EP0274142B1 - Detergent composition containing a polyamide softening agent - Google Patents

Detergent composition containing a polyamide softening agent Download PDF

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Publication number
EP0274142B1
EP0274142B1 EP87202157A EP87202157A EP0274142B1 EP 0274142 B1 EP0274142 B1 EP 0274142B1 EP 87202157 A EP87202157 A EP 87202157A EP 87202157 A EP87202157 A EP 87202157A EP 0274142 B1 EP0274142 B1 EP 0274142B1
Authority
EP
European Patent Office
Prior art keywords
groups
composition
alkyl
accordance
softening agent
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
Application number
EP87202157A
Other languages
German (de)
English (en)
French (fr)
Other versions
EP0274142A2 (en
EP0274142A3 (en
Inventor
Hans Raemdonck
Alfred Busch
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Procter and Gamble European Technical Center
Procter and Gamble Co
Original Assignee
Procter and Gamble European Technical Center
Procter and Gamble Co
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Procter and Gamble European Technical Center, Procter and Gamble Co filed Critical Procter and Gamble European Technical Center
Priority to AT87202157T priority Critical patent/ATE84063T1/de
Publication of EP0274142A2 publication Critical patent/EP0274142A2/en
Publication of EP0274142A3 publication Critical patent/EP0274142A3/en
Application granted granted Critical
Publication of EP0274142B1 publication Critical patent/EP0274142B1/en
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

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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
    • C11D1/38—Cationic compounds
    • C11D1/52—Carboxylic amides, alkylolamides or imides or their condensation products with alkylene oxides
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
    • C11D3/16—Organic compounds
    • C11D3/26—Organic compounds containing nitrogen
    • C11D3/32—Amides; Substituted amides
    • 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
    • C11D1/38—Cationic compounds
    • C11D1/52—Carboxylic amides, alkylolamides or imides or their condensation products with alkylene oxides
    • C11D1/528—Carboxylic amides (R1-CO-NR2R3), where at least one of the chains R1, R2 or R3 is interrupted by a functional group, e.g. a -NH-, -NR-, -CO-, or -CON- group

Definitions

  • the present invention relates to softening detergent compositions containing a narrowly-defined polyamide softening agent.
  • compositions herein in addition to providing good cleaning performance, exhibit excellence through-the-wash softening properties, and provide additional fabric-care benefits such as anti-static, anti-wrinkling, ease-of-ironing, color fidelity and anti-felting of wool.
  • Formulators of fabric treatment compositions have long sought means for simultaneously washing and softening fabrics.
  • various approaches suggested are methods employing clay softeners, or amine materials, or both ingredients in combination, such as described in e.g.: German Patents 24.39.541, 23.34.899 and European Patents 0 026 528 and 0 028 432.
  • Amines have been used in combination with soaps (U.K. patent 1 514 276), fatty acids (published E.P.A. 0 133 804) or phosphate esters (published E.P.A. 0 168 889) as through-the-wash softeners.
  • the formulation of the art through-the-wash softening detergent compositions can, however, be subject to flexibility problems which are often due to incompatibility between certain ingredients (between e.g. peroxyacid bleaching agents and softening agents).
  • Carboxy-amides have been used as antistatic agents in industrial textile treatment (German patent 30 43 618) and N-alkyl isostearamides as antistatic agents in laundry application (French patent 2,531,447).
  • Japanese patent J5 8144-175-A discloses the industrial treatment of textile by cationic softening agents and ethoxylated fatty acid amides.
  • Diamides having as a substituent long chain alkyl groups are described in EP-A-87 233, EP-A-94 250 and EP-A-258 500, published in 09.03.88.
  • Alkoxylated fatty amides are known as surfactants (EP-A-0 000 595) and as viscosity control agents (EP-A-0 112 719).
  • German Patent Application 19 59 007 discloses the use as softening agent of a monoethanolamide.
  • German Patent Application 33 10 417 discloses the use of fatty acids diethanolamides as antistatic/non-yellowing agents.
  • the present invention relates to detergent compositions, capable of giving through-the-wash fabric-care benefits inclusive of softness, containing detersive surfactants, a nitrogen-containing fabric softening agent and, if desired detersive additives, characterized in that the nitrogen-containing softening agent is selected from the group of :
  • the softening agents for use in the present invention are selected from the amides or sulfonamides of the formulas i) to iv) disclosed hereinabove.
  • R1, R2, R3, R4 in formula iii) or iv) are all selected from tallow and coconut alkyl groups.
  • Preferred compounds have the formula ii) with R5 being either a C1 ⁇ 5 alkylene or alkenylene group, or a phenylene or substituted phenylene group.
  • R5 is an alk(en)ylene group
  • preferred compounds include the tetra-coconut and tetra-tallow diamides derived from the following carboxylic acids : malonic, succinic, maleic, glutaric, adipic.
  • An especially preferred compound of above category is tetracoconut adipamide.
  • the amide group bearing R3 and R4 chains can be in any of the ortho, meta, or para position with regard to the amide group bearing R1 and R2 chains.
  • R5 is a phenylene or substituted phenylene group
  • preferred compounds are tetra-tallow terephtalic diamide and tetracoconut terephtalic diamide.
  • a preferred polyaromatic group for R5 is biphenylene.
  • the softening agent is generally used at levels of from 0.1% to 15% by weight, preferably from 1% to 10% by weight, most preferably from 3% to 6% by weight.
  • the softening agent is pre-mixed (predispersed) with a dispersing agent, and the resulting mixture is then added to the rest of the composition.
  • any conventional dispersing agent can be used for that purpose.
  • fatty acids are used as dispersing agents for the amide softener.
  • Fatty acids having from 10 to 20 carbon atoms in the alkyl chain like lauric, myristic, palmitic, stearic, oleic acids and mixtures thereof can advantageously be used in the present context. Especially preferred is a mixture of palmitic and stearic acids.
  • Fatty acid dispersing agents are used most preferably in a weight ratio of 1/1 to 10/1 of amide softening agent to fatty acid.
  • compositions of this invention will typically contain organic surface-active agents ("surfactants”) to provide the usual cleaning benefits associated with the use of such materials.
  • surfactants organic surface-active agents
  • Detersive surfactants useful herein include well-known synthetic anionic, nonionic, amphoteric and zwitterionic surfactants. Typical of these are the alkyl benzene sulfonates, alkyl- and alkylether sulfates, paraffin sulfonates, olefin sulfonates, alkoxylated (especially ethoxylated) alcohols and alkyl phenols, amine oxides and alpha-sulfonates of fatty acids and of fatty acid esters, which are well-known from the detergency art.
  • detersive surfactants contain an alkyl group in the C9-C18 range; the anionic detersive surfactants can be used in the form of their sodium, potassium or triethanolammonium salts; the nonionics generally contain from 5 to 17 ethylene oxide groups.
  • U.S. Patent 4.111.855 contains detailed listings of such typical detersive surfactants. C11-C16 alkyl benzene sulfonates, C12-C18 paraffin-sulfonates and alkyl sulfates, and the ethoxylated alcohols and alkyl phenols are especially preferred in the compositions of the present type.
  • surfactant are the water-soluble soaps, e.g. the common sodium and potassium coconut or tallow soaps well-known in the art.
  • the surfactant component can comprise as little as 1% of the compositions herein, but preferably the compositions will contain 5% to 40%, preferably 10% to 30%, of surfactant. Mixtures of the ethoxylated nonionics with anionics such as the alkyl benzene sulfonates, alkyl sulfates and paraffin sulfonates are preferred for through-the-wash cleansing of a broad spectrum of soils and stains from fabrics.
  • the amide softening agent is preferably, without this being an essential requirement, used in combination with a detergent-compatible clay softener.
  • clay softeners are well-known in the detergency art and are in broad commercial use, both in Europe and in the United States. Included among such clay softeners are various heat-treated kaolins and various multi-layer smectites.
  • Preferred clay softeners are smectite softener clays that are described in German Patent Application 23 34 899 and in U.K. Patent 1.400.898.
  • Softener clays are used in the preferred compositions at levels of at least 1%, generally 1-20%, preferably 2-10%.
  • compositions herein can contain other ingredients which aid in their cleaning performance.
  • the compositions herein can advantageously contain a bleaching agent, especially a peroxyacid bleaching agent, without any prejudice to the stability and overall performance, thanks to the compatibility of the amide softening agents of the invention with peroxyacid bleaching agents.
  • peroxyacid bleaching agent encompasses both peroxyacids per se and systems which are able to yield peroxyacids in situ .
  • Peroxyacids per se are meant to include the alkaline and alkaline-earth metal salts thereof.
  • Peroxyacids and diperoxyacids are commonly used; examples are diperoxydodecanoic acid (DPDA) or peroxyphthalic acid.
  • Systems capable of delivering peracids in situ consist of a peroxygen bleaching agent and an activator therefor.
  • the peroxygen bleaching agents are those capable of yielding hydrogen peroxide in an aqueous solution; those compounds are well-known in the art, and include hydrogen peroxide, alkali-metal peroxides, organic peroxide bleaching agents such as urea peroxide and inorganic persalt bleaching agents such as alkali metal perborates, percarbonates, perphosphates or persilicates.
  • sodium perborate commercially available in the form of mono- and tetra-hydrates, sodium carbonate peroxyhydrate, sodium pyrophosphate peroxyhydrate and urea peroxyhydrate.
  • the liberated hydrogen peroxide reacts with the bleach activator to form the peroxyacid bleach.
  • Classes of bleach activators include esters, imides, imidazoles, oximes, and carbonates.
  • preferred materials include methyl o-acetoxy benzoates; sodium-p-acetoxy benzene sulfonates such as sodium 4-nonanoyloxybenzene sulfonate; sodium-4-octanoyloxybenzene sulfonate, and sodium-4-decanoyloxybenzenesulfonate: bisphenol A diacetate; tetra acetyl ethylene diamine; tetra acetyl hexamethylene diamine; tetra acetyl methylene diamine.
  • alpha-substituted alkyl or alkenyl esters such as sodium-4(2-chlorooctanolyloxy)benzene sulfonate, sodium 4-(3,5,5-trimethyl hexanoyloxy)benzene sulfonate.
  • Suitable peroxyacids are also peroxygen bleach activators such as described in published European Patent Application N o 0 166 571, i.e., compounds of the general type RXAOOH and RXAL, wherein R is a hydroxycarbyl group, X is a hetero-atom, A is a carbonyl bridging group and L is a leaving group, especially oxybenzenesulfonate.
  • compositions herein may contain alternatively any other type of bleaching agent, conventionally used in detergent compositions.
  • through-the-wash detergent compositions contain a detergent builder and/or metal ion sequenstrant.
  • detergent builders include the nitrilotriacetates, polycarboxylates, citrates, water-soluble phosphates such as tri-polyphosphate and sodium ortho- and pyro-phosphates, silicates, and mixtures thereof.
  • Metal ion sequestrants include all of the above, plus materials like ethylenediaminetetraacetate, the amino-polyphosphonates and phosphates (DEQUEST®) and a wide variety of other poly-functional organic acids and salts too numerous to mention in detail here. See U.S. Patent 3.579.454 for typical examples of the use of such materials in various cleaning compositions. In general, the builder/sequestrant will comprise 0.5% to 45% of the composition.
  • the 1-10 ⁇ m size zeolite (e.g. zeolite A) builders disclosed in German Patent 24 22 655 are especially preferred for use in low-phosphate or non-phosphate compositions.
  • the laundry compositions herein also preferably contain enzymes to enhance their through-the-wash cleaning performance on a variety of soils and stains, such as amylase, protease, cellulase enzymes.
  • Amylase and protease enzymes suitable for use in detergents are well-known in the art and in commercially available liquid and granular detergents.
  • Commercial detersive enzymes preferably a mixture of amylase and protease are typically used at levels of 0.001% to 2%, and higher, in the present compositions.
  • quaternary ammonium compounds of the form R4R5R6R7N+X ⁇ , wherein R4 is alkyl having from 10 to 20, preferably from 12-18 carbon atoms, and R5, R6 and R7 are each C1 to C4 alkyl preferably methyl: X ⁇ is an anion, e.g. chloride.
  • quaternary ammonium compounds include C12-C14 alkyl trimethyl ammonium chloride and cocoalkyl trimethyl ammonium methosulfate.
  • the quaternary ammonium compounds can be used at levels from 0.5% to 5%, preferably from 1% to 3%.
  • compositions herein can contain, in addition to ingredients already mentioned, various other optional ingredients typically used in commercial products to provide aesthetic or additional product performance benefits.
  • Typical ingredients include pH regulants, perfumes, dyes, optical brighteners, soil suspending agents, hydrotropes and gel-control agents, freeze-thaw stabilizers, bactericides, preservatives, suds control agents, bleach stabilizing agents.
  • the compositions are typically used at a concentration of at least 500 ppm, preferrably 0.10% to 1.5%, in an aqueous laundry bath at pH 7-11 to launder fabrics.
  • the laundering can be carried out over the range from 5°C to the boil, with excellent results.
  • the detergent compositions of this invention can be present in any suitable physical state inclusive of granular, liquid, pasty, or sheet-like form. They may be prepared in any way, as appropriate to their physical form, by mixing the components, co-agglomerating them, micro-encapsulating them, dispersing them in a liquid carrier, and releasably adsorbing or coating them onto a non-particulate substrate, such as a non-woven or paper sheet.
  • compositions are in granular form.
  • a preferred method of preparation of said granular compositions consists in preparing a melt of the dispersing agent and the amide, dispersing the molten mixture into a stirred, aqueous crutcher mix comprising the balance of the detersive ingredients, and spray-drying in standard fashion.
  • the melt can be atomized onto the detergent granules.
  • the compositions herein may also be sprayed onto particles of, e.g., sodium perborate mono or tetrahydrate, sodium sulfate, sodium carbonate, sodium silicate, sodium phosphate, or clay of the type described above.
  • a mix of tetracoconut terepthalic diamide (total 5% of complete formulation after spray-on) and lauric acid (1.5% of complete formulation) are admixed, melted and stirred until homogeneity.
  • a standard aqueous crutcher mix comprising the following ingredients is prepared (percentages listed relate to percent ingredients in the complete formulation after spray-drying).
  • the crutcher mix is then handled in entirely standard fashion, and spray-dried. After drying, sodium perborate (20%) and bleach activator (3% 3-5-5-trimethyl hexanoic acid, sulfaphenyl ester, sodium salt***) (3%) are dry-mixed with the granules. The tetracoconut terephtalic diamide/lauric acid melt is then sprayed onto the finished product.
  • Example 1 The composition of Example 1 was compared for through-the-wash softness vs. an identical composition which did not contain the tetracoconut terepthalic diamide/lauric acid premix (reference).
  • the design of the test was such as to compare softness of textile pieces laundered 1 time (monocycle) and 4 times (multi-cycle) with invention and reference composition.
  • the testing conditions were as follows:
  • a low-P spray-dried detergent formulation is a follows :
  • Example 2 The composition of Example 2 is prepared in the manner described for Example 1.
  • the composition of Example 2 provides better softness than the composition wherein the amide/lauric acid complex has been replaced by additional sodium sulfate.

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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)
  • Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
EP87202157A 1986-11-13 1987-11-06 Detergent composition containing a polyamide softening agent Expired - Lifetime EP0274142B1 (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
AT87202157T ATE84063T1 (de) 1986-11-13 1987-11-06 Polyamid-weichmacher enthaltendes reinigungsmittel.

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
GB868627181A GB8627181D0 (en) 1986-11-13 1986-11-13 Softening detergent compositions
GB8627181 1986-11-13

Publications (3)

Publication Number Publication Date
EP0274142A2 EP0274142A2 (en) 1988-07-13
EP0274142A3 EP0274142A3 (en) 1989-06-28
EP0274142B1 true EP0274142B1 (en) 1992-12-30

Family

ID=10607298

Family Applications (1)

Application Number Title Priority Date Filing Date
EP87202157A Expired - Lifetime EP0274142B1 (en) 1986-11-13 1987-11-06 Detergent composition containing a polyamide softening agent

Country Status (13)

Country Link
EP (1) EP0274142B1 (enrdf_load_stackoverflow)
JP (1) JPS63199294A (enrdf_load_stackoverflow)
KR (1) KR880006352A (enrdf_load_stackoverflow)
CN (1) CN87107303A (enrdf_load_stackoverflow)
AT (1) ATE84063T1 (enrdf_load_stackoverflow)
AU (1) AU8115287A (enrdf_load_stackoverflow)
DE (1) DE3783352T2 (enrdf_load_stackoverflow)
DK (1) DK170117B1 (enrdf_load_stackoverflow)
FI (1) FI93468C (enrdf_load_stackoverflow)
GB (1) GB8627181D0 (enrdf_load_stackoverflow)
GR (1) GR3006782T3 (enrdf_load_stackoverflow)
IE (1) IE59906B1 (enrdf_load_stackoverflow)
NZ (1) NZ222531A (enrdf_load_stackoverflow)

Families Citing this family (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CA2092192C (en) * 1990-10-12 1998-08-18 Jeffrey John Scheibel Process for preparing n-alkyl polyhydroxy amines and fatty acid amides therefrom in hydroxy solvents
WO1998045308A1 (en) * 1997-04-09 1998-10-15 Rhodia Inc. Nonionic gemini surfactants having hydrophilic sugar groups
US6306463B1 (en) * 2000-07-20 2001-10-23 Air Products And Chemicals, Inc. Citric acid tri-alkylamide surfactants
KR100405314B1 (ko) * 2001-07-03 2003-11-12 주식회사 엘지생활건강 비이온성 계면활성제의 제조방법
DE102006036889A1 (de) * 2006-08-04 2008-02-07 Clariant International Limited Verwendung von Aminoacetonen und deren Salzen als Bleichkraftverstärker für Persauerstoffverbindungen
JP4873634B2 (ja) * 2007-01-12 2012-02-08 株式会社コルグ 調律器
JP2020063435A (ja) * 2018-10-11 2020-04-23 花王株式会社 繊維製品用洗浄剤組成物

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE3367617D1 (en) * 1982-02-04 1987-01-02 Unilever Plc Process for producing low-sudsing detergent compositions
ZA833292B (en) * 1982-05-11 1984-12-24 Unilever Plc Granules containing silicone-based anti-foam and a process for preparing them
GB8609884D0 (en) * 1986-04-23 1986-05-29 Procter & Gamble Softening detergent compositions
EP0258500A1 (en) * 1986-09-02 1988-03-09 Akzo N.V. Fabric softening composition and detergent-composition comprising the same

Also Published As

Publication number Publication date
DK170117B1 (da) 1995-05-29
FI93468C (fi) 1995-04-10
EP0274142A2 (en) 1988-07-13
IE59906B1 (en) 1994-04-20
DE3783352D1 (de) 1993-02-11
DK598687D0 (da) 1987-11-13
EP0274142A3 (en) 1989-06-28
FI874996A7 (fi) 1988-05-14
CN87107303A (zh) 1988-05-25
JPS63199294A (ja) 1988-08-17
GR3006782T3 (enrdf_load_stackoverflow) 1993-06-30
DE3783352T2 (de) 1993-05-13
DK598687A (da) 1988-05-14
FI93468B (fi) 1994-12-30
IE873056L (en) 1988-05-13
ATE84063T1 (de) 1993-01-15
KR880006352A (ko) 1988-07-22
NZ222531A (en) 1990-11-27
GB8627181D0 (en) 1986-12-10
AU8115287A (en) 1988-05-19
FI874996A0 (fi) 1987-11-12

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