CA1047692A - Amine-epichlorohydrin polymeric compositions - Google Patents

Amine-epichlorohydrin polymeric compositions

Info

Publication number: CA1047692A
Authority: CA; Canada
Prior art keywords: water; amine; soluble; epichlorohydrin; cationic
Prior art date: 1975-04-14
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

Application number

CA231,200A

Other languages

English (en)

French (fr)

Other versions

CA231200S (en

Inventor

John D. Buckman

Stanley J. Buckman

Gerald D. Mercer

John D. Pera

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Buckman Laboratories International Inc

Original Assignee

Buckman Laboratories International 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

1975-07-10

Publication date

1979-01-30

1975-07-10 Application filed by Buckman Laboratories International Inc filed Critical Buckman Laboratories International Inc

1979-01-30 Application granted granted Critical

1979-01-30 Publication of CA1047692A publication Critical patent/CA1047692A/en

Status Expired legal-status Critical Current

Links

239000000203 mixture Substances 0.000 title claims abstract description 27
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 49
238000000034 method Methods 0.000 claims abstract description 44
125000002091 cationic group Chemical group 0.000 claims abstract description 27
-1 3-chloro-2-hydroxypropyl Chemical group 0.000 claims abstract description 26
241000195493 Cryptophyta Species 0.000 claims abstract description 10
241000233866 Fungi Species 0.000 claims abstract description 9
239000004753 textile Substances 0.000 claims abstract description 9
241000894006 Bacteria Species 0.000 claims abstract description 8
238000004519 manufacturing process Methods 0.000 claims abstract description 7
229920000642 polymer Polymers 0.000 claims description 65
239000000123 paper Substances 0.000 claims description 28
239000002243 precursor Substances 0.000 claims description 21
150000003512 tertiary amines Chemical group 0.000 claims description 21
239000012704 polymeric precursor Substances 0.000 claims description 18
BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 claims description 17
230000014759 maintenance of location Effects 0.000 claims description 17
BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 claims description 14
KWYHDKDOAIKMQN-UHFFFAOYSA-N N,N,N',N'-tetramethylethylenediamine Chemical compound CN(C)CCN(C)C KWYHDKDOAIKMQN-UHFFFAOYSA-N 0.000 claims description 14
125000001931 aliphatic group Chemical group 0.000 claims description 14
239000011087 paperboard Substances 0.000 claims description 14
125000004432 carbon atom Chemical group C* 0.000 claims description 13
229910052799 carbon Inorganic materials 0.000 claims description 11
150000003141 primary amines Chemical class 0.000 claims description 11
239000000460 chlorine Substances 0.000 claims description 10
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 10
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 8
230000001070 adhesive effect Effects 0.000 claims description 8
239000007787 solid Substances 0.000 claims description 8
229910052500 inorganic mineral Inorganic materials 0.000 claims description 7
239000011707 mineral Substances 0.000 claims description 7
239000000975 dye Substances 0.000 claims description 6
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 6
239000000463 material Substances 0.000 claims description 6
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 5
239000002253 acid Substances 0.000 claims description 5
239000000853 adhesive Substances 0.000 claims description 5
125000002723 alicyclic group Chemical group 0.000 claims description 5
125000001309 chloro group Chemical group Cl* 0.000 claims description 5
150000003839 salts Chemical class 0.000 claims description 5
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 4
125000002877 alkyl aryl group Chemical group 0.000 claims description 4
229910021529 ammonia Inorganic materials 0.000 claims description 4
229910052801 chlorine Inorganic materials 0.000 claims description 4
238000004513 sizing Methods 0.000 claims description 4
230000003311 flocculating effect Effects 0.000 claims description 3
125000003118 aryl group Chemical group 0.000 claims description 2
238000005189 flocculation Methods 0.000 claims description 2
230000016615 flocculation Effects 0.000 claims description 2
238000004078 waterproofing Methods 0.000 claims description 2
230000035755 proliferation Effects 0.000 claims 4
101100037762 Caenorhabditis elegans rnh-2 gene Proteins 0.000 claims 3
230000002401 inhibitory effect Effects 0.000 claims 3
125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims 1
239000011203 carbon fibre reinforced carbon Substances 0.000 claims 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 1
239000003295 industrial effluent Substances 0.000 claims 1
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 1
239000010802 sludge Substances 0.000 claims 1
125000004079 stearyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims 1
150000001412 amines Chemical class 0.000 abstract description 10
230000008569 process Effects 0.000 abstract description 8
241000607479 Yersinia pestis Species 0.000 abstract 1
238000000746 purification Methods 0.000 abstract 1
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 42
238000006243 chemical reaction Methods 0.000 description 31
239000000243 solution Substances 0.000 description 19
239000000047 product Substances 0.000 description 12
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 10
150000002500 ions Chemical class 0.000 description 9
239000002904 solvent Substances 0.000 description 9
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 8
229910052757 nitrogen Inorganic materials 0.000 description 8
229920006317 cationic polymer Polymers 0.000 description 7
230000000694 effects Effects 0.000 description 6
238000010438 heat treatment Methods 0.000 description 6
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 5
239000011521 glass Substances 0.000 description 5
235000010755 mineral Nutrition 0.000 description 5
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
239000004927 clay Substances 0.000 description 4
150000001875 compounds Chemical class 0.000 description 4
238000001816 cooling Methods 0.000 description 4
239000004744 fabric Substances 0.000 description 4
239000008394 flocculating agent Substances 0.000 description 4
IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 4
239000000049 pigment Substances 0.000 description 4
238000006116 polymerization reaction Methods 0.000 description 4
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
230000008901 benefit Effects 0.000 description 3
239000004615 ingredient Substances 0.000 description 3
244000005700 microbiome Species 0.000 description 3
239000000178 monomer Substances 0.000 description 3
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
125000004433 nitrogen atom Chemical group N* 0.000 description 3
239000013618 particulate matter Substances 0.000 description 3
239000011541 reaction mixture Substances 0.000 description 3
238000010992 reflux Methods 0.000 description 3
239000002002 slurry Substances 0.000 description 3
GWEVSGVZZGPLCZ-UHFFFAOYSA-N titanium dioxide Inorganic materials O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 3
LTMQZVLXCLQPCT-UHFFFAOYSA-N 1,1,6-trimethyltetralin Chemical compound C1CCC(C)(C)C=2C1=CC(C)=CC=2 LTMQZVLXCLQPCT-UHFFFAOYSA-N 0.000 description 2
YUTYQYJKLOMLLV-UHFFFAOYSA-N 1-[bis(3-chloro-2-hydroxypropyl)amino]-3-chloropropan-2-ol Chemical compound ClCC(O)CN(CC(O)CCl)CC(O)CCl YUTYQYJKLOMLLV-UHFFFAOYSA-N 0.000 description 2
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 2
HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-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
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
241000195649 Chlorella <Chlorellales> Species 0.000 description 2
229920000742 Cotton Polymers 0.000 description 2
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 description 2
241000192608 Phormidium Species 0.000 description 2
WCUXLLCKKVVCTQ-UHFFFAOYSA-M Potassium chloride Chemical compound [Cl-].[K+] WCUXLLCKKVVCTQ-UHFFFAOYSA-M 0.000 description 2
229920002472 Starch Polymers 0.000 description 2
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
239000007983 Tris buffer Substances 0.000 description 2
239000004480 active ingredient Substances 0.000 description 2
238000013019 agitation Methods 0.000 description 2
125000000217 alkyl group Chemical group 0.000 description 2
238000004458 analytical method Methods 0.000 description 2
125000004429 atom Chemical group 0.000 description 2
235000011089 carbon dioxide Nutrition 0.000 description 2
229960004424 carbon dioxide Drugs 0.000 description 2
239000003153 chemical reaction reagent Substances 0.000 description 2
239000003795 chemical substances by application Substances 0.000 description 2
230000001276 controlling effect Effects 0.000 description 2
125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 2
238000004821 distillation Methods 0.000 description 2
239000000835 fiber Substances 0.000 description 2
239000000945 filler Substances 0.000 description 2
239000000706 filtrate Substances 0.000 description 2
239000012530 fluid Substances 0.000 description 2
238000009472 formulation Methods 0.000 description 2
230000006872 improvement Effects 0.000 description 2
230000005764 inhibitory process Effects 0.000 description 2
VEAZEPMQWHPHAG-UHFFFAOYSA-N n,n,n',n'-tetramethylbutane-1,4-diamine Chemical compound CN(C)CCCCN(C)C VEAZEPMQWHPHAG-UHFFFAOYSA-N 0.000 description 2
TXXWBTOATXBWDR-UHFFFAOYSA-N n,n,n',n'-tetramethylhexane-1,6-diamine Chemical compound CN(C)CCCCCCN(C)C TXXWBTOATXBWDR-UHFFFAOYSA-N 0.000 description 2
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 2
239000003960 organic solvent Substances 0.000 description 2
239000002798 polar solvent Substances 0.000 description 2
235000010482 polyoxyethylene sorbitan monooleate Nutrition 0.000 description 2
229920000053 polysorbate 80 Polymers 0.000 description 2
238000002360 preparation method Methods 0.000 description 2
150000003856 quaternary ammonium compounds Chemical class 0.000 description 2
229920005989 resin Polymers 0.000 description 2
239000011347 resin Substances 0.000 description 2
239000012266 salt solution Substances 0.000 description 2
238000000926 separation method Methods 0.000 description 2
239000008107 starch Substances 0.000 description 2
235000019698 starch Nutrition 0.000 description 2
239000000126 substance Substances 0.000 description 2
239000000758 substrate Substances 0.000 description 2
230000009182 swimming Effects 0.000 description 2
YBRBMKDOPFTVDT-UHFFFAOYSA-N tert-butylamine Chemical compound CC(C)(C)N YBRBMKDOPFTVDT-UHFFFAOYSA-N 0.000 description 2
GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 2
LWIHDJKSTIGBAC-UHFFFAOYSA-K tripotassium phosphate Chemical compound [K+].[K+].[K+].[O-]P([O-])([O-])=O LWIHDJKSTIGBAC-UHFFFAOYSA-K 0.000 description 2
239000002699 waste material Substances 0.000 description 2
229920003169 water-soluble polymer Polymers 0.000 description 2
GHPYJLCQYMAXGG-WCCKRBBISA-N (2R)-2-amino-3-(2-boronoethylsulfanyl)propanoic acid hydrochloride Chemical compound Cl.N[C@@H](CSCCB(O)O)C(O)=O GHPYJLCQYMAXGG-WCCKRBBISA-N 0.000 description 1
BMVXCPBXGZKUPN-UHFFFAOYSA-N 1-hexanamine Chemical compound CCCCCCN BMVXCPBXGZKUPN-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
PAWQVTBBRAZDMG-UHFFFAOYSA-N 2-(3-bromo-2-fluorophenyl)acetic acid Chemical compound OC(=O)CC1=CC=CC(Br)=C1F PAWQVTBBRAZDMG-UHFFFAOYSA-N 0.000 description 1
CVCPMANSVIKBFL-UHFFFAOYSA-N 2-(chloromethyl)oxirane;methanamine Chemical compound NC.ClCC1CO1 CVCPMANSVIKBFL-UHFFFAOYSA-N 0.000 description 1
239000005995 Aluminium silicate Substances 0.000 description 1
JODZCFNVBPQMEL-UHFFFAOYSA-N C(CCCCCCCCCCCCCCCCC)N.C(CCC)N Chemical compound C(CCCCCCCCCCCCCCCCC)N.C(CCC)N JODZCFNVBPQMEL-UHFFFAOYSA-N 0.000 description 1
RQLXMLXZEATFIJ-UHFFFAOYSA-N C1(CCCCC1)N.C(C)N Chemical compound C1(CCCCC1)N.C(C)N RQLXMLXZEATFIJ-UHFFFAOYSA-N 0.000 description 1
241000221955 Chaetomium Species 0.000 description 1
241001515917 Chaetomium globosum Species 0.000 description 1
101100328087 Cladosporium cladosporioides cla2 gene Proteins 0.000 description 1
241000518994 Conta Species 0.000 description 1
239000004129 EU approved improving agent Substances 0.000 description 1
241000588914 Enterobacter Species 0.000 description 1
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 1
241000588915 Klebsiella aerogenes Species 0.000 description 1
241001435619 Lile Species 0.000 description 1
241001164593 Merica Species 0.000 description 1
241001465754 Metazoa Species 0.000 description 1
OGBUOSJUUIOFOB-UHFFFAOYSA-N NCCC.C(O)CN Chemical compound NCCC.C(O)CN OGBUOSJUUIOFOB-UHFFFAOYSA-N 0.000 description 1
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
240000000064 Penicillium roqueforti Species 0.000 description 1
235000002233 Penicillium roqueforti Nutrition 0.000 description 1
239000004698 Polyethylene Substances 0.000 description 1
229920002873 Polyethylenimine Polymers 0.000 description 1
229920001131 Pulp (paper) Polymers 0.000 description 1
GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 1
150000007513 acids Chemical class 0.000 description 1
239000000654 additive Substances 0.000 description 1
230000000996 additive effect Effects 0.000 description 1
238000005054 agglomeration Methods 0.000 description 1
230000002776 aggregation Effects 0.000 description 1
150000001298 alcohols Chemical class 0.000 description 1
150000003973 alkyl amines Chemical class 0.000 description 1
235000012211 aluminium silicate Nutrition 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
229910052921 ammonium sulfate Inorganic materials 0.000 description 1
235000011130 ammonium sulphate Nutrition 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
239000007900 aqueous suspension Substances 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
VZYNTPOPCMKJEP-UHFFFAOYSA-N bis(3-chloro-2-hydroxypropyl)-dimethylazanium Chemical compound ClCC(O)C[N+](C)(C)CC(O)CCl VZYNTPOPCMKJEP-UHFFFAOYSA-N 0.000 description 1
239000000872 buffer Substances 0.000 description 1
HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 description 1
230000000711 cancerogenic effect Effects 0.000 description 1
150000001721 carbon Chemical group 0.000 description 1
231100000357 carcinogen Toxicity 0.000 description 1
239000003183 carcinogenic agent Substances 0.000 description 1
239000003054 catalyst Substances 0.000 description 1
239000001913 cellulose Substances 0.000 description 1
229920002678 cellulose Polymers 0.000 description 1
238000002485 combustion reaction Methods 0.000 description 1
238000004132 cross linking Methods 0.000 description 1
WTADDKSUAUBSRI-UHFFFAOYSA-N cyclohexanamine;hexan-1-amine Chemical compound CCCCCCN.NC1CCCCC1 WTADDKSUAUBSRI-UHFFFAOYSA-N 0.000 description 1
230000003413 degradative effect Effects 0.000 description 1
239000008367 deionised water Substances 0.000 description 1
229910021641 deionized water Inorganic materials 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
238000009826 distribution Methods 0.000 description 1
230000008030 elimination Effects 0.000 description 1
238000003379 elimination reaction Methods 0.000 description 1
239000012467 final product Substances 0.000 description 1
238000005187 foaming Methods 0.000 description 1
239000008103 glucose Substances 0.000 description 1
239000011121 hardwood Substances 0.000 description 1
ATADHKWKHYVBTJ-UHFFFAOYSA-N hydron;4-[1-hydroxy-2-(methylamino)ethyl]benzene-1,2-diol;chloride Chemical compound Cl.CNCC(O)C1=CC=C(O)C(O)=C1 ATADHKWKHYVBTJ-UHFFFAOYSA-N 0.000 description 1
125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 description 1
239000012535 impurity Substances 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
239000002655 kraft paper Substances 0.000 description 1
231100000053 low toxicity Toxicity 0.000 description 1
229910052943 magnesium sulfate Inorganic materials 0.000 description 1
235000019341 magnesium sulphate Nutrition 0.000 description 1
AWSBQWZZLBPUQH-UHFFFAOYSA-N mdat Chemical compound C1=C2CC(N)CCC2=CC2=C1OCO2 AWSBQWZZLBPUQH-UHFFFAOYSA-N 0.000 description 1
230000007246 mechanism Effects 0.000 description 1
125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 description 1
230000003641 microbiacidal effect Effects 0.000 description 1
229940124561 microbicide Drugs 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
230000017066 negative regulation of growth Effects 0.000 description 1
239000011368 organic material Substances 0.000 description 1
239000002245 particle Substances 0.000 description 1
CEKCVYXSSQJYCW-UHFFFAOYSA-N phenylmethanamine propan-2-amine Chemical compound C(C1=CC=CC=C1)N.C(C)(C)N CEKCVYXSSQJYCW-UHFFFAOYSA-N 0.000 description 1
229920000573 polyethylene Polymers 0.000 description 1
239000001103 potassium chloride Substances 0.000 description 1
235000011164 potassium chloride Nutrition 0.000 description 1
229910000160 potassium phosphate Inorganic materials 0.000 description 1
235000011009 potassium phosphates Nutrition 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
230000002035 prolonged effect Effects 0.000 description 1
239000000376 reactant Substances 0.000 description 1
238000011084 recovery Methods 0.000 description 1
230000009467 reduction Effects 0.000 description 1
230000001105 regulatory effect Effects 0.000 description 1
230000000717 retained effect Effects 0.000 description 1
NXLOLUFNDSBYTP-UHFFFAOYSA-N retene Chemical compound C1=CC=C2C3=CC=C(C(C)C)C=C3C=CC2=C1C NXLOLUFNDSBYTP-UHFFFAOYSA-N 0.000 description 1
IOVGROKTTNBUGK-SJCJKPOMSA-N ritodrine Chemical compound N([C@@H](C)[C@H](O)C=1C=CC(O)=CC=1)CCC1=CC=C(O)C=C1 IOVGROKTTNBUGK-SJCJKPOMSA-N 0.000 description 1
239000010865 sewage Substances 0.000 description 1
CMXPERZAMAQXSF-UHFFFAOYSA-M sodium;1,4-bis(2-ethylhexoxy)-1,4-dioxobutane-2-sulfonate;1,8-dihydroxyanthracene-9,10-dione Chemical compound [Na+].O=C1C2=CC=CC(O)=C2C(=O)C2=C1C=CC=C2O.CCCCC(CC)COC(=O)CC(S([O-])(=O)=O)C(=O)OCC(CC)CCCC CMXPERZAMAQXSF-UHFFFAOYSA-M 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
239000011550 stock solution Substances 0.000 description 1
239000012209 synthetic fiber Substances 0.000 description 1
229920002994 synthetic fiber Polymers 0.000 description 1
239000003760 tallow Substances 0.000 description 1
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
101150096860 thlA gene Proteins 0.000 description 1
231100000925 very toxic Toxicity 0.000 description 1
239000003643 water by type Substances 0.000 description 1
238000003911 water pollution Methods 0.000 description 1
239000008096 xylene Substances 0.000 description 1
125000005853 β-dimethylaminoethyl group Chemical group 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)
Agricultural Chemicals And Associated Chemicals (AREA)
Polymers With Sulfur, Phosphorus Or Metals In The Main Chain (AREA)
Separation Of Suspended Particles By Flocculating Agents (AREA)

CA231,200A 1975-04-14 1975-07-10 Amine-epichlorohydrin polymeric compositions Expired CA1047692A (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
CA1047692A true CA1047692A (en)	1979-01-30

Family

ID=24269798

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA231,200A Expired CA1047692A (en)	1975-04-14	1975-07-10	Amine-epichlorohydrin polymeric compositions

Country Status (20)

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

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
ATE203289T1 (de) *	1996-10-21	2001-08-15	Werner Briel	Staubbindetuch
RU2266301C1 (ru) *	2004-06-29	2005-12-20	Закрытое акционерное общество "ФИНЭКО"	Способ получения водорастворимого сополимера
ES2358298T3 (es) *	2006-08-15	2011-05-09	Dow Global Technologies Inc.	Procedimiento para preparar haluros de alquilamonio cuaternario.
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/en 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 AR AR259611A patent/AR219477A1/es active
- 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 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/xx 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
SU680655A3 (ru)	1979-08-15
NL173859B (nl)	1983-10-17
NO752546L (de)	1976-10-15
FI62113C (fi)	1982-11-10
JPS51138799A (en)	1976-11-30
BR7602024A (pt)	1977-10-18
AT362230B (de)	1981-04-27
SE7508334L (sv)	1976-10-15
AU8297075A (en)	1977-01-13
ZA754568B (en)	1976-12-29
FI752178A7 (de)	1976-10-15
NL7508495A (nl)	1976-10-18
JPS5410039B2 (de)	1979-05-01
NL173859C (nl)	1984-03-16
NO143353B (no)	1980-10-13
CH642385A5 (en)	1984-04-13
DK321375A (da)	1976-10-15
NO143353C (no)	1981-01-21
SE430509B (sv)	1983-11-21
ES440218A1 (es)	1978-12-01
AR219477A1 (es)	1980-08-29
AU501621B2 (en)	1979-06-28
IE43087L (en)	1976-10-14
IE43087B1 (en)	1980-12-17
IT1053853B (it)	1981-10-10
ATA581375A (de)	1980-09-15
BE832399A (fr)	1975-12-01
IN141819B (de)	1977-04-23
FI62113B (fi)	1982-07-30
GB1507406A (en)	1978-04-12

Publication	Publication Date	Title
US4054542A (en)	1977-10-18	Amine-epichlorohydrin polymeric compositions
US4778813A (en)	1988-10-18	Polymeric quaternary ammonium compounds, their preparation and use
KR840000375B1 (ko)	1984-03-27	4급 암모늄 중합체, 비이온 및(또는) 양이온 비닐-부가 중합체, 및 비이온 및(또는) 양이온 계면활성제의 수용성 혼합물
US3738945A (en)	1973-06-12	Polyquaternary flocculants
US5064909A (en)	1991-11-12	Vinylamine copolymer, flocculating agent and paper strength increasing agent using the same, as well as process for producing the same
CA1098523A (en)	1981-03-31	Cationic polymer flocculant
EP1124862B1 (de)	2004-10-13	Herstellung von wasserlöslichen vernetzten kationischen polymeren
EP1522556B1 (de)	2007-01-24	Dispersion von wasserlöslichem polymer, herstellungsverfahren dafür und verwendungsverfahren dafür
US5938937A (en)	1999-08-17	Hydrophilic dispersion polymers for treating wastewater
EP0071050B1 (de)	1985-05-15	Lineare, basische Polymerisate, Verfahren zu deren Herstellung und deren Verwendung
DE69210914T2 (de)	1997-01-16	Kationisches polymeres Flockungsmittel
GB2160538A (en)	1985-12-24	Ionene-type polymers
EP0172723A2 (de)	1986-02-26	Wasserlösliche Polymere
US3894946A (en)	1975-07-15	Process for treating industrial wastes
NO149391B (no)	1984-01-02	Amfotaer polyelektrolytt, fremstilling av den og anvendelse av den
DE2143355A1 (de)	1972-10-12	Hochmolekulares Irenpfropfpolymer
US4053512A (en)	1977-10-11	Process for preparing poly(allyltrialkylammonium) salt flocculants
DE3237018A1 (de)	1983-06-01	Quaternaere ammonium-pfropfpolymere
DE19607641A1 (de)	1997-09-04	Wasserlösliche Kondensationsprodukte aus Aminogruppen enthaltenden Verbindungen und halogenfreien Vernetzern, Verfahren zu ihrer Herstellung und ihre Verwendung
SU680655A3 (ru)	1979-08-15	Способ получени полимерного электролита
WO2006058732A2 (de)	2006-06-08	Verfahren zur herstellung von papieren mit hohen flächengewichten
JP4064194B2 (ja)	2008-03-19	凝集剤及びその使用方法
US4604213A (en)	1986-08-05	Polymers of 1-acryloyl-4-methyl piperazine, methyl chloride or sulfate quaternary salts as flocculants
US4217215A (en)	1980-08-12	Process for flocculation using crosslinked polysulfonium compounds
KR100606434B1 (ko)	2006-08-01	폐수 처리용 분지형 아크릴아미드 공중합체 분산액의제조방법