CA1291156C - Monomeres de type o-aminomethylenephosphonate-betaine - Google Patents

Monomeres de type o-aminomethylenephosphonate-betaine

Info

Publication number: CA1291156C
Authority: CA; Canada
Prior art keywords: hydrogen; alkyl; solution; aryl; monomers
Prior art date: 1986-12-11
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 - Lifetime

Application number

CA000615709A

Other languages

English (en)

Inventor

John C. Leighton

Carmine P. Iovine

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.)

Ablestik Laboratories

Original Assignee

Ablestik Laboratories

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.)

1986-12-11

Filing date

1990-04-23

Publication date

1991-10-22

1986-12-11 Priority claimed from US06/940,701 external-priority patent/US4707306A/en

1990-04-23 Application filed by Ablestik Laboratories filed Critical Ablestik Laboratories

1991-10-22 Application granted granted Critical

1991-10-22 Publication of CA1291156C publication Critical patent/CA1291156C/fr

2007-09-16 Anticipated expiration legal-status Critical

Status Expired - Lifetime legal-status Critical Current

Links

KWIUHFFTVRNATP-UHFFFAOYSA-N Betaine Natural products C[N+](C)(C)CC([O-])=O KWIUHFFTVRNATP-UHFFFAOYSA-N 0.000 title claims description 17
KWIUHFFTVRNATP-UHFFFAOYSA-O N,N,N-trimethylglycinium Chemical compound C[N+](C)(C)CC(O)=O KWIUHFFTVRNATP-UHFFFAOYSA-O 0.000 title claims description 17
239000000178 monomer Substances 0.000 title claims description 17
229960003237 betaine Drugs 0.000 title claims description 16
GWASTCVCPXFIQT-UHFFFAOYSA-N NC1OP(=O)O1 Chemical compound NC1OP(=O)O1 GWASTCVCPXFIQT-UHFFFAOYSA-N 0.000 title claims description 7
239000001257 hydrogen Substances 0.000 claims abstract description 14
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 14
125000003118 aryl group Chemical group 0.000 claims abstract description 10
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 10
150000001875 compounds Chemical class 0.000 claims abstract description 9
125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 9
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims abstract description 8
125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims abstract description 8
125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 6
QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical group [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims abstract description 4
150000001457 metallic cations Chemical group 0.000 claims abstract description 4
238000000034 method Methods 0.000 claims description 18
238000002360 preparation method Methods 0.000 claims description 11
229910052736 halogen Inorganic materials 0.000 claims description 4
150000002367 halogens Chemical class 0.000 claims description 4
150000002431 hydrogen Chemical group 0.000 claims description 4
125000000217 alkyl group Chemical group 0.000 claims description 2
239000003125 aqueous solvent Substances 0.000 claims description 2
239000000376 reactant Substances 0.000 claims 1
239000003795 chemical substances by application Substances 0.000 abstract description 5
239000002738 chelating agent Substances 0.000 abstract description 2
239000013078 crystal Substances 0.000 abstract description 2
239000003599 detergent Substances 0.000 abstract description 2
238000005553 drilling Methods 0.000 abstract description 2
230000005764 inhibitory process Effects 0.000 abstract description 2
239000003607 modifier Substances 0.000 abstract description 2
239000003129 oil well Substances 0.000 abstract description 2
239000000243 solution Substances 0.000 description 33
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 32
229920000642 polymer Polymers 0.000 description 30
238000006243 chemical reaction Methods 0.000 description 19
238000007792 addition Methods 0.000 description 16
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 15
239000002253 acid Substances 0.000 description 15
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 13
239000011541 reaction mixture Substances 0.000 description 12
125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 11
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 10
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 10
229910052757 nitrogen Inorganic materials 0.000 description 10
239000003999 initiator Substances 0.000 description 9
NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 8
229910052698 phosphorus Inorganic materials 0.000 description 8
238000010992 reflux Methods 0.000 description 8
SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 7
FLCAEMBIQVZWIF-UHFFFAOYSA-N 6-(dimethylamino)-2-methylhex-2-enamide Chemical compound CN(C)CCCC=C(C)C(N)=O FLCAEMBIQVZWIF-UHFFFAOYSA-N 0.000 description 7
150000007513 acids Chemical class 0.000 description 7
150000003512 tertiary amines Chemical class 0.000 description 7
SOGAXMICEFXMKE-UHFFFAOYSA-N Butylmethacrylate Chemical compound CCCCOC(=O)C(C)=C SOGAXMICEFXMKE-UHFFFAOYSA-N 0.000 description 6
238000006116 polymerization reaction Methods 0.000 description 6
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
-1 chlorohydroxypropyl Chemical group 0.000 description 5
239000003995 emulsifying agent Substances 0.000 description 5
239000000203 mixture Substances 0.000 description 5
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 5
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 4
239000000460 chlorine Substances 0.000 description 4
238000010438 heat treatment Methods 0.000 description 4
150000003254 radicals Chemical class 0.000 description 4
239000007787 solid Substances 0.000 description 4
LCPVQAHEFVXVKT-UHFFFAOYSA-N 2-(2,4-difluorophenoxy)pyridin-3-amine Chemical compound NC1=CC=CN=C1OC1=CC=C(F)C=C1F LCPVQAHEFVXVKT-UHFFFAOYSA-N 0.000 description 3
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 3
VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 3
OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 3
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
238000004458 analytical method Methods 0.000 description 3
229910052801 chlorine Inorganic materials 0.000 description 3
238000007334 copolymerization reaction Methods 0.000 description 3
239000000839 emulsion Substances 0.000 description 3
238000007720 emulsion polymerization reaction Methods 0.000 description 3
239000011574 phosphorus Substances 0.000 description 3
CHQMHPLRPQMAMX-UHFFFAOYSA-L sodium persulfate Substances [Na+].[Na+].[O-]S(=O)(=O)OOS([O-])(=O)=O CHQMHPLRPQMAMX-UHFFFAOYSA-L 0.000 description 3
239000006188 syrup Substances 0.000 description 3
235000020357 syrup Nutrition 0.000 description 3
UZKWTJUDCOPSNM-UHFFFAOYSA-N 1-ethenoxybutane Chemical compound CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 2
JLIDVCMBCGBIEY-UHFFFAOYSA-N 1-penten-3-one Chemical compound CCC(=O)C=C JLIDVCMBCGBIEY-UHFFFAOYSA-N 0.000 description 2
OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 description 2
KWSLGOVYXMQPPX-UHFFFAOYSA-N 5-[3-(trifluoromethyl)phenyl]-2h-tetrazole Chemical compound FC(F)(F)C1=CC=CC(C2=NNN=N2)=C1 KWSLGOVYXMQPPX-UHFFFAOYSA-N 0.000 description 2
NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 2
239000004342 Benzoyl peroxide Substances 0.000 description 2
OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 description 2
MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 2
CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 description 2
NGCCGMZMNVTERL-UHFFFAOYSA-N [(2-chloroethylamino)-phosphonomethyl]phosphonic acid Chemical compound OP(O)(=O)C(P(O)(O)=O)NCCCl NGCCGMZMNVTERL-UHFFFAOYSA-N 0.000 description 2
ROOXNKNUYICQNP-UHFFFAOYSA-N ammonium persulfate Chemical compound [NH4+].[NH4+].[O-]S(=O)(=O)OOS([O-])(=O)=O ROOXNKNUYICQNP-UHFFFAOYSA-N 0.000 description 2
235000019400 benzoyl peroxide Nutrition 0.000 description 2
239000003153 chemical reaction reagent Substances 0.000 description 2
239000003638 chemical reducing agent Substances 0.000 description 2
229920001577 copolymer Polymers 0.000 description 2
238000002425 crystallisation Methods 0.000 description 2
230000008025 crystallization Effects 0.000 description 2
238000000502 dialysis Methods 0.000 description 2
239000006185 dispersion Substances 0.000 description 2
238000004821 distillation Methods 0.000 description 2
150000002148 esters Chemical class 0.000 description 2
239000007789 gas Substances 0.000 description 2
WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 description 2
229920000847 nonoxynol Polymers 0.000 description 2
SNQQPOLDUKLAAF-UHFFFAOYSA-N nonylphenol Chemical class CCCCCCCCCC1=CC=CC=C1O SNQQPOLDUKLAAF-UHFFFAOYSA-N 0.000 description 2
JRKICGRDRMAZLK-UHFFFAOYSA-L peroxydisulfate Chemical compound [O-]S(=O)(=O)OOS([O-])(=O)=O JRKICGRDRMAZLK-UHFFFAOYSA-L 0.000 description 2
229920001223 polyethylene glycol Polymers 0.000 description 2
238000010926 purge Methods 0.000 description 2
239000000523 sample Substances 0.000 description 2
229910001379 sodium hypophosphite Inorganic materials 0.000 description 2
CIHOLLKRGTVIJN-UHFFFAOYSA-N tert‐butyl hydroperoxide Chemical compound CC(C)(C)OO CIHOLLKRGTVIJN-UHFFFAOYSA-N 0.000 description 2
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 2
QWUWMCYKGHVNAV-UHFFFAOYSA-N 1,2-dihydrostilbene Chemical group C=1C=CC=CC=1CCC1=CC=CC=C1 QWUWMCYKGHVNAV-UHFFFAOYSA-N 0.000 description 1
BJELTSYBAHKXRW-UHFFFAOYSA-N 2,4,6-triallyloxy-1,3,5-triazine Chemical compound C=CCOC1=NC(OCC=C)=NC(OCC=C)=N1 BJELTSYBAHKXRW-UHFFFAOYSA-N 0.000 description 1
OEPOKWHJYJXUGD-UHFFFAOYSA-N 2-(3-phenylmethoxyphenyl)-1,3-thiazole-4-carbaldehyde Chemical compound O=CC1=CSC(C=2C=C(OCC=3C=CC=CC=3)C=CC=2)=N1 OEPOKWHJYJXUGD-UHFFFAOYSA-N 0.000 description 1
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 1
PHIDEXXCOGMTBP-UHFFFAOYSA-N 3,3-diphenylprop-2-enamide Chemical compound C=1C=CC=CC=1C(=CC(=O)N)C1=CC=CC=C1 PHIDEXXCOGMTBP-UHFFFAOYSA-N 0.000 description 1
QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 description 1
HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 description 1
KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 1
239000004971 Cross linker Substances 0.000 description 1
239000004908 Emulsion polymer Substances 0.000 description 1
JIGUQPWFLRLWPJ-UHFFFAOYSA-N Ethyl acrylate Chemical compound CCOC(=O)C=C JIGUQPWFLRLWPJ-UHFFFAOYSA-N 0.000 description 1
KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 description 1
VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 1
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
WHNWPMSKXPGLAX-UHFFFAOYSA-N N-Vinyl-2-pyrrolidone Chemical compound C=CN1CCCC1=O WHNWPMSKXPGLAX-UHFFFAOYSA-N 0.000 description 1
101000986989 Naja kaouthia Acidic phospholipase A2 CM-II Proteins 0.000 description 1
239000002202 Polyethylene glycol Substances 0.000 description 1
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 description 1
BZHJMEDXRYGGRV-UHFFFAOYSA-N Vinyl chloride Chemical compound ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 description 1
QYKIQEUNHZKYBP-UHFFFAOYSA-N Vinyl ether Chemical class C=COC=C QYKIQEUNHZKYBP-UHFFFAOYSA-N 0.000 description 1
QKJGELVGISBBQC-UHFFFAOYSA-N [(1-chloro-4-hydroxybutyl)-phosphonoamino]phosphonic acid Chemical compound ClC(N(P(=O)(O)O)P(=O)(O)O)CCCO QKJGELVGISBBQC-UHFFFAOYSA-N 0.000 description 1
XRXZDNRKGKYFIS-UHFFFAOYSA-N [chloro-[3-hydroxypropyl(phosphonomethyl)amino]methyl]phosphonic acid Chemical compound OCCCN(CP(O)(O)=O)C(Cl)P(O)(O)=O XRXZDNRKGKYFIS-UHFFFAOYSA-N 0.000 description 1
150000003926 acrylamides Chemical class 0.000 description 1
238000013019 agitation Methods 0.000 description 1
150000001298 alcohols Chemical class 0.000 description 1
239000003513 alkali Substances 0.000 description 1
229910052783 alkali metal Inorganic materials 0.000 description 1
229940086737 allyl sucrose Drugs 0.000 description 1
150000001412 amines Chemical class 0.000 description 1
229910001870 ammonium persulfate Inorganic materials 0.000 description 1
238000010923 batch production Methods 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
239000004305 biphenyl Substances 0.000 description 1
235000010290 biphenyl Nutrition 0.000 description 1
125000006267 biphenyl group Chemical group 0.000 description 1
WDPDYXZEHLUZGD-UHFFFAOYSA-N bis(2-phenylethyl) 2-methylidenebutanedioate Chemical compound C=1C=CC=CC=1CCOC(=O)C(=C)CC(=O)OCCC1=CC=CC=C1 WDPDYXZEHLUZGD-UHFFFAOYSA-N 0.000 description 1
ZPOLOEWJWXZUSP-WAYWQWQTSA-N bis(prop-2-enyl) (z)-but-2-enedioate Chemical compound C=CCOC(=O)\C=C/C(=O)OCC=C ZPOLOEWJWXZUSP-WAYWQWQTSA-N 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
125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 description 1
150000001735 carboxylic acids Chemical class 0.000 description 1
229940125773 compound 10 Drugs 0.000 description 1
238000004132 cross linking Methods 0.000 description 1
150000005690 diesters Chemical class 0.000 description 1
125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
XQRLCLUYWUNEEH-UHFFFAOYSA-N diphosphonic acid Chemical compound OP(=O)OP(O)=O XQRLCLUYWUNEEH-UHFFFAOYSA-N 0.000 description 1
238000004090 dissolution Methods 0.000 description 1
UIWXSTHGICQLQT-UHFFFAOYSA-N ethenyl propanoate Chemical compound CCC(=O)OC=C UIWXSTHGICQLQT-UHFFFAOYSA-N 0.000 description 1
238000010528 free radical solution polymerization reaction Methods 0.000 description 1
229920001519 homopolymer Polymers 0.000 description 1
BHEPBYXIRTUNPN-UHFFFAOYSA-N hydridophosphorus(.) (triplet) Chemical compound [PH] BHEPBYXIRTUNPN-UHFFFAOYSA-N 0.000 description 1
230000002209 hydrophobic effect Effects 0.000 description 1
229910052500 inorganic mineral Inorganic materials 0.000 description 1
238000002955 isolation Methods 0.000 description 1
ZLVXBBHTMQJRSX-VMGNSXQWSA-N jdtic Chemical compound C1([C@]2(C)CCN(C[C@@H]2C)C[C@H](C(C)C)NC(=O)[C@@H]2NCC3=CC(O)=CC=C3C2)=CC=CC(O)=C1 ZLVXBBHTMQJRSX-VMGNSXQWSA-N 0.000 description 1
229910052744 lithium Inorganic materials 0.000 description 1
HPGPEWYJWRWDTP-UHFFFAOYSA-N lithium peroxide Chemical compound [Li+].[Li+].[O-][O-] HPGPEWYJWRWDTP-UHFFFAOYSA-N 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
150000002689 maleic acids Chemical class 0.000 description 1
238000004519 manufacturing process Methods 0.000 description 1
MBKDYNNUVRNNRF-UHFFFAOYSA-N medronic acid Chemical class OP(O)(=O)CP(O)(O)=O MBKDYNNUVRNNRF-UHFFFAOYSA-N 0.000 description 1
229910052751 metal Inorganic materials 0.000 description 1
239000002184 metal Substances 0.000 description 1
FQPSGWSUVKBHSU-UHFFFAOYSA-N methacrylamide Chemical compound CC(=C)C(N)=O FQPSGWSUVKBHSU-UHFFFAOYSA-N 0.000 description 1
125000005395 methacrylic acid group Chemical class 0.000 description 1
NQMRYBIKMRVZLB-UHFFFAOYSA-N methylamine hydrochloride Chemical compound [Cl-].[NH3+]C NQMRYBIKMRVZLB-UHFFFAOYSA-N 0.000 description 1
239000011707 mineral Substances 0.000 description 1
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical group CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 1
239000012457 nonaqueous media Substances 0.000 description 1
PNJWIWWMYCMZRO-UHFFFAOYSA-N pent‐4‐en‐2‐one Natural products CC(=O)CC=C PNJWIWWMYCMZRO-UHFFFAOYSA-N 0.000 description 1
150000004965 peroxy acids Chemical class 0.000 description 1
ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 1
UEZVMMHDMIWARA-UHFFFAOYSA-M phosphonate Chemical compound [O-]P(=O)=O UEZVMMHDMIWARA-UHFFFAOYSA-M 0.000 description 1
230000000379 polymerizing effect Effects 0.000 description 1
229920001451 polypropylene glycol Polymers 0.000 description 1
USHAGKDGDHPEEY-UHFFFAOYSA-L potassium persulfate Chemical compound [K+].[K+].[O-]S(=O)(=O)OOS([O-])(=O)=O USHAGKDGDHPEEY-UHFFFAOYSA-L 0.000 description 1
239000000843 powder Substances 0.000 description 1
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
238000005956 quaternization reaction Methods 0.000 description 1
230000009257 reactivity Effects 0.000 description 1
XWGJFPHUCFXLBL-UHFFFAOYSA-M rongalite Chemical compound [Na+].OCS([O-])=O XWGJFPHUCFXLBL-UHFFFAOYSA-M 0.000 description 1
150000003839 salts Chemical class 0.000 description 1
HRZFUMHJMZEROT-UHFFFAOYSA-L sodium disulfite Chemical compound [Na+].[Na+].[O-]S(=O)S([O-])(=O)=O HRZFUMHJMZEROT-UHFFFAOYSA-L 0.000 description 1
229940001584 sodium metabisulfite Drugs 0.000 description 1
235000010262 sodium metabisulphite Nutrition 0.000 description 1
PFUVRDFDKPNGAV-UHFFFAOYSA-N sodium peroxide Chemical compound [Na+].[Na+].[O-][O-] PFUVRDFDKPNGAV-UHFFFAOYSA-N 0.000 description 1
SPDUKHLMYVCLOA-UHFFFAOYSA-M sodium;ethaneperoxoate Chemical compound [Na+].CC(=O)O[O-] SPDUKHLMYVCLOA-UHFFFAOYSA-M 0.000 description 1
JITOKQVGRJSHHA-UHFFFAOYSA-N sodium;methylarsonic acid Chemical compound [Na+].C[As](O)(O)=O JITOKQVGRJSHHA-UHFFFAOYSA-N 0.000 description 1
239000002689 soil Substances 0.000 description 1
239000002904 solvent Substances 0.000 description 1
238000001694 spray drying Methods 0.000 description 1
238000003756 stirring Methods 0.000 description 1
239000011593 sulfur Substances 0.000 description 1
229910052717 sulfur Inorganic materials 0.000 description 1
239000004094 surface-active agent Substances 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
OPQYOFWUFGEMRZ-UHFFFAOYSA-N tert-butyl 2,2-dimethylpropaneperoxoate Chemical compound CC(C)(C)OOC(=O)C(C)(C)C OPQYOFWUFGEMRZ-UHFFFAOYSA-N 0.000 description 1
SWAXTRYEYUTSAP-UHFFFAOYSA-N tert-butyl ethaneperoxoate Chemical compound CC(=O)OOC(C)(C)C SWAXTRYEYUTSAP-UHFFFAOYSA-N 0.000 description 1
UWHCKJMYHZGTIT-UHFFFAOYSA-N tetraethylene glycol Chemical compound OCCOCCOCCOCCO UWHCKJMYHZGTIT-UHFFFAOYSA-N 0.000 description 1
238000004448 titration Methods 0.000 description 1
229920001567 vinyl ester resin Polymers 0.000 description 1
FUSUHKVFWTUUBE-UHFFFAOYSA-N vinyl methyl ketone Natural products CC(=O)C=C FUSUHKVFWTUUBE-UHFFFAOYSA-N 0.000 description 1
229920002554 vinyl polymer Polymers 0.000 description 1

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

CA000615709A 1986-12-11 1990-04-23 Monomeres de type o-aminomethylenephosphonate-betaine Expired - Lifetime CA1291156C (fr)

Applications Claiming Priority (3)

Application Number	Priority Date	Filing Date	Title
US06/940,701 US4707306A (en)	1986-12-11	1986-12-11	Alpha-aminomethylene phosphonate betaines and polymers prepared therewith
US940,701		1986-12-11
CA000547077A CA1287441C (fr)	1986-12-11	1987-09-16	O-aminoethylenephosphonatebetaines et polymeres prepares a partir de celles-ci

Related Parent Applications (1)

Application Number	Title	Priority Date	Filing Date
CA000547077A Division CA1287441C (fr)	1986-12-11	1987-09-16	O-aminoethylenephosphonatebetaines et polymeres prepares a partir de celles-ci

Publications (1)

Publication Number	Publication Date
CA1291156C true CA1291156C (fr)	1991-10-22

Family

ID=25671509

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA000615709A Expired - Lifetime CA1291156C (fr)	1986-12-11	1990-04-23	Monomeres de type o-aminomethylenephosphonate-betaine

Country Status (1)

Country	Link
CA (1)	CA1291156C (fr)

1990
- 1990-04-23 CA CA000615709A patent/CA1291156C/fr not_active Expired - Lifetime

Legal Events

Date	Code	Title	Description
1997-10-22	MKLA	Lapsed

Publication	Publication Date	Title
EP0273107B1 (fr)	1992-12-09	Alpha-aminométhylène phosphonates bétaines et polymères préparés avec elles
US5294687A (en)	1994-03-15	Low molecular weight monoalkyl substituted phosphinate and phosphonate copolymers
CA1339143C (fr)	1997-07-29	Esters des acides alcenylphosphonique et -phosphinique; methode de preparation; hydrogels obtenus avec ces esters et utilisation
US4778865A (en)	1988-10-18	Alpha-aminomethylene phosphonate betaines and polymers prepared therewith
DE60012981T2 (de)	2005-08-11	Verfahren zur herstellung von polymeren durch eine kontrollierte radikalischpolymerisation mit xanthaten
US2777872A (en)	1957-01-15	Unsaturated organic compounds
CA1165498A (fr)	1984-04-10	Polymeres, et methode de production connexe
JPH04258608A (ja)	1992-09-14	ポリマー状硼酸アンモニウムおよびその製造方法
JPH08504239A (ja)	1996-05-07	紙製造の際のｎ−ビニルカルボン酸アミドおよびモノエチレン系不飽和カルボン酸からの加水分解された共重合体の使用
JPS60218363A (ja)	1985-11-01	高電荷密度、カチオン性メタクリルアミド系モノマーおよびそのポリマー
US4996045A (en)	1991-02-26	Hair fixative compositions containing alpha-aminomethylene phosphonate betaines
CA1291156C (fr)	1991-10-22	Monomeres de type o-aminomethylenephosphonate-betaine
EP0634428B1 (fr)	1998-10-21	Procédé de préparation de polymères
JPS5867706A (ja)	1983-04-22	モノエチレン性不飽和のモノ−及びジカルボン酸からの共重合物の製法
JPH04504869A (ja)	1992-08-27	無水マレイン酸とアルキルビニルエーテルとの高固形分共重合方法
US3346545A (en)	1967-10-10	Olefinically unsaturated phosphate and phosphonate monomers and process for making same and polymers therefrom
JPH0649082A (ja)	1994-02-22	アルケニルアミノアルキレンホスホン酸エステル並びに、アルケニルアミノアルキレンホスホナートとエチレン性不飽和化合物とのコポリマーの製造方法
EP0102707B1 (fr)	1986-09-17	Procédé de préparation de dispersions aqueuses stabilisées stériquement non chargées de polymères
JPH04309511A (ja)	1992-11-02	ジアリルアミノアルキレン−ホスホナートおよび不飽和カルボン酸より成るコポリマー
CA2092757A1 (fr)	1993-09-29	Derives d'acide alcenylaminoalcane-1-1-diphosphonique et copolymeres ainsi obtenus avec des acides carboxyliques non satures
EP0356026B1 (fr)	1994-04-27	Composés azo-amide
US4486554A (en)	1984-12-04	Preparation of anionic and cationic polymers from 2-oxazolines
US4297468A (en)	1981-10-27	Allyl amido phosphorous copolymers
JPH0555526B2 (fr)	1993-08-17
US3980800A (en)	1976-09-14	Polymers of N-(chloroalkoxymethyl)acrylamides, quaternary ammonium derivates