TWI399418B - 水基二聚松香及其製備方法 - Google Patents
水基二聚松香及其製備方法 Download PDFInfo
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- TWI399418B TWI399418B TW97133645A TW97133645A TWI399418B TW I399418 B TWI399418 B TW I399418B TW 97133645 A TW97133645 A TW 97133645A TW 97133645 A TW97133645 A TW 97133645A TW I399418 B TWI399418 B TW I399418B
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- 238000000034 method Methods 0.000 title claims abstract description 28
- RSWGJHLUYNHPMX-UHFFFAOYSA-N Abietic-Saeure Natural products C12CCC(C(C)C)=CC2=CCC2C1(C)CCCC2(C)C(O)=O RSWGJHLUYNHPMX-UHFFFAOYSA-N 0.000 claims abstract description 38
- 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 claims abstract description 38
- 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 claims abstract description 38
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 18
- 239000000203 mixture Substances 0.000 claims abstract description 11
- 239000011347 resin Substances 0.000 claims abstract description 11
- 229920005989 resin Polymers 0.000 claims abstract description 11
- 239000007787 solid Substances 0.000 claims abstract description 5
- 239000003054 catalyst Substances 0.000 claims description 26
- 239000002253 acid Substances 0.000 claims description 8
- 239000004094 surface-active agent Substances 0.000 claims description 8
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 claims description 6
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 claims description 5
- 150000001412 amines Chemical class 0.000 claims description 4
- 239000011230 binding agent Substances 0.000 claims description 3
- YCPXWRQRBFJBPZ-UHFFFAOYSA-N 5-sulfosalicylic acid Chemical compound OC(=O)C1=CC(S(O)(=O)=O)=CC=C1O YCPXWRQRBFJBPZ-UHFFFAOYSA-N 0.000 claims description 2
- ULUAUXLGCMPNKK-UHFFFAOYSA-N Sulfobutanedioic acid Chemical compound OC(=O)CC(C(O)=O)S(O)(=O)=O ULUAUXLGCMPNKK-UHFFFAOYSA-N 0.000 claims description 2
- WPTFZDRBJGXAMT-UHFFFAOYSA-N 4-nonylbenzenesulfonic acid Chemical compound CCCCCCCCCC1=CC=C(S(O)(=O)=O)C=C1 WPTFZDRBJGXAMT-UHFFFAOYSA-N 0.000 claims 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims 2
- 229910052783 alkali metal Inorganic materials 0.000 claims 2
- -1 alkali metal salt Chemical class 0.000 claims 2
- XATFRRKBXKIIRM-UHFFFAOYSA-N 2-heptylbenzenesulfonic acid Chemical compound CCCCCCCC1=CC=CC=C1S(O)(=O)=O XATFRRKBXKIIRM-UHFFFAOYSA-N 0.000 claims 1
- SYSFRXFRWRDPIJ-UHFFFAOYSA-N 2-hexylbenzenesulfonic acid Chemical compound CCCCCCC1=CC=CC=C1S(O)(=O)=O SYSFRXFRWRDPIJ-UHFFFAOYSA-N 0.000 claims 1
- QWHHBVWZZLQUIH-UHFFFAOYSA-N 2-octylbenzenesulfonic acid Chemical compound CCCCCCCCC1=CC=CC=C1S(O)(=O)=O QWHHBVWZZLQUIH-UHFFFAOYSA-N 0.000 claims 1
- VBVVNLPJLRAFAI-UHFFFAOYSA-N 2-pentylbenzenesulfonic acid Chemical compound CCCCCC1=CC=CC=C1S(O)(=O)=O VBVVNLPJLRAFAI-UHFFFAOYSA-N 0.000 claims 1
- 125000000217 alkyl group Chemical group 0.000 claims 1
- 229910021529 ammonia Inorganic materials 0.000 claims 1
- 125000004432 carbon atom Chemical group C* 0.000 claims 1
- 239000000178 monomer Substances 0.000 claims 1
- 239000003377 acid catalyst Substances 0.000 abstract description 2
- 238000006471 dimerization reaction Methods 0.000 abstract description 2
- 239000000853 adhesive Substances 0.000 abstract 1
- 230000001070 adhesive effect Effects 0.000 abstract 1
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 18
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 239000006185 dispersion Substances 0.000 description 6
- 238000004458 analytical method Methods 0.000 description 5
- 238000004945 emulsification Methods 0.000 description 3
- 239000011521 glass Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- WBIQQQGBSDOWNP-UHFFFAOYSA-N 2-dodecylbenzenesulfonic acid Chemical compound CCCCCCCCCCCCC1=CC=CC=C1S(O)(=O)=O WBIQQQGBSDOWNP-UHFFFAOYSA-N 0.000 description 2
- 229910000831 Steel Inorganic materials 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 2
- 229940060296 dodecylbenzenesulfonic acid Drugs 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- 239000010959 steel Substances 0.000 description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
- RHLPAVIBWYPLRV-UHFFFAOYSA-N 2-hydroxy-4-sulfobenzoic acid Chemical compound OC(=O)C1=CC=C(S(O)(=O)=O)C=C1O RHLPAVIBWYPLRV-UHFFFAOYSA-N 0.000 description 1
- 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
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical class CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 239000000539 dimer Substances 0.000 description 1
- 230000000447 dimerizing effect Effects 0.000 description 1
- GVGUFUZHNYFZLC-UHFFFAOYSA-N dodecyl benzenesulfonate;sodium Chemical compound [Na].CCCCCCCCCCCCOS(=O)(=O)C1=CC=CC=C1 GVGUFUZHNYFZLC-UHFFFAOYSA-N 0.000 description 1
- 230000009977 dual effect Effects 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 230000003472 neutralizing effect Effects 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 238000004810 partition chromatography Methods 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
- 150000003458 sulfonic acid derivatives Chemical class 0.000 description 1
- 239000003784 tall oil Substances 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09F—NATURAL RESINS; FRENCH POLISH; DRYING-OILS; OIL DRYING AGENTS, i.e. SICCATIVES; TURPENTINE
- C09F1/00—Obtaining purification, or chemical modification of natural resins, e.g. oleo-resins
- C09F1/04—Chemical modification, e.g. esterification
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L93/00—Compositions of natural resins; Compositions of derivatives thereof
- C08L93/04—Rosin
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D11/00—Inks
- C09D11/02—Printing inks
- C09D11/08—Printing inks based on natural resins
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J193/00—Adhesives based on natural resins; Adhesives based on derivatives thereof
- C09J193/04—Rosin
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Materials Engineering (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Engineering & Computer Science (AREA)
- Adhesives Or Adhesive Processes (AREA)
- Inks, Pencil-Leads, Or Crayons (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Description
本發明係關於在極低含量之二聚酸催化劑存在下製備分散於水中之二聚松香的方法。本發明亦係關於其作為增黏樹脂(為固體或於水中)、油墨樹脂及包含該松香樹脂之黏合劑組合物及油墨組合物之用途。
許多將松香進行二聚作用的方法業已發表。先前方法所敍述者係使用強無機酸，諸如述於美國專利2,136,525、2,108,982、2,307,641、2,328,681、2,515,218、2,251,806、2,532,120以及4,105,462中作為催化劑的硫酸。
其他方法業已敍述者則係使用磺酸化聚合物，如美國專利4,414,146，或鹵化甲磺酸，美國專利4,339,377及4,172,070。
再者，於美國專利2,375,618、2,492,146、4,536,333中係敍述使用作為催化劑之甲酸的方法。
先前技術係使用包括最後水洗及催化劑除去步驟之程序，致使增加程序的複雜性及成本。
本發明一個目標係提供一種程序，該程序係使用極低含量及/或有助於其後產物應用之催化劑，因此可減除昂貴的洗滌及催化劑除去步驟之需要。
本發明藉由利用作為催化劑之羧化磺酸以產生二聚松香可解決上述經確認的缺點。本發明程序藉由本發明催化劑之高活性可減除催化劑之需要。
本發明亦係關於包括以根據本發明方法所製備之二聚松香增黏劑之黏合劑組合物。
本發明另外係關於用於油墨應用之樹脂，該樹脂包括作為結構單元之二聚松香。
本發明亦係關於一種包括油墨樹脂之油墨組合物，該油墨樹脂係以二聚松香為基礎。
用以產生二聚松香之本發明方法係以作為催化劑之羧化磺酸為基礎。在一個實施例中，係使用以松香0.1至1%重量比計之羧化磺酸衍生物作為催化劑，例如磺基琥珀酸、5-磺基水楊酸或4-磺酸鄰苯二甲酸。在較佳方法中，係使用作為催化劑之4-磺基水楊酸。該催化劑可留在最終產品中，或選擇性地與鹼中和，諸如氫氧化鉀或胺。
為其後水基分散體之應用(諸如水基增黏劑)，用以產生二聚松香之本發明方法係以作為催化劑之磺酸化介面活性劑為基礎。
水基分散體比(諸水基增黏劑)之製備確實需要介面活性劑，以促進乳化過程及穩定最終分散體。磺酸化介面活性劑為吾人所熟知者，且廣泛用於許多應用。在該實施例中，磺酸化介面活性劑係作為催化劑以產生二聚松香。該催化劑不需要分離步驟，且可使用以松香之1至5%重量比計高含量，此為一般在製備水基增黏劑之調配物中之介面活性劑含量。在後來乳化過程中，僅需要添加鹼(諸如氫氧化鉀或胺)以產生水基增黏劑分散體。該磺酸鹽介面活性劑可以達到雙重作用。首先係作為松香二聚化作用之催化劑，其後是中和反應，以形成用以製備水基增黏劑之乳化劑。
本發明方法較佳實施例中，係使用約3%重量比之十二烷基苯磺酸。該程序可製備約30%二聚松香。經以三乙醇胺中和後，可製備增黏劑分散體。
135℃下，將1000公克中國松香及20公克4-磺酸鄰苯二甲酸添加在玻璃反應器中，攪拌內容物，並持續4小時。而後，將該混合物加熱至160℃，並再持續4小時。
分析：軟化點：92℃(R&B)；
酸值：150毫克KOH/公克；
顏色(甲苯，50%)：Gardner 7；
二聚松香(GPC；RI檢測器)：41%。
140℃下，將1000公克中國橡膠及38公克十二烷基苯磺酸於玻璃反應器中，攪拌內容物，並持續4小時。
分析：軟化點：84℃(R&B)；
酸值：152毫克KOH/公克；
顏色(甲苯，50%)：Gardner 8；
二聚松香(GPC；RI檢測器)：29%。
將1000公克之範例2之松香樹脂在鋼製燒杯中於110℃下熔化。攪拌時，添加25公克三乙醇胺。攪拌時，在15分鐘內添加水(60℃)。將最終分散體冷卻。
分析：固體52%；黏度240mPas；
粒徑(平均數)：0.28μM；
pH：7.5。
使用p-TSA之實驗(與38公克範例2之十二烷基苯磺酸鈉鹽等莫耳之含量)。
135℃下，將1000公克妥爾油松香(TOR)及20公克p-TSA添加在玻璃反應器後，攪拌內容物，並持續4小時。
將溫度增加至150℃，並再持續1小時。添加13公克KOH水溶液(50%)。
分析：軟化點：83℃(R&B)；
酸值：146毫克KOH/公克；
二聚松香(氣相分配色譜法；RI檢測器)：22%。
將1000公克範例4之松香樹脂在鋼製燒杯中於110℃下熔化。攪拌時，在15分鐘內添加60℃之1000公克水。
冷卻內容物。
分析：無乳化也無轉化點。兩個階段，其中一者為固體松香樹脂，及另一者為水。
申請人援引之參考列表僅係為讀者之便利。其不會成為歐洲專利文獻的一部分。即使編者悉心編輯參考，但不能被排除誤差或遺漏，有關這方面，EPO放棄所有責任。
敍述中援引之專利文獻
美國專利：
2,136,525(第1頁，第11行)
2,108,982(第1頁，第11行)
2,307,641(第1頁，第11行)
2,328,681(第1頁，第11行)
2,515,218(第1頁，第11行)
2,251,806(第1頁，第12行)
2,532,120(第1頁，第12行)
4,105,462(第1頁，第12行)
4,414,146(第1頁，第14行)
4,339,377(第1頁，第15行)
4,172,070(第1頁，第15行)
2,375,618(第1頁，第17行)
2,492,146(第1頁，第17行)
4,536,333(第1頁，第17行)
Claims (11)
- 一種用以製備二聚松香之方法，其包含：使松香與催化劑接觸以製備二聚松香，該催化劑係羧化磺酸、烷基取代芳基磺酸，或其混合物，其中該烷基取代芳基磺酸包含具有至少5個碳原子之烷基。
- 如請求項1之方法，其中二聚松香係以鹼金屬鹽或有機胺中和以製備經中和之二聚松香，該經中和之二聚松香係分散在視需要存在介面活性劑之水中。
- 如請求項1之方法，其中該催化劑係羧化磺酸，且該催化劑以松香之量計，以介於0.1至1%重量比之含量存在。
- 如請求項1至3中任一項之方法，其中該催化劑係選自由磺基琥珀酸、5-磺基水楊酸、5-硫代間苯二甲酸及4-磺酸鄰苯二甲酸及其中任何兩種或更多種之組合所組成之群；且該催化劑以松香之量計，係以介於0.1至1%重量比之含量存在。
- 如請求項1之方法，其中該催化劑係為烷基取代芳基磺酸，且該催化劑以松香之量計，係以介於1至5%重量比之含量存在。
- 如請求項5之方法，其中該催化劑係選自戊基苯磺酸、己基苯磺酸、庚基苯磺酸、辛基苯磺酸、壬基苯磺酸、癸基苯磺酸、十二烷基苯磺酸、十二烷基二苯二磺酸或其中任兩種或更多種之組合。
- 如請求項6之方法，其中該二聚松香係經鹼金屬鹽、有 機胺或氨中和以製備經中和之二聚松香，而該經中和之二聚松香係分散在水中。
- 一種如請求項1至7中任一項所製備之二聚松香以固體或於水中之形式作為增黏劑樹脂之用途。
- 一種如請求項1至7中任一項所製備之二聚松香作為單體以改質樹脂用於油墨應用之用途。
- 一種如請求項1至7中任一項所製備之二聚松香在黏合劑組合物及墨水組合物中之用途。
- 如請求項2之方法，其中該二聚松香係在介面活性劑存在下中和。
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP20070075826 EP2039732A1 (en) | 2007-09-20 | 2007-09-20 | Waterbased dimerized rosins and the process to make them |
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| Publication Number | Publication Date |
|---|---|
| TW200930778A TW200930778A (en) | 2009-07-16 |
| TWI399418B true TWI399418B (zh) | 2013-06-21 |
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| TW97133645A TWI399418B (zh) | 2007-09-20 | 2008-09-02 | 水基二聚松香及其製備方法 |
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| Country | Link |
|---|---|
| US (2) | US8557954B2 (zh) |
| EP (3) | EP2039732A1 (zh) |
| JP (1) | JP5667443B2 (zh) |
| KR (1) | KR20100065331A (zh) |
| CN (1) | CN101802115A (zh) |
| AR (1) | AR068245A1 (zh) |
| AU (1) | AU2008300927B2 (zh) |
| BR (1) | BRPI0816834B1 (zh) |
| CA (1) | CA2700043C (zh) |
| ES (2) | ES2434826T3 (zh) |
| PL (2) | PL2570464T3 (zh) |
| PT (2) | PT2570464T (zh) |
| TW (1) | TWI399418B (zh) |
| WO (1) | WO2009036920A1 (zh) |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| EP2039732A1 (en) * | 2007-09-20 | 2009-03-25 | Hexion Specialty Chemicals Research Belgium S.A. | Waterbased dimerized rosins and the process to make them |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
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- 2008-09-11 US US12/674,747 patent/US8557954B2/en active Active
- 2008-09-11 EP EP20080802024 patent/EP2190940B1/en active Active
- 2008-09-11 CA CA 2700043 patent/CA2700043C/en active Active
- 2008-09-11 EP EP12184851.9A patent/EP2570464B1/en not_active Not-in-force
- 2008-09-11 CN CN200880107899A patent/CN101802115A/zh active Pending
- 2008-09-11 ES ES08802024T patent/ES2434826T3/es active Active
- 2008-09-11 BR BRPI0816834-2A patent/BRPI0816834B1/pt active IP Right Grant
- 2008-09-11 PT PT121848519T patent/PT2570464T/pt unknown
- 2008-09-11 JP JP2010525235A patent/JP5667443B2/ja active Active
- 2008-09-11 PT PT08802024T patent/PT2190940E/pt unknown
- 2008-09-11 PL PL12184851T patent/PL2570464T3/pl unknown
- 2008-09-11 WO PCT/EP2008/007463 patent/WO2009036920A1/en active Application Filing
- 2008-09-11 PL PL08802024T patent/PL2190940T3/pl unknown
- 2008-09-11 AU AU2008300927A patent/AU2008300927B2/en active Active
- 2008-09-11 ES ES12184851.9T patent/ES2637630T3/es active Active
- 2008-09-11 KR KR20107006101A patent/KR20100065331A/ko not_active Application Discontinuation
- 2008-09-19 AR ARP080104104 patent/AR068245A1/es active IP Right Grant
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2013
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| Publication number | Priority date | Publication date | Assignee | Title |
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| TW342347B (en) * | 1996-02-02 | 1998-10-11 | Hercules Inc | Emulsifier system for rosin sizing agents |
Also Published As
| Publication number | Publication date |
|---|---|
| US20110092667A1 (en) | 2011-04-21 |
| BRPI0816834B1 (pt) | 2018-06-12 |
| PL2190940T3 (pl) | 2014-01-31 |
| AU2008300927A1 (en) | 2009-03-26 |
| BRPI0816834A2 (pt) | 2015-03-17 |
| EP2570464B1 (en) | 2017-05-17 |
| US9012601B2 (en) | 2015-04-21 |
| JP2010539305A (ja) | 2010-12-16 |
| CA2700043A1 (en) | 2008-09-20 |
| CA2700043C (en) | 2013-11-26 |
| JP5667443B2 (ja) | 2015-02-12 |
| EP2039732A1 (en) | 2009-03-25 |
| AU2008300927B2 (en) | 2012-02-09 |
| WO2009036920A1 (en) | 2009-03-26 |
| KR20100065331A (ko) | 2010-06-16 |
| US20130345390A1 (en) | 2013-12-26 |
| PL2570464T3 (pl) | 2017-12-29 |
| CN101802115A (zh) | 2010-08-11 |
| ES2434826T3 (es) | 2013-12-17 |
| TW200930778A (en) | 2009-07-16 |
| AR068245A1 (es) | 2009-11-11 |
| EP2190940B1 (en) | 2013-08-28 |
| EP2570464A1 (en) | 2013-03-20 |
| PT2190940E (pt) | 2013-10-14 |
| US8557954B2 (en) | 2013-10-15 |
| ES2637630T3 (es) | 2017-10-13 |
| EP2190940A1 (en) | 2010-06-02 |
| PT2570464T (pt) | 2017-07-20 |
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