GB2201433A - Conditioning fabrics with quaternary ammonium polyalkyl siloxanes - Google Patents
Conditioning fabrics with quaternary ammonium polyalkyl siloxanes Download PDFInfo
- Publication number
- GB2201433A GB2201433A GB08803761A GB8803761A GB2201433A GB 2201433 A GB2201433 A GB 2201433A GB 08803761 A GB08803761 A GB 08803761A GB 8803761 A GB8803761 A GB 8803761A GB 2201433 A GB2201433 A GB 2201433A
- Authority
- GB
- United Kingdom
- Prior art keywords
- fabric
- conditioning
- fabrics
- group
- organofunctional
- 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.)
- Pending
Links
- 239000004744 fabric Substances 0.000 title claims description 38
- 230000003750 conditioning effect Effects 0.000 title claims description 24
- -1 siloxanes Chemical class 0.000 title claims description 8
- 125000001453 quaternary ammonium group Chemical group 0.000 title 1
- 239000003795 chemical substances by application Substances 0.000 claims description 13
- 238000000034 method Methods 0.000 claims description 13
- KPUWHANPEXNPJT-UHFFFAOYSA-N disiloxane Chemical class [SiH3]O[SiH3] KPUWHANPEXNPJT-UHFFFAOYSA-N 0.000 claims description 8
- 239000003608 nonionic fabric softener Substances 0.000 claims description 5
- 229920001296 polysiloxane Polymers 0.000 claims description 5
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- 125000001183 hydrocarbyl group Chemical group 0.000 claims description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims description 2
- 150000001450 anions Chemical class 0.000 claims description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 2
- 230000007935 neutral effect Effects 0.000 claims description 2
- 229910052760 oxygen Inorganic materials 0.000 claims description 2
- 239000001301 oxygen Substances 0.000 claims description 2
- 239000000203 mixture Substances 0.000 description 28
- 239000000463 material Substances 0.000 description 21
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- 239000000047 product Substances 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- 125000002091 cationic group Chemical group 0.000 description 4
- 239000002752 cationic softener Substances 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 4
- 238000005406 washing Methods 0.000 description 4
- 229920000742 Cotton Polymers 0.000 description 3
- NWGKJDSIEKMTRX-AAZCQSIUSA-N Sorbitan monooleate Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OC[C@@H](O)[C@H]1OC[C@H](O)[C@H]1O NWGKJDSIEKMTRX-AAZCQSIUSA-N 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 229920000728 polyester Polymers 0.000 description 3
- 229920000136 polysorbate Polymers 0.000 description 3
- VBICKXHEKHSIBG-UHFFFAOYSA-N 1-monostearoylglycerol Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCC(O)CO VBICKXHEKHSIBG-UHFFFAOYSA-N 0.000 description 2
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 2
- 241000004297 Draba Species 0.000 description 2
- 239000004593 Epoxy Substances 0.000 description 2
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical group C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 2
- 229920001214 Polysorbate 60 Polymers 0.000 description 2
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- 239000004902 Softening Agent Substances 0.000 description 2
- ACIAHEMYLLBZOI-ZZXKWVIFSA-N Unsaturated alcohol Chemical compound CC\C(CO)=C/C ACIAHEMYLLBZOI-ZZXKWVIFSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 239000004615 ingredient Substances 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 239000004669 nonionic softener Substances 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- LIVNPJMFVYWSIS-UHFFFAOYSA-N silicon monoxide Inorganic materials [Si-]#[O+] LIVNPJMFVYWSIS-UHFFFAOYSA-N 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- 239000004094 surface-active agent Substances 0.000 description 2
- 150000003512 tertiary amines Chemical class 0.000 description 2
- ZORQXIQZAOLNGE-UHFFFAOYSA-N 1,1-difluorocyclohexane Chemical compound FC1(F)CCCCC1 ZORQXIQZAOLNGE-UHFFFAOYSA-N 0.000 description 1
- 239000004698 Polyethylene Substances 0.000 description 1
- 229910018540 Si C Inorganic materials 0.000 description 1
- 229910018557 Si O Inorganic materials 0.000 description 1
- 239000004115 Sodium Silicate Substances 0.000 description 1
- IJCWFDPJFXGQBN-RYNSOKOISA-N [(2R)-2-[(2R,3R,4S)-4-hydroxy-3-octadecanoyloxyoxolan-2-yl]-2-octadecanoyloxyethyl] octadecanoate Chemical compound CCCCCCCCCCCCCCCCCC(=O)OC[C@@H](OC(=O)CCCCCCCCCCCCCCCCC)[C@H]1OC[C@H](O)[C@H]1OC(=O)CCCCCCCCCCCCCCCCC IJCWFDPJFXGQBN-RYNSOKOISA-N 0.000 description 1
- 239000012190 activator Substances 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 239000000443 aerosol Substances 0.000 description 1
- 125000000129 anionic group Chemical group 0.000 description 1
- 239000003945 anionic surfactant Substances 0.000 description 1
- 239000002216 antistatic agent Substances 0.000 description 1
- 239000007844 bleaching agent Substances 0.000 description 1
- 239000004665 cationic fabric softener Substances 0.000 description 1
- 239000003093 cationic surfactant Substances 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- IQDGSYLLQPDQDV-UHFFFAOYSA-N dimethylazanium;chloride Chemical compound Cl.CNC IQDGSYLLQPDQDV-UHFFFAOYSA-N 0.000 description 1
- 239000003792 electrolyte Substances 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000002979 fabric softener Substances 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- YQEMORVAKMFKLG-UHFFFAOYSA-N glycerine monostearate Natural products CCCCCCCCCCCCCCCCCC(=O)OC(CO)CO YQEMORVAKMFKLG-UHFFFAOYSA-N 0.000 description 1
- SVUQHVRAGMNPLW-UHFFFAOYSA-N glycerol monostearate Natural products CCCCCCCCCCCCCCCCC(=O)OCC(O)CO SVUQHVRAGMNPLW-UHFFFAOYSA-N 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 238000005470 impregnation Methods 0.000 description 1
- 238000005342 ion exchange Methods 0.000 description 1
- 238000010409 ironing Methods 0.000 description 1
- 239000012263 liquid product Substances 0.000 description 1
- 230000014759 maintenance of location Effects 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 239000002736 nonionic surfactant Substances 0.000 description 1
- 239000002304 perfume Substances 0.000 description 1
- 235000019271 petrolatum Nutrition 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 239000001818 polyoxyethylene sorbitan monostearate Substances 0.000 description 1
- 235000010989 polyoxyethylene sorbitan monostearate Nutrition 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 230000001376 precipitating effect Effects 0.000 description 1
- 239000003380 propellant Substances 0.000 description 1
- 229910010271 silicon carbide Inorganic materials 0.000 description 1
- 229910021647 smectite Inorganic materials 0.000 description 1
- 239000000344 soap Substances 0.000 description 1
- NTHWMYGWWRZVTN-UHFFFAOYSA-N sodium silicate Chemical compound [Na+].[Na+].[O-][Si]([O-])=O NTHWMYGWWRZVTN-UHFFFAOYSA-N 0.000 description 1
- 229910052911 sodium silicate Inorganic materials 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000001593 sorbitan monooleate Substances 0.000 description 1
- 235000011069 sorbitan monooleate Nutrition 0.000 description 1
- 229940035049 sorbitan monooleate Drugs 0.000 description 1
- 239000001589 sorbitan tristearate Substances 0.000 description 1
- 235000011078 sorbitan tristearate Nutrition 0.000 description 1
- 229960004129 sorbitan tristearate Drugs 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 239000003760 tallow Substances 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- 230000000007 visual effect Effects 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
- D06M15/643—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds containing silicon in the main chain
- D06M15/6436—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds containing silicon in the main chain containing amino groups
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)
- Silicon Polymers (AREA)
Description
1 2 2 0 1 '4353 C. 3162 Method of conditioning fabrics and compositions
therefor This invention relates to a method of conditioning fabrics and to compositions suitable for use in such methods.
_It is known to condition fabrics, particularly during or immediately following a fabric washing process, to improve the properties of the treated fabrics. Usually this treatment includes the treatment with a fabric softening agent intended to soften and reduce the harshness of washed fabrics. The fabric.softening agent may be included in a fabric washing composition, in a composition intended to be added to the rinse subsequent to washing the fabrics or included in a composition intended to be added with wet fabrics to a hot air dryer.
In all cases the conditioning process takes place in an aqueous environment.
1 R 1 R---Si- 0 1 R R 1 -Si--0 1 R R nL A 1+ _R2 R!- N C. 3162 A number of fabric conditioning materials are known, including soap, smectite clays, quaternary ammonium salts and fatty amines. All these materials have been commercially used but suffer from a variety of disadvantages. For example quaternary ammonium salts, which have been most widely used, are difficult to incorporate in liquid products except at relatively low concentrations, are not easily dispersed in cold water and may, if used in excess, render the treated fabrics water 10 repellant.
We have now discovered a class of fabric conditioning agents having particularly advantageous properties, and the invention is therefore characterised in that the is fabric conditioning agent is an organofunctional polyalkyl siloxane having the general formula (I) - R - 1 -- si-c 1!n L x R 1 ------S i -R -jp 1 - 1 3 - (I) R (Z) wherein each R is independently an alkyl group containing 1 to 4 carbon atoms, each of R 1, R 2, and R 3 ' is independently an alkyl group containing 1 to 24 carbon atoms or R 3 is the group (CH 2)q COO-where q is 0 to 10, A is a divalent hydrocarbon group interrupted by or substituted with one or more oxygen containing groups, X is an alkoxylated group,- Z is a-monovalent anion or the equivalent tlereof, n and m are positive integers, p is a 3 - C. 3162 positive integer and r is a positive integer or zero such as to render the siloxane electrically neutral.
We are aware of British Patent No. 1 549 180 (Procter and Gamble) which discloses the combination of a cationic softener and a selected siloxane of general formula (1), except that A is a divalent hydrocarbon group.
- European Patent Application No. 166 122 (Goldschmidt) 10 discloses siloxanes of general formula (I) in which the substituent R 3 is the group (CH 2)qCOO - and q is 1. Their preparation and their use in hair conditioning compositions is also disclosed.
The organosilicone compounds within the general formula (I) can be prepared by a variety of methods. For example, one may use as a starting material a polysilicone compound having hydrogenatoms in the side chain, ie a compound of the general formula (II) R 1 i R- Si-0 _Si-C 1 R R Si-O R Jn H R 1 si 1 m+p R (II) and such materials are commercially available. By reaction with a suitable alkoxylated omega unsaturated alcohol, a suitable allyl epoxy ether and the acid salt of a tertiary amine, the compound of general formula (I) is obtained. Thus, starting with a polysilicone of general formula (II) in which R is methyl, n is. 75 and m plus p is 7, reaction with suitable quantities of an alkoxylated unsaturated alcohol of the formula 4 1 CH 2 =CH-CH 2-O(C3 H 6 0) 11 (C 2 H 4 0) 2 H, an allyl epoxy ether of the formula C. 3162 CH =-CH -CH-O-CH -CH-CH 2 2 2 \ 0 1 2 and the acid salt of a tertiary amine of the formula (CH 3)2 N CH(CH 3)2 HOAC where 0Ac is acetate, will lead to the material S2 referred to below.
When the substituent R 3 is the group (CH 2)q COO-, then the preparation may include the procedure described in German Patent Application DE 3417912 (Th. Goldschmidt AG).
The compositions for use in the method according to the invention may take a variety of forms. They may for example be a liquid or solid fabric washing product which, in addition to the fabric conditioning agent, may comprise surfactants selected from anionic, nonionic and cationic surfactant materials, mixtures thereof or with other surfactant materials, detergency builder materials such as water-soluble precipitating or sequestering builder materials or ion-exchange builder materials, bleaches such as peroxybleaches, optionally together with bleach activators., alkaline materials such as sodium silicate, fillers such as sodium sulphate and also the other conventional ingredients of such compositions.
Alternatively the compositions for use according to the invention mas, be in the form of a rinse conditioning composition, for example a liquid rinse conditioning 1 4 i p 1; 7i e C. 3162 composition which in'addition to the fabric conditioning agent may comprise electrolytes, emulsifiers, viscosity modifying agents, thickeners, colourants and also the other conventional ingredients of such compositions.
Still further, the compositions for use in the method according to the invention may be in the form of a product for use in a hot air rotary dryer, for example in the form of a powder contained within a dispensing device or in the form of a coating on, or impregnation of, a flexible substrate material, which may be in sheet form.
Also the compositions for use according to the invention may be in a form suitable tor direct application to fabric, such as in the form of an aerosol spray containing at least the fabric conditioning agent and a suitable propellant.
Any of the above products may contain, in addition to the siloxane conditioning agent, other fabric conditioning agents such as other fabric softeners (especially water-insoluble cationic and nonionic softeners), anti-static agents (especially water-soluble cationic materials), perfumes. drape imparting agents, crease resistance imparting agents and ironing aids.
Suitable water-insoluble cationic and nonionic softeners are disclosed in European Patent Application 122 141 (Unilever) and European Patent Application 59 502 (Procter and Gamble) incorporated herein by reference.
When the compositions are in the form of rinse conditioning compositions, the total level of the polyalkylsiloxane and nonionic fabric softener, if present, lies between 3 to 30% by weight of the composition. In use such compositions are added to water 1 C. 3162 to form a liquor with which the fabrics to be treated are contacted. Generally, the total concentration of the polyalkyl siloxane and nonionic fabric softener will be between about 20 ppm and 500 ppm.
c The invention will now be further described in the following non-limiting examples.
P I C. 3162 EXAMPLES 1-10
In these examples the following materials are referred to:
S929 a commercially available material Silicone 929 (ex Dow Corning) containing amine side groups; PWK: a commercially available cationic fabric softener Prepagen WK, which is approximately dihardened tallow dimethyl ammonium chloride;. - -15 S2 a polysiloxane of general formula I-in 1 2 3 which R, R and R -are methyl, R. is isopropyl, A is the group -(CH 2)3 OCH 2 CH(OH)CH 2-' X is a randomly distributed group -O(C 3 H 6 0) 11 (C 2 H 4 0) 2 H, n is 75, m is ' 5, p is 2 and Z is actetate; S2A identical to S2 except that n is 94, m is 5 and p is 2; S2B: identical to S2 except that n is 75, m is and p is 4; GMS: glycerol monostearate; Tween 60: polyoxyethylene sorbitan monostearate containing 20 ethylene oxide groups per molecule;, 1 - 8 - C. 3162 1 Tween 65 polyoxylethylene sorbitan tristearate containing 20 ethylene oxide groups per molecule; Span 80: sorbitan monooleate.
In the following experiments, the softening performance.of these materials was tested and compared with a water-only treatment.
In a laboratory scale apparatus, one 50g piece of 67/33 polyester cotton measuring about 15cm x 15cm was rinsed in 1 litre of a rinse liquor containing 0.1%, 0.2% or 0.4% of the tested material based on the weight of the fabric. After treatment the tested cloths were line dried and the terry towelling pieces were assessed for softness against standards. A softness ranking was given to each test cloth. The results obtained were as follows, lower softness numbers indicating better softness.
Example No Tested material % on fabric softness ranking 1 nil (water) - 9 2 S 929 0.1% 6 3 S 929 0.2% 4 4 S 929 0.4% 3 PWK 0.1% 6.5 6 PWK 0.2% 4 7 PWK 0.4% 4 8 S2 0.1% 7.5 9 S2 0.2% 5.5 S2 0.4% 5.0 "' 5 J C C. 3162 t Examples 1 to 7 are comparative. Examples 8 to 10 are according to the invention.
11 The rewetability of the treated polyester cotton test cloths was-then asses,sed using a modified Draves test (CA. Draves, Am. Dyestu.ff Reporter 28, 421-1939) in which the time in seconds is measured for a small piece of treated fabric placed on the surface of water to sink.
The results were as follows:
Example No
Rewetability (seconds) 3 4 6 7 10 360 more than 600 2 3 0 These results demonstrate that the softening materials according to the invention provide fabric softening effects which are comparable with known softening materials, but also provide improved rewetability effects, especially in comparison with other silicone materials.
EXAMPLES 11-14.
In these examples, compositions containing a nonionic fabric softener and a polysiloxane were prepared according to the formulations given-below. The compositions were prepared by melting the active ingredients at 700C. The molten mixture thus formed was dispersed into hot water at 701IC-and cooled to room temperature.
k i C. 3162 The softness and rewetability of the treated polyester cotton cloths were tested as described above. The results obtained are as follows - Example Tested % on composition fabric So.ftness Rewetability ranking (seconds) 3 % GMS 0.2 6.1 3.6 6% S2A 6% Petroleum jelly 3% Tween 60 12 6% Span 80 0.2 4.6 3.4 1% Tween 65 9% S2A 13 9% Span 80 0.2 5.7 3.1 2% Tween 65 6% S2B 14 -8-10% 0.2 >120 conventional cationic softener A non-treated fabric had a softness ranking of 8.
Examples 11-14 w ere subjected to the following freeze/thaw test.
The test composition was stored in a screw-capped polyethylene bottle for 16 hours at a temperature of about -10"C. The composition was then allowed to thaw at ambient temperatures for 8 hours.
The state of each composition wc.s assessed visually after one freeze/thaw cycle.
i - 11 - C. 3162 i Example
State 11 No visual difference between products before and after one freezelthaw cycle 12 As for Example 11 13 Product was thicker than normal but was Pourable 14 Product had gelled These results show that the combination of the conditioning materials according to the invention with a nonionic fabric softener provide improved rewetability effects and are more freeze/thaw stable than compositions containing conventional cationic rinse conditioners.
1 C.3162
Claims (4)
- C L A I M S -1. A method of conditioning fabrics which comprises the stepof contacting fabrics in aii aqueous environment with a fabric conditioning agent, characterised in that the fabric conditioning agent is an organofunctinal polyalkyl siloxane having the general formula (I) R R X- 1 i-0- 1 i- 0 S s 1 1 - R R - R - - 1 --si- C 1 hL A i- C - Si-R 1 Jm L A JP 1 - R - 1 R 1 1+ R2:--N - 13 R (Z wherein each R is independently an alkyl group containing 1 to 4 carbon atoms, each of R 1, R 2, and R 3 is independently an alkyl group containing 1 to 24 carbon atoms, or R 3 is the group (CH 2)qCOO- where q is 0 to 10, A is divalent hydrocarbon group interrupted by or substituted with one or more oxygen containing groups, X is an alkoxylated group, Z is a monovalent anion or the equivalent thereof, n and m are positive integers, p is a positive integer and r is a positive integer or zero such 30 as to render the siloxane electrically neutral.
- 2. A method of conditioning fabrics according to Claim 1 characterised in that the fabric conditioning agent further comprises a nonionic fabric softener.
- 3. A method of conditioning fabrics according to Claims 1 or 2 characterised in that the organofunctional polyalkyl siloxane is selected from the group consisting of organofunctional polyalkyl siloxanes of formula (I) in which (i) m is. 5, n is 75, p is 2; (ii) m is 5, n is 94, p is 2; and (iii)m is 5, n is 75, p is 4.
- 4. A method of conditioning fabrics according to any of Claims 1 to 3 characterised in that the organofunctional polysiloxane is such that R, R' and R 2 are each methyl, R 3 is isopropyl, Z is acetate, A is -(CH 2)OCH 2 CH(OH)CH 2 - and X is -O(C 3 H 6 0) 11 (C 2 c 4 0) 2 H.m Published 1988 at The Patent Office, State House, 86/71 High Holborn, London WClR 4TP. Further copies may be obtained from The Patent office, Sales Branch, St Maxy Cray, Orpington, Kent BR5 3RD. Printed by Multiplex techniques ltd, St Mary Oray, Kent, Con. 1/87.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB878704002A GB8704002D0 (en) | 1987-02-20 | 1987-02-20 | Conditioning fabrics & compositions |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| GB8803761D0 GB8803761D0 (en) | 1988-03-16 |
| GB2201433A true GB2201433A (en) | 1988-09-01 |
Family
ID=10612645
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB878704002A Pending GB8704002D0 (en) | 1987-02-20 | 1987-02-20 | Conditioning fabrics & compositions |
| GB08803761A Pending GB2201433A (en) | 1987-02-20 | 1988-02-18 | Conditioning fabrics with quaternary ammonium polyalkyl siloxanes |
Family Applications Before (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB878704002A Pending GB8704002D0 (en) | 1987-02-20 | 1987-02-20 | Conditioning fabrics & compositions |
Country Status (4)
| Country | Link |
|---|---|
| EP (1) | EP0288137A3 (en) |
| JP (1) | JPS63243377A (en) |
| GB (2) | GB8704002D0 (en) |
| ZA (1) | ZA881180B (en) |
Cited By (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0404698A1 (en) * | 1989-06-22 | 1990-12-27 | Rhone-Poulenc Chimie | Amino and polyoxyalkylene functional polydiorganosiloxanes |
| EP0539447A4 (en) * | 1990-06-29 | 1993-06-16 | James P. Mccarthy | Cationic silicones |
| DE4222483A1 (en) * | 1992-07-09 | 1994-01-13 | Pfersee Chem Fab | Organosiloxanes with residues containing nitrogen and with ether groups |
| US6242554B1 (en) * | 1998-11-14 | 2001-06-05 | Th. Goldschmidt Ag | Polysiloxanes having polyether quat functions |
| US6313256B1 (en) * | 2000-12-06 | 2001-11-06 | Siltech Llc | Dimethicone copolyol amido quats |
| US6547981B2 (en) | 2001-03-29 | 2003-04-15 | Wacker-Chemie Gmbh | Process for treating organic fibers |
| US6942818B2 (en) * | 2000-10-13 | 2005-09-13 | Ciba Specialty Chemicals Corporation | Polysiloxanes with quarternary groups featuring nitrogen atoms |
| US7718268B2 (en) * | 2002-05-14 | 2010-05-18 | Momentive Performance Materials Gmbh | Softening silicone formulations for textile finishing |
| US11542458B2 (en) | 2015-12-28 | 2023-01-03 | Colgate-Palmolive Company | Fabric conditioners |
| US12441847B2 (en) * | 2020-07-01 | 2025-10-14 | Henkel Ag & Co. Kgaa | Bi-functionalized polysiloxane brush copolymers |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5723426A (en) * | 1996-02-29 | 1998-03-03 | Zhen; Yueqian | Liquid laundry detergent compositions containing surfactants and silicone emulsions |
| EP2212374A1 (en) * | 2007-11-21 | 2010-08-04 | Unilever PLC | Novel compounds for fabric treatment |
| EP2449078A1 (en) | 2009-06-30 | 2012-05-09 | The Procter & Gamble Company | Fabric care compositions comprising cationic polymers and amphoteric |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1549180A (en) * | 1975-07-16 | 1979-08-01 | Procter & Gamble | Textile treating compositions |
| GB2110258A (en) * | 1981-10-03 | 1983-06-15 | Dow Corning | Treating textile fibres |
| EP0166122A1 (en) * | 1984-05-15 | 1986-01-02 | Th. Goldschmidt AG | Betain groups containing siloxanes, their preparation and their use in cosmetic preparations |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3272905D1 (en) * | 1981-10-03 | 1986-10-02 | Dow Corning | Treating textile fibres |
-
1987
- 1987-02-20 GB GB878704002A patent/GB8704002D0/en active Pending
-
1988
- 1988-02-18 JP JP63036446A patent/JPS63243377A/en active Pending
- 1988-02-18 GB GB08803761A patent/GB2201433A/en active Pending
- 1988-02-18 EP EP88301346A patent/EP0288137A3/en not_active Withdrawn
- 1988-02-19 ZA ZA881180A patent/ZA881180B/en unknown
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1549180A (en) * | 1975-07-16 | 1979-08-01 | Procter & Gamble | Textile treating compositions |
| GB2110258A (en) * | 1981-10-03 | 1983-06-15 | Dow Corning | Treating textile fibres |
| EP0166122A1 (en) * | 1984-05-15 | 1986-01-02 | Th. Goldschmidt AG | Betain groups containing siloxanes, their preparation and their use in cosmetic preparations |
Cited By (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0404698A1 (en) * | 1989-06-22 | 1990-12-27 | Rhone-Poulenc Chimie | Amino and polyoxyalkylene functional polydiorganosiloxanes |
| FR2648821A1 (en) * | 1989-06-22 | 1990-12-28 | Rhone Poulenc Chimie | |
| US5075403A (en) * | 1989-06-22 | 1991-12-24 | Rhone-Poulenc Chimie | Amino/polyoxyalkylenated polydioganosiloxanes |
| US5147578A (en) * | 1989-06-22 | 1992-09-15 | Rhone-Poulenc Chimie | Amino/polyoxyalkylenated polydiorganosiloxanes |
| US5352817A (en) * | 1990-06-29 | 1994-10-04 | Karlshamns Ab | Cationic silicones |
| EP0539447A4 (en) * | 1990-06-29 | 1993-06-16 | James P. Mccarthy | Cationic silicones |
| DE4222483A1 (en) * | 1992-07-09 | 1994-01-13 | Pfersee Chem Fab | Organosiloxanes with residues containing nitrogen and with ether groups |
| US5612409A (en) * | 1992-07-09 | 1997-03-18 | Ciba-Geigy Corporation | Organosiloxanes having nitrogen-containing and ether group-containing radicals |
| US6242554B1 (en) * | 1998-11-14 | 2001-06-05 | Th. Goldschmidt Ag | Polysiloxanes having polyether quat functions |
| US6942818B2 (en) * | 2000-10-13 | 2005-09-13 | Ciba Specialty Chemicals Corporation | Polysiloxanes with quarternary groups featuring nitrogen atoms |
| US6313256B1 (en) * | 2000-12-06 | 2001-11-06 | Siltech Llc | Dimethicone copolyol amido quats |
| US6547981B2 (en) | 2001-03-29 | 2003-04-15 | Wacker-Chemie Gmbh | Process for treating organic fibers |
| US7718268B2 (en) * | 2002-05-14 | 2010-05-18 | Momentive Performance Materials Gmbh | Softening silicone formulations for textile finishing |
| US11542458B2 (en) | 2015-12-28 | 2023-01-03 | Colgate-Palmolive Company | Fabric conditioners |
| US12441847B2 (en) * | 2020-07-01 | 2025-10-14 | Henkel Ag & Co. Kgaa | Bi-functionalized polysiloxane brush copolymers |
Also Published As
| Publication number | Publication date |
|---|---|
| GB8803761D0 (en) | 1988-03-16 |
| GB8704002D0 (en) | 1987-03-25 |
| EP0288137A3 (en) | 1990-01-10 |
| JPS63243377A (en) | 1988-10-11 |
| ZA881180B (en) | 1989-10-25 |
| EP0288137A2 (en) | 1988-10-26 |
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