EP0288137A2 - Method of conditioning fabrics - Google Patents
Method of conditioning fabrics Download PDFInfo
- Publication number
- EP0288137A2 EP0288137A2 EP88301346A EP88301346A EP0288137A2 EP 0288137 A2 EP0288137 A2 EP 0288137A2 EP 88301346 A EP88301346 A EP 88301346A EP 88301346 A EP88301346 A EP 88301346A EP 0288137 A2 EP0288137 A2 EP 0288137A2
- Authority
- EP
- European Patent Office
- Prior art keywords
- fabric
- group
- fabrics
- conditioning
- siloxane
- 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.)
- Withdrawn
Links
Classifications
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
- D06M15/00—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment
- D06M15/19—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment with synthetic macromolecular compounds
- D06M15/37—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
- D06M15/643—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds containing silicon in the main chain
- D06M15/6436—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds containing silicon in the main chain containing amino groups
Definitions
- This invention relates to a method of conditioning fabrics and to compositions suitable for use in such methods.
- this treatment includes the treatment with a fabric softening agent intended to soften and reduce the harshness of washed fabrics.
- the fabric softening agent may be included in a fabric washing composition, in a composition intended to be added to the rinse subsequent to washing the fabrics or included in a composition intended to be added with wet fabrics to a hot air dryer. In all cases the conditioning process takes place in an aqueous environment.
- a number of fabric conditioning materials are known, including soap, smectite clays, quaternary ammonium salts and fatty amines. All these materials have been commercially used but suffer from a variety of disadvantages. For example quaternary ammonium salts, which have been most widely used, are difficult to incorporate in liquid products except at relatively low concentrations, are not easily dispersed in cold water and may, if used in excess, render the treated fabrics water repellant.
- the fabric conditioning agent is an organofunctional polyalkyl siloxane having the general formula (I) wherein each R is independently an alkyl group containing 1 to 4 carbon atoms, each of R1, R2, and R3, is independently an alkyl group containing 1 to 24 carbon atoms or R3 is the group (CH2)q C00 ⁇ where q is 0 to 10,
- A is a divalent hydrocarbon group interrupted by or substituted with one or more oxygen containing groups
- X is an alkoxylated group
- Z is a monovalent anion or the equivalent thereof
- n and m are positive integers
- p is a positive integer
- r is a positive integer or zero such as to render the siloxane electrically neutral.
- European Patent Application No. 166 122 discloses siloxanes of general formula (I) in which the substituent R3 is the group (CH2)qCOO ⁇ and q is 1. Their preparation and their use in hair conditioning compositions is also disclosed.
- the organosilicone compounds within the general formula (I) can be prepared by a variety of methods. For example, one may use as a starting material a polysilicone compound having hydrogen atoms in the side chain, ie a compound of the general formula (II) and such materials are commercially available. By reaction with a suitable alkoxylated omega unsaturated alcohol, a suitable allyl epoxy ether and the acid salt of a tertiary amine, the compound of general formula (I) is obtained.
- the preparation may include the procedure described in German Patent Application DE 3417912 (Th. Goldschmidt AG).
- compositions for use in the method according to the invention may take a variety of forms. They may for example be a liquid or solid fabric washing product which, in addition to the fabric conditioning agent, may comprise surfactants selected from anionic, nonionic and cationic surfactant materials, mixtures thereof or with other surfactant materials, detergency builder materials such as water-soluble precipitating or sequestering builder materials or ion-exchange builder materials, bleaches such as peroxybleaches, optionally together with bleach activators, alkaline materials such as sodium silicate, fillers such as sodium sulphate and also the other conventional ingredients of such compositions.
- surfactants selected from anionic, nonionic and cationic surfactant materials, mixtures thereof or with other surfactant materials, detergency builder materials such as water-soluble precipitating or sequestering builder materials or ion-exchange builder materials, bleaches such as peroxybleaches, optionally together with bleach activators, alkaline materials such as sodium silicate, fillers such as
- compositions for use according to the invention may be in the form of a rinse conditioning composition, for example a liquid rinse conditioning composition which in addition to the fabric conditioning agent may comprise electrolytes, emulsifiers, viscosity modifying agents, thickeners, colourants and also the other conventional ingredients of such compositions.
- a rinse conditioning composition for example a liquid rinse conditioning composition which in addition to the fabric conditioning agent may comprise electrolytes, emulsifiers, viscosity modifying agents, thickeners, colourants and also the other conventional ingredients of such compositions.
- compositions for use in the method according to the invention may be in the form of a product for use in a hot air rotary dryer, for example in the form of a powder contained within a dispensing device or in the form of a coating on, or impregnation of, a flexible substrate material, which may be in sheet form.
- compositions for use according to the invention may be in a form suitable for direct application to fabric, such as in the form of an aerosol spray containing at least the fabric conditioning agent and a suitable propellant.
- any of the above products may contain, in addition to the siloxane conditioning agent, other fabric conditioning agents such as other fabric softeners (especially water-insoluble cationic and nonionic softeners), anti-static agents (especially water-soluble cationic materials), perfumes, drape imparting agents, crease resistance imparting agents and ironing aids.
- fabric conditioning agents such as other fabric softeners (especially water-insoluble cationic and nonionic softeners), anti-static agents (especially water-soluble cationic materials), perfumes, drape imparting agents, crease resistance imparting agents and ironing aids.
- Suitable water-insoluble cationic and nonionic softeners are disclosed in European Patent Application 122 141 (Unilever) and European Patent Application 59 502 (Procter and Gamble) incorporated herein by reference.
- the total level of the polyalkylsiloxane and nonionic fabric softener lies between 3 to 30% by weight of the composition.
- the total concentration of the polyalkyl siloxane and nonionic fabric softener will be between about 20 ppm and 500 ppm.
- S929 a commercially available material Silicone 929 (ex Dow Corning) containing amine side groups
- PWK a commercially available cationic fabric softener Prepagen WK, which is approximately dihardened tallow dimethyl ammonium chloride
- S2 a polysiloxane of general formula I in which R, R1 and R2 are methyl, R3 is isopropyl, A is the group -(CH2)3OCH2CH(OH)CH2-, X is a randomly distributed group -0(C3H60)11 (C2H40)2H, n is 75, m is 5, p is 2 and Z is actetate;
- S2A identical to S2 except that n is 94, m is 5 and p is 2;
- S2B identical to S2 except that n is 75, m is 5 and p is 4;
- GMS glycerol monostearate; Tween 60
- Examples 1 to 7 are comparative.
- Examples 8 to 10 are according to the invention.
- compositions containing a nonionic fabric softener and a polysiloxane were prepared according to the formulations given below.
- the compositions were prepared by melting the active ingredients at 70°C.
- the molten mixture thus formed was dispersed into hot water at 70°C and cooled to room temperature.
- Examples 11-14 were subjected to the following freeze/thaw test.
- test composition was stored in a screw-capped polyethylene bottle for 16 hours at a temperature of about -10°C. The composition was then allowed to thaw at ambient temperatures for 8 hours.
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- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Textile Engineering (AREA)
- Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
- Silicon Polymers (AREA)
Abstract
A method of conditioning fabrics comprises contacting the fabrics in an aqueous environment with a fabric conditioning agent. The fabric conditioning agent comprises an organofunctional polyalkyl siloxane having the general formula (I)
wherein each R is independently an alkyl group containing 1 to 4 carbon atoms, each of R¹, R², and R³ is independently an alkyl group containing 1 to 24 carbon atoms, or R³ is the group (CH₂)qCOO⁻ where q is 0 to 10, A is divalent hydrocarbon group interrupted by or substituted with one or more oxygen containing groups, X is an alkoxylated group, Z is a monovalent anion or the equivalent thereof, n and m are positive integers, p is a positive integer and r is a positive integer or zero such as to render the siloxane electrically neutral.
Description
- This invention relates to a method of conditioning fabrics and to compositions suitable for use in such methods.
- It is known to condition fabrics, particularly during or immediately following a fabric washing process, to improve the properties of the treated fabrics. Usually this treatment includes the treatment with a fabric softening agent intended to soften and reduce the harshness of washed fabrics. The fabric softening agent may be included in a fabric washing composition, in a composition intended to be added to the rinse subsequent to washing the fabrics or included in a composition intended to be added with wet fabrics to a hot air dryer. In all cases the conditioning process takes place in an aqueous environment.
- A number of fabric conditioning materials are known, including soap, smectite clays, quaternary ammonium salts and fatty amines. All these materials have been commercially used but suffer from a variety of disadvantages. For example quaternary ammonium salts, which have been most widely used, are difficult to incorporate in liquid products except at relatively low concentrations, are not easily dispersed in cold water and may, if used in excess, render the treated fabrics water repellant.
- We have now discovered a class of fabric conditioning agents having particularly advantageous properties, and the invention is therefore characterised in that the fabric conditioning agent is an organofunctional polyalkyl siloxane having the general formula (I)
- We are aware of British Patent No. 1 549 180 (Procter and Gamble) which discloses the combination of a cationic softener and a selected siloxane of general formula (I), except that A is a divalent hydrocarbon group.
- European Patent Application No. 166 122 (Goldschmidt) discloses siloxanes of general formula (I) in which the substituent R³ is the group (CH₂)qCOO⁻ and q is 1. Their preparation and their use in hair conditioning compositions is also disclosed.
- The organosilicone compounds within the general formula (I) can be prepared by a variety of methods. For example, one may use as a starting material a polysilicone compound having hydrogen atoms in the side chain, ie a compound of the general formula (II)
CH₂=CH-CH₂-O(C₃H₆0)₁₁(C₂H₄0)₂H,
an allyl epoxy ether of the formula
(CH₃)₂N CH(CH₃)₂ HOAc
where OAc is acetate, will lead to the material S2 referred to below. - When the substituent R³ is the group (CH₂)q C00⁻, then the preparation may include the procedure described in German Patent Application DE 3417912 (Th. Goldschmidt AG).
- The compositions for use in the method according to the invention may take a variety of forms. They may for example be a liquid or solid fabric washing product which, in addition to the fabric conditioning agent, may comprise surfactants selected from anionic, nonionic and cationic surfactant materials, mixtures thereof or with other surfactant materials, detergency builder materials such as water-soluble precipitating or sequestering builder materials or ion-exchange builder materials, bleaches such as peroxybleaches, optionally together with bleach activators, alkaline materials such as sodium silicate, fillers such as sodium sulphate and also the other conventional ingredients of such compositions.
- Alternatively the compositions for use according to the invention may be in the form of a rinse conditioning composition, for example a liquid rinse conditioning composition which in addition to the fabric conditioning agent may comprise electrolytes, emulsifiers, viscosity modifying agents, thickeners, colourants and also the other conventional ingredients of such compositions.
- Still further, the compositions for use in the method according to the invention may be in the form of a product for use in a hot air rotary dryer, for example in the form of a powder contained within a dispensing device or in the form of a coating on, or impregnation of, a flexible substrate material, which may be in sheet form.
- Also the compositions for use according to the invention may be in a form suitable for direct application to fabric, such as in the form of an aerosol spray containing at least the fabric conditioning agent and a suitable propellant.
- Any of the above products may contain, in addition to the siloxane conditioning agent, other fabric conditioning agents such as other fabric softeners (especially water-insoluble cationic and nonionic softeners), anti-static agents (especially water-soluble cationic materials), perfumes, drape imparting agents, crease resistance imparting agents and ironing aids.
- Suitable water-insoluble cationic and nonionic softeners are disclosed in European Patent Application 122 141 (Unilever) and European Patent Application 59 502 (Procter and Gamble) incorporated herein by reference.
- When the compositions are in the form of rinse conditioning compositions, the total level of the polyalkylsiloxane and nonionic fabric softener, if present, lies between 3 to 30% by weight of the composition. In use such compositions are added to water to form a liquor with which the fabrics to be treated are contacted. Generally, the total concentration of the polyalkyl siloxane and nonionic fabric softener will be between about 20 ppm and 500 ppm.
- The invention will now be further described in the following non-limiting examples.
- In these examples the following materials are referred to:
S929 : a commercially available material Silicone 929 (ex Dow Corning) containing amine side groups;
PWK : a commercially available cationic fabric softener Prepagen WK, which is approximately dihardened tallow dimethyl ammonium chloride;
S2 : a polysiloxane of general formula I in which R, R¹ and R² are methyl, R³ is isopropyl, A is the group -(CH₂)₃OCH₂CH(OH)CH₂-, X is a randomly distributed group -0(C₃H₆0)₁₁ (C₂H₄0)₂H, n is 75, m is 5, p is 2 and Z is actetate;
S2A : identical to S2 except that n is 94, m is 5 and p is 2;
S2B : identical to S2 except that n is 75, m is 5 and p is 4;
GMS : glycerol monostearate;
Tween 60 : polyoxyethylene sorbitan monostearate containing 20 ethylene oxide groups per molecule;
Tween 65 : polyoxylethylene sorbitan tristearate containing 20 ethylene oxide groups per molecule;
Span 80 : sorbitan monooleate.
- In the following experiments, the softening performance of these materials was tested and compared with a water-only treatment.
- In a laboratory scale apparatus, one 50g piece of 67/33 polyester cotton measuring about 15cm × 15cm was rinsed in 1 litre of a rinse liquor containing 0.1%, 0.2% or 0.4% of the tested material based on the weight of the fabric. After treatment the tested cloths were line dried and the terry towelling pieces were assessed for softness against standards. A softness ranking was given to each test cloth. The results obtained were as follows, lower softness numbers indicating better softness.
- Examples 1 to 7 are comparative. Examples 8 to 10 are according to the invention.
- The rewetability of the treated polyester cotton test cloths was then assessed using a modified Draves test (C.Z. Draves, Am. Dyestuff Reporter 28, 421-1939) in which the time in seconds is measured for a small piece of treated fabric placed on the surface of water to sink. The results were as follows:
- These results demonstrate that the softening materials according to the invention provide fabric softening effects which are comparable with known softening materials, but also provide improved rewetability effects, especially in comparison with other silicone materials.
- In these examples, compositions containing a nonionic fabric softener and a polysiloxane were prepared according to the formulations given below. The compositions were prepared by melting the active ingredients at 70°C. The molten mixture thus formed was dispersed into hot water at 70°C and cooled to room temperature.
-
- Examples 11-14 were subjected to the following freeze/thaw test.
- The test composition was stored in a screw-capped polyethylene bottle for 16 hours at a temperature of about -10°C. The composition was then allowed to thaw at ambient temperatures for 8 hours.
-
- These results show that the combination of the conditioning materials according to the invention with a nonionic fabric softener provide improved rewetability effects and are more freeze/thaw stable than compositions containing conventional cationic rinse conditioners.
Claims (4)
1. A method of conditioning fabrics which comprises the step of contacting fabrics in an aqueous environment with a fabric conditioning agent, characterised in that the fabric conditioning agent is an organofunctinal polyalkyl siloxane having the general formula (I)
wherein each R is independently an alkyl group containing 1 to 4 carbon atoms, each of R¹ , R², and R³ is independently an alkyl group containing 1 to 24 carbon atoms, or R³ is the group (CH₂)qCOO⁻ where q is 0 to 10, A is divalent hydrocarbon group interrupted by or substituted with one or more oxygen containing groups, X is an alkoxylated group, Z is a monovalent anion or the equivalent thereof, n and m are positive integers, p is a positive integer and r is a positive integer or zero such as to render the siloxane electrically neutral.
2. A method of conditioning fabrics according to Claim 1 characterised in that the fabric conditioning agent further comprises a nonionic fabric softener.
3. A method of conditioning fabrics according to Claims 1 or 2 characterised in that the organofunctional polyalkyl siloxane is selected from the group consisting of organofunctional polyalkyl siloxanes of formula (I) in which
(i) m is 5, n is 75, p is 2;
(ii) m is 5, n is 94, p is 2; and
(iii)m is 5, n is 75, p is 4.
4. A method of conditioning fabrics according to any of Claims 1 to 3 characterised in that the organofunctional polysiloxane is such that R, R¹ and R² are each methyl, R³ is isopropyl, Z is acetate, A is -(CH₂)OCH₂CH(OH)CH₂ - and X is -O(C₃H₆O)₁₁ (C₂C₄O)₂H.
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GB878704002A GB8704002D0 (en) | 1987-02-20 | 1987-02-20 | Conditioning fabrics & compositions |
GB8704002 | 1987-02-20 |
Publications (2)
Publication Number | Publication Date |
---|---|
EP0288137A2 true EP0288137A2 (en) | 1988-10-26 |
EP0288137A3 EP0288137A3 (en) | 1990-01-10 |
Family
ID=10612645
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
EP88301346A Withdrawn EP0288137A3 (en) | 1987-02-20 | 1988-02-18 | Method of conditioning fabrics |
Country Status (4)
Country | Link |
---|---|
EP (1) | EP0288137A3 (en) |
JP (1) | JPS63243377A (en) |
GB (2) | GB8704002D0 (en) |
ZA (1) | ZA881180B (en) |
Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5723426A (en) * | 1996-02-29 | 1998-03-03 | Zhen; Yueqian | Liquid laundry detergent compositions containing surfactants and silicone emulsions |
WO2009065664A1 (en) * | 2007-11-21 | 2009-05-28 | Unilever Plc | Novel compounds for fabric treatment |
WO2011002864A1 (en) | 2009-06-30 | 2011-01-06 | The Procter & Gamble Company | Aminosilicone containing detergent compositions and methods of using same |
Families Citing this family (9)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
FR2648821A1 (en) * | 1989-06-22 | 1990-12-28 | Rhone Poulenc Chimie | |
US5164522A (en) * | 1990-06-29 | 1992-11-17 | Karlshamns Ab | Cationic silicones |
DE4222483A1 (en) * | 1992-07-09 | 1994-01-13 | Pfersee Chem Fab | Organosiloxanes with residues containing nitrogen and with ether groups |
DE59905052D1 (en) * | 1998-11-14 | 2003-05-22 | Goldschmidt Ag Th | Polyetherquat functional polysiloxanes |
DE10050933A1 (en) * | 2000-10-13 | 2002-04-25 | Ciba Sc Pfersee Gmbh | Flowable non-crosslinked polyorganosiloxane for treatment of fabrics contains at least one quaternary group comprising at least one nitrogen atom, and at least one further polar radical |
US6313256B1 (en) * | 2000-12-06 | 2001-11-06 | Siltech Llc | Dimethicone copolyol amido quats |
DE10115476A1 (en) | 2001-03-29 | 2002-10-10 | Wacker Chemie Gmbh | Process for the treatment of organic fibers |
DE10221521A1 (en) * | 2002-05-14 | 2003-12-04 | Ge Bayer Silicones Gmbh & Co | Formulations of silicone softeners for textile finishing |
CA3007929A1 (en) | 2015-12-28 | 2017-07-06 | Colgate-Palmolive Company | Fabric conditioners |
Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0076625A1 (en) * | 1981-10-03 | 1983-04-13 | Dow Corning Limited | Treating textile fibres |
EP0166122A1 (en) * | 1984-05-15 | 1986-01-02 | Th. Goldschmidt AG | Betain groups containing siloxanes, their preparation and their use in cosmetic preparations |
Family Cites Families (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
GB1549180A (en) * | 1975-07-16 | 1979-08-01 | Procter & Gamble | Textile treating compositions |
GB2110258B (en) * | 1981-10-03 | 1985-06-12 | Dow Corning | Treating textile fibres |
-
1987
- 1987-02-20 GB GB878704002A patent/GB8704002D0/en active Pending
-
1988
- 1988-02-18 GB GB08803761A patent/GB2201433A/en active Pending
- 1988-02-18 EP EP88301346A patent/EP0288137A3/en not_active Withdrawn
- 1988-02-18 JP JP63036446A patent/JPS63243377A/en active Pending
- 1988-02-19 ZA ZA881180A patent/ZA881180B/en unknown
Patent Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0076625A1 (en) * | 1981-10-03 | 1983-04-13 | Dow Corning Limited | Treating textile fibres |
EP0166122A1 (en) * | 1984-05-15 | 1986-01-02 | Th. Goldschmidt AG | Betain groups containing siloxanes, their preparation and their use in cosmetic preparations |
Cited By (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5723426A (en) * | 1996-02-29 | 1998-03-03 | Zhen; Yueqian | Liquid laundry detergent compositions containing surfactants and silicone emulsions |
WO2009065664A1 (en) * | 2007-11-21 | 2009-05-28 | Unilever Plc | Novel compounds for fabric treatment |
WO2011002864A1 (en) | 2009-06-30 | 2011-01-06 | The Procter & Gamble Company | Aminosilicone containing detergent compositions and methods of using same |
US8207105B2 (en) | 2009-06-30 | 2012-06-26 | The Procter And Gamble Company | Aminosilicone containing detergent compositions and methods of using same |
Also Published As
Publication number | Publication date |
---|---|
ZA881180B (en) | 1989-10-25 |
GB8704002D0 (en) | 1987-03-25 |
GB8803761D0 (en) | 1988-03-16 |
JPS63243377A (en) | 1988-10-11 |
EP0288137A3 (en) | 1990-01-10 |
GB2201433A (en) | 1988-09-01 |
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