CA2652242C - Michael addition adducts as additives for paper and papermaking - Google Patents
Michael addition adducts as additives for paper and papermaking Download PDFInfo
- Publication number
- CA2652242C CA2652242C CA2652242A CA2652242A CA2652242C CA 2652242 C CA2652242 C CA 2652242C CA 2652242 A CA2652242 A CA 2652242A CA 2652242 A CA2652242 A CA 2652242A CA 2652242 C CA2652242 C CA 2652242C
- Authority
- CA
- Canada
- Prior art keywords
- michael addition
- group
- acrylamide
- vinylamine
- addition adduct
- 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.)
- Active
Links
- 238000006845 Michael addition reaction Methods 0.000 title claims abstract description 85
- 239000000654 additive Substances 0.000 title abstract description 20
- UYMKPFRHYYNDTL-UHFFFAOYSA-N ethenamine Chemical class NC=C UYMKPFRHYYNDTL-UHFFFAOYSA-N 0.000 claims abstract description 74
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 claims abstract description 70
- 238000000034 method Methods 0.000 claims abstract description 24
- 230000008569 process Effects 0.000 claims abstract description 23
- 229920000642 polymer Polymers 0.000 claims description 33
- -1 alkanoxyl Chemical group 0.000 claims description 31
- 150000001875 compounds Chemical class 0.000 claims description 28
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 24
- 238000006243 chemical reaction Methods 0.000 claims description 23
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 19
- 239000011347 resin Substances 0.000 claims description 18
- 229920005989 resin Polymers 0.000 claims description 18
- 239000007787 solid Substances 0.000 claims description 18
- 229920001577 copolymer Polymers 0.000 claims description 16
- 230000014759 maintenance of location Effects 0.000 claims description 16
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 15
- 150000003857 carboxamides Chemical class 0.000 claims description 15
- 229910052739 hydrogen Inorganic materials 0.000 claims description 15
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 15
- 125000000217 alkyl group Chemical group 0.000 claims description 14
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 claims description 13
- 150000001412 amines Chemical class 0.000 claims description 13
- LDCRTTXIJACKKU-ARJAWSKDSA-N dimethyl maleate Chemical compound COC(=O)\C=C/C(=O)OC LDCRTTXIJACKKU-ARJAWSKDSA-N 0.000 claims description 13
- 125000003342 alkenyl group Chemical group 0.000 claims description 12
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 11
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 11
- 239000000853 adhesive Substances 0.000 claims description 9
- 230000001070 adhesive effect Effects 0.000 claims description 9
- 229920001519 homopolymer Polymers 0.000 claims description 9
- FQPSGWSUVKBHSU-UHFFFAOYSA-N methacrylamide Chemical compound CC(=C)C(N)=O FQPSGWSUVKBHSU-UHFFFAOYSA-N 0.000 claims description 9
- 125000000304 alkynyl group Chemical group 0.000 claims description 8
- 239000003795 chemical substances by application Substances 0.000 claims description 8
- 229920001897 terpolymer Polymers 0.000 claims description 8
- 125000005392 carboxamide group Chemical group NC(=O)* 0.000 claims description 7
- 239000000178 monomer Substances 0.000 claims description 7
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 claims description 6
- 150000003973 alkyl amines Chemical class 0.000 claims description 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 5
- 239000003960 organic solvent Substances 0.000 claims description 5
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical group C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 claims description 4
- RAHZWNYVWXNFOC-UHFFFAOYSA-N Sulphur dioxide Chemical group O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 claims description 4
- 239000003125 aqueous solvent Substances 0.000 claims description 4
- 229960003328 benzoyl peroxide Drugs 0.000 claims description 4
- 239000000701 coagulant Substances 0.000 claims description 4
- 125000005499 phosphonyl group Chemical group 0.000 claims description 4
- AEMRFAOFKBGASW-UHFFFAOYSA-N Glycolic acid Natural products OCC(O)=O AEMRFAOFKBGASW-UHFFFAOYSA-N 0.000 claims description 3
- MPNXSZJPSVBLHP-UHFFFAOYSA-N 2-chloro-n-phenylpyridine-3-carboxamide Chemical compound ClC1=NC=CC=C1C(=O)NC1=CC=CC=C1 MPNXSZJPSVBLHP-UHFFFAOYSA-N 0.000 claims 1
- GDFCSMCGLZFNFY-UHFFFAOYSA-N Dimethylaminopropyl Methacrylamide Chemical compound CN(C)CCCNC(=O)C(C)=C GDFCSMCGLZFNFY-UHFFFAOYSA-N 0.000 claims 1
- RRHXZLALVWBDKH-UHFFFAOYSA-M trimethyl-[2-(2-methylprop-2-enoyloxy)ethyl]azanium;chloride Chemical compound [Cl-].CC(=C)C(=O)OCC[N+](C)(C)C RRHXZLALVWBDKH-UHFFFAOYSA-M 0.000 claims 1
- 239000000123 paper Substances 0.000 abstract description 18
- 125000004448 alkyl carbonyl group Chemical group 0.000 abstract description 6
- 239000002253 acid Substances 0.000 abstract description 4
- 239000011087 paperboard Substances 0.000 abstract description 4
- 150000001408 amides Chemical class 0.000 abstract description 3
- 238000004519 manufacturing process Methods 0.000 abstract description 3
- 150000007513 acids Chemical class 0.000 abstract description 2
- 150000002148 esters Chemical class 0.000 abstract description 2
- 239000000203 mixture Substances 0.000 description 38
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 33
- 239000000047 product Substances 0.000 description 23
- 150000003141 primary amines Chemical group 0.000 description 20
- 239000000243 solution Substances 0.000 description 13
- 125000006575 electron-withdrawing group Chemical group 0.000 description 12
- 239000000463 material Substances 0.000 description 10
- 239000000835 fiber Substances 0.000 description 9
- 238000007259 addition reaction Methods 0.000 description 8
- 230000000996 additive effect Effects 0.000 description 7
- 125000002091 cationic group Chemical group 0.000 description 7
- 238000004458 analytical method Methods 0.000 description 6
- 239000008394 flocculating agent Substances 0.000 description 6
- ZQXSMRAEXCEDJD-UHFFFAOYSA-N n-ethenylformamide Chemical compound C=CNC=O ZQXSMRAEXCEDJD-UHFFFAOYSA-N 0.000 description 6
- 239000011541 reaction mixture Substances 0.000 description 6
- 150000003335 secondary amines Chemical class 0.000 description 6
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 5
- 125000003277 amino group Chemical group 0.000 description 5
- 230000003993 interaction Effects 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 4
- 125000003368 amide group Chemical group 0.000 description 4
- 239000012736 aqueous medium Substances 0.000 description 4
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 238000005189 flocculation Methods 0.000 description 4
- 230000016615 flocculation Effects 0.000 description 4
- 125000000524 functional group Chemical group 0.000 description 4
- LEQAOMBKQFMDFZ-UHFFFAOYSA-N glyoxal Chemical compound O=CC=O LEQAOMBKQFMDFZ-UHFFFAOYSA-N 0.000 description 4
- 230000000704 physical effect Effects 0.000 description 4
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 4
- 230000008707 rearrangement Effects 0.000 description 4
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 4
- 238000005160 1H NMR spectroscopy Methods 0.000 description 3
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 3
- KUDUQBURMYMBIJ-UHFFFAOYSA-N 2-prop-2-enoyloxyethyl prop-2-enoate Chemical compound C=CC(=O)OCCOC(=O)C=C KUDUQBURMYMBIJ-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- 238000013459 approach Methods 0.000 description 3
- 150000001728 carbonyl compounds Chemical class 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 239000012467 final product Substances 0.000 description 3
- 239000001257 hydrogen Substances 0.000 description 3
- 230000009878 intermolecular interaction Effects 0.000 description 3
- 230000008863 intramolecular interaction Effects 0.000 description 3
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 3
- QLNJFJADRCOGBJ-UHFFFAOYSA-N propionamide Chemical group CCC(N)=O QLNJFJADRCOGBJ-UHFFFAOYSA-N 0.000 description 3
- 239000000376 reactant Substances 0.000 description 3
- JKNCOURZONDCGV-UHFFFAOYSA-N 2-(dimethylamino)ethyl 2-methylprop-2-enoate Chemical compound CN(C)CCOC(=O)C(C)=C JKNCOURZONDCGV-UHFFFAOYSA-N 0.000 description 2
- RHOOUTWPJJQGSK-UHFFFAOYSA-N 2-phenylsulfanylethyl prop-2-enoate Chemical compound C=CC(=O)OCCSC1=CC=CC=C1 RHOOUTWPJJQGSK-UHFFFAOYSA-N 0.000 description 2
- HGINCPLSRVDWNT-UHFFFAOYSA-N Acrolein Chemical compound C=CC=O HGINCPLSRVDWNT-UHFFFAOYSA-N 0.000 description 2
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- 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 2
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical group C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 2
- JIGUQPWFLRLWPJ-UHFFFAOYSA-N Ethyl acrylate Chemical compound CCOC(=O)C=C JIGUQPWFLRLWPJ-UHFFFAOYSA-N 0.000 description 2
- 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 2
- DCTLJGWMHPGCOS-UHFFFAOYSA-N Osajin Chemical compound C1=2C=CC(C)(C)OC=2C(CC=C(C)C)=C(O)C(C2=O)=C1OC=C2C1=CC=C(O)C=C1 DCTLJGWMHPGCOS-UHFFFAOYSA-N 0.000 description 2
- 229920002873 Polyethylenimine Polymers 0.000 description 2
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 2
- 229920001131 Pulp (paper) Polymers 0.000 description 2
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 2
- KNUSQTXJWATMLJ-UHFFFAOYSA-N [1-(dimethylamino)-2,2-dimethylpropyl] prop-2-enoate Chemical compound CN(C)C(C(C)(C)C)OC(=O)C=C KNUSQTXJWATMLJ-UHFFFAOYSA-N 0.000 description 2
- 150000001299 aldehydes Chemical class 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 238000004132 cross linking Methods 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
- 238000011156 evaluation Methods 0.000 description 2
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 2
- 238000005227 gel permeation chromatography Methods 0.000 description 2
- 229940015043 glyoxal Drugs 0.000 description 2
- 230000007062 hydrolysis Effects 0.000 description 2
- 238000006460 hydrolysis reaction Methods 0.000 description 2
- 230000002209 hydrophobic effect Effects 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 239000011976 maleic acid Substances 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 239000012038 nucleophile Substances 0.000 description 2
- PNJWIWWMYCMZRO-UHFFFAOYSA-N pent‐4‐en‐2‐one Natural products CC(=O)CC=C PNJWIWWMYCMZRO-UHFFFAOYSA-N 0.000 description 2
- 239000004014 plasticizer Substances 0.000 description 2
- 229940080818 propionamide Drugs 0.000 description 2
- 239000012429 reaction media Substances 0.000 description 2
- 239000011342 resin composition Substances 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- HRZFUMHJMZEROT-UHFFFAOYSA-L sodium disulfite Chemical compound [Na+].[Na+].[O-]S(=O)S([O-])(=O)=O HRZFUMHJMZEROT-UHFFFAOYSA-L 0.000 description 2
- 229940001584 sodium metabisulfite Drugs 0.000 description 2
- 235000010262 sodium metabisulphite Nutrition 0.000 description 2
- VWDWKYIASSYTQR-UHFFFAOYSA-N sodium nitrate Chemical compound [Na+].[O-][N+]([O-])=O VWDWKYIASSYTQR-UHFFFAOYSA-N 0.000 description 2
- 125000000547 substituted alkyl group Chemical group 0.000 description 2
- FDDDEECHVMSUSB-UHFFFAOYSA-N sulfanilamide Chemical group NC1=CC=C(S(N)(=O)=O)C=C1 FDDDEECHVMSUSB-UHFFFAOYSA-N 0.000 description 2
- 229940124530 sulfonamide Drugs 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 2
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 2
- RFOWDPMCXHVGET-UHFFFAOYSA-N (2,3,4,5,6-pentafluorophenyl) prop-2-enoate Chemical compound FC1=C(F)C(F)=C(OC(=O)C=C)C(F)=C1F RFOWDPMCXHVGET-UHFFFAOYSA-N 0.000 description 1
- VOBUAPTXJKMNCT-UHFFFAOYSA-N 1-prop-2-enoyloxyhexyl prop-2-enoate Chemical compound CCCCCC(OC(=O)C=C)OC(=O)C=C VOBUAPTXJKMNCT-UHFFFAOYSA-N 0.000 description 1
- RHNJVKIVSXGYBD-UHFFFAOYSA-N 10-prop-2-enoyloxydecyl prop-2-enoate Chemical compound C=CC(=O)OCCCCCCCCCCOC(=O)C=C RHNJVKIVSXGYBD-UHFFFAOYSA-N 0.000 description 1
- 125000001731 2-cyanoethyl group Chemical group [H]C([H])(*)C([H])([H])C#N 0.000 description 1
- OMIGHNLMNHATMP-UHFFFAOYSA-N 2-hydroxyethyl prop-2-enoate Chemical compound OCCOC(=O)C=C OMIGHNLMNHATMP-UHFFFAOYSA-N 0.000 description 1
- NYUTUWAFOUJLKI-UHFFFAOYSA-N 3-prop-2-enoyloxypropane-1-sulfonic acid Chemical compound OS(=O)(=O)CCCOC(=O)C=C NYUTUWAFOUJLKI-UHFFFAOYSA-N 0.000 description 1
- CYUZOYPRAQASLN-UHFFFAOYSA-N 3-prop-2-enoyloxypropanoic acid Chemical compound OC(=O)CCOC(=O)C=C CYUZOYPRAQASLN-UHFFFAOYSA-N 0.000 description 1
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
- JHWGFJBTMHEZME-UHFFFAOYSA-N 4-prop-2-enoyloxybutyl prop-2-enoate Chemical compound C=CC(=O)OCCCCOC(=O)C=C JHWGFJBTMHEZME-UHFFFAOYSA-N 0.000 description 1
- 229930185605 Bisphenol Natural products 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- IMROMDMJAWUWLK-UHFFFAOYSA-N Ethenol Chemical compound OC=C IMROMDMJAWUWLK-UHFFFAOYSA-N 0.000 description 1
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical group CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 1
- WOBHKFSMXKNTIM-UHFFFAOYSA-N Hydroxyethyl methacrylate Chemical compound CC(=C)C(=O)OCCO WOBHKFSMXKNTIM-UHFFFAOYSA-N 0.000 description 1
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 description 1
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 1
- 238000005481 NMR spectroscopy Methods 0.000 description 1
- 239000002202 Polyethylene glycol Substances 0.000 description 1
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 description 1
- 238000005903 acid hydrolysis reaction Methods 0.000 description 1
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 1
- 125000005250 alkyl acrylate group Chemical group 0.000 description 1
- 238000010945 base-catalyzed hydrolysis reactiony Methods 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- KCXMKQUNVWSEMD-UHFFFAOYSA-N benzyl chloride Chemical compound ClCC1=CC=CC=C1 KCXMKQUNVWSEMD-UHFFFAOYSA-N 0.000 description 1
- 229940073608 benzyl chloride Drugs 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 229920006317 cationic polymer Polymers 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- NEHMKBQYUWJMIP-NJFSPNSNSA-N chloro(114C)methane Chemical compound [14CH3]Cl NEHMKBQYUWJMIP-NJFSPNSNSA-N 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 238000005352 clarification Methods 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 238000010276 construction Methods 0.000 description 1
- 238000001212 derivatisation Methods 0.000 description 1
- 125000004386 diacrylate group Chemical group 0.000 description 1
- AQNSVANSEBPSMK-UHFFFAOYSA-N dicyclopentenyl methacrylate Chemical compound C12CC=CC2C2CC(OC(=O)C(=C)C)C1C2.C12C=CCC2C2CC(OC(=O)C(=C)C)C1C2 AQNSVANSEBPSMK-UHFFFAOYSA-N 0.000 description 1
- VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 description 1
- YIOJGTBNHQAVBO-UHFFFAOYSA-N dimethyl-bis(prop-2-enyl)azanium Chemical compound C=CC[N+](C)(C)CC=C YIOJGTBNHQAVBO-UHFFFAOYSA-N 0.000 description 1
- GQOKIYDTHHZSCJ-UHFFFAOYSA-M dimethyl-bis(prop-2-enyl)azanium;chloride Chemical group [Cl-].C=CC[N+](C)(C)CC=C GQOKIYDTHHZSCJ-UHFFFAOYSA-M 0.000 description 1
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 1
- 238000007720 emulsion polymerization reaction Methods 0.000 description 1
- STVZJERGLQHEKB-UHFFFAOYSA-N ethylene glycol dimethacrylate Chemical compound CC(=C)C(=O)OCCOC(=O)C(C)=C STVZJERGLQHEKB-UHFFFAOYSA-N 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- VZCYOOQTPOCHFL-OWOJBTEDSA-L fumarate(2-) Chemical class [O-]C(=O)\C=C\C([O-])=O VZCYOOQTPOCHFL-OWOJBTEDSA-L 0.000 description 1
- VOZRXNHHFUQHIL-UHFFFAOYSA-N glycidyl methacrylate Chemical compound CC(=C)C(=O)OCC1CO1 VOZRXNHHFUQHIL-UHFFFAOYSA-N 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 230000010354 integration Effects 0.000 description 1
- LVHBHZANLOWSRM-UHFFFAOYSA-N itaconic acid Chemical compound OC(=O)CC(=C)C(O)=O LVHBHZANLOWSRM-UHFFFAOYSA-N 0.000 description 1
- 150000002688 maleic acid derivatives Chemical class 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 239000002609 medium Substances 0.000 description 1
- 150000002734 metacrylic acid derivatives Chemical class 0.000 description 1
- LUCXVPAZUDVVBT-UHFFFAOYSA-N methyl-[3-(2-methylphenoxy)-3-phenylpropyl]azanium;chloride Chemical compound Cl.C=1C=CC=CC=1C(CCNC)OC1=CC=CC=C1C LUCXVPAZUDVVBT-UHFFFAOYSA-N 0.000 description 1
- 239000003607 modifier Substances 0.000 description 1
- ZIUHHBKFKCYYJD-UHFFFAOYSA-N n,n'-methylenebisacrylamide Chemical compound C=CC(=O)NCNC(=O)C=C ZIUHHBKFKCYYJD-UHFFFAOYSA-N 0.000 description 1
- SWPMNMYLORDLJE-UHFFFAOYSA-N n-ethylprop-2-enamide Chemical compound CCNC(=O)C=C SWPMNMYLORDLJE-UHFFFAOYSA-N 0.000 description 1
- 238000005935 nucleophilic addition reaction Methods 0.000 description 1
- 229920000885 poly(2-vinylpyridine) Polymers 0.000 description 1
- 229920003229 poly(methyl methacrylate) Polymers 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 239000004926 polymethyl methacrylate Substances 0.000 description 1
- 150000003140 primary amides Chemical class 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 238000010526 radical polymerization reaction Methods 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 235000010344 sodium nitrate Nutrition 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 239000002351 wastewater Substances 0.000 description 1
- 238000004065 wastewater treatment Methods 0.000 description 1
- 239000003643 water by type Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
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- D21H17/54—Synthetic macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds obtained by reactions forming in the main chain of the macromolecule a linkage containing nitrogen
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- D21H17/41—Synthetic macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds containing ionic groups
- D21H17/44—Synthetic macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds containing ionic groups cationic
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- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Paper (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
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| US9266301B2 (en) | 2005-06-30 | 2016-02-23 | Nalco Company | Method to adhere and dislodge crepe paper |
| AR071441A1 (es) * | 2007-11-05 | 2010-06-23 | Ciba Holding Inc | N- vinilamida glioxilada |
| JP5370712B2 (ja) * | 2008-02-21 | 2013-12-18 | 日東電工株式会社 | 酸性水溶性標的物質吸着ポリマー及びその製造方法 |
| CA2736595C (en) | 2009-01-30 | 2015-04-14 | Hercules Incorporated | Quaternary vinylamine-containing polymers as additives in papermaking |
| US20110130508A1 (en) * | 2009-07-29 | 2011-06-02 | Alan David Pendley | Topside optical adhesive for micro-optical film embedded into paper during the papermaking process |
| WO2011090672A1 (en) * | 2009-12-29 | 2011-07-28 | Hercules Incorporated | Process to enhancing dry strength of paper by treatment with vinylamine-containing polymers and acrylamide containing polymers |
| JP5865847B2 (ja) * | 2010-02-24 | 2016-02-17 | レリプサ, インコーポレイテッド | 胆汁酸捕捉剤として使用するための架橋されたポリビニルアミン、ポリアリルアミンおよびポリエチレンイミン |
| CN103492425B (zh) | 2011-04-14 | 2016-08-31 | 索理思科技开曼公司 | 含酰化乙烯胺的聚合物的制备方法及其作为造纸添加剂的应用 |
| BR112014004225B1 (pt) | 2011-08-25 | 2021-02-02 | Solenis Technologies Cayman, L.P. | método para fabricar papel, papelão ou papel-cartão e uso |
| CN102701378A (zh) * | 2012-06-14 | 2012-10-03 | 四川师范大学 | 一种水溶性有机两性共聚物絮凝剂及制备方法 |
| EP3044365B1 (en) | 2013-09-09 | 2018-05-23 | Basf Se | High molecular weight and high cationic chargeglyoxalatedpolyacrylamide copolymers, and their methods of manufacture and use |
| ES2759450T3 (es) * | 2014-04-16 | 2020-05-11 | Solenis Tech Lp | Polímeros modificados que contienen vinilamina y su uso en la fabricación de papel |
| FI126468B (en) * | 2014-10-09 | 2016-12-30 | Kemira Oyj | POLYMER PRODUCT, METHOD FOR MANUFACTURE OF POLYMER AND USE OF POLYMER |
| EP3234259A1 (de) | 2014-12-16 | 2017-10-25 | Basf Se | Verfahren zur herstellung von papier und karton |
| US9783933B2 (en) | 2015-04-10 | 2017-10-10 | Solenis Technologies, L.P. | Modified vinylamine-containing polymers and their use in papermaking |
| CA2990318C (en) | 2015-06-25 | 2023-12-05 | Kemira Oyj | A method for producing a material with a network of at least two polymers, a product thereof and use of the product |
| WO2017147392A1 (en) | 2016-02-26 | 2017-08-31 | Ecolab Usa Inc. | Drainage management in multi-ply papermaking |
| CN109844220A (zh) | 2016-09-16 | 2019-06-04 | 索理思科技公司 | 使用微纤维化纤维素提高造纸系统的滤水性能 |
| US10618992B2 (en) * | 2017-07-31 | 2020-04-14 | Solenis Technologies, L.P. | Hydrophobic vinylamine-containing polymer compositions and their use in papermaking applications |
| CN111492108A (zh) | 2017-10-18 | 2020-08-04 | 索理思科技开曼公司 | 用于生产多层纸的方法 |
| WO2019076703A1 (de) | 2017-10-18 | 2019-04-25 | Basf Se | Verfahren zur herstellung von einlagigem oder mehrlagigem papier |
| US11332889B2 (en) | 2019-05-03 | 2022-05-17 | First Quality Tissue, Llc | Absorbent structures with high absorbency and low basis weight |
| CN111732733B (zh) * | 2020-07-17 | 2022-05-10 | 辽宁科隆精细化工股份有限公司 | 一种乙烯亚胺与聚醚双改性聚酰胺树状大分子化合物及其制备方法和应用 |
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| US2721140A (en) * | 1952-09-19 | 1955-10-18 | Hercules Powder Co Ltd | Paper of high wet strength and process therefor |
| US3728215A (en) * | 1971-03-12 | 1973-04-17 | Hercules Inc | Aminopalyamide{13 acrylamide{13 polyaldehyde resins employing an alpha, beta-unsaturated monobasic carboxylic acid or ester to make the aminopolyamide and their utility as wet and dry strengthening agents in papermaking |
| US4060570A (en) * | 1976-05-10 | 1977-11-29 | Thiokol Corporation | Curable liquid polysulfide polymer based sealants |
| DE3128478A1 (de) * | 1981-07-18 | 1983-02-03 | Basf Ag, 6700 Ludwigshafen | Verfahren zur herstellung von linearen, basischen polymerisaten |
| DE3534273A1 (de) * | 1985-09-26 | 1987-04-02 | Basf Ag | Verfahren zur herstellung von vinylamin-einheiten enthaltenden wasserloeslichen copolymerisaten und deren verwendung als nass- und trockenverfestigungsmittel fuer papier |
| CA1283748C (en) | 1986-06-25 | 1991-04-30 | Takaharu Itagaki | Vinylamine copolymer, flocculating agent and paper strength increasingagent using the same, as well as process for producing the same |
| US5630907A (en) * | 1992-12-07 | 1997-05-20 | Basf Aktiengesellschaft | Use of hydrolyzed copolymers of N-vinylcarboxamides and monoethylenically unsaturated carboxylic acids in papermaking |
| US5292441A (en) * | 1993-01-12 | 1994-03-08 | Betz Laboratories, Inc. | Quaternized polyvinylamine water clarification agents |
| EP0743172B1 (en) * | 1995-05-18 | 1999-08-04 | Fort James Corporation | Novel creping adhesive formulations, method of creping and creped fibrous web |
| DE19607674A1 (de) * | 1996-02-29 | 1997-09-04 | Basf Ag | Verwendung von hydrolysierten Polymerisaten von N-Vinylcarbonsäureamiden als Mittel zur Erhöhung der Trockenfestigkeit von Papier, Pappe und Karton |
| US5994449A (en) * | 1997-01-23 | 1999-11-30 | Hercules Incorporated | Resin compositions for making wet and dry strength paper and their use as creping adhesives |
| DE19713755A1 (de) * | 1997-04-04 | 1998-10-08 | Basf Ag | Verfahren zur Herstellung von Papier, Pappe und Karton mit hoher Trockenfestigkeit |
| DE19815127A1 (de) | 1998-04-03 | 1999-10-07 | Basf Ag | Mittel mit Copolymerisaten aus N-Vinylcarbonsäureamiden und Monomeren mit hydrophobem Rest, und Verwendung dieser Copolymerisate |
| JP2000143798A (ja) * | 1998-09-08 | 2000-05-26 | Nippon Shokubai Co Ltd | 水膨潤性架橋重合体およびその製造方法 |
| FR2791688B1 (fr) * | 1999-03-29 | 2005-03-18 | Snf Sa | Nouveaux procedes de synthese d'agents floculants et coagulants de type polyvinylamine pva, nouveaux agents obtenus, et leurs utilisations et papiers ameliores ainsi obtenus. |
| DE19931720A1 (de) * | 1999-07-08 | 2001-01-11 | Basf Ag | Hydrogel-formende Polymermischung |
| US20040059065A1 (en) * | 2000-03-09 | 2004-03-25 | Takeshi Goto | Crosslinked anion-exchange resin or salt thereof |
| AU2001241077A1 (en) * | 2000-03-09 | 2001-09-17 | Hisamitsu Pharmaceutical Co. Inc. | Crosslinked anion-exchange resin or salt thereof and phosphorus adsorbent comprising the same |
| US6706821B1 (en) * | 2000-07-18 | 2004-03-16 | Fmc Corporation | Michael addition products of amine terminated polyolefins and polyfunctional acrylates |
| US6667384B2 (en) * | 2001-12-27 | 2003-12-23 | Hercules Incorporated | Methyl acrylate-diamine based polyamide resins and processes for producing the same |
| JP4047120B2 (ja) * | 2002-09-25 | 2008-02-13 | ハイモ株式会社 | 凝集剤及びその使用方法 |
| JP2005171410A (ja) | 2003-12-10 | 2005-06-30 | Seiko Pmc Corp | 紙及び製造方法 |
| US20070261807A1 (en) * | 2006-05-12 | 2007-11-15 | Taggart Thomas E | Use of polyvinylamine to improve oil and water sizing in cellulosic products |
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Also Published As
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| KR101434689B1 (ko) | 2014-08-28 |
| WO2007136756A3 (en) | 2008-01-17 |
| AU2007254145A1 (en) | 2007-11-29 |
| CA2652242A1 (en) | 2007-11-29 |
| MX298466B (es) | 2012-04-23 |
| CN101472966B (zh) | 2011-03-30 |
| PL2021388T3 (pl) | 2012-08-31 |
| JP2009537704A (ja) | 2009-10-29 |
| ZA200810688B (en) | 2010-03-31 |
| ES2382574T3 (es) | 2012-06-11 |
| EP2021388A2 (en) | 2009-02-11 |
| ATE550361T1 (de) | 2012-04-15 |
| KR20090029217A (ko) | 2009-03-20 |
| EP2021388B1 (en) | 2012-03-21 |
| JP5431922B2 (ja) | 2014-03-05 |
| CN101472966A (zh) | 2009-07-01 |
| WO2007136756A2 (en) | 2007-11-29 |
| AU2007254145B2 (en) | 2012-05-24 |
| PT2021388E (pt) | 2012-05-11 |
| US7902312B2 (en) | 2011-03-08 |
| BRPI0712029B1 (pt) | 2018-12-11 |
| BRPI0712029A2 (pt) | 2012-01-03 |
| US20080009596A1 (en) | 2008-01-10 |
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