CA2146713A1 - Bleaching of textiles - Google Patents
Bleaching of textilesInfo
- Publication number
- CA2146713A1 CA2146713A1 CA002146713A CA2146713A CA2146713A1 CA 2146713 A1 CA2146713 A1 CA 2146713A1 CA 002146713 A CA002146713 A CA 002146713A CA 2146713 A CA2146713 A CA 2146713A CA 2146713 A1 CA2146713 A1 CA 2146713A1
- Authority
- CA
- Canada
- Prior art keywords
- bleaching
- raw material
- liquor
- textile raw
- hydrogen peroxide
- 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.)
- Abandoned
Links
Classifications
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06L—DRY-CLEANING, WASHING OR BLEACHING FIBRES, FILAMENTS, THREADS, YARNS, FABRICS, FEATHERS OR MADE-UP FIBROUS GOODS; BLEACHING LEATHER OR FURS
- D06L4/00—Bleaching fibres, filaments, threads, yarns, fabrics, feathers or made-up fibrous goods; Bleaching leather or furs
- D06L4/10—Bleaching fibres, filaments, threads, yarns, fabrics, feathers or made-up fibrous goods; Bleaching leather or furs using agents which develop oxygen
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06L—DRY-CLEANING, WASHING OR BLEACHING FIBRES, FILAMENTS, THREADS, YARNS, FABRICS, FEATHERS OR MADE-UP FIBROUS GOODS; BLEACHING LEATHER OR FURS
- D06L4/00—Bleaching fibres, filaments, threads, yarns, fabrics, feathers or made-up fibrous goods; Bleaching leather or furs
- D06L4/10—Bleaching fibres, filaments, threads, yarns, fabrics, feathers or made-up fibrous goods; Bleaching leather or furs using agents which develop oxygen
- D06L4/12—Bleaching fibres, filaments, threads, yarns, fabrics, feathers or made-up fibrous goods; Bleaching leather or furs using agents which develop oxygen combined with specific additives
Landscapes
- Engineering & Computer Science (AREA)
- Textile Engineering (AREA)
- Detergent Compositions (AREA)
- Coloring (AREA)
- Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
- Chemical Or Physical Treatment Of Fibers (AREA)
Abstract
The present invention provides a process for bleaching textile raw material with the aid of hydrogen peroxide by treating the textile raw material with an aqueous bleach-ing liquor including hydrogen peroxide and a bleach activator, which comprises using as the bleach activator an N-acyllactam of the formula I
(I)
(I)
Description
2l~6~ l3 ` -HOECHST A~-L1 N~SELLSCHAFT HOE 94/F 092 Dr.Rl/rh Description Bleaching of textiles Textile raw material is bleached to prepare it for dyeing or finishing. Hitherto it was customary to use bleaching agents such as hydrogen peroxide, sodium hypochlorite or sodium chlorite.
It has been found that the use of hypochlorites in bleaching processes gives rise to org~noh~logen compounds which can be harmful. This leads to an ever increasing renunciation of this bleaching agent.
The sodium chlorite bleach, which is carried out in the acid pH range, gives rise to the formation of chlorine dioxide, which is harmful and represents an odor nuis-ance. In addition, this bleaching agent can be used onlyon selected textile machines, made of special materials.
Owing to these disadvantages, bleaching with hydrogen peroxide is increasingly preferred.
The review "Activators and stabilizers for the peroxide bleach" by Dr. W. Ney in Textilpraxis international 1974, October and November, pages 1392 - 1565, reveals that hydrogen peroxide is today the most common bleaching agent for all natural fibers of vegetable and ~n;~-l origin.
To achieve a bleaching effect with hydrogen peroxide, it first has to be activated. Also, the bleaching solution needs to be stabilized in order that the 1088 of active oxygen may be m;n;mi zed.
It i~ generally customary and best known to activate with bases. In the bleaching of cellulose fibers, the base used for cotton is almost exclusively sodium peroxide 21~6713 while sodium carbonate is preferred for bast fibers, especially linen. The disadvantage with the use of bases is the alkali sensitivity of animal fibers.
In addition to bases, hydrogen peroxide can be activated in other ways, for example by chemical conversion of the hydrogen peroxide into organic and inorganic per-acids.
G. Rosch, Deutsche Textiltechnik 10 (1960), No. 4, pages 191-195, discloses the use of peracetic acid in textile bleaching. Peracetic acid is inflammable. The concen-trated solution, which has a pungent odor, is corrosiveand burns the skin. The biggest disadvantage of peracetic acid is its high explosivity. The use of acetic anhydride in its preparation may, under adverse conditions, give rise to the formation, as a by-product, of diacetyl peroxide which likewise tends to decompose spontaneously.
This behavior is probably the reason why peracetic acid has never found the expected success as bleaching agent.
In addition to the aforementioned methods of activation, there are also a number of chemical compounds which come into consideration for use as activators for hydrogen peroxide with the formation of per-acids.
According to W. Ney, particularly effective compounds combine a very small molecular weight with a large number of reactive acyl groups, such as tetraacetylethylene-diamine (TAED) and tetraacetylglycoluril (TAGU).
DE-A-l 695 219 discloses the use of acylated glycolurils, especially TAGU, as a bleaching agent especially in the bleaching of fibers of any kind.
EP-A-125 641 and US-A-4 544 503 disclose the use of acyloxybenzenesulfonic acid salts (AOBS) as activators for the peroxide bleach of fabrics and as dyeing assist-ant in the dyeing of acrylic fibers.
EP-A-442 549 mentions the use of phthalimidoperoxy-carboxylic acids as bleaching agents for fabrics and hard 21~6713 surfaces.
DE-A-l 291 317 describes a bleaching process which is suitable for removing stains from textiles and involves peroxide baths which include organic N-acyl compounds.
The activators mentioned for the inorganic per-salts used, such as sodium perborate tetrahydrate, sodium perborate and sodium percarbonate, also include N-acetyl-caprolactam. The disadvantage with these processes is the mandatory use of inorganic per-salts.
EP-A-0 584 710 discloses a process for bleaching textile raw material with the aid of organic per-acids and hydrogen peroxide wherein the bleaching liquor includes as bleach activator a carboxamide, a carboxylic ester or a sulfonic acid salt. The solid bleach activators described have the disadvantage that they cannot be used for the liquid metering systems employed in the textile industry.
It is an object of the present invention to provide liquid bleach activators suitable for bleaching textile raw material.
The present invention accordingly provides a process for bleaching textile raw material with the aid of hydrogen peroxide by treating the textile raw material with an aqueous bleaching liquor including hydrogen peroxide and a bleach activator, which comprises using as the bleach activator an N-acyllactam of the formula I
,~,0 -C O
(CH2)n ¦ 11 ( I ) N C R
where n is from 3 to 5, and 214671~
Rl i 8 C~ - C5-alkyl.
The preferred bleach activator is N-acetylcaprolactam.
The textile materials used are preferably cellulo8ei especially unpretreated natural cellulose, such as hemp, linen, jute, cotton, regenerated cellulose fibers, such as staple viscose, viscose acetate, rayon, animal fiber, such as wool and silk, and also synthetic fibers, such as polyamide, polyacrylonitrile or polyester fiber materials, and also fiber blends, for example those of polyacrylonitrile-cotton or polyester-cotton.
The textile material to be treated can be present in the various processing states, for example the cellulose-containing material as loose material, staple, slubbing, yarn, knitted fabric or woven fabric. The textile material i8 treated continuously (for example by impreg-nation) or batchwise (for example by means of exhaust processes in a bleaching apparatus) in aqueous liquor.
The aqueous bleaching liquor, in addition to the bleach activators mentioned, hydrogen peroxide and optionally peroxide stabilizers, includes w~h;ng and wetting agents, additives, such as defoamers and dissolution improvers, buffer systems, such as phosphate salts and citric acid, and basic salts, such as sodium bicarbonate, disodium carbonate and/or sodium hydroxide. The pH of the bleaching liquor iB within the range from 5 to 13, preferably 7 to 9.
The molar ratio of hydrogen peroxide to bleach activator i8 1.0 - 5 : 1, preferably 1.1 - 1.5 : 1, based on the active carbonyl group of the bleach activator.
The liquid bleach activators of the invention permit preparation of the bleaching liquor in the liquor makeup vessel in the above-described manner or direct metering by metering means together with the other liquid ingredients of the bleaching liquor directly into the 214671~
~_ 5 bleaching apparatus or the impregnating beck.
In the bleaching apparatus, the textile material is wetted and saturated with the bleaching liquor 80 that the weight of the liquor is usually 3 - 50 times that of the textile material. The textile raw material is treated cold with the bleaching liquor or heated together with the bleaching liquor to temperatures from 40 to 130C and treated at these temperatures. Customary treatment times range from 30 minutes to 3 hours.
In the impregnating processes, the textile raw material is impregnated, i.e. wetted and saturated, with the bleaching liquor in the impregnating beck. After impreg-nation, the textile raw material i8 either stored cold for a period from 0.5 to 24 hours, usually at room temperature, or heated in atmospheric steamers with steam at temperatures from 95C to 120C. The residence time at this temperature is 1 minute to 2 hours.
Usually, but not mandatorily, the bleach with the bleach activators of the invention is followed by a further bleaching process, for example the alkaline peroxide bleach.
It has been found that precisely the combination of activator bleach with alkaline peroxide bleach results in good whiteness of the textile material. Following the bleach, the textile material is washed.
The examples which follow illustrate the process of the invention.
Example l Bleaching of knitwear and desized woven cloth in 100%
cotton.
The first step involves the activated peroxide bleach: -8 g/l of N-acetylcaprolactam 21~671~
-5 g/l of H22 (35% strength aqueous solution) 5 g/l of calcined sodium carbonate 3 g/l of 3Lastabil TGS (peroxide stabilizer, trade-mark of Hoechst AG, mixture of organic carboxylic acid and phosphonic acid salts) 3 g/l of ~9Eostapal FA (washing and wetting agent, trademark of Hoechst AG, mixture of various fatty alcohol ethoxylates) The liquor is made up in the liquor makeup vessel. The textile material is cold-padded and steamed under satu-rated steam at 97 - 102C for 15 - 30 minutes. This is followed by a wash.
In the second step, the material is impregnated wet-on-wet with an alkaline peroxide bleaching liquor.
25 g/l of H22 (35% strength aqueous solution) 4 g/l of caustic soda 3 g/l of ~'Lastabil TGS
3 g/l of ~Hostapal FA
The impregnated material is steamed with saturated steam for 15 - 20 minutes and then washed.
Example 2 Bleaching of knitwear and desized woven cloth in 100%
cotton by exhaust method.
The liquor ratio of bleaching liquor to textile material is 10:1.
The bleaching liquor includes 1 g/l of ~Hostapal FA
1 g/l of ~ Lastabil TGS
It has been found that the use of hypochlorites in bleaching processes gives rise to org~noh~logen compounds which can be harmful. This leads to an ever increasing renunciation of this bleaching agent.
The sodium chlorite bleach, which is carried out in the acid pH range, gives rise to the formation of chlorine dioxide, which is harmful and represents an odor nuis-ance. In addition, this bleaching agent can be used onlyon selected textile machines, made of special materials.
Owing to these disadvantages, bleaching with hydrogen peroxide is increasingly preferred.
The review "Activators and stabilizers for the peroxide bleach" by Dr. W. Ney in Textilpraxis international 1974, October and November, pages 1392 - 1565, reveals that hydrogen peroxide is today the most common bleaching agent for all natural fibers of vegetable and ~n;~-l origin.
To achieve a bleaching effect with hydrogen peroxide, it first has to be activated. Also, the bleaching solution needs to be stabilized in order that the 1088 of active oxygen may be m;n;mi zed.
It i~ generally customary and best known to activate with bases. In the bleaching of cellulose fibers, the base used for cotton is almost exclusively sodium peroxide 21~6713 while sodium carbonate is preferred for bast fibers, especially linen. The disadvantage with the use of bases is the alkali sensitivity of animal fibers.
In addition to bases, hydrogen peroxide can be activated in other ways, for example by chemical conversion of the hydrogen peroxide into organic and inorganic per-acids.
G. Rosch, Deutsche Textiltechnik 10 (1960), No. 4, pages 191-195, discloses the use of peracetic acid in textile bleaching. Peracetic acid is inflammable. The concen-trated solution, which has a pungent odor, is corrosiveand burns the skin. The biggest disadvantage of peracetic acid is its high explosivity. The use of acetic anhydride in its preparation may, under adverse conditions, give rise to the formation, as a by-product, of diacetyl peroxide which likewise tends to decompose spontaneously.
This behavior is probably the reason why peracetic acid has never found the expected success as bleaching agent.
In addition to the aforementioned methods of activation, there are also a number of chemical compounds which come into consideration for use as activators for hydrogen peroxide with the formation of per-acids.
According to W. Ney, particularly effective compounds combine a very small molecular weight with a large number of reactive acyl groups, such as tetraacetylethylene-diamine (TAED) and tetraacetylglycoluril (TAGU).
DE-A-l 695 219 discloses the use of acylated glycolurils, especially TAGU, as a bleaching agent especially in the bleaching of fibers of any kind.
EP-A-125 641 and US-A-4 544 503 disclose the use of acyloxybenzenesulfonic acid salts (AOBS) as activators for the peroxide bleach of fabrics and as dyeing assist-ant in the dyeing of acrylic fibers.
EP-A-442 549 mentions the use of phthalimidoperoxy-carboxylic acids as bleaching agents for fabrics and hard 21~6713 surfaces.
DE-A-l 291 317 describes a bleaching process which is suitable for removing stains from textiles and involves peroxide baths which include organic N-acyl compounds.
The activators mentioned for the inorganic per-salts used, such as sodium perborate tetrahydrate, sodium perborate and sodium percarbonate, also include N-acetyl-caprolactam. The disadvantage with these processes is the mandatory use of inorganic per-salts.
EP-A-0 584 710 discloses a process for bleaching textile raw material with the aid of organic per-acids and hydrogen peroxide wherein the bleaching liquor includes as bleach activator a carboxamide, a carboxylic ester or a sulfonic acid salt. The solid bleach activators described have the disadvantage that they cannot be used for the liquid metering systems employed in the textile industry.
It is an object of the present invention to provide liquid bleach activators suitable for bleaching textile raw material.
The present invention accordingly provides a process for bleaching textile raw material with the aid of hydrogen peroxide by treating the textile raw material with an aqueous bleaching liquor including hydrogen peroxide and a bleach activator, which comprises using as the bleach activator an N-acyllactam of the formula I
,~,0 -C O
(CH2)n ¦ 11 ( I ) N C R
where n is from 3 to 5, and 214671~
Rl i 8 C~ - C5-alkyl.
The preferred bleach activator is N-acetylcaprolactam.
The textile materials used are preferably cellulo8ei especially unpretreated natural cellulose, such as hemp, linen, jute, cotton, regenerated cellulose fibers, such as staple viscose, viscose acetate, rayon, animal fiber, such as wool and silk, and also synthetic fibers, such as polyamide, polyacrylonitrile or polyester fiber materials, and also fiber blends, for example those of polyacrylonitrile-cotton or polyester-cotton.
The textile material to be treated can be present in the various processing states, for example the cellulose-containing material as loose material, staple, slubbing, yarn, knitted fabric or woven fabric. The textile material i8 treated continuously (for example by impreg-nation) or batchwise (for example by means of exhaust processes in a bleaching apparatus) in aqueous liquor.
The aqueous bleaching liquor, in addition to the bleach activators mentioned, hydrogen peroxide and optionally peroxide stabilizers, includes w~h;ng and wetting agents, additives, such as defoamers and dissolution improvers, buffer systems, such as phosphate salts and citric acid, and basic salts, such as sodium bicarbonate, disodium carbonate and/or sodium hydroxide. The pH of the bleaching liquor iB within the range from 5 to 13, preferably 7 to 9.
The molar ratio of hydrogen peroxide to bleach activator i8 1.0 - 5 : 1, preferably 1.1 - 1.5 : 1, based on the active carbonyl group of the bleach activator.
The liquid bleach activators of the invention permit preparation of the bleaching liquor in the liquor makeup vessel in the above-described manner or direct metering by metering means together with the other liquid ingredients of the bleaching liquor directly into the 214671~
~_ 5 bleaching apparatus or the impregnating beck.
In the bleaching apparatus, the textile material is wetted and saturated with the bleaching liquor 80 that the weight of the liquor is usually 3 - 50 times that of the textile material. The textile raw material is treated cold with the bleaching liquor or heated together with the bleaching liquor to temperatures from 40 to 130C and treated at these temperatures. Customary treatment times range from 30 minutes to 3 hours.
In the impregnating processes, the textile raw material is impregnated, i.e. wetted and saturated, with the bleaching liquor in the impregnating beck. After impreg-nation, the textile raw material i8 either stored cold for a period from 0.5 to 24 hours, usually at room temperature, or heated in atmospheric steamers with steam at temperatures from 95C to 120C. The residence time at this temperature is 1 minute to 2 hours.
Usually, but not mandatorily, the bleach with the bleach activators of the invention is followed by a further bleaching process, for example the alkaline peroxide bleach.
It has been found that precisely the combination of activator bleach with alkaline peroxide bleach results in good whiteness of the textile material. Following the bleach, the textile material is washed.
The examples which follow illustrate the process of the invention.
Example l Bleaching of knitwear and desized woven cloth in 100%
cotton.
The first step involves the activated peroxide bleach: -8 g/l of N-acetylcaprolactam 21~671~
-5 g/l of H22 (35% strength aqueous solution) 5 g/l of calcined sodium carbonate 3 g/l of 3Lastabil TGS (peroxide stabilizer, trade-mark of Hoechst AG, mixture of organic carboxylic acid and phosphonic acid salts) 3 g/l of ~9Eostapal FA (washing and wetting agent, trademark of Hoechst AG, mixture of various fatty alcohol ethoxylates) The liquor is made up in the liquor makeup vessel. The textile material is cold-padded and steamed under satu-rated steam at 97 - 102C for 15 - 30 minutes. This is followed by a wash.
In the second step, the material is impregnated wet-on-wet with an alkaline peroxide bleaching liquor.
25 g/l of H22 (35% strength aqueous solution) 4 g/l of caustic soda 3 g/l of ~'Lastabil TGS
3 g/l of ~Hostapal FA
The impregnated material is steamed with saturated steam for 15 - 20 minutes and then washed.
Example 2 Bleaching of knitwear and desized woven cloth in 100%
cotton by exhaust method.
The liquor ratio of bleaching liquor to textile material is 10:1.
The bleaching liquor includes 1 g/l of ~Hostapal FA
1 g/l of ~ Lastabil TGS
2 g/l of calcined sodium carbonate 2 g/l of H202 (35% strength aqueous solution)
3 g/1 of N-acetylcaprolactam 21~6713 The liquor i8 heated together with the textile material to 60C and held at that temperature for 1 hour. Then hydrogen peroxide and caustic soda are added 80 that the concentrations in the bleaching bath are as follows:
6 g of 35% ~trength aqueous H22 solution/l of bleaching bath 1 g/l of caustic soda.
The bleaching liquor is heated up to 95C and held at that temperature for 1 hour. The liquor is then dis-charged and the textile material is rinsed with hot water (60C) Example 3 Bleaching of woven cloth in 100% viscose fiber.
The cloth has been predesized.
The bleaching liquor includes:
8 g/l of N-acetylcaprolactam 5 g/l of H202 (35% strength aqueous solution) 5 g/l of calcined sodium carbonate 3 g/l of ~Lastabil TGS
3 g/l of ~Hostapal FA
The cloth is impregnated with the bleaching liquor and batched at room temperature (20 - 30C) for 18 hours.
Then the cloth is washed with hot water.
6 g of 35% ~trength aqueous H22 solution/l of bleaching bath 1 g/l of caustic soda.
The bleaching liquor is heated up to 95C and held at that temperature for 1 hour. The liquor is then dis-charged and the textile material is rinsed with hot water (60C) Example 3 Bleaching of woven cloth in 100% viscose fiber.
The cloth has been predesized.
The bleaching liquor includes:
8 g/l of N-acetylcaprolactam 5 g/l of H202 (35% strength aqueous solution) 5 g/l of calcined sodium carbonate 3 g/l of ~Lastabil TGS
3 g/l of ~Hostapal FA
The cloth is impregnated with the bleaching liquor and batched at room temperature (20 - 30C) for 18 hours.
Then the cloth is washed with hot water.
Claims (9)
1. A process for bleaching textile raw material with the aid of hydrogen peroxide by treating the textile raw material with an aqueous bleaching liquor including hydrogen peroxide and a bleach activator, which comprises using as the bleach activator an N-acyllactam of the formula I
(I) where n is from 3 to 5, and R1 is C1-C5-alkyl.
(I) where n is from 3 to 5, and R1 is C1-C5-alkyl.
2. The process of claim 1 wherein the molar ratio of hydrogen peroxide to bleach activator in the bleach-ing liquor is 1.0-5:1, preferably 1.1-1.5:1, based on the active carbonyl group of the bleach activator.
3. The process of claim 1 or 2 wherein the pH of the bleaching liquor is within the range from 5 to 13, preferably 7 to 9.
4. The process of any one of claims 1 to 3 wherein the textile raw material is treated by means of a continuous process.
The process of claim 4 wherein the treatment takes the form of an impregnating process.
6. The process of claim 5 wherein the textile raw material is initially treated with the bleaching liquor by wetting and saturating, then stored cold over a period of from 0.5 to 24 hours or heated with steam to a temperature from 95 to 120°C and subsequently the bleached textile raw material is washed.
7. The process of any one of claims 1 to 3 wherein the textile raw material is treated by means of a batch process.
8. The process of claim 7 wherein the treatment takes the form of an exhaust process.
9. The process of claim 8 wherein the textile raw material is wetted and saturated with bleaching liquor cold or at a temperature of from 40 to 130°C, the weight of the liquor being 3 - 50 times the weight of the raw material.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE4412390A DE4412390A1 (en) | 1994-04-11 | 1994-04-11 | Process for bleaching textiles |
| DEP4412390.6 | 1994-04-11 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2146713A1 true CA2146713A1 (en) | 1995-10-12 |
Family
ID=6515087
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002146713A Abandoned CA2146713A1 (en) | 1994-04-11 | 1995-04-10 | Bleaching of textiles |
Country Status (5)
| Country | Link |
|---|---|
| EP (1) | EP0676499A3 (en) |
| JP (1) | JPH0835171A (en) |
| KR (1) | KR950032867A (en) |
| CA (1) | CA2146713A1 (en) |
| DE (1) | DE4412390A1 (en) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE19810885A1 (en) * | 1998-03-13 | 1999-10-07 | Henkel Kgaa | Process for the gentle bleaching of textile fabrics |
| FR2790390B1 (en) * | 1999-03-05 | 2002-08-02 | Anios Lab Sarl | PROCESS FOR THE PREPARATION OF AN ANTIMICROBIAL COMPOSITION |
| EP1634990A1 (en) * | 2004-09-10 | 2006-03-15 | CHT R. Beitlich | Liquid additive for finishing textile products |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB855735A (en) * | 1958-05-09 | 1960-12-07 | Unilever Ltd | Bleaching processes and compositions |
| DE2554592C3 (en) * | 1975-12-04 | 1981-11-26 | Bosch-Siemens Hausgeräte GmbH, 7000 Stuttgart | Washing process for textiles to be carried out in an automatic washing machine and the device for carrying it out |
| DE2719235B2 (en) * | 1977-04-29 | 1980-07-17 | Bosch-Siemens Hausgeraete Gmbh, 7000 Stuttgart | Washing process and automatic washing machine to carry out the washing process |
-
1994
- 1994-04-11 DE DE4412390A patent/DE4412390A1/en not_active Withdrawn
-
1995
- 1995-04-04 EP EP95105011A patent/EP0676499A3/en not_active Withdrawn
- 1995-04-10 JP JP7084331A patent/JPH0835171A/en not_active Withdrawn
- 1995-04-10 CA CA002146713A patent/CA2146713A1/en not_active Abandoned
- 1995-04-10 KR KR1019950008227A patent/KR950032867A/en not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| KR950032867A (en) | 1995-12-22 |
| EP0676499A2 (en) | 1995-10-11 |
| JPH0835171A (en) | 1996-02-06 |
| EP0676499A3 (en) | 1996-09-11 |
| DE4412390A1 (en) | 1995-10-19 |
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