NZ234114A - A crosslinkable composition for antifelting wool and a process using it - Google Patents
A crosslinkable composition for antifelting wool and a process using itInfo
- Publication number
- NZ234114A NZ234114A NZ234114A NZ23411490A NZ234114A NZ 234114 A NZ234114 A NZ 234114A NZ 234114 A NZ234114 A NZ 234114A NZ 23411490 A NZ23411490 A NZ 23411490A NZ 234114 A NZ234114 A NZ 234114A
- Authority
- NZ
- New Zealand
- Prior art keywords
- microparticles
- wool
- weight
- units
- methacrylate
- Prior art date
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
- D06M15/21—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
- D06M15/356—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds of other unsaturated compounds containing nitrogen, sulfur, silicon or phosphorus atoms
-
- 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
- D06M23/00—Treatment of fibres, threads, yarns, fabrics or fibrous goods made from such materials, characterised by the process
- D06M23/12—Processes in which the treating agent is incorporated in microcapsules
Landscapes
- Engineering & Computer Science (AREA)
- Textile Engineering (AREA)
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
- Chemical Or Physical Treatment Of Fibers (AREA)
- Chemical And Physical Treatments For Wood And The Like (AREA)
- Building Environments (AREA)
- Treatment Of Sludge (AREA)
- Cleaning Implements For Floors, Carpets, Furniture, Walls, And The Like (AREA)
- Solid-Sorbent Or Filter-Aiding Compositions (AREA)
- Paints Or Removers (AREA)
Abstract
Crosslinkable composition for the antifelting treatment of wool, comprising, on the one hand, between 5 and 20 % by weight of microparticles and, on the other hand, between 80 and 95 % of water to which stabilisers have been added. The surface of the microparticles consists of a copolymer containing a high proportion by weight of N-alkylazetidinyl acrylate units and/or N-alkylazetidinyl methacrylate units, whereas the interior of the microparticles consists of a copolymer containing a low proportion by weight of N-alkylazetidinyl acrylate units and/or N-alkylazetidinyl methacrylate units.
Description
New Zealand Paient Spedficaiion for Paient Number £34114
2 3 4 114
PrforHy 'oUc^s): - AS?, h:. *3 °l.
>,' •' ^ S-? .Vivo
Class: {5}.S.&%.lr^yb>,[^. OobVv\\^) fLb"!,.
X}Q^)Crr^lb.Vp?? - ... .
JLoObmiQUZ ■. 1
'* ; I '• 1" k ii *- * ^ ,Vi3
wi * A*"
NEW ZEALAND PATENTS ACT, 1953
NT: - •}
pat-.y. -r,-. -;
18 JUN1990
RECEIVED
w.
No:
Date:
COMPLETE SPECIFICATION
J
COMPOSITION FOR THE ANTIFELTING OF WOOL AND FINISHING PROCESS USING IT
^'( f^/y/We CECA SA, a French body corporate, of 22 Place des Vosges, Courbevoie/* t. ,n fef France,
hereby declare the invention for which ^we pray that a patent may be granted to jXi/us, and the method by which it is to be performed, to be particularly described in and by the following statement
The invention relates to a composition for the non-felting treatment of wool.
Wool articles can undergo an irreversible shrinkage caused by felting in the course of successive wet processes 5 such as washing or dyeing, in use or during maintenance operations. This shrinkage is due to the very nature of the fibres of which wool consists. These keratin-based fibres are, in fact, made up of a multitude of scales which are caused to overlap by repeated mechanical operations. A 10 frictional force then appears between the scales of the fibres, its result being to decrease the dimensions of the finished articles.
All industrial processes for the antifelting treatment of wool are based on means which enable the 15 frictional forces to be reduced. Some of these treatments are based on the degradation of the scales of the fibres of which wool consists, generally by the action of oxidizing agents. The oxidizing agents most frequently employed are chlorine, in the form of gas or of hypochlorous acid, and 20 the sodium salt of dichlorocyanuric acid (DCCA). These oxidizing treatments have the major disadvantage of modifying the fibre and hence its appearance, and of lowering the qualities of the wool.
Other antifelting treatments for wool consist in 25 applying a polymer to the fibres. In fact, when a film of resin is deposited on the wool fibres, the scaly structure of the latter is masked. Thus, very many polymers have been
used in the antifelting treatment of wool with the aim of improving the shrinkage resistance of the latter. Some methods have consisted in forming the polymer directly on the surface of the fibre. These methods have the 5 disadvantage of resulting in a large number of bonds between the various fibres. In addition, the quantity of polymer employed is large and increases the cost of the operation.
More recent techniques have consisted in applying preformed polymers onto the wool. Among others, polymers 10 containing reactive groups have been employed with the aim of keeping the polymer on the fibre. Thus, German Patent DE 2,342,083, describes the use of a dispersion of acrylic polymers and of methylolureas in antifelting compositions. GB Patent 2,017,179, describes the use of a polyamide-15 epichlorohydrin condensation product.
These polymers must have a certain number of particular qualities; they must exhibit a resistance to washing and drying and a durability when the fibre onto which they are applied is being used (resistance to rubbing, 20 to sweat and to light).
The reactive polymers employed must also have a large number of properties. In the first place, they must not modify the intrinsic quality of the wool when they are applied. The main disadvantage of many commercial products 25 is that they roughen the wool onto which they are applied: the fibre becomes hard and difficult to wear. This phenomenon is due to the high glass transition temperature
234114
4
of the polymer. In order to obtain a compromise between the antifelting qualities and the softness of wool, the polymer should have a relatively low glass transition temperature.
The polymer must also be capable of covering the 5 fibre completely. The surface of the fibre must consequently be completely wetted by the composition containing the polymer. Although the wettability of wool can be increased by various methods, the composition containing the polymer will need to have a sufficiently low 10 surface tension to attain this objective.
Furthermore, the composition employed will need to r+'
be adaptable in use, making it possible to perform a continuous or noncontinuous treatment on combed wool tops, fabrics or knits.
Lastly, the composition must be capable of being employed at an active product concentration which allows the cost of the operation to be limited.
The antifelting compositions for wool of the state of the art do not offer these various properties 20 simultaneously.
A crosslinkable composition for the antifelting treatment of wool is provided according to the invention which offers many technical advantages and enables the treatment of the wool to be carried out continuously and
noncontinuously so as to make it unshrinkable. This composition can be employed so as to provide a low
7 MAY 1992
/
234114
of the dry product relative to the weight of wool which is treated, compared with 1 to 2 % in the case of the products generally employed) and thus offers economy which is highly advantageous for industrial application.
The composition according to the invention preserves the intrinsic qualities of the wool. While acquiring nonfeltability qualities, the wool retains its natural appearance.
Another advantage consists in the fact that the 10 composition can be applied onto the wool using mild methods, lowering the energy costs.
The composition according to the invention can be applied to many types of wool included: raw, woven,
knitted, finished or unfinished products.
Furthermore, the composition according to the invention offers a great adaptability of application,
enabling it to be employed at any stage of a finishing process after the conventional chlorination stage. When the antifelting treatment with the composition according to the 20 invention is performed, the use of a softener is no longer essential.
The invention provides a composition for the antifelting treatment of wool comprising, on the one hand,
from 5 to 20 % by weight of microparticles consisting of a 25 copolymer of acrylic and/or methacrylic monomeric units and, on the other hand, from 8 0 to 95 % by weight of water to which stabilizers have been added, in which the v 4 £^
°A
' 7MAYl992Zj
J') i i microparticles have a surface consisting of a copolymer containing a high proportion by weight of N-alkylazetidinyl aerylate units and/or of N-alkylazetidinyl methacrylate units, the interior of the said microparticles consisting of a copolymer containing a low proportion by weight of N-alkylazetidinyl acrylate units and/or of N-alkylazetidinyl methacrylate units.
The term 'N-alkylazetidinyl' as used throughout this specification includes groupings containing both linear and cyclic alky! groups.
The surface of the microparticles preferably consists of a copolymer containing a high proportion by weight of N-cyclohexylazetidinyl methacrylate units, the interior of the microparticles consisting of a copolymer containing a low proportion by weight of N-cyclohexylazetidinyl methacrylate units.
Also preferably, the microparticles consist of N-cyclohexylazetidine methacrylate units and of acrylic or methacrylic monomeric units chosen from one or more of the group consist' of methyl methacrylate, 2-ethylhexyl acrylate, butyl acrylate, butyl methacrylate, ethyl acrylate and acrylonitrile.
An advantageous alternative form of the invention consists in employing a composition in which the microparticles consist of a terpolymer of
N-cyclohexylazetidinyl methacrylate, methyl methacrylate and 2-ethylhexyl acrylate.
The microparticles, which are typically from 1 to a few microns in size, for the antifelting treatment of wool according to the invention can take various forms-*——
N.Z. F
12 K" ■ -
M
T /, 1 1 4
7
According to one embodiment, the composition of the microparticles have a gradient structure: the concentration of N-cyclohexylazetidinyl methacrylate units in the copolymer constituting the microparticles decreases from the 5 surface towards the centre of the microparticles. ^ According to a particularly advantageous embodiment, the microparticles exhibit a "core-and-shell" structure, a structure making it possible to distinguish at least two copolymer layers which have a different 10 composition: a first layer situated at the surface, called the "shell", consisting of a copolymer containing a high proportion by weight of N-alkylazetidinyl methacrylate units and/or N-alkylazetidinyl acrylate units and at least one second layer called the "core" consisting of a copolymer 15 containing a low proportion by weight of N-alkylazetidinyl methacrylate units and/or of N-alkylazetidinyl acrylate units. Thus, according to this "core-and-shell" structure, it is particularly advantageous to use a composition according to the invention which has microparticles 20 consisting of a "shell" containing 50 to 95 % by weight, w preferably 85 to 95 % by weight, of N-alkylazetidinyl methacrylate units and/or N-alkylazetidinyl acrylate units and of a "core" containing 5 to 50 %, preferably 10 to 20 % of N-alkylazetidinyl and/or N-alkylazetidinyl acrylate 25 units, the overall weight percentage of N-alkylazetidinyl units in the microparticles being from 10 to 50 %,
preferably from 20 to 3 0 %.
2 3 4 114
8
The stabilisers used in the present invention are generally non-ionic surface-active agents, preferably polyoxyethylene derivatives. An especially preferred stabiliser is that known under the trade mark Tween 60, a 5 stearyl ester of a polyoxyethylenated sorbitan.
The composition according to the invention can be produced according to a known synthesis route, such as emulsion polymerization or any other method permitting the formation of microparticles.
The present invention also provides a wool finishing process comprising an antifelting treatment with the aid of the above compositions, which can be combined very flexibly with conventional dyeing and chlorination stages. The antifelting treatment can be carried out 15 before, after or partly before and partly after the dyeing stage, provided that the conventional prechlorination stage has already been carried out. Thus, it will be possible to employ the following procedures:
1. prechlorination, dyeing, antifelting treatment;
2. prechlorination, partial antifelting treatment,
dyeing, partial antifelting treatment;
3. prechlorination, antifelting treatment, dyeing;
4. dyeing, prechlorination, antifelting treatment,
with the composition according to the invention, once 25 applied to the wool, having to be heated to a temperature of at least say, 50° C to permit the azetidine rings to open and to crosslink.
234 114
9
The composition according to the invention can be applied using any continuous or noncontinuous process.
The following Example of the embodiment which follows. The example describes the production of an 5 antifelting composition containing microparticles exhibiting a "core-and-shell" structure with a number of layers and consisting of N-cyclohexylazetidinyl methacrylate, methylmethacrylate, 2-ethylhexyl acrylate terpolymer and shows a use of this composition in antifelting. The 10 composition offers the great advantage of not being reactive at room temperature and of having a long pot life. 1./ Preparation of mixtures of monomeric units
Mixtures 1, 2 and 3 according to the following table are prepared:
--
Mixtures
N-Cyclohexyl-
azetidine methacrylate
Methyl methacrylate
2-Ethylhexyl methacrylate
I
19
73
8
II
13
12
75
III
89
2
9
2./ Synthesis bv emulsion polymerization 25 This synthesis makes it possible to obtain a latex of structured microparticles which have a shell corresponding
i
to the polymerization of mixture III and a core consisting of two layers: a first central layer obtained by polymerization of mixture I, and a second layer obtained by polymerization of mixture II.
5 litres of demineralized water, followed by 19 grams of sodium tetraborate are introduced into a 6-litre jacketed reactor fitted with a stirrer, a condenser and a nitrogen injection system. The temperature is maintained at 50° C and nitrogen is bubbled in for one hour. 50 grams of Tween 10 60 are then introduced into the reactor.
Formation of the "core". 560 grams of monomer mixture I are introduced. A stable emulsion is obtained while stirring at 250 revolutions per minute. An initiator solution of 507 grams of ammonium persulphate dissolved in 15 5 ml of water is introduced into the reactor. The polymerization lasts two hours.
Formation of the intermediate layer. 350 grams of monomer mixture II are then added with the aid of a metering pump over one hour. At the end of the addition a solution 20 of 5 grams of ammonium persulphate in 5 ml initiates the polymerization. The latter lasts two hours.
Formation of the outer "shell" layer. The shell is polymerized in the same way with the aid of the monomer mixture III. Throughout the polymerization stirring is 25 maintained at 25 revolutions per minute and a nitrogen stream sweeps the top of the reactor. At the end of the polymerization of the "shell" the latex is cooled slowly to
234 114
n room temperature.
3./ Use of the crosslinkable composition during a nonfeltino treatment
A first part of the composition is used during a 5 continuous process for the antifelting treatment of wool, and a second part during a noncontinuous process. A - Continuous process
The antifelting treatment employed is a conventional continuous industrial process. The wool is delivered in the 10 form of a top to a glazing machine made up of a series of vats containing the various solutions needed for the treatment. The wool top is successively immersed in each of these vats by means of a system of rollers.
The first stage is a conventional chlorination stage. 15 This stage enables the surface tension of the wool to be increased to improve the adhesion and the distribution of the polymer on the fibres by the incorporation of RS03H and RCOOH groups. This prechlorination is performed by soaking the wool in a bath of NaOCl, sulphuric acid and wetting 20 agent at a pH of 1.5 to 2.0 and at a temperature of 15 to 20°C.
The wool is then rinsed at a temperature of 20 to 30°C to remove the reaction products from the prechlorination stage. The following stage consists in dechlorinating the 25 wool. This dechlorination is performed at a pH of 8.5 to 9.5 and at a temperature of 20 to 35°C, using a sodium bisulphite solution. This operation improves the antifelting
12
effect and clears the wool. The wool is then rinsed at 2 0-35°C and is then treated with the antifelting composition obtained in section 2, in a proportion of 0.5 to l % by weight of active substance relative to the weight of the 5 treated wool. The temperature is maintained between 20 and 30°C and the pH is adjusted to a value of between 4 and 5 by adding acid, for example acetic acid, to the composition. The wool is then dried at 60-80°C for approximately 10 minutes. It is during this last stage that the crosslinking 10 of the azetidine groups onto the fibres takes place.
B - The noncontinuous process
The noncontinuous process employed is an immersion process using bath exhaustion.
The first stage consists of a conventional chlorination 15 stage performed by soaking the wool for 30 to 35 minutes, cold, in an aqueous solution containing 1 g/1 of wetting agent and 2 to 3 % by weight of Basolan DC» marketed by BASF, relative to the weight of treated wool <pH = 3.5-4).
The wool is then rinsed with cold water for 10 minutes 20 and is then dechlorinated in the same bath with 2 % by weight of bisulphite for 10 to 15 minutes, cold (pH = 3.5-4).
The wool is again rinsed cold for 10 minutes and is then treated at room temperature with a solution containing 0.5 25 to 1 % by weight of the composition obtained in section 2, the pH of the solution being fixed between 4 and 5 by adding
Claims (1)
- 23 4 1 1 h • ■ 13 acetic acid, and is finally dried as previously at 60-80°C for approximately 10 minutes. f*) 4 . / Results;To assess the effectiveness of the composition, the AFS 5 (Aera Felting Shrinkage) shrinkage ratio was measured after several washings of the treated wool. The results obtained ^ . .;were compared with the results obtained with wool batches treated according to an identical process using a product of the state of the art, Hercosett 125 (Hercules). The results 10 are given in the following table.;Polymer;% by weight;AFS;Hercosett 125;2 %;6.5;Composition according to the invention;0.5 %;5.6;Untreated;—;54.3;It is found that in the presence of a minimal quantity of active substance (0.5 % by weight relative to the weight of treated wool), the results obtained are comparable with those obtained with a higher percentage of product of the 25 state of the art. The antifelting power of the composition according to the invention is four times greater than that of the state of the art.;14;WHAT WE CLAIM IS:;1. A crosslinkable composition suitable for the treatment of wool which comprises 5 to 20% by weight of microparticles of an aciylic and/or methacrylic copolymer and from 80 to 95% by weight of water containing one or more stabilizers, the surface of said microparticles comprising a copolymer containing a high proportion by weight of N-alkylazetidinyl or N-cycloalkylazetidinyl acrylate units and/or of N-alkylazetidinyl or N-cycloalkylazetidinyl methacrylate units, the interior of the said microparticles containing a copolymer containing a low proportion by weight of N-alkylazetidinyl or N-cycloalkylazetidinyl acrylate units and/or of N-alkylazetidinyl or N-cycloalkylazetidinyl methacrylate units.;2. A composition according to claim 1, in which the surface of the microparticles consists of a copolymer containing a high proportion of N-cyclohexylazetidinyl methacrylate units, the remainder of said microparticles consisting of a copolymer containing a low proportion of N-cyclohexylazetidinyl methacrylate units.;3. A composition according to claim 1 or 2, in which the microparticles consist of N-cyclohexylazetidinyl methacrylate units and units chosen from one or more of the group consisting of methyl methacrylate, 2-ethylhexyl aciylate, butyl aciylate, butyl methacrylate, ethyl acrylate and acrylonitrile.;4. A composition according to claim 3, in which the microparticles consist of a terpolymer of N-cyclohexylazetidinyl methacrylate, methyl methacrylate and 2-ethylhexyl acrylate.;15;[ l-i;5. A composition according to any one of the preceding claims in which the microparticles have a core-and-shell structure consisting of distinct polymeric layers.;6. A composition according to claim 5, in which the microparticles consist of a "shell" containing 50 to 95% by weight of N-cyclohexylazetidinyl methacrylate and/or N-cyclohexylazetidinyl acrylate units, the overall weight percentage of N-cyclohexylazetidinyl units in the microparticles being from 10 to 50%.;7. A composition according to claim 1 in which the microparticles consist of a "shell" comprising 85 to 95% by weight of N-alkylazetidinyl or N-cycloalkylazetidinyl methacrylate units and of a core consisting of a copolymer comprising from 10 to 20% by weight of N-alkylazetidinyl or N-cycloalkylazetidinyl methacrylate units, the overall weight percentage of N-alkylazetidinyl or N-cycloalkylazetidinyl units in the microparticles being from 20 to 30%.;8. A composition according to any one of claims 1 to 4 in which the composition of the microparticles changes gradually from core to shell.;9. A composition according to claim 1 substantially as described in the Example.;10. A process for finishing wool which comprises prechlorination, dyeing and antifelting treatment stages in;?34114;16;any order provided that prechlorination occurs prior to antifelting, the antifelting treatment comprising the immersion of the wool in a composition as claimed in any one of claims 1 to 9 so as to provide a concentration of 5 dry active product of 0.5 to 1 % by weight relative to the wool treated and drying it at a temperature of 60 to 80°C.;11. A process according to claim 10 substantially as described in the Example.;12. Wool whenever finished by a process as claimed;10 in claim 10 or 11.;SfeTEOTMB <o*K DAY Of 0^^"" A. I. PARK & SON /) n -i ^ AftfKK m THi AIVUCAMI
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR8907971A FR2648486B1 (en) | 1989-06-16 | 1989-06-16 | COMPOSITION FOR ANTI-EUTRANT TREATMENT OF WOOL |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NZ234114A true NZ234114A (en) | 1992-12-23 |
Family
ID=9382775
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NZ234114A NZ234114A (en) | 1989-06-16 | 1990-06-18 | A crosslinkable composition for antifelting wool and a process using it |
Country Status (8)
| Country | Link |
|---|---|
| EP (1) | EP0403336B1 (en) |
| AT (1) | ATE100507T1 (en) |
| AU (1) | AU626122B2 (en) |
| DE (1) | DE69006109T2 (en) |
| DK (1) | DK0403336T3 (en) |
| ES (1) | ES2062441T3 (en) |
| FR (1) | FR2648486B1 (en) |
| NZ (1) | NZ234114A (en) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ATE234092T1 (en) | 1995-09-08 | 2003-03-15 | Novo Nordisk As | 2-ALKYLPYRROLIDINE |
| GB0201165D0 (en) | 2002-01-18 | 2002-03-06 | Unilever Plc | Azetidinium modidfied poymers and fabric treatment composition |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE234083C (en) * | ||||
| DE2342083A1 (en) * | 1973-08-21 | 1975-04-24 | Basf Ag | Anti-shrinkage and felting treatment of keratin fibres - by impregnation with soln. contg. sulphite, poly-N-methylol cpd. and reactive polymer |
| FR2395141A1 (en) * | 1977-06-21 | 1979-01-19 | Centre Tech Ind Papier | Slip resistant sheet comprising support - coated with paper coating compsn. contg. hollow microspheres of polyvinylidene chloride and opt. polyacrylonitrile |
-
1989
- 1989-06-16 FR FR8907971A patent/FR2648486B1/en not_active Expired - Fee Related
-
1990
- 1990-06-08 ES ES90401561T patent/ES2062441T3/en not_active Expired - Lifetime
- 1990-06-08 DE DE69006109T patent/DE69006109T2/en not_active Expired - Fee Related
- 1990-06-08 EP EP90401561A patent/EP0403336B1/en not_active Expired - Lifetime
- 1990-06-08 AT AT90401561T patent/ATE100507T1/en not_active IP Right Cessation
- 1990-06-08 DK DK90401561.7T patent/DK0403336T3/en active
- 1990-06-15 AU AU57191/90A patent/AU626122B2/en not_active Ceased
- 1990-06-18 NZ NZ234114A patent/NZ234114A/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| DE69006109T2 (en) | 1994-07-14 |
| FR2648486A1 (en) | 1990-12-21 |
| AU5719190A (en) | 1990-12-20 |
| EP0403336A1 (en) | 1990-12-19 |
| AU626122B2 (en) | 1992-07-23 |
| DK0403336T3 (en) | 1994-02-28 |
| DE69006109D1 (en) | 1994-03-03 |
| EP0403336B1 (en) | 1994-01-19 |
| FR2648486B1 (en) | 1991-08-30 |
| ATE100507T1 (en) | 1994-02-15 |
| ES2062441T3 (en) | 1994-12-16 |
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