US20120041117A1 - Binder Compound - Google Patents
Binder Compound Download PDFInfo
- Publication number
- US20120041117A1 US20120041117A1 US13/027,552 US201113027552A US2012041117A1 US 20120041117 A1 US20120041117 A1 US 20120041117A1 US 201113027552 A US201113027552 A US 201113027552A US 2012041117 A1 US2012041117 A1 US 2012041117A1
- Authority
- US
- United States
- Prior art keywords
- binder compound
- binder
- resin
- specifically
- compound according
- 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.)
- Abandoned
Links
- 150000001875 compounds Chemical class 0.000 title claims abstract description 134
- 239000011230 binding agent Substances 0.000 title claims abstract description 110
- 239000012528 membrane Substances 0.000 claims abstract description 54
- 239000011347 resin Substances 0.000 claims abstract description 46
- 229920005989 resin Polymers 0.000 claims abstract description 46
- 229920000642 polymer Polymers 0.000 claims abstract description 26
- 239000003921 oil Substances 0.000 claims description 44
- 235000019198 oils Nutrition 0.000 claims description 44
- 239000000853 adhesive Substances 0.000 claims description 23
- 239000000945 filler Substances 0.000 claims description 21
- 230000001070 adhesive effect Effects 0.000 claims description 20
- FACXGONDLDSNOE-UHFFFAOYSA-N buta-1,3-diene;styrene Chemical compound C=CC=C.C=CC1=CC=CC=C1.C=CC1=CC=CC=C1 FACXGONDLDSNOE-UHFFFAOYSA-N 0.000 claims description 14
- 229920000468 styrene butadiene styrene block copolymer Polymers 0.000 claims description 14
- -1 polypropylene Polymers 0.000 claims description 10
- 239000003963 antioxidant agent Substances 0.000 claims description 9
- 230000003078 antioxidant effect Effects 0.000 claims description 9
- 239000000839 emulsion Substances 0.000 claims description 7
- 229920000728 polyester Polymers 0.000 claims description 7
- 235000015112 vegetable and seed oil Nutrition 0.000 claims description 7
- 239000008158 vegetable oil Substances 0.000 claims description 7
- 239000004743 Polypropylene Substances 0.000 claims description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 6
- VSKJLJHPAFKHBX-UHFFFAOYSA-N 2-methylbuta-1,3-diene;styrene Chemical compound CC(=C)C=C.C=CC1=CC=CC=C1.C=CC1=CC=CC=C1 VSKJLJHPAFKHBX-UHFFFAOYSA-N 0.000 claims description 5
- 239000000025 natural resin Substances 0.000 claims description 5
- 229920000747 poly(lactic acid) Polymers 0.000 claims description 5
- 229920001155 polypropylene Polymers 0.000 claims description 5
- 229920001935 styrene-ethylene-butadiene-styrene Polymers 0.000 claims description 5
- 229920002367 Polyisobutene Polymers 0.000 claims description 4
- 239000003995 emulsifying agent Substances 0.000 claims description 4
- 229920000098 polyolefin Polymers 0.000 claims description 4
- 239000002904 solvent Substances 0.000 claims description 4
- 239000004952 Polyamide Substances 0.000 claims description 3
- 229920000331 Polyhydroxybutyrate Polymers 0.000 claims description 3
- 150000001244 carboxylic acid anhydrides Chemical group 0.000 claims description 3
- 125000003700 epoxy group Chemical group 0.000 claims description 3
- 125000000524 functional group Chemical group 0.000 claims description 3
- 239000005015 poly(hydroxybutyrate) Substances 0.000 claims description 3
- 229920002647 polyamide Polymers 0.000 claims description 3
- 125000002843 carboxylic acid group Chemical group 0.000 claims description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 20
- 235000014113 dietary fatty acids Nutrition 0.000 description 15
- 239000000194 fatty acid Substances 0.000 description 15
- 229930195729 fatty acid Natural products 0.000 description 15
- 239000010426 asphalt Substances 0.000 description 14
- 230000008901 benefit Effects 0.000 description 14
- 150000004665 fatty acids Chemical class 0.000 description 11
- 238000004519 manufacturing process Methods 0.000 description 11
- 229910000019 calcium carbonate Inorganic materials 0.000 description 10
- 239000003784 tall oil Substances 0.000 description 8
- 238000000576 coating method Methods 0.000 description 7
- 150000002148 esters Chemical class 0.000 description 7
- 238000000034 method Methods 0.000 description 7
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical class OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 7
- 239000000047 product Substances 0.000 description 7
- 238000002156 mixing Methods 0.000 description 6
- 239000011248 coating agent Substances 0.000 description 5
- 238000004040 coloring Methods 0.000 description 5
- 230000002787 reinforcement Effects 0.000 description 5
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- 239000004615 ingredient Substances 0.000 description 4
- 230000003993 interaction Effects 0.000 description 4
- 229920006254 polymer film Polymers 0.000 description 4
- 235000012424 soybean oil Nutrition 0.000 description 4
- 239000000758 substrate Substances 0.000 description 4
- 239000000454 talc Substances 0.000 description 4
- 229910052623 talc Inorganic materials 0.000 description 4
- 235000012222 talc Nutrition 0.000 description 4
- 235000013311 vegetables Nutrition 0.000 description 4
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
- 239000004698 Polyethylene Substances 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- 235000019486 Sunflower oil Nutrition 0.000 description 3
- 239000003925 fat Substances 0.000 description 3
- 235000019197 fats Nutrition 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 230000003647 oxidation Effects 0.000 description 3
- 238000007254 oxidation reaction Methods 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- 239000002994 raw material Substances 0.000 description 3
- 239000002600 sunflower oil Substances 0.000 description 3
- 239000000057 synthetic resin Substances 0.000 description 3
- 229920003002 synthetic resin Polymers 0.000 description 3
- 244000226021 Anacardium occidentale Species 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- 235000019738 Limestone Nutrition 0.000 description 2
- 241001465754 Metazoa Species 0.000 description 2
- RSWGJHLUYNHPMX-ONCXSQPRSA-N abietic acid Chemical compound C([C@@H]12)CC(C(C)C)=CC1=CC[C@@H]1[C@]2(C)CCC[C@@]1(C)C(O)=O RSWGJHLUYNHPMX-ONCXSQPRSA-N 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- 235000019519 canola oil Nutrition 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 235000020226 cashew nut Nutrition 0.000 description 2
- 238000010276 construction Methods 0.000 description 2
- 238000005336 cracking Methods 0.000 description 2
- 235000019387 fatty acid methyl ester Nutrition 0.000 description 2
- 150000002191 fatty alcohols Chemical class 0.000 description 2
- 230000002349 favourable effect Effects 0.000 description 2
- 239000007849 furan resin Substances 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- IPCSVZSSVZVIGE-UHFFFAOYSA-N hexadecanoic acid Chemical compound CCCCCCCCCCCCCCCC(O)=O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 description 2
- 239000006028 limestone Substances 0.000 description 2
- 235000021388 linseed oil Nutrition 0.000 description 2
- 239000000944 linseed oil Substances 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 239000012766 organic filler Substances 0.000 description 2
- 230000020477 pH reduction Effects 0.000 description 2
- 239000003973 paint Substances 0.000 description 2
- 239000002530 phenolic antioxidant Substances 0.000 description 2
- 239000000049 pigment Substances 0.000 description 2
- 239000004033 plastic Substances 0.000 description 2
- 229920003023 plastic Polymers 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 238000006722 reduction reaction Methods 0.000 description 2
- 230000000717 retained effect Effects 0.000 description 2
- 239000010454 slate Substances 0.000 description 2
- 239000000344 soap Substances 0.000 description 2
- 150000003626 triacylglycerols Chemical class 0.000 description 2
- 239000002699 waste material Substances 0.000 description 2
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 1
- JOLVYUIAMRUBRK-UHFFFAOYSA-N 11',12',14',15'-Tetradehydro(Z,Z-)-3-(8-Pentadecenyl)phenol Natural products OC1=CC=CC(CCCCCCCC=CCC=CCC=C)=C1 JOLVYUIAMRUBRK-UHFFFAOYSA-N 0.000 description 1
- KGRVJHAUYBGFFP-UHFFFAOYSA-N 2,2'-Methylenebis(4-methyl-6-tert-butylphenol) Chemical compound CC(C)(C)C1=CC(C)=CC(CC=2C(=C(C=C(C)C=2)C(C)(C)C)O)=C1O KGRVJHAUYBGFFP-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
- YLKVIMNNMLKUGJ-UHFFFAOYSA-N 3-Delta8-pentadecenylphenol Natural products CCCCCCC=CCCCCCCCC1=CC=CC(O)=C1 YLKVIMNNMLKUGJ-UHFFFAOYSA-N 0.000 description 1
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 1
- 244000188595 Brassica sinapistrum Species 0.000 description 1
- JOLVYUIAMRUBRK-UTOQUPLUSA-N Cardanol Chemical compound OC1=CC=CC(CCCCCCC\C=C/C\C=C/CC=C)=C1 JOLVYUIAMRUBRK-UTOQUPLUSA-N 0.000 description 1
- FAYVLNWNMNHXGA-UHFFFAOYSA-N Cardanoldiene Natural products CCCC=CCC=CCCCCCCCC1=CC=CC(O)=C1 FAYVLNWNMNHXGA-UHFFFAOYSA-N 0.000 description 1
- 229920003043 Cellulose fiber Polymers 0.000 description 1
- 241000195493 Cryptophyta Species 0.000 description 1
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical class OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 1
- 241000287828 Gallus gallus Species 0.000 description 1
- 241000221089 Jatropha Species 0.000 description 1
- OYHQOLUKZRVURQ-HZJYTTRNSA-N Linoleic acid Chemical compound CCCCC\C=C/C\C=C/CCCCCCCC(O)=O OYHQOLUKZRVURQ-HZJYTTRNSA-N 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
- 235000019482 Palm oil Nutrition 0.000 description 1
- 235000021314 Palmitic acid Nutrition 0.000 description 1
- 235000019483 Peanut oil Nutrition 0.000 description 1
- 229920001131 Pulp (paper) Polymers 0.000 description 1
- 235000019484 Rapeseed oil Nutrition 0.000 description 1
- 235000019485 Safflower oil Nutrition 0.000 description 1
- 235000021355 Stearic acid Nutrition 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
- RREGISFBPQOLTM-UHFFFAOYSA-N alumane;trihydrate Chemical compound O.O.O.[AlH3] RREGISFBPQOLTM-UHFFFAOYSA-N 0.000 description 1
- 239000012298 atmosphere Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 description 1
- 239000000920 calcium hydroxide Substances 0.000 description 1
- 229910001861 calcium hydroxide Inorganic materials 0.000 description 1
- 235000011116 calcium hydroxide Nutrition 0.000 description 1
- 239000000828 canola oil Substances 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- PTFIPECGHSYQNR-UHFFFAOYSA-N cardanol Natural products CCCCCCCCCCCCCCCC1=CC=CC(O)=C1 PTFIPECGHSYQNR-UHFFFAOYSA-N 0.000 description 1
- 239000004359 castor oil Substances 0.000 description 1
- 235000019438 castor oil Nutrition 0.000 description 1
- 235000019864 coconut oil Nutrition 0.000 description 1
- 239000003240 coconut oil Substances 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 239000007799 cork Substances 0.000 description 1
- 235000005687 corn oil Nutrition 0.000 description 1
- 235000012343 cottonseed oil Nutrition 0.000 description 1
- 239000002385 cottonseed oil Substances 0.000 description 1
- 230000003292 diminished effect Effects 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- 230000009970 fire resistant effect Effects 0.000 description 1
- 235000021323 fish oil Nutrition 0.000 description 1
- 229940013317 fish oils Drugs 0.000 description 1
- 235000013312 flour Nutrition 0.000 description 1
- 239000010881 fly ash Substances 0.000 description 1
- 239000000446 fuel Substances 0.000 description 1
- 125000005456 glyceride group Chemical group 0.000 description 1
- 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 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 239000011256 inorganic filler Substances 0.000 description 1
- 239000001023 inorganic pigment Substances 0.000 description 1
- JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 description 1
- 238000006317 isomerization reaction Methods 0.000 description 1
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 1
- 238000002386 leaching Methods 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
- 239000007788 liquid Substances 0.000 description 1
- 230000007774 longterm Effects 0.000 description 1
- 230000014759 maintenance of location Effects 0.000 description 1
- 235000012054 meals Nutrition 0.000 description 1
- 239000002923 metal particle Substances 0.000 description 1
- WQEPLUUGTLDZJY-UHFFFAOYSA-N n-Pentadecanoic acid Natural products CCCCCCCCCCCCCCC(O)=O WQEPLUUGTLDZJY-UHFFFAOYSA-N 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 1
- 235000021313 oleic acid Nutrition 0.000 description 1
- 239000004006 olive oil Substances 0.000 description 1
- 235000008390 olive oil Nutrition 0.000 description 1
- 239000012860 organic pigment Substances 0.000 description 1
- 239000002540 palm oil Substances 0.000 description 1
- 239000000312 peanut oil Substances 0.000 description 1
- 239000003209 petroleum derivative Substances 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 229920000139 polyethylene terephthalate Polymers 0.000 description 1
- 239000005020 polyethylene terephthalate Substances 0.000 description 1
- 239000011044 quartzite Substances 0.000 description 1
- 230000000630 rising effect Effects 0.000 description 1
- 235000005713 safflower oil Nutrition 0.000 description 1
- 239000003813 safflower oil Substances 0.000 description 1
- 239000004576 sand Substances 0.000 description 1
- 238000007127 saponification reaction Methods 0.000 description 1
- 235000003441 saturated fatty acids Nutrition 0.000 description 1
- 150000004671 saturated fatty acids Chemical class 0.000 description 1
- 235000011803 sesame oil Nutrition 0.000 description 1
- 239000008159 sesame oil Substances 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 239000004575 stone Substances 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 230000002459 sustained effect Effects 0.000 description 1
- 239000003760 tallow Substances 0.000 description 1
- 239000004753 textile Substances 0.000 description 1
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical class OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1
- 239000002383 tung oil Substances 0.000 description 1
- 150000004670 unsaturated fatty acids Chemical class 0.000 description 1
- 235000021122 unsaturated fatty acids Nutrition 0.000 description 1
- 229920006305 unsaturated polyester Polymers 0.000 description 1
- 238000010792 warming Methods 0.000 description 1
Images
Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J193/00—Adhesives based on natural resins; Adhesives based on derivatives thereof
- C09J193/04—Rosin
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L101/00—Compositions of unspecified macromolecular compounds
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L53/00—Compositions of block copolymers containing at least one sequence of a polymer obtained by reactions only involving carbon-to-carbon unsaturated bonds; Compositions of derivatives of such polymers
- C08L53/02—Compositions of block copolymers containing at least one sequence of a polymer obtained by reactions only involving carbon-to-carbon unsaturated bonds; Compositions of derivatives of such polymers of vinyl-aromatic monomers and conjugated dienes
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L93/00—Compositions of natural resins; Compositions of derivatives thereof
- C08L93/04—Rosin
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L97/00—Compositions of lignin-containing materials
- C08L97/005—Lignin
-
- E—FIXED CONSTRUCTIONS
- E04—BUILDING
- E04C—STRUCTURAL ELEMENTS; BUILDING MATERIALS
- E04C2/00—Building elements of relatively thin form for the construction of parts of buildings, e.g. sheet materials, slabs, or panels
- E04C2/02—Building elements of relatively thin form for the construction of parts of buildings, e.g. sheet materials, slabs, or panels characterised by specified materials
- E04C2/26—Building elements of relatively thin form for the construction of parts of buildings, e.g. sheet materials, slabs, or panels characterised by specified materials composed of materials covered by two or more of groups E04C2/04, E04C2/08, E04C2/10 or of materials covered by one of these groups with a material not specified in one of the groups
- E04C2/28—Building elements of relatively thin form for the construction of parts of buildings, e.g. sheet materials, slabs, or panels characterised by specified materials composed of materials covered by two or more of groups E04C2/04, E04C2/08, E04C2/10 or of materials covered by one of these groups with a material not specified in one of the groups combinations of materials fully covered by groups E04C2/04 and E04C2/08
-
- E—FIXED CONSTRUCTIONS
- E04—BUILDING
- E04D—ROOF COVERINGS; SKY-LIGHTS; GUTTERS; ROOF-WORKING TOOLS
- E04D5/00—Roof covering by making use of flexible material, e.g. supplied in roll form
- E04D5/06—Roof covering by making use of flexible material, e.g. supplied in roll form by making use of plastics
-
- E—FIXED CONSTRUCTIONS
- E04—BUILDING
- E04D—ROOF COVERINGS; SKY-LIGHTS; GUTTERS; ROOF-WORKING TOOLS
- E04D5/00—Roof covering by making use of flexible material, e.g. supplied in roll form
- E04D5/10—Roof covering by making use of flexible material, e.g. supplied in roll form by making use of compounded or laminated materials, e.g. metal foils or plastic films coated with bitumen
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L2205/00—Polymer mixtures characterised by other features
- C08L2205/02—Polymer mixtures characterised by other features containing two or more polymers of the same C08L -group
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L95/00—Compositions of bituminous materials, e.g. asphalt, tar, pitch
Definitions
- the present invention relates to a binder compound based on natural oils, polymer and resin.
- Such binder compounds can for example be used for production of roof covering membranes and similar as an environmentally friendly alternative to bituminous roof covering membranes.
- bitumen is a by-product of the petrochemical industry which offers a cheap and high quality raw material for the production of roof covering membranes or asphalt. Due to rising demand for petroleum products for use in chemistry and as fuel, the quality and availability of high quality bitumen has diminished greatly. Also the use of bituminous products has a harmful influence on the environment as its production causes great environmental pressure. Another disadvantage of the use of bitumen is the acidification of rain water as a result of interaction of UV and bitumen.
- WO 2009/071653 describes a compound which consists of resin of vegetable origin, oil of vegetable origin and a polymer that contains functional groups selected from the carboxylic acid anhydride, carboxylic acid and epoxide groups.
- the disadvantage of this compound is that only such functionalized polymers can be used, which entails a restriction in suitable polymers and in addition increases the cost price of this compound.
- the object of the present invention is to provide a binder compound in which oil of natural origin, resin and polymer are used, while allowing a wider choice of polymer.
- a binder compound comprising:
- Such a binder compound offers the advantage that it is an environmentally friendly alternative to binder compounds based on bitumen as it contains natural oil which is a source of renewable carbon and therefore has little or no influence on the CO2 balance in the atmosphere. Another important benefit is that the problem of acid leaching, which can lead to acidified rain water, is avoided because natural oil does not lead to acidification under the effect of UV. As a result the recovered rain water can be used with less further treatment for sanitary or other applications. Another benefit is that the roof covering membranes and cold adhesives which contain the binder compound according to the invention can be processed, applied or used in the same way as bituminous roof covering membranes and cold adhesives.
- the binder compound has the following viscosity, namely a viscosity of 1400 to 25000 Pa ⁇ s at 180° C. This viscosity is similar to the viscosity of modified bitumen binder compounds. Due to this viscosity the binder compound will be solid at an ambient temperature of approximately ⁇ 15° C. to approximately 40° C., which is necessary for example for the setting and hardness of roof covering membranes and cold adhesives containing the binder compound. At ambient temperatures above around 25° C. the binder compound also remains cohesive and will consequently not flow out, which again is favorable for use in roof covering membranes and road construction.
- the binder compound also has a relatively low liquefaction temperature, namely 100 to 180° C. This is the temperature at which the binder compound acquires a specific degree of plasticity as defined in the profession by the technical standard ASTM D36/D36M-09 of Dec. 15, 2009.
- the binder compound must be sufficiently plastic when for example it forms part of a roof covering membrane which is applied to a substrate or surface by means of burner lances, because this achieves a good adhesion of the roof covering membrane to the substrate.
- Burner lances typically use a flame with a flame temperature of 180 to 220° C.
- the binder compound At this liquefaction temperature, the binder compound will already be sufficiently plastic in the range of 100 to 180° C., in contrast to bituminous binder compounds which typically have a higher liquefaction temperature, namely higher than 180° C., whereby the flame lances can heat up more quickly and use less energy, which protects the environment and saves costs.
- the binder compound has adequate stability, cohesion and cold flexibility.
- Cold flexibility is defined in the industry as the temperature (° C.) at which the roof covering membrane breaks on flexion.
- a cold flexibility of ⁇ 9 to ⁇ 40° C. has the benefit that even at extremely low ambient temperatures, e.g. down to ⁇ 40° C., no breakage of the binder compound will occur. This applies both to a freshly produced binder compound and to an aged binder compound, for example after a life of twenty years during which great fluctuations in ambient temperature have occurred.
- Adequate cold flexibility will for example also allow a product, e.g. a roof covering membrane, containing the binder compound to be rolled at an ambient temperature of ⁇ 40° C. e.g. for stacking, storage or transport, and then unrolled again or applied without the binder compound breaking.
- the resin together with the natural oil ensures the formation of a cohesive whole.
- the resin is a natural resin.
- the resin is a synthetic resin.
- a binder compound forms a better cohesive whole if resin is added to natural oil.
- a better viscosity namely from 1400 to 2500 Pa ⁇ s
- better cold flexibility namely from ⁇ 9 to ⁇ 40° C.
- the binder compound according to the present invention has a resin quantity of maximum 70 w. %. This reduces the cost price of the binder compound.
- the binder compound can form part of other products which as a result acquire an environmentally friendly and renewable aspect and long term stability.
- the binder compound according to the present invention is preferably used in production of a roof covering membrane which gives such roof covering membranes favorable properties such as for example ease of handling and processing, and furthermore can also be rolled up or installed, remains crack-free and stable even if the binder compound reaches a low temperature e.g. ⁇ 40° C. In winter the binder compound which forms part of such roof covering membranes will consequently not tend to break or crack.
- Such roof covering membranes furthermore have a viscosity of 1400 to 25000 Pa ⁇ s at 180° C. so that the roof covering membrane can be processed easily and remains stable even if the binder compound reaches a high temperature e.g. 80° C.
- Such a roof covering membrane is ecologically responsible as less non-renewable CO2 occurs because the raw materials are mainly renewable.
- a roof covering membrane is halogen-free and 100% recyclable. It can be attached in combination with a cold adhesive according to the present invention which creates an ecological roof covering.
- the binder compound according to the present invention can furthermore preferably be used in the production of a road surfacing compound which contains the binder compound in a quantity of 1 to 20 w.%, more specifically in a quantity of 10 to 15 w. %, more specifically in a quantity of 1 to 10 w. %, yet more specifically in a quantity of 1 to 7 w. %, and an aggregate or filler.
- a road surfacing compound which contains the binder compound in a quantity of 1 to 20 w.%, more specifically in a quantity of 10 to 15 w. %, more specifically in a quantity of 1 to 10 w. %, yet more specifically in a quantity of 1 to 7 w. %, and an aggregate or filler.
- Such road surfacing compounds form an environmentally friendly alternative to asphalt and other bituminous surfaces.
- the binder compound according to the present invention is preferably also used in other applications such as the production of a watery emulsion.
- the watery emulsion according to the invention is characterized in that it contains the binder compound in a quantity of 40 to 70 w. %, water in a quantity of 60 to 30 w. % and an emulsifier in a quantity of 3 to 10 w. %.
- Such watery emulsions offer the advantage that they can form part of paints and coatings.
- the binder compound according to the present invention can be used for cold adhesive compounds.
- the cold adhesive compound according to the invention is characterized in that it contains the binder compound in a quantity of 25 to 70 w. %, more specifically a quantity of 40 to 50 w. %, and one or more solvents or vegetable oils or derived from vegetable oils, or a combination thereof, in a quantity of 7 to 25 w. % and a filler in a quantity of 25 to 35 w. %.
- Such cold adhesive compounds offer the advantage that they are an environmentally friendly alternative to conventional cold adhesive compounds based on bitumen.
- FIG. 1 is a graph which shows viscosity as a function of time during preparation of the binder compounds from example 5 with (+) and without (O) antioxidant, and a bituminous binder compound (x).
- binder compounds and roof covering membranes are directed amongst others at binder compounds and roof covering membranes but it will be clear that the binder compound according to the present invention can also be used in other fields such as for example in road surfacing, cold adhesive, coatings, paints, textiles and the carpet industry.
- natural oil refers to an oil derived from vegetable or similar sources.
- natural oil comprises natural oil derivatives unless specified otherwise.
- natural oils comprise but are not limited to vegetable oils, algae oils, fish oils, animal fats, tall oils, distillation fractions of these oils, derivatives of these oils such as fatty acids and fatty acid alkyl (e.g. methyl) esters, combinations of one or more of these oils and similar.
- natural oil derivatives refers to compounds or a mixture of compounds derived from natural oil using a method or a combination of methods known in the chemical industry. These methods comprise saponification, esterification, hydrogenation (partial or complete), isomerization, oxidation and reduction.
- the binder compound according to the invention comprises natural oil in a quantity of 0.1 to 25 w. %, more specifically a quantity of 14 to 19 w. %.
- the natural oil for use in the binder compound comprises for example fatty acids e.g. C 6 to C 24 fatty acids, esterified fatty acids, triacylglycerols or fatty alcohols. These natural oils offer the advantage that they show good and sustained interaction with resin and polymer so that a cohesive whole is achieved. In the quantity selected, also the natural oil does not leak or leach out of the binder compound.
- Preferred examples of vegetable oils are canola oil, rapeseed oil, coconut oil, maize oil, cottonseed oil, olive oil, palm oil, peanut oil, safflower oil, sesame oil, soya oil, sunflower oil, linseed oil, palmpit oil, tung oil, jatropha oil and castor oil.
- Preferred examples of animal fats are for example lard, tallow, chicken fat, suet and fish oil.
- Tall oils are by-products from the production of wood pulp.
- Preferred examples of natural oil derivatives comprise gums, phospholipides, soap stock, acidified soap stock, distillate or distillate slurry, fatty acids and fatty acid alkyl (e.g. methyl) esters of natural oil.
- the natural oil derivative can be a fatty acid methyl ester (FAME) derived from the glyceride of the natural oil.
- FAME fatty acid methyl ester
- the natural oil contains canola or soya oil or refined, bleached and deodorized soya oil.
- Soya oil consists of unsaturated polyesters of glycerol e.g. saturated fatty acids e.g. palmitic acid and stearic acid, and unsaturated fatty acids e.g. oleic acid, linoleic acid and linolenic acid, with around 95 w. % or higher (e.g. 99 w. % of higher) triglycerides of fatty acids.
- crude tall oil pitch CTO pitch
- a waste stream from the paper industry is used as the source of tall oil fatty acids and natural resins.
- the use of CTO pitch offers an ecological benefit because this reuses a waste stream as a “second generation” renewable raw material and consequently less “first generation” renewable natural oil and resin is required.
- the present invention relates to a binder compound which furthermore also comprises polymer in a quantity of 0.1 to 40 w. %, more specifically a quantity of 3 to 20 w. %, even more specifically a quantity of 4 to 17 w. %, and selected from the group comprising SBS, SEBS, SIS, PIB, polyhydroxybutyrate, PLA, polyolefins, polyamides, polyesters, APP and IPP and combinations thereof.
- U.S. Pat. No. 7,670,420 describes a compound which consists of vegetable oil and resin of vegetable origin. This compound however does not contain a polymer which means the softening point lies between 30° C. and 75° C., which is very low. This has the consequence that this compound has a tendency to melt at a temperature above 75° C. which makes this compound less suitable as a membrane e.g. a roof covering membrane, or as a bituminous cold adhesive on roofs which are exposed to high temperatures as a result of sunlight.
- the softening point of the binder compound in the present invention is however between 75° C. and 145° C., which makes it suitable for use as a roof covering membrane.
- SBS is a suitable choice in binder compounds because it mixes well during production of the binder compound and gives the best result in relation to cold flexibility, liquefaction properties and viscosity.
- polyolefins which are used as polymers in the binder compound are polyethylene and polypropylene.
- polyesters which are used as polymers in the binder composition is polyethyleneterephthalate.
- the present invention relates to a binder compound which furthermore also comprises resin in a quantity of 0.1 to 70 w. %, more specifically in a quantity of 20 to 50 w. %, even more specifically in a quantity of 32 to 40 w. %.
- resin both natural and synthetic resins can be used.
- natural resin examples include gum resin and derivatives of gum resin such as esters of gum resin, esters of dehydrogenated gum, resin esters of stabilized gum resin, esters of resin acids, esters of stabilized resin acids, esters of polymerized gum resin, phenolic modified esters of gum resin, pentaerythritol esters of gum resin, triethylene glycol esters of gum resin, ethylene glycol esters of gum resin, dibasic acid modified gum resin, resin oil, cardanol and other products derived from the oil of cashew nut shells (CNSL or cashew nut shell liquid), furan resins and products derived from furan resins.
- Synthetic resins can be both amorphous and crystallized
- the binder compound according to the invention is characterized in that it comprises an antioxidant e.g. a phenolic antioxidant suitable for preventing oxidation of the binder compound, more particularly the polymer in combination with the resin. As a result the viscosity and cohesion of the binder compound are retained.
- the binder compound contains an antioxidant in a quantity of 0.1 to 3 w. %, more specifically 0.5 to 1.5 w. %.
- the binder compound comprises a filler in a quantity of less than 65 w. %, more specifically in a quantity of 20 to 50 w. %, even more specifically in a quantity of 32 to 40 w. %.
- the high content of filler than usual in conventional bitumen-based binder compounds can be used because of the good cold flexibility of the binder compound and also entails an economic benefit.
- All fillers for use in bitumen-based binder compounds can be used in the binder compound according to the present invention. Examples of fillers are talcum, CaCO 3 , sand, silica, stone powder, fly ash, limestone powder, slaked lime, organic fillers such as flour, meal, sawdust and cork powder.
- the filler ensures amongst others that the binder compound is less sticky. Also the filler is normally the cheapest component which gives the binder compound an economic advantage.
- the binder compound contains a flame retarder such as e.g. ATH (aluminum trihydrate) or colmanite, whereby the binder compound and products which contain the binder compound such as roof covering membranes are more fire-resistant.
- a flame retarder such as e.g. ATH (aluminum trihydrate) or colmanite
- the binder compound contains coloring or colorings e.g. organic or inorganic pigments such as TiO 2 , Fe 2 O 3 whereby the binder compound can assume a color depending on the choice of coloring or colorings.
- coloring or colorings e.g. organic or inorganic pigments such as TiO 2 , Fe 2 O 3 whereby the binder compound can assume a color depending on the choice of coloring or colorings.
- the present invention also relates to a roof covering membrane comprising the binder compound according to the present invention.
- the roof covering membrane comprises a reinforcement.
- a glass fleece or a polyester e.g. a non-woven polyester can be used.
- One or more reinforcements can be used.
- the roof covering membrane comprises a glass fleece and a non-woven polyester. These give the membrane a dimensional stability and good resistance to cracking and perforation.
- the roof covering membrane comprises a coated reinforcement along one or more sides.
- This reinforcement can be coated with a polymer coating e.g. a coating of acrylate or another polymer such as FIB or PE. This coating ensures that the natural oil does not migrate to the surface of the roof covering membrane and then leach out.
- This coating can also be a reflective coating which reflects sunlight e.g. by the presence of metal particles such as e.g. TiO 2 .
- one or more sides of the roof covering membrane are covered with talcum or a polymer film (PE, PP, etc.) so that roof covering membranes which comes into contact with each other, e.g. when rolled onto a roll, do not stick together.
- the talcum need not be removed before the roof covering membrane is applied to the substrate.
- the roof covering membrane with talcum can therefore be applied directly to the substrate using cold adhesive, flame or hot air.
- a layer of chippings e.g. slate chippings or slate chippings mixed with red or black coloring, can be applied to the surface of the roof covering membrane to give the roof covering membrane the desired appearance.
- the present invention also relates to a road surfacing compound comprising the binder compound according to the present invention in a quantity of 1 to 20 w. %, more specifically a quantity of 10 to 15 w. %, more specifically a quantity of 1 to 10 w. %, even more specifically a quantity of 1 to 7 w. %, and an aggregate.
- an aggregate for example but without limitation, quartzite or limestone can be used.
- the present invention also relates to a watery emulsion comprising the binder compound according to the present invention in a quantity of 40 to 70 w. %, water in a quantity of 60 to 30 w. % and an emulsifier in a quantity of 3 to 10 w. %.
- an emulsifier for example surfactants can be used.
- the present invention also relates to a cold adhesive compound comprising the binder compound according to the present invention in a quantity of 25 to 70 w. %, more specifically a quantity of 40 to 50 w. %.
- the present invention also relates to a cold adhesive compound which furthermore comprises one or more solvents or natural oils or derivatives of natural oils or a combination thereof in a quantity of 7 to 25 w. %.
- solvents in the cold adhesive compound for example naphtha, petrol or white spirit can be used.
- natural oils or derivatives of natural oils in the cold adhesive compound fatty acids, triacyclgycerol, fatty acid esters, fatty alcohols can be used.
- the present invention also relates to a cold adhesive compound which furthermore contains a filler in a quantity of 25 to 35 w. %.
- a filler in the cold adhesive compound inorganic and organic fillers such as calcium carbonate and cellulose fibers can be used.
- the present example also relates to a method for preparation of a binder compound according to the present invention.
- the method is characterized by mixing at high temperature e.g. higher than or equal to 150° C. This has the benefit that the mixing can take place quickly and efficiently, a stable binder compound is achieved and less heat energy is required than for the production of a bituminous binder compound, which typically takes place at 180 to 200° C.
- binder compounds produced by mixing at 150° C., had a viscosity of around 3000 Pa ⁇ s and were therefore particularly suitable for use in “self-adhesive” roof covering membranes.
- These self-adhesive roof covering membrane could be applied to a roof by simply lightly warming to 100° C. either with hot air or with a gentle flame.
- These self-adhesive roof covering membranes were fitted with a polymer film to prevent layers on a roll from sticking together. This polymer film is removed before application.
- This binder compound produced by mixing at 150° C., had a viscosity of around 14000 Pa ⁇ s and was therefore particularly suitable for use in roof covering membranes or carpets.
- the crude tall oil pitch contained 65% fatty acids and tall oil at 35% colophonium resin.
- the use of crude tall oil pitch offered an economic benefit as consequently less resin needed to be added to the binder compound.
- With a viscosity of around 3000 Pa ⁇ s the binder compound was particularly suitable for use in watery emulsions or cold adhesives.
- these binder compounds are suitable for use as roof covering membranes or road surfacing compounds.
- the binder compound is suitable for use in watery emulsions or cold adhesives.
- a binder compound was produced with antioxidant (table 1, column 2), namely a phenolic antioxidant (Irganox).
- antioxidant table 1, column 2
- This binder compound largely retained its viscosity during the mixing process ( FIG. 1 ) thanks to the presence of the antioxidant and is therefore ideally suited for use in roof covering membranes or carpets.
- the viscosity was comparable to the viscosity of a conventional binder compound on the basis of bitumen and SBS, produced in the same manner ( FIG. 1 ).
- the cold flexibility and softening point (PEN 25° C.) were determined on binder compounds containing SBS polymer, fatty acids, pentaerythritol gum resin, antioxidant and different quantities of CaCO 3 filler. All binder compounds showed a high hardness while retaining a high cold flexibility and softening point. As a result these binder compounds were ideal for use in road surfacing amongst others.
- a roof covering membrane was produced with the following dimensions:
- This roof covering membrane contained no bitumen and was largely based on renewable carbon molecules, which was an ecological benefit. For application on a roof, this roof covering membrane also needed to be heated less whereby application could be faster and cheaper than with bituminous covering membranes.
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Abstract
The present invention relates to a binder compound based on natural oil, polymer and resin. Such binder compounds can for example be used in roof covering membranes as an environmentally friendly alternative to bituminous roof covering membranes.
Description
- The present invention relates to a binder compound based on natural oils, polymer and resin.
- Such binder compounds can for example be used for production of roof covering membranes and similar as an environmentally friendly alternative to bituminous roof covering membranes.
- In construction or road building, traditional products of bituminous and petrochemical origin are used as constituents of membranes such as roof covering membranes or as a basis for asphalt. Traditionally bitumen is a by-product of the petrochemical industry which offers a cheap and high quality raw material for the production of roof covering membranes or asphalt. Due to rising demand for petroleum products for use in chemistry and as fuel, the quality and availability of high quality bitumen has diminished greatly. Also the use of bituminous products has a harmful influence on the environment as its production causes great environmental pressure. Another disadvantage of the use of bitumen is the acidification of rain water as a result of interaction of UV and bitumen.
- WO 2009/071653 describes a compound which consists of resin of vegetable origin, oil of vegetable origin and a polymer that contains functional groups selected from the carboxylic acid anhydride, carboxylic acid and epoxide groups. The disadvantage of this compound is that only such functionalized polymers can be used, which entails a restriction in suitable polymers and in addition increases the cost price of this compound.
- The object of the present invention is to provide a binder compound in which oil of natural origin, resin and polymer are used, while allowing a wider choice of polymer.
- The above object is achieved by a binder compound comprising:
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- natural oil in a quantity of 14-19 w. %; and
- polymer in a quantity of 4 to 17 w. % and selected from the group consisting of styrene-butadiene-styrene (SBS), styrene-ethylene-butadiene-styrene (SEBS), styrene-isoprene-styrene (SIS), polyisobutylene (FIB), polyhydroxybutyrate, polylactide (PLA), polyolefins, polyamides, polyesters, atactic polypropylene (APP) and isotactic polypropylene (IPP) and combinations thereof, wherein said polymer contains no functional groups selected from a carboxylic acid anhydride group, a carboxylic acid group and an epoxy group; and
- resin in a quantity of 32 to 40 w. %.
- Such a binder compound offers the advantage that it is an environmentally friendly alternative to binder compounds based on bitumen as it contains natural oil which is a source of renewable carbon and therefore has little or no influence on the CO2 balance in the atmosphere. Another important benefit is that the problem of acid leaching, which can lead to acidified rain water, is avoided because natural oil does not lead to acidification under the effect of UV. As a result the recovered rain water can be used with less further treatment for sanitary or other applications. Another benefit is that the roof covering membranes and cold adhesives which contain the binder compound according to the invention can be processed, applied or used in the same way as bituminous roof covering membranes and cold adhesives.
- Thanks to the interaction between natural oil, resin and polymer in this concentration range of natural oil, the binder compound has the following viscosity, namely a viscosity of 1400 to 25000 Pa·s at 180° C. This viscosity is similar to the viscosity of modified bitumen binder compounds. Due to this viscosity the binder compound will be solid at an ambient temperature of approximately −15° C. to approximately 40° C., which is necessary for example for the setting and hardness of roof covering membranes and cold adhesives containing the binder compound. At ambient temperatures above around 25° C. the binder compound also remains cohesive and will consequently not flow out, which again is favorable for use in roof covering membranes and road construction.
- Thanks to the interaction between natural oil, resin and polymer in this concentration range of natural oil, the binder compound also has a relatively low liquefaction temperature, namely 100 to 180° C. This is the temperature at which the binder compound acquires a specific degree of plasticity as defined in the profession by the technical standard ASTM D36/D36M-09 of Dec. 15, 2009. The binder compound must be sufficiently plastic when for example it forms part of a roof covering membrane which is applied to a substrate or surface by means of burner lances, because this achieves a good adhesion of the roof covering membrane to the substrate. Burner lances typically use a flame with a flame temperature of 180 to 220° C. At this liquefaction temperature, the binder compound will already be sufficiently plastic in the range of 100 to 180° C., in contrast to bituminous binder compounds which typically have a higher liquefaction temperature, namely higher than 180° C., whereby the flame lances can heat up more quickly and use less energy, which protects the environment and saves costs.
- Thanks to the presence of polymer, the binder compound has adequate stability, cohesion and cold flexibility. Cold flexibility is defined in the industry as the temperature (° C.) at which the roof covering membrane breaks on flexion. A cold flexibility of −9 to −40° C. has the benefit that even at extremely low ambient temperatures, e.g. down to −40° C., no breakage of the binder compound will occur. This applies both to a freshly produced binder compound and to an aged binder compound, for example after a life of twenty years during which great fluctuations in ambient temperature have occurred. Adequate cold flexibility will for example also allow a product, e.g. a roof covering membrane, containing the binder compound to be rolled at an ambient temperature of −40° C. e.g. for stacking, storage or transport, and then unrolled again or applied without the binder compound breaking.
- The resin together with the natural oil ensures the formation of a cohesive whole. In a preferred embodiment the resin is a natural resin. In another preferred embodiment the resin is a synthetic resin.
- It is in any case known that a binder compound forms a better cohesive whole if resin is added to natural oil. However by use of the binder compound according to the present invention, even with a much lower quantity of resin, a better viscosity namely from 1400 to 2500 Pa·s, better cold flexibility namely from −9 to −40° C., can be achieved than in known binder compounds. In fact where W02009/071653 in its specific examples mentions resin concentrations of 77 w. % and 80 w. %, the binder compound according to the present invention has a resin quantity of maximum 70 w. %. This reduces the cost price of the binder compound.
- The binder compound can form part of other products which as a result acquire an environmentally friendly and renewable aspect and long term stability.
- The binder compound according to the present invention is preferably used in production of a roof covering membrane which gives such roof covering membranes favorable properties such as for example ease of handling and processing, and furthermore can also be rolled up or installed, remains crack-free and stable even if the binder compound reaches a low temperature e.g. −40° C. In winter the binder compound which forms part of such roof covering membranes will consequently not tend to break or crack. Such roof covering membranes furthermore have a viscosity of 1400 to 25000 Pa·s at 180° C. so that the roof covering membrane can be processed easily and remains stable even if the binder compound reaches a high temperature e.g. 80° C. Another important advantage is also that this viscosity falls within the range of viscosities of bituminous roof membranes available on the market, which makes for ease of use by the skilled person. In summer the binder compound which forms part of such roof covering membranes will consequently not tend to melt at an ambient temperature of 35° C. Such a roof covering membrane is water-tight, durable and stable and has a high cracking and perforation resistance.
- Such a roof covering membrane is ecologically responsible as less non-renewable CO2 occurs because the raw materials are mainly renewable. In addition such a roof covering membrane is halogen-free and 100% recyclable. It can be attached in combination with a cold adhesive according to the present invention which creates an ecological roof covering.
- The binder compound according to the present invention can furthermore preferably be used in the production of a road surfacing compound which contains the binder compound in a quantity of 1 to 20 w.%, more specifically in a quantity of 10 to 15 w. %, more specifically in a quantity of 1 to 10 w. %, yet more specifically in a quantity of 1 to 7 w. %, and an aggregate or filler. Such road surfacing compounds form an environmentally friendly alternative to asphalt and other bituminous surfaces.
- The binder compound according to the present invention is preferably also used in other applications such as the production of a watery emulsion. In a preferred embodiment the watery emulsion according to the invention is characterized in that it contains the binder compound in a quantity of 40 to 70 w. %, water in a quantity of 60 to 30 w. % and an emulsifier in a quantity of 3 to 10 w. %. Such watery emulsions offer the advantage that they can form part of paints and coatings.
- Also the binder compound according to the present invention can be used for cold adhesive compounds. In a preferred embodiment the cold adhesive compound according to the invention is characterized in that it contains the binder compound in a quantity of 25 to 70 w. %, more specifically a quantity of 40 to 50 w. %, and one or more solvents or vegetable oils or derived from vegetable oils, or a combination thereof, in a quantity of 7 to 25 w. % and a filler in a quantity of 25 to 35 w. %. Such cold adhesive compounds offer the advantage that they are an environmentally friendly alternative to conventional cold adhesive compounds based on bitumen.
- More details and features of the invention arise from the description given below and with reference to the enclosed drawing.
-
FIG. 1 is a graph which shows viscosity as a function of time during preparation of the binder compounds from example 5 with (+) and without (O) antioxidant, and a bituminous binder compound (x). - The examples are directed amongst others at binder compounds and roof covering membranes but it will be clear that the binder compound according to the present invention can also be used in other fields such as for example in road surfacing, cold adhesive, coatings, paints, textiles and the carpet industry.
- As used here, the term “natural oil” refers to an oil derived from vegetable or similar sources. The term “natural oil” comprises natural oil derivatives unless specified otherwise. Examples of natural oils comprise but are not limited to vegetable oils, algae oils, fish oils, animal fats, tall oils, distillation fractions of these oils, derivatives of these oils such as fatty acids and fatty acid alkyl (e.g. methyl) esters, combinations of one or more of these oils and similar. As used here, the term “natural oil derivatives” refers to compounds or a mixture of compounds derived from natural oil using a method or a combination of methods known in the chemical industry. These methods comprise saponification, esterification, hydrogenation (partial or complete), isomerization, oxidation and reduction.
- The binder compound according to the invention comprises natural oil in a quantity of 0.1 to 25 w. %, more specifically a quantity of 14 to 19 w. %. The natural oil for use in the binder compound comprises for example fatty acids e.g. C6 to C24 fatty acids, esterified fatty acids, triacylglycerols or fatty alcohols. These natural oils offer the advantage that they show good and sustained interaction with resin and polymer so that a cohesive whole is achieved. In the quantity selected, also the natural oil does not leak or leach out of the binder compound.
- Preferred examples of vegetable oils are canola oil, rapeseed oil, coconut oil, maize oil, cottonseed oil, olive oil, palm oil, peanut oil, safflower oil, sesame oil, soya oil, sunflower oil, linseed oil, palmpit oil, tung oil, jatropha oil and castor oil. Preferred examples of animal fats are for example lard, tallow, chicken fat, suet and fish oil. Tall oils are by-products from the production of wood pulp. Preferred examples of natural oil derivatives comprise gums, phospholipides, soap stock, acidified soap stock, distillate or distillate slurry, fatty acids and fatty acid alkyl (e.g. methyl) esters of natural oil. For example the natural oil derivative can be a fatty acid methyl ester (FAME) derived from the glyceride of the natural oil.
- Preferably the natural oil contains canola or soya oil or refined, bleached and deodorized soya oil. Soya oil consists of unsaturated polyesters of glycerol e.g. saturated fatty acids e.g. palmitic acid and stearic acid, and unsaturated fatty acids e.g. oleic acid, linoleic acid and linolenic acid, with around 95 w. % or higher (e.g. 99 w. % of higher) triglycerides of fatty acids. In a particular embodiment crude tall oil pitch (CTO pitch), a waste stream from the paper industry, is used as the source of tall oil fatty acids and natural resins. The use of CTO pitch offers an ecological benefit because this reuses a waste stream as a “second generation” renewable raw material and consequently less “first generation” renewable natural oil and resin is required.
- The present invention relates to a binder compound which furthermore also comprises polymer in a quantity of 0.1 to 40 w. %, more specifically a quantity of 3 to 20 w. %, even more specifically a quantity of 4 to 17 w. %, and selected from the group comprising SBS, SEBS, SIS, PIB, polyhydroxybutyrate, PLA, polyolefins, polyamides, polyesters, APP and IPP and combinations thereof.
- U.S. Pat. No. 7,670,420 describes a compound which consists of vegetable oil and resin of vegetable origin. This compound however does not contain a polymer which means the softening point lies between 30° C. and 75° C., which is very low. This has the consequence that this compound has a tendency to melt at a temperature above 75° C. which makes this compound less suitable as a membrane e.g. a roof covering membrane, or as a bituminous cold adhesive on roofs which are exposed to high temperatures as a result of sunlight. The softening point of the binder compound in the present invention is however between 75° C. and 145° C., which makes it suitable for use as a roof covering membrane.
- The use of polymers in the binder compound will ensure a good cold flexibility, good liquefaction properties and good viscosity. SBS is a suitable choice in binder compounds because it mixes well during production of the binder compound and gives the best result in relation to cold flexibility, liquefaction properties and viscosity.
- Functionalized polymers such as described in WO 2009/071653 are not used.
- Examples of polyolefins which are used as polymers in the binder compound are polyethylene and polypropylene. An example of polyesters which are used as polymers in the binder composition is polyethyleneterephthalate.
- The present invention relates to a binder compound which furthermore also comprises resin in a quantity of 0.1 to 70 w. %, more specifically in a quantity of 20 to 50 w. %, even more specifically in a quantity of 32 to 40 w. %. As resin both natural and synthetic resins can be used. Examples of natural resin are gum resin and derivatives of gum resin such as esters of gum resin, esters of dehydrogenated gum, resin esters of stabilized gum resin, esters of resin acids, esters of stabilized resin acids, esters of polymerized gum resin, phenolic modified esters of gum resin, pentaerythritol esters of gum resin, triethylene glycol esters of gum resin, ethylene glycol esters of gum resin, dibasic acid modified gum resin, resin oil, cardanol and other products derived from the oil of cashew nut shells (CNSL or cashew nut shell liquid), furan resins and products derived from furan resins. Synthetic resins can be both amorphous and crystallized
- In a preferred embodiment the binder compound according to the invention is characterized in that it comprises an antioxidant e.g. a phenolic antioxidant suitable for preventing oxidation of the binder compound, more particularly the polymer in combination with the resin. As a result the viscosity and cohesion of the binder compound are retained. In a further preferred embodiment the binder compound contains an antioxidant in a quantity of 0.1 to 3 w. %, more specifically 0.5 to 1.5 w. %.
- Preferably the binder compound comprises a filler in a quantity of less than 65 w. %, more specifically in a quantity of 20 to 50 w. %, even more specifically in a quantity of 32 to 40 w. %. The high content of filler than usual in conventional bitumen-based binder compounds can be used because of the good cold flexibility of the binder compound and also entails an economic benefit. All fillers for use in bitumen-based binder compounds can be used in the binder compound according to the present invention. Examples of fillers are talcum, CaCO3, sand, silica, stone powder, fly ash, limestone powder, slaked lime, organic fillers such as flour, meal, sawdust and cork powder. The filler ensures amongst others that the binder compound is less sticky. Also the filler is normally the cheapest component which gives the binder compound an economic advantage.
- In a particular embodiment the binder compound contains a flame retarder such as e.g. ATH (aluminum trihydrate) or colmanite, whereby the binder compound and products which contain the binder compound such as roof covering membranes are more fire-resistant.
- In another preferred embodiment the binder compound contains coloring or colorings e.g. organic or inorganic pigments such as TiO2, Fe2O3 whereby the binder compound can assume a color depending on the choice of coloring or colorings.
- The present invention also relates to a roof covering membrane comprising the binder compound according to the present invention. In a particular embodiment the roof covering membrane comprises a reinforcement. As reinforcement a glass fleece or a polyester e.g. a non-woven polyester can be used. One or more reinforcements can be used. In a preferred embodiment the roof covering membrane comprises a glass fleece and a non-woven polyester. These give the membrane a dimensional stability and good resistance to cracking and perforation. In a preferred embodiment the roof covering membrane comprises a coated reinforcement along one or more sides. This reinforcement can be coated with a polymer coating e.g. a coating of acrylate or another polymer such as FIB or PE. This coating ensures that the natural oil does not migrate to the surface of the roof covering membrane and then leach out. This coating can also be a reflective coating which reflects sunlight e.g. by the presence of metal particles such as e.g. TiO2.
- In another preferred embodiment one or more sides of the roof covering membrane are covered with talcum or a polymer film (PE, PP, etc.) so that roof covering membranes which comes into contact with each other, e.g. when rolled onto a roll, do not stick together. In contrast to the polymer film, the talcum need not be removed before the roof covering membrane is applied to the substrate. The roof covering membrane with talcum can therefore be applied directly to the substrate using cold adhesive, flame or hot air.
- In a preferred embodiment a layer of chippings, e.g. slate chippings or slate chippings mixed with red or black coloring, can be applied to the surface of the roof covering membrane to give the roof covering membrane the desired appearance.
- The present invention also relates to a road surfacing compound comprising the binder compound according to the present invention in a quantity of 1 to 20 w. %, more specifically a quantity of 10 to 15 w. %, more specifically a quantity of 1 to 10 w. %, even more specifically a quantity of 1 to 7 w. %, and an aggregate. As an aggregate, for example but without limitation, quartzite or limestone can be used.
- The present invention also relates to a watery emulsion comprising the binder compound according to the present invention in a quantity of 40 to 70 w. %, water in a quantity of 60 to 30 w. % and an emulsifier in a quantity of 3 to 10 w. %. As an emulsifier for example surfactants can be used.
- The present invention also relates to a cold adhesive compound comprising the binder compound according to the present invention in a quantity of 25 to 70 w. %, more specifically a quantity of 40 to 50 w. %.
- The present invention also relates to a cold adhesive compound which furthermore comprises one or more solvents or natural oils or derivatives of natural oils or a combination thereof in a quantity of 7 to 25 w. %. As solvents in the cold adhesive compound for example naphtha, petrol or white spirit can be used. As natural oils or derivatives of natural oils in the cold adhesive compound, fatty acids, triacyclgycerol, fatty acid esters, fatty alcohols can be used.
- The present invention also relates to a cold adhesive compound which furthermore contains a filler in a quantity of 25 to 35 w. %. As a filler in the cold adhesive compound, inorganic and organic fillers such as calcium carbonate and cellulose fibers can be used.
- The present example also relates to a method for preparation of a binder compound according to the present invention. The method is characterized by mixing at high temperature e.g. higher than or equal to 150° C. This has the benefit that the mixing can take place quickly and efficiently, a stable binder compound is achieved and less heat energy is required than for the production of a bituminous binder compound, which typically takes place at 180 to 200° C.
-
-
Quantity (w. %) SBS 11 10.6 Sunflower oil 16 15.4 Colophonium resin 38 0 Pentaerythritol gum resin 0 36.6 CaCO3 filler 35 29 Pigments 0 5 - These binder compounds, produced by mixing at 150° C., had a viscosity of around 3000 Pa·s and were therefore particularly suitable for use in “self-adhesive” roof covering membranes. These self-adhesive roof covering membrane could be applied to a roof by simply lightly warming to 100° C. either with hot air or with a gentle flame. These self-adhesive roof covering membranes were fitted with a polymer film to prevent layers on a roll from sticking together. This polymer film is removed before application.
-
-
Quantity (w. %) SBS 12.5 Sunflower oil 17.5 Pentaerythritol gum resin 34 CaCO3 filler 34 Pigments 5 Antioxidant 1 - This binder compound, produced by mixing at 150° C., had a viscosity of around 14000 Pa·s and was therefore particularly suitable for use in roof covering membranes or carpets.
-
-
Quantity (w. %) SBS 11 Crude tall oil pitch 25 Pentaerythritol gum resin 27 CaCO3 filler 37 - The crude tall oil pitch contained 65% fatty acids and tall oil at 35% colophonium resin. The use of crude tall oil pitch offered an economic benefit as consequently less resin needed to be added to the binder compound. With a viscosity of around 3000 Pa·s the binder compound was particularly suitable for use in watery emulsions or cold adhesives.
-
-
Quantity (w. %) SBS 11.5 11.5 Fatty acids of linseed oil 18.3 18.3 Pentaerythritol gum resin 31.8 31.8 CaCO3 filler 33.9 32.9 Antioxidant 1.5 1.5 Flame-retarder 4.5 3 Properties Softening point (° C.) 108-145 114-137 Viscosity at 180° C. (Pa · s) 17150 11775 PEN at 25° C. ( 1/10 mm) 51 61 PEN at 60° C. ( 1/10 mm) 98 109 Cold flexibility (° C.) initial −32 −24 after 7 d at 70° C. −22 −16 after 28 d at 70° C. −17 −9 - Thanks to the high viscosity and low PEN, these binder compounds are suitable for use as roof covering membranes or road surfacing compounds.
- To produce the binder compound on an industrial scale, in particular in large volumes, the following production method is used. Resin, oil and SBS are mixed for a few hours at 180° C. As a filler, CaCO3 is added. This binder compound (table 1, column 1) showed a reduction in viscosity during mixing (
FIG. 1 ). As a result the binder compound is suitable for use in watery emulsions or cold adhesives. - To prevent thermally induced oxidation of the polymer, according to this method a binder compound was produced with antioxidant (table 1, column 2), namely a phenolic antioxidant (Irganox). This binder compound largely retained its viscosity during the mixing process (
FIG. 1 ) thanks to the presence of the antioxidant and is therefore ideally suited for use in roof covering membranes or carpets. The viscosity was comparable to the viscosity of a conventional binder compound on the basis of bitumen and SBS, produced in the same manner (FIG. 1 ). -
TABLE 1 Composition and properties of binder compounds produced on large scale. Quantity (w. %) SBS 10 9.8 Fatty acids 15 14.9 Pentaerythritol gum resin 35 34.5 CaCO3 filler 40 39.4 Antioxidant 0 1.5 Properties Softening point (° C.) 75-90 89-109 Viscosity at 180° C. (Pa · s) 1416 8600 PEN at 25° C. ( 1/10 mm) 71 PEN at 60° C. ( 1/10 mm) 127 Cold flexibility (° C.) initial −27 after 7 d at 70° C. −24 after 28 d at 70° C. −24 after 28 d under UV −15 - The cold flexibility and softening point (PEN 25° C.) were determined on binder compounds containing SBS polymer, fatty acids, pentaerythritol gum resin, antioxidant and different quantities of CaCO3 filler. All binder compounds showed a high hardness while retaining a high cold flexibility and softening point. As a result these binder compounds were ideal for use in road surfacing amongst others.
-
CaCO3 Cold PEN filler (w. %) flexibility (° C.) 25° C. ( 1/10 mm) 34 −28 101 36 −28 88 38 −27 89 45 −28 50 −28 - A roof covering membrane was produced with the following dimensions:
-
- Thickness: 3 mm
- Length: 7.27 m
- Width: 1.1 m
- Surface area: 8 m2
- Roll weight: 32.5 kg
- This roof covering membrane contained no bitumen and was largely based on renewable carbon molecules, which was an ecological benefit. For application on a roof, this roof covering membrane also needed to be heated less whereby application could be faster and cheaper than with bituminous covering membranes.
Claims (8)
1. Binder compound comprising
natural oil in a quantity of 14 to 19 w. %; and
polymer in a quantity of 4 to 17 w. % and selected from the group consisting of styrene-butadiene-styrene (SBS), styrene-ethylene-butadiene-styrene (SEBS), styrene-isoprene-styrene (SIS), polyisobutylene (PIB), polyhydroxybutyrate, polylactide (PLA), polyolefins, polyamides, polyesters, atactic polypropylene (APP) and isotactic polypropylene (IPP) and combinations thereof, wherein said polymer comprises no functional group selected from a carboxylic acid anhydride group, a carboxylic acid group and an epoxy group; and
resin in a quantity of 32 to 40 w. %.
2. Binder compound according to claim 1 , comprising an antioxidant in a quantity of 0.1 to 3 w. %, more specifically 0.5 to 1.5 w. %.
3. Binder compound according to claim 1 , wherein the resin is a natural resin.
4. Binder compound according to claim 1 , comprising a filler in a quantity of maximum 65 w. %, more specifically a quantity of 20 to 50 w. %, even more specifically a quantity of 32 to 40 w. %.
5. Roof covering membrane comprising the binder compound according to claim 1 .
6. Road surfacing compound comprising the binder compound according to claim 1 in a quantity of 1 to 20 w. %, more specifically in a quantity of 10 to 15 w. %, more specifically in a quantity of 1 to 10 w. %, even more specifically in a quantity of 1 to 7 w. %, and an aggregate.
7. Aqueous emulsion comprising the binder compound according to claim 1 in a quantity of 40 to 70 w. %, water in a quantity of 60 to 30 w. % and an emulsifier in a quantity of 3 to 10 w. %.
8. Cold adhesive compound comprising
the binder compound according to claim 1 in a quantity of 25 to 70 w. %, more specifically a quantity of 40 to 50 w. %; and
one or more solvents or vegetable oils or derivatives of vegetable oils or a combination thereof in a quantity of 7 to 25 w. %; and
a filler in a quantity of 25 to 30 w. %.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US14/201,995 US20150051323A1 (en) | 2010-06-22 | 2014-03-10 | Binder compound |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| BE2010/0370 | 2010-06-22 | ||
| BE2010/0370A BE1019382A5 (en) | 2010-06-22 | 2010-06-22 | BINDING COMPOSITION. |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US14/201,995 Continuation US20150051323A1 (en) | 2010-06-22 | 2014-03-10 | Binder compound |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US20120041117A1 true US20120041117A1 (en) | 2012-02-16 |
Family
ID=42734578
Family Applications (3)
| Application Number | Title | Priority Date | Filing Date |
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| US13/027,552 Abandoned US20120041117A1 (en) | 2010-06-22 | 2011-02-15 | Binder Compound |
| US13/164,921 Expired - Fee Related US9505963B2 (en) | 2010-06-22 | 2011-06-21 | Membrane based on a binder compound with tall-oil pitch |
| US14/201,995 Abandoned US20150051323A1 (en) | 2010-06-22 | 2014-03-10 | Binder compound |
Family Applications After (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US13/164,921 Expired - Fee Related US9505963B2 (en) | 2010-06-22 | 2011-06-21 | Membrane based on a binder compound with tall-oil pitch |
| US14/201,995 Abandoned US20150051323A1 (en) | 2010-06-22 | 2014-03-10 | Binder compound |
Country Status (4)
| Country | Link |
|---|---|
| US (3) | US20120041117A1 (en) |
| EP (1) | EP2399969B1 (en) |
| BE (1) | BE1019382A5 (en) |
| DK (1) | DK2399969T3 (en) |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20160257813A1 (en) * | 2013-11-27 | 2016-09-08 | Dow Global Technologies Llc | Polyurethane Based Asphalt Composition |
| EP3081600A1 (en) | 2015-04-14 | 2016-10-19 | Soprema | Plant-based binder, compositions comprising same, and method for decreasing the amount of oil bitumen |
| EP3081599A1 (en) | 2015-04-14 | 2016-10-19 | Soprema | Plant-based binder, compositions thereof and method for reducing the amount of oil-based bitumen |
| EP3301136A1 (en) | 2016-09-30 | 2018-04-04 | S.A. Imperbel N.V. | Protective membrane composition |
| US11946254B2 (en) | 2020-08-21 | 2024-04-02 | Bmic Llc | Roofing materials with improved low temperature sealant performance and methods of making thereof |
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|---|---|---|---|---|
| RU2534539C2 (en) * | 2012-09-13 | 2014-11-27 | Общество с ограниченной ответственностью "Селена" | Amphoteric adhesive bitumen binder additive for asphalt concrete |
| FR3000087A1 (en) * | 2012-12-20 | 2014-06-27 | Total Raffinage Marketing | CLEAR SYNTHETIC BINDER COMPOSITION |
| US9744346B2 (en) * | 2014-07-17 | 2017-08-29 | Cochlear Limited | Implantable stimulating assembly arrangements |
| NL2017096B1 (en) * | 2016-07-04 | 2018-01-10 | Interface European Mfg B V | Bio-based carpet backing |
| CN113661288B (en) | 2019-01-09 | 2024-02-09 | 因特菲斯有限公司 | Surface coverings including carbon sequestration materials and methods of making the same |
| US11851813B2 (en) | 2019-01-09 | 2023-12-26 | Interface, Inc. | Surface coverings including carbon sequestering materials and methods of making |
| MX2023001832A (en) | 2020-08-14 | 2023-03-13 | Bmic Llc | Non-asphaltic coatings, non-asphaltic roofing materials, and methods of making the same. |
| WO2025214999A1 (en) * | 2024-04-08 | 2025-10-16 | Stichting Wageningen Research | Binder composition |
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| EP3081600A1 (en) | 2015-04-14 | 2016-10-19 | Soprema | Plant-based binder, compositions comprising same, and method for decreasing the amount of oil bitumen |
| EP3081599A1 (en) | 2015-04-14 | 2016-10-19 | Soprema | Plant-based binder, compositions thereof and method for reducing the amount of oil-based bitumen |
| FR3035113A1 (en) * | 2015-04-14 | 2016-10-21 | Soprema | BINDER OF VEGETABLE ORIGIN, COMPOSITIONS COMPRISING THE SAME, AND METHOD FOR REDUCING THE QUANTITY OF PETROLEUM BITUMEN |
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Also Published As
| Publication number | Publication date |
|---|---|
| BE1019382A5 (en) | 2012-06-05 |
| US9505963B2 (en) | 2016-11-29 |
| EP2399969B1 (en) | 2014-12-17 |
| US20120071597A1 (en) | 2012-03-22 |
| DK2399969T3 (en) | 2015-03-23 |
| US20150051323A1 (en) | 2015-02-19 |
| EP2399969A1 (en) | 2011-12-28 |
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| Date | Code | Title | Description |
|---|---|---|---|
| AS | Assignment |
Owner name: S.A. IMPERBEL N.V., BELGIUM Free format text: ASSIGNMENT OF ASSIGNORS INTEREST;ASSIGNORS:AERTS, HANS;MARTIN, NICOLAS;ZWIJSEN, MICHEL;AND OTHERS;REEL/FRAME:026805/0313 Effective date: 20110817 |
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| STCB | Information on status: application discontinuation |
Free format text: ABANDONED -- FAILURE TO RESPOND TO AN OFFICE ACTION |