US3926817A - Glidants and process for preparing the same - Google Patents
Glidants and process for preparing the same Download PDFInfo
- Publication number
- US3926817A US3926817A US492786A US49278674A US3926817A US 3926817 A US3926817 A US 3926817A US 492786 A US492786 A US 492786A US 49278674 A US49278674 A US 49278674A US 3926817 A US3926817 A US 3926817A
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- US
- United States
- Prior art keywords
- glidant
- surface active
- active agent
- substance
- glidants
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- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M7/00—Solid or semi-solid compositions essentially based on lubricating components other than mineral lubricating oils or fatty oils and their use as lubricants; Use as lubricants of single solid or semi-solid substances
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/20—Pills, tablets, discs, rods
- A61K9/2004—Excipients; Inactive ingredients
- A61K9/2013—Organic compounds, e.g. phospholipids, fats
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- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
- C10M2207/10—Carboxylix acids; Neutral salts thereof
- C10M2207/12—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms
- C10M2207/125—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms having hydrocarbon chains of eight up to twenty-nine carbon atoms, i.e. fatty acids
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- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
- C10M2207/10—Carboxylix acids; Neutral salts thereof
- C10M2207/12—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms
- C10M2207/129—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms having hydrocarbon chains of thirty or more carbon atoms
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- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
- C10M2207/28—Esters
- C10M2207/281—Esters of (cyclo)aliphatic monocarboxylic acids
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- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
- C10M2207/28—Esters
- C10M2207/282—Esters of (cyclo)aliphatic oolycarboxylic acids
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- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
- C10M2207/28—Esters
- C10M2207/283—Esters of polyhydroxy compounds
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- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
- C10M2207/28—Esters
- C10M2207/286—Esters of polymerised unsaturated acids
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- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
- C10M2207/28—Esters
- C10M2207/287—Partial esters
- C10M2207/289—Partial esters containing free hydroxy groups
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- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2209/00—Organic macromolecular compounds containing oxygen as ingredients in lubricant compositions
- C10M2209/10—Macromolecular compoundss obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
- C10M2209/103—Polyethers, i.e. containing di- or higher polyoxyalkylene groups
- C10M2209/104—Polyethers, i.e. containing di- or higher polyoxyalkylene groups of alkylene oxides containing two carbon atoms only
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- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2209/00—Organic macromolecular compounds containing oxygen as ingredients in lubricant compositions
- C10M2209/10—Macromolecular compoundss obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
- C10M2209/103—Polyethers, i.e. containing di- or higher polyoxyalkylene groups
- C10M2209/107—Polyethers, i.e. containing di- or higher polyoxyalkylene groups of two or more specified different alkylene oxides covered by groups C10M2209/104 - C10M2209/106
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- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2219/00—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
- C10M2219/04—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions containing sulfur-to-oxygen bonds, i.e. sulfones, sulfoxides
- C10M2219/042—Sulfate esters
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- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
- C10N2010/00—Metal present as such or in compounds
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- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
- C10N2010/00—Metal present as such or in compounds
- C10N2010/04—Groups 2 or 12
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- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
- C10N2020/00—Specified physical or chemical properties or characteristics, i.e. function, of component of lubricating compositions
- C10N2020/01—Physico-chemical properties
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- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
- C10N2040/00—Specified use or application for which the lubricating composition is intended
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- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
- C10N2040/00—Specified use or application for which the lubricating composition is intended
- C10N2040/30—Refrigerators lubricants or compressors lubricants
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- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
- C10N2040/00—Specified use or application for which the lubricating composition is intended
- C10N2040/32—Wires, ropes or cables lubricants
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- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
- C10N2040/00—Specified use or application for which the lubricating composition is intended
- C10N2040/34—Lubricating-sealants
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- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
- C10N2040/00—Specified use or application for which the lubricating composition is intended
- C10N2040/36—Release agents or mold release agents
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- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
- C10N2040/00—Specified use or application for which the lubricating composition is intended
- C10N2040/38—Conveyors or chain belts
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- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
- C10N2040/00—Specified use or application for which the lubricating composition is intended
- C10N2040/40—Generators or electric motors in oil or gas winning field
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- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
- C10N2040/00—Specified use or application for which the lubricating composition is intended
- C10N2040/42—Flashing oils or marking oils
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- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
- C10N2040/00—Specified use or application for which the lubricating composition is intended
- C10N2040/44—Super vacuum or supercritical use
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- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
- C10N2040/00—Specified use or application for which the lubricating composition is intended
- C10N2040/50—Medical uses
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- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
- C10N2050/00—Form in which the lubricant is applied to the material being lubricated
- C10N2050/08—Solids
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- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
- C10N2050/00—Form in which the lubricant is applied to the material being lubricated
- C10N2050/10—Semi-solids; greasy
Definitions
- glidants having excellent gliding properties, i.e., improving or eliminating those disadvantages encountered in the prior art, for example, capping of the finished pharmaceutical preparations, delayed disintegration of the finished pharmaceutical preparations, lowering of the dissolution-out rate of the active ingredient and the like, which comprises certain known glidants wet-treated with a surface active agent, said known glidants being selected from higher fatty acids, the metal salts thereof and hydrogenated vegetable oils.
- the present glidants are prepared by subjecting the known glidants to wet treatment with a surface active agent.
- This invention relates to improved glidants and a process for preparing the same.
- improved glidants comprising a glidant substance wherein said glidant substance is subjected to wet treatment with a surface active agent, said glidant substance being selected from the group consisting of higher fatty acids. the metal salts thereof and hydrogenated vegetable oils and with a process for the preparation of such improved glidant.
- Carbowax (Registered Trade Mark), sodium stearate and the like have been also utilized in the pharmaceutical preparations, especially those required for hydrophilic property, e.g., water-soluble tablets, but these glidant substances were known to exert a poor glidant effect as well as toxicity and hygroscopicity so that they were kept away from general utilizability.
- a certain type of the known glidant substances i.e., those selected from the group consisting of higher fatty acids, the metal salts thereof and hydrogenated vegetable oils exhibit a highly excellent glidant effect when they are subjected to wet treatment with a surface active agent.
- a glidant exhibits its glidant effect due to its surface properties and thus, when treated with a substance having no gliding property per se, such a glidant should lose its inherent glidant property.
- the improved glidant of this invention can hold inherent glidant effects such as the improvement in fluidity, the lowering of the excluding force from punches upon making tablets, the increase in bulk density, the prevention of anchoring and the like and simultaneously perform almost complete elimination of the disadvantages accompanied with the prior art glidants. e.g., poor disintegration, lower dissolution-out rate and the like, as compared with the prior art glidants. Still more surprisingly, in the case of making tablets the improved glidant of this invention can effectively prevent the low tablet hardness and the development of capping, which are believed inherent in the prior art glidant.
- the glidant of this invention has an essential feature that it comprises a glidant substance known per se, said substance being selected from the group consisting of higher fatty acids, the metal salts thereof and hydrogenated vegetable oils, which substance is subjected to wet treatment (or treat ment under a wetting condition) with a surface active agent.
- a glidant substance known per se said substance being selected from the group consisting of higher fatty acids, the metal salts thereof and hydrogenated vegetable oils, which substance is subjected to wet treatment (or treat ment under a wetting condition) with a surface active agent.
- wet treatment as used herein is contemplated to include kneading procedure and other procedures commonly employed for absorption between solid phase and liquid phase.
- the process of this invention comprises subjecting the selected glidant substance to wet treatment with a surface active agent.
- the wet treatment may be effected as set forth above.
- the drying may be suitably effected by a conventional drying procedure, e.g. hot air drying, aeration drying, vacuum drying and the like.
- the pulverization may be suitably effected by means of a conventional grinder, e.g.. impact grinder, pneumatic grinder and the like. It is desirable that the particle size of the ground glidant be in the range of 10 ,u or less, but larger particle size may also be favourably employed.
- Examples of the glidant substances to be treated according to the process of this invention include stearic acid, magnesium stearate, calcium stearate and hydrogenated castor oil [e.g. Lubriwax (trade name, available from F reund Industrial Company, Japan) and Sterotex (trade name, available from Capital City Products Company, U.S.A)]. If desired, any combination of the above-illustrated glidant substances may also be employed in this invention.
- the surface active agents which may be employed in this invention may be of any type of non-ionic, anionic and cationic type surface active agents. Of these surface active agents are preferable polyoxyethylenepolyoxypropylene block polymers, e.g., those having the structure Hon?
- H OJ1(C;,H.,O)b(C -H O)CH wherein either the sum ofa and c is 30 35 and b is 25 30 or the sum ofa and cis -150 and b is 25 30 and a molecularweight of either ca. 3000 or ca. 8,000. respectively [e.g. Pluronic F-68" and Pluronic L'64 (trade names. available from Asahi Denka Kogyo K.K.. Japan or from Wyandotte Chemical Co.. USA. )1.
- polyoxyethylene sorbitan fatty acid esters e.g.. polyoxyethylene monostearate. monolaurate. monopalmitate. monooleate and trioleate; alkyl sulfate salts.
- the amount of the surface active agent to be employed is not critical. but it is usual and effective to employ the surfactant at 20 7c by weight or less. preferably at 4 '7( by weight. based upon the total weight of the untreated glidant substance.
- the solvent which may be employed in the above wet treatment may be any of those that could dissolve the surfactant and not the untreated glidant substance. Examples of the solvents which may be employed include water. methanol. ethanol. acetone. chloroform and the like.
- EXAMPLE 1 The surface active agents indicated in the Table I below were respectively dissolved in the solvents indicated in the Table I to form the 5 7c solutions thereof.
- EXAMPLE 2 The molded products from the formulations indicated in the following Table [II and the No. 1 capsules filled with the same formulations were tested for their physical properties as below with the results which are summarized in the Table IV below.
- Lactose gmnules (PMS) 3 I d 6 d th f l Untreated StMglparts)
- PMS Lactose gmnules
- the surfactant and the StMg gives an insufficient period lauryl u (P l of disintegration time (Sample No. 7)
- the Tom] pans, 3015 glidants treated with the surfactant solution according x I r v g to this invention exert the desired effect (Sample Nos.
- Table VI Table VIII l Excluding force Amount of the active ingredient eluted ('7?) 40 Sample No ⁇ mm [hc punch g Dissolution-out time l0 min. 20 min. 30 min Sample No. 15 92 a 81 95 98 9 5 14 23 ll) I5 76 5 II It) 45 78 It Wlll be seen from the above Table ,VIII that the 3 99 formulation containing the StMg treated with the surfactant (Sample No. 14) has a reducing action against the force excluding the tablets from the punch. i.e.. a glidant action as the formulation containing the un- It will be seen from the above Table VI that. when treated StMg (Sample No. 13) has.
- One thousand and two hundred mg. of the sample as obtained above was molded under pressure of 3.3 tons by means of a conventional compression tester equipped with flat punches of 16 mm. diameter. whereupon the excluding force from the punch was determined with a load cell.
- EXAMPLE 6 The granules were prepared by incorporating a 4 starch paste to an appropriate amount of lactose and then granulating. The so otained granules were punched to the tablets having an uniform tablet height according to the formulae indicated in the Table Xl below.
- a glidant comprising a major amount of a glidant substance selected from the group consisting of a higher fatty acid. a calcium salt thereof, a magnesium salt thereof. and a solid hydrogenated vegetable oil. treated with a solvent solution containing a surface active agent in an amount sufficient to improve dissolution of the glidant substance. said solvent being a solvent for said surface activeagent and a non-solvent for said glidant substance. followed by drying and pulveri- Zation.
- glidant according to claim 1 wherein said glidant substance is stearic acid, magnesium stearate. calcium stearate or hydrogenated castor oil.
- said surface active agent is a polyoxyethylene-polyoxypropylene block polymer. a polyoxyethylene sorbitan fatty acid ester or an alkyl sulfate salt.
- said surface active agent is a polyoxyethylene-polyoxypropylene block polymer having the structure wherein either the sum of a and c is 30 35 35 and b is 25 30 or the sum ofa and c is and b is 25 30 and having a molecular weight of either about 3,000 or about 8.000; a polyoxyethylene sorbitan monoor tri-fatty acid ester having 12 18 carbon atoms in the fatty acid moiety; or sodium lauryl sulfate.
- glidant according to claim 1 wherein said surface active agent is employed in an amount of up to 20% by weight, based upon the total weight of said glidant substance.
- glidant according to claim 1 wherein said glidant substance is magnesium stearate and said surface active agent is sodium lauryl sulfate.
- glidant according to claim 1 wherein said glidant substance is magnesium stearate and said surface active agent is a polyoxyethylene-polyoxypropylene block polymer having the structure HO(C- -H O)a(CxH.;O)h(C H O)cH wherein either the sum ofa and c is 30 35 and b is 25 30 or the sum ofa and c is 140 150 and b is 25 30 and having a molecular weight of either about 3.000 or about 8.000.
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- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Biophysics (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- Veterinary Medicine (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Organic Chemistry (AREA)
- Medicinal Preparation (AREA)
- Lubricants (AREA)
Priority Applications (5)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE2115116A DE2115116C3 (de) | 1970-03-27 | 1971-03-25 | Gleitmittel und Verfahren zu dessen Herstellung |
FR7110555A FR2083622B1 (ja) | 1970-03-27 | 1971-03-25 | |
CH445071A CH562614A5 (ja) | 1970-03-27 | 1971-03-26 | |
GB1296007D GB1296007A (ja) | 1970-03-27 | 1971-04-19 | |
US492786A US3926817A (en) | 1970-03-27 | 1974-07-29 | Glidants and process for preparing the same |
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP2575670A JPS4928408B1 (ja) | 1970-03-27 | 1970-03-27 | |
US33637273A | 1973-02-27 | 1973-02-27 | |
US492786A US3926817A (en) | 1970-03-27 | 1974-07-29 | Glidants and process for preparing the same |
Publications (1)
Publication Number | Publication Date |
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US3926817A true US3926817A (en) | 1975-12-16 |
Family
ID=27285145
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US492786A Expired - Lifetime US3926817A (en) | 1970-03-27 | 1974-07-29 | Glidants and process for preparing the same |
Country Status (5)
Country | Link |
---|---|
US (1) | US3926817A (ja) |
CH (1) | CH562614A5 (ja) |
DE (1) | DE2115116C3 (ja) |
FR (1) | FR2083622B1 (ja) |
GB (1) | GB1296007A (ja) |
Cited By (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4251506A (en) * | 1977-05-25 | 1981-02-17 | Commonwealth Scientific And Industrial Research Organization | Controlled-release compositions for administration of therapeutic agents to ruminants |
US4347235A (en) * | 1981-09-03 | 1982-08-31 | Miles Laboratories, Inc. | Water-soluble tablet |
US4865851A (en) * | 1987-05-14 | 1989-09-12 | Glaxo Group Limited | Pharmaceutical composition comprising cefuroxime axetil |
US4883182A (en) * | 1985-05-31 | 1989-11-28 | Hughes Raymond J | Tamper evident capsule and insert device |
US20040082823A1 (en) * | 2002-10-24 | 2004-04-29 | Neurok Llc | Method of hydrocarbon stabilization |
US20050288276A1 (en) * | 2002-10-18 | 2005-12-29 | Stanka Perc | Pharmaceutical formulation of olanzapine |
US20070190135A1 (en) * | 1998-10-12 | 2007-08-16 | Chugai Seiyaku Kabushiki Kaisha | Phosphate-binding polymer and tablets using the same |
CN102993983A (zh) * | 2012-12-14 | 2013-03-27 | 吴江市利达上光制品有限公司 | 喷雾式杀菌皮革上光剂及其制备方法 |
Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3518345A (en) * | 1967-10-05 | 1970-06-30 | Miles Lab | Tableting lubricant |
US3518346A (en) * | 1968-01-02 | 1970-06-30 | Miles Lab | Tableting |
US3719599A (en) * | 1969-11-25 | 1973-03-06 | Lepetit Spa | Solid lubricant composition and method of preparation |
Family Cites Families (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE538387C (de) * | 1930-09-14 | 1931-11-13 | Siemens Schuckertwerke Akt Ges | Schmiermittel fuer feinste Instrumente |
US2730499A (en) * | 1951-08-01 | 1956-01-10 | Exxon Research Engineering Co | Lubricants for heavy journal bearings operating at elevated temperatures |
US2857313A (en) * | 1956-03-27 | 1958-10-21 | Ciba Pharm Prod Inc | Self-lubricating granulation |
GB954431A (en) * | 1959-07-24 | 1964-04-08 | Socony Mobil Oil Co Inc | Grease composition and method of preparation of same |
GB1291281A (en) * | 1969-03-20 | 1972-10-04 | Pfizer Ltd | Improvements in pharmaceutical compositions |
-
1971
- 1971-03-25 FR FR7110555A patent/FR2083622B1/fr not_active Expired
- 1971-03-25 DE DE2115116A patent/DE2115116C3/de not_active Expired
- 1971-03-26 CH CH445071A patent/CH562614A5/xx not_active IP Right Cessation
- 1971-04-19 GB GB1296007D patent/GB1296007A/en not_active Expired
-
1974
- 1974-07-29 US US492786A patent/US3926817A/en not_active Expired - Lifetime
Patent Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3518345A (en) * | 1967-10-05 | 1970-06-30 | Miles Lab | Tableting lubricant |
US3518346A (en) * | 1968-01-02 | 1970-06-30 | Miles Lab | Tableting |
US3719599A (en) * | 1969-11-25 | 1973-03-06 | Lepetit Spa | Solid lubricant composition and method of preparation |
Cited By (9)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4251506A (en) * | 1977-05-25 | 1981-02-17 | Commonwealth Scientific And Industrial Research Organization | Controlled-release compositions for administration of therapeutic agents to ruminants |
US4347235A (en) * | 1981-09-03 | 1982-08-31 | Miles Laboratories, Inc. | Water-soluble tablet |
US4883182A (en) * | 1985-05-31 | 1989-11-28 | Hughes Raymond J | Tamper evident capsule and insert device |
US4865851A (en) * | 1987-05-14 | 1989-09-12 | Glaxo Group Limited | Pharmaceutical composition comprising cefuroxime axetil |
US20070190135A1 (en) * | 1998-10-12 | 2007-08-16 | Chugai Seiyaku Kabushiki Kaisha | Phosphate-binding polymer and tablets using the same |
US20050288276A1 (en) * | 2002-10-18 | 2005-12-29 | Stanka Perc | Pharmaceutical formulation of olanzapine |
US20110319395A1 (en) * | 2002-10-18 | 2011-12-29 | Krka, Tovarna Zdravil, D.D. | Pharmaceutical Formulation of Olanzapine |
US20040082823A1 (en) * | 2002-10-24 | 2004-04-29 | Neurok Llc | Method of hydrocarbon stabilization |
CN102993983A (zh) * | 2012-12-14 | 2013-03-27 | 吴江市利达上光制品有限公司 | 喷雾式杀菌皮革上光剂及其制备方法 |
Also Published As
Publication number | Publication date |
---|---|
DE2115116A1 (de) | 1971-10-14 |
DE2115116C3 (de) | 1982-04-15 |
DE2115116B2 (de) | 1981-06-25 |
CH562614A5 (ja) | 1975-06-13 |
FR2083622B1 (ja) | 1975-08-22 |
GB1296007A (ja) | 1972-11-15 |
FR2083622A1 (ja) | 1971-12-17 |
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