EP2694715A2 - Nappe de fibre de laine vegetale impregnee d'une huile vegetale epoxydee - Google Patents
Nappe de fibre de laine vegetale impregnee d'une huile vegetale epoxydeeInfo
- Publication number
- EP2694715A2 EP2694715A2 EP12720250.5A EP12720250A EP2694715A2 EP 2694715 A2 EP2694715 A2 EP 2694715A2 EP 12720250 A EP12720250 A EP 12720250A EP 2694715 A2 EP2694715 A2 EP 2694715A2
- Authority
- EP
- European Patent Office
- Prior art keywords
- oil
- mixture
- fibers
- hardener
- vegetable
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Withdrawn
Links
- 239000000835 fiber Substances 0.000 title claims abstract description 42
- 210000002268 wool Anatomy 0.000 title claims abstract description 42
- 235000015112 vegetable and seed oil Nutrition 0.000 title claims abstract description 28
- 239000008158 vegetable oil Substances 0.000 title claims abstract description 28
- 235000013311 vegetables Nutrition 0.000 title claims abstract description 25
- 239000004848 polyfunctional curative Substances 0.000 claims abstract description 35
- 238000000034 method Methods 0.000 claims abstract description 17
- 238000004519 manufacturing process Methods 0.000 claims abstract description 13
- 230000015556 catabolic process Effects 0.000 claims abstract description 8
- 238000002844 melting Methods 0.000 claims abstract description 8
- 230000008018 melting Effects 0.000 claims abstract description 8
- 238000002156 mixing Methods 0.000 claims abstract description 7
- 238000000151 deposition Methods 0.000 claims abstract description 5
- 239000011230 binding agent Substances 0.000 claims description 44
- 239000000203 mixture Substances 0.000 claims description 43
- 239000003921 oil Substances 0.000 claims description 34
- 235000019198 oils Nutrition 0.000 claims description 34
- 238000009413 insulation Methods 0.000 claims description 23
- 241000196324 Embryophyta Species 0.000 claims description 18
- 125000003700 epoxy group Chemical group 0.000 claims description 17
- 150000008064 anhydrides Chemical class 0.000 claims description 9
- 238000004132 cross linking Methods 0.000 claims description 9
- 238000005507 spraying Methods 0.000 claims description 7
- 235000021122 unsaturated fatty acids Nutrition 0.000 claims description 7
- 150000004670 unsaturated fatty acids Chemical class 0.000 claims description 7
- 238000006731 degradation reaction Methods 0.000 claims description 6
- 238000009792 diffusion process Methods 0.000 claims description 6
- 235000021388 linseed oil Nutrition 0.000 claims description 6
- 239000000944 linseed oil Substances 0.000 claims description 6
- 240000006240 Linum usitatissimum Species 0.000 claims description 5
- 235000004431 Linum usitatissimum Nutrition 0.000 claims description 5
- 239000006185 dispersion Substances 0.000 claims description 4
- 238000010438 heat treatment Methods 0.000 claims description 4
- 239000002904 solvent Substances 0.000 claims description 4
- 244000105624 Arachis hypogaea Species 0.000 claims description 3
- 229920000742 Cotton Polymers 0.000 claims description 3
- 235000010469 Glycine max Nutrition 0.000 claims description 3
- 244000020551 Helianthus annuus Species 0.000 claims description 3
- 235000003222 Helianthus annuus Nutrition 0.000 claims description 3
- 240000007817 Olea europaea Species 0.000 claims description 3
- 240000002834 Paulownia tomentosa Species 0.000 claims description 3
- 235000010678 Paulownia tomentosa Nutrition 0.000 claims description 3
- 235000020226 cashew nut Nutrition 0.000 claims description 3
- 238000001802 infusion Methods 0.000 claims description 3
- 235000020232 peanut Nutrition 0.000 claims description 3
- 230000035515 penetration Effects 0.000 claims description 3
- 238000005096 rolling process Methods 0.000 claims description 3
- 239000002023 wood Substances 0.000 claims description 3
- 244000226021 Anacardium occidentale Species 0.000 claims description 2
- 240000002791 Brassica napus Species 0.000 claims description 2
- 235000004977 Brassica sinapistrum Nutrition 0.000 claims description 2
- 230000001105 regulatory effect Effects 0.000 claims description 2
- 235000017060 Arachis glabrata Nutrition 0.000 claims 1
- 235000010777 Arachis hypogaea Nutrition 0.000 claims 1
- 235000018262 Arachis monticola Nutrition 0.000 claims 1
- 235000004443 Ricinus communis Nutrition 0.000 claims 1
- 229940087559 grape seed Drugs 0.000 claims 1
- 229920000768 polyamine Polymers 0.000 description 13
- 229920000642 polymer Polymers 0.000 description 10
- 229920001169 thermoplastic Polymers 0.000 description 10
- 238000006243 chemical reaction Methods 0.000 description 9
- 229920001187 thermosetting polymer Polymers 0.000 description 9
- 150000004985 diamines Chemical class 0.000 description 8
- 230000006870 function Effects 0.000 description 8
- 239000000126 substance Substances 0.000 description 8
- 239000004416 thermosoftening plastic Substances 0.000 description 8
- -1 polyethylene Polymers 0.000 description 7
- 150000001875 compounds Chemical class 0.000 description 6
- 238000009472 formulation Methods 0.000 description 6
- 239000000463 material Substances 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 5
- 235000014113 dietary fatty acids Nutrition 0.000 description 5
- 229930195729 fatty acid Natural products 0.000 description 5
- 239000000194 fatty acid Substances 0.000 description 5
- 150000004665 fatty acids Chemical class 0.000 description 5
- 238000006116 polymerization reaction Methods 0.000 description 5
- 230000008569 process Effects 0.000 description 5
- 230000008901 benefit Effects 0.000 description 4
- 229910052500 inorganic mineral Inorganic materials 0.000 description 4
- 239000011707 mineral Substances 0.000 description 4
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 4
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 150000008065 acid anhydrides Chemical class 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 238000007906 compression Methods 0.000 description 3
- 230000006835 compression Effects 0.000 description 3
- 238000010276 construction Methods 0.000 description 3
- 238000006735 epoxidation reaction Methods 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 239000011159 matrix material Substances 0.000 description 3
- 239000011490 mineral wool Substances 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 239000002491 polymer binding agent Substances 0.000 description 3
- 150000003141 primary amines Chemical class 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 125000005457 triglyceride group Chemical group 0.000 description 3
- RNLHGQLZWXBQNY-UHFFFAOYSA-N 3-(aminomethyl)-3,5,5-trimethylcyclohexan-1-amine Chemical compound CC1(C)CC(N)CC(C)(CN)C1 RNLHGQLZWXBQNY-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- 239000004593 Epoxy Substances 0.000 description 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
- 239000004698 Polyethylene Substances 0.000 description 2
- 239000004743 Polypropylene Substances 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 125000001931 aliphatic group Chemical group 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- VHRGRCVQAFMJIZ-UHFFFAOYSA-N cadaverine Chemical compound NCCCCCN VHRGRCVQAFMJIZ-UHFFFAOYSA-N 0.000 description 2
- 239000004359 castor oil Substances 0.000 description 2
- 235000019438 castor oil Nutrition 0.000 description 2
- 230000007423 decrease Effects 0.000 description 2
- 238000013461 design Methods 0.000 description 2
- 235000013305 food Nutrition 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 239000011491 glass wool Substances 0.000 description 2
- ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 description 2
- NAQMVNRVTILPCV-UHFFFAOYSA-N hexane-1,6-diamine Chemical compound NCCCCCCN NAQMVNRVTILPCV-UHFFFAOYSA-N 0.000 description 2
- 238000005470 impregnation Methods 0.000 description 2
- 238000009776 industrial production Methods 0.000 description 2
- RTWNYYOXLSILQN-UHFFFAOYSA-N methanediamine Chemical compound NCN RTWNYYOXLSILQN-UHFFFAOYSA-N 0.000 description 2
- 239000003348 petrochemical agent Substances 0.000 description 2
- 239000003208 petroleum Substances 0.000 description 2
- 230000000704 physical effect Effects 0.000 description 2
- 229920000573 polyethylene Polymers 0.000 description 2
- 229920000139 polyethylene terephthalate Polymers 0.000 description 2
- 239000005020 polyethylene terephthalate Substances 0.000 description 2
- 229920005596 polymer binder Polymers 0.000 description 2
- 229920001155 polypropylene Polymers 0.000 description 2
- KIDHWZJUCRJVML-UHFFFAOYSA-N putrescine Chemical compound NCCCCN KIDHWZJUCRJVML-UHFFFAOYSA-N 0.000 description 2
- 239000012429 reaction media Substances 0.000 description 2
- 230000009257 reactivity Effects 0.000 description 2
- 239000011435 rock Substances 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- 230000009466 transformation Effects 0.000 description 2
- 238000009834 vaporization Methods 0.000 description 2
- 230000008016 vaporization Effects 0.000 description 2
- MUTGBJKUEZFXGO-OLQVQODUSA-N (3as,7ar)-3a,4,5,6,7,7a-hexahydro-2-benzofuran-1,3-dione Chemical compound C1CCC[C@@H]2C(=O)OC(=O)[C@@H]21 MUTGBJKUEZFXGO-OLQVQODUSA-N 0.000 description 1
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 1
- SECPZKHBENQXJG-FPLPWBNLSA-N (Z)-Palmitoleic acid Natural products CCCCCC\C=C/CCCCCCCC(O)=O SECPZKHBENQXJG-FPLPWBNLSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- CBCKQZAAMUWICA-UHFFFAOYSA-N 1,4-phenylenediamine Chemical compound NC1=CC=C(N)C=C1 CBCKQZAAMUWICA-UHFFFAOYSA-N 0.000 description 1
- PMUPSYZVABJEKC-UHFFFAOYSA-N 1-methylcyclohexane-1,2-dicarboxylic acid Chemical compound OC(=O)C1(C)CCCCC1C(O)=O PMUPSYZVABJEKC-UHFFFAOYSA-N 0.000 description 1
- VILCJCGEZXAXTO-UHFFFAOYSA-N 2,2,2-tetramine Chemical compound NCCNCCNCCN VILCJCGEZXAXTO-UHFFFAOYSA-N 0.000 description 1
- FALRKNHUBBKYCC-UHFFFAOYSA-N 2-(chloromethyl)pyridine-3-carbonitrile Chemical compound ClCC1=NC=CC=C1C#N FALRKNHUBBKYCC-UHFFFAOYSA-N 0.000 description 1
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 description 1
- OFNISBHGPNMTMS-UHFFFAOYSA-N 3-methylideneoxolane-2,5-dione Chemical compound C=C1CC(=O)OC1=O OFNISBHGPNMTMS-UHFFFAOYSA-N 0.000 description 1
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- 241000208223 Anacardiaceae Species 0.000 description 1
- 239000004475 Arginine Substances 0.000 description 1
- DCXYFEDJOCDNAF-UHFFFAOYSA-N Asparagine Natural products OC(=O)C(N)CC(N)=O DCXYFEDJOCDNAF-UHFFFAOYSA-N 0.000 description 1
- 244000025254 Cannabis sativa Species 0.000 description 1
- 235000012766 Cannabis sativa ssp. sativa var. sativa Nutrition 0.000 description 1
- 235000012765 Cannabis sativa ssp. sativa var. spontanea Nutrition 0.000 description 1
- 235000002566 Capsicum Nutrition 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- RPNUMPOLZDHAAY-UHFFFAOYSA-N Diethylenetriamine Chemical compound NCCNCCN RPNUMPOLZDHAAY-UHFFFAOYSA-N 0.000 description 1
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 1
- 244000068988 Glycine max Species 0.000 description 1
- ODKSFYDXXFIFQN-BYPYZUCNSA-P L-argininium(2+) Chemical compound NC(=[NH2+])NCCC[C@H]([NH3+])C(O)=O ODKSFYDXXFIFQN-BYPYZUCNSA-P 0.000 description 1
- DCXYFEDJOCDNAF-REOHCLBHSA-N L-asparagine Chemical compound OC(=O)[C@@H](N)CC(N)=O DCXYFEDJOCDNAF-REOHCLBHSA-N 0.000 description 1
- ZDXPYRJPNDTMRX-VKHMYHEASA-N L-glutamine Chemical compound OC(=O)[C@@H](N)CCC(N)=O ZDXPYRJPNDTMRX-VKHMYHEASA-N 0.000 description 1
- KDXKERNSBIXSRK-YFKPBYRVSA-N L-lysine Chemical compound NCCCC[C@H](N)C(O)=O KDXKERNSBIXSRK-YFKPBYRVSA-N 0.000 description 1
- KDXKERNSBIXSRK-UHFFFAOYSA-N Lysine Natural products NCCCCC(N)C(O)=O KDXKERNSBIXSRK-UHFFFAOYSA-N 0.000 description 1
- 239000004472 Lysine Substances 0.000 description 1
- 239000004640 Melamine resin Substances 0.000 description 1
- 229920000877 Melamine resin Polymers 0.000 description 1
- 239000005642 Oleic acid Substances 0.000 description 1
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 description 1
- 235000021319 Palmitoleic acid Nutrition 0.000 description 1
- 239000006002 Pepper Substances 0.000 description 1
- LGRFSURHDFAFJT-UHFFFAOYSA-N Phthalic anhydride Natural products C1=CC=C2C(=O)OC(=O)C2=C1 LGRFSURHDFAFJT-UHFFFAOYSA-N 0.000 description 1
- 235000016761 Piper aduncum Nutrition 0.000 description 1
- 235000017804 Piper guineense Nutrition 0.000 description 1
- 244000203593 Piper nigrum Species 0.000 description 1
- 235000008184 Piper nigrum Nutrition 0.000 description 1
- 239000005700 Putrescine Substances 0.000 description 1
- 241000219094 Vitaceae Species 0.000 description 1
- 235000009754 Vitis X bourquina Nutrition 0.000 description 1
- 235000012333 Vitis X labruscana Nutrition 0.000 description 1
- 240000006365 Vitis vinifera Species 0.000 description 1
- 235000014787 Vitis vinifera Nutrition 0.000 description 1
- FDLQZKYLHJJBHD-UHFFFAOYSA-N [3-(aminomethyl)phenyl]methanamine Chemical compound NCC1=CC=CC(CN)=C1 FDLQZKYLHJJBHD-UHFFFAOYSA-N 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 150000001335 aliphatic alkanes Chemical class 0.000 description 1
- DTOSIQBPPRVQHS-PDBXOOCHSA-N alpha-linolenic acid Chemical compound CC\C=C/C\C=C/C\C=C/CCCCCCCC(O)=O DTOSIQBPPRVQHS-PDBXOOCHSA-N 0.000 description 1
- 235000020661 alpha-linolenic acid Nutrition 0.000 description 1
- 230000004075 alteration Effects 0.000 description 1
- 235000001014 amino acid Nutrition 0.000 description 1
- 229940024606 amino acid Drugs 0.000 description 1
- 150000001413 amino acids Chemical class 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- IMUDHTPIFIBORV-UHFFFAOYSA-N aminoethylpiperazine Chemical compound NCCN1CCNCC1 IMUDHTPIFIBORV-UHFFFAOYSA-N 0.000 description 1
- 235000021120 animal protein Nutrition 0.000 description 1
- ODKSFYDXXFIFQN-UHFFFAOYSA-N arginine Natural products OC(=O)C(N)CCCNC(N)=N ODKSFYDXXFIFQN-UHFFFAOYSA-N 0.000 description 1
- 150000004984 aromatic diamines Chemical class 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 229960001230 asparagine Drugs 0.000 description 1
- 235000009582 asparagine Nutrition 0.000 description 1
- OTBHHUPVCYLGQO-UHFFFAOYSA-N bis(3-aminopropyl)amine Chemical compound NCCCNCCCN OTBHHUPVCYLGQO-UHFFFAOYSA-N 0.000 description 1
- GHWVXCQZPNWFRO-UHFFFAOYSA-N butane-2,3-diamine Chemical compound CC(N)C(C)N GHWVXCQZPNWFRO-UHFFFAOYSA-N 0.000 description 1
- JHIWVOJDXOSYLW-UHFFFAOYSA-N butyl 2,2-difluorocyclopropane-1-carboxylate Chemical compound CCCCOC(=O)C1CC1(F)F JHIWVOJDXOSYLW-UHFFFAOYSA-N 0.000 description 1
- 235000009120 camo Nutrition 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000011203 carbon fibre reinforced carbon Substances 0.000 description 1
- 235000005607 chanvre indien Nutrition 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- SECPZKHBENQXJG-UHFFFAOYSA-N cis-palmitoleic acid Natural products CCCCCCC=CCCCCCCCC(O)=O SECPZKHBENQXJG-UHFFFAOYSA-N 0.000 description 1
- 238000005253 cladding Methods 0.000 description 1
- 238000005056 compaction Methods 0.000 description 1
- 230000002860 competitive effect Effects 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 238000007872 degassing Methods 0.000 description 1
- 230000008021 deposition Effects 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 238000000113 differential scanning calorimetry Methods 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 235000004426 flaxseed Nutrition 0.000 description 1
- SLGWESQGEUXWJQ-UHFFFAOYSA-N formaldehyde;phenol Chemical compound O=C.OC1=CC=CC=C1 SLGWESQGEUXWJQ-UHFFFAOYSA-N 0.000 description 1
- 238000001879 gelation Methods 0.000 description 1
- ZDXPYRJPNDTMRX-UHFFFAOYSA-N glutamine Natural products OC(=O)C(N)CCC(N)=O ZDXPYRJPNDTMRX-UHFFFAOYSA-N 0.000 description 1
- 150000004676 glycans Chemical class 0.000 description 1
- PEDCQBHIVMGVHV-UHFFFAOYSA-N glycerol group Chemical group OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 1
- 235000021021 grapes Nutrition 0.000 description 1
- 230000036541 health Effects 0.000 description 1
- 239000011487 hemp Substances 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 238000010348 incorporation Methods 0.000 description 1
- 238000009434 installation Methods 0.000 description 1
- 239000011810 insulating material Substances 0.000 description 1
- 239000012774 insulation material Substances 0.000 description 1
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 1
- 229920005610 lignin Polymers 0.000 description 1
- 235000020778 linoleic acid Nutrition 0.000 description 1
- OYHQOLUKZRVURQ-IXWMQOLASA-N linoleic acid Natural products CCCCC\C=C/C\C=C\CCCCCCCC(O)=O OYHQOLUKZRVURQ-IXWMQOLASA-N 0.000 description 1
- 229960004488 linolenic acid Drugs 0.000 description 1
- KQQKGWQCNNTQJW-UHFFFAOYSA-N linolenic acid Natural products CC=CCCC=CCC=CCCCCCCCC(O)=O KQQKGWQCNNTQJW-UHFFFAOYSA-N 0.000 description 1
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 1
- 238000010907 mechanical stirring Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 150000002772 monosaccharides Chemical class 0.000 description 1
- 238000000465 moulding Methods 0.000 description 1
- 235000014571 nuts Nutrition 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 238000005192 partition Methods 0.000 description 1
- 238000005502 peroxidation Methods 0.000 description 1
- 229920001568 phenolic resin Polymers 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 229920000098 polyolefin Polymers 0.000 description 1
- 229920001282 polysaccharide Polymers 0.000 description 1
- 239000005017 polysaccharide Substances 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 230000000717 retained effect Effects 0.000 description 1
- 238000000518 rheometry Methods 0.000 description 1
- WBHHMMIMDMUBKC-XLNAKTSKSA-N ricinelaidic acid Chemical compound CCCCCC[C@@H](O)C\C=C\CCCCCCCC(O)=O WBHHMMIMDMUBKC-XLNAKTSKSA-N 0.000 description 1
- 229960003656 ricinoleic acid Drugs 0.000 description 1
- FEUQNCSVHBHROZ-UHFFFAOYSA-N ricinoleic acid Natural products CCCCCCC(O[Si](C)(C)C)CC=CCCCCCCCC(=O)OC FEUQNCSVHBHROZ-UHFFFAOYSA-N 0.000 description 1
- 150000003335 secondary amines Chemical class 0.000 description 1
- 229920006135 semi-crystalline thermoplastic polymer Polymers 0.000 description 1
- 229940014800 succinic anhydride Drugs 0.000 description 1
- FAGUFWYHJQFNRV-UHFFFAOYSA-N tetraethylenepentamine Chemical compound NCCNCCNCCNCCN FAGUFWYHJQFNRV-UHFFFAOYSA-N 0.000 description 1
- 239000004634 thermosetting polymer Substances 0.000 description 1
- 229960001124 trientine Drugs 0.000 description 1
- 239000003981 vehicle Substances 0.000 description 1
- 238000009736 wetting Methods 0.000 description 1
Classifications
-
- D—TEXTILES; PAPER
- D21—PAPER-MAKING; PRODUCTION OF CELLULOSE
- D21H—PULP COMPOSITIONS; PREPARATION THEREOF NOT COVERED BY SUBCLASSES D21C OR D21D; IMPREGNATING OR COATING OF PAPER; TREATMENT OF FINISHED PAPER NOT COVERED BY CLASS B31 OR SUBCLASS D21G; PAPER NOT OTHERWISE PROVIDED FOR
- D21H17/00—Non-fibrous material added to the pulp, characterised by its constitution; Paper-impregnating material characterised by its constitution
- D21H17/20—Macromolecular organic compounds
- D21H17/33—Synthetic macromolecular compounds
- D21H17/46—Synthetic macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
- D21H17/53—Polyethers; Polyesters
-
- D—TEXTILES; PAPER
- D04—BRAIDING; LACE-MAKING; KNITTING; TRIMMINGS; NON-WOVEN FABRICS
- D04H—MAKING TEXTILE FABRICS, e.g. FROM FIBRES OR FILAMENTARY MATERIAL; FABRICS MADE BY SUCH PROCESSES OR APPARATUS, e.g. FELTS, NON-WOVEN FABRICS; COTTON-WOOL; WADDING ; NON-WOVEN FABRICS FROM STAPLE FIBRES, FILAMENTS OR YARNS, BONDED WITH AT LEAST ONE WEB-LIKE MATERIAL DURING THEIR CONSOLIDATION
- D04H1/00—Non-woven fabrics formed wholly or mainly of staple fibres or like relatively short fibres
- D04H1/40—Non-woven fabrics formed wholly or mainly of staple fibres or like relatively short fibres from fleeces or layers composed of fibres without existing or potential cohesive properties
- D04H1/58—Non-woven fabrics formed wholly or mainly of staple fibres or like relatively short fibres from fleeces or layers composed of fibres without existing or potential cohesive properties by applying, incorporating or activating chemical or thermoplastic bonding agents, e.g. adhesives
- D04H1/64—Non-woven fabrics formed wholly or mainly of staple fibres or like relatively short fibres from fleeces or layers composed of fibres without existing or potential cohesive properties by applying, incorporating or activating chemical or thermoplastic bonding agents, e.g. adhesives the bonding agent being applied in wet state, e.g. chemical agents in dispersions or solutions
Definitions
- the announced depletion of oil resources has pushed industry players in the insulation sector to study the improvement and thermal insulation, including buildings, but also vehicles.
- the present invention is part of this field of thermal insulation, without it being possible, however, to consider that it is limited in its applications to this area alone.
- this invention may also be of interest in the context of sound insulation.
- the present invention relates more particularly to a sheet of vegetable wool fibers, which can be used to thermally and / or phonically isolate a wall.
- a sheet of vegetable wool fibers which can be used to thermally and / or phonically isolate a wall.
- thermal insulation it will be sufficient to mention the thermal insulation, but it is understood that a large part of the sheets used for thermal insulation are also useful for sound insulation, and that moreover one can implement such sheets in cases where only the sound insulation is sought.
- Vegetable insulation wools can be considered as competitive products of mineral wools (glass, rock) for application, particularly in the field of eco sustainable housing. These mineral wools are mainly based on the use of synthetic polymeric materials of a thermosetting nature, such as phenol-formaldehyde.
- FR2626597 discloses a thermal and acoustic insulation panel with a mineral wool bonded by a thermosetting melamine resin.
- FR2731243 discloses a thermal and acoustic insulation panel with a glass wool bonded with a thermoplastic, such as PVC.
- Another way has been to replace mineral wools petrochemical binders with a composition formed by a monosaccharide and / or polysaccharide with a polycarboxylic organic acid having a molar mass of less than 1000.
- Such an invention is detailed in FR2924719A1.
- Vegetable wool already marketed is very often based on hemp fiber or flax.
- a semi-crystalline thermoplastic polymer polyethylene, polypropylene, polyethylene terephthalate
- inter-fiber binder to ensure their mechanical cohesion for the design of a sheet or even a plant wool insulation panel .
- But its petrochemical origin prohibits these tablecloths or insulation boards to display a natural or ecological product label.
- each plant species is characterized by a specific proportion of cellulose-hemicellulose-lignin
- thermoplastic polymers polyolefin (polyethylene, polypropylene) or polyester (polyethylene terephthalate). Due to their semi-crystalline nature, these polymers can melt during a rise in temperature, which allows them to diffuse within the fibrous network. After cooling to room temperature, these polymers cover a high mechanical rigidity to ensure the inter-fiber cohesion necessary for the production of an insulating layer.
- the insulating plies are produced in the form of rigid or semi-rigid panels, which can be placed for example between a wall and a cladding, to improve the thermal insulation of said wall. They can also be used to insulate a non-flat wall, such as a car door. In this case, it is possible either to form a non-planar panel, for example by molding, or else to form the sheet directly on its support. To do this, one can prepare on one side the fibers, on the other the polymer. The polymer can then be deposited on the fibers and then project the assembly onto the wall to be covered. It is also possible to project at the same time, by a suitable projection device, the fibers and the polymer. The choice of the process will depend on the characteristics of the chosen polymers.
- tablecloth will be used to describe a layer of fibers, bound by a binder, with any shape, flat or not, whether preformed to form a separate part, or whether it is formed at the time of being applied to the wall of which it must improve the thermal and / or sound insulation.
- panel since the panel represents the most common application. But here too the variants described apply to any layers.
- thermoplastic binder derived from petroleum has several disadvantages. Indeed, it is not possible to recycle these materials once mixed with the plant fibers. Moreover, because of their 100% petrochemical origin, these different classes of binders can in no way give the insulating material a "green" label. Finally, the mechanical characteristics close to the various types of thermoplastics used limit the variation of a wide range of plant wools.
- the relative proportion of polymer makes it possible to vary the physical properties of the fibrous panel.
- the mass percentage of the thermoplastic matrix must not exceed 10 to 20%. This therefore strongly limits the use of this means to confer the desired properties to a panel.
- the manufacturing process can also be used to vary the physical properties of the panel.
- the compaction pressure will impact in particular the density of the plant wool, but also at the same time its insulating nature.
- the mode of dispersion of the polymer matrix (in the form of powder or fibers) within the plant network is also another element of influence.
- the means of action are, however, extremely limited.
- the present invention proposes to remedy at least some of the aforementioned drawbacks and proposes to substitute the thermoplastic binder of petrochemical origin with a thermosetting polymer formulation derived from Green Chemistry.
- the latter is based on the reactive mixture of an epoxidized vegetable oil with a hardener.
- the invention relates to a web of vegetable wool fibers.
- This sheet is impregnated with an epoxidized vegetable oil and a hardener.
- the combination of epoxidized vegetable oil and hardener is a binder allowing the web of vegetable wool fibers to be a solid and consistent. This concept allows a wide range of formulations depending on the intrinsic chemical nature of its components, the composition of the mixture or the associated polymerization conditions (time, temperature).
- the epoxidized vegetable oil may be an oil rich in unsaturated fatty acids, in particular an oil obtained from a plant of the list consisting of flax, sunflower, soya, olive, Tung wood, cotton, rapeseed, castor oil, cashew nuts, peanuts, grape seeds; these oils have been identified as excellent components for the invention. They can be used pure or as a mixture of the above-mentioned oils. Any other oil having the particularity of being rich in unsaturated fatty acids may be considered as a good candidate for the base of the present invention,
- the epoxidized vegetable oil may be an epoxidized linseed oil; this is particularly interesting because its proportion of unsaturated fatty acids exceeds 90% with in particular a high composition of linoleic and linolenic fatty acids; Moreover, since it is not edible, its valorization does not conflict with an initially oriented food production.
- Said epoxidized linseed oil may comprise from 2 to 6 epoxide groups; oils with few epoxide groups will be selected to obtain more flexible plies, and oils with more epoxide groups will allow to obtain more rigid plies.
- Said hardener may be a compound carrying a plurality of primary or secondary amines (n greater than or equal to 2).
- Said polyamine may be of biological origin, which enables the web to be produced entirely from biological components
- Said hardener may be an acid anhydride which may be mono or multifunctional. However, it should be noted that each anhydride ring may react with two epoxide units
- Said anhydride can be of biological origin, which enables the web to be produced entirely from biological components
- the present invention also relates to a thermal insulation panel comprising a sheet according to the invention, wherein said epoxidized vegetable oil and said hardener form a binder so as to impart mechanical cohesion sufficient to said panel; such a panel can be used easily in construction.
- the present invention relates to a method of manufacturing a sheet or a panel according to the invention comprising the following steps:
- a solvent can be added to said mixture before it is removed, so as to make it less viscous
- Said fibers may be deposited on a conveyor belt, the oil / fiber ratio being regulated by the oil delivery rate and the speed of travel of the treadmill, preferably a suction of the mixture through the fibers being added so as to improve penetration and diffusion of the mixture through the fibers
- Said fibers can be placed in a horizontal rotor where they are brewed and dispersed, before the said mixture is deposited by direct spraying
- the web After removal of said mixture the web may be pressed, either through a rolling mill to regulate the thickness of the fibrous mat, or by a mold formed by a set of impression / counterprint, and then subjected to a heat treatment to allow the crosslinking of the mixture.
- the advantage of the present invention is that the binder used is largely of origin biological and, according to some preferred embodiments, completely of biological origin.
- FIG. 1 represents an essential chemical formula in the process according to the invention
- the present invention relates to a web of vegetable wool fibers. Such fibers are known for their insulating characteristics. Nevertheless, to be able to be formed into a sheet or even into a panel, it is necessary to add a binder. According to the invention, this binder consists of an epoxidized vegetable oil and a hardener.
- Table 2 Typical composition of a linseed oil
- the epoxidation of a linseed oil makes it possible, for example, to give access to a molecule bearing from 2 to 6 epoxide groups, which groups will be able to react with groups of anhydride or polyamine type hardener.
- the selection of the oil can therefore affect the rigidity of the web by the choice of the number of epoxide groups present: the more epoxy groups, the greater the rigidity of the web.
- the invention encompasses two classes of hardeners. The first is formed by polyamines (molecules carrying several amino functions), the second by acid and acid anhydrides.
- a primary amine is capable of opening two epoxide groups to form two covalent bonds.
- a diamine of standard chemical formula H2N-R-NH2 can react with four epoxide groups (H2 is a primary amine end and R is the central block). This reaction can give rise to the formation of a three-dimensional polymer network if these two epoxide groups are carried by two different macromolecular chains. The transformation is called crosslinking.
- the schematic diagram is proposed in Figure 1.
- the polyamine-epoxy reaction is carried out through the mixture formed by an epoxidized vegetable oil with a diamine hardener in order to produce a thermosetting formulation.
- the proportion of each compound in the reaction mixture may be chosen depending on the desired degree of crosslinking in order to adjust the stiffness material or its default hardener pepper if necessary. But for a total consumption of the reagents leading to a stable product, it is important to work in stoichiometric quantities. For example, for an epoxidized linseed oil carrying 5.45 epoxide functions per triglyceride unit, the stoichiometry of the formulation is 1.36 moles of primary diamine per 1 mole of oil.
- the study of the reactivity can be carried out by differential scanning calorimetry by following the evolution of the heat released by the crosslinking reaction.
- Dynamic rheometry can also be used to determine the characteristics of the polymerization kinetics at a given temperature, such as its speed or the time to reach equilibrium of the reaction. This key information obtained at different temperatures is useful in order to determine the optimal factors of implementation (temperature and duration) necessary for the construction of the thermal cycle of implementation.
- a first generation of binders based on epoxidized vegetable oil can be developed by using polyamines from petrochemicals. Compared to the current thermoplastic solution, this type of binders already has the advantage of being based on a much higher renewable carbon content due to the presence of vegetable oil in the thermosetting formulation.
- central block R of the polyamine makes it possible to modulate the properties of the final matrix, in particular in terms of mechanical or thermal properties. It is then possible to decline a wide range of plant wools depending on the desired flexibility or mechanical rigidity.
- R - rigid central block
- isophorone diamine also referred to as 5-amino-1,3,3-trimethylcyclohexanemethylamine
- m-xylylenediamine m-xylylenediamine.
- the binder derived from this type of polyamine is particularly suitable for the production of dense and rigid thermal insulation wool panels. It should be noted that certain aromatic diamines of the "methylene diamine” type must be discarded because of their health risk.
- a diamine displaying an aliphatic central block will allow the manufacture of more flexible binders.
- This same flexibility can be modulated by the length of the aliphatic unit, or even the presence of flexible chemical patches of ether types. Examples include ethylene diamine, 1,4-diaminobutane, hexamethylene diamine, bis (3-aminopropyl) amine, 1- (2-aminoethyl) piperazine, Jeffamines.
- the flexibility of the binder allows the production of wool panels much more flexible and able to adapt to laying in areas of complex geometry. These same fibrous panels exhibit a much lower compression set after compression than that observed with rigid binder based panels. It is worth noting that the proportion of binder in the fibrous cluster nevertheless makes it possible to modulate the difference between the two types of hardeners.
- reaction between an amine terminus and an epoxide group can also be conducted with an epoxidized oil cured with a polyamine, i.e., a chemical compound having more than two amino functions.
- a polyamine i.e., a chemical compound having more than two amino functions.
- This solution is a new lever allowing the extension of the range of binders to meet in particular mechanical or thermal specific constraints.
- Several commercial polyamines can serve as a basis for this concept, such as diethylene triamine, triethylene tetramine, tetraethylene pentamine, T-Jeffamines.
- a second generation of vegetable wool binders can be obtained by reacting the epoxidized vegetable oil with diamines produced from biological sources.
- diamines produced from biological sources For example, the compound "1-4 diaminobutane" previously mentioned, can also be obtained by green chemistry including hydrolysis of animal proteins.
- Another compound that can be produced from biological components is 1,5-diaminopentane.
- some amino acids carry several amino functions that allow them to satisfy the hardener function. For example, lysine, arginine, asparagine, glutamine. All these hardeners allow, like their counterparts from petrochemicals, to crosslink the epoxidized oil during an increase in temperature.
- the binders thus obtained allow the design of 100% thermal insulation panels of biological origin.
- the present invention also encompasses vegetable wools whose binder has been obtained by the polymerization of the epoxidized vegetable oil with an anhydride hardener.
- Various anhydride compounds have been tested to extend the range of binders assigned to vegetable wool. Some examples can be cited namely phthalic anhydride, maleic anhydride, succinic anhydride, hexahydrophthalic anhydride or methylhexahydrophthalic acid.
- phthalic anhydride maleic anhydride, succinic anhydride, hexahydrophthalic anhydride or methylhexahydrophthalic acid.
- Each of course requires the definition of suitable crosslinking temperatures to take into account the reactivity of the mixture. In all cases, the reaction rate of the anhydride hardener with respect to the oil is slower than that observed with the polyamine hardeners. This point is important in the context of industrial production, even if the crosslinking reaction can be catalyzed, in particular by the use of an amino derivative
- the anhydride route can also be explored by Green Chemistry.
- itaconic anhydride can be obtained by treatment of citric acid.
- citric acid mixed with epoxidized vegetable oil, it allows the production of a new binder derived entirely from biological sources.
- the preparation of the binder consists in mixing the epoxidized vegetable oil and its hardener. If the latter is solid at room temperature, it may be heated beyond its melting point but below its vaporization and degradation temperature. The oil will of course be heated to the same temperature in order to avoid any crystallization of the hardener during the "oil / hardener" mixture.
- the stoichiometry of the mixture depends on the degree of epoxidation of the oil (ie the amount of epoxide groups per triglyceride group) but also on the functionality of the hardener (diamine, polyamine, acid anhydride, etc.). an amino group can react with two epoxide groups.
- the deposition temperature is chosen so as to maintain the entire reaction medium in the liquid state. It is therefore at least equal to the mixing temperature. It should not be operated at an excessive temperature at which the crosslinking process would occur too quickly. Indeed, a temperature too close to the reaction range can cause rapid gelation of the mixture and at the same time hinder the diffusion of the mixture in the web.
- the viscosity of the "oil / hardener" mixture is sufficiently low to allow its vaporization on the vegetable fibers by means of nozzles. If necessary, it can be lowered by adding solvent, the choice of which must be defined according to the type of hardener used.
- solvent the choice of which must be defined according to the type of hardener used.
- chloroform acetate of ethyl, certain alkanes (hexane, heptane), petroleum ether, diethyl ether, dichloromethane, toluene, THF or dioxane ...
- the wetting of the fibers can be effected by various methods.
- a first technique is to vaporize the thermosetting formulation on the fibers previously arranged on a conveyor belt.
- the spraying rate of the material and / or the running speed of the carpet make it possible to regulate the oil / fiber ratio.
- An aspiration of the resin through the fibrous network can be operated to allow better penetration and diffusion of the binder through the fibrous tissue.
- the previously dried plant fibers are placed in a horizontal rotor where they are brewed and dispersed.
- the impregnation phase with the oil / hardener mixture can then occur by direct spraying.
- the sheet of fibers thus moistened is then pressed either through a rolling mill to regulate the thickness of the fibrous mat, or by a mold formed by a set of imprint / counter- footprint. Then, the assembly is subjected to a heat treatment to allow the crosslinking of the "oil-hardener" mixture.
- the final heating step can be carried out by means of infrared emitting lamps, a hot air tunnel or by direct thermal contact.
- the vegetable wool panels thus produced can be used as thermal insulation elements for traditional construction as a substitute for mineral wool panels (glass or rock). Based largely or wholly on products of biological origin, wool plants offer a very interesting alternative to lignocellulosic wools based on petrochemical binder, particularly in the context of sustainable housing (timber frame house). It is important to note that, beyond the sole thermal aspect, vegetable wool panels also provide a soundproofing function. This provides several benefits:
- Vegetable wool based on a polymer binder partly or wholly derived from Green Chemistry is perfectly in line with the expectations of sustainable eco-housing, whose market shares are growing steadily in our modern society.
- thermosetting binder • The chemical synthesis of the green thermosetting binder is based on chemistry in line with the expectations of an industrial production.
- the oil-based binder disperses more easily in the plant network than the binders petrochemical thermoplastics. The amount of product to use remains low.
- the biosourced epoxy binder can be declined through a wide variety of chemical compositions. Each has specific properties (mechanical, thermal %) that allow to decline a wide range of plant wools able to adapt to very different functions (rigid or flexible wool, wool with a low compression set ).
- the biosourced binder can be deposited on the constituent plant fibers of the thermal insulation wool by processes very different from those used for the thermoplastic petrochemical binder.
- Various methods very economical in product can be used: spraying, infusion, dispersion, projection ...
- a biosourced plant wool is not synonymous with a product with a short shelf life because "biobased” is not synonymous with “biodegradable” ...
- Vegetable insulation wools are known to be more sensitive to moisture and fire than mineral wools. But, this point is in no way induced by the use of a binder derived from epoxidized vegetable oil.
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- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Dispersion Chemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Textile Engineering (AREA)
- Dry Formation Of Fiberboard And The Like (AREA)
- Paper (AREA)
- Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
- Reinforced Plastic Materials (AREA)
Abstract
Description
Claims
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR1152967A FR2973812A1 (fr) | 2011-04-06 | 2011-04-06 | Nappe de fibre de laine vegetale impregnee d'une huile vegetale epoxydee |
| FR1154264A FR2973813B1 (fr) | 2011-04-06 | 2011-05-17 | Nappe de fibre de laine vegetale impregnee d'une huile vegetale epoxydee |
| PCT/FR2012/050744 WO2012136940A2 (fr) | 2011-04-06 | 2012-04-05 | Nappe de fibre de laine vegetale impregnee d'une huile vegetale epoxydee |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| EP2694715A2 true EP2694715A2 (fr) | 2014-02-12 |
Family
ID=44543376
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| EP12720250.5A Withdrawn EP2694715A2 (fr) | 2011-04-06 | 2012-04-05 | Nappe de fibre de laine vegetale impregnee d'une huile vegetale epoxydee |
Country Status (5)
| Country | Link |
|---|---|
| US (1) | US20140083636A1 (fr) |
| EP (1) | EP2694715A2 (fr) |
| CA (1) | CA2832405A1 (fr) |
| FR (2) | FR2973812A1 (fr) |
| WO (1) | WO2012136940A2 (fr) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR3024981B1 (fr) | 2014-08-22 | 2016-09-09 | Univ Montpellier 2 Sciences Et Techniques | Derives polyesters d'acides gras de polyglycosides |
| EP3632949A1 (fr) * | 2018-10-02 | 2020-04-08 | Vito NV | Procédé de production de résines époxy |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2379163A (en) * | 1943-07-24 | 1945-06-26 | Westinghouse Electric Corp | Producing molded products |
| US3625876A (en) * | 1968-07-02 | 1971-12-07 | Continental Can Co | Vinylidene chloride polymer coating composition for thermoplastic films |
| FR2626597B1 (fr) | 1988-02-01 | 1992-07-17 | Saint Gobain Isover | Panneau d'isolation thermique et acoustique |
| FR2731243B1 (fr) | 1995-03-03 | 1997-04-04 | Saint Gobain Isover | Panneau de protection acoustique |
| DE19952364A1 (de) * | 1999-10-30 | 2001-07-19 | Cognis Deutschland Gmbh | Lagerstabile Prepregs auf Basis duroplastischer, oleochemischer Matrices |
| EP1116742A1 (fr) * | 2000-01-12 | 2001-07-18 | Fina Research S.A. | Compositions S-B-S |
| FR2924719B1 (fr) | 2007-12-05 | 2010-09-10 | Saint Gobain Isover | Composition d'encollage pour laine minerale comprenant un monosaccharide et/ou un polysaccharide et un acide organique polycarboxylique, et produits isolants obtenus. |
-
2011
- 2011-04-06 FR FR1152967A patent/FR2973812A1/fr active Pending
- 2011-05-17 FR FR1154264A patent/FR2973813B1/fr active Active
-
2012
- 2012-04-05 WO PCT/FR2012/050744 patent/WO2012136940A2/fr not_active Ceased
- 2012-04-05 EP EP12720250.5A patent/EP2694715A2/fr not_active Withdrawn
- 2012-04-05 CA CA2832405A patent/CA2832405A1/fr not_active Abandoned
- 2012-04-05 US US14/110,112 patent/US20140083636A1/en not_active Abandoned
Non-Patent Citations (1)
| Title |
|---|
| See references of WO2012136940A2 * |
Also Published As
| Publication number | Publication date |
|---|---|
| WO2012136940A2 (fr) | 2012-10-11 |
| FR2973812A1 (fr) | 2012-10-12 |
| FR2973813A1 (fr) | 2012-10-12 |
| CA2832405A1 (fr) | 2012-10-11 |
| FR2973813B1 (fr) | 2021-04-16 |
| WO2012136940A3 (fr) | 2013-02-07 |
| US20140083636A1 (en) | 2014-03-27 |
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