CH642385A5 - Process for the preparation of novel cationic, water-soluble, polymeric reaction products - Google Patents

Process for the preparation of novel cationic, water-soluble, polymeric reaction products Download PDF

Info

Publication number: CH642385A5
Authority: CH; Switzerland
Prior art keywords: formula; precursor; tertiary; group; amine
Prior art date: 1975-04-14

Application number

CH476776A

Other languages

German (de)

English (en)

Inventor

John Dustin Buckman

Stanley Joseph Buckman

Gerald Dean Mercer

John Dominic Pera

Original Assignee

Buckman Labor Inc

Priority date (The priority date 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 date listed.)

1975-04-14

Filing date

1976-04-14

Publication date

1984-04-13

1976-04-14 Application filed by Buckman Labor Inc filed Critical Buckman Labor Inc

1984-04-13 Publication of CH642385A5 publication Critical patent/CH642385A5/de

Links

238000000034 method Methods 0.000 title claims description 41
239000007795 chemical reaction product Substances 0.000 title claims description 31
125000002091 cationic group Chemical group 0.000 title claims description 13
230000008569 process Effects 0.000 title claims description 13
238000002360 preparation method Methods 0.000 title claims description 7
229910052757 nitrogen Inorganic materials 0.000 claims description 38
BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 claims description 26
BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 claims description 22
239000012704 polymeric precursor Substances 0.000 claims description 22
150000003512 tertiary amines Chemical class 0.000 claims description 21
239000002243 precursor Substances 0.000 claims description 19
229920000642 polymer Polymers 0.000 claims description 18
239000000123 paper Substances 0.000 claims description 17
150000003141 primary amines Chemical class 0.000 claims description 17
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 15
125000004433 nitrogen atom Chemical group N* 0.000 claims description 14
-1 aliphatic hydrocarbon radical Chemical class 0.000 claims description 13
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims description 8
150000001412 amines Chemical class 0.000 claims description 8
239000011111 cardboard Substances 0.000 claims description 8
150000004985 diamines Chemical group 0.000 claims description 8
KWYHDKDOAIKMQN-UHFFFAOYSA-N N,N,N',N'-tetramethylethylenediamine Chemical compound CN(C)CCN(C)C KWYHDKDOAIKMQN-UHFFFAOYSA-N 0.000 claims description 7
229910021529 ammonia Inorganic materials 0.000 claims description 7
229910052500 inorganic mineral Inorganic materials 0.000 claims description 7
239000011707 mineral Substances 0.000 claims description 7
125000004432 carbon atom Chemical group C* 0.000 claims description 5
239000011087 paperboard Substances 0.000 claims description 5
239000002253 acid Substances 0.000 claims description 4
229910052801 chlorine Inorganic materials 0.000 claims description 4
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 3
239000000460 chlorine Substances 0.000 claims description 3
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
150000002500 ions Chemical class 0.000 claims description 2
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 2
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 claims description 2
125000001302 tertiary amino group Chemical group 0.000 claims description 2
150000003254 radicals Chemical group 0.000 claims 8
101100037762 Caenorhabditis elegans rnh-2 gene Proteins 0.000 claims 4
239000011203 carbon fibre reinforced carbon Substances 0.000 claims 3
CYJBWQFWXJKKMS-UHFFFAOYSA-N 1-amino-3-chloropropan-2-ol Chemical compound NCC(O)CCl CYJBWQFWXJKKMS-UHFFFAOYSA-N 0.000 claims 2
239000004215 Carbon black (E152) Substances 0.000 claims 2
125000003710 aryl alkyl group Chemical group 0.000 claims 2
229930195733 hydrocarbon Natural products 0.000 claims 2
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 2
QGZKDVFQNNGYKY-UHFFFAOYSA-O ammonium group Chemical group [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims 1
150000001450 anions Chemical class 0.000 claims 1
125000003118 aryl group Chemical group 0.000 claims 1
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 39
239000000047 product Substances 0.000 description 33
238000006243 chemical reaction Methods 0.000 description 32
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 30
239000000243 solution Substances 0.000 description 24
GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 12
BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 12
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 11
230000000694 effects Effects 0.000 description 11
230000014759 maintenance of location Effects 0.000 description 11
239000007864 aqueous solution Substances 0.000 description 10
239000002904 solvent Substances 0.000 description 10
239000000126 substance Substances 0.000 description 10
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 9
239000011541 reaction mixture Substances 0.000 description 9
238000007792 addition Methods 0.000 description 7
150000001875 compounds Chemical class 0.000 description 7
238000004519 manufacturing process Methods 0.000 description 7
239000000203 mixture Substances 0.000 description 7
239000007787 solid Substances 0.000 description 7
239000004753 textile Substances 0.000 description 7
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical compound CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 6
239000004408 titanium dioxide Substances 0.000 description 6
QRSIATZYIUKISS-UHFFFAOYSA-N 1-chloro-3-[(3-chloro-2-hydroxypropyl)-methylamino]propan-2-ol Chemical compound ClCC(O)CN(C)CC(O)CCl QRSIATZYIUKISS-UHFFFAOYSA-N 0.000 description 5
241000233866 Fungi Species 0.000 description 5
230000015572 biosynthetic process Effects 0.000 description 5
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238000010438 heat treatment Methods 0.000 description 5
239000000463 material Substances 0.000 description 5
235000010755 mineral Nutrition 0.000 description 5
238000006116 polymerization reaction Methods 0.000 description 5
QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 5
241000195493 Cryptophyta Species 0.000 description 4
QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 4
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
239000000853 adhesive Substances 0.000 description 4
230000001070 adhesive effect Effects 0.000 description 4
WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 description 4
125000001309 chloro group Chemical group Cl* 0.000 description 4
PAFZNILMFXTMIY-UHFFFAOYSA-N cyclohexylamine Chemical compound NC1CCCCC1 PAFZNILMFXTMIY-UHFFFAOYSA-N 0.000 description 4
238000004821 distillation Methods 0.000 description 4
239000000835 fiber Substances 0.000 description 4
239000011521 glass Substances 0.000 description 4
230000005764 inhibitory process Effects 0.000 description 4
239000000178 monomer Substances 0.000 description 4
239000003960 organic solvent Substances 0.000 description 4
239000000049 pigment Substances 0.000 description 4
239000012266 salt solution Substances 0.000 description 4
239000002002 slurry Substances 0.000 description 4
GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 4
241000894006 Bacteria Species 0.000 description 3
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
229920002873 Polyethylenimine Polymers 0.000 description 3
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
238000004458 analytical method Methods 0.000 description 3
239000003795 chemical substances by application Substances 0.000 description 3
238000001816 cooling Methods 0.000 description 3
239000000975 dye Substances 0.000 description 3
238000005189 flocculation Methods 0.000 description 3
230000016615 flocculation Effects 0.000 description 3
244000005700 microbiome Species 0.000 description 3
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 3
239000002798 polar solvent Substances 0.000 description 3
239000000376 reactant Substances 0.000 description 3
150000003839 salts Chemical class 0.000 description 3
238000003756 stirring Methods 0.000 description 3
239000000758 substrate Substances 0.000 description 3
BMVXCPBXGZKUPN-UHFFFAOYSA-N 1-hexanamine Chemical compound CCCCCCN BMVXCPBXGZKUPN-UHFFFAOYSA-N 0.000 description 2
QIJIUJYANDSEKG-UHFFFAOYSA-N 2,4,4-trimethylpentan-2-amine Chemical compound CC(C)(C)CC(C)(C)N QIJIUJYANDSEKG-UHFFFAOYSA-N 0.000 description 2
CVCPMANSVIKBFL-UHFFFAOYSA-N 2-(chloromethyl)oxirane;methanamine Chemical compound NC.ClCC1CO1 CVCPMANSVIKBFL-UHFFFAOYSA-N 0.000 description 2
KDSNLYIMUZNERS-UHFFFAOYSA-N 2-methylpropanamine Chemical compound CC(C)CN KDSNLYIMUZNERS-UHFFFAOYSA-N 0.000 description 2
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
241000195652 Auxenochlorella pyrenoidosa Species 0.000 description 2
CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
241001515917 Chaetomium globosum Species 0.000 description 2
235000007091 Chlorella pyrenoidosa Nutrition 0.000 description 2
229920000742 Cotton Polymers 0.000 description 2
ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 2
PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 2
ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 description 2
WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 2
241000588915 Klebsiella aerogenes Species 0.000 description 2
PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
REYJJPSVUYRZGE-UHFFFAOYSA-N Octadecylamine Chemical compound CCCCCCCCCCCCCCCCCCN REYJJPSVUYRZGE-UHFFFAOYSA-N 0.000 description 2
241000601649 Phormidium inundatum Species 0.000 description 2
229920001131 Pulp (paper) Polymers 0.000 description 2
229920002472 Starch Polymers 0.000 description 2
239000004480 active ingredient Substances 0.000 description 2
238000004026 adhesive bonding Methods 0.000 description 2
150000003973 alkyl amines Chemical class 0.000 description 2
125000000217 alkyl group Chemical group 0.000 description 2
PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 2
HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 description 2
235000011089 carbon dioxide Nutrition 0.000 description 2
230000015556 catabolic process Effects 0.000 description 2
229920006317 cationic polymer Polymers 0.000 description 2
239000004927 clay Substances 0.000 description 2
239000000498 cooling water Substances 0.000 description 2
238000006731 degradation reaction Methods 0.000 description 2
239000008367 deionised water Substances 0.000 description 2
229910021641 deionized water Inorganic materials 0.000 description 2
125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 2
239000000945 filler Substances 0.000 description 2
239000000706 filtrate Substances 0.000 description 2
238000001914 filtration Methods 0.000 description 2
238000009472 formulation Methods 0.000 description 2
239000008103 glucose Substances 0.000 description 2
239000008235 industrial water Substances 0.000 description 2
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
239000007788 liquid Substances 0.000 description 2
VGIVLIHKENZQHQ-UHFFFAOYSA-N n,n,n',n'-tetramethylmethanediamine Chemical compound CN(C)CN(C)C VGIVLIHKENZQHQ-UHFFFAOYSA-N 0.000 description 2
IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
239000002245 particle Substances 0.000 description 2
239000011236 particulate material Substances 0.000 description 2
235000021395 porridge Nutrition 0.000 description 2
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
150000003856 quaternary ammonium compounds Chemical class 0.000 description 2
238000010992 reflux Methods 0.000 description 2
239000011347 resin Substances 0.000 description 2
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125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
238000004065 wastewater treatment Methods 0.000 description 2
VBCJJAZGEJSVTL-UHFFFAOYSA-N (Z)-18-methylnonadec-9-en-1-amine Chemical compound CC(CCCCCCCC=C/CCCCCCCCN)C VBCJJAZGEJSVTL-UHFFFAOYSA-N 0.000 description 1
ZORQXIQZAOLNGE-UHFFFAOYSA-N 1,1-difluorocyclohexane Chemical class FC1(F)CCCCC1 ZORQXIQZAOLNGE-UHFFFAOYSA-N 0.000 description 1
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WPWHSFAFEBZWBB-UHFFFAOYSA-N 1-butyl radical Chemical compound [CH2]CCC WPWHSFAFEBZWBB-UHFFFAOYSA-N 0.000 description 1
FXPAWSQSXNAZPR-UHFFFAOYSA-N 1-chloro-3-(methylamino)propan-2-ol Chemical compound CNCC(O)CCl FXPAWSQSXNAZPR-UHFFFAOYSA-N 0.000 description 1
AXFVIWBTKYFOCY-UHFFFAOYSA-N 1-n,1-n,3-n,3-n-tetramethylbutane-1,3-diamine Chemical compound CN(C)C(C)CCN(C)C AXFVIWBTKYFOCY-UHFFFAOYSA-N 0.000 description 1
RNFJDJUURJAICM-UHFFFAOYSA-N 2,2,4,4,6,6-hexaphenoxy-1,3,5-triaza-2$l^{5},4$l^{5},6$l^{5}-triphosphacyclohexa-1,3,5-triene Chemical compound N=1P(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP=1(OC=1C=CC=CC=1)OC1=CC=CC=C1 RNFJDJUURJAICM-UHFFFAOYSA-N 0.000 description 1
GTEXIOINCJRBIO-UHFFFAOYSA-N 2-[2-(dimethylamino)ethoxy]-n,n-dimethylethanamine Chemical compound CN(C)CCOCCN(C)C GTEXIOINCJRBIO-UHFFFAOYSA-N 0.000 description 1
239000005995 Aluminium silicate Substances 0.000 description 1
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 1
NOWKCMXCCJGMRR-UHFFFAOYSA-N Aziridine Chemical compound C1CN1 NOWKCMXCCJGMRR-UHFFFAOYSA-N 0.000 description 1
241001465754 Metazoa Species 0.000 description 1
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
241000228143 Penicillium Species 0.000 description 1
241000218657 Picea Species 0.000 description 1
239000004698 Polyethylene Substances 0.000 description 1
WDVSHHCDHLJJJR-UHFFFAOYSA-N Proflavine Chemical compound C1=CC(N)=CC2=NC3=CC(N)=CC=C3C=C21 WDVSHHCDHLJJJR-UHFFFAOYSA-N 0.000 description 1
239000007983 Tris buffer Substances 0.000 description 1
OCBFFGCSTGGPSQ-UHFFFAOYSA-N [CH2]CC Chemical compound [CH2]CC OCBFFGCSTGGPSQ-UHFFFAOYSA-N 0.000 description 1
150000007513 acids Chemical class 0.000 description 1
239000013543 active substance Substances 0.000 description 1
238000005054 agglomeration Methods 0.000 description 1
230000002776 aggregation Effects 0.000 description 1
230000001476 alcoholic effect Effects 0.000 description 1
150000001298 alcohols Chemical class 0.000 description 1
235000012211 aluminium silicate Nutrition 0.000 description 1
125000003277 amino group Chemical group 0.000 description 1
235000019270 ammonium chloride Nutrition 0.000 description 1
BFNBIHQBYMNNAN-UHFFFAOYSA-N ammonium sulfate Chemical compound N.N.OS(O)(=O)=O BFNBIHQBYMNNAN-UHFFFAOYSA-N 0.000 description 1
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235000011130 ammonium sulphate Nutrition 0.000 description 1
239000007900 aqueous suspension Substances 0.000 description 1
238000004380 ashing Methods 0.000 description 1
ORZPVBXQPXMSGE-UHFFFAOYSA-M azanium potassium hydrogen phosphate nitric acid Chemical compound P(=O)([O-])([O-])O.[N+](=O)(O)[O-].[NH4+].[K+] ORZPVBXQPXMSGE-UHFFFAOYSA-M 0.000 description 1
238000010533 azeotropic distillation Methods 0.000 description 1
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
238000009835 boiling Methods 0.000 description 1
239000000337 buffer salt Substances 0.000 description 1
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
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XENVCRGQTABGKY-ZHACJKMWSA-N chlorohydrin Chemical compound CC#CC#CC#CC#C\C=C\C(Cl)CO XENVCRGQTABGKY-ZHACJKMWSA-N 0.000 description 1
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238000004132 cross linking Methods 0.000 description 1
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125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
229940111685 dibasic potassium phosphate Drugs 0.000 description 1
229940061607 dibasic sodium phosphate Drugs 0.000 description 1
238000007865 diluting Methods 0.000 description 1
NAPSCFZYZVSQHF-UHFFFAOYSA-N dimantine Chemical compound CCCCCCCCCCCCCCCCCCN(C)C NAPSCFZYZVSQHF-UHFFFAOYSA-N 0.000 description 1
229950010007 dimantine Drugs 0.000 description 1
XXBDWLFCJWSEKW-UHFFFAOYSA-N dimethylbenzylamine Chemical compound CN(C)CC1=CC=CC=C1 XXBDWLFCJWSEKW-UHFFFAOYSA-N 0.000 description 1
ZPWVASYFFYYZEW-UHFFFAOYSA-L dipotassium hydrogen phosphate Chemical compound [K+].[K+].OP([O-])([O-])=O ZPWVASYFFYYZEW-UHFFFAOYSA-L 0.000 description 1
BNIILDVGGAEEIG-UHFFFAOYSA-L disodium hydrogen phosphate Chemical compound [Na+].[Na+].OP([O-])([O-])=O BNIILDVGGAEEIG-UHFFFAOYSA-L 0.000 description 1
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235000019800 disodium phosphate Nutrition 0.000 description 1
238000009826 distribution Methods 0.000 description 1
238000004043 dyeing Methods 0.000 description 1
229940092559 enterobacter aerogenes Drugs 0.000 description 1
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 1
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JJWLVOIRVHMVIS-UHFFFAOYSA-N isopropylamine Chemical compound CC(C)N JJWLVOIRVHMVIS-UHFFFAOYSA-N 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
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238000002386 leaching Methods 0.000 description 1
230000005087 leaf formation Effects 0.000 description 1
238000011068 loading method Methods 0.000 description 1
231100000053 low toxicity Toxicity 0.000 description 1
229910052943 magnesium sulfate Inorganic materials 0.000 description 1
CSNNHWWHGAXBCP-UHFFFAOYSA-L magnesium sulphate Substances [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 1
235000019341 magnesium sulphate Nutrition 0.000 description 1
AAIXGPLMFDSDPW-UHFFFAOYSA-K magnesium;potassium;chloride;sulfate Chemical compound [Mg+2].[K]Cl.[O-]S([O-])(=O)=O AAIXGPLMFDSDPW-UHFFFAOYSA-K 0.000 description 1
230000007246 mechanism Effects 0.000 description 1
230000003641 microbiacidal effect Effects 0.000 description 1
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230000002906 microbiologic effect Effects 0.000 description 1
238000002156 mixing Methods 0.000 description 1
TXXWBTOATXBWDR-UHFFFAOYSA-N n,n,n',n'-tetramethylhexane-1,6-diamine Chemical compound CN(C)CCCCCCN(C)C TXXWBTOATXBWDR-UHFFFAOYSA-N 0.000 description 1
DMQSHEKGGUOYJS-UHFFFAOYSA-N n,n,n',n'-tetramethylpropane-1,3-diamine Chemical compound CN(C)CCCN(C)C DMQSHEKGGUOYJS-UHFFFAOYSA-N 0.000 description 1
YWWNNLPSZSEZNZ-UHFFFAOYSA-N n,n-dimethyldecan-1-amine Chemical compound CCCCCCCCCCN(C)C YWWNNLPSZSEZNZ-UHFFFAOYSA-N 0.000 description 1
SFBHPFQSSDCYSL-UHFFFAOYSA-N n,n-dimethyltetradecan-1-amine Chemical compound CCCCCCCCCCCCCCN(C)C SFBHPFQSSDCYSL-UHFFFAOYSA-N 0.000 description 1
125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
ATBNMWWDBWBAHM-UHFFFAOYSA-N n-decyl-n-methyldecan-1-amine Chemical compound CCCCCCCCCCN(C)CCCCCCCCCC ATBNMWWDBWBAHM-UHFFFAOYSA-N 0.000 description 1
VFLWKHBYVIUAMP-UHFFFAOYSA-N n-methyl-n-octadecyloctadecan-1-amine Chemical compound CCCCCCCCCCCCCCCCCCN(C)CCCCCCCCCCCCCCCCCC VFLWKHBYVIUAMP-UHFFFAOYSA-N 0.000 description 1
229910052759 nickel Inorganic materials 0.000 description 1
229920000573 polyethylene Polymers 0.000 description 1
235000010482 polyoxyethylene sorbitan monooleate Nutrition 0.000 description 1
229920000053 polysorbate 80 Polymers 0.000 description 1
230000002265 prevention Effects 0.000 description 1
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
AOHJOMMDDJHIJH-UHFFFAOYSA-N propylenediamine Chemical compound CC(N)CN AOHJOMMDDJHIJH-UHFFFAOYSA-N 0.000 description 1
238000000746 purification Methods 0.000 description 1
238000005956 quaternization reaction Methods 0.000 description 1
238000011084 recovery Methods 0.000 description 1
230000001105 regulatory effect Effects 0.000 description 1
230000000717 retained effect Effects 0.000 description 1
239000005060 rubber Substances 0.000 description 1
BHRZNVHARXXAHW-UHFFFAOYSA-N sec-butylamine Chemical compound CCC(C)N BHRZNVHARXXAHW-UHFFFAOYSA-N 0.000 description 1
150000003335 secondary amines Chemical class 0.000 description 1
238000000926 separation method Methods 0.000 description 1
238000004904 shortening Methods 0.000 description 1
238000004513 sizing Methods 0.000 description 1
239000011122 softwood Substances 0.000 description 1
230000003595 spectral effect Effects 0.000 description 1
238000010183 spectrum analysis Methods 0.000 description 1
230000001954 sterilising effect Effects 0.000 description 1
238000004659 sterilization and disinfection Methods 0.000 description 1
230000001360 synchronised effect Effects 0.000 description 1
229920002994 synthetic fiber Polymers 0.000 description 1
239000004758 synthetic textile Substances 0.000 description 1
239000003760 tallow Substances 0.000 description 1
YBRBMKDOPFTVDT-UHFFFAOYSA-N tert-butylamine Chemical compound CC(C)(C)N YBRBMKDOPFTVDT-UHFFFAOYSA-N 0.000 description 1
231100000331 toxic Toxicity 0.000 description 1
230000002588 toxic effect Effects 0.000 description 1
238000005292 vacuum distillation Methods 0.000 description 1
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
229920002554 vinyl polymer Polymers 0.000 description 1
239000002351 wastewater Substances 0.000 description 1
238000003911 water pollution Methods 0.000 description 1
239000004520 water soluble gel Substances 0.000 description 1
229920003169 water-soluble polymer Polymers 0.000 description 1
238000004078 waterproofing Methods 0.000 description 1
239000002023 wood Substances 0.000 description 1
239000008096 xylene Substances 0.000 description 1

Classifications

- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N33/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic nitrogen compounds
- A01N33/02—Amines; Quaternary ammonium compounds
- A01N33/12—Quaternary ammonium compounds
- C—CHEMISTRY; METALLURGY
- C02—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
- C02F—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
- C02F1/00—Treatment of water, waste water, or sewage
- C02F1/50—Treatment of water, waste water, or sewage by addition or application of a germicide or by oligodynamic treatment
- C—CHEMISTRY; METALLURGY
- C02—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
- C02F—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
- C02F1/00—Treatment of water, waste water, or sewage
- C02F1/52—Treatment of water, waste water, or sewage by flocculation or precipitation of suspended impurities
- C02F1/54—Treatment of water, waste water, or sewage by flocculation or precipitation of suspended impurities using organic material
- 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
- C08G73/00—Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00
- C08G73/02—Polyamines
- C08G73/0206—Polyalkylene(poly)amines
- C08G73/0213—Preparatory process
- C08G73/0226—Quaternisation of polyalkylene(poly)amines
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
- D06M15/00—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment
- D06M15/19—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment with synthetic macromolecular compounds
- D06M15/37—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
- D06M15/55—Epoxy resins
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
- D06M16/00—Biochemical treatment of fibres, threads, yarns, fabrics, or fibrous goods made from such materials, e.g. enzymatic
- 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

Landscapes

Chemical & Material Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
Engineering & Computer Science (AREA)
Chemical Kinetics & Catalysis (AREA)
Organic Chemistry (AREA)
Textile Engineering (AREA)
Hydrology & Water Resources (AREA)
Environmental & Geological Engineering (AREA)
Health & Medical Sciences (AREA)
Water Supply & Treatment (AREA)
Pest Control & Pesticides (AREA)
General Health & Medical Sciences (AREA)
General Chemical & Material Sciences (AREA)
Microbiology (AREA)
Polymers & Plastics (AREA)
Agronomy & Crop Science (AREA)
Medicinal Chemistry (AREA)
Plant Pathology (AREA)
Dentistry (AREA)
Biochemistry (AREA)
Wood Science & Technology (AREA)
Zoology (AREA)
Environmental Sciences (AREA)
Macromolecular Compounds Obtained By Forming Nitrogen-Containing Linkages In General (AREA)
Paper (AREA)
Separation Of Suspended Particles By Flocculating Agents (AREA)
Agricultural Chemicals And Associated Chemicals (AREA)
Polymers With Sulfur, Phosphorus Or Metals In The Main Chain (AREA)

CH476776A 1975-04-14 1976-04-14 Process for the preparation of novel cationic, water-soluble, polymeric reaction products CH642385A5 (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
US56806675A	1975-04-14	1975-04-14

Publications (1)

Publication Number	Publication Date
CH642385A5 true CH642385A5 (en)	1984-04-13

Family

ID=24269798

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CH476776A CH642385A5 (en)	1975-04-14	1976-04-14	Process for the preparation of novel cationic, water-soluble, polymeric reaction products

Country Status (20)

Country	Link
JP (1)	JPS51138799A (fr)
AR (1)	AR219477A1 (fr)
AT (1)	AT362230B (fr)
AU (1)	AU501621B2 (fr)
BE (1)	BE832399A (fr)
BR (1)	BR7602024A (fr)
CA (1)	CA1047692A (fr)
CH (1)	CH642385A5 (fr)
DK (1)	DK321375A (fr)
ES (1)	ES440218A1 (fr)
FI (1)	FI62113C (fr)
GB (1)	GB1507406A (fr)
IE (1)	IE43087B1 (fr)
IN (1)	IN141819B (fr)
IT (1)	IT1053853B (fr)
NL (1)	NL173859C (fr)
NO (1)	NO143353C (fr)
SE (1)	SE430509B (fr)
SU (1)	SU680655A3 (fr)
ZA (1)	ZA754568B (fr)

Families Citing this family (6)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4046648A (en) *	1975-09-29	1977-09-06	E. I. Du Pont De Nemours And Company	Polyamine additives in alkaline zinc electroplating
JPH04346903A (ja) *	1991-05-24	1992-12-02	Mitsubishi Kasei Polytec Co	放線菌による病害を防除する農業用組成物
DK0837176T3 (da) *	1996-10-21	2001-09-24	Werner Briel	Støveklud
RU2266301C1 (ru) *	2004-06-29	2005-12-20	Закрытое акционерное общество "ФИНЭКО"	Способ получения водорастворимого сополимера
CA2660131A1 (fr) *	2006-08-15	2008-02-21	Dow Global Technologies Inc.	Procede de preparation d'halogenures d'alkyle ammonium quaternaire
JP2019056050A (ja) *	2017-09-20	2019-04-11	ソマール株式会社	カチオン性填料処理剤

1975
- 1975-07-07 IN IN1324/CAL/75A patent/IN141819B/en unknown
- 1975-07-10 CA CA231,200A patent/CA1047692A/fr not_active Expired
- 1975-07-11 AU AU82970/75A patent/AU501621B2/en not_active Expired
- 1975-07-15 DK DK321375A patent/DK321375A/da not_active Application Discontinuation
- 1975-07-16 NL NLAANVRAGE7508495,A patent/NL173859C/xx not_active IP Right Cessation
- 1975-07-16 ZA ZA00754568A patent/ZA754568B/xx unknown
- 1975-07-16 AR AR259611A patent/AR219477A1/es active
- 1975-07-16 NO NO752546A patent/NO143353C/no unknown
- 1975-07-22 SE SE7508334A patent/SE430509B/xx not_active IP Right Cessation
- 1975-07-28 AT AT581375A patent/AT362230B/de not_active IP Right Cessation
- 1975-07-30 FI FI752178A patent/FI62113C/fi not_active IP Right Cessation
- 1975-08-13 ES ES440218A patent/ES440218A1/es not_active Expired
- 1975-08-13 BE BE159175A patent/BE832399A/fr not_active IP Right Cessation
- 1975-09-09 SU SU752170751A patent/SU680655A3/ru active
1976
- 1976-02-13 IT IT48095/76A patent/IT1053853B/it active
- 1976-03-22 GB GB11501/76A patent/GB1507406A/en not_active Expired
- 1976-04-01 BR BR7602024A patent/BR7602024A/pt unknown
- 1976-04-12 IE IE767/76A patent/IE43087B1/en unknown
- 1976-04-13 JP JP51041762A patent/JPS51138799A/ja active Granted
- 1976-04-14 CH CH476776A patent/CH642385A5/de not_active IP Right Cessation

Also Published As

Publication number	Publication date
ES440218A1 (es)	1978-12-01
AU501621B2 (en)	1979-06-28
NO143353B (no)	1980-10-13
NO752546L (fr)	1976-10-15
DK321375A (da)	1976-10-15
IT1053853B (it)	1981-10-10
BR7602024A (pt)	1977-10-18
FI62113C (fi)	1982-11-10
SE7508334L (sv)	1976-10-15
BE832399A (fr)	1975-12-01
ZA754568B (en)	1976-12-29
JPS51138799A (en)	1976-11-30
SU680655A3 (ru)	1979-08-15
NL7508495A (nl)	1976-10-18
IE43087B1 (en)	1980-12-17
IE43087L (en)	1976-10-14
AU8297075A (en)	1977-01-13
CA1047692A (fr)	1979-01-30
FI62113B (fi)	1982-07-30
AT362230B (de)	1981-04-27
JPS5410039B2 (fr)	1979-05-01
FI752178A7 (fr)	1976-10-15
IN141819B (fr)	1977-04-23
NL173859C (nl)	1984-03-16
ATA581375A (de)	1980-09-15
NO143353C (no)	1981-01-21
NL173859B (nl)	1983-10-17
SE430509B (sv)	1983-11-21
AR219477A1 (es)	1980-08-29
GB1507406A (en)	1978-04-12

Legal Events

Date	Code	Title	Description
1995-12-15	PL	Patent ceased

Publication	Publication Date	Title
DE2616220C2 (de)	1984-11-15	Kationische wasserlösliche Amin- Epichlorhydrin-Polykondensate, Verfahren zu deren Herstellung und deren Verwendung
DE3027126C2 (fr)	1991-03-28
EP0071050B1 (fr)	1985-05-15	Des polymères linéaires, basiques, procédé pour leur préparation et leur utilisation
DE3423703C2 (de)	1995-05-18	Polymere, quartäre Ammoniumverbindungen und deren Verwendung
EP0002474B2 (fr)	1987-08-19	Polyamines contenant des groupes amides et leur utilisation dans la fabrication du papier
DE3822490A1 (de)	1990-01-04	Waessrige loesungen von polyamidoamin-epichlorhyrin-harzen, verfahren zu ihrer herstellung und ihre verwendung
CH616170A5 (en)	1980-03-14	Process for the preparation of nitrogen-containing condensation products
DE2502914A1 (de)	1975-07-31	Funktionelle ionische zusammensetzungen und ihre verwendung
DE3128478A1 (de)	1983-02-03	Verfahren zur herstellung von linearen, basischen polymerisaten
DE2835876A1 (de)	1979-03-08	Kationisches polymeres ausflockungsmittel
EP0025142B1 (fr)	1984-08-08	Composés d'ammonium polyquaternaires, leur préparation, leur utilisation dans la fabrication du papier et agents de traitement du papier les contenant
DE1802435A1 (de)	1970-05-14	Verfahren zur Herstellung von Hilfsmitteln fuer die Papierfabrikation
DE1176362B (de)	1964-08-20	Verfahren zur Herstellung von Polyaddukten
EP0061173B1 (fr)	1984-07-25	Procédé de coloration du papier
DE3486218T2 (de)	1994-04-14	Mittel zur Entwässerung einer Pulpe.
DE2544948C3 (de)	1978-11-16	Verfahren zur Herstellung von kationischen Leimungsmitteln für Papier
EP0000714B1 (fr)	1982-03-31	Agent améliorant la rétention, la séparation de l'eau et la préparation, en particulier pour la fabrication du papier
EP0005241A1 (fr)	1979-11-14	Polyalcoylènepolyamines contenant des groupements dialcoylammonium quaternaires, leur procédé de préparation et leur utilisation comme adjuvant dans la fabrication du papier
CH642385A5 (en)	1984-04-13	Process for the preparation of novel cationic, water-soluble, polymeric reaction products
CH663792A5 (de)	1988-01-15	Verfahren zur herstellung eines wasserloeslichen polyamidoaminpolyamins, dessen erzeugnis und verwendung desselben zur herstellung eines cellulosefaserproduktes.
EP0031899B1 (fr)	1984-06-06	Produits de réaction auto-réticulables et solubles dans l'eau, procédé de préparation de liants à partir de ceux-ci, et leur utilisation pour l'amélioration de la résistance à l'état humide du papier
EP0131200B1 (fr)	1991-04-24	Produits réactionnels solubles dans l'eau, qui sont essentiellement exempts de liaisons d'ester, à partir d'épihalohydrine et de polyamidoamines basiques qui sont solubles dans l'eau, procédé pour leur préparation et leur utilisation
EP0129689A2 (fr)	1985-01-02	Copolymères et leur application comme agents adhésifs
DE1770150A1 (de)	1971-09-23	Nassfestigkeitsharz auf Polyacrylamidbasis und damit hergestelltes Papier
EP0512423A2 (fr)	1992-11-11	Solutions aqueuses de résines polyamidoamine cationiques