WO2023275463A1 - Compositions de soufflage moulage a base de polyamides branches et leurs utilisations - Google Patents
Compositions de soufflage moulage a base de polyamides branches et leurs utilisations Download PDFInfo
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- WO2023275463A1 WO2023275463A1 PCT/FR2022/051246 FR2022051246W WO2023275463A1 WO 2023275463 A1 WO2023275463 A1 WO 2023275463A1 FR 2022051246 W FR2022051246 W FR 2022051246W WO 2023275463 A1 WO2023275463 A1 WO 2023275463A1
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- WIPO (PCT)
- Prior art keywords
- composition
- blow molding
- weight
- equal
- compounding
- Prior art date
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- 239000000203 mixture Substances 0.000 title claims abstract description 159
- 238000000071 blow moulding Methods 0.000 title claims abstract description 42
- 239000004952 Polyamide Substances 0.000 title description 43
- 229920002647 polyamide Polymers 0.000 title description 43
- 229920002732 Polyanhydride Polymers 0.000 claims abstract description 48
- 239000006085 branching agent Substances 0.000 claims abstract description 41
- 238000013329 compounding Methods 0.000 claims abstract description 40
- 229920006177 crystalline aliphatic polyamide Polymers 0.000 claims abstract description 34
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 33
- 229920001228 polyisocyanate Polymers 0.000 claims abstract description 33
- 239000005056 polyisocyanate Substances 0.000 claims abstract description 33
- 229910052799 carbon Inorganic materials 0.000 claims abstract description 31
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims abstract description 30
- 125000004433 nitrogen atom Chemical group N* 0.000 claims abstract description 30
- 239000000654 additive Substances 0.000 claims abstract description 23
- 238000001125 extrusion Methods 0.000 claims abstract description 22
- 230000000996 additive effect Effects 0.000 claims abstract description 21
- 239000010410 layer Substances 0.000 claims description 40
- 229910052739 hydrogen Inorganic materials 0.000 claims description 28
- 239000001257 hydrogen Substances 0.000 claims description 28
- 239000000470 constituent Substances 0.000 claims description 26
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 24
- 229920000642 polymer Polymers 0.000 claims description 23
- 239000004609 Impact Modifier Substances 0.000 claims description 19
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- 238000000034 method Methods 0.000 claims description 8
- 238000003860 storage Methods 0.000 claims description 8
- 238000004519 manufacturing process Methods 0.000 claims description 7
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- 239000000356 contaminant Substances 0.000 claims description 6
- 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 5
- 238000009826 distribution Methods 0.000 claims description 4
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- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 claims description 4
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- 230000008569 process Effects 0.000 claims description 3
- ODZHLDRQCZXQFQ-UHFFFAOYSA-N chlorferron Chemical compound C1=C(O)C=CC2=C1OC(=O)C(Cl)=C2C ODZHLDRQCZXQFQ-UHFFFAOYSA-N 0.000 claims description 2
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- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical class C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 9
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 8
- RLSSMJSEOOYNOY-UHFFFAOYSA-N m-cresol Chemical compound CC1=CC=CC(O)=C1 RLSSMJSEOOYNOY-UHFFFAOYSA-N 0.000 description 8
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- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
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- 238000011955 best available control technology Methods 0.000 description 6
- 239000003054 catalyst Substances 0.000 description 6
- HQQADJVZYDDRJT-UHFFFAOYSA-N ethene;prop-1-ene Chemical group C=C.CC=C HQQADJVZYDDRJT-UHFFFAOYSA-N 0.000 description 6
- 238000005470 impregnation Methods 0.000 description 6
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- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 6
- RNFJDJUURJAICM-UHFFFAOYSA-N 2,2,4,4,6,6-hexaphenoxy-1,3,5-triaza-2$l^{5},4$l^{5},6$l^{5}-triphosphacyclohexa-1,3,5-triene Chemical compound N=1P(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP=1(OC=1C=CC=CC=1)OC1=CC=CC=C1 RNFJDJUURJAICM-UHFFFAOYSA-N 0.000 description 5
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 5
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- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 5
- 125000004432 carbon atom Chemical group C* 0.000 description 5
- 229910052802 copper Inorganic materials 0.000 description 5
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- 238000005259 measurement Methods 0.000 description 5
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- VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical compound CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 description 4
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- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-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
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-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
- 150000001244 carboxylic acid anhydrides Chemical class 0.000 description 4
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- 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
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- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-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
- ACVYVLVWPXVTIT-UHFFFAOYSA-N phosphinic acid Chemical compound O[PH2]=O ACVYVLVWPXVTIT-UHFFFAOYSA-N 0.000 description 4
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- CXMXRPHRNRROMY-UHFFFAOYSA-N sebacic acid Chemical compound OC(=O)CCCCCCCCC(O)=O CXMXRPHRNRROMY-UHFFFAOYSA-N 0.000 description 4
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- 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
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- 150000003628 tricarboxylic acids Chemical class 0.000 description 4
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- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 3
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- YHMYGUUIMTVXNW-UHFFFAOYSA-N 1,3-dihydrobenzimidazole-2-thione Chemical compound C1=CC=C2NC(S)=NC2=C1 YHMYGUUIMTVXNW-UHFFFAOYSA-N 0.000 description 2
- PWGJDPKCLMLPJW-UHFFFAOYSA-N 1,8-diaminooctane Chemical compound NCCCCCCCCN PWGJDPKCLMLPJW-UHFFFAOYSA-N 0.000 description 2
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- DXNCZXXFRKPEPY-UHFFFAOYSA-N tridecanedioic acid Chemical compound OC(=O)CCCCCCCCCCCC(O)=O DXNCZXXFRKPEPY-UHFFFAOYSA-N 0.000 description 2
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Classifications
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- B29C49/00—Blow-moulding, i.e. blowing a preform or parison to a desired shape within a mould; Apparatus therefor
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- B32—LAYERED PRODUCTS
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- B32B1/00—Layered products having a non-planar shape
- B32B1/08—Tubular products
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- 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
- B32B27/12—Layered products comprising a layer of synthetic resin next to a fibrous or filamentary layer
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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
- B32B27/18—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
- B32B27/34—Layered products comprising a layer of synthetic resin comprising polyamides
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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
- 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
- C08G69/08—Polyamides derived from amino-carboxylic acids or from polyamines and polycarboxylic acids derived from amino-carboxylic acids
- C08G69/14—Lactams
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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
- 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
- C08G69/36—Polyamides derived from amino-carboxylic acids or from polyamines and polycarboxylic acids derived from amino acids, polyamines and 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
- C08K5/00—Use of organic ingredients
- C08K5/04—Oxygen-containing compounds
- C08K5/15—Heterocyclic compounds having oxygen in the ring
- C08K5/151—Heterocyclic compounds having oxygen in the ring having one oxygen atom in the ring
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L37/00—Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a heterocyclic ring containing oxygen; Compositions of derivatives of such polymers
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L77/00—Compositions of polyamides obtained by reactions forming a carboxylic amide link in the main chain; Compositions of derivatives of such polymers
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- 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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- 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
- B32B2307/704—Crystalline
-
- 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
- B32B2597/00—Tubular articles, e.g. hoses, pipes
-
- 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
- B32B5/00—Layered products characterised by the non- homogeneity or physical structure, i.e. comprising a fibrous, filamentary, particulate or foam layer; Layered products characterised by having a layer differing constitutionally or physically in different parts
- B32B5/02—Layered products characterised by the non- homogeneity or physical structure, i.e. comprising a fibrous, filamentary, particulate or foam layer; Layered products characterised by having a layer differing constitutionally or physically in different parts characterised by structural features of a fibrous or filamentary layer
- B32B5/024—Woven fabric
Definitions
- TITLE BLOW MOLDING COMPOSITIONS BASED ON BRANCHED POLYAMIDES AND THEIR
- the present invention relates to blow molding or extrusion compositions, in particular blow molding compositions, based on branched polyamide and their use for the preparation of single-layer or multi-layer tubular structures intended for the transport, distribution or storage of hydrogen and the process for preparing said structures.
- electric or hybrid vehicles comprising a battery aim to gradually replace thermal vehicles, such as gasoline or diesel vehicles.
- thermal vehicles such as gasoline or diesel vehicles.
- the battery is a relatively complex constituent of the vehicle. Depending on where the battery is located in the vehicle, it may need to be protected from impact and the external environment, which may be extreme temperatures and varying humidity. It is also necessary to avoid any risk of flames.
- the electric vehicle still suffers today from several problems, namely battery autonomy, the use in these batteries of rare earths whose resources are not inexhaustible, as well as a problem of electricity production in different countries to be able to recharge the batteries.
- Hydrogen therefore represents an alternative to the electric battery since hydrogen can be transformed into electricity by means of a fuel cell and thus power electric vehicles.
- Hydrogen tanks generally consist of a metal envelope (liner) which must prevent the permeation of hydrogen.
- This first casing must itself be protected by a second casing (in general made of composite materials) intended to withstand the internal pressure of the reservoir (for example, 700 bars) and resistant to possible shocks or sources of heat.
- the valve system must also be safe.
- Application EP 0495363 relates to polyamide compositions based on a polyamide alloy (PA) and special olefin-acid anhydride copolymers and their use for the production of shaped hollow bodies.
- PA polyamide alloy
- special olefin-acid anhydride copolymers and their use for the production of shaped hollow bodies.
- compositions are too fluid to allow large reservoirs to be extruded.
- PA 6 polyamide 6
- these structures are based on PA 6 (poor resistance to zinc chloride and fragile when cold) and therefore are not compatible with reservoir applications for automotive fluids such as hydrogen.
- Application FR2996556 relates to a liner for the storage of gas, in particular compressed natural gas (CNG), methane or hydrogen comprising a composition based on branched polyamide and impact modifier.
- CNG compressed natural gas
- methane methane or hydrogen
- compositions exemplified are based on PA6 and therefore present the same problems as above.
- the compositions contain too much impact modifier, which creates a risk of cavitation (blistering).
- Application CA3101967 relates to polyamide compositions for blow molding based on PA 6 and impact modifier and consequently they present the same problems as above.
- Application EP1352934 describes metal surfaces coated with a layer based on polyamide consisting of a mixture of polyamide and of a polyolefin functionalized with an unsaturated carboxylic acid anhydride.
- Application US2005/228145 describes a transparent multilayer structure comprising a first layer of polyamide consisting of a mixture of polyamide and of a polyolefin functionalized with maleic anhydride.
- Application FR3078132 describes a flexible tubular structure comprising a layer comprising a mixture of polyamide and of a polyolefin functionalized with an anhydride.
- Application EP2649130 describes a liner for storing gas comprising a composition comprising a mixture of polyamide and of a polyolefin functionalized with an anhydride.
- compositions for blow molding or extrusion, in particular blow molding, comprising by weight: a) from 88 to 99.95% , in particular from 89 to 99.9%, in particular from 93 to 99.9% of at least one semi-crystalline aliphatic polyamide having a number of carbon per nitrogen atom greater than or equal to 7, in particular greater than or equal to 8, b) from 0.05% to 10%, in particular from 0.1 to 9%, in particular from 0.1 to 5% by weight of at least one branching agent chosen from polyepoxy, polyanhydrides and polyisocyanates, in particular maleic polyanhydrides and polyepoxy, c) from 0 to 2% of at least one additive, in particular from 0.1 to 2%, the composition exhibiting after compounding a melt viscosity of between 10,000 at 300,000 Pa.s, preferably from 15,000 to 220,000 Pa.s, as measured in plane-plane geometry according to standard 6721-10
- compositions which, after compounding, have a viscosity at molten state in a range allowing extrusion-blow molding or extrusion, in particular extrusion-blow molding for the constitution of a monolayer or multilayer tubular structure intended for the transport, distribution or storage of hydrogen.
- compositions of the invention are good dimensional stability, that is to say low water uptake, good resistance to zinc chloride.
- monolayer or multilayer tubular structure a reservoir comprising or consisting of one or more layers.
- the monolayer or multilayer structure in the present invention also designates a pipe or a tube intended for transporting hydrogen to the tank or from the tank to the fuel cell and which comprises or consists of one or more layers.
- non-functionalized impact modifiers are excluded from said composition.
- non-functionalized impact modifiers and low-functionalized impact modifiers are excluded from said composition.
- low-functionalized impact modifier is meant an impact modifier having an equivalent weight per reactive function greater than 10,000 g/mol, advantageously greater than 6000 g/mol.
- non-functionalized elastomers are excluded from said composition.
- plasticizers are excluded from said composition.
- impact modifier a polymer with a modulus lower than that of the resin, exhibiting good adhesion with the matrix, so as to dissipate the cracking energy.
- the impact modifier is advantageously made up of a polymer having a flexural modulus of less than 100 MPa measured according to the ISO 178 standard and a Tg of less than 0° C. (measured according to the 11357-2 standard at the level of the inflection point of the DSC thermogram ), in particular a polyolefin.
- the polyolefin of the impact modifier can be functionalized or non-functionalized or be a mixture of at least one functionalized and/or at least one non-functionalized.
- the polyolefin has been designated by (B) and functionalized polyolefins (B1) and non-functionalized polyolefins (B2) have been described below.
- a non-functionalized polyolefin (B2) is conventionally a homopolymer or copolymer of alpha olefins or diolefins, such as, for example, ethylene, propylene, butene-1, octene-1, butadiene.
- alpha olefins or diolefins such as, for example, ethylene, propylene, butene-1, octene-1, butadiene.
- LDPE low density polyethylene
- HDPE linear low density polyethylene
- LLDPE linear low density polyethylene, or linear low density polyethylene
- VLDPE very low density polyethylene, or very low density polyethylene
- metallocene polyethylene metallocene polyethylene
- ethylene/alpha-olefin copolymers such as ethylene/propylene, EPR (abbreviation of ethylene-propylene-rubber) and ethylene/propylene/diene (EPDM).
- EPR abbreviation of ethylene-propylene-rubber
- EPDM ethylene/propylene/diene
- SEBS styrene/ethylene-butene/styrene
- SBS styrene/butadiene/styrene
- SIS styrene/isoprene/styrene
- SEPS styrene/ethylene-propylene/styrene
- the functionalized polyolefin (B1) can be a polymer of alpha olefins having reactive units (the functionalities); such reactive units are acid, anhydride or epoxy functions.
- polyolefins (B2) grafted or co- or ter-polymerized with unsaturated epoxides such as glycidyl (meth)acrylate, or with carboxylic acids or the corresponding salts or esters such as (meth)acrylic acid (the latter possibly being totally or partially neutralized by metals such as Zn, etc.) or else by carboxylic acid anhydrides such as maleic anhydride.
- unsaturated epoxides such as glycidyl (meth)acrylate
- carboxylic acids or the corresponding salts or esters such as (meth)acrylic acid (the latter possibly being totally or partially neutralized by metals such as Zn, etc.) or else by carboxylic acid anhydrides such as maleic anhydride.
- a functionalized polyolefin is, for example, a PE/EPR mixture, the weight ratio of which can vary widely, for example from 40/60 to 90/10, said mixture being co-grafted with an anhydride, in particular maleic anhydride, according to a degree of grafting for example from 0.01 to 5% by weight, advantageously from 2.8 to 5% by weight.
- the functionalized polyolefin (B1) can be chosen from the following (co)polymers, grafted with maleic anhydride or glycidyl methacrylate, in which the degree of grafting is for example from 0.01 to 5% by weight:
- ethylene/alpha-olefin copolymers such as ethylene/propylene, EPR (abbreviation of ethylene-propylene-rubber) and ethylene/propylene/diene (EPDM).
- EPR abbreviation of ethylene-propylene-rubber
- EPDM ethylene/propylene/diene
- SEBS styrene/ethylene-butene/styrene
- SBS styrene/butadiene/styrene
- SIS styrene/isoprene/styrene
- SEPS styrene/ethylene-propylene/styrene
- alkyl (meth)acrylate copolymers containing up to 40% by weight of alkyl (meth)acrylate;
- the functionalized polyolefin (B1) can also be chosen from ethylene/propylene copolymers with a majority of propylene grafted with maleic anhydride then condensed with monoamine polyamide (or a polyamide oligomer) (products described in EP-A-0342066) .
- the functionalized polyolefin (B1) can also be a co- or ter-polymer of at least the following units: (1) ethylene, (2) alkyl (meth)acrylate or saturated carboxylic acid vinyl ester and (3) anhydride such as maleic anhydride or (meth)acrylic acid or epoxy such as glycidyl (meth)acrylate.
- anhydride such as maleic anhydride or (meth)acrylic acid or epoxy such as glycidyl (meth)acrylate.
- the ethylene preferably represents at least 60% by weight and in which the ter monomer (the function) represents, for example, from 0.1 to 13% by weight of the copolymer:
- the (meth)acrylic acid can be salified with Zn or Li.
- alkyl (meth)acrylate in (B1) or (B2) denotes C1 to C8 alkyl methacrylates and acrylates, and may be chosen from methyl acrylate, ethyl acrylate , n-butyl acrylate, isobutyl acrylate, ethyl-2-hexyl acrylate, cyclohexyl acrylate, methyl methacrylate and ethyl methacrylate.
- the aforementioned polyolefins (B1) can also be crosslinked by any appropriate process or agent (diepoxy, diacid, peroxide, etc.); the term functionalized polyolefin also includes mixtures of the aforementioned polyolefins with a difunctional reagent such as diacid, dianhydride, diepoxy, etc. capable of reacting with these or mixtures of at least two functionalized polyolefins capable of reacting with each other.
- a difunctional reagent such as diacid, dianhydride, diepoxy, etc.
- copolymers mentioned above, (B1) and (B2) can be randomly or block copolymerized and have a linear or branched structure.
- the molecular weight, the MFI index, the density of these polyolefins can also vary to a large extent, which those skilled in the art will appreciate.
- MFI short for Melt Flow Index, is the Melt Flow Index. It is measured according to the ASTM 1238 or ISO 1133:2011 standard.
- the non-functionalized polyolefins (B2) are chosen from polypropylene homopolymers or copolymers and any homopolymer of ethylene or copolymer of ethylene and a comonomer of the higher alpha olefinic type such as butene, hexene, octene or 4-methyl 1-pentene.
- PP high-density PE
- medium-density PE linear low-density PE
- low-density PE very low-density PE.
- polyethylenes are known to those skilled in the art as being produced according to a “radical” process, according to a catalysis of the “Ziegler” type or, more recently, according to a so-called “metallocene” catalysis.
- the functionalized polyolefins (B1) are chosen from any polymer comprising alpha olefin units and units carrying polar reactive functions such as epoxy, carboxylic acid or carboxylic acid anhydride functions.
- polymers mention may be made of the terpolymers of ethylene, of alkyl acrylate and maleic anhydride or glycidyl methacrylate such as Lotader ® from SK global Chemical or polyolefins grafted with maleic anhydride such as Orevac ® from SK global Chemical as well as terpolymers of ethylene, acrylate alkyl and (meth)acrylic acid.
- the blow molding or extrusion composition in particular blow molding, comprises from 88 to 99.95%, in particular from 89 to 99.8% of at least one semi-crystalline aliphatic polyamide having a carbon number per nitrogen atom greater than or equal to 7, in particular greater than or equal to 8.
- the polyamide can be a homopolyamide or a copolyamide or a mixture thereof.
- Said semi-crystalline aliphatic polyamide is derived from a repeating unit obtained by polycondensation: of at least one C9 to C18 amino acid, preferably CIO to C18, more preferably CIO to C12, or at least one C9 lactam to C18, preferentially in CIO to C18, more preferentially in CIO to C12, or of at least one diamine Ca in C4-C36, preferentially C6-C18, preferentially C6-C12, more preferentially C10-C12, with at least one acid C4-C36, preferably C6-C18, preferably C6-C12, more preferably C10-C12 dicarboxylic acid Cb, or a mixture thereof, provided that the number of carbon atoms per nitrogen atom of the repeating unit is greater than or equal to 7, in particular greater than or equal to 8.
- a C9 to C18 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 acid N-heptyl-ll-aminoundecanoic acid.
- a C9 to C18 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-heptamethylenediamine, 1,8-octamethylenediamine, 1,9-nonamethylenediamine, 1,10-decamethylenediamine, 1,11-undecamethylenediamine, 1,12-dodecamethylenediamine, 1,13-tridecamethylenediamine, 1,14-tetradecamethylenediamine, 1,16-hexadecamethylenediamine and 1, 18-octadecamethylenediamine, 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-heptamethylenediamine, 1,8-octamethylenediamine, 1,9-nonamethylenediamine, 1,10-decamethylenediamine , 1,11-undecamethylenediamine, 1,12-dodecamethylenediamine, 1,13-tridecamethylenediamine, 1,14-tetradecamethylenediamine, 1,16-hexadecamethylenediamine and 1,18-octadecamethylenediamine.
- Said at least one Cb C4 to C36 dicarboxylic acid may 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 fatty acids .
- said at least one Cb dicarboxylic acid is C6 to C18 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.
- said semi-crystalline aliphatic polyamide is chosen from PA610, PA612, PA 614, PA 10, PAU and PA12, in particular PA610, PA612 and PAU.
- said semi-crystalline aliphatic polyamide is a mixture of two semi-crystalline aliphatic polyamides having a number of carbon per nitrogen atom greater than or equal to 7, in particular greater than or equal to 8, in a range of proportion by weight of 5/95 to 95/5.
- the polyamide has a concentration at the end of the amine chains of 5 to 60 peq/g, very advantageously between 10 and 50 peq/g.
- the polyamide has a concentration at the end of the acid chains comprised from 5 to 60 peq/g, very advantageously from 10 to 50 peq/g.
- the ends of the amine chains are measured according to the following method: a sample of polyamide is dissolved in metacresol. Then, this sample is assayed by potentiometry with a 0.02N perchloric acid solution. The ends of acid chains are measured according to the following method. A sample of polyamide is dissolved in benzyl alcohol. Then, this sample is assayed by potentiometry with a solution of tetrabutylammonium hydroxide at 0.02N.
- the polyamide according to the invention has an inherent viscosity in m-cresol greater than 1.45, advantageously greater than 1.55, very advantageously greater than 1.6 as determined according to standard ISO 307:2007 but using m -cresol instead of sulfuric acid, a temperature of 20°C and a concentration of 0.5% by weight.
- the branching agent is present in the composition from 0.05% to 10%, in particular from 0.1 to 9%, in particular from 0.1 to 5% by weight and is chosen from polyepoxy, polyanhydrides, and polyisocyanates in particular maleic polyanhydrides and polyepoxy.
- the branching agent is present in the composition at 0.1 to 2% by weight.
- the branching agent may be an impact modifier, in particular a polyolefin functionalized or different from an impact modifier.
- the impact modifier is different from the impact modifier. That is to say, it has a Tg greater than -30°C, very advantageously greater than 0°C.
- the equivalent weight per reactive function of the branching agent is comprised from 100 to 10000 g/mol, advantageously from 120 to 6000 g/mol, more advantageously from 140 to 3300 g/mol.
- said branching agent has an average functionality in terms of epoxy, anhydride or isocyanate functions of between 1.8 and 200, preferably between 2.1 and 150.
- the molar mass of the branching agents is between 300 and 120,000 g/mol, preferably between 400 and 100,000 g/mol.
- the molar mass is measured by gas chromatography (GPC).
- the equivalent weight per reactive functions of the branching agents is measured as follows: Isocyanates: The equivalent weight per isocyanate function is measured according to the AFNOR standard referenced NF T52-132.
- Epoxides The equivalent weight per epoxy function is measured according to standard ASTM D1652-11 (2019).
- Maleic anhydride The mass content of maleic anhydride is measured by FTIR using the method of De Roovers et al. [J Polym Sci, Part A: Polym Chem 1995;33:829] The equivalent weight is often given by the supplier on the TDS.
- the average functionality is calculated by dividing the molar mass measured by GPC by the average equivalent weight.
- the polyepoxy can be copolymers made from glycidyl maleic anhydride (GMA) or any other monomer comprising an epoxy function.
- GMA glycidyl maleic anhydride
- Examples of commercial polyepoxy are, for example, Xibond® 920 marketed by Polyscope or Joncryl® ADR 4400 marketed by BASF or lotader® AX 8900 marketed by SK Chemical.
- the polyanhydrides can be copolymers comprising a copolymerized or grafted anhydride, such as maleic anhydride or itaconic anhydride.
- polyanhydrides are maleic polyanhydrides.
- the other monomer of the copolymers comprising a copolymerized anhydride can be a vinyl aromatic monomer, such as styrene or styrenes in which the aromatic ring contains a halogen or an alkyl substituent.
- the other monomer of the copolymers comprising a copolymerized anhydride can be a vinyl monomer, such as ethylene or octadecene.
- maleic polyanhydrides are copolymers of styrene and maleic anhydride.
- Examples of commercial maleic polyanhydrides are for example Xibond ® 125 (copolymer of styrene and maleic anhydride) marketed by Polyscope or Orevac IM 800 marketed by SK Chemicals or PA 18 (copolymer of 1-octadecene and anhydride maleic acid) marketed by Chevron Phillips Chemical Company.
- the polyisocyanates are preferably oligomers of isocyanates such as isocyanurates or allophanates.
- Examples of commercial polyisocyanates are for example Desmodur 3300 marketed by Covestro.
- the additives may be present up to 2% by weight relative to the total weight of the composition, in particular they are present from 0.1 to 2% by weight relative to the total weight of the composition.
- the additive can be chosen from a catalyst, an antioxidant, a heat stabilizer, a UV stabilizer, a light stabilizer, a lubricant, a flame retardant, a nucleating agent, a chain extender and a colorant.
- the additive is selected from catalyst, antioxidant, heat stabilizer, UV stabilizer, light stabilizer, lubricant, flame retardant, chain extender, and colorant.
- catalyst denotes a polycondensation catalyst such as an inorganic or organic acid.
- the proportion by weight of catalyst is comprised from approximately 50 ppm to approximately 5000 ppm, in particular from approximately 100 to approximately 3300 ppm relative to the total weight of the composition.
- the catalyst is chosen from phosphoric acid (H3P04), phosphorous acid (H3P03), hypophosphorous acid (H3P02), or a mixture of these.
- the antioxidant can in particular be an antioxidant based on a copper complex of 0.05 to 5% by weight, preferably 0.05 to 1% by weight, preferably 0.1 to 1%.
- copper complex denotes in particular a complex between a monovalent or divalent salt of copper with an organic or inorganic acid and an organic ligand.
- the copper salt is chosen from cupric salts (Cu(II)) of hydrogen halide, cuprous salts (Cu(II)) of hydrogen halide and salts of aliphatic carboxylic acids.
- the copper salts are chosen from CuCl, CuBr, Cul, CuCN, CuCl2, Cu(OAc)2, cupric stearate.
- Said copper-based complex may further comprise a ligand chosen from phosphines, in particular triphenylphosphines, mercaptobenzimidazole, EDTA, acetylacetonate, glycine, ethylene diamine, oxalate, diethylene diamine, triethylene tetraamine, pyridine, tetrabromobisphenyl-A, tetrabisphenyl-A derivatives, such as epoxy derivatives, and chloro dimethanedibenzo(a,e)cyclooctene derivatives and mixtures thereof. diphosphone and dipyridyl or their mixtures, in particular triphenylphosphine and/or mercaptobenzimidazole.
- phosphines in particular triphenylphosphines, mercaptobenzimidazole, EDTA, acetylacetonate, glycine, ethylene diamine, oxalate, diethylene diamine
- Phosphines refer to alkylphosphines, such as tributylphosphine or arylphosphines such as triphenylphosphine (TPP).
- alkylphosphines such as tributylphosphine or arylphosphines such as triphenylphosphine (TPP).
- TPP triphenylphosphine
- said ligand is triphenylphosphine.
- the amount of copper in the composition of the invention is between 10 ppm to 1000 ppm by weight, especially from 50 to 150 ppm relative to the total weight of the composition.
- said copper-based complex further comprises a halogenated organic compound.
- the halogenated organic compound can be any halogenated organic compound.
- said halogenated organic compound is a bromine-based compound and/or an aromatic compound.
- said aromatic compound is chosen in particular from decabromediphenyl, decabromodiphenyl ether, bromo or chlorostyrene oligomers and polydibromostyrene.
- said halogenated organic compound is a bromine-based compound.
- Said halogenated organic compound is added to the composition in a proportion of 50 to 30,000 ppm by weight of halogen relative to the total weight of the composition, in particular from 100 to 10,000 in particular from 500 to 1500 ppm.
- the copper:halogen molar ratio is comprised from 1:1 to 1:3000, in particular from 1:2 to 1:100.
- said ratio is comprised from 1:1.5 to 1:15.
- the copper complex antioxidant is provided.
- the thermal stabilizer can be an organic stabilizer or more generally a combination of organic stabilizers, such as a primary antioxidant of the phenol type (for example of the type of that of irganox 245 or 1098 or 1010 from the company Ciba), a secondary antioxidant of phosphite type.
- a primary antioxidant of the phenol type for example of the type of that of irganox 245 or 1098 or 1010 from the company Ciba
- a secondary antioxidant of phosphite type such as a primary antioxidant of the phenol type (for example of the type of that of irganox 245 or 1098 or 1010 from the company Ciba), a secondary antioxidant of phosphite type.
- the UV stabilizer can be a HALS, which means Hindered Amine Light Stabilizer or an anti-UV (for example Tinuvin 312 from the company Ciba).
- the light stabilizer can be of the hindered amine type (for example Tinuvin 770 from the company Ciba), a phenolic or phosphorus-based stabilizer.
- the lubricant can be a fatty acid type lubricant such as stearic acid.
- the flame retardant may be a halogen-free flame retardant, as described in US 2008/0274355 and in particular a phosphorus-based flame retardant, for example a metal salt chosen from a metal salt of phosphinic acid, in particular salts dialkyl phosphinate, in particular diethyl phosphinate aluminum salt or diethyl phosphinate aluminum, a metal salt of diphosphinic acid, a mixture of flame retardant agent based on aluminum phosphinate and a nitrogen synergist or a mixture of an aluminum phosphinate-based flame retardant and a phosphorus synergist, a polymer containing at least one metal salt of phosphinic acid, in particular on an ammonium base, such as an ammonium polyphosphate, sulfamate or pentaborate, or on a melamine base such as melamine, melamine salts, melamine pyrophosphates and melamine cyanurates, or on
- the nucleating agent can be silica, alumina, clay or talc, in particular talc.
- chain regulators are monoamines, monocarboxylic acids, diamines, triamines, dicarboxylic acids, tricarboxylic acids, tetraamines, tetracarboxylic acids and, oligoamines or oligocarboxylic acids having respectively in each case 5 to 8 amino or carboxy groups and in particular dicarboxylic acids, tricarboxylic acids or a mixture of dicarboxylic acids and tricarboxylic acids.
- dodecanedicarboxylic acid in the form of the dicarboxylic acid and trimellitic acid as the tricarboxylic acid.
- the blow molding or extrusion composition comprises by weight: a) from 88 to 99.95%, in particular from 89 to 99.9%, in particular from 93 to 99.9% of at least one semi-crystalline aliphatic polyamide having a number of carbon per nitrogen atom greater than or equal to 7, in particular greater than or equal to 8, b) from 0.05% to 10%, in particular from 0.1 to 9%, in particular from 0.1 to 5% by weight of at least one branching agent chosen from polyepoxy, polyanhydrides and polyisocyanates, in particular maleic polyanhydrides and polyepoxy.
- composition having, after compounding, a viscosity in the molten state of between 10,000 and 300,000 Pa.s, preferentially from 15,000 to 220,000 Pa.s, as measured in plane-plane geometry according to ISO 6721-10:2015 at a temperature of 250°C, a frequency of 0.292 rad/s and a deformation of 2%, the sum of the constituents a) + b) + c) making 100% by weight.
- the blow molding or extrusion composition in particular blow molding, consists by weight of: a) from 88 to 99.95%, in particular from 89 to 99.9%, in particular from 93 to 99.9% of at least one semi-crystalline aliphatic polyamide having a carbon number per nitrogen atom greater than or equal to 7, in particular greater than or equal to 8, b) from 0.05% to 10%, in particular from 0.1 to 9%, especially from 0.1 to 5% by weight of at least one branching agent chosen from polyepoxy, polyanhydrides and polyisocyanates, in particular polymaleic anhydrides and polyepoxy.
- composition having, after compounding, a viscosity in the molten state of between 10,000 and 300,000 Pa.s, preferentially from 15,000 to 220,000 Pa.s, as measured in plane-plane geometry according to ISO 6721-10:2015 at a temperature of 250°C, a frequency of 0.292 rad/s and a deformation of 2%, the sum of the constituents a) + b) + c) making 100% by weight.
- said composition comprises: a) from 88 to 99.95% of at least one semi-crystalline aliphatic polyamide having a number of carbon per nitrogen atom greater than or equal to 7, in particular greater than or equal to 8, b) from 0.05% to 10% by weight of at least one branching agent chosen from polyepoxy, polyanhydrides and polyisocyanates, in particular polymaleic anhydrides and polyepoxy, the composition having, after compounding, a viscosity of the molten state comprised from 10,000 to 300,000 Pa.s, preferably from 15,000 to 220,000 Pa.s, as measured in plane-plane geometry according to standard ISO 6721-10:2015 at a temperature of 250°C, a frequency of 0.292 rad/s and a deformation of 2%, the sum of the constituents a) + b) making 100% by weight.
- branching agent chosen from polyepoxy, polyanhydrides and polyisocyanates, in particular polymaleic anhydrides and polyepoxy
- said composition consists of: a) from 88 to 99.95% of at least one semi-crystalline aliphatic polyamide having a number of carbon per nitrogen atom greater than or equal to 7, in particular greater than or equal to 8, b) from 0.05% to 10% by weight of at least one branching agent chosen from polyepoxy, polyanhydrides and polyisocyanates, in particular polymaleic anhydrides and polyepoxy, the composition having after compounding a melt viscosity of from 10,000 to 300,000 Pa.s, preferably from 15,000 to 220,000 Pa.s, as measured in plane-plane geometry according to standard ISO 6721-10:2015 at a temperature of 250°C, a frequency of 0.292. rad/s and a deformation of 2%, the sum of the constituents a) + b) making 100% by weight.
- branching agent chosen from polyepoxy, polyanhydrides and polyisocyanates, in particular polymaleic anhydrides and polyepoxy
- said composition comprises: a) from 88 to 99.85% of at least one semi-crystalline aliphatic polyamide having a number of carbon per nitrogen atom greater than or equal to 7, in particular greater than or equal to 8, b) from 0.05% to 10% by weight of at least one branching agent chosen from polyepoxy, polyanhydrides and polyisocyanates, in particular maleic polyanhydrides and polyepoxy c) from 0.1 to 2% of at least one additive, the composition having, after compounding, a viscosity in the molten state of between 10,000 and 300,000 Pa.s, preferably from 15,000 to 220,000 Pa.s, as measured in plane-plane geometry at a temperature of 250° C., a frequency of 0.292 rad/s and a strain of 2%, the sum of the constituents a) + b) + c) making 100% by weight.
- branching agent chosen from polyepoxy, polyanhydrides and polyisocyanates, in particular maleic polyanhydrides and polyepoxy
- said composition consists of: a) from 88 to 99.85% of at least one semi-crystalline aliphatic polyamide having a number of carbon per nitrogen atom greater than or equal to 7, in particular greater than or equal to 8, b) from 0.05% to 10% by weight of at least one branching agent chosen from polyepoxy, polyanhydrides and polyisocyanates, in particular maleic polyanhydrides and polyepoxy, c) from 0, 1 to 2% of at least one additive, the composition exhibiting, after compounding, a viscosity in the molten state of between 10,000 and 300,000 Pa.s, preferably from 15,000 to 220,000 Pa.s, as measured in plane-plane geometry according to ISO 6721-10:2015 at a temperature of 250°C, a frequency of 0.292 rad/s and a deformation of 2%, the sum of the constituents a) + b) + c) making 100% by weight.
- branching agent chosen from polyepoxy, polyanhydrides and polyisocyanates, in
- said composition comprises: a) from 89 to 99.9% of at least one semi-crystalline aliphatic polyamide having a number of carbon per nitrogen atom greater than or equal to 7, in particular greater than or equal to 8, b) from 0.1 to 9%, by weight of at least one branching agent chosen from polyepoxy, polyanhydrides and polyisocyanates, in particular maleic polyanhydrides and polyepoxy, c) from 0 to 2% of at least one additive, in particular from 0.1 to 2%, the composition exhibiting, after compounding, a viscosity in the molten state of between 10,000 and 300,000 Pa.s, preferably from 15,000 to 220,000 Pa.s, as measured by plane-plane geometry according to ISO 6721-10:2015 at a temperature of 250°C, a frequency of 0.292 rad/s and a deformation of 2%, the sum of the constituents a) + b) + c) being 100% in weight.
- said composition comprises: a) from 89 to 99.9% of at least one semi-crystalline aliphatic polyamide having a number of carbon per nitrogen atom greater than or equal to 7, in in particular greater than or equal to 8, b) from 0.1 to 9%, by weight of at least one branching agent chosen from polyepoxy, polyanhydrides and polyisocyanates, in particular polymaleic anhydrides and polyepoxy, the composition having after compounding a viscosity in the molten state of between 10,000 and 300,000 Pa.s, preferably between 15,000 and 220,000 Pa.s, as measured in plane-plane geometry according to standard ISO 6721-10:2015 at a temperature of 250° C, a frequency of 0.292 rad/s and a deformation of 2%, the sum of constituents a) + b) making 100% by weight.
- branching agent chosen from polyepoxy, polyanhydrides and polyisocyanates, in particular polymaleic anhydrides and polyepoxy
- the composition consists of: a) from 89 to 99.9% of at least one semi-crystalline aliphatic polyamide having a number of carbon per nitrogen atom greater than or equal to 7, in particular greater than or equal to 8, b) from 0.1 to 9%, by weight of at least one branching agent chosen from polyepoxy, polyanhydrides and polyisocyanates, in particular maleic polyanhydrides and polyepoxy, composition having, after compounding, a viscosity in the molten state of between 10,000 and 300,000 Pa.s, preferably from 15,000 to 220,000 Pa.s, as measured in plane-plane geometry according to standard ISO 6721-10:2015 at a temperature of 250° C., a frequency of 0.292 rad/s and a deformation of 2%, the sum of the constituents a)+b) making 100% by weight.
- branching agent chosen from polyepoxy, polyanhydrides and polyisocyanates, in particular maleic polyanhydrides and polyepoxy
- said composition comprises: a) from 89 to 99.8% of at least one semi-crystalline aliphatic polyamide having a number of carbon per nitrogen atom greater than or equal to 7, in particular greater than or equal to 8, b) from 0.1 to 9%, by weight of at least one branching agent chosen from polyepoxy, polyanhydrides and polyisocyanates, in particular maleic polyanhydrides and polyepoxy, c) of 0.1 to 2% of at least one additive, the composition exhibiting, after compounding, a viscosity in the molten state comprised from 10,000 to 300,000 Pa.s, preferably from 15,000 to 220,000 Pa.s, as measured in plane geometry - plan according to ISO 6721-10:2015 at a temperature of 250°C, a frequency of 0.292 rad/s and a deformation of 2%, the sum of the constituents a) + b) + c) making 100% by weight .
- the composition consists of: a) from 89 to 99.8% of at least one semi-crystalline aliphatic polyamide having a higher number of carbon per nitrogen atom or equal to 7, in particular greater than or equal to 8, b) from 0.1 to 9%, by weight of at least one branching agent chosen from polyepoxy, polyanhydrides and polyisocyanates, in particular maleic polyanhydrides and polyepoxy , c) from 0.1 to 2% of at least one additive, the composition having, after compounding, a viscosity in the molten state of between 10,000 and 300,000 Pa.s, preferably from 15,000 to 220,000 Pa.s, such as measured in plane-plane geometry according to standard ISO 6721-10:2015 at a temperature of 250°C, a frequency of 0.292 rad/s and a deformation of 2%, the sum of the constituents a) + b) + c) being 100% by weight.
- said composition comprises: a) from 93 to 99.9% of at least one semi-crystalline aliphatic polyamide having a number of carbon per nitrogen atom greater than or equal to 7, in in particular greater than or equal to 8, b) from 0.1 to 5% by weight of at least one branching agent chosen from polyepoxy, polyanhydrides and polyisocyanates, in particular polymaleic anhydrides and polyepoxy, the composition having after compounding a melt viscosity of from 10,000 to 300,000 Pa.s, preferably from 15,000 to 220,000 Pa.s, as measured in plane-plane geometry according to standard ISO 6721-10:2015 at a temperature of 250°C, a frequency of 0.292 rad/s and a deformation of 2%, the sum of the constituents a) + b) making 100% by weight.
- branching agent chosen from polyepoxy, polyanhydrides and polyisocyanates, in particular polymaleic anhydrides and polyepoxy
- said composition consists of: a) from 93 to 99.9% of at least one semi-crystalline aliphatic polyamide having a number of carbon per nitrogen atom greater than or equal to to 7, in particular greater than or equal to 8, b) from 0.1 to 5% by weight of at least one branching agent chosen from polyepoxy, polyanhydrides and polyisocyanates, in particular maleic polyanhydrides and polyepoxy, composition having, after compounding, a viscosity in the molten state of between 10,000 and 300,000 Pa.s, preferably from 15,000 to 220,000 Pa.s, as measured in plane geometry according to standard ISO 6721-10:2015 at a temperature of 250 °C, a frequency of 0.292 rad/s and a deformation of 2%, the sum of the constituents a) + b) making 100% by weight.
- branching agent chosen from polyepoxy, polyanhydrides and polyisocyanates, in particular maleic polyanhydrides and polyepoxy
- said composition comprises: a) from 93 to 99.8% of at least one semi-crystalline aliphatic polyamide having a number of carbon per nitrogen atom greater than or equal to 7, in particular greater than or equal to 8, b) from 0.1 to 5% by weight of at least one branching agent chosen from polyepoxy, polyanhydrides and polyisocyanates, in particular polymaleic anhydrides and polyepoxy, c) from 0.1 to 2% of au least one additive, the composition exhibiting, after compounding, a viscosity in the molten state of between 10,000 and 300,000 Pa.s, preferably from 15,000 to 220,000 Pa.s, as measured in plane-plane geometry according to standard ISO 6721-10: 2015 at a temperature of 250°C, a frequency of 0.292 rad/s and a deformation of 2%, the sum of the constituents a) + b) + c) being 100% by weight.
- branching agent chosen from polyepoxy, polyanhydrides and polyisocyanates, in particular
- said composition consists of: a) from 93 to 99.8% of at least one semi-crystalline aliphatic polyamide having a number of carbon per nitrogen atom greater than or equal to 7, in particular greater than or equal to 8, b) from 0.1 to 5% by weight of at least one branching agent chosen from polyepoxy, polyanhydrides and polyisocyanates, in particular polymaleic anhydrides and polyepoxy, c) from 0.1 to 2% of at least one additive, the composition exhibiting, after compounding, a viscosity in the molten state of between 10,000 and 300,000 Pa.s, preferably from 15,000 to 220,000 Pa.s, as measured in plane-plane geometry according to ISO 6721-10:2015 at a temperature of 250°C, a frequency of 0.292 rad/s and a deformation of 2%, the sum of the constituents a) + b) + c) being 100% in weight.
- said composition comprises: a) from 98 to 99.9% of at least one semi-crystalline aliphatic polyamide having a number of carbon per nitrogen atom greater than or equal to 7, in individual greater than or equal to 8, b) from 0.1 to 2% by weight of at least one branching agent chosen from polyepoxy, polyanhydrides and polyisocyanates, in particular polymaleic anhydrides and polyepoxy, the composition having, after compounding, a viscosity in the molten state ranging from 10,000 to 300,000 Pa.s, preferably from 15,000 to 220,000 Pa.s, as measured in plane-plane geometry according to standard ISO 6721-10:2015 at a temperature of 250°C, a frequency of 0.292 rad/s and a deformation of 2%, the sum of the constituents a) + b) making 100% by weight.
- branching agent chosen from polyepoxy, polyanhydrides and polyisocyanates, in particular polymaleic anhydrides and polyepoxy
- said composition consists of: a) from 98 to 99.9% of at least one semi-crystalline aliphatic polyamide having a number of carbon per nitrogen atom greater than or equal to to 7, in particular greater than or equal to 8, b) from 0.1 to 2% by weight of at least one branching agent chosen from polyepoxy, polyanhydrides and polyisocyanates, in particular maleic polyanhydrides and polyepoxy, composition having, after compounding, a viscosity in the molten state of between 10,000 and 300,000 Pa.s, preferably from 15,000 to 220,000 Pa.s, as measured in plane-plane geometry according to standard ISO 6721-10:2015 at a temperature of 250° C., a frequency of 0.292 rad/s and a deformation of 2%, the sum of the constituents a)+b) making 100% by weight.
- branching agent chosen from polyepoxy, polyanhydrides and polyisocyanates, in particular maleic polyanhydrides and polyepoxy
- said composition consists of: a) from 96 to 99.8% of at least one semi-crystalline aliphatic polyamide having a higher number of carbon per nitrogen atom or equal to 7, in particular greater than or equal to 8, b) from 0.1 to 2% by weight of at least one branching agent chosen from polyepoxy, polyanhydrides and polyisocyanates, in particular polymaleic anhydrides and polyepoxy, c) from 0.1 to 2% of at least one additive, the composition exhibiting, after compounding, a viscosity in the molten state of between 10,000 and 300,000 Pa.s, preferably from 15,000 to 220,000 Pa.s, as measured in plane-plane geometry according to ISO 6721-10:2015 at a temperature of 250°C, a frequency of 0.292 rad/s and a deformation of 2%, the sum of the constituents a) + b) + c) being 100% in weight.
- the MVR volume melt index
- ISO 1133:2011 with a weight of 21.6 Kg and at a temperature of 275°C is included from 2 to 25 cm 3 /10 min, advantageously from 5 to 20 cm 3 /10 min, very advantageously comprised from 6 to 18 cm 3 /10 min.
- the R of the composition is comprised from 0 to 5, advantageously from 0 to 0.1 g/10 min at 235° C., 1 kg according to ISO 1133: 2011.
- branching agent and the polyamide are linked by means of a covalent bond, advantageously the branching agent and the polyamide are linked by an amide, ester or urea function.
- the ratio of the viscosities in the molten state as measured in plane-plane geometry at 0.292 rad. s 7292 rad.s 1 of said compositions is between 10 and 200, advantageously between 25 and 150.
- This ratio makes it possible to determine the degree of branching of the polyamide of said composition. The higher the ratio, the more the polyamide is connected in the composition. Consequently, the polyamide must be fluid at 292 rad.s 1 and viscous at 0.292 rad.s 1 ; the viscosity at 292 rad.s ⁇ 1 is between 400 and 2000 and preferably between 600 and 1550;
- the rheotensive force at 250° C. of the composition after compounding is between 22 mN and 200 mN, in particular between 25 mN and 150 mN; this force determines the melt strength of the polyamide, the greater the force, the less the polyamide flows;
- the Rheotens force can for example be determined using a Rheotens 71.97 apparatus from Gottfert.
- the swelling rate is carried out according to the procedure: a 25 cm tubular parison is extruded using an extrusion blow molding line equipped with an accumulator.
- the expulsion speed is fixed at 0.1m/s, the temperature of the extrudate is checked manually using a thermal probe.
- the measurement of the diameter of the parison is carried out 10 cm below the die. 5 measurements are taken to obtain an average.
- the temperature is chosen according to the flow characteristics of the polymer to limit the creep of the parison as much as possible.
- the behavior of the parison makes it possible to analyze the capacity of the material to counterbalance the effect of gravity. Under its weight, a parison extruded horizontally or vertically will creep, thus modifying its dimensions.
- the hold of the vertical parison of the composition after compounding is between 15 and 50 s, in particular from 20 to 45 s.
- Decompression tests under Hydrogen have shown that a quantity of impact modifier in the composition of the material less than or equal to 10% by weight makes it possible to avoid and limit cavitation mechanisms (blistering).
- the sample undergoes a rise in pressure from 1 to 40 MPa with a speed of lMPa.min-1, the latter is maintained at 40 MPa for 7 days so that it reaches a saturated state.
- the decompression phase is carried out with a speed of 5 MPa.min-1.
- the samples are observed under a scanning electron microscope in order to observe any cavitations.
- compositions according to the invention are resistant to decompression tests under hydrogen.
- the present invention relates to a single-layer or multi-layer tubular structure intended for the transport, distribution or storage of hydrogen, comprising at least one sealing layer (1) comprising a composition as defined above.
- said structure further comprises at least one composite reinforcement layer (2), said innermost composite reinforcement layer being welded or not, to said outermost adjacent sealing layer .
- Said composite reinforcing layer is therefore above said sealing layer which is in contact with the hydrogen.
- the number of composite reinforcement layers is between 1 and m.
- the polymer P2j can be thermoplastic or thermosetting.
- Thermoplastic polymer P2j is a thermoplastic polymer
- Thermoplastic or thermoplastic polymer is understood to mean a material which is generally solid at room temperature, which may be semi-crystalline or amorphous, in particular semi-crystalline and which softens during an increase in temperature, in particular after passing from its temperature of glass transition (Tg) and flows at a higher temperature when it is amorphous, or which can present a frank melting on passing its so-called melting temperature (Tf) when it is semi-crystalline, and which becomes solid again when 'a decrease in temperature below its crystallization temperature, Te, (for a semi-crystalline) and below its glass transition temperature (for an amorphous).
- Tg, Te and Tf are determined by differential scanning calorimetry (DSC) according to standard 11357-2:2013 and 11357-3:2013 respectively.
- the number-average molecular mass Mn of said thermoplastic polymer is preferably in a range extending from 10,000 to 40,000, preferably from 10,000 to 30,000. These Mn values may correspond to inherent viscosities greater than or equal to 0.8 as determined in the m-cresol according to the ISO 307:2007 standard but changing the solvent (use of m-cresol instead of sulfuric acid and the temperature being 20°C).
- suitable semi-crystalline thermoplastic polymers in the present invention include: polyamides, in particular comprising an aromatic and/or cycloaliphatic structure, including copolymers, for example polyamide-polyether copolymers, polyesters, polyaryletherketones (PAEK ), polyetherether ketones (PEEK), polyetheretherketone ketones (PEKK), polyetherketoneetherketoneketones (PEKEKK), polyimides in particular polyetherimides (PEI) or polyamide-imides, polylsulfones (PSU) in particular polyarylsulfones such as polyphenylsulfones (PPSU), polyethersulfones (PES).
- semi-crystalline polymers are more particularly preferred, and in particular polyamides and their semi-crystalline copolymers.
- the polyamide can be a homopolyamide or a copolyamide or a mixture thereof.
- the semi-crystalline polyamides are semi-aromatic polyamides, in particular a semi-aromatic polyamide of formula X/YAr, as described in EP1505099, in particular a semi-aromatic polyamide of formula A/XT in which A is chosen from a unit obtained from an amino acid, a unit obtained from a lactam and a unit corresponding to the formula (diamine in Ca).
- (Cb diacid) with a representing the number of carbon atoms of the diamine and b representing the number of carbon atoms of the diacid, a and b each being comprised from 4 to 36, advantageously from 9 to 18, the unit (Ca diamine) being chosen from aliphatic, linear or branched diamines, cycloaliphatic diamines and alkylaromatic diamines and the unit (Cb diacid) being chosen from aliphatic, linear or branched diacids, cycloaliphatic diacids and aromatic diacids ;
- T stands for terephthalic acid
- MXD stands for m-xylylene diamine
- MPMD stands for methylpentamethylene diamine
- BAC stands for bis(aminomethyl)cyclohexane.
- Said semi-aromatic polyamides defined above have in particular a Tg greater than or equal to 80°C.
- thermosetting polymer
- thermosetting polymers are chosen from epoxy or epoxy-based resins, polyesters, vinyl esters, resins based on polyisocyanates, in particular polyisocyanurates, and polyurethanes, or a mixture of these in particular epoxy or epoxy-based resins or a resin based on polyisocyanates, in particular polyisocyanurates.
- each composite reinforcement layer consists of a composition comprising the same type of polymer, in particular an epoxy or epoxy-based resin or a resin based on polyisocyanates, in particular polyisocyanurates.
- Said composition comprising said polymer P2j can be transparent to radiation suitable for welding.
- these fibers forming said fibrous material are in particular fibers of mineral, organic or vegetable origin.
- said fibrous material can be sized or not sized.
- Said fibrous material can therefore comprise up to 3.5% by weight of a material of organic nature (thermosetting or thermoplastic resin type) called size.
- fibers of mineral origin mention may be made of carbon fibers, glass fibers, basalt or basalt-based fibers, silica fibers, or silicon carbide fibers for example.
- fibers of organic origin mention may be made of fibers based on a thermoplastic or thermosetting polymer, such as semi-aromatic polyamide fibers, aramid fibers, polyester fibers or polyolefin fibers for example.
- they are based on an amorphous thermoplastic polymer and have a glass transition temperature Tg higher than the Tg of the polymer or mixture of thermoplastic polymer constituting the pre-impregnation matrix when the latter is amorphous, or higher than the Tm polymer or mixture of thermoplastic polymer constituting the pre-impregnation matrix when the latter is semi-crystalline.
- they are based on a semi-crystalline thermoplastic polymer and have a melting point Tf higher than the Tg of the polymer or thermoplastic polymer mixture constituting the pre-impregnation matrix when the latter is amorphous, or higher than the Tm polymer or mixture of thermoplastic polymer constituting the pre-impregnation matrix when the latter is semi-crystalline.
- the organic fibers forming the fibrous material during impregnation by the thermoplastic matrix of the final composite.
- the fibers of plant origin mention may be made of natural fibers based on flax, hemp, lignin, bamboo, silk, in particular spider silk, sisal, and other cellulosic fibers, in particular viscose. These fibers of plant origin can be used pure, treated or even coated with a coating layer, in order to facilitate adhesion and impregnation of the thermoplastic polymer matrix.
- the fibrous material can also be a fabric, braided or woven with fibers.
- Organic fiber rovings can have several grammages. They may also have several geometries.
- the fibers making up the fibrous material may also be in the form of a mixture of these reinforcing fibers of different geometries.
- the fibers are continuous fibers.
- the fibrous material is chosen from glass fibres, carbon fibres, basalt or basalt-based fibres, or a mixture of these, in particular carbon fibres.
- It is used in the form of a wick or several wicks.
- the present invention relates to the use of 0.05% to 10%, in particular from 0.1 to 9% by weight, of at least one branching agent chosen from polyepoxy, polyanhydrides and polyisocyanates, in particular maleic polyanhydrides and polyepoxy, with 88 to 99.95%, in particular from 89 to 99.9% of at least one semi-crystalline aliphatic polyamide having a number of carbon per nitrogen atom greater than or equal to 7, in particular greater than or equal to 8, and optionally an additive for the constitution of a composition for blow molding or extrusion, in particular for blow molding, as defined above, whose viscosity in the molten state after compounding is between 10,000 to 300,000 Pa.s, preferably from 15,000 to 220,000 Pa.s, as measured in plane-plane geometry according to standard ISO 6721-10:2015 at a temperature of 250° C., a frequency of 0.292 rad/s and a strain of 2%.
- branching agent chosen from polyepoxy, polyanhydrides and polyiso
- a tank comprising or consisting of one or more layers, namely a sealing layer and optionally one or more reinforcing layers, or several sealing layers and optionally several layers reinforcement, or several sealing layers and a reinforcing layer or else a sealing layer and a reinforcing layer.
- the monolayer or multilayer tubular structure in the present invention also designates a pipe or a tube intended for the transport of hydrogen from the tank to the fuel cell and which comprises or consists of one or more layers, as defined above. .
- the present invention relates to a process for preparing a composition for blow molding or extrusion, in particular blow molding, such as defined above, characterized in that it comprises a step of compounding said composition.
- the compounding step is carried out in a special way so that the alloys have melt viscosities of between 10,000 and 300,000 Pa.s, preferably from 15,000 to 220,000 Pa.s, as measured in plane geometry according to ISO 6721-10. :2015 at a temperature of 250°C, a frequency of 0.292 rad/s and a strain of 2%.
- These viscosities can for example be obtained by compounding at a temperature of the molten polymer greater than 280° C., preferably greater than 300° C. by increasing the residence time in the compounder.
- This branching reaction is advantageously catalyzed with, for example, phosphonium salts or hindered amines.
- the average residence time being advantageously from 20 seconds to 10 minutes, more advantageously from 45 seconds to 6 minutes.
- said compounding is carried out at a temperature of the molten polymer greater than 280° C., preferably greater than 300° C. with an average residence time ranging from 20 seconds to 10 minutes, very advantageously from 45 seconds to 6 minutes .
- the present invention relates to a process for preparing a single-layer or multi-layer tubular structure as defined above, characterized in that it comprises a step of blow-molding or extrusion, in particular blow-molding , of a composition as defined above.
- the method comprises a prior step of compounding a composition as defined above.
- the prior compounding step is in particular carried out as defined above.
- the alloys were fabricated using a 40 mm ZSK twin-screw extruder (Coperion).
- the barrel temperature was set at 280°C and the screw speed was 300 rpm with a throughput of 60 kg/h.
- the PA6 used is a polyamide 6 having a concentration at the end of the acid chain of 25 peq/g and a concentration at the end of the amine chain of 22 peq/g.
- the PA610 used is a polyamide 610 having a concentration of acid chain ends of 27 peq/g and a concentration of amine chain ends of 19 peq/g.
- the PA612 used is a polyamide 612 having a concentration of acid chain ends of 22 peq/g and a concentration of amine chain ends of 20 peq/g.
- the Joncryl ADR 4400 is from BASF.
- the Xibond 125 is from Polyscope.
- the Lotader 3410 is from SK functional polymer.
- Anox NBD TL 89 stabilizer is from SI group.
- melt viscosity was measured using an Ares G2 Rotational Rheometer equipped with a 25mm plane-plane geometry at a temperature of 250°C, at 0.292 rad/s (dwell time before launch 5 min under nitrogen, deformation of 2%, scanning from 628rad/s to 0.062rad/s and 3 points per decade, taking of a point over 3 cycles, gap of 1.5mm )
- the Rheotens force is determined using a Rheotens 71.97 apparatus from Gottfert.
- the water uptake is determined either in an oven under a controlled atmosphere at 100% Rh or in water, in all cases after saturation at 70°C and the measurement of this water uptake is made by weighing the sample at 23°C, for regular sampling times, spaced out by several days, until a state of equilibrium is observed , which is reached when the mass of the sample becomes constant (within the uncertainty of the measurement) for three consecutive sampling times. In the case of conditioning in water, the equilibrium reached corresponds to the water saturation
- MFI short for Melt Flow Index
- Liners with a thickness of 2 mm according to the compositions of the invention were prepared by blow molding and the hydrogen permeability at 15° C. was tested.
- compositions according to the invention have an MFI equal to 0, which means that nothing flows into the machine.
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Abstract
Description
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Priority Applications (4)
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CA3221469A CA3221469A1 (fr) | 2021-06-28 | 2022-06-24 | Compositions de soufflage moulage a base de polyamides branches et leurs utilisations |
CN202280046268.1A CN117580700A (zh) | 2021-06-28 | 2022-06-24 | 基于支化聚酰胺的吹塑组合物及其用途 |
KR1020247003253A KR20240026512A (ko) | 2021-06-28 | 2022-06-24 | 분지형 폴리아미드를 기반으로 한 블로우 몰딩 조성물 및 이의 용도 |
EP22743850.4A EP4363191A1 (fr) | 2021-06-28 | 2022-06-24 | Compositions de soufflage moulage a base de polyamides branches et leurs utilisations |
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FRFR2106906 | 2021-06-28 | ||
FR2106906A FR3124516A1 (fr) | 2021-06-28 | 2021-06-28 | Compositions de soufflage moulage a base de polyamides branches et leurs utilisations |
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EP (1) | EP4363191A1 (fr) |
KR (1) | KR20240026512A (fr) |
CN (1) | CN117580700A (fr) |
CA (1) | CA3221469A1 (fr) |
FR (1) | FR3124516A1 (fr) |
WO (1) | WO2023275463A1 (fr) |
Citations (12)
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---|---|---|---|---|
US3505285A (en) | 1965-09-11 | 1970-04-07 | Bayer Ag | Stabilised polyamides containing a copper salt and a phosphine |
EP0342066A1 (fr) | 1988-03-24 | 1989-11-15 | Elf Atochem S.A. | Copolymère greffé à base d'alpha-mono-oléfine, son procédé de fabrication, son application à la fabrication d'alliages thermoplastiques, alliages thermoplastiques obtenus |
EP0495363A1 (fr) | 1991-01-15 | 1992-07-22 | Bayer Ag | Procédé de préparation de polyamides à haut poids moléculaire |
CA2347258A1 (fr) | 1998-10-15 | 2000-04-20 | L. Bruggemann Kg | Composition de polyamide stabilisee avec des complexes de cuivre et des composes halogenes organiques |
EP1352934A1 (fr) | 2002-04-08 | 2003-10-15 | Atofina | Surfaces métalliques revêtues de polyamide |
EP1505099A2 (fr) | 2003-08-05 | 2005-02-09 | Arkema | Polymides semi aromatiques souples à faible reprise en humidité |
US20050228145A1 (en) | 2004-01-26 | 2005-10-13 | Christophe Lacroix | Polyamide 1/interlayer/polyamide 2 multilayer structures for decorated articles |
US20080274355A1 (en) | 2007-05-03 | 2008-11-06 | Ems-Patent Ag | Semiaromatic polyamide molding compositions and their use |
EP2649130A2 (fr) | 2010-12-09 | 2013-10-16 | DSM IP Assets B.V. | Revêtement intérieur pour réservoir de stockage de gaz |
FR2996556A1 (fr) | 2012-10-10 | 2014-04-11 | Rhodia Operations | Liner pour reservoir cng |
FR3078132A1 (fr) | 2018-02-21 | 2019-08-23 | Arkema France | Structure tubulaire annelee destinee au transport de carburant dans le reservoir |
CA3101967A1 (fr) | 2018-07-31 | 2020-02-06 | Toray Industries, Inc. | Composition de resine de polyamide pour produits moules par soufflage exposes a de l'hydrogene a haute pression, et produit moule par soufflage |
-
2021
- 2021-06-28 FR FR2106906A patent/FR3124516A1/fr active Pending
-
2022
- 2022-06-24 EP EP22743850.4A patent/EP4363191A1/fr active Pending
- 2022-06-24 KR KR1020247003253A patent/KR20240026512A/ko unknown
- 2022-06-24 CN CN202280046268.1A patent/CN117580700A/zh active Pending
- 2022-06-24 CA CA3221469A patent/CA3221469A1/fr active Pending
- 2022-06-24 WO PCT/FR2022/051246 patent/WO2023275463A1/fr active Application Filing
Patent Citations (13)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3505285A (en) | 1965-09-11 | 1970-04-07 | Bayer Ag | Stabilised polyamides containing a copper salt and a phosphine |
EP0342066A1 (fr) | 1988-03-24 | 1989-11-15 | Elf Atochem S.A. | Copolymère greffé à base d'alpha-mono-oléfine, son procédé de fabrication, son application à la fabrication d'alliages thermoplastiques, alliages thermoplastiques obtenus |
EP0495363A1 (fr) | 1991-01-15 | 1992-07-22 | Bayer Ag | Procédé de préparation de polyamides à haut poids moléculaire |
CA2347258A1 (fr) | 1998-10-15 | 2000-04-20 | L. Bruggemann Kg | Composition de polyamide stabilisee avec des complexes de cuivre et des composes halogenes organiques |
EP1352934A1 (fr) | 2002-04-08 | 2003-10-15 | Atofina | Surfaces métalliques revêtues de polyamide |
EP1505099A2 (fr) | 2003-08-05 | 2005-02-09 | Arkema | Polymides semi aromatiques souples à faible reprise en humidité |
US20050228145A1 (en) | 2004-01-26 | 2005-10-13 | Christophe Lacroix | Polyamide 1/interlayer/polyamide 2 multilayer structures for decorated articles |
US20080274355A1 (en) | 2007-05-03 | 2008-11-06 | Ems-Patent Ag | Semiaromatic polyamide molding compositions and their use |
EP2649130A2 (fr) | 2010-12-09 | 2013-10-16 | DSM IP Assets B.V. | Revêtement intérieur pour réservoir de stockage de gaz |
FR2996556A1 (fr) | 2012-10-10 | 2014-04-11 | Rhodia Operations | Liner pour reservoir cng |
FR3078132A1 (fr) | 2018-02-21 | 2019-08-23 | Arkema France | Structure tubulaire annelee destinee au transport de carburant dans le reservoir |
CA3101967A1 (fr) | 2018-07-31 | 2020-02-06 | Toray Industries, Inc. | Composition de resine de polyamide pour produits moules par soufflage exposes a de l'hydrogene a haute pression, et produit moule par soufflage |
WO2020027031A1 (fr) | 2018-07-31 | 2020-02-06 | 東レ株式会社 | Composition de résine de polyamide pour produits moulés par soufflage exposés à de l'hydrogène à haute pression, et produit moulé par soufflage |
Also Published As
Publication number | Publication date |
---|---|
CN117580700A (zh) | 2024-02-20 |
FR3124516A1 (fr) | 2022-12-30 |
EP4363191A1 (fr) | 2024-05-08 |
KR20240026512A (ko) | 2024-02-28 |
CA3221469A1 (fr) | 2023-01-05 |
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