JP6376366B2 - 安定化サイズ製剤 - Google Patents
安定化サイズ製剤 Download PDFInfo
- Publication number
- JP6376366B2 JP6376366B2 JP2016549479A JP2016549479A JP6376366B2 JP 6376366 B2 JP6376366 B2 JP 6376366B2 JP 2016549479 A JP2016549479 A JP 2016549479A JP 2016549479 A JP2016549479 A JP 2016549479A JP 6376366 B2 JP6376366 B2 JP 6376366B2
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- JP
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- Prior art keywords
- polysaccharide
- food
- mixture
- stabilized
- food polysaccharide
- 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.)
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- 235000019312 arabinogalactan Nutrition 0.000 claims description 31
- PUVAFTRIIUSGLK-UHFFFAOYSA-M trimethyl(oxiran-2-ylmethyl)azanium;chloride Chemical group [Cl-].C[N+](C)(C)CC1CO1 PUVAFTRIIUSGLK-UHFFFAOYSA-M 0.000 claims description 31
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- OMDQUFIYNPYJFM-XKDAHURESA-N (2r,3r,4s,5r,6s)-2-(hydroxymethyl)-6-[[(2r,3s,4r,5s,6r)-4,5,6-trihydroxy-3-[(2s,3s,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]methoxy]oxane-3,4,5-triol Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@@H]1OC[C@@H]1[C@@H](O[C@H]2[C@H]([C@@H](O)[C@H](O)[C@@H](CO)O2)O)[C@H](O)[C@H](O)[C@H](O)O1 OMDQUFIYNPYJFM-XKDAHURESA-N 0.000 description 2
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- PYMYPHUHKUWMLA-UHFFFAOYSA-N arabinose Natural products OCC(O)C(O)C(O)C=O PYMYPHUHKUWMLA-UHFFFAOYSA-N 0.000 description 2
- PYMYPHUHKUWMLA-WDCZJNDASA-N arabinose Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)C=O PYMYPHUHKUWMLA-WDCZJNDASA-N 0.000 description 2
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- 125000000969 xylosyl group Chemical group C1([C@H](O)[C@@H](O)[C@H](O)CO1)* 0.000 description 2
- NJVOHKFLBKQLIZ-UHFFFAOYSA-N (2-ethenylphenyl) prop-2-enoate Chemical compound C=CC(=O)OC1=CC=CC=C1C=C NJVOHKFLBKQLIZ-UHFFFAOYSA-N 0.000 description 1
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- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
- RSWGJHLUYNHPMX-UHFFFAOYSA-N Abietic-Saeure Natural products C12CCC(C(C)C)=CC2=CCC2C1(C)CCCC2(C)C(O)=O RSWGJHLUYNHPMX-UHFFFAOYSA-N 0.000 description 1
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- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- WQZGKKKJIJFFOK-QTVWNMPRSA-N D-mannopyranose Chemical compound OC[C@H]1OC(O)[C@@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-QTVWNMPRSA-N 0.000 description 1
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- IAJILQKETJEXLJ-UHFFFAOYSA-N Galacturonsaeure Natural products O=CC(O)C(O)C(O)C(O)C(O)=O IAJILQKETJEXLJ-UHFFFAOYSA-N 0.000 description 1
- 229920001503 Glucan Polymers 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
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- 229920000057 Mannan Polymers 0.000 description 1
- 238000005481 NMR spectroscopy Methods 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- KHPCPRHQVVSZAH-HUOMCSJISA-N Rosin Natural products O(C/C=C/c1ccccc1)[C@H]1[C@H](O)[C@@H](O)[C@@H](O)[C@@H](CO)O1 KHPCPRHQVVSZAH-HUOMCSJISA-N 0.000 description 1
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- UGXQOOQUZRUVSS-ZZXKWVIFSA-N [5-[3,5-dihydroxy-2-(1,3,4-trihydroxy-5-oxopentan-2-yl)oxyoxan-4-yl]oxy-3,4-dihydroxyoxolan-2-yl]methyl (e)-3-(4-hydroxyphenyl)prop-2-enoate Chemical compound OC1C(OC(CO)C(O)C(O)C=O)OCC(O)C1OC1C(O)C(O)C(COC(=O)\C=C\C=2C=CC(O)=CC=2)O1 UGXQOOQUZRUVSS-ZZXKWVIFSA-N 0.000 description 1
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- WQZGKKKJIJFFOK-PHYPRBDBSA-N alpha-D-galactose Chemical compound OC[C@H]1O[C@H](O)[C@H](O)[C@@H](O)[C@H]1O WQZGKKKJIJFFOK-PHYPRBDBSA-N 0.000 description 1
- AEMOLEFTQBMNLQ-WAXACMCWSA-N alpha-D-glucuronic acid Chemical compound O[C@H]1O[C@H](C(O)=O)[C@@H](O)[C@H](O)[C@H]1O AEMOLEFTQBMNLQ-WAXACMCWSA-N 0.000 description 1
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- NEOIUIMNEOPFEP-UHFFFAOYSA-M methyl sulfate oxiran-2-ylmethyl(tripropyl)azanium Chemical compound COS(=O)(=O)[O-].C(C1CO1)[N+](CCC)(CCC)CCC NEOIUIMNEOPFEP-UHFFFAOYSA-M 0.000 description 1
- WMDIGBAWRPJQHR-UHFFFAOYSA-M methyl sulfate triethyl(oxiran-2-ylmethyl)azanium Chemical compound COS(=O)(=O)[O-].C(C1CO1)[N+](CC)(CC)CC WMDIGBAWRPJQHR-UHFFFAOYSA-M 0.000 description 1
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- YQFOHQBSENCNTR-UHFFFAOYSA-M oxiran-2-ylmethyl(tripropyl)azanium;chloride Chemical compound [Cl-].CCC[N+](CCC)(CCC)CC1CO1 YQFOHQBSENCNTR-UHFFFAOYSA-M 0.000 description 1
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- KHPCPRHQVVSZAH-UHFFFAOYSA-N trans-cinnamyl beta-D-glucopyranoside Natural products OC1C(O)C(O)C(CO)OC1OCC=CC1=CC=CC=C1 KHPCPRHQVVSZAH-UHFFFAOYSA-N 0.000 description 1
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Images
Classifications
-
- D—TEXTILES; PAPER
- D21—PAPER-MAKING; PRODUCTION OF CELLULOSE
- D21H—PULP COMPOSITIONS; PREPARATION THEREOF NOT COVERED BY SUBCLASSES D21C OR D21D; IMPREGNATING OR COATING OF PAPER; TREATMENT OF FINISHED PAPER NOT COVERED BY CLASS B31 OR SUBCLASS D21G; PAPER NOT OTHERWISE PROVIDED FOR
- D21H17/00—Non-fibrous material added to the pulp, characterised by its constitution; Paper-impregnating material characterised by its constitution
- D21H17/03—Non-macromolecular organic compounds
- D21H17/05—Non-macromolecular organic compounds containing elements other than carbon and hydrogen only
- D21H17/14—Carboxylic acids; Derivatives thereof
- D21H17/15—Polycarboxylic acids, e.g. maleic acid
- D21H17/16—Addition products thereof with hydrocarbons
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08B—POLYSACCHARIDES; DERIVATIVES THEREOF
- C08B37/00—Preparation of polysaccharides not provided for in groups C08B1/00 - C08B35/00; Derivatives thereof
- C08B37/14—Hemicellulose; Derivatives thereof
- C08B37/143—Hemicellulose; Derivatives thereof composed by pentose units, e.g. xylose, xylan, pentosans, arabinose (not used)
-
- 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
- C09J105/00—Adhesives based on polysaccharides or on their derivatives, not provided for in groups C09J101/00 or C09J103/00
- C09J105/14—Hemicellulose; Derivatives thereof
-
- 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
- D21H17/17—Ketenes, e.g. ketene dimers
-
- D—TEXTILES; PAPER
- D21—PAPER-MAKING; PRODUCTION OF CELLULOSE
- D21H—PULP COMPOSITIONS; PREPARATION THEREOF NOT COVERED BY SUBCLASSES D21C OR D21D; IMPREGNATING OR COATING OF PAPER; TREATMENT OF FINISHED PAPER NOT COVERED BY CLASS B31 OR SUBCLASS D21G; PAPER NOT OTHERWISE PROVIDED FOR
- D21H17/00—Non-fibrous material added to the pulp, characterised by its constitution; Paper-impregnating material characterised by its constitution
- D21H17/20—Macromolecular organic compounds
- D21H17/21—Macromolecular organic compounds of natural origin; Derivatives thereof
- D21H17/24—Polysaccharides
-
- D—TEXTILES; PAPER
- D21—PAPER-MAKING; PRODUCTION OF CELLULOSE
- D21H—PULP COMPOSITIONS; PREPARATION THEREOF NOT COVERED BY SUBCLASSES D21C OR D21D; IMPREGNATING OR COATING OF PAPER; TREATMENT OF FINISHED PAPER NOT COVERED BY CLASS B31 OR SUBCLASS D21G; PAPER NOT OTHERWISE PROVIDED FOR
- D21H17/00—Non-fibrous material added to the pulp, characterised by its constitution; Paper-impregnating material characterised by its constitution
- D21H17/20—Macromolecular organic compounds
- D21H17/21—Macromolecular organic compounds of natural origin; Derivatives thereof
- D21H17/24—Polysaccharides
- D21H17/31—Gums
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- 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
- D21H21/00—Non-fibrous material added to the pulp, characterised by its function, form or properties; Paper-impregnating or coating material, characterised by its function, form or properties
- D21H21/14—Non-fibrous material added to the pulp, characterised by its function, form or properties; Paper-impregnating or coating material, characterised by its function, form or properties characterised by function or properties in or on the paper
- D21H21/16—Sizing or water-repelling agents
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- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Biochemistry (AREA)
- Engineering & Computer Science (AREA)
- Molecular Biology (AREA)
- Materials Engineering (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- General Health & Medical Sciences (AREA)
- Paper (AREA)
- Polysaccharides And Polysaccharide Derivatives (AREA)
Description
WO 2008/145828 A1は、サイズ組成物中に存在していてもよいキシランエステルを開示している。このエステルは、ギ酸、酢酸、プロピオン酸、又は酪酸等の短鎖脂肪族カルボン酸とキシランとを反応させることによって製造される。
i. 帯電剤、水、及び触媒量の塩基の混合物を作り、この混合物を室温よりも高い一定温度で十分に攪拌し、
ii. 段階iで得られた混合物に非食物多糖と少量の水とを入れ、得られた混合物を一定温度で数時間攪拌し、次いで
iii.結果として得られた帯電非食物多糖を、回収の前に洗浄及び濾過する。
(例1)
市販の非食物多糖であるキシランから置換度の異なる5つの試料を作製した。
市販の非食物多糖であるアラビノガラクタンから置換度の異なる7つの試料を作製した。
料理用ミキサーを用いて2分間混合した後、150 barの圧力でホモジナイザーを通過させることによってASAエマルジョンを作製した。
(例4)
pH8.5の50/50の硬材/軟材のクラフトパルプ完成紙料に、例3で製造した安定化サイズ製剤を加えることによって、80 g/m2の実験室用ハンドシートを作製した。得られた紙の加工処理では填料を使用せず、ウェットエンドでの澱粉量は5kg/tであった。
Claims (10)
- サイズ剤と、キシラン若しくはアラビノガラクタン又はこれらの混合物を含む変性非食物多糖とを含有し、該変性非食物多糖が非食物多糖をカチオン性荷電アミノ試薬で変性することによって得られ、前記サイズ剤に対する前記変性非食物多糖の割合が0.05〜1であることを特徴とする安定化サイズ製剤。
- 前記サイズ剤が、AKD若しくはASA又はこれらの組み合わせであることを特徴とする、請求項1に記載の安定化サイズ製剤。
- 前記非食物多糖が、キシラン若しくはアラビノガラクタン又はこれらの混合物であることを特徴とする、請求項1又は2に記載の安定化サイズ製剤。
- 前記カチオン性荷電アミノ試薬がグリシジルトリメチルアンモニウムクロリドであることを特徴とする、請求項1に記載の安定化サイズ製剤。
- 前記変性非食物多糖の置換度が0.03〜1.5であることを特徴とする、請求項1〜4のいずれか一項に記載の安定化サイズ製剤。
- 前記サイズ製剤が、分散液の形態にあることを特徴とする、請求項1〜5のいずれか一項に記載の安定化サイズ製剤。
- 前記サイズ剤と、キシラン若しくはアラビノガラクタン又はこれらの混合物を含む前記変性非食物多糖であって、該変性非食物多糖が非食物多糖をカチオン性荷電アミノ試薬で変性することによって得られる変性非食物多糖とを水溶液中で接触させ、次いで、140bar〜160barの圧力で均質化させることによって分散液を形成することを特徴とする、請求項1に記載の安定化サイズ製剤の製造方法。
- 紙又は紙製品をサイズ処理するために使用される、請求項1〜6のいずれか一項に記載の安定化サイズ製剤。
- 前記安定化サイズ製剤のパルプへの投与量が0.5kg/t〜3kg/tであることを特徴とする、請求項8に記載の安定化サイズ製剤。
- カチオン性荷電アミノ試薬と反応させることによって多糖を官能基化して、変性非食物多糖を製造することを含む請求項1に記載の安定化サイズ製剤を製造する方法であって、
i.帯電剤、水、及び触媒量の塩基の混合物を作り、該混合物を室温よりも高い温度で十分に攪拌し、
ii.段階iで得られた混合物に、キシラン若しくはアラビノガラクタン又はこれらの混合物を含む前記非食物多糖と少量の水とを入れ、得られた混合物を一定温度で数時間攪拌し、次いで
iii.結果として得られたカチオン性帯電非食物多糖を、回収の前に洗浄及び濾過する段階を有することを特徴とする方法。
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
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FI20145118A FI126960B (en) | 2014-02-06 | 2014-02-06 | Stabilized adhesive formulation |
FI20145118 | 2014-02-06 | ||
PCT/FI2015/050076 WO2015118228A1 (en) | 2014-02-06 | 2015-02-06 | A stabilized sizing formulation |
Publications (3)
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JP2017505389A JP2017505389A (ja) | 2017-02-16 |
JP2017505389A5 JP2017505389A5 (ja) | 2017-08-17 |
JP6376366B2 true JP6376366B2 (ja) | 2018-08-22 |
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JP2016549479A Active JP6376366B2 (ja) | 2014-02-06 | 2015-02-06 | 安定化サイズ製剤 |
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US (1) | US10132038B2 (ja) |
EP (1) | EP3102736B1 (ja) |
JP (1) | JP6376366B2 (ja) |
CN (1) | CN105940156B (ja) |
BR (1) | BR112016017930B1 (ja) |
CA (1) | CA2938748C (ja) |
ES (1) | ES2655819T3 (ja) |
FI (1) | FI126960B (ja) |
PL (1) | PL3102736T3 (ja) |
PT (1) | PT3102736T (ja) |
RU (1) | RU2662507C2 (ja) |
WO (1) | WO2015118228A1 (ja) |
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CN111691236B (zh) * | 2020-05-26 | 2021-12-31 | 仙鹤股份有限公司 | 一种速干型圣经纸的生产方法 |
CN114907625B (zh) * | 2022-05-24 | 2023-07-14 | 天津科技大学 | 一种生物基防水防油剂的制备及应用 |
CN115323824A (zh) * | 2022-07-15 | 2022-11-11 | 龙游富田造纸精化有限公司 | 一种基于复合阳离子植物胶聚合物制备akd乳液工艺 |
WO2024134030A1 (en) * | 2022-12-21 | 2024-06-27 | Kemira Oyj | Aqueous dispersion of alkyl ketene dimer and its use |
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US4606773A (en) | 1984-12-10 | 1986-08-19 | Nalco Chemical Company | Emulsification of alkenyl succinic anhydride sizing agents |
JPH02127594A (ja) * | 1988-11-02 | 1990-05-16 | Hokuetsu Paper Mills Ltd | 置換コハク酸無水物を使用して行う製紙原料のサイズ化法 |
JP2806563B2 (ja) * | 1989-07-21 | 1998-09-30 | 日本ピー・エム・シー株式会社 | 製紙用サイズ剤組成物 |
FR2734005B1 (fr) * | 1995-05-12 | 1997-07-18 | Roquette Freres | Composition et procede pour le collage du papier |
US6093217A (en) | 1997-02-05 | 2000-07-25 | Akzo Nobel N.V. | Sizing of paper |
ID27508A (id) | 1998-04-06 | 2001-04-12 | Calgon Corp | Emulsifikasi perekat asa dengan getah alam untuk produk-produk kertas |
CA2330318A1 (en) | 1998-04-27 | 1999-11-04 | Larex, Inc. | Derivatives of arabinogalactan and compositions including the same |
US6123738A (en) | 1998-08-19 | 2000-09-26 | The Dow Chemical Company | Process for the production of low color 2,3-epoxypropyltrialkylammonium halide |
US6123760A (en) | 1998-10-28 | 2000-09-26 | Hercules Incorporated | Compositions and methods for preparing dispersions and methods for using the dispersions |
IL137887A0 (en) * | 1999-08-17 | 2001-10-31 | Nat Starch Chem Invest | Polysaccharide aldehydes prepared by oxidation method and used as strength additives in papermaking |
ATE447641T1 (de) * | 2000-01-11 | 2009-11-15 | Basf Se | Verfahren zur verbesserung drückfähigkeit und streichfähigkeit von papier und karton |
EP1314822A1 (en) * | 2001-11-19 | 2003-05-28 | Akzo Nobel N.V. | Process for sizing paper and sizing composition |
JP4379675B2 (ja) | 2002-10-28 | 2009-12-09 | 東邦化学工業株式会社 | カチオン変性多糖類及び該物質を含む組成物 |
TW200504265A (en) | 2002-12-17 | 2005-02-01 | Bayer Chemicals Corp | Alkenylsuccinic anhydride surface-applied system and uses thereof |
BRPI0409152A (pt) | 2003-04-01 | 2006-03-28 | Akzo Nobel Nv | dispersão |
DE10349727A1 (de) | 2003-10-23 | 2005-05-25 | Basf Ag | Feste Mischungen aus einem Reaktivleimungsmittel und Stärke, Verfahren zu ihrer Herstellung und ihre Verwendung |
DE102004003261A1 (de) * | 2004-01-21 | 2005-08-18 | Basf Ag | Alkenylbernsteinsäureanhydride enthaltende wässrige Polymerdispersionen, Verfahren zu ihrer Herstellung und ihre Verwendung |
WO2006096216A1 (en) | 2005-03-03 | 2006-09-14 | Kemira Oyj | Reduced shear cellulose reactive sizing agent for wet end applications |
MY146790A (en) * | 2005-12-21 | 2012-09-28 | Akzo Nobel Nv | Sizing of paper |
FI121811B (fi) * | 2007-06-01 | 2011-04-29 | Upm Kymmene Corp | Uudet dispersiot ja menetelmä niiden valmistamiseksi |
CL2008002019A1 (es) * | 2007-07-16 | 2009-01-16 | Akzo Nobel Chemicals Int Bv | Composicion de carga que comprende una carga, un compuesto inorganico cationico, un compuesto organico cationico y un polisacarido anionico; metodo para preparar dicha composicion; uso como aditivo para una suspension celulosica acuosa; procedimiento para producir papel; y papel. |
FI20096326A0 (fi) * | 2009-12-15 | 2009-12-15 | Valtion Teknillinen | Modifioitu biomateriaali, sen käytöt sekä modifiointimenetelmät |
US8236857B2 (en) * | 2010-07-08 | 2012-08-07 | Wellesley Pharmaceuticals, Llc | Extended-release formulation for reducing the frequency of urination and method of use thereof |
US20120244221A1 (en) * | 2010-07-08 | 2012-09-27 | Wellesley Pharmaceuticals, Llc | Extended-release formulation for reducing the frequency of urination and method of use thereof |
US20120135050A1 (en) * | 2010-07-08 | 2012-05-31 | Wellesley Pharmaceuticals, Llc | Extended-release formulation for reducing the frequency of urination and method of use thereof |
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- 2015-02-06 CA CA2938748A patent/CA2938748C/en active Active
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CA2938748A1 (en) | 2015-08-13 |
CN105940156B (zh) | 2019-05-10 |
PL3102736T3 (pl) | 2018-04-30 |
CA2938748C (en) | 2021-05-04 |
RU2662507C2 (ru) | 2018-07-26 |
FI20145118A (fi) | 2015-08-07 |
PT3102736T (pt) | 2018-01-30 |
CN105940156A (zh) | 2016-09-14 |
ES2655819T3 (es) | 2018-02-21 |
EP3102736A1 (en) | 2016-12-14 |
BR112016017930B1 (pt) | 2022-01-18 |
US20160348317A1 (en) | 2016-12-01 |
RU2016129033A3 (ja) | 2018-03-14 |
US10132038B2 (en) | 2018-11-20 |
RU2016129033A (ru) | 2018-03-14 |
JP2017505389A (ja) | 2017-02-16 |
EP3102736B1 (en) | 2017-11-22 |
FI126960B (en) | 2017-08-31 |
WO2015118228A1 (en) | 2015-08-13 |
BR112016017930A2 (ja) | 2017-08-08 |
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