JP2013542298A - 可架橋固形化超分岐ポリエステルおよびその固形化産物とその調製方法 - Google Patents
可架橋固形化超分岐ポリエステルおよびその固形化産物とその調製方法 Download PDFInfo
- Publication number
- JP2013542298A JP2013542298A JP2013538025A JP2013538025A JP2013542298A JP 2013542298 A JP2013542298 A JP 2013542298A JP 2013538025 A JP2013538025 A JP 2013538025A JP 2013538025 A JP2013538025 A JP 2013538025A JP 2013542298 A JP2013542298 A JP 2013542298A
- Authority
- JP
- Japan
- Prior art keywords
- hyperbranched polyester
- solidified
- product
- moles
- hyperbranched
- 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.)
- Granted
Links
- 229920006150 hyperbranched polyester Polymers 0.000 title claims abstract description 106
- 238000002360 preparation method Methods 0.000 title claims abstract description 8
- 150000001875 compounds Chemical class 0.000 claims abstract description 65
- 238000004519 manufacturing process Methods 0.000 claims abstract description 11
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 8
- 150000002148 esters Chemical class 0.000 claims abstract description 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 3
- 238000006243 chemical reaction Methods 0.000 claims description 30
- PRPINYUDVPFIRX-UHFFFAOYSA-N 1-naphthaleneacetic acid Chemical compound C1=CC=C2C(CC(=O)O)=CC=CC2=C1 PRPINYUDVPFIRX-UHFFFAOYSA-N 0.000 claims description 29
- 239000003795 chemical substances by application Substances 0.000 claims description 29
- 238000005886 esterification reaction Methods 0.000 claims description 27
- 238000007711 solidification Methods 0.000 claims description 26
- 230000008023 solidification Effects 0.000 claims description 25
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 24
- 239000000203 mixture Substances 0.000 claims description 23
- 239000000126 substance Substances 0.000 claims description 22
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 claims description 21
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims description 21
- 125000001931 aliphatic group Chemical group 0.000 claims description 18
- CERQOIWHTDAKMF-UHFFFAOYSA-N alpha-methacrylic acid Natural products CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 claims description 15
- RIWRBSMFKVOJMN-UHFFFAOYSA-N 2-methyl-1-phenylpropan-2-ol Chemical compound CC(C)(O)CC1=CC=CC=C1 RIWRBSMFKVOJMN-UHFFFAOYSA-N 0.000 claims description 9
- 230000001939 inductive effect Effects 0.000 claims description 9
- -1 naphthalene acyl halide Chemical class 0.000 claims description 9
- VFHVQBAGLAREND-UHFFFAOYSA-N diphenylphosphoryl-(2,4,6-trimethylphenyl)methanone Chemical compound CC1=CC(C)=CC(C)=C1C(=O)P(=O)(C=1C=CC=CC=1)C1=CC=CC=C1 VFHVQBAGLAREND-UHFFFAOYSA-N 0.000 claims description 3
- 230000002195 synergetic effect Effects 0.000 claims description 3
- 238000010894 electron beam technology Methods 0.000 claims description 2
- 230000001678 irradiating effect Effects 0.000 claims 1
- UFWIBTONFRDIAS-UHFFFAOYSA-N naphthalene-acid Natural products C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 claims 1
- 239000000047 product Substances 0.000 description 57
- 239000002994 raw material Substances 0.000 description 26
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 21
- 239000000178 monomer Substances 0.000 description 18
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 16
- 238000000034 method Methods 0.000 description 15
- 238000006116 polymerization reaction Methods 0.000 description 15
- 230000015572 biosynthetic process Effects 0.000 description 14
- NWVVVBRKAWDGAB-UHFFFAOYSA-N hydroquinone methyl ether Natural products COC1=CC=C(O)C=C1 NWVVVBRKAWDGAB-UHFFFAOYSA-N 0.000 description 14
- 238000003786 synthesis reaction Methods 0.000 description 14
- 239000003112 inhibitor Substances 0.000 description 12
- 230000032050 esterification Effects 0.000 description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
- 239000003054 catalyst Substances 0.000 description 9
- 125000001624 naphthyl group Chemical group 0.000 description 9
- 239000007788 liquid Substances 0.000 description 8
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 7
- 229910052753 mercury Inorganic materials 0.000 description 7
- AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 description 6
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 6
- 230000003287 optical effect Effects 0.000 description 6
- 239000012044 organic layer Substances 0.000 description 6
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 6
- 238000010526 radical polymerization reaction Methods 0.000 description 5
- 239000011347 resin Substances 0.000 description 5
- 229920005989 resin Polymers 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 4
- 230000000052 comparative effect Effects 0.000 description 4
- 238000004132 cross linking Methods 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 229920000728 polyester Polymers 0.000 description 4
- 230000035484 reaction time Effects 0.000 description 4
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 4
- CNHDIAIOKMXOLK-UHFFFAOYSA-N toluquinol Chemical compound CC1=CC(O)=CC=C1O CNHDIAIOKMXOLK-UHFFFAOYSA-N 0.000 description 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- BGNXCDMCOKJUMV-UHFFFAOYSA-N Tert-Butylhydroquinone Chemical compound CC(C)(C)C1=CC(O)=CC=C1O BGNXCDMCOKJUMV-UHFFFAOYSA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 238000000576 coating method Methods 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- 229920000587 hyperbranched polymer Polymers 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 238000000926 separation method Methods 0.000 description 3
- WSUIRDORMCYOBS-UHFFFAOYSA-N 3-chloro-2-methylprop-2-enoic acid Chemical compound ClC=C(C)C(O)=O WSUIRDORMCYOBS-UHFFFAOYSA-N 0.000 description 2
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 2
- 125000000777 acyl halide group Chemical group 0.000 description 2
- 150000001350 alkyl halides Chemical class 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 125000004185 ester group Chemical group 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- 239000011241 protective layer Substances 0.000 description 2
- 230000000717 retained effect Effects 0.000 description 2
- 238000007151 ring opening polymerisation reaction Methods 0.000 description 2
- 238000001228 spectrum Methods 0.000 description 2
- 238000001308 synthesis method Methods 0.000 description 2
- 230000002194 synthesizing effect Effects 0.000 description 2
- UFHSKEHEWFGEFH-UHFFFAOYSA-N (2,5-dioxopyrrolidin-3-yl) prop-2-enoate Chemical compound C=CC(=O)OC1CC(=O)NC1=O UFHSKEHEWFGEFH-UHFFFAOYSA-N 0.000 description 1
- SFVXEEDRZUFMND-UHFFFAOYSA-N (3-methyl-2,5-dioxopyrrolidin-3-yl) prop-2-enoate Chemical compound C=CC(=O)OC1(C)CC(=O)NC1=O SFVXEEDRZUFMND-UHFFFAOYSA-N 0.000 description 1
- WJFKNYWRSNBZNX-UHFFFAOYSA-N 10H-phenothiazine Chemical compound C1=CC=C2NC3=CC=CC=C3SC2=C1 WJFKNYWRSNBZNX-UHFFFAOYSA-N 0.000 description 1
- PTBDIHRZYDMNKB-UHFFFAOYSA-N 2,2-Bis(hydroxymethyl)propionic acid Chemical compound OCC(C)(CO)C(O)=O PTBDIHRZYDMNKB-UHFFFAOYSA-N 0.000 description 1
- JZODKRWQWUWGCD-UHFFFAOYSA-N 2,5-di-tert-butylbenzene-1,4-diol Chemical compound CC(C)(C)C1=CC(O)=C(C(C)(C)C)C=C1O JZODKRWQWUWGCD-UHFFFAOYSA-N 0.000 description 1
- RFCQDOVPMUSZMN-UHFFFAOYSA-N 2-Naphthalenethiol Chemical compound C1=CC=CC2=CC(S)=CC=C21 RFCQDOVPMUSZMN-UHFFFAOYSA-N 0.000 description 1
- BBCLXYJRPRRZQW-UHFFFAOYSA-N 2-phenylnaphthalen-1-amine Chemical compound C1=CC2=CC=CC=C2C(N)=C1C1=CC=CC=C1 BBCLXYJRPRRZQW-UHFFFAOYSA-N 0.000 description 1
- RBTBFTRPCNLSDE-UHFFFAOYSA-N 3,7-bis(dimethylamino)phenothiazin-5-ium Chemical compound C1=CC(N(C)C)=CC2=[S+]C3=CC(N(C)C)=CC=C3N=C21 RBTBFTRPCNLSDE-UHFFFAOYSA-N 0.000 description 1
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 1
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 1
- JLLMOYPIVVKFHY-UHFFFAOYSA-N Benzenethiol, 4,4'-thiobis- Chemical compound C1=CC(S)=CC=C1SC1=CC=C(S)C=C1 JLLMOYPIVVKFHY-UHFFFAOYSA-N 0.000 description 1
- UQVZNLINGOJPTL-UHFFFAOYSA-N C(=O)O.C1=CC=CC2=CC=CC=C12 Chemical compound C(=O)O.C1=CC=CC2=CC=CC=C12 UQVZNLINGOJPTL-UHFFFAOYSA-N 0.000 description 1
- IMOPCPQQQJIAIG-UHFFFAOYSA-N CC(C1=CC=CC2=CC=CC=C12)=O.Cl Chemical compound CC(C1=CC=CC2=CC=CC=C12)=O.Cl IMOPCPQQQJIAIG-UHFFFAOYSA-N 0.000 description 1
- 0 CCC(C)(CO)C([U]CC(C)(COC(C(*)(CC)COC)=O)C([U]CCNC[C@](C[O+])(COCCOC(C(C)(COCC(C)(C*)O)COC(C1(CO)CC1)=[U])O)C[U]CCOC(C(C)(COC(C(C)(C*)CO)=O)COC(C1(C*)OC1)=O)=O)=O)=O Chemical compound CCC(C)(CO)C([U]CC(C)(COC(C(*)(CC)COC)=O)C([U]CCNC[C@](C[O+])(COCCOC(C(C)(COCC(C)(C*)O)COC(C1(CO)CC1)=[U])O)C[U]CCOC(C(C)(COC(C(C)(C*)CO)=O)COC(C1(C*)OC1)=O)=O)=O)=O 0.000 description 1
- SLALDAQIGWHGJY-UHFFFAOYSA-N CCOC(C(C)(COC(C(C)(CN)CO)=O)COC(C1(CO)OC1)=O)=O Chemical compound CCOC(C(C)(COC(C(C)(CN)CO)=O)COC(C1(CO)OC1)=O)=O SLALDAQIGWHGJY-UHFFFAOYSA-N 0.000 description 1
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-M acrylate group Chemical group C(C=C)(=O)[O-] NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 1
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 1
- 125000004423 acyloxy group Chemical group 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 239000012790 adhesive layer Substances 0.000 description 1
- 239000012670 alkaline solution Substances 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- DVECBJCOGJRVPX-UHFFFAOYSA-N butyryl chloride Chemical compound CCCC(Cl)=O DVECBJCOGJRVPX-UHFFFAOYSA-N 0.000 description 1
- QGJOPFRUJISHPQ-NJFSPNSNSA-N carbon disulfide-14c Chemical compound S=[14C]=S QGJOPFRUJISHPQ-NJFSPNSNSA-N 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000004891 communication Methods 0.000 description 1
- 239000002274 desiccant Substances 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 239000000411 inducer Substances 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 239000012263 liquid product Substances 0.000 description 1
- 229910044991 metal oxide Inorganic materials 0.000 description 1
- 150000004706 metal oxides Chemical class 0.000 description 1
- 229960000907 methylthioninium chloride Drugs 0.000 description 1
- 239000002105 nanoparticle Substances 0.000 description 1
- VGKONPUVOVVNSU-UHFFFAOYSA-N naphthalen-1-yl acetate Chemical group C1=CC=C2C(OC(=O)C)=CC=CC2=C1 VGKONPUVOVVNSU-UHFFFAOYSA-N 0.000 description 1
- NSNPSJGHTQIXDO-UHFFFAOYSA-N naphthalene-1-carbonyl chloride Chemical compound C1=CC=C2C(C(=O)Cl)=CC=CC2=C1 NSNPSJGHTQIXDO-UHFFFAOYSA-N 0.000 description 1
- 239000011368 organic material Substances 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- 229950000688 phenothiazine Drugs 0.000 description 1
- 238000005498 polishing Methods 0.000 description 1
- 238000012643 polycondensation polymerization Methods 0.000 description 1
- 239000011253 protective coating Substances 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 238000007348 radical reaction Methods 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical class O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000002594 sorbent Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- 239000002344 surface layer Substances 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- LBUJPTNKIBCYBY-UHFFFAOYSA-N tetrahydroquinoline Natural products C1=CC=C2CCCNC2=C1 LBUJPTNKIBCYBY-UHFFFAOYSA-N 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Images
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
- C08G63/02—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
- C08G63/66—Polyesters containing oxygen in the form of ether groups
- C08G63/664—Polyesters containing oxygen in the form of ether groups derived from hydroxy carboxylic acids
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
- C08G63/02—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds
- C08G63/06—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds derived from hydroxycarboxylic acids
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
- C08G63/91—Polymers modified by chemical after-treatment
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
- C08G63/91—Polymers modified by chemical after-treatment
- C08G63/912—Polymers modified by chemical after-treatment derived from hydroxycarboxylic acids
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G83/00—Macromolecular compounds not provided for in groups C08G2/00 - C08G81/00
- C08G83/002—Dendritic macromolecules
- C08G83/005—Hyperbranched macromolecules
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L67/00—Compositions of polyesters obtained by reactions forming a carboxylic ester link in the main chain; Compositions of derivatives of such polymers
- C08L67/06—Unsaturated polyesters
- C08L67/07—Unsaturated polyesters having terminal carbon-to-carbon unsaturated bonds
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Polyesters Or Polycarbonates (AREA)
- Macromonomer-Based Addition Polymer (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
Abstract
Description
Claims (25)
- 前記超分岐ポリエステル骨組みはn個の末端水酸基を有する脂肪族超分岐ポリエステルから誘導される、請求項1に記載の超分岐ポリエステル。
- 前記脂肪族超分岐ポリエステルは、Boltorn H20、Boltorn H30およびBoltorn H40中の1種又は複数種の化合物からなる、請求項2に記載の超分岐ポリエステル。
- AとNの総モル数がHBP骨組み総モル数とnとの相乗積の比は0.6以上である、請求項1に記載の超分岐ポリエステル。
- AとNの総モル数がHBP骨組み総モル数とnとの相乗積の比は0.7以上である、請求項1に記載の超分岐ポリエステル。
- NがAとNの総モル数とのモル比は40モル%以上で、90モル%又はそれ以下である、請求項1〜6中のいずれかに記載の超分岐ポリエステル。
- NがAとNの総モル数とのモル比は80モル%又はそれ以下である、請求項7に記載の超分岐ポリエステル。
- NがAとNの総モル数とのモル比は40モル%以上で、75モル%又はそれ以下である、請求項7に記載の超分岐ポリエステル。
- 前記超分岐ポリエステルの屈折率は1.50〜1.60である、請求項9に記載の超分岐ポリエステル。
- n≧a+b≧0.6nである、請求項7に記載の超分岐ポリエステル。
- 前記超分岐ポリエステルはn個の末端水酸基を有する超分岐ポリエステル骨組み化合物と次の化合物との反応によって得られ、その化合物は、(メチル)アクリル酸とハロゲン化(メチル)アクリル酸中の少なくとも1種の化合物、およびナフチル酢酸とハロゲン化ナフタレンアシル中の少なくとも1種の化合物からなる、請求項1に記載の可架橋固形化超分岐ポリエステルの製造方法。
- 前記n個の末端水酸基を有する超分岐ポリエステル骨組化合物は脂肪族超分岐ポリエステルからなる、請求項12に記載の製造方法。
- 前記脂肪族超分岐ポリエステルはBoltorn H20、Boltorn H30およびBoltorn H40中の1種又は複数種の化合物からなる、請求項13に記載の製造方法。
- 前記超分岐ポリエステルは前記脂肪族超分岐ポリエステルとアクリル酸およびナフチル酢酸とのエステル化反応によって得られる、請求項13に記載の製造方法。
- 前記ナフチル酢酸がアクリル酸とナフチル酢酸の総投入量に対する比率は30〜80モル%である、請求項16に記載の製造方法。
- 前記ナフチル酢酸がアクリル酸とナフチル酢酸の総投入量に対する比率は40〜75モル%である、請求項16に記載の製造方法。
- 前記混合物には請求項1〜11中のいずれかの前記超分岐ポリエステルおよび光誘発剤が含まれる、可架橋固形化超分岐ポリエステル混合物。
- 前記光誘発剤は前記混合物中の0.5〜5重量%を占める、請求項19に記載の混合物。
- 前記光誘発剤は前記混合物中の1〜3重量%を占める、請求項19に記載の混合物。
- 前記光誘発剤はDarocur1173、Lrqacure184、Lrqacure369、Lrqacure651、Lrqacure819、Lrqacure907、Lrqacure2959および2,4,6−トリメチルベンゾイルー ジフェニルホスフィンオキシド中の1種又は複数種の誘発剤からなる、請求項19に記載の混合物。
- 前記固形化製品において、請求項19〜22のいずれかに記載の前記混合物の固形化反応によって得られる、固形化製品。
- 前記固形化製品において、屈折率は1.55〜1.65である、請求項23に記載の固形化製品。
- 前記固形化反応は紫外線ランプや、電子ビーム又は可視光照射で混合物を照射して行われる光固形化反応からなり、それによって得られる請求項23に記載の固形化製品。
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
PCT/CN2010/078739 WO2012065294A1 (zh) | 2010-11-15 | 2010-11-15 | 可交联固化的超支化聚酯及其固化产物和制备方法 |
Publications (2)
Publication Number | Publication Date |
---|---|
JP2013542298A true JP2013542298A (ja) | 2013-11-21 |
JP5729845B2 JP5729845B2 (ja) | 2015-06-03 |
Family
ID=45986228
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2013538025A Expired - Fee Related JP5729845B2 (ja) | 2010-11-15 | 2010-11-15 | 可架橋固形化超分岐ポリエステルおよびその固形化産物とその調製方法 |
Country Status (7)
Country | Link |
---|---|
US (1) | US8912246B2 (ja) |
JP (1) | JP5729845B2 (ja) |
CN (1) | CN102439061B (ja) |
GB (1) | GB2499944B (ja) |
HK (1) | HK1167871A1 (ja) |
TW (1) | TW201221578A (ja) |
WO (1) | WO2012065294A1 (ja) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN113185883A (zh) * | 2021-06-11 | 2021-07-30 | 山东高速湖北养护科技有限公司 | 一种环保高性能公路标线涂料及其制备方法 |
Families Citing this family (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP3134471B1 (en) * | 2014-04-23 | 2020-03-18 | Sun Chemical Corporation | A process for preparing polyester resins from polyethylene terephthalate and energy curable coating compositions |
CN104086756A (zh) * | 2014-07-28 | 2014-10-08 | 营口康辉石化有限公司 | 一种光学透明膜级聚酯生产方法 |
Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPH07504219A (ja) * | 1992-02-26 | 1995-05-11 | ペルストルプ アーベー | 樹枝状高分子及びその生成方法 |
JP2000075774A (ja) * | 1998-09-01 | 2000-03-14 | Toppan Printing Co Ltd | ホログラム記録材料 |
Family Cites Families (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
SE514075C2 (sv) * | 1999-04-27 | 2000-12-18 | Perstorp Ab | Förfarande för tillverkning av en akrylatkomposition innefattande minst en dendritisk polyesterakrylatoligomer och minst en akrylatmonomer |
CN1147522C (zh) * | 1999-08-06 | 2004-04-28 | 中国科学技术大学 | 辐射可固化胺基超支化聚酯的制备方法 |
TWI265937B (en) * | 2005-10-03 | 2006-11-11 | Eternal Chemical Co Ltd | Acrylated semi-crystalline hyperbranched polyester oligomer and preparation method thereof |
US8889232B2 (en) * | 2009-08-20 | 2014-11-18 | Electronics For Imaging, Inc. | Radiation curable ink compositions |
-
2010
- 2010-11-15 WO PCT/CN2010/078739 patent/WO2012065294A1/zh active Application Filing
- 2010-11-15 JP JP2013538025A patent/JP5729845B2/ja not_active Expired - Fee Related
- 2010-11-15 CN CN2010800174874A patent/CN102439061B/zh not_active Expired - Fee Related
- 2010-11-15 GB GB1310384.1A patent/GB2499944B/en not_active Expired - Fee Related
- 2010-11-15 US US13/885,399 patent/US8912246B2/en not_active Expired - Fee Related
-
2011
- 2011-11-14 TW TW100141495A patent/TW201221578A/zh unknown
-
2012
- 2012-09-03 HK HK12108563.6A patent/HK1167871A1/xx unknown
Patent Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPH07504219A (ja) * | 1992-02-26 | 1995-05-11 | ペルストルプ アーベー | 樹枝状高分子及びその生成方法 |
JP2000075774A (ja) * | 1998-09-01 | 2000-03-14 | Toppan Printing Co Ltd | ホログラム記録材料 |
Non-Patent Citations (1)
Title |
---|
JPN6014014857; APLIED OPTICS Vo.42,No.19, 2003, 3944-3949 * |
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN113185883A (zh) * | 2021-06-11 | 2021-07-30 | 山东高速湖北养护科技有限公司 | 一种环保高性能公路标线涂料及其制备方法 |
CN113185883B (zh) * | 2021-06-11 | 2022-04-15 | 山东高速湖北养护科技有限公司 | 一种环保高性能公路标线涂料及其制备方法 |
Also Published As
Publication number | Publication date |
---|---|
HK1167871A1 (en) | 2012-12-14 |
GB201310384D0 (en) | 2013-07-24 |
US20130237627A1 (en) | 2013-09-12 |
TW201221578A (en) | 2012-06-01 |
GB2499944B (en) | 2018-05-02 |
CN102439061A (zh) | 2012-05-02 |
WO2012065294A1 (zh) | 2012-05-24 |
GB2499944A (en) | 2013-09-04 |
JP5729845B2 (ja) | 2015-06-03 |
CN102439061B (zh) | 2013-05-08 |
US8912246B2 (en) | 2014-12-16 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
KR102141769B1 (ko) | 하이브리드 감광성 수지 및 그 제조방법 | |
CA2665607C (en) | Synthesis of inimers and hyperbranched polymers | |
CN108299343B (zh) | 一种用微通道反应器制备(甲基)丙烯酸-3,4-环氧环己基甲酯的方法 | |
WO2007125829A1 (ja) | 含フッ素アダマンタン誘導体、重合性基含有含フッ素アダマンタン誘導体、それを含有する樹脂組成物及び反射防止膜 | |
WO2007020901A1 (ja) | 含フッ素アダマンタン誘導体、重合性基含有含フッ素アダマンタン誘導体及びそれを含有する樹脂組成物 | |
JP5729845B2 (ja) | 可架橋固形化超分岐ポリエステルおよびその固形化産物とその調製方法 | |
JPS62265249A (ja) | カルボキシルを末端基とするラクトンアクリレ−ト | |
CN104211863A (zh) | 一种氮氧自由基聚合物刷阻聚剂的制备方法及其应用 | |
JP5136956B2 (ja) | 重合性組成物及びその重合物 | |
CN101712751B (zh) | 一种不饱和聚酯的合成方法 | |
JP2005113049A (ja) | 新規な脂環式ビニルエーテル類の重合体 | |
JP2019119715A (ja) | 多官能(メタ)アクリレート及びネットワークポリマーの製造方法。 | |
JP4644889B2 (ja) | 含フッ素多官能(メタ)アクリル酸エステル及び低屈折材料 | |
CN1194994C (zh) | 一种超支化聚合物的制备方法 | |
JPS60100537A (ja) | アダマンタンジカルボン酸ジアリル | |
JPH02193944A (ja) | (メタ)アクリル酸エステルの製造方法 | |
JP2007112764A (ja) | (メタ)アクリロイロオキシテトラヒドロフラン類およびその製造方法 | |
JP2010024388A (ja) | 重合性多分岐化合物及びその製造方法 | |
JP3900313B2 (ja) | 変性共重合体の製造方法 | |
JPH1072404A (ja) | ソルビトールの(メタ)アクリル酸エステル及びその製法 | |
CN102690198B (zh) | 一种丙烯酸五溴苄酯的制备方法 | |
CN104768939A (zh) | 高折射率(甲基)丙烯酸酯衍生物及其制备方法 | |
CN1182177C (zh) | 一种高效合成超支化聚酯-胺的方法 | |
JPH0354204A (ja) | 放射線重合可能な液晶性モノマー及びそのポリマー | |
JP2000302749A (ja) | (メタ)アクリル酸ポリオキシエチレン化ビスフェノ−ルsエステル、その製造法及び感光性樹脂組成物 |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
A977 | Report on retrieval |
Free format text: JAPANESE INTERMEDIATE CODE: A971007 Effective date: 20140331 |
|
A131 | Notification of reasons for refusal |
Free format text: JAPANESE INTERMEDIATE CODE: A131 Effective date: 20140408 |
|
A601 | Written request for extension of time |
Free format text: JAPANESE INTERMEDIATE CODE: A601 Effective date: 20140702 |
|
A602 | Written permission of extension of time |
Free format text: JAPANESE INTERMEDIATE CODE: A602 Effective date: 20140709 |
|
A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20140718 |
|
A131 | Notification of reasons for refusal |
Free format text: JAPANESE INTERMEDIATE CODE: A131 Effective date: 20150115 |
|
A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20150123 |
|
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: 20150324 |
|
A61 | First payment of annual fees (during grant procedure) |
Free format text: JAPANESE INTERMEDIATE CODE: A61 Effective date: 20150403 |
|
R150 | Certificate of patent or registration of utility model |
Ref document number: 5729845 Country of ref document: JP Free format text: JAPANESE INTERMEDIATE CODE: R150 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
LAPS | Cancellation because of no payment of annual fees |