EP0441421B1 - Treatment of wool - Google Patents
Treatment of wool Download PDFInfo
- Publication number
- EP0441421B1 EP0441421B1 EP91200072A EP91200072A EP0441421B1 EP 0441421 B1 EP0441421 B1 EP 0441421B1 EP 91200072 A EP91200072 A EP 91200072A EP 91200072 A EP91200072 A EP 91200072A EP 0441421 B1 EP0441421 B1 EP 0441421B1
- Authority
- EP
- European Patent Office
- Prior art keywords
- treatment
- wool
- process according
- resin
- silicone polymer
- 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
- 210000002268 wool Anatomy 0.000 title claims description 25
- 229920000877 Melamine resin Polymers 0.000 claims description 18
- 238000000034 method Methods 0.000 claims description 17
- 229920005989 resin Polymers 0.000 claims description 16
- 239000011347 resin Substances 0.000 claims description 16
- 239000004640 Melamine resin Substances 0.000 claims description 15
- 229920005573 silicon-containing polymer Polymers 0.000 claims description 12
- 239000004902 Softening Agent Substances 0.000 claims description 8
- 230000003647 oxidation Effects 0.000 claims description 7
- 238000007254 oxidation reaction Methods 0.000 claims description 7
- -1 polydimethylsiloxane Polymers 0.000 claims description 4
- 238000005660 chlorination reaction Methods 0.000 claims description 3
- CEJLBZWIKQJOAT-UHFFFAOYSA-N dichloroisocyanuric acid Chemical class ClN1C(=O)NC(=O)N(Cl)C1=O CEJLBZWIKQJOAT-UHFFFAOYSA-N 0.000 claims description 3
- 239000013589 supplement Substances 0.000 claims description 3
- 239000004205 dimethyl polysiloxane Substances 0.000 claims description 2
- 150000007974 melamines Chemical class 0.000 claims description 2
- 229920000435 poly(dimethylsiloxane) Polymers 0.000 claims description 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- 239000000243 solution Substances 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- WQYVRQLZKVEZGA-UHFFFAOYSA-N hypochlorite Chemical compound Cl[O-] WQYVRQLZKVEZGA-UHFFFAOYSA-N 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- 239000004698 Polyethylene Substances 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 2
- 125000002091 cationic group Chemical group 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N formic acid Substances OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
- 239000002609 medium Substances 0.000 description 2
- LYRFLYHAGKPMFH-UHFFFAOYSA-N octadecanamide Chemical class CCCCCCCCCCCCCCCCCC(N)=O LYRFLYHAGKPMFH-UHFFFAOYSA-N 0.000 description 2
- 229920000573 polyethylene Polymers 0.000 description 2
- 229920001296 polysiloxane Polymers 0.000 description 2
- GEHJYWRUCIMESM-UHFFFAOYSA-L sodium sulfite Chemical compound [Na+].[Na+].[O-]S([O-])=O GEHJYWRUCIMESM-UHFFFAOYSA-L 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
- 229920006107 Beetle™ Polymers 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- RPNUMPOLZDHAAY-UHFFFAOYSA-N Diethylenetriamine Chemical compound NCCNCCN RPNUMPOLZDHAAY-UHFFFAOYSA-N 0.000 description 1
- 239000004952 Polyamide Substances 0.000 description 1
- MBHRHUJRKGNOKX-UHFFFAOYSA-N [(4,6-diamino-1,3,5-triazin-2-yl)amino]methanol Chemical compound NC1=NC(N)=NC(NCO)=N1 MBHRHUJRKGNOKX-UHFFFAOYSA-N 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 239000001361 adipic acid Substances 0.000 description 1
- 235000011037 adipic acid Nutrition 0.000 description 1
- 230000032683 aging Effects 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000012320 chlorinating reagent Substances 0.000 description 1
- 239000000084 colloidal system Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 239000007859 condensation product Substances 0.000 description 1
- 238000007865 diluting Methods 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 239000002612 dispersion medium Substances 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 125000003700 epoxy group Chemical group 0.000 description 1
- 238000009950 felting Methods 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 230000005484 gravity Effects 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 239000004310 lactic acid Substances 0.000 description 1
- 235000014655 lactic acid Nutrition 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000007800 oxidant agent Substances 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 229920001281 polyalkylene Polymers 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 150000003254 radicals Chemical group 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 229920002379 silicone rubber Polymers 0.000 description 1
- 235000010265 sodium sulphite Nutrition 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000008247 solid mixture Substances 0.000 description 1
- 230000006641 stabilisation Effects 0.000 description 1
- 229940037312 stearamide Drugs 0.000 description 1
- 229920003002 synthetic resin Polymers 0.000 description 1
- 239000000057 synthetic resin Substances 0.000 description 1
- 230000004584 weight gain Effects 0.000 description 1
- 235000019786 weight gain Nutrition 0.000 description 1
Classifications
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
- D06M15/00—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment
- D06M15/19—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment with synthetic macromolecular compounds
- D06M15/37—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
- D06M15/39—Aldehyde resins; Ketone resins; Polyacetals
- D06M15/423—Amino-aldehyde resins
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
- D06M15/00—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment
- D06M15/19—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment with synthetic macromolecular compounds
- D06M15/37—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
- D06M15/643—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds containing silicon in the main chain
Definitions
- This invention relates to the treatment of wool, and is particularly concerned with a process for improving its resistance to shrinkage.
- a process very widely used for this purpose entails subjecting the wool to an oxidation treatment, usually a chlorination, as with free chlorine or a hypochlorite or dichloroisocyanurate salt; removing unreacted (and potentially very damaging) oxidising agent from the wool fibres, as by passage through a reducing medium such as sodium sulphite solution, followed by a water rinse; and then treating the wool with a synthetic resin to impart a resistance to shrinkage which supplements that given by the oxidation treatment.
- an oxidation treatment usually a chlorination, as with free chlorine or a hypochlorite or dichloroisocyanurate salt
- removing unreacted (and potentially very damaging) oxidising agent from the wool fibres as by passage through a reducing medium such as sodium sulphite solution, followed by a water rinse
- a synthetic resin to impart a resistance to shrinkage which supplements that given by the oxidation treatment.
- the wool is treated with a softening agent to soften the harsh handle which it would otherwise have as a result of the resin treatment; and in due course the treated wool is dried evenly at a moderate raised temperature to ensure that adequate curing of the resin has taken place.
- the process just outlined can be applied to the treatment of wool tops (ie wool fibre before it is spun) as well as to the treatment of yarn and of woollen piece goods and garments.
- the resins most used in the process are those obtained by reaction of epichlorhydrin (a compound having a reactive epoxy group attached to the radical -CH2C1) with a polyamide whose repeating unit contains basic -NH- or -NH2 groups, as distinct from the non-basic -NH- groups of the amide linkage -CO.NH-.
- a resin is for example that obtained by the reaction of epichlorhydrin with the condensation product of a polyalkylene amine, eg diethylene triamine (H2NCH2CH2NHCH2CH2NH2) and adipic acid (HO2C.CH2CH2CH2CH2CO2H).
- a treated wool product can be obtained with properties just as good as those that result when an epichlorhydrin resin is employed, by using a colloidal melamine resin as the resin to impart resistance to shrinkage.
- Colloidal melamine resins are used in the treatment of paper to improve its wet strength, and are obtained by dissolving a partially condensed melamine formaldehyde resin in an acid such as hydrochloric, formic, acetic or lactic acid under controlled conditions, and further diluting with water. The solution becomes infinitely miscible with water, and on ageing develops a bluish haze. The solution contains positively charged colloidal particles of the melamine resin.
- Such resins have also been used, in conjunction with a non-ionic silicone elastomer, in the treatment of silk, to improve crease resistance and stability to washing, as disclosed in GB-A-2217741-A.
- a process for the treatment of wool to improve its resistance to shrinkage by subjecting it first to an oxidation treatment and then to a colloidal melamine resin treatment to supplement the shrink resistance imparted by the oxidation treatment, the resin treatment being accompanied or followed by treatment with a softening agent to soften the harsh handle associated with use of the resin, in which process the softening agent employed is a silicone polymer.
- the silicone polymer is dispersed in the colloidal melamine resin,ie in the aqueous phase which constitutes the dispersion medium of that system.
- EP-A-80272 is not, however, concerned to avoid effluent problems arising from the presence of -CH2Cl or like groups in the resin conventionally used for wool treatment; nor does it mention the use of a silicone polymer as softening agent, a use which we have found has the advantage over polyethylene softeners of producing in the wool better stabilisation against shrinkage and better non-felting properties during washing.
- the silicone polymer employed as softening agent may be cationic, but is preferably non-ionic. In general the silicone polymer used shows no chemical reactivity towards the colloidal melamine resin.
- An acidic melamine resin solution was produced by mixing the following ingredients in the following proportions by weight.
- the mixture was allowed to stand for 2 hours to develop colloidal properties, and was then diluted with an equal volume of water to give a colloidal melamine resin having a shelf life of more than 6 months.
- the diluted composition (1 part by weight) was further diluted with water (4 parts) and to this mixture was added an aqueous emulsion of a non-ionic polydimethylsiloxane (0.5 parts by weight; silicone content 35% by weight).
- a non-ionic polydimethylsiloxane 0.5 parts by weight; silicone content 35% by weight.
- BC330 silicone release agent sold by Basildon Chemicals under the designation BC330 is very suitable.
- the mixed melamine resin/silicone polymer composition was then applied, from a bath adjusted with acetic acid to pH 5-6, to knitted wool garments which had been conventionally chlorinated with a dichloroisocyanurate salt, treated with antichlor, and rinsed.
- the bath temperature was slowly raised from ambient to 40° C during 10 minutes, and held at that temperature for a further 10 minutes to exhaust the melamine resin and silicone polymer onto the wool. Weight gain was about 1.5% by dry weight of the wool.
- the material was then removed from the bath, hydroextracted and tumble-dried at 60-80° C.
- Example 1 For the treatment of wool tops the procedure of Example 1 was modified as follows.
- the mixed melamine resin/silicone polymer was applied in the 4th bowl of a conventional 5-bowl unit to deposit about 1.5% of solid mixture onto the tops.
- the treated tops were then passed to the 5th bowl, in which a cationic substituted stearamide had been included as additional softener.
- the tops were finally dried at 70-80° C.
Landscapes
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Textile Engineering (AREA)
- Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
- Chemical Or Physical Treatment Of Fibers (AREA)
Description
- This invention relates to the treatment of wool, and is particularly concerned with a process for improving its resistance to shrinkage.
- A process very widely used for this purpose entails subjecting the wool to an oxidation treatment, usually a chlorination, as with free chlorine or a hypochlorite or dichloroisocyanurate salt; removing unreacted (and potentially very damaging) oxidising agent from the wool fibres, as by passage through a reducing medium such as sodium sulphite solution, followed by a water rinse; and then treating the wool with a synthetic resin to impart a resistance to shrinkage which supplements that given by the oxidation treatment. Usually thereafter, but sometimes simultaneously with the resin treatment, the wool is treated with a softening agent to soften the harsh handle which it would otherwise have as a result of the resin treatment; and in due course the treated wool is dried evenly at a moderate raised temperature to ensure that adequate curing of the resin has taken place.
- The process just outlined can be applied to the treatment of wool tops (ie wool fibre before it is spun) as well as to the treatment of yarn and of woollen piece goods and garments.
- Probably the resins most used in the process are those obtained by reaction of epichlorhydrin (a compound having a reactive epoxy group attached to the radical -CH₂C1) with a polyamide whose repeating unit contains basic -NH- or -NH₂ groups, as distinct from the non-basic -NH- groups of the amide linkage -CO.NH-. Such a resin is for example that obtained by the reaction of epichlorhydrin with the condensation product of a polyalkylene amine, eg diethylene triamine (H₂NCH₂CH₂NHCH₂CH₂NH₂) and adipic acid (HO₂C.CH₂CH₂CH₂CH₂CO₂H). Not all such resin is exhausted onto the wool from whatever medium the epichlorhydrin resin is applied, and there is now strong evidence that the resin-containing aqueous effluent from the proceed is harmful because of the presence in it of chlorine covalently bound to carbon, as in the -CH₂Cl group.
- We have found that a treated wool product can be obtained with properties just as good as those that result when an epichlorhydrin resin is employed, by using a colloidal melamine resin as the resin to impart resistance to shrinkage. Colloidal melamine resins are used in the treatment of paper to improve its wet strength, and are obtained by dissolving a partially condensed melamine formaldehyde resin in an acid such as hydrochloric, formic, acetic or lactic acid under controlled conditions, and further diluting with water. The solution becomes infinitely miscible with water, and on ageing develops a bluish haze. The solution contains positively charged colloidal particles of the melamine resin. Such resins have also been used, in conjunction with a non-ionic silicone elastomer, in the treatment of silk, to improve crease resistance and stability to washing, as disclosed in GB-A-2217741-A.
- According to the invention, there is provided a process for the treatment of wool to improve its resistance to shrinkage, by subjecting it first to an oxidation treatment and then to a colloidal melamine resin treatment to supplement the shrink resistance imparted by the oxidation treatment, the resin treatment being accompanied or followed by treatment with a softening agent to soften the harsh handle associated with use of the resin, in which process the softening agent employed is a silicone polymer.
- Preferably, the silicone polymer is dispersed in the colloidal melamine resin,ie in the aqueous phase which constitutes the dispersion medium of that system.
- There is described in EP-A-80272 a process for the shrink-resist treatment of wool, by
- a chlorinating the wool with an acidified hypochlorite
- b removing excess chlorinating agent from the wool
- c applying to the acidified wool an acid colloid solution of a methylol melamine resin, which solution may contain a suitable softening agent, such as for example those of the polyethylene type.
- EP-A-80272 is not, however, concerned to avoid effluent problems arising from the presence of -CH₂Cl or like groups in the resin conventionally used for wool treatment; nor does it mention the use of a silicone polymer as softening agent, a use which we have found has the advantage over polyethylene softeners of producing in the wool better stabilisation against shrinkage and better non-felting properties during washing.
- The silicone polymer employed as softening agent may be cationic, but is preferably non-ionic. In general the silicone polymer used shows no chemical reactivity towards the colloidal melamine resin.
- The melamine resin employed is preferably one which has at least two -CH₂OR groups per melamine nucleus, where R = H or is an alkyl group containing from one to four carbon atoms.
- The invention is further illustrated by the following Examples.
- An acidic melamine resin solution was produced by mixing the following ingredients in the following proportions by weight.
Aqueous solution (80% reactive solids; pH at 1:1 H₂O dilution=8.5) of partially condensed melamine formaldehyde resin available as BEETLE® 336 10kg Concentrated hydrochloric acid (specific gravity=1.16) 1kg Water at 40° C 36kg - The mixture was allowed to stand for 2 hours to develop colloidal properties, and was then diluted with an equal volume of water to give a colloidal melamine resin having a shelf life of more than 6 months.
- The diluted composition (1 part by weight) was further diluted with water (4 parts) and to this mixture was added an aqueous emulsion of a non-ionic polydimethylsiloxane (0.5 parts by weight; silicone content 35% by weight). (The silicone release agent sold by Basildon Chemicals under the designation BC330 is very suitable.)
- The mixed melamine resin/silicone polymer composition was then applied, from a bath adjusted with acetic acid to pH 5-6, to knitted wool garments which had been conventionally chlorinated with a dichloroisocyanurate salt, treated with antichlor, and rinsed.The bath temperature was slowly raised from ambient to 40° C during 10 minutes, and held at that temperature for a further 10 minutes to exhaust the melamine resin and silicone polymer onto the wool. Weight gain was about 1.5% by dry weight of the wool.The material was then removed from the bath, hydroextracted and tumble-dried at 60-80° C.
- For the treatment of wool tops the procedure of Example 1 was modified as follows.
- The mixed melamine resin/silicone polymer was applied in the 4th bowl of a conventional 5-bowl unit to deposit about 1.5% of solid mixture onto the tops. The treated tops were then passed to the 5th bowl, in which a cationic substituted stearamide had been included as additional softener. The tops were finally dried at 70-80° C.
Claims (9)
- A process for the treatment of wool to improve its resistance to shrinkage, by subjecting it first to an oxidation treatment and then to a colloidal melamine resin treatment to supplement the shrink resistance imparted by the oxidation treatment, the resin treatment being accompanied or followed by treatment with a softening agent to soften the harsh handle associated with use of the resin, characterised in that the softening agent is a silicone polymer.
- A process according to claim 1, in which the silicone polymer is dispersed in the colloidal melamine resin.
- A process according to claim 1 or 2, in which the silicone polymer is non-ionic.
- A process according to claim 3, in which the silicone polymer is a polydimethylsiloxane.
- A process according to any of claims 1 to 4, in which the melamine resin has at least two -CH₂OR groups per melamine nucleus, where R = H or C₁₋₄ alkyl.
- A process according to any of claims 1 to 5, in which the oxidation treatment is a chlorination.
- A process according to claim 6, in which the chlorination utilises a dichloroisocyanurate salt.
- A process according to any of claims 1 to 7, applied to the treatment of wool tops.
- A process according to any of claims 1 to 7, applied to the treatment of knitted wool garments.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB909002680A GB9002680D0 (en) | 1990-02-07 | 1990-02-07 | Treatment of wool |
| GB9002680 | 1990-02-07 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| EP0441421A1 EP0441421A1 (en) | 1991-08-14 |
| EP0441421B1 true EP0441421B1 (en) | 1995-04-05 |
Family
ID=10670536
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| EP91200072A Expired - Lifetime EP0441421B1 (en) | 1990-02-07 | 1991-01-16 | Treatment of wool |
Country Status (6)
| Country | Link |
|---|---|
| EP (1) | EP0441421B1 (en) |
| AU (1) | AU630275B2 (en) |
| DE (1) | DE69108588T2 (en) |
| GB (2) | GB9002680D0 (en) |
| NZ (1) | NZ237014A (en) |
| ZA (1) | ZA91605B (en) |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0080272A3 (en) * | 1981-10-28 | 1984-08-22 | South African Inventions Development Corporation | Shrink-resist treatment of wool |
| GB2217741B (en) * | 1988-04-21 | 1991-07-31 | Bip Chemicals Ltd | Treatment of silk fabrics |
-
1990
- 1990-02-07 GB GB909002680A patent/GB9002680D0/en active Pending
-
1991
- 1991-01-16 DE DE69108588T patent/DE69108588T2/en not_active Expired - Fee Related
- 1991-01-16 EP EP91200072A patent/EP0441421B1/en not_active Expired - Lifetime
- 1991-01-17 GB GB9101054A patent/GB2240790B/en not_active Expired - Fee Related
- 1991-01-28 ZA ZA91605A patent/ZA91605B/en unknown
- 1991-02-05 NZ NZ237014A patent/NZ237014A/en unknown
- 1991-02-07 AU AU70866/91A patent/AU630275B2/en not_active Ceased
Also Published As
| Publication number | Publication date |
|---|---|
| AU7086691A (en) | 1991-08-08 |
| NZ237014A (en) | 1992-09-25 |
| EP0441421A1 (en) | 1991-08-14 |
| GB2240790B (en) | 1993-06-02 |
| ZA91605B (en) | 1991-10-30 |
| DE69108588D1 (en) | 1995-05-11 |
| GB2240790A (en) | 1991-08-14 |
| AU630275B2 (en) | 1992-10-22 |
| DE69108588T2 (en) | 1995-10-05 |
| GB9101054D0 (en) | 1991-02-27 |
| GB9002680D0 (en) | 1990-04-04 |
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