CA2227953A1 - Water in oil emulsions containing pyrrole - Google Patents
Water in oil emulsions containing pyrrole Download PDFInfo
- Publication number
- CA2227953A1 CA2227953A1 CA002227953A CA2227953A CA2227953A1 CA 2227953 A1 CA2227953 A1 CA 2227953A1 CA 002227953 A CA002227953 A CA 002227953A CA 2227953 A CA2227953 A CA 2227953A CA 2227953 A1 CA2227953 A1 CA 2227953A1
- Authority
- CA
- Canada
- Prior art keywords
- terpene
- incorporated
- pyrrole
- emulsion
- water
- 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
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D9/00—Chemical paint or ink removers
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D9/00—Chemical paint or ink removers
- C09D9/005—Chemical paint or ink removers containing organic solvents
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/01—Hydrocarbons
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L1/00—Compositions of cellulose, modified cellulose or cellulose derivatives
- C08L1/08—Cellulose derivatives
- C08L1/26—Cellulose ethers
- C08L1/28—Alkyl ethers
- C08L1/284—Alkyl ethers with hydroxylated hydrocarbon radicals
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L91/00—Compositions of oils, fats or waxes; Compositions of derivatives thereof
- C08L91/06—Waxes
Abstract
Improvements in the rate of stripping of alkaline water-in-oil emulsions by incorporating in the organic phase thereof an effective amount of pyrrole.
Description
, CA 02227953 1998-02-24 WATER IN OIL EMULSIONS CONTAINING PYRROLE
Field of the Invention The present invention relates to improvements in the stripping rate of AlkAIine 5paint stripping formulations comprising water-in-oil emulsions contAining benzyl alcohol, the improvement resulting from incorporating in the oil phase thereof an effective amount of pyrrole.
CA 022279~3 1998-02-24 Background of the Invention Benzyl alcohol based, alkaline water-in-oil emulsicns to which this invention is directed are descri~ed, for example, in U.S. Patent No. 5,387,363 (referred to herein as "the '363 patent") and in copending U.S. Patent Application No. 08/706,850 (referred to herein as "the '850 application~), the entire specifications of which are hereby incorporated by reference. Particularly preferred are those alkaline water-in-oil emulsions which contain a wax such as paraffin wax.
Summary of the Invent;on In alkaline paint stripper formulations containing a water-in-oil emulsion having a water phase and a contin~.ous benzyl alcohol (oil) phase, but in the absence of any organic amine activator, an improvement is provide!d which comprises incorporating pyrrole in the benzyl alcohol phase in an amount effective to improve the stripping rate. Preferred embodiments include the incorporation of a terpene such as d-limonene to retard CA 022279~3 1998-02-24 the rate of water evaporation and/or anisole to further enhance the stripping rate.
Detailed Descri~t;on of the Invention It has now been found that incorporation of pyrrole into the organic, benzyl alcohol phase of an alkaline water-in-oil emulsion enhances the rate of stripping .
The wax-containing, alkaline water-in-oil emulsions described in the '850 application and the '363 patent are parl-icularly advantageous in paint removers since the emulsions, among other things, reduce odor and the wax (natural or synthetic) improves the stripping efficiency by retarding evaporation of ingredients such as water and other volatiles that enhance stripping. When wax is present, it is generally used in an amount which is slightly in excess (1~ by weight) of that which would saturate the organic phase. A preferred wax is paraffin wax (which term includes its individual components).
Paraffin or mineral oil, vegetable wax, microcrystalline wax, ceresine wax and montan wax may similarly be used.
CA 022279~3 1998-02-24 The pyrrole is generally used ln an amount of from about 1.0 to about 24.0 weight ~, based on the total weight of the emulsion (preferably from about 2 to about 24~, most preferably from about 8 to 24%), depending on the substrate to be stripped, the amount of solvents (and wax, if any) in the stripper formulation, and so on. The upper limit is a practical one, since additional pyrrole seems to have little effect on the stripping rate, while at levels below about 1~ solvency can be lost.
One or more terpenes can also be added with the pyrrole, since the presence of a terpene helps to reduce evaporation of water and other solvents from these inverse emulsion paint strippers, so that the use life of such strippers can be extended to 24 hours or more. When using this combination, the pyrrole is preferably used in amounts of- about 8-16~, while the terpene is preferably used in amounts of about 4-8~. Examples of such terpenes are d-limonene (preferred), dipentene (also known as 1-methyl-4-(1-methylethenyl)-cyclohexene), myrcene, alpha-pinene, linalool and mixtures thereof.
~ CA 022279~3 1998-02-24 Anisole can also be added with the pyrrole to enhance the stripping rate, in which event the total amount of anisole and pyrrole is from about 1 to about 24~ (preferably 2-16~), or with the pyrrole/terpene combination. When anisole, terpene(s) and pyrrole are all incorporated in the stripper, an optimized system is generally one which has about 8-16% anisole, about 5-9 terpene(s) and about 0.3-8~ pyrrole.
The amount of wax incorporated in the emulsion of the preferred strippers is normally from about 0.02 to about S.0 percent by weight, based on the total weight of the emulsion, more typically from about 0.1 to about 1.0~. Any type of commercially available paraffin wax or ceresin.e wax (or their components) can be used. Most paraffin waxes have a melting point in the range of about 47 to 65~G.
Wi.th reference to the '850 application and the '363 patent, a paint stripper formulation employing such an emulsion can be made by mixing together water; benzyl alcoho].; any wax; pyrrole; up to about 2~ by weight of CA 022279~3 1998-02-24 thickeners (such as a hydroxypropyl cellulose or methylcellulose); up to about 15% by weight of a hydrocarbon solvent (aromatic or aliphatic, including petroleum distillates) to help wet the thickener and dissolve any wax; up to about 2% by weight of surfactants (such as sodium xylene sulfonate or an imidazoline such as oleic hydroxyethyl imidazoline); up to about 15~ by weight of ammonia; up to about 5% by weight of corrosion inhibitors (such as 2-mercaptobenzotriazole, benzotriazole or sodium silicate); and, if desired, a small amount (usually no more than 0.1 to 0.3 grams per gallon) of a dye.
Examples (Nos. 1 to 7) of such paint remover formulations with optimized amounts of solvents of this invention are as follows (the ingredient amounts being listed in_parts by weight), together with a comparative example (No. C1) having no pyrrole:
CA 022279~3 1998-02-24 Example Nos:
3 4 5 6 7 Cl benzyl alcohol 40.0 40.0 40.0 40.0 40.0 40.0 40.0 40.0 hydroxypropyl cellulose* .5 .5 .5 .5 .5 .5 .5.5 aromat-c hydro-carbon solvent .5 .5 .5 .5 .5 .5 .5 .5 paraff:n wax .3 .3 .3 .3 .3 .3 .3.3 surfact:ant .7 .7 .7 .7 .7 .7 .7.7 corrosion inhibitors 3.5 3.5 3.5 3.5 3.53.5 3.5 3.5 ammonia 5.0 5.0 5.0 5.0 5.05.0 5.0 5.0 water 41.5 25.5 25.5 29.5 33.529.025.5 49.5 d-limonene 0 0 0 4.0 8.05.5 8.0 0 anisole 0 0 12.0 0 011.5 8.0 0 pyrrole 8.0 24.0 12.0 16.0 8.03.5 8.0 0 * - The amount of hydroxypropyl cellulose thickener was varied between 0.4 and 0.6 to compensate for varying viscos:ity due to varying amounts of solvent Comparative stripping tests were run on these formulations in standard performance tests on aluminum panels painted with a Polyurethane Topcoat System CA 022279~3 1998-02-24 ~polyurethane topcoat over an epoxy primer) or a Polyurel,hane Topcoat/Polyurethane Primer System (polyurethane topcoat over a polyurethane primer). The stripping tests followed MIL-R-81294, a military specification used to evaluate the effectiveness of paint strippe:rs to remove a white polyurethane paint from aluminum. While no tests were done on Epoxy Topcoat Systems (epoxy topcoats over epoxy primers), previous experie:nce has shown that results with Polyurethane Topcoat Systems are similar to that with Epoxy Topcoat Systems. The results of these tests are reported in Table I below, the data showing the percent of the panels stripped in 24 hours on each of the systems:
CA 022279~3 1998-02-24 TART,F. I
% of Panels ~ of Panels Painted with Painted with Polyurethane/Poly- Polyurethane/-Exam~le No. urethane Stripped Epoxy Stripped C1* 0 0 1* 5 0 2 10 o 3* 35 10 4* 85 20 * - These report an average of tests on two separately made fcrmulation batches Examples 1 and 2 show that pyrrole alone is effective for improved stripping on the Polyurethane Topcoat/-Polyurethane Primer System. Improved stripping on both systems results from combinations of the pyrrole with a terpene ~d-limonene) and/or anisole, the combinations containing both pyrrole and a terpene being particularly effecti.ve, as is evident from Examples 3-7.
Field of the Invention The present invention relates to improvements in the stripping rate of AlkAIine 5paint stripping formulations comprising water-in-oil emulsions contAining benzyl alcohol, the improvement resulting from incorporating in the oil phase thereof an effective amount of pyrrole.
CA 022279~3 1998-02-24 Background of the Invention Benzyl alcohol based, alkaline water-in-oil emulsicns to which this invention is directed are descri~ed, for example, in U.S. Patent No. 5,387,363 (referred to herein as "the '363 patent") and in copending U.S. Patent Application No. 08/706,850 (referred to herein as "the '850 application~), the entire specifications of which are hereby incorporated by reference. Particularly preferred are those alkaline water-in-oil emulsions which contain a wax such as paraffin wax.
Summary of the Invent;on In alkaline paint stripper formulations containing a water-in-oil emulsion having a water phase and a contin~.ous benzyl alcohol (oil) phase, but in the absence of any organic amine activator, an improvement is provide!d which comprises incorporating pyrrole in the benzyl alcohol phase in an amount effective to improve the stripping rate. Preferred embodiments include the incorporation of a terpene such as d-limonene to retard CA 022279~3 1998-02-24 the rate of water evaporation and/or anisole to further enhance the stripping rate.
Detailed Descri~t;on of the Invention It has now been found that incorporation of pyrrole into the organic, benzyl alcohol phase of an alkaline water-in-oil emulsion enhances the rate of stripping .
The wax-containing, alkaline water-in-oil emulsions described in the '850 application and the '363 patent are parl-icularly advantageous in paint removers since the emulsions, among other things, reduce odor and the wax (natural or synthetic) improves the stripping efficiency by retarding evaporation of ingredients such as water and other volatiles that enhance stripping. When wax is present, it is generally used in an amount which is slightly in excess (1~ by weight) of that which would saturate the organic phase. A preferred wax is paraffin wax (which term includes its individual components).
Paraffin or mineral oil, vegetable wax, microcrystalline wax, ceresine wax and montan wax may similarly be used.
CA 022279~3 1998-02-24 The pyrrole is generally used ln an amount of from about 1.0 to about 24.0 weight ~, based on the total weight of the emulsion (preferably from about 2 to about 24~, most preferably from about 8 to 24%), depending on the substrate to be stripped, the amount of solvents (and wax, if any) in the stripper formulation, and so on. The upper limit is a practical one, since additional pyrrole seems to have little effect on the stripping rate, while at levels below about 1~ solvency can be lost.
One or more terpenes can also be added with the pyrrole, since the presence of a terpene helps to reduce evaporation of water and other solvents from these inverse emulsion paint strippers, so that the use life of such strippers can be extended to 24 hours or more. When using this combination, the pyrrole is preferably used in amounts of- about 8-16~, while the terpene is preferably used in amounts of about 4-8~. Examples of such terpenes are d-limonene (preferred), dipentene (also known as 1-methyl-4-(1-methylethenyl)-cyclohexene), myrcene, alpha-pinene, linalool and mixtures thereof.
~ CA 022279~3 1998-02-24 Anisole can also be added with the pyrrole to enhance the stripping rate, in which event the total amount of anisole and pyrrole is from about 1 to about 24~ (preferably 2-16~), or with the pyrrole/terpene combination. When anisole, terpene(s) and pyrrole are all incorporated in the stripper, an optimized system is generally one which has about 8-16% anisole, about 5-9 terpene(s) and about 0.3-8~ pyrrole.
The amount of wax incorporated in the emulsion of the preferred strippers is normally from about 0.02 to about S.0 percent by weight, based on the total weight of the emulsion, more typically from about 0.1 to about 1.0~. Any type of commercially available paraffin wax or ceresin.e wax (or their components) can be used. Most paraffin waxes have a melting point in the range of about 47 to 65~G.
Wi.th reference to the '850 application and the '363 patent, a paint stripper formulation employing such an emulsion can be made by mixing together water; benzyl alcoho].; any wax; pyrrole; up to about 2~ by weight of CA 022279~3 1998-02-24 thickeners (such as a hydroxypropyl cellulose or methylcellulose); up to about 15% by weight of a hydrocarbon solvent (aromatic or aliphatic, including petroleum distillates) to help wet the thickener and dissolve any wax; up to about 2% by weight of surfactants (such as sodium xylene sulfonate or an imidazoline such as oleic hydroxyethyl imidazoline); up to about 15~ by weight of ammonia; up to about 5% by weight of corrosion inhibitors (such as 2-mercaptobenzotriazole, benzotriazole or sodium silicate); and, if desired, a small amount (usually no more than 0.1 to 0.3 grams per gallon) of a dye.
Examples (Nos. 1 to 7) of such paint remover formulations with optimized amounts of solvents of this invention are as follows (the ingredient amounts being listed in_parts by weight), together with a comparative example (No. C1) having no pyrrole:
CA 022279~3 1998-02-24 Example Nos:
3 4 5 6 7 Cl benzyl alcohol 40.0 40.0 40.0 40.0 40.0 40.0 40.0 40.0 hydroxypropyl cellulose* .5 .5 .5 .5 .5 .5 .5.5 aromat-c hydro-carbon solvent .5 .5 .5 .5 .5 .5 .5 .5 paraff:n wax .3 .3 .3 .3 .3 .3 .3.3 surfact:ant .7 .7 .7 .7 .7 .7 .7.7 corrosion inhibitors 3.5 3.5 3.5 3.5 3.53.5 3.5 3.5 ammonia 5.0 5.0 5.0 5.0 5.05.0 5.0 5.0 water 41.5 25.5 25.5 29.5 33.529.025.5 49.5 d-limonene 0 0 0 4.0 8.05.5 8.0 0 anisole 0 0 12.0 0 011.5 8.0 0 pyrrole 8.0 24.0 12.0 16.0 8.03.5 8.0 0 * - The amount of hydroxypropyl cellulose thickener was varied between 0.4 and 0.6 to compensate for varying viscos:ity due to varying amounts of solvent Comparative stripping tests were run on these formulations in standard performance tests on aluminum panels painted with a Polyurethane Topcoat System CA 022279~3 1998-02-24 ~polyurethane topcoat over an epoxy primer) or a Polyurel,hane Topcoat/Polyurethane Primer System (polyurethane topcoat over a polyurethane primer). The stripping tests followed MIL-R-81294, a military specification used to evaluate the effectiveness of paint strippe:rs to remove a white polyurethane paint from aluminum. While no tests were done on Epoxy Topcoat Systems (epoxy topcoats over epoxy primers), previous experie:nce has shown that results with Polyurethane Topcoat Systems are similar to that with Epoxy Topcoat Systems. The results of these tests are reported in Table I below, the data showing the percent of the panels stripped in 24 hours on each of the systems:
CA 022279~3 1998-02-24 TART,F. I
% of Panels ~ of Panels Painted with Painted with Polyurethane/Poly- Polyurethane/-Exam~le No. urethane Stripped Epoxy Stripped C1* 0 0 1* 5 0 2 10 o 3* 35 10 4* 85 20 * - These report an average of tests on two separately made fcrmulation batches Examples 1 and 2 show that pyrrole alone is effective for improved stripping on the Polyurethane Topcoat/-Polyurethane Primer System. Improved stripping on both systems results from combinations of the pyrrole with a terpene ~d-limonene) and/or anisole, the combinations containing both pyrrole and a terpene being particularly effecti.ve, as is evident from Examples 3-7.
Claims (14)
1. In an alkaline paint stripper formulation which contains a water-in-oil emulsion having a water phase and a continuous benzyl alcohol phase, but which does not contain an organic amine activator, the improvement comprising incorporating pyrrole in the benzyl alcohol phase in an amount effective to increase the rate of stripping.
2. The paint stripper formulation of Claim 1 wherein a wax is incorporated in the benzyl alcohol phase.
3. The paint stripper formulation of Claim 2 wherein a terpene is also incorporated in the benzyl alcohol phase.
4. The paint stripper formulation of Claim 3 wherein the terpene is d-limonene.
5. The paint stripper formulation of Claim 2 wherein anisole is also incorporated in the benzyl alcohol phase.
6. The paint stripper formulation of Claim 2 wherein a terpene and anisole are also incorporated in the benzyl alcohol phase.
7. The paint stripper formulation of Claim 6 wherein the terpene is d-limonene.
8. A method of increasing the stripping rate of an alkaline water-in-oil emulsion paint stripper which does not contain an organic amine activator, which method comprises incorporating into the emulsion's organic phase an effective amount of pyrrole.
9 A method as in Claim 8 wherein a wax is also incorporated into the emulsion's organic phase.
10. A method as in Claim 9 wherein a terpene is also incorporated into the emulsion's organic phase.
11. A method as in Claim 10 wherein the terpene is d-limonene.
12. A method as in Claim 9 wherein anisole is also incorporated into the emulsion's organic phase.
13. A method as in Claim 9 wherein a terpene and anisole are also incorporated into the emulsion's organic phase.
14. A method as in Claim 13 wherein the terpene is d-limonene.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US08/804,649 US5854188A (en) | 1997-02-25 | 1997-02-25 | Water in oil emulsions containing pyrrole |
| US08/804,649 | 1997-02-25 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2227953A1 true CA2227953A1 (en) | 1998-08-25 |
Family
ID=25189489
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002227953A Abandoned CA2227953A1 (en) | 1997-02-25 | 1998-02-24 | Water in oil emulsions containing pyrrole |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US5854188A (en) |
| EP (1) | EP0860481A1 (en) |
| JP (1) | JPH10330659A (en) |
| KR (1) | KR19980071670A (en) |
| CN (1) | CN1195681A (en) |
| CA (1) | CA2227953A1 (en) |
| MY (1) | MY132845A (en) |
| SG (1) | SG66436A1 (en) |
| TW (1) | TW396181B (en) |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7176174B2 (en) * | 2003-03-06 | 2007-02-13 | The Lubrizol Corporation | Water-in-oil emulsion |
| US7309684B2 (en) * | 2005-05-12 | 2007-12-18 | The Lubrizol Corporation | Oil-in-water emulsified remover comprising an ethoxylated alcohol surfactant |
| US20090211492A1 (en) * | 2005-12-10 | 2009-08-27 | Hawes Charles L | Composition for thinning of oil-based paint |
| US20070135325A1 (en) * | 2005-12-10 | 2007-06-14 | Hawes Charles L | Composition for thinning and cleanup of paint |
| CN101319105B (en) * | 2008-07-18 | 2010-04-21 | 东南大学 | Paint stripper of oil emulsion-in-water |
| US9109191B2 (en) | 2009-12-15 | 2015-08-18 | Invista North America S.A.R.L. | Emulsion compositions and a method for selecting surfactants |
| US8372794B2 (en) * | 2009-12-15 | 2013-02-12 | Invista North America S.A R.L. | Emulsion compositions and a method for selecting surfactants |
| US20110162557A1 (en) * | 2010-01-04 | 2011-07-07 | Hawes Charles L | Solvent internal composition for thinning of uncured paint |
| RU2571123C1 (en) * | 2014-06-11 | 2015-12-20 | Михаил Александрович Барабанов | Composition for removal of paint coatings |
Family Cites Families (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4732695A (en) * | 1987-02-02 | 1988-03-22 | Texo Corporation | Paint stripper compositions having reduced toxicity |
| US5011621A (en) * | 1990-06-04 | 1991-04-30 | Arco Chemical Technology, Inc. | Paint stripper compositions containing N-methyl-2-pyrrolidone and renewable resources |
| US5405548A (en) * | 1991-01-30 | 1995-04-11 | Elf Atochem North America Inc. | Methylbenzyl formate paint strippers |
| US5387363A (en) * | 1992-06-02 | 1995-02-07 | Elf Atochem North America, Inc. | Water in oil emulsions |
| US5478491A (en) * | 1992-07-09 | 1995-12-26 | Specialty Environmental Technologies, Inc. | NMP/d-limonene paint stripper with evaporation inhibitor |
| US5454985A (en) * | 1992-11-06 | 1995-10-03 | Gage Products Company | Paint stripping composition |
| KR960701958A (en) * | 1993-03-30 | 1996-03-28 | 테릴 켄트 퀄리 | Composition and method for removing coating from flooring (IMPROVED FLOOR STRIPPING COMPOSITION AND METHOD) |
| US5425893A (en) * | 1993-04-14 | 1995-06-20 | Stevens; Edwin | Photoreactive paint stripping compositions and methods |
| EP0723568B1 (en) * | 1993-10-15 | 1999-05-26 | Minnesota Mining And Manufacturing Company | Improved paint stripper |
| US5411678A (en) * | 1994-02-07 | 1995-05-02 | Mcgean-Rohco, Inc. | Paint stripper |
| US5569410A (en) * | 1994-11-17 | 1996-10-29 | Elf Atochem North America, Inc. | Ammonium bicarbonate/ammonium carbamate activated benzyl alcohol paint stripper |
-
1997
- 1997-02-25 US US08/804,649 patent/US5854188A/en not_active Expired - Fee Related
-
1998
- 1998-02-23 MY MYPI98000766A patent/MY132845A/en unknown
- 1998-02-24 JP JP10057349A patent/JPH10330659A/en not_active Withdrawn
- 1998-02-24 SG SG1998000396A patent/SG66436A1/en unknown
- 1998-02-24 CA CA002227953A patent/CA2227953A1/en not_active Abandoned
- 1998-02-25 EP EP98301400A patent/EP0860481A1/en not_active Withdrawn
- 1998-02-25 CN CN98105385A patent/CN1195681A/en active Pending
- 1998-02-25 TW TW087102731A patent/TW396181B/en not_active IP Right Cessation
- 1998-02-25 KR KR1019980005887A patent/KR19980071670A/en not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| KR19980071670A (en) | 1998-10-26 |
| JPH10330659A (en) | 1998-12-15 |
| TW396181B (en) | 2000-07-01 |
| SG66436A1 (en) | 1999-07-20 |
| US5854188A (en) | 1998-12-29 |
| EP0860481A1 (en) | 1998-08-26 |
| CN1195681A (en) | 1998-10-14 |
| MY132845A (en) | 2007-10-31 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FZDE | Dead |