CA2032184C - Use of aminoxides as antistatic agents - Google Patents
Use of aminoxides as antistatic agentsInfo
- Publication number
- CA2032184C CA2032184C CA 2032184 CA2032184A CA2032184C CA 2032184 C CA2032184 C CA 2032184C CA 2032184 CA2032184 CA 2032184 CA 2032184 A CA2032184 A CA 2032184A CA 2032184 C CA2032184 C CA 2032184C
- Authority
- CA
- Canada
- Prior art keywords
- aminoxide
- fabrics
- weight
- antistatic
- fabric
- 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 - Fee Related
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
- D06M13/00—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment
- D06M13/10—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with compounds containing oxygen
- D06M13/144—Alcohols; Metal alcoholates
-
- 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
- D06M13/00—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment
- D06M13/322—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with compounds containing nitrogen
- D06M13/388—Amine oxides
Landscapes
- Engineering & Computer Science (AREA)
- Textile Engineering (AREA)
- Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
Abstract
Aqueous antistatic composition comprising 10 - 80 % by weight of an aminoxide and 2.5 - 20 % by weight of a lower alkanol axe effective antistatic agents and cause less damage on polyester fabrics than conventional antistatic agents.
Description
~ CA 02032184 1999-08-30 ' '_ C7221 (R) USE OF AMINOXIDES AS ANTISTATIC AGENTS
The present invention relates to antistatic compositions and their pse in reducing the propensity of fabrics to accumulate electrostatic charges. More in particular, it relates to the use of aminoxides as antistatic agents on fabrics which comprise polyester..
Many types of fabric have a tendency to accumulate electrical charges. Clothes which are manufactured using such fabrics are then likely to become carriers of electrostatic charges.
This is unpleasant for the person who is wearing the clothing, as the mutual attraction of oppositely charged surfaces may lead to clinging of the clothing to the body and to undergarments. Furthermore, static charges may contribute to the soiling of garments, draperies and other textile products by attracting oppositely charged particles of dust and dirt from the atmosphere onto the charged fabric.
The generation of electrostatic charges on fabrics is also undesirable in manu:Eacturing processes of sheets, films, filaments, etc, as the charges tend to cause the articles to cling together or to the processing equipment. Electrostatic -charges are particu.'larly dangerous in the manufacturing process of integrated circuits, especially of the MOS-type, as these may be irrEwersibly damaged by such charges. It is therefore essential that the protective clothing which is worn by the laborers in this branch of industry is treated in such way that accumulation of electrostatic charges is prevented or effectively reduced.
In order to reduce the propensity of fabrics to accumulate electrostatic charges it is known to provide the fabric with a finish of substances which have a high conductivity, such as quaternary ammonium compounds. Such antistatic agents may 2032 ~8~
The present invention relates to antistatic compositions and their pse in reducing the propensity of fabrics to accumulate electrostatic charges. More in particular, it relates to the use of aminoxides as antistatic agents on fabrics which comprise polyester..
Many types of fabric have a tendency to accumulate electrical charges. Clothes which are manufactured using such fabrics are then likely to become carriers of electrostatic charges.
This is unpleasant for the person who is wearing the clothing, as the mutual attraction of oppositely charged surfaces may lead to clinging of the clothing to the body and to undergarments. Furthermore, static charges may contribute to the soiling of garments, draperies and other textile products by attracting oppositely charged particles of dust and dirt from the atmosphere onto the charged fabric.
The generation of electrostatic charges on fabrics is also undesirable in manu:Eacturing processes of sheets, films, filaments, etc, as the charges tend to cause the articles to cling together or to the processing equipment. Electrostatic -charges are particu.'larly dangerous in the manufacturing process of integrated circuits, especially of the MOS-type, as these may be irrEwersibly damaged by such charges. It is therefore essential that the protective clothing which is worn by the laborers in this branch of industry is treated in such way that accumulation of electrostatic charges is prevented or effectively reduced.
In order to reduce the propensity of fabrics to accumulate electrostatic charges it is known to provide the fabric with a finish of substances which have a high conductivity, such as quaternary ammonium compounds. Such antistatic agents may 2032 ~8~
2 C7221 (R) be added to the fabric in the rinse cycle of the fabric washing process and may provide a surface resistivity in the order of 109 ohm/square.
However, it was found that the use of quaternary ammonium compounds as antistatic agents for fabrics may lead to serious chemical damage to the fabric upon repeated washing, especially if the fabric comprises polyester. This damage was found to increase with the amount of quaternary ammonium compound used, such that a compromise must be made between an effective antistatic treatment and an economically acceptable amount of damage to the protective clothing.
We have now found that this damage may be reduced or obviated when an aminoxide is used for reducing the propensity of fabrics to accumulate electrostatic charges.
According to a first aspect, the invention provides an aqueous antistatic composition suitable to be applied during or after the rinse cycle of a wash process consisting essentially of:
10-80 % by weight of an aminoxide;
2.5-20 % by weight of isopropanol; and 0.01-1 % by weight of an antifoam agent.
According to a second aspect of the present invention, there is provided a method for reducing the propensity of fabrics to accumulate electrostatic charges which comprises treating the fabrics, preferably after or during the rinse cycle of a wash process, with an antistatic composition according to the invention.
Aminoxides are well-known surfactants having a cationic character at low and neutral pH and a nonionic character at alkaline pH. Aminoxides which are advantageously used in the present invention correspond to the general formula:
However, it was found that the use of quaternary ammonium compounds as antistatic agents for fabrics may lead to serious chemical damage to the fabric upon repeated washing, especially if the fabric comprises polyester. This damage was found to increase with the amount of quaternary ammonium compound used, such that a compromise must be made between an effective antistatic treatment and an economically acceptable amount of damage to the protective clothing.
We have now found that this damage may be reduced or obviated when an aminoxide is used for reducing the propensity of fabrics to accumulate electrostatic charges.
According to a first aspect, the invention provides an aqueous antistatic composition suitable to be applied during or after the rinse cycle of a wash process consisting essentially of:
10-80 % by weight of an aminoxide;
2.5-20 % by weight of isopropanol; and 0.01-1 % by weight of an antifoam agent.
According to a second aspect of the present invention, there is provided a method for reducing the propensity of fabrics to accumulate electrostatic charges which comprises treating the fabrics, preferably after or during the rinse cycle of a wash process, with an antistatic composition according to the invention.
Aminoxides are well-known surfactants having a cationic character at low and neutral pH and a nonionic character at alkaline pH. Aminoxides which are advantageously used in the present invention correspond to the general formula:
3 C7221 (R) Ri R3 . _ wherein R1 and R3 are independently CH3 or C2H40H and R2 is an alkyl group having 12 to 18 carbon atoms. Preferably, R2 is an alkyl group having 14 to 16 carbon atoms.
Such aminoxides are commercially available, for instance from AKZO Chemie under the trade mark "Aromox". They are supplied as solutions having an active content of 30 to 40%
by weight in water,/isopropanol (50/50) or in water.
The antistatic compositions according to the invention are aqueous compositions comprising 10 to 80% by weight of an aminoxide and 2.5 i~o 20% by weight of a lower alkanol, preferably i~opropanol. Preferably they comprise 20 to 40%
aminoxide and 5 to 10% isopropanol.
Surprisingly, it was also found that antistatic compositions containing mixture: of a dimethyl alkyl aminoxide and a bis-(2-hydroxyethyl) alkyl aminoxide, whereby the alkyl groups comprise 12 to 18 carbon atoms, exhibit a more pronounced antistatic effect than compositions which contain either one of these aminoxides;.
It is advantageous when the antistatic compositions according to the invention further comprise an anti-foam agent, preferably a silicone oil, in an amount of 0.01 to 1.0 wt%, calculated on the total composition.
The compositions according to the invention may be used after or in the rinse cycle of a wash process for the treatment of fabrics in an amount of 1 to 100 g, preferably 3 to 20 g per kg wash load. Although not exclusively, the process of the present invention is primarily suitable for industrial applications, such as the industrial cleaning of overalls.
2~32184 4 C7221 (R) However, the compositions according to the invention may also be used in the pre-wash cycle of such a fabric washing process. In that case it was surprisingly found that the number of fluffs was significantly reduced. This proved to be a significant advantage for the washing of coloured linen for surgery rooms were conventional wash processes inevitably leave a large number of fluffs which have to be removed manually.
The invention will now be further illustrated by means of the following examples in which the amounts are given as % by weight, unless otherwise indicated. In the Examples, the following abbreviation is used:
ISA . Isopropanol The following aminoxide products were used which are commercially available from Akzo Chemie:
Aromox T/12 . bis-(2-hydroxyethyl) tallow aminoxide Aromox DMCD . dimethyl coconut aminoxide Aromox DM16D dimethyl hexadecyl aminoxide .
Aromox DMMCD-W dimethyl coconut aminoxide, purified .
Aromox DM14D-W dimethyl tetradecyl aminoxide .
Aromox T/12, DMCD and DM16D contain 40 % by weight of aminoxide in a solvent mixture consisting of 50 % -isopropanol and 50 % water. Aromox DMMCD-W and DM14D-W
contain 30 % by weight of aminoxide in water.
28 kg overalls made of polyester comprising fabric were subjected to a conventional industrial fabric washing process in a Spencer O.E. washing machine. The dosage of detergent product was 5 g/kg and the water hardness was 0 degrees German Hardness. The process consisted of a prewash of 2.5 minutes at 40 °C, a main wash of 6.5 minutes at 55 °C
followed by two rinse cycles of 2.5 minutes each. After the last rinse cycle, the wash load was treated for 5 minutes at C7221 (R) 18 °C with the amounts of the various antistatic compositions as indicated in Table I. After draining the overalls were removed and dried for 20 minutes in a tumble dryer at a temperature of 50 oC. The surface resistivity of the overalls 5 was then determined by measuring the resistance of the fabric according to British Standard 5958:1980 using a Philips Model 262 resistivity meter. The results are also shown in Table I. In all cases, the chemical damage which the fabrics incurred after several washes was much less than when a conventional quaternary ammonium antistatic composition was used.
~ 6 C7221 (R) 2~32~ 8~
> \
-.-~~ o 0 0 0 0 0 0 u~ o i i i ~ i i i ~ i i ~ i l0 V'N 10d' N t0 crN CD~O COO OO~ COt0 O O InO
f~ rY.rl N M r-1N M .-1N M r-1 ~ .-1 r-1n-1 r-~ r-1 O b~
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a zs m x o 0 0 0 0 0 0 0 o N v~ ~ N o - 0 0 H O d' d'd' d'd' d'M M c7 r~ N rl N N
fU H
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.-1 N O
v v (() f-1 ~-1~,d v ~r ~-1 ~1 +~ N a~ 3 3 c~ ~ ~
3 3 it 3 3 3 ~
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vo vo A A ~ ~r .-1 U U .-i.-~
Ca U U A CaL1 x x x x x x 0 0 0 0 0 0 ..
z-~ z.~ s-~ s.~ ~ s~ ~n x 3 3 3 AC ~ ~
O ~ ~ ~ ..
[](, .. .. .. .. .... p O
-rlN N N C~C~ CaU V V N N N N N N ri N
.~ r1.--1U U U .-i r1 ~ .-1 r1.-i ~ ~ ~ ~ ~ O
\ \ \ \ \ \ \ \ \ O
H E-~H C1!> faG1 G1G1 H Ei H H H H M
w ~-o x x x x x x x x x x x x x x x o a~
0 0 0 0 0 0 0 0 0 o a~ o a~ o a~ o a~ 0 0 o a)ar S-13.rS-1S-13-1S-13-1S-13-1Sa'd S-1'L3S-1'd S-1'd 3.tf-1N 'd'd [-irQ;~',~.'R'~.'AC,~' ~.'~G'R'H d,H ~'H ~L'H ~Q,',y''-~H H
p .~ N ~ ~ ~ ~pn ~pp~ O .-1 W rl N M d'1I110I~ CO01 ~-1r1 r-1r-ir-1rl rlH rie-1 N N
7 C7221 (R) The effect of an anti-static composition according to the invention was compared with the effect caused by a conventional anti-static agent of the quaternary ammonium type. Samples of three different types of polyester fabrics were soaked for 10 minutes at 40oC and at a liquid to cloth ratio of 20 to 1, using 2 g anti-static agent per litre.
Subsequently, the samples were dried for 20 minutes at 60°C.
This procedure was repeated 25 times and then the tensile strength of a test cloth having a width of 5 cm was measured (in kg) on a Louis Schopper tensile strength meter Type MT34.
The tensile strength is believed to be a good measure of the chemical damage due to the anti-static treatment. The results for three different polyester fabrics are shown below.
TABLE II
Example 22 - Polyester Fabric I.
Anti-static Agent: None Conventional Example 20 Tensile Strength:
in kg/5 cm 140.0 137.2 139.5 % difference 0.0 2.0 0.4 Example 23 - Polyester Fabric II
Anti-static Agent: None Conventional Example 20 Tensile Strength:
in kg/5 cm 116.5 112.6 113.4 difference 0.0 3.3 2.7 _ Example 24 - Polyester Fabric III
Anti-static Agent: None Conventional Example 20 Tensile Strength:
in kg/5 cm 143.7 140.0 143.6 difference 0.0 2.6 0.1 These results show that the composition of Example 20 according to the invention leads to less chemical damage on all three different types of polyester fabric then the conventional anti-static agent of the quaternary ammonium type.
Such aminoxides are commercially available, for instance from AKZO Chemie under the trade mark "Aromox". They are supplied as solutions having an active content of 30 to 40%
by weight in water,/isopropanol (50/50) or in water.
The antistatic compositions according to the invention are aqueous compositions comprising 10 to 80% by weight of an aminoxide and 2.5 i~o 20% by weight of a lower alkanol, preferably i~opropanol. Preferably they comprise 20 to 40%
aminoxide and 5 to 10% isopropanol.
Surprisingly, it was also found that antistatic compositions containing mixture: of a dimethyl alkyl aminoxide and a bis-(2-hydroxyethyl) alkyl aminoxide, whereby the alkyl groups comprise 12 to 18 carbon atoms, exhibit a more pronounced antistatic effect than compositions which contain either one of these aminoxides;.
It is advantageous when the antistatic compositions according to the invention further comprise an anti-foam agent, preferably a silicone oil, in an amount of 0.01 to 1.0 wt%, calculated on the total composition.
The compositions according to the invention may be used after or in the rinse cycle of a wash process for the treatment of fabrics in an amount of 1 to 100 g, preferably 3 to 20 g per kg wash load. Although not exclusively, the process of the present invention is primarily suitable for industrial applications, such as the industrial cleaning of overalls.
2~32184 4 C7221 (R) However, the compositions according to the invention may also be used in the pre-wash cycle of such a fabric washing process. In that case it was surprisingly found that the number of fluffs was significantly reduced. This proved to be a significant advantage for the washing of coloured linen for surgery rooms were conventional wash processes inevitably leave a large number of fluffs which have to be removed manually.
The invention will now be further illustrated by means of the following examples in which the amounts are given as % by weight, unless otherwise indicated. In the Examples, the following abbreviation is used:
ISA . Isopropanol The following aminoxide products were used which are commercially available from Akzo Chemie:
Aromox T/12 . bis-(2-hydroxyethyl) tallow aminoxide Aromox DMCD . dimethyl coconut aminoxide Aromox DM16D dimethyl hexadecyl aminoxide .
Aromox DMMCD-W dimethyl coconut aminoxide, purified .
Aromox DM14D-W dimethyl tetradecyl aminoxide .
Aromox T/12, DMCD and DM16D contain 40 % by weight of aminoxide in a solvent mixture consisting of 50 % -isopropanol and 50 % water. Aromox DMMCD-W and DM14D-W
contain 30 % by weight of aminoxide in water.
28 kg overalls made of polyester comprising fabric were subjected to a conventional industrial fabric washing process in a Spencer O.E. washing machine. The dosage of detergent product was 5 g/kg and the water hardness was 0 degrees German Hardness. The process consisted of a prewash of 2.5 minutes at 40 °C, a main wash of 6.5 minutes at 55 °C
followed by two rinse cycles of 2.5 minutes each. After the last rinse cycle, the wash load was treated for 5 minutes at C7221 (R) 18 °C with the amounts of the various antistatic compositions as indicated in Table I. After draining the overalls were removed and dried for 20 minutes in a tumble dryer at a temperature of 50 oC. The surface resistivity of the overalls 5 was then determined by measuring the resistance of the fabric according to British Standard 5958:1980 using a Philips Model 262 resistivity meter. The results are also shown in Table I. In all cases, the chemical damage which the fabrics incurred after several washes was much less than when a conventional quaternary ammonium antistatic composition was used.
~ 6 C7221 (R) 2~32~ 8~
> \
-.-~~ o 0 0 0 0 0 0 u~ o i i i ~ i i i ~ i i ~ i l0 V'N 10d' N t0 crN CD~O COO OO~ COt0 O O InO
f~ rY.rl N M r-1N M .-1N M r-1 ~ .-1 r-1n-1 r-~ r-1 O b~
O
.~1O O O O O O O O O ~ CO 01 01 d' d' N
fdM M M M M M I~ I~l~ C~ lf) OO C~ I~ ~O CO
.~ O o 0 0 0 0 o t i ~ ov co ~r o w o ~ co -~. ~-1M M M M M M 1 1 1 r-1 rl Ql t3, J~ O
N
H O -.~
U
W N
a zs m x o 0 0 0 0 0 0 0 o N v~ ~ N o - 0 0 H O d' d'd' d'd' d'M M c7 r~ N rl N N
fU H
O
O ((f d'~a O O O
I~ d' O O ~-I
..
O O QO O
N d' O O N
- O N N -.-1 O O H ..
.-1 N O
v v (() f-1 ~-1~,d v ~r ~-1 ~1 +~ N a~ 3 3 c~ ~ ~
3 3 it 3 3 3 ~
i o A D A
vo vo A A ~ ~r .-1 U U .-i.-~
Ca U U A CaL1 x x x x x x 0 0 0 0 0 0 ..
z-~ z.~ s-~ s.~ ~ s~ ~n x 3 3 3 AC ~ ~
O ~ ~ ~ ..
[](, .. .. .. .. .... p O
-rlN N N C~C~ CaU V V N N N N N N ri N
.~ r1.--1U U U .-i r1 ~ .-1 r1.-i ~ ~ ~ ~ ~ O
\ \ \ \ \ \ \ \ \ O
H E-~H C1!> faG1 G1G1 H Ei H H H H M
w ~-o x x x x x x x x x x x x x x x o a~
0 0 0 0 0 0 0 0 0 o a~ o a~ o a~ o a~ 0 0 o a)ar S-13.rS-1S-13-1S-13-1S-13-1Sa'd S-1'L3S-1'd S-1'd 3.tf-1N 'd'd [-irQ;~',~.'R'~.'AC,~' ~.'~G'R'H d,H ~'H ~L'H ~Q,',y''-~H H
p .~ N ~ ~ ~ ~pn ~pp~ O .-1 W rl N M d'1I110I~ CO01 ~-1r1 r-1r-ir-1rl rlH rie-1 N N
7 C7221 (R) The effect of an anti-static composition according to the invention was compared with the effect caused by a conventional anti-static agent of the quaternary ammonium type. Samples of three different types of polyester fabrics were soaked for 10 minutes at 40oC and at a liquid to cloth ratio of 20 to 1, using 2 g anti-static agent per litre.
Subsequently, the samples were dried for 20 minutes at 60°C.
This procedure was repeated 25 times and then the tensile strength of a test cloth having a width of 5 cm was measured (in kg) on a Louis Schopper tensile strength meter Type MT34.
The tensile strength is believed to be a good measure of the chemical damage due to the anti-static treatment. The results for three different polyester fabrics are shown below.
TABLE II
Example 22 - Polyester Fabric I.
Anti-static Agent: None Conventional Example 20 Tensile Strength:
in kg/5 cm 140.0 137.2 139.5 % difference 0.0 2.0 0.4 Example 23 - Polyester Fabric II
Anti-static Agent: None Conventional Example 20 Tensile Strength:
in kg/5 cm 116.5 112.6 113.4 difference 0.0 3.3 2.7 _ Example 24 - Polyester Fabric III
Anti-static Agent: None Conventional Example 20 Tensile Strength:
in kg/5 cm 143.7 140.0 143.6 difference 0.0 2.6 0.1 These results show that the composition of Example 20 according to the invention leads to less chemical damage on all three different types of polyester fabric then the conventional anti-static agent of the quaternary ammonium type.
Claims (4)
1. An aqueous antistatic composition to be applied during or after the rinse cycle of a wash process, consisting essentially of:
-80% by weight of an aminoxide;
-80% by weight of an aminoxide;
2.5 -20% by weight of isopropanol; and 0.01- 1% by weight of an antifoam agent, wherein the aminoxide is a mixture of a dimethyl alkyl aminoxide and a bis-(2-hydroxyethyl) alkyl aminoxide, in which the alkyl groups comprise 12 to 18 carbon atoms.
2. Antistatic composition according to claim 1, wherein the antifoam agent is a silicone oil.
2. Antistatic composition according to claim 1, wherein the antifoam agent is a silicone oil.
3. Method of reducing the propensity of fabrics to accumulate electrostatic charges, which comprises treating the fabrics with an antistatic composition according to claim 1.
4. Method according to claim 3, wherein the fabrics are treated with antistatic composition during or after the rinse cycle of a wash process.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB8928512.6 | 1989-12-18 | ||
| GB898928512A GB8928512D0 (en) | 1989-12-18 | 1989-12-18 | Antistatic compositions |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2032184A1 CA2032184A1 (en) | 1991-06-19 |
| CA2032184C true CA2032184C (en) | 1999-11-30 |
Family
ID=10668098
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA 2032184 Expired - Fee Related CA2032184C (en) | 1989-12-18 | 1990-12-13 | Use of aminoxides as antistatic agents |
Country Status (9)
| Country | Link |
|---|---|
| EP (1) | EP0434118B2 (en) |
| AU (1) | AU633166B2 (en) |
| CA (1) | CA2032184C (en) |
| DE (1) | DE69023747T3 (en) |
| ES (1) | ES2081345T5 (en) |
| FI (1) | FI98735C (en) |
| GB (1) | GB8928512D0 (en) |
| NZ (1) | NZ236496A (en) |
| ZA (1) | ZA9010182B (en) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE102015214056A1 (en) * | 2015-07-24 | 2017-01-26 | Henkel Ag & Co. Kgaa | Detergency enhancing hydroxyamine oxides |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB538711A (en) * | 1939-10-30 | 1941-08-13 | Tootal Broadhurst Lee Co Ltd | Improvements in treating materials with alkaline reagents and reagents therefor |
| GB1066763A (en) * | 1964-05-11 | 1967-04-26 | Marconi Products Ltd | Production and'use of amine oxide surface-active agents |
| US3501335A (en) * | 1965-11-26 | 1970-03-17 | Lever Brothers Ltd | Fabric conditioner |
| FR1545719A (en) * | 1966-09-02 | 1968-11-15 | Eastman Kodak Co | Improvement of the mechanical resistance of fibrous products, and new fibrous products with improved resistance |
| ES426477A1 (en) * | 1973-05-26 | 1976-07-01 | Hoechst Ag | Fiber-lubricating compositions |
-
1989
- 1989-12-18 GB GB898928512A patent/GB8928512D0/en active Pending
-
1990
- 1990-12-07 DE DE1990623747 patent/DE69023747T3/en not_active Expired - Fee Related
- 1990-12-07 ES ES90203230T patent/ES2081345T5/en not_active Expired - Lifetime
- 1990-12-07 EP EP19900203230 patent/EP0434118B2/en not_active Expired - Lifetime
- 1990-12-12 FI FI906100A patent/FI98735C/en not_active IP Right Cessation
- 1990-12-13 CA CA 2032184 patent/CA2032184C/en not_active Expired - Fee Related
- 1990-12-14 AU AU68067/90A patent/AU633166B2/en not_active Ceased
- 1990-12-17 NZ NZ23649690A patent/NZ236496A/en unknown
- 1990-12-18 ZA ZA9010182A patent/ZA9010182B/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| FI98735B (en) | 1997-04-30 |
| ES2081345T3 (en) | 1996-03-01 |
| FI906100A0 (en) | 1990-12-12 |
| FI906100A (en) | 1991-06-19 |
| EP0434118B2 (en) | 1998-10-28 |
| AU6806790A (en) | 1991-06-20 |
| ES2081345T5 (en) | 1999-02-16 |
| DE69023747D1 (en) | 1996-01-04 |
| EP0434118A2 (en) | 1991-06-26 |
| ZA9010182B (en) | 1992-08-26 |
| FI98735C (en) | 1997-08-11 |
| AU633166B2 (en) | 1993-01-21 |
| GB8928512D0 (en) | 1990-02-21 |
| NZ236496A (en) | 1992-08-26 |
| EP0434118A3 (en) | 1991-09-11 |
| DE69023747T2 (en) | 1996-04-18 |
| EP0434118B1 (en) | 1995-11-22 |
| DE69023747T3 (en) | 1999-04-15 |
| CA2032184A1 (en) | 1991-06-19 |
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