NZ529669A - Use of reactive polymeric surfactants in the formation of emulsions - Google Patents
Use of reactive polymeric surfactants in the formation of emulsionsInfo
- Publication number
- NZ529669A NZ529669A NZ529669A NZ52966902A NZ529669A NZ 529669 A NZ529669 A NZ 529669A NZ 529669 A NZ529669 A NZ 529669A NZ 52966902 A NZ52966902 A NZ 52966902A NZ 529669 A NZ529669 A NZ 529669A
- Authority
- NZ
- New Zealand
- Prior art keywords
- group
- methacrylate
- phase
- cross
- process according
- Prior art date
Links
- 239000000839 emulsion Substances 0.000 title claims abstract description 116
- 239000004094 surface-active agent Substances 0.000 title description 139
- 230000015572 biosynthetic process Effects 0.000 title description 11
- 239000000178 monomer Substances 0.000 claims abstract description 122
- 238000000034 method Methods 0.000 claims abstract description 100
- 238000004132 cross linking Methods 0.000 claims abstract description 81
- 230000008569 process Effects 0.000 claims abstract description 72
- 239000003094 microcapsule Substances 0.000 claims abstract description 67
- 230000002209 hydrophobic effect Effects 0.000 claims abstract description 58
- 239000003381 stabilizer Substances 0.000 claims abstract description 37
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 35
- 239000007788 liquid Substances 0.000 claims abstract description 27
- 229920001400 block copolymer Polymers 0.000 claims abstract description 23
- 229920000578 graft copolymer Polymers 0.000 claims abstract description 21
- 239000000126 substance Substances 0.000 claims abstract description 20
- 238000004519 manufacturing process Methods 0.000 claims abstract description 13
- 125000002348 vinylic group Chemical group 0.000 claims abstract description 13
- 239000007764 o/w emulsion Substances 0.000 claims abstract description 11
- 238000006482 condensation reaction Methods 0.000 claims abstract description 7
- 230000000269 nucleophilic effect Effects 0.000 claims abstract description 7
- 238000007344 nucleophilic reaction Methods 0.000 claims abstract description 6
- 125000005647 linker group Chemical group 0.000 claims abstract description 4
- -1 cycloaklyl group Chemical group 0.000 claims description 64
- 238000006243 chemical reaction Methods 0.000 claims description 41
- 239000000463 material Substances 0.000 claims description 40
- WOBHKFSMXKNTIM-UHFFFAOYSA-N Hydroxyethyl methacrylate Chemical compound CC(=C)C(=O)OCCO WOBHKFSMXKNTIM-UHFFFAOYSA-N 0.000 claims description 31
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 claims description 28
- 229910052739 hydrogen Inorganic materials 0.000 claims description 28
- 239000001257 hydrogen Substances 0.000 claims description 27
- 239000012948 isocyanate Substances 0.000 claims description 26
- 150000002513 isocyanates Chemical class 0.000 claims description 25
- 150000003839 salts Chemical class 0.000 claims description 18
- 239000003999 initiator Substances 0.000 claims description 17
- 238000002360 preparation method Methods 0.000 claims description 17
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 16
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 15
- 125000000524 functional group Chemical group 0.000 claims description 15
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 14
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 claims description 14
- 229920001427 mPEG Polymers 0.000 claims description 14
- 229920001223 polyethylene glycol Polymers 0.000 claims description 14
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 13
- 239000002202 Polyethylene glycol Substances 0.000 claims description 13
- KWIUHFFTVRNATP-UHFFFAOYSA-O N,N,N-trimethylglycinium Chemical group C[N+](C)(C)CC(O)=O KWIUHFFTVRNATP-UHFFFAOYSA-O 0.000 claims description 12
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 claims description 12
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 12
- JKNCOURZONDCGV-UHFFFAOYSA-N 2-(dimethylamino)ethyl 2-methylprop-2-enoate Chemical class CN(C)CCOC(=O)C(C)=C JKNCOURZONDCGV-UHFFFAOYSA-N 0.000 claims description 11
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims description 11
- 150000001412 amines Chemical class 0.000 claims description 11
- 239000002775 capsule Substances 0.000 claims description 11
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 claims description 10
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 claims description 10
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 10
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 10
- 229920001730 Moisture cure polyurethane Polymers 0.000 claims description 9
- ZEWLHMQYEZXSBH-UHFFFAOYSA-N 4-[2-(2-methylprop-2-enoyloxy)ethoxy]-4-oxobutanoic acid Chemical compound CC(=C)C(=O)OCCOC(=O)CCC(O)=O ZEWLHMQYEZXSBH-UHFFFAOYSA-N 0.000 claims description 8
- 229920001451 polypropylene glycol Polymers 0.000 claims description 8
- 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 7
- DVKJHBMWWAPEIU-UHFFFAOYSA-N toluene 2,4-diisocyanate Chemical group CC1=CC=C(N=C=O)C=C1N=C=O DVKJHBMWWAPEIU-UHFFFAOYSA-N 0.000 claims description 7
- QLIBJPGWWSHWBF-UHFFFAOYSA-N 2-aminoethyl methacrylate Chemical compound CC(=C)C(=O)OCCN QLIBJPGWWSHWBF-UHFFFAOYSA-N 0.000 claims description 6
- IRQWEODKXLDORP-UHFFFAOYSA-N 4-ethenylbenzoic acid Chemical compound OC(=O)C1=CC=C(C=C)C=C1 IRQWEODKXLDORP-UHFFFAOYSA-N 0.000 claims description 6
- SUPCQIBBMFXVTL-UHFFFAOYSA-N ethyl 2-methylprop-2-enoate Chemical class CCOC(=O)C(C)=C SUPCQIBBMFXVTL-UHFFFAOYSA-N 0.000 claims description 6
- 239000000725 suspension Substances 0.000 claims description 6
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims description 5
- 235000011054 acetic acid Nutrition 0.000 claims description 5
- 229960000583 acetic acid Drugs 0.000 claims description 5
- 239000012868 active agrochemical ingredient Substances 0.000 claims description 5
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 5
- 150000002734 metacrylic acid derivatives Chemical class 0.000 claims description 5
- 159000000000 sodium salts Chemical class 0.000 claims description 5
- BDHFUVZGWQCTTF-UHFFFAOYSA-N sulfonic acid Chemical compound OS(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-N 0.000 claims description 5
- 239000004548 suspo-emulsion Substances 0.000 claims description 5
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 claims description 4
- JAHNSTQSQJOJLO-UHFFFAOYSA-N 2-(3-fluorophenyl)-1h-imidazole Chemical compound FC1=CC=CC(C=2NC=CN=2)=C1 JAHNSTQSQJOJLO-UHFFFAOYSA-N 0.000 claims description 4
- FUGYGGDSWSUORM-UHFFFAOYSA-N 4-hydroxystyrene Chemical compound OC1=CC=C(C=C)C=C1 FUGYGGDSWSUORM-UHFFFAOYSA-N 0.000 claims description 4
- 229920003171 Poly (ethylene oxide) Polymers 0.000 claims description 4
- 125000002877 alkyl aryl group Chemical group 0.000 claims description 4
- QHJGZUSJKGVMTF-UHFFFAOYSA-N canolol Chemical compound COC1=CC(C=C)=CC(OC)=C1O QHJGZUSJKGVMTF-UHFFFAOYSA-N 0.000 claims description 4
- 239000004490 capsule suspension Substances 0.000 claims description 4
- 150000002148 esters Chemical class 0.000 claims description 4
- 229910052736 halogen Inorganic materials 0.000 claims description 4
- LVHBHZANLOWSRM-UHFFFAOYSA-N methylenebutanedioic acid Natural products OC(=O)CC(=C)C(O)=O LVHBHZANLOWSRM-UHFFFAOYSA-N 0.000 claims description 4
- 238000000386 microscopy Methods 0.000 claims description 4
- 150000002924 oxiranes Chemical class 0.000 claims description 4
- 239000005056 polyisocyanate Substances 0.000 claims description 4
- 229920001228 polyisocyanate Polymers 0.000 claims description 4
- 229920000036 polyvinylpyrrolidone Polymers 0.000 claims description 4
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 claims description 4
- 150000003242 quaternary ammonium salts Chemical class 0.000 claims description 4
- 150000003440 styrenes Chemical class 0.000 claims description 4
- 229920001567 vinyl ester resin Polymers 0.000 claims description 4
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 4
- 229920002554 vinyl polymer Polymers 0.000 claims description 4
- PSBDWGZCVUAZQS-UHFFFAOYSA-N (dimethylsulfonio)acetate Chemical compound C[S+](C)CC([O-])=O PSBDWGZCVUAZQS-UHFFFAOYSA-N 0.000 claims description 3
- PRAMZQXXPOLCIY-UHFFFAOYSA-N 2-(2-methylprop-2-enoyloxy)ethanesulfonic acid Chemical compound CC(=C)C(=O)OCCS(O)(=O)=O PRAMZQXXPOLCIY-UHFFFAOYSA-N 0.000 claims description 3
- CWNNYYIZGGDCHS-UHFFFAOYSA-N 2-methylideneglutaric acid Chemical compound OC(=O)CCC(=C)C(O)=O CWNNYYIZGGDCHS-UHFFFAOYSA-N 0.000 claims description 3
- 229920001807 Urea-formaldehyde Polymers 0.000 claims description 3
- 125000005119 alkyl cycloalkyl group Chemical group 0.000 claims description 3
- 239000003795 chemical substances by application Substances 0.000 claims description 3
- 229920000435 poly(dimethylsiloxane) Polymers 0.000 claims description 3
- 229940117986 sulfobetaine Drugs 0.000 claims description 3
- DDKMFQGAZVMXQV-UHFFFAOYSA-N (3-chloro-2-hydroxypropyl) 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCC(O)CCl DDKMFQGAZVMXQV-UHFFFAOYSA-N 0.000 claims description 2
- CLECMSNCZUMKLM-UHFFFAOYSA-N (4-ethenylphenyl)methanol Chemical compound OCC1=CC=C(C=C)C=C1 CLECMSNCZUMKLM-UHFFFAOYSA-N 0.000 claims description 2
- TVXNKQRAZONMHJ-UHFFFAOYSA-M (4-ethenylphenyl)methyl-trimethylazanium;chloride Chemical compound [Cl-].C[N+](C)(C)CC1=CC=C(C=C)C=C1 TVXNKQRAZONMHJ-UHFFFAOYSA-M 0.000 claims description 2
- 125000004400 (C1-C12) alkyl group Chemical group 0.000 claims description 2
- ZFHGXWPMULPQSE-SZGBIDFHSA-N (Z)-(1S)-cis-tefluthrin Chemical compound FC1=C(F)C(C)=C(F)C(F)=C1COC(=O)[C@@H]1C(C)(C)[C@@H]1\C=C(/Cl)C(F)(F)F ZFHGXWPMULPQSE-SZGBIDFHSA-N 0.000 claims description 2
- QRIMLDXJAPZHJE-UHFFFAOYSA-N 2,3-dihydroxypropyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCC(O)CO QRIMLDXJAPZHJE-UHFFFAOYSA-N 0.000 claims description 2
- OLQFXOWPTQTLDP-UHFFFAOYSA-N 2-(2-hydroxyethoxy)ethyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCOCCO OLQFXOWPTQTLDP-UHFFFAOYSA-N 0.000 claims description 2
- DPBJAVGHACCNRL-UHFFFAOYSA-N 2-(dimethylamino)ethyl prop-2-enoate Chemical class CN(C)CCOC(=O)C=C DPBJAVGHACCNRL-UHFFFAOYSA-N 0.000 claims description 2
- FIQBJLHOPOSODG-UHFFFAOYSA-N 2-[2-(2-methylprop-2-enoyloxy)ethoxycarbonyl]benzoic acid Chemical compound CC(=C)C(=O)OCCOC(=O)C1=CC=CC=C1C(O)=O FIQBJLHOPOSODG-UHFFFAOYSA-N 0.000 claims description 2
- VHSHLMUCYSAUQU-UHFFFAOYSA-N 2-hydroxypropyl methacrylate Chemical compound CC(O)COC(=O)C(C)=C VHSHLMUCYSAUQU-UHFFFAOYSA-N 0.000 claims description 2
- YOMSJEATGXXYPX-UHFFFAOYSA-N 2-methoxy-4-vinylphenol Chemical compound COC1=CC(C=C)=CC=C1O YOMSJEATGXXYPX-UHFFFAOYSA-N 0.000 claims description 2
- GNSFRPWPOGYVLO-UHFFFAOYSA-N 3-hydroxypropyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCCO GNSFRPWPOGYVLO-UHFFFAOYSA-N 0.000 claims description 2
- LBSXSAXOLABXMF-UHFFFAOYSA-N 4-Vinylaniline Chemical compound NC1=CC=C(C=C)C=C1 LBSXSAXOLABXMF-UHFFFAOYSA-N 0.000 claims description 2
- OKWGNTXMGLDWLZ-UHFFFAOYSA-N 4-[3-(2-methylprop-2-enoyloxy)propoxy]benzoic acid Chemical compound CC(=C)C(=O)OCCCOC1=CC=C(C(O)=O)C=C1 OKWGNTXMGLDWLZ-UHFFFAOYSA-N 0.000 claims description 2
- YKXAYLPDMSGWEV-UHFFFAOYSA-N 4-hydroxybutyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCCCO YKXAYLPDMSGWEV-UHFFFAOYSA-N 0.000 claims description 2
- PHQYPLKSOUDDCV-UHFFFAOYSA-N 4-phenyl-n-propan-2-ylbut-3-en-1-amine Chemical compound CC(C)NCCC=CC1=CC=CC=C1 PHQYPLKSOUDDCV-UHFFFAOYSA-N 0.000 claims description 2
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 claims description 2
- FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 claims description 2
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical group C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 claims description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 2
- 239000005939 Tefluthrin Substances 0.000 claims description 2
- XZTNLXPYTOHUBH-UHFFFAOYSA-N [2-ethenyl-3-(hydroxymethyl)-5-methoxyphenyl]methanol Chemical compound COC1=CC(CO)=C(C=C)C(CO)=C1 XZTNLXPYTOHUBH-UHFFFAOYSA-N 0.000 claims description 2
- LOPVAWVHGAWUPS-UHFFFAOYSA-M [2-hydroxy-3-(2-methylprop-2-enoyloxy)propyl]-trimethylazanium;chloride Chemical compound [Cl-].CC(=C)C(=O)OCC(O)C[N+](C)(C)C LOPVAWVHGAWUPS-UHFFFAOYSA-M 0.000 claims description 2
- AKCXOKXVIWTINO-UHFFFAOYSA-N [2-hydroxy-3-(3-triethoxysilylpropylamino)propyl] 2-methylprop-2-enoate Chemical compound CCO[Si](OCC)(OCC)CCCNCC(O)COC(=O)C(C)=C AKCXOKXVIWTINO-UHFFFAOYSA-N 0.000 claims description 2
- 150000001252 acrylic acid derivatives Chemical class 0.000 claims description 2
- YIOJGTBNHQAVBO-UHFFFAOYSA-N dimethyl-bis(prop-2-enyl)azanium Chemical class C=CC[N+](C)(C)CC=C YIOJGTBNHQAVBO-UHFFFAOYSA-N 0.000 claims description 2
- AFOSIXZFDONLBT-UHFFFAOYSA-N divinyl sulfone Chemical compound C=CS(=O)(=O)C=C AFOSIXZFDONLBT-UHFFFAOYSA-N 0.000 claims description 2
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 claims description 2
- 150000004820 halides Chemical group 0.000 claims description 2
- ZZSKMNCIAKKVRB-UHFFFAOYSA-N morpholin-4-yl-(2-nitrophenyl)methanone Chemical compound [O-][N+](=O)C1=CC=CC=C1C(=O)N1CCOCC1 ZZSKMNCIAKKVRB-UHFFFAOYSA-N 0.000 claims description 2
- 229920002432 poly(vinyl methyl ether) polymer Polymers 0.000 claims description 2
- 229920002401 polyacrylamide Polymers 0.000 claims description 2
- 239000001267 polyvinylpyrrolidone Substances 0.000 claims description 2
- 239000000600 sorbitol Substances 0.000 claims description 2
- 150000003573 thiols Chemical class 0.000 claims description 2
- 239000013638 trimer Substances 0.000 claims description 2
- NLVXSWCKKBEXTG-UHFFFAOYSA-N vinylsulfonic acid Chemical compound OS(=O)(=O)C=C NLVXSWCKKBEXTG-UHFFFAOYSA-N 0.000 claims description 2
- 125000001931 aliphatic group Chemical group 0.000 claims 2
- 125000003118 aryl group Chemical group 0.000 claims 2
- ODGAOXROABLFNM-UHFFFAOYSA-N polynoxylin Chemical compound O=C.NC(N)=O ODGAOXROABLFNM-UHFFFAOYSA-N 0.000 claims 2
- MTZUIIAIAKMWLI-UHFFFAOYSA-N 1,2-diisocyanatobenzene Chemical compound O=C=NC1=CC=CC=C1N=C=O MTZUIIAIAKMWLI-UHFFFAOYSA-N 0.000 claims 1
- OKKJMXCNNZVCPO-UHFFFAOYSA-N 2-(2-methylprop-2-enoyloxy)ethylphosphonic acid Chemical compound CC(=C)C(=O)OCCP(O)(O)=O OKKJMXCNNZVCPO-UHFFFAOYSA-N 0.000 claims 1
- KUQRLZZWFINMDP-BGNLRFAXSA-N 2-[(3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyethyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCOC1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O KUQRLZZWFINMDP-BGNLRFAXSA-N 0.000 claims 1
- UDXXYUDJOHIIDZ-UHFFFAOYSA-N 2-phosphonooxyethyl prop-2-enoate Chemical compound OP(O)(=O)OCCOC(=O)C=C UDXXYUDJOHIIDZ-UHFFFAOYSA-N 0.000 claims 1
- JONLCHNLLPMMNF-UHFFFAOYSA-N 4-ethenylbenzenesulfonic acid;2-methyl-2-(prop-2-enoylamino)propane-1-sulfonic acid Chemical compound OS(=O)(=O)C1=CC=C(C=C)C=C1.OS(=O)(=O)CC(C)(C)NC(=O)C=C JONLCHNLLPMMNF-UHFFFAOYSA-N 0.000 claims 1
- 239000005057 Hexamethylene diisocyanate Substances 0.000 claims 1
- 239000005058 Isophorone diisocyanate Substances 0.000 claims 1
- UJURFSDRMQAYSU-UHFFFAOYSA-N N=C=O.N=C=O.C1=CC=CC2=C(C=CC=C3)C3=C21 Chemical class N=C=O.N=C=O.C1=CC=CC2=C(C=CC=C3)C3=C21 UJURFSDRMQAYSU-UHFFFAOYSA-N 0.000 claims 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical group [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 claims 1
- 239000003905 agrochemical Substances 0.000 claims 1
- 229940124277 aminobutyric acid Drugs 0.000 claims 1
- 239000007900 aqueous suspension Substances 0.000 claims 1
- BTCSSZJGUNDROE-UHFFFAOYSA-N gamma-aminobutyric acid Chemical compound NCCCC(O)=O BTCSSZJGUNDROE-UHFFFAOYSA-N 0.000 claims 1
- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 claims 1
- NIMLQBUJDJZYEJ-UHFFFAOYSA-N isophorone diisocyanate Chemical compound CC1(C)CC(N=C=O)CC(C)(CN=C=O)C1 NIMLQBUJDJZYEJ-UHFFFAOYSA-N 0.000 claims 1
- 229910052751 metal Inorganic materials 0.000 claims 1
- 239000002184 metal Substances 0.000 claims 1
- 102200042269 rs864309693 Human genes 0.000 claims 1
- 125000001273 sulfonato group Chemical group [O-]S(*)(=O)=O 0.000 claims 1
- 229910021653 sulphate ion Chemical group 0.000 claims 1
- 239000012071 phase Substances 0.000 description 135
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical group OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 61
- 229920000642 polymer Polymers 0.000 description 45
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 43
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 33
- 239000000203 mixture Substances 0.000 description 33
- 102100026735 Coagulation factor VIII Human genes 0.000 description 25
- 101000911390 Homo sapiens Coagulation factor VIII Proteins 0.000 description 25
- 229920001577 copolymer Polymers 0.000 description 22
- ROFVEXUMMXZLPA-UHFFFAOYSA-N Bipyridyl Chemical compound N1=CC=CC=C1C1=CC=CC=N1 ROFVEXUMMXZLPA-UHFFFAOYSA-N 0.000 description 20
- 239000002245 particle Substances 0.000 description 20
- 229910021589 Copper(I) bromide Inorganic materials 0.000 description 19
- 238000011065 in-situ storage Methods 0.000 description 19
- 239000000047 product Substances 0.000 description 18
- 239000008346 aqueous phase Substances 0.000 description 17
- 238000009472 formulation Methods 0.000 description 16
- 239000000084 colloidal system Substances 0.000 description 14
- 125000000129 anionic group Chemical group 0.000 description 13
- 238000009833 condensation Methods 0.000 description 12
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 12
- KWIUHFFTVRNATP-UHFFFAOYSA-N Betaine Natural products C[N+](C)(C)CC([O-])=O KWIUHFFTVRNATP-UHFFFAOYSA-N 0.000 description 11
- 239000002253 acid Substances 0.000 description 11
- 229960003237 betaine Drugs 0.000 description 11
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 11
- 230000005494 condensation Effects 0.000 description 10
- 239000000243 solution Substances 0.000 description 10
- MGNFYQILYYYUBS-UHFFFAOYSA-N 1-[3-(4-tert-butylphenyl)-2-methylpropyl]piperidine Chemical compound C=1C=C(C(C)(C)C)C=CC=1CC(C)CN1CCCCC1 MGNFYQILYYYUBS-UHFFFAOYSA-N 0.000 description 9
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 9
- 239000005777 Fenpropidin Substances 0.000 description 9
- 230000004888 barrier function Effects 0.000 description 9
- 239000012074 organic phase Substances 0.000 description 8
- 229910021591 Copper(I) chloride Inorganic materials 0.000 description 7
- 125000003277 amino group Chemical group 0.000 description 7
- 125000002091 cationic group Chemical group 0.000 description 7
- OXBLHERUFWYNTN-UHFFFAOYSA-M copper(I) chloride Chemical compound [Cu]Cl OXBLHERUFWYNTN-UHFFFAOYSA-M 0.000 description 7
- 239000011162 core material Substances 0.000 description 7
- IOLQWGVDEFWYNP-UHFFFAOYSA-N ethyl 2-bromo-2-methylpropanoate Chemical compound CCOC(=O)C(C)(C)Br IOLQWGVDEFWYNP-UHFFFAOYSA-N 0.000 description 7
- 229920002451 polyvinyl alcohol Polymers 0.000 description 7
- 239000007787 solid Substances 0.000 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 description 6
- WVQBLGZPHOPPFO-UHFFFAOYSA-N 2-chloro-N-(2-ethyl-6-methylphenyl)-N-(1-methoxypropan-2-yl)acetamide Chemical compound CCC1=CC=CC(C)=C1N(C(C)COC)C(=O)CCl WVQBLGZPHOPPFO-UHFFFAOYSA-N 0.000 description 6
- 150000001718 carbodiimides Chemical class 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- WVQBLGZPHOPPFO-LBPRGKRZSA-N (S)-metolachlor Chemical compound CCC1=CC=CC(C)=C1N([C@@H](C)COC)C(=O)CCl WVQBLGZPHOPPFO-LBPRGKRZSA-N 0.000 description 5
- 239000004971 Cross linker Substances 0.000 description 5
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Classifications
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- B01J13/00—Colloid chemistry, e.g. the production of colloidal materials or their solutions, not otherwise provided for; Making microcapsules or microballoons
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- B01J13/14—Polymerisation; cross-linking
- B01J13/16—Interfacial polymerisation
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K23/00—Use of substances as emulsifying, wetting, dispersing, or foam-producing agents
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K23/00—Use of substances as emulsifying, wetting, dispersing, or foam-producing agents
- C09K23/14—Derivatives of phosphoric acid
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K23/00—Use of substances as emulsifying, wetting, dispersing, or foam-producing agents
- C09K23/16—Amines or polyamines
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K23/00—Use of substances as emulsifying, wetting, dispersing, or foam-producing agents
- C09K23/54—Silicon compounds
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- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S524/00—Synthetic resins or natural rubbers -- part of the class 520 series
- Y10S524/916—Hydrogel compositions
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- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T428/00—Stock material or miscellaneous articles
- Y10T428/29—Coated or structually defined flake, particle, cell, strand, strand portion, rod, filament, macroscopic fiber or mass thereof
- Y10T428/2982—Particulate matter [e.g., sphere, flake, etc.]
- Y10T428/2984—Microcapsule with fluid core [includes liposome]
- Y10T428/2985—Solid-walled microcapsule from synthetic polymer
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Dispersion Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Manufacturing Of Micro-Capsules (AREA)
- Emulsifying, Dispersing, Foam-Producing Or Wetting Agents (AREA)
- Colloid Chemistry (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Polymers With Sulfur, Phosphorus Or Metals In The Main Chain (AREA)
- Polyamides (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GBGB0114197.7A GB0114197D0 (en) | 2001-06-11 | 2001-06-11 | Reactive polymeric surfactants |
| PCT/GB2002/002744 WO2002100525A2 (en) | 2001-06-11 | 2002-06-10 | Use of reactive polymeric surfactants in the formation of emulsions |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NZ529669A true NZ529669A (en) | 2006-08-31 |
Family
ID=9916350
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NZ529669A NZ529669A (en) | 2001-06-11 | 2002-06-10 | Use of reactive polymeric surfactants in the formation of emulsions |
Country Status (21)
| Country | Link |
|---|---|
| US (1) | US7199185B2 (OSRAM) |
| EP (1) | EP1401562B1 (OSRAM) |
| JP (1) | JP4399252B2 (OSRAM) |
| CN (1) | CN100415354C (OSRAM) |
| AT (1) | ATE410222T1 (OSRAM) |
| AU (1) | AU2002314315B2 (OSRAM) |
| BR (1) | BR0210302B1 (OSRAM) |
| CA (1) | CA2447759C (OSRAM) |
| CZ (1) | CZ304798B6 (OSRAM) |
| DE (1) | DE60229249D1 (OSRAM) |
| EA (1) | EA007354B1 (OSRAM) |
| ES (1) | ES2311057T3 (OSRAM) |
| GB (1) | GB0114197D0 (OSRAM) |
| IL (2) | IL159062A0 (OSRAM) |
| MX (1) | MXPA03011379A (OSRAM) |
| NO (1) | NO331666B1 (OSRAM) |
| NZ (1) | NZ529669A (OSRAM) |
| PL (1) | PL220597B1 (OSRAM) |
| RS (1) | RS50940B (OSRAM) |
| WO (1) | WO2002100525A2 (OSRAM) |
| ZA (1) | ZA200309057B (OSRAM) |
Families Citing this family (75)
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|---|---|---|---|---|
| GB0114197D0 (en) * | 2001-06-11 | 2001-08-01 | Syngenta Ltd | Reactive polymeric surfactants |
| US6828025B2 (en) | 2002-05-24 | 2004-12-07 | Mcmaster University | Microencapsulation of polar liquids in copolymer shells |
| FR2846973B1 (fr) * | 2002-11-07 | 2004-12-17 | Rhodia Chimie Sa | Composition d'antifroissage comprenant un copolymere a architecture controlee, pour articles en fibres textiles |
| GB0228537D0 (en) * | 2002-12-06 | 2003-01-15 | Syngenta Ltd | Particulate suspensions |
| US20040137031A1 (en) * | 2002-12-13 | 2004-07-15 | Monsanto Technology Llc | Microcapsules with amine adjusted release rates |
| WO2005025736A1 (en) * | 2003-09-05 | 2005-03-24 | University Of Massachusetts | Amphiphilic polymer capsules and related methods of interfacial assembly |
| JP4562364B2 (ja) * | 2003-09-12 | 2010-10-13 | 日本曹達株式会社 | ブロック・グラフト共重合体及びそれらを用いた高分子固体電解質 |
| AU2005253972A1 (en) * | 2004-06-14 | 2005-12-29 | Monsanto Technology Llc | Microcapsules having activated release of core material therein |
| GB0505569D0 (en) * | 2005-03-18 | 2005-04-27 | Syngenta Ltd | Formulations |
| US7363978B2 (en) * | 2005-05-20 | 2008-04-29 | Halliburton Energy Services, Inc. | Methods of using reactive surfactants in subterranean operations |
| EP1960447A4 (en) | 2005-12-08 | 2010-12-01 | Tyco Healthcare | BIOCOMPATIBLE SURGICAL COMPOSITIONS |
| BRPI0710112A2 (pt) * | 2006-03-30 | 2011-08-02 | Rhodia | agentes tensoativos reativos e seus usos em emulsõs e dispersões |
| US8119733B2 (en) | 2006-03-30 | 2012-02-21 | Rhodia Operations | Reactive monomeric surfactants |
| EA200900482A1 (ru) * | 2006-10-05 | 2009-10-30 | Басф Се | Гребенчатые полимеры и их применение для получения композиций действующего или эффективного вещества |
| EP2088855B1 (en) * | 2006-11-30 | 2010-03-24 | Basf Se | Agrochemical formulations comprising co-polymers based on ethylenically unsaturated dicarboxylic mono and diesters |
| DE102007060175A1 (de) * | 2007-12-13 | 2009-06-18 | Johannes Gutenberg-Universität Mainz | Quartärnisierung des Zusatzstoffs Aminoalkyl Methacrylat Copolymer E zur Verbesserung der Permeabilität und Löslichkeit von Arzneistoffen |
| MX339903B (es) | 2009-02-13 | 2016-06-15 | Monsanto Technology Llc | Encapsulacion de herbicidas para reducir daños en cultivos. |
| EP2421361B8 (en) | 2009-04-22 | 2019-09-18 | Nouryon Chemicals International B.V. | Dispersants for agricultural applications |
| AU2010261875B2 (en) * | 2009-06-15 | 2016-02-11 | Basf Se | Microcapsules having highly branched polymers as cross-linking agents |
| DE102009030411A1 (de) * | 2009-06-25 | 2010-12-30 | Clariant International Limited | Wasser-in-Öl-Emulsion und Verfahren zu ihrer Herstellung |
| EP2454334A1 (en) * | 2009-07-15 | 2012-05-23 | E. I. du Pont de Nemours and Company | Crosslinking pigment dispersion based on diblock polymeric dispersants |
| US8591021B2 (en) | 2009-07-15 | 2013-11-26 | E I Du Pont De Nemours And Company | Method of printing using ink jet inks comprising a crosslinking pigment dispersion based on diblock polymeric dispersants |
| US8591020B2 (en) | 2009-07-15 | 2013-11-26 | E I Du Pont De Nemours And Company | Aqueous ink jet ink comprising a crosslinking pigment dispersion based on diblock polymeric dispersants |
| EP3483610B1 (en) | 2009-11-09 | 2025-09-10 | University Of Washington Center For Commercialization | Functionalized chromophoric polymer dots and bioconjugates thereof |
| US8715544B2 (en) | 2009-12-21 | 2014-05-06 | Appvion, Inc. | Hydrophilic liquid encapsulates |
| WO2011119903A2 (en) * | 2010-03-26 | 2011-09-29 | Surmodics Pharmaceuticals Inc. | Emulsions for microencapsulation comprising biodegradable surface-active block copolymers as stabilizers |
| CN101845122B (zh) * | 2010-06-11 | 2012-07-25 | 成都达威化工科技有限公司 | 水性高分子颜料分散剂及由其制备的皮革阳离子颜料膏 |
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| BR112013004485B1 (pt) | 2010-08-18 | 2022-02-08 | Monsanto Technology Llc | Método para controle de ervas daninhas em campo de plantas de cultura |
| CN109233810B (zh) | 2010-10-18 | 2022-05-03 | 华盛顿大学商业化中心 | 发色聚合物点 |
| CN103347384B (zh) | 2011-01-24 | 2015-09-30 | 巴斯夫欧洲公司 | 包含包封农药的农业化学配制剂 |
| CN102179202A (zh) * | 2011-03-15 | 2011-09-14 | 赵争艳 | 一种两性梳形嵌段聚合物表面活性剂及其制备方法 |
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| US10465147B2 (en) * | 2011-10-17 | 2019-11-05 | Agency For Science, Technology And Research | Copolymers |
| US9797840B2 (en) | 2011-11-28 | 2017-10-24 | University Of Washington Through Its Center For Commercialization | Highly fluorescent polymer nanoparticle |
| JP6141872B2 (ja) | 2011-12-30 | 2017-06-07 | ユニバーシティ オブ ワシントン スルー イッツ センター フォー コマーシャリゼーション | 狭帯域発光を有する蛍光性ポリマードット |
| US10067139B2 (en) | 2012-02-03 | 2018-09-04 | University Of Washington Through Its Center For Commercialization | Polyelectrolyte-coated polymer dots and related methods |
| ES2480343B1 (es) * | 2013-01-25 | 2015-05-20 | Ecopol Tech, S.L. | Procedimiento para la fabricación de un microencapsulado y compuesto anfifílico reactivo, microencapsulado y composición correspondientes |
| CN111983219A (zh) | 2013-03-14 | 2020-11-24 | 华盛顿大学商业中心 | 聚合物点组合物和相关方法 |
| CN103193927B (zh) * | 2013-04-27 | 2016-01-20 | 南京构友生物材料有限公司 | 可键合的血液友好聚合物及其制法与用途 |
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| TW201613688A (en) * | 2014-02-18 | 2016-04-16 | Rohm & Haas | Microcapsules |
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| ES2778631T3 (es) * | 2015-06-22 | 2020-08-11 | Spcm Sa | Uso de un copolímero anfolito como estabilizador coloidal |
| CN107708853B (zh) * | 2015-10-27 | 2021-12-07 | 恩盖普有限公司 | 包封 |
| DE102015014912B4 (de) * | 2015-11-18 | 2017-09-28 | Urotech Gmbh | Beschichtung für ein medizinisches Instrument, Verfahren zu dessen Beschichten und mit diesem Verfahren beschichtetes medizinisches Instrument |
| JP2017190424A (ja) * | 2016-04-15 | 2017-10-19 | 竹本油脂株式会社 | ビニル共重合体 |
| CN105797660B (zh) * | 2016-04-18 | 2019-02-15 | 天津工业大学 | 一种油溶性醚化氨基树脂制备胶囊的方法 |
| AU2017272086B2 (en) | 2016-05-23 | 2019-06-27 | Ecolab Usa Inc. | Reduced misting alkaline and neutral cleaning, sanitizing, and disinfecting compositions via the use of high molecular weight water-in-oil emulsion polymers |
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| GB201612678D0 (en) * | 2016-07-21 | 2016-09-07 | Bp Exploration Operating | Process |
| EP3496759B1 (en) * | 2016-08-09 | 2022-03-16 | The University of Liverpool | Ophthalmic compositions |
| GB201615905D0 (en) * | 2016-09-19 | 2016-11-02 | Givaudan Sa | Improvements in or relating to organic compounds |
| EP3295929A1 (en) * | 2016-09-19 | 2018-03-21 | S.P.C.M. Sa | Use of an ampholyte copolymer as colloidal stabilizer in a process of encapsulating fragrance |
| CN106634548B (zh) * | 2016-12-15 | 2019-01-29 | 烟台隆达树脂有限公司 | 一种聚氨酯/丙烯酸酯杂化乳液及其制备方法 |
| JP6986571B2 (ja) * | 2017-01-24 | 2021-12-22 | アグファ・ナームローゼ・フェンノートシャップAgfa Nv | カチオン分散基により安定化されたカプセル |
| AU2018227539B2 (en) | 2017-03-01 | 2020-04-09 | Ecolab Usa Inc. | Reduced inhalation hazard sanitizers and disinfectants via high molecular weight polymers |
| WO2018231913A1 (en) | 2017-06-13 | 2018-12-20 | Monsanto Technology Llc | Microencapsulated herbicides |
| JP2021511195A (ja) * | 2017-11-06 | 2021-05-06 | ダウ グローバル テクノロジーズ エルエルシー | 非水系カプセル化 |
| GB201721584D0 (en) * | 2017-12-21 | 2018-02-07 | Givaudan Sa | Improvements in or relating to organic compounds |
| CN108586758B (zh) * | 2018-05-10 | 2020-10-16 | 宁波新斯维箱包有限公司 | 微胶囊及其制备方法 |
| CN109293811B (zh) * | 2018-09-30 | 2020-08-04 | 菏泽学院 | 一种聚甲基丙烯酸n，n-二甲氨基乙酯的液液界面合成方法及应用 |
| WO2020098981A1 (en) * | 2018-11-16 | 2020-05-22 | MAX-PLANCK-Gesellschaft zur Förderung der Wissenschaften e.V. | Surfactant-stabilized fluid interface and dispersion comprising one or more droplets having a surfactant stabilized fluid interface |
| UA129154C2 (uk) | 2019-01-30 | 2025-01-29 | Монсанто Текнолоджі Ллс | Мікрокапсульовані ацетамідні гербіциди |
| EP3997199A1 (en) | 2019-07-12 | 2022-05-18 | Ecolab USA Inc. | Reduced mist alkaline cleaner via the use of alkali soluble emulsion polymers |
| CN110745929B (zh) * | 2019-10-17 | 2021-08-06 | 苏州赛维科环保技术服务有限公司 | 一种乳液絮凝剂 |
| WO2021175691A1 (en) * | 2020-03-06 | 2021-09-10 | Basf Se | New agrochemical formulations |
| WO2022006703A1 (en) * | 2020-07-06 | 2022-01-13 | Dic Corporation | Composition, coating formulation, and multilayer body |
| CN112279970B (zh) * | 2020-10-21 | 2022-04-01 | 江苏海洋大学 | 一种端羟基聚合物在制备多功能互穿网络聚合物中的应用 |
| CN115612163A (zh) * | 2022-11-08 | 2023-01-17 | 浙江大学 | 一种发泡微胶囊的制备方法 |
| CN116178796B (zh) * | 2023-02-27 | 2025-02-11 | 山东高速路用新材料技术有限公司 | 一种包覆型硫化剂、沥青稳定剂及其制备方法和应用 |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5089259A (en) * | 1988-12-19 | 1992-02-18 | Dowelanco | Stable concentrates and emulsions of water-insoluble organic pesticides |
| CA2005883C (en) * | 1988-12-19 | 1999-10-05 | Dow Agrosciences Llc | Stable emulsions of water-insoluble organic pesticides |
| US4977059A (en) * | 1989-05-12 | 1990-12-11 | The Mead Corporation | Sulfonated-ethylene oxide dispersants for use in preparing amine-formaldehyde microcapsules |
| JPH07246329A (ja) * | 1994-03-09 | 1995-09-26 | Nippon Paint Co Ltd | マイクロカプセルの製造方法及びマイクロカプセル |
| EP0766705B1 (en) * | 1994-06-24 | 1998-05-13 | The Dow Chemical Company | Preparation of amphipathic graft copolymers, compositions thereof, and methods of their use |
| AU716712B2 (en) * | 1995-12-29 | 2000-03-02 | Ciba Specialty Chemicals Water Treatments Limited | Particles having a polymeric shell and their production |
| US6262152B1 (en) | 1998-10-06 | 2001-07-17 | E. I. Du Pont De Nemours And Company | Particles dispersed w/polymer dispersant having liquid soluble and cross-linkable insoluble segments |
| GB0114197D0 (en) * | 2001-06-11 | 2001-08-01 | Syngenta Ltd | Reactive polymeric surfactants |
-
2001
- 2001-06-11 GB GBGB0114197.7A patent/GB0114197D0/en not_active Ceased
-
2002
- 2002-06-10 CN CNB028156897A patent/CN100415354C/zh not_active Expired - Lifetime
- 2002-06-10 US US10/480,405 patent/US7199185B2/en not_active Expired - Lifetime
- 2002-06-10 EA EA200400025A patent/EA007354B1/ru not_active IP Right Cessation
- 2002-06-10 CZ CZ2003-3370A patent/CZ304798B6/cs not_active IP Right Cessation
- 2002-06-10 BR BRPI0210302-8A patent/BR0210302B1/pt not_active IP Right Cessation
- 2002-06-10 CA CA2447759A patent/CA2447759C/en not_active Expired - Fee Related
- 2002-06-10 JP JP2003503338A patent/JP4399252B2/ja not_active Expired - Fee Related
- 2002-06-10 DE DE60229249T patent/DE60229249D1/de not_active Expired - Lifetime
- 2002-06-10 WO PCT/GB2002/002744 patent/WO2002100525A2/en not_active Ceased
- 2002-06-10 PL PL366467A patent/PL220597B1/pl unknown
- 2002-06-10 RS YUP-976/03A patent/RS50940B/sr unknown
- 2002-06-10 EP EP02740885A patent/EP1401562B1/en not_active Expired - Lifetime
- 2002-06-10 ES ES02740885T patent/ES2311057T3/es not_active Expired - Lifetime
- 2002-06-10 AT AT02740885T patent/ATE410222T1/de not_active IP Right Cessation
- 2002-06-10 MX MXPA03011379A patent/MXPA03011379A/es active IP Right Grant
- 2002-06-10 AU AU2002314315A patent/AU2002314315B2/en not_active Ceased
- 2002-06-10 NZ NZ529669A patent/NZ529669A/en not_active IP Right Cessation
- 2002-06-10 IL IL15906202A patent/IL159062A0/xx active IP Right Grant
-
2003
- 2003-11-20 ZA ZA200309057A patent/ZA200309057B/en unknown
- 2003-11-26 IL IL159062A patent/IL159062A/en not_active IP Right Cessation
- 2003-12-10 NO NO20035487A patent/NO331666B1/no not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| EA007354B1 (ru) | 2006-10-27 |
| IL159062A (en) | 2007-07-04 |
| GB0114197D0 (en) | 2001-08-01 |
| WO2002100525A3 (en) | 2003-07-31 |
| DE60229249D1 (de) | 2008-11-20 |
| WO2002100525A2 (en) | 2002-12-19 |
| CN100415354C (zh) | 2008-09-03 |
| JP2004537610A (ja) | 2004-12-16 |
| US20040197357A1 (en) | 2004-10-07 |
| EP1401562A2 (en) | 2004-03-31 |
| JP4399252B2 (ja) | 2010-01-13 |
| CA2447759C (en) | 2011-04-26 |
| NO331666B1 (no) | 2012-02-20 |
| BR0210302A (pt) | 2004-07-13 |
| NO20035487D0 (no) | 2003-12-10 |
| CZ20033370A3 (cs) | 2004-05-12 |
| CZ304798B6 (cs) | 2014-10-29 |
| ZA200309057B (en) | 2004-09-17 |
| IL159062A0 (en) | 2004-05-12 |
| PL366467A1 (en) | 2005-02-07 |
| EP1401562B1 (en) | 2008-10-08 |
| CN1541136A (zh) | 2004-10-27 |
| MXPA03011379A (es) | 2004-04-05 |
| US7199185B2 (en) | 2007-04-03 |
| AU2002314315B2 (en) | 2006-12-21 |
| PL220597B1 (pl) | 2015-11-30 |
| BR0210302B1 (pt) | 2011-07-26 |
| ES2311057T3 (es) | 2009-02-01 |
| RS50940B (sr) | 2010-08-31 |
| ATE410222T1 (de) | 2008-10-15 |
| EA200400025A1 (ru) | 2004-04-29 |
| CA2447759A1 (en) | 2002-12-19 |
| YU97603A (sh) | 2006-05-25 |
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