EP0147429A1 - A method for preparing impregnated cellulose fibers having a low water retention and products hereby obtained - Google Patents
A method for preparing impregnated cellulose fibers having a low water retention and products hereby obtainedInfo
- Publication number
- EP0147429A1 EP0147429A1 EP84902199A EP84902199A EP0147429A1 EP 0147429 A1 EP0147429 A1 EP 0147429A1 EP 84902199 A EP84902199 A EP 84902199A EP 84902199 A EP84902199 A EP 84902199A EP 0147429 A1 EP0147429 A1 EP 0147429A1
- Authority
- EP
- European Patent Office
- Prior art keywords
- fibres
- silane
- cellulose
- weight
- oligomer
- 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- Withdrawn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
- 238000000034 method Methods 0.000 title claims abstract description 41
- 229920003043 Cellulose fiber Polymers 0.000 title claims abstract description 31
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 33
- 239000004568 cement Substances 0.000 claims abstract description 18
- 239000000835 fiber Substances 0.000 claims abstract description 15
- 229910000077 silane Inorganic materials 0.000 claims description 55
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 claims description 47
- 229920002678 cellulose Polymers 0.000 claims description 20
- 239000001913 cellulose Substances 0.000 claims description 20
- -1 amino compound Chemical class 0.000 claims description 15
- 239000003054 catalyst Substances 0.000 claims description 15
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 12
- 239000000123 paper Substances 0.000 claims description 11
- 238000011282 treatment Methods 0.000 claims description 10
- 239000002023 wood Substances 0.000 claims description 8
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical group N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 6
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 claims description 6
- 239000002253 acid Substances 0.000 claims description 6
- 239000011159 matrix material Substances 0.000 claims description 6
- 229910021653 sulphate ion Inorganic materials 0.000 claims description 6
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical group [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 claims description 5
- 125000004103 aminoalkyl group Chemical group 0.000 claims description 5
- 150000001412 amines Chemical class 0.000 claims description 4
- 229910021529 ammonia Inorganic materials 0.000 claims description 3
- 238000010438 heat treatment Methods 0.000 claims description 3
- 238000005470 impregnation Methods 0.000 claims description 3
- 239000000178 monomer Substances 0.000 claims description 3
- 239000002699 waste material Substances 0.000 claims description 3
- 244000198134 Agave sisalana Species 0.000 claims description 2
- 244000060011 Cocos nucifera Species 0.000 claims description 2
- 235000013162 Cocos nucifera Nutrition 0.000 claims description 2
- 229920000742 Cotton Polymers 0.000 claims description 2
- 125000005370 alkoxysilyl group Chemical group 0.000 claims description 2
- 239000000378 calcium silicate Substances 0.000 claims description 2
- 229910052918 calcium silicate Inorganic materials 0.000 claims description 2
- OYACROKNLOSFPA-UHFFFAOYSA-N calcium;dioxido(oxo)silane Chemical compound [Ca+2].[O-][Si]([O-])=O OYACROKNLOSFPA-UHFFFAOYSA-N 0.000 claims description 2
- 235000013339 cereals Nutrition 0.000 claims description 2
- 239000011093 chipboard Substances 0.000 claims description 2
- 239000000428 dust Substances 0.000 claims description 2
- 239000010440 gypsum Substances 0.000 claims description 2
- 229910052602 gypsum Inorganic materials 0.000 claims description 2
- 239000011121 hardwood Substances 0.000 claims description 2
- 238000011065 in-situ storage Methods 0.000 claims description 2
- 239000011120 plywood Substances 0.000 claims description 2
- 239000004627 regenerated cellulose Substances 0.000 claims description 2
- 239000011122 softwood Substances 0.000 claims description 2
- 239000010902 straw Substances 0.000 claims description 2
- LSNNMFCWUKXFEE-UHFFFAOYSA-L sulfite Chemical compound [O-]S([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-L 0.000 claims description 2
- 210000002268 wool Anatomy 0.000 claims description 2
- 230000002209 hydrophobic effect Effects 0.000 abstract description 5
- 239000002131 composite material Substances 0.000 abstract description 2
- 239000012783 reinforcing fiber Substances 0.000 abstract 1
- 239000003795 chemical substances by application Substances 0.000 description 17
- 238000006243 chemical reaction Methods 0.000 description 13
- 229910044991 metal oxide Inorganic materials 0.000 description 8
- 239000000203 mixture Substances 0.000 description 8
- 150000004706 metal oxides Chemical class 0.000 description 7
- 230000035515 penetration Effects 0.000 description 6
- 230000007062 hydrolysis Effects 0.000 description 5
- 238000006460 hydrolysis reaction Methods 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 4
- 238000001035 drying Methods 0.000 description 4
- 238000005507 spraying Methods 0.000 description 4
- KKEBXNMGHUCPEZ-UHFFFAOYSA-N 4-phenyl-1-(2-sulfanylethyl)imidazolidin-2-one Chemical compound N1C(=O)N(CCS)CC1C1=CC=CC=C1 KKEBXNMGHUCPEZ-UHFFFAOYSA-N 0.000 description 3
- 230000002378 acidificating effect Effects 0.000 description 3
- 239000010425 asbestos Substances 0.000 description 3
- 125000004432 carbon atom Chemical group C* 0.000 description 3
- 125000002091 cationic group Chemical group 0.000 description 3
- 238000009826 distribution Methods 0.000 description 3
- 239000002655 kraft paper Substances 0.000 description 3
- 229920000642 polymer Polymers 0.000 description 3
- 229910052895 riebeckite Inorganic materials 0.000 description 3
- RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 3
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 2
- BOTDANWDWHJENH-UHFFFAOYSA-N Tetraethyl orthosilicate Chemical compound CCO[Si](OCC)(OCC)OCC BOTDANWDWHJENH-UHFFFAOYSA-N 0.000 description 2
- 229920004482 WACKER® Polymers 0.000 description 2
- OGFYGJDCQZJOFN-UHFFFAOYSA-N [O].[Si].[Si] Chemical compound [O].[Si].[Si] OGFYGJDCQZJOFN-UHFFFAOYSA-N 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 125000003545 alkoxy group Chemical group 0.000 description 2
- 235000011114 ammonium hydroxide Nutrition 0.000 description 2
- 238000003851 corona treatment Methods 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 239000011518 fibre cement Substances 0.000 description 2
- 239000002657 fibrous material Substances 0.000 description 2
- 238000007654 immersion Methods 0.000 description 2
- 230000035484 reaction time Effects 0.000 description 2
- 150000004756 silanes Chemical class 0.000 description 2
- 235000012239 silicon dioxide Nutrition 0.000 description 2
- VXUYXOFXAQZZMF-UHFFFAOYSA-N titanium(IV) isopropoxide Chemical compound CC(C)O[Ti](OC(C)C)(OC(C)C)OC(C)C VXUYXOFXAQZZMF-UHFFFAOYSA-N 0.000 description 2
- 238000005809 transesterification reaction Methods 0.000 description 2
- NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 description 1
- 241000256844 Apis mellifera Species 0.000 description 1
- 239000004593 Epoxy Substances 0.000 description 1
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 1
- 241000286904 Leptothecata Species 0.000 description 1
- 206010058467 Lung neoplasm malignant Diseases 0.000 description 1
- 229920001410 Microfiber Polymers 0.000 description 1
- 235000008331 Pinus X rigitaeda Nutrition 0.000 description 1
- 235000011613 Pinus brutia Nutrition 0.000 description 1
- 241000018646 Pinus brutia Species 0.000 description 1
- 241000183024 Populus tremula Species 0.000 description 1
- 239000011398 Portland cement Substances 0.000 description 1
- XDXHAEQXIBQUEZ-UHFFFAOYSA-N Ropinirole hydrochloride Chemical compound Cl.CCCN(CCC)CCC1=CC=CC2=C1CC(=O)N2 XDXHAEQXIBQUEZ-UHFFFAOYSA-N 0.000 description 1
- 239000006087 Silane Coupling Agent Substances 0.000 description 1
- 201000010001 Silicosis Diseases 0.000 description 1
- 229910000831 Steel Inorganic materials 0.000 description 1
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- UGACIEPFGXRWCH-UHFFFAOYSA-N [Si].[Ti] Chemical compound [Si].[Ti] UGACIEPFGXRWCH-UHFFFAOYSA-N 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 150000004703 alkoxides Chemical class 0.000 description 1
- 239000001164 aluminium sulphate Substances 0.000 description 1
- 235000011128 aluminium sulphate Nutrition 0.000 description 1
- LFVGISIMTYGQHF-UHFFFAOYSA-N ammonium dihydrogen phosphate Chemical compound [NH4+].OP(O)([O-])=O LFVGISIMTYGQHF-UHFFFAOYSA-N 0.000 description 1
- 229910000387 ammonium dihydrogen phosphate Inorganic materials 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 125000004106 butoxy group Chemical group [*]OC([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- 239000004567 concrete Substances 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- 238000006297 dehydration reaction Methods 0.000 description 1
- BUACSMWVFUNQET-UHFFFAOYSA-H dialuminum;trisulfate;hydrate Chemical compound O.[Al+3].[Al+3].[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O BUACSMWVFUNQET-UHFFFAOYSA-H 0.000 description 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
- JKGITWJSGDFJKO-UHFFFAOYSA-N ethoxy(trihydroxy)silane Chemical class CCO[Si](O)(O)O JKGITWJSGDFJKO-UHFFFAOYSA-N 0.000 description 1
- 239000011094 fiberboard Substances 0.000 description 1
- 239000006260 foam Substances 0.000 description 1
- 239000003365 glass fiber Substances 0.000 description 1
- 239000008103 glucose Substances 0.000 description 1
- 125000001183 hydrocarbyl group Chemical group 0.000 description 1
- 239000011810 insulating material Substances 0.000 description 1
- 239000003456 ion exchange resin Substances 0.000 description 1
- 229920003303 ion-exchange polymer Polymers 0.000 description 1
- 201000005202 lung cancer Diseases 0.000 description 1
- 208000020816 lung neoplasm Diseases 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 239000003658 microfiber Substances 0.000 description 1
- 235000019837 monoammonium phosphate Nutrition 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 239000004745 nonwoven fabric Substances 0.000 description 1
- 239000005011 phenolic resin Substances 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 229920000098 polyolefin Polymers 0.000 description 1
- 239000011814 protection agent Substances 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 230000003014 reinforcing effect Effects 0.000 description 1
- 239000012779 reinforcing material Substances 0.000 description 1
- 239000005871 repellent Substances 0.000 description 1
- 125000005372 silanol group Chemical group 0.000 description 1
- 239000000344 soap Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 239000010959 steel Substances 0.000 description 1
- 150000005846 sugar alcohols Polymers 0.000 description 1
- 239000011270 tar paper Substances 0.000 description 1
- 229920001169 thermoplastic Polymers 0.000 description 1
- 229920001187 thermosetting polymer Polymers 0.000 description 1
- 239000004634 thermosetting polymer Substances 0.000 description 1
- 239000004416 thermosoftening plastic Substances 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- 238000009827 uniform distribution Methods 0.000 description 1
- 238000001291 vacuum drying Methods 0.000 description 1
Classifications
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- C—CHEMISTRY; METALLURGY
- C04—CEMENTS; CONCRETE; ARTIFICIAL STONE; CERAMICS; REFRACTORIES
- C04B—LIME, MAGNESIA; SLAG; CEMENTS; COMPOSITIONS THEREOF, e.g. MORTARS, CONCRETE OR LIKE BUILDING MATERIALS; ARTIFICIAL STONE; CERAMICS; REFRACTORIES; TREATMENT OF NATURAL STONE
- C04B41/00—After-treatment of mortars, concrete, artificial stone or ceramics; Treatment of natural stone
- C04B41/009—After-treatment of mortars, concrete, artificial stone or ceramics; Treatment of natural stone characterised by the material treated
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B27—WORKING OR PRESERVING WOOD OR SIMILAR MATERIAL; NAILING OR STAPLING MACHINES IN GENERAL
- B27K—PROCESSES, APPARATUS OR SELECTION OF SUBSTANCES FOR IMPREGNATING, STAINING, DYEING, BLEACHING OF WOOD OR SIMILAR MATERIALS, OR TREATING OF WOOD OR SIMILAR MATERIALS WITH PERMEANT LIQUIDS, NOT OTHERWISE PROVIDED FOR; CHEMICAL OR PHYSICAL TREATMENT OF CORK, CANE, REED, STRAW OR SIMILAR MATERIALS
- B27K3/00—Impregnating wood, e.g. impregnation pretreatment, for example puncturing; Wood impregnation aids not directly involved in the impregnation process
- B27K3/02—Processes; Apparatus
- B27K3/0278—Processes; Apparatus involving an additional treatment during or after impregnation
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B27—WORKING OR PRESERVING WOOD OR SIMILAR MATERIAL; NAILING OR STAPLING MACHINES IN GENERAL
- B27K—PROCESSES, APPARATUS OR SELECTION OF SUBSTANCES FOR IMPREGNATING, STAINING, DYEING, BLEACHING OF WOOD OR SIMILAR MATERIALS, OR TREATING OF WOOD OR SIMILAR MATERIALS WITH PERMEANT LIQUIDS, NOT OTHERWISE PROVIDED FOR; CHEMICAL OR PHYSICAL TREATMENT OF CORK, CANE, REED, STRAW OR SIMILAR MATERIALS
- B27K3/00—Impregnating wood, e.g. impregnation pretreatment, for example puncturing; Wood impregnation aids not directly involved in the impregnation process
- B27K3/34—Organic impregnating agents
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B27—WORKING OR PRESERVING WOOD OR SIMILAR MATERIAL; NAILING OR STAPLING MACHINES IN GENERAL
- B27K—PROCESSES, APPARATUS OR SELECTION OF SUBSTANCES FOR IMPREGNATING, STAINING, DYEING, BLEACHING OF WOOD OR SIMILAR MATERIALS, OR TREATING OF WOOD OR SIMILAR MATERIALS WITH PERMEANT LIQUIDS, NOT OTHERWISE PROVIDED FOR; CHEMICAL OR PHYSICAL TREATMENT OF CORK, CANE, REED, STRAW OR SIMILAR MATERIALS
- B27K3/00—Impregnating wood, e.g. impregnation pretreatment, for example puncturing; Wood impregnation aids not directly involved in the impregnation process
- B27K3/34—Organic impregnating agents
- B27K3/50—Mixtures of different organic impregnating agents
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B27—WORKING OR PRESERVING WOOD OR SIMILAR MATERIAL; NAILING OR STAPLING MACHINES IN GENERAL
- B27K—PROCESSES, APPARATUS OR SELECTION OF SUBSTANCES FOR IMPREGNATING, STAINING, DYEING, BLEACHING OF WOOD OR SIMILAR MATERIALS, OR TREATING OF WOOD OR SIMILAR MATERIALS WITH PERMEANT LIQUIDS, NOT OTHERWISE PROVIDED FOR; CHEMICAL OR PHYSICAL TREATMENT OF CORK, CANE, REED, STRAW OR SIMILAR MATERIALS
- B27K3/00—Impregnating wood, e.g. impregnation pretreatment, for example puncturing; Wood impregnation aids not directly involved in the impregnation process
- B27K3/52—Impregnating agents containing mixtures of inorganic and organic compounds
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B27—WORKING OR PRESERVING WOOD OR SIMILAR MATERIAL; NAILING OR STAPLING MACHINES IN GENERAL
- B27K—PROCESSES, APPARATUS OR SELECTION OF SUBSTANCES FOR IMPREGNATING, STAINING, DYEING, BLEACHING OF WOOD OR SIMILAR MATERIALS, OR TREATING OF WOOD OR SIMILAR MATERIALS WITH PERMEANT LIQUIDS, NOT OTHERWISE PROVIDED FOR; CHEMICAL OR PHYSICAL TREATMENT OF CORK, CANE, REED, STRAW OR SIMILAR MATERIALS
- B27K5/00—Treating of wood not provided for in groups B27K1/00, B27K3/00
- B27K5/007—Treating of wood not provided for in groups B27K1/00, B27K3/00 using pressure
- B27K5/0075—Vacuum
-
- C—CHEMISTRY; METALLURGY
- C04—CEMENTS; CONCRETE; ARTIFICIAL STONE; CERAMICS; REFRACTORIES
- C04B—LIME, MAGNESIA; SLAG; CEMENTS; COMPOSITIONS THEREOF, e.g. MORTARS, CONCRETE OR LIKE BUILDING MATERIALS; ARTIFICIAL STONE; CERAMICS; REFRACTORIES; TREATMENT OF NATURAL STONE
- C04B20/00—Use of materials as fillers for mortars, concrete or artificial stone according to more than one of groups C04B14/00 - C04B18/00 and characterised by shape or grain distribution; Treatment of materials according to more than one of the groups C04B14/00 - C04B18/00 specially adapted to enhance their filling properties in mortars, concrete or artificial stone; Expanding or defibrillating materials
- C04B20/10—Coating or impregnating
- C04B20/1051—Organo-metallic compounds; Organo-silicon compounds, e.g. bentone
-
- C—CHEMISTRY; METALLURGY
- C04—CEMENTS; CONCRETE; ARTIFICIAL STONE; CERAMICS; REFRACTORIES
- C04B—LIME, MAGNESIA; SLAG; CEMENTS; COMPOSITIONS THEREOF, e.g. MORTARS, CONCRETE OR LIKE BUILDING MATERIALS; ARTIFICIAL STONE; CERAMICS; REFRACTORIES; TREATMENT OF NATURAL STONE
- C04B41/00—After-treatment of mortars, concrete, artificial stone or ceramics; Treatment of natural stone
- C04B41/45—Coating or impregnating, e.g. injection in masonry, partial coating of green or fired ceramics, organic coating compositions for adhering together two concrete elements
- C04B41/46—Coating or impregnating, e.g. injection in masonry, partial coating of green or fired ceramics, organic coating compositions for adhering together two concrete elements with organic materials
- C04B41/49—Compounds having one or more carbon-to-metal or carbon-to-silicon linkages ; Organo-clay compounds; Organo-silicates, i.e. ortho- or polysilicic acid esters ; Organo-phosphorus compounds; Organo-inorganic complexes
- C04B41/4905—Compounds having one or more carbon-to-metal or carbon-to-silicon linkages ; Organo-clay compounds; Organo-silicates, i.e. ortho- or polysilicic acid esters ; Organo-phosphorus compounds; Organo-inorganic complexes containing silicon
- C04B41/4922—Compounds having one or more carbon-to-metal or carbon-to-silicon linkages ; Organo-clay compounds; Organo-silicates, i.e. ortho- or polysilicic acid esters ; Organo-phosphorus compounds; Organo-inorganic complexes containing silicon applied to the substrate as monomers, i.e. as organosilanes RnSiX4-n, e.g. alkyltrialkoxysilane, dialkyldialkoxysilane
-
- C—CHEMISTRY; METALLURGY
- C04—CEMENTS; CONCRETE; ARTIFICIAL STONE; CERAMICS; REFRACTORIES
- C04B—LIME, MAGNESIA; SLAG; CEMENTS; COMPOSITIONS THEREOF, e.g. MORTARS, CONCRETE OR LIKE BUILDING MATERIALS; ARTIFICIAL STONE; CERAMICS; REFRACTORIES; TREATMENT OF NATURAL STONE
- C04B41/00—After-treatment of mortars, concrete, artificial stone or ceramics; Treatment of natural stone
- C04B41/45—Coating or impregnating, e.g. injection in masonry, partial coating of green or fired ceramics, organic coating compositions for adhering together two concrete elements
- C04B41/46—Coating or impregnating, e.g. injection in masonry, partial coating of green or fired ceramics, organic coating compositions for adhering together two concrete elements with organic materials
- C04B41/49—Compounds having one or more carbon-to-metal or carbon-to-silicon linkages ; Organo-clay compounds; Organo-silicates, i.e. ortho- or polysilicic acid esters ; Organo-phosphorus compounds; Organo-inorganic complexes
- C04B41/4905—Compounds having one or more carbon-to-metal or carbon-to-silicon linkages ; Organo-clay compounds; Organo-silicates, i.e. ortho- or polysilicic acid esters ; Organo-phosphorus compounds; Organo-inorganic complexes containing silicon
- C04B41/495—Compounds having one or more carbon-to-metal or carbon-to-silicon linkages ; Organo-clay compounds; Organo-silicates, i.e. ortho- or polysilicic acid esters ; Organo-phosphorus compounds; Organo-inorganic complexes containing silicon applied to the substrate as oligomers or polymers
- C04B41/4977—Compounds having one or more carbon-to-metal or carbon-to-silicon linkages ; Organo-clay compounds; Organo-silicates, i.e. ortho- or polysilicic acid esters ; Organo-phosphorus compounds; Organo-inorganic complexes containing silicon applied to the substrate as oligomers or polymers characterised by the number of silicon atoms
-
- C—CHEMISTRY; METALLURGY
- C04—CEMENTS; CONCRETE; ARTIFICIAL STONE; CERAMICS; REFRACTORIES
- C04B—LIME, MAGNESIA; SLAG; CEMENTS; COMPOSITIONS THEREOF, e.g. MORTARS, CONCRETE OR LIKE BUILDING MATERIALS; ARTIFICIAL STONE; CERAMICS; REFRACTORIES; TREATMENT OF NATURAL STONE
- C04B41/00—After-treatment of mortars, concrete, artificial stone or ceramics; Treatment of natural stone
- C04B41/60—After-treatment of mortars, concrete, artificial stone or ceramics; Treatment of natural stone of only artificial stone
- C04B41/61—Coating or impregnation
- C04B41/62—Coating or impregnation with organic materials
- C04B41/64—Compounds having one or more carbon-to-metal of carbon-to-silicon linkages
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08B—POLYSACCHARIDES; DERIVATIVES THEREOF
- C08B15/00—Preparation of other cellulose derivatives or modified cellulose, e.g. complexes
- C08B15/05—Derivatives containing elements other than carbon, hydrogen, oxygen, halogens or sulfur
-
- 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
- D21H17/03—Non-macromolecular organic compounds
- D21H17/05—Non-macromolecular organic compounds containing elements other than carbon and hydrogen only
- D21H17/13—Silicon-containing compounds
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B27—WORKING OR PRESERVING WOOD OR SIMILAR MATERIAL; NAILING OR STAPLING MACHINES IN GENERAL
- B27K—PROCESSES, APPARATUS OR SELECTION OF SUBSTANCES FOR IMPREGNATING, STAINING, DYEING, BLEACHING OF WOOD OR SIMILAR MATERIALS, OR TREATING OF WOOD OR SIMILAR MATERIALS WITH PERMEANT LIQUIDS, NOT OTHERWISE PROVIDED FOR; CHEMICAL OR PHYSICAL TREATMENT OF CORK, CANE, REED, STRAW OR SIMILAR MATERIALS
- B27K2200/00—Wooden materials to be treated
- B27K2200/10—Articles made of particles or fibres consisting of wood or other lignocellulosic material
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02W—CLIMATE CHANGE MITIGATION TECHNOLOGIES RELATED TO WASTEWATER TREATMENT OR WASTE MANAGEMENT
- Y02W30/00—Technologies for solid waste management
- Y02W30/50—Reuse, recycling or recovery technologies
- Y02W30/91—Use of waste materials as fillers for mortars or concrete
Definitions
- the present invention concerns impregnated cellulose fibres in which the free hydroxy groups of the cellulose have been treated with a silane, thereby imparting the cellulose fibres a low water retention value, and to a method for preparing such impregnated cellulose fibres .
- metal oxide acylates One particular group of impregnating agents previously used are the metal oxide acylates. It is possible with metal oxide acylates to pre ⁇ pare cellulose fibres that have a very low water retention value, i . e. less 0.5%.
- the use of metal oxide acylates as an impregnating agent normally requires that the fibres have been dried to a water content of at least below 2%, and preferably in the range of about 0.01%, because the metal oxide acylates react with water forming insoluble metal soaps that prevent or impede the metal oxide acylates from reacting with the hydroxy groups of the cellulose.
- the resulting fibres may be so hydrophobic that it requires special means to dis ⁇ perse the fibres in for example an aqueous cement gel .
- cellulose fibres having a low water retention value may be prepared by reacting a silane directly with the cellulose fibre without the need for any substantial drying of the water present in the fibre (a cellulose fibre in equilibrium gene ⁇ rally contains about 7% by weight of water) .
- the present invention provides a method for preparing impregnated cellulose fibres having a low water retention value, comprising applying a tetraalkoxy silane or an oligomer thereof to cellulose .
- alkoxy denotes an alkoxy group of 1 -4 carbon atoms such as methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy and tert. butoxy, preferably ethoxy.
- oligomer means that the silane comprises a siloxane chain of preferably 2-10 silicon atoms.
- silanes have previously been used primarily as a corrosion protection agent for steel , in particular when admixed with zinc dust.
- ft is also known that for example tetraethoxy silane (which may also be regarded as a tetraethyl ester of silicic acid) may be converted into silicic acid esters of higher alcohols by a transesterif ication -type reaction .
- tetraethoxy silane which may also be regarded as a tetraethyl ester of silicic acid
- a tetraalkoxy silane may react directly with cellulose; the explanation probably resides in the fact that cellulose may also be regarded as a polyhydric alcohol .
- the method of the invention also makes it possible to prepare impregnated cellulose fibres in which the individual cellulose chains (consisting of glucose units) and/or the individual microfibres within the cellulose fibres are cross-lin ked with one another by the silicon-oxygen-silicon lin k. This reaction will greatly improve the stability and low water absorptivity of the fibres .
- Fu rthermore, hydroxysilane groups on the surface of the fibres which have not reacted with another identical group, will tend to create a hydrophil- lic milieu on the su rface of the fibre.
- Such a hydrophilicity is espe ⁇ cially useful if the fibre is to be utilized in an aqueous environment such as in a cement matrix .
- the reaction rate of the hydrolysis of the al koxysilane and hence the reaction rate of the transesterification reaction depends on the pH of the reaction environment in that the hydrolysis proceeds very slowly at neutral or near-neutral pH but is accelerated if the envi ronment is acidic or basic.
- the catalyst may be applied in the form of a solution , either aqueous or organic, or it may be present in a solid state.
- Basic catalysts are preferred since acids may tend to break down the cellulose itself .
- acidic catalysts include hydrochloric acid, ammonium dihydrogenphosphate, polyboric acid, and aluminium sulphate.
- basic catalysts include ammonia or an amine, but the catalyst may also be for example a basic polymer, such as an ion exchange resin , deposited on the fibres .
- the catalysts may optionally have been deposited on the fibres du ring the manufac ⁇ ture thereof .
- a particularly useful type of amine is an aminoal kyltrial kyloxy silane, in which the aminoal kyl moiety may have 1 -4 carbon atoms , in parti ⁇ cular 3 carbon atoms .
- This type of compound has the advantage that it seems to react in concert with the al koxy si lane thereby creating a
- An especially preferred method according to the invention is one in which the fibres are treated with a tetraalkyloxy silane or an oligomer thereof and an aminoalkyltrialkyloxy silane in ratio of about 100:0.1 - 100: 10, in particular in a ratio of about 100: 1 -100: 5. This is because a too high concentration of the catalysing aminoalkyltrialkyloxy silane mayresult in a too swift reaction causing poor penetration of the impregnating agent.
- the two compounds may be applied as a mixture or separately, in the latter case either the alkoxy silane first and the aminoalkyl trialkyloxy silane second or vice versa, or the two com- pounds may be applied simultaneously but without being in admixture initially, for example by spraying the two compounds and allowing the two sprays to mix.
- the particularly preferred type of al kyloxy silane oligomer is a mix ⁇ ture of oligomers of up to 10 silicon atoms optionally in admixture with monomer.
- Fibres treated with the above-mentioned large excess of the alkoxy silane will, since unreacted silane may also react with silane already fixed on the fibre, have the advantage of being non-flammable or at any rate only combustible with great difficulty. Consequently, such fibres are particularly useful for use as an insulating material in e. g . building wall cavities.
- the silane may take a long time to react with the fibres . Consequent ⁇ ly, it is possible to accelerate the process by treating the fibres with heat and in an atmosphere of high relative humidity after the appli ⁇ cation of the silane, or by treating the fibres with water optionally containing an acid or a base and optionally while heating .
- ples of acids and bases may be mentioned for example hydrochloric acid and ammonia .
- the treatment may be performed for a period of up to 24 hours .
- the silane may be applied when the fibres are in the form of a web of paper or cellulose pulp such as sulphate or sulphite pulp, hardwood and softwood pulp, cereal cellulose pulp, including straw cellulose pulp .
- Preferred types of fibres are for example waste fibres or vi rgin fibres .
- the cellulose fibres, to which the silane is applied may also be in the form of wood, fiber board, wood chip board, or plywood (both untreated or treated with CCA or CCP agents) , wood chips or shavings , saw dust, wood wool , synthetic or regenerated cellulose fibres, sisal , acacie, or coconut fibres, or cotton .
- the fibres may be subjected to a defibration treatment subsequent to or simultaneously with the impregnation as the defibration treatment will aid the distribution of the impregnating agent th roughout each fiber.
- the defibration treatment is preferably performed in a hammer mill or a disc defibrator.
- the silane and/or the catalyst may be applied by various means such as
- the pressure during the spraying may be in the range of 1-700 millibar, preferably in the range of 1 -100 millibar, in particular 1 -50 millibar, especially 1 -10 millibar, since the low pressure favours the formation of very small droplets.
- the catalyst in particular the amino compound, to the fibres after the silane compound and immediately prior to defibration in the hammer mill or disc defibrator.
- the silane which has a low viscosity
- the penetration may also be improved by corona treating the cellulose fibres prior to the application of the impregnating agent.
- the corona treatment will lower the surface tension of the fibres, thus ensuring an even better penetration .
- silicon-titaniumalkoxide condensed oligomer it is also interesting to apply a silicon-titaniumalkoxide condensed oligomer to the fibres in an amount of about 1 -10% calculated on the fibres together with a catalyst as described above, in particular an aminoalkyltrialkyloxysilane with the above described ratio between the condensed oligomer and the catalyzing silane.
- the silicon-titaniumal- koxide oligomer may in particular be applied prior to the catalyzing silane or in admixture with the catalyzing silane.
- the silicon-titanium ⁇ alkoxide oligomer is available as such or may be prepared for imme ⁇ diate use by reacting a tetraal koxy silane with a titanium tetraal- koxide in a predetermined ratio, usually a molar ratio of approximate- Iy 1 :2.
- the fibres may also be treated in situ when they are already em ⁇ bedded in an inorganic matrix, in particular cement, gypsum or calcium silicate.
- the matrix may be in form of for example building panels, such as wall plates or roof plates, and the application may be performed either by applying with a brush or spraying the impreg ⁇ nating agent on the plates in an amount of between 1 and 30%, prefe ⁇ rably 5-25%, in particular 10-20%, such as 15% by weight of the entire plate.
- This procedure causes the plate not to swell when subjected to water, which is an indication that the fibres have been rendered non-water absorbant, since the water-absorbing qualities of untreated fibres causes for example cement plates reinforced with untreated fibres to swell when wetted .
- the invention also concerns cellulose fibres obtainable by the process described above, that is, cellulose fibres in which the free hydroxy groups are substituted with a monomeric or oligomeric alkoxysilyl group.
- the number of substituted hydroxy groups is preferably above 75%, especially .above 85%, in particular above 90% of the total number of free hydroxy groups in the cellulose.
- the free hydroxy groups are preferably also substituted with an aminoal kyldial koxysilyl ' group.
- the fibres, whether hydrophobic or hydrophillic, prepared according to the method of the invention may, apart from the uses mentioned above, be useful for the following uses : Reinforcing material in va ⁇ rious thermoplastic or thermosetting polymers such as epoxy poly- esters, phenol resins, polyolefins etc. , polymer foams, gas or light concrete, as backing in e. g . non-woven fabrics , wallpaper, floor paper, tar paper and in any other situation where a non-absorbing fibre is needed .
- Reinforcing material in va ⁇ rious thermoplastic or thermosetting polymers such as epoxy poly- esters, phenol resins, polyolefins etc. , polymer foams, gas or light concrete, as backing in e. g . non-woven fabrics , wallpaper, floor paper, tar paper and in any other situation where a non-absorbing fibre is needed .
- TES 40 Mixture of ethyl silicic acid esters (ethyloxysi- loxanes) having 1 -9 silicon atoms per molecule, average formula S OC ⁇ H- ⁇ 33 ⁇ 0 335- Pro Wacker Chemie.
- Silane A-1100 A silane coupling agent, consisting of Y-amino- propyltriethoxysilane, from Union Carbide.
- the treating agents or combination of treating agents listed was applied to a cellulose web under reduced atmospheric pressure with immediate subsequent defibration in a hammer mill .
- the treatments were performed in a treatment plant comprising- supply rollers, a corona treatment unit, vacuum chamber fitted with application jets for the impregnating in treating agents, and a hammer mill, of the type as described in Applicants' co-pending Danish Application filed on the same day as the present application, and entitled "Fremgangsmade til impraegnering af et fibr ⁇ st scheme" (Method for impregnating a fibrous material) .
- the fibres had completed the reaction after about 10 days, after which it was not possible to extract un reacted silane.
- the fibres felt dry and were very hydrophilic, in that they were readily wettable by water.
- the fibres reacted cationic with a zeta-potential of approxi ⁇ mately + 30.
- the water retention value was below 0.50%, and the fibres dispersed easily in cement giving a uniform distribution in the matrix .
- Example 2 Using, the same conditions as in Example 1 regarding fibre type, room temperature, paper speed, and air pressu re the treated fibres listed in the following table were prepared using the listed amounts of the particular impregnating agent.
- the fibres of the Examples 11 -16 all completed their reaction within 6-20 days, after which time nothing could be extracted from the fibres .
- the fibres felt dry and reacted hydrophilic and cationic with a zeta-potential of from + 27 to + 57.
- the water retention value was below 0.50% and the fibres were easily dispersible in cement similar to the fibres of Example 1 .
- Bleached vi rgin sulphate fibres with an SR° of 16 were treated with 35% by weight of a mixtu re of TES 40 and Silane A-1100 in a ratio of 96:4.
- the fibre became hydrophilic after approximately 36 hours .
- Cement plates containing the fibres prepared according to Example 1 were prepared using 4, 5% by weight (calculated on the amount of cement) of fibres in a mixture of cement and water in a ratio of
- Kraft paper (lining paper made from unbleached pine sulphate pulp) was first treated with a 25% ammonia solution wh ich was sprayed on the paper in amounts between 10 and 20%, and was subsequently treated with TES 40 in an amount of 10-20%.
- the treatment resulted in a very dimension stable kraft paper which was first hydrophobic, but was made hydrophilic by accelerating the reaction th rough heating at 80-90 C for 5 minutes.
- a mixture was prepared of 284 g titaniumtetraisopropoxide (TPT) , 300g TES 40, and 1 ,6 g Silane A-1100.
- Kraft paper was treated with 10% by weight of the mixture, and the paper was defibrated .
- cement plates were cast using 9 g fibres, 191 g Portland ce ⁇ ment and 300 g water.
- the mixture was mixed thoroughly in a mixer for 3 minutes, and excess water was sucked off. The result was a smooth uniform fibre cement plate with a good distribution of the fibres.
- the water/cement ratio was 0.24, compared with 0. 16 for a pure Portland cement/water mixture and 0.40 for a fibre cement comprising untreated cellulose fibres indicating that the fibres only absorbed very little or no water.
- a cement plate with a thickness of 8 mm, reinforced with 4.5% un ⁇ treated virgin sulphate fibres, and a water/cement ratio of above 30 was impregnated by spraying with 15% by weight TES 40 (calculated on the weight of the plate) .
- the impregnated plate did not absorb any water and acted water-repellent.
Abstract
Procédé de préparation de fibres de cellulose ayant une faible valeur de retenue d'eau, lequel procédé consiste à appliquer un tétraalcoxysilane ou un oligomère de celui-ci sur les fibres de cellulose avec une teneur en eau comprise entre 1 et 10% en poids, en particulier entre 2 et 7% en poids, ou auxquelles l'on donne, simultanément à l'application ou après celle-ci, une teneur en eau de l'ordre de 1-10% en poids, en particulier 2-7% en poids. Les fibres préparées peuvent être hydrophobes ou hydrophiles et sont spécialement utiles en tant que fibres de renforcement dans un matériau composite mélangé à du ciment ou à d'autres matrices inorganiques.Process for the preparation of cellulose fibers having a low water retention value, which process consists in applying a tetraalkoxysilane or an oligomer thereof on the cellulose fibers with a water content of between 1 and 10% by weight, in particular between 2 and 7% by weight, or to which one gives, simultaneously to the application or after it, a water content of the order of 1-10% by weight, in particular 2-7% in weight. The fibers prepared can be hydrophobic or hydrophilic and are especially useful as reinforcing fibers in a composite material mixed with cement or other inorganic matrices.
Description
Claims
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DK2325/83 | 1983-05-24 | ||
DK232583A DK232583D0 (en) | 1983-05-24 | 1983-05-24 | IMPREGNATED CELLULOSE FIBERS |
Publications (1)
Publication Number | Publication Date |
---|---|
EP0147429A1 true EP0147429A1 (en) | 1985-07-10 |
Family
ID=8111625
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
EP84902199A Withdrawn EP0147429A1 (en) | 1983-05-24 | 1984-05-24 | A method for preparing impregnated cellulose fibers having a low water retention and products hereby obtained |
Country Status (4)
Country | Link |
---|---|
EP (1) | EP0147429A1 (en) |
AU (1) | AU3018484A (en) |
DK (1) | DK232583D0 (en) |
WO (1) | WO1984004765A1 (en) |
Cited By (8)
Publication number | Priority date | Publication date | Assignee | Title |
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US6872246B2 (en) | 2000-10-04 | 2005-03-29 | James Hardie Research Pty Limited | Fiber cement composite materials using cellulose fibers loaded with inorganic and/or organic substances |
US7658794B2 (en) | 2000-03-14 | 2010-02-09 | James Hardie Technology Limited | Fiber cement building materials with low density additives |
US7942964B2 (en) | 2003-01-09 | 2011-05-17 | James Hardie Technology Limited | Fiber cement composite materials using bleached cellulose fibers |
US7993570B2 (en) | 2002-10-07 | 2011-08-09 | James Hardie Technology Limited | Durable medium-density fibre cement composite |
US7998571B2 (en) | 2004-07-09 | 2011-08-16 | James Hardie Technology Limited | Composite cement article incorporating a powder coating and methods of making same |
US8133352B2 (en) | 2000-10-17 | 2012-03-13 | James Hardie Technology Limited | Method and apparatus for reducing impurities in cellulose fibers for manufacture of fiber reinforced cement composite materials |
US8209927B2 (en) | 2007-12-20 | 2012-07-03 | James Hardie Technology Limited | Structural fiber cement building materials |
US8993462B2 (en) | 2006-04-12 | 2015-03-31 | James Hardie Technology Limited | Surface sealed reinforced building element |
Families Citing this family (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4554215A (en) * | 1983-11-16 | 1985-11-19 | Edward Robbart | Coating of cellulosic base stocks and the product thereof |
DE19520906A1 (en) * | 1995-06-08 | 1996-12-12 | Feinchemie Gmbh Sebnitz | Modified material from renewable raw materials |
IT1296824B1 (en) * | 1997-12-02 | 1999-08-02 | Maranit S P A | FIBER SHEET PRODUCTION PROCESS - REINFORCED |
EP1068387A2 (en) | 1998-03-24 | 2001-01-17 | Avantgarb LLC | Modified textile and other materials and methods for their preparation |
KR100855848B1 (en) * | 2000-10-04 | 2008-09-01 | 제임스 하디 인터내셔널 파이낸스 비.브이. | Fiber cement composite materials using sized cellulose fibers |
EP1385801A4 (en) | 2001-04-09 | 2006-09-06 | James Hardie Int Finance Bv | Integral water resistant fibre-cement |
EP2196478A1 (en) * | 2008-12-12 | 2010-06-16 | EMPA Eidgenössische Materialprüfungs- und Forschungsanstalt | Surface modified cellulose nanofibrils |
US9850623B2 (en) | 2014-11-26 | 2017-12-26 | Sally KRIGSTIN | Water, grease and heat resistant bio-based products and method of making same |
Family Cites Families (1)
Publication number | Priority date | Publication date | Assignee | Title |
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JPS56500407A (en) * | 1979-04-24 | 1981-04-02 |
-
1983
- 1983-05-24 DK DK232583A patent/DK232583D0/en not_active Application Discontinuation
-
1984
- 1984-05-24 WO PCT/DK1984/000047 patent/WO1984004765A1/en unknown
- 1984-05-24 AU AU30184/84A patent/AU3018484A/en not_active Abandoned
- 1984-05-24 EP EP84902199A patent/EP0147429A1/en not_active Withdrawn
Non-Patent Citations (1)
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See references of WO8404765A1 * |
Cited By (12)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US7658794B2 (en) | 2000-03-14 | 2010-02-09 | James Hardie Technology Limited | Fiber cement building materials with low density additives |
US7727329B2 (en) | 2000-03-14 | 2010-06-01 | James Hardie Technology Limited | Fiber cement building materials with low density additives |
US8182606B2 (en) | 2000-03-14 | 2012-05-22 | James Hardie Technology Limited | Fiber cement building materials with low density additives |
US6872246B2 (en) | 2000-10-04 | 2005-03-29 | James Hardie Research Pty Limited | Fiber cement composite materials using cellulose fibers loaded with inorganic and/or organic substances |
US8133352B2 (en) | 2000-10-17 | 2012-03-13 | James Hardie Technology Limited | Method and apparatus for reducing impurities in cellulose fibers for manufacture of fiber reinforced cement composite materials |
US8268119B2 (en) | 2000-10-17 | 2012-09-18 | James Hardie Technology Limited | Method and apparatus for reducing impurities in cellulose fibers for manufacture of fiber reinforced cement composite materials |
US7993570B2 (en) | 2002-10-07 | 2011-08-09 | James Hardie Technology Limited | Durable medium-density fibre cement composite |
US7942964B2 (en) | 2003-01-09 | 2011-05-17 | James Hardie Technology Limited | Fiber cement composite materials using bleached cellulose fibers |
US8333836B2 (en) | 2003-01-09 | 2012-12-18 | James Hardie Technology Limited | Fiber cement composite materials using bleached cellulose fibers |
US7998571B2 (en) | 2004-07-09 | 2011-08-16 | James Hardie Technology Limited | Composite cement article incorporating a powder coating and methods of making same |
US8993462B2 (en) | 2006-04-12 | 2015-03-31 | James Hardie Technology Limited | Surface sealed reinforced building element |
US8209927B2 (en) | 2007-12-20 | 2012-07-03 | James Hardie Technology Limited | Structural fiber cement building materials |
Also Published As
Publication number | Publication date |
---|---|
WO1984004765A1 (en) | 1984-12-06 |
AU3018484A (en) | 1984-12-18 |
DK232583D0 (en) | 1983-05-24 |
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