CA1292986C - Derives de polysaccharide a teneur de groupes d'aldehyde, leur preparation a partir d'acetals correspondants, et leur emploi a titre d'adjuvants pour le papier - Google Patents

Derives de polysaccharide a teneur de groupes d'aldehyde, leur preparation a partir d'acetals correspondants, et leur emploi a titre d'adjuvants pour le papier

Info

Publication number: CA1292986C
Authority: CA; Canada
Prior art keywords: acetal; derivative; starch; polysaccharide; group
Prior art date: 1987-02-13
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 - Lifetime

Application number

CA000529698A

Other languages

English (en)

Inventor

Robert L. Billmers

Diane J. Lamb

Daniel B. Solarek

Patrick G. Jobe

Martin M. Tessler

John Ji-Hsiung Tsai

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Ablestik Laboratories

Original Assignee

Ablestik Laboratories

Priority date (The priority date 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 date listed.)

1987-02-13

Filing date

1987-02-13

Publication date

1991-12-10

1987-02-13 Application filed by Ablestik Laboratories filed Critical Ablestik Laboratories

1987-02-13 Priority to CA000529698A priority Critical patent/CA1292986C/fr

1991-12-10 Application granted granted Critical

1991-12-10 Publication of CA1292986C publication Critical patent/CA1292986C/fr

2008-12-10 Anticipated expiration legal-status Critical

Status Expired - Lifetime legal-status Critical Current

Links

150000001241 acetals Chemical class 0.000 title claims abstract description 134
229920001282 polysaccharide Polymers 0.000 title claims abstract description 67
239000005017 polysaccharide Substances 0.000 title claims abstract description 67
150000004676 glycans Chemical class 0.000 title claims abstract description 62
238000002360 preparation method Methods 0.000 title abstract description 18
239000000654 additive Substances 0.000 title abstract description 11
125000003172 aldehyde group Chemical group 0.000 title description 11
DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 claims abstract description 126
229920002472 Starch Polymers 0.000 claims abstract description 103
235000019698 starch Nutrition 0.000 claims abstract description 103
239000008107 starch Substances 0.000 claims abstract description 100
238000000034 method Methods 0.000 claims abstract description 46
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims abstract description 32
229920002678 cellulose Polymers 0.000 claims abstract description 30
-1 Polysaccharide aldehydes Chemical class 0.000 claims abstract description 29
125000000217 alkyl group Chemical group 0.000 claims abstract description 29
239000001913 cellulose Substances 0.000 claims abstract description 29
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 23
229910052736 halogen Inorganic materials 0.000 claims abstract description 13
150000002367 halogens Chemical class 0.000 claims abstract description 13
125000003710 aryl alkyl group Chemical group 0.000 claims abstract description 11
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 9
239000001257 hydrogen Substances 0.000 claims abstract description 9
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 9
125000003118 aryl group Chemical group 0.000 claims abstract description 8
125000002485 formyl group Chemical class [H]C(*)=O 0.000 claims abstract description 6
125000002877 alkyl aryl group Chemical group 0.000 claims abstract description 5
150000001450 anions Chemical class 0.000 claims abstract description 4
125000002091 cationic group Chemical group 0.000 claims description 46
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 27
LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 27
239000000203 mixture Substances 0.000 claims description 25
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 19
240000008042 Zea mays Species 0.000 claims description 19
235000002017 Zea mays subsp mays Nutrition 0.000 claims description 19
235000005824 Zea mays ssp. parviglumis Nutrition 0.000 claims description 15
235000005822 corn Nutrition 0.000 claims description 15
229920002261 Corn starch Polymers 0.000 claims description 13
BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 claims description 9
VGCXGMAHQTYDJK-UHFFFAOYSA-N Chloroacetyl chloride Chemical group ClCC(Cl)=O VGCXGMAHQTYDJK-UHFFFAOYSA-N 0.000 claims description 6
229910052794 bromium Inorganic materials 0.000 claims description 5
239000008120 corn starch Substances 0.000 claims description 5
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 4
235000016383 Zea mays subsp huehuetenangensis Nutrition 0.000 claims description 4
125000000129 anionic group Chemical group 0.000 claims description 4
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 4
MLUCVPSAIODCQM-NSCUHMNNSA-N crotonaldehyde Chemical compound C\C=C\C=O MLUCVPSAIODCQM-NSCUHMNNSA-N 0.000 claims description 4
MLUCVPSAIODCQM-UHFFFAOYSA-N crotonaldehyde Natural products CC=CC=O MLUCVPSAIODCQM-UHFFFAOYSA-N 0.000 claims description 4
STJIISDMSMJQQK-UHFFFAOYSA-N furan-3-ylmethanol Chemical compound OCC=1C=COC=1 STJIISDMSMJQQK-UHFFFAOYSA-N 0.000 claims description 4
235000009973 maize Nutrition 0.000 claims description 4
FQDIANVAWVHZIR-OWOJBTEDSA-N trans-1,4-Dichlorobutene Chemical group ClC\C=C\CCl FQDIANVAWVHZIR-OWOJBTEDSA-N 0.000 claims description 4
SSFAUOAQOOISRQ-UHFFFAOYSA-N 2,2-diethoxy-n,n-dimethylethanamine Chemical compound CCOC(CN(C)C)OCC SSFAUOAQOOISRQ-UHFFFAOYSA-N 0.000 claims description 3
RUGWIVARLJMKDM-UHFFFAOYSA-N 2-(oxiran-2-ylmethoxymethyl)furan Chemical compound C1OC1COCC1=CC=CO1 RUGWIVARLJMKDM-UHFFFAOYSA-N 0.000 claims description 3
229920002907 Guar gum Polymers 0.000 claims description 3
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 3
239000000665 guar gum Substances 0.000 claims description 3
235000010417 guar gum Nutrition 0.000 claims description 3
229960002154 guar gum Drugs 0.000 claims description 3
MELCWEWUZODSIS-UHFFFAOYSA-N 2-[2-(diethylamino)ethoxy]-n,n-diethylethanamine Chemical group CCN(CC)CCOCCN(CC)CC MELCWEWUZODSIS-UHFFFAOYSA-N 0.000 claims description 2
DRDCOQBVIBGWCZ-UHFFFAOYSA-N 2-chloro-n-(furan-2-ylmethyl)acetamide Chemical group ClCC(=O)NCC1=CC=CO1 DRDCOQBVIBGWCZ-UHFFFAOYSA-N 0.000 claims description 2
229920000856 Amylose Polymers 0.000 claims description 2
244000017020 Ipomoea batatas Species 0.000 claims description 2
235000002678 Ipomoea batatas Nutrition 0.000 claims description 2
240000003183 Manihot esculenta Species 0.000 claims description 2
235000016735 Manihot esculenta subsp esculenta Nutrition 0.000 claims description 2
240000007594 Oryza sativa Species 0.000 claims description 2
235000007164 Oryza sativa Nutrition 0.000 claims description 2
244000061456 Solanum tuberosum Species 0.000 claims description 2
235000002595 Solanum tuberosum Nutrition 0.000 claims description 2
HOPRXXXSABQWAV-UHFFFAOYSA-N anhydrous collidine Natural products CC1=CC=NC(C)=C1C HOPRXXXSABQWAV-UHFFFAOYSA-N 0.000 claims description 2
UTBIMNXEDGNJFE-UHFFFAOYSA-N collidine Natural products CC1=CC=C(C)C(C)=N1 UTBIMNXEDGNJFE-UHFFFAOYSA-N 0.000 claims description 2
235000009566 rice Nutrition 0.000 claims description 2
GFYHSKONPJXCDE-UHFFFAOYSA-N sym-collidine Natural products CC1=CN=C(C)C(C)=C1 GFYHSKONPJXCDE-UHFFFAOYSA-N 0.000 claims description 2
WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 claims 3
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims 2
HUYAEQCJNXODLQ-UHFFFAOYSA-N 2,2-dimethoxy-n,n-dimethylethanamine Chemical compound COC(OC)CN(C)C HUYAEQCJNXODLQ-UHFFFAOYSA-N 0.000 claims 1
RHLBPAKKUQILTE-UHFFFAOYSA-N 2-[2-(1,3-dioxolan-2-yl)ethoxy]ethanol Chemical compound OCCOCCC1OCCO1 RHLBPAKKUQILTE-UHFFFAOYSA-N 0.000 claims 1
WECUIJXZKLGURU-UHFFFAOYSA-N 3-(chloromethyl)furan Chemical compound ClCC=1C=COC=1 WECUIJXZKLGURU-UHFFFAOYSA-N 0.000 claims 1
DDRPCXLAQZKBJP-UHFFFAOYSA-N furfurylamine Chemical compound NCC1=CC=CO1 DDRPCXLAQZKBJP-UHFFFAOYSA-N 0.000 claims 1
DPLOXPRJCFWURN-UHFFFAOYSA-N n-(2,2-diethoxyethyl)-2,2-diethoxy-n-methylethanamine Chemical compound CCOC(OCC)CN(C)CC(OCC)OCC DPLOXPRJCFWURN-UHFFFAOYSA-N 0.000 claims 1
239000003153 chemical reaction reagent Substances 0.000 abstract description 74
150000001299 aldehydes Chemical group 0.000 abstract description 68
239000002585 base Substances 0.000 abstract description 27
230000001590 oxidative effect Effects 0.000 abstract description 11
150000002118 epoxides Chemical class 0.000 abstract description 7
230000003301 hydrolyzing effect Effects 0.000 abstract description 6
239000003513 alkali Substances 0.000 abstract description 5
150000002170 ethers Chemical class 0.000 abstract description 5
150000003944 halohydrins Chemical class 0.000 abstract description 5
125000000962 organic group Chemical group 0.000 abstract description 4
229920000591 gum Polymers 0.000 abstract 1
238000006243 chemical reaction Methods 0.000 description 84
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 78
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 52
239000000243 solution Substances 0.000 description 32
235000010980 cellulose Nutrition 0.000 description 26
229920000881 Modified starch Polymers 0.000 description 21
235000019426 modified starch Nutrition 0.000 description 21
239000002904 solvent Substances 0.000 description 20
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 18
239000000123 paper Substances 0.000 description 18
239000000047 product Substances 0.000 description 18
239000002002 slurry Substances 0.000 description 18
HGINCPLSRVDWNT-UHFFFAOYSA-N Acrolein Chemical compound C=CC=O HGINCPLSRVDWNT-UHFFFAOYSA-N 0.000 description 16
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 16
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 16
238000003756 stirring Methods 0.000 description 16
229910052757 nitrogen Inorganic materials 0.000 description 13
RAGSWDIQBBZLLL-UHFFFAOYSA-N 2-chloroethyl(diethyl)azanium;chloride Chemical compound Cl.CCN(CC)CCCl RAGSWDIQBBZLLL-UHFFFAOYSA-N 0.000 description 12
239000002253 acid Substances 0.000 description 11
239000011541 reaction mixture Substances 0.000 description 11
238000009835 boiling Methods 0.000 description 9
238000010411 cooking Methods 0.000 description 9
150000002500 ions Chemical class 0.000 description 9
239000007787 solid Substances 0.000 description 9
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 8
235000019759 Maize starch Nutrition 0.000 description 8
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 8
239000007788 liquid Substances 0.000 description 8
229910052938 sodium sulfate Inorganic materials 0.000 description 8
235000011152 sodium sulphate Nutrition 0.000 description 8
125000001424 substituent group Chemical group 0.000 description 8
238000004448 titration Methods 0.000 description 8
239000000460 chlorine Substances 0.000 description 7
150000002009 diols Chemical class 0.000 description 7
239000000499 gel Substances 0.000 description 7
239000003921 oil Substances 0.000 description 7
235000019198 oils Nutrition 0.000 description 7
239000012071 phase Substances 0.000 description 7
238000010992 reflux Methods 0.000 description 7
239000011734 sodium Substances 0.000 description 7
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 6
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
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 6
239000000835 fiber Substances 0.000 description 6
LEQAOMBKQFMDFZ-UHFFFAOYSA-N glyoxal Chemical compound O=CC=O LEQAOMBKQFMDFZ-UHFFFAOYSA-N 0.000 description 6
229910052708 sodium Inorganic materials 0.000 description 6
RZVAJINKPMORJF-UHFFFAOYSA-N Acetaminophen Chemical compound CC(=O)NC1=CC=C(O)C=C1 RZVAJINKPMORJF-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
QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 5
239000007864 aqueous solution Substances 0.000 description 5
238000001816 cooling Methods 0.000 description 5
238000001212 derivatisation Methods 0.000 description 5
125000002887 hydroxy group Chemical group [H]O* 0.000 description 5
239000000463 material Substances 0.000 description 5
KHIWWQKSHDUIBK-UHFFFAOYSA-N periodic acid Chemical compound OI(=O)(=O)=O KHIWWQKSHDUIBK-UHFFFAOYSA-N 0.000 description 5
NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 5
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 4
YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 4
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 4
239000007832 Na2SO4 Substances 0.000 description 4
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
229910052783 alkali metal Inorganic materials 0.000 description 4
230000015572 biosynthetic process Effects 0.000 description 4
239000012065 filter cake Substances 0.000 description 4
125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 4
230000003647 oxidation Effects 0.000 description 4
238000007254 oxidation reaction Methods 0.000 description 4
230000020477 pH reduction Effects 0.000 description 4
230000008569 process Effects 0.000 description 4
238000006467 substitution reaction Methods 0.000 description 4
239000004094 surface-active agent Substances 0.000 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 description 4
238000005406 washing Methods 0.000 description 4
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 3
HUMIEJNVCICTPJ-UHFFFAOYSA-N 2,2-dimethoxy-n-methylethanamine Chemical compound CNCC(OC)OC HUMIEJNVCICTPJ-UHFFFAOYSA-N 0.000 description 3
SSZWWUDQMAHNAQ-UHFFFAOYSA-N 3-chloropropane-1,2-diol Chemical compound OCC(O)CCl SSZWWUDQMAHNAQ-UHFFFAOYSA-N 0.000 description 3
ZNZYKNKBJPZETN-WELNAUFTSA-N Dialdehyde 11678 Chemical compound N1C2=CC=CC=C2C2=C1[C@H](C[C@H](/C(=C/O)C(=O)OC)[C@@H](C=C)C=O)NCC2 ZNZYKNKBJPZETN-WELNAUFTSA-N 0.000 description 3
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
LSNNMFCWUKXFEE-UHFFFAOYSA-N Sulfurous acid Chemical compound OS(O)=O LSNNMFCWUKXFEE-UHFFFAOYSA-N 0.000 description 3
125000004036 acetal group Chemical group 0.000 description 3
150000001340 alkali metals Chemical class 0.000 description 3
150000001412 amines Chemical class 0.000 description 3
AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 description 3
150000001720 carbohydrates Chemical class 0.000 description 3
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 3
229910052801 chlorine Inorganic materials 0.000 description 3
238000004132 cross linking Methods 0.000 description 3
125000004122 cyclic group Chemical group 0.000 description 3
238000004821 distillation Methods 0.000 description 3
229940015043 glyoxal Drugs 0.000 description 3
238000010438 heat treatment Methods 0.000 description 3
XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 3
229920000609 methyl cellulose Polymers 0.000 description 3
239000001923 methylcellulose Substances 0.000 description 3
235000010981 methylcellulose Nutrition 0.000 description 3
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
239000003960 organic solvent Substances 0.000 description 3
229920005989 resin Polymers 0.000 description 3
239000011347 resin Substances 0.000 description 3
238000007142 ring opening reaction Methods 0.000 description 3
GHPYJLCQYMAXGG-WCCKRBBISA-N (2R)-2-amino-3-(2-boronoethylsulfanyl)propanoic acid hydrochloride Chemical compound Cl.N[C@@H](CSCCB(O)O)C(O)=O GHPYJLCQYMAXGG-WCCKRBBISA-N 0.000 description 2
SPEUIVXLLWOEMJ-UHFFFAOYSA-N 1,1-dimethoxyethane Chemical compound COC(C)OC SPEUIVXLLWOEMJ-UHFFFAOYSA-N 0.000 description 2
WNXJIVFYUVYPPR-UHFFFAOYSA-N 1,3-dioxolane Chemical compound C1COCO1 WNXJIVFYUVYPPR-UHFFFAOYSA-N 0.000 description 2
HJKLEAOXCZIMPI-UHFFFAOYSA-N 2,2-diethoxyethanamine Chemical compound CCOC(CN)OCC HJKLEAOXCZIMPI-UHFFFAOYSA-N 0.000 description 2
DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 2
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 2
108090000790 Enzymes Proteins 0.000 description 2
102000004190 Enzymes Human genes 0.000 description 2
239000004354 Hydroxyethyl cellulose Substances 0.000 description 2
229920000663 Hydroxyethyl cellulose Polymers 0.000 description 2
229920000161 Locust bean gum Polymers 0.000 description 2
BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical group CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 description 2
229910002651 NO3 Inorganic materials 0.000 description 2
NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 2
KFSLWBXXFJQRDL-UHFFFAOYSA-N Peracetic acid Chemical compound CC(=O)OO KFSLWBXXFJQRDL-UHFFFAOYSA-N 0.000 description 2
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 2
DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 2
GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 2
238000005903 acid hydrolysis reaction Methods 0.000 description 2
238000013019 agitation Methods 0.000 description 2
125000002947 alkylene group Chemical group 0.000 description 2
239000012267 brine Substances 0.000 description 2
230000005587 bubbling Effects 0.000 description 2
239000000920 calcium hydroxide Substances 0.000 description 2
229910001861 calcium hydroxide Inorganic materials 0.000 description 2
235000011116 calcium hydroxide Nutrition 0.000 description 2
OSGAYBCDTDRGGQ-UHFFFAOYSA-L calcium sulfate Chemical compound [Ca+2].[O-]S([O-])(=O)=O OSGAYBCDTDRGGQ-UHFFFAOYSA-L 0.000 description 2
230000015556 catabolic process Effects 0.000 description 2
230000003197 catalytic effect Effects 0.000 description 2
229920003086 cellulose ether Polymers 0.000 description 2
238000006731 degradation reaction Methods 0.000 description 2
238000000502 dialysis Methods 0.000 description 2
125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 2
239000012153 distilled water Substances 0.000 description 2
238000001035 drying Methods 0.000 description 2
230000000694 effects Effects 0.000 description 2
125000004185 ester group Chemical group 0.000 description 2
IDGUHHHQCWSQLU-UHFFFAOYSA-N ethanol;hydrate Chemical compound O.CCO IDGUHHHQCWSQLU-UHFFFAOYSA-N 0.000 description 2
125000001033 ether group Chemical group 0.000 description 2
239000000284 extract Substances 0.000 description 2
239000012467 final product Substances 0.000 description 2
150000002240 furans Chemical class 0.000 description 2
150000002431 hydrogen Chemical class 0.000 description 2
235000019447 hydroxyethyl cellulose Nutrition 0.000 description 2
JGJLWPGRMCADHB-UHFFFAOYSA-N hypobromite Chemical compound Br[O-] JGJLWPGRMCADHB-UHFFFAOYSA-N 0.000 description 2
238000007654 immersion Methods 0.000 description 2
229910052740 iodine Inorganic materials 0.000 description 2
235000010420 locust bean gum Nutrition 0.000 description 2
239000000711 locust bean gum Substances 0.000 description 2
229910052943 magnesium sulfate Inorganic materials 0.000 description 2
235000019341 magnesium sulphate Nutrition 0.000 description 2
SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 description 2
230000007935 neutral effect Effects 0.000 description 2
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 2
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Polysaccharides And Polysaccharide Derivatives (AREA)

CA000529698A 1987-02-13 1987-02-13 Derives de polysaccharide a teneur de groupes d'aldehyde, leur preparation a partir d'acetals correspondants, et leur emploi a titre d'adjuvants pour le papier Expired - Lifetime CA1292986C (fr)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
CA000529698A CA1292986C (fr)	1987-02-13	1987-02-13	Derives de polysaccharide a teneur de groupes d'aldehyde, leur preparation a partir d'acetals correspondants, et leur emploi a titre d'adjuvants pour le papier

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
CA000529698A CA1292986C (fr)	1987-02-13	1987-02-13	Derives de polysaccharide a teneur de groupes d'aldehyde, leur preparation a partir d'acetals correspondants, et leur emploi a titre d'adjuvants pour le papier

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CA1292986C true CA1292986C (fr)	1991-12-10

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CA000529698A Expired - Lifetime CA1292986C (fr)	1987-02-13	1987-02-13	Derives de polysaccharide a teneur de groupes d'aldehyde, leur preparation a partir d'acetals correspondants, et leur emploi a titre d'adjuvants pour le papier

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CA (1)	CA1292986C (fr)

1987
- 1987-02-13 CA CA000529698A patent/CA1292986C/fr not_active Expired - Lifetime

Legal Events

Date	Code	Title	Description
2003-12-10	MKLA	Lapsed

Publication	Publication Date	Title
US4804769A (en)	1989-02-14	Acetals useful for the preparation of polysaccharide derivatives
US4983748A (en)	1991-01-08	Acetals useful for the preparation of polysaccharide derivatives
US4741804A (en)	1988-05-03	Polysaccharide derivatives containing aldehyde groups, their preparation from the corresponding acetals and use as paper additives
US4731162A (en)	1988-03-15	Polysaccharide derivatives containing aldehyde groups for use as paper additives
US4675394A (en)	1987-06-23	Polysaccharide derivatives containing aldehyde groups, their preparation from the corresponding acetals and use as paper additives
US4788280A (en)	1988-11-29	Polysaccharide derivatives containing aldehyde groups on an aromatic ring, their preparation from the corresponding acetals and use in paper
CA1296442C (fr)	1992-02-25	Polymeres greffes polysaccharidiques renfermant des groupements acetal et leur transformation en groupements aldehyde
US3472840A (en)	1969-10-14	Quaternary nitrogen-containing cellulose ethers
JP2558089B2 (ja)	1996-11-27	有機シロキサン含有澱粉を用いた製紙方法
US4749800A (en)	1988-06-07	Polysaccharide esters containing acetal and aldehyde groups
CA1303609C (fr)	1992-06-16	Esters de polysaccharides qui contiennent des groupements acetal et aldehyde
JP2509739B2 (ja)	1996-06-26	カチオン性ポリサッカライドおよびこれを製造するための試薬
JP5398844B2 (ja)	2014-01-29	製紙方法
JP2000178303A (ja)	2000-06-27	多糖誘導体
US5227481A (en)	1993-07-13	Cationic polysaccharides and reagents for their preparation
CA1292986C (fr)	1991-12-10	Derives de polysaccharide a teneur de groupes d'aldehyde, leur preparation a partir d'acetals correspondants, et leur emploi a titre d'adjuvants pour le papier
US3087852A (en)	1963-04-30	Cationic polymeric dialdehydes and their use in making wet strength paper
US3354034A (en)	1967-11-21	Novel cationic starch derivatives
US4992536A (en)	1991-02-12	Preparation of polycationic polysaccharides by site selective reaction
US5616800A (en)	1997-04-01	Dicationic and polycationic monoprimary alcohols and derivatives thereof
US3205125A (en)	1965-09-07	Forming paper containing periodate oxidized polygalactomannan gum and paper thereof
CA1237124A (fr)	1988-05-24	Derives de polysaccharides contenant des groupes aldehyde, leur preparation a partir des acetals correspondants et leur emploi comme additifs du papier
US20010025102A1 (en)	2001-09-27	Cold water soluble starch aldehydes and the method of preparation thereof
CA1339137C (fr)	1997-07-29	Polymeres de greffe de types polysaccharides, renfermant des groupes acetals et leur conversion en groupes aldehydes