JP4907349B2 - マレイミド官能基を含有するオキセタン化合物 - Google Patents
マレイミド官能基を含有するオキセタン化合物 Download PDFInfo
- Publication number
- JP4907349B2 JP4907349B2 JP2006532450A JP2006532450A JP4907349B2 JP 4907349 B2 JP4907349 B2 JP 4907349B2 JP 2006532450 A JP2006532450 A JP 2006532450A JP 2006532450 A JP2006532450 A JP 2006532450A JP 4907349 B2 JP4907349 B2 JP 4907349B2
- Authority
- JP
- Japan
- Prior art keywords
- oxetane
- maleimide
- functional groups
- starting
- reaction
- 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.)
- Expired - Fee Related
Links
- 125000005439 maleimidyl group Chemical group C1(C=CC(N1*)=O)=O 0.000 title claims description 11
- 150000002921 oxetanes Chemical class 0.000 title description 3
- 150000001875 compounds Chemical class 0.000 claims description 15
- AHHWIHXENZJRFG-UHFFFAOYSA-N oxetane Chemical compound C1COC1 AHHWIHXENZJRFG-UHFFFAOYSA-N 0.000 claims description 15
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
- 238000010276 construction Methods 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 description 25
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 21
- 125000000524 functional group Chemical group 0.000 description 21
- 229920000642 polymer Polymers 0.000 description 20
- 239000007858 starting material Substances 0.000 description 16
- -1 coatings Substances 0.000 description 15
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 12
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 10
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 9
- 239000000178 monomer Substances 0.000 description 8
- PEEHTFAAVSWFBL-UHFFFAOYSA-N Maleimide Chemical compound O=C1NC(=O)C=C1 PEEHTFAAVSWFBL-UHFFFAOYSA-N 0.000 description 7
- WOJKKJKETHYEAC-UHFFFAOYSA-N 6-Maleimidocaproic acid Chemical compound OC(=O)CCCCCN1C(=O)C=CC1=O WOJKKJKETHYEAC-UHFFFAOYSA-N 0.000 description 6
- SZQVEOLVJHOCMY-UHFFFAOYSA-N 2-(2,5-dioxopyrrol-1-yl)hexanoic acid Chemical compound CCCCC(C(O)=O)N1C(=O)C=CC1=O SZQVEOLVJHOCMY-UHFFFAOYSA-N 0.000 description 5
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 5
- 230000001588 bifunctional effect Effects 0.000 description 5
- KAKZBPTYRLMSJV-UHFFFAOYSA-N butadiene group Chemical group C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 5
- 150000002148 esters Chemical class 0.000 description 5
- 150000003384 small molecules Chemical class 0.000 description 5
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 5
- 229920002554 vinyl polymer Polymers 0.000 description 5
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 4
- 229930195733 hydrocarbon Natural products 0.000 description 4
- 150000002430 hydrocarbons Chemical class 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- 150000003923 2,5-pyrrolediones Chemical class 0.000 description 3
- 239000004215 Carbon black (E152) Substances 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 3
- 238000000034 method Methods 0.000 description 3
- 238000002156 mixing Methods 0.000 description 3
- 239000002861 polymer material Substances 0.000 description 3
- 238000006116 polymerization reaction Methods 0.000 description 3
- UNMJLQGKEDTEKJ-UHFFFAOYSA-N (3-ethyloxetan-3-yl)methanol Chemical compound CCC1(CO)COC1 UNMJLQGKEDTEKJ-UHFFFAOYSA-N 0.000 description 2
- NLQMSBJFLQPLIJ-UHFFFAOYSA-N (3-methyloxetan-3-yl)methanol Chemical compound OCC1(C)COC1 NLQMSBJFLQPLIJ-UHFFFAOYSA-N 0.000 description 2
- MYRTYDVEIRVNKP-UHFFFAOYSA-N 1,2-Divinylbenzene Chemical compound C=CC1=CC=CC=C1C=C MYRTYDVEIRVNKP-UHFFFAOYSA-N 0.000 description 2
- SVMIVBMALOISKL-UHFFFAOYSA-N 1-(6-hydroxyhexyl)pyrrole-2,5-dione Chemical compound OCCCCCCN1C(=O)C=CC1=O SVMIVBMALOISKL-UHFFFAOYSA-N 0.000 description 2
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 2
- OEPOKWHJYJXUGD-UHFFFAOYSA-N 2-(3-phenylmethoxyphenyl)-1,3-thiazole-4-carbaldehyde Chemical compound O=CC1=CSC(C=2C=C(OCC=3C=CC=CC=3)C=CC=2)=N1 OEPOKWHJYJXUGD-UHFFFAOYSA-N 0.000 description 2
- JGSBNCHRQGOTDU-UHFFFAOYSA-N 2-methyloxetane;pyrrole-2,5-dione Chemical compound CC1CCO1.O=C1NC(=O)C=C1 JGSBNCHRQGOTDU-UHFFFAOYSA-N 0.000 description 2
- IUTPJBLLJJNPAJ-UHFFFAOYSA-N 3-(2,5-dioxopyrrol-1-yl)propanoic acid Chemical compound OC(=O)CCN1C(=O)C=CC1=O IUTPJBLLJJNPAJ-UHFFFAOYSA-N 0.000 description 2
- YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 description 2
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 2
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 description 2
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 description 2
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 description 2
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 2
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 description 2
- BZHJMEDXRYGGRV-UHFFFAOYSA-N Vinyl chloride Chemical compound ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- 150000001408 amides Chemical class 0.000 description 2
- 125000000129 anionic group Chemical group 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 150000001732 carboxylic acid derivatives Chemical group 0.000 description 2
- 125000002091 cationic group Chemical group 0.000 description 2
- 150000001993 dienes Chemical class 0.000 description 2
- 230000009977 dual effect Effects 0.000 description 2
- FJKIXWOMBXYWOQ-UHFFFAOYSA-N ethenoxyethane Chemical compound CCOC=C FJKIXWOMBXYWOQ-UHFFFAOYSA-N 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 125000003566 oxetanyl group Chemical group 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 238000010926 purge Methods 0.000 description 2
- 238000007142 ring opening reaction Methods 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 238000004809 thin layer chromatography Methods 0.000 description 2
- XSQUKJJJFZCRTK-UHFFFAOYSA-N urea group Chemical group NC(=O)N XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 2
- 230000004580 weight loss Effects 0.000 description 2
- PMJHHCWVYXUKFD-SNAWJCMRSA-N (E)-1,3-pentadiene Chemical group C\C=C\C=C PMJHHCWVYXUKFD-SNAWJCMRSA-N 0.000 description 1
- JBESFMOSFGXJEE-UHFFFAOYSA-N 1-(3-hydroxypropyl)pyrrole-2,5-dione Chemical compound OCCCN1C(=O)C=CC1=O JBESFMOSFGXJEE-UHFFFAOYSA-N 0.000 description 1
- SCLQRRKBXAGUTF-UHFFFAOYSA-N 1-(5-isocyanatopentyl)pyrrole-2,5-dione Chemical compound O=C=NCCCCCN1C(=O)C=CC1=O SCLQRRKBXAGUTF-UHFFFAOYSA-N 0.000 description 1
- JAHNSTQSQJOJLO-UHFFFAOYSA-N 2-(3-fluorophenyl)-1h-imidazole Chemical compound FC1=CC=CC(C=2NC=CN=2)=C1 JAHNSTQSQJOJLO-UHFFFAOYSA-N 0.000 description 1
- GOXQRTZXKQZDDN-UHFFFAOYSA-N 2-Ethylhexyl acrylate Chemical compound CCCCC(CC)COC(=O)C=C GOXQRTZXKQZDDN-UHFFFAOYSA-N 0.000 description 1
- ZUQNNQJVLMADTA-UHFFFAOYSA-N 2-ethyloxetane;pyrrole-2,5-dione Chemical compound CCC1CCO1.O=C1NC(=O)C=C1 ZUQNNQJVLMADTA-UHFFFAOYSA-N 0.000 description 1
- KGIGUEBEKRSTEW-UHFFFAOYSA-N 2-vinylpyridine Chemical compound C=CC1=CC=CC=N1 KGIGUEBEKRSTEW-UHFFFAOYSA-N 0.000 description 1
- RRRHGMRCVIZIRT-UHFFFAOYSA-N 3-(bromomethyl)-3-ethyloxetane Chemical compound CCC1(CBr)COC1 RRRHGMRCVIZIRT-UHFFFAOYSA-N 0.000 description 1
- MGBZKWOJRYGRTO-UHFFFAOYSA-N 3-(bromomethyl)-3-methyloxetane Chemical compound BrCC1(C)COC1 MGBZKWOJRYGRTO-UHFFFAOYSA-N 0.000 description 1
- QYVRNXPERYZKBW-UHFFFAOYSA-N 3-ethyl-3-[(4-methylphenyl)sulfonylmethyl]oxetane Chemical compound C=1C=C(C)C=CC=1S(=O)(=O)CC1(CC)COC1 QYVRNXPERYZKBW-UHFFFAOYSA-N 0.000 description 1
- QOXOZONBQWIKDA-UHFFFAOYSA-N 3-hydroxypropyl Chemical group [CH2]CCO QOXOZONBQWIKDA-UHFFFAOYSA-N 0.000 description 1
- KLYSWDGMCLWRPE-UHFFFAOYSA-N 3-methyl-3-[(4-methylphenyl)sulfonylmethyl]oxetane Chemical compound C1=CC(C)=CC=C1S(=O)(=O)CC1(C)COC1 KLYSWDGMCLWRPE-UHFFFAOYSA-N 0.000 description 1
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 description 1
- QWXLYHRHFMULJF-UHFFFAOYSA-N CC1(CC(F)(F)F)COC1 Chemical compound CC1(CC(F)(F)F)COC1 QWXLYHRHFMULJF-UHFFFAOYSA-N 0.000 description 1
- KXDHJXZQYSOELW-UHFFFAOYSA-N Carbamic acid Chemical group NC(O)=O KXDHJXZQYSOELW-UHFFFAOYSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- JIGUQPWFLRLWPJ-UHFFFAOYSA-N Ethyl acrylate Chemical compound CCOC(=O)C=C JIGUQPWFLRLWPJ-UHFFFAOYSA-N 0.000 description 1
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 1
- GYCMBHHDWRMZGG-UHFFFAOYSA-N Methylacrylonitrile Chemical compound CC(=C)C#N GYCMBHHDWRMZGG-UHFFFAOYSA-N 0.000 description 1
- 229920000459 Nitrile rubber Polymers 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 1
- QYKIQEUNHZKYBP-UHFFFAOYSA-N Vinyl ether Chemical class C=COC=C QYKIQEUNHZKYBP-UHFFFAOYSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 125000005396 acrylic acid ester group Chemical group 0.000 description 1
- 238000007259 addition reaction Methods 0.000 description 1
- 239000000853 adhesive Substances 0.000 description 1
- 230000001070 adhesive effect Effects 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 125000005907 alkyl ester group Chemical group 0.000 description 1
- 150000001350 alkyl halides Chemical class 0.000 description 1
- XYLMUPLGERFSHI-UHFFFAOYSA-N alpha-Methylstyrene Chemical compound CC(=C)C1=CC=CC=C1 XYLMUPLGERFSHI-UHFFFAOYSA-N 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- YACLQRRMGMJLJV-UHFFFAOYSA-N chloroprene Chemical compound ClC(=C)C=C YACLQRRMGMJLJV-UHFFFAOYSA-N 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 239000002131 composite material Substances 0.000 description 1
- 238000006482 condensation reaction Methods 0.000 description 1
- 238000001723 curing Methods 0.000 description 1
- 150000004292 cyclic ethers Chemical class 0.000 description 1
- 150000001991 dicarboxylic acids Chemical class 0.000 description 1
- 239000000539 dimer Substances 0.000 description 1
- 150000002009 diols Chemical class 0.000 description 1
- 230000008034 disappearance Effects 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 239000008393 encapsulating agent Substances 0.000 description 1
- 125000001033 ether group Chemical group 0.000 description 1
- 150000002170 ethers Chemical group 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 1
- 239000010931 gold Substances 0.000 description 1
- 229910052737 gold Inorganic materials 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- AHAREKHAZNPPMI-UHFFFAOYSA-N hexa-1,3-diene Chemical compound CCC=CC=C AHAREKHAZNPPMI-UHFFFAOYSA-N 0.000 description 1
- 125000001261 isocyanato group Chemical group *N=C=O 0.000 description 1
- 125000005647 linker group Chemical group 0.000 description 1
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 1
- 125000005395 methacrylic acid group Chemical group 0.000 description 1
- LVHBHZANLOWSRM-UHFFFAOYSA-N methylenebutanedioic acid Natural products OC(=O)CC(=C)C(O)=O LVHBHZANLOWSRM-UHFFFAOYSA-N 0.000 description 1
- 150000002763 monocarboxylic acids Chemical class 0.000 description 1
- 150000002826 nitrites Chemical class 0.000 description 1
- LKEDKQWWISEKSW-UHFFFAOYSA-N nonyl 2-methylprop-2-enoate Chemical compound CCCCCCCCCOC(=O)C(C)=C LKEDKQWWISEKSW-UHFFFAOYSA-N 0.000 description 1
- ANISOHQJBAQUQP-UHFFFAOYSA-N octyl prop-2-enoate Chemical compound CCCCCCCCOC(=O)C=C ANISOHQJBAQUQP-UHFFFAOYSA-N 0.000 description 1
- DWYJHMSKXMHOAP-UHFFFAOYSA-N oxetan-2-ol Chemical compound OC1CCO1 DWYJHMSKXMHOAP-UHFFFAOYSA-N 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- PNJWIWWMYCMZRO-UHFFFAOYSA-N pent‐4‐en‐2‐one Natural products CC(=O)CC=C PNJWIWWMYCMZRO-UHFFFAOYSA-N 0.000 description 1
- PMJHHCWVYXUKFD-UHFFFAOYSA-N piperylene Natural products CC=CC=C PMJHHCWVYXUKFD-UHFFFAOYSA-N 0.000 description 1
- 238000003847 radiation curing Methods 0.000 description 1
- 238000010526 radical polymerization reaction Methods 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 229920001909 styrene-acrylic polymer Polymers 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 238000001029 thermal curing Methods 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- 125000002088 tosyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C([H])([H])[H])S(*)(=O)=O 0.000 description 1
- 229930195735 unsaturated hydrocarbon Natural products 0.000 description 1
- 229920001567 vinyl ester resin Polymers 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- 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
- C08F222/00—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 carboxyl radical and containing at least one other carboxyl radical in the molecule; Salts, anhydrides, esters, amides, imides, or nitriles thereof
- C08F222/36—Amides or imides
- C08F222/40—Imides, e.g. cyclic imides
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Pyrrole Compounds (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Epoxy Compounds (AREA)
- Polyethers (AREA)
- Plural Heterocyclic Compounds (AREA)
Description
本発明は、マレイミド官能基を含有するオキセタン化合物に関する。
オキセタンは、カチオン性およびアニオン性の両方の開環単独重合を経ることができる反応性の高い環状エーテルである。マレイミド化合物は、フリーラジカル重合をすることができる。
本発明は、オキセタン官能基およびマレイミド官能基を含有する化合物に関する。これらの化合物は、オキセタンがカチオン性もしくはアニオン性の開環を経ることができる反応において単独重合性を示すことができ、または電子供与体化合物のような化合物と重合性を示すことができる。二重の官能基は、二重の硬化処理、すなわち熱硬化または放射線硬化の両方を可能にする。この能力により、それらは、多くの用途、例えば、接着剤、コーティング、封入材および複合材での使用に関し興味深いものになっている。
一態様において、本発明の化合物は、式
(a)アルコール、例えば、3−メチル−3−ヒドロキシメチルオキセタン、3−エチル−3−ヒドロキシメチルオキセタン;
実施例1:エチルオキセタンマレイミドの調製
Claims (2)
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US10/430,085 | 2003-05-06 | ||
US10/430,085 US6982338B2 (en) | 2003-05-06 | 2003-05-06 | Oxetane compounds containing maleimide functionality |
PCT/US2004/012385 WO2004101550A1 (en) | 2003-05-06 | 2004-04-21 | Oxetane compounds containing maleimide functionality |
Publications (2)
Publication Number | Publication Date |
---|---|
JP2007502859A JP2007502859A (ja) | 2007-02-15 |
JP4907349B2 true JP4907349B2 (ja) | 2012-03-28 |
Family
ID=33416177
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2006532450A Expired - Fee Related JP4907349B2 (ja) | 2003-05-06 | 2004-04-21 | マレイミド官能基を含有するオキセタン化合物 |
Country Status (7)
Country | Link |
---|---|
US (2) | US6982338B2 (ja) |
EP (2) | EP1620430A1 (ja) |
JP (1) | JP4907349B2 (ja) |
KR (1) | KR20060008975A (ja) |
CN (1) | CN100471855C (ja) |
TW (1) | TWI340744B (ja) |
WO (1) | WO2004101550A1 (ja) |
Families Citing this family (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP4497095B2 (ja) * | 2003-10-15 | 2010-07-07 | 東亞合成株式会社 | オキセタニル基を2個以上有するポリマーを含むカチオン硬化性樹脂組成物 |
US7230055B2 (en) * | 2004-07-29 | 2007-06-12 | National Starch And Chemical Investment Holding Corporation | Compositions containing oxetane compounds for use in semiconductor packaging |
TWI378091B (en) * | 2006-03-09 | 2012-12-01 | Eisai R&D Man Co Ltd | Multi-cyclic cinnamide derivatives |
EP2044142A2 (en) * | 2006-06-29 | 2009-04-08 | Medtronic, Inc. | Poly(orthoester) polymers, and methods of making and using same |
US8324319B2 (en) * | 2007-11-20 | 2012-12-04 | Sridhar Laxmisha M | Redox-induced cationically polymerizable compositions with low cure temperature |
US8956642B2 (en) * | 2008-04-18 | 2015-02-17 | Medtronic, Inc. | Bupivacaine formulation in a polyorthoester carrier |
US8475823B2 (en) * | 2008-04-18 | 2013-07-02 | Medtronic, Inc. | Baclofen formulation in a polyorthoester carrier |
Citations (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPH0717958A (ja) * | 1993-06-30 | 1995-01-20 | Rensselaer Polytechnic Inst | オキセタン化合物 |
JPH10175973A (ja) * | 1996-12-12 | 1998-06-30 | Inst Fr Petrole | マレインイミド安息香酸エステル |
JPH11302278A (ja) * | 1998-04-17 | 1999-11-02 | Dainippon Ink & Chem Inc | マレイミド誘導体、該誘導体を含有する活性エネルギー線硬化性組成物及び該硬化性組成物の硬化方法 |
JPH11343346A (ja) * | 1998-05-29 | 1999-12-14 | Ube Ind Ltd | 熱硬化性オキセタン組成物およびその硬化方法ならびに該方法により得られる硬化物 |
JP2000143729A (ja) * | 1998-11-17 | 2000-05-26 | Dainippon Ink & Chem Inc | マレイミド誘導体を含有する活性エネルギー線硬化性樹脂組成物 |
Family Cites Families (12)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3867353A (en) | 1973-01-17 | 1975-02-18 | Phillips Petroleum Co | Polymerization of oxiranes and lactones |
US4225691A (en) | 1979-07-17 | 1980-09-30 | General Electric Company | Low temperature curable organic resin compositions |
US6403760B1 (en) | 1999-12-28 | 2002-06-11 | Omnova Solutions Inc. | Monohydric polyfluorooxetane polymer and radiation curable coatings containing a monofunctional polyfluorooxetane polymer |
US6300456B1 (en) | 2000-05-18 | 2001-10-09 | National Starch And Chemical Investment Holding Corporation | Compounds with electron donor and electron acceptor functionality |
JP2001329112A (ja) | 2000-05-23 | 2001-11-27 | Toray Ind Inc | シランカップリング剤、硬化性樹脂溶液組成物、及びそれからなる機能性硬化物 |
EP1303568B1 (en) | 2000-07-19 | 2007-05-30 | Koninklijke Philips Electronics N.V. | Method of manufacturing a replica as well as a replica obtained by carrying out a uv light-initiated cationic polymerization |
JP2002060483A (ja) * | 2000-08-22 | 2002-02-26 | Nippon Kayaku Co Ltd | 活性エネルギー線硬化性樹脂組成物 |
EP1337602B1 (en) | 2000-10-04 | 2006-04-12 | Koninklijke Philips Electronics N.V. | Polymerizable liquid crystalline dioxetanes, their preparation and use |
EP1334513A2 (en) | 2000-11-14 | 2003-08-13 | Henkel Loctite Corporation | Wafer applied fluxing and underfill material, and layered electronic assemblies manufactured therewith |
JP2002193965A (ja) * | 2000-12-22 | 2002-07-10 | Ube Ind Ltd | オキセタン環を有するフタルイミド誘導体 |
US6930136B2 (en) | 2001-09-28 | 2005-08-16 | National Starch And Chemical Investment Holding Corporation | Adhesion promoters containing benzotriazoles |
US6753434B1 (en) * | 2003-05-06 | 2004-06-22 | National Starch And Chemical Investment Holding Corporation | Oxetane compounds containing cinnamyl functionality |
-
2003
- 2003-05-06 US US10/430,085 patent/US6982338B2/en not_active Expired - Fee Related
-
2004
- 2004-04-21 JP JP2006532450A patent/JP4907349B2/ja not_active Expired - Fee Related
- 2004-04-21 EP EP04760825A patent/EP1620430A1/en not_active Withdrawn
- 2004-04-21 KR KR1020057020881A patent/KR20060008975A/ko not_active Application Discontinuation
- 2004-04-21 CN CNB2004800120262A patent/CN100471855C/zh not_active Expired - Fee Related
- 2004-04-21 WO PCT/US2004/012385 patent/WO2004101550A1/en active Application Filing
- 2004-04-21 EP EP06019766A patent/EP1736473A3/en not_active Withdrawn
- 2004-05-05 TW TW093112573A patent/TWI340744B/zh not_active IP Right Cessation
-
2005
- 2005-05-04 US US11/121,430 patent/US7319132B2/en not_active Expired - Fee Related
Patent Citations (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPH0717958A (ja) * | 1993-06-30 | 1995-01-20 | Rensselaer Polytechnic Inst | オキセタン化合物 |
JPH10175973A (ja) * | 1996-12-12 | 1998-06-30 | Inst Fr Petrole | マレインイミド安息香酸エステル |
JPH11302278A (ja) * | 1998-04-17 | 1999-11-02 | Dainippon Ink & Chem Inc | マレイミド誘導体、該誘導体を含有する活性エネルギー線硬化性組成物及び該硬化性組成物の硬化方法 |
JPH11343346A (ja) * | 1998-05-29 | 1999-12-14 | Ube Ind Ltd | 熱硬化性オキセタン組成物およびその硬化方法ならびに該方法により得られる硬化物 |
JP2000143729A (ja) * | 1998-11-17 | 2000-05-26 | Dainippon Ink & Chem Inc | マレイミド誘導体を含有する活性エネルギー線硬化性樹脂組成物 |
Also Published As
Publication number | Publication date |
---|---|
KR20060008975A (ko) | 2006-01-27 |
WO2004101550A1 (en) | 2004-11-25 |
US20040225070A1 (en) | 2004-11-11 |
JP2007502859A (ja) | 2007-02-15 |
CN1791597A (zh) | 2006-06-21 |
EP1736473A2 (en) | 2006-12-27 |
US6982338B2 (en) | 2006-01-03 |
US7319132B2 (en) | 2008-01-15 |
CN100471855C (zh) | 2009-03-25 |
TW200505908A (en) | 2005-02-16 |
TWI340744B (en) | 2011-04-21 |
EP1620430A1 (en) | 2006-02-01 |
EP1736473A3 (en) | 2007-01-31 |
US20050209437A1 (en) | 2005-09-22 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
US7319132B2 (en) | Polymer compounds containing oxetane and maleimide functionality | |
JP4685784B2 (ja) | ハイブリッドオキセタン化合物を含有する接着剤組成物 | |
JPH0649711B2 (ja) | ビスマレイミド化合物及びこれを用いたフリーラジカル硬化性配合組成物 | |
US7452943B2 (en) | Polymer compounds containing oxetane and styrenic functionality | |
JP2007500742A (ja) | シンナミル官能基を含有するオキセタン化合物 | |
Bicu et al. | Polymers from a levopimaric acid–acrylonitrile Diels–Alder adduct: Synthesis and characterization | |
TW200946560A (en) | Multifunctional nitrones in non-radical systems | |
US7034064B2 (en) | Method of attaching a die to a substrate using a hybrid oxetane compound | |
JPS6227082B2 (ja) | ||
US5260424A (en) | B-(keto or sulfonyl) esters from reaction of silylketene acetal and acyl or sulfonyl compound | |
CN110407713A (zh) | 一种二元松香基苯并环丁烯单体及其制备方法和应用 | |
JP3426058B2 (ja) | 高不飽和基価ラクトン重合体およびその製造方法 | |
JPH0639497B2 (ja) | 5−フルオロウラシル系ポリマーの製造法 | |
JPH0337213A (ja) | ジアセチレン組成物 | |
JPH069715A (ja) | 重合開始剤 | |
JPH0579242B2 (ja) | ||
JPS6079010A (ja) | 重合体の製法 | |
KR20000019999A (ko) | 순간 자발 중합성 부타디엔 유도체 및 그의 제조 방법 |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
A621 | Written request for application examination |
Free format text: JAPANESE INTERMEDIATE CODE: A621 Effective date: 20061201 |
|
A131 | Notification of reasons for refusal |
Free format text: JAPANESE INTERMEDIATE CODE: A131 Effective date: 20100517 |
|
A711 | Notification of change in applicant |
Free format text: JAPANESE INTERMEDIATE CODE: A711 Effective date: 20100730 |
|
A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20100817 |
|
A131 | Notification of reasons for refusal |
Free format text: JAPANESE INTERMEDIATE CODE: A131 Effective date: 20110302 |
|
A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20110602 |
|
TRDD | Decision of grant or rejection written | ||
A01 | Written decision to grant a patent or to grant a registration (utility model) |
Free format text: JAPANESE INTERMEDIATE CODE: A01 Effective date: 20111213 |
|
A01 | Written decision to grant a patent or to grant a registration (utility model) |
Free format text: JAPANESE INTERMEDIATE CODE: A01 |
|
A61 | First payment of annual fees (during grant procedure) |
Free format text: JAPANESE INTERMEDIATE CODE: A61 Effective date: 20120111 |
|
FPAY | Renewal fee payment (event date is renewal date of database) |
Free format text: PAYMENT UNTIL: 20150120 Year of fee payment: 3 |
|
R150 | Certificate of patent or registration of utility model |
Free format text: JAPANESE INTERMEDIATE CODE: R150 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
LAPS | Cancellation because of no payment of annual fees |