CA2380180A1 - Pigment dispersants formed by reacting an isocyanate with a poly(ethylene glycol) alkyl ether, a polyester or polyacrylate and a diamine - Google Patents
Pigment dispersants formed by reacting an isocyanate with a poly(ethylene glycol) alkyl ether, a polyester or polyacrylate and a diamine Download PDFInfo
- Publication number
- CA2380180A1 CA2380180A1 CA002380180A CA2380180A CA2380180A1 CA 2380180 A1 CA2380180 A1 CA 2380180A1 CA 002380180 A CA002380180 A CA 002380180A CA 2380180 A CA2380180 A CA 2380180A CA 2380180 A1 CA2380180 A1 CA 2380180A1
- Authority
- CA
- Canada
- Prior art keywords
- isocyanate
- dispersant
- polyester
- diamine
- reacted
- 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.)
- Abandoned
Links
- 239000002270 dispersing agent Substances 0.000 title claims abstract description 49
- 239000012948 isocyanate Substances 0.000 title claims abstract description 40
- 150000002513 isocyanates Chemical class 0.000 title claims abstract description 39
- 229920000728 polyester Polymers 0.000 title claims abstract description 35
- 239000000049 pigment Substances 0.000 title claims abstract description 33
- 229920001223 polyethylene glycol Polymers 0.000 title claims abstract description 28
- -1 poly(ethylene glycol) Polymers 0.000 title claims abstract description 22
- 150000004985 diamines Chemical class 0.000 title claims abstract description 21
- 229920000058 polyacrylate Polymers 0.000 title claims abstract description 15
- 150000005215 alkyl ethers Chemical class 0.000 title claims abstract description 13
- 239000000203 mixture Substances 0.000 claims abstract description 10
- 150000003512 tertiary amines Chemical class 0.000 claims abstract description 5
- 150000003141 primary amines Chemical class 0.000 claims abstract description 4
- MWKFXSUHUHTGQN-UHFFFAOYSA-N decan-1-ol Chemical compound CCCCCCCCCCO MWKFXSUHUHTGQN-UHFFFAOYSA-N 0.000 claims description 22
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 claims description 21
- PAPBSGBWRJIAAV-UHFFFAOYSA-N ε-Caprolactone Chemical compound O=C1CCCCCO1 PAPBSGBWRJIAAV-UHFFFAOYSA-N 0.000 claims description 13
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 12
- 239000005057 Hexamethylene diisocyanate Substances 0.000 claims description 6
- 125000000217 alkyl group Chemical group 0.000 claims description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 5
- NAQMVNRVTILPCV-UHFFFAOYSA-N hexane-1,6-diamine Chemical compound NCCCCCCN NAQMVNRVTILPCV-UHFFFAOYSA-N 0.000 claims description 4
- OHJMTUPIZMNBFR-UHFFFAOYSA-N biuret Chemical compound NC(=O)NC(N)=O OHJMTUPIZMNBFR-UHFFFAOYSA-N 0.000 claims description 3
- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 claims description 3
- 229920001600 hydrophobic polymer Polymers 0.000 claims description 3
- DVKJHBMWWAPEIU-UHFFFAOYSA-N toluene 2,4-diisocyanate Chemical compound CC1=CC=C(N=C=O)C=C1N=C=O DVKJHBMWWAPEIU-UHFFFAOYSA-N 0.000 claims description 3
- 229920006395 saturated elastomer Polymers 0.000 claims description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract description 11
- 239000002904 solvent Substances 0.000 abstract description 10
- 238000000576 coating method Methods 0.000 abstract description 9
- 239000003973 paint Substances 0.000 abstract description 4
- 239000011248 coating agent Substances 0.000 abstract description 2
- 239000002798 polar solvent Substances 0.000 abstract description 2
- 238000009472 formulation Methods 0.000 abstract 1
- 230000000087 stabilizing effect Effects 0.000 abstract 1
- 239000002202 Polyethylene glycol Substances 0.000 description 23
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 22
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 18
- 239000000243 solution Substances 0.000 description 18
- 150000001412 amines Chemical class 0.000 description 16
- 239000007787 solid Substances 0.000 description 15
- 239000006185 dispersion Substances 0.000 description 11
- 229910052757 nitrogen Inorganic materials 0.000 description 11
- 239000000047 product Substances 0.000 description 11
- 238000010992 reflux Methods 0.000 description 11
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 10
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 10
- 239000000463 material Substances 0.000 description 9
- 238000006243 chemical reaction Methods 0.000 description 8
- 229920000642 polymer Polymers 0.000 description 8
- KDHWOCLBMVSZPG-UHFFFAOYSA-N 3-imidazol-1-ylpropan-1-amine Chemical compound NCCCN1C=CN=C1 KDHWOCLBMVSZPG-UHFFFAOYSA-N 0.000 description 7
- 125000002091 cationic group Chemical group 0.000 description 7
- 239000000126 substance Substances 0.000 description 7
- OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 description 6
- DGVVWUTYPXICAM-UHFFFAOYSA-N β‐Mercaptoethanol Chemical compound OCCS DGVVWUTYPXICAM-UHFFFAOYSA-N 0.000 description 6
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 5
- OEYNWAWWSZUGDU-UHFFFAOYSA-N 1-methoxypropane-1,2-diol Chemical compound COC(O)C(C)O OEYNWAWWSZUGDU-UHFFFAOYSA-N 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 4
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 4
- 230000000052 comparative effect Effects 0.000 description 4
- 239000003999 initiator Substances 0.000 description 4
- 239000000178 monomer Substances 0.000 description 4
- 229940105325 3-dimethylaminopropylamine Drugs 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- 230000002378 acidificating effect Effects 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 239000006229 carbon black Substances 0.000 description 3
- IUNMPGNGSSIWFP-UHFFFAOYSA-N dimethylaminopropylamine Chemical compound CN(C)CCCN IUNMPGNGSSIWFP-UHFFFAOYSA-N 0.000 description 3
- 238000005227 gel permeation chromatography Methods 0.000 description 3
- 230000002209 hydrophobic effect Effects 0.000 description 3
- 238000000034 method Methods 0.000 description 3
- 239000000376 reactant Substances 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- 238000012360 testing method Methods 0.000 description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
- UIKUBYKUYUSRSM-UHFFFAOYSA-N 3-morpholinopropylamine Chemical compound NCCCN1CCOCC1 UIKUBYKUYUSRSM-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- SOGAXMICEFXMKE-UHFFFAOYSA-N Butylmethacrylate Chemical compound CCCCOC(=O)C(C)=C SOGAXMICEFXMKE-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 229920000877 Melamine resin Polymers 0.000 description 2
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 2
- 239000004698 Polyethylene Substances 0.000 description 2
- 239000004793 Polystyrene Substances 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 2
- BQONWAYJUMWNJN-UHFFFAOYSA-N acetic acid;1-methoxypropane-1,2-diol Chemical compound CC(O)=O.COC(O)C(C)O BQONWAYJUMWNJN-UHFFFAOYSA-N 0.000 description 2
- 125000002723 alicyclic group Chemical group 0.000 description 2
- 125000000129 anionic group Chemical group 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 238000007796 conventional method Methods 0.000 description 2
- 125000000524 functional group Chemical group 0.000 description 2
- 238000000227 grinding Methods 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 230000005764 inhibitory process Effects 0.000 description 2
- 239000012860 organic pigment Substances 0.000 description 2
- 229920003229 poly(methyl methacrylate) Polymers 0.000 description 2
- 229920000570 polyether Polymers 0.000 description 2
- 229920000573 polyethylene Polymers 0.000 description 2
- 239000004926 polymethyl methacrylate Substances 0.000 description 2
- 229920002223 polystyrene Polymers 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical group CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 150000003673 urethanes Chemical class 0.000 description 2
- SILNNFMWIMZVEQ-UHFFFAOYSA-N 1,3-dihydrobenzimidazol-2-one Chemical class C1=CC=C2NC(O)=NC2=C1 SILNNFMWIMZVEQ-UHFFFAOYSA-N 0.000 description 1
- CGLVZFOCZLHKOH-UHFFFAOYSA-N 8,18-dichloro-5,15-diethyl-5,15-dihydrodiindolo(3,2-b:3',2'-m)triphenodioxazine Chemical compound CCN1C2=CC=CC=C2C2=C1C=C1OC3=C(Cl)C4=NC(C=C5C6=CC=CC=C6N(C5=C5)CC)=C5OC4=C(Cl)C3=NC1=C2 CGLVZFOCZLHKOH-UHFFFAOYSA-N 0.000 description 1
- 239000004923 Acrylic lacquer Substances 0.000 description 1
- 230000005653 Brownian motion process Effects 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 239000004721 Polyphenylene oxide Substances 0.000 description 1
- NRCMAYZCPIVABH-UHFFFAOYSA-N Quinacridone Chemical compound N1C2=CC=CC=C2C(=O)C2=C1C=C1C(=O)C3=CC=CC=C3NC1=C2 NRCMAYZCPIVABH-UHFFFAOYSA-N 0.000 description 1
- 239000012963 UV stabilizer Substances 0.000 description 1
- UKLDJPRMSDWDSL-UHFFFAOYSA-L [dibutyl(dodecanoyloxy)stannyl] dodecanoate Chemical compound CCCCCCCCCCCC(=O)O[Sn](CCCC)(CCCC)OC(=O)CCCCCCCCCCC UKLDJPRMSDWDSL-UHFFFAOYSA-L 0.000 description 1
- 239000006096 absorbing agent Substances 0.000 description 1
- 238000007171 acid catalysis Methods 0.000 description 1
- YJVBLROMQZEFPA-UHFFFAOYSA-L acid red 26 Chemical compound [Na+].[Na+].CC1=CC(C)=CC=C1N=NC1=C(O)C(S([O-])(=O)=O)=CC2=CC(S([O-])(=O)=O)=CC=C12 YJVBLROMQZEFPA-UHFFFAOYSA-L 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 238000000498 ball milling Methods 0.000 description 1
- TZCXTZWJZNENPQ-UHFFFAOYSA-L barium sulfate Chemical compound [Ba+2].[O-]S([O-])(=O)=O TZCXTZWJZNENPQ-UHFFFAOYSA-L 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- UDSAIICHUKSCKT-UHFFFAOYSA-N bromophenol blue Chemical compound C1=C(Br)C(O)=C(Br)C=C1C1(C=2C=C(Br)C(O)=C(Br)C=2)C2=CC=CC=C2S(=O)(=O)O1 UDSAIICHUKSCKT-UHFFFAOYSA-N 0.000 description 1
- 238000005537 brownian motion Methods 0.000 description 1
- 150000001716 carbazoles Chemical class 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 239000008199 coating composition Substances 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 230000000536 complexating effect Effects 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 238000004132 cross linking Methods 0.000 description 1
- 239000003431 cross linking reagent Substances 0.000 description 1
- 239000012975 dibutyltin dilaurate Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000003822 epoxy resin Substances 0.000 description 1
- 230000007717 exclusion Effects 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 238000005189 flocculation Methods 0.000 description 1
- 230000016615 flocculation Effects 0.000 description 1
- 229910021485 fumed silica Inorganic materials 0.000 description 1
- 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 1
- 238000007542 hardness measurement Methods 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 125000002883 imidazolyl group Chemical group 0.000 description 1
- 235000019239 indanthrene blue RS Nutrition 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 230000000977 initiatory effect Effects 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- UQSXHKLRYXJYBZ-UHFFFAOYSA-N iron oxide Inorganic materials [Fe]=O UQSXHKLRYXJYBZ-UHFFFAOYSA-N 0.000 description 1
- 235000013980 iron oxide Nutrition 0.000 description 1
- VBMVTYDPPZVILR-UHFFFAOYSA-N iron(2+);oxygen(2-) Chemical class [O-2].[Fe+2] VBMVTYDPPZVILR-UHFFFAOYSA-N 0.000 description 1
- ZFSLODLOARCGLH-UHFFFAOYSA-N isocyanuric acid Chemical compound OC1=NC(O)=NC(O)=N1 ZFSLODLOARCGLH-UHFFFAOYSA-N 0.000 description 1
- PXZQEOJJUGGUIB-UHFFFAOYSA-N isoindolin-1-one Chemical class C1=CC=C2C(=O)NCC2=C1 PXZQEOJJUGGUIB-UHFFFAOYSA-N 0.000 description 1
- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 150000007974 melamines Chemical class 0.000 description 1
- 229910044991 metal oxide Inorganic materials 0.000 description 1
- 238000003801 milling Methods 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 150000002979 perylenes Chemical class 0.000 description 1
- 229920001490 poly(butyl methacrylate) polymer Polymers 0.000 description 1
- 229920000647 polyepoxide Polymers 0.000 description 1
- HDOUGSFASVGDCS-UHFFFAOYSA-N pyridin-3-ylmethanamine Chemical compound NCC1=CC=CN=C1 HDOUGSFASVGDCS-UHFFFAOYSA-N 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 238000000518 rheometry Methods 0.000 description 1
- 239000004576 sand Substances 0.000 description 1
- 150000004760 silicates Chemical class 0.000 description 1
- 230000006641 stabilisation Effects 0.000 description 1
- 238000011105 stabilization Methods 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 238000004381 surface treatment Methods 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- JOUDBUYBGJYFFP-FOCLMDBBSA-N thioindigo Chemical compound S\1C2=CC=CC=C2C(=O)C/1=C1/C(=O)C2=CC=CC=C2S1 JOUDBUYBGJYFFP-FOCLMDBBSA-N 0.000 description 1
- 239000004408 titanium dioxide Substances 0.000 description 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N urea group Chemical group NC(=O)N XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
- 239000003643 water by type Substances 0.000 description 1
- 229940045860 white wax Drugs 0.000 description 1
- 239000011787 zinc oxide Substances 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
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B67/00—Influencing the physical, e.g. the dyeing or printing properties of dyestuffs without chemical reactions, e.g. by treating with solvents grinding or grinding assistants, coating of pigments or dyes; Process features in the making of dyestuff preparations; Dyestuff preparations of a special physical nature, e.g. tablets, films
- C09B67/006—Preparation of organic pigments
- C09B67/0066—Aqueous dispersions of pigments containing only dispersing agents
-
- 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
-
- 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
- C08G18/2805—Compounds having only one group containing active hydrogen
- C08G18/2815—Monohydroxy compounds
-
- 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
- C08G18/77—Polyisocyanates or polyisothiocyanates having heteroatoms in addition to the isocyanate or isothiocyanate nitrogen and oxygen or sulfur
- C08G18/78—Nitrogen
- C08G18/79—Nitrogen characterised by the polyisocyanates used, these having groups formed by oligomerisation of isocyanates or isothiocyanates
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B67/00—Influencing the physical, e.g. the dyeing or printing properties of dyestuffs without chemical reactions, e.g. by treating with solvents grinding or grinding assistants, coating of pigments or dyes; Process features in the making of dyestuff preparations; Dyestuff preparations of a special physical nature, e.g. tablets, films
- C09B67/0071—Process features in the making of dyestuff preparations; Dehydrating agents; Dispersing agents; Dustfree compositions
- C09B67/0084—Dispersions of dyes
- C09B67/0085—Non common dispersing agents
-
- 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
- C09D17/00—Pigment pastes, e.g. for mixing in paints
-
- 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
- C09D7/00—Features of coating compositions, not provided for in group C09D5/00; Processes for incorporating ingredients in coating compositions
- C09D7/40—Additives
- C09D7/45—Anti-settling agents
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K23/00—Use of substances as emulsifying, wetting, dispersing, or foam-producing agents
- C09K23/16—Amines or polyamines
-
- C—CHEMISTRY; METALLURGY
- C02—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
- C02F—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
- C02F2103/00—Nature of the water, waste water, sewage or sludge to be treated
- C02F2103/14—Paint wastes
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Life Sciences & Earth Sciences (AREA)
- Wood Science & Technology (AREA)
- Dispersion Chemistry (AREA)
- Emulsifying, Dispersing, Foam-Producing Or Wetting Agents (AREA)
- Polyurethanes Or Polyureas (AREA)
- Paints Or Removers (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US09/370,416 | 1999-08-09 | ||
| US09/370,416 US6506899B1 (en) | 1999-08-09 | 1999-08-09 | Pigment dispersants formed by reacting an isocyanate with a poly (ethylene glycol) alkyl ether, a polyester or polyester or polyacrylate and a diamine |
| PCT/US2000/021720 WO2001010923A1 (en) | 1999-08-09 | 2000-08-09 | Pigment dispersants formed by reacting an isocyanate with a poly(ethylene glycol) alkyl ether, a polyester or polyacrylate and a diamine |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2380180A1 true CA2380180A1 (en) | 2001-02-15 |
Family
ID=23459568
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002380180A Abandoned CA2380180A1 (en) | 1999-08-09 | 2000-08-09 | Pigment dispersants formed by reacting an isocyanate with a poly(ethylene glycol) alkyl ether, a polyester or polyacrylate and a diamine |
Country Status (11)
| Country | Link |
|---|---|
| US (1) | US6506899B1 (https=) |
| EP (1) | EP1204690B1 (https=) |
| JP (1) | JP2003506538A (https=) |
| KR (1) | KR100483096B1 (https=) |
| CN (1) | CN1368986A (https=) |
| AU (1) | AU769420B2 (https=) |
| BR (1) | BR0013300A (https=) |
| CA (1) | CA2380180A1 (https=) |
| DE (2) | DE60036624T8 (https=) |
| MX (1) | MXPA02001399A (https=) |
| WO (1) | WO2001010923A1 (https=) |
Families Citing this family (36)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE10116767A1 (de) | 2001-04-04 | 2002-10-10 | Basf Ag | Neue polymere Dispergieradditive mit hyperverzweigten Strukturen |
| EP1364701A1 (en) * | 2002-05-21 | 2003-11-26 | Akzo Nobel N.V. | Amide-modified resin or hydrocarbyl moiety for dispersing a pigment |
| US7276555B2 (en) * | 2002-05-21 | 2007-10-02 | Hexion Specialty Chemicals, Inc. | Amide-modified resin or hydrocarbyl moiety for dispersing a pigment |
| US20040249023A1 (en) * | 2003-01-17 | 2004-12-09 | Stoffer James O. | Compounds for corrosion resistant primer coatings and protection of metal substrates |
| EP1587884A2 (en) * | 2003-01-17 | 2005-10-26 | University of Missouri Curators, Office of Tech. & Spec. Projects | Corrosion resistant coatings containing rare earth compounds |
| US7601425B2 (en) * | 2003-03-07 | 2009-10-13 | The Curators Of The University Of Missouri | Corrosion resistant coatings containing carbon |
| EP1632510A4 (en) * | 2003-06-09 | 2011-03-30 | Kyoeisha Chemical Co Ltd | RESINS HAVING A MODIFIED RING AND DISPERSANTS CONTAINING SAID RESINS |
| EP1756188B1 (de) * | 2004-06-08 | 2007-12-05 | Basf Aktiengesellschaft | Amphiphile polymerzusammensetzungen und ihre verwendung |
| EP2292668B2 (en) * | 2004-10-25 | 2025-09-10 | The Lubrizol Corporation | Process for preparing polymers and compositions thereof |
| CA2589849A1 (en) | 2004-12-10 | 2006-06-15 | Mitsui Chemicals Polyurethanes, Inc. | Aqueous polyurethane resin, method for producing aqueous polyurethane resin and film |
| AU2006298726A1 (en) * | 2005-10-04 | 2007-04-12 | Akzo Nobel Coatings International B.V. | Pigment preparation |
| US7635504B2 (en) * | 2006-05-05 | 2009-12-22 | E. I. Du Pont De Nemours And Company | Curable white inkjet ink |
| JP2008013725A (ja) * | 2006-07-10 | 2008-01-24 | Sanyo Chem Ind Ltd | 顔料分散剤および印刷インキ組成物 |
| CN101053798B (zh) * | 2007-02-13 | 2011-06-01 | 煤炭科学研究总院爆破技术研究所 | 双子型乳化剂及其制作方法 |
| JP4643693B2 (ja) * | 2007-08-28 | 2011-03-02 | 三洋化成工業株式会社 | 樹脂粒子用顔料分散剤 |
| JP5470945B2 (ja) * | 2008-03-24 | 2014-04-16 | 東洋インキＳｃホールディングス株式会社 | 分散剤、並びに、それを用いた顔料組成物、顔料分散体、及びインクジェットインキ |
| JP5415143B2 (ja) * | 2008-04-30 | 2014-02-12 | 三洋化成工業株式会社 | トナー用樹脂組成物およびトナー組成物 |
| JP5407401B2 (ja) * | 2009-02-17 | 2014-02-05 | 東洋インキＳｃホールディングス株式会社 | 分散剤、並びに、それを用いた顔料組成物及び顔料分散体 |
| JP5678389B2 (ja) * | 2009-09-02 | 2015-03-04 | 東海カーボン株式会社 | ポリウレタン樹脂付加顔料の水性分散体の製造方法、ポリウレタン樹脂付加顔料の水性分散体およびインク組成物 |
| JP2011246675A (ja) * | 2010-05-31 | 2011-12-08 | Tokai Carbon Co Ltd | ポリウレタン樹脂付着顔料、顔料分散組成物およびインクジェットインク組成物 |
| EP2392624A1 (en) * | 2010-06-01 | 2011-12-07 | Akzo Nobel Coatings International B.V. | Low VOC Colorant Compositions |
| WO2012117099A1 (de) * | 2011-03-03 | 2012-09-07 | Basf Se | Verfahren zur herstellung von biuretgruppenhaltigen polyisocyanaten |
| WO2013147168A1 (ja) * | 2012-03-30 | 2013-10-03 | 株式会社Ｄｎｐファインケミカル | トナー粒子用着色顔料分散液及び静電荷像現像用トナー |
| CN102746714A (zh) * | 2012-05-02 | 2012-10-24 | 中国皮革和制鞋工业研究院 | 一种耐迁移皮革染料的制备方法 |
| US9315615B2 (en) * | 2013-03-15 | 2016-04-19 | Tronox Llc | Titanium dioxide pigment and manufacturing method |
| JP6469356B2 (ja) * | 2013-07-29 | 2019-02-13 | 昭和電工パッケージング株式会社 | 電池ケース |
| JP6617703B2 (ja) | 2014-07-11 | 2019-12-11 | 三菱ケミカル株式会社 | 感光性樹脂組成物、硬化物、ブラックマトリックス及び画像表示装置 |
| ES2765548T3 (es) * | 2014-09-18 | 2020-06-09 | Evonik Operations Gmbh | Compuestos de adición adecuados como dispersantes o agentes antisedimentación |
| WO2016082058A1 (en) * | 2014-11-25 | 2016-06-02 | Deuchem (Shanghai) Chemical Co., Ltd. | Urethane dispersants |
| CN106554468B (zh) * | 2015-09-29 | 2019-11-12 | 常州领景新材料科技有限公司 | 一种活性聚氨酯高分子化合物 |
| TW201840635A (zh) * | 2017-01-26 | 2018-11-16 | 美商盧伯利索先進材料有限公司 | 具有改良化學及熱安定性之含有一或二個四級胺錨定基的聚合分散劑 |
| KR102401699B1 (ko) * | 2017-06-20 | 2022-05-26 | 애버리 데니슨 코포레이션 | 폴리에스테르-이소시아네이트 코팅 및 이것을 포함하는 라벨 |
| JP7262942B2 (ja) * | 2017-08-08 | 2023-04-24 | 旭化成株式会社 | 親水性ポリイソシアネート組成物、硬化剤組成物及び水系コーティング組成物 |
| WO2020185450A1 (en) * | 2019-03-12 | 2020-09-17 | Huntsman Petrochemical Llc | Dispersants made from isocyanates and amines |
| CN112778488A (zh) * | 2020-12-29 | 2021-05-11 | 江南大学 | 一种反应性支化聚氨酯高分子分散剂的制备方法 |
| 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 |
Family Cites Families (25)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3788996A (en) | 1970-05-21 | 1974-01-29 | Du Pont | Coating compositions containing polymeric dispersing aids |
| US3741941A (en) | 1971-03-03 | 1973-06-26 | Du Pont | Polyesters with terminal polyhydroxy groups |
| US3775327A (en) | 1971-04-12 | 1973-11-27 | Du Pont | Dispersions containing polyesters with terminal polyhydroxyl groups |
| US3817944A (en) | 1972-04-05 | 1974-06-18 | Du Pont | Polyesters with acid end groups |
| US4032698A (en) | 1973-02-02 | 1977-06-28 | E. I. Du Pont De Nemours And Company | Polymeric materials with substituted urea end groups |
| US4029861A (en) | 1973-02-02 | 1977-06-14 | E. I. Du Pont De Nemours And Company | Polymeric materials with acid end groups |
| US4070388A (en) | 1975-10-14 | 1978-01-24 | E. I. Du Pont De Nemours And Company | Polymeric materials with acid end groups |
| US4048207A (en) | 1975-10-14 | 1977-09-13 | E. I. Du Pont De Nemours And Company | Polymeric materials with silane end groups |
| JPS56143280A (en) | 1980-04-10 | 1981-11-07 | Nippon Urethane Service:Kk | Water-resisting adhesive |
| DE3465599D1 (en) | 1984-01-27 | 1987-10-01 | Byk Chemie Gmbh | Addition compounds suited as dispersing agents, process for their preparation, their use and solid materials coated with them |
| ATE29138T1 (de) * | 1984-01-27 | 1987-09-15 | Byk Chemie Gmbh | Als dispergiermittel geeignete additionsverbindungen, verfahren zu ihrer herstellung, ihre verwendung und damit beschichtete feststoffe. |
| DE3446084A1 (de) * | 1984-12-18 | 1986-06-19 | Hoechst Ag, 6230 Frankfurt | Additionsverbindungen und verfahren zu ihrer herstellung |
| DE3542437A1 (de) * | 1984-12-18 | 1986-06-19 | Hoechst Ag, 6230 Frankfurt | Pulverpigment mit verbesserten rheologischen eigenschaften, verfahren zu ihrer herstellung und ihre verwendung mit einem gehalt von mindestens 5 % unsubstituiertem chinacridon |
| DE3641581C3 (de) | 1986-12-05 | 1996-08-01 | Byk Chemie Gmbh | Verfahren zur Herstellung von Dispergiermitteln und deren Salzen und ihre Verwendung |
| DE3810781A1 (de) * | 1988-03-30 | 1989-10-12 | Bayer Ag | Neue polyisocyanat-polyadditionsverbindungen, verfahren zu deren herstellung und deren verwendung zur dispergierung von feststoffen |
| CA2032992C (en) | 1989-12-29 | 2001-04-10 | Peter H. Quednau | Dispersing agents, their use and solids coated therewith |
| US5425900A (en) | 1990-12-27 | 1995-06-20 | Efka-Chemicals B.V. | Dispersing agents, their use and solids coated therewith |
| ES2095002T3 (es) | 1992-02-11 | 1997-02-01 | Zeneca Ltd | Dispersion. |
| JPH05301935A (ja) | 1992-04-28 | 1993-11-16 | Sekisui Chem Co Ltd | 光硬化型樹脂組成物 |
| TW278096B (https=) | 1992-09-24 | 1996-06-11 | Dsm Nv | |
| AU659351B2 (en) | 1992-11-27 | 1995-05-11 | Basf Corporation | Copolymer dispersant composition for inorganic pigments |
| US5700867A (en) | 1993-10-01 | 1997-12-23 | Toyo Ink Manufacturing Co., Ltd. | Aqueous dispersion of an aqueous hydrazine-terminated polyurethane |
| JP2959399B2 (ja) | 1994-06-13 | 1999-10-06 | 日本ポリウレタン工業株式会社 | 自己乳化型ポリイソシアネート混合物、並びにこれを用いた水性塗料組成物および水性接着剤組成物 |
| DE19508390A1 (de) * | 1995-03-09 | 1996-09-12 | Bayer Ag | Dispergierhilfsmittel für wäßrige Lacke |
| DE19522476A1 (de) * | 1995-06-21 | 1997-01-02 | Bayer Ag | Fluor enthaltende Dispergierhilfsmittel für wäßrige Lacke |
-
1999
- 1999-08-09 US US09/370,416 patent/US6506899B1/en not_active Expired - Lifetime
-
2000
- 2000-08-09 BR BR0013300-0A patent/BR0013300A/pt not_active IP Right Cessation
- 2000-08-09 DE DE60036624T patent/DE60036624T8/de active Active
- 2000-08-09 WO PCT/US2000/021720 patent/WO2001010923A1/en not_active Ceased
- 2000-08-09 DE DE60036624A patent/DE60036624D1/de not_active Expired - Lifetime
- 2000-08-09 JP JP2001515728A patent/JP2003506538A/ja active Pending
- 2000-08-09 CA CA002380180A patent/CA2380180A1/en not_active Abandoned
- 2000-08-09 KR KR10-2002-7001764A patent/KR100483096B1/ko not_active Expired - Fee Related
- 2000-08-09 EP EP00952673A patent/EP1204690B1/en not_active Expired - Lifetime
- 2000-08-09 AU AU65328/00A patent/AU769420B2/en not_active Ceased
- 2000-08-09 MX MXPA02001399A patent/MXPA02001399A/es active IP Right Grant
- 2000-08-09 CN CN00811469A patent/CN1368986A/zh active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| DE60036624T4 (de) | 2009-02-05 |
| WO2001010923A1 (en) | 2001-02-15 |
| EP1204690B1 (en) | 2007-10-03 |
| BR0013300A (pt) | 2002-04-16 |
| KR20020019615A (ko) | 2002-03-12 |
| CN1368986A (zh) | 2002-09-11 |
| US6506899B1 (en) | 2003-01-14 |
| DE60036624T2 (de) | 2008-07-24 |
| DE60036624D1 (de) | 2007-11-15 |
| KR100483096B1 (ko) | 2005-04-14 |
| AU6532800A (en) | 2001-03-05 |
| MXPA02001399A (es) | 2002-08-12 |
| AU769420B2 (en) | 2004-01-29 |
| JP2003506538A (ja) | 2003-02-18 |
| EP1204690A1 (en) | 2002-05-15 |
| DE60036624T8 (de) | 2009-08-13 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US6506899B1 (en) | Pigment dispersants formed by reacting an isocyanate with a poly (ethylene glycol) alkyl ether, a polyester or polyester or polyacrylate and a diamine | |
| EP2132237B1 (en) | Dispersant composition | |
| JP5234782B2 (ja) | 反応性二重結合を含むポリウレタンベースの顔料分散剤 | |
| KR101656390B1 (ko) | 선형 폴리우레탄으로부터의 분산제 | |
| CN101945912B (zh) | 润湿剂和分散剂及其制备和应用 | |
| US10442884B2 (en) | Dispersants with multiple aromatic imide anchor groups | |
| KR102214416B1 (ko) | 폴리아민 부가 화합물 | |
| CN102421512B (zh) | 乙烯基聚合物润湿分散剂 | |
| US11879032B2 (en) | Reaction products containing urethane groups and urea groups | |
| US10308836B2 (en) | Dispersants with multiple aromatic imide anchor groups | |
| JP7235121B2 (ja) | ウレタン基を有するアミン官能性化合物 |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request | ||
| FZDE | Discontinued |