CA2021984A1 - Methode de preparation de copolymeres a base d'acrylamide et de chlorure de diallyldimethylammonium - Google Patents

Methode de preparation de copolymeres a base d'acrylamide et de chlorure de diallyldimethylammonium

Info

Publication number: CA2021984A1
Authority: CA; Canada
Prior art keywords: emulsion; process according; ammonium chloride; dimethyl ammonium; oil
Prior art date: 1990-05-31
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.): Abandoned

Application number

CA 2021984

Other languages

English (en)

Inventor

Fu Chen

Edward J. Connors

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.)

Veolia WTS USA Inc

Original Assignee

Betz Laboratories 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.)

1990-05-31

Filing date

1990-07-26

Publication date

1991-12-01

1990-07-26 Application filed by Betz Laboratories Inc filed Critical Betz Laboratories Inc

1991-12-01 Publication of CA2021984A1 publication Critical patent/CA2021984A1/fr

Status Abandoned legal-status Critical Current

Links

238000000034 method Methods 0.000 title claims abstract description 37
229920001577 copolymer Polymers 0.000 title claims abstract description 24
HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 title claims abstract description 17
239000000839 emulsion Substances 0.000 claims abstract description 39
WYGWHHGCAGTUCH-UHFFFAOYSA-N 2-[(2-cyano-4-methylpentan-2-yl)diazenyl]-2,4-dimethylpentanenitrile Chemical compound CC(C)CC(C)(C#N)N=NC(C)(C#N)CC(C)C WYGWHHGCAGTUCH-UHFFFAOYSA-N 0.000 claims abstract description 8
NJSSICCENMLTKO-HRCBOCMUSA-N [(1r,2s,4r,5r)-3-hydroxy-4-(4-methylphenyl)sulfonyloxy-6,8-dioxabicyclo[3.2.1]octan-2-yl] 4-methylbenzenesulfonate Chemical compound C1=CC(C)=CC=C1S(=O)(=O)O[C@H]1C(O)[C@@H](OS(=O)(=O)C=2C=CC(C)=CC=2)[C@@H]2OC[C@H]1O2 NJSSICCENMLTKO-HRCBOCMUSA-N 0.000 claims abstract description 7
238000004519 manufacturing process Methods 0.000 claims abstract description 5
229940117913 acrylamide Drugs 0.000 claims description 18
239000000178 monomer Substances 0.000 claims description 17
239000012071 phase Substances 0.000 claims description 15
239000008346 aqueous phase Substances 0.000 claims description 14
238000006116 polymerization reaction Methods 0.000 claims description 12
238000006243 chemical reaction Methods 0.000 claims description 10
239000003995 emulsifying agent Substances 0.000 claims description 9
239000007762 w/o emulsion Substances 0.000 claims description 6
238000002156 mixing Methods 0.000 claims description 2
230000000379 polymerizing effect Effects 0.000 claims 2
239000012736 aqueous medium Substances 0.000 claims 1
239000013522 chelant Substances 0.000 claims 1
239000003999 initiator Substances 0.000 abstract description 24
239000003921 oil Substances 0.000 description 29
GQOKIYDTHHZSCJ-UHFFFAOYSA-M dimethyl-bis(prop-2-enyl)azanium;chloride Chemical compound [Cl-].C=CC[N+](C)(C)CC=C GQOKIYDTHHZSCJ-UHFFFAOYSA-M 0.000 description 22
229920000642 polymer Polymers 0.000 description 19
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 16
239000000499 gel Substances 0.000 description 15
239000000243 solution Substances 0.000 description 14
OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical group N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 description 11
LXEKPEMOWBOYRF-UHFFFAOYSA-N [2-[(1-azaniumyl-1-imino-2-methylpropan-2-yl)diazenyl]-2-methylpropanimidoyl]azanium;dichloride Chemical compound Cl.Cl.NC(=N)C(C)(C)N=NC(C)(C)C(N)=N LXEKPEMOWBOYRF-UHFFFAOYSA-N 0.000 description 11
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 10
238000012360 testing method Methods 0.000 description 10
230000000052 comparative effect Effects 0.000 description 8
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 7
239000010802 sludge Substances 0.000 description 7
239000004094 surface-active agent Substances 0.000 description 7
KCXVZYZYPLLWCC-UHFFFAOYSA-N EDTA Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(O)=O)CC(O)=O KCXVZYZYPLLWCC-UHFFFAOYSA-N 0.000 description 6
NEHMKBQYUWJMIP-UHFFFAOYSA-N chloromethane Chemical compound ClC NEHMKBQYUWJMIP-UHFFFAOYSA-N 0.000 description 6
239000007787 solid Substances 0.000 description 6
OZAIFHULBGXAKX-VAWYXSNFSA-N AIBN Substances N#CC(C)(C)\N=N\C(C)(C)C#N OZAIFHULBGXAKX-VAWYXSNFSA-N 0.000 description 5
150000003839 salts Chemical class 0.000 description 5
HRZFUMHJMZEROT-UHFFFAOYSA-L sodium disulfite Chemical compound [Na+].[Na+].[O-]S(=O)S([O-])(=O)=O HRZFUMHJMZEROT-UHFFFAOYSA-L 0.000 description 5
229940001584 sodium metabisulfite Drugs 0.000 description 5
235000010262 sodium metabisulphite Nutrition 0.000 description 5
239000000203 mixture Substances 0.000 description 4
ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid group Chemical group C(CCCCCCC\C=C/CCCCCCCC)(=O)O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 4
239000011780 sodium chloride Substances 0.000 description 4
239000001593 sorbitan monooleate Substances 0.000 description 4
229940035049 sorbitan monooleate Drugs 0.000 description 4
235000011069 sorbitan monooleate Nutrition 0.000 description 4
238000003756 stirring Methods 0.000 description 4
CIHOLLKRGTVIJN-UHFFFAOYSA-N tert‐butyl hydroperoxide Chemical compound CC(C)(C)OO CIHOLLKRGTVIJN-UHFFFAOYSA-N 0.000 description 4
238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 3
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
239000004215 Carbon black (E152) Substances 0.000 description 3
239000004908 Emulsion polymer Substances 0.000 description 3
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
WYGWHHGCAGTUCH-ISLYRVAYSA-N V-65 Substances CC(C)CC(C)(C#N)\N=N\C(C)(C#N)CC(C)C WYGWHHGCAGTUCH-ISLYRVAYSA-N 0.000 description 3
239000007864 aqueous solution Substances 0.000 description 3
229910001873 dinitrogen Inorganic materials 0.000 description 3
239000000706 filtrate Substances 0.000 description 3
238000001914 filtration Methods 0.000 description 3
239000011521 glass Substances 0.000 description 3
229930195733 hydrocarbon Natural products 0.000 description 3
150000002430 hydrocarbons Chemical class 0.000 description 3
239000007788 liquid Substances 0.000 description 3
229940050176 methyl chloride Drugs 0.000 description 3
229910052757 nitrogen Inorganic materials 0.000 description 3
239000003208 petroleum Substances 0.000 description 3
-1 sorbitan fatty acid esters Chemical class 0.000 description 3
239000000758 substrate Substances 0.000 description 3
QHVBLSNVXDSMEB-UHFFFAOYSA-N 2-(diethylamino)ethyl prop-2-enoate Chemical compound CCN(CC)CCOC(=O)C=C QHVBLSNVXDSMEB-UHFFFAOYSA-N 0.000 description 2
JKNCOURZONDCGV-UHFFFAOYSA-N 2-(dimethylamino)ethyl 2-methylprop-2-enoate Chemical compound CN(C)CCOC(=O)C(C)=C JKNCOURZONDCGV-UHFFFAOYSA-N 0.000 description 2
DPBJAVGHACCNRL-UHFFFAOYSA-N 2-(dimethylamino)ethyl prop-2-enoate Chemical compound CN(C)CCOC(=O)C=C DPBJAVGHACCNRL-UHFFFAOYSA-N 0.000 description 2
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 2
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
239000002253 acid Substances 0.000 description 2
ROOXNKNUYICQNP-UHFFFAOYSA-N ammonium persulfate Chemical group [NH4+].[NH4+].[O-]S(=O)(=O)OOS([O-])(=O)=O ROOXNKNUYICQNP-UHFFFAOYSA-N 0.000 description 2
125000002091 cationic group Chemical group 0.000 description 2
239000002738 chelating agent Substances 0.000 description 2
235000014113 dietary fatty acids Nutrition 0.000 description 2
DVSDDICSXBCMQJ-UHFFFAOYSA-N diethyl 2-acetylbutanedioate Chemical compound CCOC(=O)CC(C(C)=O)C(=O)OCC DVSDDICSXBCMQJ-UHFFFAOYSA-N 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
239000000194 fatty acid Substances 0.000 description 2
229930195729 fatty acid Natural products 0.000 description 2
230000014759 maintenance of location Effects 0.000 description 2
238000012986 modification Methods 0.000 description 2
230000004048 modification Effects 0.000 description 2
238000002360 preparation method Methods 0.000 description 2
238000010791 quenching Methods 0.000 description 2
230000000171 quenching effect Effects 0.000 description 2
239000011734 sodium Substances 0.000 description 2
229910052708 sodium Inorganic materials 0.000 description 2
ZORQXIQZAOLNGE-UHFFFAOYSA-N 1,1-difluorocyclohexane Chemical compound FC1(F)CCCCC1 ZORQXIQZAOLNGE-UHFFFAOYSA-N 0.000 description 1
SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 1
JAHNSTQSQJOJLO-UHFFFAOYSA-N 2-(3-fluorophenyl)-1h-imidazole Chemical compound FC1=CC=CC(C=2NC=CN=2)=C1 JAHNSTQSQJOJLO-UHFFFAOYSA-N 0.000 description 1
SJIXRGNQPBQWMK-UHFFFAOYSA-N 2-(diethylamino)ethyl 2-methylprop-2-enoate Chemical compound CCN(CC)CCOC(=O)C(C)=C SJIXRGNQPBQWMK-UHFFFAOYSA-N 0.000 description 1
NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 1
239000004342 Benzoyl peroxide Substances 0.000 description 1
OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 description 1
LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
229920008712 Copo Polymers 0.000 description 1
XZMCDFZZKTWFGF-UHFFFAOYSA-N Cyanamide Chemical compound NC#N XZMCDFZZKTWFGF-UHFFFAOYSA-N 0.000 description 1
YIVJZNGAASQVEM-UHFFFAOYSA-N Lauroyl peroxide Chemical compound CCCCCCCCCCCC(=O)OOC(=O)CCCCCCCCCCC YIVJZNGAASQVEM-UHFFFAOYSA-N 0.000 description 1
CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 1
QPCDCPDFJACHGM-UHFFFAOYSA-N N,N-bis{2-[bis(carboxymethyl)amino]ethyl}glycine Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(=O)O)CCN(CC(O)=O)CC(O)=O QPCDCPDFJACHGM-UHFFFAOYSA-N 0.000 description 1
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
RFFFKMOABOFIDF-UHFFFAOYSA-N Pentanenitrile Chemical compound CCCCC#N RFFFKMOABOFIDF-UHFFFAOYSA-N 0.000 description 1
229920003171 Poly (ethylene oxide) Polymers 0.000 description 1
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
DWAQJAXMDSEUJJ-UHFFFAOYSA-M Sodium bisulfite Chemical compound [Na+].OS([O-])=O DWAQJAXMDSEUJJ-UHFFFAOYSA-M 0.000 description 1
NWGKJDSIEKMTRX-AAZCQSIUSA-N Sorbitan monooleate Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OC[C@@H](O)[C@H]1OC[C@H](O)[C@H]1O NWGKJDSIEKMTRX-AAZCQSIUSA-N 0.000 description 1
238000012726 Water-in-Oil Emulsion Polymerization Methods 0.000 description 1
239000000443 aerosol Substances 0.000 description 1
238000013019 agitation Methods 0.000 description 1
150000007824 aliphatic compounds Chemical class 0.000 description 1
150000001412 amines Chemical class 0.000 description 1
229910001870 ammonium persulfate Inorganic materials 0.000 description 1
150000003863 ammonium salts Chemical class 0.000 description 1
125000000129 anionic group Chemical group 0.000 description 1
150000001491 aromatic compounds Chemical class 0.000 description 1
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
235000019400 benzoyl peroxide Nutrition 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
238000005352 clarification Methods 0.000 description 1
150000001875 compounds Chemical class 0.000 description 1
238000001816 cooling Methods 0.000 description 1
238000007334 copolymerization reaction Methods 0.000 description 1
238000000354 decomposition reaction Methods 0.000 description 1
239000008367 deionised water Substances 0.000 description 1
229910021641 deionized water Inorganic materials 0.000 description 1
IQDGSYLLQPDQDV-UHFFFAOYSA-N dimethylazanium;chloride Chemical compound Cl.CNC IQDGSYLLQPDQDV-UHFFFAOYSA-N 0.000 description 1
JMGZBMRVDHKMKB-UHFFFAOYSA-L disodium;2-sulfobutanedioate Chemical compound [Na+].[Na+].OS(=O)(=O)C(C([O-])=O)CC([O-])=O JMGZBMRVDHKMKB-UHFFFAOYSA-L 0.000 description 1
238000004945 emulsification Methods 0.000 description 1
230000001804 emulsifying effect Effects 0.000 description 1
238000007720 emulsion polymerization reaction Methods 0.000 description 1
150000002148 esters Chemical class 0.000 description 1
229920001038 ethylene copolymer Polymers 0.000 description 1
150000004665 fatty acids Chemical class 0.000 description 1
150000002193 fatty amides Chemical class 0.000 description 1
239000008394 flocculating agent Substances 0.000 description 1
ZZEKMMMOHDLVRX-UHFFFAOYSA-N formaldehyde;2-nonylphenol Chemical class O=C.CCCCCCCCCC1=CC=CC=C1O ZZEKMMMOHDLVRX-UHFFFAOYSA-N 0.000 description 1
239000007789 gas Substances 0.000 description 1
PYGSKMBEVAICCR-UHFFFAOYSA-N hexa-1,5-diene Chemical group C=CCCC=C PYGSKMBEVAICCR-UHFFFAOYSA-N 0.000 description 1
238000000265 homogenisation Methods 0.000 description 1
239000012535 impurity Substances 0.000 description 1
238000010348 incorporation Methods 0.000 description 1
VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
239000011976 maleic acid Substances 0.000 description 1
239000000463 material Substances 0.000 description 1
LVHBHZANLOWSRM-UHFFFAOYSA-N methylenebutanedioic acid Natural products OC(=O)CC(=C)C(O)=O LVHBHZANLOWSRM-UHFFFAOYSA-N 0.000 description 1
239000002480 mineral oil Substances 0.000 description 1
QYZFTMMPKCOTAN-UHFFFAOYSA-N n-[2-(2-hydroxyethylamino)ethyl]-2-[[1-[2-(2-hydroxyethylamino)ethylamino]-2-methyl-1-oxopropan-2-yl]diazenyl]-2-methylpropanamide Chemical compound OCCNCCNC(=O)C(C)(C)N=NC(C)(C)C(=O)NCCNCCO QYZFTMMPKCOTAN-UHFFFAOYSA-N 0.000 description 1
SNQQPOLDUKLAAF-UHFFFAOYSA-N nonylphenol Chemical class CCCCCCCCCC1=CC=CC=C1O SNQQPOLDUKLAAF-UHFFFAOYSA-N 0.000 description 1
125000002347 octyl 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])[H] 0.000 description 1
239000001301 oxygen Substances 0.000 description 1
229910052760 oxygen Inorganic materials 0.000 description 1
239000002245 particle Substances 0.000 description 1
229960003330 pentetic acid Drugs 0.000 description 1
125000000864 peroxy group Chemical group O(O*)* 0.000 description 1
229950010765 pivalate Drugs 0.000 description 1
229920000728 polyester Polymers 0.000 description 1
239000011591 potassium Substances 0.000 description 1
229910052700 potassium Inorganic materials 0.000 description 1
238000004886 process control Methods 0.000 description 1
239000000047 product Substances 0.000 description 1
150000003254 radicals Chemical class 0.000 description 1
239000012429 reaction media Substances 0.000 description 1
239000012966 redox initiator Substances 0.000 description 1
230000010076 replication Effects 0.000 description 1
229920005989 resin Polymers 0.000 description 1
239000011347 resin Substances 0.000 description 1
150000003333 secondary alcohols Chemical class 0.000 description 1
APSBXTVYXVQYAB-UHFFFAOYSA-M sodium docusate Chemical group [Na+].CCCCC(CC)COC(=O)CC(S([O-])(=O)=O)C(=O)OCC(CC)CCCC APSBXTVYXVQYAB-UHFFFAOYSA-M 0.000 description 1
235000010267 sodium hydrogen sulphite Nutrition 0.000 description 1
239000000126 substance Substances 0.000 description 1
ISIJQEHRDSCQIU-UHFFFAOYSA-N tert-butyl 2,7-diazaspiro[4.5]decane-7-carboxylate Chemical compound C1N(C(=O)OC(C)(C)C)CCCC11CNCC1 ISIJQEHRDSCQIU-UHFFFAOYSA-N 0.000 description 1
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
239000010913 used oil Substances 0.000 description 1
239000008096 xylene Substances 0.000 description 1

Landscapes

Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)

CA 2021984 1990-05-31 1990-07-26 Methode de preparation de copolymeres a base d'acrylamide et de chlorure de diallyldimethylammonium Abandoned CA2021984A1 (fr)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US53119690A	1990-05-31	1990-05-31
US07/531,196		1990-05-31

Publications (1)

Publication Number	Publication Date
CA2021984A1 true CA2021984A1 (fr)	1991-12-01

Family

ID=24116645

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA 2021984 Abandoned CA2021984A1 (fr)	1990-05-31	1990-07-26	Methode de preparation de copolymeres a base d'acrylamide et de chlorure de diallyldimethylammonium

Country Status (1)

Country	Link
CA (1)	CA2021984A1 (fr)

1990
- 1990-07-26 CA CA 2021984 patent/CA2021984A1/fr not_active Abandoned

Legal Events

Date	Code	Title	Description
1997-05-23	EEER	Examination request
2000-07-26	FZDE	Dead

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CA1242050A (fr)	1988-09-13	Polymeres d'emulsion inverse avec incorporation de chlorure de diallyldimethylammonium amelioree
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US5750614A (en)	1998-05-12	Process for preparing stable emulsions of polyelectrolytes of high molecular weight as reverse emulsion
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CA2063656A1 (fr)	1992-12-11	Methode d'obtention de copolymeres acrylamide/chlorure de diallyldimethylammonium
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CA2021984A1 (fr)	1991-12-01	Methode de preparation de copolymeres a base d'acrylamide et de chlorure de diallyldimethylammonium
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US4461866A (en)	1984-07-24	Preparation of water-in-oil emulsions