CN106232674A - 分散树脂 - Google Patents
分散树脂 Download PDFInfo
- Publication number
- CN106232674A CN106232674A CN201580016270.4A CN201580016270A CN106232674A CN 106232674 A CN106232674 A CN 106232674A CN 201580016270 A CN201580016270 A CN 201580016270A CN 106232674 A CN106232674 A CN 106232674A
- Authority
- CN
- China
- Prior art keywords
- acid
- dispersion resin
- polyester
- group
- glycol
- 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.)
- Granted
Links
- 239000006185 dispersion Substances 0.000 title claims abstract description 107
- 229920005989 resin Polymers 0.000 title claims abstract description 96
- 239000011347 resin Substances 0.000 title claims abstract description 96
- 239000007787 solid Substances 0.000 claims abstract description 46
- 238000002360 preparation method Methods 0.000 claims abstract description 19
- 229920000728 polyester Polymers 0.000 claims description 78
- 239000002253 acid Substances 0.000 claims description 47
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 46
- 239000000203 mixture Substances 0.000 claims description 44
- 238000006243 chemical reaction Methods 0.000 claims description 33
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 claims description 31
- 150000001991 dicarboxylic acids Chemical class 0.000 claims description 22
- 150000008064 anhydrides Chemical class 0.000 claims description 20
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 claims description 17
- 238000000034 method Methods 0.000 claims description 17
- 238000006116 polymerization reaction Methods 0.000 claims description 13
- 150000003077 polyols Chemical class 0.000 claims description 13
- 229920005862 polyol Polymers 0.000 claims description 12
- 150000001875 compounds Chemical class 0.000 claims description 11
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims description 7
- 229920002873 Polyethylenimine Polymers 0.000 claims description 7
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 6
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 claims description 6
- 150000003839 salts Chemical class 0.000 claims description 6
- ARCGXLSVLAOJQL-UHFFFAOYSA-N trimellitic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C(C(O)=O)=C1 ARCGXLSVLAOJQL-UHFFFAOYSA-N 0.000 claims description 6
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 claims description 5
- ODGCZQFTJDEYNI-UHFFFAOYSA-N 2-methylcyclohex-3-ene-1,2-dicarboxylic acid Chemical compound OC(=O)C1(C)C=CCCC1C(O)=O ODGCZQFTJDEYNI-UHFFFAOYSA-N 0.000 claims description 4
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 claims description 4
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 claims description 4
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 claims description 4
- 229910052799 carbon Inorganic materials 0.000 claims description 4
- JFCQEDHGNNZCLN-UHFFFAOYSA-N glutaric acid Chemical compound OC(=O)CCCC(O)=O JFCQEDHGNNZCLN-UHFFFAOYSA-N 0.000 claims description 4
- BDJRBEYXGGNYIS-UHFFFAOYSA-N nonanedioic acid Chemical compound OC(=O)CCCCCCCC(O)=O BDJRBEYXGGNYIS-UHFFFAOYSA-N 0.000 claims description 4
- 229920001223 polyethylene glycol Polymers 0.000 claims description 4
- CYIDZMCFTVVTJO-UHFFFAOYSA-N pyromellitic acid Chemical compound OC(=O)C1=CC(C(O)=O)=C(C(O)=O)C=C1C(O)=O CYIDZMCFTVVTJO-UHFFFAOYSA-N 0.000 claims description 4
- CXMXRPHRNRROMY-UHFFFAOYSA-N sebacic acid Chemical compound OC(=O)CCCCCCCCC(O)=O CXMXRPHRNRROMY-UHFFFAOYSA-N 0.000 claims description 4
- UWHCKJMYHZGTIT-UHFFFAOYSA-N tetraethylene glycol Chemical compound OCCOCCOCCOCCO UWHCKJMYHZGTIT-UHFFFAOYSA-N 0.000 claims description 4
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims description 3
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 claims description 3
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 claims description 3
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 claims description 3
- 239000002270 dispersing agent Substances 0.000 claims description 3
- 238000007306 functionalization reaction Methods 0.000 claims description 3
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 claims description 3
- 239000011976 maleic acid Substances 0.000 claims description 3
- QFGCFKJIPBRJGM-UHFFFAOYSA-N 12-[(2-methylpropan-2-yl)oxy]-12-oxododecanoic acid Chemical compound CC(C)(C)OC(=O)CCCCCCCCCCC(O)=O QFGCFKJIPBRJGM-UHFFFAOYSA-N 0.000 claims description 2
- JAHNSTQSQJOJLO-UHFFFAOYSA-N 2-(3-fluorophenyl)-1h-imidazole Chemical compound FC1=CC=CC(C=2NC=CN=2)=C1 JAHNSTQSQJOJLO-UHFFFAOYSA-N 0.000 claims description 2
- 229920000305 Nylon 6,10 Polymers 0.000 claims description 2
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 claims description 2
- 239000001361 adipic acid Substances 0.000 claims description 2
- 235000011037 adipic acid Nutrition 0.000 claims description 2
- 125000005907 alkyl ester group Chemical group 0.000 claims description 2
- 125000005277 alkyl imino group Chemical group 0.000 claims description 2
- 229940106691 bisphenol a Drugs 0.000 claims description 2
- VEIOBOXBGYWJIT-UHFFFAOYSA-N cyclohexane;methanol Chemical compound OC.OC.C1CCCCC1 VEIOBOXBGYWJIT-UHFFFAOYSA-N 0.000 claims description 2
- TUGLVWDSALSXCF-UHFFFAOYSA-N decane;methanol Chemical compound OC.OC.CCCCCCCCCC TUGLVWDSALSXCF-UHFFFAOYSA-N 0.000 claims description 2
- SZXQTJUDPRGNJN-UHFFFAOYSA-N dipropylene glycol Chemical compound OCCCOCCCO SZXQTJUDPRGNJN-UHFFFAOYSA-N 0.000 claims description 2
- 239000001530 fumaric acid Substances 0.000 claims description 2
- XXMIOPMDWAUFGU-UHFFFAOYSA-N hexane-1,6-diol Chemical compound OCCCCCCO XXMIOPMDWAUFGU-UHFFFAOYSA-N 0.000 claims description 2
- HNEGQIOMVPPMNR-NSCUHMNNSA-N mesaconic acid Chemical compound OC(=O)C(/C)=C/C(O)=O HNEGQIOMVPPMNR-NSCUHMNNSA-N 0.000 claims description 2
- LVHBHZANLOWSRM-UHFFFAOYSA-N methylenebutanedioic acid Natural products OC(=O)CC(=C)C(O)=O LVHBHZANLOWSRM-UHFFFAOYSA-N 0.000 claims description 2
- HNEGQIOMVPPMNR-UHFFFAOYSA-N methylfumaric acid Natural products OC(=O)C(C)=CC(O)=O HNEGQIOMVPPMNR-UHFFFAOYSA-N 0.000 claims description 2
- UFDHBDMSHIXOKF-UHFFFAOYSA-N tetrahydrophthalic acid Natural products OC(=O)C1=C(C(O)=O)CCCC1 UFDHBDMSHIXOKF-UHFFFAOYSA-N 0.000 claims description 2
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 claims description 2
- HBGPNLPABVUVKZ-POTXQNELSA-N (1r,3as,4s,5ar,5br,7r,7ar,11ar,11br,13as,13br)-4,7-dihydroxy-3a,5a,5b,8,8,11a-hexamethyl-1-prop-1-en-2-yl-2,3,4,5,6,7,7a,10,11,11b,12,13,13a,13b-tetradecahydro-1h-cyclopenta[a]chrysen-9-one Chemical compound C([C@@]12C)CC(=O)C(C)(C)[C@@H]1[C@H](O)C[C@]([C@]1(C)C[C@@H]3O)(C)[C@@H]2CC[C@H]1[C@@H]1[C@]3(C)CC[C@H]1C(=C)C HBGPNLPABVUVKZ-POTXQNELSA-N 0.000 claims 5
- PFRGGOIBYLYVKM-UHFFFAOYSA-N 15alpha-hydroxylup-20(29)-en-3-one Natural products CC(=C)C1CCC2(C)CC(O)C3(C)C(CCC4C5(C)CCC(=O)C(C)(C)C5CCC34C)C12 PFRGGOIBYLYVKM-UHFFFAOYSA-N 0.000 claims 5
- SOKRNBGSNZXYIO-UHFFFAOYSA-N Resinone Natural products CC(=C)C1CCC2(C)C(O)CC3(C)C(CCC4C5(C)CCC(=O)C(C)(C)C5CCC34C)C12 SOKRNBGSNZXYIO-UHFFFAOYSA-N 0.000 claims 5
- QSAWQNUELGIYBC-UHFFFAOYSA-N cyclohexane-1,2-dicarboxylic acid Chemical compound OC(=O)C1CCCCC1C(O)=O QSAWQNUELGIYBC-UHFFFAOYSA-N 0.000 claims 2
- PMUPSYZVABJEKC-UHFFFAOYSA-N 1-methylcyclohexane-1,2-dicarboxylic acid Chemical compound OC(=O)C1(C)CCCCC1C(O)=O PMUPSYZVABJEKC-UHFFFAOYSA-N 0.000 claims 1
- 244000248349 Citrus limon Species 0.000 claims 1
- 235000005979 Citrus limon Nutrition 0.000 claims 1
- ALQSHHUCVQOPAS-UHFFFAOYSA-N Pentane-1,5-diol Chemical compound OCCCCCO ALQSHHUCVQOPAS-UHFFFAOYSA-N 0.000 claims 1
- CDQSJQSWAWPGKG-UHFFFAOYSA-N butane-1,1-diol Chemical compound CCCC(O)O CDQSJQSWAWPGKG-UHFFFAOYSA-N 0.000 claims 1
- 239000008187 granular material Substances 0.000 claims 1
- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 claims 1
- -1 tetrabutyl titanate ester Chemical class 0.000 description 28
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 24
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 18
- 239000007788 liquid Substances 0.000 description 18
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 15
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 13
- 239000000049 pigment Substances 0.000 description 13
- 239000000463 material Substances 0.000 description 12
- 239000003973 paint Substances 0.000 description 12
- 150000002762 monocarboxylic acid derivatives Chemical class 0.000 description 10
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
- POULHZVOKOAJMA-UHFFFAOYSA-N dodecanoic acid Chemical compound CCCCCCCCCCCC(O)=O POULHZVOKOAJMA-UHFFFAOYSA-N 0.000 description 8
- 239000000975 dye Substances 0.000 description 8
- 150000002148 esters Chemical class 0.000 description 8
- 239000000945 filler Substances 0.000 description 8
- VYKXQOYUCMREIS-UHFFFAOYSA-N methylhexahydrophthalic anhydride Chemical compound C1CCCC2C(=O)OC(=O)C21C VYKXQOYUCMREIS-UHFFFAOYSA-N 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- LGRFSURHDFAFJT-UHFFFAOYSA-N Phthalic anhydride Natural products C1=CC=C2C(=O)OC(=O)C2=C1 LGRFSURHDFAFJT-UHFFFAOYSA-N 0.000 description 7
- JHIWVOJDXOSYLW-UHFFFAOYSA-N butyl 2,2-difluorocyclopropane-1-carboxylate Chemical compound CCCCOC(=O)C1CC1(F)F JHIWVOJDXOSYLW-UHFFFAOYSA-N 0.000 description 7
- 239000003054 catalyst Substances 0.000 description 7
- 125000002887 hydroxy group Chemical class [H]O* 0.000 description 7
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 238000009833 condensation Methods 0.000 description 6
- 230000005494 condensation Effects 0.000 description 6
- 235000014113 dietary fatty acids Nutrition 0.000 description 6
- 239000000194 fatty acid Substances 0.000 description 6
- 229930195729 fatty acid Natural products 0.000 description 6
- 150000004665 fatty acids Chemical class 0.000 description 6
- 239000002245 particle Substances 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- 239000004793 Polystyrene Substances 0.000 description 5
- 125000003368 amide group Chemical group 0.000 description 5
- 239000003795 chemical substances by application Substances 0.000 description 5
- 239000011248 coating agent Substances 0.000 description 5
- 238000000576 coating method Methods 0.000 description 5
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 4
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
- 239000005639 Lauric acid Substances 0.000 description 4
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 4
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 4
- 239000000654 additive Substances 0.000 description 4
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- 150000001412 amines Chemical group 0.000 description 4
- 238000004821 distillation Methods 0.000 description 4
- 150000002466 imines Chemical class 0.000 description 4
- 239000003112 inhibitor Substances 0.000 description 4
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 4
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 4
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- PNEYBMLMFCGWSK-UHFFFAOYSA-N Alumina Chemical compound [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
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- 229920000877 Melamine resin Polymers 0.000 description 3
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 3
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- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 3
- PGEHNUUBUQTUJB-UHFFFAOYSA-N anthanthrone Chemical compound C1=CC=C2C(=O)C3=CC=C4C=CC=C5C(=O)C6=CC=C1C2=C6C3=C54 PGEHNUUBUQTUJB-UHFFFAOYSA-N 0.000 description 3
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 3
- 239000011230 binding agent Substances 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 230000008859 change Effects 0.000 description 3
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- 230000032050 esterification Effects 0.000 description 3
- 238000005886 esterification reaction Methods 0.000 description 3
- 239000007789 gas Substances 0.000 description 3
- 229910052736 halogen Inorganic materials 0.000 description 3
- 150000002367 halogens Chemical class 0.000 description 3
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 3
- 229910052739 hydrogen Inorganic materials 0.000 description 3
- 239000001257 hydrogen Substances 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
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- AXTGDCSMTYGJND-UHFFFAOYSA-N 1-dodecylazepan-2-one Chemical compound CCCCCCCCCCCCN1CCCCCC1=O AXTGDCSMTYGJND-UHFFFAOYSA-N 0.000 description 2
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- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 2
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- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 2
- 239000002671 adjuvant Substances 0.000 description 2
- 239000003905 agrochemical Substances 0.000 description 2
- 229920000180 alkyd Polymers 0.000 description 2
- 150000003863 ammonium salts Chemical class 0.000 description 2
- 239000006229 carbon black Substances 0.000 description 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 2
- 239000004359 castor oil Substances 0.000 description 2
- 235000019438 castor oil Nutrition 0.000 description 2
- 229910010293 ceramic material Inorganic materials 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- 229910017052 cobalt Inorganic materials 0.000 description 2
- 239000010941 cobalt Substances 0.000 description 2
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 2
- 150000004292 cyclic ethers Chemical class 0.000 description 2
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Classifications
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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
- C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
- C08G63/02—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds
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- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
- C08G63/02—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds
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- C08G63/46—Polyesters chemically modified by esterification
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- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
- C08G63/91—Polymers modified by chemical after-treatment
- C08G63/912—Polymers modified by chemical after-treatment derived from hydroxycarboxylic acids
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Abstract
本发明涉及创新性的分散树脂、其制备及其在分散固体方面的应用。
Description
本发明涉及创新性分散树脂、其制备及其在分散固体方面的应用。
使用分散树脂将固体(如填料、染料或颜料)通常分散在液体介质中以实现所述固体的有效稳定化,降低所需机械剪切力,并且从而使非常高度的填充成为可能。作为表面活性材料,分散树脂润湿和/或覆盖所要分散颗粒的表面,并稳定化它们从而不发生不想要的再结块。因此,在油漆、清漆、印刷油墨和其它涂料生产时,分散树脂有利于固体的引入,例如填料和颜料,其作为重要的配制成分基本上决定了该体系的外观和物理化学性质。为了最好的使用,这些固体一方面必须在所述配制剂中均匀地分布,另一方面所述分布一旦实现还必须被稳定化。
目前,多种不同物质被用作固体的分散剂。除低分子量的非常简单的化合物例如卵磷脂、脂肪酸和它们的盐或烷基酚乙氧基化物外,高分子量更复杂的结构也被用作分散树脂。这里,特别是氨基官能化和酰胺基官能化的体系具有广泛应用。
例如,DE 2830860、WO 00/24503和WO 01/21298描述了基于聚酯改性的多胺的分散树脂。EP 893155描述了多胺的盐及其作为颜料和填料的分散树脂的用途。所述聚酯基于羟基羧酸或内酯。
分散树脂的使用还可能导致缺点,例如在下述方面:通常需要在颜料糊剂中使用高含量的分散添加剂;所能实现的糊剂颜料化的程度为不令人满意的低;所述糊剂的稳定性及因此它们粘度的一致性不够;不可避免地要使用溶剂;或始终不能阻止发生絮凝和凝聚。类似地,通常在所述糊剂存放之后,还缺少色彩深浅的一致性,缺少与不同粘结剂和颜料的相容性。通过使用现有技术中已知的分散添加剂,在很多情况下,还在涂料的耐水性或光稳定性方面有副作用,或者在其使用时会产生不想要的泡沫。还有在很多情况下,因分散树脂在商用涂料介质中缺乏相容性,光泽受到不利影响。此外,焦点越来越被放在市售和价格低廉的、如果可能,甚至是从可再生来源获得的原材料上。
因此对于具有比现有技术更为改善性质的固体用分散树脂而言,存在不断增长的需求。在此方面一个具体的需求就是对大量不同的固体都具有非常高的稳定化作用的分散树脂。
因此,本发明的一个目的就在于提供具有改善的性能特性并可有利地被用于,例如,分散固体的分散树脂。
前述目的通过本发明的新分散树脂而实现。
本发明的第一主题因此就是通式(I)的分散树脂,
T-P-Z-T (I)
其中
T是终止聚合的基团,
Z是碱性基团或包含碱性基团的基团,
P是基于二羧酸或多羧酸和二醇或多醇的聚酯,包括式(I)化合物的盐。
本发明的分散树脂表现出有效的分散性能,对相应配制剂的粘度和流变性质没有负面影响。相应地,使用本发明树脂,可降低昂贵颜料的使用量,而不用接受色强度的减损。此外,包含染料、固体如填料和/或颜料的糊剂、油漆、清漆、印刷油墨和其它涂料基本上由所用的分散树脂共同决定。这里,本发明的分散树脂满足对生产非常低粘度的通常要求,而且保持在液体油漆和清漆中,优选牛顿粘度行为。此外,本发明的分散树脂基于廉价的市售原材料。特别是对于本发明式(I)树脂中的P部分的确如此,其中二羧酸和二醇被用于形成聚酯,从而使得其可以避免使用现有技术已知为昂贵且不便利的己内酯。使用价廉和市售的原材料,特别是对于P部分,允许了本发明的分散树脂更宽的结构变化和供应安全性。
本发明式(I)的分散树脂的一部分是基于二羧酸或多羧酸及二醇或多醇的聚酯单元P。该式(I)的分散树脂中的聚酯单元P通常是羧酸官能化的聚酯,仍可能带有自由的OH基团,该基团的一些或全部可能会在后续反应中与例如酐反应以形成羧酸官能化的聚酯。所述的聚酯,更具体而言OH-官能化的,优选是直链或轻微支化的和饱和的或不饱和的无定形共聚酯。
本发明所涉及的二羧酸或多羧酸包括游离酸、其酸酐或所述二羧酸的酯;当是酯时,优选低分子量的酯,例如甲基或乙基酯。
适用的二羧酸或多羧酸是,例如,邻苯二甲酸、间苯二甲酸、对苯二甲酸、1,2-环己烷二羧酸和异构体、琥珀酸、癸二酸、甲基四氢邻苯二甲酸、甲基六氢邻苯二甲酸、六氢邻苯二甲酸或四氢邻苯二甲酸、十二烷二酸、己二酸、戊二酸、柠康酸、富马酸、衣康酸、马来酸或中康酸、壬二酸、苯均四酸和/或偏苯三酸、它们的酸酐和/或低分子量烷基酯,例如甲基酯。
适用的二醇或多醇是,特别是,乙二醇、1,2-和/或1,3-丙二醇、二甘醇、双丙甘醇、三甘醇、四甘醇、1,2-和/或1,4-丁二醇、1,3-丁基乙基丙二醇、1,3-甲基丙二醇、1,5-戊二醇、环己基二甲醇、4,8-三环[5.2.1.O2,7]癸烷二甲醇(Dicidol)、甘油、1,6-己二醇、新戊二醇、双酚A、B、C、F、降冰片烯二醇、1,4-苄基二甲醇和1,4-苄基二乙醇和/或2,4-二甲基-2-乙基己烷-1,3-二醇。
所述聚酯单元P优选包含25-75wt%的二羧酸或多羧酸和25-75wt%的二醇或多醇,二醇或多醇之和与二羧酸或多羧酸之和构成100wt%。
聚酯的制备为技术人员所熟知。其通常是通过二羧酸或多羧酸或它们的酸酐与二醇或多醇缩合而制备。它们的性质在很大程度上取决于起始原料的性质和比例。
在本发明的内容中,所述聚酯单元是通过起始酸和起始醇的连续或(半)批量的酯化和缩合,以一步或两步法制备的。该聚酯单元优选通过熔融缩合方法合成。为此,所用的二羧酸或多羧酸与二醇或多醇发生反应。聚缩聚在130-280℃之间的温度于熔融状态下进行3-30小时。在该步骤中产生的大部分水在大气压力下被首先蒸馏除去。在反应的进一步过程中,剩余的水还有挥发性二醇或多醇也被除去直至达到目标分子量或所需酸值。可以任选地通过降低压力或通过让惰性气体流经所述反应混合物而促进该过程。可额外地通过在反应前或反应过程中添加共沸剂和/或催化剂而加速所述反应。适用的共沸剂是甲苯和二甲苯。典型的催化剂是有机钛或有机锡化合物,如四丁基钛酸酯或二丁基氧化锡。还可以想到的是基于其它金属的催化剂,如基于锌的乙酸锌,或基于锑或锆的,如异丙氧基锆,以及不含金属的酯化催化剂,如甲苯磺酸,或有机强酸如卤乙酸,例如三氟乙酸。还有可能的是其它添加剂和工艺助剂如抗氧化剂、基团稳定剂和颜色稳定剂。所述反应优选在惰性气体环境如氮气下进行。
相应制备的聚酯随后在下一步与二羧酸或其酸酐反应以得到酸官能化的聚酯。这些聚酯被称为P-COOH。基于该OH基团,20-100%,优选30-80%,更优选40-70%,与二羧酸或其酸酐反应。在本步中,优选使用酸酐。所用酸酐为,例如,邻苯二甲酸(PAn)、1,2-环己烷二羧酸、琥珀酸、马来酸、甲基四氢邻苯二甲酸、甲基六氢邻苯二甲酸(MHH-PhA)、六氢邻苯二甲酸、和或偏苯三酸的酸酐。
本发明聚酯特别地具有Mn为700-10 000g/mol,优选900-4000g/mol,和Mw为1500-40 000g/mol,优选2000-15 000g/mol。在本发明的上下文中,摩尔质量通过尺寸排阻色谱法(size exclusion chromatography,SEC)测定。为此,三个由Merck得到的颗粒尺寸为5μm的色谱柱(PS 400,250*7mm,PS 40,250*7mm,和PS 1,250*7mm)串联组合。校准后,用Rheodyne 7125注射器于40℃下注射20μl聚酯的四氢呋喃溶液(c(polyester)=20mg/ml),并用脱气的四氢呋喃作为流动相及40℃下的差示折光仪(Waters型号410)在40℃下以1ml/min(Waters 510 HPLC泵)的流速进行分析。在以上述方法用聚苯乙烯标样进行校正后进行评估。聚苯乙烯标样(标样1Mp 377400、Mp 96000、Mp 20650、Mp 1300、Mp 162;标样2 Mp283300、Mp 50400、Mp 10850、Mp 2930、Mp 980;标样3 Mp 218800、Mp 68900、Mp 10050、Mp1940、Mp 580;Mp=最大峰值分子量)为市售,例如,来自Merck或Polymer Laboratories。
此外,聚酯的OH值为30-300mg KOH/g,优选50-200mg KOH/g。在本发明中,所述OH值根据DIN 53240-2测定。在使用该方法时,样品在4-二甲基氨基吡啶催化剂的存在下与乙酸酐反应,使得羟基被乙酰基化。对于每一个羟基,这都产生一分子的乙酸,同时随后过量乙酸酐的水解产生两分子的乙酸。乙酸的消耗通过滴定法由主值和平行实验所得的空白值之间的差来确定。
此外,所述聚酯P根据DIN EN ISO 2114确定的酸值优选为小于100mgKOH/g,优选为10-80mg KOH/g,更优选20-60mg KOH/g。所述酸值(AN)是中和1克物质中所包含的羧酸所需要的氢氧化钾mg数。分析用样品被溶解在二氯甲烷中,用0.1N的氢氧化钾乙醇溶液对酚酞进行滴定。
式(I)的分散树脂的另一个组成部分是Z基团,其是碱性基团或包含碱性基团的基团(radical)。Z基团特别是多官能性的,意味着多于一个T-P基团和/或T基团可共价连接到Z上,或者作为盐。在一个优选的实施方案中,所述Z基团包含聚烯丙基胺或聚(C2-4-亚烷基亚胺),优选聚(C2-4-亚烷基亚胺)。
所述聚(C2-4-亚烷基亚胺)优选是聚亚乙基亚胺(PEI),其可以是直链或支化的。所述物质优选包含具有支化聚合物结构的多官能团、阳离子型聚亚乙基亚胺。它们的组成用经验式(CH2-CH2-NH)n-表示,其中10<n<105。其通常是透明至微浊,无色至黄色的液体。其粘度取决于分子量、浓度和支化度。
所述聚(C2-4-亚烷基亚胺),特别优选聚亚乙基亚胺,优选平均分子量Mw为200-600 000g/mol,更优选400-100 000g/mol,非常优选600-30 000g/mol。
优选的聚亚乙基亚胺为市售产品,例如BASF SE的或NipponShokubai的EPOMIN。
T基团是终止聚合的基团。在本文中,该终止聚合的基团通常被称为阻聚剂(stopper)。
终止聚合的合适基团是单羧酸,特别优选不含氨基的单羧酸。
优选的单羧酸是C1-25脂肪单羧酸,其可以是饱和的或不饱和的,可以是被羟基或C1-4烷氧基或卤素取代的。优选的脂肪族单羧酸包含8个或更多的碳原子。如果所述脂肪族单羧酸是取代的,该取代基优选是羟基。特别优选的单羧酸的实例是乙醇酸、乳酸、己酸、月桂酸、硬脂酸、甲氧基乙酸、蓖麻油酸、12-羟基硬脂酸、12-羟基十二烷酸、5-羟基十二烷酸、5-羟基癸酸和4-羟基癸酸。前述酸可单独使用或作为不同酸的混合物使用。
T作为阻聚剂的活性源于其防止网络结构的构建,并相应地抑制任何凝胶化。聚酯链的长度可以通过T阻聚剂的存在而控制,例如通过在制备过程中使用单羧酸。
在一个本发明的实施方案中,形成T基团的化合物,更具体而言是单羧酸,被添加到实际合成聚酯单元P的过程中。此时,聚酯单元T-P具有由25-80wt%二羧酸或多羧酸、25-80wt%二醇或多醇及1-25wt%的终止聚合基团更具体而言是单羧酸构成的组成,组成的总和等于100wt%。
键接到聚酯P上的T基团可以不同于直接键接到Z上的T基团。相应的,可以在聚酯制备过程中及T基团与带有Z的中间体T-P的反应过程中使用两种不同的T基团。不排除在聚酯制备和其与Z的反应过程中使用不同的T基团。
Z基团化合物,特别是聚烯丙基胺或聚(C2-4-亚烷基亚胺),对聚酯P(下文中也被称为T-P-COOH)的重量比可在宽范围内变化,取决于本发明的分散树脂随后被用于在极性还是非极性有机溶剂中分散颗粒状固体。当聚酯P(T-P-COOH)对Z基团化合物,更具体而言是聚烯丙基胺或聚(C2-4-亚烷基亚胺),的重量比在30∶1和1∶1之间时,优选在20∶1和2∶1之间和更优选在15∶1和4∶1之间,使用分散树脂得到了有利的结果。
在制备聚酯P的过程中T基团可类似地是脂肪族或芳香族醇,T-OH;直接连接到Z上的T基团始终都是单羧酸。T-OH的实例是异丙醇、异丁醇、叔丁醇、2-乙基丁醇、3-庚醇、辛醇、癸醇、十二烷醇、2-乙基己醇、3,5,5-三甲基己醇、3,7-二甲基辛醇、苯酚、烷基酚。此外,格尔伯特醇(Guerbet alcohols)也是适用的。格尔伯特醇是在相对于CH2OH基团的β位置有支化的伯醇。格尔伯特醇对技术人员为已知;许多都已经是市售可得的。其通过已知100多年的Guerbet二聚反应获得。格尔伯特醇的适当代表是商品名为Isofol(Condea GmbH)的市售醇。
T和T-P基团通过T或聚酯P的羧基与Z相连。因此优选的分散树脂衍生于聚酯的酸基团(T-P-COOH,即具有末端羧酸基团的P链)和额外的T的酸基团在Z上的缩合。所述聚酯的酸基团可以是聚酯成分的羧酸基团,或者是已经随后与二羧酸和/或酸酐反应的聚酯的羟基。下述反应步骤给出了基本的反应类型。
Z、T和P的含义如上定义。
在本发明的一个优选实施方案中,所述分散树脂包含聚烯丙基胺或聚(C2-4-亚烷基亚胺)作为Z基团,与其连接的是至少两个相同或不同的T-P型链。不同的T-P型链被连接到Z上通常是为了优化涂料体系内的相容性,并允许所述分散剂在许多配制剂体系中的广泛应用。前述T-P型的每个聚酯链通过聚酯单元P的末端羧基与聚烯丙基胺或聚(C2-4-亚烷基亚胺)的伯氨基或仲氨基间的共价酰胺键、或者通过聚酯单元P的羧酸根基与聚烯丙基胺或聚(C2-4-亚烷基亚胺)的取代铵基的带正电的氮原子间的离子盐价键优选被连接到聚烯丙基胺或聚(C2-4-亚烷基亚胺)上。因为在所述优选实施方案中,分散树脂包含至少两个T-P型聚酯链,因此可能有各自聚酯链的酰胺键和盐键的混合物,取决于制备分散树脂时为了连接聚酯链与Z基团酰胺化使用的反应条件的严格性。该优选的分散树脂可用式(II)以简化形式代表,
其中
X-*-*-X是聚烯丙基胺或聚(C2-4亚烷基亚胺),
Y是T-P聚酯链,其通过酰胺或盐键与所述聚烯丙基胺或聚(C2-4亚烷基亚胺)相连,T和P定义如上,且q为2-2000。
优选q大于2和更优选其不小于5。此外,还优选q不大于1000和优选其不大于500。
进一步优选式(II)中的单元Y对聚烯丙基胺或聚(C2-4亚烷基亚胺)(其在式(II)中用X-*-*-X代表)的重量比在30∶1和1∶1之间,非常优选在20∶1和2∶1之间,特别优选在15∶1和4∶1之间。
本发明的分散树脂可通过相应成分T、P或T-P和Z的反应制备。本发明的另一个主题相应地是制备本发明的分散树脂的方法,包含第一步二羧酸或多羧酸与二醇或多醇在终止聚合的基团的存在下缩合,第二步将第一步所得聚酯与二羧酸或其酸酐反应以形成酸官能化的聚酯,和第三步随后将第二步所得酸官能化的聚酯与Z基团的化合物反应。此外,在所述第三步中,优选类似地存在终止聚合的基团T。
在根据式(II)的本发明优选实施方案中,所述制备通过聚烯丙基胺或聚(C2-4-亚烷基亚胺),更具体而言是聚亚乙基亚胺,与键连有T基团的酸官能化聚酯单元P反应而实施,任选添加额外的T。在一个优选实施方案中,在上述反应中添加了额外的T。
例如,所述分散树脂可来源于含有至少两个伯氨基、仲氨基或叔氨基的聚烯丙基胺或聚(C2-4-亚烷基亚胺)及中间体T-P-COOH,其中中间体T-P-COOH的羧基是聚酯单元P的羧基。聚烯丙基胺或聚(C2-4-亚烷基亚胺)的氨基与聚酯P的羧基可形成酰胺或盐键。如果所述聚(C2-4-亚烷基亚胺)只含有叔氨基,则只形成盐键;否则,盐键或酰胺键的形成取决于反应条件。通常来讲,温和的反应条件如低温和/或短的反应时间支持形成盐键,而更严格的反应条件如高温和/或长的反应时间支持形成酰胺键。这些情况对技术人员而言是已知的。
在本发明方法的第三步中,得到本发明分散树脂的聚烯丙基胺或聚(C2-4-亚烷基亚胺)与中间体T-P-COOH的反应在50-250℃的温度下进行,优选在惰性气氛下并任选存在酯化催化剂。所述温度优选不小于80℃和更优选不小于100℃。为了最小化所要形成的分散树脂的碳化,所述温度优选不超过200℃和更优选不超过180℃。合适的惰性气体原则上是任何不与最终产品或起始原料反应的气体,实例是稀有气体或氮气,优选使用氮气。
优选在与聚烯丙基胺或聚(C2-4-亚烷基亚胺)反应前单独制备酸官能化聚酯。此时,二羧酸或多羧酸与二醇或多醇在惰性气氛下于150-250℃反应,优选使用单羧酸作为阻聚剂T,任选存在酯化催化剂,所得聚酯随后与二羧酸或其酸酐反应以得到酸官能化的聚酯。所得T-P-COOH型聚酯与聚烯丙基胺或聚(C2-4-亚烷基亚胺)的后续反应随后在50-250℃下实施,优选100-180℃,优选存在T。
如果通过上述制备模式所得的分散树脂包含自由氨基,其可通过与酸或季铵化试剂反应而转化成取代的铵基,意味着所述分散树脂为取代铵盐的形式。适用于此目的的试剂是矿物酸和强有机酸或酸盐如乙酸、硫酸、盐酸、烷基磺酸、烷基硫酸氢盐和芳基磺酸,例如包括酸形式的染料和颜料,和季铵盐试剂,如二烷基硫酸酯,例如硫酸二甲酯(DMS),和卤代烷,如甲基和乙基卤代物。
本发明的另一个主题是包含本发明的分散树脂的组合物。本发明的组合物特别包含本发明分散树脂及颗粒固体。在本发明的另一个实施方案中,所述组合物优选包含由式(I)的分散树脂、颗粒固体和有机介质所组成的分散体。
存在于本发明的组合物中的颗粒固体可包含任何有机或无机固体材料。更具体而言,该颗粒固体是基本上不溶于所述有机介质中的,并通过所述分散树脂以细微分散的形式稳定在其中。
合适固体的实例是染料、颜料、填料和其它固体助剂和辅剂。特别适用的细微分散的固体的实例是,特别是,用于溶解油墨的颜料,用于油漆和塑料的颜料、补充剂和填充剂,用于纺织品的染料,更具体而言是细微分散的染料,荧光增白剂和佐剂,用于液体染色浴、液体油墨和其它液体应用系统的固体颗粒,例如,用于油基钻井泥浆和逆乳化液(invertemulsion)的固体,污染物和用于干洗液体中的颗粒固体,颗粒状陶瓷材料,磁性材料和用于磁记录的物质,还有被用作有机介质中分散体的杀菌剂、农用化学品和药物。
优选使用的细微分散固体是公认颜料类别中的一种颜料,其描述于例如ColourIndex(1971)第三版及其后续修正版和补充版中的题目为‘Pigments’的部分中。无机颜料的实例是二氧化钛、氧化锌、普鲁士蓝、硫化镉、铁氧化物、朱砂、群青和铬颜料,包括铬酸盐,钼酸盐和混合的铬酸盐以及铅、锌、钡、钙的硫酸盐及其混合物,以及其可市购的改性物,名称为Primrose、Lemon、Middle、Orange、Scarlet和Red chromes的黄绿色到红色的颜料。有机颜料的实例特别选自偶氮、双偶氮、缩合偶氮、硫靛、阴丹酮、异阴丹酮、蒽嵌蒽醌(anthanthrone)、蒽醌、异蒽酮紫(isodibenzanthrone,)、三苯二嗪、喹吖酮和酞菁系列,更特别是铜酞菁和其环卤代衍生物,以及酸性、碱性和媒染染料的色淀。从其分散性质来讲,炭黑,虽然严格来讲是无机的,但其表现更像有机颜料。优选的有机颜料是酞菁,优选铜酞菁,单偶氮,双偶氮,阴丹酮,蒽嵌蒽醌,喹吖酮染料,和炭黑。
其它优选的细微分散的固体是补充剂和填料,例如滑石、高岭土、二氧化硅、重晶石和石灰,颗粒状陶瓷材料,例如氧化铝、二氧化硅、二氧化锆、二氧化钛、氮化硅、氮化硼、碳化硅、碳化硼、混合的硅铝氮化物和金属钛酸盐,尤其是磁性物质,如过渡金属优选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,优选亚铁酸钡和金属颗粒,优选金属铁、镍、钴以及其合金,以及额外的农用化学品,如杀真菌剂粉唑醇、多菌灵、百菌清和代森锰锌。
优选存在于本发明组合物中的有机介质优选包含极性有机介质或非极性芳香烃或卤代烃。涉及所述有机介质的术语“极性”指的是如Crowley等人在期刊“PaintTechnology”,卷38,1966,页269,文章题目为“A Three Dimensional Approach toSolubility”中所述的,能够形成中到强的价键的有机液体或树脂。这些种有机介质通常含有的氢键个数为五或更多,如上述文章中所定义的。
适用的极性介质的实例是胺、醚,优选低级烷基醚、有机酸、酯、酮、乙二醇、醇和酰胺。许多具有中等强度氢键的这些液体的实例报道于Ibert Mellan(1968出版于NoyesDevelopment Corporation)的名为“Compatibility and Solubility”的书中,页39-40的表2.14。该刊物中所给出的液体都属于极性有机介质的术语范畴,并因此是本公开的一部分。
优选的极性有机液体是二烷基酮、烷基羧酸的烷基酯及烷醇、二醇和二醇酯和醚、烷醇、和环醚,优选那些含有至多并包括6个碳的液体。特别优选的有机介质是二烷基和环烷基酮,如丙酮、甲基乙基酮、二乙酮、二异丙基酮、甲基异丁基酮、二异丁基酮、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、乙酸异丙酯、乙酸丁酯、甲酸乙酯、丙酸甲酯、乙酸甲氧基丙酯和丁酸乙酯,二醇类和二醇酯和醚,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-丁氧基乙酯、乙酸3-甲氧基丙酯、乙酸3-乙氧基丙酯和乙酸2-乙氧基乙酯,烷醇,如甲醇、乙醇、正丙醇、异丙醇、正丁醇和异丁醇,以及二烷基醚和环醚,如乙醚和四氢呋喃。
可以单独使用或与前述极性有机介质形成混合物使用的基本上非极性的介质是芳香烃,如甲苯和二甲苯,和卤代脂肪族和芳香族烃,如三氯乙烯、全氯乙烯和氯苯。
用于本发明分散体形式的合适的极性树脂介质的实例是那些可成膜的树脂,其适用于制备液体油墨、油漆和用于许多应用如油漆和液体油墨中的片料。这些树脂的实例包括聚酰胺,如BASF SE的VersamidTM,或纤维素醚,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油醇酸树脂/三聚氰胺-甲醛树脂、聚酯/三聚氰胺-甲醛树脂、热固性丙烯酸树脂/三聚氰胺-甲醛树脂、长油醇酸树脂、和多层树脂如丙烯酸和脲/醛树脂。
如果需要,分散体可包含其它成分,实例是树脂(如果它们没有已经构成有机介质)、粘合剂、液化试剂(如GB-A-1508576和GB-A-2108143所描述的那些)、防沉降剂、塑化剂、流平剂和防腐剂。
本发明组合物,特别是优选的分散体,通常包含5-95wt%的细微分散固体,精确的量取决于所述固体的性质,及固体和有机介质的相对密度。例如,固体为有机物质如有机颜料的分散体优选包含15-60wt%的固体,而固体为无机物质如无机颜料、填料试剂或补充剂的分散体优选包含40-90wt%的细微分散固体,基于分散体的总重量。
本发明的组合物,更具体而言本发明的分散体,可通过任何常用制备组合物和分散体的方法获得。所述固体、有机介质和本发明分散树脂可通常以任何所需的顺序混合。此时,该混合物可用机械方法将固体颗粒的尺寸降低到适当的尺寸,例如通过球磨、珠磨、砾石磨或塑料压延(plastics rolling)。所述固体,独立地或在与有机介质或者分散树脂的混合物中,可选择地被处理以降低其颗粒尺寸,之后,可添加所述组合物的其它成分,所述混合物可被搅拌以制备所述组合物,优选所述分散体。
如果需要干状的组合物,则所述液体介质优选是挥发性的,从而可通过简单的分离方法如蒸发而将其从颗粒固体中除去。然而仍然优选所述分散体包含液体介质。
如果所述干状组合物基本上由分散树脂和颗粒固体组成,其优选包含至少0.2wt%,更优选至少0.5wt%和优选至少1.0wt%的本发明分散树脂,基于颗粒固体的重量。该干状组合物优选含有不超过50wt%,更优选不超过20wt%和优选不超过10wt%的本发明分散树脂,基于颗粒固体的重量。
如上所述,本发明的分散树脂特别适用于制备研磨料。在本发明的另一个实施方案中,所述颗粒固体在本发明的分散树脂和成膜树脂粘合剂的存在下和任选存在有机介质的条件下被研磨。
因此,根据本发明的另一个方面,提供了研磨料,其包含颗粒固体、本发明的分散树脂、和成膜树脂。
所述研磨料通常包含研磨料总重量的20-70wt%的颗粒固体。所述颗粒固体的量优选不少于研磨料的30wt%和更优选不少于50wt%。
研磨料中树脂的量可在宽范围内波动,但优选不少于研磨料总重量的10wt%和更优选不少于20wt%。
研磨料中本发明分散树脂的量取决于颗粒固体的量,但优选是研磨料的0.5-5wt%。
包含本发明分散树脂的分散体和研磨料特别适用于油漆优选高固含量的油漆,和液体油墨优选柔性版印刷用的液体油墨、凹版印刷油墨和丝网印刷油墨。此外,它们可有利的适用于非水陶瓷技术中,特别是在带涂覆、使用刮刀的铺展法(spreading method)、或挤出或注塑成型方法中。
在所述的应用中,本发明分散树脂比已知的分散树脂特别是那些基于由羟基羧酸或内酯所形成的聚酯的那些分散树脂具有优势。特别是,本发明分散树脂在有机介质如溶剂中具有更大的溶解性。相应地,它们不会在4℃的长期存放下分离出来或结晶。如果存放在低温下,分离可能会在-25℃发生。然而在这些情况下,本发明分散树脂可在加热到4-10℃时很容易地重新溶解。当本发明分散树脂被引入到油漆和装饰油墨中时,它们会给予所得油漆和油墨更高的光泽度和更低的雾度。
即使没有进一步的观察,也可假设本领域技术人员能够在其最宽的范围内利用上述说明。因此,优选的实施方案和实施例应解释为仅是描述性公开,其不以任何方式限制。
下面通过实施例对本发明进行更详细的阐述。本发明的替代实施方案可类似地获得。
实施例:
在下述实施例中,所有的数量,除非另有说明,都是基于重量份数。胺值、OH值和酸值都以mg KOH/g为单位报道。所用单体和相应的用于合成聚酯和本发明分散树脂的单体的量在下表中给出,报道了所得聚酯或分散树脂的特性(OH值,酸值和分子量)。
中间体的制备
实施例A)通过添加单羧酸制备的聚酯P:
所述聚酯中间体P的制备是通过本领域技术人员已知的聚酯制备方法。为此,首先在配有机械搅拌器、温度计和回流冷凝器的玻璃反应容器中于惰性气氛下和140-160℃温度范围内实施缩合,随后反应温度被缓慢升至200-230℃以达到小于5的酸值。
表1给出了所制备的聚酯P的组成及性质。
实施例B)通过添加单醇制备的聚酯P:
所述聚酯中间体P的制备是通过本领域技术人员已知的聚酯制备方法。为此,首先在配有机械搅拌器、温度计和回流冷凝器的玻璃反应容器中于惰性气氛下和140-160℃温度范围内实施缩合,随后反应温度被缓慢升至200-230℃以达到小于5的酸值。
表2给出了所制备的聚酯P的的组成及性质。
实施例1:用实施例A)的聚酯通过添加甲基六氢邻苯二甲酸酐(MHH-PAn)制备分散树脂
上述实施例A)的聚酯中间体按顺序与酸酐(MHH-Pan)、脂肪酸(月桂酸)和聚亚乙基亚胺(BASF的PR 8515)混合并在约130-150℃下反应至酸值小于50,释放的水通过蒸馏除去。在所述反应后,形成了黄色至褐色、粘稠或甚至高度粘稠但非交联的产物,其可被用作分散树脂。
表3给出了所制备的分散树脂的组成及性质。
实施例2:用实施例A)的聚酯通过添加邻苯二甲酸酐(PAn)制备分散树脂
上述实施例A)的聚酯中间体按顺序与酸酐(PAn)、脂肪酸(月桂酸)和聚亚乙基亚胺(BASF SE的PR 8515)混合并在约130-150℃下反应至酸值小于50,释放的水通过蒸馏除去。在所述反应后,形成了黄色至褐色、粘稠或甚至高度粘稠但非交联的产物,其可被用作分散树脂。
表4给出了所制备的分散树脂的组成及性质。
实施例3:用实施例A)的聚酯通过添加甲基六氢邻苯二甲酸酐(MHH-PAn)制备分散树脂
上述实施例A)的聚酯中间体按顺序与酸酐(MHH-PAn)、脂肪酸(蓖麻油酸)和聚亚乙基亚胺(BASF SE的PR 8515)混合并在约130-150℃下反应至酸值小于50,释放的水通过蒸馏除去。在所述反应后,形成了黄色至褐色、粘稠或甚至高度粘稠但非交联的产物,其可被用作分散树脂。
表5给出了所制备的分散树脂的组成及性质。
实施例4:用实施例B)的聚酯通过添加甲基六氢邻苯二甲酸酐(MHH-PAn)制备分散树脂
上述实施例B)的聚酯中间体按顺序与酸酐(MHH-PAn)、脂肪酸(月桂酸)和聚亚乙基亚胺(BASF SE的PR 8515)混合并在约130-150℃下反应至酸值小于50,释放的水通过蒸馏除去。在所述反应后,形成了黄色至褐色、粘稠或甚至高度粘稠但非交联的产物,其可被用作分散树脂。
表6给出了所制备的分散树脂的组成及性质。
实施例5:用实施例B)的聚酯通过添加邻苯二甲酸酐(PAn)制备分散树脂
上述实施例B)的聚酯中间体按顺序与酸酐(PAn)、脂肪酸(月桂酸)和聚亚乙基亚胺(BASF SE的PR 8515)混合并在约130-150℃下反应至酸值小于50,释放的水通过蒸馏除去。在所述反应后,形成了黄色至褐色、粘稠或甚至高度粘稠但非交联的产物,其可被用作分散树脂。
表7给出了所制备的分散树脂的组成及性质。
Claims (16)
1.通式(I)的分散树脂,
T-P–Z–T (I)
其中
T是终止聚合的基团,
Z是碱性基团或包含碱性基团的基团,
P是基于二羧酸或多羧酸和二醇或多醇的聚酯,包括式(I)的化合物的盐。
2.权利要求1的分散树脂,特征在于所述二羧酸或多羧酸选自邻苯二甲酸、间苯二甲酸、对苯二甲酸、1,2-环己烷二羧酸和异构体、琥珀酸、癸二酸、甲基四氢邻苯二甲酸、甲基六氢邻苯二甲酸、六氢邻苯二甲酸或四氢邻苯二甲酸、十二烷二酸、己二酸、戊二酸、柠康酸、富马酸、衣康酸、马来酸、中康酸、壬二酸、苯均四酸和/或偏苯三酸、它们的酸酐和/或低分子量烷基酯。
3.权利要求1或2的分散树脂,特征在于所述二醇或多醇选自乙二醇、1,2-和/或1,3-丙二醇、二甘醇、双丙甘醇、三甘醇、四甘醇、1,2-和/或1,4-丁二醇、1,3-丁基乙基丙二醇、1,3-甲基丙二醇、1,5-戊二醇、环己基二甲醇、4,8-三环[5.2.1.O2,7]癸烷二甲醇、甘油、1,6-己二醇、新戊二醇、双酚A、B、C、F、降冰片烯二醇、1,4-苄基二甲醇和1,4-苄基二乙醇和/或2,4-二甲基-2-乙基己烷-1,3-二醇。
4.根据权利要求1-3中一项或多项的分散树脂,特征在于所述聚酯P的Mn为700-10000g/mol和Mw为1500-40 000g/mol。
5.根据权利要求1-4中一项或多项的分散树脂,特征在于所述终止聚合的T基团是单羧酸。
6.根据权利要求1-5中一项或多项的分散树脂,特征在于Z是聚烯丙基胺或聚(C2-4-亚烷基亚胺)。
7.根据权利要求1-6中一项或多项的分散树脂,特征在于Z是平均分子量Mw为200-600000g/mol的聚亚乙基亚胺。
8.根据权利要求1-7中一项或多项的分散树脂,特征在于聚酯P对Z基团的化合物的重量比在30:1和1:1之间。
9.权利要求1的分散树脂的制备方法,包括第一步:二羧酸或多羧酸与二醇或多醇在终止聚合的基团的存在下缩合,第二步:将第一步所得聚酯与二羧酸或其酸酐反应以形成酸官能化的聚酯,和第三步:随后将第二步所得酸官能化的聚酯与Z基团的化合物反应。
10.权利要求9的方法,特征在于终止聚合的基团T额外存在于所述第二步中。
11.权利要求9或10的方法,特征在于所述第二步在50-250℃的温度下进行。
12.根据权利要求9-11中一项或多项的方法,特征在于聚酯对Z基团的化合物的重量比在30:1和1:1之间,非常优选在20:1和2:1之间,特别优选在15:1和4:1之间。
13.包含权利要求1的分散树脂的组合物。
14.权利要求13的组合物,包含权利要求1的分散树脂和颗粒固体。
15.权利要求13或14的组合物,特征在于所述组合物是由权利要求1的分散树脂、颗粒固体和有机介质所组成的分散体。
16.权利要求1的分散树脂作为固体用分散剂的用途。
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