JPH0157149B2 - - Google Patents
Info
- Publication number
- JPH0157149B2 JPH0157149B2 JP57081559A JP8155982A JPH0157149B2 JP H0157149 B2 JPH0157149 B2 JP H0157149B2 JP 57081559 A JP57081559 A JP 57081559A JP 8155982 A JP8155982 A JP 8155982A JP H0157149 B2 JPH0157149 B2 JP H0157149B2
- Authority
- JP
- Japan
- Prior art keywords
- water
- parts
- pigment
- ink
- examples
- 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
Links
- 239000000049 pigment Substances 0.000 claims description 52
- 239000000203 mixture Substances 0.000 claims description 32
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical group NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 15
- 150000001875 compounds Chemical class 0.000 claims description 12
- OHJMTUPIZMNBFR-UHFFFAOYSA-N biuret Chemical compound NC(=O)NC(N)=O OHJMTUPIZMNBFR-UHFFFAOYSA-N 0.000 claims description 8
- 239000012860 organic pigment Substances 0.000 claims description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
- 239000000976 ink Substances 0.000 description 61
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 46
- 230000000052 comparative effect Effects 0.000 description 21
- 239000003973 paint Substances 0.000 description 14
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 13
- 238000003860 storage Methods 0.000 description 11
- VMAQYKGITHDWKL-UHFFFAOYSA-N 5-methylimidazolidine-2,4-dione Chemical compound CC1NC(=O)NC1=O VMAQYKGITHDWKL-UHFFFAOYSA-N 0.000 description 10
- 230000009974 thixotropic effect Effects 0.000 description 10
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 description 9
- 230000015572 biosynthetic process Effects 0.000 description 7
- 239000013078 crystal Substances 0.000 description 7
- 238000003786 synthesis reaction Methods 0.000 description 7
- YIROYDNZEPTFOL-UHFFFAOYSA-N 5,5-Dimethylhydantoin Chemical compound CC1(C)NC(=O)NC1=O YIROYDNZEPTFOL-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 239000003795 chemical substances by application Substances 0.000 description 6
- 229920005989 resin Polymers 0.000 description 6
- 239000011347 resin Substances 0.000 description 6
- 239000004094 surface-active agent Substances 0.000 description 6
- 239000004202 carbamide Substances 0.000 description 5
- 235000013877 carbamide Nutrition 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 5
- 229910052739 hydrogen Inorganic materials 0.000 description 5
- 238000011282 treatment Methods 0.000 description 5
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 4
- 239000011248 coating agent Substances 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 238000000921 elemental analysis Methods 0.000 description 4
- WJRBRSLFGCUECM-UHFFFAOYSA-N hydantoin Chemical compound O=C1CNC(=O)N1 WJRBRSLFGCUECM-UHFFFAOYSA-N 0.000 description 4
- 229940091173 hydantoin Drugs 0.000 description 4
- 238000002844 melting Methods 0.000 description 4
- 230000008018 melting Effects 0.000 description 4
- 238000000034 method Methods 0.000 description 4
- 238000002156 mixing Methods 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- -1 thiourea derivative compound Chemical class 0.000 description 4
- 239000002966 varnish Substances 0.000 description 4
- ATRRKUHOCOJYRX-UHFFFAOYSA-N Ammonium bicarbonate Chemical compound [NH4+].OC([O-])=O ATRRKUHOCOJYRX-UHFFFAOYSA-N 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- 150000005215 alkyl ethers Chemical class 0.000 description 3
- 239000001099 ammonium carbonate Substances 0.000 description 3
- 235000012501 ammonium carbonate Nutrition 0.000 description 3
- 238000000576 coating method Methods 0.000 description 3
- 238000000354 decomposition reaction Methods 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- DTCCVIYSGXONHU-CJHDCQNGSA-N (z)-2-(2-phenylethenyl)but-2-enedioic acid Chemical compound OC(=O)\C=C(C(O)=O)\C=CC1=CC=CC=C1 DTCCVIYSGXONHU-CJHDCQNGSA-N 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- RSWGJHLUYNHPMX-UHFFFAOYSA-N Abietic-Saeure Natural products C12CCC(C(C)C)=CC2=CCC2C1(C)CCCC2(C)C(O)=O RSWGJHLUYNHPMX-UHFFFAOYSA-N 0.000 description 2
- 239000004925 Acrylic resin Substances 0.000 description 2
- 229920000178 Acrylic resin Polymers 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- KHPCPRHQVVSZAH-HUOMCSJISA-N Rosin Natural products O(C/C=C/c1ccccc1)[C@H]1[C@H](O)[C@@H](O)[C@@H](O)[C@@H](CO)O1 KHPCPRHQVVSZAH-HUOMCSJISA-N 0.000 description 2
- 229910000831 Steel Inorganic materials 0.000 description 2
- POJWUDADGALRAB-UHFFFAOYSA-N allantoin Chemical compound NC(=O)NC1NC(=O)NC1=O POJWUDADGALRAB-UHFFFAOYSA-N 0.000 description 2
- 239000011324 bead 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
- 230000008878 coupling Effects 0.000 description 2
- 238000010168 coupling process Methods 0.000 description 2
- 238000005859 coupling reaction Methods 0.000 description 2
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 2
- JXTHNDFMNIQAHM-UHFFFAOYSA-N dichloroacetic acid Chemical compound OC(=O)C(Cl)Cl JXTHNDFMNIQAHM-UHFFFAOYSA-N 0.000 description 2
- PPSZHCXTGRHULJ-UHFFFAOYSA-N dioxazine Chemical compound O1ON=CC=C1 PPSZHCXTGRHULJ-UHFFFAOYSA-N 0.000 description 2
- IEQIEDJGQAUEQZ-UHFFFAOYSA-N phthalocyanine Chemical compound N1C(N=C2C3=CC=CC=C3C(N=C3C4=CC=CC=C4C(=N4)N3)=N2)=C(C=CC=C2)C2=C1N=C1C2=CC=CC=C2C4=N1 IEQIEDJGQAUEQZ-UHFFFAOYSA-N 0.000 description 2
- 239000002798 polar solvent Substances 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 239000010959 steel Substances 0.000 description 2
- KHPCPRHQVVSZAH-UHFFFAOYSA-N trans-cinnamyl beta-D-glucopyranoside Natural products OC1C(O)C(O)C(CO)OC1OCC=CC1=CC=CC=C1 KHPCPRHQVVSZAH-UHFFFAOYSA-N 0.000 description 2
- HXKKHQJGJAFBHI-UHFFFAOYSA-N 1-aminopropan-2-ol Chemical compound CC(O)CN HXKKHQJGJAFBHI-UHFFFAOYSA-N 0.000 description 1
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 1
- VSJRBQDMBFFHMC-UHFFFAOYSA-N 5-ethyl-5-methylimidazolidine-2,4-dione Chemical compound CCC1(C)NC(=O)NC1=O VSJRBQDMBFFHMC-UHFFFAOYSA-N 0.000 description 1
- JNGWGQUYLVSFND-UHFFFAOYSA-N 5-methyl-5-phenylimidazolidine-2,4-dione Chemical compound C=1C=CC=CC=1C1(C)NC(=O)NC1=O JNGWGQUYLVSFND-UHFFFAOYSA-N 0.000 description 1
- NXQJDVBMMRCKQG-UHFFFAOYSA-N 5-phenylimidazolidine-2,4-dione Chemical compound O=C1NC(=O)NC1C1=CC=CC=C1 NXQJDVBMMRCKQG-UHFFFAOYSA-N 0.000 description 1
- DEXFNLNNUZKHNO-UHFFFAOYSA-N 6-[3-[4-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]piperidin-1-yl]-3-oxopropyl]-3H-1,3-benzoxazol-2-one Chemical group C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C1CCN(CC1)C(CCC1=CC2=C(NC(O2)=O)C=C1)=O DEXFNLNNUZKHNO-UHFFFAOYSA-N 0.000 description 1
- POJWUDADGALRAB-PVQJCKRUSA-N Allantoin Natural products NC(=O)N[C@@H]1NC(=O)NC1=O POJWUDADGALRAB-PVQJCKRUSA-N 0.000 description 1
- 239000004593 Epoxy Substances 0.000 description 1
- 235000000177 Indigofera tinctoria Nutrition 0.000 description 1
- 229920000877 Melamine resin Polymers 0.000 description 1
- CXOFVDLJLONNDW-UHFFFAOYSA-N Phenytoin Chemical compound N1C(=O)NC(=O)C1(C=1C=CC=CC=1)C1=CC=CC=C1 CXOFVDLJLONNDW-UHFFFAOYSA-N 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
- LEHOTFFKMJEONL-UHFFFAOYSA-N Uric Acid Chemical compound N1C(=O)NC(=O)C2=C1NC(=O)N2 LEHOTFFKMJEONL-UHFFFAOYSA-N 0.000 description 1
- TVWHNULVHGKJHS-UHFFFAOYSA-N Uric acid Natural products N1C(=O)NC(=O)C2NC(=O)NC21 TVWHNULVHGKJHS-UHFFFAOYSA-N 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 239000003905 agrochemical Substances 0.000 description 1
- 238000003915 air pollution Methods 0.000 description 1
- 229920000180 alkyd Polymers 0.000 description 1
- 229960000458 allantoin Drugs 0.000 description 1
- 239000008135 aqueous vehicle Substances 0.000 description 1
- 150000001728 carbonyl compounds Chemical class 0.000 description 1
- KXZJHVJKXJLBKO-UHFFFAOYSA-N chembl1408157 Chemical compound N=1C2=CC=CC=C2C(C(=O)O)=CC=1C1=CC=C(O)C=C1 KXZJHVJKXJLBKO-UHFFFAOYSA-N 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 238000006482 condensation reaction Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 230000006866 deterioration Effects 0.000 description 1
- 229960005215 dichloroacetic acid Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- IDGUHHHQCWSQLU-UHFFFAOYSA-N ethanol;hydrate Chemical compound O.CCO IDGUHHHQCWSQLU-UHFFFAOYSA-N 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 230000036541 health Effects 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 230000001771 impaired effect Effects 0.000 description 1
- 229940097275 indigo Drugs 0.000 description 1
- COHYTHOBJLSHDF-UHFFFAOYSA-N indigo powder Natural products N1C2=CC=CC=C2C(=O)C1=C1C(=O)C2=CC=CC=C2N1 COHYTHOBJLSHDF-UHFFFAOYSA-N 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- PXZQEOJJUGGUIB-UHFFFAOYSA-N isoindolin-1-one Chemical compound C1=CC=C2C(=O)NCC2=C1 PXZQEOJJUGGUIB-UHFFFAOYSA-N 0.000 description 1
- 229940102253 isopropanolamine Drugs 0.000 description 1
- 239000002655 kraft paper Substances 0.000 description 1
- WOFDVDFSGLBFAC-UHFFFAOYSA-N lactonitrile Chemical compound CC(O)C#N WOFDVDFSGLBFAC-UHFFFAOYSA-N 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- JDSHMPZPIAZGSV-UHFFFAOYSA-N melamine Chemical compound NC1=NC(N)=NC(N)=N1 JDSHMPZPIAZGSV-UHFFFAOYSA-N 0.000 description 1
- NYGZLYXAPMMJTE-UHFFFAOYSA-M metanil yellow Chemical group [Na+].[O-]S(=O)(=O)C1=CC=CC(N=NC=2C=CC(NC=3C=CC=CC=3)=CC=2)=C1 NYGZLYXAPMMJTE-UHFFFAOYSA-M 0.000 description 1
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 description 1
- 239000011259 mixed solution Substances 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 239000012452 mother liquor Substances 0.000 description 1
- 239000004745 nonwoven fabric Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 239000000123 paper Substances 0.000 description 1
- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 description 1
- CSHWQDPOILHKBI-UHFFFAOYSA-N peryrene Natural products C1=CC(C2=CC=CC=3C2=C2C=CC=3)=C3C2=CC=CC3=C1 CSHWQDPOILHKBI-UHFFFAOYSA-N 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 239000012286 potassium permanganate Substances 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 238000010298 pulverizing process Methods 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000004753 textile Substances 0.000 description 1
- 230000008719 thickening Effects 0.000 description 1
- 150000003672 ureas Chemical group 0.000 description 1
- 229940116269 uric acid Drugs 0.000 description 1
- 239000003981 vehicle Substances 0.000 description 1
Landscapes
- Inks, Pencil-Leads, Or Crayons (AREA)
Description
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The present invention relates to a novel pigment composition, which is characterized by good fluidity, storage stability, and coating gloss when used in water-based printing inks, water-based paints, and other water-based pigment compositions. can be significantly improved. In recent years, due to issues such as air pollution caused by organic solvents contained in oil-based printing inks or paints, occupational health and disaster prevention issues, and resource conservation considerations,
Water-based printing inks or paints are becoming the dominant trend in the industry. For pigments for water-based printing inks or paints, as for oil-based printing inks or paints, fluidity, storage stability, and film gloss of the ink or paint are particularly important suitability, and these properties are important. In order to impart this, it has been proposed to modify pigments with various processing agents or additives, such as surfactants, resins such as rosin, urea, thiourea, etc. Some pigments, such as dioxazine and phthalocyanine pigments, have relatively good suitability as pigments for water-based printing inks and paints without modification, but most pigments When fluidity is improved, coating film gloss is lost, and conversely, when gloss is improved, fluidity and storage stability are impaired. This tendency is caused by oil-based printing ink,
This is also seen in pigments for paints, but it is even more significant in water-based printing inks and paints, and pigments that have been surface-treated with surfactants and resins such as rosin have problems with gloss, fluidity, and storage. It has been extremely difficult to obtain pigments that have both stability. As a result of extensive research, the present inventors discovered that biuret and the urea or thiourea derivative compound represented by the general formula () or () exhibit excellent effects as a pigment treatment agent, and completed the present invention. I came to the conclusion. Biuret, general formula for 100 parts by weight of organic pigment (In the formula, R 1 and R 2 are hydrogen atoms, lower alkyl groups,
Represents a carbamide group or a phenyl group. ) or the general formula (In the formula, n represents an integer of 2 to 4.) A pigment composition containing 0.1 to 20 parts by weight of the compound represented by the following is provided. The pigment composition of the present invention can be used as a water-based printing ink, paint, colored coating agent for textiles or non-woven fabrics,
When used as a coloring agent for paper, etc., it exhibits much better fluidity and storage stability than pigments that have been subjected to conventionally known treatments, and provides good paint film gloss. It is known that the biuret used in the present invention can be easily obtained by heating urea, which is industrially produced in large quantities. In addition, hydantoin represented by the general formula () or its substituted product at the 5-position, such as U.S. Patent No.
No. 2717252, No. 2717253, No. 2732400, British Patent No. 630139, Special Publication No. 29-2074, No. 29-
No. 2075, No. 1071, J.Am.Chem.Soc. No. 70
Volume No. 1450, Volume 64, Page 2082, Chem. Ber. No. 83
Vol. 265, J.Prakt.Chem. Vol. 140, No. 291, J.Prakt.Chem. Vol. 141, No. 5, Can.J.Research B Vol. 24, No. 301
Produced by heating a mixture of a carbonyl compound, sodium cyanide, and ammonium carbonate in a solvent such as ethanol-water, or by heating cyanohydrin together with ammonium carbonate in aqueous ethanol, as described on page 1 and elsewhere. This reaction is generally called âBušchererâ.
known as a reaction. Examples of compounds represented by the general formula () include hydantoin, 5-methylhydantoin, 5,5-dimethylhydantoin,
5-ethyl-5-methylhydantoin, 5-methyl-5-phenylhydantoin, 5-phenylhydantoin, 5,5-diphenylhydantoin,
Allantoin [in the general formula (), R 1 = H, R 2 = NH-CONH 2 ]
Not synthesized by Bušcherer reaction, Org.Syn.Coll
It can be synthesized by oxidation of uric acid with alkaline potassium permanganate as described on page 23 of vol., or by the condensation reaction of dichloroacetic acid and urea as described in U.S. Pat. No. 2,158,098. I can do it. 5-(2-hydroxyethyl)-1,4,5,6-tetrahydro-1,3, represented by general formula ()
The 5-triazine-2(1H)-thione compound is
It is novel in itself, and is useful not only as a processing agent for the pigment of the present invention but also as an intermediate in the synthesis of pharmaceuticals and agricultural chemicals. Examples of compounds represented by the general formula () include: 5-(2-hydroxyethyl)-1,4,
5,6-tetrahydro-1,3,5-triazine-2(1H)-thione 5-(2-hydroxypropyl)-1,4,
5,6-tetrahydro-1,3,5-triazine-2(1H)-thione 5-(2-hydroxybutyl)-1,4,
Examples include 5,6-tetrahydro-1,3,5-triazine-2(1H)-thione, but these compounds can be synthesized extremely easily and with good yield from alkanolamines, formaldehyde, and thiourea. I can do it. The amount of the pigment treatment agent used in the composition of the present invention is 0.1 to 20 parts by weight, preferably 3 to 10 parts by weight, based on 100 parts by weight of the pigment, and if it is less than 0.1 part by weight, a sufficient effect cannot be obtained. If the amount exceeds 20 parts by weight, the physical properties of the coating film tend to deteriorate. The pigment treatment agent can be added to the pigment by adding it directly to the pigment powder and mixing, or by adding it to a wet paste of the pigment, mixing it, then drying and pulverizing it, or adding it to the pigment composition in the desired amount. Any method can be used as long as it is uniformly blended, and it may be added at the time of pigment production. Although it is not clear why the compound added to the pigment in the present invention exhibits an excellent effect of preventing thickening over time or structural viscosity, it is possible that the pigment and the polymer in the aqueous vehicle, or the pigment and water or alcohol, etc. This is presumed to be due to its extremely strong effect as a so-called "hydrogen bond breaker" that blocks interaction with polar solvent molecules. Examples of organic pigments to which the present invention is applied include phthalocyanine-based, quinacridone-based, indigo-based, indathrene-based, perylene-based, monoazo-based,
Examples include organic pigments such as disazo, isoindolinone, and dioxazine, but azo pigments are especially effective, and disazo pigments give particularly favorable results. Furthermore, when applied to pigments that have been treated with resins such as surfactants and rosins to impart gloss properties, they exhibit excellent performance as water-based printing ink pigments. Examples of the water-soluble resin of the vehicle used when the pigment composition of the present invention is used for water-based printing ink include styrene-maleic acid, acrylic, styrene-sierac, alkyd, melamine, and epoxy ester. Examples include resins that can be diluted with water or water-soluble polar solvents such as ethanol and isopropyl alcohol. The present invention will be explained in more detail below with reference to synthesis examples of the pigment treatment agent used in the present invention and examples of the present invention, but the gist and scope of the present invention will not be limited by these examples. It is not something that will be done. In addition, all parts in use mean parts by weight. (1) Synthesis example of 5-methylhydantoin [general formula ()] 250.8 g of ammonium carbonate is mixed with 100 g of ethanol.
ml and 100 ml of water, and 53.3 g of 98% lactonitrile was added dropwise over 2 hours while stirring while maintaining the temperature at 15 to 20°C. After the dropwise addition was completed, the mixture was stirred at 20 to 25°C for 2 hours and 30 minutes, then the temperature was raised to 60°C, and the mixture was heated and stirred for 4 hours. The resulting reaction solution was concentrated to half under reduced pressure, 15 g of 35% hydrochloric acid was added, and the temperature was raised to 90°C for 30
The mixture was heated and stirred for a minute. Next, the mixture was cooled to 5°C with stirring, and the precipitated crystals were filtered, dried, and recrystallized from methanol to obtain 59.0 g of white crystalline 5-methylhydantoin with a melting point of 144-45°C. The yield was 70.3%. (2) 5-(2-hydroxypropyl)-1,4,
Synthesis example of 5,6-tetrahydro-1,3,5-triazine-2(1H)-thione [general formula ()] 35% formalin 89.0g (1.04mol) and thiourea
While mixing and stirring 38.1g (0.50mol), 37.6g (0.50mol) of isopropanolamine and 1,4-
A mixed solution with 50 ml of dioxane was gradually added dropwise over a period of 1 hour at 0 to 5°C. 20-25 minutes after completion of dripping
The mixture was stirred at â for 1 hour and further heated under reflux for 2 hours.
As the resulting reaction solution was cooled, a large amount of crystals were precipitated, and upon cooling to 0° C., the precipitated crystals were separated and dried to obtain 68.2 g of first crystals of the target product. Melting point (decomposition point) is 150-152â, yield is 78.3
It was %. Concentrate the mother liquor further to obtain a second crystal
Obtained 10.5g. Next, the first crystal was purified by recrystallization from a 50% aqueous ethanol solution. The melting point (decomposition point) was 153-155°C, and the results of elemental analysis were as follows. Elemental analysis C 6 H 13 N 3 As OS Calculated values C: 41.36%, H: 7.52%, N: 24.12% Actual values C: 40.85%, H: 7.72%, N: 23.85% (3) 5-(2- hydroxyethyl)-1,4,5,
6-tetrahydro-1,3,5-triazine-
Synthesis example of 2(1H)-thione [general formula ()] A mixture of 30.54 g (0.50 mol) of monoethanolamine and 50 ml of 1,4-dioxane was stirred into a mixture of 89.0 g (1.04 mol) of 35% formalin and 38.1 g (0.50 mol) of thiourea cooled to 0 to 5°C. The mixture was added dropwise at the same temperature over a period of 1 hour. After standing overnight at room temperature, the mixture was heated under reflux for 2 hours, and then evaporated to dryness under reduced pressure. The remaining solid was purified by recrystallization from methanol to obtain 58.6 g of white crystals.
Melting point (decomposition point) is 149.5-150.5â, yield is 72.7
%, and the results of elemental analysis were as follows. Elemental analysis C 5 H 11 N 3 OS Calculated values C: 37.25%, H: 6.88%, N: 26.06% Actual values C: 36.98%, H: 6.80%, N: 26.02% Example 1 Tetrazotization using a known method CIPigment treated with HLB14 poly(oxyethylene) alkyl ether type surfactant after coupling and coupling
Yellow 14 was filtered, washed with water and dried, and 5 parts of Biuret were added to 100 parts of this pigment, thoroughly mixed and pulverized to obtain a pigment composition of the present invention. 25 parts of the obtained pigment composition, 45 parts of styrene maleic acid resin (nonvolatile content 28%, PH8.5, Gardner method viscosity P), and 30 parts of water were mixed, and 100 parts of glass beads with a diameter of 3 mm were added to form a paint condenser. Shake and disperse for 90 minutes in an issuer to create an ink base.
60 parts of this ink base, 30 parts of styrenated Sierra Tsuk emulsion (47% non-volatile content, PH8.5) and 5 parts of water.
1 part and stir well to obtain a water-based printing ink.
The obtained aqueous printing ink had particularly excellent fluidity and storage stability, and had good gloss without deterioration. Comparative Examples 1 to 3 Conventionally known pigment compositions were obtained in exactly the same manner as in Example 1 except that the following compounds were used in place of biuret or the addition was omitted, and then water-based printing inks were obtained in the same manner. . The resulting aqueous printing ink had good gloss but was poor in fluidity and storage stability. Comparative Example 1 Urea 5 parts Comparative Example 2 Thiourea 5 parts Comparative Example 3 Not added The viscosity, thixotropic index and gloss of the water-based inks obtained in Example 1 and Comparative Examples 1 to 3 are shown in Table 1. . The viscosity is the value measured by a B-type viscometer at 20â immediately after ink preparation and after being left at 20â for 720 hours, and the thixotropic index is a B-type viscometer.
The value is the viscosity at 6 rpm divided by the viscosity at 60 rpm, and the gloss is the value measured with a gloss meter after applying ink on kraft paper with a 0.15 mm percoater.
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æ°Ž5.0éšããšã¿ããŒã«8.5éšãæ··åããçŽåŸïŒmmã®
ã¹ããŒã«ããŒãº150éšãå ããŠãã€ã³ãã³ã³ãã€
ã·ãšããŒã§60åå
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ãäœæãããã®ã€ã³ãããŒã¹35éšã«åèšæ°Žæ§ã€ã³
ãçšã¯ãã¹15éšãæ·»å ãåäžã«æ··åããŠæµåæ§ã«
åªããæ°Žæ§å°å·ã€ã³ããåŸãã
æ¯èŒäŸ ïŒ
ããŠã¬ããã®æ·»å ãçç¥ãã以å€ã¯å®æœäŸïŒãš
å
šãåæ§ã«ããŠåŸæ¥å
¬ç¥ã®é¡æãåŸã次ãã§åæ§
ã«ããŠæ°Žæ§å°å·ã€ã³ããåŸããåŸãããæ°Žæ§å°å·
ã€ã³ãã¯æµåæ§ã«å£ããã®ã§ãã€ãã
å®æœäŸïŒããã³æ¯èŒäŸïŒã§åŸãããæ°Žæ§å°å·ã€
ã³ãã®ç²åºŠããããœããããã¯ã€ã³ããã¯ã¹ã第
ïŒè¡šã«ç€ºãã[Table] Example 2 5 parts of biuret were added to 100 parts of β-type phthalocyanine blue, thoroughly mixed and pulverized to obtain a pigment composition of the present invention. 18.1 parts of the obtained pigment composition, 37.5 parts of varnish for water-based ink (water-based acrylic resin manufactured by SC Johnson),
Mix 5.0 parts of water and 8.5 parts of ethanol, add 150 parts of steel beads with a diameter of 3 mm, and thoroughly shake and disperse for 60 minutes with a paint conditioner to create an ink base. Add 35 parts of this ink base to 35 parts of the water-based ink. 15 parts of varnish was added and mixed uniformly to obtain a water-based printing ink with excellent fluidity. Comparative Example 4 A conventionally known pigment was obtained in exactly the same manner as in Example 2, except that the addition of biuret was omitted, and then a water-based printing ink was obtained in the same manner. The resulting water-based printing ink had poor fluidity. The viscosity and thixotropic index of the aqueous printing inks obtained in Example 2 and Comparative Example 4 are shown in Table 2.
ãè¡šã
å®æœäŸ ïŒãïŒ
å
¬ç¥ã®æ¹æ³ã§ããã©ãŸååã³ã«ãããªã³ã°ãè¡
ããHLB10ã®ããªïŒãªãã·ãšãã¬ã³ïŒã¢ã«ãã«
ãšãŒãã«åçé¢æŽ»æ§å€ã§åŠçããC.I.Pigment
yellow14ãéãæ°ŽæŽã也ç¥ãããã®é¡æ100éš
ã«å¯ŸããŠäžèšååç©ã¯ïŒåã¯10éšãå ãå
åã«æ··
åãç²ç ããŠæ¬çºæã®é¡æçµæç©ãåŸãã[Table] Examples 3 to 8 CIPigment which was tetrazotized and coupled by a known method and treated with a poly(oxyethylene) alkyl ether type surfactant of HLB10.
Yellow 14 was filtered, washed with water and dried, and 5 or 10 parts of the following compound was added to 100 parts of this pigment, thoroughly mixed and ground to obtain a pigment composition of the present invention.
ãè¡šã
次ãã§ããããã®é¡æçµæç©ããå®æœäŸïŒãšå
æ§ã«ããŠæ°Žæ§å°å·ã€ã³ããåŸããåŸãããæ°Žæ§å°
å·ã€ã³ãã¯ããããæµåæ§ã貯èµå®å®æ§ã«ç¹ã«åª
ããå
æ²¢ãè¯å¥œã§ãã€ãã
æ¯èŒäŸ ïŒ
ïŒïŒïŒâãžã¡ãã«ããã³ãã€ã³ã®æ·»å ãçç¥ã
ã以å€ã¯å®æœäŸïŒãšå
šãåæ§ã«ããŠåŸæ¥å
¬ç¥ã®é¡
æãåŸã次ãã§åæ§ã«ããŠæ°Žæ§å°å·ã€ã³ããåŸ
ããåŸãããæ°Žæ§å°å·ã€ã³ãã¯æµåæ§ã貯èµå®å®
æ§ãå
æ²¢ã«å£ããã®ã§ãã€ãã
å®æœäŸïŒãïŒããã³æ¯èŒäŸïŒã§åŸãããæ°Žæ§å°
å·ã€ã³ãã®ç²åºŠããããœããããã¯ã€ã³ããã¯ã¹
ããã³å
æ²¢ã第ïŒè¡šã«ç€ºããå°ãç²åºŠã¯äœæçŽåŸ
ããã³40âã§120æéæŸçœ®åŸã®20âã«ãããå
ç²åºŠèšã«ãã枬å®å€ã§ããã[Table] Next, water-based printing inks were obtained from these pigment compositions in the same manner as in Example 1. All of the obtained aqueous printing inks had particularly excellent fluidity and storage stability, and also had good gloss. Comparative Example 5 A conventionally known pigment was obtained in exactly the same manner as in Example 3, except that the addition of 5,5-dimethylhydantoin was omitted, and then a water-based printing ink was obtained in the same manner. The resulting water-based printing ink was poor in fluidity, storage stability, and gloss. The viscosity, thixotropic index and gloss of the aqueous printing inks obtained in Examples 3 to 8 and Comparative Example 5 are shown in Table 3. The viscosity is a value measured using a B-type viscometer at 20°C immediately after preparation and after being left at 40°C for 120 hours.
ãè¡šã
å®æœäŸïŒã14ããã³æ¯èŒäŸïŒ
å®æœäŸïŒãïŒããã³æ¯èŒäŸïŒã§åŸãããé¡æçµ
æç©23éšãæ°Žæ§ã€ã³ãçšã¯ãã¹ïŒS.C.Johnson瀟
補氎æ§ã¢ã¯ãªã«æš¹èïŒ50éšãæ°Ž10éšããšã¿ããŒã«
17éšãæ··åããçŽåŸïŒmmã®ã¹ããŒã«ããŒã«150éš
ãå ããŠãã€ã³ãã³ã³ãã€ã·ãšããŒã§90åéæ¯
çªãåæ£ããŠã€ã³ãããŒã¹ãäœæãããã®ã€ã³ã
ããŒã¹70éšã«åèšæ°Žæ§ã€ã³ãçšã¯ãã¹30éšãæ·»
å ãåäžã«æ··åããŠæ°Žæ§å°å·ã€ã³ããåŸããå®æœ
äŸïŒã14ã§åŸãããã€ã³ãããŒã¹ããã³æ°Žæ§å°å·
ã€ã³ãã¯æµåæ§ã«åªãããã®ã§ãã€ãããæ¯èŒäŸ
ïŒã®ããã¯æµåæ§ã«å£ããã®ã§ãã€ããå°ãå®æœ
äŸïŒã14ããã³æ¯èŒäŸïŒã§äœ¿çšããååç©ãšãã®
䜿çšéã¯äžèšã®åŠãã§ããã[Table] Examples 9 to 14 and Comparative Example 6 23 parts of the pigment composition obtained in Examples 3 to 8 and Comparative Example 5, 50 parts of water-based ink varnish (water-based acrylic resin manufactured by SC Johnson), 10 parts of water, ethanol
Mix 17 parts, add 150 parts of steel holes with a diameter of 3 mm, and shake and disperse for 90 minutes with a paint conditioner to create an ink base, and add 30 parts of the water-based ink varnish to 70 parts of this ink base. A water-based printing ink was obtained by uniformly mixing. The ink bases and water-based printing inks obtained in Examples 9 to 14 had excellent fluidity, but those of Comparative Example 6 had poor fluidity. The compounds used in Examples 9 to 14 and Comparative Example 6 and their usage amounts are as follows.
ãè¡šããtableã
ãè¡šã
å®æœäŸïŒã10ããã³æ¯èŒäŸïŒã§åŸãããã€ã³ã
ããŒã¹ãšæ°Žæ§å°å·ã€ã³ãã®ç²åºŠããã³ãããœãã
ããã¯ã€ã³ããã¯ã¹ã第ïŒè¡šã«ç€ºããTable 4 shows the viscosity and thixotropic index of the ink bases and water-based printing inks obtained in Examples 9 to 10 and Comparative Example 6.
ãè¡šããtableã
ãè¡šã
å®æœäŸ 15ã16
βåãã¿ãã·ã¢ãã³ãã«ãŒ100éšã«å¯ŸããŠäžèš
ååç©ïŒéšãå ãå
åã«æ··åãç²ç ããŠæ¬çºæã®
é¡æçµæç©ãåŸãã
å®æœäŸ15 ïŒâã¡ãã«ããã³ãã€ã³
å®æœäŸ16 ããã³ãã€ã³
次ãã§å®æœäŸïŒãšå
šãåæ§ã«ããŠæ°Žæ§å°å·ã€ã³
ããåŸããåŸãããæ°Žæ§å°å·ã€ã³ãã¯æµåæ§ã«åª
ãããã®ã§ãã€ãã
æ¯èŒäŸ ïŒ
ããã³ãã€ã³ã®æ·»å ãçç¥ãã以å€ã¯å®æœäŸ16
ãšå
šãåæ§ã«ããŠåŸæ¥å
¬ç¥ã®é¡æãåŸã次ãã§å
æ§ã«ããŠæ°Žæ§å°å·ã€ã³ããåŸããåŸãããæ°Žæ§å°
å·ã€ã³ãã¯æµåæ§ã«å£ããã®ã§ãã€ãã
å®æœäŸ15ã16ããã³æ¯èŒäŸïŒã§åŸãããæ°Žæ§å°
å·ã€ã³ãã®ç²åºŠããã³ãããœããããã¯ã€ã³ãã
ã¯ã¹ã第ïŒè¡šã«ç€ºãã[Table] Examples 15 to 16 5 parts of the following compound were added to 100 parts of β-type phthalocyanine blue, thoroughly mixed and pulverized to obtain a pigment composition of the present invention. Example 15 5-Methylhydantoin Example 16 Hydantoin Then, in exactly the same manner as in Example 9, a water-based printing ink was obtained. The obtained water-based printing ink had excellent fluidity. Comparative Example 7 Example 16 except that the addition of hydantoin was omitted.
A conventionally known pigment was obtained in exactly the same manner as above, and then a water-based printing ink was obtained in the same manner. The resulting water-based printing ink had poor fluidity. Table 5 shows the viscosity and thixotropic index of the aqueous printing inks obtained in Examples 15-16 and Comparative Example 7.
ãè¡šã
å®æœäŸ17ã18ããã³æ¯èŒäŸïŒ
HLBã®ããªïŒãªãã·ãšãã¬ã³ïŒã¢ã«ãã«ãšãŒ
ãã«åçé¢æŽ»æ§å€ã§åŠçããC.I.Pigment
yellow14ã®ä»£ããã«ãåæ§ã«åŠçããC.I.
Pigment orange16ã䜿çšããïŒïŒïŒâãžã¡ãã«
ããã³ãã€ã³ã®æ·»å éã10ãïŒãïŒéšãšãã以å€
ã¯å®æœäŸïŒãšå
šãåæ§ã«ããŠé¡æçµæç©ãåŸã次
ãã§ãã€ã³ãã³ã³ãã€ã·ãšããŒã«ããæ¯çªæéã
60åéãšãã以å€ã¯åæ§ã«ããŠã€ã³ãããŒã¹ã
åŸã以äžåæ§ã«ããŠæ°Žæ§å°å·ã€ã³ããåŸããåŸã
ããã€ã³ãããŒã¹ããã³æ°Žæ§å°å·ã€ã³ãã®æµå
æ§ã貯èµå®å®æ§ã¯ïŒïŒïŒâãžã¡ãã«ããã³ãã€ã³
ã®æ·»å éãå€ãã»ã©åªããåŸåã«ãããå
æ²¢ã¯å
çã§ãã€ããå°ãå®æœäŸ17ã18ããã³æ¯èŒäŸïŒã§
䜿çšããïŒïŒïŒâãžã¡ãã«ããã³ãã€ã³ã®äœ¿çšé
ã¯äžèšã®åŠãã§ããã
å®æœäŸ17 10éš
å®æœäŸ18 ïŒéš
æ¯èŒäŸ ïŒ æ·»å ãã
å®æœäŸ17ã18ããã³æ¯èŒäŸïŒã§åŸãããã€ã³ã
ããŒã¹ã®ç²åºŠããããœããããã¯ã€ã³ããã¯ã¹ã
第ïŒè¡šã«ãæ°Žæ§å°å·ã€ã³ãã®ç²åºŠããããœããã
ãã¯ã€ã³ããã¯ã¹ãå
æ²¢ã第ïŒè¡šã«ç€ºããå°ãã€
ã³ãããŒã¹ããã³æ°Žæ§å°å·ã€ã³ãã®è²¯èµæ¡ä»¶ã¯20
âã§ãããã96æéã168æéã§ããã[Table] Examples 17-18 and Comparative Example 8 CIPigment treated with HLB poly(oxyethylene) alkyl ether type surfactant
CI treated similarly instead of yellow14
A pigment composition was obtained in exactly the same manner as in Example 9, except that Pigment orange 16 was used and the amount of 5,5-dimethylhydantoin added was changed to 10, 5, and 0 parts.
An ink base was obtained in the same manner except that the time was 60 minutes, and a water-based printing ink was obtained in the same manner. The fluidity and storage stability of the obtained ink base and aqueous printing ink tended to be better as the amount of 5,5-dimethylhydantoin added was larger, and the gloss was the same. The amount of 5,5-dimethylhydantoin used in Examples 17 and 18 and Comparative Example 8 is as follows. Example 17 10 parts Example 18 5 parts Comparative example 8 Not added The viscosity and thixotropic index of the ink bases obtained in Examples 17 to 18 and Comparative Example 8 are shown in Table 6, and the viscosity of the water-based printing ink is shown in Table 6. , thixotropic index, and gloss are shown in Table 7. The storage conditions for ink base and water-based printing ink are 20
°C for 96 hours and 168 hours, respectively.
ãè¡šããtableã
ãè¡šã
å®æœäŸ 19ã20
ïŒïŒïŒâãžã¡ãã«ããã³ãã€ã³ã®ä»£ããã«åèš
åæäŸã§åŸãããäžèšååç©ãçšãã以å€ã¯å®æœ
äŸïŒãšå
šãåæ§ã«ããŠé¡æçµæç©ãåŸã次ãã§å
æ§ã«ããŠæ°Žæ§å°å·ã€ã³ããåŸããåŸãããæ°Žæ§å°
å·ã€ã³ãã¯æµåæ§ã«åªãããã®ã§ãã€ãã
å®æœäŸ 19
ïŒâïŒïŒâããããã·ãããã«ïŒâïŒïŒïŒïŒïŒïŒ
ïŒâããã©ãããâïŒïŒïŒïŒïŒâããªã¢ãžã³âïŒ
ïŒ1HïŒâããªã³
å®æœäŸ 20
ïŒâïŒïŒâããããã·ãšãã«ïŒâïŒïŒïŒïŒïŒïŒïŒ
âããã©ãããâïŒïŒïŒïŒïŒâããªã¢ãžã³âïŒ
ïŒ1HïŒâããªã³
å®æœäŸ19ã20ããã³æ¯èŒäŸïŒã§åŸãããæ°Žæ§å°
å·ã€ã³ãã®ç²åºŠããã³ãããœããããã¯ã€ã³ãã
ã¯ã¹ã第ïŒè¡šã«ç€ºãã[Table] Examples 19-20 A pigment composition was obtained in exactly the same manner as in Example 9, except that the following compound obtained in the above synthesis example was used in place of 5,5-dimethylhydantoin, and then aqueous printing was carried out in the same manner. Got the ink. The obtained water-based printing ink had excellent fluidity. Example 19 5-(2-hydroxypropyl)-1,4,5,
6-tetrahydro-1,3,5-triazine-2
(1H)-thione Example 20 5-(2-hydroxyethyl)-1,4,5,6
-tetrahydro-1,3,5-triazine-2
(1H)-thione The viscosity and thixotropic index of the aqueous printing inks obtained in Examples 19-20 and Comparative Example 6 are shown in Table 8.
ãè¡šã
å®æœäŸ 21
ïŒâã¡ãã«ããã³ãã€ã³ã®ä»£ããã«åèšåæäŸ
ã§åŸãããïŒâïŒïŒâããããã·ãšãã«ïŒâïŒïŒ
ïŒïŒïŒïŒïŒâããã©ãããâïŒïŒïŒïŒïŒâããªã¢
ãžã³âïŒïŒ1HïŒâããªã³ãçšãã以å€ã¯å®æœäŸ15
ãšå
šãåæ§ã«ããŠé¡æçµæç©ãåŸã次ãã§åæ§ã«
ããŠæ°Žæ§ã€ã³ããåŸãã
å®æœäŸ21ããã³å®æœäŸïŒã§åŸãããæ°Žæ§å°å·ã€
ã³ãã®ç²åºŠããã³ãããœããããã¯ã€ã³ããã¯ã¹
ã第ïŒè¡šã«ç€ºãã[Table] Example 21 5-(2-hydroxyethyl)-1, obtained in the above synthesis example, in place of 5-methylhydantoin
Example 15 except using 4,5,6-tetrahydro-1,3,5-triazine-2(1H)-thione
A pigment composition was obtained in exactly the same manner as above, and then a water-based ink was obtained in the same manner. The viscosity and thixotropic index of the aqueous printing inks obtained in Example 21 and Example 7 are shown in Table 9.
Claims (1)
ã«ã«ãããåºåã¯ããšãã«åºãè¡šãããïŒ ã§ç€ºãããååç©ãå㯠äžè¬åŒ ïŒåŒäžãïœã¯ïŒãïŒã®æŽæ°ãè¡šãããïŒ ã§ç€ºãããååç©ã0.1ã20éééšé åããŠãªã
é¡æçµæç©ã[Claims] 1 Based on 100 parts by weight of organic pigment, Biuret, general formula (In the formula, R 1 and R 2 are hydrogen atoms, lower alkyl groups,
Represents a carbamide group or a phenyl group. ) or the general formula (In the formula, n represents an integer of 2 to 4.) A pigment composition containing 0.1 to 20 parts by weight of the compound shown below.
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP57081559A JPS58198570A (en) | 1982-05-17 | 1982-05-17 | Pigment composition |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP57081559A JPS58198570A (en) | 1982-05-17 | 1982-05-17 | Pigment composition |
Publications (2)
Publication Number | Publication Date |
---|---|
JPS58198570A JPS58198570A (en) | 1983-11-18 |
JPH0157149B2 true JPH0157149B2 (en) | 1989-12-04 |
Family
ID=13749640
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP57081559A Granted JPS58198570A (en) | 1982-05-17 | 1982-05-17 | Pigment composition |
Country Status (1)
Country | Link |
---|---|
JP (1) | JPS58198570A (en) |
Families Citing this family (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
ES2186376T3 (en) * | 1998-07-29 | 2003-05-01 | Clariant Finance Bvi Ltd | AQUOUS COMPOSITIONS OF REACTIVE COLORS, THEIR PRODUCTION AND THEIR USE. |
KR100601686B1 (en) | 2004-06-04 | 2006-07-14 | ìŒì±ì ì죌ìíì¬ | Ink composition |
EP3067216B1 (en) * | 2015-03-10 | 2019-01-16 | Basf Se | Chromophoric compositions |
-
1982
- 1982-05-17 JP JP57081559A patent/JPS58198570A/en active Granted
Also Published As
Publication number | Publication date |
---|---|
JPS58198570A (en) | 1983-11-18 |
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