WO2011133378A1 - Procédé pour la fabrication d'une composition de base de détergent - Google Patents
Procédé pour la fabrication d'une composition de base de détergent Download PDFInfo
- Publication number
- WO2011133378A1 WO2011133378A1 PCT/US2011/032419 US2011032419W WO2011133378A1 WO 2011133378 A1 WO2011133378 A1 WO 2011133378A1 US 2011032419 W US2011032419 W US 2011032419W WO 2011133378 A1 WO2011133378 A1 WO 2011133378A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- detersive surfactant
- detergent
- sulphate
- neutralized
- process according
- Prior art date
Links
- 239000003599 detergent Substances 0.000 title claims abstract description 83
- 239000000203 mixture Substances 0.000 title claims abstract description 76
- 238000000034 method Methods 0.000 title claims abstract description 40
- 230000008569 process Effects 0.000 title claims abstract description 36
- 239000004094 surface-active agent Substances 0.000 claims abstract description 75
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 claims abstract description 45
- 229910021653 sulphate ion Inorganic materials 0.000 claims abstract description 38
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 26
- 239000007788 liquid Substances 0.000 claims abstract description 24
- 230000003472 neutralizing effect Effects 0.000 claims abstract description 24
- 239000006188 syrup Substances 0.000 claims abstract description 19
- 235000020357 syrup Nutrition 0.000 claims abstract description 19
- 239000002253 acid Substances 0.000 claims abstract description 8
- -1 alkyl sulphates Chemical class 0.000 claims description 35
- 125000000217 alkyl group Chemical group 0.000 claims description 16
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 15
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 claims description 14
- 239000003960 organic solvent Substances 0.000 claims description 11
- 239000004744 fabric Substances 0.000 claims description 7
- 238000010412 laundry washing Methods 0.000 claims description 5
- 238000004900 laundering Methods 0.000 claims description 4
- 150000003467 sulfuric acid derivatives Chemical class 0.000 claims description 3
- 239000007864 aqueous solution Substances 0.000 claims description 2
- 229920000642 polymer Polymers 0.000 description 26
- 239000000047 product Substances 0.000 description 18
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 17
- 239000002904 solvent Substances 0.000 description 16
- 239000000463 material Substances 0.000 description 15
- 239000002736 nonionic surfactant Substances 0.000 description 13
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 12
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 11
- 238000004140 cleaning Methods 0.000 description 10
- 239000004615 ingredient Substances 0.000 description 10
- 238000007792 addition Methods 0.000 description 9
- 150000008051 alkyl sulfates Chemical class 0.000 description 9
- 150000001412 amines Chemical class 0.000 description 9
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 9
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 9
- 125000005529 alkyleneoxy group Chemical group 0.000 description 8
- 239000004519 grease Substances 0.000 description 7
- 239000001257 hydrogen Substances 0.000 description 7
- 229910052739 hydrogen Inorganic materials 0.000 description 7
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 6
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 6
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 6
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 5
- 150000004996 alkyl benzenes Chemical class 0.000 description 5
- 238000000518 rheometry Methods 0.000 description 5
- 101001051490 Homo sapiens Neural cell adhesion molecule L1 Proteins 0.000 description 4
- 208000031300 Hydrocephalus with stenosis of the aqueduct of Sylvius Diseases 0.000 description 4
- 102100024964 Neural cell adhesion molecule L1 Human genes 0.000 description 4
- 208000026197 X-linked hydrocephalus with stenosis of the aqueduct of Sylvius Diseases 0.000 description 4
- 239000003945 anionic surfactant Substances 0.000 description 4
- JXLHNMVSKXFWAO-UHFFFAOYSA-N azane;7-fluoro-2,1,3-benzoxadiazole-4-sulfonic acid Chemical compound N.OS(=O)(=O)C1=CC=C(F)C2=NON=C12 JXLHNMVSKXFWAO-UHFFFAOYSA-N 0.000 description 4
- 238000007046 ethoxylation reaction Methods 0.000 description 4
- 150000002191 fatty alcohols Chemical class 0.000 description 4
- 230000002349 favourable effect Effects 0.000 description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
- 230000009467 reduction Effects 0.000 description 4
- 229920006395 saturated elastomer Polymers 0.000 description 4
- 125000000467 secondary amino group Chemical class [H]N([*:1])[*:2] 0.000 description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
- 102000004190 Enzymes Human genes 0.000 description 3
- 108090000790 Enzymes Proteins 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 3
- 229920002873 Polyethylenimine Polymers 0.000 description 3
- 125000002947 alkylene group Chemical group 0.000 description 3
- 125000004432 carbon atom Chemical group C* 0.000 description 3
- 235000014113 dietary fatty acids Nutrition 0.000 description 3
- 239000002270 dispersing agent Substances 0.000 description 3
- 239000000975 dye Substances 0.000 description 3
- 229930195729 fatty acid Natural products 0.000 description 3
- 239000000194 fatty acid Substances 0.000 description 3
- 150000004665 fatty acids Chemical class 0.000 description 3
- 125000004433 nitrogen atom Chemical group N* 0.000 description 3
- 229920001451 polypropylene glycol Polymers 0.000 description 3
- AFHIIJICYLMCSH-VOTSOKGWSA-N 5-amino-2-[(e)-2-(4-benzamido-2-sulfophenyl)ethenyl]benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC(N)=CC=C1\C=C\C(C(=C1)S(O)(=O)=O)=CC=C1NC(=O)C1=CC=CC=C1 AFHIIJICYLMCSH-VOTSOKGWSA-N 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- 239000004743 Polypropylene Substances 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 125000000129 anionic group Chemical group 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- 230000009286 beneficial effect Effects 0.000 description 2
- 230000008901 benefit Effects 0.000 description 2
- 229940092714 benzenesulfonic acid Drugs 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 239000007844 bleaching agent Substances 0.000 description 2
- 239000004327 boric acid Substances 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 125000000753 cycloalkyl group Chemical group 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 2
- 150000002334 glycols Chemical class 0.000 description 2
- 229920000578 graft copolymer Polymers 0.000 description 2
- 230000002209 hydrophobic effect Effects 0.000 description 2
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 239000002245 particle Substances 0.000 description 2
- 239000002304 perfume Substances 0.000 description 2
- 229920000768 polyamine Polymers 0.000 description 2
- 229920001155 polypropylene Polymers 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 239000002689 soil Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 description 1
- TZJFRKWUJOXRKM-UHFFFAOYSA-N 1-ethoxypentan-1-ol Chemical compound CCCCC(O)OCC TZJFRKWUJOXRKM-UHFFFAOYSA-N 0.000 description 1
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 1
- RZVAJINKPMORJF-UHFFFAOYSA-N Acetaminophen Chemical compound CC(=O)NC1=CC=C(O)C=C1 RZVAJINKPMORJF-UHFFFAOYSA-N 0.000 description 1
- CBOCVOKPQGJKKJ-UHFFFAOYSA-L Calcium formate Chemical compound [Ca+2].[O-]C=O.[O-]C=O CBOCVOKPQGJKKJ-UHFFFAOYSA-L 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 1
- QPCDCPDFJACHGM-UHFFFAOYSA-N N,N-bis{2-[bis(carboxymethyl)amino]ethyl}glycine Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(=O)O)CCN(CC(O)=O)CC(O)=O QPCDCPDFJACHGM-UHFFFAOYSA-N 0.000 description 1
- 239000004698 Polyethylene Substances 0.000 description 1
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 238000013019 agitation Methods 0.000 description 1
- 150000001299 aldehydes Chemical class 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 229920002214 alkoxylated polymer Polymers 0.000 description 1
- 150000005215 alkyl ethers Chemical class 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 239000012298 atmosphere Substances 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- CREXVNNSNOKDHW-UHFFFAOYSA-N azaniumylideneazanide Chemical group N[N] CREXVNNSNOKDHW-UHFFFAOYSA-N 0.000 description 1
- KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 description 1
- 239000000872 buffer Substances 0.000 description 1
- 229940044172 calcium formate Drugs 0.000 description 1
- 239000004281 calcium formate Substances 0.000 description 1
- 235000019255 calcium formate Nutrition 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- 239000013522 chelant Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 239000007859 condensation product Substances 0.000 description 1
- 230000004069 differentiation Effects 0.000 description 1
- 150000002009 diols Chemical class 0.000 description 1
- 238000011038 discontinuous diafiltration by volume reduction Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- YZSJUQIFYHUSKU-UHFFFAOYSA-N ethanol;propane-1,2-diol Chemical compound CCO.CC(O)CO YZSJUQIFYHUSKU-UHFFFAOYSA-N 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 125000003827 glycol group Chemical group 0.000 description 1
- 125000004836 hexamethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 description 1
- 230000036571 hydration Effects 0.000 description 1
- 238000006703 hydration reaction Methods 0.000 description 1
- 125000001183 hydrocarbyl group Chemical group 0.000 description 1
- 230000005764 inhibitory process Effects 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
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000010445 mica Substances 0.000 description 1
- 229910052618 mica group Inorganic materials 0.000 description 1
- 150000002762 monocarboxylic acid derivatives Chemical class 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- VMESOKCXSYNAKD-UHFFFAOYSA-N n,n-dimethylhydroxylamine Chemical compound CN(C)O VMESOKCXSYNAKD-UHFFFAOYSA-N 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
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- LQPLDXQVILYOOL-UHFFFAOYSA-I pentasodium;2-[bis[2-[bis(carboxylatomethyl)amino]ethyl]amino]acetate Chemical compound [Na+].[Na+].[Na+].[Na+].[Na+].[O-]C(=O)CN(CC([O-])=O)CCN(CC(=O)[O-])CCN(CC([O-])=O)CC([O-])=O LQPLDXQVILYOOL-UHFFFAOYSA-I 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 229920001983 poloxamer Polymers 0.000 description 1
- 229920001748 polybutylene Polymers 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 150000003138 primary alcohols Chemical class 0.000 description 1
- 150000003141 primary amines Chemical class 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 150000005846 sugar alcohols Polymers 0.000 description 1
- 239000000271 synthetic detergent Substances 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 125000001302 tertiary amino group Chemical group 0.000 description 1
- 150000004072 triols Chemical class 0.000 description 1
- 229920001567 vinyl ester resin Polymers 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
- C11D11/00—Special methods for preparing compositions containing mixtures of detergents
- C11D11/0094—Process for making liquid detergent compositions, e.g. slurries, pastes or gels
-
- 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
- C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
- C11D1/02—Anionic compounds
- C11D1/37—Mixtures of compounds all of which are anionic
-
- 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
- C11D11/00—Special methods for preparing compositions containing mixtures of detergents
- C11D11/04—Special methods for preparing compositions containing mixtures of detergents by chemical means, e.g. by sulfonating in the presence of other compounding ingredients followed by neutralising
-
- 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
- C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
- C11D1/02—Anionic compounds
- C11D1/12—Sulfonic acids or sulfuric acid esters; Salts thereof
- C11D1/14—Sulfonic acids or sulfuric acid esters; Salts thereof derived from aliphatic hydrocarbons or mono-alcohols
- C11D1/143—Sulfonic acid esters
-
- 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
- C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
- C11D1/02—Anionic compounds
- C11D1/12—Sulfonic acids or sulfuric acid esters; Salts thereof
- C11D1/14—Sulfonic acids or sulfuric acid esters; Salts thereof derived from aliphatic hydrocarbons or mono-alcohols
- C11D1/146—Sulfuric acid esters
-
- 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
- C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
- C11D1/02—Anionic compounds
- C11D1/12—Sulfonic acids or sulfuric acid esters; Salts thereof
- C11D1/29—Sulfates of polyoxyalkylene ethers
Definitions
- the present invention relates to a process for making a liquid detergent base composition, a detergent comprising the base composition and a method of laundering using the detergent.
- Compacted liquid laundry detergent products have less space to incorporate detergent ingredients; this places great constraint on the detergent formulator, especially for restricting the levels of the bulk detergent ingredients like surfactants, builders and solvents that take up much of the formulation space.
- the detergent formulator must greatly improve the efficiency of these detergent ingredients, and of the compacted liquid laundry detergent composition as a whole.
- the detergent formulator must also ensure that such products have good product storage stability profile, and desirable rheological properties to ensure that the product can be handled and dosed easily by the consumer.
- the aim of the present invention is to overcome the above described drawbacks.
- anhydrous composition is herein understood a composition having preferably less than 30%, more preferably less than 20% and especially less than 10% of water by weight thereof.
- base composition is herein understood a composition that can be used either as a finished detergent product or preferably as a building block for a finished detergent product.
- the process of the invention comprises the steps of:
- pre-neutralized surfactant is herein understood a surfactant that has been neutralized before it takes part in the process for making the detergent base composition, as opposite to be neutralized during the process for making the detergent base composition.
- sulphate detersive surfactants are not very stable in the acid form, preferably they are neutralized just after the acid form is produced. Furthermore the sulphate detersive surfactant, even after it has been neutralized, can be instabilized by the presence of acid. It has been found that by adding neutralizing agent to the pre-neutralized sulphate detersive surfactant syrup (in addition to the neutralizing agent added for the pre-neutralization) before any other acidic material the stability of the sulphate detersive surfactant is enhanced. Step c) is performed after steps a) and b) thus the pre-neutralized sulphate detersive surfactant is protected from the acid by the neutralizing agent.
- the sulphate detersive surfactant is selected from alkyl alkoxylated sulphates, mid-chain branched primary alkyl sulphates and mixtures thereof.
- the sulphate detersive surfactant comprises an alkyl ethoxylated sulphate, more preferably a C 8- i8 alkyl ethoxylated sulphate having an average degree of ethoxylation of from 0.5 to 10, preferably from 0.5 to 7, more preferably from 0.5 to 5 and most preferably from 0.5 to 4.
- At least 50%, preferably at least 70%, more preferably at least 90% and especially 100% of the sulphate detersive surfactant present in the syrup has been pre-neutralized with an organic neutralizing agent.
- the organic neutralizing agent is preferably an alkanolamine. It can be a primary, secondary or a tertiary amine. Mono-ethanolamine (MEA) is the preferred alkanolamine for use herein.
- MEA Mono-ethanolamine
- the use of an organic neutralizing agent, preferably mono- ethanolamine avoids or reduces the use of water (as compared to inorganic neutralizing agents) and contributes to the reduction of volume of the base composition as well as to a favorable rheology of the resulting base composition. These two factors (volume reduction and favorable rheology) are critical for the preparation of a compact detergent.
- the pre-neutralized sulphate detersive surfactant syrup comprises an organic solvent, preferably a non-amino functional solvent.
- a non-amino functional solvent preferably a non-amino functional solvent.
- Preferred non-amino functional solvents for use herein include primary alcohols, glycols and mixtures thereof.
- Especially preferred non- amino functional solvent is a mixture comprising ethanol and propylene glycol.
- the process of the invention comprises the step of adding an organic solvent after step a) and preferably before step b).
- This organic solvent can be the same or different to that in the pre-neutralized sulphate detersive surfactant syrup.
- Preferred organic solvent for use herein is a non-amino functional solvent, including alcohols, glycols and mixtures thereof.
- Especially preferred organic solvent to be added between step a) and b) is a mixture comprising ethanol propylene glycol and diethylene glycol.
- steps a) and b) further contributes to reduction of the water in the composition and consequently to the reduction of volume and to a favorable rheology of the resulting base composition.
- the neutralizing agent of step b) can be selected from organic neutralizing agents, inorganic neutralizing agents and mixtures thereof.
- This neutralizing agent can be the same or different to that in the pre-neutralized sulphate detersive surfactant syrup.
- This neutralizing agent is preferably an alkanolamine, more preferably mono-ethanolamine (MEA), providing the benefits cited herein above.
- more than 50%, preferably more than 60% and especially more than 70% of the anionic surfactant in the base composition is sulphate detersive surfactant.
- the sulphate detersive surfactant and the sulphonate detersive surfactant are in a weight ratio of from about 4: 1 to about 1: 1.
- the detergent base preferably comprises from 0% to 5%, more preferably less than 2% and especially less than 1% by weight of the base of citric acid and any other materials that have a large sphere of hydration associated to them.
- the detergent base delivers similar amounts of actives to those delivered in traditional detergents in a smaller dose size and because the water content is lower some chemistry that is not necessarily compatible with or in higher water content products can be made compatible in lower water products.
- a process for making a laundry liquid detergent comprising post-adding to the base composition obtainable and preferably obtained by the process of the first aspect of the invention from about 5 to about 20% of water by weight of the detergent.
- the base composition obtainable, and preferably obtained, by the process of the first aspect of the invention is robust enough to withstand water addition without negatively influencing the rheology profile of the base composition.
- a laundry detergent obtainable and preferably obtained according to the process of the first or second aspect of the invention.
- the detergent is quite compact thereby allowing for the delivery of a very small dose (volume wise) providing good cleaning results.
- Typical volumes of compacted detergents are below 30 ml, more preferably below 25 ml.
- the detergent also has a good rheological profile.
- a method of laundering fabric comprising the step of contacting the fabric in a laundry washing machine with a wash liquor comprising from about 0.2 to about 1 g/1, preferably from about 0.3 to about 0.8 g/1, of the detergent of the invention.
- the present invention envisages a process for making a detergent base composition, preferably a laundry liquid detergent base composition. It also envisages a detergent composition obtainable according to the process of the invention, and a method of laundering a fabric using the detergent composition.
- the process gives rise to a base composition that is very versatile in terms of post- addition of ingredients and presents a good rheological profile.
- the base can be used to generate a concentrated detergent, i.e., a detergent with high level of active ingredients, or it can be further diluted if desired.
- the process starts with a pre-neutralized sulfate detersive surfactant syrup.
- the syrup comprises an organic solvent, more preferably a non-amino functional solvent.
- an organic solvent is added to the pre-neutralized sulfate detersive surfactant syrup and then the neutralizing agent is added.
- the rest of the ingredients include brightener, non-ionic surfactant, dispersant polymer, surfactancy boosting polymer, chelant, etc.
- the temperature of the mixture is below 37°C (this is achieved by cooling if the temperature of the mixture is above 37°C).
- the sulphonic detersive surfactant is added to create the detergent base.
- the detergent base can be converted into a fully formulated detergent by the addition of other detergent ingredients such as enzymes and suds suppresors.
- Preferred sulfate detersive surfactant for use herein includes alkoxylated and/or un-alkoxylated alkyl sulfate materials.
- Preferred alkoxylated alkyl sulfate materials comprises ethoxylated alkyl sulfate surfactants.
- Such materials also known as alkyl ether sulfates or alkyl polyethoxylate sulfates, are those which correspond to the formula:
- R' is a Cg-C20 alkyl group, n is from about 1 to 20, and M is a salt-forming cation.
- R' is C ⁇ Q-C g alkyl and n is from about 1 to 15.
- R' is a ⁇ 2- ⁇ and n is from about 1 to 6.
- Preferred un-alkoxylated alkyl sulfate materials include mid-branched primary alkyl sulfate surfactants having an average carbon chain length of from about 14 to about 17 (“MBAS surfactants"). They provide good cleaning properties. MBAS surfactants with a carbon chain length of about 16 to 17 (also referred to as "HSAS surfactants”) generally provide better cleaning than those of other chain-lengths.
- the pre-neutralized sulfate detersive surfactant comprises a C 8- i8 alkyl ethoxylated sulphate having an average degree of ethoxylation of from 0.5 to 10, preferably from 0.5 to 7, more preferably from 0.5 to 5 and most preferably from 0.5 to 6.
- the pre-neutralized sulfate detersive surfactant comprises a HSAS surfactant.
- the pre-neutralized sulfate detersive surfactant comprises a mixture of an alkyl ehthoxylated sulphate with a HSAS surfactant, preferably the alkyl ehthoxylated sulphate and the HSAS surfactant are in a weight ratio of at least 2: 1, more preferably at least 5: 1 and specially at least 10: 1.
- Preferably at least 50%, more preferably at least 70% and especially at least 90% of the sulfate detersive surfactant is neutralized with mono- ethanolamine.
- the pre-neutralized sulfate detersive surfactant syrup comprises a non-aminofunctional solvent.
- non-aminofunctional solvent refers to any solvent which contains no amino functional groups.
- Non-aminofunctional solvent include, for example: C1-C8 alkanols such as methanol, ethanol and/or propanol and/or 1-ethoxypentanol; C2-C6 diols; C3-C8 alkylene glycols; C3-C8 alkylene glycol mono lower alkyl ethers; glycol dialkyl ether; lower molecular weight polyethylene glycols; C3-C9 triols such as glycerol; and mixtures thereof.
- non-aminofunctional solvent are liquids at ambient temperature and pressure (i.e. 21° C. and 1 atmosphere), and comprise carbon, hydrogen and oxygen.
- non- aminofunctional solvent may comprise from about 0% to about 25%, more specifically from about 1 to about 20%, even more specifically from about 5% to about 15% by weight of the syrup.
- the addition of the non-aminofunctional solvent would contribute to the favorable rheological profile of the base composition.
- Preferred sulphonic detersive surfactant is a ⁇ Q. ⁇ alkyl benzene sulfonic acid, preferably C ⁇ ⁇ .
- alkyl benzene sulfonic acid Preferably the alkyl group is linear and such linear alkyl benzene sulfonates are known as "LAS". Alkyl benzene sulfonates, and particularly LAS, are well known in the art. Such surfactants and their preparation are described for example in U.S. Patents 2,220,099 and 2,477,383.
- compositions suitable for use herein comprises from 5% to 70% by weight, preferably from 10% to 60% by weight, more preferably from 20% to 50% by weight, of a certain kind of detersive surfactant component.
- a certain kind of detersive surfactant component preferably comprises anionic surfactants (sulphate and sulphonic detersive surfactants as described herein before), nonionic surfactants, or combinations of these two surfactant types.
- the detergent comprises from about 10% to about 40%, preferably from about 15% to 30% by weight of the detergent of an alkoxylated sulfate detersive surfactant.
- the detergent comprises from 5% to 20%, more preferably from 7 to 15% by weight of the detergent of a sulphonate detersive surfactant.
- the detergent comprises from 0.1% to 10%, more preferably from 1 to 5% by weight of the detergent of a non-ionic detersive surfactant.
- the detergent comprises from 0 to 10%, more preferably from 1 to 5% by weight of the detergent of a fatty acid.
- Suitable nonionic surfactants useful herein can comprise any of the conventional nonionic surfactant types typically used in liquid detergent products. These include alkoxylated fatty alcohols, ethylene oxide (EO) -propylene oxide (PO) block polymers, and amine oxide surfactants. Preferred for use in the liquid detergent products herein are those nonionic surfactants which are normally liquid.
- Preferred nonionic surfactants for use herein include the alcohol alkoxylate nonionic surfactants.
- Alcohol alkoxylates are materials which correspond to the general formula:
- R1 is a Cg - C ⁇ g alkyl group
- m is from 2 to 4
- n ranges from about 2 to 12.
- R 1 is an alkyl group, which may be primary or secondary, that contains from about 9 to 15 carbon atoms, more preferably from about 10 to 14 carbon atoms.
- the alkoxylated fatty alcohols will be ethoxylated materials that contain from about 2 to 12 ethylene oxide moieties per molecule, more preferably from about 3 to 10 ethylene oxide moieties per molecule.
- the alkoxylated fatty alcohol materials useful in the liquid detergent compositions herein will frequently have a hydrophilic-lipophilic balance (HLB) which ranges from about 3 to 17. More preferably, the HLB of this material will range from about 6 to 15, most preferably from about 8 to 15.
- HLB hydrophilic-lipophilic balance
- Alkoxylated fatty alcohol nonionic surfactants have been marketed under the tradenames Neodol and Dobanol by the Shell Chemical Company.
- EO ethylene oxide
- PO propylene oxide
- Materials of this type are well known nonionic surfactants which have been marketed under the tradename Pluronic. These materials are formed by adding blocks of ethylene oxide moieties to the ends of polypropylene glycol chains to adjust the surface active properties of the resulting block polymers.
- Pluronic ethylene oxide moieties to the ends of polypropylene glycol chains to adjust the surface active properties of the resulting block polymers.
- EO-PO block polymer nonionics of this type are described in greater detail in Davidsohn and Milwidsky; Synthetic Detergents, 7th Ed.; Longman Scientific and Technical (1987) at pp. 34-36 and pp. 189-191 and in U.S. Patents 2,674,619 and 2,677,700.
- Nonionic surfactant useful herein comprises the amine oxide surfactants.
- Amine oxides are mateials which are often referred to in the art as "semi-polar" nonionics. Amine oxides have the formula: R(EO) x (PO) y (BO) z N(0)(CH 2 R)2-qH20.
- R is a relatively long-chain hydrocarbyl moiety which can be saturated or unsaturated, linear or branched, and can contain from 8 to 20, preferably from 10 to 16 carbon atoms, and is more preferably ⁇ 2- ⁇ primary alkyl.
- R' is a short-chain moiety preferably selected from hydrogen, methyl and - ⁇ 3 ⁇ 40 ⁇ .
- the detergent of the invention comprises from about 0.5% to about 5%, more preferably from 0.8%to 3% by weight of the detergent of an amine oxide surfactant.
- the essential detersive surfactant component may comprise combinations of anionic and nonionic surfactant materials. When this is the case, the weight ratio of anionic to nonionic is at least 2: 1, preferably 5: 1 and especially 10: 1.
- the detergent composition comprises from 0% to 5%, more preferably less than 2% and especially less than 1% by weight of the detergent of citric acid. It is also preferred that the detergent composition has a low level (i.e. below 5% and more preferably below 2% by weight of the detergent) or it is free of fatty acid.
- liquid detergent compositions herein have a pH of from about 7 to about 9, more preferably from 8 to 8.5 as measured in 5% aqueous solution at 20°C.
- the detergent compositions herein preferably in liquid form, comprise from 0.1% to 30% by weight, preferably from 0.5% to 20% by weight, more preferably from 1% to 10% by weight, of one or more of certain kinds of laundry washing adjuncts.
- laundry washing adjuncts can be selected from detersive enzymes, builders, chelants, soil release polymers, soil suspending polymers, optical brighteners, dye transfer inhibition agents, bleach, whitening agents, suds suppressors, fabric care benefit agents, solvents, stabilizers, buffers, structurants, dyes and perfumes and combinations of these adjunct types. All of these materials are of the type conventionally utilized in laundry detergent products.
- the composition preferably comprises from 1 to 10% by weight of the composition of polymer.
- Suitable polymers include dispersant polymers such as polyamines, preferably polyethylene imines, most preferably alkoxylated polyethylene imines, preferably the composition comprise from about 1% to about 5% by weight of the composition of an alkoxylated polyethylene imine.
- amphiphilic alkoxylated grease cleaning polymers refer to any alkoxylated polymers having balanced hydrophilic and hydrophobic properties such that they remove grease particles from fabrics and surfaces.
- Specific embodiments of the amphiphilic alkoxylated grease cleaning polymers suitable for use herein comprise a core structure and a plurality of alkoxylate groups attached to that core structure.
- the core structure may comprise a polyalkylenimine structure comprising, in condensed form, repeating units of formulae (I), (II), (III) and (IV):
- the core structure may alternatively comprise a polyalkanolamine structure of the condensation products of at least one compound selected from N-(hydroxyalkyl)amines of formulae (I.a) and/or (I.b),
- A are independently selected from Ci-C 6 -alkylene;
- R 1 , R 1 *, R 2 , R 2 *, R 3 , R 3 *, R 4 , R 4 *, R 5 and R 5 * are independently selected from hydrogen, alkyl, cycloalkyl or aryl, wherein the last three mentioned radicals may be optionally substituted;
- R 6 is selected from hydrogen, alkyl, cycloalkyl or aryl, wherein the last three mentioned radicals may be optionally substituted.
- the plurality of alkylenoxy groups attached to the core structure are independently selected from alkylenoxy units of the formula (V)
- a 2 is in each case independently selected from 1,2-propylene, 1,2- butylene and 1 ,2-isobutylene;
- a 3 is 1,2-propylene;
- R is in each case independently selected from hydrogen and Ci-C4-alkyl;
- m has an average value in the range of from 0 to about 2;
- n has an average value in the range of from about 20 to about 50;
- p has an average value in the range of from about 10 to about 50.
- amphiphilic alkoxylated grease cleaning polymers may be selected from alkoxylated polyalkylenimines having an inner polyethylene oxide block and an outer polypropylene oxide block, the degree of ethoxylation and the degree of propoxylation not going above or below specific limiting values.
- Specific embodiments of the alkoxylated polyalkylenimines according to the present invention have a minimum ratio of polyethylene blocks to polypropylene blocks (n/p) of about 0.6 and a maximum of about 1.5(x+2y+l) 1/2.
- Alkoxykated polyalkyenimines having an n/p ratio of from about 0.8 to about 1.2(x+2y+l) 1 2 have been found to have especially beneficial properties.
- the alkoxylated polyalkylenimines according to the present invention have a backbone which consists of primary, secondary and tertiary amine nitrogen atoms which are attached to one another by alkylene radicals A and are randomly arranged.
- Primary amino moieties which start or terminate the main chain and the side chains of the polyalkylenimine backbone and whose remaining hydrogen atoms are subsequently replaced by alkylenoxy units are referred to as repeating units of formulae (I) or (IV), respectively.
- Secondary amino moieties whose remaining hydrogen atom is subsequently replaced by alkylenoxy units are referred to as repeating units of formula (II).
- Tertiary amino moieties which branch the main chain and the side chains are referred to as repeating units of formula (III).
- cyclization can occur in the formation of the polyalkylenimine backbone, it is also possible for cyclic amino moieties to be present to a small extent in the backbone.
- Such polyalkylenimines containing cyclic amino moieties are of course alkoxylated in the same way as those consisting of the noncyclic primary and secondary amino moieties.
- the polyalkylenimine backbone consisting of the nitrogen atoms and the groups A 1 , has an average molecular weight Mw of from about 60 to about 10,000 g/mole, preferably from about 100 to about 8,000 g/mole and more preferably from about 500 to about 6,000 g/mole.
- the sum (x+2y+l) corresponds to the total number of alkylenimine units present in one individual polyalkylenimine backbone and thus is directly related to the molecular weight of the polyalkylenimine backbone.
- the values given in the specification however relate to the number average of all polyalkylenimines present in the mixture.
- the sum (x+2y+2) corresponds to the total number amino groups present in one individual polyalkylenimine backbone.
- the radicals A 1 connecting the amino nitrogen atoms may be identical or different, linear or branched C2-C6-alkylene radicals, such as 1,2-ethylene, 1 ,2-propylene, 1 ,2-butylene, 1,2- isobutylene,l,2-pentanediyl, 1,2-hexanediyl or hexamethylen.
- a preferred branched alkylene is 1,2-propylene.
- Preferred linear alkylene are ethylene and hexamethylene.
- a more preferred alkylene is 1,2-ethylene.
- a 2 in each case is selected from 1,2-propylene, 1,2-butylene and 1,2-isobutylene; preferably A 2 is 1,2-propylene.
- a 3 is 1,2-propylene; R in each case is selected from hydrogen and Ci-C4-alkyl, such as methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl and tert.-butyl; preferably R is hydrogen.
- the index m in each case has a value of 0 to about 2; preferably m is 0 or approximately 1; more preferably m is 0.
- the index n has an average value in the range of from about 20 to about 50, preferably in the range of from about 22 to about 40, and more preferably in the range of from about 24 to about 30.
- the index p has an average value in the range of from about 10 to about 50, preferably in the range of from about 11 to about 40, and more preferably in the range of from about 12 to about 30.
- the alkylenoxy unit of formula (V) is a non-random sequence of alkoxylate blocks.
- non-random sequence it is meant that the [-A 2 -0-] m is added first (i.e., closest to the bond to the nitrgen atom of the repeating unit of formula (I), (II), or (III)), the [-CH 2 -CH 2 -0-] n is added second, and the [-A 3 -0-] p is added third.
- This orientation provides the alkoxylated polyalkylenimine with an inner polyethylene oxide block and an outer polypropylene oxide block.
- the polyalkylenimine backbone saturated with hydrogen atoms may be reacted initially with small amounts of up to about 2 mol, especially from about 0.5 to about 1.5 mol, in particular from about 0.8 to about 1.2 mol, of propylene oxide or butylene oxide per mole of NH- moieties present, i.e. incipiently alkoxylated.
- This initial modification of the polyalkylenimine backbone allows, if necessary, the viscosity of the reaction mixture in the alkoxylation to be lowered.
- the modification generally does not influence the performance properties of the alkoxylated polyalkylenimine and therefore does not constitute a preferred measure.
- the composition comprise from about 0.1% to about 5%, more preferably from about 0.25% to about 2.5% by weight of the composition of an amphiphilic alkoxylated grease cleaning polymer.
- Suitable random graft co-polymers typically comprise: (i) hydrophilic backbone comprising monomers selected from the group consisting of: unsaturated Ci_C6 carboxylic acids, ethers, alcohols, aldehydes, ketones, esters, sugar units, alkoxy units, maleic anhydride, saturated polyalcohols such as glycerol, and mixtures thereof; and (ii) hydrophobic side chain(s) selected from the group consisting of: C4-C25 alkyl group, polypropylene, polybutylene, vinyl ester of a saturated Ci-C 6 mono-carboxylic acid, Ci_C 6 alkyl ester of acrylic or methacrylic acid, and mixtures thereof.
- the polymer preferably has the general formula:
- X, Y and Z are capping units independently selected from H or a Ci_6 alkyl; each R 1 is independently selected from methyl and ethyl; each R 2 is independently selected from H and methyl; each R 3 is independently a C1-4 alkyl; and each R 4 is independently selected from pyrrolidone and phenyl groups.
- the weight average molecular weight of the polyethylene oxide backbone is typically from about 1,000 g/mol to about 18,000 g/mol, or from about 3,000 g/mol to about 13,500 g/mol, or from about 4,000 g/mol to about 9,000 g/mol.
- the value of m, n, o, p and q is selected such that the pendant groups comprise, by weight of the polymer at least 50%, or from about 50% to about 98%, or from about 55% to about 95%, or from about 60% to about 90%.
- the polymer useful herein typically has a weight average molecular weight of from about 1,000 to about 100,000 g/mol, or preferably from about 2,500 g/mol to about 45,000 g/mol, or from about 7,500 g/mol to about 33,800 g/mol, or from about 10,000 g/mol to about 22,500 g/mol.
- a 10 liter batch tank with an aspect ratio of about 1.3 (height to diameter) is fitted with an impeller mixer and is charged with the following:
- organic solvent composed of ethanol; propylene glycol and diethylene glycol.
- MEA-Boric acid premix composed of Boric acid, mono-ethanolamine and water
- Cooling is applied if needed during the next addition steps to maintain a maximum temperature of less than 37 °C
- the base detergent is converted to finished detergent by continued stirring and addition of:
- the detergent presents a good rheological profile and it is very stable.
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Abstract
Priority Applications (9)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
EP11715377.5A EP2561061B2 (fr) | 2010-04-19 | 2011-04-14 | Procédé pour la fabrication d'une composition de base de détergent |
CA2795931A CA2795931C (fr) | 2010-04-19 | 2011-04-14 | Procede pour la fabrication d'une composition de base de detergent |
PL11715377T PL2561061T3 (pl) | 2010-04-19 | 2011-04-14 | Sposób wytwarzania kompozycji bazowej detergentu |
BR112012026891A BR112012026891A2 (pt) | 2010-04-19 | 2011-04-14 | processo para fazer uma composição base de detergente |
MX2012012239A MX339065B (es) | 2010-04-19 | 2011-04-14 | Proceso para elaborar una composicion detergente base. |
ES11715377.5T ES2460921T3 (es) | 2010-04-19 | 2011-04-14 | Proceso para fabricar una composición detergente base |
JP2013505125A JP5774678B2 (ja) | 2010-04-19 | 2011-04-14 | 洗剤ベース組成物の製造方法 |
CN2011800185888A CN102834501A (zh) | 2010-04-19 | 2011-04-14 | 用于制备洗涤剂基础组合物的方法 |
ZA2012/07402A ZA201207402B (en) | 2010-04-19 | 2012-10-03 | Process for making a detergent base composition |
Applications Claiming Priority (2)
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US32540410P | 2010-04-19 | 2010-04-19 | |
US61/325,404 | 2010-04-19 |
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WO2011133378A1 true WO2011133378A1 (fr) | 2011-10-27 |
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Application Number | Title | Priority Date | Filing Date |
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PCT/US2011/032419 WO2011133378A1 (fr) | 2010-04-19 | 2011-04-14 | Procédé pour la fabrication d'une composition de base de détergent |
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Country | Link |
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EP (1) | EP2561061B2 (fr) |
JP (1) | JP5774678B2 (fr) |
CN (1) | CN102834501A (fr) |
AR (1) | AR082839A1 (fr) |
BR (1) | BR112012026891A2 (fr) |
CA (1) | CA2795931C (fr) |
ES (1) | ES2460921T3 (fr) |
MX (1) | MX339065B (fr) |
PL (1) | PL2561061T3 (fr) |
WO (1) | WO2011133378A1 (fr) |
ZA (1) | ZA201207402B (fr) |
Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
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JP2015513581A (ja) * | 2012-02-27 | 2015-05-14 | ザ プロクター アンド ギャンブルカンパニー | 液体洗剤製品の製造方法 |
US9951298B2 (en) | 2014-01-20 | 2018-04-24 | The Procter & Gamble Company | Fluorescent brightener premix |
EP3819360A1 (fr) * | 2019-11-06 | 2021-05-12 | Henkel AG & Co. KGaA | Solubilité améliorée des systèmes tensioactifs par adaptation de l'ajout de la matière première |
Families Citing this family (1)
Publication number | Priority date | Publication date | Assignee | Title |
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EP2992073B1 (fr) * | 2013-04-29 | 2018-12-05 | Unilever PLC, a company registered in England and Wales under company no. 41424 | Procédé pour épaissir une composition de détergent liquide |
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US2220099A (en) | 1934-01-10 | 1940-11-05 | Gen Aniline & Flim Corp | Sulphonic acids |
US2477383A (en) | 1946-12-26 | 1949-07-26 | California Research Corp | Sulfonated detergent and its method of preparation |
US2674619A (en) | 1953-10-19 | 1954-04-06 | Wyandotte Chemicals Corp | Polyoxyalkylene compounds |
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US2091704A (en) † | 1934-08-28 | 1937-08-31 | Procter & Gamble | Detergent composition |
US3664961A (en) † | 1970-03-31 | 1972-05-23 | Procter & Gamble | Enzyme detergent composition containing coagglomerated perborate bleaching agent |
DE2236727C3 (de) † | 1972-07-26 | 1985-10-24 | Unilever N.V., Rotterdam | Toilettenseife aus synthetischen Tensiden |
DE3725030A1 (de) † | 1987-07-29 | 1989-02-09 | Henkel Kgaa | Oberflaechenaktive hydroxysulfonate |
CA2027518A1 (fr) † | 1990-10-03 | 1992-04-04 | Richard L. Tadsen | Methode de preparation de compositions detergentes a haute densite, contenant des particules tensio-actives sensibles au ph |
NZ240395A (en) † | 1990-11-21 | 1993-10-26 | Colgate Palmolive Co | Process for manufacture of concentrated liquid detergent containing magnesium alkylbenzene sulphonate and alkanolamide suds booster |
DE4216629A1 (de) * | 1992-05-20 | 1993-11-25 | Henkel Kgaa | Verfahren zur Herstellung aniontensidhaltiger Wasch- und Reinigungsmittel |
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JPH10195488A (ja) * | 1996-12-28 | 1998-07-28 | Lion Corp | 液体洗浄剤組成物 |
JPH10298597A (ja) * | 1997-04-28 | 1998-11-10 | Lion Corp | 液体洗浄剤組成物 |
DE10046363A1 (de) † | 2000-09-20 | 2002-03-28 | Cognis Deutschland Gmbh | Fließfähige wässrige Fettalkoholsulfatpasten |
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-
2011
- 2011-04-14 PL PL11715377T patent/PL2561061T3/pl unknown
- 2011-04-14 BR BR112012026891A patent/BR112012026891A2/pt not_active IP Right Cessation
- 2011-04-14 MX MX2012012239A patent/MX339065B/es active IP Right Grant
- 2011-04-14 CA CA2795931A patent/CA2795931C/fr active Active
- 2011-04-14 EP EP11715377.5A patent/EP2561061B2/fr active Active
- 2011-04-14 ES ES11715377.5T patent/ES2460921T3/es active Active
- 2011-04-14 WO PCT/US2011/032419 patent/WO2011133378A1/fr active Application Filing
- 2011-04-14 CN CN2011800185888A patent/CN102834501A/zh active Pending
- 2011-04-14 JP JP2013505125A patent/JP5774678B2/ja active Active
- 2011-04-19 AR ARP110101354A patent/AR082839A1/es not_active Application Discontinuation
-
2012
- 2012-10-03 ZA ZA2012/07402A patent/ZA201207402B/en unknown
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US2477383A (en) | 1946-12-26 | 1949-07-26 | California Research Corp | Sulfonated detergent and its method of preparation |
US2677700A (en) | 1951-05-31 | 1954-05-04 | Wyandotte Chemicals Corp | Polyoxyalkylene surface active agents |
US2674619A (en) | 1953-10-19 | 1954-04-06 | Wyandotte Chemicals Corp | Polyoxyalkylene compounds |
US4056113A (en) * | 1973-09-04 | 1977-11-01 | The Procter & Gamble Company | Liquid detergent compositions for removal of cooked-on food soils |
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Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2015513581A (ja) * | 2012-02-27 | 2015-05-14 | ザ プロクター アンド ギャンブルカンパニー | 液体洗剤製品の製造方法 |
US9951298B2 (en) | 2014-01-20 | 2018-04-24 | The Procter & Gamble Company | Fluorescent brightener premix |
EP3819360A1 (fr) * | 2019-11-06 | 2021-05-12 | Henkel AG & Co. KGaA | Solubilité améliorée des systèmes tensioactifs par adaptation de l'ajout de la matière première |
Also Published As
Publication number | Publication date |
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MX339065B (es) | 2016-05-06 |
JP2013525522A (ja) | 2013-06-20 |
BR112012026891A2 (pt) | 2016-07-19 |
JP5774678B2 (ja) | 2015-09-09 |
MX2012012239A (es) | 2012-11-23 |
EP2561061B2 (fr) | 2020-07-08 |
CA2795931A1 (fr) | 2011-10-27 |
EP2561061A1 (fr) | 2013-02-27 |
CN102834501A (zh) | 2012-12-19 |
PL2561061T3 (pl) | 2014-07-31 |
EP2561061B1 (fr) | 2014-03-05 |
CA2795931C (fr) | 2015-02-17 |
AR082839A1 (es) | 2013-01-16 |
ZA201207402B (en) | 2014-03-26 |
ES2460921T3 (es) | 2014-05-16 |
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