CA2468696A1 - Graft copolymers of methylene lactones and process for emulsion polymerization of methylene lactones - Google Patents
Graft copolymers of methylene lactones and process for emulsion polymerization of methylene lactones Download PDFInfo
- Publication number
- CA2468696A1 CA2468696A1 CA002468696A CA2468696A CA2468696A1 CA 2468696 A1 CA2468696 A1 CA 2468696A1 CA 002468696 A CA002468696 A CA 002468696A CA 2468696 A CA2468696 A CA 2468696A CA 2468696 A1 CA2468696 A1 CA 2468696A1
- Authority
- CA
- Canada
- Prior art keywords
- polymer
- monomer
- methylene
- alpha
- formula
- 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 46
- 230000008569 process Effects 0.000 title claims description 23
- -1 methylene lactones Chemical class 0.000 title claims description 16
- 238000007720 emulsion polymerization reaction Methods 0.000 title abstract description 28
- 229920000578 graft copolymer Polymers 0.000 title abstract description 17
- 229920000642 polymer Polymers 0.000 claims abstract description 109
- 239000000178 monomer Substances 0.000 claims abstract description 105
- 239000000203 mixture Substances 0.000 claims abstract description 92
- GSLDEZOOOSBFGP-UHFFFAOYSA-N alpha-methylene gamma-butyrolactone Chemical compound C=C1CCOC1=O GSLDEZOOOSBFGP-UHFFFAOYSA-N 0.000 claims abstract description 88
- 229920001577 copolymer Polymers 0.000 claims abstract description 46
- 229920001169 thermoplastic Polymers 0.000 claims abstract description 17
- 239000011347 resin Substances 0.000 claims abstract description 16
- 229920005989 resin Polymers 0.000 claims abstract description 16
- 239000000839 emulsion Substances 0.000 claims description 76
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 claims description 38
- USHAGKDGDHPEEY-UHFFFAOYSA-L potassium persulfate Chemical group [K+].[K+].[O-]S(=O)(=O)OOS([O-])(=O)=O USHAGKDGDHPEEY-UHFFFAOYSA-L 0.000 claims description 33
- 125000001183 hydrocarbyl group Chemical group 0.000 claims description 30
- 239000003999 initiator Substances 0.000 claims description 22
- 229910052739 hydrogen Inorganic materials 0.000 claims description 20
- 239000001257 hydrogen Substances 0.000 claims description 20
- 229920006037 cross link polymer Polymers 0.000 claims description 18
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 claims description 17
- 125000000524 functional group Chemical group 0.000 claims description 17
- 238000005345 coagulation Methods 0.000 claims description 16
- 230000015271 coagulation Effects 0.000 claims description 16
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical group [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 claims description 14
- 229920006243 acrylic copolymer Polymers 0.000 claims description 13
- 229910052943 magnesium sulfate Inorganic materials 0.000 claims description 13
- 150000001875 compounds Chemical class 0.000 claims description 11
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 11
- 229920002554 vinyl polymer Polymers 0.000 claims description 11
- 150000001993 dienes Chemical class 0.000 claims description 10
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 claims description 8
- 238000001914 filtration Methods 0.000 claims description 8
- 230000009477 glass transition Effects 0.000 claims description 8
- 150000002431 hydrogen Chemical class 0.000 claims description 8
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 8
- 239000004094 surface-active agent Substances 0.000 claims description 8
- 238000006243 chemical reaction Methods 0.000 claims description 7
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 7
- 239000004816 latex Substances 0.000 claims description 7
- 229920000126 latex Polymers 0.000 claims description 7
- 235000019341 magnesium sulphate Nutrition 0.000 claims description 7
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 6
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 claims description 6
- 239000004952 Polyamide Substances 0.000 claims description 6
- 125000000217 alkyl group Chemical class 0.000 claims description 6
- 239000012986 chain transfer agent Substances 0.000 claims description 6
- 229920002647 polyamide Polymers 0.000 claims description 6
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims description 5
- 230000000379 polymerizing effect Effects 0.000 claims description 5
- 239000011591 potassium Substances 0.000 claims description 5
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims description 4
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims description 4
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 claims description 4
- RAHZWNYVWXNFOC-UHFFFAOYSA-N Sulphur dioxide Chemical compound O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 claims description 4
- 229910052783 alkali metal Inorganic materials 0.000 claims description 4
- 150000001340 alkali metals Chemical class 0.000 claims description 4
- 150000003863 ammonium salts Chemical class 0.000 claims description 4
- 229920000570 polyether Polymers 0.000 claims description 4
- 229910052700 potassium Inorganic materials 0.000 claims description 4
- 239000011734 sodium Substances 0.000 claims description 4
- 150000003467 sulfuric acid derivatives Chemical class 0.000 claims description 4
- KCNKJCHARANTIP-SNAWJCMRSA-N allyl-{4-[3-(4-bromo-phenyl)-benzofuran-6-yloxy]-but-2-enyl}-methyl-amine Chemical group C=1OC2=CC(OC/C=C/CN(CC=C)C)=CC=C2C=1C1=CC=C(Br)C=C1 KCNKJCHARANTIP-SNAWJCMRSA-N 0.000 claims description 3
- 125000004432 carbon atom Chemical group C* 0.000 claims description 3
- 239000000701 coagulant Substances 0.000 claims description 3
- 238000004108 freeze drying Methods 0.000 claims description 3
- 239000004417 polycarbonate Substances 0.000 claims description 3
- 229920000515 polycarbonate Polymers 0.000 claims description 3
- 229910052708 sodium Inorganic materials 0.000 claims description 3
- CIHOLLKRGTVIJN-UHFFFAOYSA-N tert‐butyl hydroperoxide Chemical compound CC(C)(C)OO CIHOLLKRGTVIJN-UHFFFAOYSA-N 0.000 claims description 3
- AOSFMYBATFLTAQ-UHFFFAOYSA-N 1-amino-3-(benzimidazol-1-yl)propan-2-ol Chemical compound C1=CC=C2N(CC(O)CN)C=NC2=C1 AOSFMYBATFLTAQ-UHFFFAOYSA-N 0.000 claims description 2
- FRIBMENBGGCKPD-UHFFFAOYSA-N 3-(2,3-dimethoxyphenyl)prop-2-enal Chemical compound COC1=CC=CC(C=CC=O)=C1OC FRIBMENBGGCKPD-UHFFFAOYSA-N 0.000 claims description 2
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 claims description 2
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Natural products OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 claims description 2
- UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 claims description 2
- CIWBSHSKHKDKBQ-DUZGATOHSA-N D-isoascorbic acid Chemical compound OC[C@@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-DUZGATOHSA-N 0.000 claims description 2
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical class S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 claims description 2
- CWYNVVGOOAEACU-UHFFFAOYSA-N Fe2+ Chemical class [Fe+2] CWYNVVGOOAEACU-UHFFFAOYSA-N 0.000 claims description 2
- YIVJZNGAASQVEM-UHFFFAOYSA-N Lauroyl peroxide Chemical compound CCCCCCCCCCCC(=O)OOC(=O)CCCCCCCCCCC YIVJZNGAASQVEM-UHFFFAOYSA-N 0.000 claims description 2
- 239000004721 Polyphenylene oxide Substances 0.000 claims description 2
- 239000004793 Polystyrene Substances 0.000 claims description 2
- 150000001298 alcohols Chemical class 0.000 claims description 2
- 125000002877 alkyl aryl group Chemical class 0.000 claims description 2
- 229940045714 alkyl sulfonate alkylating agent Drugs 0.000 claims description 2
- 150000001408 amides Chemical class 0.000 claims description 2
- 150000001412 amines Chemical class 0.000 claims description 2
- 125000003118 aryl group Chemical class 0.000 claims description 2
- 239000001110 calcium chloride Substances 0.000 claims description 2
- 229910001628 calcium chloride Inorganic materials 0.000 claims description 2
- 239000003638 chemical reducing agent Substances 0.000 claims description 2
- SPTHWAJJMLCAQF-UHFFFAOYSA-M ctk4f8481 Chemical compound [O-]O.CC(C)C1=CC=CC=C1C(C)C SPTHWAJJMLCAQF-UHFFFAOYSA-M 0.000 claims description 2
- LSXWFXONGKSEMY-UHFFFAOYSA-N di-tert-butyl peroxide Chemical compound CC(C)(C)OOC(C)(C)C LSXWFXONGKSEMY-UHFFFAOYSA-N 0.000 claims description 2
- ZQMIGQNCOMNODD-UHFFFAOYSA-N diacetyl peroxide Chemical class CC(=O)OOC(C)=O ZQMIGQNCOMNODD-UHFFFAOYSA-N 0.000 claims description 2
- 235000014113 dietary fatty acids Nutrition 0.000 claims description 2
- WBZKQQHYRPRKNJ-UHFFFAOYSA-L disulfite Chemical compound [O-]S(=O)S([O-])(=O)=O WBZKQQHYRPRKNJ-UHFFFAOYSA-L 0.000 claims description 2
- GRWZHXKQBITJKP-UHFFFAOYSA-L dithionite(2-) Chemical compound [O-]S(=O)S([O-])=O GRWZHXKQBITJKP-UHFFFAOYSA-L 0.000 claims description 2
- 235000010350 erythorbic acid Nutrition 0.000 claims description 2
- 150000002148 esters Chemical class 0.000 claims description 2
- 239000000194 fatty acid Substances 0.000 claims description 2
- 229930195729 fatty acid Natural products 0.000 claims description 2
- 150000004665 fatty acids Chemical class 0.000 claims description 2
- 229940026239 isoascorbic acid Drugs 0.000 claims description 2
- 150000002976 peresters Chemical class 0.000 claims description 2
- JRKICGRDRMAZLK-UHFFFAOYSA-L persulfate group Chemical group S(=O)(=O)([O-])OOS(=O)(=O)[O-] JRKICGRDRMAZLK-UHFFFAOYSA-L 0.000 claims description 2
- 229920000728 polyester Polymers 0.000 claims description 2
- 229920000098 polyolefin Polymers 0.000 claims description 2
- 229920006324 polyoxymethylene Polymers 0.000 claims description 2
- 229920002223 polystyrene Polymers 0.000 claims description 2
- 229920000915 polyvinyl chloride Polymers 0.000 claims description 2
- 238000010526 radical polymerization reaction Methods 0.000 claims description 2
- 239000011780 sodium chloride Substances 0.000 claims description 2
- 238000001694 spray drying Methods 0.000 claims description 2
- 229920000058 polyacrylate Polymers 0.000 claims 4
- 239000012736 aqueous medium Substances 0.000 claims 3
- 230000001112 coagulating effect Effects 0.000 claims 3
- BZHJMEDXRYGGRV-UHFFFAOYSA-N Vinyl chloride Chemical compound ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 claims 2
- NFGODEMQGQNUKK-UHFFFAOYSA-M [6-(diethylamino)-9-(2-octadecoxycarbonylphenyl)xanthen-3-ylidene]-diethylazanium;chloride Chemical group [Cl-].CCCCCCCCCCCCCCCCCCOC(=O)C1=CC=CC=C1C1=C2C=CC(=[N+](CC)CC)C=C2OC2=CC(N(CC)CC)=CC=C21 NFGODEMQGQNUKK-UHFFFAOYSA-M 0.000 claims 2
- JYNZIOFUHBJABQ-UHFFFAOYSA-N allyl-{6-[3-(4-bromo-phenyl)-benzofuran-6-yloxy]-hexyl-}-methyl-amin Chemical group C=1OC2=CC(OCCCCCCN(C)CC=C)=CC=C2C=1C1=CC=C(Br)C=C1 JYNZIOFUHBJABQ-UHFFFAOYSA-N 0.000 claims 2
- OWHSTLLOZWTNTQ-UHFFFAOYSA-N 2-ethylhexyl 2-sulfanylacetate Chemical group CCCCC(CC)COC(=O)CS OWHSTLLOZWTNTQ-UHFFFAOYSA-N 0.000 claims 1
- 229960000878 docusate sodium Drugs 0.000 claims 1
- 238000001035 drying Methods 0.000 claims 1
- XWGJFPHUCFXLBL-UHFFFAOYSA-M rongalite Chemical compound [Na+].OCS([O-])=O XWGJFPHUCFXLBL-UHFFFAOYSA-M 0.000 claims 1
- APSBXTVYXVQYAB-UHFFFAOYSA-M sodium docusate Chemical group [Na+].CCCCC(CC)COC(=O)CC(S([O-])(=O)=O)C(=O)OCC(CC)CCCC APSBXTVYXVQYAB-UHFFFAOYSA-M 0.000 claims 1
- 238000005406 washing Methods 0.000 claims 1
- 239000011159 matrix material Substances 0.000 abstract description 14
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 abstract description 13
- 239000004416 thermosoftening plastic Substances 0.000 abstract description 12
- 230000008570 general process Effects 0.000 abstract description 2
- 239000002245 particle Substances 0.000 description 94
- 239000000243 solution Substances 0.000 description 78
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 77
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 60
- 238000002360 preparation method Methods 0.000 description 40
- 229910052757 nitrogen Inorganic materials 0.000 description 30
- 229960005419 nitrogen Drugs 0.000 description 30
- 238000003756 stirring Methods 0.000 description 30
- 238000005259 measurement Methods 0.000 description 24
- 238000006116 polymerization reaction Methods 0.000 description 24
- 239000007771 core particle Substances 0.000 description 21
- 239000010420 shell particle Substances 0.000 description 19
- 239000011162 core material Substances 0.000 description 16
- 229920001519 homopolymer Polymers 0.000 description 15
- FBCQUCJYYPMKRO-UHFFFAOYSA-N prop-2-enyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCC=C FBCQUCJYYPMKRO-UHFFFAOYSA-N 0.000 description 15
- 239000007787 solid Substances 0.000 description 14
- CQEYYJKEWSMYFG-UHFFFAOYSA-N butyl acrylate Chemical compound CCCCOC(=O)C=C CQEYYJKEWSMYFG-UHFFFAOYSA-N 0.000 description 11
- 239000002002 slurry Substances 0.000 description 10
- 241001093575 Alma Species 0.000 description 8
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 8
- 239000000463 material Substances 0.000 description 8
- 238000002156 mixing Methods 0.000 description 8
- 239000004957 Zytel Substances 0.000 description 7
- 229920006102 Zytel® Polymers 0.000 description 7
- 150000008064 anhydrides Chemical class 0.000 description 7
- 238000010438 heat treatment Methods 0.000 description 6
- 239000000543 intermediate Substances 0.000 description 6
- 238000004627 transmission electron microscopy Methods 0.000 description 6
- 230000015572 biosynthetic process Effects 0.000 description 5
- 238000002347 injection Methods 0.000 description 5
- 239000007924 injection Substances 0.000 description 5
- 238000004458 analytical method Methods 0.000 description 4
- 238000001746 injection moulding Methods 0.000 description 4
- 230000003287 optical effect Effects 0.000 description 4
- 239000008188 pellet Substances 0.000 description 4
- 229920003229 poly(methyl methacrylate) Polymers 0.000 description 4
- 229920006122 polyamide resin Polymers 0.000 description 4
- 239000004926 polymethyl methacrylate Substances 0.000 description 4
- 239000004908 Emulsion polymer Substances 0.000 description 3
- 239000004677 Nylon Substances 0.000 description 3
- 229920002302 Nylon 6,6 Polymers 0.000 description 3
- 238000000149 argon plasma sintering Methods 0.000 description 3
- 238000001125 extrusion Methods 0.000 description 3
- 238000005227 gel permeation chromatography Methods 0.000 description 3
- VOZRXNHHFUQHIL-UHFFFAOYSA-N glycidyl methacrylate Chemical compound CC(=C)C(=O)OCC1CO1 VOZRXNHHFUQHIL-UHFFFAOYSA-N 0.000 description 3
- 239000004615 ingredient Substances 0.000 description 3
- 229920001778 nylon Polymers 0.000 description 3
- 150000003254 radicals Chemical class 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- 238000012360 testing method Methods 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 239000004609 Impact Modifier Substances 0.000 description 2
- 229920002292 Nylon 6 Polymers 0.000 description 2
- 229910052770 Uranium Inorganic materials 0.000 description 2
- SOGAXMICEFXMKE-UHFFFAOYSA-N alpha-Methyl-n-butyl acrylate Natural products CCCCOC(=O)C(C)=C SOGAXMICEFXMKE-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
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- BBBFJLBPOGFECG-VJVYQDLKSA-N calcitonin Chemical compound N([C@H](C(=O)N[C@@H](CC(C)C)C(=O)NCC(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CO)C(=O)N[C@@H](CCC(N)=O)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CC=1NC=NC=1)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCC(N)=O)C(=O)N[C@@H]([C@@H](C)O)C(=O)N[C@@H](CC=1C=CC(O)=CC=1)C(=O)N1[C@@H](CCC1)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H]([C@@H](C)O)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H]([C@@H](C)O)C(=O)NCC(=O)N[C@@H](CO)C(=O)NCC(=O)N[C@@H]([C@@H](C)O)C(=O)N1[C@@H](CCC1)C(N)=O)C(C)C)C(=O)[C@@H]1CSSC[C@H](N)C(=O)N[C@@H](CO)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CO)C(=O)N[C@@H]([C@@H](C)O)C(=O)N1 BBBFJLBPOGFECG-VJVYQDLKSA-N 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- WNAHIZMDSQCWRP-UHFFFAOYSA-N dodecane-1-thiol Chemical compound CCCCCCCCCCCCS WNAHIZMDSQCWRP-UHFFFAOYSA-N 0.000 description 2
- 229920001971 elastomer Polymers 0.000 description 2
- 229920001038 ethylene copolymer Polymers 0.000 description 2
- KVFIJIWMDBAGDP-UHFFFAOYSA-N ethylpyrazine Chemical compound CCC1=CN=CC=N1 KVFIJIWMDBAGDP-UHFFFAOYSA-N 0.000 description 2
- 239000000945 filler Substances 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- YYJWBYNQJLBIGS-UHFFFAOYSA-N methyl 2-methylbut-2-enoate Chemical compound COC(=O)C(C)=CC YYJWBYNQJLBIGS-UHFFFAOYSA-N 0.000 description 2
- 230000000704 physical effect Effects 0.000 description 2
- 229920002959 polymer blend Polymers 0.000 description 2
- UCWBKJOCRGQBNW-UHFFFAOYSA-M sodium;hydroxymethanesulfinate;dihydrate Chemical compound O.O.[Na+].OCS([O-])=O UCWBKJOCRGQBNW-UHFFFAOYSA-M 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
- 229920005992 thermoplastic resin Polymers 0.000 description 2
- 239000012745 toughening agent Substances 0.000 description 2
- 238000012546 transfer Methods 0.000 description 2
- 230000007704 transition Effects 0.000 description 2
- VCGRFBXVSFAGGA-UHFFFAOYSA-N (1,1-dioxo-1,4-thiazinan-4-yl)-[6-[[3-(4-fluorophenyl)-5-methyl-1,2-oxazol-4-yl]methoxy]pyridin-3-yl]methanone Chemical compound CC=1ON=C(C=2C=CC(F)=CC=2)C=1COC(N=C1)=CC=C1C(=O)N1CCS(=O)(=O)CC1 VCGRFBXVSFAGGA-UHFFFAOYSA-N 0.000 description 1
- 229920002818 (Hydroxyethyl)methacrylate Polymers 0.000 description 1
- BYEAHWXPCBROCE-UHFFFAOYSA-N 1,1,1,3,3,3-hexafluoropropan-2-ol Chemical compound FC(F)(F)C(O)C(F)(F)F BYEAHWXPCBROCE-UHFFFAOYSA-N 0.000 description 1
- VMOIECAJAJFGGU-UHFFFAOYSA-N 2-ethyl-2-sulfanyloctanoic acid Chemical compound CCCCCCC(S)(CC)C(O)=O VMOIECAJAJFGGU-UHFFFAOYSA-N 0.000 description 1
- OFNISBHGPNMTMS-UHFFFAOYSA-N 3-methylideneoxolane-2,5-dione Chemical compound C=C1CC(=O)OC1=O OFNISBHGPNMTMS-UHFFFAOYSA-N 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 102100026735 Coagulation factor VIII Human genes 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- KCXVZYZYPLLWCC-UHFFFAOYSA-N EDTA Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(O)=O)CC(O)=O KCXVZYZYPLLWCC-UHFFFAOYSA-N 0.000 description 1
- 229920002943 EPDM rubber Polymers 0.000 description 1
- 229920003314 Elvaloy® Polymers 0.000 description 1
- 229920003317 Fusabond® Polymers 0.000 description 1
- 101000911390 Homo sapiens Coagulation factor VIII Proteins 0.000 description 1
- WOBHKFSMXKNTIM-UHFFFAOYSA-N Hydroxyethyl methacrylate Chemical compound CC(=C)C(=O)OCCO WOBHKFSMXKNTIM-UHFFFAOYSA-N 0.000 description 1
- 229920002633 Kraton (polymer) Polymers 0.000 description 1
- JHWNWJKBPDFINM-UHFFFAOYSA-N Laurolactam Chemical compound O=C1CCCCCCCCCCCN1 JHWNWJKBPDFINM-UHFFFAOYSA-N 0.000 description 1
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 description 1
- 229920000571 Nylon 11 Polymers 0.000 description 1
- 229920000299 Nylon 12 Polymers 0.000 description 1
- 229920000305 Nylon 6,10 Polymers 0.000 description 1
- 229920003182 Surlyn® Polymers 0.000 description 1
- 102100035115 Testin Human genes 0.000 description 1
- 101710070533 Testin Proteins 0.000 description 1
- 230000002730 additional effect Effects 0.000 description 1
- 238000005054 agglomeration Methods 0.000 description 1
- 230000002776 aggregation Effects 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 229910001870 ammonium persulfate Inorganic materials 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 238000010923 batch production Methods 0.000 description 1
- 125000001246 bromo group Chemical group Br* 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 238000013329 compounding Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 238000004132 cross linking Methods 0.000 description 1
- VDBXLXRWMYNMHL-UHFFFAOYSA-N decanediamide Chemical compound NC(=O)CCCCCCCCC(N)=O VDBXLXRWMYNMHL-UHFFFAOYSA-N 0.000 description 1
- 235000019329 dioctyl sodium sulphosuccinate Nutrition 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 229960001484 edetic acid Drugs 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- 239000006260 foam Substances 0.000 description 1
- LEXQFRJDSTXIKR-UHFFFAOYSA-N formaldehyde sulfanediol dihydrate Chemical compound O.O.C=O.OSO LEXQFRJDSTXIKR-UHFFFAOYSA-N 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 125000001072 heteroaryl group Chemical group 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 125000002346 iodo group Chemical group I* 0.000 description 1
- 230000005865 ionizing radiation Effects 0.000 description 1
- SURQXAFEQWPFPV-UHFFFAOYSA-L iron(2+) sulfate heptahydrate Chemical compound O.O.O.O.O.O.O.[Fe+2].[O-]S([O-])(=O)=O SURQXAFEQWPFPV-UHFFFAOYSA-L 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 229910052748 manganese Inorganic materials 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 238000010128 melt processing Methods 0.000 description 1
- FQPSGWSUVKBHSU-UHFFFAOYSA-N methacrylamide Chemical compound CC(=C)C(N)=O FQPSGWSUVKBHSU-UHFFFAOYSA-N 0.000 description 1
- 229940063557 methacrylate Drugs 0.000 description 1
- 125000005395 methacrylic acid group Chemical group 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 239000002105 nanoparticle Substances 0.000 description 1
- 229940037201 oris Drugs 0.000 description 1
- 150000002978 peroxides Chemical class 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 239000002952 polymeric resin Substances 0.000 description 1
- 235000013824 polyphenols Nutrition 0.000 description 1
- 229920002635 polyurethane Polymers 0.000 description 1
- 239000004814 polyurethane Substances 0.000 description 1
- 239000004800 polyvinyl chloride Substances 0.000 description 1
- 229910052939 potassium sulfate Inorganic materials 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 239000012966 redox initiator Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000012744 reinforcing agent Substances 0.000 description 1
- 102200017272 rs28931576 Human genes 0.000 description 1
- 239000005060 rubber Substances 0.000 description 1
- XGVXKJKTISMIOW-ZDUSSCGKSA-N simurosertib Chemical compound N1N=CC(C=2SC=3C(=O)NC(=NC=3C=2)[C@H]2N3CCC(CC3)C2)=C1C XGVXKJKTISMIOW-ZDUSSCGKSA-N 0.000 description 1
- 229940017704 sodium formaldehyde sulfoxylate dihydrate Drugs 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- XGPOMXSYOKFBHS-UHFFFAOYSA-M sodium;trifluoromethanesulfonate Chemical compound [Na+].[O-]S(=O)(=O)C(F)(F)F XGPOMXSYOKFBHS-UHFFFAOYSA-M 0.000 description 1
- 230000001954 sterilising effect Effects 0.000 description 1
- 238000004659 sterilization and disinfection Methods 0.000 description 1
- 239000011550 stock solution Substances 0.000 description 1
- 229920003002 synthetic resin Polymers 0.000 description 1
- 229920001897 terpolymer Polymers 0.000 description 1
- 229920006029 tetra-polymer Polymers 0.000 description 1
- UEUXEKPTXMALOB-UHFFFAOYSA-J tetrasodium;2-[2-[bis(carboxylatomethyl)amino]ethyl-(carboxylatomethyl)amino]acetate Chemical compound [Na+].[Na+].[Na+].[Na+].[O-]C(=O)CN(CC([O-])=O)CCN(CC([O-])=O)CC([O-])=O UEUXEKPTXMALOB-UHFFFAOYSA-J 0.000 description 1
- RYIVJKDPSXREFM-UHFFFAOYSA-N triazanium;oxido phosphate Chemical compound [NH4+].[NH4+].[NH4+].[O-]OP([O-])([O-])=O RYIVJKDPSXREFM-UHFFFAOYSA-N 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- 238000000196 viscometry Methods 0.000 description 1
- 239000003643 water by type Substances 0.000 description 1
- 238000003466 welding 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
- C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
- C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
- C08F220/10—Esters
- C08F220/12—Esters of monohydric alcohols or phenols
-
- 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
- C08F224/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a heterocyclic ring containing oxygen
-
- 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
- C08F285/00—Macromolecular compounds obtained by polymerising monomers on to preformed graft polymers
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Graft Or Block Polymers (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US33439201P | 2001-11-30 | 2001-11-30 | |
| US60/334,392 | 2001-11-30 | ||
| PCT/US2002/038338 WO2003048220A2 (en) | 2001-11-30 | 2002-11-27 | Graft copolymers of methylene lactones and process for emulsion polymerization of methylene lactones |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2468696A1 true CA2468696A1 (en) | 2003-06-12 |
Family
ID=23306990
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002468696A Abandoned CA2468696A1 (en) | 2001-11-30 | 2002-11-27 | Graft copolymers of methylene lactones and process for emulsion polymerization of methylene lactones |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US6841627B2 (https=) |
| EP (1) | EP1448635A2 (https=) |
| JP (1) | JP2005511805A (https=) |
| BR (1) | BR0214442A (https=) |
| CA (1) | CA2468696A1 (https=) |
| TW (1) | TW200302231A (https=) |
| WO (1) | WO2003048220A2 (https=) |
Families Citing this family (19)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ATE507501T1 (de) * | 2003-01-10 | 2011-05-15 | Menicon Co Ltd | Hochsicheres silikonhaltiges material für eine okularlinse und herstellungsprozess dafür |
| US20040230019A1 (en) * | 2003-01-31 | 2004-11-18 | Brandenburg Charles J. | Poly (alpha-methylene-gama-methyl-gamma-butyrolactone-c-glycidyl methacrylate): preparation, polymer blends derived therefrom, and end uses thereof |
| WO2006025360A1 (ja) * | 2004-08-30 | 2006-03-09 | Mitsubishi Rayon Co., Ltd. | 光学用共重合体及びそれからなる成形体 |
| US7465498B2 (en) * | 2005-11-30 | 2008-12-16 | Sabic Innovative Plastics Ip B.V. | Tulipalin copolymers |
| US8877250B2 (en) | 2005-12-20 | 2014-11-04 | Bridgestone Corporation | Hollow nano-particles and method thereof |
| CN102341342B (zh) * | 2008-12-31 | 2014-07-16 | 株式会社普利司通 | 核起始的纳米颗粒形成方法、纳米颗粒和组合物 |
| US9062144B2 (en) | 2009-04-03 | 2015-06-23 | Bridgestone Corporation | Hairy polymeric nanoparticles with first and second shell block polymer arms |
| CN103210014B (zh) * | 2010-11-11 | 2016-08-10 | Gf生物化学有限公司 | 离子聚合物及其制造方法和用途 |
| BR112013024928A2 (pt) * | 2011-03-30 | 2016-12-20 | Dsm Ip Assets Bv | processo para curar radicalmente uma composição |
| US20140343222A1 (en) * | 2011-11-11 | 2014-11-20 | Segetis, Inc | Poly(lactone)s, method of manufacture, and uses thereof |
| US9428604B1 (en) | 2011-12-30 | 2016-08-30 | Bridgestone Corporation | Nanoparticle fillers and methods of mixing into elastomers |
| KR20150002267A (ko) * | 2013-06-28 | 2015-01-07 | 제일모직주식회사 | 열가소성 수지 조성물 및 이를 이용한 성형품 |
| KR101931585B1 (ko) * | 2016-03-18 | 2019-02-26 | 주식회사 엘지화학 | 열가소성 수지 조성물 및 이로부터 제조된 성형품 |
| BR112020004306B1 (pt) * | 2017-09-04 | 2023-03-21 | Nouryon Chemicals International B.V. | Microesferas termicamente expansíveis processo de fabricação das microesferas, processo de preparação de microesferas expandidas e microesferas expandidas |
| KR102377565B1 (ko) * | 2018-12-13 | 2022-03-21 | 주식회사 엘지화학 | 아크릴계 공중합체, 이의 제조방법 및 이를 포함하는 아크릴계 공중합체 조성물 |
| CN114008130B (zh) * | 2019-06-28 | 2023-05-23 | 罗门哈斯公司 | 反应性丙烯酸类聚烯烃共混物 |
| JP2022140384A (ja) * | 2021-03-10 | 2022-09-26 | 株式会社日本触媒 | 共重合体粒子及びその製造方法 |
| US12282254B2 (en) | 2021-09-30 | 2025-04-22 | Dupont Electronic Materials International, Llc | Photoresist compositions and pattern formation methods |
| TW202502831A (zh) * | 2023-03-24 | 2025-01-16 | 德商巴斯夫歐洲公司 | 適合作為水性塗料組成物中黏合劑的成膜共聚物的水性聚合物膠乳 |
Family Cites Families (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3808180A (en) | 1970-04-13 | 1974-04-30 | Rohm & Haas | Composite interpolymer and low haze impact resistant thermoplastic compositions thereof |
| US3678133A (en) | 1970-04-24 | 1972-07-18 | Rohm & Haas | Modified vinyl halide polymers |
| US3793402A (en) | 1971-11-05 | 1974-02-19 | F Owens | Low haze impact resistant compositions containing a multi-stage,sequentially produced polymer |
| US3808780A (en) * | 1972-11-15 | 1974-05-07 | K Wood | Separator means for combines |
| US3825622A (en) * | 1972-11-20 | 1974-07-23 | Union Carbide Corp | Impact modified blends of vinyl chloride polymers,lactone graft copolymers and styrene-dien-styrene block copolymers |
| US3985703A (en) | 1975-06-24 | 1976-10-12 | Rohm And Haas Company | Process for manufacture of acrylic core/shell polymers |
| US4136136A (en) * | 1976-06-14 | 1979-01-23 | The University Of Akron | Graft copolymers of hydrocarbons and small ring heterocyclic compounds and process for the preparation thereof |
| US4180494A (en) | 1977-08-15 | 1979-12-25 | Rohm And Haas Company | Thermoplastic polyesters |
| DE2951045C2 (de) | 1979-12-19 | 1983-12-22 | Röhm GmbH, 6100 Darmstadt | Herstellung von schlagzähen Harzen |
| US5625001A (en) | 1992-08-18 | 1997-04-29 | Rohm And Haas Company | Toughened polar thermoplastics |
| JP3402141B2 (ja) | 1997-08-12 | 2003-04-28 | 住友化学工業株式会社 | 靭性に優れたアクリル系樹脂の製造方法 |
| GB9719060D0 (en) | 1997-09-09 | 1997-11-12 | Ici Plc | Polymer composition |
| US6642346B2 (en) * | 2000-02-28 | 2003-11-04 | E. I. Du Pont De Nemours And Company | Coating compositions containing substituted and unsubstituted exomethylene lactone or lactam monomers |
-
2002
- 2002-11-27 JP JP2003549405A patent/JP2005511805A/ja active Pending
- 2002-11-27 WO PCT/US2002/038338 patent/WO2003048220A2/en not_active Ceased
- 2002-11-27 EP EP02789952A patent/EP1448635A2/en not_active Withdrawn
- 2002-11-27 CA CA002468696A patent/CA2468696A1/en not_active Abandoned
- 2002-11-27 US US10/305,854 patent/US6841627B2/en not_active Expired - Fee Related
- 2002-11-27 BR BR0214442-5A patent/BR0214442A/pt not_active Application Discontinuation
- 2002-11-29 TW TW091134777A patent/TW200302231A/zh unknown
Also Published As
| Publication number | Publication date |
|---|---|
| JP2005511805A (ja) | 2005-04-28 |
| TW200302231A (en) | 2003-08-01 |
| BR0214442A (pt) | 2004-09-14 |
| US20030171522A1 (en) | 2003-09-11 |
| WO2003048220A2 (en) | 2003-06-12 |
| US6841627B2 (en) | 2005-01-11 |
| EP1448635A2 (en) | 2004-08-25 |
| WO2003048220A3 (en) | 2003-10-02 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CA2468696A1 (en) | Graft copolymers of methylene lactones and process for emulsion polymerization of methylene lactones | |
| US4690986A (en) | Impact-resistant thermoplastic polyorganosiloxane-based graft copolymer and process for producing same | |
| JP2726918B2 (ja) | 耐衝撃性熱可塑性樹脂組成物 | |
| JPS60229911A (ja) | 耐衝撃性熱可塑性樹脂組成物 | |
| US6723790B2 (en) | Blends of poly[α-methylenelact(one)(am] homo- and copolymers | |
| EP0482352B1 (en) | Core-shell polymer and its use | |
| JPS6221804B2 (https=) | ||
| JP2003335827A (ja) | ゴム強化熱可塑性樹脂及びゴム強化熱可塑性樹脂組成物 | |
| KR20040110322A (ko) | 열가소성 수지 조성물 | |
| JPH0320348A (ja) | 高度の耐老化性を有する重合体混合物 | |
| KR20030076662A (ko) | 열가소성 수지용 내충격성 개량제 및 이것을 함유하는수지 조성물 | |
| JP2790522B2 (ja) | グラフト共重合体を製造する方法 | |
| JP3625566B2 (ja) | 熱可塑性樹脂組成物 | |
| JP2854696B2 (ja) | ニトリル系重合体組成物の製造方法 | |
| EP0253624A2 (en) | Acrylic modified N-arylmaleimide copolymer molding composition | |
| US5459215A (en) | Process for producing a heat-resistant copolymer | |
| JPH0362853A (ja) | ポリフェニレンスルフィド系樹脂組成物 | |
| JP2613668B2 (ja) | ニトリル系重合体組成物、成形品およびその製造法 | |
| JP2854697B2 (ja) | 高ニトリル系重合体組成物の製造方法 | |
| JPH0745609B2 (ja) | 熱可塑性樹脂組成物 | |
| JPS6342940B2 (https=) | ||
| US20040230013A1 (en) | Blends of poly (alpha-methylene-gamma-methyl-gamma-butyrolactone-co-glycidyl methacrylate) and polyphenylene sulfide polymer, articles therefrom and preparation thereof | |
| JPS6011926B2 (ja) | 透明耐衝撃性メチルメタクリレ−ト樹脂の製造法 | |
| JPS627756A (ja) | 耐衝撃性メタクリル樹脂組成物 | |
| JPH04120152A (ja) | 高ニトリル系重合体組成物、成形品およびその製造法 |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FZDE | Discontinued |