TW505528B - Free-flowing dried particles - Google Patents
Free-flowing dried particles Download PDFInfo
- Publication number
- TW505528B TW505528B TW087102882A TW87102882A TW505528B TW 505528 B TW505528 B TW 505528B TW 087102882 A TW087102882 A TW 087102882A TW 87102882 A TW87102882 A TW 87102882A TW 505528 B TW505528 B TW 505528B
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- Taiwan
- Prior art keywords
- patent application
- acid
- calcium
- weight
- flowable
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- A61K9/1605—Excipients; Inactive ingredients
- A61K9/1629—Organic macromolecular compounds
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- A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
- A23L33/00—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof
- A23L33/10—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof using additives
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- A61K9/48—Preparations in capsules, e.g. of gelatin, of chocolate
- A61K9/50—Microcapsules having a gas, liquid or semi-solid filling; Solid microparticles or pellets surrounded by a distinct coating layer, e.g. coated microspheres, coated drug crystals
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Description
505528 A7 B7 五、發明説明（ 本發明係關於由至少一種親油性物質作爲活性成分所組 成的可自由流動之乾燥顆粒呈現於至少一種載體和塗膜的 基質内。 已知由至少一種親油物質作爲活性成分所組成的可自由 流動之乾燥顆粒呈現於至少一種載體和膜衣的基質内，作 爲活性成分的親油物質最大含量是重量百分比五十。 一種製造此類乾燥的方法已描述於例如德國專利特許公 開申請專案第10 35 3 19號及其相關的美國專利特許公開申 請案第2 756 177號，在此一種油性維生素作爲活性成分的 分散液噴入含有重量百分比8以下水量之額外大量的澱粉末 内，藉以乾燥的澱粉粉末補捉這些噴霧顆粒且這些喷霧顆 粒移走水量以便使其凝固和同時塗覆上澱粉。這些顆粒的 嚴重缺失是約重量百分比15的澱粉量會吸附於表面上，所 以這些顆粒僅含有極少量的活性成分。 經濟部中央標準局員工消費合作社印製 (請先閱讀背面之注意事項再填寫本頁) 、1Τ 根據描述於美國專利特許公開申請案第3 445 563號的類 似方法，爲了滅低細微分開的澱粉散發所造成爆炸危險， 澱粉由吸水和不吸水無機物質混合物所取代。爲了獲得最 佳結果20倍過量捕捉粉劑是需要的。粉劑中吸水的^分特 別稱爲碎酸舞尤其碎酸銘舞，而可溶油性活性成分這裡提 及維生素A及維生素D，至於活性成分活性介於每克 〇〇〇與532 000國際單位之間，所獲得的顆粒含有最高達重量 百分比十九的捕捉粉劑作爲塗膜。 更進-步，從德國專利特許公開申請案第〇〇74〇5〇號已知 的-種方法對於乾燥’自由流動，極易塗覆膠體的易氧化 4- 505528 A7 B7 五、發明説明.（2 ) 物質如維生素或類胡蘿蔔素粉劑的製造是有效的，此方法 包含分散這些物質衿形成薄膜膠體的水溶液中，與膠體一 起疋均勻相’具有從單，雙或醣各物中加入一種或種的分 散液和共同使用的噴助劑一起噴入嗔霧塔内，且該喷霧顆 粒收集於流動床内。藉以厭水矽酸或高度脂肪酸的金屬鹽 或與梦酸的混合物以基於分散液重量的0 02至0.15倍量在溫 度下被引入作爲噴助劑就噴霧範圍均勻分佈在流動床上， 喷霧顆粒膠體的凝固尚未發生。摻有助劑，助劑的膠體大 部分不需膠化的顆粒收集於流動床内且以本身已知的方法 在流動床内乾燥顆粒。 雖然在這方法僅產生喷霧助劑之一層厭水性薄膜，經由 喷霧所形成顆粒是足夠穩定以避免在非凝固狀況下一起產 生所造成顆粒的凝結，以便隨後可以直接在流動床乾燥機 上乾燥，這建議的方法有使用厭水的矽酸作爲噴霧輔助物 的重大缺失。在製藥或食品工業上使用自由矽酸進一步進 行加工是有問題的，因爲它危害健康且許多國家爲了此目 的不允許使用。 經濟部中央標準局員工消費合作社印裝 所以特別在製藥或食品工業上使用該方法和上述方法所 製造的可自由流動之乾燥顆粒不是滿意的。 於是本發明的目標是克服上述的缺失，特別上述含有活 性成分含量爲重量百分比50及以上，尤其重量百分比以 上的可自由流動之乾燥顆粒，換言之對於潭造如此含有高 含量活性成分的顆粒應該一起提供一種方法。除此之外: 發明的目標是爲了混合儘可能高量的活性成分於配藥形式 -5- 本紙張尺度適用中國國家標準（CNS )八4規格（2丨0x 297公釐） ⑽528 A7 --___ B7 ___ 五、發明説明,（） 〇 中’以這些可自由流動的乾燥顆粒來製備固體配藥形式。 從由至少一種親涑物質作爲活性成分所組成的可自由流 動的顆粒開始，呈現於至少一種載體和塗膜的基質内，藉 由提供矽酸鈣所組成的塗膜達成本目標。 塗膜可僅由矽酸鈣或矽酸鈣與下面混合物成分之一所組 成··微晶纖維素、矽酸鎂、氧化鎂、硬脂酸、硬脂酸鈣、 硬月曰版鎂、親水碎酸、高嶺土和/或Sterotex，僅由碎酸4¾ 所組成的塗膜是較佳的。 根據本發明含有親油物質含量爲重量百分比5 〇或以上的 顆粒且顆粒平均大小介於約8 〇微米與約1 〇〇〇微米之間，尤 其介於約100米及800微米之間。 當塗膜僅由矽酸鈣所組成，沒有上述即使微小的缺失性 質存在時，親油物質的量可達重量百分比7 〇以上。根據本 發明含有親油物質含量介於重量百分比7 4與7 8之間的顆粒 甚至可以被製造。 經濟部中央標準局員工消費合作社印製 (請先閱讀背面之注意事項再填寫本頁) 至於根據本發明的顆粒’塗膜僅由梦酸每所組成，碎酸 鈣的數量介於重量百分比2和1 2之間，約 <(小於等於）重量 百分比7較佳。在此與最新科技比較非常少量的塗膜物質存 在必要的理由是一種非常高量的活性成分即非常高量的親 油物質可以不需處理這些會被影響的顆粒而可混合於基質 内。在假定的範圍内以此目的所考慮的物質及具有化學鉞 性的物質以約相同數量全部附著於基質的《載體上，則少量 的塗膜物質是令人驚訝的。 至於含有由碎酸鈣與一種或多種上述混合成分所組成的 -6 - 本紙張尺度適用中國國家標準（CNS ) A4規格（210X 297公釐） 505528 ΑΊ B7 五 、發明説明（ 4 經濟部中央標準局員工消費合作社印製 顆粒’矽酸#5混合物的含量介於重量百分比5與2 5之間。 然而顯示出不僅f夕酸鈣顆粒的化學性質而且物理性質都 疋重要的’如此令人驚野地發現當碎酸劈顆粒大小以.2微 米尤其^0.1微米且比表面積至少約每克8〇平方米至約每克 180平方米’尤其約每克95平方米至每克ι2〇平方米較佳是 特別合適且綠聚聚集而有平均大小約5至2 〇微米，5至1 〇微 米較佳，該二氧化矽與氧化鈣比介於165與2.65之間。 此外當矽酸鈣全邵或部份以水合形式存在時是其優點， 硬酸鈣實際上是無結晶矽酸，所以本發明排除市場上，多數 可利用的矽酸鈣作爲塗膜物質因爲它們都以結晶矽酸處理 過。 親油物質至少來自下面各物之一種：親脂性維生素或其 衍生物、類胡蘿蔔素尤其冷_胡蘿蔔素和聚合不飽和脂肪酸 例如舉例把生四晞敗、ecosapentaen〇ic acid和2 2已晞酸和 特別從維生素ADE及K或其衍生物各物中至少一種維生 素，尤其維生素A乙酸酯、維生素A棕搁酸酯和/或維生素 E乙酸酯，維生素E或維生素e乙酸酯較佳。 維生素E包含以合成製造的生育酚或天然生育酚的混合 物0 載體疋纖維素、水溶性纖維素衍生物、尤其甲基纖維素 或羥基丙基甲基纖維素、麥牙糊精、特別是含有右旋糖當 量値約1 8的麥牙糊精、藻酸衍生物，尤齐納、每、丙二 醇、藻酸鹽、乳酸鈣、阿拉伯樹脂、明膠尤其魚膠糖、糖 醇、甘油、修飾過之殿粉、或預先膠化的穀類殺粉、明膠 本紙張尺度適用中國國家標準（CNS ) A4規格（2丨〇><297公釐） (請先閲讀背面之注意事項再填寫本頁)
、1T 505528 A7 _ _ B7_ 五、發明説明.（5 ) 尤其魚膠較佳，含有起霜（白化）數介於〇和約220之間的明 膠已證實是特別好蚱。載體或包含這些的基質可以另外地 包含至少一種水溶性維生素。 可自由流動之乾燥顆粒對於製造固體劑型尤其錠劑是非 常合適的，因爲這些顆粒有顯著的流動和可壓縮作用，不 需要加入平常量的壓縮輔助物。 根據本發明注意混合重量百分比7 〇或以上的活性成分量 於顆粒中的可能性（重量百分比7 4和重量百分比7 8的量及 各別的量已無問題的混合過）尤其對於製造综合維生素錠劑 及综合礦物質錠劑特別合適。所以至於儘可能高的活性成 分量配合儘可能低的活性成分體積或重量是被尋求的。多 種維生素和多種礦物質錠劑這裡也被稱爲沸騰錠或咀嚼 錠〇 根據本發明對於製造顆粒的較佳方法包含依照捕捉方法 尤其依照粉劑的捕捉方法，噴出親油物質和載體的水溶液 乳劑進入矽酸鈣或矽酸鈣與一種或多種如以上更詳細地被 描述特徵的混合物成分的捕捉媒介物，且接著以本身已知 的方法乾燥所得的顆粒。 經濟部中央標準局員工消費合作社印製 (請先閲讀背面之注意事項再填寫本頁) 固體劑型尤其综合維生素錠劑除了包含至少一種水溶性 物質作爲活性成分之外，從類胡蘿蔔素尤其胡蘿蔔素和 維生素A、D、E和K或其衍生物各物中至少一種親油物質作 爲活性成分較佳。維生素E的含量介於重韋百分比4至5〇之 間較佳’ 了一般佐藥之外，固體劑型也可包含至少一種 f量元素和/或至少_種水溶性維生素，通常以礦物質的 -8- 本紙& 度適用中國^ ------ 505528 A7 B7 五 、發明説明( 6 形式混合。 (請先閲讀背面之注意事項再填寫本頁) 微量元素這裡特別使用鎂、碘、鉀、錳、鈣、磷、鋅、 銅和鐵，拫據本發明鈣已提供顆粒的塗膜至少至某些程 度。這裡較不重要的也可使用硒、鉻、氯（如氣化物）、 鉬、鎳、錫、矽（被縛的）、釩及硼，根據本發明矽（被縛的） 像鈣至少部份混合於顆粒。基於上述的目的，從維生素 c，Β!、B2、Βό、、泛酸泛酸鈣、葉酸生物素和菸鹼酸中 使用至少一種物質作爲水溶性物質。 從下面的實例有更進一步明顯的詳述及優點。 實例1至3描述僅塗覆矽酸鈣的顆粒。 實例4描述具有矽酸鈣和微晶纖維素混合物的塗膜。 實例5至8描述综合維生素錠。 實例1 經濟部中央標準局員工消费合作社印製 :免克的乾燥魚膠（起霜數〇)置於5〇〇毫升的容器内，接著加 入9 5毫升的去離子水且此混合物在4 〇至5 〇 下同時以切碎 機圓盤每分鐘1〇〇〇轉授拌形成溶液產生基質，隨即154克的 生育紛乙酸酯在基質内乳化並攪拌1 5分鐘，在乳化期間以 每分鐘4800轉旋轉攪拌切碎機圓盤。在這段時間後，乳液 的内相平均顆粒大小約250毫米，乳液接著以130毫升的去 離子水稀釋並加熱至65 °C接下來225克的矽酸鈣（從美國 Celite公司的Micro-Cel E具有二氧化矽與氧化鈣比率爲1.65) 置於實驗室噴霧槽中冷卻到至少〇°C，乳味使用一個旋轉的 噴霧管口噴入噴霧槽内，如此獲得覆有矽酸鈣的顆粒用篩 率100至800微米將過量的矽酸鈣篩除，並且在室溫下利用 -9- 本紙張尺度適用中國國家標準（CNS ) A4規格（210X 297公釐） 505528 A7 B7 經 濟 部 中 標 準 局 員 工 消 t 合 作 社 印 製 五、發明説明（ ^巩乾燥。獲得19〇克塗覆具有顯著流動性質之矽酸鈣顆粒 疋疋王乾燥且可以被處理得很好。矽酸鈣的含量是重量百 分比7。 ’ t例2 在類似實例1的實驗中，爲了製藥上的目的以英國 去霜數220的明膠來代替魚膠，產率是195克。產物有如實 例1在工業上具有同樣良好的適應性。 實例3 類似重覆實例1，但使用二氧化矽與氧化鈣比2·65以上的 矽酸鈣。形成塗覆矽酸鈣的顆粒且生育酚乙酸酯含量僅有 重量百分比44.3，矽酸鈣的重量超越重量百分比7以上。所 以含有二氧化矽與氧化鈣比2.65以上的矽酸鈣是不適合 的0 實例4 36克南分子乾燥的魚膠（去霜數〇 N〇rian(}公司之產品）置 於500毫升的容器内接著加入9 5毫升的去離子水且此混合物 在4 0至5 0 °C下同時以切碎機圓盤每分鐘1〇〇〇轉攪拌形成溶 液產生基質，隨即156克的生育酚乙酸酯在基質内乳化並攪 拌1 5分鐘，在乳化期間以每分鐘4800轉旋轉攪拌切碎機圓 盤，在這時間後，乳液的内相平均顆粒大小約300毫米，乳 液接著以13 5毫升的去離子水稀釋並加熱至6 5 °C，接下來 410克石夕酸#5混合物（從美國Celite公司的Micro-Cel E具有二 氧化矽與氧化鈣比1.65)和微晶纖維素（VIVAPUR型105)置於 實驗室喷霧槽中。VIVAPUR型105與微膠E的比率是5.66 : 1 ’混合物冷卻到至少0 C。乳液使用一個旋轉的噴霧管口 -10- 本紙張尺度適用中國國家標举（CNS)Λ4規格（210x 297公釐） (請先閲讀背面之注意事¾再填寫本頁，> 、訂 505528 A7 B7 五、發明説明.（8 ) 噴入噴霧槽内。如此獲得覆有矽酸鈣·纖維素的顆粒以篩率 100至800微米將過暈的矽酸鈣-纖維素篩除並且在室溫下利 用空氣乾燥。獲得222· 1克塗覆具有顯著流動性質之碎酸約 -纖維素顆粒是完全乾燥且可以被處理得很好，碎酸妈的含 量是重量百分比21。 實例5 從下面成分在comprex II的製鉸機衝模1 6 X 7.42毫米在5 至5 0仟牛頓的壓力下製造多種維生素錠劑。 實例1而來的粉碑產物 147毫克 0 -錠7.5(從羅氏所得之7.5%可錠劑化之 96.0毫克 胡蘿素形態） 抗壞血酸每克90% 244.5毫克 Avicel PH 102 130毫克 乳糖DCL21 50毫克 總錠劑量 668毫克 (請先閱讀背面之注意事項再填寫本頁) 經濟部中央標準局員工消費合作社印製 所得的錠劑硬度是2 0至140牛頓，錠劑是乾燥的。 實例6 類似實例4，使用根據本發明含有重量百分比7 5含量的維 生素E作爲活性成分的顆粒來製造多種維生素錠（重量百分 比75 E之處方，包含重量百分比7 5的維生素E顆粒）與傳統 相同組成的維生素錠（重量百分比50 E之處彳方包含重量百分 比5 0的維生素顆粒）相比較。 -11 - 本紙張尺度適用中國國家標準（CNS ) Μ規格（210X 297公釐） 505528 A7 B7 、發明説明,（9) 重量百分比75 E之處方 重量百分比50 E之處方 鍵劑重 808.3毫克 948.3毫克 冷-胡蘿蔔素* 34.5毫克 34.5毫克 維生素E 280毫克 420毫克 維生素C 90 291.7毫克 291.7毫克 Avicel 161.6毫克 161.6毫克 Microcel C 24.3毫克 24.3 聚乙烯吡咯酮XL 16.2毫克 16.2毫克 (PVP XL) (請先閲讀背面之注意事項再填寫本頁) -1¾. *々-錠20(從羅氏（ROCHE)所得之20%可錠劑比的胡蘿蔔 素形態） 從這可明顯看出，根據本發明的顆粒可製成比傳統含有 維生素E顆粒所製造的錠劑有較低的重量（或相當低的體 積）。 實例7 類似實例5，使用根據本發明含有重量百分比7 5含量的維 生素E作爲活性成分的顆粒來製造多維生素錠（重量百分比 75 E之處方包含重量百分比7 5的維生素e顆粒）與傳統相同 組成的維生素E錠（重量百分比5〇 e之處方包含重量百分比 5 0的維生素顆粒）相比較。 -12-
本紙張尺度適财®巧標準（CNS 訂 經濟部中央標準局員工消費合作社印製 505528 A7 B7 五、發明説明（ 重量百分比75 E之處方重量百分比50 E之處方 維生素/礦物質混1294.8毫克 合物 1294.8毫克 維生素E 70.7毫克 106.0毫克 微晶纖維素 57.2亳克 0.0毫克 聚乙晞P比略酮 XL (PVP) 6.6毫克 30.0毫克 硬脂酸 2.0亳克 2.0亳克 硬脂酸鎂 4.2毫克 4.2毫克 所得的錠劑硬度是210牛頓。在重量百分比75 E的處方中 降低聚乙烯吡咯酮XL不會改變錠劑溶解的時間（不到5分 鐘）。 實例8 類似實例5，使用根據本發明含有重量百分比7 5含量的維 生素E作爲活性成分的顆粒來製造多種維生素錠（重量百分 比75 E之處方包含重量百分比75的維生素E顆粒）。 重量百分比75 E之處方. 經濟部中央標準局員工消費合作社印製 12.94.8 毫克 70.7毫克 58.0毫克 15.0毫克 2.0毫克 4.2毫克 (請先閱讀背面之注意事項再填寫本頁) 維生素/礦物質混合物 維生素E 微晶纖維素 澱粉 硬脂酸 硬脂酸鎂 所得的錠劑硬度是210牛頓。錠劑的溶解時間不到5分 鐘0 -13- 本纸張尺度適用中國國家標準（CNS ) A4規格（210x297公釐）
Claims (1)
- 2 8 8 2 利 請 中 87文 第中ABC 申請專利範圍 々It]无 公告衣 .一種具有平均顆粒大小介於8 0微米與1000微米之可流動 乾燥顆粒，其係由至少一種親油性物質作為活性成分存 在於至少一種載體物質之基質内和塗膜所組成，其中親 油性物質之含量為佔顆粒之5 0重量％或以上，塗膜是由 石夕酸鹤或碎酸鈣與下列混合成分之一之混合物所組成微 曰曰性纖維素、矽酸鎂、氧化鎂、硬脂酸、硬脂酸鈣、硬 知酸鎂 '親水性矽酸、高嶺土和/或思特羅特絲 (Sterotex)。 2. 如申請專利範圍第1項之可流動乾燥顆粒，其中塗膜係 由矽酸鈣所組成。 3. 如申請專利範圍第1或2項之可流動乾燥顆粒，其中親油 性物質之含量為74.0至78.0重量％，且平均顆粒大小介於 100微米和800微米之間。 4. 如申請專利範圍第丨或2項之可流動乾燥顆粒，其中碎酸 鈣含量係介於2與1 2重量％之間。 5. 如申請專利範圍第丨或2項之可流動乾燥顆粒，其中碎酸 鈣 〃 a) 具有 Si02/CaO比率為 1.65-2.65 ; b) 由以.2微米大小之顆粒所組成，此等顆粒係聚集成 具有平均大小介於5至20微米之聚集體，且具有比 表面積至少每克80平方米至每克18〇平方米.及 c) 視情況可以完全或部份是水合碎酸|弓。 6·如申請專利範圍第丨或2項之可流動乾燥顆粒，其中親油 性物質是選自維生素A、D、E和K或其衍生物之至少一 本紙張尺度適用中國國家標準(CNS) A4規格(210 X 297公釐） 505528 8 8 8 8 A B c D 六、申請專利範圍 種物質和/或得自聚未飽和脂肪酸族群之物質。 7·如申凊專利範圍第1或2項之可流動乾燥顆粒，其中載體 物質為至少一種得自以下族群之物質，纖維素；水溶性 纖維素衍生物·，麥牙糊精；藻酸衍生物；乳酸鈣；阿拉 伯膠，明膠；糖；甘油；經改質殿粉和預膠化穀類澱 粉。 8.如申凊專利範圍第1或2項之可流動乾燥顆粒，其中至少 一種水溶性維生素亦存在於基質内。 9· 一種製造如申請專利範圍第1至8項中任一項之可流動乾 燥顆粒之方法，此方法包括根據捕捉程序，將親油性物 質和載體物質之含水乳化液噴霧至矽酸鈣或矽酸鈣與一 或多種混合成分之混合物之捕捉媒質中，且接著以本身 已知之方法乾燥所得之顆粒。 10. —種固態劑型，其係製自如申請專利範圍第1至8項中至 少一項之可流動乾燥顆粒。 11·如申請專利範圍第10項之固態劑型，其為維生素錠劑， 其含有維生素E之含量係在4重量％與5 〇重量％之間。 I2·如申請專利範圍第1或2項之可流動乾燥顆粒，其係用於 f造視情況亦包含至少一種通常以礦物質形式摻入之微 量元素之多維生素錠劑。 13·如申請專利範圍第丨或2項之可流動乾燥顆粒，其係用於 醫藥或食品工業上。 ' -2- 本紙張尺錢;U中國國家標準(CNS) χ 297·π---—--
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| HUE029842T2 (en) | 2007-02-23 | 2017-04-28 | Gilead Sciences Inc | Modulation of pharmacokinetic parameters of therapeutic agents |
| PL2296633T3 (pl) * | 2008-05-02 | 2016-03-31 | Gilead Sciences Inc | Zastosowanie cząsteczek stałych nośników dla udoskonalenia przetwarzalności środka farmaceutycznego |
| GB201102557D0 (en) * | 2011-02-14 | 2011-03-30 | Univ Nottingham | Oil bodies |
| JP5791304B2 (ja) * | 2011-02-17 | 2015-10-07 | アサヒフードアンドヘルスケア株式会社 | ビタミンｃ類の反応抑制方法、及び、ビタミンｃ類を含む食品等製品 |
| EA201991467A1 (ru) * | 2016-12-15 | 2019-11-29 | Состав смеси, содержащий силикат и микробные и/или растительные клетки и полиненасыщенную жирную кислоту, имеющую по меньшей мере 20 атомов углерода (lc-pufa) | |
| ES2904834T3 (es) * | 2017-10-05 | 2022-04-06 | Purac Biochem Bv | Polvo de lactato y método para su preparación |
| CN109221869A (zh) * | 2018-10-25 | 2019-01-18 | 广州市炜鑫生物科技有限公司 | 一种复合酵素纤维素固体饮料及其制备方法 |
| CN110917071B (zh) * | 2019-12-23 | 2022-11-08 | 万华化学集团股份有限公司 | 核壳结构柔珠、其制备方法及包括其的个人护理用品 |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2756177A (en) * | 1953-03-09 | 1956-07-24 | Hoffmann La Roche | Process for making fat-soluble vitamin active powder |
| US2858215A (en) * | 1956-07-02 | 1958-10-28 | Barnett Lab Inc | Process of preparing vitamin oils in particle form |
| US3247064A (en) * | 1962-03-30 | 1966-04-19 | Shionogi & Co | Multivitamin tablet stabilized with porous silica |
| GB1142147A (en) * | 1965-05-28 | 1969-02-05 | Glaxo Lab Ltd | A process for making free-flowing gel particles |
| DE3135329A1 (de) * | 1981-09-05 | 1983-03-24 | Basf Ag, 6700 Ludwigshafen | Verfahren zur herstellung von trockenpulvern oxidationsempfindlicher substanzen |
| US4603143A (en) * | 1983-05-02 | 1986-07-29 | Basf Corporation | Free-flowing, high density, fat soluble vitamin powders with improved stability |
| US4670247A (en) * | 1983-07-05 | 1987-06-02 | Hoffman-Laroche Inc. | Process for preparing fat-soluble vitamin active beadlets |
| US4780309A (en) * | 1987-06-16 | 1988-10-25 | Warner-Lambert Company | Edible aerosol foam compositions and method of preparing same |
| US4906478A (en) * | 1988-12-12 | 1990-03-06 | Valentine Enterprises, Inc. | Simethicone/calcium silicate composition |
| FR2681248B1 (fr) * | 1991-09-13 | 1995-04-28 | Oreal | Composition pour un traitement cosmetique et/ou pharmaceutique de longue duree des couches superieures de l'epiderme par une application topique sur la peau. |
| US5837790A (en) * | 1994-10-24 | 1998-11-17 | Amcol International Corporation | Precipitation polymerization process for producing an oil adsorbent polymer capable of entrapping solid particles and liquids and the product thereof |
-
1998
- 1998-02-04 JP JP02299998A patent/JP4494539B2/ja not_active Expired - Lifetime
- 1998-02-13 CA CA002229351A patent/CA2229351C/en not_active Expired - Lifetime
- 1998-02-19 ID IDP980230A patent/ID19841A/id unknown
- 1998-02-20 DE DE59809832T patent/DE59809832D1/de not_active Expired - Lifetime
- 1998-02-20 DK DK98102962T patent/DK0867177T3/da active
- 1998-02-20 US US09/027,328 patent/US6030645A/en not_active Expired - Lifetime
- 1998-02-20 ES ES98102962T patent/ES2206770T3/es not_active Expired - Lifetime
- 1998-02-20 EP EP98102962A patent/EP0867177B1/de not_active Expired - Lifetime
- 1998-02-24 PH PH11998000410A patent/PH11998000410B1/en unknown
- 1998-02-27 KR KR1019980006371A patent/KR19980071798A/ko active Search and Examination
- 1998-02-27 CN CNB981052886A patent/CN1146405C/zh not_active Expired - Lifetime
- 1998-02-27 NO NO19980840A patent/NO320488B1/no unknown
- 1998-02-27 AU AU56384/98A patent/AU734530B2/en not_active Ceased
- 1998-02-27 BR BR9800788-2A patent/BR9800788A/pt not_active Application Discontinuation
- 1998-02-27 TW TW087102882A patent/TW505528B/zh not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| NO980840D0 (no) | 1998-02-27 |
| EP0867177B1 (de) | 2003-10-08 |
| BR9800788A (pt) | 2000-04-04 |
| CN1146405C (zh) | 2004-04-21 |
| NO980840L (no) | 1998-08-31 |
| KR19980071798A (ko) | 1998-10-26 |
| AU5638498A (en) | 1998-09-03 |
| CA2229351C (en) | 2009-04-14 |
| AU734530B2 (en) | 2001-06-14 |
| DE59809832D1 (de) | 2003-11-13 |
| DK0867177T3 (da) | 2004-01-26 |
| ID19841A (id) | 1998-08-06 |
| PH11998000410B1 (zh) | 2002-07-05 |
| MX9801512A (zh) | 1999-04-01 |
| EP0867177A1 (de) | 1998-09-30 |
| CA2229351A1 (en) | 1998-08-28 |
| NO320488B1 (no) | 2005-12-12 |
| US6030645A (en) | 2000-02-29 |
| MX205481B (zh) | 2001-12-13 |
| JP4494539B2 (ja) | 2010-06-30 |
| CN1194827A (zh) | 1998-10-07 |
| ES2206770T3 (es) | 2004-05-16 |
| JPH10245348A (ja) | 1998-09-14 |
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