CA2562777C - Improvements relating to optical brightening agents - Google Patents
Improvements relating to optical brightening agents Download PDFInfo
- Publication number
- CA2562777C CA2562777C CA2562777A CA2562777A CA2562777C CA 2562777 C CA2562777 C CA 2562777C CA 2562777 A CA2562777 A CA 2562777A CA 2562777 A CA2562777 A CA 2562777A CA 2562777 C CA2562777 C CA 2562777C
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- Canada
- Prior art keywords
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- paper
- 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 - Fee Related
Links
- 230000003287 optical effect Effects 0.000 title claims abstract description 25
- 238000005282 brightening Methods 0.000 title claims abstract description 18
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 13
- 239000008199 coating composition Substances 0.000 claims abstract description 13
- 239000004753 textile Substances 0.000 claims abstract description 6
- 239000000243 solution Substances 0.000 claims description 31
- 150000001875 compounds Chemical class 0.000 claims description 30
- 239000007864 aqueous solution Substances 0.000 claims description 20
- 229920001223 polyethylene glycol Polymers 0.000 claims description 17
- 239000002202 Polyethylene glycol Substances 0.000 claims description 16
- BHRZNVHARXXAHW-UHFFFAOYSA-N sec-butylamine Chemical compound CCC(C)N BHRZNVHARXXAHW-UHFFFAOYSA-N 0.000 claims description 15
- 239000011230 binding agent Substances 0.000 claims description 12
- 239000000203 mixture Substances 0.000 claims description 12
- 229910052739 hydrogen Inorganic materials 0.000 claims description 11
- 239000001257 hydrogen Substances 0.000 claims description 10
- 238000000034 method Methods 0.000 claims description 10
- -1 alkali metal cation Chemical class 0.000 claims description 9
- 238000004513 sizing Methods 0.000 claims description 9
- 239000000725 suspension Substances 0.000 claims description 9
- 150000004820 halides Chemical class 0.000 claims description 8
- 150000001412 amines Chemical class 0.000 claims description 7
- 125000005842 heteroatom Chemical group 0.000 claims description 6
- LDCCBULMAFILCT-UHFFFAOYSA-N 2-aminobenzene-1,4-disulfonic acid Chemical compound NC1=CC(S(O)(=O)=O)=CC=C1S(O)(=O)=O LDCCBULMAFILCT-UHFFFAOYSA-N 0.000 claims description 5
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims description 5
- 229910052783 alkali metal Inorganic materials 0.000 claims description 5
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 claims description 4
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims description 4
- 150000004982 aromatic amines Chemical class 0.000 claims description 4
- JJWLVOIRVHMVIS-UHFFFAOYSA-N isopropylamine Chemical compound CC(C)N JJWLVOIRVHMVIS-UHFFFAOYSA-N 0.000 claims description 4
- XHFGWHUWQXTGAT-UHFFFAOYSA-N n-methylpropan-2-amine Chemical compound CNC(C)C XHFGWHUWQXTGAT-UHFFFAOYSA-N 0.000 claims description 4
- 229910052708 sodium Inorganic materials 0.000 claims description 4
- 239000011734 sodium Substances 0.000 claims description 4
- 238000001035 drying Methods 0.000 claims description 3
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims description 2
- 150000004985 diamines Chemical class 0.000 claims description 2
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 claims description 2
- 238000003541 multi-stage reaction Methods 0.000 claims description 2
- 229910052700 potassium Inorganic materials 0.000 claims description 2
- 239000011591 potassium Substances 0.000 claims description 2
- 238000002360 preparation method Methods 0.000 claims description 2
- 150000002431 hydrogen Chemical class 0.000 claims 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 3
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims 2
- 125000000217 alkyl group Chemical group 0.000 claims 1
- 238000004132 cross linking Methods 0.000 claims 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract description 22
- 125000000129 anionic group Chemical group 0.000 abstract description 11
- PJANXHGTPQOBST-VAWYXSNFSA-N Stilbene Natural products C=1C=CC=CC=1/C=C/C1=CC=CC=C1 PJANXHGTPQOBST-VAWYXSNFSA-N 0.000 abstract description 3
- PJANXHGTPQOBST-UHFFFAOYSA-N stilbene Chemical compound C=1C=CC=CC=1C=CC1=CC=CC=C1 PJANXHGTPQOBST-UHFFFAOYSA-N 0.000 abstract description 3
- 235000021286 stilbenes Nutrition 0.000 abstract description 3
- 230000002087 whitening effect Effects 0.000 abstract description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 45
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 24
- 239000000123 paper Substances 0.000 description 19
- 150000003839 salts Chemical class 0.000 description 13
- 239000011780 sodium chloride Substances 0.000 description 12
- 238000006243 chemical reaction Methods 0.000 description 8
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 description 8
- 239000012463 white pigment Substances 0.000 description 8
- REJHVSOVQBJEBF-UHFFFAOYSA-N 5-azaniumyl-2-[2-(4-azaniumyl-2-sulfonatophenyl)ethenyl]benzenesulfonate Chemical compound OS(=O)(=O)C1=CC(N)=CC=C1C=CC1=CC=C(N)C=C1S(O)(=O)=O REJHVSOVQBJEBF-UHFFFAOYSA-N 0.000 description 6
- 229910006069 SO3H Inorganic materials 0.000 description 6
- 238000010992 reflux Methods 0.000 description 6
- 229920002472 Starch Polymers 0.000 description 5
- 239000002253 acid Substances 0.000 description 5
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 5
- 239000004745 nonwoven fabric Substances 0.000 description 5
- 239000008107 starch Substances 0.000 description 5
- 235000019698 starch Nutrition 0.000 description 5
- 239000002585 base Substances 0.000 description 4
- MGNCLNQXLYJVJD-UHFFFAOYSA-N cyanuric chloride Chemical compound ClC1=NC(Cl)=NC(Cl)=N1 MGNCLNQXLYJVJD-UHFFFAOYSA-N 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 3
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 3
- 230000002378 acidificating effect Effects 0.000 description 3
- 150000007513 acids Chemical class 0.000 description 3
- 235000012211 aluminium silicate Nutrition 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 239000004202 carbamide Substances 0.000 description 3
- 229910052736 halogen Inorganic materials 0.000 description 3
- 150000002367 halogens Chemical class 0.000 description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 3
- 239000005457 ice water Substances 0.000 description 3
- 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 3
- 125000003263 primary aromatic amine group Chemical group 0.000 description 3
- 159000000000 sodium salts Chemical class 0.000 description 3
- 238000006467 substitution reaction Methods 0.000 description 3
- 239000000758 substrate Substances 0.000 description 3
- BKMMTJMQCTUHRP-UHFFFAOYSA-N 2-aminopropan-1-ol Chemical compound CC(N)CO BKMMTJMQCTUHRP-UHFFFAOYSA-N 0.000 description 2
- UNBMPKNTYKDYCG-UHFFFAOYSA-N 4-methylpentan-2-amine Chemical compound CC(C)CC(C)N UNBMPKNTYKDYCG-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- 239000005995 Aluminium silicate Substances 0.000 description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- TWRXJAOTZQYOKJ-UHFFFAOYSA-L Magnesium chloride Chemical compound [Mg+2].[Cl-].[Cl-] TWRXJAOTZQYOKJ-UHFFFAOYSA-L 0.000 description 2
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 2
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 150000001340 alkali metals Chemical group 0.000 description 2
- 125000000539 amino acid group Chemical group 0.000 description 2
- TZCXTZWJZNENPQ-UHFFFAOYSA-L barium sulfate Chemical compound [Ba+2].[O-]S([O-])(=O)=O TZCXTZWJZNENPQ-UHFFFAOYSA-L 0.000 description 2
- OSGAYBCDTDRGGQ-UHFFFAOYSA-L calcium sulfate Chemical compound [Ca+2].[O-]S([O-])(=O)=O OSGAYBCDTDRGGQ-UHFFFAOYSA-L 0.000 description 2
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 2
- 239000002270 dispersing agent Substances 0.000 description 2
- 239000004816 latex Substances 0.000 description 2
- 229920000126 latex Polymers 0.000 description 2
- 238000005374 membrane filtration Methods 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- QNIVIMYXGGFTAK-UHFFFAOYSA-N octodrine Chemical compound CC(C)CCCC(C)N QNIVIMYXGGFTAK-UHFFFAOYSA-N 0.000 description 2
- 239000002245 particle Substances 0.000 description 2
- 239000000049 pigment Substances 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- 229920002451 polyvinyl alcohol Polymers 0.000 description 2
- 235000019422 polyvinyl alcohol Nutrition 0.000 description 2
- 229920001592 potato starch Polymers 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 238000001556 precipitation Methods 0.000 description 2
- 229920003002 synthetic resin Polymers 0.000 description 2
- 239000000057 synthetic resin Substances 0.000 description 2
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 2
- ZMCHBSMFKQYNKA-UHFFFAOYSA-N 2-aminobenzenesulfonic acid Chemical compound NC1=CC=CC=C1S(O)(=O)=O ZMCHBSMFKQYNKA-UHFFFAOYSA-N 0.000 description 1
- ZAJAQTYSTDTMCU-UHFFFAOYSA-N 3-aminobenzenesulfonic acid Chemical compound NC1=CC=CC(S(O)(=O)=O)=C1 ZAJAQTYSTDTMCU-UHFFFAOYSA-N 0.000 description 1
- JOZZAIIGWFLONA-UHFFFAOYSA-N 3-methylbutan-2-amine Chemical compound CC(C)C(C)N JOZZAIIGWFLONA-UHFFFAOYSA-N 0.000 description 1
- JUGFAVYVWUFUCN-UHFFFAOYSA-N 3-methylbutane-1,2-diamine Chemical compound CC(C)C(N)CN JUGFAVYVWUFUCN-UHFFFAOYSA-N 0.000 description 1
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
- IMUUNYPYNWXUBO-UHFFFAOYSA-N 4-aminobenzene-1,3-disulfonic acid Chemical compound NC1=CC=C(S(O)(=O)=O)C=C1S(O)(=O)=O IMUUNYPYNWXUBO-UHFFFAOYSA-N 0.000 description 1
- HVBSAKJJOYLTQU-UHFFFAOYSA-N 4-aminobenzenesulfonic acid Chemical compound NC1=CC=C(S(O)(=O)=O)C=C1 HVBSAKJJOYLTQU-UHFFFAOYSA-N 0.000 description 1
- 229920005789 ACRONAL® acrylic binder Polymers 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical class OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- 229920002134 Carboxymethyl cellulose Polymers 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- 229920000742 Cotton Polymers 0.000 description 1
- KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 description 1
- 235000010469 Glycine max Nutrition 0.000 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- 229920000881 Modified starch Polymers 0.000 description 1
- 239000004368 Modified starch Substances 0.000 description 1
- 239000004372 Polyvinyl alcohol Substances 0.000 description 1
- 229920002125 Sokalan® Polymers 0.000 description 1
- 239000002174 Styrene-butadiene Substances 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- SLINHMUFWFWBMU-UHFFFAOYSA-N Triisopropanolamine Chemical compound CC(O)CN(CC(C)O)CC(C)O SLINHMUFWFWBMU-UHFFFAOYSA-N 0.000 description 1
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 description 1
- 235000011054 acetic acid Nutrition 0.000 description 1
- WNROFYMDJYEPJX-UHFFFAOYSA-K aluminium hydroxide Chemical compound [OH-].[OH-].[OH-].[Al+3] WNROFYMDJYEPJX-UHFFFAOYSA-K 0.000 description 1
- 229910021502 aluminium hydroxide Inorganic materials 0.000 description 1
- 229910000323 aluminium silicate Inorganic materials 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 239000012736 aqueous medium Substances 0.000 description 1
- 239000007900 aqueous suspension Substances 0.000 description 1
- AYJRCSIUFZENHW-DEQYMQKBSA-L barium(2+);oxomethanediolate Chemical compound [Ba+2].[O-][14C]([O-])=O AYJRCSIUFZENHW-DEQYMQKBSA-L 0.000 description 1
- DQXBYHZEEUGOBF-UHFFFAOYSA-N but-3-enoic acid;ethene Chemical compound C=C.OC(=O)CC=C DQXBYHZEEUGOBF-UHFFFAOYSA-N 0.000 description 1
- MTAZNLWOLGHBHU-UHFFFAOYSA-N butadiene-styrene rubber Chemical compound C=CC=C.C=CC1=CC=CC=C1 MTAZNLWOLGHBHU-UHFFFAOYSA-N 0.000 description 1
- 229910000019 calcium carbonate Inorganic materials 0.000 description 1
- 239000001175 calcium sulphate Substances 0.000 description 1
- 235000011132 calcium sulphate Nutrition 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- 239000001768 carboxy methyl cellulose Substances 0.000 description 1
- 235000010948 carboxy methyl cellulose Nutrition 0.000 description 1
- 239000008112 carboxymethyl-cellulose Substances 0.000 description 1
- 239000005018 casein Substances 0.000 description 1
- BECPQYXYKAMYBN-UHFFFAOYSA-N casein, tech. Chemical compound NCCCCC(C(O)=O)N=C(O)C(CC(O)=O)N=C(O)C(CCC(O)=N)N=C(O)C(CC(C)C)N=C(O)C(CCC(O)=O)N=C(O)C(CC(O)=O)N=C(O)C(CCC(O)=O)N=C(O)C(C(C)O)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=O)N=C(O)C(CCC(O)=O)N=C(O)C(COP(O)(O)=O)N=C(O)C(CCC(O)=N)N=C(O)C(N)CC1=CC=CC=C1 BECPQYXYKAMYBN-UHFFFAOYSA-N 0.000 description 1
- 235000021240 caseins Nutrition 0.000 description 1
- 125000002091 cationic group Chemical group 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 239000004927 clay Substances 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 239000005038 ethylene vinyl acetate Substances 0.000 description 1
- 239000004744 fabric Substances 0.000 description 1
- XEKSTYNIJLDDAZ-JASSWCPGSA-F fondaparinux sodium Chemical compound [Na+].[Na+].[Na+].[Na+].[Na+].[Na+].[Na+].[Na+].[Na+].[Na+].O[C@@H]1[C@@H](NS([O-])(=O)=O)[C@@H](OC)O[C@H](COS([O-])(=O)=O)[C@H]1O[C@H]1[C@H](OS([O-])(=O)=O)[C@@H](O)[C@H](O[C@@H]2[C@@H]([C@@H](OS([O-])(=O)=O)[C@H](O[C@H]3[C@@H]([C@@H](O)[C@H](O[C@@H]4[C@@H]([C@@H](O)[C@H](O)[C@@H](COS([O-])(=O)=O)O4)NS([O-])(=O)=O)[C@H](O3)C(O)=O)O)[C@@H](COS([O-])(=O)=O)O2)NS([O-])(=O)=O)[C@H](C(O)=O)O1 XEKSTYNIJLDDAZ-JASSWCPGSA-F 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 229910052602 gypsum Inorganic materials 0.000 description 1
- 239000010440 gypsum Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 235000011167 hydrochloric acid Nutrition 0.000 description 1
- 239000003752 hydrotrope Substances 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- 150000004679 hydroxides Chemical class 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- NBZBKCUXIYYUSX-UHFFFAOYSA-N iminodiacetic acid Chemical compound OC(=O)CNCC(O)=O NBZBKCUXIYYUSX-UHFFFAOYSA-N 0.000 description 1
- 239000001023 inorganic pigment Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 229910001629 magnesium chloride Inorganic materials 0.000 description 1
- 230000014759 maintenance of location Effects 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000002609 medium Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 235000019426 modified starch Nutrition 0.000 description 1
- RIVIDPPYRINTTH-UHFFFAOYSA-N n-ethylpropan-2-amine Chemical compound CCNC(C)C RIVIDPPYRINTTH-UHFFFAOYSA-N 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 239000001254 oxidized starch Substances 0.000 description 1
- 235000013808 oxidized starch Nutrition 0.000 description 1
- 239000010893 paper waste Substances 0.000 description 1
- PQPFFKCJENSZKL-UHFFFAOYSA-N pentan-3-amine Chemical compound CCC(N)CC PQPFFKCJENSZKL-UHFFFAOYSA-N 0.000 description 1
- 229920001200 poly(ethylene-vinyl acetate) Polymers 0.000 description 1
- 239000004584 polyacrylic acid Substances 0.000 description 1
- 229940068917 polyethylene glycols Drugs 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 238000005185 salting out Methods 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 230000003381 solubilizing effect Effects 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000011115 styrene butadiene Substances 0.000 description 1
- 229920003048 styrene butadiene rubber Polymers 0.000 description 1
- 229920001909 styrene-acrylic polymer Polymers 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000001117 sulphuric acid Substances 0.000 description 1
- 235000011149 sulphuric acid Nutrition 0.000 description 1
- 239000004408 titanium dioxide Substances 0.000 description 1
- 238000000108 ultra-filtration Methods 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 239000011592 zinc chloride Substances 0.000 description 1
- 235000005074 zinc chloride Nutrition 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D251/00—Heterocyclic compounds containing 1,3,5-triazine rings
- C07D251/02—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings
- C07D251/12—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
- C07D251/26—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with only hetero atoms directly attached to ring carbon atoms
- C07D251/40—Nitrogen atoms
- C07D251/54—Three nitrogen atoms
- C07D251/68—Triazinylamino stilbenes
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Paper (AREA)
- Photoreceptors In Electrophotography (AREA)
- Luminescent Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Detergent Compositions (AREA)
- Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
- Optical Fibers, Optical Fiber Cores, And Optical Fiber Bundles (AREA)
- Glass Compositions (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP04015099A EP1612209A1 (en) | 2004-06-28 | 2004-06-28 | Improvements relating to optical brightening agents |
| EP04015099.7 | 2004-06-28 | ||
| PCT/EP2005/052960 WO2006000573A1 (en) | 2004-06-28 | 2005-06-24 | Improvements relating to optical brightening agents |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2562777A1 CA2562777A1 (en) | 2006-01-05 |
| CA2562777C true CA2562777C (en) | 2013-08-06 |
Family
ID=34925510
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2562777A Expired - Fee Related CA2562777C (en) | 2004-06-28 | 2005-06-24 | Improvements relating to optical brightening agents |
Country Status (14)
| Country | Link |
|---|---|
| US (1) | US7812156B2 (https=) |
| EP (2) | EP1612209A1 (https=) |
| JP (1) | JP4875615B2 (https=) |
| CN (1) | CN101094842B (https=) |
| AT (1) | ATE383346T1 (https=) |
| AU (1) | AU2005256643B2 (https=) |
| BR (1) | BRPI0510140B1 (https=) |
| CA (1) | CA2562777C (https=) |
| DE (1) | DE602005004290T2 (https=) |
| ES (1) | ES2296200T3 (https=) |
| NO (1) | NO20065773L (https=) |
| PT (1) | PT1763519E (https=) |
| WO (1) | WO2006000573A1 (https=) |
| ZA (1) | ZA200609273B (https=) |
Families Citing this family (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1712677A1 (en) * | 2005-04-08 | 2006-10-18 | Clariant International Ltd. | Aqueous solutions of optical brighteners |
| AU2014259497B2 (en) * | 2008-03-26 | 2016-05-12 | Archroma Ip Gmbh | Improved optical brightening compositions |
| WO2009118247A1 (en) * | 2008-03-26 | 2009-10-01 | Clariant International Ltd | Improved optical brightening compositions |
| EP2192231A1 (en) * | 2008-11-27 | 2010-06-02 | Clariant International Ltd. | Improved optical brightening compositions for high quality inkjet printing |
| ES2390932T5 (es) † | 2008-11-27 | 2020-09-14 | Archroma Ip Gmbh | Composiciones abrillantadoras ópticas para la impresión por chorro de tinta de alta calidad |
| WO2010060569A1 (en) * | 2008-11-27 | 2010-06-03 | Clariant International Ltd | Improved optical brightening compositions for high quality ink jet printing |
| CN102245719B (zh) * | 2008-12-08 | 2014-01-29 | 惠普开发有限公司 | 用于喷墨介质的表面涂料组合物 |
| WO2011066955A1 (en) * | 2009-12-02 | 2011-06-09 | Clariant International Ltd | Concentrated storage-stable aqueous optical brightening solutions |
| TWI506183B (zh) * | 2010-02-11 | 2015-11-01 | Clariant Finance Bvi Ltd | 於施漿壓印應用中用於調色光之水性上漿組成物 |
| EP2588666B1 (en) * | 2010-07-01 | 2018-08-08 | Archroma IP GmbH | Aqueous compositions for whitening and shading in coating applications |
| ITMI20112003A1 (it) * | 2011-11-04 | 2013-05-05 | 3V Sigma Spa | Composizioni di agenti sbiancanti fluorescenti |
| CN102964864B (zh) * | 2012-11-28 | 2013-12-25 | 华南师范大学 | 一种多功能呋喃酮荧光增白剂及其制备方法 |
| CN103205134B (zh) * | 2013-03-14 | 2014-04-23 | 浙江传化华洋化工有限公司 | 一种dsd酸三嗪类荧光增白剂的合成方法 |
| PT2781648E (pt) * | 2013-03-21 | 2016-03-07 | Clariant Int Ltd | Agentes de branqueamento ótico para impressão a jato de tinta de alta qualidade |
| US9109331B2 (en) * | 2013-11-07 | 2015-08-18 | Meng Jun Li | Fluorescent brighter #71 used for the papermaking process |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CH532686A (de) | 1968-07-10 | 1973-01-15 | Ciba Geigy Ag | Verwendung von Bis-s-triazinylamino-stilben-2,2'-disulfonsäuren zum optischen Aufhellen von nichttextilen Cellulosesubstraten |
| JPS5278235A (en) * | 1975-12-25 | 1977-07-01 | Showa Kagaku Kougiyou Kk | Process for manufacture of 4*4**bistriazinylaminoo stilbenee2*22disulfonic acid derivatives |
| JPS62106965A (ja) | 1985-11-05 | 1987-05-18 | Shin Nisso Kako Co Ltd | 螢光増白剤 |
| GB9412590D0 (en) * | 1994-06-23 | 1994-08-10 | Sandoz Ltd | Organic compounds |
| ATE244227T1 (de) * | 1997-03-25 | 2003-07-15 | Ciba Sc Holding Ag | 4,4'-diaminostilben-2,2'-disulfonsäurederivate |
| DE69920409T2 (de) * | 1998-02-20 | 2005-10-06 | Ciba Speciality Chemicals Holding Inc. | Verfahren zur herstellung von stilbenverbindungen |
| GB9930247D0 (en) | 1999-12-22 | 2000-02-09 | Clariant Int Ltd | Improvements in or relating to organic compounds |
| GB0100610D0 (en) | 2001-01-10 | 2001-02-21 | Clariant Int Ltd | Improvements in or relating to organic compounds |
| GB0127903D0 (en) * | 2001-11-21 | 2002-01-16 | Clariant Int Ltd | Improvements relating to organic compounds |
-
2004
- 2004-06-28 EP EP04015099A patent/EP1612209A1/en not_active Withdrawn
-
2005
- 2005-06-24 WO PCT/EP2005/052960 patent/WO2006000573A1/en not_active Ceased
- 2005-06-24 DE DE602005004290T patent/DE602005004290T2/de not_active Expired - Lifetime
- 2005-06-24 PT PT05756774T patent/PT1763519E/pt unknown
- 2005-06-24 CN CN2005800212004A patent/CN101094842B/zh not_active Expired - Fee Related
- 2005-06-24 AT AT05756774T patent/ATE383346T1/de active
- 2005-06-24 EP EP05756774A patent/EP1763519B1/en not_active Expired - Lifetime
- 2005-06-24 US US11/630,424 patent/US7812156B2/en active Active
- 2005-06-24 CA CA2562777A patent/CA2562777C/en not_active Expired - Fee Related
- 2005-06-24 AU AU2005256643A patent/AU2005256643B2/en not_active Ceased
- 2005-06-24 BR BRPI0510140-9A patent/BRPI0510140B1/pt not_active IP Right Cessation
- 2005-06-24 JP JP2007517302A patent/JP4875615B2/ja not_active Expired - Fee Related
- 2005-06-24 ES ES05756774T patent/ES2296200T3/es not_active Expired - Lifetime
-
2006
- 2006-11-07 ZA ZA200609273A patent/ZA200609273B/en unknown
- 2006-12-13 NO NO20065773A patent/NO20065773L/no not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| BRPI0510140A (pt) | 2007-10-02 |
| AU2005256643A1 (en) | 2006-01-05 |
| ATE383346T1 (de) | 2008-01-15 |
| ES2296200T3 (es) | 2008-04-16 |
| BRPI0510140B1 (pt) | 2014-05-20 |
| JP2008505856A (ja) | 2008-02-28 |
| PT1763519E (pt) | 2008-04-08 |
| US7812156B2 (en) | 2010-10-12 |
| HK1116175A1 (en) | 2008-12-19 |
| US20070245503A1 (en) | 2007-10-25 |
| CN101094842B (zh) | 2010-11-03 |
| ZA200609273B (en) | 2008-06-25 |
| AU2005256643B2 (en) | 2011-10-13 |
| EP1612209A1 (en) | 2006-01-04 |
| NO20065773L (no) | 2007-01-29 |
| WO2006000573A1 (en) | 2006-01-05 |
| EP1763519A1 (en) | 2007-03-21 |
| DE602005004290T2 (de) | 2009-01-08 |
| CA2562777A1 (en) | 2006-01-05 |
| EP1763519B1 (en) | 2008-01-09 |
| DE602005004290D1 (de) | 2008-02-21 |
| JP4875615B2 (ja) | 2012-02-15 |
| CN101094842A (zh) | 2007-12-26 |
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