CN1806021A - 稳定化的含水着色剂制剂 - Google Patents
稳定化的含水着色剂制剂 Download PDFInfo
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- CN1806021A CN1806021A CNA2004800161582A CN200480016158A CN1806021A CN 1806021 A CN1806021 A CN 1806021A CN A2004800161582 A CNA2004800161582 A CN A2004800161582A CN 200480016158 A CN200480016158 A CN 200480016158A CN 1806021 A CN1806021 A CN 1806021A
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- 241000588777 Providencia rettgeri Species 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- ABBQHOQBGMUPJH-UHFFFAOYSA-M Sodium salicylate Chemical compound [Na+].OC1=CC=CC=C1C([O-])=O ABBQHOQBGMUPJH-UHFFFAOYSA-M 0.000 description 1
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- 150000008065 acid anhydrides Chemical group 0.000 description 1
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- 125000000751 azo group Chemical group [*]N=N[*] 0.000 description 1
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- LFZDEAVRTJKYAF-UHFFFAOYSA-L barium(2+) 2-[(2-hydroxynaphthalen-1-yl)diazenyl]naphthalene-1-sulfonate Chemical compound [Ba+2].C1=CC=CC2=C(S([O-])(=O)=O)C(N=NC3=C4C=CC=CC4=CC=C3O)=CC=C21.C1=CC=CC2=C(S([O-])(=O)=O)C(N=NC3=C4C=CC=CC4=CC=C3O)=CC=C21 LFZDEAVRTJKYAF-UHFFFAOYSA-L 0.000 description 1
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- NSFKBZXCXCJZDQ-UHFFFAOYSA-N cumene;sodium Chemical compound [Na].CC(C)C1=CC=CC=C1 NSFKBZXCXCJZDQ-UHFFFAOYSA-N 0.000 description 1
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- 230000008021 deposition Effects 0.000 description 1
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- 238000006193 diazotization reaction Methods 0.000 description 1
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 1
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- VYXSBFYARXAAKO-UHFFFAOYSA-N ethyl 2-[3-(ethylamino)-6-ethylimino-2,7-dimethylxanthen-9-yl]benzoate;hydron;chloride Chemical compound [Cl-].C1=2C=C(C)C(NCC)=CC=2OC2=CC(=[NH+]CC)C(C)=CC2=C1C1=CC=CC=C1C(=O)OCC VYXSBFYARXAAKO-UHFFFAOYSA-N 0.000 description 1
- 239000004744 fabric Substances 0.000 description 1
- JEIPFZHSYJVQDO-UHFFFAOYSA-N ferric oxide Chemical compound O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 description 1
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- 239000006232 furnace black Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- CATSNJVOTSVZJV-UHFFFAOYSA-N heptan-2-one Chemical compound CCCCCC(C)=O CATSNJVOTSVZJV-UHFFFAOYSA-N 0.000 description 1
- XXMIOPMDWAUFGU-UHFFFAOYSA-N hexane-1,6-diol Chemical compound OCCCCCCO XXMIOPMDWAUFGU-UHFFFAOYSA-N 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 150000002460 imidazoles Chemical class 0.000 description 1
- 239000012770 industrial material Substances 0.000 description 1
- 230000000968 intestinal effect Effects 0.000 description 1
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 1
- BSIHWSXXPBAGTC-UHFFFAOYSA-N isoviolanthrone Chemical compound C12=CC=CC=C2C(=O)C2=CC=C3C(C4=C56)=CC=C5C5=CC=CC=C5C(=O)C6=CC=C4C4=C3C2=C1C=C4 BSIHWSXXPBAGTC-UHFFFAOYSA-N 0.000 description 1
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- GYNNXHKOJHMOHS-UHFFFAOYSA-N methyl-cycloheptane Natural products CC1CCCCCC1 GYNNXHKOJHMOHS-UHFFFAOYSA-N 0.000 description 1
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- 238000012986 modification Methods 0.000 description 1
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- 210000003097 mucus Anatomy 0.000 description 1
- 150000004780 naphthols Chemical class 0.000 description 1
- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 description 1
- 229920003986 novolac Polymers 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- FDPIMTJIUBPUKL-UHFFFAOYSA-N pentan-3-one Chemical compound CCC(=O)CC FDPIMTJIUBPUKL-UHFFFAOYSA-N 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
- 229940104573 pigment red 5 Drugs 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 229920002492 poly(sulfone) Polymers 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 229920001155 polypropylene Polymers 0.000 description 1
- 229920001451 polypropylene glycol Polymers 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- LLBIOIRWAYBCKK-UHFFFAOYSA-N pyranthrene-8,16-dione Chemical compound C12=CC=CC=C2C(=O)C2=CC=C3C=C4C5=CC=CC=C5C(=O)C5=C4C4=C3C2=C1C=C4C=C5 LLBIOIRWAYBCKK-UHFFFAOYSA-N 0.000 description 1
- WPPDXAHGCGPUPK-UHFFFAOYSA-N red 2 Chemical compound C1=CC=CC=C1C(C1=CC=CC=C11)=C(C=2C=3C4=CC=C5C6=CC=C7C8=C(C=9C=CC=CC=9)C9=CC=CC=C9C(C=9C=CC=CC=9)=C8C8=CC=C(C6=C87)C(C=35)=CC=2)C4=C1C1=CC=CC=C1 WPPDXAHGCGPUPK-UHFFFAOYSA-N 0.000 description 1
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- 102220032811 rs367543159 Human genes 0.000 description 1
- 239000005060 rubber Substances 0.000 description 1
- 230000011218 segmentation Effects 0.000 description 1
- 238000005204 segregation Methods 0.000 description 1
- 229910052708 sodium Chemical group 0.000 description 1
- WXMKPNITSTVMEF-UHFFFAOYSA-M sodium benzoate Chemical compound [Na+].[O-]C(=O)C1=CC=CC=C1 WXMKPNITSTVMEF-UHFFFAOYSA-M 0.000 description 1
- 235000010234 sodium benzoate Nutrition 0.000 description 1
- 239000004299 sodium benzoate Substances 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 229960004025 sodium salicylate Drugs 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 229940048842 sodium xylenesulfonate Drugs 0.000 description 1
- QUCDWLYKDRVKMI-UHFFFAOYSA-M sodium;3,4-dimethylbenzenesulfonate Chemical compound [Na+].CC1=CC=C(S([O-])(=O)=O)C=C1C QUCDWLYKDRVKMI-UHFFFAOYSA-M 0.000 description 1
- KVCGISUBCHHTDD-UHFFFAOYSA-M sodium;4-methylbenzenesulfonate Chemical compound [Na+].CC1=CC=C(S([O-])(=O)=O)C=C1 KVCGISUBCHHTDD-UHFFFAOYSA-M 0.000 description 1
- MZSDGDXXBZSFTG-UHFFFAOYSA-M sodium;benzenesulfonate Chemical compound [Na+].[O-]S(=O)(=O)C1=CC=CC=C1 MZSDGDXXBZSFTG-UHFFFAOYSA-M 0.000 description 1
- DAJSVUQLFFJUSX-UHFFFAOYSA-M sodium;dodecane-1-sulfonate Chemical compound [Na+].CCCCCCCCCCCCS([O-])(=O)=O DAJSVUQLFFJUSX-UHFFFAOYSA-M 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000011115 styrene butadiene Substances 0.000 description 1
- 229920003048 styrene butadiene rubber Polymers 0.000 description 1
- 229920005792 styrene-acrylic resin Polymers 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
- 238000006277 sulfonation reaction Methods 0.000 description 1
- 230000002195 synergetic effect Effects 0.000 description 1
- 239000004753 textile Substances 0.000 description 1
- 229920002803 thermoplastic polyurethane Polymers 0.000 description 1
- 239000004408 titanium dioxide Substances 0.000 description 1
- JLGLQAWTXXGVEM-UHFFFAOYSA-N triethylene glycol monomethyl ether Chemical compound COCCOCCOCCO JLGLQAWTXXGVEM-UHFFFAOYSA-N 0.000 description 1
- JSPLKZUTYZBBKA-UHFFFAOYSA-N trioxidane Chemical compound OOO JSPLKZUTYZBBKA-UHFFFAOYSA-N 0.000 description 1
- 229960004418 trolamine Drugs 0.000 description 1
- 239000004034 viscosity adjusting agent Substances 0.000 description 1
- 210000002268 wool Anatomy 0.000 description 1
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Classifications
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/02—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms
- A01N43/04—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom
- A01N43/06—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom five-membered rings
- A01N43/08—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom five-membered rings with oxygen as the ring hetero atom
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D11/00—Inks
- C09D11/30—Inkjet printing inks
- C09D11/38—Inkjet printing inks characterised by non-macromolecular additives other than solvents, pigments or dyes
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N31/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic oxygen or sulfur compounds
- A01N31/08—Oxygen or sulfur directly attached to an aromatic ring system
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
- A01N43/80—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,2
-
- 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
-
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Abstract
本发明涉及抗微生物有效量的由5-氯-2-甲基-4-异噻唑啉-3-酮、2-甲基-4-异噻唑啉-3-酮和2-溴-2-硝基丙烷-1,3-二醇形成的混合物在具有重金属离子浓度大于或等于20ppm的含水着色剂制剂中作为抗微生物剂的用途。本发明这样有效地防止了沉淀物的形成。
Description
本发明涉及着色剂领域,该着色剂特别地用于书写工具和记录工具用的记录液体中,例如用于喷墨印刷工艺的记录液体中。
喷墨工艺是无接触式印刷工艺,其中将记录液体的小滴从-个或多个喷嘴导引到要印刷的基材上。为获得高锐度和良好分辨率的印刷物,记录液体和其中包含的着色剂必须满足高要求,特别地关于纯度,粒子游离度(Partikelfreiheit),溶解性,贮存稳定性,粘度,表面张力以及传导率。
用于油墨中的染料在此是最重要的。尽管已开发了许多染料,但仅有少数满足现代喷墨印刷操作对其提出的要求。重金属配合物着色剂在此起重要的作用,特别地铜配合物染料和颜料。除了染料基油墨以外,着色的油墨近来也渐增地在喷墨印刷中使用。
已知向含水着色剂制剂和油墨,例如喷墨油墨中掺混入抗微生物的活性物质,以防止不期望的微生物如细菌和霉菌、酵母和黏液微生物的侵害。DE-A-10112367公开了使用甲基-2H-异噻唑-3-酮和2-溴硝基丙二醇组成的协同混合物以控制工业材料中的微生物生长。JP2000226545-A中提出了-系列用于喷墨油墨中的其它抗微生物剂。
然而,表现出的现象是对于包含配位结合的重金属离子的着色剂或自身无重金属但被重金属离子污染的着色剂,可能由于重金属离子与通常的抗微生物剂或通常的抗微生物剂混合物的反应而形成沉淀物,由此可能特别在喷墨印刷中堵塞印刷头中的喷嘴(“nozzleclogging”)。这样的重金属离子,特别地带多个电荷的金属阳离子,例如Cu2+、Fe3+或Al3+,可能在染料溶液中,在颜料粉末中或在颜料压滤饼中作为残余杂质存在,和通过分散操作而引入相应的油墨中。另外,在所用分散剂或其它油墨添加剂中也可能存在重金属杂质。由于上述抗微生物剂-重金属配合物经常还具有显著的固有着色,所以这可能对相应油墨的色彩性能和由此生产的喷墨油墨印刷物具有不利的影响。除了印刷机喷嘴的堵塞,不溶性配合物也可能导致在印刷机的加热元件上沉积(“cogation”)或导致在过滤操作方面的问题。
因此本发明的目的是提供用于含水的含重金属的着色剂制剂和油墨的有效抗微生物组合物,该组合物丝毫不引起任何沉淀物。此外,因为由于稳定性原因而经常在酸性或碱性环境中销售这样的着色剂制剂,所以抗微生物组合物应当在宽pH范围内,特别地在pH3和10之间,保护所述的着色剂制剂和油墨免受病菌的侵害。
已经发现,由5-氯-2-甲基-4-异噻唑啉-3-酮(称为CMIT),2-甲基-4-异噻唑啉-3-酮(称为MIT)和2-溴-2-硝基丙烷-1,3-二醇(称为溴硝丙二醇(Bronopol))形成的混合物令人惊奇地达到了这些目的。
本发明因此提供抗微生物有效量的由5-氯-2-甲基-4-异噻唑啉-3-酮,2-甲基-4-异噻唑啉-3-酮和2-溴-2-硝基丙烷-1,3-二醇形成的混合物在具有重金属离子浓度大于或等于20ppm和特别地是大于或等于50ppm的含水着色剂制剂,优选含水记录液体,特别地喷墨油墨中作为抗微生物剂的用途。当然,重金属离子浓度的上限不应当高于抗微生物剂混合物的最大浓度。在约500ppm的金属浓度下仍然有效防止了重金属沉积物,而不必须提高抗微生物混合物的数量到超过经济上正当合理的量度。抗微生物混合物当然也可用于含水着色剂制剂中,在该制剂中重金属沉淀物的问题不存在或仅在很低程度上存在,例如在低于20ppm的重金属离子浓度下。
所述混合物的抗微生物有效量经证实有利地为0.001wt%-0.1wt%,优选0.01wt%-0.05wt%的含量,作为固体形式计算和基于含水着色剂制剂的总重量计。各组分的用量比例CMIT∶MIT∶溴硝丙二醇优选为(0.005-0.1)∶(0.005-0.05)∶1,特别地(0.03-0.065)∶(0.01-0.025)∶1。为简化计量,通常以稀释的,例如5wt%-15wt%水溶液的形式使用抗微生物混合物,该水溶液可进-步包含少量无机盐,例如硝酸镁和/或氯化镁。这样用于着色剂制剂中的此溶液的数量优选为0.01wt%-1wt%和特别地0.1wt%-0.2wt%,基于着色剂制剂的总重量计。
对于本发明的目的特别感兴趣的是包含配位结合的重金属的着色剂。
可使用的重金属配合物着色剂包括活性染料、直接染料、酸性染料、分散染料和颜料,它们特别以配位结合方式包含选自Cu、Co、Ni、Fe、Cr和Al的重金属。特别优选是铜配合物染料和颜料。
这样的活性染料的例子是C.I.活性黑8、C.I.活性黑31;C.I.活性蓝7、C.I.活性蓝14、C.I.活性蓝21、C.I.活性蓝28、C.I.活性蓝38、C.I.活性蓝82、C.I.活性蓝89、C.I.活性蓝158、C.I.活性蓝182、C.I.活性蓝190、C.I.活性蓝203、C.I.活性蓝216、C.I.活性蓝220、C.I.活性蓝244;C.I.活性紫1、C.I.活性紫5;C.I.活性红6、C.I.活性红23和C.I.活性棕18。
直接染料的例子是C.I.直接蓝76、C.I.直接蓝84、C.I.直接蓝86、C.I.直接蓝87、C.I.直接蓝98、C.I.直接蓝199、C.I.直接蓝202、C.I.直接蓝290;C.I.直接黑112;C.I.直接棕95和C.I.直接紫47。
酸性染料的例子是C.I.酸性蓝87、C.I.酸性蓝185和C.I.酸性蓝249。
重金属配合物颜料的例子是C.I.颜料蓝15:1-15:4、C.I.颜料蓝17、C.I.颜料绿7、C.I.颜料绿37、C.I.颜料红257、C.I.颜料红271、C.I.颜料橙65、C.I.颜料橙68、C.I.颜料黄117、C.I.颜料黄129和C.I.颜料黄153。
对于本发明目的特别优选是C.I.直接蓝199(5a)(铜配合物)、C.I.活性黑31(5b)(铜配合物)、C.I.活性黑8(铜/钴配合物)和C.I.活性红23(铜配合物)。
X=H,SO2NH2,SO3Na (5a)
铜配合物染料的其它例子是如下结构式(5c)-(5l)的化合物:
在结构式(5b)-(5l)的染料中,依赖于pH值而定,M优选是氢和/或钠。
可能被重金属离子污染的有用的有机颜料包括单偶氮、双偶氮、色淀偶氮、β-萘酚、萘酚AS、苯并咪唑酮、双偶氮缩合颜料、偶氮-金属配合物颜料和多环颜料,例如酞菁、喹吖啶酮、花、萘环酮(Perinon)、硫靛、二苯并[cd,jk]芘-5,10-二酮、蒽醌、黄烷士酮、阴丹酮、异宜和蓝酮、皮蒽酮、二噁嗪、喹诺酞酮、异吲哚啉酮、异吲哚啉和二酮基吡咯并吡咯颜料或炭黑。
可能被重金属离子污染的有用的无机颜料包括例如二氧化钛、锌的硫化物、铁的氧化物、铬的氧化物、群青、镍或铬的锑钛氧化物、钴的氧化物以及钒酸铋。
特别优选的有机颜料的例举性选择在此是炭黑颜料,例如气黑或炉黑;单偶氮和双偶氮颜料,特别是染料索引颜料颜料黄1、颜料黄3、颜料黄12、颜料黄13、颜料黄14、颜料黄16、颜料黄17、颜料黄73、颜料黄74、颜料黄81、颜料黄83、颜料黄87、颜料黄97、颜料黄111、颜料黄126、颜料黄127、颜料黄128、颜料黄155、颜料黄174、颜料黄176、颜料黄191、颜料红38、颜料红144、颜料红214、颜料红242、颜料红262、颜料红266、颜料红269、颜料红274、颜料橙13、颜料橙34或颜料棕41;β-萘酚和萘酚AS颜料,特别是染料索引颜料颜料红2、颜料红3、颜料红4、颜料红5、颜料红9、颜料红12、颜料红14、颜料红53:1、颜料红112、颜料红146、颜料红147、颜料红170、颜料红184、颜料红187、颜料红188、颜料红210、颜料红247、颜料红253、颜料红256、颜料橙5、颜料橙38或颜料棕1;色淀偶氮和金属配合物颜料,特别是染料索引颜料颜料红48:2、颜料红48:3、颜料红48:4、颜料红57:1、颜料红257、颜料橙68或颜料橙70;苯并咪唑啉颜料,特别是染料索引颜料颜料黄120、颜料黄151、颜料黄154、颜料黄175、颜料黄180、颜料黄181、颜料黄194、颜料红175、颜料红176、颜料红185、颜料红208、颜料紫32、颜料橙36、颜料橙62、颜料橙72或颜料棕25;异吲哚啉酮和异吲哚啉颜料,特别是染料索引颜料颜料黄139或颜料黄173;酞菁颜料,特别是染料索引颜料颜料蓝15、颜料蓝15:1、颜料蓝15:2、颜料蓝15:3、颜料蓝15:4、颜料蓝16、颜料绿7或颜料绿36;二苯并[cd,jk]芘-5,10-二酮、蒽醌、喹吖啶酮、二噁嗪、阴丹酮、苝、萘环酮和硫靛颜料,特别是染料索引颜料颜料黄196、颜料红122、颜料红149、颜料红168、颜料红177、颜料红179、颜料红181、颜料红207、颜料红209、颜料红263、颜料蓝60、颜料紫19、颜料紫23或颜料橙43;三芳基碳鎓颜料,特别是染料索引颜料颜料红169、颜料蓝56或颜料蓝61;二酮基吡咯并吡咯颜料,特别是染料索引颜料颜料红254。
在此,颜料在液体介质中单独或由分散助剂稳定化地以细分粒子形式存在。平均粒径在此是优选1-1000nm,特别优选10-100hm。可以不采用分散助剂稳定化的颜料已知称为可自分散的颜料。这些颜料正常是指表面改性的颜料,其表面已经通过化学工艺例如磺化或重氮化而改变并具有官能性的、带电荷或不带电荷的基团或聚合物链(也已知为自分散性或接枝颜料)。
在此,非离子、两性、阳离子或阴离子表面活性剂或聚合物可用作分散助剂。
本发明也提供包含0.1wt%-50wt%,优选0.5wt%-20wt%至少一种重金属配合物着色剂,0.001wt%-0.1wt%,优选0.01wt%-0.05wt%所述抗微生物混合物,和10wt%-90wt%,优选30wt%-80wt%去离子水的含水着色剂制剂,优选记录液体,特别地喷墨油墨,每种情况下基于着色剂制剂的总重量(100wt%)计。
本发明也提供包含至少20ppm重金属离子和0.1wt%-50wt%和优选0.5wt%-20wt%至少一种着色剂,0.001wt%-0.1wt%,优选0.01wt%-0.05wt%所述抗微生物混合物,和10wt%-90wt%,优选30wt%-80wt%去离子水的含水着色剂制剂,优选记录液体,特别地喷墨油墨,每种情况下基于着色剂制剂的总重量(100wt%)计。
用于生产记录液体的水优选以蒸馏水或软化水的形式使用。
依赖于使用的染料,本发明的着色剂制剂可额外还包含配色着色剂(Nuancierfarbmittel),其优选选自如下:C.I.酸性黄17和C.I.酸性黄23;C.I.直接黄86、C.I.直接黄98和C.I.直接黄132;C.I.活性黄37;C.I.颜料黄17、C.I.颜料黄74、C.I.颜料黄83、C.I.颜料黄97、C.I.颜料黄120、C.I.颜料黄139、C.I.颜料黄151、C.I.颜料黄155和C.I.颜料黄180;C.I.直接红1、C.I.直接红11、C.I.直接红37、C.I.直接红62、C.I.直接红75、C.I.直接红81、C.I.直接红87、C.I.直接红89、C.I.直接红95和C.I.直接红227;C.I.酸性红1、C.I.酸性红8、C.I.酸性红80、C.I.酸性红81、C.I.酸性红82、C.I.酸性红87、C.I.酸性红94、C.I.酸性红115、C.I.酸性红131、C.I.酸性红144、C.I.酸性红152、C.I.酸性红154、C.I.酸性红186、C.I.酸性红245、C.I.酸性红249和C.I.酸性红289;C.I.活性红21、C.I.活性红22、C.I.活性红23、C.I.活性红35、C.I.活性红63、C.I.活性红106、C.I.活性红107、C.I.活性红112、C.I.活性红113、C.I.活性红114、C.I.活性红126、C.I.活性红127、C.I.活性红128、C.I.活性红129、C.I.活性红130、C.I.活性红131、C.I.活性红137、C.I.活性红160、C.I.活性红161、C.I.活性红174和C.I.活性红180;C.I.颜料红122、C.I.颜料红176、C.I.颜料红184、C.I.颜料红185和C.I.颜料红269;C.I.直接蓝199;C.I.酸性蓝9和C.I.颜料蓝15:1-15:4。该配色着色剂优选以0.001-5wt%,特别是0.01-1wt%的量存在,基于总着色剂的干重。
本发明的着色剂制剂可以通常的数量进一步包含有机溶剂、保湿剂、有机或无机碱或酸、阳离子、阴离子或非离子表面活性物质(表面活性剂和湿润剂),以及粘度调节剂,例如聚乙烯醇,纤维素衍生物或水溶性天然或人造树脂作为成膜剂或粘结剂以提高粘附强度和耐磨强度,以及光稳定剂。
合适的保湿剂例如有甲酰胺、脲、四甲基脲、ε-己内酰胺、乙二醇、丙二醇、二甘醇、三甘醇、聚乙二醇、丁基乙二醇、甲基溶纤剂、甘油、N-甲基-吡咯烷酮、1,3-二乙基-2-咪唑啉酮、硫代二甘醇、苯磺酸钠、甲苯磺酸钠、二甲苯磺酸钠、异丙苯磺酸钠、十二烷基磺酸钠、苯甲酸钠、水杨酸钠和丁基一甘醇硫酸钠。
合适的溶剂例如有一元醇或多元醇,它们的醚和酯,例如甲醇、乙醇、丙醇、异丙醇、丁醇、异丁醇;二元醇或三元醇,特别是具有2-6个碳原子的此类醇,例如乙二醇、丙二醇、1,3-丙二醇、1,4-丁二醇、1,5-戊二醇、1,6-己二醇、新戊二醇、1,2,6-己三醇、甘油、2-乙基-2-羟甲基-1,3-丙二醇、二甘醇、二丙二醇、三甘醇、聚乙二醇、三丙二醇、聚丙二醇;多元醇的低级烷基醚,例如乙二醇单甲基醚、乙二醇单乙基醚、乙二醇单丁基醚、三甘醇单甲基醚或三甘醇单乙基醚;酮和酮醇例如丙酮、甲乙酮、二乙基酮、甲基异丁基酮、甲基戊基酮、环戊酮、环己酮、双丙酮醇;酰胺,例如二甲基甲酰胺、二甲基乙酰胺、N-甲基吡咯烷酮;此外还有脲、四甲基脲、硫代二甘醇、ε-己内酰胺。
合适的碱例如有乙醇胺、二乙醇胺、三乙醇胺、N,N-二甲基乙醇胺、二异丙胺。
依赖于喷墨印刷工艺的实施方式,例如作为连续喷射、间歇喷射、脉冲喷射或复合喷射工艺,用于喷墨印刷工艺的记录液体还可添加进一步的添加剂,例如用于缓冲pH值,用于调节电导率、比热、热膨胀系数和传导率。
可以通过以干燥粉末、它们的溶液、水湿或溶剂湿的压滤饼形式将上述的组分彼此混合而生产本发明的着色剂制剂。
为用于记录液体,根据上文所述的要求处理所述的着色剂。可以从首先获得的,优选含水的反应混合物中,通过盐析和过滤或通过喷雾干燥,非必要地在借助膜过滤的部分或完全脱盐之后,分离出染料。然而,也可以省略分离步骤,和通过加入有机和/或无机碱,可能还有保湿剂,防腐剂,和非必要地在借助膜过滤的部分或完全脱盐之后,将含染料的反应混合物直接转化成浓缩的染料溶液。或者,染料也可以作为压滤饼形式(非必要地还在冲洗工艺中)或作为粉末形式使用。有利地,以尽可能无盐的形式,即没有NaCl或在染料合成过程中形成的其它通常的无机盐,使用本发明的染料混合物。
在颜料着色剂的情况下,在此优选这样进行,使得在第一步骤中,将至少一种颜料(作为粉末或作为压滤饼形式),非必要地与至少一种分散剂一起,非必要地与至少一种有机溶剂,非必要地与至少一种助水溶性物质和非必要地其它添加剂一起在去离子水中糊化,和随后使用溶解器或其它合适的设备均化和预分散。随后使用珠磨机或其它合适的分散设备组进行细分散,在此在冷却下进行细分散或研磨直到所需的着色剂粒子,特别地颜料粒子的粒度分布。在细分散之后,可以采用去离子水进一步稀释分散体。
本发明的着色剂制剂可用于将天然和合成纤维材料(例如聚酯、丝、羊毛、混纺织物)染色和印花,特别地用于在各种记录介质上记录文字和图像,以及用于纸或纤维素的本体染色。当贮存根据本发明的记录液体时,没有出现导致模糊印刷图像或导致喷嘴堵塞的沉淀物的离析。本发明的记录液体在粘度和表面张力方面处于适于喷墨工艺的范围内。它们提供高光学密度的具有优异耐晒牢度和耐水牢度的印刷图像。根据本发明的着色剂制剂也适用作电子照相调色剂和显影剂,例如单组分或双组分粉末调色剂(也称为单组分或双组分显影剂)、磁性调色剂、液体调色剂、胶乳调色剂、聚合调色剂以及特种调色剂中的着色剂。典型的调色剂粘结剂是加成聚合、聚加成和缩聚树脂,如苯乙烯树脂、苯乙烯-丙烯酸酯树脂、苯乙烯-丁二烯树脂、丙烯酸酯树脂、聚酯树脂、酚醛环氧树脂、聚砜、聚氨酯,它们单独或组合使用,以及聚乙烯和聚丙烯,它们还可包含进-步的成分,如电荷控制剂,蜡或流动助剂,或后续用这些添加剂改性。
本发明的着色剂制剂进一步适用作粉末和粉末涂料中,特别地可摩擦电或动电喷涂的粉末涂料中的着色剂,该粉末涂料用于涂覆例如由金属、木材、塑料、玻璃、陶瓷、混凝土、纺织品材料、纸或橡胶制成的制品的表面。有用的粉末涂料树脂典型地包括环氧树脂、含羧基和羟基的聚酯树脂、聚氨酯和丙烯酸类树脂,其与通常的固化剂一起使用。也使用树脂的组合。例如,环氧树脂经常与含羧基和羟基的聚酯树脂结合使用。典型的固化剂组分(依赖于树脂体系)例如是酸酐、咪唑以及双氰胺和其衍生物、封端的异氰酸酯、双酰基氨基甲酸酯、酚醛树脂和蜜胺树脂、异氰脲酸三缩水甘油酯、噁唑啉和二羧酸。
此外,根据本发明的着色剂制剂也适用作滤色器用的着色剂,该滤色器既可以是用于加法色生成的,也可以是用于减法色生成的,本发明着色剂制剂还适用作电子油墨(“e-油墨”)或电子纸(“e-纸”)用的着色剂。
根据本发明使用的抗微生物混合物在宽pH范围内显示出抗多种通常病菌的高效力。甚至在较长时间贮存时也没有出现重金属活性物质配合物的沉淀物。
在以下的实施例中,份数表示重量份数。
实施例1
向1000份直接蓝199(5a)(由合成决定的离子铜含量:80ppm)的10wt%水溶液中掺混入各种抗微生物剂直到表1中描述的浓度。在其它测试中加入另外100ppm二价阳离子(以它们的金属盐的形式)。在搅拌之后,将形成的溶液通过纸滤器(Schleicher&Schuell Ref.No.14812)吸滤出。检查纸滤器由于相应的抗微生物剂-重金属配合物的形成引起的沉淀物的出现情况。结果示于表1中。
表1(直接蓝199的10%浓度的溶液)
活性物质 | 商品名 | 纯染料溶液 | Cu2+ | Zn2+ | Fe3+ |
0.01%BIT | Mergal K10N(Troy) | + | ++ | ++ | ++ |
0.01%BIT | NipacideBIT20(Clariant) | + | ++ | ++ | ++ |
0.01%BIT | Proxel GXL(Avecia) | + | ++ | ++ | ++ |
0.018%溴硝丙二醇0.0011%CMIT0.00037%MIT | Nipacide IB(Clariant) | --- | --- | --- | --- |
---无沉淀物
+沉淀物形成
++沉淀物严重形成
BIT 1,2-苯并异噻唑啉-3-酮
表明,本发明的抗微生物剂混合物,与常规抗微生物剂相反,没有与研究的任何重金属阳离子形成不溶性配合物。在Cu2+、Zn2+或Fe3+存在的情况下对比抗微生物剂导致沉淀物的严重形成。
实施例2
将1000份直接蓝199(5a)的10wt%水溶液与0.18份2-溴-2-硝基丙烷-1,3-二醇、0.011份5-氯-2-甲基-4-异噻唑啉-3-酮和0.0037份2-甲基-4-异噻唑啉-3-酮以及0.018份硝酸镁和0.01份氯化镁混合。
实施例3
将1000份活性黑31(5b)的15wt%水溶液与0.18份2-溴-2-硝基丙烷-1,3-二醇、0.011份5-氯-2-甲基-4-异噻唑啉-3-酮和0.0037份2-甲基-4-异噻唑啉-3-酮以及0.018份硝酸镁和0.01份氯化镁混合。
在负荷试验中每周一次向直接蓝199和活性黑31两种染料溶液以及没有抗微生物剂的相应的对照染料溶液中掺混入由如下的细菌、真菌和酵母形成的微生物混合物:
细菌:
杂色假单胞菌(Pseudomonas versicolor)
粪产碱菌
产气肠杆菌
大肠杆菌
雷氏普罗威登斯菌
真菌:
茄病镰刀菌
白地霉
土曲霉
酵母:
深红酵母
随后通过测定在合适培养基上的病菌数目测试病菌负荷。在没有抗微生物剂的两个对照样品情况下,仅在几天之后就已检测到严重的病菌生长,而在含有抗微生物剂混合物的染料溶液的情况下,甚至在5周之后也不能检出能繁殖的微生物。
实施例4-7(颜料)
将作为粉末或作为压滤饼形式的颜料,与分散剂、有机溶剂和其它添加剂一起在去离子水中糊化和然后使用溶解器均化和预分散。使用珠磨机进行随后的细分散,其中在冷却下进行研磨直到所需的颜料粒子的粒度分布。随后,采用去离子水将分散体调节到所需的最终颜料浓度。
按前述方法生产在以下实施例4-7中描述的颜料制剂,其中以所规定的数量使用如下组分,使得形成100份各自的颜料制剂:
实施例4
20份 颜料黄155
2.5份 丙烯酸酯树脂,钠盐(分散剂)
1.2份 聚乙二醇烷基醚,钠盐(分散剂)
0.018份 2-溴-2-硝基丙烷-1,3-二醇
0.0011份 5-氯-2-甲基-4-异噻唑啉-3-酮
0.00037份 2-甲基-4-异噻唑啉-3-酮
0.0018份 硝酸镁
0.001份 氯化镁
余量 去离子水(E-水)
实施例5
20份 颜料红122
2.5份 丙烯酸酯树脂,钠盐(分散剂)
1.2份 聚乙二醇烷基醚,钠盐(分散剂)
0.018份 2-溴-2-硝基丙烷-1,3-二醇
0.0011份 5-氯-2-甲基-4-异噻唑啉-3-酮
0.00037份 2-甲基-4-异噻唑啉-3-酮
0.0018份 硝酸镁
0.001份 氯化镁
余量 去离子水
实施例6
20份 颜料蓝15:3
2.5份 丙烯酸酯树脂,钠盐(分散剂)
1.2份 聚乙二醇烷基醚,钠盐(分散剂)
0.018份 2-溴-2-硝基丙烷-1,3-二醇
0.0011份 5-氯-2-甲基-4-异噻唑啉-3-酮
0.00037份 2-甲基-4-异噻唑啉-3-酮
0.0018份 硝酸镁
0.001份 氯化镁
余量 去离子水
实施例7
15份 炭黑(颜料黑7)
2.5份 丙烯酸酯树脂,钠盐(分散剂)
0.6份 聚乙二醇烷基醚,钠盐(分散剂)
0.018份 2-溴-2-硝基丙烷-1,3-二醇
0.0011份 5-氯-2-甲基-4-异噻唑啉-3-酮
0.00037份 2-甲基-4-异噻唑啉-3-酮
0.0018份 硝酸镁
0.001份 氯化镁
余量 去离子水
对比例
重复实施例4,只是与其相反,省略抗微生物剂,使得得到如下组合物:
20份 颜料黄155
2.5份 丙烯酸酯树脂,钠盐(分散剂)
1.2份 聚乙二醇烷基醚,钠盐(分散剂)
余量 去离子水
随后通过测定在合适培养基上的病菌数目测试病菌负荷。在没有抗微生物剂的对照样品(对比例)情况下,仅在几天之后就已检测到严重的病菌生长,而在含有抗微生物剂混合物的颜料分散体(实施例4-7)的情况下,甚至在1周之后也不能检出能繁殖的微生物。
Claims (9)
1.抗微生物有效量的由5-氯-2-甲基-4-异噻唑啉-3-酮、2-甲基-4-异噻唑啉-3-酮和2-溴-2-硝基丙烷-1,3-二醇形成的混合物在具有重金属离子浓度大于或等于20ppm的含水着色剂制剂中作为抗微生物剂的用途。
2.根据权利要求1的用途,其特征在于着色剂制剂是记录液体,特别是喷墨油墨。
3.根据权利要求1或2的用途,其特征在于抗微生物有效量是0.001wt%-0.1wt%,优选0.02wt%,作为固体形式计算和基于着色剂制剂的总重量计。
4.根据权利要求1-3中至少一项的用途,其特征在于各组分5-氯-2-甲基-4-异噻唑啉-3-酮、2-甲基-4-异噻唑啉-3-酮和2-溴-2-硝基丙烷-1,3-二醇的用量比例是(0.005-0.1)∶(0.005-0.05)∶1。
5.根据权利要求1-4中至少一项的用途,其特征在于着色剂是活性染料、直接染料、酸性染料、分散染料或颜料,并以配位结合方式包含选自Cu、Co、Ni、Fe、Cr和Al的重金属。
6.根据权利要求5的用途,其特征在于着色剂是C.I.活性黑8、C.I.活性黑31、C.I.活性蓝7、C.I.活性蓝14、C.I.活性蓝21、C.I.活性蓝28、C.I.活性蓝38、C.I.活性蓝82、C.I.活性蓝89、C.I.活性蓝158、C.I.活性蓝182、C.I.活性蓝190、C.I.活性蓝203、C.I.活性蓝216、C.I.活性蓝220、C.I.活性蓝244、C.I.活性紫1、C.I.活性紫5、C.I.活性红6、C.I.活性红23、C.I.活性棕18、C.I.直接蓝76、C.I.直接蓝84、C.I.直接蓝86、C.I.直接蓝87、C.I.直接蓝98、C.I.直接蓝199、C.I.直接蓝202、C.I.直接蓝290、C.I.直接黑112、C.I.直接棕95、C.I.直接紫47、C.I.酸性蓝87、C.I.酸性蓝185、C.I.酸性蓝249、C.I.颜料蓝15∶1-15∶4、C.I.颜料蓝17、C.I.颜料绿7、C.I.颜料绿37、C.I.颜料红257、C.I.颜料红271、C.I.颜料橙65、C.I.颜料橙68、C.I.颜料黄117、C.I.颜料黄129或C.I.颜料黄153。
7.一种含水着色剂制剂,其包含0.1wt%-50wt%至少一种重金属配合物着色剂,0.001wt%-0.1wt%根据权利要求1-4中一项或多项的抗微生物混合物和10wt%-90wt%去离子水,每种情况下基于着色剂制剂的总重量(100wt%)计。
8.一种含水着色剂制剂,其包含至少20ppm重金属离子和0.1wt%-50wt%至少一种着色剂,0.001wt%-0.1wt%根据权利要求1-4中一项或多项的抗微生物混合物和10wt%-90wt%去离子水,每种情况下基于着色剂制剂的总重量(100wt%)计。
9.根据权利要求7或8的着色剂制剂,其以0.001wt%-5wt%,特别是0.01wt%-1wt%的数量包含选自如下的配色着色剂:C.I.酸性黄17和C.I.酸性黄23;C.I.直接黄86、C.I.直接黄98和C.I.直接黄132;C.I.活性黄37;C.I.颜料黄17、C.I.颜料黄74、C.I.颜料黄83、C.I.颜料黄97、C.I.颜料黄120、C.I.颜料黄139、C.I.颜料黄151、C.I.颜料黄155和C.I.颜料黄180;C.I.直接红1、C.I.直接红11、C.I.直接红37、C.I.直接红62、C.I.直接红75、C.I.直接红81、C.I.直接红87、C.I.直接红89、C.I.直接红95和C.I.直接红227;C.I.酸性红1、C.I.酸性红8、C.I.酸性红80、C.I.酸性红81、C.I.酸性红82、C.I.酸性红87、C.I.酸性红94、C.I.酸性红115、C.I.酸性红131、C.I.酸性红144、C.I.酸性红152、C.I.酸性红154、C.I.酸性红186、C.I.酸性红245、C.I.酸性红249和C.I.酸性红289;C.I.活性红21、C.I.活性红22、C.I.活性红23、C.I.活性红35、C.I.活性红63、C.I.活性红106、C.I.活性红107、C.I.活性红112、C.I.活性红113、C.I.活性红114、C.I.活性红126、C.I.活性红127、C.I.活性红128、C.I.活性红129、C.I.活性红130、C.I.活性红131、C.I.活性红137、C.I.活性红160、C.I.活性红161、C.I.活性红174和C.I.活性红180;C.I.颜料红122、C.I.颜料红176、C.I.颜料红184、C.I.颜料红185和C.I.颜料红269;C.I.直接蓝199;C.I.酸性蓝9和C.I.颜料蓝15∶1-15∶4,基于总着色剂的干重计。
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JP5296295B2 (ja) * | 2006-02-16 | 2013-09-25 | ブラザー工業株式会社 | インクジェット記録用インク |
JP5296296B2 (ja) * | 2006-02-16 | 2013-09-25 | ブラザー工業株式会社 | インクジェット記録用インク |
JP5242013B2 (ja) * | 2006-02-16 | 2013-07-24 | ブラザー工業株式会社 | インクジェット記録用インク |
JP5296306B2 (ja) * | 2006-09-19 | 2013-09-25 | ブラザー工業株式会社 | インクジェット記録用インク |
JP5296305B2 (ja) * | 2006-09-19 | 2013-09-25 | ブラザー工業株式会社 | インクジェット記録用インク |
KR100863482B1 (ko) * | 2008-01-02 | 2008-10-16 | 주식회사 컴베이스 | 이미지 재현 기기의 토너 이송용 롤러 재생을 위한 코팅 조성물 |
PL2272348T3 (pl) | 2009-07-07 | 2015-08-31 | Lanxess Deutschland Gmbh | Kompozycje biobójcze |
US8586272B2 (en) * | 2009-07-28 | 2013-11-19 | Xerox Corporation | Toner compositions |
US8933134B2 (en) | 2010-06-09 | 2015-01-13 | L'oreal | Compositions containing agar and a softening agent |
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JP3855569B2 (ja) * | 1998-12-04 | 2006-12-13 | コニカミノルタホールディングス株式会社 | インクジェット用インク |
CN1236542A (zh) * | 1999-05-04 | 1999-12-01 | 王兴民 | 异噻唑啉酮衍生物的应用 |
DE60042091D1 (de) * | 1999-06-09 | 2009-06-04 | Seiko Epson Corp | Tintenstrahldruckfarbe mit Fungizid |
GB0004527D0 (en) * | 2000-02-26 | 2000-04-19 | Avecia Ltd | Inks |
US20030176591A1 (en) * | 2000-07-28 | 2003-09-18 | Bo Haggman | Dendritic macromolecule with improved polyether polyol solubility and process for production thereof |
DE10112367A1 (de) * | 2001-03-15 | 2002-09-26 | Bayer Ag | Mikrobizide Mischungen |
US6556470B1 (en) * | 2001-07-31 | 2003-04-29 | Hewlett-Packard Company | Field addressable rewritable media |
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2004
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- 2004-05-21 JP JP2006515782A patent/JP2006527218A/ja active Pending
- 2004-05-21 DE DE502004003623T patent/DE502004003623D1/de not_active Expired - Lifetime
- 2004-05-21 AT AT04734214T patent/ATE360667T1/de not_active IP Right Cessation
- 2004-05-21 ES ES04734214T patent/ES2284014T3/es not_active Expired - Lifetime
- 2004-05-21 US US10/560,091 patent/US20060127272A1/en not_active Abandoned
- 2004-05-21 EP EP04734214A patent/EP1636319B1/de not_active Expired - Lifetime
- 2004-05-21 KR KR1020057023849A patent/KR20060017642A/ko not_active Application Discontinuation
- 2004-05-21 WO PCT/EP2004/005458 patent/WO2004108841A1/de active IP Right Grant
- 2004-05-21 CN CNB2004800161582A patent/CN100560661C/zh not_active Expired - Lifetime
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CN108882710A (zh) * | 2016-04-05 | 2018-11-23 | 托尔有限公司 | 含有5-氯-2-甲基异噻唑啉-3-酮的协同杀生物剂组合物 |
CN108882710B (zh) * | 2016-04-05 | 2024-01-26 | 托尔有限公司 | 含有5-氯-2-甲基异噻唑啉-3-酮的协同杀生物剂组合物 |
CN109418262A (zh) * | 2017-08-29 | 2019-03-05 | 三博生化科技(上海)有限公司 | 一种防腐剂及其制备方法 |
CN109221175A (zh) * | 2018-09-30 | 2019-01-18 | 高菠 | 一种水稻恶苗病杀菌剂组合物及制备方法 |
CN111134136A (zh) * | 2019-12-14 | 2020-05-12 | 嘉兴沃特泰科环保科技股份有限公司 | 一种ro非氧化粘泥控制及杀菌剂及其制备方法和应用 |
CN113956680A (zh) * | 2021-11-24 | 2022-01-21 | 浙江纳美新材料股份有限公司 | 一种净味水油通用色精及其制备方法 |
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CN114716845A (zh) * | 2022-02-25 | 2022-07-08 | 青岛英杰泰新材料有限公司 | 一种酸性喷墨数码印花墨水、制备方法及应用 |
CN116005472A (zh) * | 2022-05-25 | 2023-04-25 | 浙江天台锦豪印花材料有限公司 | 水溶性升华转印花油墨及其制备方法 |
CN116005472B (zh) * | 2022-05-25 | 2023-10-27 | 浙江天台锦豪印花材料有限公司 | 水溶性升华转印花油墨及其制备方法 |
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CA2528859A1 (en) | 2004-12-16 |
DE502004003623D1 (de) | 2007-06-06 |
CN100560661C (zh) | 2009-11-18 |
EP1636319A1 (de) | 2006-03-22 |
ES2284014T3 (es) | 2007-11-01 |
ATE360667T1 (de) | 2007-05-15 |
JP2006527218A (ja) | 2006-11-30 |
KR20060017642A (ko) | 2006-02-24 |
WO2004108841A1 (de) | 2004-12-16 |
EP1636319B1 (de) | 2007-04-25 |
DE10326210A1 (de) | 2004-12-30 |
US20060127272A1 (en) | 2006-06-15 |
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