US3547679A - Dimensionally stabilized wood and method of making such wood - Google Patents
Dimensionally stabilized wood and method of making such wood Download PDFInfo
- Publication number
- US3547679A US3547679A US662576A US3547679DA US3547679A US 3547679 A US3547679 A US 3547679A US 662576 A US662576 A US 662576A US 3547679D A US3547679D A US 3547679DA US 3547679 A US3547679 A US 3547679A
- Authority
- US
- United States
- Prior art keywords
- wood
- glyoxal
- glycol
- treatment
- hydroxyethyl
- 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.)
- Expired - Lifetime
Links
- 239000002023 wood Substances 0.000 title abstract description 75
- 238000004519 manufacturing process Methods 0.000 title description 3
- LEQAOMBKQFMDFZ-UHFFFAOYSA-N glyoxal Chemical compound O=CC=O LEQAOMBKQFMDFZ-UHFFFAOYSA-N 0.000 abstract description 62
- 229940015043 glyoxal Drugs 0.000 abstract description 31
- 229920001515 polyalkylene glycol Polymers 0.000 abstract description 20
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 abstract description 14
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 abstract description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 abstract description 5
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical group OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 abstract description 4
- 102000008186 Collagen Human genes 0.000 abstract description 3
- 108010035532 Collagen Proteins 0.000 abstract description 3
- 239000004372 Polyvinyl alcohol Substances 0.000 abstract description 3
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 abstract description 3
- 239000005018 casein Substances 0.000 abstract description 3
- BECPQYXYKAMYBN-UHFFFAOYSA-N casein, tech. Chemical compound NCCCCC(C(O)=O)N=C(O)C(CC(O)=O)N=C(O)C(CCC(O)=N)N=C(O)C(CC(C)C)N=C(O)C(CCC(O)=O)N=C(O)C(CC(O)=O)N=C(O)C(CCC(O)=O)N=C(O)C(C(C)O)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=O)N=C(O)C(CCC(O)=O)N=C(O)C(COP(O)(O)=O)N=C(O)C(CCC(O)=N)N=C(O)C(N)CC1=CC=CC=C1 BECPQYXYKAMYBN-UHFFFAOYSA-N 0.000 abstract description 3
- 235000021240 caseins Nutrition 0.000 abstract description 3
- 239000003054 catalyst Substances 0.000 abstract description 3
- 229920001436 collagen Polymers 0.000 abstract description 3
- 238000004132 cross linking Methods 0.000 abstract description 3
- 239000000835 fiber Substances 0.000 abstract description 3
- 229920002451 polyvinyl alcohol Polymers 0.000 abstract description 3
- LCZVSXRMYJUNFX-UHFFFAOYSA-N 2-[2-(2-hydroxypropoxy)propoxy]propan-1-ol Chemical compound CC(O)COC(C)COC(C)CO LCZVSXRMYJUNFX-UHFFFAOYSA-N 0.000 abstract description 2
- SZXQTJUDPRGNJN-UHFFFAOYSA-N dipropylene glycol Chemical group OCCCOCCCO SZXQTJUDPRGNJN-UHFFFAOYSA-N 0.000 abstract description 2
- WBHQBSYUUJJSRZ-UHFFFAOYSA-M sodium bisulfate Chemical compound [Na+].OS([O-])(=O)=O WBHQBSYUUJJSRZ-UHFFFAOYSA-M 0.000 abstract description 2
- 238000005507 spraying Methods 0.000 abstract description 2
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical group OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 abstract description 2
- -1 methyl-hydroxyethyl Chemical group 0.000 abstract 3
- GAWIXWVDTYZWAW-UHFFFAOYSA-N C[CH]O Chemical group C[CH]O GAWIXWVDTYZWAW-UHFFFAOYSA-N 0.000 abstract 1
- 229920002153 Hydroxypropyl cellulose Polymers 0.000 abstract 1
- 239000003125 aqueous solvent Substances 0.000 abstract 1
- 125000002057 carboxymethyl group Chemical group [H]OC(=O)C([H])([H])[*] 0.000 abstract 1
- 239000001863 hydroxypropyl cellulose Substances 0.000 abstract 1
- 238000007654 immersion Methods 0.000 abstract 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 1
- 239000003960 organic solvent Substances 0.000 abstract 1
- 239000004289 sodium hydrogen sulphite Substances 0.000 abstract 1
- 239000001117 sulphuric acid Substances 0.000 abstract 1
- 235000011149 sulphuric acid Nutrition 0.000 abstract 1
- 238000000034 method Methods 0.000 description 17
- 239000000463 material Substances 0.000 description 8
- 229920001223 polyethylene glycol Polymers 0.000 description 8
- 239000000126 substance Substances 0.000 description 8
- 238000001035 drying Methods 0.000 description 7
- 239000002202 Polyethylene glycol Substances 0.000 description 6
- 239000001913 cellulose Substances 0.000 description 6
- 229920002678 cellulose Polymers 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- 238000005470 impregnation Methods 0.000 description 3
- 229920005610 lignin Polymers 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- 230000000087 stabilizing effect Effects 0.000 description 3
- 230000008961 swelling Effects 0.000 description 3
- 239000002253 acid Substances 0.000 description 2
- 150000001299 aldehydes Chemical class 0.000 description 2
- 125000002947 alkylene group Chemical group 0.000 description 2
- 150000004677 hydrates Chemical class 0.000 description 2
- 238000011065 in-situ storage Methods 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 239000011120 plywood Substances 0.000 description 2
- 229940093430 polyethylene glycol 1500 Drugs 0.000 description 2
- 229920001451 polypropylene glycol Polymers 0.000 description 2
- 229920002689 polyvinyl acetate Polymers 0.000 description 2
- 239000011118 polyvinyl acetate Substances 0.000 description 2
- 238000004381 surface treatment Methods 0.000 description 2
- 229920002134 Carboxymethyl cellulose Polymers 0.000 description 1
- 239000004129 EU approved improving agent Substances 0.000 description 1
- 229920000896 Ethulose Polymers 0.000 description 1
- 239000001859 Ethyl hydroxyethyl cellulose Substances 0.000 description 1
- 240000000731 Fagus sylvatica Species 0.000 description 1
- 235000010099 Fagus sylvatica Nutrition 0.000 description 1
- 229920000663 Hydroxyethyl cellulose Polymers 0.000 description 1
- 239000004354 Hydroxyethyl cellulose Substances 0.000 description 1
- 229920001479 Hydroxyethyl methyl cellulose Polymers 0.000 description 1
- 229920001807 Urea-formaldehyde Polymers 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- GZCGUPFRVQAUEE-SLPGGIOYSA-N aldehydo-D-glucose Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C=O GZCGUPFRVQAUEE-SLPGGIOYSA-N 0.000 description 1
- ZHNUHDYFZUAESO-OUBTZVSYSA-N aminoformaldehyde Chemical compound N[13CH]=O ZHNUHDYFZUAESO-OUBTZVSYSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 230000001680 brushing effect Effects 0.000 description 1
- 239000001768 carboxy methyl cellulose Substances 0.000 description 1
- 235000010948 carboxy methyl cellulose Nutrition 0.000 description 1
- 239000008112 carboxymethyl-cellulose Substances 0.000 description 1
- 238000004040 coloring Methods 0.000 description 1
- 230000002301 combined effect Effects 0.000 description 1
- 238000007598 dipping method Methods 0.000 description 1
- BXUKAXFDABMVND-UHFFFAOYSA-L disodium;1,2-dihydroxyethane-1,2-disulfonate Chemical compound [Na+].[Na+].[O-]S(=O)(=O)C(O)C(O)S([O-])(=O)=O BXUKAXFDABMVND-UHFFFAOYSA-L 0.000 description 1
- 235000019326 ethyl hydroxyethyl cellulose Nutrition 0.000 description 1
- 239000011094 fiberboard Substances 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 230000000855 fungicidal effect Effects 0.000 description 1
- 239000003292 glue Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 235000019447 hydroxyethyl cellulose Nutrition 0.000 description 1
- 230000001771 impaired effect Effects 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 230000000749 insecticidal effect Effects 0.000 description 1
- 239000004922 lacquer Substances 0.000 description 1
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 description 1
- 229920000609 methyl cellulose Polymers 0.000 description 1
- 239000001923 methylcellulose Substances 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 239000000025 natural resin Substances 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 229920006324 polyoxymethylene Polymers 0.000 description 1
- 238000009877 rendering Methods 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 230000000717 retained effect Effects 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 229910000342 sodium bisulfate Inorganic materials 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 230000006641 stabilisation Effects 0.000 description 1
- 238000011105 stabilization Methods 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 150000005846 sugar alcohols Polymers 0.000 description 1
- 230000002522 swelling effect Effects 0.000 description 1
- 239000010876 untreated wood Substances 0.000 description 1
Classifications
-
- 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
- B27K3/15—Impregnating involving polymerisation including use of polymer-containing impregnating agents
-
- 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
- C08L97/02—Lignocellulosic material, e.g. wood, straw or bagasse
-
- 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
- B27K3/08—Impregnating by pressure, e.g. vacuum impregnation
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L71/00—Compositions of polyethers obtained by reactions forming an ether link in the main chain; Compositions of derivatives of such polymers
- C08L71/02—Polyalkylene oxides
Definitions
- Another chemical method of achieving cross-linkages comprises treating the wood aldehyde vapours, primarily formaldehyde, in the presence of a mineral acid which acts as a catalyst. As a result of such treatment the wood will obtain a good dimensional stability at an increase in Weight of about 5%. However, the treatment with formaldehyde also results in a reduction of the mechanical characteristics of the wood, and the wood becomes brittle, wherefore this method has not been used in practice on a major scale.
- the present invention relates to a method which removes the above disadvantages.
- this method comprises carrying out stabilization by cross-linking with glyoxal and simultaneously swelling the wood with polyalkylene glycols or derivatives thereof. It was found, surprisingly, that by means of this invention it is possible to stabilize wood with a considerably reduced amount of chemicals as compared to treatment with polyalkylene glycols alone, and at the same time the undesirable brittleness which results from treatment with aldehyde alone, is eliminated.
- glyoxal is supplied by dipping the wood into a solution of glyoxal and polyalcohol in water or other solvent or by spraying or brushing the solution on the wood. Impregnation in vacuum and/or superatmospheric pressure can also be employed. In the subsequent drying of the wood, the portion of the glyoxal which has not been consumed to form cross-linkages between cellulose or lignin mole cules of the wood, will be hydrated and polymerized to form a mixture of hydrates of the formulae.
- n is an integer of the order of from 1 to 100.
- hydrates will function in the same manner as, e.g. polyethylene glycol in the treatment of the wood and will have a swelling action on the cell tissues, because the molecules are not greater than that they are capable of diffusing into the Wood.
- the polyalkylene glycol When drying wood treated with a combination of glyoxal and polyalkylene glycol, the polyalkylene glycol will react to some extent with glyoxal at elevated drying temperatures to form linear polyacetals, which may be tag. of the following composition, when the polyalkylene glycol is polyethylene glycol: Ho(o2H,oC2H4)..0oH-o(o2H,oozH4)n-oCHo Ho(o2H,-oo2Hr).0CHo(o2Hi-o-o2Hr)..o-oH0- Surprisingly, these products have also been found to have a dimensionally stabilizing effect on wood and other celluloisc materials, although they remain soluble in water.
- the advantage is obtained that the wood, when it is fully impregnated, will obtain an improved surface which does not feel greasy. Also, its tendency of taking up moisture is.reduced. On the other hand, it is softer and smoother than wood treated with glyoxal alone as the stabilizing agent.
- Examples of such substances which can either be caused to diffuse into the cell tissues or be deposited in the cell cavities include water-soluble cellulose derivatives, such as hydroxyethylcellulose, ethyl-hydroxyethylcellulose, methylhydroxyethylcellulose, methylcellulose, ethylhydroxypropylcellulose, carboxymethyl cellulose, as well as other polymeric compounds, such as polyvinyl alcohol and partially hydrolyzed polyvinyl acetate, and also collagen and casein. Particularly suitable for addition in this manner are water-soluble cellulose derivatives having a viscosity below 20 cp. in 2% aqueous solution at 20 C.
- Polyalkylene glycols and derivatives thereof which can be according to this invention, include e.g. diethylene glycol, triethylene glycol, dipropylene glycol, tripropylene glycol, and higher polyethylene glycols and polypropylene glycols. Particularly suitable are polyethylene glycols and polypropylene glycols having molecular weights 'between 200 and 6000.
- Glyoxal is used according to this invention e.g. in the form of technically pure aqueous solutions, which are sold commercially, usually having a glyoxal content of 30 to 40%.
- Chemical products which liberate glyoxal can also be used, e.g. glyoxal-sodium bisulfite, which is available in pulverulent form and contains about 20% glyoxal.
- partially polymerized glyoxal which is available in pulverulent form, can also be used.
- the present invention is not limited to stabilizing the dimensions of fresh wood or sawn wood, but can be applied also to other wood articles, such as veneer, plywood, laminated wood, particle board, fiberboard and glued wood structures.
- organic or inorganic acids or acid salts may be used, e.g. acetic acid, sulfuric acid, sodium hydrogen sulfate.
- acetic acid, sulfuric acid, sodium hydrogen sulfate may be used, e.g. acetic acid, sulfuric acid, sodium hydrogen sulfate.
- compositions according to this invention to glues for wood, plywood and other wood products as well as to paints and lacquers for surface treatment of wood or wood products.
- the treatment according to this invention can be carried out as a surface treatment or impregnation with polyalkylene glycol and glyoxal. Impregnation can be carried out at normal pressure, superatmospheric pressure or vacuum or as a combined vacuum-pressure impregnating procedure.
- polyalkylene glycol by treating the wood with an alkylene oxide and effecting -a polymerization thereof in situ in a suitable manner, whereby a polyalkylene glycol is formed by reaction with water present in the wood.
- EXAMPLE 1 Beech veneer having a thickness of 2.5 mm. and a moisture ratio of about 50% was immersed for 4 hours in an aqueous solution containing 6% by weight of glyoxal and 15% by weight of polyethylene glycol 1500 (A). Other veneers of the same grade were impregnated with anaqueous solution containing 30% by weight of polyethylene glycol 1500 (B). After drying at 100 C. to moisture ratio, a width shrinkage of 0.9% was found in veneer according to A and 2.0% according to B. Corresponding untreated samples showed a width shrinkage of 8.9%.
- a method of treating wood to improve dimensional stability and inhibit the development of checks in wood upon drying thereof which comprises applying to the wood a polyalkylene glycol or glycol-forming material in an amount within the range from about 1 to about by weight glycol, based on the dry weight of the wood, sutficient to cause the wood to swell, and glyoxal or a glyoxal-liberating material and in an amount within the range from about 0.5 to about 20% glyoxal, based on the dry weight of the wood, suflicient to react with itself, the polyalkylene glycol, lignin, and/or cellulose, and impregnating the wood therewith and effecting such reaction of the polyalkylene glycol and glyoxal to improve dimensional stability and inhibit development of checks.
- a method of treating wood in accordance with claim 1 including the step of drying the wood, after application of the glycol and glyoxal thereto.
- a method of treating wood in accordance with claim 1 comprising applying the polyalkylene glycol or glycol forming material and glyoxal simultaneously.
- a method of treating wood in accordance with claim 1 comprising separately applying the polyalkylene glycol or glycol forming material and glyoxal.
- a method of treating wood in accordance with claim 1 comprising only surface-treating the wood.
- a method of treating wood in accordance with claim 1 which comprises applying a vacuum to the wood to be treated, prior to applying the glycol and glyoxal thereto.
- a method of treating wood in accordance with claim 1 which comprises applying a pressure greater than atmos pheric pressure to the wood to be treated, prior to applying the glycol and glyoxal thereto.
- a method of treating wood in accordance with claim 1 including, in addition, the steps of applying to the wood a water-soluble glyoXal-reactive material, selected from the group consisting of water-soluble cellulose derivatives, polyvinyl alcohol, partially hydrolyzed polyvinyl acetate, collagen and casein, and effecting reaction of the material with glyoxal, thereby rendering the material less soluble in water.
- a water-soluble glyoXal-reactive material selected from the group consisting of water-soluble cellulose derivatives, polyvinyl alcohol, partially hydrolyzed polyvinyl acetate, collagen and casein, and effecting reaction of the material with glyoxal, thereby rendering the material less soluble in water.
- a method of treating wood in accordance with claim 1 which comprises treating the wood with an alkylene oxide, and effecting reaction thereof with itself and with water present in the wood, to form the corresponding polyalkylene glycol in situ in the wood.
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Chemical & Material Sciences (AREA)
- Wood Science & Technology (AREA)
- Forests & Forestry (AREA)
- Materials Engineering (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Chemical And Physical Treatments For Wood And The Like (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| SE11578/66A SE320480B (enrdf_load_stackoverflow) | 1966-08-26 | 1966-08-26 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US3547679A true US3547679A (en) | 1970-12-15 |
Family
ID=20294216
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US662576A Expired - Lifetime US3547679A (en) | 1966-08-26 | 1967-08-23 | Dimensionally stabilized wood and method of making such wood |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US3547679A (enrdf_load_stackoverflow) |
| AT (1) | AT278340B (enrdf_load_stackoverflow) |
| DE (1) | DE1642187A1 (enrdf_load_stackoverflow) |
| DK (1) | DK120257B (enrdf_load_stackoverflow) |
| FI (1) | FI45835C (enrdf_load_stackoverflow) |
| GB (1) | GB1164689A (enrdf_load_stackoverflow) |
| NL (1) | NL6711761A (enrdf_load_stackoverflow) |
| NO (1) | NO121867B (enrdf_load_stackoverflow) |
| SE (1) | SE320480B (enrdf_load_stackoverflow) |
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3912836A (en) * | 1972-04-27 | 1975-10-14 | Eriksson Erik Gustav L | Procedure for surface treatment of wood |
| US5916418A (en) * | 1997-04-28 | 1999-06-29 | International Paper Company | Improving the lay flat properties of paper for printing |
| US6444134B1 (en) * | 2000-02-22 | 2002-09-03 | The Flecto Company, Inc. | Wood floor refinishing process and product |
| WO2011085453A1 (en) * | 2010-01-18 | 2011-07-21 | Arch Wood Protection Pty Ltd | Reduced drying carrier formulation |
| AU2016219540B2 (en) * | 2011-01-18 | 2017-08-24 | Arch Wood Protection Pty Ltd | Reduced drying carrier formulation |
| CN108080237A (zh) * | 2017-11-28 | 2018-05-29 | 太和县鎏禧木业有限公司 | 一种榆木家具的表面涂饰方法 |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5789087A (en) * | 1997-01-08 | 1998-08-04 | Dow Corning Corporation | Method of conserving waterlogged materials |
Citations (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2140981A (en) * | 1935-04-11 | 1938-12-20 | Philip C P Booty | Process of impregnating wood and the like |
| US2572070A (en) * | 1945-03-27 | 1951-10-23 | Alfred J Stamm | Method of stabilizing wood |
| US2629674A (en) * | 1949-07-07 | 1953-02-24 | Upson Co | Method for treating cellulose and product thereof |
| US2643236A (en) * | 1950-12-29 | 1953-06-23 | American Cyanamid Co | Method of preparing condensation products of pentaerythritol and glyoxal |
| US2895923A (en) * | 1956-11-30 | 1959-07-21 | Quaker Chemical Products Corp | Aminotriazine modified polyacetals |
| US2902470A (en) * | 1956-11-30 | 1959-09-01 | Quaker Chemical Products Corp | Phenol modified polyacetals |
| US3183114A (en) * | 1961-04-24 | 1965-05-11 | American Mach & Foundry | Treatment of wood with ethylene oxide gas or propylene oxide gas |
| US3277058A (en) * | 1962-12-10 | 1966-10-04 | Shell Oil Co | Aldehyde copolymers and their preparation |
-
1966
- 1966-08-26 SE SE11578/66A patent/SE320480B/xx unknown
-
1967
- 1967-08-19 NO NO169431A patent/NO121867B/no unknown
- 1967-08-22 DK DK424067AA patent/DK120257B/da unknown
- 1967-08-23 US US662576A patent/US3547679A/en not_active Expired - Lifetime
- 1967-08-24 AT AT778767A patent/AT278340B/de not_active IP Right Cessation
- 1967-08-24 DE DE19671642187 patent/DE1642187A1/de not_active Withdrawn
- 1967-08-25 GB GB39301/67A patent/GB1164689A/en not_active Expired
- 1967-08-25 FI FI672288A patent/FI45835C/fi active
- 1967-08-27 NL NL6711761A patent/NL6711761A/xx unknown
Patent Citations (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2140981A (en) * | 1935-04-11 | 1938-12-20 | Philip C P Booty | Process of impregnating wood and the like |
| US2572070A (en) * | 1945-03-27 | 1951-10-23 | Alfred J Stamm | Method of stabilizing wood |
| US2629674A (en) * | 1949-07-07 | 1953-02-24 | Upson Co | Method for treating cellulose and product thereof |
| US2643236A (en) * | 1950-12-29 | 1953-06-23 | American Cyanamid Co | Method of preparing condensation products of pentaerythritol and glyoxal |
| US2895923A (en) * | 1956-11-30 | 1959-07-21 | Quaker Chemical Products Corp | Aminotriazine modified polyacetals |
| US2902470A (en) * | 1956-11-30 | 1959-09-01 | Quaker Chemical Products Corp | Phenol modified polyacetals |
| US3183114A (en) * | 1961-04-24 | 1965-05-11 | American Mach & Foundry | Treatment of wood with ethylene oxide gas or propylene oxide gas |
| US3277058A (en) * | 1962-12-10 | 1966-10-04 | Shell Oil Co | Aldehyde copolymers and their preparation |
Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3912836A (en) * | 1972-04-27 | 1975-10-14 | Eriksson Erik Gustav L | Procedure for surface treatment of wood |
| US5916418A (en) * | 1997-04-28 | 1999-06-29 | International Paper Company | Improving the lay flat properties of paper for printing |
| US6444134B1 (en) * | 2000-02-22 | 2002-09-03 | The Flecto Company, Inc. | Wood floor refinishing process and product |
| WO2011085453A1 (en) * | 2010-01-18 | 2011-07-21 | Arch Wood Protection Pty Ltd | Reduced drying carrier formulation |
| US9045681B2 (en) | 2010-01-18 | 2015-06-02 | Arch Wood Protection Pty Ltd | Reduced drying carrier formulation |
| AU2016219540B2 (en) * | 2011-01-18 | 2017-08-24 | Arch Wood Protection Pty Ltd | Reduced drying carrier formulation |
| CN108080237A (zh) * | 2017-11-28 | 2018-05-29 | 太和县鎏禧木业有限公司 | 一种榆木家具的表面涂饰方法 |
Also Published As
| Publication number | Publication date |
|---|---|
| GB1164689A (en) | 1969-09-17 |
| AT278340B (de) | 1970-01-26 |
| DK120257B (da) | 1971-05-03 |
| SE320480B (enrdf_load_stackoverflow) | 1970-02-09 |
| FI45835C (fi) | 1972-10-10 |
| NL6711761A (enrdf_load_stackoverflow) | 1968-02-27 |
| NO121867B (enrdf_load_stackoverflow) | 1971-04-19 |
| FI45835B (enrdf_load_stackoverflow) | 1972-06-30 |
| DE1642187A1 (de) | 1971-06-09 |
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