CA2645436A1 - Water-soluble macromonomers containing terminal unsaturation and a process for the preparation thereof - Google Patents
Water-soluble macromonomers containing terminal unsaturation and a process for the preparation thereof Download PDFInfo
- Publication number
- CA2645436A1 CA2645436A1 CA002645436A CA2645436A CA2645436A1 CA 2645436 A1 CA2645436 A1 CA 2645436A1 CA 002645436 A CA002645436 A CA 002645436A CA 2645436 A CA2645436 A CA 2645436A CA 2645436 A1 CA2645436 A1 CA 2645436A1
- Authority
- CA
- Canada
- Prior art keywords
- amsd
- water
- polymerization
- soluble
- complex
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Abandoned
Links
- 238000000034 method Methods 0.000 title claims description 28
- 238000002360 preparation method Methods 0.000 title claims description 22
- 230000008569 process Effects 0.000 title claims description 15
- 239000000178 monomer Substances 0.000 claims abstract description 79
- 238000006116 polymerization reaction Methods 0.000 claims abstract description 59
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims abstract description 34
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 31
- 229920002554 vinyl polymer Polymers 0.000 claims abstract description 22
- 239000012986 chain transfer agent Substances 0.000 claims abstract description 21
- 239000012736 aqueous medium Substances 0.000 claims abstract description 8
- 229920000642 polymer Polymers 0.000 claims description 46
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 37
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 claims description 16
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical group OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 15
- 239000003999 initiator Substances 0.000 claims description 14
- 239000011541 reaction mixture Substances 0.000 claims description 14
- JKNCOURZONDCGV-UHFFFAOYSA-N 2-(dimethylamino)ethyl 2-methylprop-2-enoate Chemical compound CN(C)CCOC(=O)C(C)=C JKNCOURZONDCGV-UHFFFAOYSA-N 0.000 claims description 13
- 239000004159 Potassium persulphate Substances 0.000 claims description 13
- 235000019394 potassium persulphate Nutrition 0.000 claims description 13
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 12
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 claims description 11
- XYLMUPLGERFSHI-UHFFFAOYSA-N alpha-Methylstyrene Chemical compound CC(=C)C1=CC=CC=C1 XYLMUPLGERFSHI-UHFFFAOYSA-N 0.000 claims description 11
- WHNWPMSKXPGLAX-UHFFFAOYSA-N N-Vinyl-2-pyrrolidone Chemical compound C=CN1CCCC1=O WHNWPMSKXPGLAX-UHFFFAOYSA-N 0.000 claims description 10
- USHAGKDGDHPEEY-UHFFFAOYSA-L potassium persulfate Chemical compound [K+].[K+].[O-]S(=O)(=O)OOS([O-])(=O)=O USHAGKDGDHPEEY-UHFFFAOYSA-L 0.000 claims description 9
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims description 8
- 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 claims description 8
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 claims description 7
- 239000002904 solvent Substances 0.000 claims description 7
- XHZPRMZZQOIPDS-UHFFFAOYSA-N 2-Methyl-2-[(1-oxo-2-propenyl)amino]-1-propanesulfonic acid Chemical compound OS(=O)(=O)CC(C)(C)NC(=O)C=C XHZPRMZZQOIPDS-UHFFFAOYSA-N 0.000 claims description 6
- 230000002378 acidificating effect Effects 0.000 claims description 6
- 230000007935 neutral effect Effects 0.000 claims description 6
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 6
- 238000001035 drying Methods 0.000 claims description 5
- 239000003960 organic solvent Substances 0.000 claims description 5
- 239000008139 complexing agent Substances 0.000 claims description 4
- 230000000379 polymerizing effect Effects 0.000 claims description 3
- 239000012966 redox initiator Substances 0.000 claims description 3
- HRZFUMHJMZEROT-UHFFFAOYSA-L sodium disulfite Chemical compound [Na+].[Na+].[O-]S(=O)S([O-])(=O)=O HRZFUMHJMZEROT-UHFFFAOYSA-L 0.000 claims description 3
- 239000004296 sodium metabisulphite Substances 0.000 claims description 3
- 235000010262 sodium metabisulphite Nutrition 0.000 claims description 3
- SJIXRGNQPBQWMK-UHFFFAOYSA-N 2-(diethylamino)ethyl 2-methylprop-2-enoate Chemical compound CCN(CC)CCOC(=O)C(C)=C SJIXRGNQPBQWMK-UHFFFAOYSA-N 0.000 claims description 2
- ZAWQXWZJKKICSZ-UHFFFAOYSA-N 3,3-dimethyl-2-methylidenebutanamide Chemical compound CC(C)(C)C(=C)C(N)=O ZAWQXWZJKKICSZ-UHFFFAOYSA-N 0.000 claims description 2
- MAGFQRLKWCCTQJ-UHFFFAOYSA-N 4-ethenylbenzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=C(C=C)C=C1 MAGFQRLKWCCTQJ-UHFFFAOYSA-N 0.000 claims description 2
- 239000004160 Ammonium persulphate Substances 0.000 claims description 2
- ROOXNKNUYICQNP-UHFFFAOYSA-N ammonium persulfate Chemical compound [NH4+].[NH4+].[O-]S(=O)(=O)OOS([O-])(=O)=O ROOXNKNUYICQNP-UHFFFAOYSA-N 0.000 claims description 2
- 235000019395 ammonium persulphate Nutrition 0.000 claims description 2
- 125000000751 azo group Chemical group [*]N=N[*] 0.000 claims description 2
- WHGYBXFWUBPSRW-FOUAGVGXSA-N beta-cyclodextrin Chemical class OC[C@H]([C@H]([C@@H]([C@H]1O)O)O[C@H]2O[C@@H]([C@@H](O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O3)[C@H](O)[C@H]2O)CO)O[C@@H]1O[C@H]1[C@H](O)[C@@H](O)[C@@H]3O[C@@H]1CO WHGYBXFWUBPSRW-FOUAGVGXSA-N 0.000 claims description 2
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 2
- 238000001914 filtration Methods 0.000 claims description 2
- 238000010528 free radical solution polymerization reaction Methods 0.000 claims description 2
- WFKDPJRCBCBQNT-UHFFFAOYSA-N n,2-dimethylprop-2-enamide Chemical compound CNC(=O)C(C)=C WFKDPJRCBCBQNT-UHFFFAOYSA-N 0.000 claims description 2
- NRTBZBYBLPEOCE-UHFFFAOYSA-L potassium;sodium;sulfite Chemical compound [Na+].[K+].[O-]S([O-])=O NRTBZBYBLPEOCE-UHFFFAOYSA-L 0.000 claims description 2
- 230000001376 precipitating effect Effects 0.000 claims description 2
- 238000003756 stirring Methods 0.000 claims description 2
- 238000005406 washing Methods 0.000 claims description 2
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical class CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 claims 1
- 239000002253 acid Substances 0.000 claims 1
- HFHDHCJBZVLPGP-UHFFFAOYSA-N schardinger α-dextrin Chemical class O1C(C(C2O)O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC(C(O)C2O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC2C(O)C(O)C1OC2CO HFHDHCJBZVLPGP-UHFFFAOYSA-N 0.000 abstract description 8
- 229920000858 Cyclodextrin Polymers 0.000 abstract description 7
- 238000007334 copolymerization reaction Methods 0.000 abstract description 7
- 230000002209 hydrophobic effect Effects 0.000 abstract description 7
- ZOKCNEIWFQCSCM-UHFFFAOYSA-N (2-methyl-4-phenylpent-4-en-2-yl)benzene Chemical group C=1C=CC=CC=1C(C)(C)CC(=C)C1=CC=CC=C1 ZOKCNEIWFQCSCM-UHFFFAOYSA-N 0.000 abstract description 3
- 238000010668 complexation reaction Methods 0.000 abstract 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 25
- 238000012546 transfer Methods 0.000 description 21
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 20
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 19
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 18
- -1 Poly(acrylic acid) Polymers 0.000 description 18
- 150000003254 radicals Chemical class 0.000 description 15
- 239000000243 solution Substances 0.000 description 15
- 238000005481 NMR spectroscopy Methods 0.000 description 14
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 13
- 238000005033 Fourier transform infrared spectroscopy Methods 0.000 description 13
- 230000015572 biosynthetic process Effects 0.000 description 12
- 239000012153 distilled water Substances 0.000 description 12
- 238000010526 radical polymerization reaction Methods 0.000 description 12
- 238000012360 testing method Methods 0.000 description 12
- 239000003795 chemical substances by application Substances 0.000 description 11
- 238000003786 synthesis reaction Methods 0.000 description 11
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 9
- 238000000576 coating method Methods 0.000 description 9
- 239000000203 mixture Substances 0.000 description 8
- 101150041968 CDC13 gene Proteins 0.000 description 7
- 229910001873 dinitrogen Inorganic materials 0.000 description 7
- 229920002451 polyvinyl alcohol Polymers 0.000 description 7
- 229920002125 Sokalan® Polymers 0.000 description 6
- 238000006062 fragmentation reaction Methods 0.000 description 6
- 230000008901 benefit Effects 0.000 description 5
- 229920000578 graft copolymer Polymers 0.000 description 5
- IRLPACMLTUPBCL-KQYNXXCUSA-N 5'-adenylyl sulfate Chemical compound C1=NC=2C(N)=NC=NC=2N1[C@@H]1O[C@H](COP(O)(=O)OS(O)(=O)=O)[C@@H](O)[C@H]1O IRLPACMLTUPBCL-KQYNXXCUSA-N 0.000 description 4
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical class S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 4
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 4
- 241001229135 Nassa Species 0.000 description 4
- 229920001577 copolymer Polymers 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 238000013467 fragmentation Methods 0.000 description 4
- 239000004584 polyacrylic acid Substances 0.000 description 4
- 239000002243 precursor Substances 0.000 description 4
- HXHCOXPZCUFAJI-UHFFFAOYSA-N prop-2-enoic acid;styrene Chemical compound OC(=O)C=C.C=CC1=CC=CC=C1 HXHCOXPZCUFAJI-UHFFFAOYSA-N 0.000 description 4
- RPACBEVZENYWOL-XFULWGLBSA-M sodium;(2r)-2-[6-(4-chlorophenoxy)hexyl]oxirane-2-carboxylate Chemical compound [Na+].C=1C=C(Cl)C=CC=1OCCCCCC[C@]1(C(=O)[O-])CO1 RPACBEVZENYWOL-XFULWGLBSA-M 0.000 description 4
- VWXLCWNPSOUPPE-UHFFFAOYSA-N (1-amino-2-methylpropylidene)azanium;chloride Chemical compound Cl.CC(C)C(N)=N VWXLCWNPSOUPPE-UHFFFAOYSA-N 0.000 description 3
- 238000004566 IR spectroscopy Methods 0.000 description 3
- ZDWZXBJFITXZBL-UHFFFAOYSA-N S(=O)(=O)(O)C=CC1=CC=CC=C1.[Na] Chemical compound S(=O)(=O)(O)C=CC1=CC=CC=C1.[Na] ZDWZXBJFITXZBL-UHFFFAOYSA-N 0.000 description 3
- 238000004458 analytical method Methods 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 239000002270 dispersing agent Substances 0.000 description 3
- 239000007789 gas Substances 0.000 description 3
- 229920000126 latex Polymers 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 239000003973 paint Substances 0.000 description 3
- 229920005989 resin Polymers 0.000 description 3
- 239000011347 resin Substances 0.000 description 3
- 244000043261 Hevea brasiliensis Species 0.000 description 2
- PWKSKIMOESPYIA-BYPYZUCNSA-N L-N-acetyl-Cysteine Chemical compound CC(=O)N[C@@H](CS)C(O)=O PWKSKIMOESPYIA-BYPYZUCNSA-N 0.000 description 2
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 2
- 125000000746 allylic group Chemical group 0.000 description 2
- 229910021529 ammonia Inorganic materials 0.000 description 2
- 239000011230 binding agent Substances 0.000 description 2
- 229920001400 block copolymer Polymers 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 230000003197 catalytic effect Effects 0.000 description 2
- 239000011248 coating agent Substances 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 239000004567 concrete Substances 0.000 description 2
- 229920001971 elastomer Polymers 0.000 description 2
- 229910052500 inorganic mineral Inorganic materials 0.000 description 2
- 239000004816 latex Substances 0.000 description 2
- 229920002521 macromolecule Polymers 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 239000011707 mineral Substances 0.000 description 2
- 229920003052 natural elastomer Polymers 0.000 description 2
- 229920001194 natural rubber Polymers 0.000 description 2
- 238000012705 nitroxide-mediated radical polymerization Methods 0.000 description 2
- 238000005498 polishing Methods 0.000 description 2
- QROGIFZRVHSFLM-UHFFFAOYSA-N prop-1-enylbenzene Chemical class CC=CC1=CC=CC=C1 QROGIFZRVHSFLM-UHFFFAOYSA-N 0.000 description 2
- 230000035484 reaction time Effects 0.000 description 2
- 230000009257 reactivity Effects 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- 239000002002 slurry Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- CWERGRDVMFNCDR-UHFFFAOYSA-N thioglycolic acid Chemical compound OC(=O)CS CWERGRDVMFNCDR-UHFFFAOYSA-N 0.000 description 2
- LLVWLCAZSOLOTF-UHFFFAOYSA-N 1-methyl-4-[1,4,4-tris(4-methylphenyl)buta-1,3-dienyl]benzene Chemical compound C1=CC(C)=CC=C1C(C=1C=CC(C)=CC=1)=CC=C(C=1C=CC(C)=CC=1)C1=CC=C(C)C=C1 LLVWLCAZSOLOTF-UHFFFAOYSA-N 0.000 description 1
- 238000005160 1H NMR spectroscopy Methods 0.000 description 1
- NICLKHGIKDZZGV-UHFFFAOYSA-N 2-cyanopentanoic acid Chemical compound CCCC(C#N)C(O)=O NICLKHGIKDZZGV-UHFFFAOYSA-N 0.000 description 1
- JLBJTVDPSNHSKJ-UHFFFAOYSA-N 4-Methylstyrene Chemical class CC1=CC=C(C=C)C=C1 JLBJTVDPSNHSKJ-UHFFFAOYSA-N 0.000 description 1
- 239000005995 Aluminium silicate Substances 0.000 description 1
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 1
- LSDPWZHWYPCBBB-UHFFFAOYSA-N Methanethiol Chemical group SC LSDPWZHWYPCBBB-UHFFFAOYSA-N 0.000 description 1
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 229910006069 SO3H Inorganic materials 0.000 description 1
- 238000005299 abrasion Methods 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 125000004453 alkoxycarbonyl group Chemical group 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 239000004411 aluminium Substances 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- 239000005030 aluminium foil Substances 0.000 description 1
- 235000012211 aluminium silicate Nutrition 0.000 description 1
- 125000003368 amide group Chemical group 0.000 description 1
- 125000000129 anionic group Chemical group 0.000 description 1
- 238000013459 approach Methods 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- IQIXQINTSRHNDE-UHFFFAOYSA-N butanimidamide;dihydrochloride Chemical compound Cl.Cl.CCCC(N)=N IQIXQINTSRHNDE-UHFFFAOYSA-N 0.000 description 1
- STYCVEYASXULRN-UHFFFAOYSA-N butanimidamide;hydrochloride Chemical compound [Cl-].CCCC(N)=[NH2+] STYCVEYASXULRN-UHFFFAOYSA-N 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000011203 carbon fibre reinforced carbon Substances 0.000 description 1
- 125000002091 cationic group Chemical group 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 239000004568 cement Substances 0.000 description 1
- LBFUKZWYPLNNJC-UHFFFAOYSA-N cobalt(ii,iii) oxide Chemical compound [Co]=O.O=[Co]O[Co]=O LBFUKZWYPLNNJC-UHFFFAOYSA-N 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 230000000536 complexating effect Effects 0.000 description 1
- 238000004132 cross linking Methods 0.000 description 1
- 229940097362 cyclodextrins Drugs 0.000 description 1
- 238000006356 dehydrogenation reaction Methods 0.000 description 1
- 238000013461 design Methods 0.000 description 1
- 239000003599 detergent Substances 0.000 description 1
- 229920003244 diene elastomer Polymers 0.000 description 1
- 229960001760 dimethyl sulfoxide Drugs 0.000 description 1
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- 238000009826 distribution Methods 0.000 description 1
- 125000005022 dithioester group Chemical group 0.000 description 1
- WNAHIZMDSQCWRP-UHFFFAOYSA-N dodecane-1-thiol Chemical compound CCCCCCCCCCCCS WNAHIZMDSQCWRP-UHFFFAOYSA-N 0.000 description 1
- 239000000806 elastomer Substances 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
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- 238000009472 formulation Methods 0.000 description 1
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- 239000010440 gypsum Substances 0.000 description 1
- 229910052602 gypsum Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
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- 238000011835 investigation Methods 0.000 description 1
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- 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
- 239000004922 lacquer Substances 0.000 description 1
- 238000010550 living polymerization reaction Methods 0.000 description 1
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- 239000002609 medium Substances 0.000 description 1
- 150000002734 metacrylic acid derivatives Chemical class 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 239000012764 mineral filler 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
- 238000006902 nitrogenation reaction Methods 0.000 description 1
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- 239000004800 polyvinyl chloride Substances 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 230000001902 propagating effect Effects 0.000 description 1
- KCXFHTAICRTXLI-UHFFFAOYSA-N propane-1-sulfonic acid Chemical compound CCCS(O)(=O)=O KCXFHTAICRTXLI-UHFFFAOYSA-N 0.000 description 1
- KOODSCBKXPPKHE-UHFFFAOYSA-N propanethioic s-acid Chemical compound CCC(S)=O KOODSCBKXPPKHE-UHFFFAOYSA-N 0.000 description 1
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 238000005086 pumping Methods 0.000 description 1
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- 230000002441 reversible effect Effects 0.000 description 1
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- 239000000565 sealant Substances 0.000 description 1
- 238000007789 sealing Methods 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- 210000002966 serum Anatomy 0.000 description 1
- 238000004513 sizing Methods 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 230000003381 solubilizing effect Effects 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 229920001169 thermoplastic Polymers 0.000 description 1
- 239000004416 thermosoftening plastic Substances 0.000 description 1
- 230000008719 thickening Effects 0.000 description 1
- HIZCIEIDIFGZSS-UHFFFAOYSA-L trithiocarbonate Chemical class [S-]C([S-])=S HIZCIEIDIFGZSS-UHFFFAOYSA-L 0.000 description 1
- 238000004078 waterproofing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F2/00—Processes of polymerisation
- C08F2/38—Polymerisation using regulators, e.g. chain terminating agents, e.g. telomerisation
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F290/00—Macromolecular compounds obtained by polymerising monomers on to polymers modified by introduction of aliphatic unsaturated end or side groups
- C08F290/02—Macromolecular compounds obtained by polymerising monomers on to polymers modified by introduction of aliphatic unsaturated end or side groups on to polymers modified by introduction of unsaturated end groups
- C08F290/04—Polymers provided for in subclasses C08C or C08F
- C08F290/046—Polymers of unsaturated carboxylic acids or derivatives thereof
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- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Macromonomer-Based Addition Polymer (AREA)
- Polymerisation Methods In General (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IN848DE2006 | 2006-03-28 | ||
| IN848/DEL/2006 | 2006-03-28 | ||
| PCT/IN2007/000125 WO2007110882A1 (en) | 2006-03-28 | 2007-03-28 | Water-soluble macromonomers containing terminal unsaturation and a process for the preparation thereof |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2645436A1 true CA2645436A1 (en) | 2007-10-04 |
Family
ID=38134765
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002645436A Abandoned CA2645436A1 (en) | 2006-03-28 | 2007-03-28 | Water-soluble macromonomers containing terminal unsaturation and a process for the preparation thereof |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US7875659B2 (enExample) |
| EP (1) | EP1999162B1 (enExample) |
| JP (1) | JP5388841B2 (enExample) |
| AT (1) | ATE486893T1 (enExample) |
| CA (1) | CA2645436A1 (enExample) |
| DE (1) | DE602007010256D1 (enExample) |
| WO (1) | WO2007110882A1 (enExample) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2012236797A (ja) * | 2011-05-12 | 2012-12-06 | Adeka Corp | 複合体及びその製造方法 |
| KR20140088895A (ko) * | 2011-11-01 | 2014-07-11 | 루브리졸 어드밴스드 머티어리얼스, 인코포레이티드 | 아크릴레이트올레핀 공중합체，이를 생산하는 방법 및 이를 이용한 조성물 |
| WO2013162019A1 (ja) * | 2012-04-27 | 2013-10-31 | 国立大学法人大阪大学 | 自己修復性及び形状記憶性を有するゲル、及びその製造方法 |
| CN109060979A (zh) * | 2018-08-02 | 2018-12-21 | 成都中医药大学 | 一种亚甲二氧苯丙烯类毒素的测定方法 |
| EP3906263A4 (en) | 2019-01-03 | 2022-08-31 | Underdog Pharmaceuticals, Inc. | CYCLODEXTRIN DIMERS, COMPOSITIONS THEREOF AND USES THEREOF |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4000220A (en) * | 1971-07-09 | 1976-12-28 | Hitachi, Ltd. | Method for producing thermoplastic resin |
| IT1007901B (it) * | 1974-04-12 | 1976-10-30 | Montedison Spa | Procedimento per la produzione di polisterolo resistente all urto |
| JPS5839161B2 (ja) * | 1976-08-03 | 1983-08-27 | 大日本インキ化学工業株式会社 | 分散樹脂組成物の製造法 |
| DE3023721A1 (de) * | 1980-06-25 | 1982-01-21 | Basf Ag, 6700 Ludwigshafen | Verfahren zur kontinuierlichen herstellung von mit kautschuk modifizierten polymerisaten von vinylaromaten |
| US4547327A (en) * | 1980-12-08 | 1985-10-15 | Medical Biological Sciences, Inc. | Method for producing a porous prosthesis |
| US4694054A (en) * | 1985-03-01 | 1987-09-15 | E. I. Du Pont De Nemours And Company | Cobalt(II) chelates as chain transfer agents in free radical polymerizations |
| US4680352A (en) * | 1985-03-01 | 1987-07-14 | E. I. Du Pont De Nemours And Company | Cobalt (II) chelates as chain transfer agents in free radical polymerizations |
| US4808656A (en) * | 1987-05-04 | 1989-02-28 | Ppg Industries, Inc. | High solids coating compositions |
| JP2613482B2 (ja) * | 1989-11-16 | 1997-05-28 | 第一工業製薬株式会社 | ロジン系エマルジョンサイズ剤用乳化分散剤及びサイズ剤 |
| JP2646770B2 (ja) * | 1989-12-13 | 1997-08-27 | 日本合成ゴム株式会社 | 共重合体ラテックスの製造方法 |
| JP2709658B2 (ja) * | 1991-04-30 | 1998-02-04 | 第一工業製薬株式会社 | ロジン系エマルジョンサイズ剤用乳化分散剤及びサイズ剤 |
| US5264530A (en) * | 1992-05-01 | 1993-11-23 | E. I. Du Pont De Nemours And Company | Process of polymerization in an aqueous system |
| JPH06172459A (ja) * | 1992-12-09 | 1994-06-21 | Nippon Oil & Fats Co Ltd | 変性ポリオレフィンの製造方法 |
| JPH0910686A (ja) * | 1995-06-27 | 1997-01-14 | Nippon Paint Co Ltd | 複層塗膜の形成方法 |
| US6100350A (en) * | 1996-02-23 | 2000-08-08 | E. I. Du Pont De Nemours And Company | Branched polymer synthesis |
| JP3763008B2 (ja) * | 1996-12-09 | 2006-04-05 | 第一工業製薬株式会社 | 紙塗被剤用保水剤 |
| JPH10333269A (ja) * | 1997-06-02 | 1998-12-18 | Fuji Photo Film Co Ltd | ハロゲン化銀写真感光材料 |
| JP3799779B2 (ja) * | 1997-10-17 | 2006-07-19 | 第一工業製薬株式会社 | 紙塗被剤用保水剤 |
| US6884562B1 (en) * | 1998-10-27 | 2005-04-26 | E. I. Du Pont De Nemours And Company | Photoresists and processes for microlithography |
| JP2000169531A (ja) * | 1998-12-03 | 2000-06-20 | Kansai Paint Co Ltd | ブロック共重合体の製造方法 |
| JP2000239334A (ja) * | 1999-02-23 | 2000-09-05 | Kansai Paint Co Ltd | 分岐ポリマーの製造方法 |
| US20020072580A1 (en) * | 2000-01-26 | 2002-06-13 | Aert Huub Van | Method of emulsion polymerization |
| JP2002005887A (ja) * | 2000-06-26 | 2002-01-09 | Kawamura Inst Of Chem Res | 親水性接液部を有する微小ケミカルデバイスの製造方法 |
| US6395850B1 (en) * | 2000-09-28 | 2002-05-28 | Symyx Technologies, Inc. | Heterocycle containing control agents for living-type free radical polymerization |
| JP2002194037A (ja) * | 2000-10-13 | 2002-07-10 | Kansai Paint Co Ltd | 顔料分散樹脂及びこの樹脂を含有する水性顔料分散体 |
| JP2003055416A (ja) * | 2001-08-22 | 2003-02-26 | Kansai Paint Co Ltd | 顔料分散樹脂の製造方法 |
| US6872789B2 (en) * | 2001-11-07 | 2005-03-29 | Akzo Nobel N.V. | Cross-linkable polymer composition |
| JP3928416B2 (ja) * | 2001-11-19 | 2007-06-13 | 星光Ｐｍｃ株式会社 | ロジン系エマルション組成物、紙のサイジング方法及び紙 |
| AU2003219972A1 (en) * | 2002-03-04 | 2003-09-22 | Symyx Technologies, Inc. | Copolymers for use in capillary electrophoretic separation media |
| JP2004099627A (ja) * | 2002-07-16 | 2004-04-02 | Kansai Paint Co Ltd | 非水系重合体微粒子分散液、非水系ポリウレタン微粒子分散液およびそれらを用いた塗料組成物 |
| JP2005112878A (ja) * | 2003-10-02 | 2005-04-28 | Nippon Shokubai Co Ltd | 重合体の水系分散体の製造方法 |
| JP5110764B2 (ja) * | 2003-10-07 | 2012-12-26 | キヤノン株式会社 | インクジェット用顔料分散インク、インクセット、インクタンク、記録ユニット、インクジェット記録装置、インクジェット記録方法及びインクジェット用顔料分散インクの製造方法 |
| JP2006169345A (ja) * | 2004-12-15 | 2006-06-29 | Canon Inc | インクジェット用顔料インク、インクセット、画像形成方法及び画像記録装置 |
-
2007
- 2007-03-28 JP JP2009502335A patent/JP5388841B2/ja not_active Expired - Fee Related
- 2007-03-28 DE DE602007010256T patent/DE602007010256D1/de active Active
- 2007-03-28 AT AT07736581T patent/ATE486893T1/de not_active IP Right Cessation
- 2007-03-28 WO PCT/IN2007/000125 patent/WO2007110882A1/en not_active Ceased
- 2007-03-28 EP EP07736581A patent/EP1999162B1/en not_active Not-in-force
- 2007-03-28 US US12/280,225 patent/US7875659B2/en not_active Expired - Fee Related
- 2007-03-28 CA CA002645436A patent/CA2645436A1/en not_active Abandoned
Also Published As
| Publication number | Publication date |
|---|---|
| EP1999162A1 (en) | 2008-12-10 |
| JP2009531514A (ja) | 2009-09-03 |
| EP1999162B1 (en) | 2010-11-03 |
| DE602007010256D1 (de) | 2010-12-16 |
| US7875659B2 (en) | 2011-01-25 |
| WO2007110882A1 (en) | 2007-10-04 |
| JP5388841B2 (ja) | 2014-01-15 |
| US20090221729A1 (en) | 2009-09-03 |
| ATE486893T1 (de) | 2010-11-15 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FZDE | Discontinued |
Effective date: 20130328 |