CA2737567C - Ink compositions and methods - Google Patents
Ink compositions and methods Download PDFInfo
- Publication number
- CA2737567C CA2737567C CA2737567A CA2737567A CA2737567C CA 2737567 C CA2737567 C CA 2737567C CA 2737567 A CA2737567 A CA 2737567A CA 2737567 A CA2737567 A CA 2737567A CA 2737567 C CA2737567 C CA 2737567C
- Authority
- CA
- Canada
- Prior art keywords
- group
- groups
- ink
- gel
- curable
- 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
Links
- 238000000034 method Methods 0.000 title claims abstract description 40
- 239000000203 mixture Substances 0.000 title claims description 132
- 239000003349 gelling agent Substances 0.000 claims abstract description 75
- 239000000178 monomer Substances 0.000 claims abstract description 47
- 239000003086 colorant Substances 0.000 claims abstract description 27
- 239000000758 substrate Substances 0.000 claims description 34
- 125000002947 alkylene group Chemical group 0.000 claims description 29
- 150000001875 compounds Chemical class 0.000 claims description 29
- 125000003118 aryl group Chemical group 0.000 claims description 26
- 125000000732 arylene group Chemical group 0.000 claims description 20
- 125000000217 alkyl group Chemical group 0.000 claims description 17
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 10
- 125000002877 alkyl aryl group Chemical group 0.000 claims description 9
- 238000010438 heat treatment Methods 0.000 claims description 7
- 229920000223 polyglycerol Polymers 0.000 claims description 6
- 238000007639 printing Methods 0.000 claims description 6
- 238000002156 mixing Methods 0.000 claims description 5
- 238000001816 cooling Methods 0.000 claims description 4
- 239000011874 heated mixture Substances 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 3
- 238000002844 melting Methods 0.000 claims description 2
- 230000008018 melting Effects 0.000 claims description 2
- 239000000976 ink Substances 0.000 abstract description 182
- 125000004432 carbon atom Chemical group C* 0.000 description 75
- 239000001993 wax Substances 0.000 description 74
- 239000000049 pigment Substances 0.000 description 30
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 26
- 239000002904 solvent Substances 0.000 description 26
- -1 triglyceride fatty esters Chemical class 0.000 description 23
- 239000007787 solid Substances 0.000 description 22
- 239000007822 coupling agent Substances 0.000 description 21
- 238000006243 chemical reaction Methods 0.000 description 19
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 17
- 239000003054 catalyst Substances 0.000 description 17
- 238000001723 curing Methods 0.000 description 17
- 150000004985 diamines Chemical class 0.000 description 17
- 230000005855 radiation Effects 0.000 description 17
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 16
- 239000000463 material Substances 0.000 description 16
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 14
- 239000012071 phase Substances 0.000 description 14
- 239000004952 Polyamide Substances 0.000 description 13
- 239000003822 epoxy resin Substances 0.000 description 13
- 229920002647 polyamide Polymers 0.000 description 13
- 229920000647 polyepoxide Polymers 0.000 description 13
- 239000000126 substance Substances 0.000 description 12
- 238000012546 transfer Methods 0.000 description 11
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 10
- 239000007788 liquid Substances 0.000 description 10
- 239000000047 product Substances 0.000 description 10
- 239000002253 acid Substances 0.000 description 9
- 150000001408 amides Chemical class 0.000 description 9
- 125000004122 cyclic group Chemical group 0.000 description 9
- 239000003999 initiator Substances 0.000 description 9
- 230000007704 transition Effects 0.000 description 9
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 8
- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 8
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 8
- 239000006185 dispersion Substances 0.000 description 8
- 238000009472 formulation Methods 0.000 description 8
- 125000000524 functional group Chemical group 0.000 description 8
- 239000003921 oil Substances 0.000 description 8
- 235000019198 oils Nutrition 0.000 description 8
- 229910052760 oxygen Inorganic materials 0.000 description 8
- 239000001301 oxygen Substances 0.000 description 8
- 229920006122 polyamide resin Polymers 0.000 description 8
- 235000013871 bee wax Nutrition 0.000 description 7
- 239000012166 beeswax Substances 0.000 description 7
- 239000002131 composite material Substances 0.000 description 7
- 239000000539 dimer Substances 0.000 description 7
- 125000005842 heteroatom Chemical group 0.000 description 7
- 239000011541 reaction mixture Substances 0.000 description 7
- 239000003981 vehicle Substances 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- 150000007513 acids Chemical class 0.000 description 6
- 150000001298 alcohols Chemical class 0.000 description 6
- 239000003963 antioxidant agent Substances 0.000 description 6
- 230000000694 effects Effects 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- 230000035515 penetration Effects 0.000 description 6
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 5
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 5
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 5
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 5
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 5
- 239000004698 Polyethylene Substances 0.000 description 5
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 5
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 5
- 125000002015 acyclic group Chemical group 0.000 description 5
- 229910052796 boron Inorganic materials 0.000 description 5
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 5
- 239000003795 chemical substances by application Substances 0.000 description 5
- 239000000975 dye Substances 0.000 description 5
- 238000005259 measurement Methods 0.000 description 5
- 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 5
- 229910052757 nitrogen Inorganic materials 0.000 description 5
- 239000002245 particle Substances 0.000 description 5
- 239000011574 phosphorus Substances 0.000 description 5
- 229910052698 phosphorus Inorganic materials 0.000 description 5
- 229920000573 polyethylene Polymers 0.000 description 5
- 230000008569 process Effects 0.000 description 5
- 229920005989 resin Polymers 0.000 description 5
- 239000011347 resin Substances 0.000 description 5
- 229920006395 saturated elastomer Polymers 0.000 description 5
- 229910052710 silicon Inorganic materials 0.000 description 5
- 239000010703 silicon Substances 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- 229910052717 sulfur Inorganic materials 0.000 description 5
- 239000011593 sulfur Substances 0.000 description 5
- 239000012958 Amine synergist Substances 0.000 description 4
- UKMSUNONTOPOIO-UHFFFAOYSA-N Behenic acid Natural products CCCCCCCCCCCCCCCCCCCCCC(O)=O UKMSUNONTOPOIO-UHFFFAOYSA-N 0.000 description 4
- UTOPWMOLSKOLTQ-UHFFFAOYSA-N Octacosancarbonsaeure Natural products CCCCCCCCCCCCCCCCCCCCCCCCCCCC(O)=O UTOPWMOLSKOLTQ-UHFFFAOYSA-N 0.000 description 4
- 239000002202 Polyethylene glycol Substances 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- UTGPYHWDXYRYGT-UHFFFAOYSA-N Tetratriacontanoic acid Natural products CCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCC(O)=O UTGPYHWDXYRYGT-UHFFFAOYSA-N 0.000 description 4
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 4
- 239000006227 byproduct Substances 0.000 description 4
- 229910052799 carbon Inorganic materials 0.000 description 4
- 230000008859 change Effects 0.000 description 4
- VKOBVWXKNCXXDE-UHFFFAOYSA-N ethyl stearic acid Natural products CCCCCCCCCCCCCCCCCCCC(O)=O VKOBVWXKNCXXDE-UHFFFAOYSA-N 0.000 description 4
- 238000007641 inkjet printing Methods 0.000 description 4
- ICAIHSUWWZJGHD-UHFFFAOYSA-N n-dotriacontanoic acid Natural products CCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCC(O)=O ICAIHSUWWZJGHD-UHFFFAOYSA-N 0.000 description 4
- KEMQGTRYUADPNZ-UHFFFAOYSA-N n-heptadecanoic acid Natural products CCCCCCCCCCCCCCCCC(O)=O KEMQGTRYUADPNZ-UHFFFAOYSA-N 0.000 description 4
- XMHIUKTWLZUKEX-UHFFFAOYSA-N n-hexacosanoic acid Natural products CCCCCCCCCCCCCCCCCCCCCCCCCC(O)=O XMHIUKTWLZUKEX-UHFFFAOYSA-N 0.000 description 4
- IPCSVZSSVZVIGE-UHFFFAOYSA-N n-hexadecanoic acid Natural products CCCCCCCCCCCCCCCC(O)=O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 description 4
- VHOCUJPBKOZGJD-UHFFFAOYSA-N n-triacontanoic acid Natural products CCCCCCCCCCCCCCCCCCCCCCCCCCCCCC(O)=O VHOCUJPBKOZGJD-UHFFFAOYSA-N 0.000 description 4
- RZFODFPMOHAYIR-UHFFFAOYSA-N oxepan-2-one;prop-2-enoic acid Chemical compound OC(=O)C=C.O=C1CCCCCO1 RZFODFPMOHAYIR-UHFFFAOYSA-N 0.000 description 4
- 229920001223 polyethylene glycol Polymers 0.000 description 4
- 238000006116 polymerization reaction Methods 0.000 description 4
- 238000002360 preparation method Methods 0.000 description 4
- 241000894007 species Species 0.000 description 4
- 238000005406 washing Methods 0.000 description 4
- TXBCBTDQIULDIA-UHFFFAOYSA-N 2-[[3-hydroxy-2,2-bis(hydroxymethyl)propoxy]methyl]-2-(hydroxymethyl)propane-1,3-diol Chemical compound OCC(CO)(CO)COCC(CO)(CO)CO TXBCBTDQIULDIA-UHFFFAOYSA-N 0.000 description 3
- 239000004593 Epoxy Substances 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- HQRWEDFDJHDPJC-UHFFFAOYSA-N Psyllic acid Chemical compound CCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCC(O)=O HQRWEDFDJHDPJC-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
- 238000002835 absorbance Methods 0.000 description 3
- 239000000654 additive Substances 0.000 description 3
- 230000003078 antioxidant effect Effects 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 3
- 125000002843 carboxylic acid group Chemical group 0.000 description 3
- 150000001735 carboxylic acids Chemical class 0.000 description 3
- 238000004132 cross linking Methods 0.000 description 3
- 235000014113 dietary fatty acids Nutrition 0.000 description 3
- GYZLOYUZLJXAJU-UHFFFAOYSA-N diglycidyl ether Chemical class C1OC1COCC1CO1 GYZLOYUZLJXAJU-UHFFFAOYSA-N 0.000 description 3
- 238000010894 electron beam technology Methods 0.000 description 3
- 150000002148 esters Chemical class 0.000 description 3
- 239000000194 fatty acid Substances 0.000 description 3
- 229930195729 fatty acid Natural products 0.000 description 3
- 150000004665 fatty acids Chemical class 0.000 description 3
- LNEPOXFFQSENCJ-UHFFFAOYSA-N haloperidol Chemical compound C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 LNEPOXFFQSENCJ-UHFFFAOYSA-N 0.000 description 3
- 150000002430 hydrocarbons Chemical group 0.000 description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 3
- 230000000977 initiatory effect Effects 0.000 description 3
- 230000003993 interaction Effects 0.000 description 3
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 3
- 229910052753 mercury Inorganic materials 0.000 description 3
- WNWZKKBGFYKSGA-UHFFFAOYSA-N n-(4-chloro-2,5-dimethoxyphenyl)-2-[[2,5-dimethoxy-4-(phenylsulfamoyl)phenyl]diazenyl]-3-oxobutanamide Chemical compound C1=C(Cl)C(OC)=CC(NC(=O)C(N=NC=2C(=CC(=C(OC)C=2)S(=O)(=O)NC=2C=CC=CC=2)OC)C(C)=O)=C1OC WNWZKKBGFYKSGA-UHFFFAOYSA-N 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- VKWNTWQXVLKCSG-UHFFFAOYSA-N n-ethyl-1-[(4-phenyldiazenylphenyl)diazenyl]naphthalen-2-amine Chemical compound CCNC1=CC=C2C=CC=CC2=C1N=NC(C=C1)=CC=C1N=NC1=CC=CC=C1 VKWNTWQXVLKCSG-UHFFFAOYSA-N 0.000 description 3
- 230000002441 reversible effect Effects 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 238000012360 testing method Methods 0.000 description 3
- SCCCIUGOOQLDGW-UHFFFAOYSA-N 1,1-dicyclohexylurea Chemical compound C1CCCCC1N(C(=O)N)C1CCCCC1 SCCCIUGOOQLDGW-UHFFFAOYSA-N 0.000 description 2
- 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 2
- 239000012956 1-hydroxycyclohexylphenyl-ketone Substances 0.000 description 2
- 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 2
- TXWSZJSDZKWQAU-UHFFFAOYSA-N 2,9-dimethyl-5,12-dihydroquinolino[2,3-b]acridine-7,14-dione Chemical compound N1C2=CC=C(C)C=C2C(=O)C2=C1C=C(C(=O)C=1C(=CC=C(C=1)C)N1)C1=C2 TXWSZJSDZKWQAU-UHFFFAOYSA-N 0.000 description 2
- LEJBBGNFPAFPKQ-UHFFFAOYSA-N 2-(2-prop-2-enoyloxyethoxy)ethyl prop-2-enoate Chemical compound C=CC(=O)OCCOCCOC(=O)C=C LEJBBGNFPAFPKQ-UHFFFAOYSA-N 0.000 description 2
- INQDDHNZXOAFFD-UHFFFAOYSA-N 2-[2-(2-prop-2-enoyloxyethoxy)ethoxy]ethyl prop-2-enoate Chemical compound C=CC(=O)OCCOCCOCCOC(=O)C=C INQDDHNZXOAFFD-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
- RZVINYQDSSQUKO-UHFFFAOYSA-N 2-phenoxyethyl prop-2-enoate Chemical compound C=CC(=O)OCCOC1=CC=CC=C1 RZVINYQDSSQUKO-UHFFFAOYSA-N 0.000 description 2
- 235000021357 Behenic acid Nutrition 0.000 description 2
- HVUCKZJUWZBJDP-UHFFFAOYSA-N Ceroplastic acid Chemical compound CCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCC(O)=O HVUCKZJUWZBJDP-UHFFFAOYSA-N 0.000 description 2
- OWYWGLHRNBIFJP-UHFFFAOYSA-N Ipazine Chemical compound CCN(CC)C1=NC(Cl)=NC(NC(C)C)=N1 OWYWGLHRNBIFJP-UHFFFAOYSA-N 0.000 description 2
- 235000021353 Lignoceric acid Nutrition 0.000 description 2
- CQXMAMUUWHYSIY-UHFFFAOYSA-N Lignoceric acid Natural products CCCCCCCCCCCCCCCCCCCCCCCC(=O)OCCC1=CC=C(O)C=C1 CQXMAMUUWHYSIY-UHFFFAOYSA-N 0.000 description 2
- CZDZMHVFCAQERK-MRCUOEKSSA-N OC(=O)C=C.OC(=O)C=C.OC(=O)C=C.OC(=O)C=C.OC[C@H](O)[C@H](O)CO.OC[C@H](O)[C@H](O)CO.OC[C@H](O)[C@H](O)CO.OC[C@H](O)[C@H](O)CO.OC[C@H](O)[C@H](O)CO Chemical class OC(=O)C=C.OC(=O)C=C.OC(=O)C=C.OC(=O)C=C.OC[C@H](O)[C@H](O)CO.OC[C@H](O)[C@H](O)CO.OC[C@H](O)[C@H](O)CO.OC[C@H](O)[C@H](O)CO.OC[C@H](O)[C@H](O)CO CZDZMHVFCAQERK-MRCUOEKSSA-N 0.000 description 2
- 235000021314 Palmitic acid Nutrition 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 235000019484 Rapeseed oil Nutrition 0.000 description 2
- 235000021355 Stearic acid Nutrition 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- DAKWPKUUDNSNPN-UHFFFAOYSA-N Trimethylolpropane triacrylate Chemical compound C=CC(=O)OCC(CC)(COC(=O)C=C)COC(=O)C=C DAKWPKUUDNSNPN-UHFFFAOYSA-N 0.000 description 2
- 150000001336 alkenes Chemical class 0.000 description 2
- QFFVPLLCYGOFPU-UHFFFAOYSA-N barium chromate Chemical compound [Ba+2].[O-][Cr]([O-])(=O)=O QFFVPLLCYGOFPU-UHFFFAOYSA-N 0.000 description 2
- 229940116226 behenic acid Drugs 0.000 description 2
- 239000012965 benzophenone Substances 0.000 description 2
- 239000011230 binding agent Substances 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
- 239000006229 carbon black Substances 0.000 description 2
- 235000019241 carbon black Nutrition 0.000 description 2
- JBTHDAVBDKKSRW-UHFFFAOYSA-N chembl1552233 Chemical compound CC1=CC(C)=CC=C1N=NC1=C(O)C=CC2=CC=CC=C12 JBTHDAVBDKKSRW-UHFFFAOYSA-N 0.000 description 2
- ZLFVRXUOSPRRKQ-UHFFFAOYSA-N chembl2138372 Chemical compound [O-][N+](=O)C1=CC(C)=CC=C1N=NC1=C(O)C=CC2=CC=CC=C12 ZLFVRXUOSPRRKQ-UHFFFAOYSA-N 0.000 description 2
- 239000012141 concentrate Substances 0.000 description 2
- 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 2
- 150000002009 diols Chemical class 0.000 description 2
- VFHVQBAGLAREND-UHFFFAOYSA-N diphenylphosphoryl-(2,4,6-trimethylphenyl)methanone Chemical compound CC1=CC(C)=CC(C)=C1C(=O)P(=O)(C=1C=CC=CC=1)C1=CC=CC=C1 VFHVQBAGLAREND-UHFFFAOYSA-N 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 150000002118 epoxides Chemical group 0.000 description 2
- 125000003700 epoxy group Chemical group 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 230000006870 function Effects 0.000 description 2
- 230000004927 fusion Effects 0.000 description 2
- 125000005843 halogen group Chemical group 0.000 description 2
- 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 2
- VXZBFBRLRNDJCS-UHFFFAOYSA-N heptacosanoic acid Chemical compound CCCCCCCCCCCCCCCCCCCCCCCCCCC(O)=O VXZBFBRLRNDJCS-UHFFFAOYSA-N 0.000 description 2
- 239000012943 hotmelt Substances 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 2
- 238000002386 leaching Methods 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 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
- 230000003647 oxidation Effects 0.000 description 2
- 238000007254 oxidation reaction Methods 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
- FSDNTQSJGHSJBG-UHFFFAOYSA-N piperidine-4-carbonitrile Chemical compound N#CC1CCNCC1 FSDNTQSJGHSJBG-UHFFFAOYSA-N 0.000 description 2
- 229920003023 plastic Polymers 0.000 description 2
- 239000004033 plastic Substances 0.000 description 2
- 239000002985 plastic film Substances 0.000 description 2
- 229920006255 plastic film Polymers 0.000 description 2
- 229920005862 polyol Polymers 0.000 description 2
- 150000003077 polyols Chemical class 0.000 description 2
- 150000008442 polyphenolic compounds Chemical class 0.000 description 2
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- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- 239000002540 palm oil Substances 0.000 description 1
- FZUGPQWGEGAKET-UHFFFAOYSA-N parbenate Chemical compound CCOC(=O)C1=CC=C(N(C)C)C=C1 FZUGPQWGEGAKET-UHFFFAOYSA-N 0.000 description 1
- 229940059574 pentaerithrityl Drugs 0.000 description 1
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 1
- 230000000737 periodic effect Effects 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- HPAFOABSQZMTHE-UHFFFAOYSA-N phenyl-(2,4,6-trimethylphenyl)methanone Chemical compound CC1=CC(C)=CC(C)=C1C(=O)C1=CC=CC=C1 HPAFOABSQZMTHE-UHFFFAOYSA-N 0.000 description 1
- MTZWHHIREPJPTG-UHFFFAOYSA-N phorone Chemical compound CC(C)=CC(=O)C=C(C)C MTZWHHIREPJPTG-UHFFFAOYSA-N 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 229940068065 phytosterols Drugs 0.000 description 1
- 229940110337 pigment blue 1 Drugs 0.000 description 1
- 229940099800 pigment red 48 Drugs 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 229920000233 poly(alkylene oxides) Polymers 0.000 description 1
- 229920000768 polyamine Polymers 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 229920000570 polyether Polymers 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 229920001296 polysiloxane Polymers 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 238000012113 quantitative test Methods 0.000 description 1
- 238000003847 radiation curing Methods 0.000 description 1
- 238000007348 radical reaction Methods 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 239000013557 residual solvent Substances 0.000 description 1
- 230000003938 response to stress Effects 0.000 description 1
- 238000000518 rheometry Methods 0.000 description 1
- 238000005096 rolling process Methods 0.000 description 1
- 230000003678 scratch resistant effect Effects 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000012176 shellac wax Substances 0.000 description 1
- 238000004088 simulation Methods 0.000 description 1
- 239000012748 slip agent Substances 0.000 description 1
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 1
- 230000003381 solubilizing effect Effects 0.000 description 1
- 230000003595 spectral effect Effects 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 235000019385 spermaceti wax Nutrition 0.000 description 1
- 230000006641 stabilisation Effects 0.000 description 1
- 238000011105 stabilization Methods 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 230000000638 stimulation Effects 0.000 description 1
- 125000000547 substituted alkyl group Chemical group 0.000 description 1
- 125000005156 substituted alkylene group Chemical group 0.000 description 1
- 150000005846 sugar alcohols Polymers 0.000 description 1
- 229940124530 sulfonamide Drugs 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 229920002994 synthetic fiber Polymers 0.000 description 1
- QZZGJDVWLFXDLK-UHFFFAOYSA-N tetracosanoic acid Chemical compound CCCCCCCCCCCCCCCCCCCCCCCC(O)=O QZZGJDVWLFXDLK-UHFFFAOYSA-N 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 1
- 239000004753 textile Substances 0.000 description 1
- 238000001029 thermal curing Methods 0.000 description 1
- 125000002813 thiocarbonyl group Chemical group *C(*)=S 0.000 description 1
- 125000000101 thioether group Chemical group 0.000 description 1
- 239000013008 thixotropic agent Substances 0.000 description 1
- 210000003813 thumb Anatomy 0.000 description 1
- XOALFFJGWSCQEO-UHFFFAOYSA-N tridecyl prop-2-enoate Chemical compound CCCCCCCCCCCCCOC(=O)C=C XOALFFJGWSCQEO-UHFFFAOYSA-N 0.000 description 1
- WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical compound [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 description 1
- 229910052721 tungsten Inorganic materials 0.000 description 1
- 239000010937 tungsten Substances 0.000 description 1
- JABYJIQOLGWMQW-UHFFFAOYSA-N undec-4-ene Chemical compound CCCCCCC=CCCC JABYJIQOLGWMQW-UHFFFAOYSA-N 0.000 description 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N urea group Chemical group NC(=O)N XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
- JOYRKODLDBILNP-UHFFFAOYSA-N urethane group Chemical group NC(=O)OCC JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
- 238000010792 warming Methods 0.000 description 1
- 238000009736 wetting Methods 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
- 229910052724 xenon Inorganic materials 0.000 description 1
- FHNFHKCVQCLJFQ-UHFFFAOYSA-N xenon atom Chemical compound [Xe] FHNFHKCVQCLJFQ-UHFFFAOYSA-N 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
- C09D11/02—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
-
- 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
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S522/00—Synthetic resins or natural rubbers -- part of the class 520 series
- Y10S522/909—Solventless ink
Landscapes
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Wood Science & Technology (AREA)
- Organic Chemistry (AREA)
- Inks, Pencil-Leads, Or Crayons (AREA)
- Ink Jet Recording Methods And Recording Media Thereof (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US12/765,341 | 2010-04-22 | ||
| US12/765,341 US8097661B2 (en) | 2010-04-22 | 2010-04-22 | Ink compositions and methods |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2737567A1 CA2737567A1 (en) | 2011-10-22 |
| CA2737567C true CA2737567C (en) | 2014-06-17 |
Family
ID=44816021
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2737567A Expired - Fee Related CA2737567C (en) | 2010-04-22 | 2011-04-15 | Ink compositions and methods |
Country Status (5)
| Country | Link |
|---|---|
| US (1) | US8097661B2 (OSRAM) |
| JP (1) | JP5611885B2 (OSRAM) |
| CN (1) | CN102234461B (OSRAM) |
| CA (1) | CA2737567C (OSRAM) |
| DE (1) | DE102011007383B4 (OSRAM) |
Families Citing this family (22)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US8507584B2 (en) * | 2010-04-22 | 2013-08-13 | Xerox Corporation | Phase change inks containing amide gellant compounds with aromatic end groups |
| US8603612B2 (en) | 2010-04-22 | 2013-12-10 | Xerox Corporation | Curable compositions for three-dimensional printing |
| US20120190765A1 (en) * | 2011-01-20 | 2012-07-26 | Xerox Corporation | Robust curable solid inks |
| US8690305B2 (en) * | 2011-05-11 | 2014-04-08 | Xerox Corporation | High reactivity curable paste ink compositions |
| US8714723B2 (en) * | 2011-05-11 | 2014-05-06 | Xerox Corporation | Robust curable solid inks and methods for using the same |
| US8581000B2 (en) * | 2011-06-06 | 2013-11-12 | Xerox Corporation | Process for preparing amide gellant compounds with aromatic end groups |
| US8772416B2 (en) * | 2012-04-09 | 2014-07-08 | Xerox Corporation | Ink compositions containing isosorbide-capped amide gellant |
| 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 |
| US8686062B1 (en) * | 2012-11-02 | 2014-04-01 | Xerox Corporation | Radiation curable red gel ink formulations |
| US9096767B2 (en) * | 2012-11-06 | 2015-08-04 | Xerox Corporation | Curable solid inks containing cyclohexyl-based crystalline gellants |
| US8669298B1 (en) * | 2012-12-18 | 2014-03-11 | Xerox Corporation | Green curable ink |
| US20140171537A1 (en) * | 2012-12-18 | 2014-06-19 | Xerox Corporation | Orange Curable Ink |
| US8991992B2 (en) | 2013-01-22 | 2015-03-31 | Xerox Corporation | Inkjet ink containing sub 100 nm latexes |
| US9453139B2 (en) * | 2013-08-20 | 2016-09-27 | Rohm And Haas Electronic Materials Llc | Hot melt compositions with improved etch resistance |
| WO2015134024A1 (en) * | 2014-03-06 | 2015-09-11 | Hewlett-Packard Development Company, L.P. | Non-newtonian inkjet inks |
| JP6819298B2 (ja) * | 2015-02-09 | 2021-01-27 | コニカミノルタ株式会社 | インクジェットインクおよび画像形成方法 |
| WO2016153035A1 (ja) * | 2015-03-26 | 2016-09-29 | コニカミノルタ株式会社 | 活性光線硬化型インクジェットインク及びインクジェット記録方法 |
| WO2017144463A1 (en) * | 2016-02-23 | 2017-08-31 | OCE Holding B.V. | Radiation-curable inkjet ink composition |
| US11193027B2 (en) | 2017-03-31 | 2021-12-07 | Kao Corporation | Radiation curable ink compositions, printed articles, and methods of using the same |
| US10696857B2 (en) | 2017-12-14 | 2020-06-30 | Xerox Corporation | Curable gellant ink |
| JP7740251B2 (ja) | 2020-09-18 | 2025-09-17 | コニカミノルタ株式会社 | 硬化性組成物、ソルダーレジスト用インク及びプリント回路基板 |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
| US5372852A (en) | 1992-11-25 | 1994-12-13 | Tektronix, Inc. | Indirect printing process for applying selective phase change ink compositions to substrates |
| 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 |
| 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 |
| US20020001698A1 (en) * | 1998-05-06 | 2002-01-03 | Blankenship Robert Mitchell | Low gloss coating composition |
| JP2003041166A (ja) * | 2001-07-27 | 2003-02-13 | Seiren Co Ltd | インクジェットプリント用ホットメルトインク組成物、それを用いたインクジェットプリント方法、及びインクジェットプリント物 |
| US6994845B2 (en) | 2003-04-08 | 2006-02-07 | Colgate-Palmolive Company | Soft solid compositions with reduced syneresis |
| US7690782B2 (en) | 2004-12-07 | 2010-04-06 | Xerox Corporation | Apparatus and process for printing ultraviolet curable inks |
| US7172276B2 (en) * | 2004-12-10 | 2007-02-06 | Xerox Corporation | Heterogeneous low energy gel ink composition |
| US7270408B2 (en) | 2005-01-14 | 2007-09-18 | Xerox Corporation | Low level cure transfuse assist for printing with radiation curable ink |
| AU2006203245A1 (en) * | 2005-09-01 | 2007-03-15 | Oce-Technologies B.V. | A method for printing a substrate with radiation curable ink, and an ink suitable for application in the said method |
| US7279587B2 (en) | 2005-11-30 | 2007-10-09 | Xerox Corporation | Photoinitiator with phase change properties and gellant affinity |
| US7276614B2 (en) | 2005-11-30 | 2007-10-02 | Xerox Corporation | Curable amide gellant compounds |
| 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 |
| US7665835B2 (en) * | 2005-11-30 | 2010-02-23 | Xerox Corporation | Phase change inks and methods for making same |
| US7632546B2 (en) | 2005-11-30 | 2009-12-15 | Xerox Corporation | Radiation curable phase change inks containing gellants |
| US7563489B2 (en) | 2005-11-30 | 2009-07-21 | Xerox Corporation | Radiation curable phase change inks containing curable epoxy-polyamide composite gellants |
| US7655084B2 (en) * | 2005-12-12 | 2010-02-02 | Xerox Corporation | Carbon black inks and method for making same |
| US7820731B2 (en) * | 2005-12-15 | 2010-10-26 | Xerox Corporation | Radiation curable inks |
| US8142557B2 (en) * | 2006-06-28 | 2012-03-27 | Xerox Corporation | Radiation curable ink containing gellant and radiation curable wax |
| US7531582B2 (en) * | 2006-08-23 | 2009-05-12 | Xerox Corporation | Radiation curable phase change inks containing curable epoxy-polyamide composite gellants |
| US8061791B2 (en) | 2007-03-07 | 2011-11-22 | Xerox Corporation | Dual printer for regular and raised print |
| US7812064B2 (en) * | 2007-08-07 | 2010-10-12 | Xerox Corporation | Phase change ink compositions |
| US7905948B2 (en) * | 2007-08-14 | 2011-03-15 | Xerox Corporation | Phase change ink compositions |
| US20090136681A1 (en) * | 2007-11-28 | 2009-05-28 | Xerox Corporation | Phase Change Curable Inks |
| US8916084B2 (en) | 2008-09-04 | 2014-12-23 | Xerox Corporation | Ultra-violet curable gellant inks for three-dimensional printing and digital fabrication applications |
-
2010
- 2010-04-22 US US12/765,341 patent/US8097661B2/en active Active
-
2011
- 2011-04-14 DE DE102011007383.3A patent/DE102011007383B4/de not_active Expired - Fee Related
- 2011-04-15 CA CA2737567A patent/CA2737567C/en not_active Expired - Fee Related
- 2011-04-18 JP JP2011092425A patent/JP5611885B2/ja not_active Expired - Fee Related
- 2011-04-22 CN CN201110103965.XA patent/CN102234461B/zh not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| US8097661B2 (en) | 2012-01-17 |
| CA2737567A1 (en) | 2011-10-22 |
| DE102011007383A1 (de) | 2011-12-01 |
| JP2011225876A (ja) | 2011-11-10 |
| CN102234461B (zh) | 2016-02-24 |
| DE102011007383B4 (de) | 2018-12-06 |
| CN102234461A (zh) | 2011-11-09 |
| JP5611885B2 (ja) | 2014-10-22 |
| US20110262643A1 (en) | 2011-10-27 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request | ||
| MKLA | Lapsed |
Effective date: 20210415 |