ZA200202685B - Fabric care composition. - Google Patents
Fabric care composition. Download PDFInfo
- Publication number
- ZA200202685B ZA200202685B ZA200202685A ZA200202685A ZA200202685B ZA 200202685 B ZA200202685 B ZA 200202685B ZA 200202685 A ZA200202685 A ZA 200202685A ZA 200202685 A ZA200202685 A ZA 200202685A ZA 200202685 B ZA200202685 B ZA 200202685B
- Authority
- ZA
- South Africa
- Prior art keywords
- composition
- fabric
- polymeric material
- polymer
- formula
- Prior art date
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- 239000000203 mixture Substances 0.000 title claims description 88
- 239000004744 fabric Substances 0.000 title claims description 79
- 239000000463 material Substances 0.000 claims description 48
- 150000001875 compounds Chemical class 0.000 claims description 42
- 238000000034 method Methods 0.000 claims description 27
- 229920000642 polymer Polymers 0.000 claims description 25
- 125000000217 alkyl group Chemical group 0.000 claims description 20
- 230000008569 process Effects 0.000 claims description 18
- 238000004900 laundering Methods 0.000 claims description 17
- 239000003599 detergent Substances 0.000 claims description 16
- -1 poly(oxyalkylene) Polymers 0.000 claims description 15
- 239000004753 textile Substances 0.000 claims description 12
- 125000002947 alkylene group Chemical group 0.000 claims description 10
- 125000003277 amino group Chemical group 0.000 claims description 9
- 239000000969 carrier Substances 0.000 claims description 8
- 239000003431 cross linking reagent Substances 0.000 claims description 8
- 238000006243 chemical reaction Methods 0.000 claims description 6
- 230000003750 conditioning effect Effects 0.000 claims description 6
- 238000005406 washing Methods 0.000 claims description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 6
- 229920001296 polysiloxane Polymers 0.000 claims description 5
- 125000002843 carboxylic acid group Chemical group 0.000 claims description 4
- 239000006187 pill Substances 0.000 claims description 4
- 239000000654 additive Substances 0.000 claims description 3
- 230000000996 additive effect Effects 0.000 claims description 3
- 239000001913 cellulose Substances 0.000 claims description 3
- 229920002678 cellulose Polymers 0.000 claims description 3
- 238000004132 cross linking Methods 0.000 claims description 3
- 125000005702 oxyalkylene group Chemical group 0.000 claims description 3
- 239000002304 perfume Substances 0.000 claims description 3
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 3
- 125000000732 arylene group Chemical group 0.000 claims description 2
- 125000005647 linker group Chemical group 0.000 claims description 2
- 125000005373 siloxane group Chemical group [SiH2](O*)* 0.000 claims description 2
- 239000007787 solid Substances 0.000 claims description 2
- 150000002118 epoxides Chemical class 0.000 claims 2
- GVNVAWHJIKLAGL-UHFFFAOYSA-N 2-(cyclohexen-1-yl)cyclohexan-1-one Chemical compound O=C1CCCCC1C1=CCCCC1 GVNVAWHJIKLAGL-UHFFFAOYSA-N 0.000 claims 1
- 101150065749 Churc1 gene Proteins 0.000 claims 1
- 101100113485 Neurospora crassa (strain ATCC 24698 / 74-OR23-1A / CBS 708.71 / DSM 1257 / FGSC 987) chs-3 gene Proteins 0.000 claims 1
- 102100038239 Protein Churchill Human genes 0.000 claims 1
- 238000011282 treatment Methods 0.000 description 14
- 125000002091 cationic group Chemical group 0.000 description 9
- 125000003342 alkenyl group Chemical group 0.000 description 8
- 230000008901 benefit Effects 0.000 description 7
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 6
- 239000003795 chemical substances by application Substances 0.000 description 6
- 239000000047 product Substances 0.000 description 5
- 125000001453 quaternary ammonium group Chemical group 0.000 description 5
- 229910000323 aluminium silicate Inorganic materials 0.000 description 4
- 150000002148 esters Chemical class 0.000 description 4
- 229920000768 polyamine Polymers 0.000 description 4
- 239000000344 soap Substances 0.000 description 4
- 239000003381 stabilizer Substances 0.000 description 4
- 210000002268 wool Anatomy 0.000 description 4
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- 239000004902 Softening Agent Substances 0.000 description 3
- 239000003945 anionic surfactant Substances 0.000 description 3
- 239000002736 nonionic surfactant Substances 0.000 description 3
- 150000002924 oxiranes Chemical class 0.000 description 3
- 150000003856 quaternary ammonium compounds Chemical class 0.000 description 3
- 239000004094 surface-active agent Substances 0.000 description 3
- VBICKXHEKHSIBG-UHFFFAOYSA-N 1-monostearoylglycerol Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCC(O)CO VBICKXHEKHSIBG-UHFFFAOYSA-N 0.000 description 2
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 2
- 229910000503 Na-aluminosilicate Inorganic materials 0.000 description 2
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical class OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 125000000129 anionic group Chemical group 0.000 description 2
- 150000001768 cations Chemical class 0.000 description 2
- 238000004140 cleaning Methods 0.000 description 2
- 235000014113 dietary fatty acids Nutrition 0.000 description 2
- IQDGSYLLQPDQDV-UHFFFAOYSA-N dimethylazanium;chloride Chemical compound Cl.CNC IQDGSYLLQPDQDV-UHFFFAOYSA-N 0.000 description 2
- HNPSIPDUKPIQMN-UHFFFAOYSA-N dioxosilane;oxo(oxoalumanyloxy)alumane Chemical compound O=[Si]=O.O=[Al]O[Al]=O HNPSIPDUKPIQMN-UHFFFAOYSA-N 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 239000002979 fabric softener Substances 0.000 description 2
- 239000000194 fatty acid Substances 0.000 description 2
- 229930195729 fatty acid Natural products 0.000 description 2
- 125000002768 hydroxyalkyl group Chemical group 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 description 2
- UMSVPCYSAUKCAZ-UHFFFAOYSA-N propane;hydrochloride Chemical compound Cl.CCC UMSVPCYSAUKCAZ-UHFFFAOYSA-N 0.000 description 2
- 230000009467 reduction Effects 0.000 description 2
- 235000012217 sodium aluminium silicate Nutrition 0.000 description 2
- 239000003760 tallow Substances 0.000 description 2
- 230000007704 transition Effects 0.000 description 2
- JNYAEWCLZODPBN-JGWLITMVSA-N (2r,3r,4s)-2-[(1r)-1,2-dihydroxyethyl]oxolane-3,4-diol Chemical class OC[C@@H](O)[C@H]1OC[C@H](O)[C@H]1O JNYAEWCLZODPBN-JGWLITMVSA-N 0.000 description 1
- GAWIXWVDTYZWAW-UHFFFAOYSA-N C[CH]O Chemical group C[CH]O GAWIXWVDTYZWAW-UHFFFAOYSA-N 0.000 description 1
- BHPQYMZQTOCNFJ-UHFFFAOYSA-N Calcium cation Chemical group [Ca+2] BHPQYMZQTOCNFJ-UHFFFAOYSA-N 0.000 description 1
- RKWGIWYCVPQPMF-UHFFFAOYSA-N Chloropropamide Chemical compound CCCNC(=O)NS(=O)(=O)C1=CC=C(Cl)C=C1 RKWGIWYCVPQPMF-UHFFFAOYSA-N 0.000 description 1
- 229920000742 Cotton Polymers 0.000 description 1
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- 239000004166 Lanolin Substances 0.000 description 1
- 239000000232 Lipid Bilayer Substances 0.000 description 1
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical class C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 1
- 229920000297 Rayon Polymers 0.000 description 1
- 239000004115 Sodium Silicate Substances 0.000 description 1
- ULUAUXLGCMPNKK-UHFFFAOYSA-N Sulfobutanedioic acid Chemical class OC(=O)CC(C(O)=O)S(O)(=O)=O ULUAUXLGCMPNKK-UHFFFAOYSA-N 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 230000029936 alkylation Effects 0.000 description 1
- 238000005804 alkylation reaction Methods 0.000 description 1
- ANBBXQWFNXMHLD-UHFFFAOYSA-N aluminum;sodium;oxygen(2-) Chemical compound [O-2].[O-2].[Na+].[Al+3] ANBBXQWFNXMHLD-UHFFFAOYSA-N 0.000 description 1
- 125000003368 amide group Chemical group 0.000 description 1
- 239000002280 amphoteric surfactant Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 230000001588 bifunctional effect Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 229910001424 calcium ion Inorganic materials 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 150000001767 cationic compounds Chemical class 0.000 description 1
- 239000004665 cationic fabric softener Substances 0.000 description 1
- 239000002752 cationic softener Substances 0.000 description 1
- 239000003093 cationic surfactant Substances 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 239000007859 condensation product Substances 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 230000008021 deposition Effects 0.000 description 1
- 150000004985 diamines Chemical class 0.000 description 1
- REZZEXDLIUJMMS-UHFFFAOYSA-M dimethyldioctadecylammonium chloride Chemical compound [Cl-].CCCCCCCCCCCCCCCCCC[N+](C)(C)CCCCCCCCCCCCCCCCCC REZZEXDLIUJMMS-UHFFFAOYSA-M 0.000 description 1
- 239000004664 distearyldimethylammonium chloride (DHTDMAC) Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 238000005187 foaming Methods 0.000 description 1
- 229940083124 ganglion-blocking antiadrenergic secondary and tertiary amines Drugs 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
- WNLRTRBMVRJNCN-UHFFFAOYSA-N hexanedioic acid Chemical class OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 1
- 125000001183 hydrocarbyl group Chemical group 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 150000002462 imidazolines Chemical class 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 238000005342 ion exchange Methods 0.000 description 1
- 238000010409 ironing Methods 0.000 description 1
- 229940039717 lanolin Drugs 0.000 description 1
- 235000019388 lanolin Nutrition 0.000 description 1
- 239000000787 lecithin Substances 0.000 description 1
- 235000010445 lecithin Nutrition 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 239000004669 nonionic softener Substances 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 1
- 229940055076 parasympathomimetics choline ester Drugs 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 229920002959 polymer blend Polymers 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 150000003138 primary alcohols Chemical class 0.000 description 1
- 150000003141 primary amines Chemical class 0.000 description 1
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 239000004627 regenerated cellulose Substances 0.000 description 1
- 150000003333 secondary alcohols Chemical class 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910001388 sodium aluminate Inorganic materials 0.000 description 1
- 239000000429 sodium aluminium silicate Substances 0.000 description 1
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 1
- 159000000000 sodium salts Chemical class 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
- 239000007921 spray Substances 0.000 description 1
- TYFQFVWCELRYAO-UHFFFAOYSA-N suberic acid Chemical class OC(=O)CCCCCCC(O)=O TYFQFVWCELRYAO-UHFFFAOYSA-N 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- 150000004072 triols Chemical class 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
- C11D3/16—Organic compounds
- C11D3/37—Polymers
- C11D3/3703—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
- C11D3/3707—Polyethers, e.g. polyalkyleneoxides
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
- C11D3/16—Organic compounds
- C11D3/20—Organic compounds containing oxygen
- C11D3/22—Carbohydrates or derivatives thereof
- C11D3/222—Natural or synthetic polysaccharides, e.g. cellulose, starch, gum, alginic acid or cyclodextrin
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
- C11D3/16—Organic compounds
- C11D3/37—Polymers
- C11D3/3703—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
- C11D3/3723—Polyamines or polyalkyleneimines
Landscapes
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Wood Science & Technology (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- Emergency Medicine (AREA)
- Detergent Compositions (AREA)
- Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
Description
FABRIC CARE COMPOSITION
This invention relates to fabric care compositions and to methods of treating fabric using the compositions or the polymeric materials they contain.
Background and Prior Art
The laundry process generally has several benefits for fabric, the most common being to remove dirt and stains from the fabric during the wash cycle and to soften the fabric . during the rinse cycle. However, there are numerous V4 disadvantages associated with repeated use of conventional oo laundry treatment compositions and/or the actual laundry process; one of these being a fairly harsh treatment of : fabric in the laundry process.
Fabrics can be damaged in several ways as a result of repeated laundering and/or wear. Fabric pilling and loss of fabric surface appearance e.g. fuzzing, shrinkage (or expansion), loss of colour from the fabric or running of colour on the fabric (usually termed dye transfer) are some of the common problems associated with repeated laundering.
These problems may occur merely from repeated hand washing as well as the more vigorous machine washing process.
Furthermore, problems relating to damage of fabric over time through normal use, such as loss of shape and increased likelihood of wrinkling are also significant.
* + WO 01/27232 PCT/GB00/03695
The present invention is directed towards alleviating one or more of the problems referred to hereinabove.
The principal advantage of the present invention relates to improving the surface colour definition of a fabric after multiple washings and/or to imparting pill and/or fuzz resistance to fabric during laundering. The invention can have further advantages in the treatment of fabric. For example, other aspects of the overall appearance of the fabric can be improved, such as a reduction in the tendency of the fabric to become creased and/or wrinkled.
Laundry detergent compositions containing polyamide- polyamine fabric treatment agents are described in WO 98/29530. The compositions are claimed to impart improved ) overall appearance to fabrics laundered using the detergent compositions, in terms of surface appearance properties such as pill/fuzz reduction and antifading. Laundry compositions containing polyamide-polyamine treatment agents of similar types are taught in WO 97/42287.
Laundry compositions containing polyamide-polyamine fabric treatment agents can exhibit increased dye pick-up (ie, increased dye transfer) and poor stain removal properties compared to other conventional laundry compositions.
US 5571286 (Connell et al) discloses certain polymers and prepolymers derived from polyoxyalkyleneamines and their use in a process for shrink-proofing wool. The treated wool may also have a softer handle than untreated wool. This document does not mention the treatment of cellulosic i fabrics or the problems of loss of fabric surface appearance that they can experience following laundering. Furthermore, it deals entirely with treatment of wool on an industrial scale and does not mention the application of the compositions to fabric in the context of laundering processes.
The present invention is based on the surprising finding that certain polymeric materials, including those described in US 5571286, can impart improved surface appearance to cellulosic fabrics. The polymeric materials can have the further advantage of reduced adverse side-effects, in terms of increased dye transfer and poor stain removal, for example, compared to certain compositions containing polyamide-polyamine fabric treatment agents.
According to the present invention, there is provided the use of a fabric care composition to improve the surface colour definition of a fabric after multiple washings and/or to impart pill and/or fuzz resistance to fabric during laundering, wherein the composition comprises a polymeric : material which is capable of self cross-linking and/or of : reacting with cellulose together with one or more textile compatible carriers, wherein the polymeric material comprises one or more poly(oxyalkylene) groups having an end group which comprises one or more amino groups or derivatives of said amino groups, and wherein when the textile compatible carrier is water a further additive : suitable for use in laundry compositions is present. ; - = = = — — — —- =~ . _Fmended Sheet 28/03/2003 ,
The compositions of the present invention comprise a polymeric material which is capable of self cross-linking and/or of reacting with cellulose together with one or more textile compatible carriers, wherein the polymeric material comprises one or more poly (oxyalkylene) groups having an end group which comprises one or more amino groups Or derivatives of said amino groups.
LE] _ i. : ~. Amended Sheet 28/03/2003 —
The compositions of the invention have the surprising advantage of imparting wear resistance to fabrics, and thereby causing improved surface colour definition of the fabric after laundering, particularly after multiple washings. Furthermore, the polymeric materials contained in the compositions need not cause unacceptable dye transfer and/or stain removal problems.
The polymeric material which can be used in the present invention can be any of the polymers or prepolymers derived from polyoxyalkyleneamines that are described in US 5571286, the contents of which are incorporated herein by reference.
Methods for preparing the polymeric materials are described in US 5571286. Hence the polymeric material can be, for example, the reaction product of a diamine or triamine oo polyoxyalkylene polymer having a polymerisation degree of from 4 to 50 or a mixture thereof with epichlorohydrin in a ratio of epichlorohydrin to amino nitrogen of from 1:1 to 3:1.
The amino groups in the polymeric material of the invention may wholly or partly in the form of derivatives of amino groups. Derivatives include, for example, adducts formed by alkylation or hydroxyalkylation at the nitrogen atom or by the formation of an amide group at the nitrogen atom. The derivatives may be formed by the reaction of the amino groups with a bifunctional bridging agent or with a cross- linking agent.
Preferably, the polymeric material is obtainable by the reaction of a polymer of formula B(R),, wherein n is from 1 to 20, B is a backbone group to which each R is covalently bonded and R is a group comprising a poly(oxyalkylene) chain, which chain comprises an amino end group, the polymer being optionally reacted with a bridging compound, with a cross-linking agent. It will thus be appreciated that the polymeric material of the invention is a relatively complex mixture comprising a number of different compounds, some or all of which may be cross-linked.
The poly(oxyalkylene) chain which forms a part of the R group may be, for example, a poly(oxyethylene), poly (oxybutylene) or poly (oxyprop-1l,2-ylene) chain. The length of the chain can vary from 2 to 100 repeat units.
Conveniently,n is 2 or 3. It will be appreciated that n may : not be a whole number where the polymeric material of the invention comprises a mixture of different polymers of formula B(R),.
In some of the polymeric materials which may be used in the invention,B is -0-CH; (CH) p,—CH,-0O- (ie, B is the residue of glycerol when m is 1) and m is equal 0 to n-2.
However, B can also represent other values such as , for example, the residue of other triols or the residue of a di- , tetra-, penta- or hexa- hydroxy compound. Alternatively,
B can represent the residue of a di-, tri- or poly- amine.
. - 7 =
Preferably, at least one R group has the formula - (CH2CH (R') (CH2) a0) p-A-NHR'', wherein: R' is H or CHs; a is 0, 1 or 2; p is an integer from 5 to 30; A is an alkylene group; and R'' is H or alkyl. More preferably, p is from 10 to 25.
The term “alkyl”, as used herein, includes C; to C¢ alkyl, optionally substituted on the alkyl chain, which may be branched or unbranched and, for C3; to Cg alkyl, may be cyclic. The term “alkylene” is defined similarly but refers to a divalent radical.
It will be appreciated that the term “end group” refers to the group at or near to the end of the poly(oxyalkylene) chain, which end, when the polymer is of formula B(R),, is at the other end of the polymer chain from the end which is attached to B.
Suitable polymers of formula B(R), include those having the following structure:
H,C-O (CH,CH(R') 0) p—A-NH;
HC-O (CH,CH(R'") 0) —A-NH;
H2,C=O (CH,CH(R')O0) ,~A-NH, wherein R' is as defined herein before, P, q and r are integers which may be the same or different and may be from 5 to 30 and A is branched or unbranched lower alkylene.
Other suitable polymers of formula B(R),, in which n is equal to 2, include those having the following formula:
HaN- (CHz) p= (O (CHz) 4) =O (CHz) cO- ( (CH2) 40) g2— (CH2) p~NH, wherein: b is an integer from 1 to 6, preferably 3; c is an integer from 1 to 6, preferably 4; and d and d2 are the same or different and are integers from 10 to 15.
The cross-linking agent which is used to form the polymeric material of the invention by reaction with the polymer, or the polymer after prior reaction with the bridging compound, preferably comprises an epihalohydrin. Epichlorohydrin is a suitable epihalohydrin.
Preferably the molar ratio of cross-linking agent to polymer of formula B(R), is from 0.5:1 to 4:1. Other amounts of cross-linking agent may be present in the polymeric material of the invention.
Suitable bridging compounds comprise two epoxide or carboxylic acid groups. The epoxide or carboxylic acid groups may be linked by a linker comprising alkylene, arylene, poly(oxyalkylene) or siloxane groups or combinations thereof. Examples of bridging compounds therefore include benzene-1,4-dicarboxylic acid, hexane-1, 6- dicarboxylic acid and poly (oxyethylene) compounds terminated at both ends of the molecule by an epoxide group. Other suitable bridging compounds are disclosed in US 5571286.
The composition of the invention can contain the polymeric material, optionally together with other polymeric materials. The compositions may further comprise a silicone
- 9g = which is capable of reacting with the polymeric material.
Suitable reactive silicones include those having amino or hydroxyl groups which are well-known to those skilled in the art.
Preferably, the polymeric material is capable of increasing the wet strength of paper by at least 200% compared to untreated paper when applied to paper having a weight of 80 g/m’ at a level of 1% solids by weight based on weight of paper, according to the test method described hereinafter. ] Polymeric materials which are suitable for use in the } present invention are available from Precision Processes
Textiles (Ambergate, Derbyshire, UK) under the trade marks
POLYMER AM and POLYMER MRSM. The polymeric materials of the invention are preferably in the form of aqueous solutions.
Polymer AM is a polymer having the following structure:
C2Hs C,H; C2Hs
HO PN CH,
CH,CI OH HO OH
CH,CI CH,CI
POLYMER AM
Polymer MRSM has the same structures as polymer AM but has silicone added to the polymer mixture.
The nature of the textile compatible carrier will be dictated to a large extent by the stage at which the composition of the invention is used in a laundering process, the compositions being capable of being used, in principle, at any stage of the process. For example, where the compositions are for use as main wash detergent compositions, the one or more textile compatible carriers comprise a detergent active compound. Where the compositions are for use in the rinsing step of a laundering process, the one or more textile compatible carriers may comprise a fabric softening and/or conditioning compound.
The compositions of the invention preferably comprise a perfume, such as of the type which is conventionally used in fabric care compositions. The compositions may be packaged and labelled for use in a domestic laundering process.
The polymeric material is preferably present in the product in a sufficient quantity to give an amount of 0.0005% to 5% by weight on the fabric based on the weight of the fabric, more preferably 0.001% to 2% by weight on fabric. The amount of the polymeric material in the composition required to achieve the above % by weight on fabric will typically be in the range 0.01% to 35% by weight, preferably 0.1 to 13.5% by weight.
The compositions of the invention, when applied to a fabric, can impart benefits to the fabric when uncured. However, they may be cured by a domestic curing step including ironing and/or domestic tumble drying, preferably tumble drying. The curing is preferably carried out at a temperature in the range of from 50 to 100°C, more preferably from 80 to 100°C.
In the context of the present invention the term “textile compatible carrier” is a component which can assist in the interaction of the first component with the fabric. The carrier can also provide benefits in addition to those provided by the first component e.g. softening, cleaning . etc. The carrier may be water, in which case the composition of the invention will contain another additive, . suitable for use in laundry compositions such as perfume, for example, or the carrier may be a detergent-active compound or a fabric softener or conditioning compound or other suitable detergent or fabric treatment agent.
If the composition of the invention is to be used in a laundry process as part of a conventional fabric treatment product, such as a detergent composition, the textile- compatible carrier will typically be a detergent-active compound. Whereas, if the fabric treatment product is a rinse conditioner, the textile-compatible carrier will be a fabric softening and/or conditioning compound.
If the composition of the invention is to be used before, or after, the laundry process it may be in the form of a spray or foaming product.
y +. WO 01/27232 PCT/GB00/03695 - 12 =
The fabrics which may be treated in the present invention include those which comprise cellulosic fibres, preferably from 1% to 100% cellulosic fibres (more preferably 5% to 100% cellulosic fibres, most preferably 40% to 100%). The fabric may be in the form of a garment, in which case the method of the invention may represent a method of laundering a garment. When the fabric contains less than 100% cellulosic fibres, the balance comprises other fibres or blends of fibres suitable for use in garments such as polyester, for example. Preferably, the cellulosic fibres are of cotton or regenerated cellulose such as viscose.
The laundering processes of the present invention include the large scale and small scale (eg domestic) cleaning of fabrics. Preferably, the processes are domestic.
In the invention, the polymeric material or the composition of the invention may be used at any stage of the laundering process. Preferably, the composition or the polymeric material is used to treat the fabric in the rinse cycle of a laundering process. The rinse cycle preferably follows the treatment of the fabric with a detergent composition.
Detergent Active Compounds
If the composition of the present invention is in the form of a detergent composition, the textile-compatible carrier may be chosen from soap and non-soap anionic, cationic, nonionic, amphoteric and zwitterionic detergent active compounds, and mixtures thereof.
Many suitable detergent active compounds are available and are fully described in the literature, for example, in “Surface-Active Agents and Detergents”, Volumes I and II, by
Schwartz, Perry and Berch.
The preferred textile-compatible carriers that can be used are soaps and synthetic non-soap anionic and nonionic compounds.
Anionic surfactants are well-known to those skilled in the art. Examples include alkylbenzene sulphonates, particularly linear alkylbenzene sulphonates having an alkyl chain length of Cg-C;s; primary and secondary alkylsulphates, particularly Cg-C;s primary alkyl sulphates; alkyl ether sulphates; olefin sulphonates; alkyl xylene sulphonates; dialkyl sulphosuccinates; and fatty acid ester sulphonates.
Sodium salts are generally preferred.
Nonionic surfactants that may be used include the primary and secondary alcohol ethoxylates, especially the Cg-Cag aliphatic alcohols ethoxylated with an average of from 1 to 20 moles of ethylene oxide per mole of alcohol, and more especially the C10-C;s primary and secondary aliphatic alcohols ethoxylated with an average of from 1 to 10 moles of ethylene oxide per mole of alcohol. Non-ethoxylated nonionic surfactants include alkylpolyglycosides, glycerol monoethers, and polyhydroxyamides (glucamide).
Cationic surfactants that may be used include quaternary ammonium salts of the general formula R1R2R3R4N* X~ wherein the R groups are independently hydrocarbyl chains of C1-C»; length, typically alkyl, hydroxyalkyl or ethoxylated alkyl groups, and X is a solubilising cation (for example, compounds in which R; is a Cg-Cjp alkyl group, preferably a
Cg—Cio or C;2-Ci4 alkyl group, R, is a methyl group, and R; and
R4, which may be the same or different, are methyl or hydroxyethyl groups); and cationic esters (for example, choline esters) and pyridinium salts.
The total quantity of detergent surfactant in the composition is suitably from 0.1 to 60 wt$ e.g. 0.5-55 wtg, such as 5-50wt%.
Preferably, the quantity of anionic surfactant (when present) is in the range of from 1 to 50% by weight of the total composition. More preferably, the quantity of anionic surfactant is in the range of from 3 to 35% by weight, e.g. 5 to 30% by weight.
Preferably, the quantity of nonionic surfactant when present is in the range of from 2 to 25% by weight, more preferably from 5S to 20% by weight.
Amphoteric surfactants may also be used, for example amine oxides or betaines.
The compositions may suitably contain from 10 to 70%, preferably from 15 to 70% by weight, of detergency builder.
Preferably, the quantity of builder is in the range of from 15 to 50% by weight.
The detergent composition may contain as builder a crystalline aluminosilicate, preferably an alkali metal aluminosilicate, more preferably a sodium aluminosilicate.
The aluminosilicate may generally be incorporated in amounts of from 10 to 70% by weight (anhydrous basis), preferably from 25 to 50%. Aluminosilicates are materials having the general formula: 0.8-1.5 MO. Al,0;. 0.8-6 SiO; where M is a monovalent cation, preferably sodium. These materials contain some bound water and are required to have a calcium ion exchange capacity of at least 50 mg CaO/g.
The preferred sodium aluminosilicates contain 1.5-3.5 SiO, units in the formula above. They can be prepared readily by reaction between sodium silicate and sodium aluminate, as amply described in the literature.
Fabric Softening and/or Conditioner Compounds
If the composition of the present invention is in the form of a fabric conditioner composition, the textile-compatible carrier will be a fabric softening and/or conditioning compound (hereinafter referred to as “fabric softening compound”), which may be a cationic or nonionic compound.
The softening and/or conditioning compounds may be water insoluble quaternary ammonium compounds. The compounds may be present in amounts of up to 8% by weight (based on the total amount of the composition) in which case the compositions are considered dilute, or at levels from 8% to about 50% by weight, in which case the compositions are considered concentrates.
Compositions suitable for delivery during the rinse cycle . may also be delivered to the fabric in the tumble dryer if used in a suitable form. Thus, another product form is a composition (for example, a paste) suitable for coating onto, and delivery from, a substrate e.g. a flexible sheet or sponge or a suitable dispenser during a tumble dryer cycle.
Suitable cationic fabric softening compounds are substantially water-insoluble quaternary ammonium materials comprising a single alkyl or alkenyl long chain having an average chain length greater than or equal to Cy or, more preferably, compounds comprising a polar head group and two alkyl or alkenyl chains having an average chain length greater than or equal to Cis. Preferably the fabric softening compounds have two long chain alkyl or alkenyl chains each having an average chain length greater than or equal to Cj¢. Most preferably at least 50% of the long chain alkyl or alkenyl groups have a chain length of C;3 or above.
It is preferred if the long chain alkyl or alkenyl groups of the fabric softening compound are predominantly linear.
Quaternary ammonium compounds having two long-chain aliphatic groups, for example, distearyldimethyl ammonium chloride and di (hardened tallow alkyl) dimethyl ammonium chloride, are widely used in commercially available rinse conditioner compositions. Other examples of these cationic compounds are to be found in “Surface-Active Agents and
Detergents”, Volumes I and II, by Schwartz, Perry and Berch.
Any of the conventional types of such compounds may be used in the compositions of the present invention.
The fabric softening compounds are preferably compounds that provide excellent softening, and are characterised by a chain melting LP to La transition temperature greater than 25°, preferably greater than 35°C, most preferably greater than 45°C. This LP to La transition can be measured by DSC as defined in “Handbook of Lipid Bilayers”, D Marsh, CRC
Press, Boca Raton, Florida, 1990 (pages 137 and 337).
Substantially water-insoluble fabric softening compounds are defined as fabric softening compounds having a solubility of less than 1 x 10° wt % in demineralised water at 20°C.
Preferably the fabric softening compounds have a solubility of less than 1 x 107! wt%, more preferably less than 1 x 10° to 1 x 107% wts%.
Especially preferred are cationic fabric softening compounds that are water-insoluble quaternary ammonium materials having two Cj;-3; alkyl or alkenyl groups connected to the molecule via at least one ester link, preferably two ester links. An especially preferred ester-linked quaternary ammonium material can be represented by the formula II:
R;
Ri — —— N' _____ R;-T-R, (II) (CH2) p~T-R; wherein each R; group is independently selected from Ci-4 alkyl or hydroxyalkyl groups or C,.4 alkenyl groups; each R; : group is independently selected from Cg. alkyl or alkenyl groups; and wherein R3 is a linear or branched alkylene group of 1 to 5 carbon atoms, T is
Oo o
I I
-0-C- or -C-0-; and p is 0 or is an integer from 1 to 5.
Di (tallowoxyloxyethyl) dimethyl ammonium chloride and/or its hardened tallow analogue is especially preferred of the compounds of formula (II).
A second preferred type of quaternary ammonium material can be represented by the formula (III):
OOCR, rors (III)
CH,00CR? wherein R;, p and R; are as defined above.
It is advantageous if the quaternary ammonium material is biologically biodegradable.
Preferred materials of this class such as 1,2-bis (hardened tallowoyloxy)-3-trimethylammonium propane chloride and their . methods of preparation are, for example, described in
US 4 137 180 (Lever Brothers Co). Preferably these materials comprise small amounts of the corresponding monoester as described in US 4 137 180, for example, l-hardened tallowoyloxy-2-hydroxy-3-trimethylammonium propane chloride.
Other useful cationic softening agents are alkyl pyridinium salts and substituted imidazoline species. Also useful are primary, secondary and tertiary amines and the condensation products of fatty acids with alkylpolyamines.
The compositions may alternatively or additionally contain water-soluble cationic fabric softeners, as described in
GB 2 039 556B (Unilever).
The compositions may comprise a cationic fabric softening compound and an oil, for example as disclosed in EP-A- 0829531.
The compositions may alternatively or additionally contain nonionic fabric softening agents such as lanolin and derivatives thereof.
Lecithins are also suitable softening compounds.
Nonionic softeners include LP phase forming sugar esters (as described in M Hato et al Langmuir 12, 1659, 1666, (1996)) and related materials such as glycerol monostearate or : sorbitan esters. Often these materials are used in conjunction with cationic materials to assist deposition . (see, for example, GB 2 202 244). Silicones are used in a similar way as a co-softener with a cationic softener in rinse treatments (see, for example, GB 1 549 180).
The compositions may also suitably contain a nonionic stabilising agent. Suitable nonionic stabilising agents are linear Cg to Cz; alcohols alkoxylated with 10 to 20 moles of alkylene oxide, Cio to Cz alcohols, or mixtures thereof.
Advantageously the nonionic stabilising agent is a linear Cg to Cz; alcohol alkoxylated with 10 to 20 moles of alkylene oxide. Preferably, the level of nonionic stabiliser is within the range from 0.1 to 10% by weight, more preferably from 0.5 to 5% by weight, most preferably from 1 to 4% by weight. The mole ratio of the quaternary ammonium compound and/or other cationic softening agent to the nonionic
Claims (25)
1. Fabric care composition comprising a polymeric material which is capable of self cross-linking and/or of reacting with cellulose together with one or more textile compatible carriers, wherein the polymeric material comprises one or more poly (oxyalkylene) groups having an end group which comprises one or more amino groups or derivatives of said amino groups, wherein when the textile compatible carrier is water a further additive suitable for use in laundry compositions is present.
2. Composition as claimed in Claim 1, wherein the . polymeric material is obtainable by the reaction of a polymer of formula B(R),, wherein n is from 1 to 20, B is a } backbone group to which each R is covalently bonded and R is a group comprising a poly (oxyalkylene) chain, which chain comprises an amino end group, the polymer being optionally reacted with a bridging compound, with a cross-linking agent.
3. Composition as claimed in Claim 2, wherein n is 2 or 3.
4. Composition as claimed in Claim 2 or Claim 3, wherein B is -0-CH, (CH) m~CH2-0- and m is equal to n-2. 0)
5. Composition as claimed in any one of Claims 2 to 4, wherein at least one R group has the formula - (CHCH(R') (CHz) a0) p~A-NHR'', wherein: R' is H or CHs3; a is 0,
l or 2; p is an integer from 5 to 30; A is an alkylene group; and R'' is H or alkyl.
6. Composition as claimed in any one of Claims 2 to 5, wherein p is from 10 to 25.
7. Composition as claimed in any one of Claims 2 to 6, wherein the polymer of formula B(R), is H,C-O(CH,CH(R')O)p—A-NH, HC-O (CH,CH (R') 0) q—~A-NH; H,C-O (CH2CH(R') 0) —A-NH, . 15 ; wherein p, gq and r are integers which may be the same or : different and may be from 5 to 30 and A is branched or unbranched lower alkylene.
8. Composition as claimed in any one of Claims 2 to 6, wherein the polymer of formula B(R), is HzN- (CHz) b= (O (CHz2) 4) =O (CH2) cO- ( (CH2) 40) q2— (CH,) ,~NH, wherein: b is an integer from 1 to 6; c is an integer from 1 to 6; and d and d2 are the same or different and are integers from 10 to 15.
9. Composition as claimed in Claim 8, wherein b is 3 and/or c is 4.
10. Composition as claimed in any one of Claims 2 to 9, wherein the cross-linking agent comprises an epihalohydrin.
11. Composition as claimed in any one of Claims 2 to 10 wherein the molar ratio of cross-linking agent to polymer of formula B(R), is from 0.5:1 to 4:1.
12. Composition as claimed in any one of Claims 2 to 11, wherein the bridging compound comprises two epoxide or carboxylic acid groups.
13. Composition as claimed in Claim 11, wherein the epoxide or carboxylic acid groups are linked by a linker comprising alkylene, arylene, poly(oxyalkylene) or siloxane groups or combinations thereof. B
14. Composition as claimed in any one of Claims 1 to 13 further comprising a silicone which is capable of reacting with the polymeric material.
15. Composition as claimed in any one of Claims 1 to 14, : wherein the polymeric material is capable of increasing the wet strength of paper by at least 200% compared to untreated paper when applied to paper having a weight of 80 g/m? at a level of 1% solids by weight based on weight of paper.
16. Composition as claimed in any one of Claims 1 to 15, wherein the one or more textile compatible carriers comprise a detergent active compound.
17. Composition as claimed in any one of Claims 1 to 15, wherein the one or more textile compatible carriers comprise a fabric softening and/or conditioning compound.
.
J. 34 -
18. Composition as claimed in any one of Claims 1 to 17, further comprising a perfume.
19. A method of treating fabric, as part of a laundering process, which comprises applying to the fabric a fabric care composition according to any one of Claims 1 to 18.
20. A method of treating fabric, as part of a laundering process, which comprises applying to the fabric a polymeric material as defined in any one of Claims 1 to 18.
21. A method as claimed in Claim 19 or Claim 20 wherein the composition is applied to the fabric during a wash cycle.
22. A method as claimed in Claim 19, or Claim 20, wherein the composition is applied to the fabric during a rinse cycle.
23. Use of a fabric care composition according to any one of Claims 1 to 18 or a polymeric material as defined in any one of Claims 1 to 18 to improve the surface colour definition of a fabric after multiple washings.
24. Use of a fabric care composition according to any one of Claims 1 to 18 or a polymeric material as defined in any one of Claims 1 to 18 to impart pill and/or fuzz resistance to fabric during laundering.
25. Use as claimed in Claim 23 or Claim 24, wherein the fabric comprises cellulosic fibres.
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
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GBGB9923921.2A GB9923921D0 (en) | 1999-10-08 | 1999-10-08 | Fabric care composition |
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ZA200202685B true ZA200202685B (en) | 2003-06-25 |
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ZA200202685A ZA200202685B (en) | 1999-10-08 | 2002-04-05 | Fabric care composition. |
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EP (1) | EP1218477B1 (en) |
CN (1) | CN100457881C (en) |
AR (1) | AR025970A1 (en) |
AT (1) | ATE301703T1 (en) |
AU (1) | AU7305000A (en) |
BR (1) | BR0014560B1 (en) |
CA (1) | CA2386553C (en) |
CZ (1) | CZ20021239A3 (en) |
DE (1) | DE60021903T2 (en) |
ES (1) | ES2245647T3 (en) |
GB (1) | GB9923921D0 (en) |
HU (1) | HUP0203581A2 (en) |
PL (1) | PL354930A1 (en) |
TR (1) | TR200200925T2 (en) |
WO (1) | WO2001027232A1 (en) |
ZA (1) | ZA200202685B (en) |
Families Citing this family (22)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP1387878B1 (en) * | 2001-05-17 | 2004-10-06 | Unilever Plc | Laundry composition |
GB2378960A (en) * | 2001-08-22 | 2003-02-26 | Unilever Plc | Fabric care composition |
GB0122825D0 (en) * | 2001-09-21 | 2001-11-14 | Unilever Plc | Fabric care composition |
GB0201165D0 (en) | 2002-01-18 | 2002-03-06 | Unilever Plc | Azetidinium modidfied poymers and fabric treatment composition |
WO2003078504A1 (en) | 2002-03-20 | 2003-09-25 | Ge Bayer Silicones Gmbh & Co. Kg | Branched polyorganosiloxane polymers |
DE10316662A1 (en) | 2003-04-11 | 2004-11-11 | Ge Bayer Silicones Gmbh & Co. Kg | Reactive amino and / or ammonium polysiloxane compounds |
WO2013032479A1 (en) * | 2011-09-01 | 2013-03-07 | Colgate-Palmolive Company | Method for providing fast dry to fabric |
US9758927B2 (en) | 2011-09-01 | 2017-09-12 | Colgate-Palmolive Company | Method for ease of ironing |
WO2013032481A1 (en) * | 2011-09-01 | 2013-03-07 | Colgate-Palmolive Company | Method for increased fragrance release during ironing |
WO2013032480A1 (en) * | 2011-09-01 | 2013-03-07 | Colgate-Palmolive Company | Method for ease of ironing |
MX2015013672A (en) | 2013-03-28 | 2016-02-16 | Procter & Gamble | Cleaning compositions containing a polyetheramine, a soil release polymer, and a carboxymethylcellulose. |
EP3039112B1 (en) | 2013-08-26 | 2019-03-20 | The Procter and Gamble Company | Cleaning compositions containing a polyetheramine |
US9719052B2 (en) | 2014-03-27 | 2017-08-01 | The Procter & Gamble Company | Cleaning compositions containing a polyetheramine |
EP3122848A1 (en) | 2014-03-27 | 2017-02-01 | The Procter & Gamble Company | Cleaning compositions containing a polyetheramine |
WO2016028257A1 (en) * | 2014-08-18 | 2016-02-25 | Colgate-Palmolive Company | Hair products containing polyetheramine |
US9617502B2 (en) | 2014-09-15 | 2017-04-11 | The Procter & Gamble Company | Detergent compositions containing salts of polyetheramines and polymeric acid |
US9631163B2 (en) | 2014-09-25 | 2017-04-25 | The Procter & Gamble Company | Liquid laundry detergent composition |
US9752101B2 (en) | 2014-09-25 | 2017-09-05 | The Procter & Gamble Company | Liquid laundry detergent composition |
JP6430632B2 (en) | 2014-09-25 | 2018-11-28 | ザ プロクター アンド ギャンブル カンパニー | Fabric care composition containing polyetheramine |
EP3197988B1 (en) | 2014-09-25 | 2018-08-01 | The Procter & Gamble Company | Cleaning compositions containing a polyetheramine |
US9388368B2 (en) | 2014-09-26 | 2016-07-12 | The Procter & Gamble Company | Cleaning compositions containing a polyetheramine |
US20170275565A1 (en) | 2016-03-24 | 2017-09-28 | The Procter & Gamble Company | Compositions containing an etheramine |
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CH541595A (en) * | 1970-06-05 | 1973-09-15 | Sandoz Ag | Process for the production of new polyether amines |
GB8916906D0 (en) * | 1989-07-24 | 1989-09-06 | Precision Proc Textiles Ltd | New prepolymers and their use in a method for the treatment of wool |
US5858023A (en) * | 1990-10-15 | 1999-01-12 | Precision Processes Textiles | Softening agents |
GB9022305D0 (en) * | 1990-10-15 | 1990-11-28 | Precision Proc Textiles Ltd | Softening agents |
GB9626572D0 (en) * | 1996-12-20 | 1997-02-05 | Lucas Ind Plc | Control system |
WO1998029530A2 (en) * | 1996-12-31 | 1998-07-09 | The Procter & Gamble Company | Laundry detergent compositions with polyamide-polyamines |
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1999
- 1999-10-08 GB GBGB9923921.2A patent/GB9923921D0/en not_active Ceased
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- 2000-09-26 EP EP00960893A patent/EP1218477B1/en not_active Expired - Lifetime
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- 2000-09-26 DE DE60021903T patent/DE60021903T2/en not_active Expired - Lifetime
- 2000-09-26 WO PCT/GB2000/003695 patent/WO2001027232A1/en active IP Right Grant
- 2000-09-26 ES ES00960893T patent/ES2245647T3/en not_active Expired - Lifetime
- 2000-09-26 CA CA2386553A patent/CA2386553C/en not_active Expired - Fee Related
- 2000-09-26 AU AU73050/00A patent/AU7305000A/en not_active Abandoned
- 2000-09-26 AT AT00960893T patent/ATE301703T1/en not_active IP Right Cessation
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- 2000-09-26 PL PL00354930A patent/PL354930A1/en unknown
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AR025970A1 (en) | 2002-12-26 |
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ES2245647T3 (en) | 2006-01-16 |
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GB9923921D0 (en) | 1999-12-08 |
CN100457881C (en) | 2009-02-04 |
WO2001027232A1 (en) | 2001-04-19 |
EP1218477B1 (en) | 2005-08-10 |
CN1409753A (en) | 2003-04-09 |
CA2386553C (en) | 2010-02-16 |
HUP0203581A2 (en) | 2003-03-28 |
BR0014560B1 (en) | 2010-08-24 |
TR200200925T2 (en) | 2002-06-21 |
ATE301703T1 (en) | 2005-08-15 |
BR0014560A (en) | 2002-06-11 |
DE60021903D1 (en) | 2005-09-15 |
CZ20021239A3 (en) | 2002-10-16 |
EP1218477A1 (en) | 2002-07-03 |
DE60021903T2 (en) | 2006-03-30 |
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