AU2012210727B2 - Benzoxazine resins - Google Patents
Benzoxazine resins Download PDFInfo
- Publication number
- AU2012210727B2 AU2012210727B2 AU2012210727A AU2012210727A AU2012210727B2 AU 2012210727 B2 AU2012210727 B2 AU 2012210727B2 AU 2012210727 A AU2012210727 A AU 2012210727A AU 2012210727 A AU2012210727 A AU 2012210727A AU 2012210727 B2 AU2012210727 B2 AU 2012210727B2
- Authority
- AU
- Australia
- Prior art keywords
- benzoxazine
- component
- composition according
- polyarylsulphone
- group
- 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.)
- Ceased
Links
- CMLFRMDBDNHMRA-UHFFFAOYSA-N 2h-1,2-benzoxazine Chemical compound C1=CC=C2C=CNOC2=C1 CMLFRMDBDNHMRA-UHFFFAOYSA-N 0.000 title claims abstract description 141
- 229920005989 resin Polymers 0.000 title claims abstract description 67
- 239000011347 resin Substances 0.000 title claims abstract description 67
- 239000000203 mixture Substances 0.000 claims abstract description 119
- 229920000642 polymer Polymers 0.000 claims abstract description 41
- 229920001169 thermoplastic Polymers 0.000 claims abstract description 35
- 239000004416 thermosoftening plastic Substances 0.000 claims abstract description 35
- 239000012745 toughening agent Substances 0.000 claims abstract description 34
- 239000002243 precursor Substances 0.000 claims abstract description 27
- 229920001187 thermosetting polymer Polymers 0.000 claims abstract description 25
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 51
- 150000001875 compounds Chemical class 0.000 claims description 36
- 125000000217 alkyl group Chemical group 0.000 claims description 32
- -1 benzoxazine compound Chemical class 0.000 claims description 26
- 125000003118 aryl group Chemical group 0.000 claims description 25
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims description 23
- 150000005130 benzoxazines Chemical class 0.000 claims description 18
- 239000002131 composite material Substances 0.000 claims description 16
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 16
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 13
- 229910052739 hydrogen Inorganic materials 0.000 claims description 13
- 239000000126 substance Substances 0.000 claims description 13
- 125000000732 arylene group Chemical group 0.000 claims description 12
- 150000003568 thioethers Chemical class 0.000 claims description 12
- 229910052799 carbon Inorganic materials 0.000 claims description 11
- 239000001257 hydrogen Substances 0.000 claims description 10
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 9
- 239000004593 Epoxy Substances 0.000 claims description 9
- 239000003822 epoxy resin Substances 0.000 claims description 9
- 229920000647 polyepoxide Polymers 0.000 claims description 9
- XLJMAIOERFSOGZ-UHFFFAOYSA-M cyanate Chemical compound [O-]C#N XLJMAIOERFSOGZ-UHFFFAOYSA-M 0.000 claims description 7
- 239000003085 diluting agent Substances 0.000 claims description 7
- 239000011521 glass Substances 0.000 claims description 7
- 150000002431 hydrogen Chemical class 0.000 claims description 7
- 230000000694 effects Effects 0.000 claims description 6
- 229920001568 phenolic resin Polymers 0.000 claims description 6
- 125000004432 carbon atom Chemical group C* 0.000 claims description 5
- 238000004132 cross linking Methods 0.000 claims description 5
- 239000012948 isocyanate Substances 0.000 claims description 5
- 150000002513 isocyanates Chemical class 0.000 claims description 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 5
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims description 4
- MQJKPEGWNLWLTK-UHFFFAOYSA-N Dapsone Chemical compound C1=CC(N)=CC=C1S(=O)(=O)C1=CC=C(N)C=C1 MQJKPEGWNLWLTK-UHFFFAOYSA-N 0.000 claims description 4
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- 150000008064 anhydrides Chemical class 0.000 claims description 4
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 claims description 4
- 125000000623 heterocyclic group Chemical group 0.000 claims description 4
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims description 4
- 125000001174 sulfone group Chemical group 0.000 claims description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
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- LNEPOXFFQSENCJ-UHFFFAOYSA-N haloperidol Chemical compound C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 LNEPOXFFQSENCJ-UHFFFAOYSA-N 0.000 claims description 3
- 230000003014 reinforcing effect Effects 0.000 claims description 3
- LJGHYPLBDBRCRZ-UHFFFAOYSA-N 3-(3-aminophenyl)sulfonylaniline Chemical compound NC1=CC=CC(S(=O)(=O)C=2C=C(N)C=CC=2)=C1 LJGHYPLBDBRCRZ-UHFFFAOYSA-N 0.000 claims description 2
- 229920000265 Polyparaphenylene Polymers 0.000 claims description 2
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 claims description 2
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- HBMJWWWQQXIZIP-UHFFFAOYSA-N silicon carbide Chemical compound [Si+]#[C-] HBMJWWWQQXIZIP-UHFFFAOYSA-N 0.000 claims description 2
- 229910010271 silicon carbide Inorganic materials 0.000 claims description 2
- MHSKRLJMQQNJNC-UHFFFAOYSA-N terephthalamide Chemical compound NC(=O)C1=CC=C(C(N)=O)C=C1 MHSKRLJMQQNJNC-UHFFFAOYSA-N 0.000 claims description 2
- 239000005007 epoxy-phenolic resin Substances 0.000 claims 1
- 150000002430 hydrocarbons Chemical group 0.000 claims 1
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical class C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 27
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 26
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 21
- PXKLMJQFEQBVLD-UHFFFAOYSA-N bisphenol F Chemical compound C1=CC(O)=CC=C1CC1=CC=C(O)C=C1 PXKLMJQFEQBVLD-UHFFFAOYSA-N 0.000 description 19
- 238000000034 method Methods 0.000 description 18
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- 239000000463 material Substances 0.000 description 14
- 239000007787 solid Substances 0.000 description 14
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- 239000002904 solvent Substances 0.000 description 13
- 239000003795 chemical substances by application Substances 0.000 description 12
- 125000001424 substituent group Chemical group 0.000 description 11
- 229930185605 Bisphenol Natural products 0.000 description 10
- 229940106691 bisphenol a Drugs 0.000 description 10
- 239000000047 product Substances 0.000 description 10
- 230000015572 biosynthetic process Effects 0.000 description 9
- 238000001802 infusion Methods 0.000 description 9
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 8
- 235000019256 formaldehyde Nutrition 0.000 description 8
- 239000000243 solution Substances 0.000 description 8
- 229960004132 diethyl ether Drugs 0.000 description 7
- 230000009477 glass transition Effects 0.000 description 7
- 125000001183 hydrocarbyl group Chemical group 0.000 description 7
- 239000011159 matrix material Substances 0.000 description 7
- 239000000178 monomer Substances 0.000 description 7
- 238000005191 phase separation Methods 0.000 description 7
- 238000003756 stirring Methods 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- 239000003054 catalyst Substances 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 6
- 239000003921 oil Substances 0.000 description 6
- 229960003742 phenol Drugs 0.000 description 6
- 239000005011 phenolic resin Substances 0.000 description 6
- 239000012744 reinforcing agent Substances 0.000 description 6
- 238000003786 synthesis reaction Methods 0.000 description 6
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 5
- 150000001412 amines Chemical class 0.000 description 5
- 229910052736 halogen Inorganic materials 0.000 description 5
- 150000002367 halogens Chemical class 0.000 description 5
- 230000000269 nucleophilic effect Effects 0.000 description 5
- IWDCLRJOBJJRNH-UHFFFAOYSA-N p-cresol Chemical compound CC1=CC=C(O)C=C1 IWDCLRJOBJJRNH-UHFFFAOYSA-N 0.000 description 5
- 150000002989 phenols Chemical class 0.000 description 5
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 4
- 230000008901 benefit Effects 0.000 description 4
- 230000000052 comparative effect Effects 0.000 description 4
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- 229910002804 graphite Inorganic materials 0.000 description 4
- 239000010439 graphite Substances 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
- 229920003986 novolac Polymers 0.000 description 4
- 239000001301 oxygen Substances 0.000 description 4
- 229910052760 oxygen Inorganic materials 0.000 description 4
- KJFMBFZCATUALV-UHFFFAOYSA-N phenolphthalein Chemical compound C1=CC(O)=CC=C1C1(C=2C=CC(O)=CC=2)C2=CC=CC=C2C(=O)O1 KJFMBFZCATUALV-UHFFFAOYSA-N 0.000 description 4
- 238000002360 preparation method Methods 0.000 description 4
- 230000008569 process Effects 0.000 description 4
- 230000002787 reinforcement Effects 0.000 description 4
- 239000011342 resin composition Substances 0.000 description 4
- 239000005060 rubber Substances 0.000 description 4
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 4
- 229920002554 vinyl polymer Polymers 0.000 description 4
- KXGFMDJXCMQABM-UHFFFAOYSA-N 2-methoxy-6-methylphenol Chemical compound [CH]OC1=CC=CC([CH])=C1O KXGFMDJXCMQABM-UHFFFAOYSA-N 0.000 description 3
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 3
- VPWNQTHUCYMVMZ-UHFFFAOYSA-N 4,4'-sulfonyldiphenol Chemical class C1=CC(O)=CC=C1S(=O)(=O)C1=CC=C(O)C=C1 VPWNQTHUCYMVMZ-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- PEEHTFAAVSWFBL-UHFFFAOYSA-N Maleimide Chemical compound O=C1NC(=O)C=C1 PEEHTFAAVSWFBL-UHFFFAOYSA-N 0.000 description 3
- KWYHDKDOAIKMQN-UHFFFAOYSA-N N,N,N',N'-tetramethylethylenediamine Chemical compound CN(C)CCN(C)C KWYHDKDOAIKMQN-UHFFFAOYSA-N 0.000 description 3
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- YCIMNLLNPGFGHC-UHFFFAOYSA-N catechol Chemical compound OC1=CC=CC=C1O YCIMNLLNPGFGHC-UHFFFAOYSA-N 0.000 description 3
- 229910052801 chlorine Inorganic materials 0.000 description 3
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- 238000012545 processing Methods 0.000 description 3
- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 description 3
- XMTQQYYKAHVGBJ-UHFFFAOYSA-N 3-(3,4-DICHLOROPHENYL)-1,1-DIMETHYLUREA Chemical compound CN(C)C(=O)NC1=CC=C(Cl)C(Cl)=C1 XMTQQYYKAHVGBJ-UHFFFAOYSA-N 0.000 description 2
- PLIKAWJENQZMHA-UHFFFAOYSA-N 4-aminophenol Chemical compound NC1=CC=C(O)C=C1 PLIKAWJENQZMHA-UHFFFAOYSA-N 0.000 description 2
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- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- 101100373011 Drosophila melanogaster wapl gene Proteins 0.000 description 2
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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
- C08L81/00—Compositions of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing sulfur with or without nitrogen, oxygen or carbon only; Compositions of polysulfones; Compositions of derivatives of such polymers
- C08L81/06—Polysulfones; Polyethersulfones
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D265/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom and one oxygen atom as the only ring hetero atoms
- C07D265/04—1,3-Oxazines; Hydrogenated 1,3-oxazines
- C07D265/12—1,3-Oxazines; Hydrogenated 1,3-oxazines condensed with carbocyclic rings or ring systems
- C07D265/14—1,3-Oxazines; Hydrogenated 1,3-oxazines condensed with carbocyclic rings or ring systems condensed with one six-membered ring
- C07D265/16—1,3-Oxazines; Hydrogenated 1,3-oxazines condensed with carbocyclic rings or ring systems condensed with one six-membered ring with only hydrogen or carbon atoms directly attached in positions 2 and 4
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
-
- 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
- C08G73/00—Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00
- C08G73/02—Polyamines
- C08G73/0233—Polyamines derived from (poly)oxazolines, (poly)oxazines or having pendant acyl groups
-
- 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
- C08G73/00—Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00
- C08G73/02—Polyamines
- C08G73/026—Wholly aromatic polyamines
-
- 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
- C08G73/00—Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00
- C08G73/06—Polycondensates having nitrogen-containing heterocyclic rings in the main chain of the macromolecule
- C08G73/22—Polybenzoxazoles
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J5/00—Manufacture of articles or shaped materials containing macromolecular substances
- C08J5/24—Impregnating materials with prepolymers which can be polymerised in situ, e.g. manufacture of prepregs
-
- 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
- C08K7/00—Use of ingredients characterised by shape
- C08K7/02—Fibres or whiskers
- C08K7/04—Fibres or whiskers inorganic
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L79/00—Compositions of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing nitrogen with or without oxygen or carbon only, not provided for in groups C08L61/00 - C08L77/00
- C08L79/02—Polyamines
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L79/00—Compositions of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing nitrogen with or without oxygen or carbon only, not provided for in groups C08L61/00 - C08L77/00
- C08L79/04—Polycondensates having nitrogen-containing heterocyclic rings in the main chain; Polyhydrazides; Polyamide acids or similar polyimide precursors
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L2205/00—Polymer mixtures characterised by other features
- C08L2205/03—Polymer mixtures characterised by other features containing three or more polymers in a blend
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L2205/00—Polymer mixtures characterised by other features
- C08L2205/08—Polymer mixtures characterised by other features containing additives to improve the compatibility between two polymers
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Manufacturing & Machinery (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Phenolic Resins Or Amino Resins (AREA)
- Reinforced Plastic Materials (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GBGB1101302.6A GB201101302D0 (en) | 2011-01-25 | 2011-01-25 | Benzoxazine resins |
| GB1101302.6 | 2011-01-25 | ||
| PCT/EP2012/050307 WO2012100980A1 (en) | 2011-01-25 | 2012-01-10 | Benzoxazine resins |
Publications (2)
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| AU2012210727A1 AU2012210727A1 (en) | 2013-04-04 |
| AU2012210727B2 true AU2012210727B2 (en) | 2014-04-03 |
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| EP (1) | EP2668238B1 (enExample) |
| JP (2) | JP5931089B2 (enExample) |
| KR (1) | KR101840506B1 (enExample) |
| CN (1) | CN103339202B (enExample) |
| AU (1) | AU2012210727B2 (enExample) |
| BR (1) | BR112013018415B1 (enExample) |
| CA (1) | CA2825451C (enExample) |
| ES (1) | ES2530626T3 (enExample) |
| GB (1) | GB201101302D0 (enExample) |
| MY (1) | MY160730A (enExample) |
| TW (1) | TWI540150B (enExample) |
| WO (1) | WO2012100980A1 (enExample) |
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| GB201101302D0 (en) * | 2011-01-25 | 2011-03-09 | Cytec Tech Corp | Benzoxazine resins |
| KR20150125003A (ko) * | 2013-03-04 | 2015-11-06 | 헌츠만 어드밴스드 머티리얼스 아메리카스 엘엘씨 | 폴리설폰계 강인화제를 함유하는 벤족사진 경화성 조성물 |
| GB201322758D0 (en) * | 2013-12-20 | 2014-02-05 | Cytec Ind Inc | Multifunctional benzoxazines and composite materials incorporating then same |
| WO2015104973A1 (ja) * | 2014-01-07 | 2015-07-16 | Dic株式会社 | ポリアリーレンエーテル樹脂、ポリアリーレンエーテル樹脂の製造方法、硬化性樹脂材料、その硬化物、半導体封止材料、プリプレグ、回路基板、及びビルドアップフィルム |
| CN103937157A (zh) * | 2014-03-05 | 2014-07-23 | 浙江华正新材料股份有限公司 | 无卤树脂组合物及采用其制造半固化片及层压板的方法 |
| WO2016003167A1 (ko) * | 2014-06-30 | 2016-01-07 | 코오롱인더스트리 주식회사 | 폴리벤족사진 전구체 및 그 제조방법 |
| TWI573820B (zh) | 2014-06-30 | 2017-03-11 | 可隆股份有限公司 | 聚氧代氮代苯并環己烷前驅物及其製備方法 |
| US9751966B2 (en) | 2014-12-22 | 2017-09-05 | The Boeing Company | Rapid cure polymeric resins |
| TWI685534B (zh) * | 2014-12-29 | 2020-02-21 | 美商塞特工業公司 | 苯并化物及含彼之組合物 |
| CN107108885B (zh) * | 2014-12-29 | 2019-09-03 | 塞特工业公司 | 三官能苯并噁嗪以及其在可固化树脂组合物和复合材料中的用途 |
| GB201509294D0 (en) | 2015-05-29 | 2015-07-15 | Cytec Ind Inc | Process for preparing moulded articles from fibre-reinforced composite materials - I |
| GB201509292D0 (en) | 2015-05-29 | 2015-07-15 | Cytec Ind Inc | Process for preparing moulded articles from fibre-reinforced composite materials - II |
| BR112018001264B1 (pt) | 2015-07-23 | 2022-04-19 | Huntsman Advanced Materials Americas Llc | Composição curável, processo para produção de uma composição curável, artigo curado, e, método para produção de um prepreg ou towpreg. |
| CN106565746B (zh) * | 2015-10-12 | 2021-06-15 | 3M创新有限公司 | 苯并噁嗪化合物、其聚合物及其制法和由其制得的粘合剂 |
| US10273369B2 (en) * | 2015-12-07 | 2019-04-30 | Raytheon Company | Use of benzoxazine as a structural thermal protective system (TPS) and heat shield material |
| JP6824699B2 (ja) * | 2015-12-11 | 2021-02-03 | 本州化学工業株式会社 | 新規ベンゾオキサジン化合物 |
| CN108431134B (zh) * | 2015-12-15 | 2021-03-09 | 3M创新有限公司 | 苯并噁嗪和酞腈树脂共混物 |
| US10975044B2 (en) * | 2017-05-24 | 2021-04-13 | Compagnie Generale Des Etablissements Michelin | Halogenated benzoxazine for use in the synthesis of polybenzoxazine |
| CN110691778B (zh) | 2017-05-24 | 2023-06-30 | 米其林集团总公司 | 用于合成聚苯并噁嗪的卤代苯并噁嗪 |
| CN108409681B (zh) * | 2018-05-22 | 2023-11-03 | 成都科宜高分子科技有限公司 | 一种连续化制备苯并噁嗪的方法 |
| CN109435374B (zh) * | 2018-09-17 | 2019-10-29 | 杭州铠恒新材料有限公司 | 一种建筑用苯并噁嗪树脂基金属箔复合板及其制备方法 |
| JP2020063223A (ja) | 2018-10-19 | 2020-04-23 | 本州化学工業株式会社 | 芳香族テトラカルボン酸化合物 |
| CN110204857A (zh) * | 2019-06-06 | 2019-09-06 | 江门建滔积层板有限公司 | 一种基于苯并噁嗪树脂的低介电覆铜板的制备方法 |
| GB202211309D0 (en) * | 2022-08-03 | 2022-09-14 | Jones Paul | Ortho-substituted difunctional bio-benzoxazine compounds,preparation methods and uses thereof |
| CN117004180B (zh) * | 2023-09-27 | 2023-12-26 | 常州宏巨电子科技有限公司 | 一种主链型苯并噁嗪泡棉材料及其制备方法和应用 |
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| TWI295288B (en) | 2006-08-17 | 2008-04-01 | Univ Nat Chunghsing | New route for the synthesis of benzoxazine |
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| JP5421630B2 (ja) * | 2008-03-26 | 2014-02-19 | 積水化学工業株式会社 | 熱硬化性樹脂、熱硬化性樹脂を含む熱硬化性組成物及びその成形体、硬化体、硬化成形体、並びにそれらを含む電子機器 |
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-
2011
- 2011-01-25 GB GBGB1101302.6A patent/GB201101302D0/en not_active Ceased
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2012
- 2012-01-10 EP EP12700270.7A patent/EP2668238B1/en active Active
- 2012-01-10 CA CA2825451A patent/CA2825451C/en active Active
- 2012-01-10 JP JP2013550817A patent/JP5931089B2/ja active Active
- 2012-01-10 BR BR112013018415A patent/BR112013018415B1/pt not_active IP Right Cessation
- 2012-01-10 US US13/981,640 patent/US9255075B2/en active Active
- 2012-01-10 MY MYPI2013002646A patent/MY160730A/en unknown
- 2012-01-10 CN CN201280006411.0A patent/CN103339202B/zh active Active
- 2012-01-10 KR KR1020137022224A patent/KR101840506B1/ko not_active Expired - Fee Related
- 2012-01-10 AU AU2012210727A patent/AU2012210727B2/en not_active Ceased
- 2012-01-10 WO PCT/EP2012/050307 patent/WO2012100980A1/en not_active Ceased
- 2012-01-10 ES ES12700270T patent/ES2530626T3/es active Active
- 2012-01-20 TW TW101102353A patent/TWI540150B/zh not_active IP Right Cessation
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- 2015-12-31 US US14/985,550 patent/US9732225B2/en active Active
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2016
- 2016-04-18 JP JP2016082734A patent/JP6033484B2/ja active Active
Also Published As
| Publication number | Publication date |
|---|---|
| US9255075B2 (en) | 2016-02-09 |
| US9732225B2 (en) | 2017-08-15 |
| AU2012210727A1 (en) | 2013-04-04 |
| US20130345352A1 (en) | 2013-12-26 |
| TW201235379A (en) | 2012-09-01 |
| MY160730A (en) | 2017-03-15 |
| CA2825451C (en) | 2019-03-19 |
| CN103339202A (zh) | 2013-10-02 |
| JP6033484B2 (ja) | 2016-11-30 |
| CN103339202B (zh) | 2015-04-22 |
| WO2012100980A1 (en) | 2012-08-02 |
| JP5931089B2 (ja) | 2016-06-08 |
| BR112013018415B1 (pt) | 2020-04-14 |
| BR112013018415A2 (pt) | 2016-10-11 |
| TWI540150B (zh) | 2016-07-01 |
| ES2530626T3 (es) | 2015-03-04 |
| EP2668238B1 (en) | 2014-11-19 |
| KR101840506B1 (ko) | 2018-03-20 |
| US20160115317A1 (en) | 2016-04-28 |
| JP2014503669A (ja) | 2014-02-13 |
| GB201101302D0 (en) | 2011-03-09 |
| CA2825451A1 (en) | 2012-08-02 |
| JP2016166364A (ja) | 2016-09-15 |
| EP2668238A1 (en) | 2013-12-04 |
| KR20140007856A (ko) | 2014-01-20 |
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