JP2016539216A - リグニンを処理するためおよび結合剤組成物を生成するための方法 - Google Patents
リグニンを処理するためおよび結合剤組成物を生成するための方法 Download PDFInfo
- Publication number
- JP2016539216A JP2016539216A JP2016526363A JP2016526363A JP2016539216A JP 2016539216 A JP2016539216 A JP 2016539216A JP 2016526363 A JP2016526363 A JP 2016526363A JP 2016526363 A JP2016526363 A JP 2016526363A JP 2016539216 A JP2016539216 A JP 2016539216A
- Authority
- JP
- Japan
- Prior art keywords
- composition
- value
- temperature
- lignin
- maintained
- 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.)
- Granted
Links
- 239000000203 mixture Substances 0.000 title claims abstract description 217
- 229920005610 lignin Polymers 0.000 title claims abstract description 171
- 238000000034 method Methods 0.000 title claims abstract description 80
- 239000011230 binding agent Substances 0.000 title claims description 71
- 239000003513 alkali Substances 0.000 claims abstract description 26
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims abstract description 26
- 238000010438 heat treatment Methods 0.000 claims abstract description 20
- 150000008044 alkali metal hydroxides Chemical class 0.000 claims abstract description 4
- 238000004519 manufacturing process Methods 0.000 claims description 20
- 230000001070 adhesive effect Effects 0.000 claims description 17
- 239000000853 adhesive Substances 0.000 claims description 16
- 150000001875 compounds Chemical class 0.000 claims description 16
- 150000002989 phenols Chemical class 0.000 claims description 16
- 239000011120 plywood Substances 0.000 claims description 14
- 239000002023 wood Substances 0.000 claims description 11
- 238000002156 mixing Methods 0.000 claims description 8
- 229930040373 Paraformaldehyde Natural products 0.000 claims description 7
- 239000003431 cross linking reagent Substances 0.000 claims description 7
- 229920002866 paraformaldehyde Polymers 0.000 claims description 7
- 239000000463 material Substances 0.000 claims description 6
- 239000011490 mineral wool Substances 0.000 claims description 6
- 239000002245 particle Substances 0.000 claims description 6
- 238000000465 moulding Methods 0.000 claims description 4
- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 claims description 4
- 239000003082 abrasive agent Substances 0.000 claims description 3
- 238000005266 casting Methods 0.000 claims description 3
- 239000003733 fiber-reinforced composite Substances 0.000 claims description 3
- 239000011094 fiberboard Substances 0.000 claims description 3
- 239000002783 friction material Substances 0.000 claims description 3
- 239000011491 glass wool Substances 0.000 claims description 3
- -1 intrellum Substances 0.000 claims description 3
- 239000011253 protective coating Substances 0.000 claims description 3
- QTWJRLJHJPIABL-UHFFFAOYSA-N 2-methylphenol;3-methylphenol;4-methylphenol Chemical compound CC1=CC=C(O)C=C1.CC1=CC=CC(O)=C1.CC1=CC=CC=C1O QTWJRLJHJPIABL-UHFFFAOYSA-N 0.000 claims description 2
- 229930003836 cresol Natural products 0.000 claims description 2
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 claims description 2
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims 1
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 39
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 15
- 239000002028 Biomass Substances 0.000 description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
- 239000007787 solid Substances 0.000 description 8
- 239000004615 ingredient Substances 0.000 description 7
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 6
- 229920002488 Hemicellulose Polymers 0.000 description 6
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
- 230000008901 benefit Effects 0.000 description 6
- 239000000284 extract Substances 0.000 description 6
- 238000005259 measurement Methods 0.000 description 6
- 238000004537 pulping Methods 0.000 description 6
- 238000000926 separation method Methods 0.000 description 6
- 238000012360 testing method Methods 0.000 description 6
- 150000001299 aldehydes Chemical class 0.000 description 5
- 229920001568 phenolic resin Polymers 0.000 description 5
- 238000004679 31P NMR spectroscopy Methods 0.000 description 4
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 4
- 238000004458 analytical method Methods 0.000 description 4
- 229910021538 borax Inorganic materials 0.000 description 4
- 239000003054 catalyst Substances 0.000 description 4
- HHEAADYXPMHMCT-UHFFFAOYSA-N dpph Chemical compound [O-][N+](=O)C1=CC([N+](=O)[O-])=CC([N+]([O-])=O)=C1[N]N(C=1C=CC=CC=1)C1=CC=CC=C1 HHEAADYXPMHMCT-UHFFFAOYSA-N 0.000 description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- 238000002360 preparation method Methods 0.000 description 4
- 238000012545 processing Methods 0.000 description 4
- 229920005989 resin Polymers 0.000 description 4
- 239000011347 resin Substances 0.000 description 4
- 239000004328 sodium tetraborate Substances 0.000 description 4
- 235000010339 sodium tetraborate Nutrition 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 125000001931 aliphatic group Chemical group 0.000 description 3
- 235000014633 carbohydrates Nutrition 0.000 description 3
- 150000001720 carbohydrates Chemical class 0.000 description 3
- 238000004880 explosion Methods 0.000 description 3
- 238000000605 extraction Methods 0.000 description 3
- 239000000945 filler Substances 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- XPFVYQJUAUNWIW-UHFFFAOYSA-N furfuryl alcohol Chemical compound OCC1=CC=CO1 XPFVYQJUAUNWIW-UHFFFAOYSA-N 0.000 description 3
- 238000001879 gelation Methods 0.000 description 3
- 235000011187 glycerol Nutrition 0.000 description 3
- 229920005611 kraft lignin Polymers 0.000 description 3
- 239000002655 kraft paper Substances 0.000 description 3
- 235000011837 pasties Nutrition 0.000 description 3
- 229920001467 poly(styrenesulfonates) Polymers 0.000 description 3
- 235000013824 polyphenols Nutrition 0.000 description 3
- 238000001556 precipitation Methods 0.000 description 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
- 150000003254 radicals Chemical class 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- NLZUEZXRPGMBCV-UHFFFAOYSA-N Butylhydroxytoluene Chemical compound CC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 NLZUEZXRPGMBCV-UHFFFAOYSA-N 0.000 description 2
- 239000004971 Cross linker Substances 0.000 description 2
- AEMRFAOFKBGASW-UHFFFAOYSA-N Glycolic acid Chemical compound OCC(O)=O AEMRFAOFKBGASW-UHFFFAOYSA-N 0.000 description 2
- 230000002292 Radical scavenging effect Effects 0.000 description 2
- 238000002835 absorbance Methods 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 150000003934 aromatic aldehydes Chemical class 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 239000001569 carbon dioxide Substances 0.000 description 2
- 229910002092 carbon dioxide Inorganic materials 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 239000003153 chemical reaction reagent Substances 0.000 description 2
- 238000010586 diagram Methods 0.000 description 2
- 238000009826 distribution Methods 0.000 description 2
- JBKVHLHDHHXQEQ-UHFFFAOYSA-N epsilon-caprolactam Chemical compound O=C1CCCCCN1 JBKVHLHDHHXQEQ-UHFFFAOYSA-N 0.000 description 2
- LEQAOMBKQFMDFZ-UHFFFAOYSA-N glyoxal Chemical compound O=CC=O LEQAOMBKQFMDFZ-UHFFFAOYSA-N 0.000 description 2
- 239000011121 hardwood Substances 0.000 description 2
- VKYKSIONXSXAKP-UHFFFAOYSA-N hexamethylenetetramine Chemical group C1N(C2)CN3CN1CN2C3 VKYKSIONXSXAKP-UHFFFAOYSA-N 0.000 description 2
- 239000011159 matrix material Substances 0.000 description 2
- 229910000000 metal hydroxide Inorganic materials 0.000 description 2
- 150000004692 metal hydroxides Chemical class 0.000 description 2
- 239000000123 paper Substances 0.000 description 2
- 239000005011 phenolic resin Substances 0.000 description 2
- 239000000376 reactant Substances 0.000 description 2
- 239000011122 softwood Substances 0.000 description 2
- BGJSXRVXTHVRSN-UHFFFAOYSA-N 1,3,5-trioxane Chemical compound C1OCOCO1 BGJSXRVXTHVRSN-UHFFFAOYSA-N 0.000 description 1
- 102000004190 Enzymes Human genes 0.000 description 1
- 108090000790 Enzymes Proteins 0.000 description 1
- 239000004606 Fillers/Extenders Substances 0.000 description 1
- 229940123457 Free radical scavenger Drugs 0.000 description 1
- 238000005481 NMR spectroscopy Methods 0.000 description 1
- 229920001131 Pulp (paper) Polymers 0.000 description 1
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000002535 acidifier Substances 0.000 description 1
- 150000001447 alkali salts Chemical class 0.000 description 1
- 238000005571 anion exchange chromatography Methods 0.000 description 1
- 230000003078 antioxidant effect Effects 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 229920001222 biopolymer Polymers 0.000 description 1
- KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 description 1
- 239000004327 boric acid Substances 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- 238000010000 carbonizing Methods 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- 238000001311 chemical methods and process Methods 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- MJSNUBOCVAKFIJ-LNTINUHCSA-N chromium;(z)-4-oxoniumylidenepent-2-en-2-olate Chemical compound [Cr].C\C(O)=C\C(C)=O.C\C(O)=C\C(C)=O.C\C(O)=C\C(C)=O MJSNUBOCVAKFIJ-LNTINUHCSA-N 0.000 description 1
- 238000002485 combustion reaction Methods 0.000 description 1
- 238000010924 continuous production Methods 0.000 description 1
- 238000010411 cooking Methods 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- 239000011162 core material Substances 0.000 description 1
- 230000000593 degrading effect Effects 0.000 description 1
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 239000003480 eluent Substances 0.000 description 1
- 230000002255 enzymatic effect Effects 0.000 description 1
- 239000004744 fabric Substances 0.000 description 1
- 235000013312 flour Nutrition 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- SLGWESQGEUXWJQ-UHFFFAOYSA-N formaldehyde;phenol Chemical compound O=C.OC1=CC=CC=C1 SLGWESQGEUXWJQ-UHFFFAOYSA-N 0.000 description 1
- 239000000446 fuel Substances 0.000 description 1
- HYBBIBNJHNGZAN-UHFFFAOYSA-N furfural Chemical compound O=CC1=CC=CO1 HYBBIBNJHNGZAN-UHFFFAOYSA-N 0.000 description 1
- 150000002334 glycols Chemical class 0.000 description 1
- 229940015043 glyoxal Drugs 0.000 description 1
- 239000004312 hexamethylene tetramine Substances 0.000 description 1
- 235000010299 hexamethylene tetramine Nutrition 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 239000002650 laminated plastic Substances 0.000 description 1
- 229920002521 macromolecule Polymers 0.000 description 1
- 239000000401 methanolic extract Substances 0.000 description 1
- 229920005615 natural polymer Polymers 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 239000011368 organic material Substances 0.000 description 1
- 239000005416 organic matter Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 230000021962 pH elevation Effects 0.000 description 1
- 238000005731 phosphitylation reaction Methods 0.000 description 1
- 239000004848 polyfunctional curative Substances 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 230000000379 polymerizing effect Effects 0.000 description 1
- 239000011970 polystyrene sulfonate Substances 0.000 description 1
- 229960002796 polystyrene sulfonate Drugs 0.000 description 1
- 238000002203 pretreatment Methods 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 238000003908 quality control method Methods 0.000 description 1
- 238000011002 quantification Methods 0.000 description 1
- 239000002516 radical scavenger Substances 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 239000011342 resin composition Substances 0.000 description 1
- 238000009416 shuttering Methods 0.000 description 1
- 238000001542 size-exclusion chromatography Methods 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000012086 standard solution Substances 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 229920002994 synthetic fiber Polymers 0.000 description 1
- 229920001864 tannin Polymers 0.000 description 1
- 235000018553 tannin Nutrition 0.000 description 1
- 239000001648 tannin Substances 0.000 description 1
- 229920001187 thermosetting polymer Polymers 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Images
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07G—COMPOUNDS OF UNKNOWN CONSTITUTION
- C07G1/00—Lignin; Lignin derivatives
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B27—WORKING OR PRESERVING WOOD OR SIMILAR MATERIAL; NAILING OR STAPLING MACHINES IN GENERAL
- B27N—MANUFACTURE BY DRY PROCESSES OF ARTICLES, WITH OR WITHOUT ORGANIC BINDING AGENTS, MADE FROM PARTICLES OR FIBRES CONSISTING OF WOOD OR OTHER LIGNOCELLULOSIC OR LIKE ORGANIC MATERIAL
- B27N3/00—Manufacture of substantially flat articles, e.g. boards, from particles or fibres
- B27N3/002—Manufacture of substantially flat articles, e.g. boards, from particles or fibres characterised by the type of binder
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08H—DERIVATIVES OF NATURAL MACROMOLECULAR COMPOUNDS
- C08H6/00—Macromolecular compounds derived from lignin, e.g. tannins, humic acids
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/0008—Organic ingredients according to more than one of the "one dot" groups of C08K5/01 - C08K5/59
- C08K5/0025—Crosslinking or vulcanising agents; including accelerators
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/04—Oxygen-containing compounds
- C08K5/07—Aldehydes; Ketones
-
- 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
-
- 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
- C09J197/00—Adhesives based on lignin-containing materials
- C09J197/005—Lignin
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B27—WORKING OR PRESERVING WOOD OR SIMILAR MATERIAL; NAILING OR STAPLING MACHINES IN GENERAL
- B27N—MANUFACTURE BY DRY PROCESSES OF ARTICLES, WITH OR WITHOUT ORGANIC BINDING AGENTS, MADE FROM PARTICLES OR FIBRES CONSISTING OF WOOD OR OTHER LIGNOCELLULOSIC OR LIKE ORGANIC MATERIAL
- B27N3/00—Manufacture of substantially flat articles, e.g. boards, from particles or fibres
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Life Sciences & Earth Sciences (AREA)
- Materials Engineering (AREA)
- Polymers & Plastics (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Forests & Forestry (AREA)
- Biochemistry (AREA)
- Wood Science & Technology (AREA)
- Manufacturing & Machinery (AREA)
- Adhesives Or Adhesive Processes (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Compounds Of Unknown Constitution (AREA)
- Paints Or Removers (AREA)
Abstract
Description
a)水性組成物の温度を40〜85℃に維持しながら、リグニンを水性組成物に溶解するステップであって、水性組成物はフェノール類から選択される化合物およびアルカリを含有し、アルカリはアルカリ金属の水酸化物を含む、ステップと、
b)組成物のpHを6〜14のpH値に維持しながら、組成物の温度が100℃を超えないという条件で、ステップa)における組成物の温度より高い温度で組成物を加熱するステップと
を含む方法に関する。
a)水性組成物の温度を40〜85℃に維持しながら、リグニンを水性組成物に溶解するステップであって、水性組成物はフェノール類から選択される化合物およびアルカリを含有し、アルカリはアルカリ金属の水酸化物を含む、ステップと、
b)組成物のpHを6〜14のpH値に維持しながら、組成物の温度が100℃を超えないという条件で、ステップa)における組成物の温度より高い温度で組成物を加熱するステップと、
c)ステップb)において形成された組成物を架橋剤と混合し、組成物のpHを6〜14のpH値に維持しながら組成物を60〜100℃の温度で加熱するステップと
を含む方法にさらに関する。
実施例1において生成された結合剤組成物を、粘着性組成物の製造のために用いた。結合剤組成物を、その例として例えばデンプン、木粉および硬化剤(例えばタンニンまたは炭酸塩)が言及され得る、したがって粘着性組成物を形成する、増量剤、充填剤、触媒、添加剤と混合した。その後、1.5mm未満の厚さを有する単板を、9−ベニヤ板を生成するために生成した粘着性組成物と合わせて接着した。8分後、冷間プレスパネルを、130℃で熱プレスした。結果は、接着効果が、単板を接着するために十分に良好であったことを示した。
実施例2において生成された結合剤組成物を、シャッターフィルムの製造のために用いた。42g/m2の重量を有するクラフト紙を、結合剤組成物を含浸させて130℃で乾燥させた。含浸した紙を、ベニヤ板の片側上で145℃で6分間加圧した。結果は、シャッターフィルムが、十分に良好に機能したことを示し、表面上の膨れまたは剥離は観察されなかった。
Claims (25)
- a)水性組成物の温度を40〜85℃に維持しながら、リグニンを前記水性組成物に溶解するステップであって、前記水性組成物はフェノール類から選択される化合物およびアルカリを含有し、前記アルカリはアルカリ金属の水酸化物を含む、ステップと、
b)前記組成物のpHを6〜14のpH値に維持しながら、前記組成物の温度が100℃を超えないという条件で、ステップa)における前記組成物の温度より高い温度で、前記組成物を加熱するステップと
を含むことを特徴とする、リグニンを処理するための方法。 - フェノール類から選択される前記化合物が、フェノール、クレゾール、レゾルシノールおよびそれらの組み合わせからなる群から選択される、請求項1に記載の方法。
- ステップa)において、前記組成物の温度が、65〜80℃の温度、好ましくは70〜75℃の温度に維持される、請求項1〜2のいずれか一項に記載の方法。
- ステップb)が、ステップa)における前記組成物の温度より少なくとも5℃、好ましくは少なくとも10℃、より好ましくは少なくとも20℃高い温度で前記組成物を加熱することを含む、請求項1〜3のいずれか一項に記載の方法。
- ステップa)において、前記組成物のpHが、4〜10のpH値、好ましくは4.5〜9.5のpH値、より好ましくは5〜9のpH値、さらにより好ましくは5.5〜8.5のpH値に維持される、請求項1〜4のいずれか一項に記載の方法。
- ステップb)において、前記組成物のpHが、好ましくは6〜10のpH値、より好ましくは6.5〜9.5のpH値、さらにより好ましくは7〜9のpH値に維持される、請求項5に記載の方法。
- ステップa)において、前記組成物のpHが、4〜14のpH値、好ましくは7〜13.5のpH値、より好ましくは8.5〜13のpH値に維持される、請求項1〜4のいずれか一項に記載の方法。
- ステップb)において、前記組成物のpHが、好ましくは7〜14のpH値、より好ましくは9〜13.5のpH値、さらにより好ましくは10〜13のpH値に維持される、請求項7に記載の方法。
- ステップb)において、前記組成物が、60〜100℃の温度で、好ましくは70〜95℃の温度で、より好ましくは75〜90℃の温度で加熱される、請求項1〜8のいずれか一項に記載の方法。
- a)水性組成物の温度を40〜85℃に維持しながら、リグニンを前記水性組成物に溶解するステップであって、前記水性組成物はフェノール類から選択される化合物およびアルカリを含有し、前記アルカリはアルカリ金属の水酸化物を含む、ステップと、
b)前記組成物のpHを6〜14のpH値に維持しながら、前記組成物の温度が100℃を超えないという条件で、ステップa)における前記組成物の温度より高い温度で、前記組成物を加熱するステップと、
c)ステップb)において形成された前記組成物を架橋剤と混合し、前記組成物のpHを6〜14のpH値に維持しながら前記組成物を60〜100℃の温度で加熱するステップと
を含むことを特徴とする結合剤組成物を生成するための方法。 - ステップb)が、ステップa)における前記組成物の前記温度より少なくとも5℃、好ましくは少なくとも10℃、より好ましくは少なくとも20℃高い、温度で前記組成物を加熱することを含む、請求項10に記載の方法。
- ステップc)が、好ましくは65〜95℃の温度で、より好ましくは70〜90℃の温度で、さらにより好ましくは75〜85℃の温度で前記組成物を加熱することを含む、請求項10〜11のいずれか一項に記載の方法。
- ステップa)において、前記組成物のpHが、4〜10のpH値、好ましくは4.5〜9.5のpH値、より好ましくは5〜9のpH値、さらにより好ましくは5.5〜8.5のpH値に維持される、請求項10〜12のいずれか一項に記載の方法。
- ステップb)において、前記組成物のpHが、好ましくは6〜10のpH値、より好ましくは6.5〜9.5のpH値、さらにより好ましくは7〜9のpH値に維持される、請求項13に記載の方法。
- ステップa)において、前記組成物のpHが、4〜14のpH値、好ましくは7〜13.5のpH値、より好ましくは8.5〜13のpH値に維持される、請求項10〜12のいずれか一項に記載の方法。
- ステップb)において、前記組成物のpHが、好ましくは7〜14のpH値、より好ましくは9〜13.5のpH値、さらにより好ましくは10〜13のpH値に維持される、請求項15に記載の方法。
- ステップc)において、前記組成物のpHが、6〜10のpH値、好ましくは6.5〜9.5のpH値、より好ましくは7〜9のpH値に維持される、請求項10〜16のいずれか一項に記載の方法。
- ステップc)において、前記組成物のpHが、7〜14のpH値、より好ましくは9〜13.5のpH値、さらにより好ましくは10〜13のpH値に維持される、請求項10〜16のいずれか一項に記載の方法。
- 前記架橋剤が、アルデヒド、好ましくはホルムアルデヒド、パラホルムアルデヒドまたはそれらの組み合わせである、請求項10〜18のいずれか一項に記載の方法。
- 結合剤組成物の製造のための請求項1〜9のいずれか一項に記載の方法によって処理されたリグニンの使用。
- 請求項10〜19のいずれか一項に記載の方法によって取得可能な結合剤組成物。
- 請求項21に記載の結合剤組成物を含む粘着性組成物。
- 積層物、好ましくは高圧積層物の生成のための請求項14または請求項17に記載の方法によって取得可能な結合剤組成物の使用。
- 鋳造材料、保護コーティング、摩擦材料、研磨材料、グラスウール、岩綿、プリプレグ、シャッターフィルム、上張り、成形成分または繊維強化合成物を生成するための請求項14または請求項17に記載の方法によって取得可能な結合剤組成物の使用。
- パーティクルボード、配向性ストランドボード、合板、イントレルラム、接着合板、ハードボード、ウェハーボード、ファイバーボード、ベニヤ板、または木材粘着剤を生成するための請求項16または請求項18に記載の方法によって取得可能な結合剤組成物の使用。
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
FI20136178A FI126737B (en) | 2013-11-26 | 2013-11-26 | Process for treating lignin and preparing a binder composition |
FI20136178 | 2013-11-26 | ||
PCT/FI2014/050902 WO2015079107A1 (en) | 2013-11-26 | 2014-11-25 | A method for treating lignin and for producing a binder composition |
Publications (2)
Publication Number | Publication Date |
---|---|
JP2016539216A true JP2016539216A (ja) | 2016-12-15 |
JP6538674B2 JP6538674B2 (ja) | 2019-07-03 |
Family
ID=52014142
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2016526363A Active JP6538674B2 (ja) | 2013-11-26 | 2014-11-25 | リグニンを処理するためおよび結合剤組成物を生成するための方法 |
Country Status (14)
Country | Link |
---|---|
US (1) | US10301437B2 (ja) |
EP (2) | EP3074410B1 (ja) |
JP (1) | JP6538674B2 (ja) |
CN (2) | CN105793272A (ja) |
BR (1) | BR112016009537B1 (ja) |
CA (1) | CA2927313C (ja) |
DE (1) | DE202014011173U1 (ja) |
ES (1) | ES2962503T3 (ja) |
FI (3) | FI126737B (ja) |
LT (1) | LT3783008T (ja) |
PL (1) | PL3783008T3 (ja) |
PT (1) | PT3783008T (ja) |
SI (1) | SI3783008T1 (ja) |
WO (1) | WO2015079107A1 (ja) |
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2021182542A1 (ja) * | 2020-03-11 | 2021-09-16 | 株式会社ブリヂストン | 接着剤組成物、ゴム-有機繊維コード複合体及びタイヤ |
WO2022145280A1 (ja) * | 2020-12-28 | 2022-07-07 | 出光興産株式会社 | リグニン組成物及びその使用 |
Families Citing this family (20)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
FI123936B2 (en) * | 2012-03-29 | 2019-03-29 | Upm Kymmene Corp | A method for increasing the reactivity of lignin |
FI126736B (en) | 2013-11-26 | 2017-04-28 | Upm Kymmene Corp | A process for treating lignin and preparing a binder composition |
FI126737B (en) | 2013-11-26 | 2017-04-28 | Upm Kymmene Corp | Process for treating lignin and preparing a binder composition |
SE539761C2 (en) | 2016-03-21 | 2017-11-21 | Stora Enso Oyj | Liquid lignin composition, lignin-based resin, and method of increasing the solubility of equation |
SE541735C2 (en) | 2016-07-11 | 2019-12-03 | Stora Enso Oyj | Method of manufacturing an oriented strand board product using a lignin-based phenolic resin |
CN106279874A (zh) * | 2016-08-10 | 2017-01-04 | 吴迪 | 一种木质素基聚乙烯材料的制备方法 |
EP3583223A4 (en) | 2017-02-16 | 2020-12-23 | Sweetwater Energy, Inc. | HIGH PRESSURE ZONES FOR PRE-TREATMENT |
NL2018722B1 (en) | 2017-04-14 | 2018-10-24 | Trespa Int Bv | A method for preparing an activated lignin composition |
SE541439C2 (en) * | 2017-07-18 | 2019-10-01 | Stora Enso Oyj | Liquid lignin composition |
US11033867B2 (en) * | 2017-09-27 | 2021-06-15 | Sustainable Fiber Technologies, LLC | Aqueous lignin and hemicellulose dispersion |
US11066588B2 (en) | 2017-11-21 | 2021-07-20 | Sustainable Fiber Technologies, LLC | Deicing composition comprising lignocellulosic byproducts |
US11091697B2 (en) | 2017-11-29 | 2021-08-17 | Sustainable Fiber Technologies, LLC | Dust suppressant and soil stabilization composition comprising lignocellulosic byproducts |
SE542796C2 (en) * | 2018-10-08 | 2020-07-07 | Stora Enso Oyj | Process for preparing a resin |
SE542795C2 (en) * | 2018-10-08 | 2020-07-07 | Stora Enso Oyj | Process for preparing a resin |
SE543103C2 (en) * | 2018-11-27 | 2020-10-06 | Stora Enso Oyj | Process for preparing a solution of lignin in an aqueous medium by partial methylolation |
EP4077490A1 (en) * | 2019-12-22 | 2022-10-26 | Sweetwater Energy, Inc. | Methods of making specialized lignin and lignin products from biomass |
FI130110B (en) | 2020-02-12 | 2023-03-02 | Upm Kymmene Corp | Binder composition |
US11572474B2 (en) | 2020-05-22 | 2023-02-07 | Sustainable Fiber Technologies, LLC | Compositions comprising lignocellulosic byproducts for tire ballasts and associated methods |
EP4001376A1 (en) | 2020-11-13 | 2022-05-25 | Wilsonart LLC | Multi-part lignin-based resin system for decorative laminates |
SI26246A (sl) * | 2021-09-28 | 2023-03-31 | Fenolit d.d | Nov postopek priprave rezolne smole z aktiviranim Kraft ligninom |
Citations (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2013144454A1 (en) * | 2012-03-29 | 2013-10-03 | Upm-Kymmene Corporation | A method for increasing the reactivity of lignin |
Family Cites Families (51)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4017430A (en) * | 1975-06-23 | 1977-04-12 | Georgia-Pacific Corporation | Coating composition |
US4306999A (en) | 1979-11-23 | 1981-12-22 | American Can Company | High solids, low viscosity lignin solutions |
CA1185238A (en) | 1981-06-16 | 1985-04-09 | Stephen Y. Lin | Sulfonated lignin dispersants and dyestuffs and methods utlizing the same |
DE3142047A1 (de) | 1981-10-23 | 1983-05-11 | Skf Kugellagerfabriken Gmbh, 8720 Schweinfurt | Vorrichtung zum druckgiessen eines waelzlagerkaefigs |
US4476193A (en) | 1982-09-14 | 1984-10-09 | Westinghouse Electric Corp. | Sulfur containing lignin modified alkaline earth treated phenolic impregnating resins for core layers of humidity resistant laminates |
CA1229334A (en) | 1983-09-29 | 1987-11-17 | Ronnie S. Roberts | Biomass fractionation process |
CA1284637C (en) | 1987-08-24 | 1991-06-04 | George S. Faass | Biomass fractionation process |
US5010156A (en) * | 1988-05-23 | 1991-04-23 | Eastman Kodak Company | Organosolv lignin-modified phenolic resins and method for their preparation |
CA2043313A1 (en) | 1989-04-03 | 1992-11-28 | Herbert A. Schroeder | Method for recovering and using lignin in adhesive resins |
US5196460A (en) | 1990-05-29 | 1993-03-23 | Repap Technologies Inc. | Rubber compositions containing high purity lignin derivatives |
CA2070500C (en) | 1991-06-13 | 1997-10-14 | Ted Mcvay | Reactive phenolic resin modifier |
CA2551418C (en) | 1997-09-12 | 2010-09-28 | Kabushiki Kaisha Maruto | Novel lignin derivatives, molded products using the same and processes for making the same |
CA2355808A1 (en) | 2001-08-24 | 2003-02-24 | 3926044 Canada Inc. | Process for preparing a black liquor-phenol formaldehyde thermoset resin |
JP2003159703A (ja) | 2001-11-27 | 2003-06-03 | Kono Shinsozai Kaihatsu Kk | ボードの製造方法 |
US6689737B2 (en) | 2002-01-17 | 2004-02-10 | The Procter & Gamble Company | Household cleaning and/or laundry detergent compositions comprising lignin-derived materials |
WO2005042586A1 (ja) | 2003-10-31 | 2005-05-12 | Functional Wood Material Research Association | リグノフェノール誘導体の製造方法及び装置 |
JP4316536B2 (ja) | 2005-06-07 | 2009-08-19 | 独立行政法人科学技術振興機構 | リグニン誘導体の分離及び回収方法 |
CN101440170B (zh) * | 2008-12-17 | 2012-02-22 | 中国林业科学研究院林产化学工业研究所 | 生物质改性酚醛泡沫塑料的制备方法 |
CN101492522B (zh) | 2009-02-27 | 2010-09-01 | 中国林业科学研究院林产化学工业研究所 | 碱木质素改性酚醛树脂的制备方法 |
CA2798256C (en) | 2009-05-28 | 2018-04-24 | Lignol Innovations Ltd. | Derivatives of native lignin from hardwood feedstocks |
US9580454B2 (en) | 2009-11-13 | 2017-02-28 | Fpinnovations | Biomass fractionation process for bioproducts |
CN102656214B (zh) | 2009-12-16 | 2015-09-16 | 多姆斯乔工厂股份公司 | 一定品质的木素磺酸盐以及制备一定品质的木素磺酸盐的方法 |
CN102844357B (zh) | 2010-02-15 | 2016-09-07 | 丽格诺新创有限公司 | 含有木素衍生物的碳纤维组合物 |
CA2812685A1 (en) | 2010-09-23 | 2012-03-29 | Toho Tenax Europe Gmbh | Thermoplastic lignin for producing carbon fibers |
FI125991B (fi) | 2010-10-15 | 2016-05-13 | Upm Kymmene Corp | Menetelmä ja laitteisto ligniinin jatkuvatoimiseksi saostamiseksi mustalipeästä |
AT510812A1 (de) | 2010-10-29 | 2012-06-15 | Annikki Gmbh | Verfahren zur gewinnung von lignin |
CA2822105A1 (en) | 2010-12-20 | 2012-06-28 | Shell Internationale Research Maatschappij B.V. | Process to produce biofuels from biomass |
US8692041B2 (en) | 2010-12-20 | 2014-04-08 | Shell Oil Company | Process to produce biofuels from biomass |
CA2821520A1 (en) | 2010-12-20 | 2012-06-28 | Joseph Broun Powell | Process to produce biofuels from biomass |
US20150159061A1 (en) | 2011-02-11 | 2015-06-11 | Lamfeddal KOUISNI | Phenol-formaldehyde and lignin phenol-formaldehyde adhesive polymers with carbon black, and method of making same |
FI124944B (fi) * | 2011-04-08 | 2015-03-31 | Upm Kymmene Corp | Menetelmä sideainekoostumuksen valmistamiseksi, sideainekoostumus, liima-ainekoostumus, kerrostettu komposiittirakenne, ja sideainekoostumuksen ja liimakoostumuksen käyttöjä |
CN102268833B (zh) * | 2011-07-26 | 2013-08-21 | 中国科学院过程工程研究所 | 一种农作物秸秆蒸汽爆破预水解硫酸盐法制备溶解浆的方法 |
FI20125362L (fi) | 2012-03-29 | 2013-09-30 | Upm Kymmene Corp | Ligniini sekä menetelmä ja järjestelmä ligniinin käsittelemiseksi |
FI123934B (en) | 2012-03-29 | 2013-12-31 | Upm Kymmene Corp | Use of low molecular weight lignin to prepare a binder composition |
US20150051385A1 (en) | 2012-04-26 | 2015-02-19 | Archer Daniels Midland Company | Liquid / Liquid Separation of Lignocellulosic Biomass to Produce Sugar Syrups and Lignin Fractions |
FI127816B (en) | 2012-06-06 | 2019-03-15 | Upm Kymmene Corp | Process for fractionating lignin |
CN102936323A (zh) * | 2012-12-03 | 2013-02-20 | 山东圣泉化工股份有限公司 | 木质素酚醛树脂的制备方法及木质素酚醛树脂泡沫的制备方法 |
JP2014133817A (ja) * | 2013-01-10 | 2014-07-24 | Sumitomo Bakelite Co Ltd | リグニン誘導体法の製造方法、およびリグニン樹脂成形体 |
WO2014172042A1 (en) | 2013-03-15 | 2014-10-23 | Sandia Corporation | Synthesis of novel ionic liquids from lignin-derived compounds |
WO2014142289A1 (ja) | 2013-03-15 | 2014-09-18 | 出光興産株式会社 | リグニン分解物の製造方法 |
EP3004455A4 (en) | 2013-05-29 | 2017-01-18 | SunCarbon AB | A method for the treatment of spent pulping liquor for the removal and production of a lignin containing product |
US20150045543A1 (en) | 2013-08-12 | 2015-02-12 | Melvin Mitchell | Isolation method for water insoluble components of a biomass and products provided therefrom |
ES2701849T3 (es) | 2013-09-27 | 2019-02-26 | Stora Enso Oyj | Una composición que comprende compuesto de lignina y epoxi para recubrimiento y método para su fabricación y su uso |
FI129414B (en) | 2013-09-30 | 2022-02-15 | Upm Kymmene Corp | Method for increasing the reactivity of lignin |
FI126736B (en) | 2013-11-26 | 2017-04-28 | Upm Kymmene Corp | A process for treating lignin and preparing a binder composition |
FI126737B (en) | 2013-11-26 | 2017-04-28 | Upm Kymmene Corp | Process for treating lignin and preparing a binder composition |
AU2014361863B2 (en) | 2013-12-12 | 2018-05-31 | Solenis Technologies, L.P. | Lignin nanoparticle dispersions and methods for producing and using the same |
FI126195B (en) | 2014-01-28 | 2016-08-15 | Upm Kymmene Corp | Fiber-based product |
US10767308B2 (en) | 2014-07-09 | 2020-09-08 | Virdia, Inc. | Methods for separating and refining lignin from black liquor and compositions thereof |
SE539887C2 (en) | 2014-10-03 | 2018-01-02 | Stora Enso Oyj | A method to purify lignin from Sulfur by using an electric field |
SE538572C2 (en) | 2014-12-22 | 2016-09-20 | Innventia Ab | Method of producing lignin with reduced amount of odorous substances |
-
2013
- 2013-11-26 FI FI20136178A patent/FI126737B/en active IP Right Review Request
-
2014
- 2014-11-25 WO PCT/FI2014/050902 patent/WO2015079107A1/en active Application Filing
- 2014-11-25 SI SI201432047T patent/SI3783008T1/sl unknown
- 2014-11-25 EP EP14809072.3A patent/EP3074410B1/en active Active
- 2014-11-25 FI FIEP20199803.6T patent/FI3783008T3/fi active
- 2014-11-25 LT LTEP20199803.6T patent/LT3783008T/lt unknown
- 2014-11-25 EP EP20199803.6A patent/EP3783008B1/en active Active
- 2014-11-25 DE DE202014011173.1U patent/DE202014011173U1/de active Active
- 2014-11-25 CN CN201480064472.1A patent/CN105793272A/zh active Pending
- 2014-11-25 CN CN202010633917.0A patent/CN111647171B/zh active Active
- 2014-11-25 PL PL20199803.6T patent/PL3783008T3/pl unknown
- 2014-11-25 ES ES20199803T patent/ES2962503T3/es active Active
- 2014-11-25 US US15/033,732 patent/US10301437B2/en active Active
- 2014-11-25 JP JP2016526363A patent/JP6538674B2/ja active Active
- 2014-11-25 CA CA2927313A patent/CA2927313C/en active Active
- 2014-11-25 PT PT201998036T patent/PT3783008T/pt unknown
- 2014-11-25 BR BR112016009537-5A patent/BR112016009537B1/pt active IP Right Grant
-
2017
- 2017-11-22 FI FIU20174265U patent/FI12008U1/fi active IP Right Grant
Patent Citations (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2013144454A1 (en) * | 2012-03-29 | 2013-10-03 | Upm-Kymmene Corporation | A method for increasing the reactivity of lignin |
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2021182542A1 (ja) * | 2020-03-11 | 2021-09-16 | 株式会社ブリヂストン | 接着剤組成物、ゴム-有機繊維コード複合体及びタイヤ |
WO2022145280A1 (ja) * | 2020-12-28 | 2022-07-07 | 出光興産株式会社 | リグニン組成物及びその使用 |
Also Published As
Publication number | Publication date |
---|---|
LT3783008T (lt) | 2023-11-10 |
CN105793272A (zh) | 2016-07-20 |
CA2927313C (en) | 2018-04-24 |
DE202014011173U1 (de) | 2018-05-16 |
EP3783008A1 (en) | 2021-02-24 |
EP3074410B1 (en) | 2020-11-11 |
US10301437B2 (en) | 2019-05-28 |
FI3783008T3 (fi) | 2023-12-18 |
JP6538674B2 (ja) | 2019-07-03 |
FI20136178A (fi) | 2015-05-27 |
BR112016009537B1 (pt) | 2021-05-25 |
EP3783008B1 (en) | 2023-09-27 |
PT3783008T (pt) | 2023-10-19 |
CA2927313A1 (en) | 2015-06-04 |
WO2015079107A1 (en) | 2015-06-04 |
EP3074410A1 (en) | 2016-10-05 |
SI3783008T1 (sl) | 2023-11-30 |
CN111647171A (zh) | 2020-09-11 |
US20160257791A1 (en) | 2016-09-08 |
FI126737B (en) | 2017-04-28 |
PL3783008T3 (pl) | 2024-01-29 |
FI12008U1 (fi) | 2018-03-23 |
CN111647171B (zh) | 2022-05-17 |
ES2962503T3 (es) | 2024-03-19 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
JP6538674B2 (ja) | リグニンを処理するためおよび結合剤組成物を生成するための方法 | |
US20230339998A1 (en) | Method of making a binder composition, and binder composition | |
US10894855B2 (en) | Method for increasing the reactivity of lignin | |
JP2024513600A (ja) | フェノール化合物を含まないバインダー組成物 | |
JP2024513597A (ja) | フェノール化合物を含まないバインダー組成物 |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
A621 | Written request for application examination |
Free format text: JAPANESE INTERMEDIATE CODE: A621 Effective date: 20171109 |
|
A977 | Report on retrieval |
Free format text: JAPANESE INTERMEDIATE CODE: A971007 Effective date: 20180726 |
|
A131 | Notification of reasons for refusal |
Free format text: JAPANESE INTERMEDIATE CODE: A131 Effective date: 20180821 |
|
A601 | Written request for extension of time |
Free format text: JAPANESE INTERMEDIATE CODE: A601 Effective date: 20181017 |
|
A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20190117 |
|
TRDD | Decision of grant or rejection written | ||
A01 | Written decision to grant a patent or to grant a registration (utility model) |
Free format text: JAPANESE INTERMEDIATE CODE: A01 Effective date: 20190514 |
|
A61 | First payment of annual fees (during grant procedure) |
Free format text: JAPANESE INTERMEDIATE CODE: A61 Effective date: 20190606 |
|
R150 | Certificate of patent or registration of utility model |
Ref document number: 6538674 Country of ref document: JP Free format text: JAPANESE INTERMEDIATE CODE: R150 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |