BR112014002564B1 - Composição de polímero curável, e, material compósito - Google Patents
Composição de polímero curável, e, material compósito Download PDFInfo
- Publication number
- BR112014002564B1 BR112014002564B1 BR112014002564-9A BR112014002564A BR112014002564B1 BR 112014002564 B1 BR112014002564 B1 BR 112014002564B1 BR 112014002564 A BR112014002564 A BR 112014002564A BR 112014002564 B1 BR112014002564 B1 BR 112014002564B1
- Authority
- BR
- Brazil
- Prior art keywords
- polymer
- aromatic
- thermosetting resin
- composition according
- block copolymer
- Prior art date
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- 229920000642 polymer Polymers 0.000 title claims abstract description 202
- 239000000203 mixture Substances 0.000 title claims abstract description 132
- 239000002131 composite material Substances 0.000 title claims abstract description 27
- 239000002861 polymer material Substances 0.000 title 1
- 229920005989 resin Polymers 0.000 claims abstract description 150
- 239000011347 resin Substances 0.000 claims abstract description 150
- 229920001187 thermosetting polymer Polymers 0.000 claims abstract description 100
- 229920001400 block copolymer Polymers 0.000 claims abstract description 85
- 239000002243 precursor Substances 0.000 claims abstract description 71
- 125000003118 aryl group Chemical group 0.000 claims abstract description 57
- 229920001169 thermoplastic Polymers 0.000 claims abstract description 35
- 239000004416 thermosoftening plastic Substances 0.000 claims abstract description 22
- 230000009477 glass transition Effects 0.000 claims abstract description 19
- 239000003822 epoxy resin Substances 0.000 claims description 54
- 229920000647 polyepoxide Polymers 0.000 claims description 54
- 239000003795 chemical substances by application Substances 0.000 claims description 33
- -1 cyclic aliphatic alcohols Chemical class 0.000 claims description 31
- 238000000034 method Methods 0.000 claims description 29
- 125000004432 carbon atom Chemical group C* 0.000 claims description 28
- 239000011342 resin composition Substances 0.000 claims description 20
- 238000006243 chemical reaction Methods 0.000 claims description 19
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 18
- 239000002253 acid Substances 0.000 claims description 14
- 150000002118 epoxides Chemical group 0.000 claims description 14
- 229920000728 polyester Polymers 0.000 claims description 14
- 239000000126 substance Substances 0.000 claims description 14
- 125000001931 aliphatic group Chemical group 0.000 claims description 13
- 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 12
- 229910052757 nitrogen Inorganic materials 0.000 claims description 12
- CWLKGDAVCFYWJK-UHFFFAOYSA-N 3-aminophenol Chemical compound NC1=CC=CC(O)=C1 CWLKGDAVCFYWJK-UHFFFAOYSA-N 0.000 claims description 11
- 229910052799 carbon Inorganic materials 0.000 claims description 11
- 125000005647 linker group Chemical group 0.000 claims description 10
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 claims description 10
- 150000001298 alcohols Chemical class 0.000 claims description 9
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 claims description 9
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 9
- 150000003457 sulfones Chemical class 0.000 claims description 9
- PLIKAWJENQZMHA-UHFFFAOYSA-N 4-aminophenol Chemical compound NC1=CC=C(O)C=C1 PLIKAWJENQZMHA-UHFFFAOYSA-N 0.000 claims description 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 8
- PXKLMJQFEQBVLD-UHFFFAOYSA-N bisphenol F Chemical compound C1=CC(O)=CC=C1CC1=CC=C(O)C=C1 PXKLMJQFEQBVLD-UHFFFAOYSA-N 0.000 claims description 8
- 239000003153 chemical reaction reagent Substances 0.000 claims description 8
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- 125000003277 amino group Chemical group 0.000 claims description 7
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- 150000001412 amines Chemical class 0.000 claims description 6
- 229910052760 oxygen Inorganic materials 0.000 claims description 6
- LCFVJGUPQDGYKZ-UHFFFAOYSA-N Bisphenol A diglycidyl ether Chemical compound C=1C=C(OCC2OC2)C=CC=1C(C)(C)C(C=C1)=CC=C1OCC1CO1 LCFVJGUPQDGYKZ-UHFFFAOYSA-N 0.000 claims description 5
- 235000014113 dietary fatty acids Nutrition 0.000 claims description 5
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- 125000003055 glycidyl group Chemical group C(C1CO1)* 0.000 claims description 5
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- 229920001002 functional polymer Polymers 0.000 claims description 4
- 229910052717 sulfur Inorganic materials 0.000 claims description 4
- WZCQRUWWHSTZEM-UHFFFAOYSA-N 1,3-phenylenediamine Chemical compound NC1=CC=CC(N)=C1 WZCQRUWWHSTZEM-UHFFFAOYSA-N 0.000 claims description 3
- CDAWCLOXVUBKRW-UHFFFAOYSA-N 2-aminophenol Chemical class NC1=CC=CC=C1O CDAWCLOXVUBKRW-UHFFFAOYSA-N 0.000 claims description 3
- YBRVSVVVWCFQMG-UHFFFAOYSA-N 4,4'-diaminodiphenylmethane Chemical compound C1=CC(N)=CC=C1CC1=CC=C(N)C=C1 YBRVSVVVWCFQMG-UHFFFAOYSA-N 0.000 claims description 3
- 150000001875 compounds Chemical class 0.000 claims description 3
- GYZLOYUZLJXAJU-UHFFFAOYSA-N diglycidyl ether Chemical class C1OC1COCC1CO1 GYZLOYUZLJXAJU-UHFFFAOYSA-N 0.000 claims description 3
- DEQUKPCANKRTPZ-UHFFFAOYSA-N (2,3-dihydroxyphenyl)-phenylmethanone Chemical compound OC1=CC=CC(C(=O)C=2C=CC=CC=2)=C1O DEQUKPCANKRTPZ-UHFFFAOYSA-N 0.000 claims description 2
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 claims description 2
- CBCKQZAAMUWICA-UHFFFAOYSA-N 1,4-phenylenediamine Chemical compound NC1=CC=C(N)C=C1 CBCKQZAAMUWICA-UHFFFAOYSA-N 0.000 claims description 2
- DGRGLKZMKWPMOH-UHFFFAOYSA-N 4-methylbenzene-1,2-diamine Chemical compound CC1=CC=C(N)C(N)=C1 DGRGLKZMKWPMOH-UHFFFAOYSA-N 0.000 claims description 2
- 150000008065 acid anhydrides Chemical class 0.000 claims description 2
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- 150000004984 aromatic diamines Chemical class 0.000 claims description 2
- XUCHXOAWJMEFLF-UHFFFAOYSA-N bisphenol F diglycidyl ether Chemical compound C1OC1COC(C=C1)=CC=C1CC(C=C1)=CC=C1OCC1CO1 XUCHXOAWJMEFLF-UHFFFAOYSA-N 0.000 claims description 2
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- 125000004122 cyclic group Chemical group 0.000 claims description 2
- 150000002989 phenols Chemical class 0.000 claims description 2
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- FAUAZXVRLVIARB-UHFFFAOYSA-N 4-[[4-[bis(oxiran-2-ylmethyl)amino]phenyl]methyl]-n,n-bis(oxiran-2-ylmethyl)aniline Chemical compound C1OC1CN(C=1C=CC(CC=2C=CC(=CC=2)N(CC2OC2)CC2OC2)=CC=1)CC1CO1 FAUAZXVRLVIARB-UHFFFAOYSA-N 0.000 claims 1
- NLZUEZXRPGMBCV-UHFFFAOYSA-N Butylhydroxytoluene Chemical compound CC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 NLZUEZXRPGMBCV-UHFFFAOYSA-N 0.000 claims 1
- 238000001723 curing Methods 0.000 description 47
- 239000000243 solution Substances 0.000 description 42
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 36
- 239000000463 material Substances 0.000 description 34
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- 229920006393 polyether sulfone Polymers 0.000 description 31
- 239000003351 stiffener Substances 0.000 description 28
- 239000004695 Polyether sulfone Substances 0.000 description 24
- 239000002245 particle Substances 0.000 description 22
- 239000002904 solvent Substances 0.000 description 21
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 18
- 239000004593 Epoxy Substances 0.000 description 13
- 230000015572 biosynthetic process Effects 0.000 description 13
- 239000003054 catalyst Substances 0.000 description 13
- 239000003607 modifier Substances 0.000 description 13
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 12
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- 238000004627 transmission electron microscopy Methods 0.000 description 12
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- 238000002156 mixing Methods 0.000 description 9
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 9
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 8
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 8
- 235000011089 carbon dioxide Nutrition 0.000 description 8
- 238000001802 infusion Methods 0.000 description 8
- 229920005906 polyester polyol Polymers 0.000 description 8
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- 238000012360 testing method Methods 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 6
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 6
- 101000605126 Mus musculus Prostaglandin G/H synthase 2 Proteins 0.000 description 6
- WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 description 6
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- 239000002086 nanomaterial Substances 0.000 description 6
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- LXEJRKJRKIFVNY-UHFFFAOYSA-N terephthaloyl chloride Chemical compound ClC(=O)C1=CC=C(C(Cl)=O)C=C1 LXEJRKJRKIFVNY-UHFFFAOYSA-N 0.000 description 6
- 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 5
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- FIJSKXFJFGTBRV-UHFFFAOYSA-N 2-[[2-[[2-(oxiran-2-ylmethoxy)phenyl]methyl]phenoxy]methyl]oxirane Chemical compound C1OC1COC1=CC=CC=C1CC1=CC=CC=C1OCC1CO1 FIJSKXFJFGTBRV-UHFFFAOYSA-N 0.000 description 4
- CMLFRMDBDNHMRA-UHFFFAOYSA-N 2h-1,2-benzoxazine Chemical compound C1=CC=C2C=CNOC2=C1 CMLFRMDBDNHMRA-UHFFFAOYSA-N 0.000 description 4
- 240000005369 Alstonia scholaris Species 0.000 description 4
- 229910015900 BF3 Inorganic materials 0.000 description 4
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 4
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- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
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- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 4
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- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 3
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- C08G63/688—Polyesters containing atoms other than carbon, hydrogen and oxygen containing sulfur
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- 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
- C08J2363/00—Characterised by the use of epoxy resins; Derivatives of epoxy resins
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- 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
- C08J2467/00—Characterised by the use of polyesters obtained by reactions forming a carboxylic ester link in the main chain; Derivatives of such polymers
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- 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
- C08J2481/00—Characterised by the use 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; Polysulfones; Derivatives of such polymers
- C08J2481/06—Polysulfones; Polyethersulfones
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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
- C08L67/00—Compositions of polyesters obtained by reactions forming a carboxylic ester link in the main chain; Compositions of derivatives of such polymers
-
- 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
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- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Materials Engineering (AREA)
- Engineering & Computer Science (AREA)
- Manufacturing & Machinery (AREA)
- Inorganic Chemistry (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Other Resins Obtained By Reactions Not Involving Carbon-To-Carbon Unsaturated Bonds (AREA)
- Graft Or Block Polymers (AREA)
- Epoxy Resins (AREA)
- Polyesters Or Polycarbonates (AREA)
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| GBGB1113196.8A GB201113196D0 (en) | 2011-08-01 | 2011-08-01 | Thermoset resin compositions with increased toughness |
| GB1113196.8 | 2011-08-01 | ||
| PCT/GB2012/051779 WO2013017843A2 (en) | 2011-08-01 | 2012-07-25 | Thermoset resin compositions with increased toughness |
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| BR112014002564B1 true BR112014002564B1 (pt) | 2021-04-06 |
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| BR112014002564-9A BR112014002564B1 (pt) | 2011-08-01 | 2012-07-25 | Composição de polímero curável, e, material compósito |
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| WO (1) | WO2013017843A2 (https=) |
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| EP2808353A1 (en) * | 2013-05-31 | 2014-12-03 | Huntsman International Llc | A method for improving toughness of polyisocyanate polyaddition reaction products |
| JP5852633B2 (ja) * | 2013-07-04 | 2016-02-03 | 太陽インキ製造株式会社 | 硬化性樹脂組成物、その硬化物、これを有するプリント配線板、及び硬化物の製造方法 |
| JP2017523256A (ja) * | 2014-05-22 | 2017-08-17 | サイテック インダストリーズ インコーポレイテッド | 強化剤として使用するための官能化重合体粒子 |
| US9957345B2 (en) | 2014-08-18 | 2018-05-01 | International Business Machines Corporation | 3D printing with PHT based materials |
| US10023735B2 (en) | 2014-08-18 | 2018-07-17 | International Business Machines Corporation | 3D printing with PHT/PHA based materials and polymerizable monomers |
| KR102408039B1 (ko) * | 2014-12-18 | 2022-06-13 | 사이텍 인더스트리스 인코포레이티드 | 액상 수지 주입에 적합한 개질된 수지 시스템 |
| WO2017019979A1 (en) * | 2015-07-30 | 2017-02-02 | University Of Massachusetts | Impact modified compositions methods of manufacture thereof and articles comprisng the same |
| US9758620B2 (en) | 2015-09-03 | 2017-09-12 | International Business Machines Corporation | Tailorable viscoelastic properties of PEG-hemiaminal organogel networks |
| KR101720563B1 (ko) * | 2015-11-05 | 2017-03-29 | 국방과학연구소 | 폴리술폰계 고분자 강인화제를 함유하는 폴리술폰계 고분자 강인화 에폭시 수지 조성물 및 이의 제조 방법 |
| US9873766B2 (en) | 2015-11-24 | 2018-01-23 | International Business Machines Corporation | Systems chemistry approach to polyhexahydrotriazine polymeric structures |
| CN108473633B (zh) | 2016-11-08 | 2020-12-01 | H.B.富乐公司 | 可低温固化的粘合剂组合物和包含其的制品 |
| WO2018131580A1 (ja) * | 2017-01-13 | 2018-07-19 | 東レ株式会社 | エポキシ樹脂組成物、エポキシ樹脂硬化物、プリプレグ、繊維強化複合材料、ブロック共重合体およびその製造方法 |
| US10213642B2 (en) * | 2017-04-28 | 2019-02-26 | Katie Swarts | Terrain belt for use with a treadmill |
| CN110914355A (zh) * | 2017-07-12 | 2020-03-24 | 赫克塞尔合成有限公司 | 树脂组合物 |
| MY208152A (en) * | 2018-03-16 | 2025-04-18 | Huntsman Adv Mat Licensing Switzerland Gmbh | Storage stable and curable resin compositions |
| KR102311641B1 (ko) | 2018-11-23 | 2021-10-13 | 주식회사 엘지화학 | 수지 조성물, 이를 포함하는 프리프레그, 이를 포함하는 적층판, 및 이를 포함하는 수지 부착 금속박 |
| US11086200B2 (en) | 2019-03-20 | 2021-08-10 | Ticona Llc | Polymer composition for use in a camera module |
| CN113710738A (zh) * | 2019-03-20 | 2021-11-26 | 提克纳有限责任公司 | 用于相机模块的致动器组件 |
| EP4296297B1 (en) * | 2021-02-18 | 2025-11-05 | Toray Industries, Inc. | Epoxy resin composition for fiber-reinforced composite material, fiber-reinforced composite material, and method for producing fiber-reinforced composite material |
| US12209163B2 (en) | 2021-05-06 | 2025-01-28 | Ticona Llc | Polymer composition for use in a camera module |
| DE102021121497A1 (de) | 2021-08-19 | 2023-02-23 | Fraunhofer-Gesellschaft zur Förderung der angewandten Forschung eingetragener Verein | Zusammensetzung zur Herstellung eines flächigen Halbzeugs |
| TW202340697A (zh) | 2021-12-13 | 2023-10-16 | 美商堤康那責任有限公司 | 樣品之滾珠凹部性質之測試技術 |
| JP7541419B2 (ja) * | 2022-04-22 | 2024-08-28 | エル・コーポレイション | アクリレート官能基を有する線状ブロック共重合体強化剤 |
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| DE3275637D1 (en) | 1981-01-21 | 1987-04-16 | Ici Plc | Fibre-reinforced compositions and methods for producing such compositions |
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| EP0367158B1 (en) * | 1988-11-03 | 1993-12-01 | The Dow Chemical Company | Preparation of poly(aryl ether/thioether)-polyester block copolymers |
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| US9567426B2 (en) | 2009-05-29 | 2017-02-14 | Cytec Technology Corp. | Engineered crosslinked thermoplastic particles for interlaminar toughening |
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| CA2843659C (en) | 2020-01-14 |
| MX343157B (es) | 2016-10-26 |
| GB201113196D0 (en) | 2011-09-14 |
| US20130184376A1 (en) | 2013-07-18 |
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| JP6184951B2 (ja) | 2017-08-23 |
| US8907049B2 (en) | 2014-12-09 |
| TW201307479A (zh) | 2013-02-16 |
| CN103906793B (zh) | 2016-04-27 |
| KR20140063647A (ko) | 2014-05-27 |
| TWI548698B (zh) | 2016-09-11 |
| ES2562106T3 (es) | 2016-03-02 |
| WO2013017843A3 (en) | 2013-06-13 |
| BR112014002564A2 (pt) | 2017-02-21 |
| IN2014CN00768A (https=) | 2015-04-03 |
| JP2014521800A (ja) | 2014-08-28 |
| AU2012291863A1 (en) | 2014-01-23 |
| RU2611628C2 (ru) | 2017-02-28 |
| EP2739672B1 (en) | 2015-11-18 |
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| KR102000655B1 (ko) | 2019-07-16 |
| WO2013017843A2 (en) | 2013-02-07 |
| AU2012291863B2 (en) | 2015-06-25 |
| EP2739672A2 (en) | 2014-06-11 |
| CA2843659A1 (en) | 2013-02-07 |
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