CA2737612C - Phase change inks containing amide gellant compounds with aromatic end groups - Google Patents
Phase change inks containing amide gellant compounds with aromatic end groups Download PDFInfo
- Publication number
- CA2737612C CA2737612C CA2737612A CA2737612A CA2737612C CA 2737612 C CA2737612 C CA 2737612C CA 2737612 A CA2737612 A CA 2737612A CA 2737612 A CA2737612 A CA 2737612A CA 2737612 C CA2737612 C CA 2737612C
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- Canada
- Prior art keywords
- group
- ink
- groups
- formula
- phase change
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Fee Related
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- 230000008859 change Effects 0.000 title claims abstract description 76
- 150000001875 compounds Chemical class 0.000 title claims abstract description 76
- 125000003118 aryl group Chemical group 0.000 title claims abstract description 67
- 239000000976 ink Substances 0.000 title description 203
- 239000003349 gelling agent Substances 0.000 title description 95
- 150000001408 amides Chemical class 0.000 title description 22
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 75
- 125000002947 alkylene group Chemical group 0.000 claims abstract description 67
- 125000000732 arylene group Chemical group 0.000 claims abstract description 46
- 238000000034 method Methods 0.000 claims abstract description 28
- 125000002877 alkyl aryl group Chemical group 0.000 claims abstract description 25
- 239000003086 colorant Substances 0.000 claims abstract description 25
- 125000003710 aryl alkyl group Chemical group 0.000 claims abstract description 24
- 239000000178 monomer Substances 0.000 claims abstract description 23
- 239000003999 initiator Substances 0.000 claims abstract description 18
- 239000000203 mixture Substances 0.000 claims description 66
- 125000004122 cyclic group Chemical group 0.000 claims description 39
- 239000000758 substrate Substances 0.000 claims description 28
- 230000008569 process Effects 0.000 claims description 21
- -1 methacrylate compound Chemical class 0.000 claims description 16
- 230000005855 radiation Effects 0.000 claims description 14
- 238000007641 inkjet printing Methods 0.000 claims description 12
- 238000002844 melting Methods 0.000 claims description 11
- 230000008018 melting Effects 0.000 claims description 11
- RZFODFPMOHAYIR-UHFFFAOYSA-N oxepan-2-one;prop-2-enoic acid Chemical compound OC(=O)C=C.O=C1CCCCCO1 RZFODFPMOHAYIR-UHFFFAOYSA-N 0.000 claims description 9
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims description 8
- PSGCQDPCAWOCSH-UHFFFAOYSA-N (4,7,7-trimethyl-3-bicyclo[2.2.1]heptanyl) prop-2-enoate Chemical compound C1CC2(C)C(OC(=O)C=C)CC1C2(C)C PSGCQDPCAWOCSH-UHFFFAOYSA-N 0.000 claims description 3
- RZVINYQDSSQUKO-UHFFFAOYSA-N 2-phenoxyethyl prop-2-enoate Chemical compound C=CC(=O)OCCOC1=CC=CC=C1 RZVINYQDSSQUKO-UHFFFAOYSA-N 0.000 claims description 3
- NQSLZEHVGKWKAY-UHFFFAOYSA-N 6-methylheptyl 2-methylprop-2-enoate Chemical compound CC(C)CCCCCOC(=O)C(C)=C NQSLZEHVGKWKAY-UHFFFAOYSA-N 0.000 claims description 3
- DXPPIEDUBFUSEZ-UHFFFAOYSA-N 6-methylheptyl prop-2-enoate Chemical compound CC(C)CCCCCOC(=O)C=C DXPPIEDUBFUSEZ-UHFFFAOYSA-N 0.000 claims description 3
- COCLLEMEIJQBAG-UHFFFAOYSA-N 8-methylnonyl 2-methylprop-2-enoate Chemical compound CC(C)CCCCCCCOC(=O)C(C)=C COCLLEMEIJQBAG-UHFFFAOYSA-N 0.000 claims description 3
- LVGFPWDANALGOY-UHFFFAOYSA-N 8-methylnonyl prop-2-enoate Chemical compound CC(C)CCCCCCCOC(=O)C=C LVGFPWDANALGOY-UHFFFAOYSA-N 0.000 claims description 3
- IAXXETNIOYFMLW-COPLHBTASA-N [(1s,3s,4s)-4,7,7-trimethyl-3-bicyclo[2.2.1]heptanyl] 2-methylprop-2-enoate Chemical compound C1C[C@]2(C)[C@@H](OC(=O)C(=C)C)C[C@H]1C2(C)C IAXXETNIOYFMLW-COPLHBTASA-N 0.000 claims description 3
- CQEYYJKEWSMYFG-UHFFFAOYSA-N butyl acrylate Chemical compound CCCCOC(=O)C=C CQEYYJKEWSMYFG-UHFFFAOYSA-N 0.000 claims description 3
- GMSCBRSQMRDRCD-UHFFFAOYSA-N dodecyl 2-methylprop-2-enoate Chemical compound CCCCCCCCCCCCOC(=O)C(C)=C GMSCBRSQMRDRCD-UHFFFAOYSA-N 0.000 claims description 3
- 229940119545 isobornyl methacrylate Drugs 0.000 claims description 3
- PBOSTUDLECTMNL-UHFFFAOYSA-N lauryl acrylate Chemical compound CCCCCCCCCCCCOC(=O)C=C PBOSTUDLECTMNL-UHFFFAOYSA-N 0.000 claims description 3
- 238000007639 printing Methods 0.000 abstract description 17
- 239000012071 phase Substances 0.000 description 68
- 125000005842 heteroatom Chemical group 0.000 description 51
- 125000004432 carbon atom Chemical group C* 0.000 description 43
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 41
- 239000002904 solvent Substances 0.000 description 38
- 125000002015 acyclic group Chemical group 0.000 description 36
- 239000007787 solid Substances 0.000 description 35
- 239000000499 gel Substances 0.000 description 34
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 32
- 229920006395 saturated elastomer Polymers 0.000 description 32
- 238000006243 chemical reaction Methods 0.000 description 31
- 238000003756 stirring Methods 0.000 description 25
- 239000000126 substance Substances 0.000 description 24
- 239000007822 coupling agent Substances 0.000 description 21
- 239000000047 product Substances 0.000 description 21
- 230000000052 comparative effect Effects 0.000 description 20
- 239000003054 catalyst Substances 0.000 description 17
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 16
- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 16
- 239000000725 suspension Substances 0.000 description 16
- 150000004985 diamines Chemical class 0.000 description 15
- 239000000049 pigment Substances 0.000 description 15
- 239000000463 material Substances 0.000 description 14
- 239000006227 byproduct Substances 0.000 description 13
- 150000002148 esters Chemical class 0.000 description 13
- 238000012546 transfer Methods 0.000 description 13
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 12
- 239000000243 solution Substances 0.000 description 12
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 11
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 11
- 239000002243 precursor Substances 0.000 description 11
- 239000011541 reaction mixture Substances 0.000 description 11
- SCCCIUGOOQLDGW-UHFFFAOYSA-N 1,1-dicyclohexylurea Chemical compound C1CCCCC1N(C(=O)N)C1CCCCC1 SCCCIUGOOQLDGW-UHFFFAOYSA-N 0.000 description 10
- 125000001931 aliphatic group Chemical group 0.000 description 10
- 229910052799 carbon Inorganic materials 0.000 description 10
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 9
- 238000002835 absorbance Methods 0.000 description 9
- 239000000975 dye Substances 0.000 description 9
- 239000000706 filtrate Substances 0.000 description 9
- 239000007788 liquid Substances 0.000 description 9
- 239000013557 residual solvent Substances 0.000 description 9
- QJNLUNBGDFUULX-UHFFFAOYSA-N 4-n,4-n'-dimethyl-3h-pyridine-4,4-diamine Chemical compound CNC1(NC)CC=NC=C1 QJNLUNBGDFUULX-UHFFFAOYSA-N 0.000 description 8
- 101150041968 CDC13 gene Proteins 0.000 description 8
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 8
- 239000006185 dispersion Substances 0.000 description 8
- 230000002829 reductive effect Effects 0.000 description 8
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 7
- 238000001723 curing Methods 0.000 description 7
- PCKZAVNWRLEHIP-UHFFFAOYSA-N 2-hydroxy-1-[4-[[4-(2-hydroxy-2-methylpropanoyl)phenyl]methyl]phenyl]-2-methylpropan-1-one Chemical compound C1=CC(C(=O)C(C)(O)C)=CC=C1CC1=CC=C(C(=O)C(C)(C)O)C=C1 PCKZAVNWRLEHIP-UHFFFAOYSA-N 0.000 description 6
- QCDWFXQBSFUVSP-UHFFFAOYSA-N 2-phenoxyethanol Chemical compound OCCOC1=CC=CC=C1 QCDWFXQBSFUVSP-UHFFFAOYSA-N 0.000 description 6
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 6
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 6
- 239000002253 acid Substances 0.000 description 6
- 230000000694 effects Effects 0.000 description 6
- 238000010438 heat treatment Methods 0.000 description 6
- 239000012943 hotmelt Substances 0.000 description 6
- 125000001424 substituent group Chemical group 0.000 description 6
- 239000003981 vehicle Substances 0.000 description 6
- 238000005160 1H NMR spectroscopy Methods 0.000 description 5
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 5
- 230000001965 increasing effect Effects 0.000 description 5
- 229910052760 oxygen Inorganic materials 0.000 description 5
- 239000001301 oxygen Substances 0.000 description 5
- 241000894007 species Species 0.000 description 5
- 230000003595 spectral effect Effects 0.000 description 5
- 230000007704 transition Effects 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- 229910019142 PO4 Inorganic materials 0.000 description 4
- 239000004952 Polyamide Substances 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- 239000003963 antioxidant agent Substances 0.000 description 4
- 238000001816 cooling Methods 0.000 description 4
- 239000003085 diluting agent Substances 0.000 description 4
- 239000000539 dimer Substances 0.000 description 4
- 238000001879 gelation Methods 0.000 description 4
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 4
- 239000010452 phosphate Substances 0.000 description 4
- 229910000073 phosphorus hydride Inorganic materials 0.000 description 4
- 229920002647 polyamide Polymers 0.000 description 4
- 238000006116 polymerization reaction Methods 0.000 description 4
- 238000012360 testing method Methods 0.000 description 4
- 238000005406 washing Methods 0.000 description 4
- 229920002799 BoPET Polymers 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 3
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
- 239000005041 Mylar™ Substances 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 238000005481 NMR spectroscopy Methods 0.000 description 3
- JKIJEFPNVSHHEI-UHFFFAOYSA-N Phenol, 2,4-bis(1,1-dimethylethyl)-, phosphite (3:1) Chemical compound CC(C)(C)C1=CC(C(C)(C)C)=CC=C1OP(OC=1C(=CC(=CC=1)C(C)(C)C)C(C)(C)C)OC1=CC=C(C(C)(C)C)C=C1C(C)(C)C JKIJEFPNVSHHEI-UHFFFAOYSA-N 0.000 description 3
- UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 150000008065 acid anhydrides Chemical class 0.000 description 3
- 125000002252 acyl group Chemical group 0.000 description 3
- 239000000654 additive Substances 0.000 description 3
- 150000001299 aldehydes Chemical class 0.000 description 3
- 230000003078 antioxidant effect Effects 0.000 description 3
- 150000001540 azides Chemical class 0.000 description 3
- 125000000751 azo group Chemical group [*]N=N[*] 0.000 description 3
- 239000004202 carbamide Substances 0.000 description 3
- 239000006229 carbon black Substances 0.000 description 3
- 235000019241 carbon black Nutrition 0.000 description 3
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 3
- 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 description 3
- 230000003993 interaction Effects 0.000 description 3
- 150000002576 ketones Chemical class 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 150000002825 nitriles Chemical class 0.000 description 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 3
- XYFCBTPGUUZFHI-UHFFFAOYSA-O phosphonium Chemical compound [PH4+] XYFCBTPGUUZFHI-UHFFFAOYSA-O 0.000 description 3
- 150000003254 radicals Chemical class 0.000 description 3
- 230000002441 reversible effect Effects 0.000 description 3
- PXQLVRUNWNTZOS-UHFFFAOYSA-N sulfanyl Chemical class [SH] PXQLVRUNWNTZOS-UHFFFAOYSA-N 0.000 description 3
- 125000002813 thiocarbonyl group Chemical group *C(*)=S 0.000 description 3
- 239000001993 wax Substances 0.000 description 3
- 239000012956 1-hydroxycyclohexylphenyl-ketone Substances 0.000 description 2
- GJKGAPPUXSSCFI-UHFFFAOYSA-N 2-Hydroxy-4'-(2-hydroxyethoxy)-2-methylpropiophenone Chemical compound CC(C)(O)C(=O)C1=CC=C(OCCO)C=C1 GJKGAPPUXSSCFI-UHFFFAOYSA-N 0.000 description 2
- FDSUVTROAWLVJA-UHFFFAOYSA-N 2-[[3-hydroxy-2,2-bis(hydroxymethyl)propoxy]methyl]-2-(hydroxymethyl)propane-1,3-diol;prop-2-enoic acid Chemical compound OC(=O)C=C.OC(=O)C=C.OC(=O)C=C.OC(=O)C=C.OC(=O)C=C.OCC(CO)(CO)COCC(CO)(CO)CO FDSUVTROAWLVJA-UHFFFAOYSA-N 0.000 description 2
- WRMNZCZEMHIOCP-UHFFFAOYSA-N 2-phenylethanol Chemical compound OCCC1=CC=CC=C1 WRMNZCZEMHIOCP-UHFFFAOYSA-N 0.000 description 2
- 239000012958 Amine synergist Substances 0.000 description 2
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 2
- 239000004215 Carbon black (E152) Substances 0.000 description 2
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 2
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 description 2
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 2
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 230000002411 adverse Effects 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 230000008901 benefit Effects 0.000 description 2
- 235000019445 benzyl alcohol Nutrition 0.000 description 2
- 230000005540 biological transmission Effects 0.000 description 2
- MQDJYUACMFCOFT-UHFFFAOYSA-N bis[2-(1-hydroxycyclohexyl)phenyl]methanone Chemical compound C=1C=CC=C(C(=O)C=2C(=CC=CC=2)C2(O)CCCCC2)C=1C1(O)CCCCC1 MQDJYUACMFCOFT-UHFFFAOYSA-N 0.000 description 2
- 229910052796 boron Inorganic materials 0.000 description 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical class OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 2
- 239000000969 carrier Substances 0.000 description 2
- 239000012876 carrier material Substances 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- VVOLVFOSOPJKED-UHFFFAOYSA-N copper phthalocyanine Chemical compound [Cu].N=1C2=NC(C3=CC=CC=C33)=NC3=NC(C3=CC=CC=C33)=NC3=NC(C3=CC=CC=C33)=NC3=NC=1C1=CC=CC=C12 VVOLVFOSOPJKED-UHFFFAOYSA-N 0.000 description 2
- 238000004132 cross linking Methods 0.000 description 2
- 235000014113 dietary fatty acids Nutrition 0.000 description 2
- 238000009792 diffusion process Methods 0.000 description 2
- 238000010017 direct printing Methods 0.000 description 2
- 239000002270 dispersing agent Substances 0.000 description 2
- 239000000194 fatty acid Substances 0.000 description 2
- 229930195729 fatty acid Natural products 0.000 description 2
- 150000004665 fatty acids Chemical class 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 238000009472 formulation Methods 0.000 description 2
- 230000008014 freezing Effects 0.000 description 2
- 238000007710 freezing Methods 0.000 description 2
- 230000004927 fusion Effects 0.000 description 2
- 229930195733 hydrocarbon Natural products 0.000 description 2
- 150000002430 hydrocarbons Chemical class 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
- 239000004615 ingredient Substances 0.000 description 2
- 239000007791 liquid phase Substances 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
- YDKNBNOOCSNPNS-UHFFFAOYSA-N methyl 1,3-benzoxazole-2-carboxylate Chemical compound C1=CC=C2OC(C(=O)OC)=NC2=C1 YDKNBNOOCSNPNS-UHFFFAOYSA-N 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 125000000018 nitroso group Chemical group N(=O)* 0.000 description 2
- 230000003647 oxidation Effects 0.000 description 2
- 238000007254 oxidation reaction Methods 0.000 description 2
- GVKCHTBDSMQENH-UHFFFAOYSA-L phloxine B Chemical compound [Na+].[Na+].[O-]C(=O)C1=C(Cl)C(Cl)=C(Cl)C(Cl)=C1C1=C2C=C(Br)C(=O)C(Br)=C2OC2=C(Br)C([O-])=C(Br)C=C21 GVKCHTBDSMQENH-UHFFFAOYSA-L 0.000 description 2
- 229910052698 phosphorus Inorganic materials 0.000 description 2
- 239000011574 phosphorus Substances 0.000 description 2
- 239000004033 plastic Substances 0.000 description 2
- 229920003023 plastic Polymers 0.000 description 2
- 229920001343 polytetrafluoroethylene Polymers 0.000 description 2
- 239000004810 polytetrafluoroethylene Substances 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 238000012545 processing Methods 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-O pyridinium Chemical compound C1=CC=[NH+]C=C1 JUJWROOIHBZHMG-UHFFFAOYSA-O 0.000 description 2
- 238000010526 radical polymerization reaction Methods 0.000 description 2
- 230000004044 response Effects 0.000 description 2
- 238000002390 rotary evaporation Methods 0.000 description 2
- 229910052710 silicon Inorganic materials 0.000 description 2
- 239000010703 silicon Substances 0.000 description 2
- 239000000377 silicon dioxide Substances 0.000 description 2
- 239000007790 solid phase Substances 0.000 description 2
- 239000000992 solvent dye Substances 0.000 description 2
- 239000003381 stabilizer Substances 0.000 description 2
- 229910052717 sulfur Inorganic materials 0.000 description 2
- 239000011593 sulfur Substances 0.000 description 2
- QNODIIQQMGDSEF-UHFFFAOYSA-N (1-hydroxycyclohexyl)-phenylmethanone Chemical compound C=1C=CC=CC=1C(=O)C1(O)CCCCC1 QNODIIQQMGDSEF-UHFFFAOYSA-N 0.000 description 1
- WXPWZZHELZEVPO-UHFFFAOYSA-N (4-methylphenyl)-phenylmethanone Chemical compound C1=CC(C)=CC=C1C(=O)C1=CC=CC=C1 WXPWZZHELZEVPO-UHFFFAOYSA-N 0.000 description 1
- MYWOJODOMFBVCB-UHFFFAOYSA-N 1,2,6-trimethylphenanthrene Chemical compound CC1=CC=C2C3=CC(C)=CC=C3C=CC2=C1C MYWOJODOMFBVCB-UHFFFAOYSA-N 0.000 description 1
- YFKBXYGUSOXJGS-UHFFFAOYSA-N 1,3-Diphenyl-2-propanone Chemical class C=1C=CC=CC=1CC(=O)CC1=CC=CC=C1 YFKBXYGUSOXJGS-UHFFFAOYSA-N 0.000 description 1
- ZDQNWDNMNKSMHI-UHFFFAOYSA-N 1-[2-(2-prop-2-enoyloxypropoxy)propoxy]propan-2-yl prop-2-enoate Chemical compound C=CC(=O)OC(C)COC(C)COCC(C)OC(=O)C=C ZDQNWDNMNKSMHI-UHFFFAOYSA-N 0.000 description 1
- VOBUAPTXJKMNCT-UHFFFAOYSA-N 1-prop-2-enoyloxyhexyl prop-2-enoate Chemical compound CCCCCC(OC(=O)C=C)OC(=O)C=C VOBUAPTXJKMNCT-UHFFFAOYSA-N 0.000 description 1
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- B01F23/00—Mixing according to the phases to be mixed, e.g. dispersing or emulsifying
- B01F23/20—Mixing gases with liquids
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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
- C09D11/02—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
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D11/00—Inks
- C09D11/30—Inkjet printing inks
- C09D11/34—Hot-melt inks
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B41—PRINTING; LINING MACHINES; TYPEWRITERS; STAMPS
- B41M—PRINTING, DUPLICATING, MARKING, OR COPYING PROCESSES; COLOUR PRINTING
- B41M7/00—After-treatment of prints, e.g. heating, irradiating, setting of the ink, protection of the printed stock
- B41M7/0072—After-treatment of prints, e.g. heating, irradiating, setting of the ink, protection of the printed stock using mechanical wave energy, e.g. ultrasonics; using magnetic or electric fields, e.g. electric discharge, plasma
Landscapes
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- Materials Engineering (AREA)
- Wood Science & Technology (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Inks, Pencil-Leads, Or Crayons (AREA)
- Ink Jet Recording Methods And Recording Media Thereof (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US12/765,138 | 2010-04-22 | ||
| US12/765,138 US8507584B2 (en) | 2010-04-22 | 2010-04-22 | Phase change inks containing amide gellant compounds with aromatic end groups |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2737612A1 CA2737612A1 (en) | 2011-10-22 |
| CA2737612C true CA2737612C (en) | 2015-06-30 |
Family
ID=44816330
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2737612A Expired - Fee Related CA2737612C (en) | 2010-04-22 | 2011-04-15 | Phase change inks containing amide gellant compounds with aromatic end groups |
Country Status (5)
| Country | Link |
|---|---|
| US (1) | US8507584B2 (enExample) |
| JP (1) | JP5628733B2 (enExample) |
| CN (1) | CN102234462B (enExample) |
| CA (1) | CA2737612C (enExample) |
| DE (1) | DE102011006968B4 (enExample) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US8603612B2 (en) | 2010-04-22 | 2013-12-10 | Xerox Corporation | Curable compositions for three-dimensional printing |
| US8581000B2 (en) | 2011-06-06 | 2013-11-12 | Xerox Corporation | Process for preparing amide gellant compounds with aromatic end groups |
| US8702221B2 (en) * | 2012-05-08 | 2014-04-22 | Xerox Corporation | Gellant compositions with aromatic end-caps and oligomeric molecular weight distributions |
| US8882256B2 (en) * | 2012-06-11 | 2014-11-11 | Xerox Corporation | Low molecular weight amide gellants and methods for making the same |
| JP6712271B2 (ja) | 2014-12-18 | 2020-06-17 | キャノン・プロダクション・プリンティング・ネザーランズ・ベー・フェー | インク組成物 |
| US10696857B2 (en) * | 2017-12-14 | 2020-06-30 | Xerox Corporation | Curable gellant ink |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5194638A (en) | 1987-09-18 | 1993-03-16 | Union Camp Corporation | Resinous binders for use in ink compositions for ink jet printing |
| US4889560A (en) | 1988-08-03 | 1989-12-26 | Tektronix, Inc. | Phase change ink composition and phase change ink produced therefrom |
| US4889761A (en) | 1988-08-25 | 1989-12-26 | Tektronix, Inc. | Substrates having a light-transmissive phase change ink printed thereon and methods for producing same |
| US5195430A (en) | 1989-05-24 | 1993-03-23 | Tektronix, Inc. | Dual roller apparatus for pressure fixing sheet material |
| US5221335A (en) | 1990-05-23 | 1993-06-22 | Coates Electrographics Limited | Stabilized pigmented hot melt ink containing nitrogen-modified acrylate polymer as dispersion-stabilizer agent |
| US5389958A (en) | 1992-11-25 | 1995-02-14 | Tektronix, Inc. | Imaging process |
| US5621022A (en) | 1992-11-25 | 1997-04-15 | Tektronix, Inc. | Use of polymeric dyes in hot melt ink jet inks |
| US5372852A (en) | 1992-11-25 | 1994-12-13 | Tektronix, Inc. | Indirect printing process for applying selective phase change ink compositions to substrates |
| US5783657A (en) | 1996-10-18 | 1998-07-21 | Union Camp Corporation | Ester-terminated polyamides of polymerized fatty acids useful in formulating transparent gels in low polarity liquids |
| US6350889B1 (en) | 1999-06-24 | 2002-02-26 | Arizona Chemical Company | Ink jet printing compositions containing ester-terminated dimer acid-based oligo (ester/amide) |
| US6492458B1 (en) | 2000-05-16 | 2002-12-10 | Arizona Chemical Company | Polyalkyleneoxydiamine polyamides useful for formulating inks for phase-change jet printing |
| DE60122903T2 (de) | 2000-08-07 | 2006-12-21 | Eastman Chemical Co., Kingsport | Thermisch stabile anthrachinonfarbstoffe mit copolymerisierbaren vinylgruppen |
| US6399713B1 (en) | 2001-01-24 | 2002-06-04 | Arizona Chemical Company | Hydrocarbon-terminated polyether-polyamide block copolymers and uses thereof |
| US6870011B2 (en) | 2001-01-24 | 2005-03-22 | Arizona Chemical Company | Hydrocarbon-terminated polyether-polyamide block copolymers and uses thereof |
| US6989052B1 (en) | 2004-06-30 | 2006-01-24 | Xerox Corporation | Phase change ink printing process |
| US7033424B2 (en) * | 2004-07-23 | 2006-04-25 | Xerox Corporation | Phase change inks |
| US7317122B2 (en) | 2004-12-04 | 2008-01-08 | Xerox Corporation | Curable trans-1,2-cyclohexane bis(urea-urethane) compounds |
| US7293868B2 (en) | 2004-12-22 | 2007-11-13 | Xerox Corporation | Curable phase change ink composition |
| US7563313B2 (en) | 2005-07-13 | 2009-07-21 | Xerox Corporation | Ink carriers, phase change inks including same and methods for making same |
| US7276614B2 (en) | 2005-11-30 | 2007-10-02 | Xerox Corporation | Curable amide gellant compounds |
| US7538145B2 (en) | 2005-11-30 | 2009-05-26 | Xerox Corporation | Curable phase change compositions and methods for using such compositions |
| US7563314B2 (en) | 2005-11-30 | 2009-07-21 | Xerox Corporation | Ink carriers containing nanoparticles, phase change inks including same and methods for making same |
| US7571999B2 (en) | 2005-11-30 | 2009-08-11 | Xerox Corporation | Overcoat compositions, oil-based ink compositions, and processes for ink-jet recording using overcoat and oil-based ink compositions |
| US7665835B2 (en) | 2005-11-30 | 2010-02-23 | Xerox Corporation | Phase change inks and methods for making same |
| US7279587B2 (en) | 2005-11-30 | 2007-10-09 | Xerox Corporation | Photoinitiator with phase change properties and gellant affinity |
| US7578587B2 (en) | 2005-11-30 | 2009-08-25 | Xerox Corporation | Curable overcoat for wax-based inks |
| US7259275B2 (en) | 2005-11-30 | 2007-08-21 | Xerox Corporation | Method for preparing curable amide gellant compounds |
| US7674842B2 (en) | 2005-11-30 | 2010-03-09 | Xerox Corporation | Phase change inks containing curable isocyanate-derived compounds and phase change inducing components |
| US7572325B2 (en) | 2005-11-30 | 2009-08-11 | Xerox Corporation | Ink carriers, phase change inks including same and methods for making same |
| US7541406B2 (en) | 2005-11-30 | 2009-06-02 | Xerox Corporation | Phase change inks containing curable isocyanate-derived compounds |
| US7449515B2 (en) | 2005-11-30 | 2008-11-11 | Xerox Corporation | Phase change inks containing compounds derived from isocyanate, unsaturated alcohol, and polyol |
| US7632546B2 (en) | 2005-11-30 | 2009-12-15 | Xerox Corporation | Radiation curable phase change inks containing gellants |
| US7531033B2 (en) | 2005-11-30 | 2009-05-12 | Xerox Corporation | Pre-treatment compositions, oil-based ink compositions, and processes for ink-jet recording using pre-treatment compositions and oil-based ink compositions |
| US7559639B2 (en) | 2005-11-30 | 2009-07-14 | Xerox Corporation | Radiation curable ink containing a curable wax |
| US7625956B2 (en) | 2005-11-30 | 2009-12-01 | Xerox Corporation | Phase change inks containing photoinitiator with phase change properties and gellant affinity |
| US7501015B2 (en) | 2005-11-30 | 2009-03-10 | Xerox Corporation | Phase change inks |
| US7271284B2 (en) | 2005-11-30 | 2007-09-18 | Xerox Corporation | Process for making curable amide gellant compounds |
| US7578875B2 (en) | 2005-11-30 | 2009-08-25 | Xerox Corporation | Black inks and method for making same |
| US7563489B2 (en) | 2005-11-30 | 2009-07-21 | Xerox Corporation | Radiation curable phase change inks containing curable epoxy-polyamide composite gellants |
| US7699922B2 (en) | 2006-06-13 | 2010-04-20 | Xerox Corporation | Organic phase change carriers containing nanoparticles, phase change inks including same and methods for making same |
| US8142557B2 (en) | 2006-06-28 | 2012-03-27 | Xerox Corporation | Radiation curable ink containing gellant and radiation curable wax |
| US7812064B2 (en) * | 2007-08-07 | 2010-10-12 | Xerox Corporation | Phase change ink compositions |
| US8097661B2 (en) * | 2010-04-22 | 2012-01-17 | Xerox Corporation | Ink compositions and methods |
-
2010
- 2010-04-22 US US12/765,138 patent/US8507584B2/en active Active
-
2011
- 2011-04-07 DE DE102011006968.2A patent/DE102011006968B4/de not_active Expired - Fee Related
- 2011-04-15 CA CA2737612A patent/CA2737612C/en not_active Expired - Fee Related
- 2011-04-20 JP JP2011094524A patent/JP5628733B2/ja not_active Expired - Fee Related
- 2011-04-22 CN CN201110103983.8A patent/CN102234462B/zh not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| US20110263769A1 (en) | 2011-10-27 |
| DE102011006968B4 (de) | 2018-12-06 |
| CA2737612A1 (en) | 2011-10-22 |
| JP2011225879A (ja) | 2011-11-10 |
| DE102011006968A1 (de) | 2011-12-29 |
| CN102234462B (zh) | 2015-08-19 |
| CN102234462A (zh) | 2011-11-09 |
| US8507584B2 (en) | 2013-08-13 |
| JP5628733B2 (ja) | 2014-11-19 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request | ||
| MKLA | Lapsed |
Effective date: 20210415 |