JP5782434B2 - エステル化物の製造方法 - Google Patents
エステル化物の製造方法 Download PDFInfo
- Publication number
- JP5782434B2 JP5782434B2 JP2012517139A JP2012517139A JP5782434B2 JP 5782434 B2 JP5782434 B2 JP 5782434B2 JP 2012517139 A JP2012517139 A JP 2012517139A JP 2012517139 A JP2012517139 A JP 2012517139A JP 5782434 B2 JP5782434 B2 JP 5782434B2
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- JP
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- Prior art keywords
- alkene
- carbon atoms
- alcohol
- esterified product
- copolymer
- 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.)
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- 238000004519 manufacturing process Methods 0.000 title description 9
- 125000004432 carbon atom Chemical group C* 0.000 claims description 33
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- 238000000034 method Methods 0.000 claims description 19
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- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 claims description 18
- 239000011541 reaction mixture Substances 0.000 claims description 17
- GLDOVTGHNKAZLK-UHFFFAOYSA-N octadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCO GLDOVTGHNKAZLK-UHFFFAOYSA-N 0.000 claims description 16
- ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical compound OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 0.000 claims description 15
- 125000001931 aliphatic group Chemical group 0.000 claims description 8
- GOQYKNQRPGWPLP-UHFFFAOYSA-N n-heptadecyl alcohol Natural products CCCCCCCCCCCCCCCCCO GOQYKNQRPGWPLP-UHFFFAOYSA-N 0.000 claims description 8
- 150000001875 compounds Chemical class 0.000 claims description 5
- 238000007334 copolymerization reaction Methods 0.000 claims description 5
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- 125000001183 hydrocarbyl group Chemical group 0.000 claims 1
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- 239000010949 copper Substances 0.000 description 5
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- OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 description 4
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- 239000011342 resin composition Substances 0.000 description 4
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- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 4
- WMZHDICSCDKPFS-UHFFFAOYSA-N triacont-1-ene Chemical compound CCCCCCCCCCCCCCCCCCCCCCCCCCCCC=C WMZHDICSCDKPFS-UHFFFAOYSA-N 0.000 description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
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- 229910052799 carbon Inorganic materials 0.000 description 3
- BIKNBCLBACEKIM-UHFFFAOYSA-N hexacont-1-ene Chemical compound CCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCC=C BIKNBCLBACEKIM-UHFFFAOYSA-N 0.000 description 3
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- AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 description 2
- BVOSSZSHBZQJOI-UHFFFAOYSA-N 1-Hexen-3-ol Chemical compound CCCC(O)C=C BVOSSZSHBZQJOI-UHFFFAOYSA-N 0.000 description 2
- AFFLGGQVNFXPEV-UHFFFAOYSA-N 1-decene Chemical compound CCCCCCCCC=C AFFLGGQVNFXPEV-UHFFFAOYSA-N 0.000 description 2
- SPURMHFLEKVAAS-UHFFFAOYSA-N 1-docosene Chemical compound CCCCCCCCCCCCCCCCCCCCC=C SPURMHFLEKVAAS-UHFFFAOYSA-N 0.000 description 2
- CRSBERNSMYQZNG-UHFFFAOYSA-N 1-dodecene Chemical compound CCCCCCCCCCC=C CRSBERNSMYQZNG-UHFFFAOYSA-N 0.000 description 2
- LIKMAJRDDDTEIG-UHFFFAOYSA-N 1-hexene Chemical compound CCCCC=C LIKMAJRDDDTEIG-UHFFFAOYSA-N 0.000 description 2
- KWKAKUADMBZCLK-UHFFFAOYSA-N 1-octene Chemical compound CCCCCCC=C KWKAKUADMBZCLK-UHFFFAOYSA-N 0.000 description 2
- 239000004342 Benzoyl peroxide Substances 0.000 description 2
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 description 2
- 239000004593 Epoxy Substances 0.000 description 2
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- 230000000052 comparative effect Effects 0.000 description 2
- MWKFXSUHUHTGQN-UHFFFAOYSA-N decan-1-ol Chemical compound CCCCCCCCCCO MWKFXSUHUHTGQN-UHFFFAOYSA-N 0.000 description 2
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 2
- NOPFSRXAKWQILS-UHFFFAOYSA-N docosan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCCCCCO NOPFSRXAKWQILS-UHFFFAOYSA-N 0.000 description 2
- WMRDPJYQERQCEP-UHFFFAOYSA-N dotriacont-1-ene Chemical compound CCCCCCCCCCCCCCCCCCCCCCCCCCCCCCC=C WMRDPJYQERQCEP-UHFFFAOYSA-N 0.000 description 2
- 238000011156 evaluation Methods 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- YITPJHKSILJOFQ-UHFFFAOYSA-N hentriacont-1-ene Chemical compound CCCCCCCCCCCCCCCCCCCCCCCCCCCCCC=C YITPJHKSILJOFQ-UHFFFAOYSA-N 0.000 description 2
- BXWNKGSJHAJOGX-UHFFFAOYSA-N hexadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCO BXWNKGSJHAJOGX-UHFFFAOYSA-N 0.000 description 2
- ZSIAUFGUXNUGDI-UHFFFAOYSA-N hexan-1-ol Chemical compound CCCCCCO ZSIAUFGUXNUGDI-UHFFFAOYSA-N 0.000 description 2
- BTFJIXJJCSYFAL-UHFFFAOYSA-N icosan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCCCO BTFJIXJJCSYFAL-UHFFFAOYSA-N 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 239000012452 mother liquor Substances 0.000 description 2
- VAMFXQBUQXONLZ-UHFFFAOYSA-N n-alpha-eicosene Natural products CCCCCCCCCCCCCCCCCCC=C VAMFXQBUQXONLZ-UHFFFAOYSA-N 0.000 description 2
- CCCMONHAUSKTEQ-UHFFFAOYSA-N octadec-1-ene Chemical compound CCCCCCCCCCCCCCCCC=C CCCMONHAUSKTEQ-UHFFFAOYSA-N 0.000 description 2
- RZQSSURCROHARM-UHFFFAOYSA-N pentacont-1-ene Chemical compound CCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCC=C RZQSSURCROHARM-UHFFFAOYSA-N 0.000 description 2
- YWAKXRMUMFPDSH-UHFFFAOYSA-N pentene Chemical compound CCCC=C YWAKXRMUMFPDSH-UHFFFAOYSA-N 0.000 description 2
- 239000005011 phenolic resin Substances 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 230000035484 reaction time Effects 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- HLZKNKRTKFSKGZ-UHFFFAOYSA-N tetradecan-1-ol Chemical compound CCCCCCCCCCCCCCO HLZKNKRTKFSKGZ-UHFFFAOYSA-N 0.000 description 2
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 2
- DRJAAODMPBOZLH-UHFFFAOYSA-N tritriacont-1-ene Chemical compound CCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCC=C DRJAAODMPBOZLH-UHFFFAOYSA-N 0.000 description 2
- JHEPBQHNVNUAFL-AATRIKPKSA-N (e)-hex-1-en-1-ol Chemical compound CCCC\C=C\O JHEPBQHNVNUAFL-AATRIKPKSA-N 0.000 description 1
- KBPLFHHGFOOTCA-UHFFFAOYSA-N 1-Octanol Chemical compound CCCCCCCCO KBPLFHHGFOOTCA-UHFFFAOYSA-N 0.000 description 1
- 229940106006 1-eicosene Drugs 0.000 description 1
- FIKTURVKRGQNQD-UHFFFAOYSA-N 1-eicosene Natural products CCCCCCCCCCCCCCCCCC=CC(O)=O FIKTURVKRGQNQD-UHFFFAOYSA-N 0.000 description 1
- QNMCWJOEQBZQHB-UHFFFAOYSA-N 2-Hexyl-1-octanol Chemical compound CCCCCCC(CO)CCCCCC QNMCWJOEQBZQHB-UHFFFAOYSA-N 0.000 description 1
- LTHQZRHTXDZWGX-UHFFFAOYSA-N 2-ethyldecan-1-ol Chemical compound CCCCCCCCC(CC)CO LTHQZRHTXDZWGX-UHFFFAOYSA-N 0.000 description 1
- JZEUFFFBEMAJHS-UHFFFAOYSA-N 2-methyldecan-1-ol Chemical compound CCCCCCCCC(C)CO JZEUFFFBEMAJHS-UHFFFAOYSA-N 0.000 description 1
- OVRDLJJMKGWDHY-UHFFFAOYSA-N 2-methylpent-1-en-1-ol Chemical compound CCCC(C)=CO OVRDLJJMKGWDHY-UHFFFAOYSA-N 0.000 description 1
- WKDDRXZBLMIWBY-UHFFFAOYSA-N 3,4-dimethyltriacont-1-ene Chemical compound CCCCCCCCCCCCCCCCCCCCCCCCCCC(C)C(C)C=C WKDDRXZBLMIWBY-UHFFFAOYSA-N 0.000 description 1
- IRSNFDDXBLNTMA-UHFFFAOYSA-N 3-methyltetracont-1-ene Chemical compound CCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCC(C)C=C IRSNFDDXBLNTMA-UHFFFAOYSA-N 0.000 description 1
- JGMDZPLIPRQLGS-UHFFFAOYSA-N CCCCCCCCCCCCCCCCCCCCCCCCCCCC(C)C=C Chemical compound CCCCCCCCCCCCCCCCCCCCCCCCCCCC(C)C=C JGMDZPLIPRQLGS-UHFFFAOYSA-N 0.000 description 1
- AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical compound CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- 125000002529 biphenylenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C12)* 0.000 description 1
- 239000006229 carbon black Substances 0.000 description 1
- 229960000541 cetyl alcohol Drugs 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000007822 coupling agent Substances 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 229960000735 docosanol Drugs 0.000 description 1
- LQZZUXJYWNFBMV-UHFFFAOYSA-N dodecan-1-ol Chemical compound CCCCCCCCCCCCO LQZZUXJYWNFBMV-UHFFFAOYSA-N 0.000 description 1
- 229940069096 dodecene Drugs 0.000 description 1
- VOKZNQGTPUQQIK-UHFFFAOYSA-N dopentacont-1-ene Chemical compound CCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCC=C VOKZNQGTPUQQIK-UHFFFAOYSA-N 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
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- JLGYYCZMQQXPMF-UHFFFAOYSA-N heptacont-1-ene Chemical compound CCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCC=C JLGYYCZMQQXPMF-UHFFFAOYSA-N 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
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- ACTWLIVMURMPFW-UHFFFAOYSA-N octacont-1-ene Chemical compound CCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCC=C ACTWLIVMURMPFW-UHFFFAOYSA-N 0.000 description 1
- QEXZDYLACYKGOM-UHFFFAOYSA-N octacos-1-ene Chemical compound CCCCCCCCCCCCCCCCCCCCCCCCCCC=C QEXZDYLACYKGOM-UHFFFAOYSA-N 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- LHTVMBMETNGEAN-UHFFFAOYSA-N pent-1-en-1-ol Chemical compound CCCC=CO LHTVMBMETNGEAN-UHFFFAOYSA-N 0.000 description 1
- NOCIDIARFGFRSA-UHFFFAOYSA-N pentatriacont-1-ene Chemical compound CCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCC=C NOCIDIARFGFRSA-UHFFFAOYSA-N 0.000 description 1
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 description 1
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- 238000007789 sealing Methods 0.000 description 1
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- YQPZJBVEKZISEF-UHFFFAOYSA-N tetracont-1-ene Chemical compound CCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCC=C YQPZJBVEKZISEF-UHFFFAOYSA-N 0.000 description 1
- WVGANVWRDOEITC-UHFFFAOYSA-N tetratetracont-1-ene Chemical compound CCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCC=C WVGANVWRDOEITC-UHFFFAOYSA-N 0.000 description 1
- AQUWSCLUQRAMPO-UHFFFAOYSA-N tetratriacont-1-ene Chemical compound CCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCC=C AQUWSCLUQRAMPO-UHFFFAOYSA-N 0.000 description 1
- BPSIOYPQMFLKFR-UHFFFAOYSA-N trimethoxy-[3-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CO[Si](OC)(OC)CCCOCC1CO1 BPSIOYPQMFLKFR-UHFFFAOYSA-N 0.000 description 1
- SLFXTKZGJHDEKI-UHFFFAOYSA-N tripentacont-1-ene Chemical compound CCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCC=C SLFXTKZGJHDEKI-UHFFFAOYSA-N 0.000 description 1
- MDJGEODRKKEELW-UHFFFAOYSA-N tritetracont-1-ene Chemical compound CCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCC=C MDJGEODRKKEELW-UHFFFAOYSA-N 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L63/00—Compositions of epoxy resins; Compositions of derivatives of epoxy resins
- C08L63/04—Epoxynovolacs
-
- 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
- C08F20/00—Homopolymers and 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
-
- 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
- C08F210/14—Monomers containing five or more carbon atoms
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- 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
- C08F222/04—Anhydrides, e.g. cyclic anhydrides
- C08F222/06—Maleic anhydride
-
- 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
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- C08F222/12—Esters of phenols or saturated alcohols
- C08F222/16—Esters having free carboxylic acid groups, e.g. monoalkyl maleates or fumarates
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- 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
- C08F222/10—Esters
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- C08F222/16—Esters having free carboxylic acid groups, e.g. monoalkyl maleates or fumarates
- C08F222/165—Esters having free carboxylic acid groups, e.g. monoalkyl maleates or fumarates the ester chains containing seven or more carbon atoms
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- 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
- C08F8/00—Chemical modification by after-treatment
- C08F8/12—Hydrolysis
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- 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
- C08F8/00—Chemical modification by after-treatment
- C08F8/14—Esterification
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K3/00—Use of inorganic substances as compounding ingredients
- C08K3/01—Use of inorganic substances as compounding ingredients characterized by their specific function
- C08K3/013—Fillers, pigments or reinforcing additives
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L61/00—Compositions of condensation polymers of aldehydes or ketones; Compositions of derivatives of such polymers
- C08L61/04—Condensation polymers of aldehydes or ketones with phenols only
- C08L61/06—Condensation polymers of aldehydes or ketones with phenols only of aldehydes with phenols
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- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
- H01L23/00—Details of semiconductor or other solid state devices
- H01L23/28—Encapsulations, e.g. encapsulating layers, coatings, e.g. for protection
- H01L23/29—Encapsulations, e.g. encapsulating layers, coatings, e.g. for protection characterised by the material, e.g. carbon
- H01L23/293—Organic, e.g. plastic
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- 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
- C08F2800/00—Copolymer characterised by the proportions of the comonomers expressed
- C08F2800/20—Copolymer characterised by the proportions of the comonomers expressed as weight or mass percentages
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- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
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Description
(式(c)〜(f)中、Rは炭素数3〜78の脂肪族炭化水素基を示し、R2は炭素数5〜25の炭化水素基を示し、mは、前記1−アルケン(X)と前記無水マレイン酸(Y)の共重合モル比X/Yを示し、1/2〜10/1であり、nは1以上の整数である。)
本発明のエステル化物の製造方法は、以下の工程を含む。
(a)炭素数5〜80の1−アルケンと無水マレイン酸とを共重合して共重合物を得る工程;および
(b)工程(a)で得られた共重合物と、炭素数5〜25のアルコールとを、トリフルオロメタンスルホン酸の存在下でエステル化反応させて、式(c)〜(f)から選択される少なくとも1つの繰り返し単位を含むエステル化物を含有する反応混合物を得る工程。
(式(c)〜(f)中、Rは炭素数3〜78の脂肪族炭化水素基を示し、R2は炭素数5〜25の炭化水素基を示し、mは、上記1−アルケン(X)と上記無水マレイン酸(Y)の共重合モル比X/Yを示し、1/2〜10/1であり、nは1以上の整数である。)
炭素数28〜60の1−アルケンと無水マレイン酸との共重合物(ダイヤカルナR30、三菱化学株式会社製)100.0g、およびステアリルアルコール47.0gを、300mlの4つ口セパラブルフラスコに仕込み、70℃で溶解させた後に、10wt%トリフルオロメタンスルホン酸水溶液0.5gを添加した。得られた反応混合物を150℃で5時間攪拌した。
その後、液温を120℃まで冷却して、30Torrの減圧下で、2時間減圧蒸留することにより、遊離のトリフルオロメタンスルホン酸と水を除去して、エステル化物Aを144g得た。GPC測定結果から、エステル化物A中の1−アルケン含有量は15質量%であった。またエステル化物Aの硫黄含有量は74ppmであった。
炭素数28〜60の1−アルケンと無水マレイン酸との共重合物(ダイヤカルナR30、三菱化学株式会社製)100.0g、およびステアリルアルコール47.0gを、300mlの4つ口セパラブルフラスコに仕込み、70℃で溶解させた後に、p−トルエンスルホン酸一水和物1.5gを添加した。得られた反応混合物を150℃で4時間攪拌した。
その後、液温を80℃まで冷却して、アセトン131.7gを還流下で60分間かけて滴下した。滴下後は攪拌を止め、液温70℃で60分間静置させると、反応母液が2層に分離した。未反応のステアリルアルコールおよびスルホン酸成分を含む上層のアセトン層は除去した。残る下層を30Torrの減圧下で、90℃で6時間減圧留去を行うことにより、残存するアセトンを除去して、エステル化物Bを144g得た。GPC測定結果から、エステル化物B中の1−アルケン含有量は10質量%であった。またエステル化物Bの硫黄含有量は800ppmであった。
炭素数28〜60の1−アルケンと無水マレイン酸との共重合物(ダイヤカルナR30、三菱化学株式会社製)100.0g、およびステアリルアルコール47.0gを、コンデンサーを装着した300mlの4つ口セパラブスフラスコに仕込み、70℃で溶解させた後に、p−トルエンスルホン酸一水和物1.5gを添加した。得られた反応混合物を150℃で4時間攪拌した。
その後、液温を80℃まで冷却して、アセトン131.7gを還流下で60分間かけて滴下した。滴下後は攪拌を止め、液温70℃で60分間静置させると、反応母液が2層に分離した。未反応のステアリルアルコールおよびスルホン酸成分を含む上層のアセトン層は除去した。この洗浄操作を3回行った後、残る下層を30Torrの減圧下で、90℃で6時間減圧留去を行うことにより、残存するアセトンを除去して、エステル化物Cを135g得た。GPC測定結果から、エステル化物C中の1−アルケン含有量は7質量%であった。またエステル化物Cの硫黄含有量は400ppmであった。
(実施例1)
上記合成例1で得られたエステル化物A、および以下の表に示す成分を、表に示す質量部で配合し、混練温度100℃、混練時間30分の条件で二軸混練して冷却後粉砕し、樹脂組成物を作製した。得られた樹脂組成物を、半導体封止材としての性能(連続成形性)について評価した。結果を表1に示す。
(比較例1〜2)
上記合成例2および3で得られたエステル化物BおよびC、および以下の表に示す成分を、表に示す質量部で配合し、混練温度100℃、混練時間30分の条件で二軸混練して冷却後粉砕し、樹脂組成物を作製した。得られた樹脂組成物を、半導体封止材としての性能(連続成形性)について評価した。結果を表1に示す。
エポキシ樹脂1:エポキシ当量185g/eq、融点108℃のビフェニル型エポキシ樹脂(ジャパンエポキシ株式会社製商品名エピコートYX−4000K)
エポキシ樹脂2:エポキシ当量237g/eq、軟化点52℃のフェニレン骨格を有するフェノールアラルキル型エポキシ樹脂(日本化薬製商品名NC2000)
フェノール樹脂系硬化剤1:水酸基当量199g/eq、軟化点64℃のビフェニレン骨格を有するフェノールアラルキル型フェノール樹脂(明和化成株式会社製商品名MEH−7851SS)
無機充填材1:平均粒径10.8μm、比表面積5.1m2/gの球状溶融シリカ
硬化促進剤1:トリフェニルホスフィンとp−ベンゾキノンとの付加物
カップリング剤1:γ−グリシドキシプロピルトリメトキシシラン(チッソ製商品名S510=GPS−M)
着色剤1:カーボンブラック(三菱化学株式会社製商品名カーボン#5)
低圧トランスファー自動成形機(第一精工(株)製、GP−ELF)を用いて、金型温度175℃、注入圧力9.8MPa、硬化時間70秒の条件で、エポキシ樹脂組成物によりチップなどを封止して80ピンクワッドフラットパッケージ(80pQFP;銅製リードフレーム、パッケージ外寸:14mm×20mm×2mm厚、パッドサイズ:6.5mm×6.5mm、チップサイズ6.0mm×6.0mm×0.35mm厚)を得る成形を、連続で400ショットまで行った。
エアベントブロックの評価については、50ショット毎に金型を目視により観察することで、エアベントブロック(エアベント(幅0.5mm、厚さ50μm)部に樹脂硬化物が固着してエアベントを塞いだ状態)の有無を確認し、次の4段階で評価した。好ましい順は、A、B、C・・・の順であるが、Cランク以上であれば実用可能範囲である。評価結果を下記に示した。
A:400ショットまで問題なし
B:300ショットまでにエアベントブロック発生
C:200ショットまでにエアベントブロック発生
D:100ショットまでにエアベントブロック発生
型汚れについては、400ショット成形後の金型を観察し、ゲート口からの汚れの広がり具合の程度から、次の5段階で評価した。好ましい順は、A、B、C・・・の順であるが、Cランク以上であれば実用可能範囲である。
A:汚れなし
B:汚れの広がりがキャビティ表面の20面積%以下
C:汚れの広がりがキャビティ表面の20面積%超〜40面積%以下
D:汚れの広がりがキャビティ表面の40面積%超〜60面積%以下
E:汚れの広がりがキャビティ表面の60面積%超
Claims (7)
- エステル化物を含有する反応混合物を得る前記工程の後に、遊離トリフルオロメタンスルホン酸を減圧処理により除去する工程をさらに含む、請求項1に記載の方法。
- 前記反応混合物が、前記炭素数5〜80の1−アルケンを含有する、請求項1に記載の方法。
- GPCにより測定される、前記反応混合物中の前記炭素数5〜80の1−アルケンの含有割合が、8質量%以上、20質量%以下である、請求項3に記載の方法。
- 前記1−アルケンが、炭素数28〜60の1−アルケンである、請求項1に記載の方法。
- 前記アルコールが、ステアリルアルコールである、請求項1に記載の方法。
- 前記トリフルオロメタンスルホン酸が、前記共重合物と前記炭素数5〜25のアルコールとの全質量に対し、100ppm以上、1000ppm以下の量である、請求項1に記載の方法。
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US20150014729A1 (en) * | 2012-03-27 | 2015-01-15 | Sumitomo Bakelite Company Limited | Resin composition for reflecting light, substrate for mounting optical semiconductor element, and optical semiconductor device |
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JP2014091744A (ja) * | 2012-10-31 | 2014-05-19 | 3M Innovative Properties Co | アンダーフィル組成物、半導体装置およびその製造方法 |
CN104276938B (zh) * | 2013-07-02 | 2017-02-08 | 北京大学 | 制备γ‑羰基羧酸、氨基酸、氨基酸酯及酰胺类化合物的方法 |
US9868751B2 (en) * | 2014-10-22 | 2018-01-16 | Samsung Sdi Co., Ltd. | Phosphonium compound, epoxy resin composition including the same and semiconductor device prepared from the same |
RU2626412C1 (ru) * | 2016-02-25 | 2017-07-27 | Федеральное государственное бюджетное образовательное учреждение высшего профессионального образования "Уфимский государственный авиационный технический университет" | Магнитотепловой генератор для космического аппарата |
JP6900749B2 (ja) * | 2017-04-04 | 2021-07-07 | 住友ベークライト株式会社 | カーボンブラック分散フェノール樹脂組成物、エポキシ樹脂組成物およびこれらの製造方法 |
TWI672764B (zh) * | 2018-11-07 | 2019-09-21 | 國立成功大學 | 晶片封裝裝置及其對位壓合方法 |
US11107791B2 (en) * | 2019-03-14 | 2021-08-31 | Advanced Semiconductor Engineering, Inc. | Semiconductor package structure and method for manufacturing the same |
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CN116444273A (zh) * | 2022-01-10 | 2023-07-18 | 山东圣泉新材料股份有限公司 | 树脂炭素阳极生坯及制备方法、生坯中间体及制备方法、炭素阳极及制备方法 |
CN116535568B (zh) * | 2023-06-15 | 2024-02-27 | 长江大学 | 一种防蜡剂及其制备方法和应用 |
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TW201211138A (en) | 2012-03-16 |
WO2011148627A1 (ja) | 2011-12-01 |
WO2011148628A1 (ja) | 2011-12-01 |
TWI520972B (zh) | 2016-02-11 |
KR20130124175A (ko) | 2013-11-13 |
US9070628B2 (en) | 2015-06-30 |
JPWO2011148628A1 (ja) | 2013-07-25 |
TWI499629B (zh) | 2015-09-11 |
TW201211076A (en) | 2012-03-16 |
CN104250313A (zh) | 2014-12-31 |
CN102918106B (zh) | 2015-09-16 |
US20130059983A1 (en) | 2013-03-07 |
KR101756499B1 (ko) | 2017-07-10 |
JPWO2011148627A1 (ja) | 2013-07-25 |
JP5874633B2 (ja) | 2016-03-02 |
US20130062748A1 (en) | 2013-03-14 |
SG185503A1 (en) | 2012-12-28 |
KR20130113335A (ko) | 2013-10-15 |
CN103080144A (zh) | 2013-05-01 |
US8648479B2 (en) | 2014-02-11 |
CN103080144B (zh) | 2015-02-25 |
CN102918106A (zh) | 2013-02-06 |
SG185505A1 (en) | 2012-12-28 |
KR101835902B1 (ko) | 2018-03-07 |
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