularly has a bulk density in the typical and preferred amounts described above, the ink composition of the present invention exhibits favourable properties such as particle size stability and viscosity stability.
In some embodiments, the beta-form copper phthalocyanine in the ink composition of the present invention is Lionol Blue FG-7400-G (15:4), available from Toyocolor Co., Ltd.
The amount of the beta-form copper phthalocyanine present in the ink composition of the present invention is not particularly limited. The amount of the beta-form copper phthalocyanine present in the ink composition of the present invention may be around 2 wt％ or more, based on the total weight of the composition, for example 4 wt％ or more, 6 wt％ or more, or 8 wt％ or more, based on the total weight of the composition. The amount of the beta-form copper phthalocyanine present in the ink composition of the present invention may be around 18 wt％ or less, based on the total weight of the composition, for example 16 wt％ or less, 14 wt％ or less, or 12 wt％ or less, based on the total weight of the composition. The amount of the beta-form copper phthalocyanine present in the ink composition of the present invention may be from 2 wt％ to 18 wt％, from 4 wt％ to 16 wt％, from 6 wt％ to 14 wt％, or from 8 wt％ to 12 wt％, based on the total weight of the composition.
The ink composition of the present invention comprises a C14-C18 hydrocarbon. The C14-C18 hydrocarbon may act as a dispersant in the ink composition of the present invention.
As used herein a C14-C18 hydrocarbon is a compound having 14 to 18 carbon atoms, and containing only carbon and hydrogen atoms. The C14-C18 hydrocarbon may be branched or unbranched. Branched C14-C18 hydrocarbons include C14-C18 isoalkanes. Unbranched C14-C18 hydrocarbons include C14-C18 n-alkanes. The C14-C18 hydrocarbon may be saturated or unsaturated. The C14-C18 hydrocarbon may be linear or cyclic. Cyclic C14-C18 hydrocarbons comprise one or more cyclic moiety and optionally further comprise one or more linear moiety. The one or more cyclic moiety may be aromatic or non- aromatic.
The C14-C18 hydrocarbon preferably has a flashpoint of 93℃ or more, for example 93℃ to 120℃, 93℃ to 110℃, or 93℃ to 100℃. The flashpoint of the C14-C18 hydrocarbon can be measured by appropriate techniques known in the art, for example according to ISO 2719:2016.
The C14-C18 hydrocarbon may be a single compound or a mixture of compounds. Preferably, the C14-C18 hydrocarbon is a mixture of compounds selected from the group consisting of:
- C14-C18 n-alkanes;
- C14-C18 isoalkanes;
- non-aromatic cyclic C14-C18 hydrocarbons; and
- aromatic C14-C18 hydrocarbons.
- C14-C18 n-alkanes;
- C14-C18 isoalkanes;
- non-aromatic cyclic C14-C18 hydrocarbons; and
- aromatic C14-C18 hydrocarbons.
When the C14-C18 hydrocarbon is a mixture of compounds and comprises one or more aromatic C14-C18 hydrocarbon, the aromatic C14-C18 hydrocarbon is preferably present in an amount of 2 wt％ to 30wt％, based on the total weight of the C14-C18 hydrocarbon.
More preferably the C14-C18 hydrocarbon is a mixture of compounds and comprises one or more C14-C18 n-alkane, one or more C14-C18 isoalkane, one or more non-aromatic cyclic C14-C18 hydrocarbon, and one or more aromatic C14-C18 hydrocarbon. Still more preferably the C14-C18 hydrocarbon is a mixture of compounds and comprises one or more C14-C18 n-alkane, one or more C14-C18 isoalkane, one or more non-aromatic cyclic C14-C18 hydrocarbon, and one or more aromatic C14-C18 hydrocarbon, wherein the one or more aromatic C14-C18 hydrocarbon is present in an amount of 2 wt％ to 30 wt％, based on the total weight of the C14-C18 hydrocarbon.
Suitable C14-C18 hydrocarbons are available commercially and include Solsperse 13940 from The Lubrizol Corporation. In some embodiments the C14-C18 hydrocarbon in the ink composition of the present invention is Solsperse 13940 from The Lubrizol Corporation.
The absolute amount of the C14-C18 hydrocarbon in the ink composition of the present invention is not particularly limited. The amount of the C14-C18 hydrocarbon present in the ink composition of the present invention may be around 4 wt％ or more, based on the total weight of the composition, for example 6 wt％ or more, 8 wt％ or more, or 10 wt％ or more, based on the total weight of the composition. The amount of the C14- C18 hydrocarbon present in the ink composition of the present invention may be around 18 wt％ or less, based on the total weight of the composition, for example 16 wt％ or less, 14 wt％ or less, or 12 wt％ or less, based on the total weight of the composition. The amount of the C14-C18 hydrocarbon present in the ink composition of the present invention may be from 4 wt％ to 18 wt％, from 6 wt％ to 16 wt％, from 8 wt％ to 14 wt％, or from 10 wt％ to 12 wt％, based on the total weight of the composition.
The ink composition of the present invention comprises a fatty acid amine salt of sulfonated copper phthalocyanine. The fatty acid amine salt of sulfonated copper phthalocyanine may act as a dispersant synergist in the ink composition of the present invention. The presence of a fatty acid amine salt of sulfonated copper phthalocyanine in the ink composition of the present invention results in favourable properties such as particle size stability and viscosity stability.
As used herein a fatty acid amine salt of sulfonated copper phthalocyanine comprises a copper phthalocyanine sulfonate anion, and a quaternary ammonium cation.
The copper phthalocyanine sulfonate anion comprises one or more sulfonate group attached to a carbon atom in an isoindole unit of the phthalocyanine macrocycle. The copper phthalocyanine sulfonate anion may for example have one, two, three or four sulfonate groups. Each sulfonate group may be attached to a carbon atom in an isoindole unit of the phthalocyanine macrocycle. In some embodiments the copper phthalocyanine sulfonate anion has one sulfonate group attached to a carbon atom in an isoindole unit of the phthalocyanine macrocycle.
The quaternary ammonium cation in the fatty acid amine salt comprises n C8 to C22 hydrocarbon groups attached to the quaternary nitrogen atom, wherein n is from 1 to 4. In addition to the n C8 to C22 hydrocarbon groups, the quaternary ammonium cation in the fatty acid amine salt comprises 4-n other groups attached to the quaternary nitrogen atom. The 4-n other groups may, for example, be independently selected from hydrogen and C1 to C7 alkyl. The quaternary ammonium cation in the fatty acid amine salt may for example comprise:
- 1 C8 to C22 hydrocarbon group attached to the quaternary nitrogen atom, and 3 groups independently selected from hydrogen and C1 to C7 alkyl attached to the quaternary nitrogen atom; or
- 2 C8 to C22 hydrocarbon groups attached to the quaternary nitrogen atom, and 2 groups independently selected from hydrogen and C1 to C7 alkyl attached to the quaternary nitrogen atom; or
- 3 C8 to C22 hydrocarbon groups attached to the quaternary nitrogen atom, and 1 group independently selected from hydrogen and C1 to C7 alkyl attached to the quaternary nitrogen atom; or
- 4 C8 to C22 hydrocarbon groups attached to the quaternary nitrogen atom, and no further groups attached to the quaternary nitrogen atom.
- 1 C8 to C22 hydrocarbon group attached to the quaternary nitrogen atom, and 3 groups independently selected from hydrogen and C1 to C7 alkyl attached to the quaternary nitrogen atom; or
- 2 C8 to C22 hydrocarbon groups attached to the quaternary nitrogen atom, and 2 groups independently selected from hydrogen and C1 to C7 alkyl attached to the quaternary nitrogen atom; or
- 3 C8 to C22 hydrocarbon groups attached to the quaternary nitrogen atom, and 1 group independently selected from hydrogen and C1 to C7 alkyl attached to the quaternary nitrogen atom; or
- 4 C8 to C22 hydrocarbon groups attached to the quaternary nitrogen atom, and no further groups attached to the quaternary nitrogen atom.
The n C8 to C22 hydrocarbon groups in the quaternary ammonium cation in the fatty acid amine salt may be the same or different and may each be, for example, a C14 to C22 hydrocarbon group, C16 to C20 hydrocarbon group, or C18 hydrocarbon group, such as a C14 to C22 alkyl group, C16 to C20 alkyl group, or C18 alkyl group. The 4-n other groups in the quaternary ammonium cation in the fatty acid amine salt may be the same or different and may each be, for example a hydrogen atom or a C1 to C2 alkyl group; such as for example a methyl group. In some embodiments the quaternary ammonium cation comprises 2 C18 alkyl groups attached to the quaternary nitrogen atom, and 2 methyl groups attached to the quaternary nitrogen atom.
In some embodiments, the fatty acid amine salt of sulfonated copper phthalocyanine comprising a copper phthalocyanine sulfonate anion having one, two, three or four sulfonate groups, and a quaternary ammonium cation having, attached to the quaternary nitrogen atom, n C8 to C22 hydrocarbon groups and 4-n groups selected from hydrogen and C1 to C7 alkyl, wherein n is from 1 to 4. In some embodiments, the fatty acid amine salt of sulfonated copper phthalocyanine comprises a copper phthalocyanine sulfonate anion having one sulfonate group, and a quaternary ammonium cation having, attached to the quaternary nitrogen atom, 2 C16 to C20 hydrocarbon groups and 2 groups selected from hydrogen and C1 to C2 alkyl.
Suitable fatty acid amine salts of sulfonated copper phthalocyanine are available commercially and include Solsperse 5000S available from The Lubrizol Corporation. In some embodiments, the fatty acid amine salt of sulfonated copper phthalocyanine in the ink composition of the present invention is Solsperse 5000S available from The Lubrizol Corporation.
The absolute amount of the fatty acid amine salt of sulfonated copper phthalocyanine in the ink composition of the present invention is not particularly limited. The amount of the fatty acid amine salt of sulfonated copper phthalocyanine present in the ink composition of the present invention may be around 0.06 wt％ or more, based on the total weight of the composition, for example 0.09 wt％ or more, 0.12 wt％ or more, or 0.15 wt％ or more, based on the total weight of the composition. The amount of the fatty acid amine salt of sulfonated copper phthalocyanine present in the ink composition of the present invention may be around 0.50 wt％ or less, based on the total weight of the composition, for example 0.45 wt％ or less, 0.40 wt％ or less, or 0.35 wt％ or less, based on the total weight of the composition. The amount of the fatty acid amine salt of sulfonated copper phthalocyanine present in the ink composition of the present invention may be from 0.06 wt％ to 0.50 wt％, from 0.09 wt％ to 0.45 wt％, from 0.12 wt％ to 0.40 wt％, or from 0.15 wt％ to 0.35 wt％, based on the total weight of the composition.
The presence of a fatty acid amine salt of sulfonated copper phthalocyanine in the ink composition of the present invention, particularly with the composition and in the amounts discussed above, results in favourable properties such as particle size stability and viscosity stability.
The ink composition of the present invention may further comprise an alkyd resin. As used herein, an alkyd resin comprises an ester (hereinafter referred to as a second ester). The second ester is derived from an acid (hereinafter the acid component of the second ester) and an alcohol (hereinafter the alcohol component of the second ester). The second ester may be a plant-based material as defined elsewhere herein.
In some embodiments, the acid component of the second ester is an unsaturated fatty acid. Preferably the acid component of the second ester is a di-unsaturated fatty acid. Di-unsaturated fatty acids may be obtained, for example, by hydrolysis of vegetable oils (e.g. soy oil). Examples of suitable di-unsaturated fatty acids include linoleic acid, eicosadienoic acid, docosadienoic acid and linolelaidic acid. Linoleic acid is preferred as the acid component of the second ester. Linoleic acid can be obtained by hydrolysis of soy oil.
In some embodiments, the alcohol component of the second ester is a polyhydric alcohol. Examples of suitable polyhydric alcohols include glycerol, trimethylolpropane, and pentaerythritol. Pentaerythritol is preferred as the alcohol component of the second ester.
The second ester may be an ester of a di-unsaturated fatty acid and a polyhydric alcohol, and examples of the second ester include glyceryl esters of linoleic acid (e.g. glyceryl monolinleate, glyceryl dilonleate, glyceryl trilinoleate, or any mixture thereof) , glyceryl esters of eicosadienoic acid (e.g. glyceryl monoeicosadienoate, glyceryl dieicosadienoate, glyceryl trieicosadienoate or any mixture thereof), trimethylolpropyl esters of linoleic acid (e.g. trimethylolpropyl monolinoleate, trimethylolpropyl dilinoleate, trimethylolpropyl trilinoleate or any mixture thereof), trimethylolpropyl esters of eicosadienoic acid (e.g. trimethylolpropyl monoeicosadienoate, trimethylolpropyl dieicosadienoate, trimethylolpropyl trieicosadienoate or any mixture thereof), trimethylolpropyl esters of docosadienoic acid (e.g. trimethylolpropyl monodocosadienoate, trimethylolpropyl didocosadienoate, trimethylolpropyl tridocosadienoate or any mixture thereof), pentaerythrityl esters of linoleic acid (e.g. pentaerythrityl monolinoleate, pentaerythrityl dilinoleate, pentaerythrityl trilinoleate, pentaerythrityl tetralinoleate, or any mixture thereof), pentaerythrityl esters of eicosadienoic acid (e.g. pentaerythrityl monoeicosadienoate, pentaerythrityl dieicosadienoate, pentaerythrityl trieicosadienoate, pentaerythrityl tetraeicosadienoate, or any mixture thereof), and pentaerythrityl esters of docosadienoic acid (e.g. pentaerythrityl monodocosadienoate, pentaerythrityl didocosadienoate, pentaerythrityl tridocosadienoate, pentaerythrityl tetradocosadienoate, or any mixture thereof). Pentaerythrityl esters of tetralinoleic acid are preferred as the second ester. Mixtures comprising pentaerythrityl monolinoleate and pentaerythrityl dilinoleate are particularly preferred.
The alkyd resin may be a single substance, or a mixture of different substances. The one or more further substances may be other esters (e.g. other esters of unsaturated fatty acids and polyhydric alcohols), or other substances of the types commonly found in alkyd resins.
In certain embodiments the alkyd resin is Vilkyd 782, available from Vil Resins Ltd.
In some embodiments, the alkyd resin, if present, is present in an amount of 0.5wt％ or more, based on the total weight of the composition. In preferred embodiments of the ink composition of the present invention the alkyd resin, if present, is present in an amount of 0.5 to 8 wt％, based on the total weight of the composition. In some preferred embodiments, the alkyd resin, if present, is present in amount of 1 to 6 wt％, based on the total weight of the composition. In particularly preferred embodiments, the alkyd resin, if present, is present in an amount of 2 to 4 wt％, based on the total weight of the composition.
The weight ratio of the C14-C18 hydrocarbon to the fatty acid amine salt of sulfonated copper phthalocyanine in the ink composition of the present invention is from 6:1 to 45:1. Preferably, the weight ratio of the C14-C18 hydrocarbon to the fatty acid amine salt of sulfonated copper phthalocyanine is from 6:1 to 40:1. More preferably, the weight ratio of the C14-C18 hydrocarbon to the fatty acid amine salt of sulfonated copper phthalocyanine is from 6.25:1 to 40:1. When the weight ratio of the C14-C18 hydrocarbon to the fatty acid amine salt of sulfonated copper phthalocyanine is from 6:1 to 45:1, and particularly from 6:1 to 40:1 or from 6.25:1 to 40:1, the ink composition of the present invention exhibits favourable properties such as particle size stability and viscosity stability.
In some embodiments, the ink composition comprises
- a methyl ester of a C16-C18 monounsaturated fatty acid;
- beta-form copper phthalocyanine having a bulk density of from 0.42 kgL-1 to 1.00 kgL-1;
- a C14-C18 hydrocarbon which is a mixture of compounds selected from the group consisting of C14-C18 n-alkanes, C14-C18 isoalkanes, non-aromatic cyclic C14-C18 hydrocarbons, and aromatic C14-C18 hydrocarbons;
- a fatty acid amine salt of sulfonated copper phthalocyanine comprising a copper phthalocyanine sulfonate anion having one, two, three or four sulfonate groups, and a quaternary ammonium cation having, attached to the quaternary nitrogen atom, n C8 to C22 hydrocarbon groups and 4-n groups selected from hydrogen and C1 to C7 alkyl, wherein n is from 1 to 4; and
- an alkyd resin; wherein the weight ratio of the C14-C18 hydrocarbon to the fatty acid amine salt of sulfonated copper phthalocyanine is from 6:1 to 45:1.
- a methyl ester of a C16-C18 monounsaturated fatty acid;
- beta-form copper phthalocyanine having a bulk density of from 0.42 kgL-1 to 1.00 kgL-1;
- a C14-C18 hydrocarbon which is a mixture of compounds selected from the group consisting of C14-C18 n-alkanes, C14-C18 isoalkanes, non-aromatic cyclic C14-C18 hydrocarbons, and aromatic C14-C18 hydrocarbons;
- a fatty acid amine salt of sulfonated copper phthalocyanine comprising a copper phthalocyanine sulfonate anion having one, two, three or four sulfonate groups, and a quaternary ammonium cation having, attached to the quaternary nitrogen atom, n C8 to C22 hydrocarbon groups and 4-n groups selected from hydrogen and C1 to C7 alkyl, wherein n is from 1 to 4; and
- an alkyd resin; wherein the weight ratio of the C14-C18 hydrocarbon to the fatty acid amine salt of sulfonated copper phthalocyanine is from 6:1 to 45:1.
In some embodiments, the ink composition comprises
- a methyl ester of a C18 monounsaturated fatty acid;
- beta-form copper phthalocyanine having a bulk density of from 0.46 kgL-1 to 0.60 kgL-1;
- a C14-C18 hydrocarbon which is a mixture of one or more C14-C18 n-alkane, one or more C14-C18 isoalkane, one or more non-aromatic cyclic C14-C18 hydrocarbon, and one or more aromatic C14-C18 hydrocarbon;
- a fatty acid amine salt of sulfonated copper phthalocyanine comprising a copper phthalocyanine sulfonate anion having one sulfonate groups, and a quaternary ammonium cation having, attached to the quaternary nitrogen atom, 2 C16 to C20 hydrocarbon groups and 2 groups selected from hydrogen and C1 to C2 alkyl; and
- an alkyd resin comprising an ester of a di-unsaturated fatty acid and a polyhydric alcohol; wherein the weight ratio of the C14-C18 hydrocarbon to the fatty acid amine salt of sulfonated copper phthalocyanine is from 6:1 to 45:1.
- a methyl ester of a C18 monounsaturated fatty acid;
- beta-form copper phthalocyanine having a bulk density of from 0.46 kgL-1 to 0.60 kgL-1;
- a C14-C18 hydrocarbon which is a mixture of one or more C14-C18 n-alkane, one or more C14-C18 isoalkane, one or more non-aromatic cyclic C14-C18 hydrocarbon, and one or more aromatic C14-C18 hydrocarbon;
- a fatty acid amine salt of sulfonated copper phthalocyanine comprising a copper phthalocyanine sulfonate anion having one sulfonate groups, and a quaternary ammonium cation having, attached to the quaternary nitrogen atom, 2 C16 to C20 hydrocarbon groups and 2 groups selected from hydrogen and C1 to C2 alkyl; and
- an alkyd resin comprising an ester of a di-unsaturated fatty acid and a polyhydric alcohol; wherein the weight ratio of the C14-C18 hydrocarbon to the fatty acid amine salt of sulfonated copper phthalocyanine is from 6:1 to 45:1.
In some embodiments, the ink composition comprises
- 60 wt％ to 90 wt％, based on the total weight of the composition, of a methyl ester of a C16-C18 monounsaturated fatty acid;
- 2 wt％ to 18 wt％, based on the total weight of the composition, of beta-form copper phthalocyanine having a bulk density of from 0.42 kgL-1 to 1.00 kgL-1;4 wt％ to 18 wt％, based on the total weight of the composition, of a C14-C18 hydrocarbon which is a mixture of compounds selected from the group consisting of C14-C18 n-alkanes, C14-C18 isoalkanes, non-aromatic cyclic C14-C18 hydrocarbons, and aromatic C14-C18 hydrocarbons;
- 0.06 wt％ to 0.50 wt％, based on the total weight of the composition, of a fatty acid amine salt of sulfonated copper phthalocyanine comprising a copper phthalocyanine sulfonate anion having one, two, three or four sulfonate groups, and a quaternary ammonium cation having, attached to the quaternary nitrogen atom, n C8 to C22 hydrocarbon groups and 4-n groups selected from hydrogen and C1 to C7 alkyl, wherein n is from 1 to 4; and
- 1 wt％ to 6 wt％, based on the total weight of the composition, of an alkyd resin; wherein the weight ratio of the C14-C18 hydrocarbon to the fatty acid amine salt of sulfonated copper phthalocyanine is from 6:1 to 45:1.
- 60 wt％ to 90 wt％, based on the total weight of the composition, of a methyl ester of a C16-C18 monounsaturated fatty acid;
- 2 wt％ to 18 wt％, based on the total weight of the composition, of beta-form copper phthalocyanine having a bulk density of from 0.42 kgL-1 to 1.00 kgL-1;4 wt％ to 18 wt％, based on the total weight of the composition, of a C14-C18 hydrocarbon which is a mixture of compounds selected from the group consisting of C14-C18 n-alkanes, C14-C18 isoalkanes, non-aromatic cyclic C14-C18 hydrocarbons, and aromatic C14-C18 hydrocarbons;
- 0.06 wt％ to 0.50 wt％, based on the total weight of the composition, of a fatty acid amine salt of sulfonated copper phthalocyanine comprising a copper phthalocyanine sulfonate anion having one, two, three or four sulfonate groups, and a quaternary ammonium cation having, attached to the quaternary nitrogen atom, n C8 to C22 hydrocarbon groups and 4-n groups selected from hydrogen and C1 to C7 alkyl, wherein n is from 1 to 4; and
- 1 wt％ to 6 wt％, based on the total weight of the composition, of an alkyd resin; wherein the weight ratio of the C14-C18 hydrocarbon to the fatty acid amine salt of sulfonated copper phthalocyanine is from 6:1 to 45:1.
In some embodiments, the ink composition comprises
- 70 wt％ to 80 wt％, based on the total weight of the composition, of a methyl ester of a C18 monounsaturated fatty acid;
- 6 wt％ to 14 wt％, based on the total weight of the composition, of beta-form copper phthalocyanine having a bulk density of from 0.46 kgL-1 to 0.60 kgL-1;
- 8 wt％ to 14 wt％, based on the total weight of the composition, of a C14-C18 hydrocarbon which is a mixture of one or more C14-C18 n-alkane, one or more C14-C18 isoalkane, one or more non-aromatic cyclic C14-C18 hydrocarbon, and one or more aromatic C14-C18 hydrocarbon, wherein the one or more aromatic C14-C18 hydrocarbon is present in an amount of 2 wt％ to 30wt％, based on the total weight of the C14-C18 hydrocarbon;
- 0.12 wt％ to 0.40 wt％, based on the total weight of the composition, of a fatty acid amine salt of sulfonated copper phthalocyanine comprising a copper phthalocyanine sulfonate anion having one sulfonate groups, and a quaternary ammonium cation having, attached to the quaternary nitrogen atom, 2 C16 to C20 hydrocarbon groups and 2 groups selected from hydrogen and C1 to C2 alkyl; and
- 2 wt％ to 4 wt％, based on the total weight of the composition, of an alkyd resin comprising an ester of a di-unsaturated fatty acid and a polyhydric alcohol; wherein the weight ratio of the C14-C18 hydrocarbon to the fatty acid amine salt of sulfonated copper phthalocyanine is from 6:1 to 40:1 (or from 6.25:1 to 40:1).
- 70 wt％ to 80 wt％, based on the total weight of the composition, of a methyl ester of a C18 monounsaturated fatty acid;
- 6 wt％ to 14 wt％, based on the total weight of the composition, of beta-form copper phthalocyanine having a bulk density of from 0.46 kgL-1 to 0.60 kgL-1;
- 8 wt％ to 14 wt％, based on the total weight of the composition, of a C14-C18 hydrocarbon which is a mixture of one or more C14-C18 n-alkane, one or more C14-C18 isoalkane, one or more non-aromatic cyclic C14-C18 hydrocarbon, and one or more aromatic C14-C18 hydrocarbon, wherein the one or more aromatic C14-C18 hydrocarbon is present in an amount of 2 wt％ to 30wt％, based on the total weight of the C14-C18 hydrocarbon;
- 0.12 wt％ to 0.40 wt％, based on the total weight of the composition, of a fatty acid amine salt of sulfonated copper phthalocyanine comprising a copper phthalocyanine sulfonate anion having one sulfonate groups, and a quaternary ammonium cation having, attached to the quaternary nitrogen atom, 2 C16 to C20 hydrocarbon groups and 2 groups selected from hydrogen and C1 to C2 alkyl; and
- 2 wt％ to 4 wt％, based on the total weight of the composition, of an alkyd resin comprising an ester of a di-unsaturated fatty acid and a polyhydric alcohol; wherein the weight ratio of the C14-C18 hydrocarbon to the fatty acid amine salt of sulfonated copper phthalocyanine is from 6:1 to 40:1 (or from 6.25:1 to 40:1).
The ink compositions of the present invention can be prepared by techniques known in the art, for example by providing the components of the composition. The components of the composition may be milled and/or subjected to ultrasonic dispersion (e.g. in an ultrasonic dispersion bath).
The ink compositions of the present invention can be used as inkjet inks. For example they can be printed onto a substrate using an inkjet printer according to techniques known in the art. The substrate is not particularly limited and includes, for example, paper, card, and board. A printed article comprising a substrate and an ink composition of the present invention can be obtained by printing the ink onto the substrate, e.g. by inkjet printing.
The invention is illustrated below by means of the following non-limiting examples. All Examples and Comparative Examples used methyl oleate (METHYL OLEATE P, from Mosselman S.A) as the carrier, a C14-C18 hydrocarbon with a flash point of 96℃ (Solsperse 13940 from The Lubrizol Corporation) as the dispersant, and an alkyd resin (Vilkyd 782) as a resin.
Examples 1 to 4 and Comparative Examples 2 and 3 used a fatty acid amine salt of sulfonated copper phthalocyanine (Solsperse 5000S from The Lubrizol Corporation; Dispersant Synergist 1) as a dispersant synergist. Comparative Example 4 used a VOC free fatty acid-based polymer (ADD-6245 from ADD Additives BV; Dispersant Synergist 2) as a dispersant synergist.
Examples 1 to 4 and Comparative Examples 1, 2 and 4 used a beta-form copper phthalocyanine having a bulk density of 0.48 kgL-1 (Lionol Blue FG-7400G (15:4) from Toyocolor Co., Ltd.; bulk density measured according to ASTM D1895-17; Pigment 1) as the pigment. Comparative Example 3 used a beta-form copper phthalocyanine having a bulk density of 0.33 kgL-1 (Heliogen Blue L 7101F (15:4) from Sun Chemical Colors & Effects GmbH; bulk density measured according to ASTM D1895-17; Pigment 2) as the pigment.
Ink compositions having the components set out in Table 1 were prepared as Examples 1 to 4. Ink compositions having the components set out in Table 2 were prepared as Comparative Examples 1 to 4. The compositions of Examples 1, 2 and 4, and Comparative Examples 1 2 and 3, were prepared by milling components in a MiniZeta laboratory mill. The compositions of Example 3 and Comparative Example 4 were prepared by dispersion in an ultrasonic bath.
The inks of Examples 1 to 4 and Comparative Examples 1 to 4 were evaluated for stability of particle size and stability of viscosity. The results are set out in Table 3.
As evidenced in the examples, the combination of dispersant synergist and dispersant according to the present invention produces good particle size stability and viscosity stability when using a plant-based carrier fluid and a high flashpoint dispersant.
The invention is described above with reference to certain embodiments. However, those embodiments are merely illustrative and a skilled person will appreciate that various modifications are possible, including combinations of features which are described above with reference to separate embodiments, without departing from the scope of the invention as defined in the following claims (with due account being taken of equivalents thereto).
The present application is based on and claims priority of United Kingdom Priority Application No. GB 2218413.9 filed on December 7, 2022, the entire contents of which are hereby incorporated herein by reference.
Claims (15)
- An ink composition comprising:
- a methyl ester of a C16-C18 fatty acid;
- beta-form copper phthalocyanine having a bulk density of 0.40 kgL-1 or more;
- a C14-C18 hydrocarbon; and
- a fatty acid amine salt of sulfonated copper phthalocyanine; wherein the weight ratio of the C14-C18 hydrocarbon to the fatty acid amine salt of sulfonated copper phthalocyanine is from 6:1 to 45:1.
- An ink composition according to claim 1, wherein the weight ratio of the C14-C18 hydrocarbon to the fatty acid amine salt of sulfonated copper phthalocyanine is from 6.25:1 to 40:1.
- An ink composition according to claim 1 or 2, wherein the methyl ester of a C16-C18 fatty acid is present in an amount of 60 wt％ to 90 wt％, based on the total weight of the composition.
- An ink composition according to any one of claims 1 to 3, wherein the methyl ester of a C16-C18 fatty acid is a plant-based material.
- An ink composition according to any one of claims 1 to 4, wherein the beta-form copper phthalocyanine is present in an amount of 2 wt％ to 18 wt％, based on the total weight of the composition.
- An ink composition according to any one of claims 1 to 5, wherein the beta-form copper phthalocyanine has a bulk density of from 0.42 kgL-1 to 1.00 kgL-1.
- An ink composition according to any one of claims 1 to 6, wherein the C14-C18 hydrocarbon is present in an amount of 4 wt％ to 18 wt％, based on the total weight of the composition.
- An ink composition according to any one of claims 1 to 7, wherein the C14-C18 hydrocarbon is is a mixture of compounds selected from the group consisting of C14-C18 n- alkanes, C14-C18 isoalkanes, non-aromatic cyclic C14-C18 hydrocarbons, and aromatic C14- C18 hydrocarbons.
- An ink composition according to any one of claims 1 to 8, further comprising:
- an alkyd resin.
- An ink composition according to claim 9, wherein the alkyd resin is present in an amount of 1 wt％ to 6 wt％, based on the total weight of the composition.
- An ink composition according to claim 9, wherein the alkyd resin is present in an amount of 1 wt％ to 6 wt％, based on the total weight of the composition.
- A method of manufacturing an ink composition comprising:
- providing a methyl ester of a C16-C18 fatty acid;
- providing beta-form copper phthalocyanine having a bulk density of 0.40 kgL-1 or more;
- providing a C14-C18 hydrocarbon; and
- providing a fatty acid amine salt of sulfonated copper phthalocyanine; wherein the weight ratio of the C14-C18 hydrocarbon to the fatty acid amine salt of sulfonated copper phthalocyanine is from 6:1 to 45:1.
- A method according to claim 12, wherein the methyl ester of a C16-C18 fatty acid; the beta-form copper phthalocyanine; the C14-C18 hydrocarbon; and/or the fatty acid amine salt of sulfonated copper phthalocyanine is as defined in any one of claims 2 to 11.
- A method of printing comprising:
- providing an ink composition as defined in any one of claims 1 to 11; and
- using an inkjet printer to print the ink composition onto a substrate.
- A printed article comprising a substrate and an ink composition as defined in any one of claims 1 to 11.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB2218413.9 | 2022-12-07 | ||
| GBGB2218413.9A GB202218413D0 (en) | 2022-12-07 | 2022-12-07 | Ink compositions |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| WO2024122422A1 true WO2024122422A1 (en) | 2024-06-13 |
Family
ID=84926594
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PCT/JP2023/042658 WO2024122422A1 (en) | 2022-12-07 | 2023-11-29 | Ink compositions |
Country Status (2)
| Country | Link |
|---|---|
| GB (1) | GB202218413D0 (en) |
| WO (1) | WO2024122422A1 (en) |
Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1997015633A1 (en) * | 1995-10-23 | 1997-05-01 | Xaar Technology Limited | Ink jet printer dispersion inks |
| US5837046A (en) * | 1995-02-08 | 1998-11-17 | Xaar Technology Limited | Ink jet printer ink composition |
| JP2001031900A (en) * | 1999-05-20 | 2001-02-06 | Hitachi Maxell Ltd | Dispersion composition and its production |
| JP2004137315A (en) * | 2002-10-16 | 2004-05-13 | Hitachi Maxell Ltd | Ink composition |
| JP2005290064A (en) * | 2004-03-31 | 2005-10-20 | Riso Kagaku Corp | Oily ink for ink-jet recording |
-
2022
- 2022-12-07 GB GBGB2218413.9A patent/GB202218413D0/en not_active Ceased
-
2023
- 2023-11-29 WO PCT/JP2023/042658 patent/WO2024122422A1/en unknown
Patent Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5837046A (en) * | 1995-02-08 | 1998-11-17 | Xaar Technology Limited | Ink jet printer ink composition |
| WO1997015633A1 (en) * | 1995-10-23 | 1997-05-01 | Xaar Technology Limited | Ink jet printer dispersion inks |
| JP2001031900A (en) * | 1999-05-20 | 2001-02-06 | Hitachi Maxell Ltd | Dispersion composition and its production |
| JP2004137315A (en) * | 2002-10-16 | 2004-05-13 | Hitachi Maxell Ltd | Ink composition |
| JP2005290064A (en) * | 2004-03-31 | 2005-10-20 | Riso Kagaku Corp | Oily ink for ink-jet recording |
Non-Patent Citations (2)
| Title |
|---|
| "CRC Handbook of Chemistry and Physics", 1979, CRC PRESS |
| J. M. ROBERTSON, J. CHEM. SOC., no. 67762-38-3, 1935, pages 615 |
Also Published As
| Publication number | Publication date |
|---|---|
| GB202218413D0 (en) | 2023-01-18 |
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