GB2199855A - Fabric conditioners - Google Patents
Fabric conditioners Download PDFInfo
- Publication number
- GB2199855A GB2199855A GB08800280A GB8800280A GB2199855A GB 2199855 A GB2199855 A GB 2199855A GB 08800280 A GB08800280 A GB 08800280A GB 8800280 A GB8800280 A GB 8800280A GB 2199855 A GB2199855 A GB 2199855A
- Authority
- GB
- United Kingdom
- Prior art keywords
- alkyl
- formulation
- formulation according
- groups
- 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.)
- Granted
Links
- 239000002979 fabric softener Substances 0.000 title description 6
- 239000000203 mixture Substances 0.000 claims abstract description 41
- 238000009472 formulation Methods 0.000 claims abstract description 30
- 229920001083 polybutene Polymers 0.000 claims abstract description 16
- 239000004744 fabric Substances 0.000 claims abstract description 15
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 14
- 239000002752 cationic softener Substances 0.000 claims abstract description 11
- 239000003792 electrolyte Substances 0.000 claims abstract description 9
- 239000004669 nonionic softener Substances 0.000 claims abstract description 9
- -1 alkyl imidazolinium salt Chemical class 0.000 claims abstract description 7
- 125000000217 alkyl group Chemical group 0.000 claims description 21
- 125000003342 alkenyl group Chemical group 0.000 claims description 18
- 125000001424 substituent group Chemical group 0.000 claims description 10
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 6
- 150000001450 anions Chemical group 0.000 claims description 6
- 150000003839 salts Chemical class 0.000 claims description 6
- QLAJNZSPVITUCQ-UHFFFAOYSA-N 1,3,2-dioxathietane 2,2-dioxide Chemical compound O=S1(=O)OCO1 QLAJNZSPVITUCQ-UHFFFAOYSA-N 0.000 claims description 5
- 230000003750 conditioning effect Effects 0.000 claims description 5
- 238000002156 mixing Methods 0.000 claims description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
- VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical compound CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 claims description 3
- 150000004820 halides Chemical class 0.000 claims description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims description 3
- 238000002844 melting Methods 0.000 claims description 3
- 230000008018 melting Effects 0.000 claims description 3
- 238000010008 shearing Methods 0.000 claims description 3
- 229920002367 Polyisobutene Polymers 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- 125000000524 functional group Chemical group 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 2
- 238000000034 method Methods 0.000 claims description 2
- 150000001805 chlorine compounds Chemical group 0.000 claims 1
- IQDGSYLLQPDQDV-UHFFFAOYSA-N dimethylazanium;chloride Chemical compound Cl.CNC IQDGSYLLQPDQDV-UHFFFAOYSA-N 0.000 description 7
- 230000000052 comparative effect Effects 0.000 description 6
- 239000000243 solution Substances 0.000 description 6
- MTNDZQHUAFNZQY-UHFFFAOYSA-N imidazoline Chemical class C1CN=CN1 MTNDZQHUAFNZQY-UHFFFAOYSA-N 0.000 description 5
- 239000012085 test solution Substances 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 4
- 239000006185 dispersion Substances 0.000 description 4
- 235000013162 Cocos nucifera Nutrition 0.000 description 3
- 244000060011 Cocos nucifera Species 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 2
- VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical class CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 description 2
- TWRXJAOTZQYOKJ-UHFFFAOYSA-L Magnesium chloride Chemical compound [Mg+2].[Cl-].[Cl-] TWRXJAOTZQYOKJ-UHFFFAOYSA-L 0.000 description 2
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 2
- PGZPBNJYTNQMAX-UHFFFAOYSA-N dimethylazanium;methyl sulfate Chemical compound C[NH2+]C.COS([O-])(=O)=O PGZPBNJYTNQMAX-UHFFFAOYSA-N 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- KWGKDLIKAYFUFQ-UHFFFAOYSA-M lithium chloride Chemical compound [Li+].[Cl-] KWGKDLIKAYFUFQ-UHFFFAOYSA-M 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- 239000003760 tallow Substances 0.000 description 2
- WECIKJKLCDCIMY-UHFFFAOYSA-N 2-chloro-n-(2-cyanoethyl)acetamide Chemical compound ClCC(=O)NCCC#N WECIKJKLCDCIMY-UHFFFAOYSA-N 0.000 description 1
- UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 1
- OWYWGLHRNBIFJP-UHFFFAOYSA-N Ipazine Chemical compound CCN(CC)C1=NC(Cl)=NC(NC(C)C)=N1 OWYWGLHRNBIFJP-UHFFFAOYSA-N 0.000 description 1
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 238000013019 agitation Methods 0.000 description 1
- 235000019270 ammonium chloride Nutrition 0.000 description 1
- 150000003863 ammonium salts Chemical class 0.000 description 1
- 239000001110 calcium chloride Substances 0.000 description 1
- 229910001628 calcium chloride Inorganic materials 0.000 description 1
- 125000002091 cationic group Chemical group 0.000 description 1
- 210000004534 cecum Anatomy 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 239000003599 detergent Substances 0.000 description 1
- VKKVMDHHSINGTJ-UHFFFAOYSA-M di(docosyl)-dimethylazanium;chloride Chemical compound [Cl-].CCCCCCCCCCCCCCCCCCCCCC[N+](C)(C)CCCCCCCCCCCCCCCCCCCCCC VKKVMDHHSINGTJ-UHFFFAOYSA-M 0.000 description 1
- OCTAKUVKMMLTHX-UHFFFAOYSA-M di(icosyl)-dimethylazanium;chloride Chemical compound [Cl-].CCCCCCCCCCCCCCCCCCCC[N+](C)(C)CCCCCCCCCCCCCCCCCCCC OCTAKUVKMMLTHX-UHFFFAOYSA-M 0.000 description 1
- HPDYVEVTJANPRA-UHFFFAOYSA-M diethyl(dihexadecyl)azanium;chloride Chemical compound [Cl-].CCCCCCCCCCCCCCCC[N+](CC)(CC)CCCCCCCCCCCCCCCC HPDYVEVTJANPRA-UHFFFAOYSA-M 0.000 description 1
- ZCPCLAPUXMZUCD-UHFFFAOYSA-M dihexadecyl(dimethyl)azanium;chloride Chemical compound [Cl-].CCCCCCCCCCCCCCCC[N+](C)(C)CCCCCCCCCCCCCCCC ZCPCLAPUXMZUCD-UHFFFAOYSA-M 0.000 description 1
- 238000007865 diluting Methods 0.000 description 1
- REZZEXDLIUJMMS-UHFFFAOYSA-M dimethyldioctadecylammonium chloride Chemical compound [Cl-].CCCCCCCCCCCCCCCCCC[N+](C)(C)CCCCCCCCCCCCCCCCCC REZZEXDLIUJMMS-UHFFFAOYSA-M 0.000 description 1
- 239000013020 final formulation Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 229910001629 magnesium chloride Inorganic materials 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 239000002736 nonionic surfactant Substances 0.000 description 1
- 239000002304 perfume Substances 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- 238000005406 washing Methods 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
- D06M15/21—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
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)
Abstract
An aqueous based fabric softening formulation comprises a water dispersible cationic softener, a non-ionic softener and an electrolyte. The non-ionic softener is a polybutene. The cationic softener may be a dihydrocarbyl-dialkyl ammonium salt or an alkyl imidazolinium salt. The combination of non-ionic and cationic softener now used enables the viscosity of the formulation to be lowered significantly. It also enables lower temperatures to be used to produce the formulation.
Description
FABRIC CONDITIONERS
This invention relates to compositions suitable for use in fabric conditioning.
Fabric softener formulations are usually aqueous based, contain a water dispersible cat ionic softener, a non-ionic surfactant and an electrolyte which enables the viscosity of the formulation to be controlled.
It has now been found that good fabric softening formulations may be formed by using a specific non-ionic softener without adversely affecting the fabric being softened or the softening process.
Accordingly, the present invention is an aqueous based fabric softening formulation comprising a water dispersible cationic softener, a non-ionic softener and optionally an electrolyte, characterised in that the non-ionic softener comprises a polybutene.
In the polybutene,-Ne .non-olefinic chain portion may consist of n-butyl and/or isobutyl monomer units. The terminal unit may however have one of several structures falling under the generic formula (I):
wherein R1 is the long, branched alkyl chain in the polymer, and
R2, R3 and R4 aren, or -CH3 groups such that at least one
of them is H and at least one of them is -CH3.
Thus the polybutene used in the present invention may be a poly n-butene, polyisobutene or any combinations thereof. A mixed polymer of n- and isobutenes can be produced by polymerising a raffinate containing n-butenes and isobutenes.
The polybutenes used preferably have a number average molecular weight in the range of 250 - 5000, preferably from 300 - 2000. Such polybutenes have a viscosity at 40"C in the range of 15 150,000 centistokes.
Use of polybutenes has the advantage that it facilitates handling and enables the melting point of the mixture containing the quaternary ammonium salt to be reduced, e.g. to about 35"C thereby facilitating the blending of the softener in the final formulation.
The polybutene non-ionic softener is suitably used in conjunction with conventional water-dispersible cationic softeners such as the quaternary ammonium halides or the imidazolinium halides.
Thus, according to a further embodiment the present invention is an aqueous based fabric conditioning formulation comprising: (a) a water-dispersible cat ionic softener selected from
(i) dihydrocarbyldialkylammonium salt of the formula:
wherein R5 and R6 are the same or different C12 to C24
alkyl or alkenyl groups, which may optionally carry
additional functional groups selected from -OH, -O-, -CONH and -COO- either as substituents or as
part of the main alkyl or alkenyl chain,
R7 and R8 are the same or different C1-C4 alkyl groups, and X is an anion selected from a halide, methosulphate and
ethosulphate and (ii) an alkylimidazolinium salt of the formula (III)::
wherein Rg is a C1-C4 alkyl or hydroxyalkyl group, R10 and R11 are the same or different alkyl or alkenyl groups containing from 8 to 25 carbon atoms, and R12 is hydrogen or a C1-C4 alkyl group and X- is an anion, selected from a halide methosulphate or ethosulphate and (b) a polybutene as defined above, and optionally (c) an electrolyte.
Examples of these cationic softeners of formula (II) above include ditallow dimethyl ammonium chloride; ditallow dimethyl ammonium methyl sulphate; dihexadecyl dimethyl ammonium chloride; dioctadecyl dimethyl ammonium chloride; dieicosyl dimethyl ammonium chloride; didocosyl dimethyl ammonium chloride; di(hydrogenated tallow) dimethyl ammonium methyl sulphate; dihexadecyl diethyl ammonium chloride; di(coconut alkyl) dimethyl ammonium chloride.
Ditallow dimethyl ammonium chloride, di(hydrogenated tallow alkyl) dimethyl ammonium chloride, di(coconut alkyl) dimethyl ammonium chloride and di(coconut alkyl) dimethyl ammonium methosulphate are preferred.
In a formulation containing both components (a) and (b) above if the component (a) is represented by formula (II) each of R5 and
R6 suitably represent a substituent in which more than 50%, preferably more than 75Z of the groups are C16 or C18 alkyl or alkenyl groups. More preferably, each of the substituent groups R5 and R6 represent a mixture of alkyl and alkenyl groups, namely from 50-90% C18 alkyl or alkenyl groups and from 10 to 50Z C16 alkyl or alkenyl groups.
Thus, the substituents R5 and R6 are most preferably represented by ditallow groupings, and substituents R7 and R8 are preferably methyl groups and the anion is preferably a chloride.
Thus, the preferred component (a) of formula (II) is ditallowdimethyl ammonium chloride.
Examples of the imidazolinium salts of formula (III) above include l-methyl-l-(tallowylamido-) ethyl -2-tallowyl- 4,5-dihydro imidazolinium methosulphate and l-methyl-l-(palmitoylamido)ethyl -2-octadecyl-4,5- dihydro-imidazolinium chloride. Other useful imidazolinium materials are 2-heptadecyl-1-methyl-l- (2-stearylamido)-ethyl-imidazolinium chloride and 2-lauryl-lhydroxyethyl-1-oleyl-imidazolinium chloride. Such imidazolinium fabric softening components are described more fully in US Patent No. 4 127 489 and can be used in the formulations of the present invention.
The cationic quaternary salt components falling within (a) above are commercially available materials under the following trade names or Registered Trade Marks: Arquad 2HT (ex AKZO); Noramium M2SH (ex CECA); Aliquat-2HT and the imidazolinium compounds falling within (a) are Varisoft 475 and Rewoquat W7500.
The formulations of the present invention may optionally include specific electrolytes to assist in controlling the viscosity of the product. The amount of electrolyte in the formulation is suitably from 0.01% to 0.5%, most preferably from about 0.02% to about 0.2%, measured as the anhydrous salt. Examples of electrolytes that may be used include lithium chloride, calcium chloride, magnesium chloride, aluminium chloride and mixtures thereof.
When using a fabric conditioning formulation in which both the components (a) and (b) are normally present, the following weight percentages of each based on the total weight of (a) and (b) are suitably used:
(a) 70 to 90%
(b) 30 to 104: In component (a) each of R5 and R6 preferably represent more than 50% C16 or C18 alkyl or alkenyl group, more preferably, each of R5 and R6 represent a mixture of 50 to 90% C18 alkyl or alkenyl group and 10 to 50% C16 alkyl or alkenyl group.
Preferably (a) and (b) are present in the following weight percentages based on the total weight of (a) and (b).
(a) 75 to 85Z (b) 25 to 15%
More preferably, (a) and (b) are present in the following weight percentages based on the total weight of (a) and (b)
(a) about 80%
(b) about 20%
Compositions according to the present invention may be prepared by blending, e.g. by melting (a) and (b) at temperatures under 40C.
The compositions according to the present invention may be dispersed in water by mixing the components (a) and (b) in water with moderate shearing at elevated temperature, for example, in the range 30 to 400C.
The total amount of (a) and (b) in the water is preferably from 2 to 10% by weight.
Thus as another aspect of the present invention, a fabric conditioner comprises a total of 2 to 10% by weight of (a) and (b) in an aqueous dispersion.
Other components present in the fabric conditioner formulation may include a dye and a perfume.
EXAMPLES 1. Preparation of Ditallow dimethylammonium chloride
Ditallowdimethylammonium chloride (each of R5 and R6 I more than 75% C18 or C16 alkyl or alkenyl group) can be prepared in various ways well known in the art and is a commercially available material, for example, Ciba Geigy Arquad 2HT (Regd TM).
2. Softening Test
Test Solution
Ditallowdimethylammonium chloride (available as a 75% mixture of the ammonium halide art 25% propan-2-ol) was heated at 35-400C and mixed under low shear conditions with a polybutene (Hyvis 10,
Registered Trade Mark, Mn = 1000, viscosity at 400C 7800 centistokes).
A 5Z (by total weight) dispersion was formed in water heated to 35"C, with moderate shearing and contained 4Z by weight of ditallow dimethylammonium chloride, 1% by weight of the polybutene.
When cool, 4g of this 5X dispersion was further diluted with 996g of water to obtain a test solution which simulates a typical concentration of fabric conditioner existing in a washing machine rinse cycle.
Comparative Solution
A comparative solution was prepared by diluting 4g of 5% by weight in water dispersion of the ditallowdimethylammonium chloride in 996g of water.
The test solution and the comparative solution were used to soften test cloths.
Sixteen terry towel cloths were washed twice in a commercial heavy duty detergent powder (not containing softener) to remove any coating applied during manufacture. Eight of the cloths were soaked in the test solution and eight of the cloths were soaked in the comparative solution at a cloth/liquor ratio of 150g/1.5 litres for 10 minutes with gentle agitation using a glass rod. They were subsequently removed, tumble dried and divided into eight in order that each of the softening panellists used the same sample.
Pair Comparison Tests
The softening test procedure entitled pair comparison tests was carried out using panels of 8 persons.
Panel members were required to compare the softness of two cloths A and B (one being a test cloth, the other a comparison cloth) and rank them as follows:
A is definitely softer than B Score +2
A is possibly softer than B Score +1
No difference Score 0 A is possibly harsher than B Score -1
A is definitely harsher than B Score -2
Scores for each cloth were totalled, averaged and the 95% confidence limit calculated.
On a scale of -2 to +2 the test solution scored +0.22 in a panel test compared with +0.22 for the comparative solution.
The viscosity of this new formulation at a shear rate of 1 sec-l was 95 milliPascal, compared with 550 milliPascal for the comparative solution.
The results show that the use of polybutene in the fabric conditioning formulation enables the viscosity of the formulation to be lowered significantly. It also enables lower blending temperatures to be used to produce the mixture of ingredients. The amount of ammonium salts used is also reduced.
Claims (11)
1. An aqueous based fabric softening formulation comprising a water dispersible cationic softener, a non-ionic softener and optionally an electrolyte, characterised in that the non-ionic softener comprises a polybutene.
2. A formulation according to claim 1 wherein in the polybutene is poly-n-butene, polyisobutene or mixtures thereof having a number average molecular weight in the range of 250-5000 and a viscosity of 15-150,000 centistokes at 40"C.
3. A formulation according to claim 1 or 2 wherein the polybutene is used in conjunction with a water-dispersible cationic softener selected from the quaternary ammonium halides and the imidazolinium halides.
4. An aqueous based fabric conditioning formulation according to claim 3, said formulation comprising: (a) a water-dispers ible-cationic softener selected from
(i) dihydrocarbyldialkylammonium salt of the formula:
wherein R5 and R6 are the same or different C12 to C24 alkyl or alkenyl groups, which may optionally carry additional functional groups selected from -OH, -0-, -CONH and -COO- either as substituents or as part of the main alkyl or alkenyl chain,
R7 and R8 are the same or different C1-C4 alkyl groups,
and X is an anion selected from a halide, methosulphate and
ethosulphate and (ii) an alkylimidazolinium salt of the formula (III)::
wherein Rg is a C1-C4 alkyl or hydroxyalkyl group, R10 and R11 are the same or different alkyl or alkenyl groups containing from 8 to 25 carbon atoms, and R12 is hydrogen or a C1-C4 alkyl group and X is an anion, selected from a halide, methosulphate or ethosulphate and (b) a polybutene and optionally (c) an electrolyte.
5. A formulation according to claim 4 wherein in the component (a) represented by formula (II), each of R5 and R6 is a substituent in which more than 50% of the groups are C16 or C18 alkyl or alkenyl groups.
6. A formulation according to claim 4 wherein in the component (a) represented by formula (II), each of the substituent groups R5 and
R6 represent a mixture of alkyl and alkenyl groups, whereby from 50-90% are C18 alkyl or alkenyl groups and from 10 to 50% are C16 alkyl or alkenyl groups:
7. A formulation according to claim 4 wherein in the component (a) represented by formula (II), the substituents R5 and R6 are di(hydrogenatedtallow) groupings, the substituents R7 and R8 are methyl groups, and the anion X is a chloride.
8. A formulation according to any one of the preceding claims 4-7 wherein the components (a) and (b) are present in the following percentages by weight based on the total weight of (a) and (b):
(a) 70 - 90%
(b) 30 - 10%
9. A process according to any one of the preceding claims 4-8 wherein the formulation is prepared by melting (a) and (b) at a temperature below 40"C.
10. A formulation according to any one of the preceding claims 4-8 wherein said formulation is dispersed in water by mixing components (a) and (b) in water with moderate shearing at elevated temperature.
11. A formulation according to claim 10 wherein the total amount of components (a) and (b) dispersed in water is from 2-10% w/w.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB878700538A GB8700538D0 (en) | 1987-01-10 | 1987-01-10 | Fabric conditioners |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| GB8800280D0 GB8800280D0 (en) | 1988-02-10 |
| GB2199855A true GB2199855A (en) | 1988-07-20 |
| GB2199855B GB2199855B (en) | 1990-05-30 |
Family
ID=10610529
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB878700538A Pending GB8700538D0 (en) | 1987-01-10 | 1987-01-10 | Fabric conditioners |
| GB8800280A Expired - Fee Related GB2199855B (en) | 1987-01-10 | 1988-01-07 | Fabric conditioners |
Family Applications Before (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB878700538A Pending GB8700538D0 (en) | 1987-01-10 | 1987-01-10 | Fabric conditioners |
Country Status (1)
| Country | Link |
|---|---|
| GB (2) | GB8700538D0 (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE102008053883A1 (en) | 2008-10-30 | 2010-05-06 | Henkel Ag & Co. Kgaa | new thickening system |
| US7807616B2 (en) | 2004-11-11 | 2010-10-05 | Henkel Ag & Co. Kgaa | Geranonitrile substitute |
-
1987
- 1987-01-10 GB GB878700538A patent/GB8700538D0/en active Pending
-
1988
- 1988-01-07 GB GB8800280A patent/GB2199855B/en not_active Expired - Fee Related
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7807616B2 (en) | 2004-11-11 | 2010-10-05 | Henkel Ag & Co. Kgaa | Geranonitrile substitute |
| DE102008053883A1 (en) | 2008-10-30 | 2010-05-06 | Henkel Ag & Co. Kgaa | new thickening system |
Also Published As
| Publication number | Publication date |
|---|---|
| GB8800280D0 (en) | 1988-02-10 |
| GB2199855B (en) | 1990-05-30 |
| GB8700538D0 (en) | 1987-02-11 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PCNP | Patent ceased through non-payment of renewal fee |
Effective date: 19930107 |