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CN1075332A - In the sulfonic acid and make the method for granulated detergent - Google Patents

In the sulfonic acid and make the method for granulated detergent Download PDF

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Publication number
CN1075332A
CN1075332A CN 93101600 CN93101600A CN1075332A CN 1075332 A CN1075332 A CN 1075332A CN 93101600 CN93101600 CN 93101600 CN 93101600 A CN93101600 A CN 93101600A CN 1075332 A CN1075332 A CN 1075332A
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CN
China
Prior art keywords
aggregate
neutralizing agent
anion surfactant
detergent
composition
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.)
Granted
Application number
CN 93101600
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Chinese (zh)
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CN1054632C (en
Inventor
A·多塞特
O·帕奎特
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Procter and Gamble Co
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Procter and Gamble Co
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Publication of CN1075332A publication Critical patent/CN1075332A/en
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Publication of CN1054632C publication Critical patent/CN1054632C/en
Anticipated expiration legal-status Critical
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    • 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
    • C11D17/00—Detergent materials or soaps characterised by their shape or physical properties
    • C11D17/06—Powder; Flakes; Free-flowing mixtures; Sheets
    • C11D17/065—High-density particulate detergent compositions
    • 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
    • C11D11/00—Special methods for preparing compositions containing mixtures of detergents
    • C11D11/04—Special methods for preparing compositions containing mixtures of detergents by chemical means, e.g. by sulfonating in the presence of other compounding ingredients followed by neutralising

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  • Chemical & Material Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Wood Science & Technology (AREA)
  • Organic Chemistry (AREA)
  • Detergent Compositions (AREA)

Abstract

Making the method for granulated detergent, is that the anion surfactant of sour form is used the neutralization of fine powdered neutralizing agent in high shear mixer, and its consumption is for being in excess in stoichiometry, and the powder median size is less than 5 microns.Also comprise the free-pouring detergent composition of method manufacturing thus.

Description

In the sulfonic acid and make the method for granulated detergent
The present invention relates in the dry method and the method for sulfonic acid and the detergent composition of manufactured thus.
Granulated detergent is mainly spray-drying process so far and makes.When spraying drying, each detergent component for example tensio-active agent and washing assistant and nearly the water of 35-50% be mixed into slip.Slip heating and spraying drying need be consumed big energy and use expensive equipment.If have and need not make water slurry exsiccant effective ways again, will be that expense is lower.
" dry method " neutralization (promptly not moisture in fact) has been known and has been the granulated detergent, the particularly anion surfactant of neutralizing acid form of detergent factory's family expenses in the production high bulk density.
Yet what need reach is that made its clean-up performance of aggregate is equally matched with conventional spray-dried granules.
Have found that the speed of described neutralization reaction and completeness can influence the performance and the dissolution rate of detergent particles, therefore in the industrial application of this method, above-mentioned two aspects are important requirements.
Now be surprised to find that, if employed neutralizing agent is the levigated particle, and its granular size makes neutralization reaction reach optimization at the close limit that limits, and the performance and the dissolution rate of the high bulk density detergent particles that makes of " dry method " neutralization all acquire benefit like this.The loose density of pressing the inventive method gained detergent particles is greater than 650 grams per liters.
On May 7th, 1985, disclosed US 4515707 described a kind of dry method neutralization method, was that washing composition sulfuric acid or sulfonic acid are neutralized with powdered sodium carbonate in high shear mixer in the presence of the powder tripoly phosphate sodium STPP.The gained powdered product can be used for making solid block detergent.
Japanese Patent 60 072999 has disclosed a kind of batch processes, selects for use composition to mix washing composition sulfonic acid, yellow soda ash, water and other in high shear mixer, and be cooled to 40 ℃ or following then, and make powder with zeolite powder, and with it granulation.
On April 3rd, 1991, disclosed EPA 0420317 disclosed a kind of continuation method, selected for use composition to mix washing composition sulfonic acid, particulate inorganic raw material, water and other in high-speed mixer/enrichment machine.Then material is handled in the tablets press/enrichment machine of middling speed.Add fine powder in second step or the first step and between second step, it is introduced is of value to this accumulation process.
On June 5th, 1991, disclosed EPA 0430603 disclosed a kind of method for preparing high reactivity thing washing composition aggregate, was to use the very high stopping composition of a kind of fine-grannular and oily absorption value as the processing aid of assembling operation.
The present invention relates to a kind of method of making granulated detergent, is that the anion surfactant with a kind of sour form neutralizes in high shear mixer, and the excessive fine particulate neutralizing agent of stoichiometry is used in neutralization, and its median size is less than 5 microns.
The present invention also comprises the free-pouring detergent composition of method manufacturing thus.
A dry powder streams is sent into height cut mixing machine, in wherein mixing, and optionally mix with other liquid adhesive material with liquid or paste anionic surfactant acid.This powder logistics comprises a kind of particulate state neutralizing agent, generally is alkaline, inorganic salts, and begins neutralization in this high shear mixer, and continues.The invention is characterized in that the granular neutralizing agent in this powder logistics is the porphyrize powder type.
Described powder logistics contains a kind of particulate state neutralizing agent.Preferred neutralizing agent comprises any carbon salt or supercarbonate or its mixture.It is excessive that the neutralizing agent consumption should be stoichiometry with respect to this anionic surfactant acid.Preferably should there be at least 5 times in stoichiometry and required neutralizing agent.
This flow of powder also can contain any other detergent powder that is suitable for.Preferred powder be in washing process activated those, comprise that zeolite, tripoly phosphate sodium STPP, silicon oxide, silicate, polymer class comprise toxilic acid and acrylic acid multipolymer, carboxymethyl cellulose, white dyes, ethylenediamine tetraacetic acid (EDTA) and inorganic salt such as vitriol.The composition that can be used as the solid operation that other are suitable comprises additional surfactant, and it is described to see below.
Have found that, use the fine powdered neutralizing agent can improve the cake strength of clean-up performance, dissolving characteristic and final detergent composition.The median size of this neutralizing agent should be less than 5 microns.The definition of described median size sees below described.
Believe that this neutralizing agent particulate specific surface area can improve the efficient of neutralization reaction greatly.Best its narrow diameter distribution, and median size is little.Preferred 90%(volume) particulate equivalent particle diameter is less than 10 microns.
Term particle diameter used herein and median size are defined as follows:
Any given particle grain size is: with the diameter of this particle with the spheroid of volume.
On average (or intermediate value) particle diameter is: get such particle diameter, making has the 50%(volume) its particle diameter of particle less than getting particle diameter.
Whole particle size data of used neutralizing agent particulate are to measure with Malvern 2600 serial optical lasers in this.
Can use the pulverizer that is suitable for the neutralizing agent particle is ground to form any kind of the particle diameter that requires.Have found that, Trade Micronizer(Britain, the elutriation pulverizer that the dish that Kent) provides-sheet jet mill and Hosokawa Micron provide is a particularly suitable.
The anionic surfactant acid that is suitable for is included in has one about 9 to the alkyl of about 20 carbon atoms and the organosulfur acid-respons product of a sulfonic acid in the molecular structure.The example of this type of synthetic surfactant has alkyl benzene sulphonate (ABS), and its alkyl is a straight or branched, has an appointment 9 to about 15 carbon atoms.
The anionic surfactant acid of particularly suitable is alkyl 11 linear alkyl benzene sulphonic acid to about 13 carbon atoms of having an appointment.
Other available surfactant acids comprise α-Huang Huazhifangsuanjiazhi, alkene class sulfonate and β-alkoxyl group alkyl sulfonate.
Also can use above-mentioned various mixture.
Also other class I liquid I binders can be sprayed onto in this high shear mixer, comprise amino polyphosphate, diethylenetriamine pentaacetic acid and additional anion surfactant (salt form after the neutralization), nonionic, positively charged ion, both sexes and zwitterionics.
The aminopolyphosphonic acid salt of particularly suitable comprises Diethylenetriamine pentamethylene phosphonic acids and ethylenediamine tetramethylene phosphonic acid.
The additional anion surfactant of particularly suitable is the water-soluble salt of higher fatty acid.These comprise " soap ", they are anion surfactants useful in the present composition, comprise alkali metal soap, for example the sodium salt of higher fatty acid, sylvite, ammonium salt and alkylammonium salt, contain about 8 in the lipid acid to about 24 carbon atoms, preferred about 12 to 18 carbon atoms.Making soap can be by oil or directly saponification of fat, or free fatty acids is neutralized.Particularly suitable be the sodium salt or the sylvite of cocounut oil and tallow fatty acid mixture, that is the soda soap of Tallow Inedible Grade and cocounut oil or potash soap.
The available anion surfactant also comprises the water-soluble salt of organic sulfuric acid reaction product, and preferred as alkali salt, ammonium salt and alkylammonium salt contain in this molecular structure and have an appointment 10 to about 20 carbon atoms and sulphonate or sulfate group.(the moieties that in " alkyl " speech, comprises acyl group.) this type of synthetic surfactant for example alkylsurfuric acid sodium salt and sylvite, particularly higher alcohols (C 8-C 18) through the sulfation products therefrom, these alcohol for example are that the glyceryl ester of Tallow Inedible Grade or cocounut oil is through reduction gained person.
Other anion surfactants also have the sodium or the sylvite of alkylphenol oxygen ethyleneether sulfuric ester, and its each molecule contains about 1 to about 10 ethylene oxide units, and its alkyl contains about 8 to about 12 carbon atoms.Also have the sodium or the sylvite of alkyl oxygen ethyleneether sulfuric ester, its each molecule contains about 1 to about 10 ethylene oxide units, and its alkyl contains about 10 to about 20 carbon atoms.
Also can use water miscible nonionogenic tenside as the second surface promoting agent in the composition of the present invention.The blend that contains nonionic and anion surfactant in a kind of particularly preferred lotion, its ratio are about 0.01: 1 to about 1: 1, are preferably about 0.05: 1.The nonionogenic tenside consumption can reach at most and major surfaces promoting agent equivalent.These non-ionic type raw materials comprise the polycondensation product by organic hydrophobic compound and alkylene oxide (tool water-wet behavior), and the former can be compound aliphatic series or aromatics.The polyoxy alkylidene chain length of polycondensation on the hydrophobic group is easy to regulate, and obtains the water-soluble products of required hydrophilic and lipophilic balance.
The ionic surfactant pack that is suitable for is drawn together the oxygen ethylidene polycondensate of alkylphenol, and for example alkyl is the polycondensation product of the alkylphenol of about 6-16 carbon atom, and its alkyl can be a straight or branched, every mole of about 4-25 moles of ethylene oxide of alkylphenol.
Preferred nonionic is the water-soluble polycondensation product of 8-22 carbon atom fatty alcohol, and it can be a straight or branched, every mol of alcohol 4-25 moles of ethylene oxide.Particularly preferably be by C 1-C 15Alcohol gained polycondensation product, and the polycondensation product of propylene glycol and oxyethane.
Semi-polar ionic surfactant pack is drawn together water-soluble amine oxides, and it contains an about C 10-C 18Moieties and two be selected from about C 1-C 3The part of alkyl and hydroxyalkyl; The water soluble oxidized phosphine, it contains an about C 10-C 18Moieties and two be selected from about C 1-C 3Alkyl and hydroxyalkyl part; And water-soluble sulfone, it contains an about C 10-C 18Moieties and one are selected from about C 1-C 3Alkyl and hydroxyalkyl part.
Amphoterics comprises the aliphatic series of heterocyclic secondary and tertiary amine or the derivative of aliphatic derivatives, and wherein the aliphatic series part can be straight or branched, and wherein one of each aliphatic composition is about C 8-C 18, at least one aliphatic composition contains an anionic water-soluble group.
Zwitterionics comprises the quaternary ammonium, Phosphonium and the sulfonium compound of aliphatic series, and wherein one of each aliphatic composition is about C 8-C 18
The available cats product comprises water miscible R 4R 5R 6R 7N +X -The quaternary ammonium compound of form, wherein R 4Be C 10-C 20Alkyl, preferred C 12-C 18, R 5, R 6, R 7Each is C naturally 1-C 7Alkyl; X -It is for example chlorion of a kind of negatively charged ion.The example of this type of trimethyl ammonium compound comprises C 12-C 14Alkyl trimethyl ammonium chloride, and cocounut oil alkyl trimethyl-methylsulfuric acid ammonium.
Should point out that wherein some component can be operated by solid-state form, at this moment it should be thought of as the part of this powder material stream, rather than the liquid adhesive material.
Anion surfactant/binder is to the ratio of powder material stream
Liquid component (anionic surfactant acid and binder) is subject to the tackiness of made powder to the ratio of powder composition.Being preferably 1: 1 to 1: 4, most preferably is 1: 2 to 1: 3.
Preferred high shear mixer is a Loedige R CB series, is by Loedige Maschinenbau GmbH(Paderhorn, Germany) manufacturing.Its machine speed scope is 500-2000 rev/min, preferred about 10 seconds.The gained particulate matter needs further processing, obtains aggregate products, and is as mentioned below.Other high shear mixers that are suitable for are thought Zig-Zig Blender(blending machine in a zigzag, and Denmark P K Niro makes).Also have Eirich R batch-type mixing machine also to be suitable for (Gustau Eirich makes, German Hardheim).In this kind batch blender, can directly obtain aggregate with about 1 minute mixing time, do not need further processing.
Can send into powder material in this high shear mixer with suitable powder carrying and delivery system.
Anionic surfactant acid and other liquid materials generally are to pump into high shear mixer, by conventional formula nozzle, comprise and use fog nozzle when pumping into.
The particle made from above-mentioned method is applicable to and further is processed into the washing composition aggregate.Described further processing comprises and utilizes this particle neutralizing agent this anionic surfactant acid that neutralizes continuously.This can further mix in a middling speed tablets press.The mixing machine that is suitable for comprises described Loedige R KM mixing machine.
The residence time therein is 1-20 minute, preferred about 5 minutes, if need, adds cooling.
Additional liquid or powder material can be chosen wantonly and be added in this middling speed tablets press, or add between twice mixing.Can use any suitable detergent ingredients material, comprise aforesaid any.
Then, become particle to carry out drying with one or multi-channel cooling or drying process.The equipment that is suitable for comprises fluidized bed dryer and the airlift that industry member can get.
The fine particle (less than about 150 microns) that exists can be removed from final powder material stream, and can be recycled in the technological process via high shear mixer.The air separation equipment that can use any industry member to get can share with appropriate filters if need.The technology those skilled in the art that are suitable for are very familiar.Fine powder separates and recirculation if carried out effectively, then detects less than levigated particulate state neutralizing agent in final product composition having or only measures seldom.But if do not take fine powder to separate and the recirculation measure, or arrange put effective inadequately, then can some levigated particulate state neutralizing agents of existence in final product composition having.
Its loose density of the aggregate of gained should be greater than 650 grams per liters, and should be the brittle particles of low porosity.
The detergent composition finished product
This aggregate can mix with other powder compositions, obtains the free flowing granule detergent composition.Perhaps, just this aggregate as final product composition having.Detergent composition by the inventive method manufacturing should comprise 50-100%(weight) this aggregate, preferred 80-100%.
Other detergent ingredients can be sprayed onto on this detergent particles, for example, nonionogenic tenside, spices or join in this aggregate with the dry powder powder, for example SYNTHETIC OPTICAL WHITNER and bleach activator, enzyme, polymkeric substance comprise polyoxyethylene glycol.
Embodiment
Use C 11-C 13The washing composition aggregate is produced in linear alkyl benzene sulphonic acid and yellow soda ash neutralization.This yellow soda ash (the light body SODA ASH LIGHT 99.2 of ICI) is prepared into 5 kinds of particle diameters, and promptly A to E is 5 kinds.
A). ground yellow soda ash in disc jet mill (Trade Micronizing is produced);
B). ground yellow soda ash in elutriation masher (Hosokawa Micron is produced);
C). ground yellow soda ash in pin-type mill (Alpine is produced);
D). ground yellow soda ash in hammer mill (Alpine is produced);
E) the commercially available yellow soda ash of .ICI supply (light body SODA ASH LIGHT 99.2).
Yellow soda ash particle diameter (micron) * A B C D E
Intermediate value＜50% 3.4 5.7 18.3 59.6 73.2
<90% 4.2 15.3 69.1 152.8 209
Specific surface area (rice/centimetre 3) 1.68 1.31 0.98 0.25 0.25
* the mensuration of yellow soda ash particle diameter is used MALVERN 2600 serial laser particle testers.Described intermediate value is meant this particulate 50%(volume) be less than the particle diameter of being given.According to this,＜and the 90%(volume) be less than the particle diameter of being given.
With the blending in Eirich batch-type mixing machine of following each composition.Choosing joins the powder composition in the mixing machine.Add liquid component at last.Mixing time formed this aggregate in 1 minute.
The liquid material
Linear alkyl benzene sulphonic acid 23%
Phosphonic acids 2%
The powder material
Carbonate 21%
Zeolite 4-6%
Pentasodium triphosphate 40%
Water glass 6%
Other (polymkeric substance or the like) surpluses
To prepare to carry out physical property measurement by the aggregate of discharging in the Eirich mixing machine, and make whole finished product then and, list as follows for performance test:
A B C D E
Can float the dirty clearance (PSU) that fades 10-0.8-0.6-0.7-1.0
The aggregate bulk strength 20 2.5 6.4 10.5 9.4
The solvability grade 331220
Density (grams per liter) 850 822 602 600 664
Aggregate median size (micron) 4370 336 333 337 347
1. can float the dirty clearance that fades by following mensuration: 85%(is heavy) this aggregate and 15%(weight) Sodium peroxoborate that is mixed with bleach-activating agent mixes, and obtains end product.Use the semi-automatic double flute Lab of Japanese NATIONAL J28 washing machine.In above-mentioned finished product 70 gram impourings 30 premium on currency, the water hardness 2.0 mmole Ca 2+/ liter, 30 ℃ of water temperatures, the clothing and the cover that wherein contain 1-2 kilogram optimization pollution can float the dirt of fading (coffee, tea, Black Grape or the like).The whole finished product of this aggregate to can float fade dirty removal effect with compare with the washing composition of prescription with complete with conventional spray-drying process.Listed mark is to assess group institute's mark of giving (PUS), and by-4 to+4, it is identical with the look dirt removal effect of contrast that mark 0 is represented, negative value is represented poorer than contrast.
2. the aggregate bulk strength is by following mensuration: 100 gram aggregates are placed in the test panel, apply 10 kilogram load, last 2 minutes.Break formed with crossing pin then.Record breaks the required power of this piece, record 0-11 pound.Between the regulation 0-3 is qualified, and 0 expression piece is easy to break, the upper limit of the qualified bulk strength of 3 expressions.
3. the solvability grade is by following mensuration: will pour in the acrylic acid or the like textile bags by made finished product 90 grams of " 2 " same way as, this bag is 20 * 40 centimetres), sack is sewed, put into " 2 " used washing machine, add 30 premium on currency in the machine, 30 ℃, the clothing of 1.5 kilograms of cleanings is arranged.Slight stir 10 minutes after, sack is opened, check and stay on the fabric not dissolving detergent amount, and be divided into grade, scoring is 0 to 4,0 for the poorest, 4 is excellent.Based on evaluation to commercially available granulated detergent, the regulation grading system 3 and above be qualified.
4. the aggregate median size is measured with standard Tyler sieve.Corresponding composition weight is converted into the logarithm normal distributes, note median size thus.
From above seeing, by sample A(of the present invention the thinnest grind yellow soda ash) final product composition having of made aggregate providing apparent benefit aspect clean-up performance and the physical property, this is to exceed the scope of the invention with B to E(yellow soda ash particle diameter) the result that compares with final product composition having of aggregate.Above result shows that also the clean-up performance of pressing the made identical component composition of made finished product detergent composition (sample A) its clean-up performance of the present invention and conventional spray-drying process is equally matched.

Claims (10)

1, a kind of method of making granulated detergent, comprise that the anion surfactant (a) with sour form neutralizes with the excessive particulate state neutralizing agent (b) of stoichiometry in high shear mixer, it is characterized in that described particulate state neutralizing agent has its particle diameter of particle of 50% (volume) less than 5 microns.
2, the method for claim 1 is characterized in that, the 90%(volume of described particulate state neutralizing agent) its particle diameter is less than 10 microns.
3, the method for claim 1 is characterized in that, described anion surfactant (a) is an alkyl benzene sulphonate (ABS).
4, the method for claim 1 is characterized in that, described neutralizing agent (b) is a kind of sodium salt or the calcium salt of carbonic acid.
5, make the method for washing composition aggregate by claim 1, further comprise:
(I) reunites this detergent particles in the tablets press/enrichment machine of middling speed, and has or do not have another powder material stream;
(II) carries out drying and/or cooling.
6, by the loose density of the method manufacturing of claim 5 washing composition aggregate greater than 650 grams per liters.
7, by the washing composition aggregate of the method manufacturing of claim 5, it is characterized in that, be less than the 40%(weight of this aggregate by the sour form anion surfactant (a) and the content of particulate state neutralizing agent (b) neutral salt form anion surfactant).
8, by the washing aggregate of the method manufacturing of claim 5, it is characterized in that, be less than the 28%(weight of this aggregate by the sour form anion surfactant (a) and the content of particulate state neutralizing agent (b) neutral salt form anion surfactant).
9, a kind of free flowing granule shape cleaning composition wherein contains 50-100%(weight) the washing composition aggregate of claim 1.
10, a kind of free flowing granule shape detergent composition wherein contains 80-100%(weight) the washing composition aggregate of claim 6.
CN93101600A 1992-02-14 1993-02-13 Process for making detergent granules by neutralisation of sulphonic acids Expired - Fee Related CN1054632C (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
EP19920870026 EP0555622B1 (en) 1992-02-14 1992-02-14 Process for making detergent granules by neutralisation of sulphonic acids
EP92870026.9 1992-02-14

Publications (2)

Publication Number Publication Date
CN1075332A true CN1075332A (en) 1993-08-18
CN1054632C CN1054632C (en) 2000-07-19

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EP (1) EP0555622B1 (en)
JP (1) JP3295083B2 (en)
CN (1) CN1054632C (en)
AU (1) AU3595593A (en)
CA (1) CA2130007C (en)
DE (1) DE69220773T2 (en)
EG (1) EG20243A (en)
ES (1) ES2104884T3 (en)
MA (1) MA22796A1 (en)
MX (1) MX9300770A (en)
MY (1) MY130067A (en)
PH (1) PH31576A (en)
TR (1) TR26854A (en)
WO (1) WO1993016154A1 (en)

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CN103773618A (en) * 2014-02-12 2014-05-07 浙江赞宇科技股份有限公司 Process and device for continuously preparing powdery washing powder particles
CN103773618B (en) * 2014-02-12 2015-04-01 浙江赞宇科技股份有限公司 Process and device for continuously preparing powdery washing powder particles
WO2015176290A1 (en) * 2014-05-23 2015-11-26 The Procter & Gamble Company Two-stage neutralization process for forming detergent granules, and products containing the same
CN106459852A (en) * 2014-05-23 2017-02-22 宝洁公司 Two-stage neutralization process for forming detergent granules, and products containing the same
CN106459852B (en) * 2014-05-23 2020-01-31 宝洁公司 Two-step neutralization process for forming detergent particles, and products comprising said detergent particles

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PH31576A (en) 1998-11-03
MX9300770A (en) 1993-09-30
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EP0555622B1 (en) 1997-07-09
ES2104884T3 (en) 1997-10-16
EP0555622A1 (en) 1993-08-18
WO1993016154A1 (en) 1993-08-19
EG20243A (en) 1998-05-31
CA2130007C (en) 1998-08-25
MY130067A (en) 2007-05-31
JP3295083B2 (en) 2002-06-24
JPH07503750A (en) 1995-04-20
CA2130007A1 (en) 1993-08-15
TR26854A (en) 1994-08-19
CN1054632C (en) 2000-07-19
DE69220773T2 (en) 1998-02-12

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