DE69218606T2 - Anstrichstoff enthaltend Celluloseacetoacetate - Google Patents
Anstrichstoff enthaltend CelluloseacetoacetateInfo
- Publication number
- DE69218606T2 DE69218606T2 DE69218606T DE69218606T DE69218606T2 DE 69218606 T2 DE69218606 T2 DE 69218606T2 DE 69218606 T DE69218606 T DE 69218606T DE 69218606 T DE69218606 T DE 69218606T DE 69218606 T2 DE69218606 T2 DE 69218606T2
- Authority
- DE
- Germany
- Prior art keywords
- coating composition
- cellulose
- water
- weight
- acetoacetate
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Fee Related
Links
- 229920002678 cellulose Polymers 0.000 title claims abstract description 73
- 239000001913 cellulose Substances 0.000 title claims abstract description 71
- WDJHALXBUFZDSR-UHFFFAOYSA-M acetoacetate Chemical compound CC(=O)CC([O-])=O WDJHALXBUFZDSR-UHFFFAOYSA-M 0.000 title claims description 37
- 239000003973 paint Substances 0.000 title 1
- 238000000576 coating method Methods 0.000 claims abstract description 22
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 22
- 239000002904 solvent Substances 0.000 claims abstract description 18
- 239000003431 cross linking reagent Substances 0.000 claims abstract description 14
- -1 alkyl acetoacetate Chemical compound 0.000 claims abstract description 13
- 239000000203 mixture Substances 0.000 claims abstract description 8
- 235000010980 cellulose Nutrition 0.000 claims description 68
- 239000008199 coating composition Substances 0.000 claims description 38
- 238000000034 method Methods 0.000 claims description 31
- 239000011248 coating agent Substances 0.000 claims description 18
- 239000000758 substrate Substances 0.000 claims description 14
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 claims description 11
- 239000008186 active pharmaceutical agent Substances 0.000 claims description 9
- 239000000654 additive Substances 0.000 claims description 8
- 229920000877 Melamine resin Polymers 0.000 claims description 6
- 239000002253 acid Substances 0.000 claims description 5
- 230000000996 additive effect Effects 0.000 claims description 5
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 claims description 4
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 claims description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
- 239000004640 Melamine resin Substances 0.000 claims description 3
- 229920001807 Urea-formaldehyde Polymers 0.000 claims description 3
- 150000001412 amines Chemical class 0.000 claims description 3
- 239000001257 hydrogen Substances 0.000 claims description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims description 3
- 229910052751 metal Inorganic materials 0.000 claims description 3
- 239000002184 metal Substances 0.000 claims description 3
- 239000002562 thickening agent Substances 0.000 claims description 3
- DEUGOISHWHDTIR-UHFFFAOYSA-N (1-hydroxy-5,5-dimethylhexyl) 2-methylpropanoate Chemical compound C(C(C)C)(=O)OC(CCCC(C)(C)C)O DEUGOISHWHDTIR-UHFFFAOYSA-N 0.000 claims description 2
- BNCADMBVWNPPIZ-UHFFFAOYSA-N 2-n,2-n,4-n,4-n,6-n,6-n-hexakis(methoxymethyl)-1,3,5-triazine-2,4,6-triamine Chemical group COCN(COC)C1=NC(N(COC)COC)=NC(N(COC)COC)=N1 BNCADMBVWNPPIZ-UHFFFAOYSA-N 0.000 claims description 2
- ZQCIMPBZCZUDJM-UHFFFAOYSA-N 2-octoxyethanol Chemical compound CCCCCCCCOCCO ZQCIMPBZCZUDJM-UHFFFAOYSA-N 0.000 claims description 2
- 229920002134 Carboxymethyl cellulose Polymers 0.000 claims description 2
- 229920000896 Ethulose Polymers 0.000 claims description 2
- 239000001859 Ethyl hydroxyethyl cellulose Substances 0.000 claims description 2
- 229920002907 Guar gum Polymers 0.000 claims description 2
- 229920003171 Poly (ethylene oxide) Polymers 0.000 claims description 2
- 239000004952 Polyamide Substances 0.000 claims description 2
- 229920006311 Urethane elastomer Polymers 0.000 claims description 2
- AUNAPVYQLLNFOI-UHFFFAOYSA-L [Pb++].[Pb++].[Pb++].[O-]S([O-])(=O)=O.[O-][Cr]([O-])(=O)=O.[O-][Mo]([O-])(=O)=O Chemical compound [Pb++].[Pb++].[Pb++].[O-]S([O-])(=O)=O.[O-][Cr]([O-])(=O)=O.[O-][Mo]([O-])(=O)=O AUNAPVYQLLNFOI-UHFFFAOYSA-L 0.000 claims description 2
- TZCXTZWJZNENPQ-UHFFFAOYSA-L barium sulfate Chemical compound [Ba+2].[O-]S([O-])(=O)=O TZCXTZWJZNENPQ-UHFFFAOYSA-L 0.000 claims description 2
- 239000010428 baryte Substances 0.000 claims description 2
- 229910052601 baryte Inorganic materials 0.000 claims description 2
- 239000003139 biocide Substances 0.000 claims description 2
- 229910000019 calcium carbonate Inorganic materials 0.000 claims description 2
- 239000006229 carbon black Substances 0.000 claims description 2
- 239000001768 carboxy methyl cellulose Substances 0.000 claims description 2
- 235000010948 carboxy methyl cellulose Nutrition 0.000 claims description 2
- 239000008112 carboxymethyl-cellulose Substances 0.000 claims description 2
- 239000004927 clay Substances 0.000 claims description 2
- 239000003086 colorant Substances 0.000 claims description 2
- XCJYREBRNVKWGJ-UHFFFAOYSA-N copper(II) phthalocyanine Chemical compound [Cu+2].C12=CC=CC=C2C(N=C2[N-]C(C3=CC=CC=C32)=N2)=NC1=NC([C]1C=CC=CC1=1)=NC=1N=C1[C]3C=CC=CC3=C2[N-]1 XCJYREBRNVKWGJ-UHFFFAOYSA-N 0.000 claims description 2
- 229940028356 diethylene glycol monobutyl ether Drugs 0.000 claims description 2
- 235000019326 ethyl hydroxyethyl cellulose Nutrition 0.000 claims description 2
- 239000011521 glass Substances 0.000 claims description 2
- 239000000665 guar gum Substances 0.000 claims description 2
- 235000010417 guar gum Nutrition 0.000 claims description 2
- 229960002154 guar gum Drugs 0.000 claims description 2
- 239000001866 hydroxypropyl methyl cellulose Substances 0.000 claims description 2
- 235000010979 hydroxypropyl methyl cellulose Nutrition 0.000 claims description 2
- 229920003088 hydroxypropyl methyl cellulose Polymers 0.000 claims description 2
- UFVKGYZPFZQRLF-UHFFFAOYSA-N hydroxypropyl methyl cellulose Chemical compound OC1C(O)C(OC)OC(CO)C1OC1C(O)C(O)C(OC2C(C(O)C(OC3C(C(O)C(O)C(CO)O3)O)C(CO)O2)O)C(CO)O1 UFVKGYZPFZQRLF-UHFFFAOYSA-N 0.000 claims description 2
- 150000002497 iodine compounds Chemical class 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- JCGNDDUYTRNOFT-UHFFFAOYSA-N oxolane-2,4-dione Chemical compound O=C1COC(=O)C1 JCGNDDUYTRNOFT-UHFFFAOYSA-N 0.000 claims description 2
- 229920002647 polyamide Polymers 0.000 claims description 2
- 229920006254 polymer film Polymers 0.000 claims description 2
- 229920001451 polypropylene glycol Polymers 0.000 claims description 2
- 229920001296 polysiloxane Polymers 0.000 claims description 2
- 150000003856 quaternary ammonium compounds Chemical class 0.000 claims description 2
- 229920005989 resin Polymers 0.000 claims description 2
- 239000011347 resin Substances 0.000 claims description 2
- 150000003606 tin compounds Chemical class 0.000 claims description 2
- 239000004408 titanium dioxide Substances 0.000 claims description 2
- YNJBWRMUSHSURL-UHFFFAOYSA-N trichloroacetic acid Chemical compound OC(=O)C(Cl)(Cl)Cl YNJBWRMUSHSURL-UHFFFAOYSA-N 0.000 claims description 2
- ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical compound OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 0.000 claims description 2
- 230000003115 biocidal effect Effects 0.000 claims 1
- NBVXSUQYWXRMNV-UHFFFAOYSA-N fluoromethane Chemical compound FC NBVXSUQYWXRMNV-UHFFFAOYSA-N 0.000 claims 1
- KWGKDLIKAYFUFQ-UHFFFAOYSA-M lithium chloride Chemical compound [Li+].[Cl-] KWGKDLIKAYFUFQ-UHFFFAOYSA-M 0.000 abstract description 20
- WASQWSOJHCZDFK-UHFFFAOYSA-N diketene Chemical compound C=C1CC(=O)O1 WASQWSOJHCZDFK-UHFFFAOYSA-N 0.000 abstract description 11
- 239000000463 material Substances 0.000 abstract description 5
- 150000004729 acetoacetic acid derivatives Chemical class 0.000 abstract description 3
- XFRBXZCBOYNMJP-UHFFFAOYSA-N 2,2,6-trimethyl-1,3-dioxin-4-one Chemical compound CC1=CC(=O)OC(C)(C)O1 XFRBXZCBOYNMJP-UHFFFAOYSA-N 0.000 abstract description 2
- 125000003917 carbamoyl group Chemical class [H]N([H])C(*)=O 0.000 abstract 1
- 239000000047 product Substances 0.000 description 24
- 239000003054 catalyst Substances 0.000 description 19
- 238000006243 chemical reaction Methods 0.000 description 17
- 238000010561 standard procedure Methods 0.000 description 16
- 239000003153 chemical reaction reagent Substances 0.000 description 14
- 229920000642 polymer Polymers 0.000 description 14
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 12
- 238000004458 analytical method Methods 0.000 description 12
- 239000000243 solution Substances 0.000 description 12
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 11
- 238000012360 testing method Methods 0.000 description 11
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 8
- 239000006185 dispersion Substances 0.000 description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- 229910000831 Steel Inorganic materials 0.000 description 6
- 239000004615 ingredient Substances 0.000 description 6
- 239000000049 pigment Substances 0.000 description 6
- 239000010959 steel Substances 0.000 description 6
- 238000006467 substitution reaction Methods 0.000 description 6
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 5
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 5
- 229920000742 Cotton Polymers 0.000 description 5
- 150000003857 carboxamides Chemical class 0.000 description 5
- 238000004132 cross linking Methods 0.000 description 5
- 238000004817 gas chromatography Methods 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- 229910000398 iron phosphate Inorganic materials 0.000 description 4
- WBJZTOZJJYAKHQ-UHFFFAOYSA-K iron(3+) phosphate Chemical compound [Fe+3].[O-]P([O-])([O-])=O WBJZTOZJJYAKHQ-UHFFFAOYSA-K 0.000 description 4
- 238000002360 preparation method Methods 0.000 description 4
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 125000002339 acetoacetyl group Chemical group O=C([*])C([H])([H])C(=O)C([H])([H])[H] 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 150000002081 enamines Chemical class 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- JDSHMPZPIAZGSV-UHFFFAOYSA-N melamine Chemical compound NC1=NC(N)=NC(N)=N1 JDSHMPZPIAZGSV-UHFFFAOYSA-N 0.000 description 3
- 239000001632 sodium acetate Substances 0.000 description 3
- 235000017281 sodium acetate Nutrition 0.000 description 3
- 238000005507 spraying Methods 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- QPUYECUOLPXSFR-UHFFFAOYSA-N 1-methylnaphthalene Chemical compound C1=CC=C2C(C)=CC=CC2=C1 QPUYECUOLPXSFR-UHFFFAOYSA-N 0.000 description 2
- 238000005160 1H NMR spectroscopy Methods 0.000 description 2
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 2
- REIYHFWZISXFKU-UHFFFAOYSA-N Butyl acetoacetate Chemical compound CCCCOC(=O)CC(C)=O REIYHFWZISXFKU-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 229920000168 Microcrystalline cellulose Polymers 0.000 description 2
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- 239000004793 Polystyrene Substances 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- WDJHALXBUFZDSR-UHFFFAOYSA-N acetoacetic acid Chemical group CC(=O)CC(O)=O WDJHALXBUFZDSR-UHFFFAOYSA-N 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 229920003180 amino resin Polymers 0.000 description 2
- 239000011230 binding agent Substances 0.000 description 2
- BWRFQFVRMJWEQW-UHFFFAOYSA-N but-1-ene-1,3-dione Chemical compound CC(=O)C=C=O BWRFQFVRMJWEQW-UHFFFAOYSA-N 0.000 description 2
- 229920002301 cellulose acetate Polymers 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 238000005227 gel permeation chromatography Methods 0.000 description 2
- 238000013035 low temperature curing Methods 0.000 description 2
- 230000014759 maintenance of location Effects 0.000 description 2
- 150000007974 melamines Chemical class 0.000 description 2
- 235000019813 microcrystalline cellulose Nutrition 0.000 description 2
- 239000008108 microcrystalline cellulose Substances 0.000 description 2
- 229940016286 microcrystalline cellulose Drugs 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 229920002223 polystyrene Polymers 0.000 description 2
- 230000035484 reaction time Effects 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 239000002002 slurry Substances 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- WTFAGPBUAGFMQX-UHFFFAOYSA-N 1-[2-[2-(2-aminopropoxy)propoxy]propoxy]propan-2-amine Chemical compound CC(N)COCC(C)OCC(C)OCC(C)N WTFAGPBUAGFMQX-UHFFFAOYSA-N 0.000 description 1
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 1
- XGJZQNMUVTZITK-UHFFFAOYSA-N 2-n,2-n,4-n,4-n,6-n,6-n-hexamethoxy-1,3,5-triazine-2,4,6-triamine Chemical compound CON(OC)C1=NC(N(OC)OC)=NC(N(OC)OC)=N1 XGJZQNMUVTZITK-UHFFFAOYSA-N 0.000 description 1
- 229920002749 Bacterial cellulose Polymers 0.000 description 1
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 description 1
- 239000004971 Cross linker Substances 0.000 description 1
- XZMCDFZZKTWFGF-UHFFFAOYSA-N Cyanamide Chemical compound NC#N XZMCDFZZKTWFGF-UHFFFAOYSA-N 0.000 description 1
- 229920003270 Cymel® Polymers 0.000 description 1
- 229910001335 Galvanized steel Inorganic materials 0.000 description 1
- 238000004566 IR spectroscopy Methods 0.000 description 1
- 239000004594 Masterbatch (MB) Substances 0.000 description 1
- MHABMANUFPZXEB-UHFFFAOYSA-N O-demethyl-aloesaponarin I Natural products O=C1C2=CC=CC(O)=C2C(=O)C2=C1C=C(O)C(C(O)=O)=C2C MHABMANUFPZXEB-UHFFFAOYSA-N 0.000 description 1
- 239000004698 Polyethylene Substances 0.000 description 1
- 239000004721 Polyphenylene oxide Substances 0.000 description 1
- 239000004743 Polypropylene Substances 0.000 description 1
- APQHKWPGGHMYKJ-UHFFFAOYSA-N Tributyltin oxide Chemical compound CCCC[Sn](CCCC)(CCCC)O[Sn](CCCC)(CCCC)CCCC APQHKWPGGHMYKJ-UHFFFAOYSA-N 0.000 description 1
- 240000000581 Triticum monococcum Species 0.000 description 1
- 238000007171 acid catalysis Methods 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 230000010933 acylation Effects 0.000 description 1
- 238000005917 acylation reaction Methods 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 238000000889 atomisation Methods 0.000 description 1
- 239000005016 bacterial cellulose Substances 0.000 description 1
- 230000001580 bacterial effect Effects 0.000 description 1
- 238000005815 base catalysis Methods 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 238000004364 calculation method Methods 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 239000007809 chemical reaction catalyst Substances 0.000 description 1
- 239000007810 chemical reaction solvent Substances 0.000 description 1
- 229910052570 clay Inorganic materials 0.000 description 1
- 238000004040 coloring Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000006184 cosolvent Substances 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000001723 curing Methods 0.000 description 1
- PZQGSZRQKQZCOJ-UHFFFAOYSA-N cyclobutane-1,3-dione Chemical compound O=C1CC(=O)C1 PZQGSZRQKQZCOJ-UHFFFAOYSA-N 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- 238000002845 discoloration Methods 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000000921 elemental analysis Methods 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 239000008397 galvanized steel Substances 0.000 description 1
- 239000011121 hardwood Substances 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 238000010348 incorporation Methods 0.000 description 1
- 238000009776 industrial production Methods 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 239000002198 insoluble material Substances 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- TWNIBLMWSKIRAT-VFUOTHLCSA-N levoglucosan Chemical group O[C@@H]1[C@@H](O)[C@H](O)[C@H]2CO[C@@H]1O2 TWNIBLMWSKIRAT-VFUOTHLCSA-N 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 229920000609 methyl cellulose Polymers 0.000 description 1
- 239000001923 methylcellulose Substances 0.000 description 1
- 235000010981 methylcellulose Nutrition 0.000 description 1
- 239000011707 mineral Chemical class 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 239000012038 nucleophile Substances 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 229920000768 polyamine Polymers 0.000 description 1
- 229920000570 polyether Polymers 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 229920001155 polypropylene Polymers 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 150000003138 primary alcohols Chemical class 0.000 description 1
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 239000012048 reactive intermediate Substances 0.000 description 1
- 239000004627 regenerated cellulose Substances 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 239000006254 rheological additive Substances 0.000 description 1
- 238000000518 rheometry Methods 0.000 description 1
- 238000007761 roller coating Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000013341 scale-up Methods 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 239000011122 softwood Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 230000003381 solubilizing effect Effects 0.000 description 1
- 239000012086 standard solution Substances 0.000 description 1
- 239000006228 supernatant Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- JKUYRAMKJLMYLO-UHFFFAOYSA-N tert-butyl 3-oxobutanoate Chemical compound CC(=O)CC(=O)OC(C)(C)C JKUYRAMKJLMYLO-UHFFFAOYSA-N 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- 238000001029 thermal curing Methods 0.000 description 1
- 229920001187 thermosetting polymer Polymers 0.000 description 1
- 239000008154 viscoelastic solution Substances 0.000 description 1
- 229920003169 water-soluble polymer Polymers 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08B—POLYSACCHARIDES; DERIVATIVES THEREOF
- C08B3/00—Preparation of cellulose esters of organic acids
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08B—POLYSACCHARIDES; DERIVATIVES THEREOF
- C08B3/00—Preparation of cellulose esters of organic acids
- C08B3/14—Preparation of cellulose esters of organic acids in which the organic acid residue contains substituents, e.g. NH2, Cl
-
- C—CHEMISTRY; METALLURGY
- 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
- C09D101/00—Coating compositions based on cellulose, modified cellulose, or cellulose derivatives
- C09D101/08—Cellulose derivatives
- C09D101/10—Esters of organic acids
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biochemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Wood Science & Technology (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Polysaccharides And Polysaccharide Derivatives (AREA)
- Paints Or Removers (AREA)
- Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US74282191A | 1991-08-09 | 1991-08-09 | |
| PCT/US1992/006304 WO1993003063A1 (en) | 1991-08-09 | 1992-07-30 | Cellulose acetoacetates |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE69218606D1 DE69218606D1 (de) | 1997-04-30 |
| DE69218606T2 true DE69218606T2 (de) | 1997-07-03 |
Family
ID=24986380
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE69218606T Expired - Fee Related DE69218606T2 (de) | 1991-08-09 | 1992-07-30 | Anstrichstoff enthaltend Celluloseacetoacetate |
Country Status (11)
| Country | Link |
|---|---|
| US (2) | US5292877A (enExample) |
| EP (1) | EP0598038B1 (enExample) |
| JP (1) | JPH06510805A (enExample) |
| AT (1) | ATE150768T1 (enExample) |
| CA (1) | CA2106189A1 (enExample) |
| DE (1) | DE69218606T2 (enExample) |
| DK (1) | DK0598038T3 (enExample) |
| ES (1) | ES2099276T3 (enExample) |
| GR (1) | GR3023538T3 (enExample) |
| TW (1) | TW218384B (enExample) |
| WO (1) | WO1993003063A1 (enExample) |
Families Citing this family (54)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5420267A (en) * | 1991-08-09 | 1995-05-30 | Eastman Chemical Company | Cellulose acetoacetate esters |
| US5750677A (en) * | 1994-12-30 | 1998-05-12 | Eastman Chemical Company | Direct process for the production of cellulose esters |
| MX9704973A (es) * | 1994-12-30 | 1997-10-31 | Eastman Chem Co | Proceso para la preparacion de esteres de celulosa utilizando un catalizador de resina de acido sulfonico. |
| US5770726A (en) * | 1997-03-10 | 1998-06-23 | Eastman Chemical Company | Process for preparing a cellllose acetoacetate alkanoates |
| US5770711A (en) * | 1996-09-30 | 1998-06-23 | Kimberly-Clark Worldwide, Inc. | Polysaccharides substituted with polycarboxylated moieties |
| JP2002544658A (ja) | 1998-08-21 | 2002-12-24 | マイクロン テクノロジー， インク． | 電界効果トランジスタ、集積回路、電界効果トランジスタのゲートを形成する方法、及び集積回路を形成する方法 |
| US6207224B1 (en) | 1999-10-06 | 2001-03-27 | E. I. Du Pont De Nemours And Company | Process for coating thermoplastic substrates with a coating composition containing a non-aggressive solvent |
| US6528643B1 (en) * | 2000-05-05 | 2003-03-04 | Hercules Incorporated | Esterified polysaccharide products and B-lactone ring opened ketene dimer products containing the compositions, and process of making the same |
| US6528644B1 (en) | 2001-09-26 | 2003-03-04 | Hercules Incorporated | Acetoacetylated saccharides and process of making the same |
| DE602005026516D1 (de) * | 2004-05-12 | 2011-04-07 | Akzo Nobel Coatings Int Bv | Ammensetzungen |
| US20070053855A1 (en) * | 2004-09-16 | 2007-03-08 | Shelton Michael C | Personal care products incorporating cellulosic fatty acid esters |
| US20060062749A1 (en) * | 2004-09-16 | 2006-03-23 | Shelton Michael C | personal care products incorporating cellulosic fatty acid esters |
| DE102006028165A1 (de) * | 2006-06-16 | 2007-12-20 | Basf Ag | Verfahren zur Acylierung von Cellulose |
| US7855261B2 (en) * | 2006-12-08 | 2010-12-21 | Eastman Chemical Company | Aldehyde removal |
| US20080135058A1 (en) * | 2006-12-08 | 2008-06-12 | Ted Calvin Germroth | Tobacco smoke filter and method for removal of aldehydes from tobacco smoke |
| US20080134893A1 (en) * | 2006-12-08 | 2008-06-12 | Thauming Kuo | Particulate filter media |
| US9068063B2 (en) | 2010-06-29 | 2015-06-30 | Eastman Chemical Company | Cellulose ester/elastomer compositions |
| US9273195B2 (en) | 2010-06-29 | 2016-03-01 | Eastman Chemical Company | Tires comprising cellulose ester/elastomer compositions |
| US20130150501A1 (en) | 2011-12-07 | 2013-06-13 | Eastman Chemical Company | Cellulose esters in highly-filled elastomaric systems |
| CN105121495A (zh) | 2013-02-15 | 2015-12-02 | 英派尔科技开发有限公司 | 酚类环氧化合物 |
| US9868683B2 (en) | 2013-06-13 | 2018-01-16 | Empire Technology Development Llc | Multi-functional phenolic resins |
| EP3077364A4 (en) | 2013-12-02 | 2017-11-08 | Empire Technology Development LLC | Novel gemini surfactants and their use |
| JP6378316B2 (ja) * | 2014-03-19 | 2018-08-22 | 株式会社ダイセル | セルロースアシレート−オキソアルカノエート |
| CN105524350B (zh) * | 2014-10-21 | 2017-08-25 | 中国石油化工股份有限公司 | 一种聚丙烯用voc抑制母粒及其制备方法与应用 |
| CN105524349B (zh) * | 2014-10-21 | 2017-08-25 | 中国石油化工股份有限公司 | 一种低voc聚丙烯树脂组合物及其制备方法 |
| CN104497150A (zh) * | 2014-11-27 | 2015-04-08 | 河南中烟工业有限责任公司 | 一种脂溶性纤维素混合酯的制备方法 |
| US10077342B2 (en) | 2016-01-21 | 2018-09-18 | Eastman Chemical Company | Elastomeric compositions comprising cellulose ester additives |
| JP7692682B2 (ja) | 2016-11-11 | 2025-06-16 | イーストマン ケミカル カンパニー | セルロースエステルと耐衝撃性改良剤の組成物及びこれらの組成物を用いて製造される物品 |
| WO2018089575A1 (en) | 2016-11-11 | 2018-05-17 | Eastman Chemical Company | Cellulose ester and ethylene vinyl acetate compositions and articles made using these compositions |
| US11655309B2 (en) | 2016-11-11 | 2023-05-23 | Eastman Chemical Company | Polymer-based resin compositions derived from cellulose and articles made using these compositions |
| TWI786231B (zh) * | 2017-12-21 | 2022-12-11 | 德商漢高股份有限及兩合公司 | 過濾薄膜組件之封裝或接合組成物 |
| CN111684004B (zh) | 2018-02-13 | 2023-06-27 | 伊士曼化工公司 | 纤维素酯以及聚合脂族聚酯组合物和制品 |
| CN108641003A (zh) * | 2018-04-13 | 2018-10-12 | 东华大学 | 一种非均相制备乙酰乙酸化纤维素材料的方法 |
| WO2020018614A2 (en) | 2018-07-19 | 2020-01-23 | Eastman Chemical Company | Cellulose ester and elastomer compositions |
| US11286436B2 (en) | 2019-02-04 | 2022-03-29 | Eastman Chemical Company | Feed location for gasification of plastics and solid fossil fuels |
| EP3976661A4 (en) | 2019-05-24 | 2023-03-29 | Eastman Chemical Company | CELLULOSIC ESTERS WITH RECYCLED CONTENT |
| US11365357B2 (en) | 2019-05-24 | 2022-06-21 | Eastman Chemical Company | Cracking C8+ fraction of pyoil |
| WO2020247192A1 (en) | 2019-05-24 | 2020-12-10 | Eastman Chemical Company | Recycle content cracked effluent |
| US11946000B2 (en) | 2019-05-24 | 2024-04-02 | Eastman Chemical Company | Blend small amounts of pyoil into a liquid stream processed into a gas cracker |
| WO2021021847A1 (en) | 2019-07-29 | 2021-02-04 | Eastman Chemical Company | Recycle content (c4)alkanal |
| WO2021021855A1 (en) | 2019-07-29 | 2021-02-04 | Eastman Chemical Company | Recycle content cyclobutane diol polyester |
| US11319262B2 (en) | 2019-10-31 | 2022-05-03 | Eastman Chemical Company | Processes and systems for making recycle content hydrocarbons |
| US12528995B2 (en) | 2019-10-31 | 2026-01-20 | ExxonMobil Product Solutions Company | Pyrolysis method and system for recycled waste |
| WO2021087057A1 (en) | 2019-10-31 | 2021-05-06 | Eastman Chemical Company | Pyrolysis method and system for recycled waste |
| US11945998B2 (en) | 2019-10-31 | 2024-04-02 | Eastman Chemical Company | Processes and systems for making recycle content hydrocarbons |
| US12104121B2 (en) | 2019-11-07 | 2024-10-01 | Eastman Chemical Company | Recycle content mixed esters and solvents |
| CN114728868B (zh) | 2019-11-07 | 2024-09-03 | 伊士曼化工公司 | 回收成分羰基合成醇和羰基合成增塑剂 |
| EP4054998A4 (en) | 2019-11-07 | 2024-04-03 | Eastman Chemical Company | PROPANOL WITH RECYCLED CONTENT |
| WO2021092306A1 (en) | 2019-11-07 | 2021-05-14 | Eastman Chemical Company | Recycle content alpha olefins and fatty alcohols |
| US12195674B2 (en) | 2021-09-21 | 2025-01-14 | Eastman Chemical Company | Using spent caustic solution from pygas treatment to neutralize halogens from liquified waste plastic |
| JP2025520397A (ja) | 2022-06-13 | 2025-07-03 | レゴ エー／エス | 低摩擦係数を有するセルロースエステルポリマー組成物 |
| FR3142898B1 (fr) | 2022-12-13 | 2026-02-06 | Oreal | Procédé de traitement des matières kératiniques mettant en œuvre au moins un composé polysaccharide à fonctions acétoacétates |
| FR3163265A1 (fr) * | 2024-06-14 | 2025-12-19 | L'oreal | Procédé de maquillage des matières kératiniques comprenant l’application d’au moins un composé polysaccharide acétoacétate et un agent réticulant |
| FR3163267A1 (fr) | 2024-06-14 | 2025-12-19 | L'oreal | Procédé de traitement des matières kératiniques mettant en œuvre au moins un composé polysaccharide silicié à fonctions acétoacétates |
Family Cites Families (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2103505A (en) * | 1934-04-17 | 1937-12-28 | Standard Oil Dev Co | Production of polymers of ketene and preparation of esters thereof |
| US2521897A (en) * | 1947-04-30 | 1950-09-12 | Eastman Kodak Co | Method of preparing aceto acetic acid esters of cellulose |
| US2500029A (en) * | 1947-04-30 | 1950-03-07 | Eastman Kodak Co | Cellulose ester materials insoluble in organic solvents |
| DE1016249B (de) * | 1952-07-03 | 1957-09-26 | Lonza Werke Elektrochemische F | Verfahren zur Herstellung von Acetoacetaten von Cellulose |
| US3345313A (en) * | 1963-02-20 | 1967-10-03 | Trojan Powder Co | Alkyd resins and their preparation from reaction mixtures comprising a polymethylolalkanoic acid |
| US3347951A (en) * | 1965-02-16 | 1967-10-17 | Du Pont | Coating compositions |
| US4278790A (en) * | 1978-07-31 | 1981-07-14 | Hopkins Agricultural Chemical Co. | Novel cellulose solutions |
| US4302252A (en) * | 1979-07-25 | 1981-11-24 | International Telephone And Telegraph Corp. | Solvent system for cellulose |
| DE3609928A1 (de) * | 1985-03-27 | 1986-10-09 | Hoechst Gosei K.K., Tokio/Tokyo | Waessrige gelzusammensetzung, verfahren zu ihrer herstellung und ihre verwendung in der metallbearbeitung |
| US4737551A (en) * | 1986-06-23 | 1988-04-12 | E. I. Dupont De Nemours And Company | Coating composition of a hydroxy group-containing modified polyester with polymerized lactone monomers |
| US4698391A (en) * | 1986-07-30 | 1987-10-06 | Eastman Kodak Company | Crosslinked polymers with lowered resistivity and materials and methods for their preparation |
| DE3723897A1 (de) * | 1987-07-18 | 1989-01-26 | Akzo Gmbh | Cellulosederivate und daraus hergestellte fasern und membranen |
| EP0339200A1 (de) * | 1988-02-25 | 1989-11-02 | Akzo Nobel N.V. | Modifizierte Cellulose für biocompatible Dialysemembranen III und Verfahren zu deren Herstellung |
| EP0330134A1 (de) * | 1988-02-25 | 1989-08-30 | Akzo Nobel N.V. | Modifizierte Cellulose für biocompatible Dialysemembranen IV und Verfahren zu deren Herstellung |
| EP0330106A1 (de) * | 1988-02-25 | 1989-08-30 | Akzo Nobel N.V. | Modifizierte Cellulose für biocompatible Dialysemembranen II und Verfahren zu deren Herstellung |
-
1992
- 1992-07-29 TW TW081106011A patent/TW218384B/zh active
- 1992-07-30 DE DE69218606T patent/DE69218606T2/de not_active Expired - Fee Related
- 1992-07-30 ES ES92917835T patent/ES2099276T3/es not_active Expired - Lifetime
- 1992-07-30 WO PCT/US1992/006304 patent/WO1993003063A1/en not_active Ceased
- 1992-07-30 DK DK92917835.8T patent/DK0598038T3/da active
- 1992-07-30 AT AT92917835T patent/ATE150768T1/de not_active IP Right Cessation
- 1992-07-30 EP EP92917835A patent/EP0598038B1/en not_active Expired - Lifetime
- 1992-07-30 CA CA002106189A patent/CA2106189A1/en not_active Abandoned
- 1992-07-30 JP JP5503714A patent/JPH06510805A/ja active Pending
-
1993
- 1993-08-19 US US08/109,205 patent/US5292877A/en not_active Expired - Lifetime
- 1993-12-02 US US08/160,989 patent/US5360843A/en not_active Expired - Lifetime
-
1997
- 1997-05-23 GR GR970401188T patent/GR3023538T3/el unknown
Also Published As
| Publication number | Publication date |
|---|---|
| GR3023538T3 (en) | 1997-08-29 |
| DE69218606D1 (de) | 1997-04-30 |
| US5292877A (en) | 1994-03-08 |
| EP0598038A1 (en) | 1994-05-25 |
| DK0598038T3 (da) | 1997-10-06 |
| WO1993003063A1 (en) | 1993-02-18 |
| ATE150768T1 (de) | 1997-04-15 |
| JPH06510805A (ja) | 1994-12-01 |
| EP0598038B1 (en) | 1997-03-26 |
| TW218384B (enExample) | 1994-01-01 |
| ES2099276T3 (es) | 1997-05-16 |
| US5360843A (en) | 1994-11-01 |
| CA2106189A1 (en) | 1993-02-10 |
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| 8364 | No opposition during term of opposition | ||
| 8339 | Ceased/non-payment of the annual fee |