CA2394660A1 - Comb polymers from atrp macromonomers - Google Patents
Comb polymers from atrp macromonomers Download PDFInfo
- Publication number
- CA2394660A1 CA2394660A1 CA002394660A CA2394660A CA2394660A1 CA 2394660 A1 CA2394660 A1 CA 2394660A1 CA 002394660 A CA002394660 A CA 002394660A CA 2394660 A CA2394660 A CA 2394660A CA 2394660 A1 CA2394660 A1 CA 2394660A1
- Authority
- CA
- Canada
- Prior art keywords
- acrylic
- acid
- salts
- alkyl esters
- alkylacrylic
- 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.)
- Abandoned
Links
- 229920000642 polymer Polymers 0.000 title claims abstract description 131
- 239000000203 mixture Substances 0.000 claims abstract description 107
- 239000000049 pigment Substances 0.000 claims abstract description 58
- 238000000034 method Methods 0.000 claims abstract description 56
- 239000002245 particle Substances 0.000 claims abstract description 12
- 239000012860 organic pigment Substances 0.000 claims abstract description 9
- 239000001023 inorganic pigment Substances 0.000 claims abstract description 7
- 238000010560 atom transfer radical polymerization reaction Methods 0.000 claims abstract 4
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims description 145
- 239000000178 monomer Substances 0.000 claims description 86
- 150000003839 salts Chemical class 0.000 claims description 76
- -1 arene sulphonyl chlorides Chemical class 0.000 claims description 72
- 239000002253 acid Substances 0.000 claims description 64
- 239000003999 initiator Substances 0.000 claims description 59
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 claims description 41
- 229920001577 copolymer Polymers 0.000 claims description 36
- 239000012634 fragment Substances 0.000 claims description 36
- 239000006185 dispersion Substances 0.000 claims description 27
- 239000003054 catalyst Substances 0.000 claims description 25
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 24
- 150000008064 anhydrides Chemical class 0.000 claims description 22
- 238000002360 preparation method Methods 0.000 claims description 22
- 230000008569 process Effects 0.000 claims description 21
- 239000011230 binding agent Substances 0.000 claims description 20
- LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 20
- 150000002148 esters Chemical class 0.000 claims description 17
- 239000007788 liquid Substances 0.000 claims description 17
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 14
- 150000003440 styrenes Chemical class 0.000 claims description 14
- PNEYBMLMFCGWSK-UHFFFAOYSA-N Alumina Chemical compound [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 claims description 13
- 150000001408 amides Chemical class 0.000 claims description 13
- 125000000623 heterocyclic group Chemical group 0.000 claims description 13
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 12
- 229920002554 vinyl polymer Polymers 0.000 claims description 12
- 239000003795 chemical substances by application Substances 0.000 claims description 11
- 239000003960 organic solvent Substances 0.000 claims description 11
- 229910052723 transition metal Inorganic materials 0.000 claims description 11
- AGBXYHCHUYARJY-UHFFFAOYSA-N 2-phenylethenesulfonic acid Chemical compound OS(=O)(=O)C=CC1=CC=CC=C1 AGBXYHCHUYARJY-UHFFFAOYSA-N 0.000 claims description 10
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 claims description 10
- 150000003624 transition metals Chemical class 0.000 claims description 10
- XUDBVJCTLZTSDC-UHFFFAOYSA-N 2-ethenylbenzoic acid Chemical compound OC(=O)C1=CC=CC=C1C=C XUDBVJCTLZTSDC-UHFFFAOYSA-N 0.000 claims description 9
- LBSXSAXOLABXMF-UHFFFAOYSA-N 4-Vinylaniline Chemical compound NC1=CC=C(C=C)C=C1 LBSXSAXOLABXMF-UHFFFAOYSA-N 0.000 claims description 9
- GYCMBHHDWRMZGG-UHFFFAOYSA-N Methylacrylonitrile Chemical compound CC(=C)C#N GYCMBHHDWRMZGG-UHFFFAOYSA-N 0.000 claims description 9
- 125000001931 aliphatic group Chemical group 0.000 claims description 9
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 claims description 9
- 238000006116 polymerization reaction Methods 0.000 claims description 9
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 claims description 8
- 229920000180 alkyd Polymers 0.000 claims description 8
- 238000001035 drying Methods 0.000 claims description 8
- 230000000977 initiatory effect Effects 0.000 claims description 8
- ZQXSMRAEXCEDJD-UHFFFAOYSA-N n-ethenylformamide Chemical compound C=CNC=O ZQXSMRAEXCEDJD-UHFFFAOYSA-N 0.000 claims description 7
- 239000000654 additive Substances 0.000 claims description 6
- 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 claims description 6
- 239000003381 stabilizer Substances 0.000 claims description 6
- 239000004814 polyurethane Substances 0.000 claims description 5
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 claims description 4
- QDOXWKRWXJOMAK-UHFFFAOYSA-N dichromium trioxide Chemical compound O=[Cr]O[Cr]=O QDOXWKRWXJOMAK-UHFFFAOYSA-N 0.000 claims description 4
- 239000004014 plasticizer Substances 0.000 claims description 4
- 229920000058 polyacrylate Polymers 0.000 claims description 4
- 239000004094 surface-active agent Substances 0.000 claims description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 3
- 229910019142 PO4 Inorganic materials 0.000 claims description 3
- 229910052782 aluminium Inorganic materials 0.000 claims description 3
- 239000004411 aluminium Substances 0.000 claims description 3
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 claims description 3
- 239000006229 carbon black Chemical group 0.000 claims description 3
- 239000013078 crystal Chemical group 0.000 claims description 3
- 239000000975 dye Substances 0.000 claims description 3
- 239000010439 graphite Chemical group 0.000 claims description 3
- 229910002804 graphite Inorganic materials 0.000 claims description 3
- 235000021317 phosphate Nutrition 0.000 claims description 3
- 229920000728 polyester Polymers 0.000 claims description 3
- 150000004760 silicates Chemical class 0.000 claims description 3
- 239000013008 thixotropic agent Substances 0.000 claims description 3
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 claims description 2
- KHUFHLFHOQVFGB-UHFFFAOYSA-N 1-aminoanthracene-9,10-dione Chemical class O=C1C2=CC=CC=C2C(=O)C2=C1C=CC=C2N KHUFHLFHOQVFGB-UHFFFAOYSA-N 0.000 claims description 2
- XQGDNRFLRLSUFQ-UHFFFAOYSA-N 2H-pyranthren-1-one Chemical class C1=C(C2=C3C4=C56)C=CC3=CC5=C3C=CC=CC3=CC6=CC=C4C=C2C2=C1C(=O)CC=C2 XQGDNRFLRLSUFQ-UHFFFAOYSA-N 0.000 claims description 2
- 235000000177 Indigofera tinctoria Nutrition 0.000 claims description 2
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 claims description 2
- 239000005083 Zinc sulfide Substances 0.000 claims description 2
- MCMNRKCIXSYSNV-UHFFFAOYSA-N Zirconium dioxide Chemical compound O=[Zr]=O MCMNRKCIXSYSNV-UHFFFAOYSA-N 0.000 claims description 2
- 150000004056 anthraquinones Chemical class 0.000 claims description 2
- 239000002518 antifoaming agent Substances 0.000 claims description 2
- MYONAGGJKCJOBT-UHFFFAOYSA-N benzimidazol-2-one Chemical compound C1=CC=CC2=NC(=O)N=C21 MYONAGGJKCJOBT-UHFFFAOYSA-N 0.000 claims description 2
- 229910052980 cadmium sulfide Inorganic materials 0.000 claims description 2
- CJOBVZJTOIVNNF-UHFFFAOYSA-N cadmium sulfide Chemical group [Cd]=S CJOBVZJTOIVNNF-UHFFFAOYSA-N 0.000 claims description 2
- ZCDOYSPFYFSLEW-UHFFFAOYSA-N chromate(2-) Chemical group [O-][Cr]([O-])(=O)=O ZCDOYSPFYFSLEW-UHFFFAOYSA-N 0.000 claims description 2
- 150000004696 coordination complex Chemical class 0.000 claims description 2
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 claims description 2
- PPSZHCXTGRHULJ-UHFFFAOYSA-N dioxazine Chemical compound O1ON=CC=C1 PPSZHCXTGRHULJ-UHFFFAOYSA-N 0.000 claims description 2
- 239000000839 emulsion Substances 0.000 claims description 2
- 150000004338 hydroxy anthraquinones Chemical class 0.000 claims description 2
- 235000019239 indanthrene blue RS Nutrition 0.000 claims description 2
- 229940097275 indigo Drugs 0.000 claims description 2
- COHYTHOBJLSHDF-UHFFFAOYSA-N indigo powder Natural products N1C2=CC=CC=C2C(=O)C1=C1C(=O)C2=CC=CC=C2N1 COHYTHOBJLSHDF-UHFFFAOYSA-N 0.000 claims description 2
- PXZQEOJJUGGUIB-UHFFFAOYSA-N isoindolin-1-one Chemical compound C1=CC=C2C(=O)NCC2=C1 PXZQEOJJUGGUIB-UHFFFAOYSA-N 0.000 claims description 2
- GWVMLCQWXVFZCN-UHFFFAOYSA-N isoindoline Chemical compound C1=CC=C2CNCC2=C1 GWVMLCQWXVFZCN-UHFFFAOYSA-N 0.000 claims description 2
- 229910003455 mixed metal oxide Inorganic materials 0.000 claims description 2
- 230000004048 modification Effects 0.000 claims description 2
- 238000012986 modification Methods 0.000 claims description 2
- OBJNZHVOCNPSCS-UHFFFAOYSA-N naphtho[2,3-f]quinazoline Chemical class C1=NC=C2C3=CC4=CC=CC=C4C=C3C=CC2=N1 OBJNZHVOCNPSCS-UHFFFAOYSA-N 0.000 claims description 2
- 150000002979 perylenes Chemical class 0.000 claims description 2
- 150000003013 phosphoric acid derivatives Chemical group 0.000 claims description 2
- 125000003367 polycyclic group Chemical group 0.000 claims description 2
- IZMJMCDDWKSTTK-UHFFFAOYSA-N quinoline yellow Chemical compound C1=CC=CC2=NC(C3C(C4=CC=CC=C4C3=O)=O)=CC=C21 IZMJMCDDWKSTTK-UHFFFAOYSA-N 0.000 claims description 2
- 229910052814 silicon oxide Inorganic materials 0.000 claims description 2
- PTISTKLWEJDJID-UHFFFAOYSA-N sulfanylidenemolybdenum Chemical group [Mo]=S PTISTKLWEJDJID-UHFFFAOYSA-N 0.000 claims description 2
- JOUDBUYBGJYFFP-FOCLMDBBSA-N thioindigo Chemical compound S\1C2=CC=CC=C2C(=O)C/1=C1/C(=O)C2=CC=CC=C2S1 JOUDBUYBGJYFFP-FOCLMDBBSA-N 0.000 claims description 2
- 235000010215 titanium dioxide Nutrition 0.000 claims description 2
- LSGOVYNHVSXFFJ-UHFFFAOYSA-N vanadate(3-) Chemical group [O-][V]([O-])([O-])=O LSGOVYNHVSXFFJ-UHFFFAOYSA-N 0.000 claims description 2
- 239000011787 zinc oxide Substances 0.000 claims description 2
- LRXTYHSAJDENHV-UHFFFAOYSA-H zinc phosphate Chemical compound [Zn+2].[Zn+2].[Zn+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O LRXTYHSAJDENHV-UHFFFAOYSA-H 0.000 claims description 2
- 229910000165 zinc phosphate Inorganic materials 0.000 claims description 2
- DRDVZXDWVBGGMH-UHFFFAOYSA-N zinc;sulfide Chemical compound [S-2].[Zn+2] DRDVZXDWVBGGMH-UHFFFAOYSA-N 0.000 claims description 2
- 239000003505 polymerization initiator Substances 0.000 claims 8
- 238000010526 radical polymerization reaction Methods 0.000 claims 2
- 125000000609 carbazolyl group Chemical class C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 claims 1
- UCNNJGDEJXIUCC-UHFFFAOYSA-L hydroxy(oxo)iron;iron Chemical compound [Fe].O[Fe]=O.O[Fe]=O UCNNJGDEJXIUCC-UHFFFAOYSA-L 0.000 claims 1
- 229920000915 polyvinyl chloride Polymers 0.000 claims 1
- 239000004800 polyvinyl chloride Substances 0.000 claims 1
- 239000002904 solvent Substances 0.000 abstract description 29
- 229910052751 metal Inorganic materials 0.000 abstract description 10
- 239000002184 metal Substances 0.000 abstract description 10
- 150000001252 acrylic acid derivatives Chemical class 0.000 abstract description 9
- 229920003023 plastic Polymers 0.000 abstract description 6
- 239000004033 plastic Substances 0.000 abstract description 6
- 239000002023 wood Substances 0.000 abstract description 5
- 239000000758 substrate Substances 0.000 abstract description 3
- 229910010293 ceramic material Inorganic materials 0.000 abstract description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 56
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 47
- 238000006243 chemical reaction Methods 0.000 description 42
- 239000011541 reaction mixture Substances 0.000 description 35
- 239000003973 paint Substances 0.000 description 27
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 26
- 238000000576 coating method Methods 0.000 description 26
- WADSJYLPJPTMLN-UHFFFAOYSA-N 3-(cycloundecen-1-yl)-1,2-diazacycloundec-2-ene Chemical compound C1CCCCCCCCC=C1C1=NNCCCCCCCC1 WADSJYLPJPTMLN-UHFFFAOYSA-N 0.000 description 25
- 235000013350 formula milk Nutrition 0.000 description 25
- VMQMZMRVKUZKQL-UHFFFAOYSA-N Cu+ Chemical compound [Cu+] VMQMZMRVKUZKQL-UHFFFAOYSA-N 0.000 description 23
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 21
- 239000011347 resin Substances 0.000 description 21
- 229920005989 resin Polymers 0.000 description 21
- 239000008199 coating composition Substances 0.000 description 18
- 230000015572 biosynthetic process Effects 0.000 description 17
- 239000002270 dispersing agent Substances 0.000 description 17
- JROGBPMEKVAPEH-GXGBFOEMSA-N emetine dihydrochloride Chemical compound Cl.Cl.N1CCC2=CC(OC)=C(OC)C=C2[C@H]1C[C@H]1C[C@H]2C3=CC(OC)=C(OC)C=C3CCN2C[C@@H]1CC JROGBPMEKVAPEH-GXGBFOEMSA-N 0.000 description 17
- OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 description 15
- OZAIFHULBGXAKX-VAWYXSNFSA-N AIBN Substances N#CC(C)(C)\N=N\C(C)(C)C#N OZAIFHULBGXAKX-VAWYXSNFSA-N 0.000 description 15
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 15
- 235000019439 ethyl acetate Nutrition 0.000 description 15
- 229940093499 ethyl acetate Drugs 0.000 description 15
- 239000000243 solution Substances 0.000 description 15
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 14
- CQEYYJKEWSMYFG-UHFFFAOYSA-N butyl acrylate Chemical compound CCCCOC(=O)C=C CQEYYJKEWSMYFG-UHFFFAOYSA-N 0.000 description 14
- 150000003254 radicals Chemical class 0.000 description 14
- UKODFQOELJFMII-UHFFFAOYSA-N pentamethyldiethylenetriamine Chemical compound CN(C)CCN(C)CCN(C)C UKODFQOELJFMII-UHFFFAOYSA-N 0.000 description 13
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 12
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 12
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 description 12
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 12
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
- 229940048053 acrylate Drugs 0.000 description 12
- 239000011248 coating agent Substances 0.000 description 12
- 238000001914 filtration Methods 0.000 description 12
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 11
- 150000001875 compounds Chemical class 0.000 description 11
- 229940063559 methacrylic acid Drugs 0.000 description 11
- 238000003786 synthesis reaction Methods 0.000 description 11
- 238000005160 1H NMR spectroscopy Methods 0.000 description 10
- DPBJAVGHACCNRL-UHFFFAOYSA-N 2-(dimethylamino)ethyl prop-2-enoate Chemical compound CN(C)CCOC(=O)C=C DPBJAVGHACCNRL-UHFFFAOYSA-N 0.000 description 10
- 230000000875 corresponding effect Effects 0.000 description 10
- 238000001723 curing Methods 0.000 description 10
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- 229940043232 butyl acetate Drugs 0.000 description 9
- 238000001816 cooling Methods 0.000 description 9
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 9
- 239000000463 material Substances 0.000 description 9
- 238000010907 mechanical stirring Methods 0.000 description 9
- 229940063557 methacrylate Drugs 0.000 description 9
- 239000000843 powder Substances 0.000 description 9
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 8
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 8
- 238000009472 formulation Methods 0.000 description 8
- 239000000976 ink Substances 0.000 description 8
- 239000003446 ligand Substances 0.000 description 8
- 238000007639 printing Methods 0.000 description 8
- 229920000877 Melamine resin Polymers 0.000 description 7
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 7
- 238000004458 analytical method Methods 0.000 description 7
- 229920001400 block copolymer Polymers 0.000 description 7
- 230000002209 hydrophobic effect Effects 0.000 description 7
- ACEONLNNWKIPTM-UHFFFAOYSA-N methyl 2-bromopropanoate Chemical compound COC(=O)C(C)Br ACEONLNNWKIPTM-UHFFFAOYSA-N 0.000 description 7
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 7
- VMGSQCIDWAUGLQ-UHFFFAOYSA-N n',n'-bis[2-(dimethylamino)ethyl]-n,n-dimethylethane-1,2-diamine Chemical compound CN(C)CCN(CCN(C)C)CCN(C)C VMGSQCIDWAUGLQ-UHFFFAOYSA-N 0.000 description 7
- 229940088644 n,n-dimethylacrylamide Drugs 0.000 description 7
- YLGYACDQVQQZSW-UHFFFAOYSA-N n,n-dimethylprop-2-enamide Chemical compound CN(C)C(=O)C=C YLGYACDQVQQZSW-UHFFFAOYSA-N 0.000 description 7
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 7
- 239000003921 oil Substances 0.000 description 7
- 238000003756 stirring Methods 0.000 description 7
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 6
- 150000001412 amines Chemical class 0.000 description 6
- 125000004429 atom Chemical group 0.000 description 6
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 6
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 6
- 238000005755 formation reaction Methods 0.000 description 6
- 238000000227 grinding Methods 0.000 description 6
- 150000007524 organic acids Chemical class 0.000 description 6
- 239000001301 oxygen Chemical group 0.000 description 6
- 229910052760 oxygen Chemical group 0.000 description 6
- 238000004448 titration Methods 0.000 description 6
- 238000012546 transfer Methods 0.000 description 6
- JKNCOURZONDCGV-UHFFFAOYSA-N 2-(dimethylamino)ethyl 2-methylprop-2-enoate Chemical compound CN(C)CCOC(=O)C(C)=C JKNCOURZONDCGV-UHFFFAOYSA-N 0.000 description 5
- 150000001450 anions Chemical class 0.000 description 5
- 229910052794 bromium Inorganic materials 0.000 description 5
- 239000003153 chemical reaction reagent Substances 0.000 description 5
- 239000006184 cosolvent Substances 0.000 description 5
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 5
- 239000000835 fiber Substances 0.000 description 5
- 239000011521 glass Substances 0.000 description 5
- 238000004519 manufacturing process Methods 0.000 description 5
- JDSHMPZPIAZGSV-UHFFFAOYSA-N melamine Chemical compound NC1=NC(N)=NC(N)=N1 JDSHMPZPIAZGSV-UHFFFAOYSA-N 0.000 description 5
- 229940091868 melamine Drugs 0.000 description 5
- 125000005395 methacrylic acid group Chemical group 0.000 description 5
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 5
- 238000005580 one pot reaction Methods 0.000 description 5
- 230000003647 oxidation Effects 0.000 description 5
- 238000007254 oxidation reaction Methods 0.000 description 5
- 238000012360 testing method Methods 0.000 description 5
- ARXJGSRGQADJSQ-UHFFFAOYSA-N 1-methoxypropan-2-ol Chemical compound COCC(C)O ARXJGSRGQADJSQ-UHFFFAOYSA-N 0.000 description 4
- YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 description 4
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 4
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 4
- JPVYNHNXODAKFH-UHFFFAOYSA-N Cu2+ Chemical compound [Cu+2] JPVYNHNXODAKFH-UHFFFAOYSA-N 0.000 description 4
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 4
- LSDPWZHWYPCBBB-UHFFFAOYSA-N Methanethiol Chemical compound SC LSDPWZHWYPCBBB-UHFFFAOYSA-N 0.000 description 4
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 4
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 4
- 229960000583 acetic acid Drugs 0.000 description 4
- 125000003277 amino group Chemical group 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Substances C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 4
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 4
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- 150000001768 cations Chemical class 0.000 description 4
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- 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 1
- 150000002576 ketones Chemical class 0.000 description 1
- 239000004973 liquid crystal related substance Substances 0.000 description 1
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- 238000005259 measurement Methods 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
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- 229910021645 metal ion Inorganic materials 0.000 description 1
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- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- JLEJCNOTNLZCHQ-UHFFFAOYSA-N methyl 2-chloropropanoate Chemical compound COC(=O)C(C)Cl JLEJCNOTNLZCHQ-UHFFFAOYSA-N 0.000 description 1
- NQVJUHCFWKRBCA-UHFFFAOYSA-N methyl 2-hydroxy-2-(2-methylprop-2-enoylamino)acetate Chemical compound COC(=O)C(O)NC(=O)C(C)=C NQVJUHCFWKRBCA-UHFFFAOYSA-N 0.000 description 1
- CRVGTESFCCXCTH-UHFFFAOYSA-N methyl diethanolamine Chemical compound OCCN(C)CCO CRVGTESFCCXCTH-UHFFFAOYSA-N 0.000 description 1
- YACKEPLHDIMKIO-UHFFFAOYSA-N methylphosphonic acid Chemical compound CP(O)(O)=O YACKEPLHDIMKIO-UHFFFAOYSA-N 0.000 description 1
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- KGHYGBGIWLNFAV-UHFFFAOYSA-N n,n'-ditert-butylethane-1,2-diamine Chemical compound CC(C)(C)NCCNC(C)(C)C KGHYGBGIWLNFAV-UHFFFAOYSA-N 0.000 description 1
- YKYONYBAUNKHLG-UHFFFAOYSA-N n-Propyl acetate Natural products CCCOC(C)=O YKYONYBAUNKHLG-UHFFFAOYSA-N 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 125000005186 naphthyloxy group Chemical group C1(=CC=CC2=CC=CC=C12)O* 0.000 description 1
- 229930014626 natural product Natural products 0.000 description 1
- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 description 1
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 125000001400 nonyl group Chemical class [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 230000000269 nucleophilic effect Effects 0.000 description 1
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 1
- 125000005474 octanoate group Chemical class 0.000 description 1
- 125000002347 octyl group Chemical class [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000007645 offset printing Methods 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 239000013110 organic ligand Substances 0.000 description 1
- 229920000620 organic polymer Polymers 0.000 description 1
- 150000002918 oxazolines Chemical class 0.000 description 1
- 229960003903 oxygen Drugs 0.000 description 1
- 238000004806 packaging method and process Methods 0.000 description 1
- 125000001147 pentyl group Chemical class C(CCCC)* 0.000 description 1
- VLTRZXGMWDSKGL-UHFFFAOYSA-M perchlorate Inorganic materials [O-]Cl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-M 0.000 description 1
- VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 1
- 229940038597 peroxide anti-acne preparations for topical use Drugs 0.000 description 1
- 150000002978 peroxides Chemical class 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- 229920001568 phenolic resin Polymers 0.000 description 1
- 229950000688 phenothiazine Drugs 0.000 description 1
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 1
- NIXKBAZVOQAHGC-UHFFFAOYSA-N phenylmethanesulfonic acid Chemical class OS(=O)(=O)CC1=CC=CC=C1 NIXKBAZVOQAHGC-UHFFFAOYSA-N 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- UEZVMMHDMIWARA-UHFFFAOYSA-M phosphonate Chemical compound [O-]P(=O)=O UEZVMMHDMIWARA-UHFFFAOYSA-M 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
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- 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 description 1
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- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
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- 229920002545 silicone oil Polymers 0.000 description 1
- OLRJXMHANKMLTD-UHFFFAOYSA-N silyl Chemical compound [SiH3] OLRJXMHANKMLTD-UHFFFAOYSA-N 0.000 description 1
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- 125000002730 succinyl group Chemical group C(CCC(=O)*)(=O)* 0.000 description 1
- 150000003871 sulfonates Chemical class 0.000 description 1
- 125000001174 sulfone group Chemical group 0.000 description 1
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- 239000000725 suspension Substances 0.000 description 1
- 239000012209 synthetic fiber Substances 0.000 description 1
- 229920002994 synthetic fiber Polymers 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- CBXCPBUEXACCNR-UHFFFAOYSA-N tetraethylammonium Chemical compound CC[N+](CC)(CC)CC CBXCPBUEXACCNR-UHFFFAOYSA-N 0.000 description 1
- ZUHZGEOKBKGPSW-UHFFFAOYSA-N tetraglyme Chemical compound COCCOCCOCCOCCOC ZUHZGEOKBKGPSW-UHFFFAOYSA-N 0.000 description 1
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 description 1
- 125000005958 tetrahydrothienyl group Chemical group 0.000 description 1
- 238000007669 thermal treatment Methods 0.000 description 1
- GVIJJXMXTUZIOD-UHFFFAOYSA-N thianthrene Chemical compound C1=CC=C2SC3=CC=CC=C3SC2=C1 GVIJJXMXTUZIOD-UHFFFAOYSA-N 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
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- IBBLKSWSCDAPIF-UHFFFAOYSA-N thiopyran Chemical compound S1C=CC=C=C1 IBBLKSWSCDAPIF-UHFFFAOYSA-N 0.000 description 1
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1
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- GZBUMTPCIKCWFW-UHFFFAOYSA-N triethylcholine Chemical class CC[N+](CC)(CC)CCO GZBUMTPCIKCWFW-UHFFFAOYSA-N 0.000 description 1
- ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical compound OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 0.000 description 1
- YFNKIDBQEZZDLK-UHFFFAOYSA-N triglyme Chemical compound COCCOCCOCCOC YFNKIDBQEZZDLK-UHFFFAOYSA-N 0.000 description 1
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- JSPLKZUTYZBBKA-UHFFFAOYSA-N trioxidane Chemical class OOO JSPLKZUTYZBBKA-UHFFFAOYSA-N 0.000 description 1
- 229960004418 trolamine Drugs 0.000 description 1
- 125000002948 undecyl group Chemical class [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- JOYRKODLDBILNP-UHFFFAOYSA-N urethane group Chemical group NC(=O)OCC JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 1
- 229940077935 zinc phosphate Drugs 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L51/00—Compositions of graft polymers in which the grafted component is obtained by reactions only involving carbon-to-carbon unsaturated bonds; Compositions of derivatives of such polymers
- C08L51/003—Compositions of graft polymers in which the grafted component is obtained by reactions only involving carbon-to-carbon unsaturated bonds; Compositions of derivatives of such polymers grafted on to macromolecular compounds obtained by reactions only involving unsaturated carbon-to-carbon bonds
-
- 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
- C08F293/00—Macromolecular compounds obtained by polymerisation on to a macromolecule having groups capable of inducing the formation of new polymer chains bound exclusively at one or both ends of the starting macromolecule
-
- 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
- C08F293/00—Macromolecular compounds obtained by polymerisation on to a macromolecule having groups capable of inducing the formation of new polymer chains bound exclusively at one or both ends of the starting macromolecule
- C08F293/005—Macromolecular compounds obtained by polymerisation on to a macromolecule having groups capable of inducing the formation of new polymer chains bound exclusively at one or both ends of the starting macromolecule using free radical "living" or "controlled" polymerisation, e.g. using a complexing agent
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L53/00—Compositions of block copolymers containing at least one sequence of a polymer obtained by reactions only involving carbon-to-carbon unsaturated bonds; Compositions of derivatives of such polymers
-
- 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
- C08F2438/00—Living radical polymerisation
- C08F2438/01—Atom Transfer Radical Polymerization [ATRP] or reverse ATRP
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Graft Or Block Polymers (AREA)
- Macromonomer-Based Addition Polymer (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Paints Or Removers (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP00810023.2 | 2000-01-11 | ||
| EP00810023 | 2000-01-11 | ||
| PCT/EP2001/000053 WO2001051534A1 (en) | 2000-01-11 | 2001-01-04 | Comb polymers from atrp macromonomers |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2394660A1 true CA2394660A1 (en) | 2001-07-19 |
Family
ID=8174521
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002394660A Abandoned CA2394660A1 (en) | 2000-01-11 | 2001-01-04 | Comb polymers from atrp macromonomers |
Country Status (10)
| Country | Link |
|---|---|
| US (1) | US6936656B2 (https=) |
| EP (1) | EP1254185A1 (https=) |
| JP (1) | JP5290485B2 (https=) |
| KR (1) | KR100673429B1 (https=) |
| CN (2) | CN100549055C (https=) |
| AU (1) | AU2001237275A1 (https=) |
| BR (1) | BR0107548A (https=) |
| CA (1) | CA2394660A1 (https=) |
| MX (1) | MXPA02006782A (https=) |
| WO (1) | WO2001051534A1 (https=) |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6376597B1 (en) * | 1999-12-16 | 2002-04-23 | Ppg Industries Ohio, Inc. | Pigment dispersions containing dispersants having pendent hydrophilic polymeric segments prepared by controlled radical polymerization |
| TW200407363A (en) * | 2001-11-29 | 2004-05-16 | Ciba Sc Holding Ag | Pigment compositions with modified ATRP copolymer dispersants |
| US6582510B1 (en) * | 2002-04-16 | 2003-06-24 | Arco Chemical Technology, L.P. | Use of comb-branched copolymers as pigment dispersants |
| DE10237286A1 (de) | 2002-08-14 | 2004-02-26 | Degussa Construction Chemicals Gmbh | Verwendung von Blockcopolymeren als Dilpergiermittel für wässrige Feststoff-Suspensionen |
| MXPA05008832A (es) * | 2003-02-20 | 2005-10-05 | Ciba Sc Holding Ag | Composicion de pigmento facilmente dispersable. |
| WO2004078839A1 (en) * | 2003-03-03 | 2004-09-16 | Ciba Specialty Chemicals Holding Inc. | Process for intercalating natural or sznthetic clays with block or comb copolymers |
| KR20060056900A (ko) * | 2003-06-24 | 2006-05-25 | 폴리머스 오스트레일리아 프로프라이어터리 리미티드 | 나노복합체 중의 아크릴 분산제 |
| GB2418204A (en) * | 2004-09-21 | 2006-03-22 | Sun Chemical Ltd | Energy-curable intaglio printing inks |
| US7535642B2 (en) * | 2004-04-09 | 2009-05-19 | Kimoto Co., Ltd. | Light control sheet and surface light source using the same |
| WO2006007364A2 (en) * | 2004-06-10 | 2006-01-19 | Degussa Corporation | Heat-stable colorant compositions for polymers |
| JP2006016488A (ja) * | 2004-07-01 | 2006-01-19 | Toyo Ink Mfg Co Ltd | 樹脂のグラフトされた有機顔料およびその製造方法 |
| WO2006104097A1 (ja) * | 2005-03-28 | 2006-10-05 | Kaneka Corporation | アクリル系ブロック共重合体、反応性ホットメルト接着剤組成物 |
| JP2007002122A (ja) * | 2005-06-24 | 2007-01-11 | Fuji Xerox Co Ltd | インクジェット用インク、インクジェット用処理液、インクジェット用インクセット、インクジェット用インクタンク、インクジェット記録方法、及びインクジェット記録装置 |
| US8349943B2 (en) | 2006-03-15 | 2013-01-08 | Kao Corporation | Pigment dispersant containing a copolymer with constituent units derived from polymerizable macromonomers |
| JP4963031B2 (ja) * | 2006-03-15 | 2012-06-27 | 花王株式会社 | 非水系顔料分散剤 |
| WO2007123231A1 (ja) | 2006-04-21 | 2007-11-01 | Nippon Sheet Glass Company, Limited | 光輝性顔料およびその製造方法、並びに該光輝性顔料を含む水性樹脂組成物 |
| CN101511948B (zh) * | 2006-08-29 | 2013-01-02 | 日本板硝子株式会社 | 珍珠光泽颜料 |
| ES2395891T3 (es) | 2006-12-28 | 2013-02-15 | Nuplex Resins B.V. | Dispersiones polimericas a base de agua |
| US9107834B2 (en) * | 2007-04-18 | 2015-08-18 | Nippon Sheet Glass Company, Limited | Bright pigment and cosmetic composition using the same |
| EP2145927B1 (en) * | 2007-04-27 | 2018-03-07 | Nippon Sheet Glass Company, Limited | Use of a bright pigment in an automotive body coating |
| CN101827898B (zh) * | 2007-10-18 | 2013-03-27 | 日本板硝子株式会社 | 发光性颜料 |
| WO2010108837A1 (en) | 2009-03-24 | 2010-09-30 | Basf Se | Preparation of shaped metal particles and their uses |
| CN101845129B (zh) * | 2010-05-21 | 2012-07-04 | 中科院广州化学有限公司 | 有机硅(甲基)丙烯酸酯aba型嵌段共聚物及其制备方法和应用 |
| CN101899132B (zh) * | 2010-07-26 | 2012-04-25 | 鲁东大学 | 一种聚丙烯腈吸附材料的制备方法 |
| WO2012033226A1 (ja) * | 2010-09-08 | 2012-03-15 | 関西ペイント株式会社 | 水性エポキシ樹脂塗料組成物用キット、水性エポキシ樹脂塗料組成物、塗装物品の形成方法、及び塗装物品 |
| CN102010491B (zh) * | 2010-11-11 | 2012-05-30 | 常州大学 | 甲基丙烯酸二甲氨基乙酯-丙烯酸丁酯共聚物的制备方法 |
| CN102700260B (zh) * | 2012-05-27 | 2014-12-10 | 沈玉琴 | 一种瓷砖喷墨前的处理方法 |
| EP2935348A4 (en) | 2012-12-18 | 2016-06-29 | Henkel IP & Holding GmbH | METHOD FOR CONTROLLED RADICAL POLYMERIZATION OF BRANCHED POLYACRYLATES |
| EP3033361A4 (en) * | 2013-08-12 | 2017-05-03 | Henkel IP & Holding GmbH | Alkoxysilane-functionalized polyacrylate compositions and methods of preparation thereof |
| JP6739334B2 (ja) | 2013-11-04 | 2020-08-12 | ルブリゾル アドバンスド マテリアルズ， インコーポレイテッド | 縮合芳香族イミドアンカー基を有するアクリル系分散剤 |
| CN114591469B (zh) * | 2013-11-29 | 2025-06-06 | 三菱化学株式会社 | (甲基)丙烯酸系共聚物、含有该(甲基)丙烯酸系共聚物的粘合剂组合物以及粘合片 |
| FR3018814B1 (fr) * | 2014-03-24 | 2016-03-04 | Rhodia Operations | Polymeres amphiphiles multibloc |
| WO2015155965A1 (ja) * | 2014-04-08 | 2015-10-15 | 東洋ゴム工業株式会社 | ゴム組成物及び空気入りタイヤ |
| TWI516520B (zh) | 2014-10-31 | 2016-01-11 | 財團法人工業技術研究院 | 波長轉換聚合物、其製法及包含其之波長轉換裝置 |
| CN104387841A (zh) * | 2014-11-11 | 2015-03-04 | 合肥皖为电气设备工程有限责任公司 | 一种添加聚乙烯蜡的新型印刷油墨及其制作方法 |
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| CN108602034B (zh) | 2016-01-29 | 2021-01-26 | 路博润先进材料公司 | 具有改进的化学和热稳定性的含有多个胺基团的聚合物分散剂 |
| CN105694697A (zh) * | 2016-04-27 | 2016-06-22 | 柳州申通汽车科技有限公司 | 水性汽车纳米涂料及其加工工艺 |
| CN105694564A (zh) * | 2016-04-27 | 2016-06-22 | 柳州申通汽车科技有限公司 | 汽车涂料及其加工工艺 |
| WO2018082970A1 (en) * | 2016-11-04 | 2018-05-11 | Basf Se | Novel monomers and polymers |
| CN108079980A (zh) * | 2016-11-21 | 2018-05-29 | 中国科学院大连化学物理研究所 | 一种具有疏水性刷型聚合物涂层的色谱柱及制备和应用 |
| WO2018132582A1 (en) * | 2017-01-12 | 2018-07-19 | Carnegie Mellon University | Surfactant assisted formation of a catalyst complex for emulsion atom transfer radical polymerization processes |
| AU2019331373B2 (en) * | 2018-08-31 | 2025-04-24 | Dow Global Technologies Llc | Branched polymeric dispersants, aqueous pigment dispersions, and aqueous coating compositions thereof |
| CN111704696B (zh) * | 2020-06-24 | 2022-10-18 | 新乡学院 | 一种氟硅接枝改性丙烯酸树脂的制备方法 |
| CN112608406A (zh) * | 2020-11-27 | 2021-04-06 | 浙江可思克高新材料股份有限公司 | 一种重钙研磨分散剂及其制备方法 |
| CN114262414B (zh) * | 2022-01-24 | 2024-07-05 | 长春市兆兴新材料技术有限责任公司 | 一种梳型超高分子量聚合物及合成方法 |
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| DE3486145T2 (de) * | 1983-07-11 | 1993-09-23 | Commw Scient Ind Res Org | Verfahren zur polymerisation und nach diesem verfahren hergestellte polymere. |
| US4656226A (en) * | 1985-09-30 | 1987-04-07 | E. I. Du Pont De Nemours And Company | Acrylic pigment dispersants made by group transfer polymerization |
| US5109075A (en) * | 1988-06-06 | 1992-04-28 | The B. F. Goodrich Company | Comb-shaped graft copolymers of allyl terminated macromolecular monomers of polyethers |
| ES2110321T3 (es) * | 1994-04-30 | 1998-02-01 | Wacker Chemie Gmbh | Producto de revestimiento acuoso y proceso para la preparacion de revestimientos barnizados multicapa cuya sensacion de color depende del angulo de observacion. |
| US5763548A (en) * | 1995-03-31 | 1998-06-09 | Carnegie-Mellon University | (Co)polymers and a novel polymerization process based on atom (or group) transfer radical polymerization |
| US5807937A (en) * | 1995-11-15 | 1998-09-15 | Carnegie Mellon University | Processes based on atom (or group) transfer radical polymerization and novel (co) polymers having useful structures and properties |
| US5789487A (en) * | 1996-07-10 | 1998-08-04 | Carnegie-Mellon University | Preparation of novel homo- and copolymers using atom transfer radical polymerization |
| US5859113A (en) * | 1997-07-17 | 1999-01-12 | E. I. Du Pont De Nemours And Company | Pigment dispersions containing hydroxylated AB-block polymer dispersant |
| FR2770219A1 (fr) * | 1997-10-24 | 1999-04-30 | Atochem Elf Sa | Procede de fabrication de copolymeres a architecture controlee a l'aide d'amorceurs radicalaires fonctionnels en polymerisation radicalaire vivante, et composes amorceurs et copolymeres correspondants |
| CA2321784A1 (en) | 1998-02-27 | 1999-09-02 | Kaneka Corporation | Polymer and curable composition |
| DE69935259T2 (de) * | 1998-06-19 | 2007-10-25 | Kaneka Corp. | Verfahren zur herstellung von verzweigtem polymer |
| WO2000011055A1 (fr) * | 1998-08-21 | 2000-03-02 | Elf Atochem S.A. | Procede de fabrication de copolymers a architecture controlee et copolymeres obtenus |
| ATE279447T1 (de) | 1998-09-29 | 2004-10-15 | Ciba Sc Holding Ag | Verfahren zur herstellung von polymeren enthaltend endständige n-0 gruppen |
| BR9916725A (pt) | 1998-12-31 | 2001-09-11 | Ciba Sc Holding Ag | Composição de pigmento contendo polìmeros atrp |
| US6462125B1 (en) * | 1999-12-16 | 2002-10-08 | Ppg Industries Ohio, Inc. | Pigment dispersions containing dispersants prepared by controlled radical polymerization having hydrophilic and hydrophobic segments |
| CN1228789C (zh) * | 2003-06-05 | 2005-11-23 | 北京英纳超导技术有限公司 | 一种超导导线及其制备方法 |
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2001
- 2001-01-04 CN CNB2003101047562A patent/CN100549055C/zh not_active Expired - Fee Related
- 2001-01-04 CN CNB018036414A patent/CN100497420C/zh not_active Expired - Fee Related
- 2001-01-04 WO PCT/EP2001/000053 patent/WO2001051534A1/en not_active Ceased
- 2001-01-04 CA CA002394660A patent/CA2394660A1/en not_active Abandoned
- 2001-01-04 JP JP2001551118A patent/JP5290485B2/ja not_active Expired - Fee Related
- 2001-01-04 KR KR1020027008859A patent/KR100673429B1/ko not_active Expired - Fee Related
- 2001-01-04 MX MXPA02006782A patent/MXPA02006782A/es not_active Application Discontinuation
- 2001-01-04 AU AU2001237275A patent/AU2001237275A1/en not_active Abandoned
- 2001-01-04 EP EP01909579A patent/EP1254185A1/en not_active Withdrawn
- 2001-01-04 BR BR0107548-9A patent/BR0107548A/pt not_active Application Discontinuation
- 2001-01-04 US US10/169,884 patent/US6936656B2/en not_active Expired - Lifetime
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| Publication number | Publication date |
|---|---|
| KR100673429B1 (ko) | 2007-01-24 |
| EP1254185A1 (en) | 2002-11-06 |
| MXPA02006782A (es) | 2002-10-23 |
| AU2001237275A1 (en) | 2001-07-24 |
| JP2003519703A (ja) | 2003-06-24 |
| US6936656B2 (en) | 2005-08-30 |
| US20030166755A1 (en) | 2003-09-04 |
| BR0107548A (pt) | 2002-10-08 |
| CN100549055C (zh) | 2009-10-14 |
| CN100497420C (zh) | 2009-06-10 |
| WO2001051534A1 (en) | 2001-07-19 |
| CN1395587A (zh) | 2003-02-05 |
| JP5290485B2 (ja) | 2013-09-18 |
| CN1506390A (zh) | 2004-06-23 |
| KR20020070335A (ko) | 2002-09-05 |
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