CA1051880A - Esters of polyhydroxy polymers and processes for their preparation - Google Patents
Esters of polyhydroxy polymers and processes for their preparationInfo
- Publication number
- CA1051880A CA1051880A CA231,223A CA231223A CA1051880A CA 1051880 A CA1051880 A CA 1051880A CA 231223 A CA231223 A CA 231223A CA 1051880 A CA1051880 A CA 1051880A
- Authority
- CA
- Canada
- Prior art keywords
- cellulose
- ester
- nitrite
- sulfate
- solvent
- 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
Links
- 229920000642 polymer Polymers 0.000 title claims abstract description 124
- 238000000034 method Methods 0.000 title claims abstract description 73
- 150000002148 esters Chemical class 0.000 title claims abstract description 57
- 230000008569 process Effects 0.000 title claims abstract description 53
- 238000002360 preparation method Methods 0.000 title description 17
- -1 alkyl nitrite Chemical compound 0.000 claims abstract description 222
- 229920002678 cellulose Polymers 0.000 claims abstract description 212
- 239000001913 cellulose Substances 0.000 claims abstract description 208
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 108
- 239000000203 mixture Substances 0.000 claims abstract description 76
- 229920002451 polyvinyl alcohol Polymers 0.000 claims abstract description 49
- IOVCWXUNBOPUCH-UHFFFAOYSA-M Nitrite anion Chemical compound [O-]N=O IOVCWXUNBOPUCH-UHFFFAOYSA-M 0.000 claims abstract description 46
- 239000005017 polysaccharide Substances 0.000 claims abstract description 45
- 239000004372 Polyvinyl alcohol Substances 0.000 claims abstract description 42
- 150000004804 polysaccharides Polymers 0.000 claims abstract description 38
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 claims abstract description 28
- 150000004676 glycans Polymers 0.000 claims abstract 7
- WFPZPJSADLPSON-UHFFFAOYSA-N dinitrogen tetraoxide Chemical compound [O-][N+](=O)[N+]([O-])=O WFPZPJSADLPSON-UHFFFAOYSA-N 0.000 claims description 138
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical group CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 82
- 239000002904 solvent Substances 0.000 claims description 72
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 68
- AKEJUJNQAAGONA-UHFFFAOYSA-N sulfur trioxide Chemical compound O=S(=O)=O AKEJUJNQAAGONA-UHFFFAOYSA-N 0.000 claims description 67
- 238000006243 chemical reaction Methods 0.000 claims description 47
- 239000000835 fiber Substances 0.000 claims description 44
- 238000006467 substitution reaction Methods 0.000 claims description 44
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 38
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 36
- 239000011541 reaction mixture Substances 0.000 claims description 31
- 239000003586 protic polar solvent Substances 0.000 claims description 28
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 21
- VPCDQGACGWYTMC-UHFFFAOYSA-N nitrosyl chloride Chemical compound ClN=O VPCDQGACGWYTMC-UHFFFAOYSA-N 0.000 claims description 21
- 235000019392 nitrosyl chloride Nutrition 0.000 claims description 21
- 239000004157 Nitrosyl chloride Substances 0.000 claims description 18
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 18
- 239000003054 catalyst Substances 0.000 claims description 17
- 238000013019 agitation Methods 0.000 claims description 16
- 230000002378 acidificating effect Effects 0.000 claims description 14
- 150000003839 salts Chemical class 0.000 claims description 14
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 claims description 13
- 229910017604 nitric acid Inorganic materials 0.000 claims description 13
- 239000000376 reactant Substances 0.000 claims description 12
- 239000000020 Nitrocellulose Substances 0.000 claims description 11
- 229920001220 nitrocellulos Polymers 0.000 claims description 11
- 230000008961 swelling Effects 0.000 claims description 11
- 238000004519 manufacturing process Methods 0.000 claims description 9
- 150000003512 tertiary amines Chemical class 0.000 claims description 7
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 claims description 6
- 230000003472 neutralizing effect Effects 0.000 claims description 5
- 230000003381 solubilizing effect Effects 0.000 claims description 5
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- 229910001959 inorganic nitrate Inorganic materials 0.000 claims description 4
- 239000003880 polar aprotic solvent Substances 0.000 claims description 4
- 239000000010 aprotic solvent Substances 0.000 claims description 3
- 239000011872 intimate mixture Substances 0.000 claims description 3
- 230000003213 activating effect Effects 0.000 claims 3
- 239000007810 chemical reaction solvent Substances 0.000 claims 3
- 150000007529 inorganic bases Chemical class 0.000 claims 1
- 235000019422 polyvinyl alcohol Nutrition 0.000 abstract description 48
- 229920001282 polysaccharide Polymers 0.000 abstract description 41
- 229910002651 NO3 Inorganic materials 0.000 abstract description 40
- 150000003467 sulfuric acid derivatives Chemical class 0.000 abstract description 30
- NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 abstract description 19
- 150000002823 nitrates Chemical class 0.000 abstract description 14
- 239000012736 aqueous medium Substances 0.000 abstract description 6
- 235000010980 cellulose Nutrition 0.000 description 165
- 239000000243 solution Substances 0.000 description 124
- 239000000047 product Substances 0.000 description 98
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 75
- 235000019441 ethanol Nutrition 0.000 description 46
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 36
- 229940068984 polyvinyl alcohol Drugs 0.000 description 36
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 32
- 239000010408 film Substances 0.000 description 30
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 27
- 238000007034 nitrosation reaction Methods 0.000 description 26
- 150000002826 nitrites Chemical class 0.000 description 25
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 24
- 229920002472 Starch Polymers 0.000 description 24
- 230000009935 nitrosation Effects 0.000 description 24
- 239000008107 starch Substances 0.000 description 24
- 235000019698 starch Nutrition 0.000 description 24
- 239000002244 precipitate Substances 0.000 description 22
- 239000007858 starting material Substances 0.000 description 22
- 230000019635 sulfation Effects 0.000 description 22
- 238000005670 sulfation reaction Methods 0.000 description 22
- 229940032330 sulfuric acid Drugs 0.000 description 22
- 229920002488 Hemicellulose Polymers 0.000 description 21
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 21
- 229920000615 alginic acid Polymers 0.000 description 17
- 239000007864 aqueous solution Substances 0.000 description 17
- 239000000463 material Substances 0.000 description 17
- 229920000742 Cotton Polymers 0.000 description 16
- 241000219146 Gossypium Species 0.000 description 16
- 238000003756 stirring Methods 0.000 description 16
- 239000000370 acceptor Substances 0.000 description 15
- 239000000783 alginic acid Substances 0.000 description 15
- 229960001126 alginic acid Drugs 0.000 description 15
- 239000002585 base Substances 0.000 description 15
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 14
- 235000010443 alginic acid Nutrition 0.000 description 14
- 230000015572 biosynthetic process Effects 0.000 description 14
- 229910052708 sodium Inorganic materials 0.000 description 14
- 239000011734 sodium Substances 0.000 description 14
- 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 13
- 239000002253 acid Substances 0.000 description 12
- 239000007789 gas Substances 0.000 description 12
- 229920002907 Guar gum Polymers 0.000 description 11
- 150000004781 alginic acids Chemical class 0.000 description 11
- 230000000875 corresponding effect Effects 0.000 description 11
- 230000007717 exclusion Effects 0.000 description 11
- 239000000706 filtrate Substances 0.000 description 11
- 235000010417 guar gum Nutrition 0.000 description 11
- 239000000665 guar gum Substances 0.000 description 11
- 229960002154 guar gum Drugs 0.000 description 11
- 238000006386 neutralization reaction Methods 0.000 description 11
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 10
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 10
- 239000003513 alkali Substances 0.000 description 10
- 239000005457 ice water Substances 0.000 description 10
- 229920002230 Pectic acid Polymers 0.000 description 9
- 206010042674 Swelling Diseases 0.000 description 9
- 238000004821 distillation Methods 0.000 description 9
- 238000002156 mixing Methods 0.000 description 9
- 230000002829 reductive effect Effects 0.000 description 9
- 239000007787 solid Substances 0.000 description 9
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
- 238000004458 analytical method Methods 0.000 description 8
- 239000003153 chemical reaction reagent Substances 0.000 description 8
- 230000032050 esterification Effects 0.000 description 8
- 238000005886 esterification reaction Methods 0.000 description 8
- 235000019439 ethyl acetate Nutrition 0.000 description 8
- 229940093499 ethyl acetate Drugs 0.000 description 8
- 239000007788 liquid Substances 0.000 description 8
- 239000012429 reaction media Substances 0.000 description 8
- 238000000926 separation method Methods 0.000 description 8
- 230000001180 sulfating effect Effects 0.000 description 8
- 150000001875 compounds Chemical class 0.000 description 7
- 238000002474 experimental method Methods 0.000 description 7
- 150000004679 hydroxides Chemical class 0.000 description 7
- 239000000543 intermediate Substances 0.000 description 7
- 229920000609 methyl cellulose Polymers 0.000 description 7
- 235000010981 methylcellulose Nutrition 0.000 description 7
- 239000001923 methylcellulose Substances 0.000 description 7
- 239000002023 wood Substances 0.000 description 7
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 6
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical class OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 6
- UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 6
- 229920002134 Carboxymethyl cellulose Polymers 0.000 description 6
- 244000303965 Cyamopsis psoralioides Species 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 6
- 229920000161 Locust bean gum Polymers 0.000 description 6
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 6
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 6
- 150000001298 alcohols Chemical class 0.000 description 6
- 125000005233 alkylalcohol group Chemical group 0.000 description 6
- 239000006227 byproduct Substances 0.000 description 6
- 239000001110 calcium chloride Substances 0.000 description 6
- 229910001628 calcium chloride Inorganic materials 0.000 description 6
- 235000010948 carboxy methyl cellulose Nutrition 0.000 description 6
- 239000001768 carboxy methyl cellulose Substances 0.000 description 6
- 239000008112 carboxymethyl-cellulose Substances 0.000 description 6
- 239000003795 chemical substances by application Substances 0.000 description 6
- 238000001035 drying Methods 0.000 description 6
- 125000004185 ester group Chemical group 0.000 description 6
- 235000010420 locust bean gum Nutrition 0.000 description 6
- 239000000711 locust bean gum Substances 0.000 description 6
- 239000010318 polygalacturonic acid Substances 0.000 description 6
- 229910052700 potassium Inorganic materials 0.000 description 6
- 239000011591 potassium Substances 0.000 description 6
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 6
- 238000011084 recovery Methods 0.000 description 6
- VWDWKYIASSYTQR-UHFFFAOYSA-N sodium nitrate Chemical compound [Na+].[O-][N+]([O-])=O VWDWKYIASSYTQR-UHFFFAOYSA-N 0.000 description 6
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 6
- 241000609240 Ambelania acida Species 0.000 description 5
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 5
- IOVCWXUNBOPUCH-UHFFFAOYSA-N Nitrous acid Chemical compound ON=O IOVCWXUNBOPUCH-UHFFFAOYSA-N 0.000 description 5
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 5
- FJWGYAHXMCUOOM-QHOUIDNNSA-N [(2s,3r,4s,5r,6r)-2-[(2r,3r,4s,5r,6s)-4,5-dinitrooxy-2-(nitrooxymethyl)-6-[(2r,3r,4s,5r,6s)-4,5,6-trinitrooxy-2-(nitrooxymethyl)oxan-3-yl]oxyoxan-3-yl]oxy-3,5-dinitrooxy-6-(nitrooxymethyl)oxan-4-yl] nitrate Chemical compound O([C@@H]1O[C@@H]([C@H]([C@H](O[N+]([O-])=O)[C@H]1O[N+]([O-])=O)O[C@H]1[C@@H]([C@@H](O[N+]([O-])=O)[C@H](O[N+]([O-])=O)[C@@H](CO[N+]([O-])=O)O1)O[N+]([O-])=O)CO[N+](=O)[O-])[C@@H]1[C@@H](CO[N+]([O-])=O)O[C@@H](O[N+]([O-])=O)[C@H](O[N+]([O-])=O)[C@H]1O[N+]([O-])=O FJWGYAHXMCUOOM-QHOUIDNNSA-N 0.000 description 5
- 150000007513 acids Chemical class 0.000 description 5
- 239000010905 bagasse Substances 0.000 description 5
- 229920002301 cellulose acetate Polymers 0.000 description 5
- 238000010438 heat treatment Methods 0.000 description 5
- 239000005076 polymer ester Substances 0.000 description 5
- 229920002689 polyvinyl acetate Polymers 0.000 description 5
- 239000011118 polyvinyl acetate Substances 0.000 description 5
- 239000004627 regenerated cellulose Substances 0.000 description 5
- 239000000725 suspension Substances 0.000 description 5
- 238000012360 testing method Methods 0.000 description 5
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 5
- 238000005406 washing Methods 0.000 description 5
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 4
- 229920003043 Cellulose fiber Polymers 0.000 description 4
- 240000008886 Ceratonia siliqua Species 0.000 description 4
- 235000013912 Ceratonia siliqua Nutrition 0.000 description 4
- ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 description 4
- AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical compound CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 description 4
- WCUXLLCKKVVCTQ-UHFFFAOYSA-M Potassium chloride Chemical compound [Cl-].[K+] WCUXLLCKKVVCTQ-UHFFFAOYSA-M 0.000 description 4
- TZCXTZWJZNENPQ-UHFFFAOYSA-L barium sulfate Chemical compound [Ba+2].[O-]S([O-])(=O)=O TZCXTZWJZNENPQ-UHFFFAOYSA-L 0.000 description 4
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 4
- 235000010418 carrageenan Nutrition 0.000 description 4
- 239000000679 carrageenan Substances 0.000 description 4
- 229920001525 carrageenan Polymers 0.000 description 4
- 229940113118 carrageenan Drugs 0.000 description 4
- 229920000891 common polymer Polymers 0.000 description 4
- 238000001816 cooling Methods 0.000 description 4
- 229920001577 copolymer Polymers 0.000 description 4
- 239000011521 glass Substances 0.000 description 4
- 239000003292 glue Substances 0.000 description 4
- 239000008187 granular material Substances 0.000 description 4
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 4
- 238000002955 isolation Methods 0.000 description 4
- AWJUIBRHMBBTKR-UHFFFAOYSA-N isoquinoline Chemical compound C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 description 4
- 229920002521 macromolecule Polymers 0.000 description 4
- 150000001455 metallic ions Chemical class 0.000 description 4
- 230000007935 neutral effect Effects 0.000 description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- 230000003647 oxidation Effects 0.000 description 4
- 238000007254 oxidation reaction Methods 0.000 description 4
- LCLHHZYHLXDRQG-ZNKJPWOQSA-N pectic acid Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)O[C@H](C(O)=O)[C@@H]1OC1[C@H](O)[C@@H](O)[C@@H](OC2[C@@H]([C@@H](O)[C@@H](O)[C@H](O2)C(O)=O)O)[C@@H](C(O)=O)O1 LCLHHZYHLXDRQG-ZNKJPWOQSA-N 0.000 description 4
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- 230000009257 reactivity Effects 0.000 description 4
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- 238000003860 storage Methods 0.000 description 4
- 239000002562 thickening agent Substances 0.000 description 4
- 229920002554 vinyl polymer Polymers 0.000 description 4
- CWGBFIRHYJNILV-UHFFFAOYSA-N (1,4-diphenyl-1,2,4-triazol-4-ium-3-yl)-phenylazanide Chemical compound C=1C=CC=CC=1[N-]C1=NN(C=2C=CC=CC=2)C=[N+]1C1=CC=CC=C1 CWGBFIRHYJNILV-UHFFFAOYSA-N 0.000 description 3
- 244000215068 Acacia senegal Species 0.000 description 3
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
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- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 3
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- 229920000569 Gum karaya Polymers 0.000 description 3
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- 238000004566 IR spectroscopy Methods 0.000 description 3
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- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical class [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 235000010489 acacia gum Nutrition 0.000 description 3
- 239000000205 acacia gum Substances 0.000 description 3
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 3
- 239000012670 alkaline solution Substances 0.000 description 3
- 150000001412 amines Chemical class 0.000 description 3
- 235000011114 ammonium hydroxide Nutrition 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
- 239000007806 chemical reaction intermediate Substances 0.000 description 3
- 238000000354 decomposition reaction Methods 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- 239000003517 fume Substances 0.000 description 3
- 229920000591 gum Polymers 0.000 description 3
- 229940050526 hydroxyethylstarch Drugs 0.000 description 3
- 235000010494 karaya gum Nutrition 0.000 description 3
- TWNIBLMWSKIRAT-VFUOTHLCSA-N levoglucosan Chemical compound O[C@@H]1[C@@H](O)[C@H](O)[C@H]2CO[C@@H]1O2 TWNIBLMWSKIRAT-VFUOTHLCSA-N 0.000 description 3
- 230000007246 mechanism Effects 0.000 description 3
- 239000002609 medium Substances 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- 238000006396 nitration reaction Methods 0.000 description 3
- 229920001778 nylon Polymers 0.000 description 3
- 239000003960 organic solvent Substances 0.000 description 3
- 230000036961 partial effect Effects 0.000 description 3
- 229920001277 pectin Polymers 0.000 description 3
- 229920002239 polyacrylonitrile Polymers 0.000 description 3
- 229920002959 polymer blend Polymers 0.000 description 3
- 238000006116 polymerization reaction Methods 0.000 description 3
- 108090000623 proteins and genes Proteins 0.000 description 3
- 102000004169 proteins and genes Human genes 0.000 description 3
- 230000008929 regeneration Effects 0.000 description 3
- 238000011069 regeneration method Methods 0.000 description 3
- 229920006395 saturated elastomer Polymers 0.000 description 3
- 235000010344 sodium nitrate Nutrition 0.000 description 3
- 239000004317 sodium nitrate Substances 0.000 description 3
- 235000010288 sodium nitrite Nutrition 0.000 description 3
- 238000009827 uniform distribution Methods 0.000 description 3
- 235000013311 vegetables Nutrition 0.000 description 3
- UHVMMEOXYDMDKI-JKYCWFKZSA-L zinc;1-(5-cyanopyridin-2-yl)-3-[(1s,2s)-2-(6-fluoro-2-hydroxy-3-propanoylphenyl)cyclopropyl]urea;diacetate Chemical compound [Zn+2].CC([O-])=O.CC([O-])=O.CCC(=O)C1=CC=C(F)C([C@H]2[C@H](C2)NC(=O)NC=2N=CC(=CC=2)C#N)=C1O UHVMMEOXYDMDKI-JKYCWFKZSA-L 0.000 description 3
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 2
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- 235000005985 organic acids Nutrition 0.000 description 1
- 230000003204 osmotic effect Effects 0.000 description 1
- 239000005022 packaging material Substances 0.000 description 1
- 238000004806 packaging method and process Methods 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 235000010987 pectin Nutrition 0.000 description 1
- 239000001814 pectin Substances 0.000 description 1
- 229920001568 phenolic resin Polymers 0.000 description 1
- 239000005011 phenolic resin Substances 0.000 description 1
- 235000011007 phosphoric acid Nutrition 0.000 description 1
- 150000003014 phosphoric acid esters Chemical class 0.000 description 1
- 150000003016 phosphoric acids Chemical class 0.000 description 1
- XNGIFLGASWRNHJ-UHFFFAOYSA-M phthalate(1-) Chemical compound OC(=O)C1=CC=CC=C1C([O-])=O XNGIFLGASWRNHJ-UHFFFAOYSA-M 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 229920003229 poly(methyl methacrylate) Polymers 0.000 description 1
- 239000004584 polyacrylic acid Substances 0.000 description 1
- 229920001515 polyalkylene glycol Polymers 0.000 description 1
- 229920000570 polyether Polymers 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 235000013824 polyphenols Nutrition 0.000 description 1
- 229920001290 polyvinyl ester Polymers 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 150000003138 primary alcohols Chemical class 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 238000011027 product recovery Methods 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- 235000010409 propane-1,2-diol alginate Nutrition 0.000 description 1
- 239000000770 propane-1,2-diol alginate Substances 0.000 description 1
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 1
- 229960004063 propylene glycol Drugs 0.000 description 1
- 235000013772 propylene glycol Nutrition 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000012264 purified product Substances 0.000 description 1
- 125000001453 quaternary ammonium group Chemical group 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 235000009566 rice Nutrition 0.000 description 1
- 239000011833 salt mixture Substances 0.000 description 1
- 239000012047 saturated solution Substances 0.000 description 1
- 235000013580 sausages Nutrition 0.000 description 1
- 150000003333 secondary alcohols Chemical class 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- 235000010413 sodium alginate Nutrition 0.000 description 1
- 239000000661 sodium alginate Substances 0.000 description 1
- 229940005550 sodium alginate Drugs 0.000 description 1
- 229910001388 sodium aluminate Inorganic materials 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- HVTHJRMZXBWFNE-UHFFFAOYSA-J sodium zincate Chemical compound [OH-].[OH-].[OH-].[OH-].[Na+].[Na+].[Zn+2] HVTHJRMZXBWFNE-UHFFFAOYSA-J 0.000 description 1
- 230000007480 spreading Effects 0.000 description 1
- 238000003892 spreading Methods 0.000 description 1
- 239000001119 stannous chloride Substances 0.000 description 1
- 235000011150 stannous chloride Nutrition 0.000 description 1
- 229910001631 strontium chloride Inorganic materials 0.000 description 1
- AHBGXTDRMVNFER-UHFFFAOYSA-L strontium dichloride Chemical compound [Cl-].[Cl-].[Sr+2] AHBGXTDRMVNFER-UHFFFAOYSA-L 0.000 description 1
- UUCCCPNEFXQJEL-UHFFFAOYSA-L strontium dihydroxide Chemical compound [OH-].[OH-].[Sr+2] UUCCCPNEFXQJEL-UHFFFAOYSA-L 0.000 description 1
- 229910001866 strontium hydroxide Inorganic materials 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 229920001059 synthetic polymer Polymers 0.000 description 1
- ISXSCDLOGDJUNJ-UHFFFAOYSA-N tert-butyl prop-2-enoate Chemical compound CC(C)(C)OC(=O)C=C ISXSCDLOGDJUNJ-UHFFFAOYSA-N 0.000 description 1
- 150000003509 tertiary alcohols Chemical class 0.000 description 1
- 210000001550 testis Anatomy 0.000 description 1
- 239000004753 textile Substances 0.000 description 1
- 230000008719 thickening Effects 0.000 description 1
- SWZDQOUHBYYPJD-UHFFFAOYSA-N tridodecylamine Chemical compound CCCCCCCCCCCCN(CCCCCCCCCCCC)CCCCCCCCCCCC SWZDQOUHBYYPJD-UHFFFAOYSA-N 0.000 description 1
- 229920006163 vinyl copolymer Polymers 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- NWONKYPBYAMBJT-UHFFFAOYSA-L zinc sulfate Chemical compound [Zn+2].[O-]S([O-])(=O)=O NWONKYPBYAMBJT-UHFFFAOYSA-L 0.000 description 1
- 229910000368 zinc sulfate Inorganic materials 0.000 description 1
- 229960001763 zinc sulfate Drugs 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F8/00—Chemical modification by after-treatment
- C08F8/34—Introducing sulfur atoms or sulfur-containing groups
- C08F8/36—Sulfonation; Sulfation
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08B—POLYSACCHARIDES; DERIVATIVES THEREOF
- C08B31/00—Preparation of derivatives of starch
- C08B31/02—Esters
- C08B31/06—Esters of inorganic acids
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08B—POLYSACCHARIDES; DERIVATIVES THEREOF
- C08B37/00—Preparation of polysaccharides not provided for in groups C08B1/00 - C08B35/00; Derivatives thereof
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08B—POLYSACCHARIDES; DERIVATIVES THEREOF
- C08B5/00—Preparation of cellulose esters of inorganic acids, e.g. phosphates
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08B—POLYSACCHARIDES; DERIVATIVES THEREOF
- C08B5/00—Preparation of cellulose esters of inorganic acids, e.g. phosphates
- C08B5/02—Cellulose nitrate, i.e. nitrocellulose
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08B—POLYSACCHARIDES; DERIVATIVES THEREOF
- C08B5/00—Preparation of cellulose esters of inorganic acids, e.g. phosphates
- C08B5/14—Cellulose sulfate
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F8/00—Chemical modification by after-treatment
- C08F8/30—Introducing nitrogen atoms or nitrogen-containing groups
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F8/00—Chemical modification by after-treatment
- C08F8/42—Introducing metal atoms or metal-containing groups
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Chemistry (AREA)
- Polymers & Plastics (AREA)
- Medicinal Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biochemistry (AREA)
- Materials Engineering (AREA)
- Engineering & Computer Science (AREA)
- General Chemical & Material Sciences (AREA)
- Inorganic Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- Polysaccharides And Polysaccharide Derivatives (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US48719674A | 1974-07-10 | 1974-07-10 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1051880A true CA1051880A (en) | 1979-04-03 |
Family
ID=23934765
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA231,223A Expired CA1051880A (en) | 1974-07-10 | 1975-07-10 | Esters of polyhydroxy polymers and processes for their preparation |
Country Status (17)
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS53134191U (enrdf_load_stackoverflow) * | 1977-03-30 | 1978-10-24 | ||
| JPS57160590A (en) * | 1981-03-31 | 1982-10-02 | Matsushita Electric Works Ltd | Welding method for contact point |
| DE102007035322B4 (de) * | 2007-07-25 | 2011-11-17 | Friedrich-Schiller-Universität Jena | Verfahren zur Herstellung wasserlöslicher, niedrig substituierter Cellulosesulfate |
-
1975
- 1975-07-02 PH PH17356A patent/PH14624A/en unknown
- 1975-07-03 FI FI751951A patent/FI62542C/fi not_active IP Right Cessation
- 1975-07-03 FI FI792994A patent/FI792994A7/fi not_active Application Discontinuation
- 1975-07-08 DE DE19752530451 patent/DE2530451A1/de not_active Ceased
- 1975-07-08 BR BR5531/75D patent/BR7504317A/pt unknown
- 1975-07-08 EG EG398/75A patent/EG12431A/xx active
- 1975-07-08 GB GB28676/75A patent/GB1521125A/en not_active Expired
- 1975-07-08 IT IT50411/75A patent/IT1045532B/it active
- 1975-07-09 SE SE7507871A patent/SE7507871L/xx not_active Application Discontinuation
- 1975-07-09 AU AU82881/75A patent/AU504059B2/en not_active Expired
- 1975-07-09 NO NO752460A patent/NO141994C/no unknown
- 1975-07-09 JP JP8435075A patent/JPS5328345B2/ja not_active Expired
- 1975-07-10 HU HU75SCHE525A patent/HU175674B/hu unknown
- 1975-07-10 BE BE7000681A patent/BE831238A/nl unknown
- 1975-07-10 CA CA231,223A patent/CA1051880A/en not_active Expired
- 1975-07-10 RO RO7597354A patent/RO76171A/ro unknown
- 1975-07-10 AR AR259524A patent/AR215842A1/es active
- 1975-07-10 NL NLAANVRAGE7508261,A patent/NL169884C/xx not_active IP Right Cessation
-
1979
- 1979-04-26 NO NO791389A patent/NO791389L/no unknown
Also Published As
| Publication number | Publication date |
|---|---|
| FI62542C (fi) | 1983-01-10 |
| NL7508261A (nl) | 1976-01-13 |
| AU504059B2 (en) | 1979-10-04 |
| NO141994B (no) | 1980-03-03 |
| PH14624A (en) | 1981-10-12 |
| FI792994A7 (fi) | 1981-01-01 |
| RO76171A (ro) | 1981-11-04 |
| HU175674B (hu) | 1980-09-28 |
| EG12431A (en) | 1979-06-30 |
| NL169884C (nl) | 1982-09-01 |
| GB1521125A (en) | 1978-08-16 |
| JPS5131787A (enrdf_load_stackoverflow) | 1976-03-18 |
| DE2530451A1 (de) | 1976-01-29 |
| BR7504317A (pt) | 1976-07-06 |
| NO791389L (no) | 1976-01-13 |
| FI751951A7 (enrdf_load_stackoverflow) | 1976-01-11 |
| BE831238A (nl) | 1976-01-12 |
| JPS5328345B2 (enrdf_load_stackoverflow) | 1978-08-14 |
| NL169884B (nl) | 1982-04-01 |
| NO141994C (no) | 1980-06-25 |
| AU8288175A (en) | 1977-02-10 |
| SE7507871L (sv) | 1976-01-12 |
| FI62542B (fi) | 1982-09-30 |
| IT1045532B (it) | 1980-05-10 |
| NO752460L (enrdf_load_stackoverflow) | 1976-01-13 |
| AR215842A1 (es) | 1979-11-15 |
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