RU2016109460A - Многослойный композит, содержащий слой фторполимера - Google Patents
Многослойный композит, содержащий слой фторполимера Download PDFInfo
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- RU2016109460A RU2016109460A RU2016109460A RU2016109460A RU2016109460A RU 2016109460 A RU2016109460 A RU 2016109460A RU 2016109460 A RU2016109460 A RU 2016109460A RU 2016109460 A RU2016109460 A RU 2016109460A RU 2016109460 A RU2016109460 A RU 2016109460A
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- 239000002131 composite material Substances 0.000 title claims 19
- 229920002313 fluoropolymer Polymers 0.000 title claims 3
- 239000004811 fluoropolymer Substances 0.000 title claims 3
- NAQMVNRVTILPCV-UHFFFAOYSA-N hexane-1,6-diamine Chemical compound NCCCCCCN NAQMVNRVTILPCV-UHFFFAOYSA-N 0.000 claims 8
- 229920001577 copolymer Polymers 0.000 claims 6
- 239000012778 molding material Substances 0.000 claims 5
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 claims 4
- 239000000654 additive Substances 0.000 claims 4
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims 3
- -1 ethylene-chlorotrifluoroethylene Chemical group 0.000 claims 3
- BQCIDUSAKPWEOX-UHFFFAOYSA-N 1,1-Difluoroethene Chemical compound FC(F)=C BQCIDUSAKPWEOX-UHFFFAOYSA-N 0.000 claims 2
- 239000002033 PVDF binder Substances 0.000 claims 2
- QQONPFPTGQHPMA-UHFFFAOYSA-N Propene Chemical compound CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 claims 2
- 125000001931 aliphatic group Chemical group 0.000 claims 2
- 125000004432 carbon atom Chemical group C* 0.000 claims 2
- 239000000446 fuel Substances 0.000 claims 2
- 239000000203 mixture Substances 0.000 claims 2
- 239000000178 monomer Substances 0.000 claims 2
- 238000000465 moulding Methods 0.000 claims 2
- 229920002493 poly(chlorotrifluoroethylene) Polymers 0.000 claims 2
- 239000005023 polychlorotrifluoroethylene (PCTFE) polymer Substances 0.000 claims 2
- 229920002981 polyvinylidene fluoride Polymers 0.000 claims 2
- 239000003381 stabilizer Substances 0.000 claims 2
- BFKJFAAPBSQJPD-UHFFFAOYSA-N tetrafluoroethene Chemical group FC(F)=C(F)F BFKJFAAPBSQJPD-UHFFFAOYSA-N 0.000 claims 2
- LVGUZGTVOIAKKC-UHFFFAOYSA-N 1,1,1,2-tetrafluoroethane Chemical compound FCC(F)(F)F LVGUZGTVOIAKKC-UHFFFAOYSA-N 0.000 claims 1
- PXGZQGDTEZPERC-UHFFFAOYSA-N 1,4-cyclohexanedicarboxylic acid Chemical compound OC(=O)C1CCC(C(O)=O)CC1 PXGZQGDTEZPERC-UHFFFAOYSA-N 0.000 claims 1
- 239000004953 Aliphatic polyamide Substances 0.000 claims 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims 1
- 229920000089 Cyclic olefin copolymer Polymers 0.000 claims 1
- 229920001780 ECTFE Polymers 0.000 claims 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims 1
- 239000005977 Ethylene Substances 0.000 claims 1
- 229920000219 Ethylene vinyl alcohol Polymers 0.000 claims 1
- 230000000996 additive effect Effects 0.000 claims 1
- 239000002318 adhesion promoter Substances 0.000 claims 1
- 229920003231 aliphatic polyamide Polymers 0.000 claims 1
- 125000003118 aryl group Chemical group 0.000 claims 1
- 239000002826 coolant Substances 0.000 claims 1
- 229910052802 copper Inorganic materials 0.000 claims 1
- 239000010949 copper Substances 0.000 claims 1
- 230000008878 coupling Effects 0.000 claims 1
- 238000010168 coupling process Methods 0.000 claims 1
- 238000005859 coupling reaction Methods 0.000 claims 1
- 150000004985 diamines Chemical class 0.000 claims 1
- UFRKOOWSQGXVKV-UHFFFAOYSA-N ethene;ethenol Chemical compound C=C.OC=C UFRKOOWSQGXVKV-UHFFFAOYSA-N 0.000 claims 1
- 239000004715 ethylene vinyl alcohol Substances 0.000 claims 1
- 239000012530 fluid Substances 0.000 claims 1
- XUCNUKMRBVNAPB-UHFFFAOYSA-N fluoroethene Chemical compound FC=C XUCNUKMRBVNAPB-UHFFFAOYSA-N 0.000 claims 1
- 238000010438 heat treatment Methods 0.000 claims 1
- HCDGVLDPFQMKDK-UHFFFAOYSA-N hexafluoropropylene Chemical compound FC(F)=C(F)C(F)(F)F HCDGVLDPFQMKDK-UHFFFAOYSA-N 0.000 claims 1
- 150000003951 lactams Chemical class 0.000 claims 1
- 230000008018 melting Effects 0.000 claims 1
- 238000002844 melting Methods 0.000 claims 1
- 230000003647 oxidation Effects 0.000 claims 1
- 238000007254 oxidation reaction Methods 0.000 claims 1
- 229920000728 polyester Polymers 0.000 claims 1
- 239000000565 sealant Substances 0.000 claims 1
- 229920006024 semi-aromatic copolyamide Polymers 0.000 claims 1
Classifications
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B32—LAYERED PRODUCTS
- B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
- B32B27/00—Layered products comprising a layer of synthetic resin
- B32B27/06—Layered products comprising a layer of synthetic resin as the main or only constituent of a layer, which is next to another layer of the same or of a different material
- B32B27/08—Layered products comprising a layer of synthetic resin as the main or only constituent of a layer, which is next to another layer of the same or of a different material of synthetic resin
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B32—LAYERED PRODUCTS
- B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
- B32B27/00—Layered products comprising a layer of synthetic resin
- B32B27/18—Layered products comprising a layer of synthetic resin characterised by the use of special additives
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B32—LAYERED PRODUCTS
- B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
- B32B27/00—Layered products comprising a layer of synthetic resin
- B32B27/30—Layered products comprising a layer of synthetic resin comprising vinyl (co)polymers; comprising acrylic (co)polymers
- B32B27/304—Layered products comprising a layer of synthetic resin comprising vinyl (co)polymers; comprising acrylic (co)polymers comprising vinyl halide (co)polymers, e.g. PVC, PVDC, PVF, PVDF
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B32—LAYERED PRODUCTS
- B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
- B32B27/00—Layered products comprising a layer of synthetic resin
- B32B27/32—Layered products comprising a layer of synthetic resin comprising polyolefins
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- B—PERFORMING OPERATIONS; TRANSPORTING
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- B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
- B32B27/00—Layered products comprising a layer of synthetic resin
- B32B27/32—Layered products comprising a layer of synthetic resin comprising polyolefins
- B32B27/322—Layered products comprising a layer of synthetic resin comprising polyolefins comprising halogenated polyolefins, e.g. PTFE
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- B—PERFORMING OPERATIONS; TRANSPORTING
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- B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
- B32B27/00—Layered products comprising a layer of synthetic resin
- B32B27/34—Layered products comprising a layer of synthetic resin comprising polyamides
-
- 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
- C08G69/00—Macromolecular compounds obtained by reactions forming a carboxylic amide link in the main chain of the macromolecule
- C08G69/02—Polyamides derived from amino-carboxylic acids or from polyamines and polycarboxylic acids
- C08G69/26—Polyamides derived from amino-carboxylic acids or from polyamines and polycarboxylic acids derived from polyamines and polycarboxylic acids
- C08G69/265—Polyamides derived from amino-carboxylic acids or from polyamines and polycarboxylic acids derived from polyamines and polycarboxylic acids from at least two different diamines or at least two different dicarboxylic acids
-
- 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
- C08K3/00—Use of inorganic substances as compounding ingredients
- C08K3/02—Elements
- C08K3/04—Carbon
-
- 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
- C08K5/04—Oxygen-containing compounds
- C08K5/09—Carboxylic acids; Metal salts thereof; Anhydrides thereof
- C08K5/098—Metal salts of carboxylic acids
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L51/00—Compositions of graft polymers in which the grafted component is obtained by reactions only involving carbon-to-carbon unsaturated bonds; Compositions of derivatives of such polymers
- C08L51/04—Compositions of graft polymers in which the grafted component is obtained by reactions only involving carbon-to-carbon unsaturated bonds; Compositions of derivatives of such polymers grafted on to rubbers
-
- 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
- C08L77/02—Polyamides derived from omega-amino carboxylic acids or from lactams thereof
-
- 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
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- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D177/00—Coating compositions based on polyamides obtained by reactions forming a carboxylic amide link in the main chain; Coating compositions based on derivatives of such polymers
- C09D177/06—Polyamides derived from polyamines and polycarboxylic acids
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- F—MECHANICAL ENGINEERING; LIGHTING; HEATING; WEAPONS; BLASTING
- F16—ENGINEERING ELEMENTS AND UNITS; GENERAL MEASURES FOR PRODUCING AND MAINTAINING EFFECTIVE FUNCTIONING OF MACHINES OR INSTALLATIONS; THERMAL INSULATION IN GENERAL
- F16L—PIPES; JOINTS OR FITTINGS FOR PIPES; SUPPORTS FOR PIPES, CABLES OR PROTECTIVE TUBING; MEANS FOR THERMAL INSULATION IN GENERAL
- F16L11/00—Hoses, i.e. flexible pipes
-
- F—MECHANICAL ENGINEERING; LIGHTING; HEATING; WEAPONS; BLASTING
- F16—ENGINEERING ELEMENTS AND UNITS; GENERAL MEASURES FOR PRODUCING AND MAINTAINING EFFECTIVE FUNCTIONING OF MACHINES OR INSTALLATIONS; THERMAL INSULATION IN GENERAL
- F16L—PIPES; JOINTS OR FITTINGS FOR PIPES; SUPPORTS FOR PIPES, CABLES OR PROTECTIVE TUBING; MEANS FOR THERMAL INSULATION IN GENERAL
- F16L9/00—Rigid pipes
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B32—LAYERED PRODUCTS
- B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
- B32B2250/00—Layers arrangement
- B32B2250/24—All layers being polymeric
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B32—LAYERED PRODUCTS
- B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
- B32B2307/00—Properties of the layers or laminate
- B32B2307/30—Properties of the layers or laminate having particular thermal properties
- B32B2307/306—Resistant to heat
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B32—LAYERED PRODUCTS
- B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
- B32B2307/00—Properties of the layers or laminate
- B32B2307/50—Properties of the layers or laminate having particular mechanical properties
- B32B2307/558—Impact strength, toughness
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B32—LAYERED PRODUCTS
- B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
- B32B2307/00—Properties of the layers or laminate
- B32B2307/70—Other properties
- B32B2307/724—Permeability to gases, adsorption
- B32B2307/7242—Non-permeable
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B32—LAYERED PRODUCTS
- B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
- B32B2439/00—Containers; Receptacles
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- B—PERFORMING OPERATIONS; TRANSPORTING
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- B32B2597/00—Tubular articles, e.g. hoses, pipes
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- 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
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- C08K3/041—Carbon nanotubes
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- Polymers & Plastics (AREA)
- Engineering & Computer Science (AREA)
- General Engineering & Computer Science (AREA)
- Mechanical Engineering (AREA)
- Life Sciences & Earth Sciences (AREA)
- Materials Engineering (AREA)
- Wood Science & Technology (AREA)
- Laminated Bodies (AREA)
- Rigid Pipes And Flexible Pipes (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Ceramic Engineering (AREA)
- Polyamides (AREA)
Claims (27)
1. Многослойный композит, содержащий следующие слои:
I. первый слой (слой I) из формовочной массы, содержащей по меньшей мере 40 вес.% следующих компонентов:
1) 60-99 вес.ч. полуароматического сополиамида, включающего мономерные звенья, которые получены из
α) 30-90 мол.% комбинации гексаметилендиамина и терефталевой кислоты и
β) 70-10 мол.% комбинации гексаметилендиамина и линейной алифатической дикарбоновой кислоты с 8-19 атомами углерода;
где величины в мол.% относятся к сумме α) и β), и где не более 20% гексаметилендиамина могут быть заменены эквивалентным количеством другого диамина, и/или где не более 20% терефталевой кислоты могут быть заменены эквивалентным количеством другой ароматической дикарбоновой кислоты и/или 1,4-циклогександикарбоновой кислоты, и/или где не более 20% повторяющихся звеньев, состоящих из гексаметилендиамина и линейной алифатической дикарбоновой кислоты, могут быть заменены эквивалентным числом звеньев, полученных из лактама/ω-аминокарбоновой кислоты с 6-12 атомами углерода,
2) 40-1 вес.ч. олефинового сополимера в качестве модифицирующей добавки, увеличивающей ударную прочность,
где сумма вес.ч. в 1) и 2) равна 100; и
II. второй слой (слой II) из формовочной массы, содержащей по меньшей мере 60 вес.% фторполимера.
2. Многослойный композит по п. 1, отличающийся тем, что формовочная масса для слоя I содержит 0,01-60 вес.% дополнительных добавок.
3. Многослойный композит по п. 2, отличающийся тем, что одна из дополнительных добавок представляет собой медьсодержащий стабилизатор.
4. Многослойный композит по любому из п. 2 и 3, отличающийся тем, что одна из дополнительных добавок представляет собой стабилизатор окисления.
5. Многослойный композит по п. 1, отличающийся тем, что температура плавления Tm кристаллитов сополиамида для слоя I находится диапазоне от 220 до 300°С при измерении в соответствии с ISO 11357 при 2-ом нагревании.
6. Многослойный композит по п. 1, отличающийся тем, что фторполимер в формовочной массе для слоя II выбран из поливинилиденфторида (PVDF), сополимера на основе винилиденфторида, содержащего до 40 вес.% других мономеров, сополимера этилена и тетрафторэтилена (ETFE), ETFE, модифицированного теркомпонентом, таким как пропен, гексафторпропен, винилфторид или винилиденфторид, сополимера этилена и хлортрифторэтилена (E-CTFE), полихлортрифторэтилена (PCTFE), сополимера тетрафторэтилен-гексафторпропен-винилиденфторид (THV), сополимера тетрафторэтилена и гексафторпропена (FEP) или сополимера тетрафторэтилена и перфторалкил-винилового простого эфира (PFA).
7. Многослойный композит по п. 1, отличающийся тем, что указанный композит содержит один или более дополнительный слоев.
8. Многослойный композит по п. 7, отличающийся тем, что дополнительный слой или дополнительные слои выбраны из
дополнительного слоя I,
дополнительного слоя II,
слоя усилителя адгезии,
слоя из формовочной массы на основе алифатического полиамида,
слоя из формовочной массы со сложным полиэфиром и
слоя из формовочной массы с EVOH.
9. Многослойный композит по п. 1, отличающийся тем, что указанный композит представляет собой пленку, лист или полое изделие.
10. Многослойный композит по п. 9, отличающийся тем, что полое изделие представляет собой полый профиль, в частности трубку или емкость.
11. Многослойный композит по п. 10, отличающийся тем, что указанный композит содержит один или более дополнительных слоев, выбранных из электропроводящего слоя и эластомерной оболочки.
12. Многослойный композит по любому из п. 10 и 11, отличающийся тем, что указанный композит представляет собой топливопровод, гидравлический трубопровод, трубопровод тормозной системы, трубопровод муфты, трубопровод охлаждающей жидкости, уплотнитель для жестких или гибких трубок в нефте- или газодобывающей промышленности или трубопровод для шлангокабеля.
13. Многослойный композит по любому из п. 10 и 11, отличающийся тем, что указанный композит представляет собой емкость для тормозной жидкости или топливную емкость.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP15159426.4A EP3069875B1 (de) | 2015-03-17 | 2015-03-17 | Mehrschichtverbund mit einer fluorpolymerschicht |
| EPEP15159426 | 2015-03-17 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| RU2016109460A true RU2016109460A (ru) | 2017-09-19 |
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| RU2016109460A RU2016109460A (ru) | 2015-03-17 | 2016-03-16 | Многослойный композит, содержащий слой фторполимера |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US11135821B2 (ru) |
| EP (1) | EP3069875B1 (ru) |
| JP (1) | JP6868966B2 (ru) |
| KR (1) | KR102357013B1 (ru) |
| CN (1) | CN105984192A (ru) |
| BR (1) | BR102016005778B1 (ru) |
| MX (1) | MX2016003331A (ru) |
| RU (1) | RU2016109460A (ru) |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN107603086B (zh) * | 2017-08-04 | 2019-12-03 | 青岛正大环保科技有限公司 | 一种高分子多层式防水薄膜的制备方法 |
| CN107627703B (zh) * | 2017-08-04 | 2019-09-10 | 成都兆丰斯诺科技有限公司 | 一种高分子多层式防水薄膜 |
| EP3477176A1 (de) | 2017-10-25 | 2019-05-01 | Evonik Degussa GmbH | Verfahren zur herstellung eines mit einem inliner ausgekleideten rohres |
| CN109161190B (zh) * | 2018-07-19 | 2021-02-19 | 广东顺德顺炎新材料股份有限公司 | 一种玻纤增强pa66汽车进气歧管材料及其制备方法 |
| EP3626764B1 (de) * | 2018-09-21 | 2021-02-24 | Evonik Operations GmbH | Composite mit thermoplastischer matrix |
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- 2016-03-16 RU RU2016109460A patent/RU2016109460A/ru not_active Application Discontinuation
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- 2016-03-17 JP JP2016054434A patent/JP6868966B2/ja active Active
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|---|---|
| KR20160111870A (ko) | 2016-09-27 |
| EP3069875A1 (de) | 2016-09-21 |
| JP6868966B2 (ja) | 2021-05-12 |
| MX2016003331A (es) | 2016-09-16 |
| KR102357013B1 (ko) | 2022-01-28 |
| EP3069875B1 (de) | 2017-07-05 |
| CN105984192A (zh) | 2016-10-05 |
| US20160271918A1 (en) | 2016-09-22 |
| BR102016005778B1 (pt) | 2020-11-24 |
| JP2016172448A (ja) | 2016-09-29 |
| BR102016005778A2 (pt) | 2017-01-24 |
| US11135821B2 (en) | 2021-10-05 |
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