EP0754217B1 - Fabric softening composition - Google Patents
Fabric softening composition Download PDFInfo
- Publication number
- EP0754217B1 EP0754217B1 EP95914296A EP95914296A EP0754217B1 EP 0754217 B1 EP0754217 B1 EP 0754217B1 EP 95914296 A EP95914296 A EP 95914296A EP 95914296 A EP95914296 A EP 95914296A EP 0754217 B1 EP0754217 B1 EP 0754217B1
- Authority
- EP
- European Patent Office
- Prior art keywords
- fabric softening
- compound
- composition according
- softening composition
- compositions
- 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.)
- Expired - Lifetime
Links
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
- C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
- C11D3/0005—Other compounding ingredients characterised by their effect
- C11D3/001—Softening 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
- C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
- C11D1/38—Cationic compounds
- C11D1/62—Quaternary ammonium compounds
-
- 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
- C11D1/88—Ampholytes; Electroneutral compounds
- C11D1/94—Mixtures with anionic, cationic or non-ionic compounds
-
- 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
- C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
- C11D3/0005—Other compounding ingredients characterised by their effect
- C11D3/001—Softening compositions
- C11D3/0015—Softening compositions liquid
-
- 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
- C11D1/88—Ampholytes; Electroneutral compounds
- C11D1/90—Betaines
-
- 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
- C11D1/88—Ampholytes; Electroneutral compounds
- C11D1/92—Sulfobetaines ; Sulfitobetaines
Definitions
- the present invention relates to fabric softening compositions.
- the invention relates to fabric softening compositions that have excellent stability, dispensing and dispersing properties.
- Rinse added fabric softener compositions are well known. Typically such compositions contain a water insoluble fabric softening agent dispersed in water at a level of softening agent up to 7% by weight in which case the compositions are considered dilute, or at levels from 7% to 30% in which case the compositions are considered concentrates. Fabrics can also be softened by the use of sheets coated with softening compound for use in tumble dryers. In more detail the commercially available fabric softening compounds generally form stacked lamellar structures in water which have characteristic L ⁇ to L ⁇ phase transition temperatures.
- liquid fabric softening compositions are in the form of dispersed colloidal particles of the fabric softening compound.
- Fabric softening compositions comprising dissolved fabric softening compound in organic solvent and powder or granular compositions have also been described.
- Physical instability manifests itself as a thickening on storage of the composition to a level where the composition is no longer pourable, and can even lead to the irreversible formation of a gel.
- the formation of a gel can also occur in the dispensing drawer of a washing machine when the temperature of the drawer is increased by the influx of warm water. The thickening is very undesirable since the composition can no longer be conveniently used.
- Physical instability can also manifest itself as phase separation into two or more separate layers.
- FR-A-1 447 334 discloses a general procedure for increasing the dispersibility and solubility of cationic compounds by the use of specific betaines but makes no reference to cationic based rinse conditioners.
- GB-A-2 163 771 discloses wash cycle detergent compositions comprising a nonionic surfactant and a cationic quaternary ammonium compound which does not contain an ester link or a single long chain.
- EP-A-0 354 011 discloses a fabric conditioning composition
- a fabric conditioning composition comprising a cationic fabric conditioner having two C 15-22 alkyl or alkenyl groups and sufficient nonionic or amphoteric surfactant to lower the viscosity of the composition.
- EP-A-0 125 031 discloses a liquid fabric softening composition comprising a cationic fabric softening agent, an amphoteric compound and a non-aqueous solvent.
- EP-A-0 326 213 discloses a rinse conditioner comprising a water soluble amphoteric conditioning material and a co-active material. No reference is made to quaternary ammonium compounds having a single C 20 or above chain or two C 12-22 alkyl or alkenyl groups connected to the head group via at least one ester link.
- EP-A-0 569 847 discloses a fabric conditioning composition which may comprise cationic actives and amphoteric surfactants, although no disclosure is made of the cationic actives being solubilised by the amphoteric surfactants.
- US-A-4 789 491 discloses a specific process for the formulation of aqueous dispersions of cationic softening compounds. The process is said to overcome the difficulties of product viscosity and poor dispensing and dispersing on storage.
- the physical stability of rinse added fabric softener compositions has been improved by the addition of viscosity control agents or anti-gelling agents.
- viscosity control agents are added to certain concentrated compositions.
- the agents may include C 10 -C 18 fatty alcohols.
- EP-A-280 550 Unilever
- EP-A-507 478 discloses a physically stable fabric softening composition comprising a water insoluble, biodegradable, ester-linked quaternary ammonium compounds and a nonionic stabilising agent.
- EP-A-111074 is typical and uses a silica to carry the softener.
- a disadvantage of using a carrier such as silica is that it bulks up the product and serves no function beyond making the powder compatible with other ingredients that may be contained in a washing powder.
- EP-A-569 184 discloses use of a granular composition to form a pre-dilute which is then added to the dispenser drawer of the washing machine.
- WO-A-92/18593 discloses a granular fabric softening composition which can be added to water to form an aqueous emulsion.
- the composition contains a nonionic fabric softener such as a sorbitan ester and a mono-long chain alkyl cationic surfactant.
- WO-A-93/23510 discloses liquid and solid fabric softeners comprising biodegradable diester quaternary ammonium fabric softening compounds and a viscosity and/or dispersibility modifier, the application also discloses specific processes for making these products.
- the viscosity and/or dispersibility modifier may be a single long chain, alkyl cationic or a nonionic surfactant.
- the solid composition when added to water forms an emulsion or dispersion.
- US-A-3 892 669 discloses a clear, homogeneous, aqueous based liquid fabric softening composition and is limited to solubilised tetraalkyl quaternary ammonium salts having two short-chain alkyl groups and two long-chain alkyl groups, the longer chain groups having some methyl and ethyl branching.
- the solubilisers comprise of aryl sulphonates, diols, ethers, low molecular weight quaternaries, sulphobetaines, and nonionic surfactants.
- nonionic surfactants and phosphine oxides are not suitable for use alone and only have utility as auxiliary solubilisers.
- the present invention discloses fabric softening compositions having excellent softening properties yet which exhibit excellent storage stability at both high and low temperatures, good freeze thaw recovery and excellent dispensability and dispersibility when the composition is concentrated and even when the fabric softening compound is concentrated to levels greater than 30 wt%. Furthermore compositions prepared according to our invention do not suffer from loss of softening performance.
- a fabric softening composition comprising
- the fabric conditioner of the invention is not in conventional lamellar form, and when contacted with water may be solubilised partially in the form of self-size-limiting molecular aggregates, such as micelles or micellar solutions with solid or liquid interiors or mixtures thereof.
- self-size-limiting molecular aggregates such as micelles or micellar solutions with solid or liquid interiors or mixtures thereof.
- the composition is in a form containing water the composition itself may be at least partially in the form of self-size-limiting molecular aggregates. It is thought that it is this new structure of the fabric softening compositions that overcomes the problems of the prior art.
- the fabric softening compound and solubilising agent form a transparent mix.
- the following tests may be used to determine definitely whether or not a composition falls within the present invention.
- the fabric softening compositions according to the invention may be translucent.
- Translucent in the context of this invention means that when a cell 1cm in depth is filled with the fabric softening composition, "Courier 12 point" typeface can be read through the cell.
- the fabric softening compound is suitably a water insoluble quaternary ammonium material comprising a single alkyl or alkenyl chain length equal to or greater than C 20 or, more preferably, the softening compound comprising a polar head group and two alkyl or alkenyl chains each having an average chain length equal to or greater than C 12 such as a quaternary ammonium material having two C 12-22 alkyl or alkenyl groups connected to the quaternary ammonium head group via at least one ester link.
- the fabric softening compound of the invention has two long chain alkyl or alkenyl chains with an average chain length equal to or greater than C 14 . More preferably each chain has an average chain length equal or greater than C 16 . Most preferably at least 50% of each long chain alkyl or alkenyl group has a chain length of C 18 .
- Substantially insoluble fabric softening compounds in the context of this invention are defined as fabric softening compounds having a solubility less than 1 x 10 -3 wt% in demineralised water at 20°C.
- the fabric softening compounds Preferably have a solubility less than 1 x 10 -4
- the fabric softening compounds have a solubility at 20°C in demineralised water from 1 x 10 -8 to 1 x 10 -6 .
- the fabric softening compound is a water insoluble quaternary ammonium material which comprises a compound having two C 12-18 alkyl or alkenyl groups connected to the molecule via at least one an ester link. It is more preferred if the quaternary ammonium material has two ester links present.
- the especially preferred ester-linked quaternary ammonium material for use in the invention can be represented by the formula: wherein each R 1 group is independently selected from C 1-4 alkyl, hydroxyalkyl or C 2-4 alkenyl groups; and wherein each R 2 group is independently selected from C 8-28 alkyl or alkenyl groups;
- a second preferred type of quaternary ammonium material can be represented by the formula: wherein R 1 , n X - and R 2 are as defined above.
- Preferred materials of this class such as 1,2 bis[hardened tallowoyloxy]-3- trimethylammonium propane chloride and their method of preparation are, for example, described in US-A-4 137 180 (Lever Brothers).
- these materials comprise small amounts of the corresponding monoester as described in US-A-4 137 180 for example 1-hardened tallowoyloxy -2-hydroxy -3-trimethylammonium propane chloride.
- the solubilising agent is an amphoteric surfactant, and is characterised in terms of its phase behaviour.
- Suitable solubilising agents are amphoteric surfactants for which, when contacted within water, the first lyotropic liquid crystalline phase formed is normal cubic (I1) or normal cubic-bicontinuous (V1) or hexagonal (H1) or nematic (Ne1), or intermediate (Int1) phase as defined in the article by G J T Tiddy et al, J Chem Soc. Faraday Trans. 1., 79, 975, 1983 and G J T Tiddy , "Modern Trends of Colloid Science in Chemistry and Biology", Ed. H-F Eicke, 1985 Birkhauser Verlag Basel].
- Surfactants forming L ⁇ phases at concentrations of less than 20 wt% are not suitable.
- amphoteric surfactants are defined as substances with molecular structures consisting of a hydrophilic and hydrophobic part.
- the hydrophobic part consists of a hydrocarbon and the hydrophilic part consists of both a positive and a negative group.
- Preferred amphoteric surfactants include amine oxides, betaines including sulphobetaines and tegobetaines, phosphine oxides and sulphoxides.
- Mixtures of solubilising agents may be used.
- the solubilising is desirably solid at room temperature as this provides crisp composition particles.
- the solubilising agent further comprises a non-surfactant co-solubiliser.
- co-solubilisers include propylene glycol, urea , acid amides up to and including chain lengths of C 6, citric acid and other poly carboxylic acids as disclosed in EP-A-0 404 471 (Unilever), glycerol, sorbitol and sucrose.
- Particularly preferred are polyethylene glycols (PEG) having a molecular weight ranging from 200 - 6000, most preferably from 1000 to 2000.
- the ratio of co-solubiliser to amphoteric surfactant is from to 2:1 to 1:40.
- the ratio of co-solubiliser to nonionic surfactant is less than 1:1, more preferably 1:5.
- the weight ratio of solubilising agent (where relevant this would also include the co-solvent) to fabric softening compound is greater than 1:4, preferably equal to or greater than 2:3. It is advantageous if the ratio of solubilising agent to fabric softening compound is equal to or below 4:1, more preferably below 3:2.
- solubilising agent/ co-solubiliser is present at a level greater than 5 wt% of the total composition, preferably at a level greater than 10 wt%.
- the solubilising agent/ co-solubiliser may be present at a level greater than 20 wt% of the total composition, or even at a level greater than 30 wt%. Such higher levels are especially preferred where the fabric softening composition is a solid.
- compositions of the invention preferably have a pH of more than 1.5, more preferably less than 5.
- the composition can also contain fatty acids, for example C 8 - C 24 alkyl or alkenyl monocarboxylic acids, or polymeric carboxylic acids.
- fatty acids for example C 8 - C 24 alkyl or alkenyl monocarboxylic acids, or polymeric carboxylic acids.
- saturated fatty acids are used, in particular, hardened tallow C 16 -C 18 fatty acids.
- the level of fatty acid material is preferably more than 0.1% by weight, more preferably more than 0.2% by weight. Especially preferred are concentrates comprising from 0.5 to 20% by weight of fatty acid, more preferably 1% to 10% by weight.
- the weight ratio of fabric softening compound to fatty acid material is preferably from 10:1 to 1:10.
- composition is substantially free of nonionic hydrophobic organic materials such as hydrocarbons and hydrocarbyl esters of fatty acids.
- the composition can also contain one or more optional ingredients, selected from non-aqueous solvents, pH buffering agents, perfumes, perfume carriers, fluorescers, colorants, hydrotropes, antifoaming agents, antiredeposition agents, polymeric or other thickeners, enzymes, optical brightening agents, opacifiers, anti-shrinking agents, anti-wrinkle agents, anti-spotting agents, germicides, fungicides, antioxidants, anti-corrosion agents, drape imparting agents, antistatic agents and ironing aids.
- optional ingredients selected from non-aqueous solvents, pH buffering agents, perfumes, perfume carriers, fluorescers, colorants, hydrotropes, antifoaming agents, antiredeposition agents, polymeric or other thickeners, enzymes, optical brightening agents, opacifiers, anti-shrinking agents, anti-wrinkle agents, anti-spotting agents, germicides, fungicides, antioxidants, anti-corrosion agents, drape imparting agents, antistatic agents and
- the product may be in any product form. Particularly preferred forms are liquid and solid compositions and compositions suitable for coating onto a dryer sheet.
- Solid composition in this context includes compositions in the form of a tablet, a gel, a paste and preferably granules or a powder.
- the invention further provides a process for preparing a rinse conditioner, as described above, which comprises the steps of:
- composition may be prepared by the independent addition of the water insoluble fabric softening compound and the solubilising agent to conventional ingredients.
- compositions in solid form may be prepared by spray drying, freeze drying, milling, extraction, cryogenic grinding or any other suitable means.
- Softening performance was evaluated by adding 0.lg of fabric softening compound (2ml of a 5% a.d. dispersion) for liquids to 1 litre of tap water, 10°FH, at ambient temperature containing 0.001% (w/w) sodium alkyl benzene sulphonate (ABS) in a tergotometer.
- ABS sodium alkyl benzene sulphonate
- Three pieces of terry towelling (8cm x 8cm, 40g total weight) were added to the tergotometer pot. The cloths were treated for 5 minutes at 65 rpm, spin dried to remove excess liquor and line dried overnight.
- Each panel member assessed four sets of test cloths. Each set of test cloths contained one cloth of each test system under a evaluation. Panel members were asked to assess softness on a 8 point scale. Softness scores were calculated using an "Analysis of Variance" technique. Lower values are indicative of better softening.
- compositions having a range of fabric softening compound to solubilising agent ratios were prepared according to the either of the methods described above in Preparation of Examples. The softening performance was determined. Softening Results HT TMAPC:L5351 (wt ratio) Softness Score A 5:0 2.5 4 4:1 2.75 5 3:2 3.0 6 2:3 3.25 7 1:4 5.5 B 0:5 7.25
- compositions 4 to 7 all exhibited good softening performance and good stability.
- Composition A set under a freeze/thaw test as described under Test III above.
- compositions were prepared by either one of the methods described for Preparation of Examples.
- compositions 8 to 14 The storage stability of compositions 8 to 14 was determined by storing the compositions under a variety of conditions including a freeze/thaw regime and measuring the viscosity thereof using a Carri-med rheometer at a shear rate of 110 sec -1 . The results are shown below.
- the comparative compositions all set or the components separated illustrating poor stability.
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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)
- Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
- Detergent Compositions (AREA)
Applications Claiming Priority (7)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GB9406826A GB9406826D0 (en) | 1994-04-07 | 1994-04-07 | Fabric softening composition |
GB9406826 | 1994-04-07 | ||
GB9406825A GB9406825D0 (en) | 1994-04-07 | 1994-04-07 | Fabric softening composition |
GB9406832 | 1994-04-07 | ||
GB9406825 | 1994-04-07 | ||
GB9406832A GB9406832D0 (en) | 1994-04-07 | 1994-04-07 | Fabric softening composition |
PCT/EP1995/001085 WO1995027771A1 (en) | 1994-04-07 | 1995-03-22 | Fabric softening composition |
Publications (2)
Publication Number | Publication Date |
---|---|
EP0754217A1 EP0754217A1 (en) | 1997-01-22 |
EP0754217B1 true EP0754217B1 (en) | 1999-03-03 |
Family
ID=27267137
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
EP95914296A Expired - Lifetime EP0754217B1 (en) | 1994-04-07 | 1995-03-22 | Fabric softening composition |
Country Status (14)
Country | Link |
---|---|
EP (1) | EP0754217B1 (sk) |
CN (1) | CN1078244C (sk) |
AU (1) | AU703439B2 (sk) |
BR (1) | BR9507284A (sk) |
CA (1) | CA2184069C (sk) |
CZ (1) | CZ288956B6 (sk) |
DE (1) | DE69508069T2 (sk) |
ES (1) | ES2128723T3 (sk) |
HU (1) | HU218969B (sk) |
PL (1) | PL181174B1 (sk) |
RU (1) | RU2130522C1 (sk) |
SK (1) | SK281689B6 (sk) |
TW (1) | TW340883B (sk) |
WO (1) | WO1995027771A1 (sk) |
Families Citing this family (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
GB9520519D0 (en) * | 1995-10-04 | 1995-12-13 | Unilever Plc | Detergent composition |
US5830845A (en) * | 1996-03-22 | 1998-11-03 | The Procter & Gamble Company | Concentrated fabric softening composition with good freeze/thaw recovery and highly unsaturated fabric softener compound therefor |
JP5038444B2 (ja) * | 2007-03-22 | 2012-10-03 | エルジー ハウスホールド アンド ヘルスケア リミテッド | 低温活性を持つ繊維柔軟用組成物及びこれを含む繊維柔軟用シート |
CN101818105B (zh) * | 2010-05-17 | 2012-01-18 | 北京绿伞化学股份有限公司 | 一种兼有去污和柔软功能的洗涤剂及其制备方法 |
KR101050726B1 (ko) * | 2011-03-22 | 2011-07-20 | 주식회사 선진화학 | 섬유유연제 및 이의 제조방법 |
ES2633486T3 (es) | 2014-10-08 | 2017-09-21 | The Procter & Gamble Company | Composición mejoradora de tejidos |
Family Cites Families (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
FR1447334A (fr) * | 1965-06-15 | 1966-07-29 | Prod Chim D Auby Soc D | Procédé pour améliorer la dispersibilité et la solubilité d'agents tensio-actifs cationiques |
US3892669A (en) * | 1972-10-27 | 1975-07-01 | Lever Brothers Ltd | Clear fabric-softening composition |
US4556502A (en) * | 1983-04-08 | 1985-12-03 | Lever Brothers Company | Liquid fabric-softening composition |
GB2163771B (en) * | 1984-08-31 | 1989-01-18 | Colgate Palmolive Co | Wash cycle detergent-softener compositions |
GB2188653A (en) * | 1986-04-02 | 1987-10-07 | Procter & Gamble | Biodegradable fabric softeners |
DE68919236T2 (de) * | 1988-01-28 | 1995-04-06 | Unilever Nv | Textilbehandlungszubereitung und deren Herstellung. |
GB8818593D0 (en) * | 1988-08-04 | 1988-09-07 | Albright & Wilson | Fabric conditioners |
GB9323268D0 (en) * | 1993-11-11 | 1994-01-05 | Unilever Plc | Fabric comditioning composition |
-
1995
- 1995-03-22 AU AU21354/95A patent/AU703439B2/en not_active Ceased
- 1995-03-22 HU HU9602726A patent/HU218969B/hu not_active IP Right Cessation
- 1995-03-22 PL PL95316652A patent/PL181174B1/pl not_active IP Right Cessation
- 1995-03-22 CA CA002184069A patent/CA2184069C/en not_active Expired - Fee Related
- 1995-03-22 ES ES95914296T patent/ES2128723T3/es not_active Expired - Lifetime
- 1995-03-22 CN CN95192438A patent/CN1078244C/zh not_active Expired - Lifetime
- 1995-03-22 WO PCT/EP1995/001085 patent/WO1995027771A1/en active IP Right Grant
- 1995-03-22 DE DE69508069T patent/DE69508069T2/de not_active Expired - Lifetime
- 1995-03-22 EP EP95914296A patent/EP0754217B1/en not_active Expired - Lifetime
- 1995-03-22 CZ CZ19962902A patent/CZ288956B6/cs not_active IP Right Cessation
- 1995-03-22 BR BR9507284A patent/BR9507284A/pt not_active IP Right Cessation
- 1995-03-22 SK SK1256-96A patent/SK281689B6/sk not_active IP Right Cessation
- 1995-03-22 RU RU96119952A patent/RU2130522C1/ru not_active IP Right Cessation
- 1995-04-12 TW TW084103569A patent/TW340883B/zh active
Also Published As
Publication number | Publication date |
---|---|
HU9602726D0 (en) | 1996-11-28 |
CA2184069C (en) | 2000-11-07 |
CZ290296A3 (en) | 1997-03-12 |
ES2128723T3 (es) | 1999-05-16 |
SK281689B6 (sk) | 2001-06-11 |
RU2130522C1 (ru) | 1999-05-20 |
TW340883B (en) | 1998-09-21 |
DE69508069D1 (de) | 1999-04-08 |
AU2135495A (en) | 1995-10-30 |
CN1145091A (zh) | 1997-03-12 |
CN1078244C (zh) | 2002-01-23 |
AU703439B2 (en) | 1999-03-25 |
CZ288956B6 (cs) | 2001-10-17 |
DE69508069T2 (de) | 1999-06-24 |
EP0754217A1 (en) | 1997-01-22 |
HU218969B (hu) | 2001-01-29 |
PL181174B1 (pl) | 2001-06-29 |
MX9604035A (es) | 1998-10-31 |
SK125696A3 (en) | 1997-07-09 |
PL316652A1 (en) | 1997-02-03 |
BR9507284A (pt) | 1997-09-23 |
CA2184069A1 (en) | 1995-10-19 |
WO1995027771A1 (en) | 1995-10-19 |
HUT75194A (en) | 1997-04-28 |
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