CA1042133A - Cationic polyurethanes - Google Patents
Cationic polyurethanesInfo
- Publication number
- CA1042133A CA1042133A CA215,808A CA215808A CA1042133A CA 1042133 A CA1042133 A CA 1042133A CA 215808 A CA215808 A CA 215808A CA 1042133 A CA1042133 A CA 1042133A
- Authority
- CA
- Canada
- Prior art keywords
- aliphatic
- chain
- process according
- sizing
- paper
- 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
- 239000004814 polyurethane Substances 0.000 title claims abstract description 60
- 229920002635 polyurethane Polymers 0.000 title claims abstract description 57
- 125000002091 cationic group Chemical group 0.000 title claims abstract description 39
- 238000006243 chemical reaction Methods 0.000 claims abstract description 32
- 150000001875 compounds Chemical class 0.000 claims abstract description 28
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims abstract description 27
- 125000001931 aliphatic group Chemical group 0.000 claims abstract description 26
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 26
- 150000003868 ammonium compounds Chemical class 0.000 claims abstract description 18
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims abstract description 16
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 15
- 229920001228 polyisocyanate Polymers 0.000 claims abstract description 12
- 239000005056 polyisocyanate Substances 0.000 claims abstract description 12
- 150000002009 diols Chemical class 0.000 claims abstract description 11
- 238000004513 sizing Methods 0.000 claims description 66
- 238000000034 method Methods 0.000 claims description 36
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical group CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 24
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 17
- 239000006185 dispersion Substances 0.000 claims description 16
- 239000002253 acid Substances 0.000 claims description 10
- -1 glycerin fatty acid Chemical class 0.000 claims description 10
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 10
- 239000002904 solvent Substances 0.000 claims description 10
- 125000004429 atom Chemical group 0.000 claims description 8
- VBICKXHEKHSIBG-UHFFFAOYSA-N 1-monostearoylglycerol Chemical group CCCCCCCCCCCCCCCCCC(=O)OCC(O)CO VBICKXHEKHSIBG-UHFFFAOYSA-N 0.000 claims description 7
- 239000000203 mixture Substances 0.000 claims description 7
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 7
- 125000001424 substituent group Chemical group 0.000 claims description 7
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 claims description 6
- 238000001035 drying Methods 0.000 claims description 6
- CRVGTESFCCXCTH-UHFFFAOYSA-N methyl diethanolamine Chemical compound OCCN(C)CCO CRVGTESFCCXCTH-UHFFFAOYSA-N 0.000 claims description 6
- 229910052799 carbon Inorganic materials 0.000 claims description 5
- 125000005442 diisocyanate group Chemical group 0.000 claims description 5
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerol Natural products OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims description 4
- 125000003118 aryl group Chemical group 0.000 claims description 4
- 235000014113 dietary fatty acids Nutrition 0.000 claims description 4
- 239000000194 fatty acid Substances 0.000 claims description 4
- 229930195729 fatty acid Natural products 0.000 claims description 4
- 235000011187 glycerol Nutrition 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 3
- DVKJHBMWWAPEIU-UHFFFAOYSA-N toluene 2,4-diisocyanate Chemical compound CC1=CC=C(N=C=O)C=C1N=C=O DVKJHBMWWAPEIU-UHFFFAOYSA-N 0.000 claims description 3
- NDLNTMNRNCENRZ-UHFFFAOYSA-N 2-[2-hydroxyethyl(octadecyl)amino]ethanol Chemical compound CCCCCCCCCCCCCCCCCCN(CCO)CCO NDLNTMNRNCENRZ-UHFFFAOYSA-N 0.000 claims description 2
- BYNVYIUJKRRNNC-UHFFFAOYSA-N docosanoic acid;propane-1,2,3-triol Chemical group OCC(O)CO.CCCCCCCCCCCCCCCCCCCCCC(O)=O BYNVYIUJKRRNNC-UHFFFAOYSA-N 0.000 claims description 2
- 239000007788 liquid Substances 0.000 claims description 2
- IXPJJKQWVAWRQS-UHFFFAOYSA-N octadecane-1,4-diol Chemical compound CCCCCCCCCCCCCCC(O)CCCO IXPJJKQWVAWRQS-UHFFFAOYSA-N 0.000 claims description 2
- 125000002947 alkylene group Chemical group 0.000 claims 2
- 229920000881 Modified starch Polymers 0.000 claims 1
- 150000001450 anions Chemical class 0.000 claims 1
- 239000012736 aqueous medium Substances 0.000 claims 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 claims 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 claims 1
- 235000019426 modified starch Nutrition 0.000 claims 1
- 239000003795 chemical substances by application Substances 0.000 abstract description 31
- 238000004026 adhesive bonding Methods 0.000 abstract 1
- 239000000123 paper Substances 0.000 description 33
- 239000000047 product Substances 0.000 description 32
- 239000011436 cob Substances 0.000 description 20
- 239000000243 solution Substances 0.000 description 19
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 19
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 9
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 7
- 230000014759 maintenance of location Effects 0.000 description 7
- 229960000443 hydrochloric acid Drugs 0.000 description 6
- 235000011167 hydrochloric acid Nutrition 0.000 description 6
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 description 6
- 150000003839 salts Chemical class 0.000 description 6
- 229940100198 alkylating agent Drugs 0.000 description 5
- 239000002168 alkylating agent Substances 0.000 description 5
- 230000015572 biosynthetic process Effects 0.000 description 5
- 125000005842 heteroatom Chemical group 0.000 description 5
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 5
- 229920000642 polymer Polymers 0.000 description 5
- 239000007858 starting material Substances 0.000 description 5
- 229920002472 Starch Polymers 0.000 description 4
- 238000000576 coating method Methods 0.000 description 4
- 230000002349 favourable effect Effects 0.000 description 4
- 239000001257 hydrogen Substances 0.000 description 4
- 229910052739 hydrogen Inorganic materials 0.000 description 4
- 150000003254 radicals Chemical class 0.000 description 4
- 239000008107 starch Substances 0.000 description 4
- 235000019698 starch Nutrition 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 150000001721 carbon Chemical group 0.000 description 3
- 239000003054 catalyst Substances 0.000 description 3
- 239000001913 cellulose Substances 0.000 description 3
- 229920002678 cellulose Polymers 0.000 description 3
- 239000011248 coating agent Substances 0.000 description 3
- 239000000839 emulsion Substances 0.000 description 3
- 239000010419 fine particle Substances 0.000 description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 3
- 239000002245 particle Substances 0.000 description 3
- 229920003023 plastic Polymers 0.000 description 3
- 239000004033 plastic Substances 0.000 description 3
- 125000005628 tolylene group Chemical group 0.000 description 3
- 239000004970 Chain extender Substances 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical group CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-O ammonium group Chemical group [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 2
- 239000011230 binding agent Substances 0.000 description 2
- 229920001577 copolymer Polymers 0.000 description 2
- 238000004132 cross linking Methods 0.000 description 2
- VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 229920000554 ionomer Polymers 0.000 description 2
- 239000010985 leather Substances 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 239000000155 melt Substances 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 230000003647 oxidation Effects 0.000 description 2
- 238000007254 oxidation reaction Methods 0.000 description 2
- 230000035484 reaction time Effects 0.000 description 2
- 238000001694 spray drying Methods 0.000 description 2
- 238000003860 storage Methods 0.000 description 2
- 229910021653 sulphate ion Inorganic materials 0.000 description 2
- 150000003512 tertiary amines Chemical class 0.000 description 2
- 238000010998 test method Methods 0.000 description 2
- 239000004753 textile Substances 0.000 description 2
- 238000005303 weighing Methods 0.000 description 2
- XXZCIYUJYUESMD-UHFFFAOYSA-N 2-[4-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]-3-(morpholin-4-ylmethyl)pyrazol-1-yl]-1-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)ethanone Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C=1C(=NN(C=1)CC(=O)N1CC2=C(CC1)NN=N2)CN1CCOCC1 XXZCIYUJYUESMD-UHFFFAOYSA-N 0.000 description 1
- XHJGXOOOMKCJPP-UHFFFAOYSA-N 2-[tert-butyl(2-hydroxyethyl)amino]ethanol Chemical compound OCCN(C(C)(C)C)CCO XHJGXOOOMKCJPP-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- 229920002134 Carboxymethyl cellulose Polymers 0.000 description 1
- 241000518994 Conta Species 0.000 description 1
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 1
- 229920000965 Duroplast Polymers 0.000 description 1
- CYTYCFOTNPOANT-UHFFFAOYSA-N Perchloroethylene Chemical group ClC(Cl)=C(Cl)Cl CYTYCFOTNPOANT-UHFFFAOYSA-N 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- 235000008331 Pinus X rigitaeda Nutrition 0.000 description 1
- 235000011613 Pinus brutia Nutrition 0.000 description 1
- 241000018646 Pinus brutia Species 0.000 description 1
- 239000004952 Polyamide Substances 0.000 description 1
- 239000004372 Polyvinyl alcohol Substances 0.000 description 1
- ISKQADXMHQSTHK-UHFFFAOYSA-N [4-(aminomethyl)phenyl]methanamine Chemical compound NCC1=CC=C(CN)C=C1 ISKQADXMHQSTHK-UHFFFAOYSA-N 0.000 description 1
- JJLKTTCRRLHVGL-UHFFFAOYSA-L [acetyloxy(dibutyl)stannyl] acetate Chemical compound CC([O-])=O.CC([O-])=O.CCCC[Sn+2]CCCC JJLKTTCRRLHVGL-UHFFFAOYSA-L 0.000 description 1
- UKLDJPRMSDWDSL-UHFFFAOYSA-L [dibutyl(dodecanoyloxy)stannyl] dodecanoate Chemical compound CCCCCCCCCCCC(=O)O[Sn](CCCC)(CCCC)OC(=O)CCCCCCCCCCC UKLDJPRMSDWDSL-UHFFFAOYSA-L 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000002318 adhesion promoter Substances 0.000 description 1
- 239000000853 adhesive Substances 0.000 description 1
- 230000001070 adhesive effect Effects 0.000 description 1
- 229920000615 alginic acid Polymers 0.000 description 1
- 235000010443 alginic acid Nutrition 0.000 description 1
- 229940037003 alum Drugs 0.000 description 1
- 239000010425 asbestos Substances 0.000 description 1
- 239000010426 asphalt Substances 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000001768 carboxy methyl cellulose Substances 0.000 description 1
- 235000010948 carboxy methyl cellulose Nutrition 0.000 description 1
- 239000008112 carboxymethyl-cellulose Substances 0.000 description 1
- 229940105329 carboxymethylcellulose Drugs 0.000 description 1
- 229920003086 cellulose ether Polymers 0.000 description 1
- 239000000919 ceramic Substances 0.000 description 1
- 229910010293 ceramic material Inorganic materials 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000011362 coarse particle Substances 0.000 description 1
- 239000004567 concrete Substances 0.000 description 1
- 238000005520 cutting process Methods 0.000 description 1
- KORSJDCBLAPZEQ-UHFFFAOYSA-N dicyclohexylmethane-4,4'-diisocyanate Chemical compound C1CC(N=C=O)CCC1CC1CCC(N=C=O)CC1 KORSJDCBLAPZEQ-UHFFFAOYSA-N 0.000 description 1
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 229960001760 dimethyl sulfoxide Drugs 0.000 description 1
- CZZYITDELCSZES-UHFFFAOYSA-N diphenylmethane Chemical compound C=1C=CC=CC=1CC1=CC=CC=C1 CZZYITDELCSZES-UHFFFAOYSA-N 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 238000004043 dyeing Methods 0.000 description 1
- 229920001971 elastomer Polymers 0.000 description 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N ethyl acetate Substances CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 1
- 239000004744 fabric Substances 0.000 description 1
- 238000000855 fermentation Methods 0.000 description 1
- 230000004151 fermentation Effects 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 238000005187 foaming Methods 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 239000003365 glass fiber Substances 0.000 description 1
- 150000002334 glycols Chemical class 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 125000004836 hexamethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 239000012948 isocyanate Substances 0.000 description 1
- 150000002513 isocyanates Chemical class 0.000 description 1
- 238000010030 laminating Methods 0.000 description 1
- 238000011031 large-scale manufacturing process Methods 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- AQKAXAHWPVKCSB-UHFFFAOYSA-N n,n-dihydroxyicosan-1-amine Chemical compound CCCCCCCCCCCCCCCCCCCCN(O)O AQKAXAHWPVKCSB-UHFFFAOYSA-N 0.000 description 1
- GEMHFKXPOCTAIP-UHFFFAOYSA-N n,n-dimethyl-n'-phenylcarbamimidoyl chloride Chemical compound CN(C)C(Cl)=NC1=CC=CC=C1 GEMHFKXPOCTAIP-UHFFFAOYSA-N 0.000 description 1
- 239000004745 nonwoven fabric Substances 0.000 description 1
- VJQGGZWPOMJLTP-UHFFFAOYSA-N octadecane-1,1-diol Chemical compound CCCCCCCCCCCCCCCCCC(O)O VJQGGZWPOMJLTP-UHFFFAOYSA-N 0.000 description 1
- 238000005580 one pot reaction Methods 0.000 description 1
- 238000011022 operating instruction Methods 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 229920003009 polyurethane dispersion Polymers 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- 229910052573 porcelain Inorganic materials 0.000 description 1
- 229920001592 potato starch Polymers 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- 239000001294 propane Substances 0.000 description 1
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 229910052895 riebeckite Inorganic materials 0.000 description 1
- 238000005096 rolling process Methods 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000004575 stone Substances 0.000 description 1
- 239000010902 straw Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-L sulfite Chemical compound [O-]S([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-L 0.000 description 1
- 238000004381 surface treatment Methods 0.000 description 1
- 229950011008 tetrachloroethylene Drugs 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- RUELTTOHQODFPA-UHFFFAOYSA-N toluene 2,6-diisocyanate Chemical compound CC1=C(N=C=O)C=CC=C1N=C=O RUELTTOHQODFPA-UHFFFAOYSA-N 0.000 description 1
- 229940086542 triethylamine Drugs 0.000 description 1
- 238000005292 vacuum distillation Methods 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
- CHJMFFKHPHCQIJ-UHFFFAOYSA-L zinc;octanoate Chemical compound [Zn+2].CCCCCCCC([O-])=O.CCCCCCCC([O-])=O CHJMFFKHPHCQIJ-UHFFFAOYSA-L 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
- D21H17/57—Polyureas; Polyurethanes
-
- 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
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/08—Processes
- C08G18/0804—Manufacture of polymers containing ionic or ionogenic groups
- C08G18/0809—Manufacture of polymers containing ionic or ionogenic groups containing cationic or cationogenic groups
- C08G18/0814—Manufacture of polymers containing ionic or ionogenic groups containing cationic or cationogenic groups containing ammonium groups or groups forming them
-
- 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
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/08—Processes
- C08G18/10—Prepolymer processes involving reaction of isocyanates or isothiocyanates with compounds having active hydrogen in a first reaction step
-
- 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
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/30—Low-molecular-weight compounds
- C08G18/36—Hydroxylated esters of higher fatty acids
Landscapes
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Manufacturing & Machinery (AREA)
- Polyurethanes Or Polyureas (AREA)
- Paper (AREA)
- Macromolecular Compounds Obtained By Forming Nitrogen-Containing Linkages In General (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2400490A DE2400490C2 (de) | 1974-01-05 | 1974-01-05 | Kationische Polyurethane und Verfahren zu deren Herstellung |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1042133A true CA1042133A (en) | 1978-11-07 |
Family
ID=5904240
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA215,808A Expired CA1042133A (en) | 1974-01-05 | 1974-12-10 | Cationic polyurethanes |
Country Status (25)
| Country | Link |
|---|---|
| JP (2) | JPS5514088B2 (en, 2012) |
| AR (1) | AR208899A1 (en, 2012) |
| AT (1) | AT339607B (en, 2012) |
| BE (1) | BE824067A (en, 2012) |
| BR (1) | BR7410962D0 (en, 2012) |
| CA (1) | CA1042133A (en, 2012) |
| CH (1) | CH621807A5 (en, 2012) |
| CS (1) | CS194713B2 (en, 2012) |
| DD (2) | DD119803A5 (en, 2012) |
| DE (1) | DE2400490C2 (en, 2012) |
| ES (1) | ES432957A1 (en, 2012) |
| FI (1) | FI58783C (en, 2012) |
| FR (1) | FR2256937B1 (en, 2012) |
| GB (1) | GB1491091A (en, 2012) |
| HU (1) | HU170930B (en, 2012) |
| IE (1) | IE40449B1 (en, 2012) |
| IL (1) | IL46283A (en, 2012) |
| IT (1) | IT1026224B (en, 2012) |
| NL (1) | NL177218C (en, 2012) |
| NO (1) | NO141167C (en, 2012) |
| PL (1) | PL99474B1 (en, 2012) |
| SE (1) | SE422804B (en, 2012) |
| SU (1) | SU944507A3 (en, 2012) |
| YU (1) | YU36535B (en, 2012) |
| ZA (1) | ZA747909B (en, 2012) |
Families Citing this family (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2537653B2 (de) * | 1975-08-23 | 1977-10-27 | Bayer Ag, 5090 Leverkusen | Papierleimungsmittel und verfahren zur papierleimung |
| DE3102038A1 (de) * | 1980-01-28 | 1981-12-10 | W.R. Grace & Co., 02140 Cambridge, Mass. | Polyurethanpolymeraminsalz als papieradditiv |
| DE3017599C2 (de) * | 1980-05-08 | 1985-01-10 | Akzo Gmbh, 5600 Wuppertal | Brennstoffbriketts |
| AU542545B2 (en) * | 1980-05-08 | 1985-02-28 | Akzo N.V. | Fuel briquettes |
| SE8200472L (sv) * | 1981-02-23 | 1982-08-24 | Grace W R & Co | Forfarande for att forbettra vatdraghallfastheten hos papper |
| FR2565267B1 (fr) * | 1984-06-05 | 1987-10-23 | Atochem | Latex de polyurethanne comme agent de collage en industrie papetiere, son procede de fabrication |
| JPS61174884A (ja) * | 1985-01-30 | 1986-08-06 | Canon Inc | 撮像装置 |
| DE3523856A1 (de) * | 1985-07-04 | 1987-01-08 | Bayer Ag | Waessrige loesungen oder dispersionen von polyisocyanat-additionsprodukten, ein verfahren zu ihrer herstellung, sowie ihre verwendung als beschichtungsmittel oder als leimungsmittel fuer papier |
| CA1316957C (en) * | 1986-12-18 | 1993-04-27 | John Brian Cooper | Pressure sensitive record material |
| CA2255844A1 (en) * | 1996-05-28 | 1997-12-04 | Eka Chemicals Ab | Quaternary ammonium compounds |
| GB9901597D0 (en) * | 1999-01-26 | 1999-03-17 | Ciba Spec Chem Water Treat Ltd | Sizing compositions |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DD5381A (en, 2012) * | ||||
| DD5379A (en, 2012) * | ||||
| DE953012C (de) * | 1952-07-04 | 1956-11-22 | Bayer Ag | Verfahren zur Herstellung von loeslichen, vorzugsweise hoehermolekularen und zur weiteren Umsetzung befaehigten Polyisocyanaten |
| US2966472A (en) * | 1957-06-26 | 1960-12-27 | Allied Chem | Non-cellular polyurethane coating resistant to discoloration |
| GB953357A (en) * | 1960-11-08 | 1964-03-25 | Textron Inc | A process for the preparation of urethane modified vegetable oils |
| DE1570602A1 (de) * | 1965-09-03 | 1969-08-14 | Bayer Ag | Verfahren zur Herstellung von waessrigen Polyurethan-Dispersionen |
| DE1595602A1 (de) * | 1966-03-12 | 1969-09-18 | Bayer Ag | Verfahren zur Herstellung von Polyurethan-Kunststoffen |
| DE2019324C3 (de) * | 1970-04-22 | 1979-02-22 | Bayer Ag, 5090 Leverkusen | Verfahren zur Herstellung von lichtechten Polyurethanionomeren |
-
1974
- 1974-01-05 DE DE2400490A patent/DE2400490C2/de not_active Expired
- 1974-11-25 AT AT942674A patent/AT339607B/de not_active IP Right Cessation
- 1974-12-05 FR FR7439765A patent/FR2256937B1/fr not_active Expired
- 1974-12-10 IE IE2539/74A patent/IE40449B1/xx unknown
- 1974-12-10 NO NO744454A patent/NO141167C/no unknown
- 1974-12-10 CA CA215,808A patent/CA1042133A/en not_active Expired
- 1974-12-11 ZA ZA00747909A patent/ZA747909B/xx unknown
- 1974-12-16 ES ES432957A patent/ES432957A1/es not_active Expired
- 1974-12-18 IL IL46283A patent/IL46283A/en unknown
- 1974-12-19 DD DD183222A patent/DD119803A5/xx unknown
- 1974-12-19 DD DD189369A patent/DD121659A5/xx unknown
- 1974-12-23 CH CH1701374A patent/CH621807A5/de not_active IP Right Cessation
- 1974-12-25 JP JP754212A patent/JPS5514088B2/ja not_active Expired
- 1974-12-26 AR AR257086A patent/AR208899A1/es active
- 1974-12-30 FI FI3787/74A patent/FI58783C/fi active
- 1974-12-30 BR BR10962/74A patent/BR7410962D0/pt unknown
- 1974-12-31 NL NLAANVRAGE7417024,A patent/NL177218C/xx not_active IP Right Cessation
- 1974-12-31 YU YU03526/74A patent/YU36535B/xx unknown
-
1975
- 1975-01-02 IT IT47512/75A patent/IT1026224B/it active
- 1975-01-02 GB GB4/75A patent/GB1491091A/en not_active Expired
- 1975-01-03 BE BE152116A patent/BE824067A/xx not_active IP Right Cessation
- 1975-01-03 SE SE7500052A patent/SE422804B/xx not_active IP Right Cessation
- 1975-01-03 SU SU752095620A patent/SU944507A3/ru active
- 1975-01-03 CS CS7571A patent/CS194713B2/cs unknown
- 1975-01-03 HU HU75AO00000398A patent/HU170930B/hu unknown
- 1975-01-04 PL PL1975177151A patent/PL99474B1/pl unknown
-
1979
- 1979-11-21 JP JP15011279A patent/JPS55107599A/ja active Granted
Also Published As
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US3971764A (en) | Process for producing a cationic polyurethane | |
| CA1042133A (en) | Cationic polyurethanes | |
| US4670100A (en) | Aqueous solutions or dispersions of polyisocyanate addition products, a process for their preparation, and their use as coating compounds or as sizing agents for paper | |
| JP3287660B2 (ja) | 紙仕上げ用の無塩素多官能樹脂 | |
| US3988278A (en) | Stable polymer latex and process for making same | |
| KR100296784B1 (ko) | 친수성폴리우레탄 | |
| US3686108A (en) | Light fast quaternized or amine salt polyurethanes from 2-alkyl - 2 - dialkylaminomethyl-1,3-propane diols | |
| GB1564259A (en) | Electrolytestable water-dispersible cationic polyurethane elastomers | |
| CS198254B2 (en) | Method of producing anionic polyurethans | |
| EP1555276B1 (de) | Dispersionen enthaltend Organopolysiloxan-Polyharnstoff-Copoymere | |
| DE3234590A1 (de) | Thermisch reaktives, wasserloesliches urethanprepolymerisat | |
| US6090871A (en) | Paper finishing aid | |
| EP0148970A2 (en) | Stable, aqueous dispersions of polyurethane-ureas and coatings and films prepared therefrom | |
| EP1319032A2 (en) | Low-temperature, heat-activated adhesives with high heat resistance properties | |
| JPS60243163A (ja) | ポリウレタン―尿素水性被覆組成物 | |
| JPS6075699A (ja) | 紙のサイズ方法 | |
| RU2079531C1 (ru) | Водная полиуретановая эмульсия для отделки кожевенного сырья | |
| CA2023840A1 (en) | Aqueous polyurethane dispersions and adhesives based thereon | |
| US5718804A (en) | Process for the production of cellulose-containing sheet-like structures which have been given a dry strength and/or wet strength treatment | |
| US3779994A (en) | Method for preparing polyurethane from polyisocyanate and polyalkanolamine using a blocking acid salt | |
| US3932561A (en) | Adhesives comprising solutions of a mixture of a terpene urethane resin with thermoplastic polyether polyurethanes containing tertiary amine group | |
| DE4419572A1 (de) | Mehrkomponenten-Systeme für die Papierveredelung | |
| US3518113A (en) | Polyurethane latices as paper-making additives | |
| CA2101389A1 (en) | Anionically modified polyurethane ureas having reduced tackiness for the coating of leather | |
| USRE29623E (en) | Polyurethane-ureas based on cis-trans-1,4-diaminocyclohexane |