JP5346299B2 - アルコキシレート混合物界面活性剤 - Google Patents
アルコキシレート混合物界面活性剤 Download PDFInfo
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- 239000004094 surface-active agent Substances 0.000 title claims description 87
- 239000000203 mixture Substances 0.000 title claims description 79
- 125000000217 alkyl group Chemical group 0.000 claims description 27
- 238000009826 distribution Methods 0.000 claims description 15
- 229910052799 carbon Inorganic materials 0.000 claims description 14
- 235000015112 vegetable and seed oil Nutrition 0.000 claims description 14
- 239000003599 detergent Substances 0.000 claims description 13
- 239000002736 nonionic surfactant Substances 0.000 claims description 11
- 125000004432 carbon atom Chemical group C* 0.000 claims description 6
- 239000012459 cleaning agent Substances 0.000 claims 2
- 230000000052 comparative effect Effects 0.000 description 37
- 239000000499 gel Substances 0.000 description 37
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 26
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 26
- 238000012360 testing method Methods 0.000 description 26
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 26
- 150000001298 alcohols Chemical class 0.000 description 24
- 238000002360 preparation method Methods 0.000 description 20
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 17
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 15
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 15
- 238000004090 dissolution Methods 0.000 description 11
- 239000003054 catalyst Substances 0.000 description 10
- 238000007046 ethoxylation reaction Methods 0.000 description 10
- MWKFXSUHUHTGQN-UHFFFAOYSA-N decan-1-ol Chemical compound CCCCCCCCCCO MWKFXSUHUHTGQN-UHFFFAOYSA-N 0.000 description 8
- 239000003209 petroleum derivative Substances 0.000 description 8
- KBPLFHHGFOOTCA-UHFFFAOYSA-N 1-Octanol Chemical compound CCCCCCCCO KBPLFHHGFOOTCA-UHFFFAOYSA-N 0.000 description 7
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 7
- LQZZUXJYWNFBMV-UHFFFAOYSA-N dodecan-1-ol Chemical compound CCCCCCCCCCCCO LQZZUXJYWNFBMV-UHFFFAOYSA-N 0.000 description 7
- 239000003345 natural gas Substances 0.000 description 7
- 239000012141 concentrate Substances 0.000 description 6
- 239000008367 deionised water Substances 0.000 description 6
- 229910021641 deionized water Inorganic materials 0.000 description 6
- 239000007788 liquid Substances 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
- -1 ethoxy, propoxy, butoxy Chemical group 0.000 description 5
- 239000003921 oil Substances 0.000 description 5
- 235000019198 oils Nutrition 0.000 description 5
- 239000003208 petroleum Substances 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- 238000005406 washing Methods 0.000 description 5
- 238000009736 wetting Methods 0.000 description 5
- 230000015572 biosynthetic process Effects 0.000 description 4
- 230000008859 change Effects 0.000 description 4
- 238000004140 cleaning Methods 0.000 description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- 239000000693 micelle Substances 0.000 description 4
- 238000012545 processing Methods 0.000 description 4
- HLZKNKRTKFSKGZ-UHFFFAOYSA-N tetradecan-1-ol Chemical compound CCCCCCCCCCCCCCO HLZKNKRTKFSKGZ-UHFFFAOYSA-N 0.000 description 4
- 241000004297 Draba Species 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- 239000012043 crude product Substances 0.000 description 3
- 230000007423 decrease Effects 0.000 description 3
- 235000014113 dietary fatty acids Nutrition 0.000 description 3
- 239000000194 fatty acid Substances 0.000 description 3
- 229930195729 fatty acid Natural products 0.000 description 3
- 239000000835 fiber Substances 0.000 description 3
- 239000003349 gelling agent Substances 0.000 description 3
- 238000000034 method Methods 0.000 description 3
- 238000006386 neutralization reaction Methods 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 229920000742 Cotton Polymers 0.000 description 2
- IGFHQQFPSIBGKE-UHFFFAOYSA-N Nonylphenol Natural products CCCCCCCCCC1=CC=C(O)C=C1 IGFHQQFPSIBGKE-UHFFFAOYSA-N 0.000 description 2
- 125000003545 alkoxy group Chemical group 0.000 description 2
- 125000002947 alkylene group Chemical group 0.000 description 2
- 238000013459 approach Methods 0.000 description 2
- 238000010790 dilution Methods 0.000 description 2
- 239000012895 dilution Substances 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 238000004945 emulsification Methods 0.000 description 2
- 239000003995 emulsifying agent Substances 0.000 description 2
- 150000004665 fatty acids Chemical class 0.000 description 2
- 239000006260 foam Substances 0.000 description 2
- BXWNKGSJHAJOGX-UHFFFAOYSA-N hexadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCO BXWNKGSJHAJOGX-UHFFFAOYSA-N 0.000 description 2
- 239000013067 intermediate product Substances 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- TVMXDCGIABBOFY-UHFFFAOYSA-N n-Octanol Natural products CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 2
- SNQQPOLDUKLAAF-UHFFFAOYSA-N nonylphenol Chemical compound CCCCCCCCCC1=CC=CC=C1O SNQQPOLDUKLAAF-UHFFFAOYSA-N 0.000 description 2
- 239000010695 polyglycol Substances 0.000 description 2
- 229920000151 polyglycol Polymers 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 239000004753 textile Substances 0.000 description 2
- 239000005968 1-Decanol Substances 0.000 description 1
- RZVAJINKPMORJF-UHFFFAOYSA-N Acetaminophen Chemical compound CC(=O)NC1=CC=C(O)C=C1 RZVAJINKPMORJF-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 229920002257 Plurafac® Polymers 0.000 description 1
- 229920005830 Polyurethane Foam Polymers 0.000 description 1
- 241000347389 Serranus cabrilla Species 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 208000034699 Vitreous floaters Diseases 0.000 description 1
- DPXJVFZANSGRMM-UHFFFAOYSA-N acetic acid;2,3,4,5,6-pentahydroxyhexanal;sodium Chemical compound [Na].CC(O)=O.OCC(O)C(O)C(O)C(O)C=O DPXJVFZANSGRMM-UHFFFAOYSA-N 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 239000002671 adjuvant Substances 0.000 description 1
- 238000013019 agitation Methods 0.000 description 1
- 239000003905 agrochemical Substances 0.000 description 1
- 125000000129 anionic group Chemical group 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 150000001721 carbon Chemical group 0.000 description 1
- 239000001768 carboxy methyl cellulose Substances 0.000 description 1
- 125000002091 cationic group Chemical group 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 239000004064 cosurfactant Substances 0.000 description 1
- 239000002761 deinking Substances 0.000 description 1
- 238000004851 dishwashing Methods 0.000 description 1
- 238000004043 dyeing Methods 0.000 description 1
- 238000004453 electron probe microanalysis Methods 0.000 description 1
- 230000001804 emulsifying effect Effects 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- UFZOPKFMKMAWLU-UHFFFAOYSA-N ethoxy(methyl)phosphinic acid Chemical compound CCOP(C)(O)=O UFZOPKFMKMAWLU-UHFFFAOYSA-N 0.000 description 1
- 150000002191 fatty alcohols Chemical class 0.000 description 1
- 238000007667 floating Methods 0.000 description 1
- 238000005188 flotation Methods 0.000 description 1
- 238000005187 foaming Methods 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 239000008233 hard water Substances 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 239000003752 hydrotrope Substances 0.000 description 1
- 239000002563 ionic surfactant Substances 0.000 description 1
- 238000010412 laundry washing Methods 0.000 description 1
- 238000012417 linear regression Methods 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 1
- 229910052753 mercury Inorganic materials 0.000 description 1
- 229920000847 nonoxynol Polymers 0.000 description 1
- 125000006353 oxyethylene group Chemical group 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 238000004806 packaging method and process Methods 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 239000011496 polyurethane foam Substances 0.000 description 1
- 150000003138 primary alcohols Chemical class 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
- 238000010926 purge Methods 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 238000002310 reflectometry Methods 0.000 description 1
- 210000002374 sebum Anatomy 0.000 description 1
- 238000004904 shortening Methods 0.000 description 1
- 239000000344 soap Substances 0.000 description 1
- 235000019812 sodium carboxymethyl cellulose Nutrition 0.000 description 1
- 229920001027 sodium carboxymethylcellulose Polymers 0.000 description 1
- 235000019832 sodium triphosphate Nutrition 0.000 description 1
- KVCGISUBCHHTDD-UHFFFAOYSA-M sodium;4-methylbenzenesulfonate Chemical compound [Na+].CC1=CC=C(S([O-])(=O)=O)C=C1 KVCGISUBCHHTDD-UHFFFAOYSA-M 0.000 description 1
- 239000010902 straw Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- FBWNMEQMRUMQSO-UHFFFAOYSA-N tergitol NP-9 Chemical compound CCCCCCCCCC1=CC=C(OCCOCCOCCOCCOCCOCCOCCOCCOCCO)C=C1 FBWNMEQMRUMQSO-UHFFFAOYSA-N 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- GPRLSGONYQIRFK-MNYXATJNSA-N triton Chemical compound [3H+] GPRLSGONYQIRFK-MNYXATJNSA-N 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 239000012224 working solution Substances 0.000 description 1
- 239000002888 zwitterionic surfactant Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
- C11D1/66—Non-ionic compounds
- C11D1/722—Ethers of polyoxyalkylene glycols having mixed oxyalkylene groups; Polyalkoxylated fatty alcohols or polyalkoxylated alkylaryl alcohols with mixed oxyalkylele groups
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K23/00—Use of substances as emulsifying, wetting, dispersing, or foam-producing agents
- C09K23/42—Ethers, e.g. polyglycol ethers of alcohols or phenols
Description
R−O−(C3H6O)x(C2H4O)y−H (I)
[式中、xは0.5〜3の範囲内の実数であり、yは2〜10の範囲内の実数であり、およびRは以下のアルキル成分分布:
成分中の炭素原子 量
C6 0重量%〜40重量%
C8 20重量%〜40重量%
C10 20重量%〜45重量%
C12 10重量%〜45重量%
C14 0重量%〜40重量%
C16−C18 0重量%〜15重量%
(ここで、各重量%は分布中に存在する全アルキル成分の重量に基づいており、各分布についての全重量%は計100重量%である。)を備える種油ベースの直鎖状アルキル成分の混合物である]で示される少なくとも1つの非イオン性界面活性剤を含む界面活性剤組成物である。
R−O−(C3H6O)x(C2H4O)y−H (I)
によって表される非イオン性界面活性剤を含む。
C8−10O(PO)3(EO)5.5Hの調製
等量(各1,000g(グラム))の1−オクタノール(99%)(Aldrich社、カタログ番号47232−8)(CAS番号111−87−5)および1−デカノール(デシルアルコール)Aldrich社、カタログ番号12−058−4(CAS番号112−30−1)を結合してアルコール混合物を形成する。3gのフレーク状水酸化カリウム(KOH)を1,000gのアルコール混合物へ加えて、触媒混合物を形成する。部分真空(50mmHg(mmの水銀))下で触媒混合物を45分間にわたり100℃の温度で、または触媒混合物が触媒混合物の100万分の1重量部で500ppm未満の含水量を有するまで、窒素パージにより蒸留する。
C12−C14O(PO)2(EO)7Hの調製
C12およびC14アルコールの混合物を形成するために、等量(各1,000g)の1−ドデカノール(98%)(Aldrich社、44381−6)(CAS番号112−53−8)と1−テトラデカノ−ル(Aldrich社、T−960−5)(CAS番号112−72−1)を結合する。2gのフレーク状KOHを900gの混合物に加えて実施例1に記載の触媒混合物を形成する。
混合アルコール流を生成するために、約386のヒドロキシル数を備える500gの種油由来C8−10アルコール(約55%のn−デカノールおよび約45%のn−オクタノールからなる混合物に対応する)を、約288のヒドロキシル値を有する500gの種油由来C12−16混合物(約70%のn−ドデカノール、25%のn−テトラデカノ−ルおよび5%のn−ヘキサデカノールからなる混合物に対応する)を合わせる。混合アルコール流は、以下のようなアルキル成分の重量パーセンテージ分布を提供する:C8=22.5%、C10=27.5%、C12=35%、C14=12.5およびC16=2.5%。
C8−10O(PO)2.5(EO) 5 H
1,035gの種油由来C8−10アルコールをプロポキシル化およびエトキシル化した界面活性剤へ転換する変更を加えて実施例1を繰り返す。アルコールは、約386(約55%のn−デカノールおよび約45%のn−オクタノールからなる混合物に対応する)のヒドロキシル数を有する。この変更は、200ppm未満の含水量を達成するために、比較例Aにおけるような50mmHgで45分間ではなく5mmHgで30分間にわたる蒸留を含む。この変更はさらに、1,050gのPO、1,590gのEO、残留もしくは未反応POが50ppm未満のレベルに達する点までプロポキシル化が進行する前のEOの添加および2.7gへの酢酸の量の増加も含む。
C12−14O(PO)2.5(EO)8H
約288のヒドロキシル値(約70%のn−ドデカノール、25%のn−テトラデカノールおよび5%のn−ヘキサデカノールからなる混合物に対応する)を備える998gの種油由来C12−16混合物からプロポキシル化およびエトキシル化した界面活性剤を調製するための変更を加えて比較例Cを繰り返す。この変更は、蒸留時間を15分間に短縮すること、750gのPOを用いたプロポキシル化、1,815gのEOを用いたエトキシル化、および2.6gの酢酸を用いた中和を含む。
比較例A(C8−10O(PO)3(EO)5.5H)および比較例B(C12−C14O(PO)2(EO)7H)の50:50混合物
100gの比較例Aの界面活性剤を100gの比較例Bの界面活性剤と混合することによって、2つの別個に調製した界面活性剤の単純混合物を生成する。
130gの比較例Cの界面活性剤および70gの比較例Dの界面活性剤混合物を用いて比較例Eを繰り返す。結果として生じる種油ベースの界面活性剤の混合物は、以下のようなR基分布を有する:C8=28.09重量%、C10=34.34重量%;C12=26.30重量%;C14=9.39重量%およびC16=1.88重量%、各重量%は、総分布量に基づく。
Draves湿潤試験、米国繊維化学技術・染色技術協会(AATCC)試験17(ASTM D2281)−脱イオン水中で界面活性剤の0.05重量%、0.10重量%および0.15重量%溶液を調製する。各溶液中に綿かせ糸(Testfabrics社製の40/2コーマピーラーヤーン)を配置し、かせ糸が崩壊するまでの経過時間を測定する。さらに、0.05重量%、0.10重量%および0.15重量%溶液試験からのデータに基づいて構築された対数時間体対数濃度プロットの線形回帰に基づいて20秒間にわたる湿潤のために必要な界面活性剤の濃度を計算する。
Ross−Miles気泡高さ試験−ASTM D1173
溶解時間試験−50gの界面活性剤を1分間当たり500回転(rpm)の攪拌速度で作動するオーバーヘッドスターラーを用いて攪拌しながら、20℃で1リットル(L)の水中へ溶解させるために必要とした時間を測定する。
洗濯試験は、以下のとおりの試験条件を備えるTerg−O−Meterを用いて実施する:攪拌速度=100サイクル/分;洗浄温度=40℃;洗浄浴サイズ=1L;Testrabrics(登録商標)からのSebum/Pigment(STC EMPA 119)を用いて、ピンキング切断した辺縁を備える3インチ×3インチ(7.5cm×7.5cm)の正方形ポリエステル/綿材料見本。織物材料見本は、300ppmの界面活性剤を含む脱イオン水を用いて洗浄する。デルタ反射率は、Hunter比色計を「反射率」モードで使用して測定する。試験結果は以下の表5にまとめる。比較例A〜Eおよび実施例1〜2からの界面活性剤ならびに市販の界面活性剤(比較例Fおよび比較例G)を使用することに加えて、比較例Iは脱イオン水だけを含むコントロールを表す。
Claims (5)
- 式(I):
R−O−(C3H6O)x(C2H4O)y−H (I)
[式中、xは0.5〜4未満の範囲内の実数であり、yは2〜10の範囲内の実数であり、およびRは、種油ベースの直鎖状アルキル成分の混合物であって、前記混合物は、以下のアルキル成分分布:
アルキル成分中の炭素原子 量
C6 0重量%〜40重量%
C8 20重量%〜40重量%
C10 20重量%〜45重量%
C12 10重量%〜45重量%
C14 0重量%〜40重量%
C16−C18 0重量%〜15重量%
(ここで、各重量%は分布中に存在する全アルキル成分の重量に基づいており、各分布についての全重量%を合計すると100重量%になる。)を有する。]で示される少なくとも1つの非イオン性界面活性剤を含む界面活性剤組成物。 - xが、3以下の実数である、請求項1に記載の組成物。
- xが、yより小さい、請求項1に記載の組成物。
- 洗剤の総重量に基づいて、1重量%〜99.1重量%の範囲内の量で請求項1から3のいずれか一項に記載の組成物を含む、洗剤。
- 洗浄剤の総重量に基づいて、1重量%〜99.1重量%の範囲内の量で請求項1から3のいずれか一項に記載の組成物を含む、洗浄剤。
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US87987607P | 2007-01-11 | 2007-01-11 | |
US60/879,876 | 2007-01-11 | ||
PCT/US2007/088023 WO2008088647A1 (en) | 2007-01-11 | 2007-12-19 | Alkoxylate blend surfactants |
Publications (3)
Publication Number | Publication Date |
---|---|
JP2010515805A JP2010515805A (ja) | 2010-05-13 |
JP2010515805A5 JP2010515805A5 (ja) | 2011-02-03 |
JP5346299B2 true JP5346299B2 (ja) | 2013-11-20 |
Family
ID=39410495
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2009545554A Active JP5346299B2 (ja) | 2007-01-11 | 2007-12-19 | アルコキシレート混合物界面活性剤 |
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BRPI0720328A2 (pt) | 2013-12-24 |
WO2008088647A1 (en) | 2008-07-24 |
MX2009007475A (es) | 2009-08-13 |
TW200843843A (en) | 2008-11-16 |
BRPI0720328B1 (pt) | 2018-06-12 |
CN101578130A (zh) | 2009-11-11 |
EP2117693B1 (en) | 2014-03-26 |
TWI405607B (zh) | 2013-08-21 |
JP2010515805A (ja) | 2010-05-13 |
US20100081607A1 (en) | 2010-04-01 |
AR064847A1 (es) | 2009-04-29 |
EP2117693A1 (en) | 2009-11-18 |
US7906474B2 (en) | 2011-03-15 |
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