CA1058794A - Crosslinked polyamidoamine condensation products for papermaking - Google Patents
Crosslinked polyamidoamine condensation products for papermakingInfo
- Publication number
- CA1058794A CA1058794A CA231,008A CA231008A CA1058794A CA 1058794 A CA1058794 A CA 1058794A CA 231008 A CA231008 A CA 231008A CA 1058794 A CA1058794 A CA 1058794A
- Authority
- CA
- Canada
- Prior art keywords
- resin
- weight
- water
- parts
- addition
- 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
- 229920000962 poly(amidoamine) Polymers 0.000 title claims abstract description 16
- 239000007859 condensation product Substances 0.000 title claims description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 32
- 239000000243 solution Substances 0.000 claims abstract description 31
- 238000006243 chemical reaction Methods 0.000 claims abstract description 22
- 239000007864 aqueous solution Substances 0.000 claims abstract description 20
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 claims abstract description 18
- 239000007795 chemical reaction product Substances 0.000 claims abstract description 15
- 229920000768 polyamine Polymers 0.000 claims abstract description 14
- NOWKCMXCCJGMRR-UHFFFAOYSA-N Aziridine Chemical group C1CN1 NOWKCMXCCJGMRR-UHFFFAOYSA-N 0.000 claims abstract description 13
- 229920000233 poly(alkylene oxides) Polymers 0.000 claims abstract description 13
- 239000007787 solid Substances 0.000 claims abstract description 13
- 229920001281 polyalkylene Polymers 0.000 claims abstract description 11
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 9
- 125000002947 alkylene group Chemical group 0.000 claims abstract description 7
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 7
- 239000002841 Lewis acid Substances 0.000 claims abstract description 6
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 6
- 150000007517 lewis acids Chemical class 0.000 claims abstract description 6
- 125000004433 nitrogen atom Chemical group N* 0.000 claims abstract description 5
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims abstract description 4
- 239000003960 organic solvent Substances 0.000 claims abstract description 4
- 239000000203 mixture Substances 0.000 claims description 24
- 239000000047 product Substances 0.000 claims description 24
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 claims description 20
- 238000000034 method Methods 0.000 claims description 20
- 238000004519 manufacturing process Methods 0.000 claims description 14
- 238000009833 condensation Methods 0.000 claims description 12
- 230000005494 condensation Effects 0.000 claims description 12
- 230000008569 process Effects 0.000 claims description 11
- 239000001361 adipic acid Substances 0.000 claims description 10
- 235000011037 adipic acid Nutrition 0.000 claims description 10
- 239000000835 fiber Substances 0.000 claims description 10
- RPNUMPOLZDHAAY-UHFFFAOYSA-N Diethylenetriamine Chemical compound NCCNCCN RPNUMPOLZDHAAY-UHFFFAOYSA-N 0.000 claims description 9
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 4
- 239000007900 aqueous suspension Substances 0.000 claims 1
- 239000011347 resin Substances 0.000 description 115
- 229920005989 resin Polymers 0.000 description 115
- 239000000123 paper Substances 0.000 description 57
- 239000001913 cellulose Substances 0.000 description 40
- 229920002678 cellulose Polymers 0.000 description 40
- 239000000945 filler Substances 0.000 description 30
- 229940037003 alum Drugs 0.000 description 29
- 238000003359 percent control normalization Methods 0.000 description 19
- 239000002253 acid Substances 0.000 description 17
- 230000014759 maintenance of location Effects 0.000 description 17
- 230000003287 optical effect Effects 0.000 description 16
- 239000004971 Cross linker Substances 0.000 description 15
- 230000001133 acceleration Effects 0.000 description 15
- 230000009467 reduction Effects 0.000 description 14
- 229920002873 Polyethylenimine Polymers 0.000 description 12
- 239000000654 additive Substances 0.000 description 12
- 230000000996 additive effect Effects 0.000 description 12
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 11
- 150000001412 amines Chemical class 0.000 description 11
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- 230000000694 effects Effects 0.000 description 8
- 239000000463 material Substances 0.000 description 8
- 150000001875 compounds Chemical class 0.000 description 7
- 238000004132 cross linking Methods 0.000 description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- 239000003795 chemical substances by application Substances 0.000 description 6
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 6
- VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 6
- KIAPWMKFHIKQOZ-UHFFFAOYSA-N 2-[[(4-fluorophenyl)-oxomethyl]amino]benzoic acid methyl ester Chemical compound COC(=O)C1=CC=CC=C1NC(=O)C1=CC=C(F)C=C1 KIAPWMKFHIKQOZ-UHFFFAOYSA-N 0.000 description 5
- GKQPCPXONLDCMU-CCEZHUSRSA-N lacidipine Chemical compound CCOC(=O)C1=C(C)NC(C)=C(C(=O)OCC)C1C1=CC=CC=C1\C=C\C(=O)OC(C)(C)C GKQPCPXONLDCMU-CCEZHUSRSA-N 0.000 description 5
- 239000000725 suspension Substances 0.000 description 5
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 4
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- 230000007935 neutral effect Effects 0.000 description 4
- 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 3
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 3
- 229960000583 acetic acid Drugs 0.000 description 3
- -1 alkenyl diamines Chemical class 0.000 description 3
- 235000019253 formic acid Nutrition 0.000 description 3
- 239000012362 glacial acetic acid Substances 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 238000011084 recovery Methods 0.000 description 3
- 235000011121 sodium hydroxide Nutrition 0.000 description 3
- RTBFRGCFXZNCOE-UHFFFAOYSA-N 1-methylsulfonylpiperidin-4-one Chemical compound CS(=O)(=O)N1CCC(=O)CC1 RTBFRGCFXZNCOE-UHFFFAOYSA-N 0.000 description 2
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical group C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 2
- 239000005977 Ethylene Substances 0.000 description 2
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- 239000002202 Polyethylene glycol Substances 0.000 description 2
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 2
- JFCQEDHGNNZCLN-UHFFFAOYSA-N anhydrous glutaric acid Natural products OC(=O)CCCC(O)=O JFCQEDHGNNZCLN-UHFFFAOYSA-N 0.000 description 2
- 229920001400 block copolymer Polymers 0.000 description 2
- MCWXGJITAZMZEV-UHFFFAOYSA-N dimethoate Chemical compound CNC(=O)CSP(=S)(OC)OC MCWXGJITAZMZEV-UHFFFAOYSA-N 0.000 description 2
- UPCIBFUJJLCOQG-UHFFFAOYSA-L ethyl-[2-[2-[ethyl(dimethyl)azaniumyl]ethyl-methylamino]ethyl]-dimethylazanium;dibromide Chemical compound [Br-].[Br-].CC[N+](C)(C)CCN(C)CC[N+](C)(C)CC UPCIBFUJJLCOQG-UHFFFAOYSA-L 0.000 description 2
- 239000008394 flocculating agent Substances 0.000 description 2
- 230000006872 improvement Effects 0.000 description 2
- 229920001223 polyethylene glycol Polymers 0.000 description 2
- 229920001451 polypropylene glycol Polymers 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- CXMXRPHRNRROMY-UHFFFAOYSA-N sebacic acid Chemical compound OC(=O)CCCCCCCCC(O)=O CXMXRPHRNRROMY-UHFFFAOYSA-N 0.000 description 2
- TYFQFVWCELRYAO-UHFFFAOYSA-N suberic acid Chemical compound OC(=O)CCCCCCC(O)=O TYFQFVWCELRYAO-UHFFFAOYSA-N 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 2
- VILCJCGEZXAXTO-UHFFFAOYSA-N 2,2,2-tetramine Chemical compound NCCNCCNCCN VILCJCGEZXAXTO-UHFFFAOYSA-N 0.000 description 1
- FZQZRBQKXXGAMZ-UHFFFAOYSA-N 2-benzyl-3-nitropyridine Chemical compound [O-][N+](=O)C1=CC=CN=C1CC1=CC=CC=C1 FZQZRBQKXXGAMZ-UHFFFAOYSA-N 0.000 description 1
- ZAXCZCOUDLENMH-UHFFFAOYSA-N 3,3,3-tetramine Chemical compound NCCCNCCCNCCCN ZAXCZCOUDLENMH-UHFFFAOYSA-N 0.000 description 1
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 1
- 101100087530 Caenorhabditis elegans rom-1 gene Proteins 0.000 description 1
- 241000905957 Channa melasoma Species 0.000 description 1
- 102220628222 Coagulation factor IX_R46T_mutation Human genes 0.000 description 1
- 241000350052 Daniellia ogea Species 0.000 description 1
- UDSFAEKRVUSQDD-UHFFFAOYSA-N Dimethyl adipate Chemical compound COC(=O)CCCCC(=O)OC UDSFAEKRVUSQDD-UHFFFAOYSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 241001024304 Mino Species 0.000 description 1
- 101100305983 Mus musculus Rom1 gene Proteins 0.000 description 1
- 235000018734 Sambucus australis Nutrition 0.000 description 1
- 244000180577 Sambucus australis Species 0.000 description 1
- 241000364027 Sinoe Species 0.000 description 1
- DWAQJAXMDSEUJJ-UHFFFAOYSA-M Sodium bisulfite Chemical compound [Na+].OS([O-])=O DWAQJAXMDSEUJJ-UHFFFAOYSA-M 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-N Sulfurous acid Chemical compound OS(O)=O LSNNMFCWUKXFEE-UHFFFAOYSA-N 0.000 description 1
- 229910000611 Zinc aluminium Inorganic materials 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 125000004069 aziridinyl group Chemical group 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- FOCAUTSVDIKZOP-UHFFFAOYSA-N chloroacetic acid Chemical compound OC(=O)CCl FOCAUTSVDIKZOP-UHFFFAOYSA-N 0.000 description 1
- 229940106681 chloroacetic acid Drugs 0.000 description 1
- XENVCRGQTABGKY-ZHACJKMWSA-N chlorohydrin Chemical compound CC#CC#CC#CC#C\C=C\C(Cl)CO XENVCRGQTABGKY-ZHACJKMWSA-N 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- JJCFRYNCJDLXIK-UHFFFAOYSA-N cyproheptadine Chemical compound C1CN(C)CCC1=C1C2=CC=CC=C2C=CC2=CC=CC=C21 JJCFRYNCJDLXIK-UHFFFAOYSA-N 0.000 description 1
- 150000001991 dicarboxylic acids Chemical class 0.000 description 1
- 125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 1
- GYZLOYUZLJXAJU-UHFFFAOYSA-N diglycidyl ether Chemical class C1OC1COCC1CO1 GYZLOYUZLJXAJU-UHFFFAOYSA-N 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 230000005284 excitation Effects 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 230000003311 flocculating effect Effects 0.000 description 1
- 238000005189 flocculation Methods 0.000 description 1
- 230000016615 flocculation Effects 0.000 description 1
- ACCCMOQWYVYDOT-UHFFFAOYSA-N hexane-1,1-diol Chemical compound CCCCCC(O)O ACCCMOQWYVYDOT-UHFFFAOYSA-N 0.000 description 1
- 229920001519 homopolymer Polymers 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 150000002500 ions Chemical class 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
- 125000005647 linker group Chemical group 0.000 description 1
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 1
- UOBSVARXACCLLH-UHFFFAOYSA-N monomethyl adipate Chemical compound COC(=O)CCCCC(O)=O UOBSVARXACCLLH-UHFFFAOYSA-N 0.000 description 1
- VOVZXURTCKPRDQ-CQSZACIVSA-N n-[4-[chloro(difluoro)methoxy]phenyl]-6-[(3r)-3-hydroxypyrrolidin-1-yl]-5-(1h-pyrazol-5-yl)pyridine-3-carboxamide Chemical compound C1[C@H](O)CCN1C1=NC=C(C(=O)NC=2C=CC(OC(F)(F)Cl)=CC=2)C=C1C1=CC=NN1 VOVZXURTCKPRDQ-CQSZACIVSA-N 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 150000002924 oxiranes Chemical class 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 229920000333 poly(propyleneimine) Polymers 0.000 description 1
- 229920000151 polyglycol Polymers 0.000 description 1
- 239000010695 polyglycol Substances 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 230000036647 reaction Effects 0.000 description 1
- 238000009877 rendering Methods 0.000 description 1
- 235000010267 sodium hydrogen sulphite Nutrition 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- FAGUFWYHJQFNRV-UHFFFAOYSA-N tetraethylenepentamine Chemical compound NCCNCCNCCNCCN FAGUFWYHJQFNRV-UHFFFAOYSA-N 0.000 description 1
- 238000004448 titration Methods 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- YNDXUCZADRHECN-JNQJZLCISA-N triamcinolone acetonide Chemical compound C1CC2=CC(=O)C=C[C@]2(C)[C@]2(F)[C@@H]1[C@@H]1C[C@H]3OC(C)(C)O[C@@]3(C(=O)CO)[C@@]1(C)C[C@@H]2O YNDXUCZADRHECN-JNQJZLCISA-N 0.000 description 1
- 229960001124 trientine Drugs 0.000 description 1
- 239000002351 wastewater Substances 0.000 description 1
- 235000005074 zinc chloride Nutrition 0.000 description 1
- 239000011592 zinc chloride Substances 0.000 description 1
Classifications
-
- 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
- D21H17/46—Synthetic macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
- 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
- D21H17/55—Polyamides; Polyaminoamides; Polyester-amides
-
- 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
- C08G69/00—Macromolecular compounds obtained by reactions forming a carboxylic amide link in the main chain of the macromolecule
- C08G69/40—Polyamides containing oxygen in the form of ether groups
-
- 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
- D21H21/06—Paper forming aids
- D21H21/10—Retention agents or drainage improvers
Landscapes
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Paper (AREA)
- Macromolecular Compounds Obtained By Forming Nitrogen-Containing Linkages In General (AREA)
- Other Resins Obtained By Reactions Not Involving Carbon-To-Carbon Unsaturated Bonds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Transition And Organic Metals Composition Catalysts For Addition Polymerization (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2434816A DE2434816C3 (de) | 1974-07-19 | 1974-07-19 | Verfahren zur Herstellung von stickstoffhaltigen Kondensationsprodukten und deren Verwendung als Retentionsmittel, Flockungsmittel und Entwässerungsbeschleuniger bei der Papierherstellung |
| DE2515760A DE2515760C2 (de) | 1974-07-19 | 1975-04-10 | Verfahren zur Herstellung von stickstoffhaltigen Kondensationsprodukten |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1058794A true CA1058794A (en) | 1979-07-17 |
Family
ID=25767443
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA231,008A Expired CA1058794A (en) | 1974-07-19 | 1975-07-08 | Crosslinked polyamidoamine condensation products for papermaking |
Country Status (12)
Families Citing this family (34)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2736651A1 (de) * | 1977-08-13 | 1979-02-15 | Wolff Walsrode Ag | Hilfsmittel zur verbesserung der retention, entwaesserung und aufbereitung, insbesondere bei der papierherstellung |
| JPS5630184Y2 (enrdf_load_stackoverflow) * | 1978-07-03 | 1981-07-17 | ||
| DE2934854A1 (de) * | 1979-08-29 | 1981-09-10 | Basf Ag, 6700 Ludwigshafen | Verfahren zur herstellung von stickstoffhaltigen kondensationsprodukten und deren verwendung |
| DE3003648A1 (de) | 1980-02-01 | 1981-08-06 | Basf Ag, 6700 Ludwigshafen | Verfahren zur zerstellung von wasserloeslichen, stickstoffhaltigen kondensationsprodukten und deren verwendung bei der papierherstellung |
| DE3135830A1 (de) * | 1981-09-10 | 1983-03-24 | Basf Ag, 6700 Ludwigshafen | Verfahren zur herstellung von wasserloeslichen, stickstoffhaltigen kondensationsprodukten und deren verwendung bei der papierherstellung |
| DE3316179A1 (de) * | 1983-05-04 | 1984-11-08 | Basf Ag, 6700 Ludwigshafen | Verfahren zur masseleimung von papier |
| DE3413567A1 (de) * | 1984-04-11 | 1985-10-24 | Bayer Ag, 5090 Leverkusen | Papierhilfsmittel |
| DE3732981A1 (de) * | 1987-09-30 | 1989-04-13 | Basf Ag | Verfahren zum faerben von papier |
| DE3822490A1 (de) * | 1988-07-02 | 1990-01-04 | Hoechst Ag | Waessrige loesungen von polyamidoamin-epichlorhyrin-harzen, verfahren zu ihrer herstellung und ihre verwendung |
| DE4240110A1 (de) * | 1992-11-28 | 1994-06-01 | Basf Ag | Kondensationsprodukte von Polyalkylenpolyaminen, Verfahren zu ihrer Herstellung und ihre Verwendung bei der Herstellung von Papier |
| DE4407496A1 (de) * | 1994-03-07 | 1995-09-14 | Basf Ag | Wäßrige Farbstoffpräparationen, enthaltend Cumarinfarbstoffe |
| DE19715832A1 (de) | 1997-04-16 | 1998-10-22 | Basf Ag | Verfahren zur Herstellung von Papier, Pappe und Karton |
| US6011134A (en) * | 1998-01-30 | 2000-01-04 | E. I. Du Pont De Nemours And Company | Method for manufacturing poly(hexamethylene adipamide) from monomethyladipate and hexamethylenediamine |
| CN100436707C (zh) | 2001-06-11 | 2008-11-26 | 巴斯福股份公司 | 用于纸张的湿强度整理剂 |
| DE102004058587A1 (de) | 2004-12-03 | 2006-06-14 | Basf Ag | Verfahren zur Herstellung von Papieren mit hohen Flächengewichten |
| JP4748794B2 (ja) * | 2006-04-03 | 2011-08-17 | 伯東株式会社 | ピッチコントロール剤及びピッチコントロール方法 |
| JP5693230B2 (ja) | 2007-12-20 | 2015-04-01 | ビーエーエスエフ ソシエタス・ヨーロピアＢａｓｆ Ｓｅ | オリゴアルキレンイミン側鎖を有するグラフトポリマー、それらの製造方法及びそれらの使用 |
| CA2733503C (en) | 2008-08-18 | 2018-07-03 | Basf Se | Process for increasing the dry strength of paper, board and cardboard |
| EP2334871B1 (de) | 2008-09-02 | 2018-07-18 | Basf Se | Verfahren zur herstellung von papier, pappe und karton unter verwendung von endo-beta-1,4-glucanasen als entwässerungsmittel |
| EP2395041A1 (en) * | 2010-06-10 | 2011-12-14 | F. Hoffmann-La Roche AG | Polymers for delivery of nucleic acids |
| WO2011154331A1 (en) * | 2010-06-10 | 2011-12-15 | F. Hoffmann-La Roche Ag | Polymers for delivery of nucleic acids |
| DE102010026490A1 (de) | 2010-07-07 | 2012-01-12 | Basf Se | Verfahren zur Herstellung von feinstrukturierten Oberflächen |
| US8486427B2 (en) | 2011-02-11 | 2013-07-16 | Kimberly-Clark Worldwide, Inc. | Wipe for use with a germicidal solution |
| EP2688405B1 (en) | 2011-03-23 | 2017-11-22 | Basf Se | Compositions containing polymeric, ionic compounds comprising imidazolium groups |
| CA2862095C (en) | 2012-02-01 | 2017-04-11 | Basf Se | Process for the manufacture of paper and paperboard |
| EP2820189B2 (en) | 2012-03-01 | 2024-05-15 | Basf Se | Process for the manufacture of paper and paperboard |
| WO2014108844A1 (en) | 2013-01-11 | 2014-07-17 | Basf Se | Process for the manufacture of paper and paperboard |
| US20170362776A1 (en) | 2014-12-16 | 2017-12-21 | Basf Se | Production of paper and board |
| KR102135652B1 (ko) | 2015-09-30 | 2020-07-20 | 후루카와 덴키 고교 가부시키가이샤 | 와이어 공구용 다이아몬드 지립 및 와이어 공구 |
| EP3173449A1 (de) | 2015-11-27 | 2017-05-31 | BASF Coatings GmbH | Verbund aus zwei festkörpern |
| WO2017194331A1 (en) | 2016-05-12 | 2017-11-16 | Basf Se | Use of polyimidazolium salts as dye transfer inhibitors |
| WO2018042060A1 (de) | 2016-09-05 | 2018-03-08 | Drei Lilien Pvg Gmbh & Co. Kg | Offenporige membran mit innerem raumdurchspannendem polymerem strukturnetzwerk zur elektrophoretischen stoffselektiven separation sowie verfahren zu deren herstellung und anwendung |
| US20200171214A1 (en) | 2017-07-07 | 2020-06-04 | Drei Lilien Pvg Gmbh & Co. Kg | Bioresorbable surface coating for delaying degradation |
| JP6696532B2 (ja) * | 2018-06-18 | 2020-05-20 | 栗田工業株式会社 | 紙の製造方法 |
-
1974
- 1974-07-19 DE DE2434816A patent/DE2434816C3/de not_active Expired
-
1975
- 1975-04-10 DE DE2515760A patent/DE2515760C2/de not_active Expired
- 1975-07-08 CA CA231,008A patent/CA1058794A/en not_active Expired
- 1975-07-10 FI FI752009A patent/FI61904C/fi not_active IP Right Cessation
- 1975-07-10 NO NO752474A patent/NO143028C/no unknown
- 1975-07-16 CH CH931375A patent/CH616170A5/de not_active IP Right Cessation
- 1975-07-16 JP JP8625575A patent/JPS575813B2/ja not_active Expired
- 1975-07-17 FR FR7522379A patent/FR2330799A1/fr active Granted
- 1975-07-17 BE BE158399A patent/BE831481A/xx not_active IP Right Cessation
- 1975-07-17 SE SE7508201A patent/SE450958B/xx not_active IP Right Cessation
- 1975-07-18 GB GB30188/75A patent/GB1509967A/en not_active Expired
- 1975-07-18 NL NLAANVRAGE7508636,A patent/NL180222C/xx not_active IP Right Cessation
- 1975-07-18 AT AT559275A patent/AT350272B/de not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| AT350272B (de) | 1979-05-25 |
| AU8280075A (en) | 1977-01-13 |
| GB1509967A (en) | 1978-05-10 |
| SE7508201L (sv) | 1976-01-20 |
| JPS575813B2 (enrdf_load_stackoverflow) | 1982-02-02 |
| NO143028B (no) | 1980-08-25 |
| BE831481A (fr) | 1976-01-19 |
| NL7508636A (nl) | 1976-01-21 |
| DE2434816A1 (de) | 1976-02-05 |
| DE2434816C3 (de) | 1981-01-22 |
| ATA559275A (de) | 1978-10-15 |
| FR2330799B1 (enrdf_load_stackoverflow) | 1978-10-13 |
| NL180222B (nl) | 1986-08-18 |
| DE2434816B2 (de) | 1980-05-14 |
| JPS5184895A (enrdf_load_stackoverflow) | 1976-07-24 |
| NL180222C (nl) | 1987-01-16 |
| CH616170A5 (en) | 1980-03-14 |
| FI61904B (fi) | 1982-06-30 |
| NO752474L (enrdf_load_stackoverflow) | 1976-01-20 |
| DE2515760C2 (de) | 1984-03-15 |
| NO143028C (no) | 1980-12-03 |
| DE2515760A1 (de) | 1976-10-21 |
| FR2330799A1 (fr) | 1977-06-03 |
| FI61904C (fi) | 1982-10-11 |
| SE450958B (sv) | 1987-08-17 |
| FI752009A7 (enrdf_load_stackoverflow) | 1976-01-20 |
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