EP0924291B1 - Wässrige Weichspülmittel mit verbessertem Weichgriff - Google Patents
Wässrige Weichspülmittel mit verbessertem Weichgriff Download PDFInfo
- Publication number
- EP0924291B1 EP0924291B1 EP98119569A EP98119569A EP0924291B1 EP 0924291 B1 EP0924291 B1 EP 0924291B1 EP 98119569 A EP98119569 A EP 98119569A EP 98119569 A EP98119569 A EP 98119569A EP 0924291 B1 EP0924291 B1 EP 0924291B1
- Authority
- EP
- European Patent Office
- Prior art keywords
- component
- fatty acid
- approx
- test
- 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.)
- Expired - Lifetime
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
- C11D1/38—Cationic compounds
- C11D1/62—Quaternary ammonium compounds
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
- C11D3/0005—Other compounding ingredients characterised by their effect
- C11D3/001—Softening compositions
- C11D3/0015—Softening compositions liquid
Definitions
- the present invention relates to fabric softener in the form of aqueous emulsions or dispersions.
- Cationic compounds are usually used as fabric softener, for example quaternary ammonium compounds, which are in addition to long-chain Alkyl radicals can also contain ester or amide groups, for example as in U.S. Patent 3,349,033, 3,644,203, 3,946,115, 3,997,453, 4,073,735, 4,119,545. These components are used alone or in Mixtures with other cationic or neutral substances in Form of aqueous dispersions added to the rinsing bath.
- Ammonium compounds containing ester bonds are frequently used as for example in EP-A-0 239 910, US-PS 3 915 867, US-PS 4 137 180, U.S. Patent 4,830,771.
- WO-A-94/20597 relates to concentrated fabric softeners containing quaternary ammonium compounds, in which the long-chain fatty acid residues contain 11 to 21 carbon atoms and have iodine numbers in the range from 5 to 100.
- US-A-5,637,743 discloses the provision of a fabric softener containing quaternary ammonium salts, wherein the Fatty acids contain 5 to 23 carbon atoms ratio of fatty acid: amine is 1.85 to 1.40 and Iodine numbers range from 10 to 33.
- Ester compounds based on triethanolamine such as N-methyl-N, N-bis (beta-C 14-18 -acyloxyethyl), N-beta-hydroxyethyl ammonium methosulfate, which are sold under trade names such as TETRANYL® AT 75 (trademark of KAO Corp.), STEPANTEX® VRH 90 (trademark of Stepan Corp.) or REWOQUAT® WE 18 (trademark of Witco Surfactants GmbH).
- the absorption of moisture is generally considered to be a rewetting ability understood by the fiber. Inadequate back network assets have an effect but detrimental from where larger amounts of moisture from the skin surface should be included. z. B. with hand or bath towels and at Body or bed linen.
- the object of the invention was to make the above-mentioned disadvantages more conventional To overcome fabric softener formulations and to provide fabric softener, which, in addition to good biodegradability, is significantly improved Level of good soft feel while maintaining good rewetting ability exhibit.
- the object was achieved by using quaternary fatty acid amino alcohol esters from triethanolamine in relation to partially hydrogenated fatty acids from 1: 1.6 to 1: 2 in alcohols or glycols.
- the invention therefore relates to aqueous fabric softeners containing at least one of the compounds of the general formula (I) wherein R is the residue of a fatty acid with 14 to 18 carbon atoms and iodine numbers in the range of 15-25 and a can be 1, 2, 3.
- quaternary compounds of general use which are also used according to the invention Formula I are made according to those well known in the art Process by esterification of triethanolamine with fatty acid and subsequent Quaternization manufactured.
- fat components for the esterification or transesterification are the known and customary monobasic fatty acids based in this field natural vegetable and animal oils with in particular 14-18 Carbon atoms used, such as tallow fatty acids and palm fatty acids or their methyl or ethyl esters.
- the iodine number as a measure of the average degree of saturation of a Fatty acid, is the amount of iodine, which is from 100 g of the compound for saturation of the double bonds.
- Partially hydrogenated tallow fatty acids and palm fatty acids are preferred according to the invention with iodine numbers between 15-25. They are commercial products and are offered by various companies under their respective trade names.
- the esterification or transesterification is carried out according to known methods.
- the triethanolamine with the desired degree of esterification appropriate amount of fatty acid or fatty acid ester, if appropriate in the presence of a catalyst, e.g. B. methanesulfonic acid, under nitrogen 160-240 ° C implemented and the water of reaction or the Alcohol was continuously distilled off, thereby completing the reaction if necessary, the pressure can be reduced.
- a catalyst e.g. B. methanesulfonic acid
- the subsequent quaternization is also carried out using known methods.
- the ester if appropriate using a solvent, preferably with in particular Isopropanol, ethanol, 1,2-propylene glycol and / or dipropylene glycol, at 60-90 ° C with equimolar amounts of the quaternizing agent with stirring, possibly under pressure, and the completion of the Reaction is monitored by checking the total number of amines.
- a solvent preferably with in particular Isopropanol, ethanol, 1,2-propylene glycol and / or dipropylene glycol
- Examples of the quaternizing agents used are short-chain dialkyl phosphates and sulfates such as diethyl sulfate, dimethyl phosphate, diethyl phosphate, short chain halogenated hydrocarbons; in particular is according to the invention Dimethyl sulfate used.
- Triethanolamine was used to produce the quaternary ammonium compounds (TEA) and fatty acids implemented according to the usual procedures and quaternized.
- Fatty acid I Tallow fatty acid with an acid number of 200-210, an iodine number of 15-25 and a carbon chain distribution of ⁇ C - 16 approx. 2% C - 16 approx. 26% C - 16 ' approx. 2% C - 17 approx. 3% C - 18 approx. 48% C - 18 ' approx. 15% C - 18 " ⁇ 1% Fatty acid II Palm fatty acid with an acid number of 205-215, an iodine number of 15-25 and a C chain distribution of ⁇ C - 16 approx. 3% C - 16 approx. 47% C - 16 ' - C - 17 - C - 18 approx.
- Component A TEA: fatty acid I 1: 2 Component B: TEA: fatty acid I 1: 1.6 Component C: TEA: fatty acid II 1: 2 Component D: TEA: fatty acid II 1: 1.6 Component E: TEA: fatty acid III 1: 2 Component F: TEA: fatty acid III 1: 1.6
- the fabric softener is produced by emulsifying or dispersing of the individual components in water. This can be done on this Conventional procedures are applied.
- the fabric softeners according to the invention can be the specified ones Contain components within the usual limits in this area, such as 15-22% by weight of the compounds of the general formula (I); 2-5% by weight of a solvent, such as in particular isopropanol, Ethanol, propylene glycol, dipropylene glycol; 0.5-1.5% by weight of an alkali and / or alkaline earth metal salt; 0.5-1.5% by weight of perfume oil and the rest of 100 % By weight (ad 100) water.
- a solvent such as in particular isopropanol, Ethanol, propylene glycol, dipropylene glycol
- 0.5-1.5% by weight of an alkali and / or alkaline earth metal salt 0.5-1.5% by weight of perfume oil and the rest of 100 % By weight (ad 100) water.
- the application concentration after dilution with water lies in the range depending on the application 0.1-10 g of fabric softener per liter of treatment liquor.
- test fabric (approx. 3 kg cotton twill, 100% cotton; Supplier: WFK-Testgewebe GmbH, Krefeld) washed twice with 100 g test detergent and then without detergent (each 95 ° C program with prewash). The test fabric will hung up to dry for one day at room temperature. After drying test strips about 25 cm long and 1.5 cm wide are cut. It is important to ensure that all test strips in a test series are the same Have thread course.
- test strips are marked with a ballpoint pen. At both ends holes are punched into the test strip; there should be a 5 cm thick fabric edge remain.
- the corresponding amount of demineralized water is in the beakers submitted and 0.025%, based on the solids content, of the test Product stirred.
- a blind test is carried out by demineralizing Water is presented in the immersion bath.
- test strips are placed in each of these fleets, 5 minutes at approx. 50 rpm stirred with a magnetic stirrer and then 5 min without stirring leave in it.
- the test strips are then left for 24 hours at room temperature hanging dried. After this time, use a water-soluble marker pen on the smooth side of each strip, a line parallel to the long one Outer edges drawn.
- the test strips treated in this way are now on attached to the immersion device. It should be noted that there is no stretching the streak occurs.
- the immersion device with the strips is in the a height of 8 cm filled with demineralized water (corresponds to about 10 l) Put the tub and leave it there for 5 min. 10 min after removing the Immersion device from the tub will increase the height of the water that is at the running felt pen color can be seen, determined in mm It is on it to ensure that the lower edge of the hole with the upper side directly on the (Suspended) hook is present to avoid reading errors.
- the demineralized Water must be replaced after every attempt.
- test fabric 3 kg of the test fabric ("Duosoft" fabric, 100% cotton; supplier: Fa. Vossen) twice with 100 g of test detergent and then twice washed without detergent (each 95 ° C program with prewash, Duration approx. 2 h); Spin speed: 1200 rpm.
- test fabric Due to a fixed rotting size of 15 (Miele W 719) a liquor ratio of 1: 5. After washing, the test fabric becomes a Hung up to dry at room temperature and then until Processing stored at room temperature.
- a blind test is carried out using pure tap water in the immersion bath is presented. 1 piece of test fabric is dipped in each rinse bath. After 10 min the tissue is removed from the rinsing bath, slightly wrung out, three times gently shaken and dried hanging in one layer at room temperature for 48 h.
- test fabric treated in this way is cut into 10 pieces of the same size (approx. 16x25 cm) cut. Each test person receives a new test piece for assessment. It must be prevented that the test pieces after a few attempts are "softly gripped".
- test fabrics treated with different fabric softeners are now compared in pairs.
- the test subjects can use whole points as an evaluation distribute between 0 and 5, with 0 points bad (hard) and 5 points good (soft) mean.
Landscapes
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Wood Science & Technology (AREA)
- Organic Chemistry (AREA)
- Detergent Compositions (AREA)
- Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
Description
Fettsäure I: | |
Talgfettsäure mit einer Säurezahl von 200-210, einer Jodzahl von 15-25 und einer C-Kettenverteilung von | |
<C-16 | ca. 2 % |
C-16 | ca. 26 % |
C-16' | ca. 2 % |
C-17 | ca. 3 % |
C-18 | ca. 48 % |
C-18' | ca. 15 % |
C-18" | <1 % |
Fettsäure II | |
Palmfettsäure mit einer Säurezahl von 205-215, einer Jodzahl von 15-25 und einer C-Kettenverteilung von | |
<C-16 | ca. 3 % |
C-16 | ca. 47 % |
C-16' | - |
C-17 | - |
C-18 | ca. 28 % |
C-18' | ca. 17 % |
C-18" | ca. 2 % |
>C-18 | ca. 2% |
Fettsäure III | |
Talgfettsäure mit einer Säurezahl von 200-210, einer Jodzahl von 45-55 und einer C-Kettenverteilung von | |
<C-16 | ca. 4 % |
C-16 | ca. 26 % |
C-16' | ca. 2 % |
C-17 | ca. 3 % |
C-18 | ca. 17 % |
C-18' | ca. 41 % |
C-18" | <4 % |
>C-18 | ca. 2 % |
Komponente A: TEA : Fettsäure I | 1 : 2 |
Komponente B: TEA : Fettsäure I | 1 : 1,6 |
Komponente C: TEA : Fettsäure II | 1 : 2 |
Komponente D: TEA: Fettsäure II | 1 : 1,6 |
Komponente E: TEA: Fettsäure III | 1 : 2 |
Komponente F: TEA: Fettsäure III | 1 : 1,6 |
- BW:
- Steighöhe des Wassers (Farbstoffes) in mm der Blindproben im arithmetischen Mittel
- A:
- Steighöhe des Wassers (Farbstoffes) in mm der Proben eines Weichspülers im arithmetischen Mittel
22.0 g | Komponente A |
0.60 g | Farbstoff (1 %ige Lösung SANDOLAN® Walkblau NBL 150 der Fa. Sandoz) |
0.20 g | Entschäumungsmittel (SAG 220 der Fa. OSI) |
0.80 g | Parfümöl Fragrance®(D 60515 W der Fa. Haarmann und Reimer GmbH) |
0.20 g | CaCl2 |
ad 100 | Wasser, 9 °dH |
19.2 g | Komponente B |
0.60 g | Farbstoff (1 %ige Lösung SANDOLAN® Walkblau NBL 150 der Fa. Sandoz) |
0.20 g | Entschäumungsmittel (SAG 220 der Fa. OSI) |
0.80 g | Parfümöl Fragrance®(D 60515 W der Fa. Haarmann und Reimer GmbH) |
0.20 g | CaCl2 |
ad 100 | Wasser, 9 °dH |
22.0 g | Komponente C |
0.60 g | Farbstoff (1 %ige Lösung SANDOLAN® Walkblau NBL 150 der Fa. Sandoz) |
0.20 g | Entschäumungsmittel (SAG 220 der Fa. OSI) |
0.80 g | Parfümöl Fragrance®(D 60515 W der Fa. Haarmann und Reimer |
0.20 g | CaCl 2 |
ad 100 | Wasser, 9 °dH |
19.2 g | Komponente D |
0.60 g | Farbstoff (1 %ige Lösung SANDOLAN® Walkblau NBL 150 der Fa. Sandoz) |
0.20 g | Entschäumungsmittel (SAG 220 der Fa. OSI) |
0.80 g | Parfümöl Fragrance®(D 60515 W der Fa. Haarmann und Reimer GmbH) |
0.20 g | CaCl2 |
ad 100 | Wasser, 9 °dH |
22.0 g | Komponente E |
0.60 g | Farbstoff (1 %ige Lösung SANDOLAN® Walkblau NBL 150 der Fa. Sandoz) |
0.20 g | Entschäumungsmittel (SAG 220 der Fa. OSI) |
0.80 g | Parfümöl Fragrance®(D 60515 W der Fa. Haarmann und Reimer GmbH) |
0.20 g | CaCl2 |
ad 100 | Wasser, 9 °dH |
19.2 g | Komponente F |
0.60 g | Farbstoff (1 %ige Lösung SANDOLAN® Walkblau NBL 150 der Fa. Sandoz) |
0.20 g | Entschäumungsmittel (SAG 220 der Fa. OSI) |
0.80 g | Parfümöl Fragrance®(D 60515 W der Fa. Haarmann und Reimer GmbH) |
0.20 g | CaCl2 |
ad 100 | Wasser, 9 °dH |
Weichgriff [Punkte] | Rücknetzvermögen [%] | |
Komponente A | 42 | 56 |
Komponente B | 40 | 58 |
Komponente C | 40 | 61 |
Komponente D | 38 | 63 |
Komponente E | 32 | 62 |
Komponente F | 29 | 65 |
Weichgriff [Differenzpunkte] | ||
Komponente A : | Komponente B | 6 : 4 |
Komponente A : | Komponente C | 6 : 4 |
Komponente A : | Komponente D | 5 : 1 |
Komponente A : | Komponente E | 10 : 0 |
Komponente A : | Komponente F | 13 : 0 |
Komponente B : | Komponente C | 6 : 6 |
Komponente B : | Komponente D | 5 : 3 |
Komponente B : | Komponente E | 9 : 1 |
Komponente B : | Komponente F | 11 : 0 |
Komponente C : | Komponente D | 6 : 4 |
Komponente C : | Komponente E | 10 : 2 |
Komponente C : | Komponente F | 11 : 0 |
Komponente D : | Komponente E | 8 : 2 |
Komponente D : | Komponente F | 10 : 1 |
Komponente E : | Komponente F | 6 : 3 |
Claims (3)
- Wäßrige Weichspülmittel gemäß Anspruch 1, worin das Verhältnis von Triethanolamin : Fettsäure = 1 : 1,6 bis 1 2 ist.
- Wäßrige Weichspülmittel gemäß Anspruch 1, worin R der Rest einer Talgfettsäure oder Palmfettsäure mit Jodzahlen von 15 bis ist.
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE19756434A DE19756434A1 (de) | 1997-12-18 | 1997-12-18 | Wäßrige Weichspülmittel mit verbessertem Weichgriff |
DE19756434 | 1997-12-18 |
Publications (3)
Publication Number | Publication Date |
---|---|
EP0924291A1 EP0924291A1 (de) | 1999-06-23 |
EP0924291B1 true EP0924291B1 (de) | 2003-09-03 |
EP0924291B2 EP0924291B2 (de) | 2006-07-26 |
Family
ID=7852465
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
EP98119569A Expired - Lifetime EP0924291B2 (de) | 1997-12-18 | 1998-10-16 | Wässrige Weichspülmittel mit verbessertem Weichgriff |
Country Status (6)
Country | Link |
---|---|
US (1) | US6110887A (de) |
EP (1) | EP0924291B2 (de) |
CA (1) | CA2254399C (de) |
DE (2) | DE19756434A1 (de) |
ES (1) | ES2206808T5 (de) |
PL (1) | PL195045B1 (de) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP2576743B1 (de) | 2010-05-28 | 2015-11-11 | Colgate-Palmolive Company | Fettsäurekettensättigung bei einem esterquat auf alkanolaminbasis |
Families Citing this family (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE19855366A1 (de) * | 1998-12-01 | 2000-06-08 | Witco Surfactants Gmbh | Niedrigkonzentrierte, hochviskose wäßrige Weichspülmittel |
WO2001002338A1 (en) * | 1999-07-01 | 2001-01-11 | The Procter & Gamble Company | Quaternary nitrogen compound, fabric care composition containing same, and process for forming same |
US7371718B2 (en) * | 2005-04-22 | 2008-05-13 | The Dial Corporation | Liquid fabric softener |
EP2997959B1 (de) | 2014-09-22 | 2019-12-25 | Evonik Operations GmbH | Formulierung enthaltend esterquats basierend auf isopropanolamin und tetrahydroxypropylethylenediamin |
ES2864951T3 (es) | 2014-09-22 | 2021-10-14 | Evonik Degussa Gmbh | Emulsión que contiene esterquats líquidos y espesantes poliméricos |
Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE4400927A1 (de) * | 1994-01-14 | 1995-07-20 | Henkel Kgaa | Wäßrige Lösungen von quaternierten Fettsäuretriethanolaminester-Salze |
EP0669391A2 (de) * | 1994-02-23 | 1995-08-30 | Witco Surfactants GmbH | Hochkonzentrierte wässrige Weichspülmittel mit verbesserter Lagerstabilität |
EP0768369A1 (de) * | 1995-10-11 | 1997-04-16 | The Procter & Gamble Company | Weichspülerzusammensetzungen |
Family Cites Families (11)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
ES2021900A6 (es) * | 1989-07-17 | 1991-11-16 | Pulcra Sa | Procedimiento de obtencion de tensioactivos cationicos derivados de amonio cuaternario con funcion amino-ester. |
DE4101251A1 (de) * | 1991-01-17 | 1992-07-23 | Huels Chemische Werke Ag | Fettsaeureester des n-methyl-n,n,n-trihydroxyethyl-ammonium-methyl- sulfat enthaltende waessrige emulsionen |
ES2094893T3 (es) * | 1991-12-31 | 1997-02-01 | Stepan Europe | Tensioactivos a base de compuestos de amonio cuaternario, procedimientos de preparacion, bases, y composiciones suavizantes derivadas. |
CN1066188C (zh) * | 1993-03-01 | 2001-05-23 | 普罗格特-甘布尔公司 | 浓的可生物降解季铵织物柔软剂组合物和含有中等碘值不饱和脂肪酸链的化合物 |
JP3235915B2 (ja) * | 1993-07-13 | 2001-12-04 | ファナック株式会社 | ワイヤ結線状態表示装置 |
DE4339643C1 (de) * | 1993-11-20 | 1995-06-08 | Henkel Kgaa | Verfahren zur Herstellung von festen Esterquats |
US5869716A (en) * | 1994-03-18 | 1999-02-09 | Henkel Kommanditgesellschaft Auf Aktien | Process for the production of esterquats |
US5503756A (en) * | 1994-09-20 | 1996-04-02 | The Procter & Gamble Company | Dryer-activated fabric conditioning compositions containing unsaturated fatty acid |
DE4446137A1 (de) * | 1994-12-23 | 1996-06-27 | Huels Chemische Werke Ag | Quaternierte Triethanolamindifettsäureester |
MX9801520A (es) * | 1995-08-31 | 1998-05-31 | Colgate Palmolive Co | Composiciones suavizadoras de telas estables. |
US5916863A (en) * | 1996-05-03 | 1999-06-29 | Akzo Nobel Nv | High di(alkyl fatty ester) quaternary ammonium compound from triethanol amine |
-
1997
- 1997-12-18 DE DE19756434A patent/DE19756434A1/de not_active Ceased
-
1998
- 1998-10-16 ES ES98119569T patent/ES2206808T5/es not_active Expired - Lifetime
- 1998-10-16 EP EP98119569A patent/EP0924291B2/de not_active Expired - Lifetime
- 1998-10-16 DE DE59809482T patent/DE59809482D1/de not_active Expired - Lifetime
- 1998-11-23 US US09/198,181 patent/US6110887A/en not_active Expired - Lifetime
- 1998-11-24 CA CA002254399A patent/CA2254399C/en not_active Expired - Lifetime
- 1998-12-17 PL PL330381A patent/PL195045B1/pl unknown
Patent Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE4400927A1 (de) * | 1994-01-14 | 1995-07-20 | Henkel Kgaa | Wäßrige Lösungen von quaternierten Fettsäuretriethanolaminester-Salze |
EP0669391A2 (de) * | 1994-02-23 | 1995-08-30 | Witco Surfactants GmbH | Hochkonzentrierte wässrige Weichspülmittel mit verbesserter Lagerstabilität |
EP0768369A1 (de) * | 1995-10-11 | 1997-04-16 | The Procter & Gamble Company | Weichspülerzusammensetzungen |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP2576743B1 (de) | 2010-05-28 | 2015-11-11 | Colgate-Palmolive Company | Fettsäurekettensättigung bei einem esterquat auf alkanolaminbasis |
Also Published As
Publication number | Publication date |
---|---|
ES2206808T5 (es) | 2007-04-01 |
DE19756434A1 (de) | 1999-06-24 |
ES2206808T3 (es) | 2004-05-16 |
PL330381A1 (en) | 1999-06-21 |
PL195045B1 (pl) | 2007-08-31 |
CA2254399C (en) | 2007-07-10 |
EP0924291A1 (de) | 1999-06-23 |
EP0924291B2 (de) | 2006-07-26 |
DE59809482D1 (de) | 2003-10-09 |
US6110887A (en) | 2000-08-29 |
CA2254399A1 (en) | 1999-06-18 |
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