JP2011521096A - 尿素末端封止ポリウレタン分散剤 - Google Patents
尿素末端封止ポリウレタン分散剤 Download PDFInfo
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- JP2011521096A JP2011521096A JP2011511740A JP2011511740A JP2011521096A JP 2011521096 A JP2011521096 A JP 2011521096A JP 2011511740 A JP2011511740 A JP 2011511740A JP 2011511740 A JP2011511740 A JP 2011511740A JP 2011521096 A JP2011521096 A JP 2011521096A
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- Prior art keywords
- polyurethane
- urea
- group
- alkyl
- diol
- 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.)
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- 229920002635 polyurethane Polymers 0.000 title claims abstract description 158
- 239000004814 polyurethane Substances 0.000 title claims abstract description 158
- 239000002270 dispersing agent Substances 0.000 title claims abstract description 90
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 title claims abstract description 56
- 239000004202 carbamide Substances 0.000 title claims abstract description 54
- 239000000049 pigment Substances 0.000 claims abstract description 98
- 239000006185 dispersion Substances 0.000 claims abstract description 97
- 150000002009 diols Chemical class 0.000 claims abstract description 79
- 239000000986 disperse dye Substances 0.000 claims abstract description 9
- 239000002245 particle Substances 0.000 claims description 69
- 239000000976 ink Substances 0.000 claims description 67
- 239000000203 mixture Substances 0.000 claims description 50
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 45
- 125000000217 alkyl group Chemical group 0.000 claims description 40
- 238000000034 method Methods 0.000 claims description 34
- -1 carbonate diol Chemical class 0.000 claims description 33
- 239000003086 colorant Substances 0.000 claims description 26
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 23
- 239000012948 isocyanate Substances 0.000 claims description 22
- 239000000376 reactant Substances 0.000 claims description 22
- 125000003010 ionic group Chemical group 0.000 claims description 21
- 125000005442 diisocyanate group Chemical group 0.000 claims description 20
- 150000002513 isocyanates Chemical class 0.000 claims description 18
- 229920000728 polyester Polymers 0.000 claims description 18
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 claims description 17
- 150000001875 compounds Chemical class 0.000 claims description 16
- 239000001257 hydrogen Substances 0.000 claims description 14
- 229910052739 hydrogen Inorganic materials 0.000 claims description 14
- 125000000547 substituted alkyl group Chemical group 0.000 claims description 14
- 230000008569 process Effects 0.000 claims description 13
- 125000003277 amino group Chemical group 0.000 claims description 10
- 238000009472 formulation Methods 0.000 claims description 10
- 239000005056 polyisocyanate Substances 0.000 claims description 10
- 229920001228 polyisocyanate Polymers 0.000 claims description 10
- 125000003118 aryl group Chemical group 0.000 claims description 9
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 9
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims description 9
- 239000004417 polycarbonate Substances 0.000 claims description 9
- 229920000515 polycarbonate Polymers 0.000 claims description 9
- 239000007788 liquid Substances 0.000 claims description 8
- 239000003960 organic solvent Substances 0.000 claims description 8
- 239000008135 aqueous vehicle Substances 0.000 claims description 7
- 238000002156 mixing Methods 0.000 claims description 7
- 229920000058 polyacrylate Polymers 0.000 claims description 7
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 6
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 6
- 150000001408 amides Chemical class 0.000 claims description 5
- 230000003993 interaction Effects 0.000 claims description 5
- PXQLVRUNWNTZOS-UHFFFAOYSA-N sulfanyl Chemical class [SH] PXQLVRUNWNTZOS-UHFFFAOYSA-N 0.000 claims description 5
- 229920001730 Moisture cure polyurethane Polymers 0.000 claims description 3
- 239000008365 aqueous carrier Substances 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 3
- 125000000467 secondary amino group Chemical class [H]N([*:1])[*:2] 0.000 claims description 2
- 229920003009 polyurethane dispersion Polymers 0.000 abstract description 32
- 238000002360 preparation method Methods 0.000 abstract description 19
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 35
- 229920000642 polymer Polymers 0.000 description 33
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 29
- 239000002253 acid Substances 0.000 description 24
- 239000002904 solvent Substances 0.000 description 21
- 238000006243 chemical reaction Methods 0.000 description 19
- NIMLQBUJDJZYEJ-UHFFFAOYSA-N isophorone diisocyanate Chemical compound CC1(C)CC(N=C=O)CC(C)(CN=C=O)C1 NIMLQBUJDJZYEJ-UHFFFAOYSA-N 0.000 description 19
- 229920000570 polyether Polymers 0.000 description 19
- 239000007787 solid Substances 0.000 description 19
- 239000005058 Isophorone diisocyanate Substances 0.000 description 18
- 239000004721 Polyphenylene oxide Substances 0.000 description 16
- 150000001412 amines Chemical class 0.000 description 16
- 239000003795 chemical substances by application Substances 0.000 description 16
- 230000003472 neutralizing effect Effects 0.000 description 15
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- 125000000129 anionic group Chemical group 0.000 description 10
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- UKLDJPRMSDWDSL-UHFFFAOYSA-L [dibutyl(dodecanoyloxy)stannyl] dodecanoate Chemical compound CCCCCCCCCCCC(=O)O[Sn](CCCC)(CCCC)OC(=O)CCCCCCCCCCC UKLDJPRMSDWDSL-UHFFFAOYSA-L 0.000 description 9
- PSGAAPLEWMOORI-PEINSRQWSA-N medroxyprogesterone acetate Chemical compound C([C@@]12C)CC(=O)C=C1[C@@H](C)C[C@@H]1[C@@H]2CC[C@]2(C)[C@@](OC(C)=O)(C(C)=O)CC[C@H]21 PSGAAPLEWMOORI-PEINSRQWSA-N 0.000 description 9
- 239000012071 phase Substances 0.000 description 9
- 229920000909 polytetrahydrofuran Polymers 0.000 description 9
- 150000003335 secondary amines Chemical class 0.000 description 9
- ZUHZGEOKBKGPSW-UHFFFAOYSA-N tetraglyme Chemical compound COCCOCCOCCOCCOC ZUHZGEOKBKGPSW-UHFFFAOYSA-N 0.000 description 9
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
- 239000012975 dibutyltin dilaurate Substances 0.000 description 8
- 229910001873 dinitrogen Inorganic materials 0.000 description 8
- 229920005862 polyol Polymers 0.000 description 8
- 150000003077 polyols Chemical class 0.000 description 8
- YPFDHNVEDLHUCE-UHFFFAOYSA-N 1,3-propanediol Substances OCCCO YPFDHNVEDLHUCE-UHFFFAOYSA-N 0.000 description 7
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 7
- 230000000052 comparative effect Effects 0.000 description 7
- 239000004744 fabric Substances 0.000 description 7
- 229920000166 polytrimethylene carbonate Polymers 0.000 description 7
- 229920005989 resin Polymers 0.000 description 7
- 239000011347 resin Substances 0.000 description 7
- DNIAPMSPPWPWGF-VKHMYHEASA-N (+)-propylene glycol Chemical compound C[C@H](O)CO DNIAPMSPPWPWGF-VKHMYHEASA-N 0.000 description 6
- 239000004215 Carbon black (E152) Substances 0.000 description 6
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 6
- 239000003513 alkali Substances 0.000 description 6
- 230000015572 biosynthetic process Effects 0.000 description 6
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- 150000003839 salts Chemical group 0.000 description 6
- 239000000126 substance Substances 0.000 description 6
- 150000003512 tertiary amines Chemical class 0.000 description 6
- 238000012360 testing method Methods 0.000 description 6
- ARSRBNBHOADGJU-UHFFFAOYSA-N 7,12-dimethyltetraphene Chemical compound C1=CC2=CC=CC=C2C2=C1C(C)=C(C=CC=C1)C1=C2C ARSRBNBHOADGJU-UHFFFAOYSA-N 0.000 description 5
- VFZRZRDOXPRTSC-UHFFFAOYSA-N DMBA Natural products COC1=CC(OC)=CC(C=O)=C1 VFZRZRDOXPRTSC-UHFFFAOYSA-N 0.000 description 5
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 5
- 125000002091 cationic group Chemical group 0.000 description 5
- 150000002431 hydrogen Chemical class 0.000 description 5
- 238000003801 milling Methods 0.000 description 5
- VZXPHDGHQXLXJC-UHFFFAOYSA-N 1,6-diisocyanato-5,6-dimethylheptane Chemical compound O=C=NC(C)(C)C(C)CCCCN=C=O VZXPHDGHQXLXJC-UHFFFAOYSA-N 0.000 description 4
- UPMLOUAZCHDJJD-UHFFFAOYSA-N 4,4'-Diphenylmethane Diisocyanate Chemical compound C1=CC(N=C=O)=CC=C1CC1=CC=C(N=C=O)C=C1 UPMLOUAZCHDJJD-UHFFFAOYSA-N 0.000 description 4
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 4
- 229920006309 Invista Polymers 0.000 description 4
- UEEJHVSXFDXPFK-UHFFFAOYSA-N N-dimethylaminoethanol Chemical compound CN(C)CCO UEEJHVSXFDXPFK-UHFFFAOYSA-N 0.000 description 4
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 4
- 150000001298 alcohols Chemical class 0.000 description 4
- 125000001931 aliphatic group Chemical group 0.000 description 4
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 4
- 150000007942 carboxylates Chemical group 0.000 description 4
- JQVDAXLFBXTEQA-UHFFFAOYSA-N dibutylamine Chemical compound CCCCNCCCC JQVDAXLFBXTEQA-UHFFFAOYSA-N 0.000 description 4
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 4
- 238000009826 distribution Methods 0.000 description 4
- 125000000524 functional group Chemical group 0.000 description 4
- 239000002609 medium Substances 0.000 description 4
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- 230000003287 optical effect Effects 0.000 description 4
- 239000012860 organic pigment Substances 0.000 description 4
- 150000003141 primary amines Chemical class 0.000 description 4
- 239000000758 substrate Substances 0.000 description 4
- 125000001273 sulfonato group Chemical group [O-]S(*)(=O)=O 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 3
- AHVYPIQETPWLSZ-UHFFFAOYSA-N N-methyl-pyrrolidine Natural products CN1CC=CC1 AHVYPIQETPWLSZ-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000000654 additive Substances 0.000 description 3
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- 125000004432 carbon atom Chemical group C* 0.000 description 3
- 125000002843 carboxylic acid group Chemical group 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 239000012141 concentrate Substances 0.000 description 3
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- SBJCUZQNHOLYMD-UHFFFAOYSA-N 1,5-Naphthalene diisocyanate Chemical compound C1=CC=C2C(N=C=O)=CC=CC2=C1N=C=O SBJCUZQNHOLYMD-UHFFFAOYSA-N 0.000 description 2
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- PAMIQIKDUOTOBW-UHFFFAOYSA-N 1-methylpiperidine Chemical compound CN1CCCCC1 PAMIQIKDUOTOBW-UHFFFAOYSA-N 0.000 description 2
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- PTBDIHRZYDMNKB-UHFFFAOYSA-N 2,2-Bis(hydroxymethyl)propionic acid Chemical compound OCC(C)(CO)C(O)=O PTBDIHRZYDMNKB-UHFFFAOYSA-N 0.000 description 2
- GVZNXUAPPLHUOM-UHFFFAOYSA-N 2-[1-(1-methoxypropan-2-yloxy)propan-2-yloxy]propan-1-ol Chemical compound COCC(C)OCC(C)OC(C)CO GVZNXUAPPLHUOM-UHFFFAOYSA-N 0.000 description 2
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Classifications
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- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/30—Low-molecular-weight compounds
- C08G18/34—Carboxylic acids; Esters thereof with monohydroxyl compounds
- C08G18/341—Dicarboxylic acids, esters of polycarboxylic acids containing two carboxylic acid groups
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/08—Processes
- C08G18/0804—Manufacture of polymers containing ionic or ionogenic groups
- C08G18/0819—Manufacture of polymers containing ionic or ionogenic groups containing anionic or anionogenic groups
- C08G18/0823—Manufacture of polymers containing ionic or ionogenic groups containing anionic or anionogenic groups containing carboxylate salt groups or groups forming them
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- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/08—Processes
- C08G18/10—Prepolymer processes involving reaction of isocyanates or isothiocyanates with compounds having active hydrogen in a first reaction step
- C08G18/12—Prepolymer processes involving reaction of isocyanates or isothiocyanates with compounds having active hydrogen in a first reaction step using two or more compounds having active hydrogen in the first polymerisation step
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/30—Low-molecular-weight compounds
- C08G18/32—Polyhydroxy compounds; Polyamines; Hydroxyamines
- C08G18/3271—Hydroxyamines
- C08G18/3275—Hydroxyamines containing two hydroxy groups
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/30—Low-molecular-weight compounds
- C08G18/34—Carboxylic acids; Esters thereof with monohydroxyl compounds
- C08G18/348—Hydroxycarboxylic acids
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/40—High-molecular-weight compounds
- C08G18/42—Polycondensates having carboxylic or carbonic ester groups in the main chain
- C08G18/4205—Polycondensates having carboxylic or carbonic ester groups in the main chain containing cyclic groups
- C08G18/4208—Polycondensates having carboxylic or carbonic ester groups in the main chain containing cyclic groups containing aromatic groups
- C08G18/4211—Polycondensates having carboxylic or carbonic ester groups in the main chain containing cyclic groups containing aromatic groups derived from aromatic dicarboxylic acids and dialcohols
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/40—High-molecular-weight compounds
- C08G18/42—Polycondensates having carboxylic or carbonic ester groups in the main chain
- C08G18/44—Polycarbonates
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/65—Low-molecular-weight compounds having active hydrogen with high-molecular-weight compounds having active hydrogen
- C08G18/66—Compounds of groups C08G18/42, C08G18/48, or C08G18/52
- C08G18/6633—Compounds of group C08G18/42
- C08G18/6659—Compounds of group C08G18/42 with compounds of group C08G18/34
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/70—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
- C08G18/72—Polyisocyanates or polyisothiocyanates
- C08G18/74—Polyisocyanates or polyisothiocyanates cyclic
- C08G18/75—Polyisocyanates or polyisothiocyanates cyclic cycloaliphatic
- C08G18/751—Polyisocyanates or polyisothiocyanates cyclic cycloaliphatic containing only one cycloaliphatic ring
- C08G18/752—Polyisocyanates or polyisothiocyanates cyclic cycloaliphatic containing only one cycloaliphatic ring containing at least one isocyanate or isothiocyanate group linked to the cycloaliphatic ring by means of an aliphatic group
- C08G18/753—Polyisocyanates or polyisothiocyanates cyclic cycloaliphatic containing only one cycloaliphatic ring containing at least one isocyanate or isothiocyanate group linked to the cycloaliphatic ring by means of an aliphatic group containing one isocyanate or isothiocyanate group linked to the cycloaliphatic ring by means of an aliphatic group having a primary carbon atom next to the isocyanate or isothiocyanate group
- C08G18/755—Polyisocyanates or polyisothiocyanates cyclic cycloaliphatic containing only one cycloaliphatic ring containing at least one isocyanate or isothiocyanate group linked to the cycloaliphatic ring by means of an aliphatic group containing one isocyanate or isothiocyanate group linked to the cycloaliphatic ring by means of an aliphatic group having a primary carbon atom next to the isocyanate or isothiocyanate group and at least one isocyanate or isothiocyanate group linked to a secondary carbon atom of the cycloaliphatic ring, e.g. isophorone diisocyanate
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Engineering & Computer Science (AREA)
- Manufacturing & Machinery (AREA)
- Life Sciences & Earth Sciences (AREA)
- Materials Engineering (AREA)
- Wood Science & Technology (AREA)
- Inks, Pencil-Leads, Or Crayons (AREA)
- Polyurethanes Or Polyureas (AREA)
- Pigments, Carbon Blacks, Or Wood Stains (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US12863708P | 2008-05-23 | 2008-05-23 | |
| US61/128,637 | 2008-05-23 | ||
| PCT/US2009/044994 WO2009143433A1 (en) | 2008-05-23 | 2009-05-22 | Urea-terminated polyurethane dispersants |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2011521096A true JP2011521096A (ja) | 2011-07-21 |
| JP2011521096A5 JP2011521096A5 (enExample) | 2012-07-12 |
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2011511740A Withdrawn JP2011521096A (ja) | 2008-05-23 | 2009-05-22 | 尿素末端封止ポリウレタン分散剤 |
Country Status (4)
| Country | Link |
|---|---|
| US (1) | US20110060102A1 (enExample) |
| EP (1) | EP2294103B1 (enExample) |
| JP (1) | JP2011521096A (enExample) |
| WO (1) | WO2009143433A1 (enExample) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2013538275A (ja) * | 2010-08-31 | 2013-10-10 | イー・アイ・デュポン・ドウ・ヌムール・アンド・カンパニー | 被架橋顔料分散物およびポリマーバインダーを含むインクジェットインク |
| JP2015063582A (ja) * | 2013-09-24 | 2015-04-09 | Dic株式会社 | 水性顔料組成物の製造方法及び捺染用のインキ |
| JP2016044282A (ja) * | 2014-08-26 | 2016-04-04 | 東洋インキＳｃホールディングス株式会社 | グラビア印刷用水性印刷インキ組成物 |
| JP2017206623A (ja) * | 2016-05-19 | 2017-11-24 | 株式会社リコー | 微粒子分散体、インク、インク入り容器、画像形成装置、及び画像形成方法 |
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| US9410010B2 (en) * | 2007-12-10 | 2016-08-09 | E I Du Pont De Nemours And Company | Urea-terminated polyurethane dispersants |
| US20100048811A1 (en) * | 2008-08-20 | 2010-02-25 | Marc Chilla | Process for the production of polyurethane urea resin dispersions |
| EP2504395A4 (en) * | 2009-11-23 | 2014-06-04 | Du Pont | DISPERSION OF A CROSSLINKED PIGMENT OBTAINED BY DISPERSANTS BASED ON POLYURETHANE |
| US20110293898A1 (en) * | 2010-05-28 | 2011-12-01 | Seiko Epson Corporation | Ink set, textile printing method and printed textile |
| US8613509B2 (en) * | 2010-05-28 | 2013-12-24 | Seiko Epson Corporation | Ink jet recording ink composition |
| WO2012009415A2 (en) * | 2010-07-16 | 2012-01-19 | E. I. Du Pont De Nemours And Company | In-jet ink comprising cross-linked pigment dispersion based on polyurethane dispersants |
| WO2012039716A1 (en) | 2010-09-23 | 2012-03-29 | Hewlett-Packard Development Company, L.P. | Ink jet ink with high structure pigment particles |
| WO2012042968A1 (ja) * | 2010-09-29 | 2012-04-05 | Dic株式会社 | インクジェット印刷インク用バインダー、それを含むインクジェット印刷用インク及び印刷物 |
| WO2012058094A1 (en) * | 2010-10-29 | 2012-05-03 | E. I. Du Pont De Nemours And Company | Inkjet inks with polyurethane additive with a limited amount of branching |
| US20130201250A1 (en) * | 2010-10-29 | 2013-08-08 | E I Du Pont De Nemours And Company | Polyurethane dispersants based on asymmetric branched trisubstituted isocyanate reactive compounds. |
| GB201111585D0 (en) | 2011-07-07 | 2011-08-24 | Fujifilm Imaging Colorants Ltd | Process for preparing polymers, polymers, dispersions, inks and uses |
| GB201111583D0 (en) | 2011-07-07 | 2011-08-24 | Fujifilm Imaging Colorants Ltd | Process for preparing polymers,polymers,dispersions,inks and uses |
| EP3409731B1 (de) | 2017-05-30 | 2021-08-11 | Artech GmbH design + production in plastic | Wasserbasierte tintenzusammensetzung zum bedrucken von kunststoffoberflächen |
| CN108864407B (zh) * | 2018-08-02 | 2020-12-22 | 北京中纺化工股份有限公司 | 一种耐洗涤拒水增效剂及其制备方法与应用 |
| CN113480712A (zh) * | 2021-07-20 | 2021-10-08 | 昆山九璨新材料科技有限公司 | 一种分散剂及光固化3d打印油墨 |
| CN114106288B (zh) * | 2021-11-04 | 2022-12-06 | 江南大学 | 一种水性聚氨酯分散剂的制备方法及其应用 |
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| US5310778A (en) * | 1992-08-25 | 1994-05-10 | E. I. Du Pont De Nemours And Company | Process for preparing ink jet inks having improved properties |
| DE4314111A1 (de) * | 1993-04-29 | 1994-11-03 | Goldschmidt Ag Th | alpha,omega-Polymethacrylatdiole, Verfahren zu ihrer Herstellung und deren Verwendung zur Herstellung von Polymeren, insbesondere Polyurethanen und Polyestern |
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| DE19849321A1 (de) * | 1998-10-26 | 2000-04-27 | Herberts Gmbh | Pigmentpaste, Pastenharz und Beschichtungsmittel unter deren Verwendung |
| US6133890A (en) * | 1999-03-02 | 2000-10-17 | Damiani; Sylvio Mauro | Self-resonant folded unipole antenna |
| US20010012574A1 (en) * | 2000-01-21 | 2001-08-09 | Victor Company Of Japan, Ltd. | Magnetic recording medium |
| US6494569B2 (en) * | 2000-06-21 | 2002-12-17 | Canon Kabushiki Kaisha | Ink-jet printing method |
| US6316586B1 (en) * | 2000-08-15 | 2001-11-13 | E. I. Du Pont De Nemours And Company | Copolyether composition and processes therefor and therewith |
| US20040176530A1 (en) * | 2001-07-13 | 2004-09-09 | Michel Tielemans | Energy curable polymeric ink compositions |
| EP1465956A1 (en) * | 2002-01-16 | 2004-10-13 | E.I. Du Pont De Nemours And Company | Smear resistant inkjet inks |
| US20030160851A1 (en) * | 2002-02-12 | 2003-08-28 | Baccay Romeo A. | Inkjet printed textiles with improved durability |
| US20040092622A1 (en) * | 2002-07-01 | 2004-05-13 | Pearlstine Kathryn Amy | Inkjet ink with reduced bronzing |
| US20040030095A1 (en) * | 2002-08-09 | 2004-02-12 | Sunkara Hari B. | Poly(trimethylene-ethylene ether) glycols |
| DE10245209A1 (de) * | 2002-09-27 | 2004-04-08 | Basf Ag | Aufzeichnungsflüssigkeiten |
| US20040201658A1 (en) * | 2003-01-16 | 2004-10-14 | Christian Jackson | Inkjet ink set and method of using same |
| EP1454968B1 (en) * | 2003-03-04 | 2010-04-28 | Seiko Epson Corporation | Pigment-dispersed aqueous recording liquid and printed material |
| AU2004223820A1 (en) * | 2003-03-21 | 2004-10-07 | E. I. Du Pont De Nemours And Company | Polytrimethylene ether diol containing coating compositions |
| US8470741B2 (en) * | 2003-05-07 | 2013-06-25 | Croda Americas Llc | Homogeneous liquid saccharide and oil systems |
| EP1477850A1 (en) * | 2003-05-13 | 2004-11-17 | ASML Netherlands B.V. | Lithographic apparatus and device manufacturing method |
| US20050137375A1 (en) * | 2003-12-19 | 2005-06-23 | 3M Innovative Properties Company | Polyurethane-based pressure sensitive adhesives and methods of manufacture |
| US20050182154A1 (en) * | 2004-01-21 | 2005-08-18 | Berge Charles T. | Inkjet inks containing crosslinked polyurethanes |
| US8492456B2 (en) * | 2004-02-09 | 2013-07-23 | Hewlett-Packard Development Company, L.P. | Ink compositions for ink-jet printing |
| GB0420112D0 (en) * | 2004-09-10 | 2004-10-13 | Avecia Ltd | Polyurethanes |
| US7240371B2 (en) * | 2005-02-11 | 2007-07-10 | Invista North America S.A.R.L. | Solvent free aqueous polyurethane dispersions and adhesive films therefrom for stretch fabrics |
| JP5244789B2 (ja) * | 2006-05-02 | 2013-07-24 | イー・アイ・デュポン・ドウ・ヌムール・アンド・カンパニー | インクジェットインク、インクセットおよび印刷方法 |
| US20080175875A1 (en) * | 2006-09-25 | 2008-07-24 | Hari Babu Sunkara | Cosmetic compositions |
| US20090259012A1 (en) * | 2007-12-10 | 2009-10-15 | Roberts C Chad | Urea-terminated ether polyurethanes and aqueous dispersions thereof |
| US20130022746A9 (en) * | 2007-12-10 | 2013-01-24 | Harry Joseph Spinelli | Aqueous inkjet inks with ionically stabilized dispersions and polyurethane ink additives |
| US8759418B2 (en) * | 2008-05-23 | 2014-06-24 | E I Du Pont De Nemours And Company | Urea-terminated polyurethane dispersants |
| EP2285918B1 (en) * | 2008-05-23 | 2012-08-01 | E. I. du Pont de Nemours and Company | Inkjet ink with self dispersed pigments and polyurethane ink additives |
-
2009
- 2009-05-22 WO PCT/US2009/044994 patent/WO2009143433A1/en not_active Ceased
- 2009-05-22 JP JP2011511740A patent/JP2011521096A/ja not_active Withdrawn
- 2009-05-22 EP EP09751661.1A patent/EP2294103B1/en not_active Not-in-force
- 2009-05-22 US US12/990,954 patent/US20110060102A1/en not_active Abandoned
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2013538275A (ja) * | 2010-08-31 | 2013-10-10 | イー・アイ・デュポン・ドウ・ヌムール・アンド・カンパニー | 被架橋顔料分散物およびポリマーバインダーを含むインクジェットインク |
| JP2015063582A (ja) * | 2013-09-24 | 2015-04-09 | Dic株式会社 | 水性顔料組成物の製造方法及び捺染用のインキ |
| JP2016044282A (ja) * | 2014-08-26 | 2016-04-04 | 東洋インキＳｃホールディングス株式会社 | グラビア印刷用水性印刷インキ組成物 |
| JP2017206623A (ja) * | 2016-05-19 | 2017-11-24 | 株式会社リコー | 微粒子分散体、インク、インク入り容器、画像形成装置、及び画像形成方法 |
Also Published As
| Publication number | Publication date |
|---|---|
| US20110060102A1 (en) | 2011-03-10 |
| EP2294103A1 (en) | 2011-03-16 |
| WO2009143433A1 (en) | 2009-11-26 |
| EP2294103B1 (en) | 2014-06-18 |
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