CA2320244A1 - Method for producing aqueous polymer dispersions containing colorants - Google Patents
Method for producing aqueous polymer dispersions containing colorants Download PDFInfo
- Publication number
- CA2320244A1 CA2320244A1 CA002320244A CA2320244A CA2320244A1 CA 2320244 A1 CA2320244 A1 CA 2320244A1 CA 002320244 A CA002320244 A CA 002320244A CA 2320244 A CA2320244 A CA 2320244A CA 2320244 A1 CA2320244 A1 CA 2320244A1
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- Prior art keywords
- dye
- alkyl
- monomers
- polymer
- formula
- Prior art date
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- 229920000642 polymer Polymers 0.000 title claims abstract 27
- 239000006185 dispersion Substances 0.000 title claims abstract 5
- 238000004519 manufacturing process Methods 0.000 title claims abstract 3
- 239000003086 colorant Substances 0.000 title abstract 7
- 239000000178 monomer Substances 0.000 claims abstract 42
- 238000000034 method Methods 0.000 claims abstract 16
- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 claims abstract 9
- CSHWQDPOILHKBI-UHFFFAOYSA-N peryrene Natural products C1=CC(C2=CC=CC=3C2=C2C=CC=3)=C3C2=CC=CC3=C1 CSHWQDPOILHKBI-UHFFFAOYSA-N 0.000 claims abstract 9
- 239000007764 o/w emulsion Substances 0.000 claims abstract 6
- 239000003999 initiator Substances 0.000 claims abstract 4
- 230000003287 optical effect Effects 0.000 claims abstract 4
- 239000000839 emulsion Substances 0.000 claims abstract 2
- 239000000975 dye Substances 0.000 claims 27
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 13
- 238000009472 formulation Methods 0.000 claims 13
- 239000000203 mixture Substances 0.000 claims 13
- 239000004815 dispersion polymer Substances 0.000 claims 11
- 229910052736 halogen Inorganic materials 0.000 claims 11
- 150000002367 halogens Chemical class 0.000 claims 11
- 229910052739 hydrogen Inorganic materials 0.000 claims 10
- 239000001257 hydrogen Substances 0.000 claims 9
- 125000003118 aryl group Chemical group 0.000 claims 8
- 150000001875 compounds Chemical class 0.000 claims 8
- 229920001577 copolymer Polymers 0.000 claims 8
- 150000002431 hydrogen Chemical group 0.000 claims 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims 8
- 239000002245 particle Substances 0.000 claims 7
- 229910052698 phosphorus Inorganic materials 0.000 claims 7
- 229910052717 sulfur Inorganic materials 0.000 claims 7
- 150000003839 salts Chemical class 0.000 claims 5
- 125000000217 alkyl group Chemical group 0.000 claims 4
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 claims 4
- 125000001841 imino group Chemical group [H]N=* 0.000 claims 4
- 239000011159 matrix material Substances 0.000 claims 4
- 125000004430 oxygen atom Chemical group O* 0.000 claims 4
- 125000004434 sulfur atom Chemical group 0.000 claims 4
- 125000004400 (C1-C12) alkyl group Chemical group 0.000 claims 3
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 3
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims 3
- -1 1,4-xylylene Chemical group 0.000 claims 3
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 claims 3
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims 3
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims 3
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 claims 3
- WHNWPMSKXPGLAX-UHFFFAOYSA-N N-Vinyl-2-pyrrolidone Chemical compound C=CN1CCCC1=O WHNWPMSKXPGLAX-UHFFFAOYSA-N 0.000 claims 3
- 239000007983 Tris buffer Substances 0.000 claims 3
- 239000002253 acid Substances 0.000 claims 3
- 125000002091 cationic group Chemical group 0.000 claims 3
- ZYGHJZDHTFUPRJ-UHFFFAOYSA-N coumarin Chemical compound C1=CC=C2OC(=O)C=CC2=C1 ZYGHJZDHTFUPRJ-UHFFFAOYSA-N 0.000 claims 3
- 125000004093 cyano group Chemical group *C#N 0.000 claims 3
- 125000000753 cycloalkyl group Chemical group 0.000 claims 3
- 239000000843 powder Substances 0.000 claims 3
- 150000003254 radicals Chemical class 0.000 claims 3
- 125000004916 (C1-C6) alkylcarbonyl group Chemical group 0.000 claims 2
- 125000002030 1,2-phenylene group Chemical group [H]C1=C([H])C([*:1])=C([*:2])C([H])=C1[H] 0.000 claims 2
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 claims 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 claims 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 claims 2
- 125000005129 aryl carbonyl group Chemical group 0.000 claims 2
- 235000001671 coumarin Nutrition 0.000 claims 2
- 238000004132 cross linking Methods 0.000 claims 2
- LPIQUOYDBNQMRZ-UHFFFAOYSA-N cyclopentene Chemical compound C1CC=CC1 LPIQUOYDBNQMRZ-UHFFFAOYSA-N 0.000 claims 2
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims 2
- 125000000524 functional group Chemical group 0.000 claims 2
- 125000001072 heteroaryl group Chemical group 0.000 claims 2
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims 2
- 150000002790 naphthalenes Chemical class 0.000 claims 2
- 230000007935 neutral effect Effects 0.000 claims 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 2
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 claims 1
- 150000000183 1,3-benzoxazoles Chemical class 0.000 claims 1
- 125000001140 1,4-phenylene group Chemical group [H]C1=C([H])C([*:2])=C([H])C([H])=C1[*:1] 0.000 claims 1
- FXNDIJDIPNCZQJ-UHFFFAOYSA-N 2,4,4-trimethylpent-1-ene Chemical compound CC(=C)CC(C)(C)C FXNDIJDIPNCZQJ-UHFFFAOYSA-N 0.000 claims 1
- 229920000536 2-Acrylamido-2-methylpropane sulfonic acid Polymers 0.000 claims 1
- XHZPRMZZQOIPDS-UHFFFAOYSA-N 2-Methyl-2-[(1-oxo-2-propenyl)amino]-1-propanesulfonic acid Chemical compound OS(=O)(=O)CC(C)(C)NC(=O)C=C XHZPRMZZQOIPDS-UHFFFAOYSA-N 0.000 claims 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims 1
- BCHZICNRHXRCHY-UHFFFAOYSA-N 2h-oxazine Chemical compound N1OC=CC=C1 BCHZICNRHXRCHY-UHFFFAOYSA-N 0.000 claims 1
- MXRGSJAOLKBZLU-UHFFFAOYSA-N 3-ethenylazepan-2-one Chemical compound C=CC1CCCCNC1=O MXRGSJAOLKBZLU-UHFFFAOYSA-N 0.000 claims 1
- 125000004649 C2-C8 alkynyl group Chemical group 0.000 claims 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims 1
- 230000002378 acidificating effect Effects 0.000 claims 1
- 150000001336 alkenes Chemical class 0.000 claims 1
- 125000000129 anionic group Chemical group 0.000 claims 1
- 239000001000 anthraquinone dye Substances 0.000 claims 1
- 125000004104 aryloxy group Chemical group 0.000 claims 1
- 239000000987 azo dye Substances 0.000 claims 1
- 239000003638 chemical reducing agent Substances 0.000 claims 1
- 239000011248 coating agent Substances 0.000 claims 1
- 238000000576 coating method Methods 0.000 claims 1
- 229960000956 coumarin Drugs 0.000 claims 1
- 150000004775 coumarins Chemical class 0.000 claims 1
- 125000000000 cycloalkoxy group Chemical group 0.000 claims 1
- 125000000596 cyclohexenyl group Chemical group C1(=CCCCC1)* 0.000 claims 1
- 238000009826 distribution Methods 0.000 claims 1
- 238000001035 drying Methods 0.000 claims 1
- 238000007720 emulsion polymerization reaction Methods 0.000 claims 1
- 125000005677 ethinylene group Chemical group [*:2]C#C[*:1] 0.000 claims 1
- 229920001519 homopolymer Polymers 0.000 claims 1
- 239000011256 inorganic filler Substances 0.000 claims 1
- 229910003475 inorganic filler Inorganic materials 0.000 claims 1
- PXZQEOJJUGGUIB-UHFFFAOYSA-N isoindolin-1-one Chemical compound C1=CC=C2C(=O)NCC2=C1 PXZQEOJJUGGUIB-UHFFFAOYSA-N 0.000 claims 1
- GWVMLCQWXVFZCN-UHFFFAOYSA-N isoindoline Chemical compound C1=CC=C2CNCC2=C1 GWVMLCQWXVFZCN-UHFFFAOYSA-N 0.000 claims 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 claims 1
- 239000011976 maleic acid Substances 0.000 claims 1
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 claims 1
- 125000005394 methallyl group Chemical group 0.000 claims 1
- 125000001434 methanylylidene group Chemical group [H]C#[*] 0.000 claims 1
- PSZYNBSKGUBXEH-UHFFFAOYSA-N naphthalene-1-sulfonic acid Chemical compound C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1 PSZYNBSKGUBXEH-UHFFFAOYSA-N 0.000 claims 1
- RGSFGYAAUTVSQA-UHFFFAOYSA-N pentamethylene Natural products C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 claims 1
- DGBWPZSGHAXYGK-UHFFFAOYSA-N perinone Chemical compound C12=NC3=CC=CC=C3N2C(=O)C2=CC=C3C4=C2C1=CC=C4C(=O)N1C2=CC=CC=C2N=C13 DGBWPZSGHAXYGK-UHFFFAOYSA-N 0.000 claims 1
- 150000002978 peroxides Chemical class 0.000 claims 1
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 1
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims 1
- 125000005575 polycyclic aromatic hydrocarbon group Chemical group 0.000 claims 1
- 150000004032 porphyrins Chemical class 0.000 claims 1
- 150000003220 pyrenes Chemical class 0.000 claims 1
- FYNROBRQIVCIQF-UHFFFAOYSA-N pyrrolo[3,2-b]pyrrole-5,6-dione Chemical compound C1=CN=C2C(=O)C(=O)N=C21 FYNROBRQIVCIQF-UHFFFAOYSA-N 0.000 claims 1
- 125000001453 quaternary ammonium group Chemical group 0.000 claims 1
- GGVMPKQSTZIOIU-UHFFFAOYSA-N quaterrylene Chemical group C12=C3C4=CC=C2C(C2=C56)=CC=C5C(C=57)=CC=CC7=CC=CC=5C6=CC=C2C1=CC=C3C1=CC=CC2=CC=CC4=C21 GGVMPKQSTZIOIU-UHFFFAOYSA-N 0.000 claims 1
- 150000001629 stilbenes Chemical class 0.000 claims 1
- 235000021286 stilbenes Nutrition 0.000 claims 1
- 125000001424 substituent group Chemical group 0.000 claims 1
- 229920001897 terpolymer Polymers 0.000 claims 1
- BIGSSBUECAXJBO-UHFFFAOYSA-N terrylene Chemical group C12=C3C4=CC=C2C(C=25)=CC=CC5=CC=CC=2C1=CC=C3C1=CC=CC2=CC=CC4=C21 BIGSSBUECAXJBO-UHFFFAOYSA-N 0.000 claims 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 claims 1
- 238000002604 ultrasonography Methods 0.000 claims 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims 1
- 229920002554 vinyl polymer Polymers 0.000 claims 1
- 229920003176 water-insoluble polymer Polymers 0.000 claims 1
- 229920003169 water-soluble polymer Polymers 0.000 claims 1
- 239000012463 white pigment Substances 0.000 claims 1
- 238000002360 preparation method Methods 0.000 abstract 2
- 239000000049 pigment Substances 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F2/00—Processes of polymerisation
- C08F2/32—Polymerisation in water-in-oil emulsions
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F2/00—Processes of polymerisation
- C08F2/44—Polymerisation in the presence of compounding ingredients, e.g. plasticisers, dyestuffs, fillers
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K3/00—Use of inorganic substances as compounding ingredients
-
- 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
- C09B69/00—Dyes not provided for by a single group of this subclass
- C09B69/10—Polymeric dyes; Reaction products of dyes with monomers or with macromolecular compounds
- C09B69/101—Polymeric dyes; Reaction products of dyes with monomers or with macromolecular compounds containing an anthracene dye
- C09B69/102—Polymeric dyes; Reaction products of dyes with monomers or with macromolecular compounds containing an anthracene dye containing a perylene dye
Abstract
The invention relates to a method for producing aqueous polymer dispersions containing colorants by radical aqueous emulsion polymerisation of ethylenically unsaturated monomers in the presence of radical-forming initiators. At least a proportion of the monomers is used in the form of an oil-in-water emulsion E1 whose disperse phase contains at least one oilsoluble colorant. The inventive method is characterised in that the disperse phase of E1 is essentially made up of colorant-containing monomer droplets with a diameter < 500 nm. The invention also relates to perylene colorants of general formula (III) in accordance with claim 35, and to colorant-containing preparations which contain the inventive colorant-containing polymers and pigment-containing preparations which contain an inventive polymer with an optical brightener.
Claims (40)
1. A process for preparing dye-comprising aqueous polymer dispersions by aqueous emulsion polymerization of ethylenically unsaturated monomers in the presence of free-radical initiators, in which process at least some of the monomers are employed in the form of an oil-in-water emulsion E1 whose disperse phase comprises at least one oil-soluble dye, wherein the disperse phase of E1 is formed essentially of dye-comprising monomer droplets having a diameter < 500 nm.
2. A process as claimed in claim 1, wherein the ethylenically unsaturated monomers comprise at least one monoethylenically unsaturated monomer A having a water solubility > 0.01 g/l and at least one monoethylenically unsaturated monomer B
having a water solubility < 0.01 g/l.
having a water solubility < 0.01 g/l.
3. A process as claimed in either of the preceding claims, wherein the oil droplets of the oil-in-water emulsion E1 comprise a noncopolymerizable compound B' having a water solubility < 0.01 g/l.
4. A process as claimed in any of the preceding claims, wherein the ethylenically unsaturated monomers comprise at least one monomer C which has at least two nonconjugated double bonds.
5. A process as claimed in any of the preceding claims, wherein the ethylenically unsaturated monomers comprise at least one monoethylenically unsaturated monomer D which is different from the monomers C and has a crosslinking action.
6. A process as claimed in any of the preceding claims, wherein the oil-soluble dye is selected from oil-soluble derivatives of naphthalene, perylene, terrylene, quaterrylene, diketopyrrolopyrrole, from perinone dyes, coumarin dyes, oxazine dyes, anthracene dyes, azo dyes, anthraquinone dyes, methine dyes, azamethine dyes, isoindoline dyes and isoindolinone dyes, porphyrins, phthalocyanines and naphthalocyanines.
7. A process as claimed in any of the preceding claims, wherein the oil-soluble dye is an optical brightener.
8. A process as claimed in claim 7, wherein the optical brightener is selected from compounds from the classes of the bisstyrylbenzenes, stilbenes, benzoxazoles, coumarins, pyrenes and naphthalenes.
9. A process as claimed in any of the preceding claims, wherein the oil-soluble dye has at least one copolymerizable, ethylenically unsaturated double bond which does not belong to the chromophore of the dye.
10. A process as claimed in claim 9, wherein the oil-soluble organic dye is selected from perylene dyes of the formula III
in which one or two of the groups X1 to X4, Y1 to Y4 is or are a radical of the formula IV
~X~S~P (IV) in which X is selected from a single bond, ethynylene or -(CH2)k-X'- where k = 0, 1, 2, 3 or 4 and X' is selected from -O-;
-N(R)-; -S-; -O-C(O)-; -O-C(O)-O-; -O-C(O)-N(R')-;
-N(R')-C(O)-; -N(R')-C(O)-O-; -N(R')-C(O)-N(R")-; -C(O)-;
-C(O)-O-; -C(O)-N(R')-; -S(O)2-O-; -S(O)2-N(R')-;
-O-S(O)2-; -N(R')-S(O)2-;
in which R is hydrogen, linear or branched C1-C6-alkyl, aryl, aryl-C1-C6-alkyl, C1-C6-alkylcarbonyl, arylcarbonyl or formyl and R', R" independently of one another are hydrogen, linear or branched C1-C6-alkyl, aryl or aryl-C1-C6-alkyl which are optionally substituted by OH, halogen, C1-C4-alkyl or C1-C4-alkyloxy, S is selected from a single bond, C1-C12-alkylene which can be interrupted by one or more nonadjacent oxygen atoms, sulfur atoms or (alkyl)imino groups, or is 1,2-, 1,3- or 1,4-phenylene which optionally has one or two substituents selected from C1-C4-alkyl, C1-C4-alkyloxy or halogen, or is 1,2-, 1,3- or 1,4-xylylene which is optionally substituted as for phenylene, and P is a polymerizable group of the formula II
in which A and B independently of one another are hydrogen, C1-C6-alkyl or phenyl, or A and B together with the double bond to which they are attached form a cyclopentene or cyclohexene ring, m is 0, 1, 2 or 3, and Z is a single bond or possesses one of the definitions indicated above for X', or X1 together with X4 and/or X2 together with X3 are a group of the formula V
in which S and P possess one of the above-mentioned definitions, and the remaining groups X1 to X4, Y1 to Y4 independently of one another are selected from hydrogen, linear or branched C1-C12-alkyl which can if desired be interrupted by one or more nonadjacent oxygen atoms, sulfur atoms or by (alkyl)imino groups and/or can be substituted by OH and/or halogen, or are cycloalkyl, heterocycloalkyl, aryl, hetaryl, aryl-C1-C6-alkyl, hetaryl-C1-C6-alkyl, C2-C18-alkynyl, arylethynyl, tris(C1-C4-alkyl)silylethynyl, cyano, nitro, halogen;
and/or atomic groups selected from:
-O-R; -O-C(O)-R'; -N(R')-C(O)-R''; -NRR'; -C(O)-R; -C(O)-OR';
-C(O)-NR'R''; -N(R')-C(O)-OR; -N(R')C(O)-NR'R", -O-S(O)2-R, -N(R')-S(O)2-R'', in which R, R' and R" have the definitions indicated above, the remaining groups X1 together with X4 and/or X2 together with X3 can furthermore be -X"-C(O)-, -C(O)-N(R''')-C(O)- or -C(O)-O-C(O)-, in which R''' has the definitions indicated for R' and X" is -CH=CH-, 1,2-phenylene, 1,2-naphthylene, 2,3-naphthylene or 2,3-pyridinylene, each of which is unsubstituted or substituted once or twice by C1-C4-alkylene, C1-C4-alkoxy or halogen.
in which one or two of the groups X1 to X4, Y1 to Y4 is or are a radical of the formula IV
~X~S~P (IV) in which X is selected from a single bond, ethynylene or -(CH2)k-X'- where k = 0, 1, 2, 3 or 4 and X' is selected from -O-;
-N(R)-; -S-; -O-C(O)-; -O-C(O)-O-; -O-C(O)-N(R')-;
-N(R')-C(O)-; -N(R')-C(O)-O-; -N(R')-C(O)-N(R")-; -C(O)-;
-C(O)-O-; -C(O)-N(R')-; -S(O)2-O-; -S(O)2-N(R')-;
-O-S(O)2-; -N(R')-S(O)2-;
in which R is hydrogen, linear or branched C1-C6-alkyl, aryl, aryl-C1-C6-alkyl, C1-C6-alkylcarbonyl, arylcarbonyl or formyl and R', R" independently of one another are hydrogen, linear or branched C1-C6-alkyl, aryl or aryl-C1-C6-alkyl which are optionally substituted by OH, halogen, C1-C4-alkyl or C1-C4-alkyloxy, S is selected from a single bond, C1-C12-alkylene which can be interrupted by one or more nonadjacent oxygen atoms, sulfur atoms or (alkyl)imino groups, or is 1,2-, 1,3- or 1,4-phenylene which optionally has one or two substituents selected from C1-C4-alkyl, C1-C4-alkyloxy or halogen, or is 1,2-, 1,3- or 1,4-xylylene which is optionally substituted as for phenylene, and P is a polymerizable group of the formula II
in which A and B independently of one another are hydrogen, C1-C6-alkyl or phenyl, or A and B together with the double bond to which they are attached form a cyclopentene or cyclohexene ring, m is 0, 1, 2 or 3, and Z is a single bond or possesses one of the definitions indicated above for X', or X1 together with X4 and/or X2 together with X3 are a group of the formula V
in which S and P possess one of the above-mentioned definitions, and the remaining groups X1 to X4, Y1 to Y4 independently of one another are selected from hydrogen, linear or branched C1-C12-alkyl which can if desired be interrupted by one or more nonadjacent oxygen atoms, sulfur atoms or by (alkyl)imino groups and/or can be substituted by OH and/or halogen, or are cycloalkyl, heterocycloalkyl, aryl, hetaryl, aryl-C1-C6-alkyl, hetaryl-C1-C6-alkyl, C2-C18-alkynyl, arylethynyl, tris(C1-C4-alkyl)silylethynyl, cyano, nitro, halogen;
and/or atomic groups selected from:
-O-R; -O-C(O)-R'; -N(R')-C(O)-R''; -NRR'; -C(O)-R; -C(O)-OR';
-C(O)-NR'R''; -N(R')-C(O)-OR; -N(R')C(O)-NR'R", -O-S(O)2-R, -N(R')-S(O)2-R'', in which R, R' and R" have the definitions indicated above, the remaining groups X1 together with X4 and/or X2 together with X3 can furthermore be -X"-C(O)-, -C(O)-N(R''')-C(O)- or -C(O)-O-C(O)-, in which R''' has the definitions indicated for R' and X" is -CH=CH-, 1,2-phenylene, 1,2-naphthylene, 2,3-naphthylene or 2,3-pyridinylene, each of which is unsubstituted or substituted once or twice by C1-C4-alkylene, C1-C4-alkoxy or halogen.
11. A process as claimed in any of the preceding claims, wherein the initiator is soluble in water.
12. A process as claimed in claim 11, wherein the water-soluble initiator comprises a nonionic peroxide, especially hydrogen peroxide, and, if desired, one or more reducing agents.
13. A process as claimed in any of the preceding claims, wherein the dye-comprising monomer droplets of the oil-in-water emulsion E1 have an average diameter ~ z in the range from 100 to 400 nm.
14. A process as claimed in any of the preceding claims, wherein the oil-in-water emulsion E1 is prepared by homogenizing a conventional, dye-comprising oil-in-water emulsion of the monomers by means of ultrasound, the dye in the monomer droplets of the conventional emulsion being in dissolved or molecularly disperse form.
15. A dye-comprising aqueous polymer dispersion in which the polymer particles have an average diameter d z < 1000 nm and comprise at least 0.01% by weight of at least one oil-soluble dye in molecularly disperse form and which, furthermore, is composed of at least one monoethylenically unsaturated monomer A having a water solubility > 0.01 g/1 and at least one further, polymerization-active compound which is selected from - monoethylenically unsaturated monomers B having a water solubility < 0.01 g/l, - monomers C which have at least two nonconjugated, ethylenically unsaturated double bonds, - crosslinking monomers D, and - copolymerizable dyes from either of claims 9 and 10, except for those dye-comprising aqueous polymer dispersions which contain up to 3% by weight, based on the polymer matrix, of a polycyclic aromatic hydrocarbon, selected from naphthalene, anthracene and their substituted aromatic derivatives.
16. A dye-comprising aqueous polymer dispersion as claimed in claim 15, wherein the polymeric matrix formed from the copolymerized monomers A, B and, if desired, C and D is composed of - from 50 to 99.5% by weight of monomers A, - from 0.5 to 50% by weight of monomers B, - from 0 to 30% by weight of monomers C, and - from 0 to 30% by weight of monomers D
17. A dye-comprising aqueous polymer dispersion as claimed in claim 15 or 16, comprising at least one noncopolymerizable dye, wherein the polymer matrix comprises, in copolymerized form, at least one compound selected from the monomers C and the compounds D, in amounts of > 0.1% by weight, based on the polymer matrix.
18. A dye-comprising aqueous polymer dispersion as claimed in any of claims 15 to 17, comprising at least one copolymerizable dye from either of claims 9 and 10.
19. A dye-comprising aqueous polymer dispersion as claimed in any of claims 15 to 18, wherein the polymer particles have a monomodal particle size distribution with an average particle diameter d2 in the range from 100 to 400 nm.
20. A dye-comprising aqueous polymer dispersion as claimed in any of claims 15 to 19, wherein the monomers A copolymerized in the polymer particles comprise - from 0.5 to 30% by weight of at least one monomer A1 having a water solubility > 60 g/l (in each case at 25°C
and 1 atm), based on the total monomer amount, and - from 70 to 99.5% by weight of at least one monomer A2 having a water solubility < 60 g/l (in each case at 25°C
and 1 atm), based on the total monomer amount.
and 1 atm), based on the total monomer amount, and - from 70 to 99.5% by weight of at least one monomer A2 having a water solubility < 60 g/l (in each case at 25°C
and 1 atm), based on the total monomer amount.
21. A dye-comprising aqueous polymer dispersion as claimed in claim 20, wherein the monomers A2 are selected from monoethylenically unsaturated cationic monomers.
22. A dye-comprising aqueous polymer dispersion as claimed in claim 20, wherein the momomers A2 are selected from monoethylenically unsaturated monomers which have at least one acid group, possibly in deprotonated form.
23. A dye-comprising polymer powder obtainable by drying an aqueous polymer dispersion as claimed in any of claims 15 to 22.
24. An aqueous dye-comprising formulation comprising:
i. at least one dye-comprising polymer which is present in the formulation in the form of dispersed polymer particles and is selected from the polymers present in the aqueous, dye-comprising polymer dispersion as claimed in any of claims 15 to 22, and the polymer powder as claimed in claim 23 and ii. customary auxiliaries.
i. at least one dye-comprising polymer which is present in the formulation in the form of dispersed polymer particles and is selected from the polymers present in the aqueous, dye-comprising polymer dispersion as claimed in any of claims 15 to 22, and the polymer powder as claimed in claim 23 and ii. customary auxiliaries.
25. A formulation as claimed in claim 24, additionally comprising at least one water-soluble polymer PW.
26. A formulation as claimed in claim 25, wherein the polymer PW
has cationic groups.
has cationic groups.
27. A formulation as claimed in claim 26, wherein the polymer PW
is a copolymer which is composed of at least one monoethylenically unsaturated, cationic monomer, especially a monomer having at least one quaternary ammonium or immonium group, and at least one further, neutral monomer.
is a copolymer which is composed of at least one monoethylenically unsaturated, cationic monomer, especially a monomer having at least one quaternary ammonium or immonium group, and at least one further, neutral monomer.
28. A formulation as claimed in claim 27, wherein the polymer PW
is selected from:
- copolymers of 1-vinylpyrrolidone with 1-vinyl-3-alkylimidazolium salts, - copolymers of 1-vinylpyrrolidone with methacryloyloxyethyltrialkylammonium salts, - terpolymers of vinylpyrrolidone and vinylcaprolactam with 1-vinyl-3-alkylimidazolium salts.
is selected from:
- copolymers of 1-vinylpyrrolidone with 1-vinyl-3-alkylimidazolium salts, - copolymers of 1-vinylpyrrolidone with methacryloyloxyethyltrialkylammonium salts, - terpolymers of vinylpyrrolidone and vinylcaprolactam with 1-vinyl-3-alkylimidazolium salts.
29. A formulation as claimed in claim 25, wherein the polymer PW
has acidic functional groups and/or anionic functional groups.
has acidic functional groups and/or anionic functional groups.
30. A formulation as claimed in claim 29, wherein the polymer PW
is a copolymer composed of - at least one monoethylenically unsaturated monomer MA
selected from monomers having at least one acid group and salts thereof, and - at least one further, neutral monomer.
is a copolymer composed of - at least one monoethylenically unsaturated monomer MA
selected from monomers having at least one acid group and salts thereof, and - at least one further, neutral monomer.
31. A formulation as claimed in claim 29 or 30, wherein the polymer PW is selected from - homopolymers and copolymers of 2-acrylamido-2-methylpropanesulfonic acid, - copolymers of acrylic acid and/or of methacrylic acid with styrene, - copolymers of acrylic acid and/or of methacrylic acid with C1-C10-alkyl esters of acrylic acid and/or of methacrylic acid, - copolymers of maleic acid or of maleic anhydride with olefins, especially with diisobutene, - the formaldehyde condensates of an arylsulfonic acid, especially a naphthalenesulfonic acid and salts thereof.
32. The use of an aqueous, dye-comprising formulation as claimed in any of claims 24 to 31 as an ink, especially for the inkjet process.
33. An aqueous pigmented formulation comprising i. at least one dye-comprising polymer which is present in the formulation in the form of dispersed polymer particles and is selected from the polymers of the aqueous dye-comprising polymer dispersion as claimed in any of claims 15 to 22 and from the polymer powder as claimed in claim 23, and whose oil-soluble dye comprises at least one optical brightener, ii. at least one dye-free, film-forming water-insoluble polymer which is composed of ethylenically unsaturated monomers, in the form of its aqueous dispersion, iii. at least one inorganic white pigment alone or together with an inorganic filler, and iv. auxiliaries.
34. The use of a formulation as claimed in claim 33 as a paper coating slip.
35. A perylene dye of the formula III
in which one or two of the groups X1 to X4, Y1 to Y4 is or are a radical of the formula IV
~X~S~P (IV) in which X, S and P possess the meanings as defined in claim 10, or X1 together with X4 or X2 together with X3 is a group of the formula V
in which S and P possess the meanings as defined in claim 10, and the remaining groups X1 to X4, Y1 to Y4 independently of one another are selected from hydrogen, linear or branched C1-C12-alkyl which can if desired be interrupted by one or more nonadjacent oxygen atoms, sulfur atoms or by (alkyl)imino groups and/or can be substituted by OH and/or halogen, or are cycloalkyl, heterocycloalkyl, aryl, hetaryl, aryl-C1-C6-alkyl, hetaryl-C1-C6-alkyl, C2-C18-alkynyl, arylethynyl, tris(C1-C4-alkyl)silylethynyl, cyano, nitro, halogen;
and/or atomic groups selected from:
-O-R; -O-C(O)-R'; -N(R')-C(O)-R"; -NRR'; -C(O)-R; -C(O)-OR';
-C(O)-NR'R"; -N(R')-C(O)-OR; -N(R')C(O)-NR'R", -O-S(O)2-R, -N(R')-S(O)2-R" , in which R is hydrogen, linear or branched C1-C6-alkyl, aryl, aryl-C1-C6-alkyl, C1-C6-alkylcarbonyl, arylcarbonyl or formyl and R' and R" independently of one another are hydrogen, linear or branched C1-C6-alkyl, aryl, or aryl-C1-C6-alkyl which may be substituted by OH, halogen, C1-C4-alkyl or C1-C4-alkoxy, the remaining groups X1 together with X4 and/or X2 together with X3 can furthermore be -X"-C(O)-, -C(O)-N(R"')-C(O)- or -C(O)-O-C(O)-, in which R"' has the definitions indicated for R' and X" is -CH=CH-, 1,2-phenylene, 1,2-naphthylene, 2,3-naphthylene or 2,3-pyridinylene, each of which is unsubstituted or substituted once or twice by C1-C4-alkylene, C1-C4-alkoxy or halogen, except for those compounds of formula III, in which X1 together with X4 is a group of the formula V as defined in claim 10 and X2 together with X3 is a group of the formula -C(O)-N(R"')-C(O)-, further except for those compounds of the formula III, in which X1 is a radical of the formula -X-S-P and X2, X3, X4 and Y1 to Y4 are all hydrogen.
in which one or two of the groups X1 to X4, Y1 to Y4 is or are a radical of the formula IV
~X~S~P (IV) in which X, S and P possess the meanings as defined in claim 10, or X1 together with X4 or X2 together with X3 is a group of the formula V
in which S and P possess the meanings as defined in claim 10, and the remaining groups X1 to X4, Y1 to Y4 independently of one another are selected from hydrogen, linear or branched C1-C12-alkyl which can if desired be interrupted by one or more nonadjacent oxygen atoms, sulfur atoms or by (alkyl)imino groups and/or can be substituted by OH and/or halogen, or are cycloalkyl, heterocycloalkyl, aryl, hetaryl, aryl-C1-C6-alkyl, hetaryl-C1-C6-alkyl, C2-C18-alkynyl, arylethynyl, tris(C1-C4-alkyl)silylethynyl, cyano, nitro, halogen;
and/or atomic groups selected from:
-O-R; -O-C(O)-R'; -N(R')-C(O)-R"; -NRR'; -C(O)-R; -C(O)-OR';
-C(O)-NR'R"; -N(R')-C(O)-OR; -N(R')C(O)-NR'R", -O-S(O)2-R, -N(R')-S(O)2-R" , in which R is hydrogen, linear or branched C1-C6-alkyl, aryl, aryl-C1-C6-alkyl, C1-C6-alkylcarbonyl, arylcarbonyl or formyl and R' and R" independently of one another are hydrogen, linear or branched C1-C6-alkyl, aryl, or aryl-C1-C6-alkyl which may be substituted by OH, halogen, C1-C4-alkyl or C1-C4-alkoxy, the remaining groups X1 together with X4 and/or X2 together with X3 can furthermore be -X"-C(O)-, -C(O)-N(R"')-C(O)- or -C(O)-O-C(O)-, in which R"' has the definitions indicated for R' and X" is -CH=CH-, 1,2-phenylene, 1,2-naphthylene, 2,3-naphthylene or 2,3-pyridinylene, each of which is unsubstituted or substituted once or twice by C1-C4-alkylene, C1-C4-alkoxy or halogen, except for those compounds of formula III, in which X1 together with X4 is a group of the formula V as defined in claim 10 and X2 together with X3 is a group of the formula -C(O)-N(R"')-C(O)-, further except for those compounds of the formula III, in which X1 is a radical of the formula -X-S-P and X2, X3, X4 and Y1 to Y4 are all hydrogen.
36. A perylene dye as claimed in claim 35, of the formula III, in which X1, X3 and X4 independently of one another are selected from hydrogen, linear or branched C1-C12-alkyl which can be uninterrupted or interrupted by one or more nonadjacent oxygen atoms, sulfur atoms or by (alkyl)imino groups and/or can be unsubstituted or substituted by OH and/or halogen, and from cycloalkyl, cycloalkyloxy, C2-C8-alkynyl, tris(C1-C4-alkyl)silylethynyl, aryl, aryloxy, halogen and cyano, X2 is a group of the formula IV
~X~S~P (IV) in which X, S and P are as defined in claim 10, and Y1 to Y4 possess the definitions indicated in claim 10 other than -X-S-P.
~X~S~P (IV) in which X, S and P are as defined in claim 10, and Y1 to Y4 possess the definitions indicated in claim 10 other than -X-S-P.
37. A perylene dye as claimed in claim 35, in which X1 together with X4 is -C(O)-N(R"')-C(O)- or -C(O)-O-C(O)- in which R"' is as defined in claim 10, X2 is a group of the formula IV
~X~S~P (IV) in which X, S and P are as defined in claim 10 and X3, Y1 to Y4 have the definitions indicated in claim 10 other than X-S-P.
~X~S~P (IV) in which X, S and P are as defined in claim 10 and X3, Y1 to Y4 have the definitions indicated in claim 10 other than X-S-P.
38. A perylene dye as claimed in claim 35, in which X2 together with X3 is a group of the formula V
in which S and P are as defined in claim 10, and X1, X4 and Y1 to Y4 are as defined in claim 10 other than -X-S-P.
in which S and P are as defined in claim 10, and X1, X4 and Y1 to Y4 are as defined in claim 10 other than -X-S-P.
39. A perylene dye of the formula III, in which X1 together with X4 and X3 together with X2 are a group of the formula V
in which S and P are as defined in claim 10 and Y1 to Y4 have the definitions indicated in claim 10 other than -X-S-P, except for those compounds, in which Y1=Y2=Y3=Y4 are H, Cl or phenoxy.
in which S and P are as defined in claim 10 and Y1 to Y4 have the definitions indicated in claim 10 other than -X-S-P, except for those compounds, in which Y1=Y2=Y3=Y4 are H, Cl or phenoxy.
40. A perylene dye as claimed in any of claims 35 to 39, in which P in formula (IV) or (V) is vinyl, allyl, methallyl, acrylamido, methacrylamido, acryloxy, methacryloxy, 3-vinylureido, 3-allylureido, 3-methallylureido, N-vinylaminocarbonyloxy, N-allylaminocarbonyloxy or N-methallylaminocarbonyloxy.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19805121.2 | 1998-02-09 | ||
| DE19805121A DE19805121A1 (en) | 1998-02-09 | 1998-02-09 | Process for the preparation of dye-containing, aqueous polymer dispersions |
| PCT/EP1999/000157 WO1999040123A2 (en) | 1998-02-09 | 1999-01-13 | Method for producing aqueous polymer dispersions containing colorants |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2320244A1 true CA2320244A1 (en) | 1999-08-12 |
| CA2320244C CA2320244C (en) | 2009-11-10 |
Family
ID=7857095
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002320244A Expired - Fee Related CA2320244C (en) | 1998-02-09 | 1999-01-13 | Method for producing aqueous polymer dispersions containing colorants |
Country Status (9)
| Country | Link |
|---|---|
| US (2) | US6727318B1 (en) |
| EP (1) | EP1054907B1 (en) |
| JP (1) | JP4383657B2 (en) |
| KR (1) | KR20010040768A (en) |
| CN (1) | CN100357326C (en) |
| CA (1) | CA2320244C (en) |
| DE (2) | DE19805121A1 (en) |
| ES (1) | ES2220045T3 (en) |
| WO (1) | WO1999040123A2 (en) |
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- 1999-01-13 WO PCT/EP1999/000157 patent/WO1999040123A2/en active IP Right Grant
- 1999-01-13 DE DE59909181T patent/DE59909181D1/en not_active Expired - Lifetime
- 1999-01-13 CA CA002320244A patent/CA2320244C/en not_active Expired - Fee Related
- 1999-01-13 US US09/600,868 patent/US6727318B1/en not_active Expired - Fee Related
- 1999-01-13 KR KR1020007008657A patent/KR20010040768A/en not_active Application Discontinuation
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- 1999-01-13 CN CNB998041947A patent/CN100357326C/en not_active Expired - Fee Related
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| ES2220045T3 (en) | 2004-12-01 |
| US20050075453A1 (en) | 2005-04-07 |
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| WO1999040123A2 (en) | 1999-08-12 |
| EP1054907A2 (en) | 2000-11-29 |
| DE59909181D1 (en) | 2004-05-19 |
| KR20010040768A (en) | 2001-05-15 |
| WO1999040123A3 (en) | 1999-10-28 |
| US6727318B1 (en) | 2004-04-27 |
| EP1054907B1 (en) | 2004-04-14 |
| CN100357326C (en) | 2007-12-26 |
| JP2002502893A (en) | 2002-01-29 |
| CN1293680A (en) | 2001-05-02 |
| DE19805121A1 (en) | 1999-08-12 |
| JP4383657B2 (en) | 2009-12-16 |
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