RU2684387C2 - Photopolymer composition for the production of thermal-resistant objects by the method of laser stereolithography - Google Patents
Photopolymer composition for the production of thermal-resistant objects by the method of laser stereolithography Download PDFInfo
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- 239000000203 mixture Substances 0.000 title claims abstract description 17
- 238000004519 manufacturing process Methods 0.000 title claims abstract 6
- 238000000034 method Methods 0.000 title description 3
- YCGKJPVUGMBDDS-UHFFFAOYSA-N 3-(6-azabicyclo[3.1.1]hepta-1(7),2,4-triene-6-carbonyl)benzamide Chemical compound NC(=O)C1=CC=CC(C(=O)N2C=3C=C2C=CC=3)=C1 YCGKJPVUGMBDDS-UHFFFAOYSA-N 0.000 claims abstract description 9
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 claims abstract description 5
- 230000005855 radiation Effects 0.000 claims description 8
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 6
- WFKDPJRCBCBQNT-UHFFFAOYSA-N n,2-dimethylprop-2-enamide Chemical compound CNC(=O)C(C)=C WFKDPJRCBCBQNT-UHFFFAOYSA-N 0.000 claims description 6
- 239000003779 heat-resistant material Substances 0.000 claims 1
- 239000011159 matrix material Substances 0.000 abstract description 2
- 206010034972 Photosensitivity reaction Diseases 0.000 abstract 2
- 238000005516 engineering process Methods 0.000 abstract 2
- 230000036211 photosensitivity Effects 0.000 abstract 2
- 239000000126 substance Substances 0.000 abstract 1
- 239000000047 product Substances 0.000 description 7
- 238000001035 drying Methods 0.000 description 4
- 238000000265 homogenisation Methods 0.000 description 4
- 239000003999 initiator Substances 0.000 description 4
- CHDKQNHKDMEASZ-UHFFFAOYSA-N n-prop-2-enoylprop-2-enamide Chemical compound C=CC(=O)NC(=O)C=C CHDKQNHKDMEASZ-UHFFFAOYSA-N 0.000 description 4
- 238000005406 washing Methods 0.000 description 4
- UHFFVFAKEGKNAQ-UHFFFAOYSA-N 2-benzyl-2-(dimethylamino)-1-(4-morpholin-4-ylphenyl)butan-1-one Chemical compound C=1C=C(N2CCOCC2)C=CC=1C(=O)C(CC)(N(C)C)CC1=CC=CC=C1 UHFFVFAKEGKNAQ-UHFFFAOYSA-N 0.000 description 2
- 238000004132 cross linking Methods 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- -1 4-morpholinophenyl Chemical group 0.000 description 1
- 239000004952 Polyamide Substances 0.000 description 1
- 150000003926 acrylamides Chemical class 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 230000006378 damage Effects 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 229920002521 macromolecule Polymers 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 125000005395 methacrylic acid group Chemical class 0.000 description 1
- 238000000016 photochemical curing Methods 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 230000008092 positive effect Effects 0.000 description 1
- 238000005086 pumping Methods 0.000 description 1
- 230000001360 synchronised effect Effects 0.000 description 1
- 238000002076 thermal analysis method Methods 0.000 description 1
Classifications
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- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03C—PHOTOSENSITIVE MATERIALS FOR PHOTOGRAPHIC PURPOSES; PHOTOGRAPHIC PROCESSES, e.g. CINE, X-RAY, COLOUR, STEREO-PHOTOGRAPHIC PROCESSES; AUXILIARY PROCESSES IN PHOTOGRAPHY
- G03C1/00—Photosensitive materials
- G03C1/005—Silver halide emulsions; Preparation thereof; Physical treatment thereof; Incorporation of additives therein
- G03C1/04—Silver halide emulsions; Preparation thereof; Physical treatment thereof; Incorporation of additives therein with macromolecular additives; with layer-forming substances
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F2/00—Processes of polymerisation
- C08F2/46—Polymerisation initiated by wave energy or particle radiation
-
- 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
- C08K5/00—Use of organic ingredients
- C08K5/16—Nitrogen-containing compounds
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L77/00—Compositions of polyamides obtained by reactions forming a carboxylic amide link in the main chain; Compositions of derivatives of such polymers
- C08L77/06—Polyamides derived from polyamines and polycarboxylic acids
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/004—Photosensitive materials
- G03F7/027—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/004—Photosensitive materials
- G03F7/027—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds
- G03F7/032—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds with binders
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- Physics & Mathematics (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
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- Health & Medical Sciences (AREA)
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- General Physics & Mathematics (AREA)
- Engineering & Computer Science (AREA)
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Abstract
Description
Изобретение относится к фотополимеризующимся композициям (ФПК) на основе акриламидного компонентов, фотоинициатора - 2-бензил-2-диметиламино-1-(4-морфолинофенил)-бутанона-1 и поли-м-фениленизофталамида используемого в качестве термостойкой матрицы. Такая композиция при действии лазерного импульсного излучения образовывает трехмерные структуры заданной архитектуры с повышенной термо- и теплостойкостью, которые могут быть использованы в различных отраслях промышленности.The invention relates to photopolymerizable compositions (FPK) based on acrylamide components, photoinitiator - 2-benzyl-2-dimethylamino-1- (4-morpholinophenyl) butanone-1 and poly-m-phenyleneisophthalamide used as a heat-resistant matrix. Such a composition under the action of laser pulsed radiation forms three-dimensional structures of a given architecture with increased heat and heat resistance, which can be used in various industries.
Наиболее пригодными ФПК для лазерной стереолитографии традиционно являются составы на основе акриловых и метакриловых кислот, описанные, например, в патентах РФ 2244335 и 2515991. Однако, общим недостатком таких ФПК является низкие значения термо- и теплостойкости получаемых изделий на их основе.The most suitable FPCs for laser stereolithography are traditionally compositions based on acrylic and methacrylic acids, described, for example, in RF patents 2244335 and 2515991. However, a common drawback of such FPCs is the low heat and heat resistance of the obtained products based on them.
Техническим результатом настоящего изобретения является создание ФПК, которые при действии лазерного излучения с длинной волны 405 нм, образуют трехмерные изделия с температурой эксплуатации 370-390°С и прочностью при разрыве 86,8-90,3 МПа (ГОСТ 11262-80, 14359-69). Такой результат достигается за счет использования ФПК на основе поли-м-фениленизофталамида с молекулярной массой 60 кДа и акриламидных соединений. Последние при действии лазерного излучения полимеризуются и переплетаются с макромолекулами полиамида в момент получения В результате формируются химически не связаные, но механически не разделимые полувзаимопроникающие полимерные сетки, обеспечивающие комплекс эксплуатационных характеристик.The technical result of the present invention is the creation of FPK, which under the action of laser radiation with a wavelength of 405 nm, form three-dimensional products with an operating temperature of 370-390 ° C and a tensile strength of 86.8-90.3 MPa (GOST 11262-80, 14359- 69). This result is achieved through the use of FPK based on poly-m-phenyleneisophthalamide with a molecular weight of 60 kDa and acrylamide compounds. The latter under the action of laser radiation polymerize and intertwine with the polyamide macromolecules at the time of receipt. As a result, chemically unrelated but mechanically inseparable semi-interpenetrating polymer networks are formed, providing a set of operational characteristics.
В качестве акриламидных сшивающих компонентов используются:As acrylamide crosslinking components are used:
диакриламид [ди(4,4'-дифенилоксидизофталоиламидо)]-фенил-4'-фенилоксидаdiacrylamide [di (4,4'-diphenyloxyisophthaloylamido)] - phenyl-4'-phenyl oxide
диакриламид [пента(4,4'-дифенилоксидизофталоиламидо)]-фенил-4'-фенилоксидаdiacrylamide [penta (4,4'-diphenyloxyisophthaloylamido)] - phenyl-4'-phenyl oxide
4,4'-диакриламидодифенилфталид4,4'-diacrylamidodiphenylphthalide
4,4'-диакриламидодифениловый эфир4,4'-diacrylamidodiphenyl ether
ФПК имеет следующий состав (%, мас.):FPK has the following composition (%, wt.):
поли-м-фениленизофталамид - 20;poly-m-phenyleneisophthalamide - 20;
акриламидный компонент - 2;acrylamide component - 2;
N,N'-диметилакриламид - 76;N, N'-dimethylacrylamide - 76;
2-бензил-2-диметиламино-1-(4-морфолинофенил)-бутанон-1 - 2.2-benzyl-2-dimethylamino-1- (4-morpholinophenyl) butanone-1 - 2.
Фотоотверждение композиций осуществляли с использованием твердотельного лазерного модуля с диодной накачкой MDL-III-405 (CNIlaser) со следующими характеристиками: длина волны 405 нм, мощность излучения от 1 до 100 мВт, диаметр пучка на выходной апертуре ~ 2,5 мм, расходимость пучка (полный угол) 0,5 мрад. Подвод лазерного излучения производили снизу, перпендикулярно поверхности фотокомпозиции. Фокусировку лазерного излучения осуществляли при помощи F-theta объектива (фокусное расстояние 160 мм), а для перемещения лазерного излучения использовали однозеркальный гальваносканер LScanH-10 (Атеко) с основными параметрами: диапазон сканирования ± 6°; максимальная скорость сканирования - до 480%; поле обработки (в текущем эксперименте) 30×30 мм.Photo curing of the compositions was performed using an MDL-III-405 solid-state laser module with diode pumping (CNIlaser) with the following characteristics: wavelength 405 nm, radiation power from 1 to 100 mW, beam diameter at the output aperture ~ 2.5 mm, beam divergence ( full angle) 0.5 mrad. Laser radiation was supplied from below, perpendicular to the surface of the photocomposition. Laser radiation was focused using an F-theta lens (focal length 160 mm), and LScanH-10 (Ateko) single-mirror galvanoscanner with basic parameters was used to move the laser radiation: scanning range ± 6 °; maximum scanning speed - up to 480%; processing field (in the current experiment) 30 × 30 mm.
Полученные таким образом материалы заданной геометрической формы согласно данным синхронного термического анализа (ТГ-ДТА/ДСК STA 449 C14/G Jupiter (Netzsch), на воздухе при скорости нагревания 5 град/мин) не плавятся вплоть до начала деструкции, которая происходит при 370-390°С, что свидетельствует об их высокой термостойкости.Thus obtained materials of a given geometric shape according to the data of synchronous thermal analysis (TG-DTA / DSC STA 449 C14 / G Jupiter (Netzsch), do not melt in air at a heating rate of 5 deg / min until the start of destruction, which occurs at 370- 390 ° C, which indicates their high heat resistance.
Предлагаемый способ подтверждается следующими нижеприведенными примерами.The proposed method is confirmed by the following examples.
Пример 1. В 4,3675 г N,N'-диметилакриламида добавляли 1,1493 г поли-м-фениленизофталамида и 0,1149 г 4,4'-диакриламидодифенилфталида и смешивали с 0,1149 г инициатором фотополимеризации 2-бензил-2-диметиламино-1-(4-морфолинофенил)-бутанона-1 и интенсивно перемешивали до полной гомогенизации. Полученную композицию подвергали лазерной стереолитографии с λ=405 нм. В результате получали изделие, которое после тщательного промывания и сушки начинало деструктировать на воздухе при 370°С. Образцы имеют следующие механические характеристики: прочность на разрыв 87,9±0,9 МПа, относительное удлинение при разрыве 3,6±0,1%, модуль Юнга 2115,2±1,5МПа.Example 1. 1.1493 g of poly-m-phenyleneisophthalamide and 0.1149 g of 4,4'-diacrylamidodiphenylphthalide were added to 4.3675 g of N, N'-dimethylacrylamide and mixed with 0.1149 g of 2-benzyl-2- photopolymerization initiator dimethylamino-1- (4-morpholinophenyl) -butanone-1 and was vigorously stirred until complete homogenization. The resulting composition was subjected to laser stereolithography with λ = 405 nm. The result was a product that, after thorough washing and drying, began to degrade in air at 370 ° C. Samples have the following mechanical characteristics: tensile strength 87.9 ± 0.9 MPa, elongation at break 3.6 ± 0.1%, Young's modulus 2115.2 ± 1.5 MPa.
Пример 2. В 4,3675 г N,N'-диметилакриламида добавляли 1,1493 г поли-м-фениленизофталамида и 0,1149 г г 4,4'-диакриламидодифенилового эфира и смешивали с 0,1149 г г инициатором фотополимеризации 2-бензил-2-диметиламино-1-(4-морфолинофенил)-бутанона-1 и интенсивно перемешивали до полной гомогенизации. Полученную композицию подвергали лазерной стереолитографии с λ=405 нм. В результате получали изделие, которое после тщательного промывания и сушки начинало деструктировать на воздухе при 375°С. Образцы имеют следующие механические характеристики: прочность на разрыв 88,5±1,3 МПа, относительное удлинение 3,1±0,2%, модуль Юнга 1887,7±1,4МПа.Example 2. 1.1493 g of poly-m-phenyleneisophthalamide and 0.1149 g of 4,4'-diacrylamidodiphenyl ether were added to 4.3675 g of N, N'-dimethylacrylamide and mixed with 0.1149 g of 2-benzyl photopolymerization initiator -2-dimethylamino-1- (4-morpholinophenyl) -butanone-1 and was intensively mixed until complete homogenization. The resulting composition was subjected to laser stereolithography with λ = 405 nm. As a result, a product was obtained which, after thorough washing and drying, began to degrade in air at 375 ° C. The samples have the following mechanical characteristics: tensile strength 88.5 ± 1.3 MPa, elongation 3.1 ± 0.2%, Young's modulus 1887.7 ± 1.4 MPa.
Пример 3. В 4,3675 г N,N'-диметилакриламида добавляли 1,1493 г поли-м-фениленизофталамида и 0,1149 г диакриламида [ди(4,4'-дифенилоксидизофталоиламидо)]-фенил-4'-фенилоксида и смешивали с 0,1149 г инициатором фотополимеризации 2-бензил-2-диметиламино-1-(4-морфолинофенил)-бутаноиа-1 и интенсивно перемешивали до полной гомогенизации. Полученную композицию подвергали лазерной стереолитографии с λ=405 нм. В результате получали изделие, которое после тщательного промывания и сушки начинало деструктировать на воздухе при 378°С. Образцы имеют следующие механические характеристики: прочность на разрыв 87,9±1,1 МПа относительное удлинение 3,5±0,2%, модуль Юнга 2153,8±1,9 МПа.Example 3. To 4.3675 g of N, N'-dimethylacrylamide was added 1.1493 g of poly-m-phenyleneisophthalamide and 0.1149 g of diacrylamide [di (4,4'-diphenyloxyisophthaloylamide)] - phenyl-4'-phenyl oxide and mixed with 0.1149 g of photopolymerization initiator 2-benzyl-2-dimethylamino-1- (4-morpholinophenyl) butanoia-1 and was intensively mixed until complete homogenization. The resulting composition was subjected to laser stereolithography with λ = 405 nm. As a result, a product was obtained which, after thorough washing and drying, began to degrade in air at 378 ° C. The samples have the following mechanical characteristics: tensile strength 87.9 ± 1.1 MPa, elongation 3.5 ± 0.2%, Young's modulus 2153.8 ± 1.9 MPa.
Пример 4. В 4,3675 г N,N'-диметилакриламида добавляли 1,1493 г поли-м-фениленизофталамида и 0,1149 г диакриламида [пента(4,4'-дифенилоксидизофталоиламидо)]-фенил-4'-фенилоксида и смешивали с 0,1149 г инициатором фотополимеризации 2-бензил-2-диметиламино-1-(4-морфолинофенил)-бутанона-1 и интенсивно перемешивали до полной гомогенизации. Полученную композицию подвергали лазерной стереолитографии с λ=405 нм. В результате получали изделие, которое после тщательного промывания и сушки начинало деструктировать на воздухе при 390°С. Образцы имеют следующие механические характеристики: прочность на разрыв 88,9±1,4 МПа, относительное удлинение 3,7±0,3%, модуль Юнга 2147,4±3,6 МПа.Example 4. To 4.3675 g of N, N'-dimethylacrylamide was added 1.1493 g of poly-m-phenyleneisophthalamide and 0.1149 g of diacrylamide [penta (4,4'-diphenyloxyisophthaloylamide)] -phenyl-4'-phenyl oxide and mixed with 0.1149 g of photopolymerization initiator 2-benzyl-2-dimethylamino-1- (4-morpholinophenyl) butanone-1 and was intensively mixed until complete homogenization. The resulting composition was subjected to laser stereolithography with λ = 405 nm. As a result, a product was obtained which, after thorough washing and drying, began to degrade in air at 390 ° C. The samples have the following mechanical characteristics: tensile strength 88.9 ± 1.4 MPa, elongation 3.7 ± 0.3%, Young's modulus 2147.4 ± 3.6 MPa.
Как видно из приведенных примеров, фотополимерная композиция выгодно отличается тем, что проста в получении, не требует эксикатора и вакуума для удаления пузырьков. В процессе фотополимеризации отсутствует выделение побочных продуктов. Полученные структуры после сшивки по кратным связям в трехмерный полимер обладают термостойкостью до 390°С.As can be seen from the above examples, the photopolymer composition favorably differs in that it is easy to obtain, does not require a desiccator and a vacuum to remove bubbles. In the process of photopolymerization, no by-products are isolated. The structures obtained after crosslinking via multiple bonds into a three-dimensional polymer are heat resistant up to 390 ° C.
Вышеперечисленный комплекс практически полезных свойств, полученных ФПК определяет положительный эффект изобретения. Полученные ФПК могут быть использованы в стериолитографии для получения термо- и теплостойких изделий заданной архитектуры.The above complex of practically useful properties obtained by FPK determines the positive effect of the invention. The obtained FPK can be used in sterolithography to obtain thermally and heat-resistant products of a given architecture.
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RU2760736C1 (en) * | 2021-04-19 | 2021-11-30 | Федеральное государственное бюджетное учреждение науки Байкальский институт природопользования Сибирского отделения Российской академии наук (БИП СО РАН) | Curable resins for making heat-resistant 3d objects using dlp 3d printing |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| RU2760736C1 (en) * | 2021-04-19 | 2021-11-30 | Федеральное государственное бюджетное учреждение науки Байкальский институт природопользования Сибирского отделения Российской академии наук (БИП СО РАН) | Curable resins for making heat-resistant 3d objects using dlp 3d printing |
| RU2790249C1 (en) * | 2021-11-29 | 2023-02-15 | Федеральное государственное бюджетное учреждение науки Байкальский институт природопользования Сибирского отделения Российской академии наук (БИП СО РАН) | Photo-curable compositions for manufacture of heat-resistant three-dimensional objects by dlp 3d printing |
Also Published As
| Publication number | Publication date |
|---|---|
| RU2017115737A3 (en) | 2018-11-06 |
| RU2017115737A (en) | 2018-11-06 |
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