CA2106189A1 - Cellulose acetoacetates - Google Patents
Cellulose acetoacetatesInfo
- Publication number
- CA2106189A1 CA2106189A1 CA002106189A CA2106189A CA2106189A1 CA 2106189 A1 CA2106189 A1 CA 2106189A1 CA 002106189 A CA002106189 A CA 002106189A CA 2106189 A CA2106189 A CA 2106189A CA 2106189 A1 CA2106189 A1 CA 2106189A1
- Authority
- CA
- Canada
- Prior art keywords
- percent
- cellulose
- coating composition
- 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.)
- Abandoned
Links
- 229920002678 cellulose Polymers 0.000 title claims abstract description 99
- 239000001913 cellulose Substances 0.000 title claims abstract description 97
- 150000004729 acetoacetic acid derivatives Chemical class 0.000 title abstract description 8
- KWGKDLIKAYFUFQ-UHFFFAOYSA-M lithium chloride Chemical compound [Li+].[Cl-] KWGKDLIKAYFUFQ-UHFFFAOYSA-M 0.000 claims abstract description 48
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 41
- 238000000576 coating method Methods 0.000 claims abstract description 21
- WASQWSOJHCZDFK-UHFFFAOYSA-N diketene Chemical compound C=C1CC(=O)O1 WASQWSOJHCZDFK-UHFFFAOYSA-N 0.000 claims abstract description 18
- -1 alkyl acetoacetate Chemical compound 0.000 claims abstract description 17
- 239000000203 mixture Substances 0.000 claims abstract description 17
- 239000003431 cross linking reagent Substances 0.000 claims abstract description 11
- 239000000463 material Substances 0.000 claims abstract description 11
- 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 claims abstract description 4
- 235000010980 cellulose Nutrition 0.000 claims description 94
- 238000000034 method Methods 0.000 claims description 47
- WDJHALXBUFZDSR-UHFFFAOYSA-M acetoacetate Chemical compound CC(=O)CC([O-])=O WDJHALXBUFZDSR-UHFFFAOYSA-M 0.000 claims description 42
- 239000002904 solvent Substances 0.000 claims description 32
- 239000008199 coating composition Substances 0.000 claims description 31
- 230000008569 process Effects 0.000 claims description 30
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 claims description 28
- 239000003054 catalyst Substances 0.000 claims description 24
- 239000000758 substrate Substances 0.000 claims description 20
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 16
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical group O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 claims description 13
- 239000011248 coating agent Substances 0.000 claims description 13
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical group OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 12
- 239000002253 acid Substances 0.000 claims description 10
- 239000000049 pigment Substances 0.000 claims description 10
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 9
- 150000001412 amines Chemical class 0.000 claims description 9
- 150000003857 carboxamides Chemical class 0.000 claims description 9
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 8
- 239000000654 additive Substances 0.000 claims description 8
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 8
- 229920000877 Melamine resin Polymers 0.000 claims description 7
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 claims description 7
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 7
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 6
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 6
- 229920005989 resin Polymers 0.000 claims description 6
- 239000011347 resin Substances 0.000 claims description 6
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims description 5
- 230000015572 biosynthetic process Effects 0.000 claims description 5
- 238000004519 manufacturing process Methods 0.000 claims description 5
- 239000001632 sodium acetate Substances 0.000 claims description 5
- 235000017281 sodium acetate Nutrition 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
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 claims description 4
- 229910052500 inorganic mineral Inorganic materials 0.000 claims description 4
- 230000014759 maintenance of location Effects 0.000 claims description 4
- 239000011707 mineral Substances 0.000 claims description 4
- 239000002562 thickening agent Substances 0.000 claims description 4
- 239000004640 Melamine resin Substances 0.000 claims description 3
- 229920001807 Urea-formaldehyde Polymers 0.000 claims description 3
- 239000003139 biocide Substances 0.000 claims description 3
- 229910052751 metal Inorganic materials 0.000 claims description 3
- 239000002184 metal Substances 0.000 claims description 3
- JOXIMZWYDAKGHI-UHFFFAOYSA-N p-toluenesulfonic acid Substances CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 claims description 3
- 230000003381 solubilizing effect Effects 0.000 claims description 3
- 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
- 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
- 239000003377 acid catalyst Substances 0.000 claims description 2
- 239000003513 alkali Substances 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
- 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
- 230000003197 catalytic effect Effects 0.000 claims description 2
- 239000004927 clay Substances 0.000 claims description 2
- XCJYREBRNVKWGJ-UHFFFAOYSA-N copper(II) phthalocyanine Chemical group [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
- JCGNDDUYTRNOFT-UHFFFAOYSA-N oxolane-2,4-dione Chemical group 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
- 238000001029 thermal curing Methods 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
- 239000008186 active pharmaceutical agent Substances 0.000 claims 7
- 230000000996 additive effect Effects 0.000 claims 5
- 230000003115 biocidal effect Effects 0.000 claims 2
- 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 1
- 229910052601 baryte Inorganic materials 0.000 claims 1
- 239000010428 baryte Substances 0.000 claims 1
- 229940105329 carboxymethylcellulose Drugs 0.000 claims 1
- NBVXSUQYWXRMNV-UHFFFAOYSA-N fluoromethane Chemical compound FC NBVXSUQYWXRMNV-UHFFFAOYSA-N 0.000 claims 1
- 125000005489 p-toluenesulfonic acid group Chemical group 0.000 claims 1
- 150000003839 salts Chemical class 0.000 claims 1
- 125000003917 carbamoyl group Chemical class [H]N([H])C(*)=O 0.000 abstract 1
- 239000000047 product Substances 0.000 description 24
- 239000003153 chemical reaction reagent Substances 0.000 description 23
- 238000004458 analytical method Methods 0.000 description 21
- 238000006243 chemical reaction Methods 0.000 description 18
- 238000010561 standard procedure Methods 0.000 description 16
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 15
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 13
- 229920000642 polymer Polymers 0.000 description 13
- 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
- 210000003298 dental enamel Anatomy 0.000 description 8
- 239000007787 solid Substances 0.000 description 8
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- 238000004132 cross linking Methods 0.000 description 6
- 239000006185 dispersion Substances 0.000 description 6
- JKUYRAMKJLMYLO-UHFFFAOYSA-N tert-butyl 3-oxobutanoate Chemical compound CC(=O)CC(=O)OC(C)(C)C JKUYRAMKJLMYLO-UHFFFAOYSA-N 0.000 description 6
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 5
- 229920000742 Cotton Polymers 0.000 description 5
- 229910000831 Steel Inorganic materials 0.000 description 5
- 239000011230 binding agent Substances 0.000 description 5
- 238000004817 gas chromatography Methods 0.000 description 5
- JDSHMPZPIAZGSV-UHFFFAOYSA-N melamine Chemical compound NC1=NC(N)=NC(N)=N1 JDSHMPZPIAZGSV-UHFFFAOYSA-N 0.000 description 5
- 239000010959 steel Substances 0.000 description 5
- 238000006467 substitution reaction Methods 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- 239000004971 Cross linker Substances 0.000 description 4
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 4
- 150000002081 enamines Chemical class 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
- 239000007788 liquid Substances 0.000 description 4
- XZMCDFZZKTWFGF-UHFFFAOYSA-N Cyanamide Chemical compound NC#N XZMCDFZZKTWFGF-UHFFFAOYSA-N 0.000 description 3
- 229920003270 Cymel® Polymers 0.000 description 3
- 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 3
- 125000002339 acetoacetyl group Chemical group O=C([*])C([H])([H])C(=O)C([H])([H])[H] 0.000 description 3
- BWRFQFVRMJWEQW-UHFFFAOYSA-N but-1-ene-1,3-dione Chemical compound CC(=O)C=C=O BWRFQFVRMJWEQW-UHFFFAOYSA-N 0.000 description 3
- 238000009472 formulation 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
- 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
- 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
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 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
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 2
- 229920003180 amino resin Polymers 0.000 description 2
- 230000008901 benefit Effects 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 239000006184 cosolvent Substances 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 238000005227 gel permeation chromatography Methods 0.000 description 2
- 239000011121 hardwood Substances 0.000 description 2
- 238000013035 low temperature curing Methods 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
- 235000010755 mineral Nutrition 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 229920002223 polystyrene Polymers 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 238000007761 roller coating Methods 0.000 description 2
- 239000002002 slurry Substances 0.000 description 2
- 238000005507 spraying Methods 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- 239000010936 titanium Substances 0.000 description 2
- 229910052719 titanium Inorganic materials 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
- 229920002134 Carboxymethyl cellulose Polymers 0.000 description 1
- 229910001335 Galvanized steel Inorganic materials 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 238000004566 IR spectroscopy Methods 0.000 description 1
- 239000004594 Masterbatch (MB) 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
- 238000006640 acetylation reaction Methods 0.000 description 1
- 238000007171 acid catalysis Methods 0.000 description 1
- 230000010933 acylation Effects 0.000 description 1
- 238000005917 acylation reaction Methods 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
- 239000007864 aqueous solution Substances 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
- 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
- 229920002301 cellulose acetate Polymers 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 239000007810 chemical reaction solvent Substances 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 238000001816 cooling Methods 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
- 238000010908 decantation Methods 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 230000029087 digestion Effects 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
- 238000010438 heat treatment Methods 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 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
- 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
- 238000002156 mixing Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 239000012038 nucleophile Substances 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 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
- 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
- 230000035484 reaction time Effects 0.000 description 1
- 239000012048 reactive intermediate Substances 0.000 description 1
- 230000009467 reduction Effects 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
- 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
- 238000004611 spectroscopical analysis Methods 0.000 description 1
- 238000010186 staining Methods 0.000 description 1
- 239000012086 standard solution Substances 0.000 description 1
- 235000011149 sulphuric acid Nutrition 0.000 description 1
- 239000006228 supernatant Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000010998 test method 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)
- Life Sciences & Earth Sciences (AREA)
- Materials Engineering (AREA)
- Biochemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Health & Medical Sciences (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 | |
| US07/742,821 | 1991-08-09 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2106189A1 true CA2106189A1 (en) | 1993-02-10 |
Family
ID=24986380
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002106189A Abandoned CA2106189A1 (en) | 1991-08-09 | 1992-07-30 | Cellulose acetoacetates |
Country Status (11)
| Country | Link |
|---|---|
| US (2) | US5292877A (cg-RX-API-DMAC10.html) |
| EP (1) | EP0598038B1 (cg-RX-API-DMAC10.html) |
| JP (1) | JPH06510805A (cg-RX-API-DMAC10.html) |
| AT (1) | ATE150768T1 (cg-RX-API-DMAC10.html) |
| CA (1) | CA2106189A1 (cg-RX-API-DMAC10.html) |
| DE (1) | DE69218606T2 (cg-RX-API-DMAC10.html) |
| DK (1) | DK0598038T3 (cg-RX-API-DMAC10.html) |
| ES (1) | ES2099276T3 (cg-RX-API-DMAC10.html) |
| GR (1) | GR3023538T3 (cg-RX-API-DMAC10.html) |
| TW (1) | TW218384B (cg-RX-API-DMAC10.html) |
| WO (1) | WO1993003063A1 (cg-RX-API-DMAC10.html) |
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 |
| CA2208273A1 (en) * | 1994-12-30 | 1996-07-11 | Kevin Joseph Edgar | Process for preparing cellulose esters using a sulfonic acid resin catalyst |
| 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 |
| AU5682399A (en) | 1998-08-21 | 2000-03-14 | Micron Technology, Inc. | Field effect transistors, integrated circuitry, methods of forming field effect transistor gates, and methods of forming integrated circuitry |
| 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 |
| ATE499416T1 (de) * | 2004-05-12 | 2011-03-15 | Akzo Nobel Coatings Int Bv | Antimikrobielle säurekatalysierte beschichtungszusammensetzungen |
| US20060062749A1 (en) * | 2004-09-16 | 2006-03-23 | Shelton Michael C | personal care products incorporating cellulosic fatty acid esters |
| US20070053855A1 (en) * | 2004-09-16 | 2007-03-08 | 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 |
| US20080134893A1 (en) * | 2006-12-08 | 2008-06-12 | Thauming Kuo | Particulate filter media |
| US20080135058A1 (en) * | 2006-12-08 | 2008-06-12 | Ted Calvin Germroth | Tobacco smoke filter and method for removal of aldehydes from tobacco smoke |
| US7855261B2 (en) * | 2006-12-08 | 2010-12-21 | Eastman Chemical Company | Aldehyde removal |
| US20110319531A1 (en) | 2010-06-29 | 2011-12-29 | Eastman Chemical Company | Cellulose ester compositions |
| US9273195B2 (en) | 2010-06-29 | 2016-03-01 | Eastman Chemical Company | Tires comprising cellulose ester/elastomer compositions |
| US9708475B2 (en) | 2011-12-07 | 2017-07-18 | Eastman Chemical Company | Cellulose esters in highly-filled elastomeric systems |
| WO2014126626A1 (en) | 2013-02-15 | 2014-08-21 | Empire Technology Development Llc | Phenolic epoxy compounds |
| WO2014200486A1 (en) | 2013-06-13 | 2014-12-18 | Empire Technology Development Llc | Multi-functional phenolic resins |
| US10106494B2 (en) | 2013-12-02 | 2018-10-23 | Empire Technology Development Llc | Gemini surfactant and their use |
| WO2015140965A1 (ja) * | 2014-03-19 | 2015-09-24 | 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 |
| US10077343B2 (en) | 2016-01-21 | 2018-09-18 | Eastman Chemical Company | Process to produce elastomeric compositions comprising cellulose ester additives |
| CN110168006B (zh) | 2016-11-11 | 2023-04-11 | 伊士曼化工公司 | 纤维素酯和乙烯-乙酸乙烯酯组合物及使用这些组合物制造的制品 |
| EP3538601A1 (en) | 2016-11-11 | 2019-09-18 | Eastman Chemical Company | Cellulose ester and impact modifier compositions and articles made using these compositions |
| EP3538605A1 (en) | 2016-11-11 | 2019-09-18 | 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 |
| EP3752557A1 (en) | 2018-02-13 | 2020-12-23 | Eastman Chemical Company | Cellulose ester and polymeric aliphatic polyester compositions and articles |
| 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 |
| EP3824027A2 (en) | 2018-07-19 | 2021-05-26 | Eastman Chemical Company | Cellulose ester and elastomer compositions |
| US11312914B2 (en) | 2019-02-04 | 2022-04-26 | Eastman Chemical Company | Gasification of plastics and solid fossil fuels to produce organic compounds |
| US12031091B2 (en) | 2019-05-24 | 2024-07-09 | Eastman Chemical Company | Recycle content cracked effluent |
| EP3976732A4 (en) | 2019-05-24 | 2023-05-17 | Eastman Chemical Company | MIXING SMALL QUANTITIES OF PYROLYTIC OIL INTO A LIQUID STREAM WHICH IS PROCESSED INTO A GAS CRACKER |
| WO2020242921A1 (en) | 2019-05-24 | 2020-12-03 | Eastman Chemical Company | Recycle content cellulose ester |
| US11365357B2 (en) | 2019-05-24 | 2022-06-21 | Eastman Chemical Company | Cracking C8+ fraction of pyoil |
| TW202112716A (zh) | 2019-07-29 | 2021-04-01 | 美商伊士曼化學公司 | 回收物環丁烷二醇聚酯 |
| CN114206820B (zh) | 2019-07-29 | 2024-05-10 | 伊士曼化工公司 | 回收成分(c4)烷醛 |
| US11945998B2 (en) | 2019-10-31 | 2024-04-02 | Eastman Chemical Company | Processes and systems for making recycle content hydrocarbons |
| US11319262B2 (en) | 2019-10-31 | 2022-05-03 | Eastman Chemical Company | Processes and systems for making recycle content hydrocarbons |
| US12312540B2 (en) | 2019-10-31 | 2025-05-27 | Eastman Chemical Company | Pyrolysis method and system for recycled waste |
| US12528995B2 (en) | 2019-10-31 | 2026-01-20 | ExxonMobil Product Solutions Company | Pyrolysis method and system for recycled waste |
| EP4055001A4 (en) | 2019-11-07 | 2024-02-14 | Eastman Chemical Company | MIXED ESTERS AND SOLVENTS WITH RECYCLED CONTENTS |
| US12522548B2 (en) | 2019-11-07 | 2026-01-13 | ExxonMobil Product Solutions Company | Recycle content oxo alcohols and oxo plasticizers |
| CN118851872A (zh) | 2019-11-07 | 2024-10-29 | 伊士曼化工公司 | 回收成分丙醇 |
| 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 |
| WO2023242076A1 (en) | 2022-06-13 | 2023-12-21 | Lego A/S | Cellulose ester polymer composition having low coefficient of friction |
| FR3142898A1 (fr) | 2022-12-13 | 2024-06-14 | L'oreal | Procédé de traitement des matières kératiniques mettant en œuvre au moins un composé polysaccharide à fonctions acétoacétates |
| 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 |
| 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 |
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 EP EP92917835A patent/EP0598038B1/en not_active Expired - Lifetime
- 1992-07-30 JP JP5503714A patent/JPH06510805A/ja active Pending
- 1992-07-30 WO PCT/US1992/006304 patent/WO1993003063A1/en not_active Ceased
- 1992-07-30 AT AT92917835T patent/ATE150768T1/de not_active IP Right Cessation
- 1992-07-30 DK DK92917835.8T patent/DK0598038T3/da active
- 1992-07-30 DE DE69218606T patent/DE69218606T2/de not_active Expired - Fee Related
- 1992-07-30 CA CA002106189A patent/CA2106189A1/en not_active Abandoned
- 1992-07-30 ES ES92917835T patent/ES2099276T3/es not_active Expired - Lifetime
-
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 |
|---|---|
| US5292877A (en) | 1994-03-08 |
| EP0598038B1 (en) | 1997-03-26 |
| WO1993003063A1 (en) | 1993-02-18 |
| EP0598038A1 (en) | 1994-05-25 |
| DE69218606D1 (de) | 1997-04-30 |
| ATE150768T1 (de) | 1997-04-15 |
| DE69218606T2 (de) | 1997-07-03 |
| GR3023538T3 (en) | 1997-08-29 |
| DK0598038T3 (da) | 1997-10-06 |
| US5360843A (en) | 1994-11-01 |
| JPH06510805A (ja) | 1994-12-01 |
| TW218384B (cg-RX-API-DMAC10.html) | 1994-01-01 |
| ES2099276T3 (es) | 1997-05-16 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| EP0598038B1 (en) | Coating compositon comprising cellulose acetoacetate | |
| US5595591A (en) | Cellulose acetoacetate esters used in coating compositions | |
| EP1603953B1 (en) | Low molecular weight carboxyalkycellulose esters and their use as low viscosity binders and modifiers in coating compositions | |
| AU722534B2 (en) | Carboxyalkyl cellulose esters | |
| US4011392A (en) | Mixed starch esters and the use thereof | |
| US5973139A (en) | Carboxylated cellulose esters | |
| US5792856A (en) | Process for preparing carboxyalkyl cellulose esters | |
| JP2012207227A (ja) | 低分子量セルロース混合エステル並びにそれらのコーティング組成物中の低粘度結合剤及び改質剤としての使用 | |
| US4061610A (en) | Coating compositions containing starch half-esters and process for preparing same | |
| US4061611A (en) | Aqueous compositions containing starch ester dispersants | |
| JPH1135601A (ja) | エステルエーテル混合セルロース誘導体及びその製造法 | |
| JP2015134924A (ja) | 低分子量セルロース混合エステルを含むベースコート組成物 | |
| EP2411478B1 (en) | Refinish coating compositions comprising low molecular weight cellulose mixed esters | |
| KR20000070676A (ko) | 카복시알킬 셀룰로즈 에스테르 |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request | ||
| FZDE | Discontinued |