AU2007293922B2 - Glyoxalation of vinylamide polymer - Google Patents
Glyoxalation of vinylamide polymer Download PDFInfo
- Publication number
- AU2007293922B2 AU2007293922B2 AU2007293922A AU2007293922A AU2007293922B2 AU 2007293922 B2 AU2007293922 B2 AU 2007293922B2 AU 2007293922 A AU2007293922 A AU 2007293922A AU 2007293922 A AU2007293922 A AU 2007293922A AU 2007293922 B2 AU2007293922 B2 AU 2007293922B2
- Authority
- AU
- Australia
- Prior art keywords
- vinylamide polymer
- polymer
- vinylamide
- reaction
- 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.)
- Ceased
Links
- 229920000642 polymer Polymers 0.000 title claims description 213
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 title claims description 191
- LEQAOMBKQFMDFZ-UHFFFAOYSA-N glyoxal Chemical compound O=CC=O LEQAOMBKQFMDFZ-UHFFFAOYSA-N 0.000 claims abstract description 139
- 238000006243 chemical reaction Methods 0.000 claims abstract description 95
- 238000000034 method Methods 0.000 claims abstract description 85
- 229940015043 glyoxal Drugs 0.000 claims abstract description 69
- 229920002678 cellulose Polymers 0.000 claims abstract description 39
- 239000001913 cellulose Substances 0.000 claims abstract description 39
- 239000011541 reaction mixture Substances 0.000 claims description 46
- 239000000178 monomer Substances 0.000 claims description 44
- 125000002091 cationic group Chemical group 0.000 claims description 38
- 239000003795 chemical substances by application Substances 0.000 claims description 23
- 125000000129 anionic group Chemical group 0.000 claims description 18
- 230000015572 biosynthetic process Effects 0.000 claims description 18
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 claims description 12
- 230000007423 decrease Effects 0.000 claims description 10
- 229920001187 thermosetting polymer Polymers 0.000 claims description 10
- -1 2-hyroxyadipaldehyde Chemical compound 0.000 claims description 8
- 239000002202 Polyethylene glycol Substances 0.000 claims description 8
- 229920001223 polyethylene glycol Polymers 0.000 claims description 8
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims description 7
- 229920001577 copolymer Polymers 0.000 claims description 7
- MYRTYDVEIRVNKP-UHFFFAOYSA-N 1,2-Divinylbenzene Chemical compound C=CC1=CC=CC=C1C=C MYRTYDVEIRVNKP-UHFFFAOYSA-N 0.000 claims description 6
- 239000002253 acid Substances 0.000 claims description 6
- 150000003926 acrylamides Chemical class 0.000 claims description 6
- 235000019270 ammonium chloride Nutrition 0.000 claims description 6
- 229920005989 resin Polymers 0.000 claims description 6
- 239000011347 resin Substances 0.000 claims description 6
- KGRVJHAUYBGFFP-UHFFFAOYSA-N 2,2'-Methylenebis(4-methyl-6-tert-butylphenol) Chemical compound CC(C)(C)C1=CC(C)=CC(CC=2C(=C(C=C(C)C=2)C(C)(C)C)O)=C1O KGRVJHAUYBGFFP-UHFFFAOYSA-N 0.000 claims description 3
- PHZSUOPYLUNLDX-UHFFFAOYSA-N 2,2-bis(prop-2-enoxy)acetic acid Chemical compound C=CCOC(C(=O)O)OCC=C PHZSUOPYLUNLDX-UHFFFAOYSA-N 0.000 claims description 3
- HCLJOFJIQIJXHS-UHFFFAOYSA-N 2-[2-[2-(2-prop-2-enoyloxyethoxy)ethoxy]ethoxy]ethyl prop-2-enoate Chemical compound C=CC(=O)OCCOCCOCCOCCOC(=O)C=C HCLJOFJIQIJXHS-UHFFFAOYSA-N 0.000 claims description 3
- KGIGUEBEKRSTEW-UHFFFAOYSA-N 2-vinylpyridine Chemical class C=CC1=CC=CC=N1 KGIGUEBEKRSTEW-UHFFFAOYSA-N 0.000 claims description 3
- HVVWZTWDBSEWIH-UHFFFAOYSA-N [2-(hydroxymethyl)-3-prop-2-enoyloxy-2-(prop-2-enoyloxymethyl)propyl] prop-2-enoate Chemical compound C=CC(=O)OCC(CO)(COC(=O)C=C)COC(=O)C=C HVVWZTWDBSEWIH-UHFFFAOYSA-N 0.000 claims description 3
- 150000001299 aldehydes Chemical group 0.000 claims description 3
- 150000001412 amines Chemical class 0.000 claims description 3
- 150000001875 compounds Chemical class 0.000 claims description 3
- 125000004386 diacrylate group Chemical group 0.000 claims description 3
- ILCQQHAOOOVHQJ-UHFFFAOYSA-N n-ethenylprop-2-enamide Chemical compound C=CNC(=O)C=C ILCQQHAOOOVHQJ-UHFFFAOYSA-N 0.000 claims description 3
- CNPHCSFIDKZQAK-UHFFFAOYSA-N n-prop-2-enylprop-2-enamide Chemical compound C=CCNC(=O)C=C CNPHCSFIDKZQAK-UHFFFAOYSA-N 0.000 claims description 3
- UYWLALLBUXELFT-UHFFFAOYSA-N 2-methyl-1-(4-methylpiperazin-1-yl)prop-2-en-1-one Chemical compound CN1CCN(C(=O)C(C)=C)CC1 UYWLALLBUXELFT-UHFFFAOYSA-N 0.000 claims description 2
- 229920002085 Dialdehyde starch Polymers 0.000 claims description 2
- SXRSQZLOMIGNAQ-UHFFFAOYSA-N Glutaraldehyde Chemical compound O=CCCCC=O SXRSQZLOMIGNAQ-UHFFFAOYSA-N 0.000 claims description 2
- PCSMJKASWLYICJ-UHFFFAOYSA-N Succinic aldehyde Chemical compound O=CCCC=O PCSMJKASWLYICJ-UHFFFAOYSA-N 0.000 claims description 2
- 150000001252 acrylic acid derivatives Chemical class 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 125000004985 dialkyl amino alkyl group Chemical group 0.000 claims description 2
- AHIXHWRUDZFHEZ-UHFFFAOYSA-N furan-2,3-dicarbaldehyde Chemical compound O=CC=1C=COC=1C=O AHIXHWRUDZFHEZ-UHFFFAOYSA-N 0.000 claims description 2
- 229920001519 homopolymer Polymers 0.000 claims description 2
- 150000003242 quaternary ammonium salts Chemical class 0.000 claims description 2
- 159000000000 sodium salts Chemical class 0.000 claims 2
- 125000004663 dialkyl amino group Chemical group 0.000 claims 1
- 239000000123 paper Substances 0.000 abstract description 31
- 239000000203 mixture Substances 0.000 abstract description 14
- 238000005728 strengthening Methods 0.000 abstract description 8
- 239000011087 paperboard Substances 0.000 abstract description 3
- UYMKPFRHYYNDTL-UHFFFAOYSA-N ethenamine Chemical class NC=C UYMKPFRHYYNDTL-UHFFFAOYSA-N 0.000 abstract description 2
- 238000001879 gelation Methods 0.000 abstract description 2
- 238000002360 preparation method Methods 0.000 abstract 1
- 239000000243 solution Substances 0.000 description 32
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 18
- 239000000047 product Substances 0.000 description 14
- 238000007792 addition Methods 0.000 description 13
- 150000001408 amides Chemical group 0.000 description 12
- 229920002401 polyacrylamide Polymers 0.000 description 11
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 10
- 239000003921 oil Substances 0.000 description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- NJSSICCENMLTKO-HRCBOCMUSA-N [(1r,2s,4r,5r)-3-hydroxy-4-(4-methylphenyl)sulfonyloxy-6,8-dioxabicyclo[3.2.1]octan-2-yl] 4-methylbenzenesulfonate Chemical compound C1=CC(C)=CC=C1S(=O)(=O)O[C@H]1C(O)[C@@H](OS(=O)(=O)C=2C=CC(C)=CC=2)[C@@H]2OC[C@H]1O2 NJSSICCENMLTKO-HRCBOCMUSA-N 0.000 description 7
- 230000008901 benefit Effects 0.000 description 7
- 238000006555 catalytic reaction Methods 0.000 description 7
- 239000007787 solid Substances 0.000 description 7
- 239000002585 base Substances 0.000 description 6
- 239000000499 gel Substances 0.000 description 6
- 229920002554 vinyl polymer Polymers 0.000 description 6
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 5
- 239000000654 additive Substances 0.000 description 5
- 238000004458 analytical method Methods 0.000 description 5
- 239000007864 aqueous solution Substances 0.000 description 5
- 239000000463 material Substances 0.000 description 5
- 229920000371 poly(diallyldimethylammonium chloride) polymer Polymers 0.000 description 5
- 239000000376 reactant Substances 0.000 description 5
- 238000012360 testing method Methods 0.000 description 5
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 4
- 238000004132 cross linking Methods 0.000 description 4
- 239000003431 cross linking reagent Substances 0.000 description 4
- 239000006185 dispersion Substances 0.000 description 4
- 239000000835 fiber Substances 0.000 description 4
- 229920000768 polyamine Polymers 0.000 description 4
- 239000002002 slurry Substances 0.000 description 4
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 4
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000012736 aqueous medium Substances 0.000 description 3
- 239000012530 fluid Substances 0.000 description 3
- HHLFWLYXYJOTON-UHFFFAOYSA-M glyoxylate Chemical compound [O-]C(=O)C=O HHLFWLYXYJOTON-UHFFFAOYSA-M 0.000 description 3
- 238000005259 measurement Methods 0.000 description 3
- FQPSGWSUVKBHSU-UHFFFAOYSA-N methacrylamide Chemical compound CC(=C)C(N)=O FQPSGWSUVKBHSU-UHFFFAOYSA-N 0.000 description 3
- 239000004530 micro-emulsion Substances 0.000 description 3
- 238000012544 monitoring process Methods 0.000 description 3
- 239000002245 particle Substances 0.000 description 3
- 238000003860 storage Methods 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- 239000012855 volatile organic compound Substances 0.000 description 3
- 239000007762 w/o emulsion Substances 0.000 description 3
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 2
- OFNISBHGPNMTMS-UHFFFAOYSA-N 3-methylideneoxolane-2,5-dione Chemical compound C=C1CC(=O)OC1=O OFNISBHGPNMTMS-UHFFFAOYSA-N 0.000 description 2
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 2
- 229920003043 Cellulose fiber Polymers 0.000 description 2
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 2
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 2
- 239000004593 Epoxy Substances 0.000 description 2
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- 239000008351 acetate buffer Substances 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
- 230000000996 additive effect Effects 0.000 description 2
- 238000000149 argon plasma sintering Methods 0.000 description 2
- 239000000872 buffer Substances 0.000 description 2
- 230000003197 catalytic effect Effects 0.000 description 2
- 229920006317 cationic polymer Polymers 0.000 description 2
- 239000002738 chelating agent Substances 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- NEHMKBQYUWJMIP-UHFFFAOYSA-N chloromethane Chemical compound ClC NEHMKBQYUWJMIP-UHFFFAOYSA-N 0.000 description 2
- 239000013065 commercial product Substances 0.000 description 2
- 238000007906 compression Methods 0.000 description 2
- 230000006835 compression Effects 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 239000003792 electrolyte Substances 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 238000007306 functionalization reaction Methods 0.000 description 2
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- 238000006116 polymerization reaction Methods 0.000 description 2
- 238000010791 quenching Methods 0.000 description 2
- 239000012070 reactive reagent Substances 0.000 description 2
- 150000003839 salts Chemical group 0.000 description 2
- 238000005507 spraying Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 239000000758 substrate Substances 0.000 description 2
- 239000004094 surface-active agent Substances 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- 239000004634 thermosetting polymer Substances 0.000 description 2
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
- 238000012546 transfer Methods 0.000 description 2
- 229920003169 water-soluble polymer Polymers 0.000 description 2
- DGVVWUTYPXICAM-UHFFFAOYSA-N β‐Mercaptoethanol Chemical compound OCCS DGVVWUTYPXICAM-UHFFFAOYSA-N 0.000 description 2
- NPPUWKCCXAPWKH-UHFFFAOYSA-M (4-ethenylphenyl)-trimethylazanium;chloride Chemical compound [Cl-].C[N+](C)(C)C1=CC=C(C=C)C=C1 NPPUWKCCXAPWKH-UHFFFAOYSA-M 0.000 description 1
- BJEPYKJPYRNKOW-REOHCLBHSA-N (S)-malic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O BJEPYKJPYRNKOW-REOHCLBHSA-N 0.000 description 1
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 1
- JAHNSTQSQJOJLO-UHFFFAOYSA-N 2-(3-fluorophenyl)-1h-imidazole Chemical compound FC1=CC=CC(C=2NC=CN=2)=C1 JAHNSTQSQJOJLO-UHFFFAOYSA-N 0.000 description 1
- DPBJAVGHACCNRL-UHFFFAOYSA-N 2-(dimethylamino)ethyl prop-2-enoate Chemical compound CN(C)CCOC(=O)C=C DPBJAVGHACCNRL-UHFFFAOYSA-N 0.000 description 1
- 229920000536 2-Acrylamido-2-methylpropane sulfonic acid Polymers 0.000 description 1
- GOXQRTZXKQZDDN-UHFFFAOYSA-N 2-Ethylhexyl acrylate Chemical compound CCCCC(CC)COC(=O)C=C GOXQRTZXKQZDDN-UHFFFAOYSA-N 0.000 description 1
- XHZPRMZZQOIPDS-UHFFFAOYSA-N 2-Methyl-2-[(1-oxo-2-propenyl)amino]-1-propanesulfonic acid Chemical compound OS(=O)(=O)CC(C)(C)NC(=O)C=C XHZPRMZZQOIPDS-UHFFFAOYSA-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
- 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
- KWSLGOVYXMQPPX-UHFFFAOYSA-N 5-[3-(trifluoromethyl)phenyl]-2h-tetrazole Chemical compound FC(F)(F)C1=CC=CC(C2=NNN=N2)=C1 KWSLGOVYXMQPPX-UHFFFAOYSA-N 0.000 description 1
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 1
- GAWIXWVDTYZWAW-UHFFFAOYSA-N C[CH]O Chemical group C[CH]O GAWIXWVDTYZWAW-UHFFFAOYSA-N 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- 102100031237 Cystatin-A Human genes 0.000 description 1
- JIGUQPWFLRLWPJ-UHFFFAOYSA-N Ethyl acrylate Chemical compound CCOC(=O)C=C JIGUQPWFLRLWPJ-UHFFFAOYSA-N 0.000 description 1
- 101000921786 Homo sapiens Cystatin-A Proteins 0.000 description 1
- 229910021578 Iron(III) chloride Inorganic materials 0.000 description 1
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 description 1
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 1
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 1
- WHNWPMSKXPGLAX-UHFFFAOYSA-N N-Vinyl-2-pyrrolidone Chemical compound C=CN1CCCC1=O WHNWPMSKXPGLAX-UHFFFAOYSA-N 0.000 description 1
- 229920002873 Polyethylenimine Polymers 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- BJEPYKJPYRNKOW-UHFFFAOYSA-N alpha-hydroxysuccinic acid Natural products OC(=O)C(O)CC(O)=O BJEPYKJPYRNKOW-UHFFFAOYSA-N 0.000 description 1
- DIZPMCHEQGEION-UHFFFAOYSA-H aluminium sulfate (anhydrous) Chemical compound [Al+3].[Al+3].[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O DIZPMCHEQGEION-UHFFFAOYSA-H 0.000 description 1
- 125000003368 amide group Chemical group 0.000 description 1
- 150000003863 ammonium salts Chemical class 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- 230000003466 anti-cipated effect Effects 0.000 description 1
- 239000007900 aqueous suspension Substances 0.000 description 1
- 238000010420 art technique Methods 0.000 description 1
- 239000002199 base oil Substances 0.000 description 1
- 239000011324 bead Substances 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
- 239000007853 buffer solution Substances 0.000 description 1
- CQEYYJKEWSMYFG-UHFFFAOYSA-N butyl acrylate Chemical compound CCCCOC(=O)C=C CQEYYJKEWSMYFG-UHFFFAOYSA-N 0.000 description 1
- 239000012986 chain transfer agent Substances 0.000 description 1
- NEHMKBQYUWJMIP-NJFSPNSNSA-N chloro(114C)methane Chemical compound [14CH3]Cl NEHMKBQYUWJMIP-NJFSPNSNSA-N 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 229920006037 cross link polymer Polymers 0.000 description 1
- 238000007766 curtain coating Methods 0.000 description 1
- 239000008367 deionised water Substances 0.000 description 1
- 229910021641 deionized water Inorganic materials 0.000 description 1
- 238000013461 design Methods 0.000 description 1
- LVYZJEPLMYTTGH-UHFFFAOYSA-H dialuminum chloride pentahydroxide dihydrate Chemical compound [Cl-].[Al+3].[OH-].[OH-].[Al+3].[OH-].[OH-].[OH-].O.O LVYZJEPLMYTTGH-UHFFFAOYSA-H 0.000 description 1
- 238000000502 dialysis Methods 0.000 description 1
- 239000000385 dialysis solution Substances 0.000 description 1
- QGBSISYHAICWAH-UHFFFAOYSA-N dicyandiamide Chemical compound NC(N)=NC#N QGBSISYHAICWAH-UHFFFAOYSA-N 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 description 1
- KDJDBBUMQVLTGP-UHFFFAOYSA-N dimethyl(oxiran-2-ylmethyl)azanium;chloride Chemical compound [Cl-].C[NH+](C)CC1CO1 KDJDBBUMQVLTGP-UHFFFAOYSA-N 0.000 description 1
- 230000003292 diminished effect Effects 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 125000003700 epoxy group Chemical group 0.000 description 1
- ZKQFHRVKCYFVCN-UHFFFAOYSA-N ethoxyethane;hexane Chemical compound CCOCC.CCCCCC ZKQFHRVKCYFVCN-UHFFFAOYSA-N 0.000 description 1
- UXYBXUYUKHUNOM-UHFFFAOYSA-M ethyl(trimethyl)azanium;chloride Chemical compound [Cl-].CC[N+](C)(C)C UXYBXUYUKHUNOM-UHFFFAOYSA-M 0.000 description 1
- 230000007717 exclusion Effects 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 239000008394 flocculating agent Substances 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 238000010528 free radical solution polymerization reaction Methods 0.000 description 1
- 239000000295 fuel oil Substances 0.000 description 1
- 239000001530 fumaric acid Substances 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 150000004676 glycans Chemical class 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 125000002768 hydroxyalkyl group Chemical group 0.000 description 1
- 238000005470 impregnation Methods 0.000 description 1
- 238000010348 incorporation Methods 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 239000003999 initiator Substances 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 description 1
- 239000003350 kerosene Substances 0.000 description 1
- 239000002655 kraft paper Substances 0.000 description 1
- 238000011005 laboratory method Methods 0.000 description 1
- 239000004310 lactic acid Substances 0.000 description 1
- 235000014655 lactic acid Nutrition 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- 239000001630 malic acid Substances 0.000 description 1
- 235000011090 malic acid Nutrition 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000002609 medium Substances 0.000 description 1
- 239000012528 membrane Substances 0.000 description 1
- 150000002736 metal compounds Chemical class 0.000 description 1
- 229940050176 methyl chloride Drugs 0.000 description 1
- LVHBHZANLOWSRM-UHFFFAOYSA-N methylenebutanedioic acid Natural products OC(=O)CC(=C)C(O)=O LVHBHZANLOWSRM-UHFFFAOYSA-N 0.000 description 1
- 238000012703 microemulsion polymerization Methods 0.000 description 1
- 239000011859 microparticle Substances 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 239000002480 mineral oil Substances 0.000 description 1
- 235000010446 mineral oil Nutrition 0.000 description 1
- WFKDPJRCBCBQNT-UHFFFAOYSA-N n,2-dimethylprop-2-enamide Chemical compound CNC(=O)C(C)=C WFKDPJRCBCBQNT-UHFFFAOYSA-N 0.000 description 1
- YPHQUSNPXDGUHL-UHFFFAOYSA-N n-methylprop-2-enamide Chemical compound CNC(=O)C=C YPHQUSNPXDGUHL-UHFFFAOYSA-N 0.000 description 1
- XFHJDMUEHUHAJW-UHFFFAOYSA-N n-tert-butylprop-2-enamide Chemical compound CC(C)(C)NC(=O)C=C XFHJDMUEHUHAJW-UHFFFAOYSA-N 0.000 description 1
- 230000009965 odorless effect Effects 0.000 description 1
- 239000012053 oil suspension Substances 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 238000001139 pH measurement Methods 0.000 description 1
- 239000013054 paper strength agent Substances 0.000 description 1
- 239000013618 particulate matter Substances 0.000 description 1
- PNJWIWWMYCMZRO-UHFFFAOYSA-N pent‐4‐en‐2‐one Natural products CC(=O)CC=C PNJWIWWMYCMZRO-UHFFFAOYSA-N 0.000 description 1
- ACVYVLVWPXVTIT-UHFFFAOYSA-N phosphinic acid Chemical class O[PH2]=O ACVYVLVWPXVTIT-UHFFFAOYSA-N 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 229920000962 poly(amidoamine) Polymers 0.000 description 1
- 229920001515 polyalkylene glycol Polymers 0.000 description 1
- 229920000647 polyepoxide Polymers 0.000 description 1
- 229920001282 polysaccharide Polymers 0.000 description 1
- 239000005017 polysaccharide Substances 0.000 description 1
- 230000002028 premature Effects 0.000 description 1
- 238000007639 printing Methods 0.000 description 1
- UIIIBRHUICCMAI-UHFFFAOYSA-N prop-2-ene-1-sulfonic acid Chemical compound OS(=O)(=O)CC=C UIIIBRHUICCMAI-UHFFFAOYSA-N 0.000 description 1
- 125000001453 quaternary ammonium group Chemical group 0.000 description 1
- 239000002516 radical scavenger Substances 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 229910000077 silane Inorganic materials 0.000 description 1
- 150000004756 silanes Chemical class 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 229910001379 sodium hypophosphite Inorganic materials 0.000 description 1
- RPACBEVZENYWOL-XFULWGLBSA-M sodium;(2r)-2-[6-(4-chlorophenoxy)hexyl]oxirane-2-carboxylate Chemical compound [Na+].C=1C=C(Cl)C=CC=1OCCCCCC[C@]1(C(=O)[O-])CO1 RPACBEVZENYWOL-XFULWGLBSA-M 0.000 description 1
- MNCGMVDMOKPCSQ-UHFFFAOYSA-M sodium;2-phenylethenesulfonate Chemical compound [Na+].[O-]S(=O)(=O)C=CC1=CC=CC=C1 MNCGMVDMOKPCSQ-UHFFFAOYSA-M 0.000 description 1
- 125000006850 spacer group Chemical group 0.000 description 1
- 235000015096 spirit Nutrition 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 125000004079 stearyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000010557 suspension polymerization reaction Methods 0.000 description 1
- 229920001897 terpolymer Polymers 0.000 description 1
- 150000003512 tertiary amines Chemical group 0.000 description 1
- FZGFBJMPSHGTRQ-UHFFFAOYSA-M trimethyl(2-prop-2-enoyloxyethyl)azanium;chloride Chemical compound [Cl-].C[N+](C)(C)CCOC(=O)C=C FZGFBJMPSHGTRQ-UHFFFAOYSA-M 0.000 description 1
- NRWCNEBHECBWRJ-UHFFFAOYSA-M trimethyl(propyl)azanium;chloride Chemical compound [Cl-].CCC[N+](C)(C)C NRWCNEBHECBWRJ-UHFFFAOYSA-M 0.000 description 1
- NLVXSWCKKBEXTG-UHFFFAOYSA-N vinylsulfonic acid Chemical compound OS(=O)(=O)C=C NLVXSWCKKBEXTG-UHFFFAOYSA-N 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
- C08F8/28—Condensation with aldehydes or ketones
-
- 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
- C08F20/00—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride, ester, amide, imide or nitrile thereof
- C08F20/02—Monocarboxylic acids having less than ten carbon atoms, Derivatives thereof
- C08F20/52—Amides or imides
- C08F20/54—Amides, e.g. N,N-dimethylacrylamide or N-isopropylacrylamide
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J11/00—Recovery or working-up of waste materials
- C08J11/04—Recovery or working-up of waste materials of polymers
- C08J11/10—Recovery or working-up of waste materials of polymers by chemically breaking down the molecular chains of polymers or breaking of crosslinks, e.g. devulcanisation
- C08J11/16—Recovery or working-up of waste materials of polymers by chemically breaking down the molecular chains of polymers or breaking of crosslinks, e.g. devulcanisation by treatment with inorganic material
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L33/00—Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides or nitriles thereof; Compositions of derivatives of such polymers
- C08L33/24—Homopolymers or copolymers of amides or imides
-
- D—TEXTILES; PAPER
- D21—PAPER-MAKING; PRODUCTION OF CELLULOSE
- D21H—PULP COMPOSITIONS; PREPARATION THEREOF NOT COVERED BY SUBCLASSES D21C OR D21D; IMPREGNATING OR COATING OF PAPER; TREATMENT OF FINISHED PAPER NOT COVERED BY CLASS B31 OR SUBCLASS D21G; PAPER NOT OTHERWISE PROVIDED FOR
- D21H17/00—Non-fibrous material added to the pulp, characterised by its constitution; Paper-impregnating material characterised by its constitution
- D21H17/20—Macromolecular organic compounds
- D21H17/33—Synthetic macromolecular compounds
- D21H17/34—Synthetic macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
- D21H17/37—Polymers of unsaturated acids or derivatives thereof, e.g. polyacrylates
-
- D—TEXTILES; PAPER
- D21—PAPER-MAKING; PRODUCTION OF CELLULOSE
- D21H—PULP COMPOSITIONS; PREPARATION THEREOF NOT COVERED BY SUBCLASSES D21C OR D21D; IMPREGNATING OR COATING OF PAPER; TREATMENT OF FINISHED PAPER NOT COVERED BY CLASS B31 OR SUBCLASS D21G; PAPER NOT OTHERWISE PROVIDED FOR
- D21H21/00—Non-fibrous material added to the pulp, characterised by its function, form or properties; Paper-impregnating or coating material, characterised by its function, form or properties
- D21H21/14—Non-fibrous material added to the pulp, characterised by its function, form or properties; Paper-impregnating or coating material, characterised by its function, form or properties characterised by function or properties in or on the paper
- D21H21/18—Reinforcing agents
-
- 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
- C08F2800/00—Copolymer characterised by the proportions of the comonomers expressed
- C08F2800/10—Copolymer characterised by the proportions of the comonomers expressed as molar percentages
-
- 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
- C08F2800/00—Copolymer characterised by the proportions of the comonomers expressed
- C08F2800/20—Copolymer characterised by the proportions of the comonomers expressed as weight or mass percentages
-
- 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
- C08F2810/00—Chemical modification of a polymer
- C08F2810/10—Chemical modification of a polymer including a reactive processing step which leads, inter alia, to morphological and/or rheological modifications, e.g. visbreaking
-
- 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
- C08F2810/00—Chemical modification of a polymer
- C08F2810/20—Chemical modification of a polymer leading to a crosslinking, either explicitly or inherently
Landscapes
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- General Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Sustainable Development (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Paper (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Phenolic Resins Or Amino Resins (AREA)
Priority Applications (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| AU2013202746A AU2013202746B2 (en) | 2006-09-07 | 2013-04-06 | Glyoxalation of vinylamide polymer |
| AU2013204379A AU2013204379B2 (en) | 2006-09-07 | 2013-04-12 | Glyoxalation of vinylamide polymer |
| AU2013204365A AU2013204365C1 (en) | 2006-09-07 | 2013-04-12 | Glyoxalation of vinylamide polymer |
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US84315606P | 2006-09-07 | 2006-09-07 | |
| US60/843,156 | 2006-09-07 | ||
| US85118806P | 2006-10-12 | 2006-10-12 | |
| US60/851,188 | 2006-10-12 | ||
| PCT/EP2007/059096 WO2008028865A2 (en) | 2006-09-07 | 2007-08-31 | Glyoxalation of vinylamide polymer |
Related Child Applications (3)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AU2013202746A Division AU2013202746B2 (en) | 2006-09-07 | 2013-04-06 | Glyoxalation of vinylamide polymer |
| AU2013204365A Division AU2013204365C1 (en) | 2006-09-07 | 2013-04-12 | Glyoxalation of vinylamide polymer |
| AU2013204379A Division AU2013204379B2 (en) | 2006-09-07 | 2013-04-12 | Glyoxalation of vinylamide polymer |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| AU2007293922A1 AU2007293922A1 (en) | 2008-03-13 |
| AU2007293922B2 true AU2007293922B2 (en) | 2013-07-18 |
Family
ID=38805744
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AU2007293922A Ceased AU2007293922B2 (en) | 2006-09-07 | 2007-08-31 | Glyoxalation of vinylamide polymer |
Country Status (19)
| Country | Link |
|---|---|
| US (3) | US7875676B2 (enExample) |
| EP (4) | EP2386580B1 (enExample) |
| JP (1) | JP2010502800A (enExample) |
| KR (2) | KR101598388B1 (enExample) |
| CN (1) | CN102408519B (enExample) |
| AR (1) | AR062708A1 (enExample) |
| AT (1) | ATE533793T1 (enExample) |
| AU (1) | AU2007293922B2 (enExample) |
| BR (2) | BRPI0716253B1 (enExample) |
| CA (3) | CA2661967C (enExample) |
| CL (1) | CL2007002581A1 (enExample) |
| ES (4) | ES2870665T3 (enExample) |
| MX (1) | MX2009002486A (enExample) |
| NO (1) | NO20091034L (enExample) |
| PL (4) | PL2386580T3 (enExample) |
| PT (3) | PT2386579T (enExample) |
| RU (1) | RU2009112537A (enExample) |
| TW (1) | TW200838890A (enExample) |
| WO (1) | WO2008028865A2 (enExample) |
Families Citing this family (30)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7875676B2 (en) | 2006-09-07 | 2011-01-25 | Ciba Specialty Chemicals Corporation | Glyoxalation of vinylamide polymer |
| US8088250B2 (en) | 2008-11-26 | 2012-01-03 | Nalco Company | Method of increasing filler content in papermaking |
| AR071441A1 (es) * | 2007-11-05 | 2010-06-23 | Ciba Holding Inc | N- vinilamida glioxilada |
| CN101818464B (zh) * | 2010-03-16 | 2011-11-09 | 华泰集团有限公司 | 一种多臂支化阳离子聚合物造纸助留助滤剂及其制备方法与应用 |
| CN101962425B (zh) * | 2010-09-10 | 2011-12-21 | 山东轻工业学院 | 一种树核星形阴离子垃圾捕捉剂及应用 |
| CN102020754B (zh) * | 2010-10-29 | 2012-01-04 | 山东轻工业学院 | 一种阳离子树核星形聚合物造纸助剂的制备方法 |
| US8709207B2 (en) | 2010-11-02 | 2014-04-29 | Nalco Company | Method of using aldehyde-functionalized polymers to increase papermachine performance and enhance sizing |
| WO2013026578A1 (en) | 2011-08-25 | 2013-02-28 | Ashland Licensing And Intellectual Property Llc | Method for increasing the advantages of strength aids in the production of paper and paperboard |
| CN103987746B (zh) * | 2011-12-06 | 2018-04-20 | 巴斯夫欧洲公司 | 聚乙烯基酰胺纤维素反应性加成物的制备 |
| KR102295282B1 (ko) * | 2013-09-09 | 2021-08-31 | 바스프 에스이 | 고 분자량 및 고 양이온성 전하 글리옥살화된 폴리아크릴아미드 공중합체, 및 그의 제조 및 사용 방법 |
| US8894817B1 (en) * | 2014-01-16 | 2014-11-25 | Ecolab Usa Inc. | Wet end chemicals for dry end strength |
| US9567708B2 (en) * | 2014-01-16 | 2017-02-14 | Ecolab Usa Inc. | Wet end chemicals for dry end strength in paper |
| US9920482B2 (en) | 2014-10-06 | 2018-03-20 | Ecolab Usa Inc. | Method of increasing paper strength |
| US9702086B2 (en) | 2014-10-06 | 2017-07-11 | Ecolab Usa Inc. | Method of increasing paper strength using an amine containing polymer composition |
| FI126610B (en) * | 2015-01-27 | 2017-03-15 | Kemira Oyj | Particulate polymer product and its use |
| KR102063409B1 (ko) | 2015-12-25 | 2020-01-07 | 세이코 피엠씨 가부시키가이샤 | 폴리아크릴아미드계 제지용 첨가제 및 그의 제조 방법, 및 종이의 제조 방법 |
| AT518624B1 (de) * | 2016-04-25 | 2018-10-15 | Applied Chemicals Handels Gmbh | Verfahren zur Herstellung eines Trockenverfestigers, insbesondere von glyoxyliertem Polyacrylamid |
| US10648133B2 (en) | 2016-05-13 | 2020-05-12 | Ecolab Usa Inc. | Tissue dust reduction |
| WO2017209105A1 (ja) * | 2016-05-31 | 2017-12-07 | 三菱ケミカル株式会社 | 重合体、重合体の製造方法及び高分子凝集剤 |
| EP3335689B1 (en) * | 2016-12-14 | 2025-03-19 | DENTSPLY DETREY GmbH | Dental composition |
| WO2018122443A1 (en) * | 2016-12-28 | 2018-07-05 | Kemira Oyj | Glyoxylated polyacrylamide polymer composition, its use and method for increasing the strength properties of paper, board or the like |
| CN110268114B (zh) * | 2017-01-18 | 2022-12-13 | 索理思科技开曼公司 | 用于纸张的高分子量临时湿强度树脂 |
| FR3079516B1 (fr) * | 2018-03-30 | 2020-04-24 | S.P.C.M. Sa | Procede de fabrication de polymeres anioniques et utilisation comme agents de resistance dans un procede papetier |
| US11028538B2 (en) * | 2019-02-28 | 2021-06-08 | Solenis Technologies, L.P. | Composition and method for increasing wet and dry paper strength |
| FR3094980B1 (fr) | 2019-04-10 | 2021-04-09 | S N F Sa | Nouvel additif a base de polymeres hydrosolubles et ses utilisations |
| CN111622017B (zh) * | 2020-05-08 | 2022-02-08 | 仙鹤股份有限公司 | 一种低透气度ctp版衬纸及其制备方法 |
| CN116964147A (zh) | 2021-01-04 | 2023-10-27 | 索理思科技开曼公司 | 水性乙醛酸化聚丙烯酰胺组合物 |
| EP4405525A1 (en) | 2021-09-22 | 2024-07-31 | Kemira Oyj | Method for on-site glyoxylation of polyacrylamide |
| US20230235509A1 (en) * | 2022-01-21 | 2023-07-27 | Solenis Technologies, L.P. | Additive compositions for papermaking |
| WO2025101544A1 (en) * | 2023-11-06 | 2025-05-15 | Solenis Technologies Cayman, L.P. | Methods and compositions for papermaking |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4155405A (en) * | 1976-12-30 | 1979-05-22 | Societe Nationale Elf Aquitaine (Production) | Prevention of inflow of water into wells or shafts which have already been drilled or are being drilled |
| US4603176A (en) * | 1985-06-25 | 1986-07-29 | The Procter & Gamble Company | Temporary wet strength resins |
Family Cites Families (52)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3556932A (en) * | 1965-07-12 | 1971-01-19 | American Cyanamid Co | Water-soluble,ionic,glyoxylated,vinylamide,wet-strength resin and paper made therewith |
| GB1148005A (en) * | 1965-07-12 | 1969-04-10 | American Cyanamid Co | Wet strength resins and paper |
| US3580736A (en) * | 1967-04-26 | 1971-05-25 | Atlantic Richfield Co | Paperboard impregnated with a petroleum wax-polyurethane blend |
| US3556392A (en) | 1969-01-21 | 1971-01-19 | Dorothy Robin | Coffee bag |
| US3728214A (en) * | 1971-03-12 | 1973-04-17 | Hercules Inc | Polyamine-acrylamide-polyaldehyde resins having utility as wet and dry strengthening agents in papermaking |
| US3759197A (en) * | 1971-09-22 | 1973-09-18 | W Bracke | Process for the agglomeration of particulate materials |
| US4144123A (en) * | 1974-07-19 | 1979-03-13 | Basf Aktiengesellschaft | Incorporating a crosslinked polyamidoamine condensation product into paper-making pulp |
| US4103742A (en) * | 1975-12-24 | 1978-08-01 | Phillips Petroleum Company | Method for acidizing subterranean formations |
| DE2721960A1 (de) | 1976-05-26 | 1977-12-08 | Sandoz Ag | Polyamidaminverbindungen, deren herstellung und verwendung |
| US4217425A (en) | 1978-11-06 | 1980-08-12 | Nalco Chemical Company | Paper fiber additive containing polyacrylamide blended with glyoxal and polymeric diallyldimethyl ammonium chloride as a cationic regulator |
| DE3128478A1 (de) * | 1981-07-18 | 1983-02-03 | Basf Ag, 6700 Ludwigshafen | Verfahren zur herstellung von linearen, basischen polymerisaten |
| US4506062A (en) | 1982-08-09 | 1985-03-19 | Allied Colloids Limited | Inverse suspension polymerization process |
| GB8309275D0 (en) | 1983-04-06 | 1983-05-11 | Allied Colloids Ltd | Dissolution of water soluble polymers in water |
| GB8401206D0 (en) | 1984-01-17 | 1984-02-22 | Allied Colloids Ltd | Polymers and aqueous solutions |
| US4699379A (en) * | 1984-02-03 | 1987-10-13 | Robert E. Chateau | Athletic monitoring device |
| US4605702A (en) | 1984-06-27 | 1986-08-12 | American Cyanamid Company | Temporary wet strength resin |
| GB8416453D0 (en) | 1984-06-28 | 1984-08-01 | Allied Colloids Ltd | Aqueous polymer dispersions |
| JPS61207699A (ja) * | 1985-03-13 | 1986-09-16 | 日本カ−リツト株式会社 | ｐＨ依存性の少ない紙力増強剤 |
| JPH0676462B2 (ja) * | 1986-06-30 | 1994-09-28 | 三菱化成株式会社 | ビニルアミン共重合体およびその製法 |
| US4782900A (en) * | 1987-04-24 | 1988-11-08 | Pfizer Inc. | Aminoalkylated polyacrylamide aldehyde gels, their preparation and use in oil recovery |
| US5008344A (en) * | 1988-07-05 | 1991-04-16 | The Procter & Gamble Company | Temporary wet strength resins and paper products containing same |
| US5041503A (en) | 1988-12-19 | 1991-08-20 | American Cyanamid Company | Micro-emulsified glyoxalated acrylamide polymers |
| US4954538A (en) | 1988-12-19 | 1990-09-04 | American Cyanamid Company | Micro-emulsified glyoxalated acrylamide polymers |
| US5085787A (en) * | 1989-11-29 | 1992-02-04 | Air Products And Chemicals, Inc. | Crosslinked vinylamine polymer in enhanced oil recovery |
| DE4007312C2 (de) * | 1990-03-08 | 2000-04-27 | Basf Ag | Verfahren zur Herstellung von feinteiligen, wasserlöslichen, Vinylamin-Einheiten enthaltenden Polymerisaten |
| JP2979741B2 (ja) * | 1991-06-13 | 1999-11-15 | 荒川化学工業株式会社 | 製紙用添加剤の製造法 |
| US5281307A (en) * | 1993-01-13 | 1994-01-25 | Air Products And Chemicals, Inc. | Crosslinked vinyl alcohol/vinylamine copolymers for dry end paper addition |
| US5374334A (en) * | 1993-12-06 | 1994-12-20 | Nalco Chemical Company | Class of polymeric adhesives for yankee dryer applications |
| DE4413720A1 (de) | 1994-04-20 | 1995-10-26 | Basf Ag | Farbstoffübertragungsinhibitoren für Waschmittel |
| 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 |
| US5723022A (en) * | 1996-07-11 | 1998-03-03 | Cytec Technology Corp. | Temporary wet strength resins |
| MY118538A (en) | 1997-01-20 | 2004-12-31 | Ciba Spec Chem Water Treat Ltd | Polymeric compositions and their production and uses |
| MY120719A (en) | 1997-01-20 | 2005-11-30 | Ciba Spec Chem Water Treat Ltd | Polymeric compositions and their production and uses |
| DE19713755A1 (de) * | 1997-04-04 | 1998-10-08 | Basf Ag | Verfahren zur Herstellung von Papier, Pappe und Karton mit hoher Trockenfestigkeit |
| DE19719059A1 (de) * | 1997-05-06 | 1998-11-12 | Basf Ag | Verfahren zur Herstellung von Papier, Pappe und Karton |
| WO1999005167A1 (en) * | 1997-07-25 | 1999-02-04 | University Of Massachusetts | Designed protein pores as components for biosensors |
| US5951719A (en) * | 1998-06-15 | 1999-09-14 | Callaway Corporation | Process of after-treating dyed cellulose fabrics with a glyoxalated acrylamide polymer |
| WO2000011046A1 (en) | 1998-08-19 | 2000-03-02 | Hercules Incorporated | Dialdehyde-modified anionic and amphoteric polyacrylamides for improving strength of paper |
| DE19851024A1 (de) * | 1998-11-05 | 2000-05-11 | Basf Ag | Wäßrige Dispersionen von wasserlöslichen Polymerisaten von N-Vinylcarbonsäureamiden, Verfahren zu ihrer Herstellung und ihre Verwendung |
| CO5180563A1 (es) * | 1999-01-25 | 2002-07-30 | Kimberly Clark Co | Polimeros de vinilo modificados que contienen medios de hidrocarbono anfifilico de y el metodo para su fabricacion |
| 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. |
| JP4013188B2 (ja) * | 2002-02-22 | 2007-11-28 | 星光Ｐｍｃ株式会社 | （メタ）アクリルアミド系ポリマー、その製造方法、製紙用薬品、及びそれを含有する紙 |
| US7090745B2 (en) * | 2002-09-13 | 2006-08-15 | University Of Pittsburgh | Method for increasing the strength of a cellulosic product |
| US20040118540A1 (en) * | 2002-12-20 | 2004-06-24 | Kimberly-Clark Worlwide, Inc. | Bicomponent strengtheninig system for paper |
| US7641766B2 (en) * | 2004-01-26 | 2010-01-05 | Nalco Company | Method of using aldehyde-functionalized polymers to enhance paper machine dewatering |
| US7119148B2 (en) * | 2004-02-25 | 2006-10-10 | Georgia-Pacific Resins, Inc. | Glyoxylated polyacrylamide composition strengthening agent |
| JP4325589B2 (ja) | 2004-07-06 | 2009-09-02 | 株式会社デンソー | コモンレール用インジェクタ |
| WO2006016906A1 (en) | 2004-07-08 | 2006-02-16 | Lanxess Corporation | High-performance strength resins in papermaking industries |
| GB0425102D0 (en) * | 2004-11-15 | 2004-12-15 | Ciba Spec Chem Water Treat Ltd | Polymeric compositions and methods of employing them in papermaking processes |
| US20060162886A1 (en) * | 2005-01-24 | 2006-07-27 | Paradigm Chemical & Consulting, Llc | Process for improving dry strength and drainage of paper and paperboard |
| US20090223645A1 (en) | 2005-03-24 | 2009-09-10 | Naijie Zhang | Method and composition for improved temporary wet strength |
| US7875676B2 (en) * | 2006-09-07 | 2011-01-25 | Ciba Specialty Chemicals Corporation | Glyoxalation of vinylamide polymer |
-
2007
- 2007-08-28 US US11/895,923 patent/US7875676B2/en active Active
- 2007-08-31 ES ES16182870T patent/ES2870665T3/es active Active
- 2007-08-31 AT AT07803101T patent/ATE533793T1/de active
- 2007-08-31 EP EP11173866.2A patent/EP2386580B1/en active Active
- 2007-08-31 PT PT111738639T patent/PT2386579T/pt unknown
- 2007-08-31 PT PT07803101T patent/PT2059539E/pt unknown
- 2007-08-31 EP EP16182870.2A patent/EP3130615B1/en active Active
- 2007-08-31 CA CA2661967A patent/CA2661967C/en active Active
- 2007-08-31 KR KR1020147005290A patent/KR101598388B1/ko active Active
- 2007-08-31 CA CA2885393A patent/CA2885393C/en active Active
- 2007-08-31 WO PCT/EP2007/059096 patent/WO2008028865A2/en not_active Ceased
- 2007-08-31 CN CN201110281485.2A patent/CN102408519B/zh active Active
- 2007-08-31 PL PL11173866T patent/PL2386580T3/pl unknown
- 2007-08-31 EP EP07803101A patent/EP2059539B1/en active Active
- 2007-08-31 PL PL16182870T patent/PL3130615T3/pl unknown
- 2007-08-31 BR BRPI0716253A patent/BRPI0716253B1/pt active IP Right Grant
- 2007-08-31 BR BR122018003172A patent/BR122018003172B8/pt active IP Right Grant
- 2007-08-31 PT PT111738662T patent/PT2386580T/pt unknown
- 2007-08-31 KR KR1020097004834A patent/KR101428501B1/ko active Active
- 2007-08-31 JP JP2009527120A patent/JP2010502800A/ja active Pending
- 2007-08-31 MX MX2009002486A patent/MX2009002486A/es unknown
- 2007-08-31 PL PL07803101T patent/PL2059539T3/pl unknown
- 2007-08-31 CA CA2885391A patent/CA2885391C/en active Active
- 2007-08-31 AU AU2007293922A patent/AU2007293922B2/en not_active Ceased
- 2007-08-31 ES ES11173866.2T patent/ES2610614T3/es active Active
- 2007-08-31 EP EP11173863.9A patent/EP2386579B1/en active Active
- 2007-08-31 RU RU2009112537/04A patent/RU2009112537A/ru not_active Application Discontinuation
- 2007-08-31 PL PL11173863T patent/PL2386579T3/pl unknown
- 2007-08-31 ES ES07803101T patent/ES2377082T3/es active Active
- 2007-08-31 ES ES11173863.9T patent/ES2610612T3/es active Active
- 2007-09-05 TW TW096133004A patent/TW200838890A/zh unknown
- 2007-09-05 CL CL200702581A patent/CL2007002581A1/es unknown
- 2007-09-07 AR ARP070103966A patent/AR062708A1/es unknown
-
2009
- 2009-03-09 NO NO20091034A patent/NO20091034L/no not_active Application Discontinuation
-
2010
- 2010-12-16 US US12/969,783 patent/US8222343B2/en active Active
-
2012
- 2012-06-15 US US13/524,741 patent/US8703847B2/en active Active
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4155405A (en) * | 1976-12-30 | 1979-05-22 | Societe Nationale Elf Aquitaine (Production) | Prevention of inflow of water into wells or shafts which have already been drilled or are being drilled |
| US4603176A (en) * | 1985-06-25 | 1986-07-29 | The Procter & Gamble Company | Temporary wet strength resins |
Also Published As
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| AU2007293922B2 (en) | Glyoxalation of vinylamide polymer | |
| CA2858310C (en) | Preparation of polyvinylamide cellulose reactive adducts | |
| CN101553508B (zh) | 乙烯基酰胺聚合物的乙二醛化 | |
| CA2921043A1 (en) | High molecular weight and high cationic charge glyoxalated polyacrylamide copolymers, and thier methods of manufacture and use | |
| AU2013204365C1 (en) | Glyoxalation of vinylamide polymer |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PC1 | Assignment before grant (sect. 113) |
Owner name: BASF SE Free format text: FORMER APPLICANT(S): CIBA HOLDING INC. |
|
| FGA | Letters patent sealed or granted (standard patent) | ||
| MK14 | Patent ceased section 143(a) (annual fees not paid) or expired |