RU2017111045A - Способ улучшения трещиностойкости полиизоциануратсодержащих продуктов реакции - Google Patents
Способ улучшения трещиностойкости полиизоциануратсодержащих продуктов реакции Download PDFInfo
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- RU2017111045A RU2017111045A RU2017111045A RU2017111045A RU2017111045A RU 2017111045 A RU2017111045 A RU 2017111045A RU 2017111045 A RU2017111045 A RU 2017111045A RU 2017111045 A RU2017111045 A RU 2017111045A RU 2017111045 A RU2017111045 A RU 2017111045A
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- Prior art keywords
- curable composition
- paragraphs
- composition according
- polyisocyanurate
- range
- Prior art date
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- 238000000034 method Methods 0.000 title claims 13
- 239000007795 chemical reaction product Substances 0.000 title 1
- 238000005336 cracking Methods 0.000 title 1
- 239000000203 mixture Substances 0.000 claims 36
- 239000000463 material Substances 0.000 claims 11
- 229920001228 polyisocyanate Polymers 0.000 claims 9
- 239000005056 polyisocyanate Substances 0.000 claims 9
- 229920000582 polyisocyanurate Polymers 0.000 claims 9
- 239000011495 polyisocyanurate Substances 0.000 claims 9
- -1 aromatic polyols Chemical class 0.000 claims 8
- 229920001400 block copolymer Polymers 0.000 claims 7
- 239000012948 isocyanate Substances 0.000 claims 7
- 150000002513 isocyanates Chemical class 0.000 claims 7
- 239000000654 additive Substances 0.000 claims 4
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- 150000001875 compounds Chemical class 0.000 claims 4
- 150000002009 diols Chemical class 0.000 claims 4
- SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 claims 4
- 238000005829 trimerization reaction Methods 0.000 claims 4
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- 230000009477 glass transition Effects 0.000 claims 3
- 238000000465 moulding Methods 0.000 claims 3
- 239000005062 Polybutadiene Substances 0.000 claims 2
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims 2
- HIFVAOIJYDXIJG-UHFFFAOYSA-N benzylbenzene;isocyanic acid Chemical class N=C=O.N=C=O.C=1C=CC=CC=1CC1=CC=CC=C1 HIFVAOIJYDXIJG-UHFFFAOYSA-N 0.000 claims 2
- 229910052799 carbon Inorganic materials 0.000 claims 2
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- HBGGXOJOCNVPFY-UHFFFAOYSA-N diisononyl phthalate Chemical compound CC(C)CCCCCCOC(=O)C1=CC=CC=C1C(=O)OCCCCCCC(C)C HBGGXOJOCNVPFY-UHFFFAOYSA-N 0.000 claims 2
- 239000000835 fiber Substances 0.000 claims 2
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- 238000004519 manufacturing process Methods 0.000 claims 2
- 229920002857 polybutadiene Polymers 0.000 claims 2
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- FPIVAWNGRDHRSQ-UHFFFAOYSA-N 2-[di(propan-2-yloxy)methoxy]propane Chemical compound CC(C)OC(OC(C)C)OC(C)C FPIVAWNGRDHRSQ-UHFFFAOYSA-N 0.000 claims 1
- 244000198134 Agave sisalana Species 0.000 claims 1
- 244000025254 Cannabis sativa Species 0.000 claims 1
- 235000012766 Cannabis sativa ssp. sativa var. sativa Nutrition 0.000 claims 1
- 235000012765 Cannabis sativa ssp. sativa var. spontanea Nutrition 0.000 claims 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 1
- 240000006240 Linum usitatissimum Species 0.000 claims 1
- 235000004431 Linum usitatissimum Nutrition 0.000 claims 1
- 239000004952 Polyamide Substances 0.000 claims 1
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- 239000004743 Polypropylene Substances 0.000 claims 1
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- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 claims 1
- 239000004280 Sodium formate Substances 0.000 claims 1
- 239000012963 UV stabilizer Substances 0.000 claims 1
- 239000006096 absorbing agent Substances 0.000 claims 1
- 239000000370 acceptor Substances 0.000 claims 1
- 150000001252 acrylic acid derivatives Chemical class 0.000 claims 1
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims 1
- 230000000996 additive effect Effects 0.000 claims 1
- 125000001931 aliphatic group Chemical group 0.000 claims 1
- 239000003513 alkali Substances 0.000 claims 1
- 150000001342 alkaline earth metals Chemical class 0.000 claims 1
- 125000000217 alkyl group Chemical group 0.000 claims 1
- 229910052782 aluminium Inorganic materials 0.000 claims 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 claims 1
- 239000004599 antimicrobial Substances 0.000 claims 1
- 125000003118 aryl group Chemical group 0.000 claims 1
- 239000011324 bead Substances 0.000 claims 1
- 235000009120 camo Nutrition 0.000 claims 1
- 239000004202 carbamide Substances 0.000 claims 1
- 125000004432 carbon atom Chemical group C* 0.000 claims 1
- 150000001735 carboxylic acids Chemical class 0.000 claims 1
- 239000004568 cement Substances 0.000 claims 1
- 235000005607 chanvre indien Nutrition 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 claims 1
- 239000003795 chemical substances by application Substances 0.000 claims 1
- 239000004927 clay Substances 0.000 claims 1
- 238000010276 construction Methods 0.000 claims 1
- 238000011437 continuous method Methods 0.000 claims 1
- 238000007907 direct compression Methods 0.000 claims 1
- 239000002270 dispersing agent Substances 0.000 claims 1
- 239000000975 dye Substances 0.000 claims 1
- 229920001971 elastomer Polymers 0.000 claims 1
- 239000003822 epoxy resin Substances 0.000 claims 1
- SLFUXNFVAANERW-UHFFFAOYSA-N ethyl hexanoate;potassium Chemical compound [K].CCCCCC(=O)OCC SLFUXNFVAANERW-UHFFFAOYSA-N 0.000 claims 1
- 238000001125 extrusion Methods 0.000 claims 1
- 239000011152 fibreglass Substances 0.000 claims 1
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- 150000002334 glycols Chemical class 0.000 claims 1
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- 239000011487 hemp Substances 0.000 claims 1
- 238000001802 infusion Methods 0.000 claims 1
- 239000004615 ingredient Substances 0.000 claims 1
- 229910052809 inorganic oxide Inorganic materials 0.000 claims 1
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 claims 1
- 229910052744 lithium Inorganic materials 0.000 claims 1
- 239000002923 metal particle Substances 0.000 claims 1
- 239000002557 mineral fiber Substances 0.000 claims 1
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- 239000011087 paperboard Substances 0.000 claims 1
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- 229920003229 poly(methyl methacrylate) Polymers 0.000 claims 1
- 229920002647 polyamide Polymers 0.000 claims 1
- 229920001748 polybutylene Polymers 0.000 claims 1
- 229920000647 polyepoxide Polymers 0.000 claims 1
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- 229920001223 polyethylene glycol Polymers 0.000 claims 1
- 229920001195 polyisoprene Polymers 0.000 claims 1
- 239000004926 polymethyl methacrylate Substances 0.000 claims 1
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- ZUFQCVZBBNZMKD-UHFFFAOYSA-M potassium 2-ethylhexanoate Chemical compound [K+].CCCCC(CC)C([O-])=O ZUFQCVZBBNZMKD-UHFFFAOYSA-M 0.000 claims 1
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 claims 1
- 239000004300 potassium benzoate Substances 0.000 claims 1
- 235000010235 potassium benzoate Nutrition 0.000 claims 1
- 229940103091 potassium benzoate Drugs 0.000 claims 1
- WFIZEGIEIOHZCP-UHFFFAOYSA-M potassium formate Chemical compound [K+].[O-]C=O WFIZEGIEIOHZCP-UHFFFAOYSA-M 0.000 claims 1
- PHZLMBHDXVLRIX-UHFFFAOYSA-M potassium lactate Chemical compound [K+].CC(O)C([O-])=O PHZLMBHDXVLRIX-UHFFFAOYSA-M 0.000 claims 1
- 239000001521 potassium lactate Substances 0.000 claims 1
- 235000011085 potassium lactate Nutrition 0.000 claims 1
- 229960001304 potassium lactate Drugs 0.000 claims 1
- BLGUIMKBRCQORR-UHFFFAOYSA-M potassium;hexanoate Chemical compound [K+].CCCCCC([O-])=O BLGUIMKBRCQORR-UHFFFAOYSA-M 0.000 claims 1
- RLEFZEWKMQQZOA-UHFFFAOYSA-M potassium;octanoate Chemical compound [K+].CCCCCCCC([O-])=O RLEFZEWKMQQZOA-UHFFFAOYSA-M 0.000 claims 1
- 229920005604 random copolymer Polymers 0.000 claims 1
- 239000006254 rheological additive Substances 0.000 claims 1
- 239000005060 rubber Substances 0.000 claims 1
- 150000003839 salts Chemical class 0.000 claims 1
- 239000004576 sand Substances 0.000 claims 1
- 150000004760 silicates Chemical class 0.000 claims 1
- 239000000779 smoke Substances 0.000 claims 1
- 239000001632 sodium acetate Substances 0.000 claims 1
- 235000017281 sodium acetate Nutrition 0.000 claims 1
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 claims 1
- HLBBKKJFGFRGMU-UHFFFAOYSA-M sodium formate Chemical compound [Na+].[O-]C=O HLBBKKJFGFRGMU-UHFFFAOYSA-M 0.000 claims 1
- 235000019254 sodium formate Nutrition 0.000 claims 1
- 239000002904 solvent Substances 0.000 claims 1
- 239000004575 stone Substances 0.000 claims 1
- 239000004094 surface-active agent Substances 0.000 claims 1
- 239000012209 synthetic fiber Substances 0.000 claims 1
- 229920002994 synthetic fiber Polymers 0.000 claims 1
- 239000004753 textile Substances 0.000 claims 1
- 229920001169 thermoplastic Polymers 0.000 claims 1
- 229920001187 thermosetting polymer Polymers 0.000 claims 1
- 239000004416 thermosoftening plastic Substances 0.000 claims 1
- DVKJHBMWWAPEIU-UHFFFAOYSA-N toluene 2,4-diisocyanate Chemical compound CC1=CC=C(N=C=O)C=C1N=C=O DVKJHBMWWAPEIU-UHFFFAOYSA-N 0.000 claims 1
- 229910052902 vermiculite Inorganic materials 0.000 claims 1
- 239000010455 vermiculite Substances 0.000 claims 1
- 235000019354 vermiculite Nutrition 0.000 claims 1
- 239000000080 wetting agent Substances 0.000 claims 1
- 210000002268 wool Anatomy 0.000 claims 1
Classifications
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- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
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- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
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- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
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- 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
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/70—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
- C08G18/72—Polyisocyanates or polyisothiocyanates
- C08G18/77—Polyisocyanates or polyisothiocyanates having heteroatoms in addition to the isocyanate or isothiocyanate nitrogen and oxygen or sulfur
- C08G18/78—Nitrogen
- C08G18/79—Nitrogen characterised by the polyisocyanates used, these having groups formed by oligomerisation of isocyanates or isothiocyanates
- C08G18/791—Nitrogen characterised by the polyisocyanates used, these having groups formed by oligomerisation of isocyanates or isothiocyanates containing isocyanurate groups
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- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/70—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
- C08G18/72—Polyisocyanates or polyisothiocyanates
- C08G18/77—Polyisocyanates or polyisothiocyanates having heteroatoms in addition to the isocyanate or isothiocyanate nitrogen and oxygen or sulfur
- C08G18/78—Nitrogen
- C08G18/79—Nitrogen characterised by the polyisocyanates used, these having groups formed by oligomerisation of isocyanates or isothiocyanates
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- C08G18/794—Nitrogen characterised by the polyisocyanates used, these having groups formed by oligomerisation of isocyanates or isothiocyanates containing isocyanurate groups formed by oligomerisation of aromatic isocyanates or isothiocyanates
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Claims (28)
1. Отверждаемая композиция для получения полиизоциануратсодержащих продуктов, полученная в результате объединения и смешивания при изоцианатном индексе, составляющем по меньшей мере 100:
а) полиизоцианатной композиции,
b) композиции, реакционно-способной по отношению к изоцианату и содержащей по меньшей мере 50% (моль.), предпочтительно по меньшей мере 70% (моль.), более предпочтительно по меньшей мере 90% (моль.) диолов из расчета на совокупное количество молей соединений, реакционно-способных по отношению к изоцианату, в композиции, реакционно-способной по отношению к изоцианату,
с) добавки, повышающей ударопрочность и содержащей акриловые блок-сополимеры,
d) композиции катализатора тримеризации и
е) необязательно дополнительных добавок и/или вспомогательных соединений,
где количество полиизоцианатов в отверждаемой композиции составляет по меньшей мере 50% (мас.) полиизоцианатов из расчета на совокупную массу реакционно-способной отверждаемой композиции,
где блок-сополимерная добавка, повышающая ударопрочность, представляет собой самособираемый блок-сополимер, где по меньшей мере одним блоком является полиизоцианат-/полиизоциануратсмешиваемый блок, имеющий температуру стеклования (Tg) более чем 100°С, и по меньшей мере одним блоком является полиизоцианат-/полиизоциануратнесмешиваемый блок, характеризующийся значением Tg ниже 0°С.
2. Отверждаемая композиция по п. 1, где количество полиизоцианатов в отверждаемой композиции составляет по меньшей мере 60% (мас.) полиизоцианатов из расчета на совокупную массу реакционно-способной отверждаемой композиции.
3. Отверждаемая композиция по любому из пп. 1, 2, где композиция, реакционно-способная по отношению к изоцианату, содержит ароматические полиолы, предпочтительно ароматические полиэфирполиолы на основе сложного эфира, более предпочтительно ароматические полиэфирдиолы на основе сложного эфира.
4. Отверждаемая композиция по любому из пп. 1, 2, где диолы имеют молекулярную массу (ММ) меньше чем 1000 г/моль, предпочтительно меньше чем 500 г/моль, и включают алкиленгликоли и/или оксиалкиленгликоли, описывающиеся формулами CnH2n(OH)2 и CnH2nO(ОH)2.
5. Отверждаемая композиция по любому из пп. 1, 2, где диолы выбирают из полиэтиленгликоля и/или полипропиленгликоля-(1,2) и -(1,3), полибутиленгликоля-(1,4) и -(2,3), полигександиола-(1,6), полиоктандиола-(1,8) и их смесей.
6. Отверждаемая композиция по любому из пп. 1, 2, где полиизоцианат-/полиизоциануратнесмешиваемый блок характеризуюется значением Tg ниже - 40°С, и где сополимер в отверждаемой композиции присутствует в количестве в диапазоне от 0,1 до 30% (мас.), предпочтительно от 0,5 до 15% (мас.), более предпочтительно от 1% (мас.) до 10% (мас.), из расчета на совокупную массу отверждаемой композиции.
7. Отверждаемая композиция по любому из пп. 1, 2, где блок-сополимерная добавка, повышающая ударопрочность, представляет собой самособираемый блок-сополимер, имеющий среднечисловую молекулярную массу (ММ), составляющую по меньшей мере 1000 г/моль, предпочтительно находящуюся в диапазоне 10000-500000 г/моль, более предпочтительно в диапазоне 20000-200000 г/моль.
8. Отверждаемая композиция по любому из пп. 1-7, где полиизоцианат-/полиизоциануратсмешиваемый блок блок-сополимера выбирают из полиметилметакрилата (Tg=105°C) и/или полистирола (Tg=100°С), и полиизоцианат-/полиизоциануратнесмешиваемый блок блок-сополимера выбирают из полиалкилакрилатов и/или полидиенов, в частности полибутадиена, такого как 1,4-полибутадиен, и/или полиизопрена, и их статистических сополимеров.
9. Отверждаемая композиция по любому из пп. 1, 2, где полиизоцианаты выбирают из алифатических, циклоалифатических, аралифатических, а предпочтительно ароматических полиизоцианатов, таких как толуолдиизоцианат в форме его 2,4- и 2,6-изомеров и их смесей, дифенилметандиизоцианаты и их варианты и смеси из дифенилметандиизоцианатов (MDI) и их олигомеров, характеризующихся изоцианатной функциональностью, большей чем 2.
10. Отверждаемая композиция по любому из пп. 1, 2, где композицию катализатора тримеризации выбирают из солей, образованных из щелочных и/или щелочноземельных металлов и органических карбоновых кислот, предпочтительно содержащих 1-12 атомов углерода, таких как ацетат калия или 2-этилгексаноат калия, таких как ацетат калия, гексаноат калия, этилгексаноат калия, октаноат калия, лактат калия, этоксид натрия, формиат натрия, формиат калия, ацетат натрия, бензоат калия и их смеси.
11. Отверждаемая композиция по любому из пп. 1-2, где композицию катализатора тримеризации выбирают из композиции, содержащей галогенид лития (предпочтительно LiCl), эпоксидную смолу и необязательно соединение мочевины.
12. Отверждаемая композиция по любому из пп. 1, 2, где композицию катализатора тримеризации используют в количестве в диапазоне от 0,001 до 10% (мас.), предпочтительно от 0,1 до 5% (мас.), наиболее предпочтительно от 0,5 до 2,0% (мас.), из расчета на совокупную массу отверждаемой композиции.
13. Отверждаемая композиция по любому из пп. 1, 2, где вспомогательные соединения выбирают из нереакционно-способных по отношению к изоцианату растворителей, поверхностно-активных веществ, акцепторов (поглотителей), подобных алкилортоформиату, а в частности триизопропилортоформиату, противомикробных средств, антипиренов, противодымных добавок, УФ-стабилизаторов, красителей, пластификаторов, внутренних разделительных смазок для форм, реологических модификаторов, смачивателей, диспергаторов и наполнителей.
14. Отверждаемая композиция по любому из пп. 1, 2, где вспомогательные соединения включают материалы наполнителей, которые выбирают из древесной щепы, древесных опилок, древесных стружек, деревянных пластинок; бумаги и картона как нарезанных, так и наслоенных; песка, вермикулита, глины, цемента и других силикатов; резиновой муки, измельченных термопластов, измельченных термореактивных материалов; сотовых конструкций из любого материала, подобного картону, алюминию, древесине и пластмассам; металлических частиц и пластинок; пробки в дисперсной форме или в виде слоев; натуральных волокон, подобных волокнам льна, пеньки и сизаля; синтетических волокон, подобных волокнам из полиамида, полиолефина, полиарамида, сложного полиэфира и углерода; минеральных волокон, подобных стекловолокну и волокну каменной ваты; минеральных наполнителей, подобных BaSO4 и СаСО3; наночастиц, подобных глинам, неорганическим оксидам и углеродам; стеклянной дроби, измельченного стекла, пустотелых стеклянных шариков; вспененных или вспениваемых шариков; не подвергнутых или подвергнутых обработке отходов, подобных размолотым, разрубленным, раздробленным или измельченным отходам, а в частности зольной пыли; тканых и нетканых текстильных материалов; и комбинаций из двух и более данных материалов.
15. Способ получения отверждаемой композиции по любому из пп. 1-14, который включает объединение и смешивание ингредиентов от (а) до (е) при давлении окружающей среды и при температуре в диапазоне от 5 до 45°С, а более предпочтительно от 5 до 30°С.
16. Способ получения полиизоциануратсодержащих материалов, характеризующихся улучшенной ударопрочностью, включающий, по меньшей мере, стадии обеспечения прохождения реакции для отверждаемой композиции по любому из пп. 1-14 при изоцианатном индексе, составляющем по меньшей мере 100, и при температуре отверждения, более 50°С, а предпочтительно более 80°С.
17. Способ получения полиизоциануратсодержащих материалов по п. 16, где способ является периодическим, полунепрерывным или непрерывным способом, способом литья под давлением, экструдирования, пултрузии или способом формования, таким как способ прямого прессования, способ литьевого прессования смол, способ формования при использовании вакуума, способ инфузионного формования смол, способ препрегирования.
18. Способ получения полиизоциануратсодержащих материалов по любому из пп. 16, 17, где изоцианатный индекс находится в диапазоне от 100 вплоть до 15000, предпочтительно в диапазоне 100-500, более предпочтительно в диапазоне 100-300.
19. Способ получения полиизоциануратсодержащих материалов по любому из пп. 16-17, где температура отверждения находится в диапазоне от 50 до 350°С, а наиболее предпочтительно в диапазоне от 125 до 250°С.
20. Полиизоциануратсодержащий материал, полученный при использовании способа по любому из пп. 16-19, характеризующийся температурой стеклования > 100°С, значением трещиностойкости Glc > 1000 Дж/м2, предпочтительно Glc > 1500 Дж/м2, и/или значением ударопрочности Klc > 2 МПа⋅м1/2.
21. Полиизоциануратсодержащий материал, полученный способом по любому из пп. 16-19, характеризующийся температурой стеклования > 150°C, значением ударопрочности Glc > 500 Дж/м2, более предпочтительно Glc > 600 Дж/м2, и/или значением ударопрочности Klc > 1 МПа⋅м1/2.
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EP14183799.7A EP2993195A1 (en) | 2014-09-05 | 2014-09-05 | A method for improving fracture toughness of polyisocyanurate comprising reaction products |
PCT/EP2015/065675 WO2016034313A1 (en) | 2014-09-05 | 2015-07-09 | A method for improving fracture toughness of polyisocyanurate comprising reaction products |
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US20200190245A1 (en) * | 2016-11-14 | 2020-06-18 | Covestro Deutschland Ag | Composite materials based on dual-curing isocyanurate polymers |
CN107973897A (zh) * | 2017-11-30 | 2018-05-01 | 华南理工大学 | 一种水可分散的混合改性tdi三聚体固化剂及其制备方法 |
CN109181280A (zh) * | 2018-09-05 | 2019-01-11 | 安徽省华腾农业科技有限公司 | 一种聚氨酯弹性体及其制备方法 |
KR102481812B1 (ko) | 2018-12-11 | 2022-12-28 | 트라이머 테크놀로지스, 엘엘씨 | 폴리이소시아누레이트 기재 중합체 및 섬유 강화된 복합재 |
US11702499B2 (en) | 2018-12-11 | 2023-07-18 | Trimer Technologies Llc | Polyisocyanurate based polymers and fiber reinforced composites |
CN110790893B (zh) * | 2019-11-20 | 2021-12-28 | 常熟理工学院 | 一种提高聚异氰脲酸酯的韧性与阻燃性能的方法 |
US20220220307A1 (en) * | 2021-01-14 | 2022-07-14 | Covestro Llc | Polyisocyanurate thermosets with improved mechanical properties |
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- 2014-09-05 EP EP14183799.7A patent/EP2993195A1/en not_active Ceased
-
2015
- 2015-07-09 US US15/505,771 patent/US10544253B2/en active Active
- 2015-07-09 MX MX2017002783A patent/MX2017002783A/es unknown
- 2015-07-09 WO PCT/EP2015/065675 patent/WO2016034313A1/en active Application Filing
- 2015-07-09 CN CN201580047500.3A patent/CN106795270B/zh active Active
- 2015-07-09 PL PL15736822T patent/PL3189088T3/pl unknown
- 2015-07-09 EP EP15736822.6A patent/EP3189088B1/en active Active
- 2015-07-09 BR BR112017004158-8A patent/BR112017004158B1/pt not_active IP Right Cessation
- 2015-07-09 RU RU2017111045A patent/RU2669384C2/ru active
- 2015-07-09 CA CA2960308A patent/CA2960308C/en active Active
- 2015-07-31 TW TW104124978A patent/TWI674294B/zh active
Also Published As
Publication number | Publication date |
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PL3189088T3 (pl) | 2020-11-16 |
CA2960308C (en) | 2020-07-21 |
TW201612241A (en) | 2016-04-01 |
CN106795270B (zh) | 2020-12-15 |
EP3189088A1 (en) | 2017-07-12 |
US10544253B2 (en) | 2020-01-28 |
CN106795270A (zh) | 2017-05-31 |
EP3189088B1 (en) | 2020-04-01 |
CA2960308A1 (en) | 2016-03-10 |
RU2017111045A3 (ru) | 2018-10-05 |
WO2016034313A1 (en) | 2016-03-10 |
MX2017002783A (es) | 2017-05-30 |
BR112017004158A2 (pt) | 2017-12-05 |
TWI674294B (zh) | 2019-10-11 |
US20170283545A1 (en) | 2017-10-05 |
EP2993195A1 (en) | 2016-03-09 |
RU2669384C2 (ru) | 2018-10-11 |
BR112017004158B1 (pt) | 2021-12-21 |
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