CA1114094A - Quaternary ammonium salts of epihalohydrin polymers as additives for fibrous materials - Google Patents
Quaternary ammonium salts of epihalohydrin polymers as additives for fibrous materialsInfo
- Publication number
- CA1114094A CA1114094A CA268,769A CA268769A CA1114094A CA 1114094 A CA1114094 A CA 1114094A CA 268769 A CA268769 A CA 268769A CA 1114094 A CA1114094 A CA 1114094A
- Authority
- CA
- Canada
- Prior art keywords
- polyether
- hydrogen
- alkyl
- composition
- hydrocarbyl
- 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
- 239000002657 fibrous material Substances 0.000 title abstract description 5
- 229920000642 polymer Polymers 0.000 title description 23
- 239000000654 additive Substances 0.000 title description 19
- 150000003242 quaternary ammonium salts Chemical class 0.000 title 1
- 229920000570 polyether Polymers 0.000 claims abstract description 101
- 239000004721 Polyphenylene oxide Substances 0.000 claims abstract description 72
- 239000001257 hydrogen Substances 0.000 claims abstract description 29
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 29
- 125000002091 cationic group Chemical group 0.000 claims abstract description 28
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 19
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims abstract description 12
- 125000001183 hydrocarbyl group Chemical group 0.000 claims abstract description 11
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical group [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 9
- 150000003863 ammonium salts Chemical group 0.000 claims abstract description 7
- 150000001450 anions Chemical class 0.000 claims abstract description 7
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 7
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 6
- 150000002367 halogens Chemical group 0.000 claims abstract description 6
- 239000000835 fiber Substances 0.000 claims description 27
- 239000000203 mixture Substances 0.000 claims description 16
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 claims description 10
- 229920006318 anionic polymer Polymers 0.000 claims description 8
- 125000003700 epoxy group Chemical group 0.000 claims description 8
- 150000002431 hydrogen Chemical class 0.000 claims description 8
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 7
- 125000002947 alkylene group Chemical group 0.000 claims description 6
- 229920002401 polyacrylamide Polymers 0.000 claims description 6
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 6
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 claims description 4
- 239000004215 Carbon black (E152) Substances 0.000 claims description 3
- 125000003118 aryl group Chemical group 0.000 claims description 3
- 229930195733 hydrocarbon Natural products 0.000 claims description 3
- 239000003999 initiator Substances 0.000 claims description 3
- 125000000467 secondary amino group Chemical group [H]N([*:1])[*:2] 0.000 claims description 3
- 125000001424 substituent group Chemical group 0.000 claims description 3
- 125000001302 tertiary amino group Chemical group 0.000 claims description 3
- 229910052799 carbon Inorganic materials 0.000 claims description 2
- 125000002993 cycloalkylene group Chemical group 0.000 claims description 2
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims 1
- -1 alkyl Chemical class 0.000 abstract description 10
- 239000000123 paper Substances 0.000 description 26
- 239000000243 solution Substances 0.000 description 19
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 18
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 16
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 16
- 239000004753 textile Substances 0.000 description 13
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 12
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
- 125000001453 quaternary ammonium group Chemical group 0.000 description 10
- 238000006243 chemical reaction Methods 0.000 description 9
- 238000000034 method Methods 0.000 description 9
- 239000002904 solvent Substances 0.000 description 9
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 8
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 8
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 8
- 238000004519 manufacturing process Methods 0.000 description 8
- 150000001412 amines Chemical class 0.000 description 7
- HONIICLYMWZJFZ-UHFFFAOYSA-N azetidine Chemical group C1CNC1 HONIICLYMWZJFZ-UHFFFAOYSA-N 0.000 description 7
- 239000000725 suspension Substances 0.000 description 7
- 229920001131 Pulp (paper) Polymers 0.000 description 6
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 6
- 230000000996 additive effect Effects 0.000 description 6
- 239000003795 chemical substances by application Substances 0.000 description 6
- 239000008367 deionised water Substances 0.000 description 6
- 229910021641 deionized water Inorganic materials 0.000 description 6
- 125000002768 hydroxyalkyl group Chemical group 0.000 description 6
- 239000007787 solid Substances 0.000 description 6
- 239000004593 Epoxy Substances 0.000 description 5
- 239000007864 aqueous solution Substances 0.000 description 5
- 150000002118 epoxides Chemical group 0.000 description 5
- 150000003335 secondary amines Chemical class 0.000 description 5
- 229910001868 water Inorganic materials 0.000 description 5
- 239000002023 wood Substances 0.000 description 5
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 4
- 125000003277 amino group Chemical group 0.000 description 4
- 125000004103 aminoalkyl group Chemical group 0.000 description 4
- HONIICLYMWZJFZ-UHFFFAOYSA-O azetidin-1-ium Chemical compound C1C[NH2+]C1 HONIICLYMWZJFZ-UHFFFAOYSA-O 0.000 description 4
- 229910000019 calcium carbonate Inorganic materials 0.000 description 4
- 235000010216 calcium carbonate Nutrition 0.000 description 4
- 239000000460 chlorine Substances 0.000 description 4
- 239000004744 fabric Substances 0.000 description 4
- 239000000178 monomer Substances 0.000 description 4
- 238000006116 polymerization reaction Methods 0.000 description 4
- 238000002360 preparation method Methods 0.000 description 4
- 239000002002 slurry Substances 0.000 description 4
- 238000004448 titration Methods 0.000 description 4
- 239000002253 acid Substances 0.000 description 3
- 238000004458 analytical method Methods 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 125000001188 haloalkyl group Chemical group 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 150000003141 primary amines Chemical class 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- 239000011780 sodium chloride Substances 0.000 description 3
- 238000005728 strengthening Methods 0.000 description 3
- IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
- LSNNMFCWUKXFEE-UHFFFAOYSA-N Sulfurous acid Chemical compound OS(O)=O LSNNMFCWUKXFEE-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 238000013019 agitation Methods 0.000 description 2
- 125000003282 alkyl amino group Chemical group 0.000 description 2
- 125000005529 alkyleneoxy group Chemical group 0.000 description 2
- 238000005576 amination reaction Methods 0.000 description 2
- 229910021529 ammonia Inorganic materials 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-O ammonium group Chemical group [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 2
- 239000002216 antistatic agent Substances 0.000 description 2
- 239000007900 aqueous suspension Substances 0.000 description 2
- 125000002393 azetidinyl group Chemical group 0.000 description 2
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 2
- WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 125000004218 chloromethyl group Chemical group [H]C([H])(Cl)* 0.000 description 2
- 238000007334 copolymerization reaction Methods 0.000 description 2
- 150000004292 cyclic ethers Chemical class 0.000 description 2
- GYZLOYUZLJXAJU-UHFFFAOYSA-N diglycidyl ether Chemical class C1OC1COCC1CO1 GYZLOYUZLJXAJU-UHFFFAOYSA-N 0.000 description 2
- 230000008034 disappearance Effects 0.000 description 2
- 239000006185 dispersion Substances 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 238000004817 gas chromatography Methods 0.000 description 2
- 238000005227 gel permeation chromatography Methods 0.000 description 2
- 239000002655 kraft paper Substances 0.000 description 2
- 230000014759 maintenance of location Effects 0.000 description 2
- 239000000049 pigment Substances 0.000 description 2
- 238000004513 sizing Methods 0.000 description 2
- 239000011550 stock solution Substances 0.000 description 2
- 150000003512 tertiary amines Chemical class 0.000 description 2
- RBACIKXCRWGCBB-UHFFFAOYSA-N 1,2-Epoxybutane Chemical compound CCC1CO1 RBACIKXCRWGCBB-UHFFFAOYSA-N 0.000 description 1
- KWKAKUADMBZCLK-UHFFFAOYSA-N 1-octene Chemical group CCCCCCC=C KWKAKUADMBZCLK-UHFFFAOYSA-N 0.000 description 1
- GELKGHVAFRCJNA-UHFFFAOYSA-N 2,2-Dimethyloxirane Chemical compound CC1(C)CO1 GELKGHVAFRCJNA-UHFFFAOYSA-N 0.000 description 1
- PQXKWPLDPFFDJP-UHFFFAOYSA-N 2,3-dimethyloxirane Chemical compound CC1OC1C PQXKWPLDPFFDJP-UHFFFAOYSA-N 0.000 description 1
- STMDPCBYJCIZOD-UHFFFAOYSA-N 2-(2,4-dinitroanilino)-4-methylpentanoic acid Chemical compound CC(C)CC(C(O)=O)NC1=CC=C([N+]([O-])=O)C=C1[N+]([O-])=O STMDPCBYJCIZOD-UHFFFAOYSA-N 0.000 description 1
- YSUQLAYJZDEMOT-UHFFFAOYSA-N 2-(butoxymethyl)oxirane Chemical compound CCCCOCC1CO1 YSUQLAYJZDEMOT-UHFFFAOYSA-N 0.000 description 1
- LKMJVFRMDSNFRT-UHFFFAOYSA-N 2-(methoxymethyl)oxirane Chemical compound COCC1CO1 LKMJVFRMDSNFRT-UHFFFAOYSA-N 0.000 description 1
- MSWONMWDQHSVIY-UHFFFAOYSA-N 2-[(4-dodecylphenoxy)methyl]oxirane Chemical compound C1=CC(CCCCCCCCCCCC)=CC=C1OCC1OC1 MSWONMWDQHSVIY-UHFFFAOYSA-N 0.000 description 1
- 239000005995 Aluminium silicate Substances 0.000 description 1
- 229910015900 BF3 Inorganic materials 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- 229920000742 Cotton Polymers 0.000 description 1
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
- 238000005727 Friedel-Crafts reaction Methods 0.000 description 1
- CTKINSOISVBQLD-UHFFFAOYSA-N Glycidol Chemical compound OCC1CO1 CTKINSOISVBQLD-UHFFFAOYSA-N 0.000 description 1
- 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 1
- 239000005909 Kieselgur Substances 0.000 description 1
- 239000004677 Nylon Substances 0.000 description 1
- FQYUMYWMJTYZTK-UHFFFAOYSA-N Phenyl glycidyl ether Chemical compound C1OC1COC1=CC=CC=C1 FQYUMYWMJTYZTK-UHFFFAOYSA-N 0.000 description 1
- 239000004952 Polyamide Substances 0.000 description 1
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 1
- 229920002125 Sokalan® Polymers 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 150000001299 aldehydes Chemical class 0.000 description 1
- 150000001336 alkenes Chemical class 0.000 description 1
- 125000003342 alkenyl group Chemical group 0.000 description 1
- 150000001350 alkyl halides Chemical class 0.000 description 1
- 235000012211 aluminium silicate Nutrition 0.000 description 1
- 125000003368 amide group Chemical group 0.000 description 1
- 239000003957 anion exchange resin Substances 0.000 description 1
- 125000000129 anionic group Chemical group 0.000 description 1
- 238000010009 beating Methods 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 229940106691 bisphenol a Drugs 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 125000001246 bromo group Chemical group Br* 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 239000004927 clay Substances 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- 238000004132 cross linking Methods 0.000 description 1
- 125000000753 cycloalkyl group Chemical group 0.000 description 1
- 125000004663 dialkyl amino group Chemical group 0.000 description 1
- 150000004985 diamines Chemical class 0.000 description 1
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 1
- 229940043237 diethanolamine Drugs 0.000 description 1
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
- 238000007865 diluting Methods 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- WEHWNAOGRSTTBQ-UHFFFAOYSA-N dipropylamine Chemical compound CCCNCCC WEHWNAOGRSTTBQ-UHFFFAOYSA-N 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- GKIPXFAANLTWBM-UHFFFAOYSA-N epibromohydrin Chemical compound BrCC1CO1 GKIPXFAANLTWBM-UHFFFAOYSA-N 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 150000003944 halohydrins Chemical class 0.000 description 1
- 125000004970 halomethyl group Chemical group 0.000 description 1
- 239000011121 hardwood Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 150000002391 heterocyclic compounds Chemical class 0.000 description 1
- 239000003456 ion exchange resin Substances 0.000 description 1
- 229920003303 ion-exchange polymer Polymers 0.000 description 1
- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- DYUWTXWIYMHBQS-UHFFFAOYSA-N n-prop-2-enylprop-2-en-1-amine Chemical compound C=CCNCC=C DYUWTXWIYMHBQS-UHFFFAOYSA-N 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 230000003472 neutralizing effect Effects 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 229920001778 nylon Polymers 0.000 description 1
- AHHWIHXENZJRFG-UHFFFAOYSA-N oxetane Chemical compound C1COC1 AHHWIHXENZJRFG-UHFFFAOYSA-N 0.000 description 1
- 239000010893 paper waste Substances 0.000 description 1
- 239000004584 polyacrylic acid Substances 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 230000000379 polymerizing effect Effects 0.000 description 1
- 229920000098 polyolefin Polymers 0.000 description 1
- 239000013055 pulp slurry Substances 0.000 description 1
- 238000005956 quaternization reaction Methods 0.000 description 1
- 238000004064 recycling Methods 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- UIIMBOGNXHQVGW-UHFFFAOYSA-N sodium;hydron;carbonate Chemical compound [Na+].OC(O)=O UIIMBOGNXHQVGW-UHFFFAOYSA-N 0.000 description 1
- 239000011122 softwood Substances 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 239000008399 tap water Substances 0.000 description 1
- 235000020679 tap water Nutrition 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 238000001029 thermal curing Methods 0.000 description 1
- 150000003568 thioethers Chemical class 0.000 description 1
- 150000004684 trihydrates Chemical class 0.000 description 1
- 210000002268 wool Anatomy 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
- C08G65/02—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
- C08G65/32—Polymers modified by chemical after-treatment
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
- C08G65/02—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
- C08G65/32—Polymers modified by chemical after-treatment
- C08G65/329—Polymers modified by chemical after-treatment with organic compounds
- C08G65/333—Polymers modified by chemical after-treatment with organic compounds containing nitrogen
- C08G65/33303—Polymers modified by chemical after-treatment with organic compounds containing nitrogen containing amino group
- C08G65/33306—Polymers modified by chemical after-treatment with organic compounds containing nitrogen containing amino group acyclic
Landscapes
- Chemical & Material Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Paper (AREA)
- Polyethers (AREA)
- Epoxy Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US05/652,599 US4156775A (en) | 1976-01-26 | 1976-01-26 | Quaternary ammonium salts of epihalohydrin polymers as additives for fibrous materials |
| US652,599 | 1976-01-26 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1114094A true CA1114094A (en) | 1981-12-08 |
Family
ID=24617417
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA268,769A Expired CA1114094A (en) | 1976-01-26 | 1976-12-24 | Quaternary ammonium salts of epihalohydrin polymers as additives for fibrous materials |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US4156775A (cg-RX-API-DMAC7.html) |
| JP (1) | JPS5293500A (cg-RX-API-DMAC7.html) |
| AU (1) | AU511737B2 (cg-RX-API-DMAC7.html) |
| CA (1) | CA1114094A (cg-RX-API-DMAC7.html) |
| DE (1) | DE2702712A1 (cg-RX-API-DMAC7.html) |
| FR (1) | FR2338959A1 (cg-RX-API-DMAC7.html) |
| GB (1) | GB1527582A (cg-RX-API-DMAC7.html) |
| IT (1) | IT1079552B (cg-RX-API-DMAC7.html) |
| SE (1) | SE7700782L (cg-RX-API-DMAC7.html) |
Families Citing this family (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2820488A1 (de) * | 1978-05-10 | 1979-11-15 | Bayer Ag | Quaternaere dialkylammoniumgruppen enthaltende polyalkylenpolyamine |
| US4416729A (en) * | 1982-01-04 | 1983-11-22 | The Dow Chemical Company | Ammonium polyamidoamines |
| US4404377A (en) * | 1982-03-08 | 1983-09-13 | Nalco Chemical Company | Heterocyclic/aromatic fluorocarbon surfactants |
| JPH0542908A (ja) * | 1991-08-02 | 1993-02-23 | Watanabe Kikai Kogyo Kk | 細長い植物の自動結束方法及び装置 |
| US6177577B1 (en) | 1991-11-15 | 2001-01-23 | The Dow Chemical Company | Dicationic and polycationic monoprimary alcohols and derivatives thereof |
| GB0201165D0 (en) * | 2002-01-18 | 2002-03-06 | Unilever Plc | Azetidinium modidfied poymers and fabric treatment composition |
| GB0205277D0 (en) * | 2002-03-06 | 2002-04-17 | Unilever Plc | Azetidinium-functionalised polymer and compositions containing the same |
| US7423112B2 (en) * | 2004-05-27 | 2008-09-09 | Bayer Materialscience Llc | Polyether polyols containing pendant amine groups and a process for their preparation |
| CN101225163B (zh) * | 2008-02-21 | 2011-05-11 | 河南科技大学 | 由聚环氧氯丙烷制备聚醚型大分子离子液体的方法 |
| WO2018151162A1 (ja) * | 2017-02-15 | 2018-08-23 | 日本ゼオン株式会社 | 帯電防止剤、ならびにそれを用いた成形体用組成物および架橋性組成物 |
| US10662586B2 (en) | 2017-06-28 | 2020-05-26 | Gpcp Ip Holdings Llc | Cationic polyetheramine dispersants for preparing papermaking stock |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3428680A (en) * | 1964-01-03 | 1969-02-18 | Procter & Gamble | Polyquaternary ammonium salts of polymerized epichlorohydrin |
| GB1208474A (en) * | 1968-04-29 | 1970-10-14 | Agfa Gevaert Nv | Electroconductive layers for use in electrographic and electrophotographic recording elements |
| BE757509A (fr) * | 1969-10-15 | 1971-04-14 | Rhone Poulenc Sa | Nouveaux copolymeres azotes |
| US3640766A (en) * | 1970-01-07 | 1972-02-08 | Nalco Chemical Co | Electrophotographic-recording member and process of producing the same |
| US3746678A (en) * | 1971-09-13 | 1973-07-17 | Dow Chemical Co | Amine-modified polyalkylene oxides |
| US3824158A (en) * | 1973-01-26 | 1974-07-16 | Hull R & Co Inc | Composition of baths for electrodeposition of bright zinc |
| US3864288A (en) * | 1973-10-15 | 1975-02-04 | Goodrich Co B F | Quaternized polyepihalohydrin thickening agent |
-
1976
- 1976-01-26 US US05/652,599 patent/US4156775A/en not_active Expired - Lifetime
- 1976-12-24 CA CA268,769A patent/CA1114094A/en not_active Expired
-
1977
- 1977-01-10 AU AU21179/77A patent/AU511737B2/en not_active Expired
- 1977-01-18 GB GB1988/77A patent/GB1527582A/en not_active Expired
- 1977-01-24 JP JP670277A patent/JPS5293500A/ja active Pending
- 1977-01-24 DE DE19772702712 patent/DE2702712A1/de not_active Withdrawn
- 1977-01-25 SE SE7700782A patent/SE7700782L/ not_active Application Discontinuation
- 1977-01-25 IT IT19590/77A patent/IT1079552B/it active
- 1977-01-25 FR FR7702050A patent/FR2338959A1/fr active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| SE7700782L (sv) | 1977-07-27 |
| FR2338959A1 (fr) | 1977-08-19 |
| US4156775A (en) | 1979-05-29 |
| AU511737B2 (en) | 1980-09-04 |
| JPS5293500A (en) | 1977-08-05 |
| IT1079552B (it) | 1985-05-13 |
| FR2338959B1 (cg-RX-API-DMAC7.html) | 1981-11-06 |
| AU2117977A (en) | 1978-07-20 |
| DE2702712A1 (de) | 1977-07-28 |
| GB1527582A (en) | 1978-10-04 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US5783041A (en) | Method for imparting strength to paper | |
| US4198269A (en) | Quaternary ammonium salts of epihalohydrin polymers as additives for fibrous cellulosic materials | |
| EP0910700B1 (en) | Temporary wet strength resins | |
| US5674362A (en) | Method for imparting strength to paper | |
| CA1114094A (en) | Quaternary ammonium salts of epihalohydrin polymers as additives for fibrous materials | |
| EP0362770B1 (en) | Dry strength additive for paper | |
| US3893885A (en) | Auxiliaries for the manufacture of paper | |
| US4066494A (en) | Nitrogenous condensation products used as retention aids in papermaking | |
| GB1509967A (en) | Crosslinked polyamidoamine condensation products for papermaking | |
| EP0553575B1 (en) | Novel cationic polyamines useful as drainage aids and stabilizers for rosin-based sizing agents | |
| CA1113208A (en) | Preparation of hydrophilic polyolefin fibers for use in papermaking | |
| US4056510A (en) | Amine-modified polyethers | |
| US3932363A (en) | Polyamines containing acid groups | |
| CA1218664A (en) | Ammonium polyamidoamines | |
| US3305493A (en) | Condensation products and methods of making them | |
| US5912306A (en) | Cationic compounds useful as drainage aids and stabilizers for rosin-based sizing agents | |
| CA2591299C (en) | Method for producing paper sheets with a high basis weight using amino-containing polymer and cationic polyacrylamide | |
| US3642663A (en) | Soluble quaternized condensation products of epihalohydrins and polyamines | |
| NZ200410A (en) | Branched polyamidoamines and use in increasing the wet strength of paper | |
| US3520774A (en) | Epichlorodydrin-polyethyleneimine wet strength additive for paper | |
| US3247048A (en) | Nitrogen prepolymers as wet and dry strength improvers for paper | |
| US4673729A (en) | Paper auxiliary from condensation product of aliphatic polyol-ether-amine and compound polyfunctional toward amino groups | |
| US3635842A (en) | Short life paper size from modified polyalkylene-imines | |
| US5382324A (en) | Method for enhancing paper strength | |
| US4536552A (en) | Polyamidoamine containing pendant ammonium moiety having crosslinking functionality |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEX | Expiry |