CA2435284A1 - Ethylene alkyl acrylate copolymers with improved heat resistance - Google Patents
Ethylene alkyl acrylate copolymers with improved heat resistance Download PDFInfo
- Publication number
- CA2435284A1 CA2435284A1 CA002435284A CA2435284A CA2435284A1 CA 2435284 A1 CA2435284 A1 CA 2435284A1 CA 002435284 A CA002435284 A CA 002435284A CA 2435284 A CA2435284 A CA 2435284A CA 2435284 A1 CA2435284 A1 CA 2435284A1
- Authority
- CA
- Canada
- Prior art keywords
- copolymer
- acrylate
- melt
- alkyl
- ethylene
- 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
- 239000005977 Ethylene Substances 0.000 title claims abstract description 55
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 title claims abstract description 39
- 229920000800 acrylic rubber Polymers 0.000 title description 2
- 229920001577 copolymer Polymers 0.000 claims abstract description 224
- 238000002844 melting Methods 0.000 claims abstract description 68
- 230000008018 melting Effects 0.000 claims abstract description 68
- 238000000034 method Methods 0.000 claims abstract description 53
- -1 alkyl methacrylate Chemical compound 0.000 claims abstract description 40
- 125000005250 alkyl acrylate group Chemical group 0.000 claims abstract description 38
- 239000000155 melt Substances 0.000 claims abstract description 22
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 5
- 239000003999 initiator Substances 0.000 claims description 33
- 239000000203 mixture Substances 0.000 claims description 23
- CQEYYJKEWSMYFG-UHFFFAOYSA-N butyl acrylate Chemical compound CCCCOC(=O)C=C CQEYYJKEWSMYFG-UHFFFAOYSA-N 0.000 claims description 16
- 239000000178 monomer Substances 0.000 claims description 16
- 230000009257 reactivity Effects 0.000 claims description 13
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical group CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 claims description 12
- 238000006243 chemical reaction Methods 0.000 claims description 12
- 150000003254 radicals Chemical class 0.000 claims description 9
- 238000005516 engineering process Methods 0.000 claims description 8
- 229920001567 vinyl ester resin Polymers 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 6
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims description 6
- JIGUQPWFLRLWPJ-UHFFFAOYSA-N Ethyl acrylate Chemical compound CCOC(=O)C=C JIGUQPWFLRLWPJ-UHFFFAOYSA-N 0.000 claims description 6
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 claims description 6
- PNJWIWWMYCMZRO-UHFFFAOYSA-N pent‐4‐en‐2‐one Natural products CC(=O)CC=C PNJWIWWMYCMZRO-UHFFFAOYSA-N 0.000 claims description 6
- 238000006116 polymerization reaction Methods 0.000 claims description 6
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 claims description 4
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 claims description 4
- 229910002091 carbon monoxide Inorganic materials 0.000 claims description 4
- 150000002148 esters Chemical class 0.000 claims description 4
- GOXQRTZXKQZDDN-UHFFFAOYSA-N 2-Ethylhexyl acrylate Chemical compound CCCCC(CC)COC(=O)C=C GOXQRTZXKQZDDN-UHFFFAOYSA-N 0.000 claims description 3
- JGRXEBOFWPLEAV-UHFFFAOYSA-N 2-ethylbutyl prop-2-enoate Chemical compound CCC(CC)COC(=O)C=C JGRXEBOFWPLEAV-UHFFFAOYSA-N 0.000 claims description 3
- CFVWNXQPGQOHRJ-UHFFFAOYSA-N 2-methylpropyl prop-2-enoate Chemical compound CC(C)COC(=O)C=C CFVWNXQPGQOHRJ-UHFFFAOYSA-N 0.000 claims description 3
- LNMQRPPRQDGUDR-UHFFFAOYSA-N hexyl prop-2-enoate Chemical compound CCCCCCOC(=O)C=C LNMQRPPRQDGUDR-UHFFFAOYSA-N 0.000 claims description 3
- ISXSCDLOGDJUNJ-UHFFFAOYSA-N tert-butyl prop-2-enoate Chemical compound CC(C)(C)OC(=O)C=C ISXSCDLOGDJUNJ-UHFFFAOYSA-N 0.000 claims description 3
- 150000001875 compounds Chemical class 0.000 claims description 2
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 claims 1
- 239000011976 maleic acid Substances 0.000 claims 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 claims 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 abstract description 3
- 238000000113 differential scanning calorimetry Methods 0.000 description 36
- 230000000052 comparative effect Effects 0.000 description 33
- 238000002347 injection Methods 0.000 description 17
- 239000007924 injection Substances 0.000 description 17
- 229920000642 polymer Polymers 0.000 description 14
- 239000000523 sample Substances 0.000 description 12
- 229910052799 carbon Inorganic materials 0.000 description 9
- IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 description 8
- 239000003795 chemical substances by application Substances 0.000 description 8
- 238000012546 transfer Methods 0.000 description 7
- 229920006225 ethylene-methyl acrylate Polymers 0.000 description 6
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 6
- 239000000126 substance Substances 0.000 description 6
- 239000004831 Hot glue Substances 0.000 description 5
- 239000005043 ethylene-methyl acrylate Substances 0.000 description 5
- 238000001757 thermogravimetry curve Methods 0.000 description 5
- 238000005033 Fourier transform infrared spectroscopy Methods 0.000 description 4
- 239000000853 adhesive Substances 0.000 description 4
- 230000001070 adhesive effect Effects 0.000 description 4
- 229920006244 ethylene-ethyl acrylate Polymers 0.000 description 4
- 230000004927 fusion Effects 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- 238000010998 test method Methods 0.000 description 4
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 238000002425 crystallisation Methods 0.000 description 3
- 230000008025 crystallization Effects 0.000 description 3
- 239000005038 ethylene vinyl acetate Substances 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 238000003860 storage Methods 0.000 description 3
- KVNYFPKFSJIPBJ-UHFFFAOYSA-N 1,2-diethylbenzene Chemical compound CCC1=CC=CC=C1CC KVNYFPKFSJIPBJ-UHFFFAOYSA-N 0.000 description 2
- VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical compound CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 description 2
- AQKYLAIZOGOPAW-UHFFFAOYSA-N 2-methylbutan-2-yl 2,2-dimethylpropaneperoxoate Chemical compound CCC(C)(C)OOC(=O)C(C)(C)C AQKYLAIZOGOPAW-UHFFFAOYSA-N 0.000 description 2
- IFXDUNDBQDXPQZ-UHFFFAOYSA-N 2-methylbutan-2-yl 2-ethylhexaneperoxoate Chemical compound CCCCC(CC)C(=O)OOC(C)(C)CC IFXDUNDBQDXPQZ-UHFFFAOYSA-N 0.000 description 2
- ZIDNXYVJSYJXPE-UHFFFAOYSA-N 2-methylbutan-2-yl 7,7-dimethyloctaneperoxoate Chemical compound CCC(C)(C)OOC(=O)CCCCCC(C)(C)C ZIDNXYVJSYJXPE-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 2
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
- NBBJYMSMWIIQGU-UHFFFAOYSA-N Propionic aldehyde Chemical compound CCC=O NBBJYMSMWIIQGU-UHFFFAOYSA-N 0.000 description 2
- 238000002835 absorbance Methods 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-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
- 238000007906 compression Methods 0.000 description 2
- 230000006835 compression Effects 0.000 description 2
- 238000013461 design Methods 0.000 description 2
- HGVPOWOAHALJHA-UHFFFAOYSA-N ethene;methyl prop-2-enoate Chemical compound C=C.COC(=O)C=C HGVPOWOAHALJHA-UHFFFAOYSA-N 0.000 description 2
- GFJVXXWOPWLRNU-UHFFFAOYSA-N ethenyl formate Chemical compound C=COC=O GFJVXXWOPWLRNU-UHFFFAOYSA-N 0.000 description 2
- UIWXSTHGICQLQT-UHFFFAOYSA-N ethenyl propanoate Chemical compound CCC(=O)OC=C UIWXSTHGICQLQT-UHFFFAOYSA-N 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 229920006228 ethylene acrylate copolymer Polymers 0.000 description 2
- 238000009472 formulation Methods 0.000 description 2
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 238000010348 incorporation Methods 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
- 125000005397 methacrylic acid ester group Chemical group 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- FDPIMTJIUBPUKL-UHFFFAOYSA-N pentan-3-one Chemical compound CCC(=O)CC FDPIMTJIUBPUKL-UHFFFAOYSA-N 0.000 description 2
- 230000000704 physical effect Effects 0.000 description 2
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 2
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- FVQMJJQUGGVLEP-UHFFFAOYSA-N (2-methylpropan-2-yl)oxy 2-ethylhexaneperoxoate Chemical compound CCCCC(CC)C(=O)OOOC(C)(C)C FVQMJJQUGGVLEP-UHFFFAOYSA-N 0.000 description 1
- QEQBMZQFDDDTPN-UHFFFAOYSA-N (2-methylpropan-2-yl)oxy benzenecarboperoxoate Chemical compound CC(C)(C)OOOC(=O)C1=CC=CC=C1 QEQBMZQFDDDTPN-UHFFFAOYSA-N 0.000 description 1
- QVLAWKAXOMEXPM-DICFDUPASA-N 1,1,1,2-tetrachloro-2,2-dideuterioethane Chemical compound [2H]C([2H])(Cl)C(Cl)(Cl)Cl QVLAWKAXOMEXPM-DICFDUPASA-N 0.000 description 1
- AYMDJPGTQFHDSA-UHFFFAOYSA-N 1-(2-ethenoxyethoxy)-2-ethoxyethane Chemical compound CCOCCOCCOC=C AYMDJPGTQFHDSA-UHFFFAOYSA-N 0.000 description 1
- MIRQGKQPLPBZQM-UHFFFAOYSA-N 2-hydroperoxy-2,4,4-trimethylpentane Chemical compound CC(C)(C)CC(C)(C)OO MIRQGKQPLPBZQM-UHFFFAOYSA-N 0.000 description 1
- KFGFVPMRLOQXNB-UHFFFAOYSA-N 3,5,5-trimethylhexanoyl 3,5,5-trimethylhexaneperoxoate Chemical compound CC(C)(C)CC(C)CC(=O)OOC(=O)CC(C)CC(C)(C)C KFGFVPMRLOQXNB-UHFFFAOYSA-N 0.000 description 1
- ZPQAKYPOZRXKFA-UHFFFAOYSA-N 6-Undecanone Chemical compound CCCCCC(=O)CCCCC ZPQAKYPOZRXKFA-UHFFFAOYSA-N 0.000 description 1
- 239000004342 Benzoyl peroxide Substances 0.000 description 1
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical group CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 description 1
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- IKHGUXGNUITLKF-XPULMUKRSA-N acetaldehyde Chemical compound [14CH]([14CH3])=O IKHGUXGNUITLKF-XPULMUKRSA-N 0.000 description 1
- 125000005396 acrylic acid ester group Chemical group 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 150000001491 aromatic compounds Chemical class 0.000 description 1
- 235000019400 benzoyl peroxide Nutrition 0.000 description 1
- QYMGIIIPAFAFRX-UHFFFAOYSA-N butyl prop-2-enoate;ethene Chemical compound C=C.CCCCOC(=O)C=C QYMGIIIPAFAFRX-UHFFFAOYSA-N 0.000 description 1
- JXEJTZZJRBVQKV-UHFFFAOYSA-N butyl prop-2-enoate;ethene;ethenyl acetate Chemical compound C=C.CC(=O)OC=C.CCCCOC(=O)C=C JXEJTZZJRBVQKV-UHFFFAOYSA-N 0.000 description 1
- ZTQSAGDEMFDKMZ-UHFFFAOYSA-N butyric aldehyde Natural products CCCC=O ZTQSAGDEMFDKMZ-UHFFFAOYSA-N 0.000 description 1
- 239000012986 chain transfer agent Substances 0.000 description 1
- 238000005352 clarification Methods 0.000 description 1
- 229920006026 co-polymeric resin Polymers 0.000 description 1
- 238000010924 continuous production Methods 0.000 description 1
- 238000013480 data collection Methods 0.000 description 1
- XJOBOFWTZOKMOH-UHFFFAOYSA-N decanoyl decaneperoxoate Chemical compound CCCCCCCCCC(=O)OOC(=O)CCCCCCCCC XJOBOFWTZOKMOH-UHFFFAOYSA-N 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- LSXWFXONGKSEMY-UHFFFAOYSA-N di-tert-butyl peroxide Chemical compound CC(C)(C)OOC(C)(C)C LSXWFXONGKSEMY-UHFFFAOYSA-N 0.000 description 1
- RHMZKSWPMYAOAZ-UHFFFAOYSA-N diethyl peroxide Chemical compound CCOOCC RHMZKSWPMYAOAZ-UHFFFAOYSA-N 0.000 description 1
- 238000001938 differential scanning calorimetry curve Methods 0.000 description 1
- 230000009189 diving Effects 0.000 description 1
- 239000005042 ethylene-ethyl acrylate Substances 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 229920001519 homopolymer Polymers 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 230000000977 initiatory effect Effects 0.000 description 1
- 230000014759 maintenance of location Effects 0.000 description 1
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 description 1
- 239000003607 modifier Substances 0.000 description 1
- 150000001451 organic peroxides Chemical class 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 238000004886 process control Methods 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 238000003908 quality control method Methods 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- OPQYOFWUFGEMRZ-UHFFFAOYSA-N tert-butyl 2,2-dimethylpropaneperoxoate Chemical compound CC(C)(C)OOC(=O)C(C)(C)C OPQYOFWUFGEMRZ-UHFFFAOYSA-N 0.000 description 1
- NMOALOSNPWTWRH-UHFFFAOYSA-N tert-butyl 7,7-dimethyloctaneperoxoate Chemical compound CC(C)(C)CCCCCC(=O)OOC(C)(C)C NMOALOSNPWTWRH-UHFFFAOYSA-N 0.000 description 1
- SWAXTRYEYUTSAP-UHFFFAOYSA-N tert-butyl ethaneperoxoate Chemical compound CC(=O)OOC(C)(C)C SWAXTRYEYUTSAP-UHFFFAOYSA-N 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L33/00—Compositions of homopolymers or 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 of salts, anhydrides, esters, amides, imides or nitriles thereof; Compositions of derivatives of such polymers
- C08L33/04—Homopolymers or copolymers of esters
- C08L33/06—Homopolymers or copolymers of esters of esters containing only carbon, hydrogen and oxygen, which oxygen atoms are present only as part of the carboxyl radical
- C08L33/10—Homopolymers or copolymers of methacrylic acid esters
-
- 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
- C08F210/00—Copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond
- C08F210/02—Ethene
Landscapes
- 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)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US26300201P | 2001-01-19 | 2001-01-19 | |
| US60/263,002 | 2001-01-19 | ||
| PCT/US2002/001471 WO2002057354A2 (en) | 2001-01-19 | 2002-01-18 | Ethylene alkyl acrylate copolymers with improved heat resistance |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2435284A1 true CA2435284A1 (en) | 2002-07-25 |
Family
ID=22999976
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002435284A Abandoned CA2435284A1 (en) | 2001-01-19 | 2002-01-18 | Ethylene alkyl acrylate copolymers with improved heat resistance |
Country Status (8)
| Country | Link |
|---|---|
| EP (1) | EP1409559A4 (https=) |
| JP (1) | JP2004527595A (https=) |
| KR (1) | KR20030072600A (https=) |
| CN (1) | CN1551892A (https=) |
| AU (1) | AU2002243591A1 (https=) |
| CA (1) | CA2435284A1 (https=) |
| TW (1) | TW593358B (https=) |
| WO (1) | WO2002057354A2 (https=) |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20040266927A1 (en) * | 2003-06-27 | 2004-12-30 | Prejean George Wyatt | Filled blends of tubular reactor produced ethylene/alkyl acrylate copolymers modified with organic acids |
| WO2009114661A1 (en) | 2008-03-13 | 2009-09-17 | Dow Global Technologies Inc. | Long chain branched (lcb), block or interconnected copolymers of ethylene in combination with one other polymer |
| CN104203394B (zh) * | 2012-04-13 | 2019-06-07 | 埃克森美孚化学专利公司 | 含极性共聚单体的聚乙烯聚合物和聚合物组合物的制造方法 |
| KR102502365B1 (ko) * | 2014-11-13 | 2023-02-23 | 다우 글로벌 테크놀로지스 엘엘씨 | 개선된 고압 자유 라디칼 중합을 위한 윤활제 조성물 |
| JP6785685B2 (ja) * | 2016-04-19 | 2020-11-18 | 宇部丸善ポリエチレン株式会社 | エチレン−アクリル酸エチル共重合体の製造方法 |
| KR102334926B1 (ko) * | 2017-07-31 | 2021-12-07 | 엑손모빌 케미칼 패턴츠 인코포레이티드 | 에틸렌 공중합체를 제조하기 위한 고압 중합 방법 |
| EP4004065A1 (en) * | 2019-07-31 | 2022-06-01 | Dow Global Technologies LLC | Ethylene-based polymer composition with branching |
| CN120051497A (zh) * | 2022-11-30 | 2025-05-27 | 住友化学株式会社 | 乙烯-（甲基）丙烯酸酯共聚物及其制造方法、以及组合物 |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3217973A1 (de) * | 1982-05-13 | 1983-11-17 | Basf Ag, 6700 Ludwigshafen | Verfahren zur herstellung von copolymerisaten des ethylens mit acrylsaeureestern in einem zweizonenreaktor bei druecken oberhalb 500 bar |
| DE3404744A1 (de) * | 1984-02-10 | 1985-08-14 | Basf Ag, 6700 Ludwigshafen | Copolymerisate des ethylens mit carboxylgruppenhaltigen comonomeren |
| CA1281828C (en) * | 1986-04-25 | 1991-03-19 | Akio Daimon | Filler-containing polypropylene resin composition and process for producing the same |
| US4988781A (en) * | 1989-02-27 | 1991-01-29 | The Dow Chemical Company | Process for producing homogeneous modified copolymers of ethylene/alpha-olefin carboxylic acids or esters |
| US5234986A (en) * | 1992-03-02 | 1993-08-10 | E. I. Du Pont De Nemours And Company | Hot-melt adhesives for PVC with good high temperature utility |
| US5482977A (en) * | 1995-05-08 | 1996-01-09 | Eastman Chemical Company | Foamable branched polyesters |
| US6388026B1 (en) * | 1997-08-05 | 2002-05-14 | S. C. Johnson Commercial Markets, Inc. | Process for the preparation of macromers |
| US6294264B1 (en) * | 1999-03-30 | 2001-09-25 | Cryovac, Inc. | Oriented cook-in film with good interply adhesion |
-
2002
- 2002-01-18 JP JP2002558422A patent/JP2004527595A/ja active Pending
- 2002-01-18 CA CA002435284A patent/CA2435284A1/en not_active Abandoned
- 2002-01-18 CN CNA028051327A patent/CN1551892A/zh active Pending
- 2002-01-18 AU AU2002243591A patent/AU2002243591A1/en not_active Abandoned
- 2002-01-18 WO PCT/US2002/001471 patent/WO2002057354A2/en not_active Ceased
- 2002-01-18 KR KR10-2003-7009597A patent/KR20030072600A/ko not_active Withdrawn
- 2002-01-18 EP EP02709086A patent/EP1409559A4/en not_active Withdrawn
- 2002-01-21 TW TW091100875A patent/TW593358B/zh not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| EP1409559A2 (en) | 2004-04-21 |
| AU2002243591A1 (en) | 2002-07-30 |
| TW593358B (en) | 2004-06-21 |
| KR20030072600A (ko) | 2003-09-15 |
| WO2002057354A2 (en) | 2002-07-25 |
| CN1551892A (zh) | 2004-12-01 |
| EP1409559A4 (en) | 2004-06-02 |
| JP2004527595A (ja) | 2004-09-09 |
| WO2002057354A3 (en) | 2004-02-26 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US9150681B2 (en) | Ethylene-based polymers and processes for the same | |
| US10301403B2 (en) | Low density ethylene-based polymers with broad molecular weight distributions and low extractables | |
| JP7066319B2 (ja) | 抽出分量と溶融弾性との改善された均衡を有する管状低密度エチレン系ポリマー | |
| US10442878B2 (en) | Ethylene-based polymers and processes for the same | |
| KR20150087235A (ko) | 높은 용융 강도를 갖는 저밀도 에틸렌-기재 중합체 | |
| EP2751146A1 (en) | Polymerization processes with fresh ethylene distributions for preparation of low density ethylene-based polymers | |
| KR20160031456A (ko) | 개선된 용융 강도, 출력 및 기계적 특성을 갖는 저밀도 에틸렌계 조성물 | |
| EP2794675A1 (en) | Ethylene-based polymers with improved melt strength and processes for the same | |
| US6946528B2 (en) | Hot melt adhesives | |
| CA2435284A1 (en) | Ethylene alkyl acrylate copolymers with improved heat resistance | |
| US7112624B2 (en) | Ethylene alkyl acrylate copolymers with improved heat resistance | |
| JP7702383B2 (ja) | 分岐を有するエチレン系ポリマー組成物 | |
| WO2002060993A1 (en) | Hot melt adhesives | |
| JPH02255884A (ja) | 接着剤用の改質エチレンコポリマー |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FZDE | Discontinued |