WO2022234223A1 - Compositions a base de polyamides et de fibres de verre et leur utilisation dans le domaine du medical - Google Patents
Compositions a base de polyamides et de fibres de verre et leur utilisation dans le domaine du medical Download PDFInfo
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- WO2022234223A1 WO2022234223A1 PCT/FR2022/050828 FR2022050828W WO2022234223A1 WO 2022234223 A1 WO2022234223 A1 WO 2022234223A1 FR 2022050828 W FR2022050828 W FR 2022050828W WO 2022234223 A1 WO2022234223 A1 WO 2022234223A1
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- WIPO (PCT)
- Prior art keywords
- equal
- composition
- polyamide
- composition according
- cis
- Prior art date
Links
- 239000000203 mixture Substances 0.000 title claims abstract description 81
- 239000003365 glass fiber Substances 0.000 title claims abstract description 35
- 239000004952 Polyamide Substances 0.000 title claims abstract description 32
- 229920002647 polyamide Polymers 0.000 title claims abstract description 32
- 239000004953 Aliphatic polyamide Substances 0.000 claims abstract description 23
- 229920003231 aliphatic polyamide Polymers 0.000 claims abstract description 23
- 239000000654 additive Substances 0.000 claims abstract description 21
- 238000000465 moulding Methods 0.000 claims abstract description 18
- 230000000996 additive effect Effects 0.000 claims abstract description 17
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 16
- 125000004433 nitrogen atom Chemical group N* 0.000 claims abstract description 14
- 239000000470 constituent Substances 0.000 claims abstract description 13
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 12
- 230000001954 sterilising effect Effects 0.000 claims description 32
- 238000004659 sterilization and disinfection Methods 0.000 claims description 32
- 239000000243 solution Substances 0.000 claims description 16
- 239000000835 fiber Substances 0.000 claims description 14
- 239000003381 stabilizer Substances 0.000 claims description 9
- GHOKWGTUZJEAQD-ZETCQYMHSA-N (D)-(+)-Pantothenic acid Chemical compound OCC(C)(C)[C@@H](O)C(=O)NCCC(O)=O GHOKWGTUZJEAQD-ZETCQYMHSA-N 0.000 claims description 8
- 229920000299 Nylon 12 Polymers 0.000 claims description 8
- -1 aliphatic diamine Chemical class 0.000 claims description 5
- 150000001413 amino acids Chemical class 0.000 claims description 5
- 150000004985 diamines Chemical class 0.000 claims description 5
- 238000001746 injection moulding Methods 0.000 claims description 5
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims description 4
- 238000006068 polycondensation reaction Methods 0.000 claims description 4
- LHBHZALHFIQJGJ-UHFFFAOYSA-N 3-hydroxy-2-(4-methoxyphenyl)-3,5-dihydro-2h-1,5-benzothiazepin-4-one Chemical compound C1=CC(OC)=CC=C1C1C(O)C(=O)NC2=CC=CC=C2S1 LHBHZALHFIQJGJ-UHFFFAOYSA-N 0.000 claims description 3
- 239000003963 antioxidant agent Substances 0.000 claims description 3
- 239000000945 filler Substances 0.000 claims description 3
- 239000000049 pigment Substances 0.000 claims description 3
- 239000004014 plasticizer Substances 0.000 claims description 3
- 229920006396 polyamide 1012 Polymers 0.000 claims description 3
- 229920006152 PA1010 Polymers 0.000 claims description 2
- 239000003063 flame retardant Substances 0.000 claims description 2
- 238000010330 laser marking Methods 0.000 claims description 2
- 239000000314 lubricant Substances 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 239000002667 nucleating agent Substances 0.000 claims description 2
- 239000004094 surface-active agent Substances 0.000 claims description 2
- 239000001993 wax Substances 0.000 claims description 2
- 239000000975 dye Substances 0.000 claims 1
- 238000002347 injection Methods 0.000 description 7
- 239000007924 injection Substances 0.000 description 7
- 229910052751 metal Inorganic materials 0.000 description 5
- 239000002184 metal Substances 0.000 description 5
- 239000004033 plastic Substances 0.000 description 5
- 229920003023 plastic Polymers 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- BTZVDPWKGXMQFW-UHFFFAOYSA-N Pentadecanedioic acid Chemical compound OC(=O)CCCCCCCCCCCCCC(O)=O BTZVDPWKGXMQFW-UHFFFAOYSA-N 0.000 description 4
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 4
- 229910052799 carbon Inorganic materials 0.000 description 4
- QQHJDPROMQRDLA-UHFFFAOYSA-N hexadecanedioic acid Chemical compound OC(=O)CCCCCCCCCCCCCCC(O)=O QQHJDPROMQRDLA-UHFFFAOYSA-N 0.000 description 4
- NAQMVNRVTILPCV-UHFFFAOYSA-N hexane-1,6-diamine Chemical compound NCCCCCCN NAQMVNRVTILPCV-UHFFFAOYSA-N 0.000 description 4
- BDJRBEYXGGNYIS-UHFFFAOYSA-N nonanedioic acid Chemical compound OC(=O)CCCCCCCC(O)=O BDJRBEYXGGNYIS-UHFFFAOYSA-N 0.000 description 4
- BNJOQKFENDDGSC-UHFFFAOYSA-N octadecanedioic acid Chemical compound OC(=O)CCCCCCCCCCCCCCCCC(O)=O BNJOQKFENDDGSC-UHFFFAOYSA-N 0.000 description 4
- CXMXRPHRNRROMY-UHFFFAOYSA-N sebacic acid Chemical compound OC(=O)CCCCCCCCC(O)=O CXMXRPHRNRROMY-UHFFFAOYSA-N 0.000 description 4
- TYFQFVWCELRYAO-UHFFFAOYSA-N suberic acid Chemical compound OC(=O)CCCCCCC(O)=O TYFQFVWCELRYAO-UHFFFAOYSA-N 0.000 description 4
- HQHCYKULIHKCEB-UHFFFAOYSA-N tetradecanedioic acid Chemical compound OC(=O)CCCCCCCCCCCCC(O)=O HQHCYKULIHKCEB-UHFFFAOYSA-N 0.000 description 4
- LWBHHRRTOZQPDM-UHFFFAOYSA-N undecanedioic acid Chemical compound OC(=O)CCCCCCCCCC(O)=O LWBHHRRTOZQPDM-UHFFFAOYSA-N 0.000 description 4
- 239000011575 calcium Substances 0.000 description 3
- 150000001721 carbon Chemical group 0.000 description 3
- 229910052802 copper Inorganic materials 0.000 description 3
- 239000010949 copper Substances 0.000 description 3
- 239000011152 fibreglass Substances 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 238000000034 method Methods 0.000 description 3
- QFGCFKJIPBRJGM-UHFFFAOYSA-N 12-[(2-methylpropan-2-yl)oxy]-12-oxododecanoic acid Chemical compound CC(C)(C)OC(=O)CCCCCCCCCCC(O)=O QFGCFKJIPBRJGM-UHFFFAOYSA-N 0.000 description 2
- PBLZLIFKVPJDCO-UHFFFAOYSA-N 12-aminododecanoic acid Chemical compound NCCCCCCCCCCCC(O)=O PBLZLIFKVPJDCO-UHFFFAOYSA-N 0.000 description 2
- DPUOLQHDNGRHBS-UHFFFAOYSA-N Brassidinsaeure Natural products CCCCCCCCC=CCCCCCCCCCCCC(O)=O DPUOLQHDNGRHBS-UHFFFAOYSA-N 0.000 description 2
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 239000001361 adipic acid Substances 0.000 description 2
- 235000011037 adipic acid Nutrition 0.000 description 2
- 125000004429 atom Chemical group 0.000 description 2
- 238000004140 cleaning Methods 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- LJOSESICVCVVCK-UHFFFAOYSA-N docosane-1,1-diamine Chemical compound CCCCCCCCCCCCCCCCCCCCCC(N)N LJOSESICVCVVCK-UHFFFAOYSA-N 0.000 description 2
- 150000003951 lactams Chemical class 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
- KIDHWZJUCRJVML-UHFFFAOYSA-N putrescine Chemical compound NCCCCN KIDHWZJUCRJVML-UHFFFAOYSA-N 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 238000009864 tensile test Methods 0.000 description 2
- DXNCZXXFRKPEPY-UHFFFAOYSA-N tridecanedioic acid Chemical compound OC(=O)CCCCCCCCCCCC(O)=O DXNCZXXFRKPEPY-UHFFFAOYSA-N 0.000 description 2
- RTBFRGCFXZNCOE-UHFFFAOYSA-N 1-methylsulfonylpiperidin-4-one Chemical compound CS(=O)(=O)N1CCC(=O)CC1 RTBFRGCFXZNCOE-UHFFFAOYSA-N 0.000 description 1
- XAUQWYHSQICPAZ-UHFFFAOYSA-N 10-amino-decanoic acid Chemical compound NCCCCCCCCCC(O)=O XAUQWYHSQICPAZ-UHFFFAOYSA-N 0.000 description 1
- DWHXNKJKNIHNOI-UHFFFAOYSA-N 10-azaniumylundecanoate Chemical compound CC(N)CCCCCCCCC(O)=O DWHXNKJKNIHNOI-UHFFFAOYSA-N 0.000 description 1
- GNHLOUIICBHQIT-UHFFFAOYSA-N 11-(heptylamino)undecanoic acid Chemical compound CCCCCCCNCCCCCCCCCCC(O)=O GNHLOUIICBHQIT-UHFFFAOYSA-N 0.000 description 1
- GUOSQNAUYHMCRU-UHFFFAOYSA-N 11-Aminoundecanoic acid Chemical compound NCCCCCCCCCCC(O)=O GUOSQNAUYHMCRU-UHFFFAOYSA-N 0.000 description 1
- VWPQCOZMXULHDM-UHFFFAOYSA-N 9-aminononanoic acid Chemical compound NCCCCCCCCC(O)=O VWPQCOZMXULHDM-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- GUTLYIVDDKVIGB-OUBTZVSYSA-N Cobalt-60 Chemical compound [60Co] GUTLYIVDDKVIGB-OUBTZVSYSA-N 0.000 description 1
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
- JHWNWJKBPDFINM-UHFFFAOYSA-N Laurolactam Chemical compound O=C1CCCCCCCCCCCN1 JHWNWJKBPDFINM-UHFFFAOYSA-N 0.000 description 1
- 229920000571 Nylon 11 Polymers 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 1
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 1
- 239000012963 UV stabilizer Substances 0.000 description 1
- BGYHLZZASRKEJE-UHFFFAOYSA-N [3-[3-(3,5-ditert-butyl-4-hydroxyphenyl)propanoyloxy]-2,2-bis[3-(3,5-ditert-butyl-4-hydroxyphenyl)propanoyloxymethyl]propyl] 3-(3,5-ditert-butyl-4-hydroxyphenyl)propanoate Chemical compound CC(C)(C)C1=C(O)C(C(C)(C)C)=CC(CCC(=O)OCC(COC(=O)CCC=2C=C(C(O)=C(C=2)C(C)(C)C)C(C)(C)C)(COC(=O)CCC=2C=C(C(O)=C(C=2)C(C)(C)C)C(C)(C)C)COC(=O)CCC=2C=C(C(O)=C(C=2)C(C)(C)C)C(C)(C)C)=C1 BGYHLZZASRKEJE-UHFFFAOYSA-N 0.000 description 1
- 150000001242 acetic acid derivatives Chemical class 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 229910001508 alkali metal halide Inorganic materials 0.000 description 1
- 150000008045 alkali metal halides Chemical class 0.000 description 1
- 239000003708 ampul Substances 0.000 description 1
- JFCQEDHGNNZCLN-UHFFFAOYSA-N anhydrous glutaric acid Natural products OC(=O)CCCC(O)=O JFCQEDHGNNZCLN-UHFFFAOYSA-N 0.000 description 1
- 230000003078 antioxidant effect Effects 0.000 description 1
- 239000008280 blood Substances 0.000 description 1
- 210000004369 blood Anatomy 0.000 description 1
- 210000000988 bone and bone Anatomy 0.000 description 1
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 1
- VHRGRCVQAFMJIZ-UHFFFAOYSA-N cadaverine Chemical compound NCCCCCN VHRGRCVQAFMJIZ-UHFFFAOYSA-N 0.000 description 1
- CJZGTCYPCWQAJB-UHFFFAOYSA-L calcium stearate Chemical compound [Ca+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O CJZGTCYPCWQAJB-UHFFFAOYSA-L 0.000 description 1
- 239000008116 calcium stearate Substances 0.000 description 1
- 235000013539 calcium stearate Nutrition 0.000 description 1
- 239000006229 carbon black Substances 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 238000013329 compounding Methods 0.000 description 1
- 230000001143 conditioned effect Effects 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- 229920006177 crystalline aliphatic polyamide Polymers 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000010894 electron beam technology Methods 0.000 description 1
- 238000001125 extrusion Methods 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 229920006017 homo-polyamide Polymers 0.000 description 1
- 238000010102 injection blow moulding Methods 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 125000003717 m-cresyl group Chemical group [H]C1=C([H])C(O*)=C([H])C(=C1[H])C([H])([H])[H] 0.000 description 1
- RLSSMJSEOOYNOY-UHFFFAOYSA-N m-methyl-PhOH Natural products CC1=CC=CC(O)=C1 RLSSMJSEOOYNOY-UHFFFAOYSA-N 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 229910044991 metal oxide Inorganic materials 0.000 description 1
- 150000004706 metal oxides Chemical class 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- YNVQYOQLKGNUBZ-UHFFFAOYSA-N octadecane-1,1-diamine Chemical compound CCCCCCCCCCCCCCCCCC(N)N YNVQYOQLKGNUBZ-UHFFFAOYSA-N 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 210000004915 pus Anatomy 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 238000001175 rotational moulding Methods 0.000 description 1
- 238000004626 scanning electron microscopy Methods 0.000 description 1
- 229920006114 semi-crystalline semi-aromatic polyamide Polymers 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 231100000732 tissue residue Toxicity 0.000 description 1
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
- 238000011282 treatment Methods 0.000 description 1
Classifications
-
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61L—METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES
- A61L2/00—Methods or apparatus for disinfecting or sterilising materials or objects other than foodstuffs or contact lenses; Accessories therefor
- A61L2/02—Methods or apparatus for disinfecting or sterilising materials or objects other than foodstuffs or contact lenses; Accessories therefor using physical phenomena
- A61L2/04—Heat
- A61L2/06—Hot gas
- A61L2/07—Steam
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61L—METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES
- A61L2/00—Methods or apparatus for disinfecting or sterilising materials or objects other than foodstuffs or contact lenses; Accessories therefor
- A61L2/26—Accessories or devices or components used for biocidal treatment
- A61L2/28—Devices for testing the effectiveness or completeness of sterilisation, e.g. indicators which change colour
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B29—WORKING OF PLASTICS; WORKING OF SUBSTANCES IN A PLASTIC STATE IN GENERAL
- B29C—SHAPING OR JOINING OF PLASTICS; SHAPING OF MATERIAL IN A PLASTIC STATE, NOT OTHERWISE PROVIDED FOR; AFTER-TREATMENT OF THE SHAPED PRODUCTS, e.g. REPAIRING
- B29C45/00—Injection moulding, i.e. forcing the required volume of moulding material through a nozzle into a closed mould; Apparatus therefor
- B29C45/0005—Injection moulding, i.e. forcing the required volume of moulding material through a nozzle into a closed mould; Apparatus therefor using fibre reinforcements
-
- 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
- C08J5/04—Reinforcing macromolecular compounds with loose or coherent fibrous material
- C08J5/0405—Reinforcing macromolecular compounds with loose or coherent fibrous material with inorganic fibres
- C08J5/043—Reinforcing macromolecular compounds with loose or coherent fibrous material with inorganic fibres with glass fibres
-
- 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
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/04—Oxygen-containing compounds
- C08K5/10—Esters; Ether-esters
- C08K5/12—Esters; Ether-esters of cyclic polycarboxylic 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
- C08K7/00—Use of ingredients characterised by shape
- C08K7/02—Fibres or whiskers
- C08K7/04—Fibres or whiskers inorganic
- C08K7/14—Glass
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61L—METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES
- A61L2202/00—Aspects relating to methods or apparatus for disinfecting or sterilising materials or objects
- A61L2202/20—Targets to be treated
- A61L2202/24—Medical instruments, e.g. endoscopes, catheters, sharps
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B29—WORKING OF PLASTICS; WORKING OF SUBSTANCES IN A PLASTIC STATE IN GENERAL
- B29K—INDEXING SCHEME ASSOCIATED WITH SUBCLASSES B29B, B29C OR B29D, RELATING TO MOULDING MATERIALS OR TO MATERIALS FOR MOULDS, REINFORCEMENTS, FILLERS OR PREFORMED PARTS, e.g. INSERTS
- B29K2077/00—Use of PA, i.e. polyamides, e.g. polyesteramides or derivatives thereof, as moulding material
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B29—WORKING OF PLASTICS; WORKING OF SUBSTANCES IN A PLASTIC STATE IN GENERAL
- B29K—INDEXING SCHEME ASSOCIATED WITH SUBCLASSES B29B, B29C OR B29D, RELATING TO MOULDING MATERIALS OR TO MATERIALS FOR MOULDS, REINFORCEMENTS, FILLERS OR PREFORMED PARTS, e.g. INSERTS
- B29K2995/00—Properties of moulding materials, reinforcements, fillers, preformed parts or moulds
- B29K2995/0012—Properties of moulding materials, reinforcements, fillers, preformed parts or moulds having particular thermal properties
- B29K2995/0017—Heat stable
-
- 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
- C08J2377/00—Characterised by the use of polyamides obtained by reactions forming a carboxylic amide link in the main chain; Derivatives of such polymers
- C08J2377/02—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
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K2201/00—Specific properties of additives
- C08K2201/002—Physical properties
- C08K2201/004—Additives being defined by their length
Definitions
- the present invention relates to molding compositions based on polyamides and glass fibers and their use in the medical field.
- Medical and surgical instruments are typically made of metal and must be carefully maintained to avoid corrosion, especially with regard to surgical residues adhering and drying on the instruments (encrustations) or the presence of blood, pus, tissue residues and bones on instruments after use.
- the rigidity of these plastic instruments must however be high because it replaces metal.
- the plastic must therefore have a high modulus and a high stress.
- This plastic material must also be easily processable by an injection process; with in particular a low mold temperature (for example ⁇ 100° C.); to make these instruments.
- a low mold temperature for example ⁇ 100° C.
- the injected parts must have a good shine (gloss) as well as a low warpage, in particular for thin parts, and they must also resist sterilization treatments, in particular steam sterilization, gamma sterilization , sterilization with ethylene oxide and sterilization by electron beams (ebeam) while having a low moisture uptake.
- sterilization treatments in particular steam sterilization, gamma sterilization , sterilization with ethylene oxide and sterilization by electron beams (ebeam) while having a low moisture uptake.
- the injected parts must have good chemical resistance to the cleaning products used in hospitals.
- the present invention therefore relates to a molding composition, comprising by weight: a) 20 to 60%, in particular from 20 to 50%, in particular 25 to 39.9% of at least one long-chain aliphatic polyamide having a number of carbon atom per nitrogen atom greater than or equal to 9, in particular greater than or equal to 10, said at least one polyamide having an inherent viscosity in solution of less than or equal to 1.3, in particular less than or equal to 1.25, as determined according to standard ISO 307: 2007 at a temperature of 20°C.
- the inventors have therefore found that the selection of at least one long-chain aliphatic polyamide having a particular inherent viscosity in solution with a particular range of glass fibers makes it possible to form a composition which, after injection, exhibits the compromise of properties defined above. .
- the inherent viscosity in solution is determined according to ISO 307:2007 modified in that the solvent is m-cresol rather than sulfuric acid, and that the concentration is 0.5% by weight and that the temperature is 20°C.
- a molding composition according to the invention is a composition transformed for example by injection, injection blow molding, expansion molding and rotational molding.
- the molding composition comprises from 20 to 60%, in particular from 20 to 50%, in particular 25 to 39.9% of at least one long-chain aliphatic polyamide having a higher number of carbon atoms per nitrogen atom or equal to 9, in particular greater than or equal to 10.
- the polyamide can be a homopolyamide or a copolyamide or a mixture thereof.
- said polyamide is a semi-crystalline polyamide or copolyamide.
- melt-crystalline within the meaning of the invention, denotes a polyamide or a copolyamide which has a melting point (Tm) in DSC according to standard ISO 11357-3: 2013, and an enthalpy of crystallization during the cooling step at a speed of 20 K/min in DSC measured according to standard ISO 11357-3 of 2013 greater than 20 J/g, preferably greater than 30 J/g.
- Said polyamide is derived from a repeating unit obtained by polycondensation: of at least one amino acid in Cg to Cis, preferentially in Cio to Cis, more preferentially in Cio to C12, or of at least one lactam in Cg to Cis, preferentially in Cio to Cis, more preferably in Cio to C 12 , or at least one C 4 -C 36 , preferably C 6 -C 18 , preferably C 6 -C 12 , more preferably C10-C12 diamine Ca, with at least one Cb C 4 -C 36 dicarboxylic acid, preferably C 6 -C 18 , preferably C6-C12, more preferably C10-C12, or a mixture thereof, provided that the number of carbon atoms per nitrogen atom of the repeating unit is greater than or equal to 9, in individual greater than or equal to 10.
- the long-chain aliphatic polyamide is obtained by polycondensation: of at least one Cg to Cis amino acid, preferentially Cio to Cis, in particular Cio to C 12 , or of at least one Cg to Cis lactam, preferentially in Cio to Cis, in particular in Cio to C 12 .
- a Cg to C 12 amino acid is in particular 9-aminononanoic acid, 10-aminodecanoic acid, 10-aminoundecanoic acid, 12-aminododecanoic acid and 11-aminoundecanoic acid as well as its derivatives, in particular N-heptyl-ll-aminoundecanoic acid.
- a Cg to C 12 lactam is in particular lauryllactam.
- Said at least one C4-C36 diamine Ca can be chosen in particular from 1,4-butanediamine, 1,5-pentamethylenediamine, 1,6-hexamethylenediamine, 1,7-heptamethylediamine, 1,8-octamethylediamine, 1,9-nonamethyldiamine, 1,10-decamethyldiamine, 1,11-undecamethyldiamine, 1,12-dodecamethyldiamine, 1,13-tridecamethyldiamine, 1,14-tetradecamethyldiamine, 1,16-hexadecamethyldiamine and 1, 18-octadecamethylediamine, octadecenediamine, eicosanediamine, docosanediamine and diamines obtained from fatty acids.
- said at least one diamine Ca is C6-C18 and chosen from 1,6-hexamethylenediamine, 1,7-heptamethylediamine, 1,8-octamethylediamine, 1,9-nonamethylediamine, 1,10-decamethylediamine , 1,11-undecamethyldiamine, 1,12-dodecamethyldiamine, 1,13-tridecamethyldiamine, 1,14-tetradecamethyldiamine, 1,16-hexadecamethyldiamine and 1,18-octadecamethyldiamine.
- Said at least one Cb C 4 to C 36 dicarboxylic acid can be chosen from succinic acid, glutaric acid, adipic acid, suberic acid, azelaic acid, sebacic acid, undecanedioic acid , dodecanedioic acid, brassylic acid, tetradecanedioic acid, pentadecanedioic acid, hexadecanedioic acid, octadecanedioic acid, octadecanediamine, eicosanediamine, docosanediamine and diamines obtained from acids bold.
- said at least one Cb dicarboxylic acid is C 6 to Cis and is chosen from adipic acid, suberic acid, azelaic acid, sebacic acid, undecanedioic acid, dodecanedioic acid, brassylic acid, tetradecanedioic acid, pentadecanedioic acid, hexadecanedioic acid, octadecanedioic acid.
- the long-chain aliphatic polyamide is chosen from: polyamide 1010 (PA1010), polyamide 1012 (PA1012), polyamide 1212 (PA1012), polyamide 11 (PAU), polyamide 12 (PA12), or a mixture thereof or a copolyamide thereof.
- the polyamide is in particular PAU and PA12.
- said long chain aliphatic polyamide is a mixture of two polyamides in a range of proportion by weight of 5/95 to 95/5.
- said mixture is a mixture of two identical polyamides having the same number of carbon atoms per nitrogen atom but with an inherent viscosity in solution of one of the two polyamides greater than 1.3 but on the condition that the mixture meets the condition of having an inherent viscosity in solution of less than or equal to 1.3, in particular less than or equal to 1.25.
- the glass fibers are present from 40% to 75%, in particular from 50 to 75%, in particular from 60 to 70% by weight relative to the total weight of the composition.
- the glass fibers can be solid and/or hollow, advantageously they are solid.
- the glass fibers are advantageously short.
- the short glass fibers preferably have a length of between 2 and 13 mm, preferably of 3 to 8 mm before the compositions are implemented.
- the short glass fibers have a fiber length of 120 to 350 ⁇ m.
- This fiber length of 120 to 350 ⁇ m is measured on the compound.
- the short glass fibers can be circular or non-circular in section.
- a fiber with a circular section is defined as a fiber having at any point of its circumference a distance equal to the center of the fiber and therefore represents a perfect or almost perfect circle.
- Any fiberglass that does not have this perfect or near-perfect circle is therefore defined as a fiber with a non-circular section.
- non-circular fibers having for example an elliptical, oval or cocoon shape, star fibers, flake fibers, fibers plates, cruciforms, a polygon and a ring.
- Fiberglass can be:
- L and D can be measured by scanning electron microscopy (SEM).
- SEM scanning electron microscopy
- the at least one additive is optionally present from 0 to 5% by weight, in particular from 0.1 to 5%, relative to the total weight of the composition.
- the additive is selected from fillers, colorants, stabilizers, plasticizers, surfactants, nucleating agents, pigments, brighteners, antioxidants, lubricants, flame retardants, natural waxes, additives for laser marking , and mixtures thereof.
- the stabilizer can be a UV stabilizer, an organic stabilizer or more generally a combination of organic stabilizers, such as a phenol-type antioxidant (for example of the type of that of irganox ® 1010 from the company Ciba- BASF).
- a phenol-type antioxidant for example of the type of that of irganox ® 1010 from the company Ciba- BASF.
- This stabilizer can also be an inorganic stabilizer, such as a copper-based stabilizer.
- a copper-based stabilizer By way of example of such mineral stabilizers, mention may be made of copper halides and acetates. Incidentally, other metals such as silver can be considered, but these are known to be less effective. These copper-based compounds are typically associated with alkali metal halides, particularly potassium.
- the fillers can be chosen from carbon black, talc, pigments, metal oxides (titanium oxide).
- the molding composition comprises by weight: a) 20 to 60%, in particular from 20 to 50%, in particular 25 to 39.9% of at least one long-chain aliphatic polyamide having a number of carbon atoms per nitrogen atom greater than or equal to 9, in particular greater than or equal to 10, said at least one polyamide having an inherent viscosity in solution less than or equal to 1.3 , in particular less than or equal to 1.25, as determined according to standard ISO 307: 2007 at a temperature of 20°C.
- a polyamide other than an aliphatic polyamide, in particular a semi-crystalline one, is excluded from the composition.
- the molding composition consists of (by weight): a) 20 to 60%, in particular from 20 to 50%, in particular 25 to 39.9% of at least one long-chain aliphatic polyamide having a number of carbon atoms per nitrogen atom greater than or equal to 9 , in particular greater than or equal to 10, said at least one polyamide having an inherent viscosity in solution less than or equal to 1.3, in particular less than or equal to 1.25, as determined according to standard ISO 307: 2007 at a temperature of 20°C.
- the molding composition comprises by weight: a) 20 to 50%, in particular 25 to 39.9% of at least one long-chain aliphatic polyamide having a number of carbon atoms per atom of nitrogen greater than or equal to 9, in particular greater than or equal to 10, said at least one polyamide having an inherent viscosity in solution less than or equal to 1.3, in particular less than or equal to 1.25, as determined according to the standard ISO 307: 2007 at a temperature of 20°C. b) 50 to 75%, in particular 60 to 70% of glass fibres, and c) 0 to 5% by weight, preferably 0.1 to 5% by weight of at least one additive, the sum of the proportions of each constituent of said composition being equal to 100%.
- the molding composition comprises by weight: a) 20 to 49.9%, in particular 25 to 39.9% of at least one long-chain aliphatic polyamide having a number of carbon atom per nitrogen atom greater than or equal to 9, in particular greater than or equal to 10, said at least one polyamide having an inherent viscosity in solution less than or equal to 1.3, in particular less than or equal to 1.25 , as determined according to ISO 307: 2007 at a temperature of 20°C. b) 50 to 75%, in particular 60 to 70%, of glass fibres, and c) 0.1 to 5% by weight of at least one additive, the sum of the proportions of each constituent of the said composition being equal to 100%.
- the composition consists of: a) 20 to 50%, in particular 25 to 39.9% of at least one long-chain aliphatic polyamide having a number of carbon atoms per nitrogen atom greater than or equal to 9, in particular greater than or equal to 10, said at least one polyamide having an inherent viscosity in solution of less than or equal to 1.3, in particular less than or equal to 1.25, as determined according to standard ISO 307: 2007 at a temperature of 20°C. b) 50 to 75%, in particular 60 to 70% of glass fibres, and c) 0 to 5% by weight, preferably 0.1 to 5% by weight of at least one additive, the sum of the proportions of each constituent of said composition being equal to 100%.
- the composition consists of: a) 20 to 49.9%, in particular 25 to 39.9% of at least one long-chain aliphatic polyamide having a number of carbon atom per nitrogen atom greater than or equal to 9, in particular greater than or equal to 10, said at least one polyamide having an inherent viscosity in solution less than or equal to 1.3, in particular less than or equal to 1.25 , as determined according to ISO 307: 2007 at a temperature of 20°C. b) 50 to 75%, in particular 60 to 70%, of glass fibres, and c) 0.1 to 5% by weight of at least one additive, the sum of the proportions of each constituent of the said composition being equal to 100%.
- the molding composition comprises by weight: a) 25 to 40%, in particular 25 to 39.9% of at least one long-chain aliphatic polyamide having a number of carbon atoms per atom of nitrogen greater than or equal to 9, in particular greater than or equal to 10, said at least one polyamide having an inherent viscosity in solution less than or equal to 1.3, in particular less than or equal to 1.25, as determined according to the standard ISO 307: 2007 at a temperature of 20°C. b) 60 to 70% of glass fibres, and c) 0 to 5% by weight, preferably 0.1 to 5% by weight of at least one additive, the sum of the proportions of each constituent of the said composition being equal 100%.
- the molding composition comprises by weight: a) 25 to 39.9% of at least one long-chain aliphatic polyamide having a higher number of carbon atoms per nitrogen atom or equal to 9, in particular greater than or equal to 10, said at least one polyamide having an inherent viscosity in solution less than or equal to 1.3, in particular less than or equal to 1.25, as determined according to standard ISO 307 : 2007 at a temperature of 20°C. b) 60 to 70% glass fibers, and c) 0.1 to 5% by weight of at least one additive, the sum of the proportions of each constituent of said composition being equal to 100%.
- the molding composition consists of: a) 25 to 40%, in particular 25 to 39.9% of at least one long-chain aliphatic polyamide having an atomic number of carbon per nitrogen atom greater than or equal to 9, in particular greater than or equal to 10, said at least one polyamide having an inherent viscosity in solution less than or equal to 1.3, in particular less than or equal to 1.25, as determined according to ISO 307: 2007 at a temperature of 20°C. b) 60 to 70% of glass fibres, and c) 0 to 5% by weight, preferably 0.1 to 5% by weight of at least one additive, the sum of the proportions of each constituent of the said composition being equal 100%.
- the molding composition consists of: a) 25 to 39.9% of at least one long-chain aliphatic polyamide having a number of carbon atoms per nitrogen atom greater than or equal to 9, in particular greater than or equal to 10, said at least one polyamide having an inherent viscosity in solution of less than or equal to 1.3, in particular less than or equal to 1.25, as determined according to the ISO standard 307:2007 at a temperature of 20°C. b) 60 to 70% of glass fibers, and c) 0.1 to 5% by weight of at least one additive, the sum of the proportions of each constituent of said composition being equal to 100%.
- the present invention relates to the use of a composition as defined above, for the manufacture of an article for the medical field, in particular for single or multiple use. All the embodiments described above are valid for this “use” paragraph.
- article for the medical field denotes, for example, a retractor, scissors, forceps, tweezers, clamps, a hook, a needle holder, a stylet, forceps, a cannula, a trocar, a syringe, a scalpel, an extractor, a spoon, a curette, an ampoule, a catheter, a stapler, a gynecological instrument (such as a speculum), a clamp, handles of surgical instruments, a suction tube, a dilator , a sterilization tray, a cap and any other medical item traditionally made of metal.
- single-use medical article means an article which is used only once and discarded after use, such as a retractor, scissors, pliers, tweezers, pliers, a hook, a needle holder, a stylet, forceps, a cannula, a trocar, a syringe, a scalpel, extractor, spoon, curette, bulb, catheter, gynecological instrument (such as a speculum), clamp, handles of surgical instruments, suction tube, dilator, plug and any other items disposable medical device traditionally made of metal.
- multiple-use medical article refers to an article which is reused after use, and which requires cleaning and/or sterilization in order to be able to be reused.
- Sterilization can be done by steam or by gamma rays.
- said article is a surgical instrument.
- the article after steam sterilization has a cross-sectional variation of less than 3% relative to the cross-section before sterilization, determined on a type IA specimen with a cross-section of 4 ⁇ 10 mm 2 .
- the article exhibits very good resistance to gamma sterilization.
- the article after steam sterilization has a stress variation of less than 20% relative to the breaking stress before sterilization, determined according to the ISO 527: 2012 standard on a type IA specimen.
- the article is made by injection molding.
- the present invention relates to an article obtained by injection molding with a composition as defined above.
- compositions of Table 1 were prepared by mixing in the molten state the polyamide granules, with the glass fibers and optionally the additives.
- compositions based on PAU and PA12 were implemented by compounding on a co-rotating twin-screw extruder with a diameter of 40 mm with a temperature profile (T°) flat at 250°C.
- the screw speed is 300 rpm and the throughput 100 kg/h.
- the compositions based on PA66 were used for their part with a flat temperature profile at 300° C. The other parameters remain unchanged.
- the introduction of the glass fibers is carried out by lateral force-feeding.
- the semi-crystalline aliphatic polyamide and possibly the additives are added in the main hopper.
- compositions were then molded on an injection molding machine (Engel brand) at a set temperature of 260° C. (for the compositions based on PAU and PA12) and a mold temperature of 70° C. in the form of dumbbells or , bars in order to study the properties of the compositions according to the standards below. below.
- the PA66-based compositions were injected at a temperature of 300°C with a mold temperature of 110°C.
- the tensile modulus was measured at 23°C according to the ISO 527-1: 2012 standard on type IA dumbbells, before sterilization (i.e. at tO, on dry samples), after steam sterilization or after gamma sterilization.
- the elongation and the stress at break were also measured at 23° C. according to this same ISO 527-1: 2012 standard before sterilization, after steam sterilization or after gamma sterilization.
- the crosshead speed was set at 1 mm/min for the modulus measurement and 5 mm/min for the elongation and stress measurement.
- the machine used is of the INSTRON 5966 type.
- test conditions are 23°C +/- 2°C, on dry samples (before the sterilization step, i.e. at tO) and on conditioned samples (i.e. after the sterilization step). sterilization).
- the steam sterilization of the specimens is carried out in the following manner: the IA dumbbells underwent 25 sterilization cycles, under 134° C., 2 bars, for 12 minutes. Between each cycle, the sample is maintained at 50° C. for 5 minutes.
- the gloss was determined visually. Two levels of appearance have been assigned: glossy or matte appearance.
- Impact resistance was determined according to ISO 179-1: 2010 / leA (Charpy impact) on bars measuring 80mm x 10mm x 4mm, V-notched, dry, at a temperature of 23°C +/- 2°C under relative humidity of 50% +/- 10%
- “Gamma” sterilization consists of applying an ionizing dose of 50,000 Gray (using gamma radiation (cobalt 60)) to IA dumbbells (for each composition). At the end of this sterilization, we carried out a tensile test for each composition, according to the ISO 527-1: 2012 standard. Plates of 100*100*1 mm3 were also prepared by injection of the different compositions:
- warping (%) (difference between the support and the plate (in mm) / 100 mm x 100).
- FoodContactTM 295-10 fiberglass (circular section diameter 10m) is marketed by Owens Corning.
- the CSG3PA820 glass fiber (with a non-circular cross-section of 7 ⁇ 28 ⁇ m cross-section) is marketed by the company Nitto Boseki.
- the PAU and PA12 are produced by the applicant.
- Calcium stearate is marketed by the company Greven.
- Licowax E is marketed by the company Clariant.
- Irganox 1010 is marketed by BASF
- PA66 (Stabamid reference 25AE1) is marketed by Domo Chemicals. [Table 2] lOOxlOOxlmm, men weak after injection 1% 1%
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Abstract
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Priority Applications (5)
Application Number | Priority Date | Filing Date | Title |
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US18/558,856 US20240228748A1 (en) | 2021-05-05 | 2022-04-29 | Compositions based on polyamides and glass fibers and use thereof in the medical field |
CN202280032670.4A CN117242132A (zh) | 2021-05-05 | 2022-04-29 | 基于聚酰胺和玻璃纤维的组合物及其在医学领域中的用途 |
EP22728264.7A EP4334388A1 (fr) | 2021-05-05 | 2022-04-29 | Compositions a base de polyamides et de fibres de verre et leur utilisation dans le domaine du medical |
JP2023567944A JP2024516038A (ja) | 2021-05-05 | 2022-04-29 | ポリアミド及びガラス繊維に基づく組成物並びに医療分野におけるその使用 |
KR1020237040638A KR20240004622A (ko) | 2021-05-05 | 2022-04-29 | 폴리아미드 및 유리 섬유에 기반한 조성물 및 의료 분야에서의 이의 용도 |
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FR2104729A FR3122660B1 (fr) | 2021-05-05 | 2021-05-05 | Compositions a base de polyamides et de fibres de verre et leur utilisation dans le domaine du medical |
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EP (1) | EP4334388A1 (fr) |
JP (1) | JP2024516038A (fr) |
KR (1) | KR20240004622A (fr) |
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Publication number | Priority date | Publication date | Assignee | Title |
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US20170107337A1 (en) * | 2006-12-28 | 2017-04-20 | Ems-Chemie Ag | Polyamide molding materials reinforced with glass fibers and injection molded parts thereof |
WO2019058077A1 (fr) * | 2017-09-25 | 2019-03-28 | Arkema France | Utilisation d'une composition de copolyamide comme matrice de materiau charge avec des fibres de verre a section circulaire pour limiter le gauchissement |
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2021
- 2021-05-05 FR FR2104729A patent/FR3122660B1/fr active Active
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2022
- 2022-04-29 EP EP22728264.7A patent/EP4334388A1/fr active Pending
- 2022-04-29 WO PCT/FR2022/050828 patent/WO2022234223A1/fr active Application Filing
- 2022-04-29 CN CN202280032670.4A patent/CN117242132A/zh active Pending
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Publication number | Priority date | Publication date | Assignee | Title |
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US20170107337A1 (en) * | 2006-12-28 | 2017-04-20 | Ems-Chemie Ag | Polyamide molding materials reinforced with glass fibers and injection molded parts thereof |
WO2019058077A1 (fr) * | 2017-09-25 | 2019-03-28 | Arkema France | Utilisation d'une composition de copolyamide comme matrice de materiau charge avec des fibres de verre a section circulaire pour limiter le gauchissement |
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JP2024516038A (ja) | 2024-04-11 |
KR20240004622A (ko) | 2024-01-11 |
US20240228748A1 (en) | 2024-07-11 |
FR3122660A1 (fr) | 2022-11-11 |
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