CN101175558B - 分散剂 - Google Patents
分散剂 Download PDFInfo
- Publication number
- CN101175558B CN101175558B CN200680017116XA CN200680017116A CN101175558B CN 101175558 B CN101175558 B CN 101175558B CN 200680017116X A CN200680017116X A CN 200680017116XA CN 200680017116 A CN200680017116 A CN 200680017116A CN 101175558 B CN101175558 B CN 101175558B
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- CN
- China
- Prior art keywords
- acid
- dispersion agent
- general formula
- residue
- alkyl
- 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.)
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- 239000002270 dispersing agent Substances 0.000 title abstract description 5
- 239000002253 acid Substances 0.000 claims abstract description 52
- 239000007787 solid Substances 0.000 claims abstract description 38
- 239000000203 mixture Substances 0.000 claims abstract description 34
- 150000002596 lactones Chemical class 0.000 claims abstract description 17
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims abstract description 16
- 150000001875 compounds Chemical class 0.000 claims abstract description 16
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 claims abstract description 11
- 239000003973 paint Substances 0.000 claims abstract description 11
- 239000001257 hydrogen Substances 0.000 claims abstract description 10
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 10
- 239000004202 carbamide Substances 0.000 claims abstract description 9
- KXDHJXZQYSOELW-UHFFFAOYSA-N Carbamic acid Chemical compound NC(O)=O KXDHJXZQYSOELW-UHFFFAOYSA-N 0.000 claims abstract description 8
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims abstract description 6
- 150000003839 salts Chemical class 0.000 claims abstract description 6
- 239000006185 dispersion Substances 0.000 claims description 112
- 239000003795 chemical substances by application Substances 0.000 claims description 95
- 239000007788 liquid Substances 0.000 claims description 28
- 238000006243 chemical reaction Methods 0.000 claims description 21
- 125000000217 alkyl group Chemical group 0.000 claims description 20
- JBFHTYHTHYHCDJ-UHFFFAOYSA-N gamma-caprolactone Chemical group CCC1CCC(=O)O1 JBFHTYHTHYHCDJ-UHFFFAOYSA-N 0.000 claims description 18
- 150000007520 diprotic acids Chemical class 0.000 claims description 13
- 229920005989 resin Polymers 0.000 claims description 13
- 239000011347 resin Substances 0.000 claims description 13
- 150000008065 acid anhydrides Chemical class 0.000 claims description 12
- 229920000570 polyether Polymers 0.000 claims description 12
- BTCSSZJGUNDROE-UHFFFAOYSA-N gamma-aminobutyric acid Chemical compound NCCCC(O)=O BTCSSZJGUNDROE-UHFFFAOYSA-N 0.000 claims description 11
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 10
- 238000006116 polymerization reaction Methods 0.000 claims description 9
- 238000007639 printing Methods 0.000 claims description 9
- UCMIRNVEIXFBKS-UHFFFAOYSA-N beta-alanine Chemical compound NCCC(O)=O UCMIRNVEIXFBKS-UHFFFAOYSA-N 0.000 claims description 8
- 150000002170 ethers Chemical class 0.000 claims description 7
- 238000002360 preparation method Methods 0.000 claims description 7
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 claims description 6
- 125000001931 aliphatic group Chemical group 0.000 claims description 6
- 150000001408 amides Chemical class 0.000 claims description 6
- 125000004432 carbon atom Chemical group C* 0.000 claims description 6
- 150000001735 carboxylic acids Chemical class 0.000 claims description 6
- 238000000034 method Methods 0.000 claims description 6
- 125000003118 aryl group Chemical group 0.000 claims description 5
- 229960003692 gamma aminobutyric acid Drugs 0.000 claims description 5
- 229940000635 beta-alanine Drugs 0.000 claims description 4
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 claims description 3
- 239000011230 binding agent Substances 0.000 claims description 3
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- 238000005984 hydrogenation reaction Methods 0.000 claims description 2
- 125000005647 linker group Chemical group 0.000 claims 1
- 150000008064 anhydrides Chemical class 0.000 abstract description 2
- 230000002378 acidificating effect Effects 0.000 abstract 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 1
- 125000001841 imino group Chemical group [H]N=* 0.000 abstract 1
- 239000000976 ink Substances 0.000 abstract 1
- -1 and millbase Substances 0.000 description 45
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 30
- POULHZVOKOAJMA-UHFFFAOYSA-N dodecanoic acid Chemical compound CCCCCCCCCCCC(O)=O POULHZVOKOAJMA-UHFFFAOYSA-N 0.000 description 18
- 229920002873 Polyethylenimine Polymers 0.000 description 17
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 16
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 16
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 15
- 239000000049 pigment Substances 0.000 description 15
- 239000002904 solvent Substances 0.000 description 15
- 150000001412 amines Chemical class 0.000 description 11
- 150000002466 imines Chemical class 0.000 description 11
- 239000003153 chemical reaction reagent Substances 0.000 description 10
- 239000000975 dye Substances 0.000 description 10
- 229910052757 nitrogen Inorganic materials 0.000 description 10
- 229920000083 poly(allylamine) Polymers 0.000 description 10
- 229920000768 polyamine Polymers 0.000 description 10
- 229920000728 polyester Polymers 0.000 description 10
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 9
- 238000003756 stirring Methods 0.000 description 9
- 239000005639 Lauric acid Substances 0.000 description 8
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 8
- 239000004721 Polyphenylene oxide Substances 0.000 description 8
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 8
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 7
- 239000002585 base Substances 0.000 description 7
- 150000002148 esters Chemical class 0.000 description 7
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 7
- 239000003921 oil Substances 0.000 description 7
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 6
- OZJPLYNZGCXSJM-UHFFFAOYSA-N 5-valerolactone Chemical compound O=C1CCCCO1 OZJPLYNZGCXSJM-UHFFFAOYSA-N 0.000 description 6
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 239000004952 Polyamide Substances 0.000 description 6
- 125000002947 alkylene group Chemical group 0.000 description 6
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 6
- 239000012299 nitrogen atmosphere Substances 0.000 description 6
- 239000001301 oxygen Substances 0.000 description 6
- 229910052760 oxygen Inorganic materials 0.000 description 6
- 229920002647 polyamide Polymers 0.000 description 6
- UWIULCYKVGIOPW-UHFFFAOYSA-N Glycolone Natural products CCOC1=C(CC=CC)C(=O)N(C)c2c(O)cccc12 UWIULCYKVGIOPW-UHFFFAOYSA-N 0.000 description 5
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 5
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical group O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 5
- 150000001336 alkenes Chemical class 0.000 description 5
- 239000000945 filler Substances 0.000 description 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 5
- 150000003014 phosphoric acid esters Chemical class 0.000 description 5
- 229920006149 polyester-amide block copolymer Polymers 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- CCTFMNIEFHGTDU-UHFFFAOYSA-N 3-methoxypropyl acetate Chemical compound COCCCOC(C)=O CCTFMNIEFHGTDU-UHFFFAOYSA-N 0.000 description 4
- XEUCQOBUZPQUMQ-UHFFFAOYSA-N Glycolone Chemical compound COC1=C(CC=C(C)C)C(=O)NC2=C1C=CC=C2OC XEUCQOBUZPQUMQ-UHFFFAOYSA-N 0.000 description 4
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 description 4
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 4
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 4
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 4
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 4
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 4
- QCWXUUIWCKQGHC-UHFFFAOYSA-N Zirconium Chemical compound [Zr] QCWXUUIWCKQGHC-UHFFFAOYSA-N 0.000 description 4
- 239000003054 catalyst Substances 0.000 description 4
- 238000011156 evaluation Methods 0.000 description 4
- 239000011521 glass Substances 0.000 description 4
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 4
- 239000000543 intermediate Substances 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- 229940043265 methyl isobutyl ketone Drugs 0.000 description 4
- BDERNNFJNOPAEC-UHFFFAOYSA-N n-propyl alcohol Natural products CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 4
- 125000004433 nitrogen atom Chemical group N* 0.000 description 4
- 235000011007 phosphoric acid Nutrition 0.000 description 4
- 229910052726 zirconium Inorganic materials 0.000 description 4
- 101100123574 Arabidopsis thaliana HDA19 gene Proteins 0.000 description 3
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 239000004606 Fillers/Extenders Substances 0.000 description 3
- 101150083200 HDA1 gene Proteins 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- 229920000877 Melamine resin Polymers 0.000 description 3
- 101100297422 Schizosaccharomyces pombe (strain 972 / ATCC 24843) phd1 gene Proteins 0.000 description 3
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 3
- 125000003277 amino group Chemical group 0.000 description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Natural products N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 3
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 3
- 239000012298 atmosphere Substances 0.000 description 3
- 125000002843 carboxylic acid group Chemical group 0.000 description 3
- XPPKVPWEQAFLFU-UHFFFAOYSA-J diphosphate(4-) Chemical compound [O-]P([O-])(=O)OP([O-])([O-])=O XPPKVPWEQAFLFU-UHFFFAOYSA-J 0.000 description 3
- 235000011180 diphosphates Nutrition 0.000 description 3
- IVJISJACKSSFGE-UHFFFAOYSA-N formaldehyde;1,3,5-triazine-2,4,6-triamine Chemical compound O=C.NC1=NC(N)=NC(N)=N1 IVJISJACKSSFGE-UHFFFAOYSA-N 0.000 description 3
- JMOLZNNXZPAGBH-UHFFFAOYSA-N hexyldecanoic acid Chemical compound CCCCCCCCC(C(O)=O)CCCCCC JMOLZNNXZPAGBH-UHFFFAOYSA-N 0.000 description 3
- 229950004531 hexyldecanoic acid Drugs 0.000 description 3
- 235000019239 indanthrene blue RS Nutrition 0.000 description 3
- UHOKSCJSTAHBSO-UHFFFAOYSA-N indanthrone blue Chemical compound C1=CC=C2C(=O)C3=CC=C4NC5=C6C(=O)C7=CC=CC=C7C(=O)C6=CC=C5NC4=C3C(=O)C2=C1 UHOKSCJSTAHBSO-UHFFFAOYSA-N 0.000 description 3
- 229910052500 inorganic mineral Inorganic materials 0.000 description 3
- UQSXHKLRYXJYBZ-UHFFFAOYSA-N iron oxide Inorganic materials [Fe]=O UQSXHKLRYXJYBZ-UHFFFAOYSA-N 0.000 description 3
- 150000002576 ketones Chemical class 0.000 description 3
- 229910052751 metal Inorganic materials 0.000 description 3
- 239000002184 metal Substances 0.000 description 3
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- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
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- WBHHMMIMDMUBKC-QJWNTBNXSA-N ricinoleic acid Chemical compound CCCCCC[C@@H](O)C\C=C/CCCCCCCC(O)=O WBHHMMIMDMUBKC-QJWNTBNXSA-N 0.000 description 3
- 229960003656 ricinoleic acid Drugs 0.000 description 3
- FEUQNCSVHBHROZ-UHFFFAOYSA-N ricinoleic acid Natural products CCCCCCC(O[Si](C)(C)C)CC=CCCCCCCCC(=O)OC FEUQNCSVHBHROZ-UHFFFAOYSA-N 0.000 description 3
- PAPBSGBWRJIAAV-UHFFFAOYSA-N ε-Caprolactone Chemical compound O=C1CCCCCO1 PAPBSGBWRJIAAV-UHFFFAOYSA-N 0.000 description 3
- TXWSZJSDZKWQAU-UHFFFAOYSA-N 2,9-dimethyl-5,12-dihydroquinolino[2,3-b]acridine-7,14-dione Chemical compound N1C2=CC=C(C)C=C2C(=O)C2=C1C=C(C(=O)C=1C(=CC=C(C=1)C)N1)C1=C2 TXWSZJSDZKWQAU-UHFFFAOYSA-N 0.000 description 2
- MSWZFWKMSRAUBD-UHFFFAOYSA-N 2-Amino-2-Deoxy-Hexose Chemical compound NC1C(O)OC(CO)C(O)C1O MSWZFWKMSRAUBD-UHFFFAOYSA-N 0.000 description 2
- OXQGTIUCKGYOAA-UHFFFAOYSA-N 2-Ethylbutanoic acid Chemical compound CCC(CC)C(O)=O OXQGTIUCKGYOAA-UHFFFAOYSA-N 0.000 description 2
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- AEUBCEDJMLUFGL-UHFFFAOYSA-N 4-anthracen-2-ylbutanoic acid Chemical compound C1=CC=CC2=CC3=CC(CCCC(=O)O)=CC=C3C=C21 AEUBCEDJMLUFGL-UHFFFAOYSA-N 0.000 description 2
- IGFHQQFPSIBGKE-UHFFFAOYSA-N 4-nonylphenol Chemical compound CCCCCCCCCC1=CC=C(O)C=C1 IGFHQQFPSIBGKE-UHFFFAOYSA-N 0.000 description 2
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- NSOXQYCFHDMMGV-UHFFFAOYSA-N Tetrakis(2-hydroxypropyl)ethylenediamine Chemical compound CC(O)CN(CC(C)O)CCN(CC(C)O)CC(C)O NSOXQYCFHDMMGV-UHFFFAOYSA-N 0.000 description 2
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- 125000003710 aryl alkyl group Chemical group 0.000 description 2
- YHWCPXVTRSHPNY-UHFFFAOYSA-N butan-1-olate;titanium(4+) Chemical compound [Ti+4].CCCC[O-].CCCC[O-].CCCC[O-].CCCC[O-] YHWCPXVTRSHPNY-UHFFFAOYSA-N 0.000 description 2
- 125000004106 butoxy group Chemical group [*]OC([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 2
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- BQFCCCIRTOLPEF-UHFFFAOYSA-N chembl1976978 Chemical compound CC1=CC=CC=C1N=NC1=C(O)C=CC2=CC=CC=C12 BQFCCCIRTOLPEF-UHFFFAOYSA-N 0.000 description 2
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- 239000011651 chromium Substances 0.000 description 2
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- 125000000753 cycloalkyl group Chemical group 0.000 description 2
- 239000000412 dendrimer Substances 0.000 description 2
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- IUNMPGNGSSIWFP-UHFFFAOYSA-N dimethylaminopropylamine Chemical compound CN(C)CCCN IUNMPGNGSSIWFP-UHFFFAOYSA-N 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
- GNTDGMZSJNCJKK-UHFFFAOYSA-N divanadium pentaoxide Chemical compound O=[V](=O)O[V](=O)=O GNTDGMZSJNCJKK-UHFFFAOYSA-N 0.000 description 2
- LQZZUXJYWNFBMV-UHFFFAOYSA-N dodecan-1-ol Chemical compound CCCCCCCCCCCCO LQZZUXJYWNFBMV-UHFFFAOYSA-N 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 239000003063 flame retardant Substances 0.000 description 2
- 238000000227 grinding Methods 0.000 description 2
- 229910052736 halogen Inorganic materials 0.000 description 2
- 150000002367 halogens Chemical class 0.000 description 2
- RBTKNAXYKSUFRK-UHFFFAOYSA-N heliogen blue Chemical compound [Cu].[N-]1C2=C(C=CC=C3)C3=C1N=C([N-]1)C3=CC=CC=C3C1=NC([N-]1)=C(C=CC=C3)C3=C1N=C([N-]1)C3=CC=CC=C3C1=N2 RBTKNAXYKSUFRK-UHFFFAOYSA-N 0.000 description 2
- CATSNJVOTSVZJV-UHFFFAOYSA-N heptan-2-one Chemical compound CCCCCC(C)=O CATSNJVOTSVZJV-UHFFFAOYSA-N 0.000 description 2
- 125000001072 heteroaryl group Chemical group 0.000 description 2
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- 239000012634 fragment Substances 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 239000003292 glue Substances 0.000 description 1
- VANNPISTIUFMLH-UHFFFAOYSA-N glutaric anhydride Chemical compound O=C1CCCC(=O)O1 VANNPISTIUFMLH-UHFFFAOYSA-N 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 230000026030 halogenation Effects 0.000 description 1
- 238000005658 halogenation reaction Methods 0.000 description 1
- BXWNKGSJHAJOGX-UHFFFAOYSA-N hexadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCO BXWNKGSJHAJOGX-UHFFFAOYSA-N 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- UCNNJGDEJXIUCC-UHFFFAOYSA-L hydroxy(oxo)iron;iron Chemical compound [Fe].O[Fe]=O.O[Fe]=O UCNNJGDEJXIUCC-UHFFFAOYSA-L 0.000 description 1
- LMHJFKYQYDSOQO-UHFFFAOYSA-N hydroxydecanoic acid Natural products CCCCCC(O)CCCC(O)=O LMHJFKYQYDSOQO-UHFFFAOYSA-N 0.000 description 1
- SEOVTRFCIGRIMH-UHFFFAOYSA-N indole-3-acetic acid Chemical compound C1=CC=C2C(CC(=O)O)=CNC2=C1 SEOVTRFCIGRIMH-UHFFFAOYSA-N 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 229910010272 inorganic material Inorganic materials 0.000 description 1
- 239000011147 inorganic material Substances 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 239000001034 iron oxide pigment Substances 0.000 description 1
- DCYOBGZUOMKFPA-UHFFFAOYSA-N iron(2+);iron(3+);octadecacyanide Chemical compound [Fe+2].[Fe+2].[Fe+2].[Fe+3].[Fe+3].[Fe+3].[Fe+3].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-] DCYOBGZUOMKFPA-UHFFFAOYSA-N 0.000 description 1
- JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 description 1
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- FGKJLKRYENPLQH-UHFFFAOYSA-M isocaproate Chemical compound CC(C)CCC([O-])=O FGKJLKRYENPLQH-UHFFFAOYSA-M 0.000 description 1
- OQAGVSWESNCJJT-UHFFFAOYSA-N isovaleric acid methyl ester Natural products COC(=O)CC(C)C OQAGVSWESNCJJT-UHFFFAOYSA-N 0.000 description 1
- BSIHWSXXPBAGTC-UHFFFAOYSA-N isoviolanthrone Chemical compound C12=CC=CC=C2C(=O)C2=CC=C3C(C4=C56)=CC=C5C5=CC=CC=C5C(=O)C6=CC=C4C4=C3C2=C1C=C4 BSIHWSXXPBAGTC-UHFFFAOYSA-N 0.000 description 1
- 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
- 239000004310 lactic acid Substances 0.000 description 1
- 235000014655 lactic acid Nutrition 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 229920002521 macromolecule Polymers 0.000 description 1
- VTHJTEIRLNZDEV-UHFFFAOYSA-L magnesium dihydroxide Chemical compound [OH-].[OH-].[Mg+2] VTHJTEIRLNZDEV-UHFFFAOYSA-L 0.000 description 1
- 239000000347 magnesium hydroxide Substances 0.000 description 1
- 229910001862 magnesium hydroxide Inorganic materials 0.000 description 1
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 1
- 239000013528 metallic particle Substances 0.000 description 1
- NYGZLYXAPMMJTE-UHFFFAOYSA-M metanil yellow Chemical group [Na+].[O-]S(=O)(=O)C1=CC=CC(N=NC=2C=CC(NC=3C=CC=CC=3)=CC=2)=C1 NYGZLYXAPMMJTE-UHFFFAOYSA-M 0.000 description 1
- HZVOZRGWRWCICA-UHFFFAOYSA-N methanediyl Chemical compound [CH2] HZVOZRGWRWCICA-UHFFFAOYSA-N 0.000 description 1
- 229940017219 methyl propionate Drugs 0.000 description 1
- DYGOPFFOGFHOIB-UHFFFAOYSA-N methylperoxyethane Chemical compound CCOOC DYGOPFFOGFHOIB-UHFFFAOYSA-N 0.000 description 1
- 239000002480 mineral oil Substances 0.000 description 1
- 235000010446 mineral oil Nutrition 0.000 description 1
- 239000003607 modifier Substances 0.000 description 1
- 239000012778 molding material Substances 0.000 description 1
- MEFBJEMVZONFCJ-UHFFFAOYSA-N molybdate Chemical compound [O-][Mo]([O-])(=O)=O MEFBJEMVZONFCJ-UHFFFAOYSA-N 0.000 description 1
- 239000000983 mordant dye Substances 0.000 description 1
- 229940031815 mycocide Drugs 0.000 description 1
- KVKFRMCSXWQSNT-UHFFFAOYSA-N n,n'-dimethylethane-1,2-diamine Chemical compound CNCCNC KVKFRMCSXWQSNT-UHFFFAOYSA-N 0.000 description 1
- DIOQZVSQGTUSAI-UHFFFAOYSA-N n-butylhexane Natural products CCCCCCCCCC DIOQZVSQGTUSAI-UHFFFAOYSA-N 0.000 description 1
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- GOQYKNQRPGWPLP-UHFFFAOYSA-N n-heptadecyl alcohol Natural products CCCCCCCCCCCCCCCCCO GOQYKNQRPGWPLP-UHFFFAOYSA-N 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 150000004767 nitrides Chemical class 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
- 229940055577 oleyl alcohol Drugs 0.000 description 1
- XMLQWXUVTXCDDL-UHFFFAOYSA-N oleyl alcohol Natural products CCCCCCC=CCCCCCCCCCCO XMLQWXUVTXCDDL-UHFFFAOYSA-N 0.000 description 1
- 239000011368 organic material Substances 0.000 description 1
- 239000012860 organic pigment Substances 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 1
- AJCDFVKYMIUXCR-UHFFFAOYSA-N oxobarium;oxo(oxoferriooxy)iron Chemical compound [Ba]=O.O=[Fe]O[Fe]=O.O=[Fe]O[Fe]=O.O=[Fe]O[Fe]=O.O=[Fe]O[Fe]=O.O=[Fe]O[Fe]=O.O=[Fe]O[Fe]=O AJCDFVKYMIUXCR-UHFFFAOYSA-N 0.000 description 1
- 125000005702 oxyalkylene group Chemical group 0.000 description 1
- FDPIMTJIUBPUKL-UHFFFAOYSA-N pentan-3-one Chemical compound CCC(=O)CC FDPIMTJIUBPUKL-UHFFFAOYSA-N 0.000 description 1
- YWAKXRMUMFPDSH-UHFFFAOYSA-N pentene Chemical compound CCCC=C YWAKXRMUMFPDSH-UHFFFAOYSA-N 0.000 description 1
- 230000000737 periodic effect Effects 0.000 description 1
- 239000012071 phase Substances 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
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 125000002467 phosphate group Chemical group [H]OP(=O)(O[H])O[*] 0.000 description 1
- RLOWWWKZYUNIDI-UHFFFAOYSA-N phosphinic chloride Chemical group ClP=O RLOWWWKZYUNIDI-UHFFFAOYSA-N 0.000 description 1
- 150000003008 phosphonic acid esters Chemical class 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 229920003229 poly(methyl methacrylate) Polymers 0.000 description 1
- 229920000333 poly(propyleneimine) Polymers 0.000 description 1
- 229920001281 polyalkylene Polymers 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- ZGSOBQAJAUGRBK-UHFFFAOYSA-N propan-2-olate;zirconium(4+) Chemical compound [Zr+4].CC(C)[O-].CC(C)[O-].CC(C)[O-].CC(C)[O-] ZGSOBQAJAUGRBK-UHFFFAOYSA-N 0.000 description 1
- 229960000380 propiolactone Drugs 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- 239000013225 prussian blue Substances 0.000 description 1
- 229960003351 prussian blue Drugs 0.000 description 1
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 1
- 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
- 150000003254 radicals Chemical class 0.000 description 1
- 239000001054 red pigment Substances 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- RCTGMCJBQGBLKT-PAMTUDGESA-N scarlet red Chemical compound CC1=CC=CC=C1\N=N\C(C=C1C)=CC=C1\N=N\C1=C(O)C=CC2=CC=CC=C12 RCTGMCJBQGBLKT-PAMTUDGESA-N 0.000 description 1
- 238000007650 screen-printing Methods 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- HBMJWWWQQXIZIP-UHFFFAOYSA-N silicon carbide Chemical compound [Si+]#[C-] HBMJWWWQQXIZIP-UHFFFAOYSA-N 0.000 description 1
- 229910010271 silicon carbide Inorganic materials 0.000 description 1
- HQVNEWCFYHHQES-UHFFFAOYSA-N silicon nitride Chemical compound N12[Si]34N5[Si]62N3[Si]51N64 HQVNEWCFYHHQES-UHFFFAOYSA-N 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- FPSFKBGHBCHTOE-UHFFFAOYSA-N sodium 3-hydroxy-4-[(3-methyl-5-oxo-1-phenyl-4H-pyrazol-4-yl)diazenyl]naphthalene-1-sulfonic acid Chemical compound [Na+].O=C1C(N=NC=2C3=CC=CC=C3C(=CC=2O)S(O)(=O)=O)C(C)=NN1C1=CC=CC=C1 FPSFKBGHBCHTOE-UHFFFAOYSA-N 0.000 description 1
- 239000011343 solid material Substances 0.000 description 1
- 239000000992 solvent dye Substances 0.000 description 1
- 235000011150 stannous chloride Nutrition 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 239000004575 stone Substances 0.000 description 1
- XTHPWXDJESJLNJ-UHFFFAOYSA-N sulfurochloridic acid Chemical group OS(Cl)(=O)=O XTHPWXDJESJLNJ-UHFFFAOYSA-N 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- ISXSCDLOGDJUNJ-UHFFFAOYSA-N tert-butyl prop-2-enoate Chemical compound CC(C)(C)OC(=O)C=C ISXSCDLOGDJUNJ-UHFFFAOYSA-N 0.000 description 1
- 229950011008 tetrachloroethylene Drugs 0.000 description 1
- FAGUFWYHJQFNRV-UHFFFAOYSA-N tetraethylenepentamine Chemical compound NCCNCCNCCNCCN FAGUFWYHJQFNRV-UHFFFAOYSA-N 0.000 description 1
- AGGKEGLBGGJEBZ-UHFFFAOYSA-N tetramethylenedisulfotetramine Chemical compound C1N(S2(=O)=O)CN3S(=O)(=O)N1CN2C3 AGGKEGLBGGJEBZ-UHFFFAOYSA-N 0.000 description 1
- 229920001187 thermosetting polymer Polymers 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- 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 description 1
- AXZWODMDQAVCJE-UHFFFAOYSA-L tin(II) chloride (anhydrous) Chemical compound [Cl-].[Cl-].[Sn+2] AXZWODMDQAVCJE-UHFFFAOYSA-L 0.000 description 1
- KSBAEPSJVUENNK-UHFFFAOYSA-L tin(ii) 2-ethylhexanoate Chemical compound [Sn+2].CCCCC(CC)C([O-])=O.CCCCC(CC)C([O-])=O KSBAEPSJVUENNK-UHFFFAOYSA-L 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- 239000004408 titanium dioxide Substances 0.000 description 1
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
- VXUYXOFXAQZZMF-UHFFFAOYSA-N titanium(IV) isopropoxide Chemical compound CC(C)O[Ti](OC(C)C)(OC(C)C)OC(C)C VXUYXOFXAQZZMF-UHFFFAOYSA-N 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- 229910052723 transition metal Inorganic materials 0.000 description 1
- 150000003624 transition metals Chemical class 0.000 description 1
- 229920006337 unsaturated polyester resin Polymers 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
- LXNOENXQFNYMGT-UHFFFAOYSA-N xi-5-Hydroxydodecanoic acid Chemical compound CCCCCCCC(O)CCCC(O)=O LXNOENXQFNYMGT-UHFFFAOYSA-N 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 239000004246 zinc acetate Substances 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
- CHNQZRKUZPNOOH-UHFFFAOYSA-J zinc;manganese(2+);n-[2-(sulfidocarbothioylamino)ethyl]carbamodithioate Chemical compound [Mn+2].[Zn+2].[S-]C(=S)NCCNC([S-])=S.[S-]C(=S)NCCNC([S-])=S CHNQZRKUZPNOOH-UHFFFAOYSA-J 0.000 description 1
Classifications
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B67/00—Influencing the physical, e.g. the dyeing or printing properties of dyestuffs without chemical reactions, e.g. by treating with solvents grinding or grinding assistants, coating of pigments or dyes; Process features in the making of dyestuff preparations; Dyestuff preparations of a special physical nature, e.g. tablets, films
- C09B67/006—Preparation of organic pigments
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G73/00—Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00
- C08G73/02—Polyamines
- C08G73/0206—Polyalkylene(poly)amines
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- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B67/00—Influencing the physical, e.g. the dyeing or printing properties of dyestuffs without chemical reactions, e.g. by treating with solvents grinding or grinding assistants, coating of pigments or dyes; Process features in the making of dyestuff preparations; Dyestuff preparations of a special physical nature, e.g. tablets, films
- C09B67/006—Preparation of organic pigments
- C09B67/0069—Non aqueous dispersions of pigments containing only a solvent and a dispersing agent
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- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B67/00—Influencing the physical, e.g. the dyeing or printing properties of dyestuffs without chemical reactions, e.g. by treating with solvents grinding or grinding assistants, coating of pigments or dyes; Process features in the making of dyestuff preparations; Dyestuff preparations of a special physical nature, e.g. tablets, films
- C09B67/0071—Process features in the making of dyestuff preparations; Dehydrating agents; Dispersing agents; Dustfree compositions
- C09B67/0084—Dispersions of dyes
- C09B67/0085—Non common dispersing agents
- C09B67/009—Non common dispersing agents polymeric dispersing agent
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- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D11/00—Inks
- C09D11/02—Printing inks
- C09D11/03—Printing inks characterised by features other than the chemical nature of the binder
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- C09D177/00—Coating compositions based on polyamides obtained by reactions forming a carboxylic amide link in the main chain; Coating compositions based on derivatives of such polymers
- C09D177/12—Polyester-amides
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- C09D7/00—Features of coating compositions, not provided for in group C09D5/00; Processes for incorporating ingredients in coating compositions
- C09D7/40—Additives
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- C09K23/00—Use of substances as emulsifying, wetting, dispersing, or foam-producing agents
- C09K23/16—Amines or polyamines
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- Polyamides (AREA)
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Abstract
本发明涉及用于分散研磨基料、油漆和油墨的颗粒状固体的分散剂。本发明提供包含颗粒状固体、极性有机介质和通式T-(A)m(B)n-X-Z-Q(0-p)的化合物或其盐的组合物,其中T是氢或聚合终止基团;A是羟基羧酸或其内酯的残基;B是氨基羧酸的残基;X是直接键或二价基;Z是酸性或碱性基团或包含酸性或碱性基团的结构部分;Q是任选的氧化物、脲或二元酸或其酸酐的残基;m和n是正整数;p表示Z中残留氨基和/或亚氨基的数目。
Description
相关申请的交叉引用
本申请要求于2005年4月13日提交的美国临时申请序列号60/671,010的优先权。
发明领域
本发明涉及用于将颗粒状固体如颜料或填料分散在极性介质中的分散剂,和研磨基料、油漆和油墨。
发明背景
专利文献中有许多描述分散剂的出版物,所述分散剂或者是含封端羟基的聚酯链的磷酸酯,或者是通过使具有封端羧酸基的聚酯链与聚胺或聚亚胺如聚亚乙基亚胺反应获得的聚酯胺。例如,WO94/21368公开了一种包含聚亚乙基亚胺残基的分散剂,该聚亚乙基亚胺残基携带衍生自己内酯和至少一种另外规定的内酯或羟基羧酸的聚酯链;WO 99/55763公开了一种类似的胺分散剂,其中聚酯链衍生自两种或更多种不同的线形羟基羧酸或其内酯以及烯属不饱和基团的残基;WO 98/19784公开了一种通式T-(A)n-(B)p-Z的分散剂,A和B各自独立地是可衍生自各种内酯的氧亚烷基羰基,Z是酸性或碱性基团如聚亚乙基亚胺或磷酸酯。虽然此类分散剂可以经调节用于极性或非极性液体介质,但是现已发现极性液体介质中进一步改进的性能可以通过用聚酯/聚酰胺链替代该聚酯链来获得。
发明内容
根据本发明的第一个方面,提供通式1的分散剂:
T-(A)m(B)n-X-Z-Q(0-p) 通式(1)
包括它的盐在内
其中
T是氢或聚合终止基团;
A是羟基羧酸或其内酯的残基;
B是氨基羧酸的残基;
X是直接键或二价基;
Z是酸性或碱性基团或包含酸性或碱性基团的结构部分;
Q是氧化物、脲或二元酸或其酸酐的残基,它与含由Z表示的碱性基团的碱性基团或结构部分连接;
m和n是正整数(理想地非零);
m+n为4-2000;
符号(0-p)是指从0值到p的值;和
p表示Z中不携带基团T-(A)m(B)n-X-的氨基和/或亚氨基的最大可利用数目。
当Z是多价的时,可以存在多于一个与Z连接的基团T-(A)m(B)n-X-,并且这些基团可以是相同的或不同的。还应理解,A或B可以与T连接。
当T是聚合终止基团时,它优选是羧酸R-COOH或醇R-OH的残基,其中R是C1-50-烃基,该烃基是任选取代的。
优选地,R含有不大于40,更优选不大于30,尤其是不大于20个碳原子。
R可以是芳基、芳烷基、杂芳基、环烷基,尤其是烷(烯)基,它们可以是线形或支化的。非常优选R是烷基。
当R是芳基时,它优选是任选地被C1-20-烷基、C1-20-烷氧基、卤素、腈或苯氧基取代的苯基或萘基。R-OH的具体实例是苯酚、2-萘酚、4-辛基苯酚和4-壬基苯酚。R-COOH的具体实例是苯甲酸和萘-2-羧酸。
当R是芳烷基时,它优选是苯甲醇、2-羟基乙基苯基或2-羧乙基苯基。
当R是杂芳基时,它优选是噻吩基。
当R是环烷基时,它优选是C3-8-环烷基,如环丙基,尤其是环己基,其任选地被一个或多个C1-6-烷基取代。
如在上文中指出,尤其优选R是任选取代的烷基,特别是含一个或多个醚基的烷基。R-COOH的具体实例是甲氧基乙酸、丙酸、丁酸、己酸、辛酸、月桂酸、十二烷酸、硬脂酸、2-乙基丁酸、2-乙基己酸、2-丁基辛酸、2-己基癸酸、2-辛基十二烷酸和2-癸基十四烷酸。这类支化烷基羧酸也可以以商标Isocarb(得自Condea GmbH)获得并且具体实例是Isocarb 12、16、20、28、32、34T和36。许多羧酸可作为混合物商购。
当R是取代的时,它优选在R-COOH中含有一个或多个醚基,特别是至少两个醚基。所述醚基可以构成含丙氧基、乙氧基或丁氧基(包括它们的混合物)的聚C1-4-氧化烯链。优选的混合物是丙氧基/乙氧基聚醚链。当聚醚链含有多于一个不同的氧化烯单元时,优选以该聚醚链的重量计氧化乙烯的量不小于50wt%,更优选不少于70wt%,特别是不少于90wt%。然而,非常优选该聚醚链完全由氧化乙烯单元组成。
当R-COOH含有聚醚链时,它优选是聚亚烷氧基一C1-24-烷基醚。聚亚乙氧基一烷基醚的重均分子量优选不大于2000,更优选不大于1000,特别是不大于600。通式R1-O-(CH2CH2)q-CH2-COOH的一烷基醚羧酸可以Kao Chemicals GmbH的商品名AkypoTM获得。具体实例是AkypoTMLF1(R1是C8,q=5),AkypoTMLF2(R1是C8,q=8),AkypoTM RLM25(R1是C12/C14,q=2.5),AkypoTM RLM 45 CA(R1是C12/C14,n=4.5),AkypoTM RO 20 VG(R1是C16/C18,n=2)和AkypoTM RO 50 VG(R1是C16/C18,n=5)。
R-OH的实例是甲醇、乙醇、正丁醇、正己醇、正辛醇、正癸醇、正十二烷醇、正十四醇、正十六醇、正十八醇、油醇、异丙醇、异丁醇、叔丁醇、2-乙基丁醇、3-庚醇、2-乙基己醇、3,5,5-三甲基己醇、3,7-二甲基辛醇和所谓的Guerbet醇,如可以商品名Isofol(得自Condea GmbH)商购的那些,包括它们的混合物。Gue rbe t醇的具体实例是Isofol 12、14T、16、18T、18E、20、24、28、32、32T和36。
当R-OH中的R是取代的烷基时,它优选含有一个或多个醚基,特别是不少于两个醚基。所述醚基可以构成含丙氧基、亚乙氧基或亚丁氧基重复单元(包括它们的混合物)的聚C1-4-亚烷氧基链。当聚醚链含有多于一个不同的亚烷氧基重复单元时,优选该聚醚链的至少50wt%,更优选至少70wt%,特别是至少90wt%由亚乙氧基单元组成。特别优选该聚醚链仅由亚乙氧基单元组成。这类优选的醇是聚亚乙氧基一C1-24-烷基醚,优选C1-12-一烷基醚,特别是C1-6-一烷基醚。由于它们的可容易获得,所以一甲基醚是非常优选的。聚亚烷氧基一烷基醚的重均分子量优选不大于2000,特别是不大于1000。聚亚乙氧基一甲基醚的具体实例具有350、550和750的重均分子量。聚醚一烷基醚的其它实例是与氧化乙烯起反应的Guerbet醇,特别是重均分子量为250-750的那些。
A由其衍生的羟基羧酸在一个实施方案中是羟基-C2-20-亚烯基羧酸,特别是羟基-C1-20-亚烷基羧酸。所述亚烷(烯)基(其中(烯)表示亚烷基或亚烯基)可以是线形或支化的。羟基羧酸的具体实例是蓖麻油酸、12-羟基硬脂酸、6-羟基己酸、5-羟基戊酸、12-羟基十二烷酸、5-羟基十二烷酸、5-羟基癸酸、4-羟基癸酸、10-羟基十一烷酸、乳酸和乙醇酸。
如在上文中所指出,A可以衍生自内酯。适合的内酯的实例β-丙内酯,任选烷基取代的ε-己内酯和任选烷基取代的δ-戊内酯。ε-己内酯和δ-戊内酯中的烷基取代基优选是C1-6-烷基,特别是C1-4-烷基,并且可以是线形或支化的。适合的内酯的实例是ε-己内酯和它们的7-甲基-、3-甲基-、5-甲基-、6-甲基-、4-甲基-、5-叔丁基-、4,4,6-三甲基-和4,6,6-三甲基-其类似物。
可以使用羟基羧酸和/或内酯的混合物。
当A衍生自任选取代的ε-己内酯和-种或多种其它的内酯时,该ε-己内酯优选以内酯总量的至少50wt%,更优选至少70wt%,特别是至少90wt%存在。非常优选A衍生自ε-己内酯本身。
B由其衍生的氨基羧酸优选是氨基-C2-20-亚烯基羧酸,特别是氨基-C1-20-亚烷基羧酸。该亚烷(烯)基可以是线形或支化的。优选地,所述氨基羧酸的亚烷(烯)基含有不大于12个碳原子。具体实例是11-氨基十一烷酸,特别是6-氨基己酸、4-氨基丁酸、β-丙氨酸和肌氨酸。可以使用氨基羧酸的混合物。
当X是二价键时,若Z是碱性基团或含碱性基团的结构部分时,X优选是烯属不饱和基团的残基。优选的含烯属不饱和基团的残基含有羟基并且优选衍生自(甲基)丙烯酸。含烯属不饱和基团和羟基的化合物的实例是(甲基)丙烯酸羟乙基酯、(甲基)丙烯酸羟丙基酯、(甲基)丙烯酸羟丁酯、聚乙二醇一(甲基)丙烯酸酯、聚丙二醇一(甲基)丙烯酸酯、聚乙二醇聚丁二醇一(甲基)丙烯酸酯和聚丙二醇聚丁二醇一(甲基)丙烯酸酯(例如,得自Nihon Yushi Co.Ltd的BlemmerTMPE、BlemmerTMPP)。优选地,所述烯属不饱和基团可衍生自(甲基)丙烯酸羟乙酯。
当Z是酸性基团或含酸性基团的结构部分时,所述酸性基团优选是磺酸酯、硫酸酯、膦酸酯或磷酸酯,包括焦磷酸酯在内。在一个优选实施方案中,Z是正磷酸酯基团。
当Z是碱性基团或含碱性基团的结构部分时,该碱性基团优选是胺、聚胺或聚亚胺。适合的胺的实例是乙二胺、二亚乙基三胺、亚甲基四胺、四亚乙基五胺、五亚乙基六胺、N,N’-二甲基亚乙基二胺、哌嗪、2-甲基哌嗪、2,5-二甲基-哌嗪、1,4-双(3-氨基丙基)哌嗪、N-氨基乙基哌嗪、异佛尔酮二胺、聚氧丙基乙二胺、聚氧乙二胺、双(4-氨基-3-甲基二环己基)甲烷、二氨基二环己基甲烷、双(氨基甲基)环己烷、间苯二甲基二胺、α-(间氨基苯基)乙胺、α-(对氨基苯基)乙胺、间苯二胺、二氨基二苯甲烷、二氨基二苯砜和降冰片烷二胺。
Z也可以是取代的脂族叔胺如3-二甲基氨基丙胺和N,N-二甲基乙醇胺的残基。
聚胺的实例是聚乙烯胺和聚烯丙胺。
聚亚胺优选是聚(C2-6-亚烷基亚胺),特别是聚乙烯亚胺(下文中称为PEI)。聚亚胺可以是线形的或优选支化的。线形聚乙烯亚胺可以通过将聚(N-酰基)亚烷基亚胺水解来制备,例如由TakeoSaegusa等人在Macromolecules,1972,第5卷,第4470页中描述的那样。不同分子量的支化聚乙烯亚胺可从BASF和Nippon Shokubai商购。不同分子量的聚烯丙胺和聚(N-烷基)烯丙胺可从Nitto Boseki商购。不同分子量的聚乙烯胺可以从MitsubishiKasai获得。聚(丙烯亚胺)树枝状体可从DSM Fine Chemicals商购,聚(酰氨胺)树枝状体可从Aldrich Chemical Co.以“Starburst”枝状体获得。
当Z是碱性基团或含碱性基团的结构部分时,它优选是聚烯丙胺、聚乙烯胺特别是聚亚烷基亚胺如PEI的残基。
所述聚胺或聚亚胺的数均分子量优选为500-600,000,更优选为1,000-200,000,更优选为1,000-100,000,特别是1200-100,000。
当Q是二元酸或其酸酐的残基时,该二元酸或酸酐可以是芳族或脂族的,其任选被C1-6-烷基或卤素取代。优选地,它具有小于500的重均分子量。适合的二元酸或酸酐的实例是琥珀酸酐、马来酸酐、苹果酸酐、邻苯二甲酸酐、戊二酸酐、六氢邻苯二甲酸酐、琥珀酸和对苯二甲酸。
优选地,m+n不大于1000,更优选不大于100,更优选不大于50,特别是不大于20。
当Z是聚胺或聚亚胺时,任何游离亚氨基或氨基可以与氧或过氧化物、脲或二元酸或酸酐起反应。当Q是脲的残基时,当与脲起反应时Z中的游离亚氨基或氨基的数目可以在宽限度内变化直到不携带基团T-(A)m(B)n-X-的最大可利用的氮原子。类似地,当Q是二元酸或酸酐的残基时,与该二元酸或酸酐起反应的Z中游离氨基或亚氨基的数目也可以在宽的限度内变化,在这种情况下,非常优选Z中没有携带基团T-(A)m(B)n-X-的大部分氮原子与二元酸或酸酐起反应。
当Q是氧化物的残基时,在Z中不携带基团T-(A)m(B)n-X-的任何氨基或亚氨基可以通过与氧(包括空气)或过氧化物如过氧化氢或过硫酸铵反应而转变成N-氧化物。
当T是酸R-COOH的残基并且X是直接键时,分散剂优选可衍生自通式2的酸:
R-CO(A)m(B)n-OH 通式(2)
下文中将它称为TPOAC酸。
当T是醇T-OH的残基并且X是直接键时,分散剂优选可衍生自通式3的醇:
RO(A)m(B)n-H 通式(3)
下文中将它称为TPOAC醇。
根据本发明的第一个方面,分散剂包括携带至少两个通式4的链的聚乙烯胺、聚烯丙胺或特别是聚(C2-4-亚烷基亚胺)(下文中,PAI):
T-(A)m(B)n- 通式(4)
其中T、A、B、m和n如上文中所述。
由通式4表示的每个链可以经由TPOAC酸中的封端羰基和聚乙烯胺、聚烯丙胺或PAI中的伯或仲氮原子之间形成的共价酰胺连接基-CON<或经由TPOAC酸中的封端-COOH和聚烯丙胺、聚乙烯胺或PAI中的取代的铵基团的带正电氮原子之间形成的离子键-COO-HN+=与聚烯丙胺、聚乙烯胺或PAI连接。因为分散剂含有两个或更多个链T-(A)m(B)n-,所以它可以含有酰胺和其盐键的混合物,这取决于其制备中使用的反应条件。
本发明第一个方面的分散剂可以适宜地由通式5表示:
其中
X-*-*-X表示聚乙烯胺、聚烯丙胺或PAI;
Y表示经由酰胺和/或其盐键连接的链T-(A)m-(B)n-;
r为4-2000;和
T、A、B、m和n如上文中所述。
由Y表示的链可以相同或不同。
r优选不少于10。还优选r不大于1000特别是不大于500。
[0 042] Y与X-*-*-X的重量比为30∶1-1∶1,更优选20∶1和5∶1,特别是17∶1-7∶1也是优选的。
PAI优选是聚乙烯亚胺(PEI),它可以是线形或优选支化的。
该PAI优选具有500-600,000,更优选为1,000-200,000,更优选为1,000-100,000,特别是1,200-50,000的数均分子量。
优选地,A是ε-己内酯的残基,B是6-氨基己酸、4-氨基丁酸、β-丙氨酸或肌氨酸的残基。
本发明第一个方面的尤其有用的分散剂具有3∶1-1∶3的m∶n比率并且其中m+n不大于20。
作为基于通式5的分散剂的另一个变体,提供了通式6的分散剂:
通式(6)
其中
X-*-*-X和Y如上文中所限定;和
Y1表示链T-(A)m-X-,其中T、A、X和m如上文中所限定。r2是正非零整数。
由Y1中的由A表示的聚酯链可以衍生自多于一种不同的羟基羧酸或其内酯。尤其优选的是,T-(A)m-X-衍生自任选地烷基取代的ε-己内酯、取代的δ-戊内酯、12-羟基硬脂酸或蓖麻油酸和它们的混合物。
本发明第一个方面的分散剂优选如下制备:在100℃-150℃的温度下,优选在惰性气氛中使预先形成的TPOAC酸与聚烯丙胺、聚乙烯胺或PAI反应。
TPOAC酸优选如下制备:在50℃-250℃的温度下,任选在羧酸R-COOH存在下,且任选在酯化催化剂存在下,使至少一种羟基羧酸或其内酯与至少一种氨基羧酸反应。优选该温度不小于100℃特别是不少于150℃。为了使最终产物的任何焦烧最小化,优选该温度不大于200℃。该惰性气氛可以由元素周期表的任何惰性气体提供,但是,优选氮气。
酯化催化剂可以是本技术领域任何过去已知的酯化催化剂并且包括钛酸四烷基酯例如钛酸四丁酯,有机酸的锌盐例如乙酸锌,脂肪醇的锆盐例如异丙醇锆,甲苯磺酸或强有机酸如三氟乙酸。
在本发明另一个优选的方面,提供了通式5和6的分散剂,其中Y表示通式7的链残基:
其中
A、B、R、m和n如上文中所限定;和
R2是氢或C1-4-烷基;和
R3是含至多10个碳原子的脂族或芳族残基,其任选地含有可衍生自氧化丙烯和/或氧化乙烯的聚醚残基。
当R2是C1-4-烷基时,它优选是甲基。
R3优选是C2-6-亚烷基,特别是C2-4-亚烷基。
含通式7的链残基的分散剂可以适宜地通过将胺、聚胺或聚亚胺迈克尔加成到通式8的化合物上的反应制备:
其中A、B、R、R2、R3、m和n如上文中所限定。
通式8的化合物可以适宜地如下制备:在50℃-150℃,优选80℃-120℃的温度下,在空气或氧气存在下使含羟基的(烷基)丙烯酸衍生物与预先形成的通式2的TPOAC酸反应。优选地,在酯化催化剂如钛酸四烷基酯例如钛酸四丁酯,金属醇盐如钛酸四异丙酯,锡催化剂如氯化亚锡、辛酸亚锡或氧化一丁锡或酸催化剂如甲苯磺酸或三氟乙酸的存在下进行该反应。还优选在聚合抑制剂的存在下进行该反应以抑制通式8的化合物或(烷基)丙烯酸衍生物的自聚合。聚合抑制剂的实例是(甲基)氢醌和吩噻嗪。氧也充当聚合抑制剂。
胺、聚胺或聚亚胺和通式8的化合物之间的反应优选通过在10℃-130℃之间,特别是在20℃-100℃之间加热来进行。可以使用胺和通式8的化合物的化学当量用量,但是优选使通式8的化合物与聚胺或聚亚胺,特别是PEI反应。
通式8的化合物和胺、聚胺或聚亚胺之间的反应可以任选地在对反应物呈惰性的溶剂存在下进行。适合的溶剂的实例是烃如甲苯、二甲苯和芳烃油溶剂,酮如丙酮、甲乙酮和甲基异丁基酮,链烷醇如正丁醇和异丙醇和酯如乙酸丁酯、己二酸二甲酯、丁二酸二甲酯和戊二酸二甲酯。
当本发明第一个方面的分散剂包含游离氨基或亚氨基时,这些基团可以通过与有机酸或优选无机酸如乙酸、硫酸、盐酸、烷基磺酸、烷基氢硫酸盐和芳基磺酸,包括阴离子染料的盐在内起反应而转化成盐。所述游离氨基或亚氨基也可以通过与硫酸二烷基酯如硫酸二甲酯,烷基卤如乙基溴或苄基卤如苄基氯起反应而转变成季铵盐。
如上文中所公开,分散剂中的游离氨基和/或亚氨基还可以与氧(空气)、脲或二元酸或其酸酐起反应。
还可以使用呈季铵形式的分散剂和呈与氧、脲和二元酸或其酸酐的反应产物形式的分散剂的混合物。
根据本发明的第二个方面,提供了作为通式3的TPOAC醇的磷酸酯的分散剂。该磷酸酯可以是正磷酸或焦磷酸(包括其混合物在内)的酯。
在本发明第二个方面的一个优选的实施方案中,分散剂可以是通式9的化合物:
[RO(A)m(B)n]w-LM 通式(9)
其中R、A、B、m和n如上文中所限定;
L是硫酸根、焦磷酸根或特别是正磷酸根;
m是阳离子;和
w是1或2,包括它们的混合。
在通式9的分散剂中,R优选是任选取代的烷基。当R是取代的时,该取代基优选是一个或多个醚基并且RO-特别是聚亚烷基醚一烷基醚并且特别是聚乙二醇一烷基醚的残基。
通式9的分散剂可以适宜地通过使通式3的TPOAC醇与硫酸盐化或磷酸盐化试剂反应来制备。该反应可以在惰性溶剂中进行,但是优选在没有溶剂的情况下在无水条件下进行,优选在惰性气氛如氮气中进行。与磷酸盐化或硫酸盐化试剂的反应优选在50℃-150℃的温度下,特别是在大于80℃的温度下进行。为了避免使最终分散剂焦烧,温度优选不大于100℃。
当通式9的分散剂呈磷酸酯形式,通式3的TPOAC醇与磷酸盐化试剂的每个磷原子的比率通常为1∶3-3∶1并且该分散剂可以是正磷酸酯和焦磷酸酯的混合物。在通式9的分散剂的特定情况下,当分散剂是正磷酸的一酯和二酯的混合物时,TPOAC醇与磷酸盐化试剂的每个磷原子的比率为1∶1-3∶1,特别是1∶1-2∶1。
优选的硫酸盐化试剂是氯磺酸,发烟硫酸,特别是浓硫酸。优选的磷酸盐化试剂是POCl3、P2O5,特别是多磷酸。
本发明第二个方面的分散剂可以呈游离酸或金属盐、有机胺或季铵盐形式。所述金属优选是碱金属如锂、钾和钠,包括它们的混合物在内。适合的有机胺包括烷基胺,特别是链烷醇胺如一和二乙醇胺。
然而,优选由通式2的TPOAC酸制备本发明第一个方面的分散剂,也可以从通式3的TPOAC醇开始并通过与二元酸或其酸酐反应将它转化成羧酸封端的聚合物,它随后可以与胺、聚胺或聚亚胺起反应。此类分散剂是通式1的那些,其中X是二元酸或其酸酐的残基。按同样地方式,也可以通过从通式2的TPOAC酸开始如下制备硫酸酯或磷酸酯分散剂:通过首先使它与二醇如乙二醇反应以产生羟基封端的聚合物,接着可以使该聚合物与硫酸盐化或磷酸盐化试剂起反应。此类分散剂对应于通式1,其中X是二醇的残基。
在当通式1中的T是氢的特定情形下,由-(A)m(B)n-表示的聚合物链将具有封端用羟基和羧酸基。该羧酸基可以通过与二醇反应转变成封端羟基。这样产生包含聚合物链-(A)m(B)n-的二醇,该聚合物链当与硫酸盐化或磷酸盐化试剂起反应时可以在含序列-(A)m(B)n-的链的两端携带硫酸酯或磷酸酯基团。
用来制备本发明分散剂的一些中间体是新颖的。因此,作为本发明的另一个方面,提供了通式2、3和8的化合物。
如上文中所指出,该分散剂尤其可用于分散有机介质特别是极性有机介质中的颗粒状固体。
根据本发明的另一个方面,提供了包含颗粒状固体和通式1的分散剂的组合物。
根据本发明的又一个方面,提供了包含通式1的分散剂、颗粒状固体和有机介质的分散体。
存在于该分散体中的固体可以是任何无机或有机固体材料,它在相关的温度下基本上不溶于有机介质并且希望它以细碎形式在该有机介质中稳定。
适合的固体的实例是用于溶剂油墨的颜料;用于油漆和塑料材料的颜料、增量剂和填料;染料,特别是分散染料;用于溶剂染浴、油墨和其它溶剂应用体系的荧光增白剂和织物助剂;用于油基和反相-乳液钻孔泥浆的固体;干洗液中的尘土和固体颗粒;颗粒状陶瓷材料;磁性材料和磁记录介质;阻燃剂如用于塑料材料中的那些和在有机介质中用作分散体的杀生物剂、农用化学品和药物。
优选的固体是得自任何公认类别颜料的颜料,所述公认类别颜料例如在Colour Index(1971)的第三版以及随后的修订版和对其的增补版中在段头“Pigments”下进行了描述。无机颜料的实例是二氧化钛,氧化锌,普鲁士蓝,硫化镉,氧化铁,朱砂,群青和铬颜料,包括铅、锌、钡、钙的铬酸盐、钼酸盐和混合铬酸盐和硫酸盐和它们的混合物和改性物,它们可作为浅绿-黄色至红色颜料以品名樱草、柠檬、中铬、橙、猩红和铬红商购。有机颜料的实例是选自偶氮、二偶氮、缩合偶氮、硫靛、阴丹酮、异阴丹酮、蒽嵌蒽醌、蒽醌、异二苯并蒽酮(sodibenzanthrone)、三苯二嗪、喹吖啶酮和酞菁系列,特别是铜酞菁及其环卤化衍生物,以及酸的色淀、碱性和酸性媒介染料。炭黑虽然严格来说是无机的,但是其分散性能方面的表现更像有机颜料。优选的有机颜料是酞菁特别是铜酞菁,单偶氮,二偶氮,阴丹酮,蒽嵌蒽醌,喹吖啶酮和炭黑。
其它优选的固体是:增量剂和填料如滑石、高岭土、二氧化硅、重晶石和白垩;颗粒状陶瓷材料如氧化铝、二氧化硅、氧化锆、氧化钛、氮化硅、氮化硼、碳化硅、碳化硼、混合氮化硅-铝和金属钛酸盐;颗粒状磁性材料如过渡金属特别是铁和铬的磁性氧化物,例如γ-Fe2O3、Fe3O4,和钴掺杂的氧化铁、氧化钙、铁酸盐尤其是铁酸钡;和金属颗粒,特别是金属铁、镍、钴和它们的合金;农用化学品如杀真菌剂flutriafen、多菌灵、百菌清和代森锰锌和阻燃剂如三水合铝和氢氧化镁。
存在于本发明分散体中的有机介质优选是极性有机介质或基本上非极性的芳族烃或卤化烃。与有机介质有关的术语“极性”是指能够形成中等至强的键的有机液体或树脂,如在Crowley等人在Journal of Paint Technology,38卷,1966第269页文章标题为“AThree Dimensional Approach to Solubility”的文章中所述。此类有机介质通常具有如上述文章中所限定的5个或更多的氢键数目。
适合的极性有机液体的实例是胺、醚,尤其是低级烷基醚、有机酸、酯、酮、二醇、醇和酰胺。此类中等强度氢键的液体的许多具体实例在Ibert Mellan的标题为“Compatibility and Solubility”的书本(由Noyes Development Corporation在1968年出版)第39-40页上的表2.14中给出,这些液体都属于本文所使用的术语极性有机液体的范围内。
优选的极性有机液体是二烷基酮、烷烃羧酸和链烷醇的烷基酯,特别是那些包含至多(和包括)总共6个碳原子的液体。作为优选和特别优选的液体的实例,可以提及二烷基和环烷基酮,如丙酮、甲基乙基酮、二乙基酮、二异丙酮、甲基异丁基酮、二异丁酮、甲基异戊基酮、甲基正戊基酮和环己酮;烷基酯如乙酸甲酯、乙酸乙酯、醋酸异丙酯、乙酸丁酯、甲酸乙酯、丙酸甲酯、乙酸甲氧基丙基酯和丁酸乙酯;二醇和二醇酯和醚、如乙二醇、2-乙氧基乙醇、3-甲氧基丙基丙醇、3-乙氧基丙基丙醇、乙酸2-丁氧基乙基酯、乙酸3-甲氧基丙基酯、乙酸3-乙氧基丙基酯和乙酸2-乙氧基乙基酯;链烷醇如甲醇、乙醇、正丙醇、异丙醇、正丁醇和异丁醇和二烷基醚和环状醚如二乙醚和四氢呋喃。
可以单独使用或与上述极性溶剂的混合物使用的基本上非极性的有机液体是芳族烃,如甲苯和二甲苯,脂族烃如己烷、庚烷、辛烷、癸烷、石油馏出液如白油精、矿物油、植物油和卤化脂族和芳族烃,如三氯乙烯、全氯乙烯和氯苯。
作为用于本发明分散体形式的介质,适合的极性树脂的实例是成膜树脂如适合于制备用于各种应用如油漆和油墨的油墨、油漆和碎片的那些。此类树脂的实例包括聚酰胺如VersamidTM和WolfamidTM,和纤维素醚如乙基纤维素和乙基羟乙基纤维素。油漆树脂的实例包括短链油醇酸树脂/蜜胺-甲醛、聚酯/蜜胺-甲醛、热固性丙烯酸系树脂/蜜胺-甲醛、长油醇酸树脂和多介质树脂如丙烯酸系树脂和脲/醛。
树脂还可以是不饱和聚酯树脂,包括所谓的片材模塑料和块体模塑料,它们可以与增强纤维和填料一起配制。此类模塑料在DE3,643,007和P F Bruins的标题为“Unsaturated PolyesterTechnology”的专题论文,Gordon and Breach Sciencepublishers,1976,第211-238页中进行了描述。
如果需要的话,分散体可以包含其它成分,例如,树脂(当它们还没有构成有机介质时)粘结剂、流化剂(如GB-A-1508576和GB-A-2108143中描述的那些)、抗沉降剂、增塑剂、均化剂和防腐剂。
所述分散体通常包含5-95wt%固体,其中精确的量取决于固体的性质并且该量取决于固体的性质和固体的相对密度和有机介质。例如,基于分散体的总重量,其中固体是有机材料,如有机颜料的分散体优选包含15-60wt%所述固体,而其中固体是无机材料,如无机颜料、填料或增量剂的分散体优选包含40-90wt%所述固体。
所述分散体可以通过已知用于制备分散体的任何常规方法获得。因此,可以按任何次序将固体、有机介质和分散剂混合,然后让该混合物经受机械处理以将固体的颗粒减小到合适的尺寸,例如通过球磨、珠磨、石磨或塑料研磨,直到形成分散体。或者,可以将固体独立地或以与有机介质或分散剂的混合物形式进行处理以减小其颗粒尺寸,然后添加其它成分并搅拌该混合物以提供分散体。
如果要求组合物呈干燥形式,则该液体介质优选是挥发性的从而它可以通过简单的分离手段如蒸发容易地从颗粒状固体中除去。然而,优选所述分散体包含液体介质。
如果干燥组合物主要由分散剂和颗粒状固体构成,则基于颗粒状固体的重量该组合物优选包含至少0.2%,更优选至少0.5%特别是至少1.0%分散剂。优选地,基于颗粒状固体的重量,干燥组合物包含不大于100wt%,优选不大于50wt%,更优选不大于20wt%,特别是不大于10wt%分散剂。
如上文中所述,本发明的分散剂尤其适合于制备研磨基料,其中在颗粒状固体和成膜树脂粘结剂同时存在下在有机液体中研磨颗粒状固体。
因此,根据本发明的又一个方面,提供了包含颗粒状固体、分散剂和成膜树脂的研磨基料。
通常,基于研磨基料的总重量,所述研磨基料包含20-70wt%颗粒状固体。优选地,颗粒状固体不少于研磨基料的30wt%或不少于50wt%。
在研磨基料中树脂的量可以在宽的限度内变化但是优选不少于所述研磨基料的连续/液相的10wt%,特别是不少于20wt%。优选地,树脂的量不大于研磨基料的连续/液相的50wt%,特别是不大于40wt%。
研磨基料中的分散剂的量取决于颗粒状固体的量但是优选为研磨基料的0.5-5wt%。
包含本发明分散剂的分散体和研磨基料尤其适合用于油漆,特别是高固含量油漆;油墨,特别是苯胺印刷、凹版印刷和丝网印刷油墨;和无水陶瓷加工,特别是带涂、刮刀、挤出和注射模塑型加工。
本发明的分散剂显示优于类似的含聚酯链而不是所述聚酯/聚酰胺链的分散剂。这些优点包括含颗粒状固体、分散剂和极性有机介质的分散体的改进的流动性,尤其是当所述颗粒状固体是有机颜料时。
将通过以下实施例进一步说明本发明,其中对用量的所有引用以重量份为单位,除非有相反表示。
实施例
碱性分散剂
实施例1 LA1,Cap 6,ACA 6,PEI(13∶1)
将6-氨基己酸(26.24份,0.2M,得自Aldrich)和ε-己内酯(22.83份,0.2M,得自Aldrich)加热到190℃并在氮气下搅拌15分钟。所得的聚酯/聚酰胺具有216.03mgKOH/g的酸值。在109℃下添加月桂酸(6.67份,0.033M,得自Aldrich)接着添加丁醇锆(0.2份)。通过在200℃下搅拌4小时使反应继续进行以产生酸值为36.52mgKOH/g的TPOAC酸。然后将温度降低至120℃并添加聚乙烯亚胺(3.2份,SP 200,MW 10,000,得自Nippon Shokubai)并且在氮气下在120℃下搅拌该反应物6小时。获得为浅黄色液体的产物,该产物在冷却至20℃后变成浅黄色蜡(44份)。这是分散剂1。
实施例2-6
重复实施例1,不同在于使用下表1所示的起始材料代替实施例1中使用的氨基己酸、月桂酸和ε-己内酯。组分的摩尔比如表1所示。表1中的所有分散剂使用聚乙烯亚胺SP 200(PEI),其中TPOAC酸与PEI的重量比为13∶1。
表1
实施例 | 分散剂 | TPOAC酸 | TPOAC酸的酸值 (mgKOH/g) |
2 | 2 | LA1,cap7.2,4-ABA7.2 | 27.82 |
3 | 3 | LA1,cap7.2,4-ABA7.2 | 34.19 |
4 | 4 | LA1,cap4,11-AUDA4 | 40.0 |
5 | 5 | LA1,cap8,AL8 | 30.57 |
6 | 6 | LA1,cap8,SA8 | 36.96 |
表1的脚注
LA是得自Aldrich的月桂酸
cap是得自Aldrich的ε-己内酯
4-ABA是得自Aldrich的4-氨基丁酸
11-AUDA是得自Aldrich的11-氨基十一烷酸
AL是得自Aldrich的β-丙氨酸
SA是得自Aldrich的肌氨酸
实施例7-10 应用
在搅拌下将分散剂(0.45份)溶于溶剂(7.55份),根据需要进行加热。在冷却到20℃后,添加颜料(2份,得自Heubach的MonoliteRubine 3B)和3mm直径的玻璃珠(16份)并且在水平摇动器上研磨该分散体16小时。通过手摇使用A(好)至E(差)的任意等级评价流动性。
结果在下表2中给出。
表2
流动性
实施例 | 分散剂 | 溶剂A | 溶剂B | 溶剂C | 溶剂D |
7 | 1 | D | D/E | A | A |
8 | 2 | A/B | D | A/B | A/B |
9 | 3 | A/B | C | A/B | A/B |
10 | 6 | A/B | C/D | A | A |
对照1 | B | A | D/E | E | |
对照2 | E | E | E | E |
表2的脚注
溶剂A是乙酸甲氧基丙基酯/正丁醇(4∶1)
溶剂B是甲苯
溶剂C是乙酸甲氧基丙基酯/正丁醇(1∶4)
溶剂D是乙醇
对照1是与月桂酸聚合并与PEI(MW 10,000)起反应的ε-己内酯。对照2是没有所添加的试剂并且该配制剂用额外的溶剂补充。
实施例11
将6-氨基己酸(201份,1.53M,得自Aldrich)和ε-己内酯(175份,1.53M,得自Aldrich)加热到190℃并在氮气下搅拌30分钟。所得的聚酯/聚酰胺具有179mgKOH/g的酸值。在109℃下添加月桂酸(51.24份,0.25M,得自Aldrich)接着添加丁醇锆(1份)。通过在185℃下搅拌6小时使反应继续进行以产生酸值为39.15mgKOH/g的TPOAC酸。然后将温度降低至120℃并添加聚乙烯亚胺(101份,SP 200,MW 10,000,得自Nippon Shokubai)并且在氮气下在120℃下搅拌该反应物6小时。获得为浅黄色液体的产物,该产物在冷却至20℃后变成棕色胶(500份)。这是分散剂7。
实施例12-15
重复实施例1,不同在于使用下表3所示的起始材料代替实施例1中使用的氨基己酸、月桂酸、ε-己内酯和聚乙烯亚胺SP 200(PEI)。组分的摩尔比和聚酯聚酰胺(TPOAC酸)与PEI的重量比在下表3中示出。
表3
实施例 | 分散剂 | TPOA℃酸 | TPOAC酸∶ PEI重量比 |
12 | 8 | MAA1,cap7,6-ACA7 | 9∶1 SP030 |
13 | 9 | HA1,cap5,6-ACA5 | 12∶1 PAA15 |
14 | 10 | HDA1,cap5,4-ABA5 | 15∶1 SP075 |
15 | 11 | HDA1,cap5,4-ABA5 | 11∶1 SP200 |
表3的脚注
MAA是得自Aldrich的甲氧基乙酸
cap是得自Aldrich的ε-己内酯
6-ACA是得自Aldrich的6-氨基己酸
4-ABA是得自Aldrich的4-氨基丁酸
HDA是得自Sasol的Isocarb 16(2-己基癸酸)
SP030和SP075是得自Nippon Shokubai的Mn分别为3000和7500的聚乙烯亚胺
PAA15是得自Nitto Boseki Co Ltd.的MW 15000的聚烯丙胺
实施例16
在80℃下在氮气气氛下将分散剂10(32份)与琥珀酸酐(0.8份)搅拌3小时以产生金色液体(31份)。这是分散剂12。
实施例17
在90℃下在氮气气氛下将分散剂10的TPOAC酸(HDA1,cap5,4-ABA5)(40份)和通过US6,787,600的聚酯11中概括的方法制备的含蓖麻油酸和己内酯的聚酯链(10份)搅拌在一起然后添加聚乙烯亚胺SP050(Mn 5000,得自Nippon Shokubai)(3.85份)。在120℃下搅拌整个混合物6小时而获得金色粘性液体。这是分散剂13。
实施例18
将6-氨基己酸(52.24份,0.398M,得自Aldrich)和ε-己内酯(45.45份,0.398M,得自Aldrich)加热到190℃并在氮气下搅拌30分钟。所得的聚酯/聚酰胺具有179mgKOH/g的酸值。在109℃下添加月桂酸(13.29份,0.066M,得自Aldrich)接着添加丁醇锆(1份)。通过在185℃下搅拌6小时使反应继续进行以产生酸值为36.9mgKOH/g的TPOAC酸。然后将温度降低到115℃并添加3-二甲基氨基丙胺(3.35份,0.033M)并在氮气下在185℃下搅拌反应物8小时。当冷却后获得酸值为20.3mgKOH/g的为米黄色蜡的产物。这是分散剂14。
实施例19
在90℃下在氮气气氛下搅拌分散剂14(50份)和硫酸二甲酯(1.63份,0.013M,得自Aldrich)6小时而获得冷却后的米黄色蜡(50份)。这是分散剂15。
实施例20
在190℃下在氮气气氛下将聚乙二醇一甲醚(105份,0.3M,得自Aldrich)、4-氨基丁酸(55.68份,0.54M,得自Aldrich)和ε-己内酯(61.63份,0.54M,得自Aldrich)搅拌20分钟而获得酸值为69.1mg KOH/g和碱当量16135的金色液体。将温度降低到150℃并添加丁醇锆(0.5份)。将该混合物的温度提高到190℃并搅拌6小时。获得了酸值为1.1mg KOH/g的浅棕色液体(210份)。这是中间体1。
将多磷酸(3.85份)添加到中间体1(50份)中并在90℃下在氮气气氛下将整个混合物搅拌6小时而获得棕色液体(53份)。这是分散剂16。
将多磷酸(6.46份)添加到中间体1(42份)中并在90℃下在氮气气氛下将整个混合物搅拌6小时而获得棕色液体(53份)。这是分散剂17。
实施例21-29
应用
在搅拌下将分散剂(0.45份)溶于溶剂(7.55份),根据需要进行加热。在冷却到20℃后,添加颜料(2份,得自Heubach的MonoliteRubine 3 B)和3mm直径的玻璃珠(16份)并且在水平摇动器上研磨该分散体16小时。通过手摇使用A(好)至E(差)的任意等级评价流动性。
结果在下表4中给出。
表4
流动性
实施例 | 分散剂 | 乙醇 74OP |
21 | 2 | A/B |
22 | 3 | A/B |
23 | 6 | A/B |
24 | 8 | B |
25 | 9 | A/B |
26 | 10 | C/D |
27 | 11 | C/D |
28 | 12 | C/D |
29 | 13 | D |
对照1 | E | |
对照2 | E |
实施例30-31
应用
将分散剂(0.25份)溶于乙醇74OP(6.75份)中,根据需要进行搅拌。添加红色氧化铁颜料(3份,Sicotrans Red L 2817,得自BASF)和3mm直径的玻璃珠(16份)并在水平摇动器上研磨该分散体16小时。通过手摇使用A(好)至E(差)的任意等级评价流动性。
结果在下表5中给出。
将分散剂(0.2份)溶于乙醇74OP(2.3份)中,根据需要进行搅拌。添加二氧化钛颜料(7.5份,Tioxide TR92,得自Huntsman)和3mm直径的玻璃珠(16份)并在水平摇动器上研磨该分散体16小时。通过手摇使用A(好)至E(差)的任意等级评价流动性。
结果在下表5中给出。
表5
流动性
实施例 | 分散剂 | Sicotrans Red L2817 | Tioxide TR92 |
30 | 16 | B/C | B/C |
31 | 17 | B/C | C |
对照2 | B | E | |
对照3 | E | E |
表5的脚注
对照2没有所添加的试剂并且该配制剂用额外的溶剂补充。
对照3是与十二烷醇聚合并与五氧化二磷起反应的ε-己内酯。
Claims (21)
1.通式1的分散剂:
T-(A)m(B)n-X-Z-Q(0-P) 通式(1)
包括它的盐
其中
T是氢或聚合终止基团;
A是羟基羧酸或其内酯的残基;
B是氨基羧酸的残基;
X是直接键或二价连接基;
Z是选自聚乙烯胺或聚(C2-4-亚烷基亚胺)的碱性基团,或包含所述碱性基团的结构部分;
Q是氧化物、脲或二元酸或其酸酐的残基,它与由Z表示的碱性基团或包含碱性基团的结构部分连接;
m和n是非零正整数;
m+n为4-2000;
(0-p)是指从0值到p的值;
p表示Z中不携带基团T-(A)m(B)n-X-的氨基和/或亚氨基的最大可利用数目;
当Z是多价的时,任选地存在多于一个与Z连接的基团T-(A)m(B)n-X-,并且所述多于一个基团是化学上相同或不同的。
2.根据权利要求1的分散剂,其中T是羧酸R-COOH或醇R-OH的残基,其中R是任选地取代的C1-50-烃基。
3.根据权利要求2的分散剂,其中R是任选地取代的烷基,其是线形或支化的。
4.根据权利要求2的分散剂,其中R含有一个或多个醚基。
5.根据权利要求1的分散剂,其中A是羟基-C2-20-亚烯基羧酸或羟基-C1-20-亚烷基羧酸或其内酯的残基。
6.根据权利要求5的分散剂,其中所述内酯是ε-己内酯。
7.根据权利要求2的分散剂,其中B是氨基-C2-20-亚烯基羧酸或氨基-C1-20-亚烷基羧酸的残基。
8.根据权利要求7的分散剂,其中所述氨基-C1-20-亚烷基羧酸是6-氨基己酸、4-氨基丁酸、β-丙氨酸或肌氨酸。
9.根据权利要求1的分散剂,其中m+n不大于20。
10.根据权利要求1-9中任一项的分散剂,其中m∶n的比为3∶1至1∶3。
11.根据权利要求1的分散剂,其包含携带至少两个通式4的链的聚乙烯胺或聚(C2-4-亚烷基亚胺):
T-(A)m(B)n- 通式(4)
其中T、A、B、m和n如权利要求1所述。
13.根据权利要求12的分散剂,其中Y与X-*-*-X的重量比为20∶1-5∶1。
14.根据权利要求12的分散剂,其中Y表示通式7的链残基:
通式(7)
其中
R2是氢或C1-4-烷基;和
R3是含至多10个碳原子的脂族或芳族残基,其任选地含有可衍生自氧化丙烯和/或氧化乙烯的聚醚残基,并且其中R是C1-50的任选取代的烃基。
15.根据权利要求1-13中任一项的分散剂的制备方法,该方法包括:在50-250℃的温度下使通式2的TPOAC酸与聚乙烯胺或聚(C2-4-亚烷基亚胺)反应:
R-CO(A)m(B)n-OH 通式(2)
其中R是C1-50的任选取代的烃基。
16.根据权利要求14的分散剂的制备方法,该方法包括:在10-130℃的温度下使通式8的化合物与聚乙烯胺或聚(C2-4-亚烷基亚胺)反应
通式(8)
其中R2、R3和R如权利要求14中所定义。
17.包含颗粒状固体和根据权利要求1-14中任一项的分散剂的组合物。
18.根据权利要求17的组合物,其还包含有机液体。
19.包含颗粒状固体、有机液体、成膜粘结剂树脂和根据权利要求1-14中任一项的分散剂的研磨基料、油漆或油墨。
20.根据权利要求18的组合物或根据权利要求19的研磨基料、油漆或油墨,其中所述有机液体是极性有机液体。
21.通式8的化合物:
通式(8)
其中
R2是氢或C1-4-烷基;
R3是含至多10个碳原子的脂族或芳族残基,其任选地含有可衍生自氧化丙烯和/或氧化乙烯的聚醚残基;
R是任选取代的C1-50-烃基;
A是羟基羧酸或其内酯的残基;
B是氨基羧酸的残基;
m和n是正整数;和
m+n为4-2000。
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EP1871515A2 (en) | 2008-01-02 |
US8772435B2 (en) | 2014-07-08 |
US20080163790A1 (en) | 2008-07-10 |
TWI402097B (zh) | 2013-07-21 |
TW200702045A (en) | 2007-01-16 |
WO2006113258A3 (en) | 2007-03-15 |
WO2006113258A2 (en) | 2006-10-26 |
CN102974264A (zh) | 2013-03-20 |
CN101175558A (zh) | 2008-05-07 |
EP1871515B1 (en) | 2015-09-30 |
JP5340723B2 (ja) | 2013-11-13 |
KR101334798B1 (ko) | 2013-11-29 |
JP2008536664A (ja) | 2008-09-11 |
CN102974264B (zh) | 2015-09-02 |
KR20070120597A (ko) | 2007-12-24 |
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