EP0586323B1 - Detergent composition and method for its preparation - Google Patents
Detergent composition and method for its preparation Download PDFInfo
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- EP0586323B1 EP0586323B1 EP93500108A EP93500108A EP0586323B1 EP 0586323 B1 EP0586323 B1 EP 0586323B1 EP 93500108 A EP93500108 A EP 93500108A EP 93500108 A EP93500108 A EP 93500108A EP 0586323 B1 EP0586323 B1 EP 0586323B1
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- EP
- European Patent Office
- Prior art keywords
- detergent composition
- formula
- nonionic
- ester
- preferebly
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
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- 239000000203 mixture Substances 0.000 title claims abstract description 53
- 239000003599 detergent Substances 0.000 title claims abstract description 28
- 238000000034 method Methods 0.000 title claims description 7
- 238000002360 preparation method Methods 0.000 title claims description 4
- 150000001875 compounds Chemical class 0.000 claims abstract description 13
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 6
- 150000005690 diesters Chemical class 0.000 claims abstract description 4
- 125000003342 alkenyl group Chemical group 0.000 claims abstract description 3
- 150000005691 triesters Chemical class 0.000 claims abstract 2
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims description 18
- -1 tri-ester compounds Chemical class 0.000 claims description 17
- 235000014113 dietary fatty acids Nutrition 0.000 claims description 10
- 239000000194 fatty acid Substances 0.000 claims description 10
- 229930195729 fatty acid Natural products 0.000 claims description 10
- 235000011187 glycerol Nutrition 0.000 claims description 9
- 239000003054 catalyst Substances 0.000 claims description 7
- 238000006243 chemical reaction Methods 0.000 claims description 6
- 150000004665 fatty acids Chemical class 0.000 claims description 6
- UFTFJSFQGQCHQW-UHFFFAOYSA-N triformin Chemical compound O=COCC(OC=O)COC=O UFTFJSFQGQCHQW-UHFFFAOYSA-N 0.000 claims description 6
- 125000002947 alkylene group Chemical group 0.000 claims description 4
- 239000011541 reaction mixture Substances 0.000 claims description 4
- 235000019387 fatty acid methyl ester Nutrition 0.000 claims description 2
- 238000009884 interesterification Methods 0.000 claims description 2
- 238000012546 transfer Methods 0.000 abstract description 11
- 239000006260 foam Substances 0.000 abstract description 6
- 239000002085 irritant Substances 0.000 abstract description 4
- 231100000021 irritant Toxicity 0.000 abstract description 4
- 231100000252 nontoxic Toxicity 0.000 abstract description 4
- 230000003000 nontoxic effect Effects 0.000 abstract description 4
- 230000005764 inhibitory process Effects 0.000 abstract description 2
- 239000000975 dye Substances 0.000 description 9
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical class C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 7
- 239000003921 oil Substances 0.000 description 7
- 235000019198 oils Nutrition 0.000 description 7
- 235000019333 sodium laurylsulphate Nutrition 0.000 description 6
- 239000004141 Sodium laurylsulphate Substances 0.000 description 5
- 150000001298 alcohols Chemical class 0.000 description 5
- 238000009472 formulation Methods 0.000 description 5
- 238000012360 testing method Methods 0.000 description 5
- 238000005406 washing Methods 0.000 description 5
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 4
- 239000004744 fabric Substances 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- 206010040880 Skin irritation Diseases 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 235000019197 fats Nutrition 0.000 description 3
- 230000007794 irritation Effects 0.000 description 3
- XOFYZVNMUHMLCC-ZPOLXVRWSA-N prednisone Chemical compound O=C1C=C[C@]2(C)[C@H]3C(=O)C[C@](C)([C@@](CC4)(O)C(=O)CO)[C@@H]4[C@@H]3CCC2=C1 XOFYZVNMUHMLCC-ZPOLXVRWSA-N 0.000 description 3
- 231100000475 skin irritation Toxicity 0.000 description 3
- 239000003760 tallow Substances 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- 241000251468 Actinopterygii Species 0.000 description 2
- 235000019737 Animal fat Nutrition 0.000 description 2
- KWIUHFFTVRNATP-UHFFFAOYSA-N Betaine Natural products C[N+](C)(C)CC([O-])=O KWIUHFFTVRNATP-UHFFFAOYSA-N 0.000 description 2
- 241000195493 Cryptophyta Species 0.000 description 2
- 241000238578 Daphnia Species 0.000 description 2
- KWIUHFFTVRNATP-UHFFFAOYSA-O N,N,N-trimethylglycinium Chemical class C[N+](C)(C)CC(O)=O KWIUHFFTVRNATP-UHFFFAOYSA-O 0.000 description 2
- 150000001408 amides Chemical class 0.000 description 2
- 125000000129 anionic group Chemical group 0.000 description 2
- 229960003237 betaine Drugs 0.000 description 2
- 238000004140 cleaning Methods 0.000 description 2
- 239000012467 final product Substances 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 238000013508 migration Methods 0.000 description 2
- 230000005012 migration Effects 0.000 description 2
- HLERILKGMXJNBU-UHFFFAOYSA-N norvaline betaine Chemical compound CCCC(C([O-])=O)[N+](C)(C)C HLERILKGMXJNBU-UHFFFAOYSA-N 0.000 description 2
- 239000002304 perfume Substances 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 239000002453 shampoo Substances 0.000 description 2
- 230000036556 skin irritation Effects 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 239000002689 soil Substances 0.000 description 2
- 238000006467 substitution reaction Methods 0.000 description 2
- 230000002195 synergetic effect Effects 0.000 description 2
- 231100000419 toxicity Toxicity 0.000 description 2
- 230000001988 toxicity Effects 0.000 description 2
- AVBJHQDHVYGQLS-AWEZNQCLSA-N (2s)-2-(dodecanoylamino)pentanedioic acid Chemical compound CCCCCCCCCCCC(=O)N[C@H](C(O)=O)CCC(O)=O AVBJHQDHVYGQLS-AWEZNQCLSA-N 0.000 description 1
- LDVVTQMJQSCDMK-UHFFFAOYSA-N 1,3-dihydroxypropan-2-yl formate Chemical compound OCC(CO)OC=O LDVVTQMJQSCDMK-UHFFFAOYSA-N 0.000 description 1
- QTDIEDOANJISNP-UHFFFAOYSA-N 2-dodecoxyethyl hydrogen sulfate Chemical compound CCCCCCCCCCCCOCCOS(O)(=O)=O QTDIEDOANJISNP-UHFFFAOYSA-N 0.000 description 1
- 235000013162 Cocos nucifera Nutrition 0.000 description 1
- 244000060011 Cocos nucifera Species 0.000 description 1
- 206010015946 Eye irritation Diseases 0.000 description 1
- 206010058667 Oral toxicity Diseases 0.000 description 1
- 235000019482 Palm oil Nutrition 0.000 description 1
- 239000002202 Polyethylene glycol Substances 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 125000005466 alkylenyl group Chemical group 0.000 description 1
- 125000003368 amide group Chemical group 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 239000002280 amphoteric surfactant Substances 0.000 description 1
- 239000003945 anionic surfactant Substances 0.000 description 1
- 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 1
- 235000015278 beef Nutrition 0.000 description 1
- 210000000988 bone and bone Anatomy 0.000 description 1
- 239000004359 castor oil Substances 0.000 description 1
- 235000019438 castor oil Nutrition 0.000 description 1
- 230000003749 cleanliness Effects 0.000 description 1
- 239000003240 coconut oil Substances 0.000 description 1
- 235000019864 coconut oil Nutrition 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000013461 design Methods 0.000 description 1
- 230000002542 deteriorative effect Effects 0.000 description 1
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 238000004453 electron probe microanalysis Methods 0.000 description 1
- 230000001804 emulsifying effect Effects 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 231100000584 environmental toxicity Toxicity 0.000 description 1
- 125000004185 ester group Chemical group 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 231100000013 eye irritation Toxicity 0.000 description 1
- 125000005313 fatty acid group Chemical group 0.000 description 1
- ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 description 1
- 150000002314 glycerols Chemical class 0.000 description 1
- MTNDZQHUAFNZQY-UHFFFAOYSA-N imidazoline Chemical compound C1CN=CN1 MTNDZQHUAFNZQY-UHFFFAOYSA-N 0.000 description 1
- 238000010348 incorporation Methods 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 150000008040 ionic compounds Chemical class 0.000 description 1
- 238000004900 laundering Methods 0.000 description 1
- KJPHTXTWFHVJIG-UHFFFAOYSA-N n-ethyl-2-[(6-methoxypyridin-3-yl)-(2-methylphenyl)sulfonylamino]-n-(pyridin-3-ylmethyl)acetamide Chemical compound C=1C=C(OC)N=CC=1N(S(=O)(=O)C=1C(=CC=CC=1)C)CC(=O)N(CC)CC1=CC=CN=C1 KJPHTXTWFHVJIG-UHFFFAOYSA-N 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 150000002829 nitrogen Chemical class 0.000 description 1
- 239000002736 nonionic surfactant Substances 0.000 description 1
- 229920000847 nonoxynol Polymers 0.000 description 1
- SNQQPOLDUKLAAF-UHFFFAOYSA-N nonylphenol Chemical class CCCCCCCCCC1=CC=CC=C1O SNQQPOLDUKLAAF-UHFFFAOYSA-N 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 231100000418 oral toxicity Toxicity 0.000 description 1
- 239000002540 palm oil Substances 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 238000005063 solubilization Methods 0.000 description 1
- 230000007928 solubilization Effects 0.000 description 1
- 239000003549 soybean oil Substances 0.000 description 1
- 235000012424 soybean oil Nutrition 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil 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
- C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
- C11D1/66—Non-ionic compounds
- C11D1/74—Carboxylates or sulfonates esters of polyoxyalkylene glycols
Definitions
- the present invention relates to novel liquid detergent compositions which are biodegradable, non-toxic, and non-irritant, while improves its detergency, foam stability and colour protection in case of heavy and light duty detergent.
- These detergent compositions are particulary useful to formulate shampoos, body shampoos, washing up, all purpose cleaners, heavy and light duty detergents.
- the present invention relates to cleaning formulations comprising a specific nonionic compound.
- the present invention relates to a method for preparing the above mentioned nonionic.
- detergent compositions involve a combination of anionic, amphoteric and/or nonionic surfactants, in order to get better properties according to final product in terms of irritation, detergency and foam profile.
- the nonionics employed in the detergent compositions were conventionally ethoxylated nonylphenols, C12 ⁇ 18 alcohols ethoxylated with approximately 12 moles of ethylene oxides, lately C12 ⁇ 15 alcohols ethoxylated with 2 to 9 moles of ethylene oxides and EO/OP derivatives.
- Japanese Patent Laid-Open No. 55-86894 discloses the use of a secondary C6 ⁇ 14 alcohols ethoxylated with 4-15 moles of ethylene oxides on average.
- Japanese Patent Laid-Open No. 52-22007, and Japanese Patent Publication No. 83037356 disclose the use of middle alcohol ethoxylated of formula R1O(C2H4O)nH, wherein R1 is straight chain or branched alkyl radicals and n is 1-12 on average in detergent compositions.
- European Patent No. 80749 discloses the use of ethoxylated alkyl phenols in detergent compositions.
- US Patent 4908150 discloses the use of polyethylene glycol ether of a glycerol ester compositions.
- Japanese Patent Laid-Open No. 55-133495 discloses the use of a polyoxyethylene hardened castor oil or fatty acid ester, thereof, polyoxyethylene glyceryl ether fatty acid ester, polyoxyethylene trimethylol propane fatty acid ester and polyoxyethylene alkylether diester of N-lauroylglutamic acid etc, in detergent compositions.
- US Patent 4247425 discloses the use of alkoxylated partial glycerol esters of a detergent grade fatty acid in light duty detergent compositions.
- EP Patent 0007120 discloses an emulsifying system, to be used in a handwashing composition, mainly consisting of mono and diglycerides of higher natural fatty acids and ethoxylated glycerine esterified by fatty acids.
- US Patent 4897214 discloses the use of monoesters of fatty acids with polyoxyethylene hexitan derivatives in skin cleaning preparations.
- WO Patent 92/00945 discloses the use of octadienyl glycerin ethers with polyoxyethylene.
- UK Patent 21973308 discloses the use of polyoxyalkylene alkyl- or alkenyl ethers and polyoxyalkylene glycerol fatty acid esters in detergent compositions.
- the present inventors have carried out research on the developement of a detergent composition, which will exhibit the outstanding biodegradable, non-toxic, non-irritant performance, foam stability and better dye inhibition transfer maintaining and even improving detergency.
- the present invention relates to a detergent compositions comprising the mono-, di- and tri-ester compounds represented by the formula (I), where the mono-di-tri-ester proportion is 46-90/9-30/1-15 wherein:
- Ratio (I)/(II) has a value between 3 to 0.33 preferebly 1.3 to 0.75.
- the compound mixture of the formula (I) + (II) in the present invention can be obtained by conventional method for preparating it.
- the compound can be obtained by following the reaction processes.
- Triglyceride which can be used in process (A) includes natural fat and oil as well as a synthetic triglyceride.
- the fat and oil include vegetable oil such as coconut oil, palm oil, soybean oil; and animal fat and oil such as beef tallow, bone oil; aquatic animal fat and oil; hardened oils and semihardened oil thereof.
- the compound mixture of the formula (I)+(II) can be incorporated in an amount of from 0.2% to 40%, preferebly from 3% to 20% by weight based on the whole of the detergent composition.
- compositions containing the nonionic of the present invention provide a more superior colour care than usual ethoxylated alcohol.
- the nonionic from the present invention performs better than alcohol ethoxylated preventing dye transfer.
- polyvinylpirrolidone typically dye-tranfer inhibitor.
- the especific amount to be saved will depend on the effect of other components, that means, on formulation design. It seems to the applicant that a synergistic effect exists between the nonionic of present invention and PVP.
- test 1 and 2 were corroborated using a 5 people panel, who evaluate the results according to a scale.
- compositions containing the nonionic of the present invention prevent better the colour transfer even in HDL where the ph is neutral and no optical brighters are used. (Note that HDL were used as colour save detergents before appearing the new segment of colour saving H.D.P.D..
- compositions containing Levenol® shows a better detergency and fat dispersion, allowing the supresion of nitrogen derivatives (alkanol amide and amine oxide) and also the complete substitution of ethoxylated alcohol. Other key point is the partial substitution of betaine.
- the nonionic of the present invention gives also a creamy foam compared to other compositions.
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- 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)
- Detergent Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Description
- The present invention relates to novel liquid detergent compositions which are biodegradable, non-toxic, and non-irritant, while improves its detergency, foam stability and colour protection in case of heavy and light duty detergent. These detergent compositions are particulary useful to formulate shampoos, body shampoos, washing up, all purpose cleaners, heavy and light duty detergents.
- In fact, the present invention relates to cleaning formulations comprising a specific nonionic compound.
- In addition to that, the present invention relates to a method for preparing the above mentioned nonionic.
- Most of detergent compositions involve a combination of anionic, amphoteric and/or nonionic surfactants, in order to get better properties according to final product in terms of irritation, detergency and foam profile.
- One of the current problems in the whole field of chemicals is the question of ecotoxicity and the duality cleanliness/damage, that is how to get a good performance without interact seriously with the surface (fabrics or skin).
- The nonionics employed in the detergent compositions were conventionally ethoxylated nonylphenols, C₁₂₋₁₈ alcohols ethoxylated with approximately 12 moles of ethylene oxides, lately C₁₂₋₁₅ alcohols ethoxylated with 2 to 9 moles of ethylene oxides and EO/OP derivatives.
- For instance:
- Japanese Patent Laid-Open No. 55-86894, discloses the use of a secondary C₆₋₁₄ alcohols ethoxylated with 4-15 moles of ethylene oxides on average.
- Japanese Patent Laid-Open No. 52-22007, and Japanese Patent Publication No. 83037356, disclose the use of middle alcohol ethoxylated of formula R₁O(C₂H₄O)nH, wherein R₁ is straight chain or branched alkyl radicals and n is 1-12 on average in detergent compositions.
- European Patent No. 80749, discloses the use of ethoxylated alkyl phenols in detergent compositions.
- US Patent 4908150, discloses the use of polyethylene glycol ether of a glycerol ester compositions.
- Japanese Patent Laid-Open No. 55-133495, discloses the use of a polyoxyethylene hardened castor oil or fatty acid ester, thereof, polyoxyethylene glyceryl ether fatty acid ester, polyoxyethylene trimethylol propane fatty acid ester and polyoxyethylene alkylether diester of N-lauroylglutamic acid etc, in detergent compositions.
- However, use of such nonionics deteriorates detergency ability of detergent formulation. Also in case of heavy and light duty liquids detergents tends to cause dye transfer, especially upon repeated laundering. In addition to the above mentioned points, current nonionics cause skin and eye irritation, and values of fish toxicity, daphnia inmobilization and algae are not acceptable under the present environmental requirements.
- Others patents describe the use of specific non-ionic compounds, different from the usual ones, in particular applications and/or conditions.
- US Patent 4247425, discloses the use of alkoxylated partial glycerol esters of a detergent grade fatty acid in light duty detergent compositions.
- EP Patent 0007120, discloses an emulsifying system, to be used in a handwashing composition, mainly consisting of mono and diglycerides of higher natural fatty acids and ethoxylated glycerine esterified by fatty acids.
- US Patent 4897214, discloses the use of monoesters of fatty acids with polyoxyethylene hexitan derivatives in skin cleaning preparations.
- WO Patent 92/00945, discloses the use of octadienyl glycerin ethers with polyoxyethylene.
- UK Patent 2197338, discloses the use of polyoxyalkylene alkyl- or alkenyl ethers and polyoxyalkylene glycerol fatty acid esters in detergent compositions.
- In none of disclosures mentioned above it is taught a nonionic like the one described in the present invention.
- The present inventors have carried out research on the developement of a detergent composition, which will exhibit the outstanding biodegradable, non-toxic, non-irritant performance, foam stability and better dye inhibition transfer maintaining and even improving detergency.
- It was unexpectedly found that the above mentioned requirements can be met when the specified nonionic compound is incorporated into detergent composition.
- This finding has led to the present invention.
-
- "B" represents "H" or the group represented by
- "n","m" and "l" may have a value between 0 and 40 provided that (n+m+l) = 2 - 100 preferebly 9 - 19.
- R` represents H or CH₃ respectively and the compound represented by the formula (II)
- "n", "m" and "l" may have a value between 0 and 40 provided that (n+m+l) = 2 - 100 preferebly 9 - 19.
- R` represents H or CH₃ respectively.
- Being the high content of ethoxylated monoester in compound (I) and ratio (I)/(II) the key parameters to get the above mentioned properties.
- Ratio (I)/(II) has a value between 3 to 0.33 preferebly 1.3 to 0.75.
- The compound mixture of the formula (I) + (II) in the present invention can be obtained by conventional method for preparating it.
- For example the compound can be obtained by following the reaction processes.
- (A) The interesterification reaction between triglyceride and glycerine, in a molar ratio in the proportion of 0.1-10/1, preferebly 0.15-3.5 (in presence of alkaline catalyst), and the reaction with alkylene oxide C₂₋₃ or viceversa will lead to a mono- di- and triglyceride mixture (I) and (I)/(II) ratio of specific composition and structure, due to migration and exchange phenomena, with an HLB higher than 2.
- (B) The reaction of glycerine with alkylene oxide C₂₋₃, in presence of alkaline catalysts and the later reaction with fatty acid in a molar ratio in the proportion of 0.1-10/1, preferebly 0,7-3.5/1 in presence of acidic or alkaline catalysts will lead to a mono- di-and triglyceride mixture of a specific composition and structure, due to migration and exchange phenomena, with an HLB higher than 2.
- Triglyceride which can be used in process (A) includes natural fat and oil as well as a synthetic triglyceride.
- The fat and oil include vegetable oil such as coconut oil, palm oil, soybean oil; and animal fat and oil such as beef tallow, bone oil; aquatic animal fat and oil; hardened oils and semihardened oil thereof.
- In the present invention the compound mixture of the formula (I)+(II) can be incorporated in an amount of from 0.2% to 40%, preferebly from 3% to 20% by weight based on the whole of the detergent composition.
- The reason why the present invention exhibits the outstanding biodegradable, non-toxic and non-irritant performance without deteriorating its detergeny is not certain, but it seems to applicant that good performance of the present composition comes partially from the fact that existence of fatty acid groups facilitates its biodegradability and its very low skin irritation, oral toxicity, fish toxicity, algae and daphnia inmobilization compared with conventional nonionics.
- Furthermore incorporation of the formula of the new nonionic described in the patent, considerably improves its foam profile, anti dye transfer and perfume solubilization properties compared with conventional formulations, due to EO monoglyceride high ratio and the synergistic effect between (I) and (II).
- The surface active agents like anionic, other nonionic, amphoteric etc and the rest of additive useful in the practice of this invention depends a great deal on kind of final product to be formulated. At the same time they are standard items of commerce so they will be not further comments upon herein.
- The present invention is described in detail by way of the following examples. The present invention, however, is not limited to these examples.
- The compound mixture of the formula ( (I)+(II) ) is obtained, for instance by means of the following process:
-
-
- "B" represents "H" or the group represented by
- "R" represents a coco alkyl chain.
- (I)/(II) ratio is 1.
- 500 g (0.76 moles) of coco TRG, 210.7 g (2.29 moles) of glycerine 99% and 1.2 g of KOH 85% as catalyst are placed in a 3 kg flask properly equipped. System is purged several times with N₂, vacuum stripping till 110°C, and continued heating to 140°C. When temperature reaches 140°C the reactor is pressurized to 2-3 kg/cm with ethylene oxide added until a total of 2013 gr (45.7 moles).
- After the final charge of ethylene oxide the reaction mixture is allowed to react for about 1/2 hour; cooled and discharged from reactor. A product like ( (I) + (II) ) is obtained.
- The compound mixture of the formula ( (I)+(II) ) is obtained, for instance by means of the following process:
-
-
- "B" represents "H" or the group represented by
- R` represents CH₃.
- R means tallow alkyl chain.
- Ratio (I)/(II) = 1.3
- 14.3 g (0.1554 moles) of glycerine 99% and 1.2 g of KOH 85% as catalyst are placed in a 250 gr flask properly equipped. System is purged several times with N₂, vacuum stripping till 110°C, and continued heating to 140°C. When temperature reaches 140°C the reactor is pressurized to 2-3 kg/cm with ethylene oxide added until a total of 67,9 gr (1.54 moles). After the final charge of ethylene oxide, the reaction mixture is allowed to react for about 1/2 hour; 52.3 gr (0.15 mol) of a methyl ester of fatty acid derived from tallow, is added and mixed for 45 minutes. Finally product is cooled and discharged from reactor. Thus a compound mixture of the formula (I) + (II) is obtained.
-
- Detergency evaluation test:
- Washing machine:
- Temperature: 30°C and 60°C.
- Dosage: 6 gr/l.
- Water hardness: 2 mmol/L Ca⁺ and 4 mmol/L Ca⁺ (20°HF and 40°HF).
- Washing load: 2kg of not soiled cotton-polyester cloth and EMPA 101,104,117 + particulated soil.
- No pre-washing program.
- Detergent ability was evaluated on detergent compositions appearing in table 1.
- All variables considered, that is, temperature, water hardness and soil type the nonionic described in this patent shows in the worst of cases equivalent eficiency in terms of detergency.
- However, on the other hand, compositions containing the nonionic of the present invention provide a more superior colour care than usual ethoxylated alcohol.
- The following test have been conducted at 30°C. 1.- Using Reactive dyestuff.
- After 15 washings, differences appeared in terms of colour transfer.
- Dye transfer was evaluated measuring delta E values (L + a + b)1/2 by Hunter-Lab. The resulting discolouration of fabrics is shown in table below:
Table 1. Compositions Blue Green Red 1 8.0 14.0 6.0 2 5.7 10.3 5.0 3 6.0 8.0 4.5 4 5.0 6.5 4.0 5 1.3 0.9 0.5 6 1.2 1.0 0.5 - The lower delta E, the better composition is able to prevent dye transfer. Therefore can be concluded from the above results that the nonionic from the present invention performs better than alcohol ethoxylated preventing dye transfer. In addition to that it is possible to save some amount of polyvinylpirrolidone (typical dye-tranfer inhibitor). The especific amount to be saved will depend on the effect of other components, that means, on formulation design. It seems to the applicant that a synergistic effect exists between the nonionic of present invention and PVP.
- References:
Yellow: Solar Yellow 3LG 160%
Blue: Solar Blue 2GLN 350%Formulations: Blue Green Yellow Solar Blue 2GLN 350% 1% 1% -- Solar Yellow 3LG 160% -- 1% 1% SO₄Na₂ 20 g/l 20 g/l 20 g/l Sandofix R 3% 3% 3% - After 3 washings, differences appeared in terms of colour transfer.
- Dye transfer was evaluated measuring delta E values (L + a + b )1/2 by Hunter-Lab. The resulting dicoloration of fabrics is shown in table below:
Table 2. Compositions Blue Green Yellow 1 2.0 2.5 4.0 2 1.3 1.7 3.0 3 1.6 8.0 3.2 4 0.9 6.5 2.0 5 1.3 0.9 0.7 6 1.2 1.0 0.7 - Those results, test 1 and 2, were corroborated using a 5 people panel, who evaluate the results according to a scale.
-
- Following the same test conditions than explained above for HDPD, (adapting the dosage according to the composition) the following results were obtained:
- Good enough detergency in all cases.
- Colour appearance results are shown in table 3.
- In short, compositions containing the nonionic of the present invention prevent better the colour transfer even in HDL where the ph is neutral and no optical brighters are used. (Note that HDL were used as colour save detergents before appearing the new segment of colour saving H.D.P.D..
-
COMPOSITIONS Raw materials 1 2 3 4 Na lauryl ether sulphate 10 10 7 7 Na Alfa-olephine sulphonate -- -- 4 4 Alkyl amido propyl betaine 5.3 4.5 5.7 2.5 Ethoxylated (7) C₁₃₋₁₅ alcohol 13 -- -- -- Nonionic of present invention. (from referential example 1) -- 7 -- 7 Coconut diethanol amide 5 -- -- -- Amine oxide -- -- 3.3 -- Perfume 1 1 1 1 Water bal. bal. bal. bal. - Compositions containing Levenol® shows a better detergency and fat dispersion, allowing the supresion of nitrogen derivatives (alkanol amide and amine oxide) and also the complete substitution of ethoxylated alcohol. Other key point is the partial substitution of betaine. The nonionic of the present invention gives also a creamy foam compared to other compositions.
- In order to check the effect on the skin of the nonionic of the present invention, a primary skin irritation test was conducted:
-
COMPOSITION IRRITATION INDEX 1.- Sodium lauryl sulphate 6.25% 1.88 2.- Sodium lauryl sulphate 4.25% + Nonionic (1) 2.00% 1.00 3.- Sodium lauryl sulphate 4.25% 1.38 -
COMPOSITION IRRITATION INDEX 1.- Sodium lauryl sulphate 4.25% + Coco imidazoline betaine 2.00% 1.08 2.- Sodium lauryl sulphate 4.25% + Alkylamide propyl betaine 2.00% 0.96 3.- Sodium lauryl sulfate 4.25% + Nonionic (1) 2.00% 1.00 - (1) Represents nonionic of the present invention from the referential example 2.
- From the comparison of the above compositions, can be inferred the mild effect of the nonionic of the present invention.
Compositions | Blue | Green | Red |
1 | 0.9 | 4.0 | 3.2 |
2 | 1.5 | 5.0 | 3.8 |
3 | 1.6 | 5.1 | 3.8 |
4 | 3.0 | 6.0 | 4.5 |
Claims (4)
- Detergent composition comprising the mono-, di-and tri-ester compounds represented by the formula (I) wherein the weight ratio of mono, di and tri-ester is 46-90/9-30/1-15,- "B" represents "H" or the group represented by- "n","m" and "l" may have a value between 0 and 40 provided that (n+m+l) = 2 - 100 preferebly 9 - 19.- R' represents H or CH₃ respectively,in which the weight ratio (I)/(II) has a value between 3 to 0.33.
- Detergent composition according to claim 1 in which the ratio (I)/(II) has a value between 1.3 to 0.75.
- Method for the preparation of a detergent composition, according to claim 1 which is produced by the following steps (a) and (b):a) The mixture of triglyceride, and glycerine is subjected to a inter-esterification reaction,b) The reaction mixture obtained in the step (a) is subjected to alkoxylation using alkylene oxide having C₂₋₃ in the presence of alkaline catalyst to produce the compounds represented by the general formula (I) + (II).
- Method for the preparation of a detergent composition, according to claim 1 which is produced by the following steps (c) and (d):c) The mixture of glycerine and alkylene oxide C₂₋₃, in presence of alkaline catalysts,d) The reaction mixture obtained in the step (c) reacted with methyl ester of fatty acid or fatty acid.
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
EP93500108A EP0586323B2 (en) | 1992-07-20 | 1993-07-20 | Detergent composition and method for its preparation |
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
EP92500092 | 1992-07-20 | ||
EP92500092 | 1992-07-20 | ||
EP93500108A EP0586323B2 (en) | 1992-07-20 | 1993-07-20 | Detergent composition and method for its preparation |
Publications (3)
Publication Number | Publication Date |
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EP0586323A1 EP0586323A1 (en) | 1994-03-09 |
EP0586323B1 true EP0586323B1 (en) | 1996-04-10 |
EP0586323B2 EP0586323B2 (en) | 2005-11-02 |
Family
ID=8211823
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
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EP93500108A Expired - Lifetime EP0586323B2 (en) | 1992-07-20 | 1993-07-20 | Detergent composition and method for its preparation |
Country Status (4)
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---|---|
EP (1) | EP0586323B2 (en) |
AT (1) | ATE136579T1 (en) |
DE (1) | DE69302151T3 (en) |
ES (1) | ES2088254T5 (en) |
Cited By (1)
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US5549840A (en) * | 1993-08-04 | 1996-08-27 | Colgate-Palmolive Co. | Cleaning composition in microemulsion, liquid crystal or aqueous solution form comprising mixture of partially esterified, full esterified and non-esterified ethoxylated polyhydric alcohols |
US5854193A (en) * | 1993-08-04 | 1998-12-29 | Colgate Palmolive Company | Microemulsion/all purpose liquid cleaning composition based on EO-PO nonionic surfactant |
US5861367A (en) * | 1993-08-04 | 1999-01-19 | Colgate Palmolive Company | Cleaning and disinfecting composition in microemulsion/liquid crystal form comprising aldehyde and mixture of partially esterified, fully esterified and non-esterified polyhydric alcohols |
NZ264113A (en) * | 1993-08-04 | 1996-06-25 | Colgate Palmolive Co | Liquid crystal or microemulsion liquid cleaners containing esterified polyethoxyether nonionic surfactant, anionic surfactant, cosurfactant, optionally a fatty acid, and water-insoluble hydrocarbon or perfume |
US5593958A (en) * | 1995-02-06 | 1997-01-14 | Colgate-Palmolive Co. | Cleaning composition in microemulsion, crystal or aqueous solution form based on ethoxylated polyhydric alcohols and option esters's thereof |
US5741760A (en) * | 1993-08-04 | 1998-04-21 | Colgate-Palmolive Company | Aqueous cleaning composition which may be in microemulsion form comprising polyalkylene oxide-polydimethyl siloxane |
WO1995014765A1 (en) * | 1993-11-22 | 1995-06-01 | Colgate-Palmolive Company | Microemulsion all purpose liquid cleaning compositions |
US5571459A (en) * | 1994-02-07 | 1996-11-05 | Colgate-Palmolive Co. | Microemulsion all purpose liquid cleaning compositions |
AU1925795A (en) * | 1994-02-28 | 1995-09-11 | Colgate-Palmolive Company, The | Liquid detergent |
ES2141862T3 (en) * | 1994-05-28 | 2000-04-01 | Goldschmidt Ag Th | AQUAUS CONCENTRATES FLUIDS OF PEARL LUSTER. |
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US5767050A (en) * | 1995-01-17 | 1998-06-16 | Colgate-Palmolive Co. | Light duty liquid cleaning compositions comprising partially esterified polyhydric alcohol solubilizing agent |
US5476614A (en) * | 1995-01-17 | 1995-12-19 | Colgate Palmolive Co. | High foaming nonionic surfactant based liquid detergent |
EP0815194A1 (en) * | 1995-02-23 | 1998-01-07 | Colgate-Palmolive Company | Microemulsion light duty liquid cleaning compositions |
DE19509752A1 (en) * | 1995-03-17 | 1996-09-19 | Henkel Kgaa | Compressed washing and cleaning agents with high powder density |
CA2274567A1 (en) * | 1996-12-12 | 1998-06-18 | Colgate-Palmolive Company | Chemical linker compositions |
WO1998059031A1 (en) * | 1997-06-23 | 1998-12-30 | Colgate-Palmolive Company | Microemulsion all purpose liquid cleaning compositions |
US5866527A (en) * | 1997-08-01 | 1999-02-02 | Colgate Palmolive Company | All purpose liquid cleaning compositions comprising anionic EO nonionic and EO-BO nonionic surfactants |
US5858956A (en) * | 1997-12-03 | 1999-01-12 | Colgate-Palmolive Company | All purpose liquid cleaning compositions comprising anionic, EO nonionic and EO-BO nonionic surfactants |
PT1045021E (en) * | 1999-04-13 | 2004-05-31 | Kao Corp Sa | COMPOSITION INCLUDING A MIXTURE OF ALCOXYLATED MONO- DI- AND TRIGLYCERIDES AND GLYCERIN |
ES2185497B1 (en) * | 2001-07-30 | 2004-03-16 | Kao Corp Sa | CONCENTRATED WATERNESS NACARANT COMPOSITIONS. |
US6544938B1 (en) | 2001-10-02 | 2003-04-08 | Unilever Home & Personal Care Usa, Division Of Conopco, Inc. | Soap bar comprising high levels of specific alkoxylated triglycerides which provide enhanced sensory properties and process well |
ATE364741T1 (en) * | 2004-05-26 | 2007-07-15 | Boehme Chem Fab Kg | HYDROPHILATING MATERIALS CONTAINING POLYOLEFIN AND/OR POLYESTER |
ES2293825B1 (en) * | 2006-06-07 | 2008-12-16 | Kao Corporation, S.A. | COMPOSITION CONTAINING A MONO-DI MIXTURE, AND TRIGLICERIDS AND GLYCERINE. |
EP2202219A1 (en) | 2008-12-24 | 2010-06-30 | Kao Corporation, S.A. | Mixture of amides and cosmetic compositions comprising said mixture |
EP2497844A1 (en) | 2011-03-10 | 2012-09-12 | Kao Corporation, S.A. | Quaternary ammonium esters (Esterquats) containing composition for inhibiting corrosion of metal surface |
CN103764611B (en) * | 2011-08-17 | 2016-01-20 | 陶氏环球技术有限责任公司 | Biorenewable and biodegradable tensio-active agent |
DK2666848T3 (en) | 2012-05-22 | 2017-10-23 | Kao Corp Sa | Diluent surfactant composition |
US10045529B2 (en) | 2012-06-29 | 2018-08-14 | Ecolab Usa Inc. | Quat cleaner with glycerin ether ethoxylates |
GB201316619D0 (en) * | 2013-09-19 | 2013-10-30 | Croda Int Plc | A stain treatment additive |
WO2018085064A1 (en) | 2016-11-04 | 2018-05-11 | Huntsman Petrochemical Llc | Estolides of vegetable oil alkoxylates and methods of making and using |
US11505746B2 (en) | 2016-12-15 | 2022-11-22 | Indorama Ventures Oxides Llc | Vegetable oil-based alkoxylates and methods of making such |
EP4442327A1 (en) | 2023-04-05 | 2024-10-09 | Kao Corporation, S.A. | Composition which contains a mixture of mono-, di-, and triglycerides and glycerine |
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JPS6050238B2 (en) * | 1979-04-04 | 1985-11-07 | ライオン株式会社 | cleaning composition |
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JPS591600A (en) * | 1982-06-28 | 1984-01-06 | 日本エマルジヨン株式会社 | Detergent |
IT1193614B (en) * | 1983-01-24 | 1988-07-21 | Crinos Industria Farmaco | PREPARATION FOR THE HYGIENE AND CLEANING OF THE SKIN OF THE HAIR AND HAIR |
JPS6386798A (en) * | 1986-09-30 | 1988-04-18 | 花王株式会社 | Liquid detergent composition |
JPH01135714A (en) * | 1987-11-20 | 1989-05-29 | Lion Corp | Creamy skin cleaning agent |
DE4021478A1 (en) * | 1990-07-05 | 1992-01-09 | Henkel Kgaa | UNSATURATED POLYALKYLENE GLYCOLETHER |
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- 1993-07-20 EP EP93500108A patent/EP0586323B2/en not_active Expired - Lifetime
- 1993-07-20 DE DE69302151T patent/DE69302151T3/en not_active Expired - Lifetime
- 1993-07-20 AT AT93500108T patent/ATE136579T1/en active
- 1993-07-20 ES ES93500108T patent/ES2088254T5/en not_active Expired - Lifetime
Non-Patent Citations (1)
Title |
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CHEMICAL ABSTRACTS, vol. 100, no. 24, 11 June 1984, Columbus, Ohio, US; abstract no. 194041r, page 121 ; & JP-A-5 901 600 (NIHON EMARUJON K K) 6 January 1984 * |
Cited By (1)
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---|---|---|---|---|
US9663431B2 (en) | 2012-06-29 | 2017-05-30 | Ecolab Usa Inc. | Glycerin ether ethoxylate solfactants |
Also Published As
Publication number | Publication date |
---|---|
ES2088254T3 (en) | 1996-08-01 |
ES2088254T5 (en) | 2006-04-16 |
DE69302151T2 (en) | 1996-12-05 |
ATE136579T1 (en) | 1996-04-15 |
DE69302151T3 (en) | 2006-06-14 |
EP0586323B2 (en) | 2005-11-02 |
EP0586323A1 (en) | 1994-03-09 |
DE69302151D1 (en) | 1996-05-15 |
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