JP5787996B2 - 紙を染色するための蛍光染料 - Google Patents
紙を染色するための蛍光染料 Download PDFInfo
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- JP5787996B2 JP5787996B2 JP2013517153A JP2013517153A JP5787996B2 JP 5787996 B2 JP5787996 B2 JP 5787996B2 JP 2013517153 A JP2013517153 A JP 2013517153A JP 2013517153 A JP2013517153 A JP 2013517153A JP 5787996 B2 JP5787996 B2 JP 5787996B2
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- aqueous formulation
- hydrogen
- cellulose
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- 238000004043 dyeing Methods 0.000 title claims description 12
- 239000007850 fluorescent dye Substances 0.000 title description 3
- 239000013011 aqueous formulation Substances 0.000 claims description 35
- 239000000463 material Substances 0.000 claims description 29
- 150000001875 compounds Chemical class 0.000 claims description 27
- 239000001257 hydrogen Substances 0.000 claims description 27
- 229910052739 hydrogen Inorganic materials 0.000 claims description 27
- 229920002678 cellulose Polymers 0.000 claims description 26
- 239000001913 cellulose Substances 0.000 claims description 26
- 150000002431 hydrogen Chemical group 0.000 claims description 19
- 239000002270 dispersing agent Substances 0.000 claims description 18
- 238000000576 coating method Methods 0.000 claims description 11
- 239000004952 Polyamide Substances 0.000 claims description 10
- 239000011248 coating agent Substances 0.000 claims description 10
- 238000000034 method Methods 0.000 claims description 10
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 10
- 229920002647 polyamide Polymers 0.000 claims description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 10
- 125000003118 aryl group Chemical group 0.000 claims description 7
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 5
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 5
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims description 4
- 150000003863 ammonium salts Chemical class 0.000 claims description 4
- 125000003107 substituted aryl group Chemical group 0.000 claims description 4
- 125000003277 amino group Chemical group 0.000 claims description 3
- 150000001768 cations Chemical class 0.000 claims description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
- 125000000547 substituted alkyl group Chemical group 0.000 claims description 3
- 229910052783 alkali metal Inorganic materials 0.000 claims description 2
- 150000001340 alkali metals Chemical class 0.000 claims description 2
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims description 2
- 150000001342 alkaline earth metals Chemical class 0.000 claims description 2
- 125000003545 alkoxy group Chemical group 0.000 claims description 2
- 229910052794 bromium Inorganic materials 0.000 claims description 2
- 229910052801 chlorine Inorganic materials 0.000 claims description 2
- 125000000623 heterocyclic group Chemical group 0.000 claims description 2
- 229910052740 iodine Inorganic materials 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 2
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims 1
- 239000000975 dye Substances 0.000 description 9
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 4
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 3
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 229910052796 boron Inorganic materials 0.000 description 3
- -1 methoxy, ethoxy, phenoxy Chemical group 0.000 description 3
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
- 229920001131 Pulp (paper) Polymers 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- YXVFYQXJAXKLAK-UHFFFAOYSA-N biphenyl-4-ol Chemical group C1=CC(O)=CC=C1C1=CC=CC=C1 YXVFYQXJAXKLAK-UHFFFAOYSA-N 0.000 description 2
- WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 239000008199 coating composition Substances 0.000 description 2
- 239000003086 colorant Substances 0.000 description 2
- 239000006185 dispersion Substances 0.000 description 2
- JBKVHLHDHHXQEQ-UHFFFAOYSA-N epsilon-caprolactam Chemical compound O=C1CCCCCN1 JBKVHLHDHHXQEQ-UHFFFAOYSA-N 0.000 description 2
- 239000000835 fiber Substances 0.000 description 2
- 229910052736 halogen Inorganic materials 0.000 description 2
- 150000002367 halogens Chemical class 0.000 description 2
- 238000002372 labelling Methods 0.000 description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- YJDOOZAXSYRWPY-UHFFFAOYSA-N 2-(4-methoxyphenyl)-4h-furo[3,2-b]pyrrole-5-carboxylic acid Chemical compound C1=CC(OC)=CC=C1C(O1)=CC2=C1C=C(C(O)=O)N2 YJDOOZAXSYRWPY-UHFFFAOYSA-N 0.000 description 1
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 description 1
- 229910015900 BF3 Inorganic materials 0.000 description 1
- 235000018185 Betula X alpestris Nutrition 0.000 description 1
- 235000018212 Betula X uliginosa Nutrition 0.000 description 1
- 229920000742 Cotton Polymers 0.000 description 1
- 241000196324 Embryophyta Species 0.000 description 1
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
- 235000008331 Pinus X rigitaeda Nutrition 0.000 description 1
- 235000011613 Pinus brutia Nutrition 0.000 description 1
- 241000018646 Pinus brutia Species 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-N Sulfurous acid Chemical compound OS(O)=O LSNNMFCWUKXFEE-UHFFFAOYSA-N 0.000 description 1
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
- 239000006096 absorbing agent Substances 0.000 description 1
- 239000002671 adjuvant Substances 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 125000000129 anionic group Chemical group 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000012472 biological sample Substances 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 125000000753 cycloalkyl group Chemical group 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 239000002917 insecticide Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 229920001281 polyalkylene Polymers 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- IIACRCGMVDHOTQ-UHFFFAOYSA-N sulfamic acid Chemical compound NS(O)(=O)=O IIACRCGMVDHOTQ-UHFFFAOYSA-N 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 239000004753 textile Substances 0.000 description 1
- NLOUTGCXBXLQIA-UHFFFAOYSA-N trichloro phosphate Chemical compound ClOP(=O)(OCl)OCl NLOUTGCXBXLQIA-UHFFFAOYSA-N 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
- 210000002268 wool Anatomy 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
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F5/00—Compounds containing elements of Groups 3 or 13 of the Periodic Table
- C07F5/02—Boron compounds
- C07F5/022—Boron compounds without C-boron linkages
-
- 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
- C09B57/00—Other synthetic dyes of known constitution
-
- 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
- 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
- C09B67/0089—Non common dispersing agents non ionic dispersing agent, e.g. EO or PO addition products
-
- D—TEXTILES; PAPER
- D21—PAPER-MAKING; PRODUCTION OF CELLULOSE
- D21H—PULP COMPOSITIONS; PREPARATION THEREOF NOT COVERED BY SUBCLASSES D21C OR D21D; IMPREGNATING OR COATING OF PAPER; TREATMENT OF FINISHED PAPER NOT COVERED BY CLASS B31 OR SUBCLASS D21G; PAPER NOT OTHERWISE PROVIDED FOR
- D21H21/00—Non-fibrous material added to the pulp, characterised by its function, form or properties; Paper-impregnating or coating material, characterised by its function, form or properties
- D21H21/14—Non-fibrous material added to the pulp, characterised by its function, form or properties; Paper-impregnating or coating material, characterised by its function, form or properties characterised by function or properties in or on the paper
- D21H21/28—Colorants ; Pigments or opacifying agents
-
- D—TEXTILES; PAPER
- D21—PAPER-MAKING; PRODUCTION OF CELLULOSE
- D21H—PULP COMPOSITIONS; PREPARATION THEREOF NOT COVERED BY SUBCLASSES D21C OR D21D; IMPREGNATING OR COATING OF PAPER; TREATMENT OF FINISHED PAPER NOT COVERED BY CLASS B31 OR SUBCLASS D21G; PAPER NOT OTHERWISE PROVIDED FOR
- D21H21/00—Non-fibrous material added to the pulp, characterised by its function, form or properties; Paper-impregnating or coating material, characterised by its function, form or properties
- D21H21/14—Non-fibrous material added to the pulp, characterised by its function, form or properties; Paper-impregnating or coating material, characterised by its function, form or properties characterised by function or properties in or on the paper
- D21H21/30—Luminescent or fluorescent substances, e.g. for optical bleaching
-
- D—TEXTILES; PAPER
- D21—PAPER-MAKING; PRODUCTION OF CELLULOSE
- D21H—PULP COMPOSITIONS; PREPARATION THEREOF NOT COVERED BY SUBCLASSES D21C OR D21D; IMPREGNATING OR COATING OF PAPER; TREATMENT OF FINISHED PAPER NOT COVERED BY CLASS B31 OR SUBCLASS D21G; PAPER NOT OTHERWISE PROVIDED FOR
- D21H21/00—Non-fibrous material added to the pulp, characterised by its function, form or properties; Paper-impregnating or coating material, characterised by its function, form or properties
- D21H21/14—Non-fibrous material added to the pulp, characterised by its function, form or properties; Paper-impregnating or coating material, characterised by its function, form or properties characterised by function or properties in or on the paper
- D21H21/40—Agents facilitating proof of genuineness or preventing fraudulent alteration, e.g. for security paper
-
- D—TEXTILES; PAPER
- D21—PAPER-MAKING; PRODUCTION OF CELLULOSE
- D21H—PULP COMPOSITIONS; PREPARATION THEREOF NOT COVERED BY SUBCLASSES D21C OR D21D; IMPREGNATING OR COATING OF PAPER; TREATMENT OF FINISHED PAPER NOT COVERED BY CLASS B31 OR SUBCLASS D21G; PAPER NOT OTHERWISE PROVIDED FOR
- D21H21/00—Non-fibrous material added to the pulp, characterised by its function, form or properties; Paper-impregnating or coating material, characterised by its function, form or properties
- D21H21/06—Paper forming aids
- D21H21/08—Dispersing agents for fibres
-
- D—TEXTILES; PAPER
- D21—PAPER-MAKING; PRODUCTION OF CELLULOSE
- D21H—PULP COMPOSITIONS; PREPARATION THEREOF NOT COVERED BY SUBCLASSES D21C OR D21D; IMPREGNATING OR COATING OF PAPER; TREATMENT OF FINISHED PAPER NOT COVERED BY CLASS B31 OR SUBCLASS D21G; PAPER NOT OTHERWISE PROVIDED FOR
- D21H23/00—Processes or apparatus for adding material to the pulp or to the paper
- D21H23/02—Processes or apparatus for adding material to the pulp or to the paper characterised by the manner in which substances are added
- D21H23/22—Addition to the formed paper
- D21H23/52—Addition to the formed paper by contacting paper with a device carrying the material
- D21H23/56—Rolls
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Dispersion Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Paper (AREA)
- Coloring (AREA)
- Inks, Pencil-Leads, Or Crayons (AREA)
Description
[式中、
R1は、水素、CN、CF3、Br、Cl、I;置換されていてもよいアリール;または置換されていてもよいアルキルを表し;
R2およびR3は互いに独立に、水素;C1〜5−アルキル;C1〜5−アルコキシル;置換されていてもよいアリール;置換されていてもよいフェニル;p−C1〜5−アルコキシフェニル;ジ(C1〜5−アルキル)アミノ基;または−SO3Mを表し、ここで、Mは、カチオン、好ましくは水素、アルカリ金属、アルカリ土類金属、アンモニウムまたはモノ−、ジ−、トリ−もしくはテトラ置換アンモニウム、詳細にはモノ−C1〜5−アルキル−、ジ−C1〜5−アルキル−、トリ−C1〜5−アルキル−、テトラ−C1〜5−アルキルアンモニウム、モノ−C1〜5−ヒドロキシアルキル−、ジ−C1〜5−ヒドロキシアルキル−、トリ−C1〜5−ヒドロキシアルキル−、テトラ−C1〜5−ヒドロキシアルキルアンモニウムもしくはベンジルトリ−C1〜5−ヒドロキシアルキルアンモニウムまたは、ピロリジン、ピペリジン、モルホリンもしくはピペラジンまたはそのN−モノアルキル−もしくはN,N−ジアルキル置換生成物などの窒素含有の5員または6員の飽和複素環に由来するアミンをベースとするアンモニウムであり;R2およびR3は、任意の位置で芳香環に結合しており;
k、mは互いに独立に、1から3の整数、好ましくは1または2、最も好ましくは1である]、
水および場合によって分散剤を含有するが、
但し、水性配合物が分散剤を含有せずR1が水素である場合、R2およびR3のうちの少なくとも1個が水素ではなく、好ましくはR2およびR3の両方ともが水素ではないことを条件とする水性配合物に関する。
[式中、
R1、R2およびR3は互いに独立に、水素、置換されていてもよいシクロヘキシルまたはフェニルであり、ここで、残基R1からR3のうちの少なくとも1個は水素ではなく、
R4およびR5は互いに独立に、メチルまたは水素であり、かつ
nは、21から40の整数である]。
化学的に漂白された松材亜硫酸セルロース7重量部および化学的に漂白されたカバノキ材亜硫酸セルロース3重量部を水と共にミキサー中で叩解する。液体染料配合物1重量部をこの紙料に加え、続いて、20分間混合し、そこから、手すき紙(handsheet)を製造する。得られた紙は青緑色を有する。
Claims (16)
- 式(1)の化合物
R1は、水素、CN、CF3、Br、Cl、I;置換されていてもよいアリール;また
は置換されていてもよいアルキルを表し;
R2およびR3は互いに独立に、水素;C1〜5−アルキル;C1〜5−アルコキシル;置換されていてもよいアリール;置換されていてもよいフェニル;p−C1〜5−アルコキシフェニル;ジ(C1〜5−アルキル)アミノ基;または−SO3Mを表し、ここで、Mはカチオンであり、;R2およびR3は、任意の位置で芳香環に結合しており;R2およびR3の少なくとも1つは−SO 3 Mであり;
k、mは互いに独立に、1から3の整数である]、
水および場合によって分散剤を含むが、
但し、水性配合物が分散剤を含有せずR1が水素である場合、R2およびR3のうちの少なくとも1つが水素ではないことを条件とする水性配合物。 - 前記カチオンが、水素、アルカリ金属、アルカリ土類金属、アンモニウム、または、モノ−、ジ−、トリ−もしくはテトラ置換アンモニウムである、請求項1に記載の水性配合物。
- 前記モノ−、ジ−、トリ−もしくはテトラ置換アンモニウムが、C 1 〜 5 −アルキルおよび/またはC 1 〜 5 −ヒドロキシアルキルによって置換されている、または、窒素含有の5員もしくは6員の飽和複素環に由来するアミンをベースとするアンモニウムである、請求項2に記載の水性配合物。
- R2およびR3が互いに独立に、水素、C1〜3−アルコキシルまたは−SO3Mを表す、請求項1〜3のいずれかに記載の水性配合物。
- R1が水素、CNまたはCF3を表す、請求項1〜4のいずれかに記載の水性配合物。
- 式(1)の化合物が、それぞれp−位に1個のR2基および1個のR3基を含有する、請求項1〜5のいずれかに記載の水性配合物。
- R1が水素であり、R2およびR3が両方とも−SO 3 Mである、請求項1〜6のいずれかに記載の水性配合物。
- 式(1)の化合物を0.01から50重量%および分散剤を0から10重量%含有する、請求項1〜8のいずれかに記載の水性配合物。
- セルロースおよび/またはポリアミド含有材料を染色または印刷するための請求項1〜9のいずれかに記載の水性配合物の使用。
- セルロース含有材料が、パルプ、または、セルロース材料を含有するシートである、請求項10に記載の使用。
- 水性配合物を、セルロース含有材料を染色するためにパルプ中で、サイズプレス中で、かつ/またはコーティング塗布によって使用する、請求項10または11に記載の使用。
- セルロースおよび/またはポリアミド含有材料を請求項1〜9のいずれかに記載の水性配合物と接触させる、セルロースおよび/またはポリアミド含有材料を染色または印刷する方法。
- セルロース含有材料が、パルプ、または、セルロース材料を含有するシートである、請求項13に記載の方法。
- セルロース含有材料との接触をパルプ中で、サイズプレス中で、かつ/またはコーティング塗布によって実施する、請求項13または14に記載の方法。
- 請求項13〜15のいずれかに記載の方法によって得られる紙または製品。
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
EP10167519A EP2399962B1 (en) | 2010-06-28 | 2010-06-28 | Fluorescent dyes for paper dyeing |
EP10167519.7 | 2010-06-28 | ||
PCT/EP2011/059955 WO2012000794A1 (en) | 2010-06-28 | 2011-06-15 | Fluorescent dyes for paper dyeing |
Publications (2)
Publication Number | Publication Date |
---|---|
JP2013534556A JP2013534556A (ja) | 2013-09-05 |
JP5787996B2 true JP5787996B2 (ja) | 2015-09-30 |
Family
ID=42752358
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2013517153A Expired - Fee Related JP5787996B2 (ja) | 2010-06-28 | 2011-06-15 | 紙を染色するための蛍光染料 |
Country Status (4)
Country | Link |
---|---|
US (1) | US9057015B2 (ja) |
EP (1) | EP2399962B1 (ja) |
JP (1) | JP5787996B2 (ja) |
WO (1) | WO2012000794A1 (ja) |
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US9012871B2 (en) | 2013-05-02 | 2015-04-21 | Delphax Technologies Inc. | Use of fluorescent inks for document authentication |
DE102019118872A1 (de) * | 2019-07-11 | 2021-01-14 | Heliatek Gmbh | Organische Verbindung, und optoelektronisches Bauelement mit einer solchen organischen Verbindung |
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JPS4829802B1 (ja) * | 1970-01-26 | 1973-09-13 | ||
FR2365656A1 (fr) | 1976-05-25 | 1978-04-21 | Arjomari Prioux | Papier de securite |
JPS5455612A (en) * | 1977-10-08 | 1979-05-02 | Mitsubishi Paper Mills Ltd | Pigment coated paper for printing |
JPS5580600A (en) * | 1978-12-07 | 1980-06-17 | Oji Paper Co | Paper for preventing forgery |
JPH04202863A (ja) * | 1990-11-29 | 1992-07-23 | Unitika Ltd | ポリアミド繊維の蛍光増白染色方法 |
JPH0693600A (ja) | 1992-09-09 | 1994-04-05 | Mitsubishi Paper Mills Ltd | 装飾用シート |
DE10042730A1 (de) | 2000-08-31 | 2002-03-14 | Bayer Ag | Alkoxylierte Phenolderivate |
EP1285941A1 (de) | 2001-08-21 | 2003-02-26 | Bayer Aktiengesellschaft | Verwendung alkoxylierter Phenolderivate |
DE10356341A1 (de) | 2003-11-28 | 2005-06-23 | Bayer Chemicals Ag | Alkoxylierte Polyalkylenimine mit anionischen Gruppen und ihre Verwendung |
WO2007044866A2 (en) | 2005-10-11 | 2007-04-19 | The Regents Of The University Of California | Water-soluble, fluorescent compounds for detection of potassium ions |
EP2022794B1 (en) | 2006-04-28 | 2017-08-23 | Keio University | Fluorescent compound and labeling agent comprising the same |
US20090084510A1 (en) * | 2007-05-16 | 2009-04-02 | Buckman Laboratories International, Inc. | Methods To Detect Organic Contaminants In Pulp and Fiber |
US20100231125A1 (en) * | 2009-03-12 | 2010-09-16 | Sheng Li | Organic light emitting device to emit in near infrared |
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US20130105099A1 (en) | 2013-05-02 |
JP2013534556A (ja) | 2013-09-05 |
EP2399962A1 (en) | 2011-12-28 |
EP2399962B1 (en) | 2013-02-13 |
WO2012000794A1 (en) | 2012-01-05 |
US9057015B2 (en) | 2015-06-16 |
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