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GB1374989A - Surface treating method - Google Patents

Surface treating method

Info

Publication number
GB1374989A
GB1374989A GB1488371*[A GB1488371A GB1374989A GB 1374989 A GB1374989 A GB 1374989A GB 1488371 A GB1488371 A GB 1488371A GB 1374989 A GB1374989 A GB 1374989A
Authority
GB
United Kingdom
Prior art keywords
agent
cationic
alkyl
agents
cationic form
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
Application number
GB1488371*[A
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 Ltd
Original Assignee
Procter and Gamble Ltd
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
Priority to GB669971A priority Critical patent/GB1370111A/en
Priority to US00203415A priority patent/US3809646A/en
Priority to DE19712160411 priority patent/DE2160411A1/en
Priority to FR7143907A priority patent/FR2117493A5/fr
Priority to BE776343A priority patent/BE776343A/en
Priority to AT1053271A priority patent/AT324514B/en
Priority to NL7116806A priority patent/NL7116806A/xx
Priority to CA129,534A priority patent/CA999596A/en
Application filed by Procter and Gamble Ltd filed Critical Procter and Gamble Ltd
Priority to GB1488371*[A priority patent/GB1374989A/en
Priority to GB5822570A priority patent/GB1344634A/en
Priority to FR7208507A priority patent/FR2128852B1/fr
Priority to CH357472A priority patent/CH549685A/en
Priority to NL7203246A priority patent/NL7203246A/xx
Priority to SE7203106A priority patent/SE378817B/xx
Priority to CA136,804A priority patent/CA970781A/en
Priority to AT204272A priority patent/AT323302B/en
Priority to DE2211576A priority patent/DE2211576C3/en
Priority to NLAANVRAGE7203245,A priority patent/NL168281C/en
Priority to DE19722211577 priority patent/DE2211577A1/en
Priority to FR7208508A priority patent/FR2129614A5/fr
Priority to BE780516A priority patent/BE780516A/en
Priority to AT204372A priority patent/AT321906B/en
Priority to BE780512A priority patent/BE780512A/en
Priority to US00361740A priority patent/US3856684A/en
Publication of GB1374989A publication Critical patent/GB1374989A/en
Expired legal-status Critical Current

Links

Classifications

    • CCHEMISTRY; METALLURGY
    • C11ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11DDETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D1/00Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
    • C11D1/88Ampholytes; Electroneutral compounds
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D235/00Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings
    • C07D235/02Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings condensed with carbocyclic rings or ring systems
    • C07D235/04Benzimidazoles; Hydrogenated benzimidazoles
    • C07D235/06Benzimidazoles; Hydrogenated benzimidazoles with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached in position 2
    • C07D235/14Radicals substituted by nitrogen atoms
    • CCHEMISTRY; METALLURGY
    • C11ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11DDETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D1/00Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
    • C11D1/38Cationic compounds
    • C11D1/62Quaternary ammonium compounds
    • CCHEMISTRY; METALLURGY
    • C11ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11DDETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D3/00Other compounding ingredients of detergent compositions covered in group C11D1/00
    • C11D3/0005Other compounding ingredients characterised by their effect
    • C11D3/001Softening compositions
    • DTEXTILES; PAPER
    • D06TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06MTREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
    • D06M13/00Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment
    • D06M13/322Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with compounds containing nitrogen
    • D06M13/325Amines
    • D06M13/335Amines having an amino group bound to a carbon atom of a six-membered aromatic ring
    • DTEXTILES; PAPER
    • D06TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06MTREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
    • D06M13/00Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment
    • D06M13/322Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with compounds containing nitrogen
    • D06M13/46Compounds containing quaternary nitrogen atoms
    • DTEXTILES; PAPER
    • D06TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06MTREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
    • D06M13/00Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment
    • D06M13/322Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with compounds containing nitrogen
    • D06M13/46Compounds containing quaternary nitrogen atoms
    • D06M13/47Compounds containing quaternary nitrogen atoms derived from heterocyclic compounds
    • DTEXTILES; PAPER
    • D06TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06MTREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
    • D06M13/00Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment
    • D06M13/322Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with compounds containing nitrogen
    • D06M13/46Compounds containing quaternary nitrogen atoms
    • D06M13/47Compounds containing quaternary nitrogen atoms derived from heterocyclic compounds
    • D06M13/473Compounds containing quaternary nitrogen atoms derived from heterocyclic compounds having five-membered heterocyclic rings
    • DTEXTILES; PAPER
    • D06TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06MTREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
    • D06M16/00Biochemical treatment of fibres, threads, yarns, fabrics, or fibrous goods made from such materials, e.g. enzymatic
    • GPHYSICS
    • G08SIGNALLING
    • G08BSIGNALLING OR CALLING SYSTEMS; ORDER TELEGRAPHS; ALARM SYSTEMS
    • G08B13/00Burglar, theft or intruder alarms
    • G08B13/02Mechanical actuation
    • G08B13/12Mechanical actuation by the breaking or disturbance of stretched cords or wires

Landscapes

  • Chemical & Material Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Organic Chemistry (AREA)
  • Textile Engineering (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Wood Science & Technology (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Physics & Mathematics (AREA)
  • General Physics & Mathematics (AREA)
  • Biochemistry (AREA)
  • General Chemical & Material Sciences (AREA)
  • Microbiology (AREA)
  • Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
  • Detergent Compositions (AREA)

Abstract

1374989 Treating surfaces with convertible surfactants PROCTER & GAMBLE Ltd 8 Dec 1971 [8 Dec 1970 12 March 1971 14 May 1971] 57019/71 57020/71 and 14883/71 Divided out of 1344634 and 1370111 Heading D1P [Also in Divisions A5 and C5] A method of treating a surface which has a negative charge when washed comprises (a) wetting the surface with an aqueous solution containing a convertible surface active agent which is able to exist in cationic and non- cationic (i.e. nonionic, anionic or zwitterionic) forms and which has a pKa (defined as being the pH at which 50 mole per cent of the agent is present in cationic form) of 4-9, the solution having a pH below or not more than 2 units above the pKa value of the agent; and (b) subsequently washing the surface with a wash liquor having a pH at least 2 units above the pKa value of the agent. In its cationic form, the agent is substantive to the surface. In its non-cationic form it is non substantive to the surface thus facilitating its removal during step (b). The surface may be a textile (e.g. cotton) and the agent may confer softening, antistatic, soil repellant, soil release, dye transfer resistance and bactericidal properties. The agent may have the formula I: where R<SP>1</SP> is in general a long chain alkyl or alkyl aryl group (up to 26C), R<SP>3</SP> is a short chain alkyl or aryl group (up to 6C), optionally substituted by hydroxy, or cyano, and R<SP>2</SP> may be the same as R<SP>1</SP> or R<SP>3</SP>. X is an anion e.g. halogen or methosulphate and n may be 1-4. Q is an optionally substituted homo- or hetero-cyclic ring having a weakly acidic character. Q may be a phenolic, imidazole or benzimidazole ring. Substituents for Q may be halogen, alkyl or alkoxy (1-6C), nitro, amino, amido, keto, hydroxy or cyano. Other suitable agents include polyoxyalkylene amines, nitrogen ylides as disclosed in Specification 1003926 and 1360233 and quaternary ammonio imides as disclosed in Specification 1359673. Typical compounds are cetylamide trimethylammonium iodide, octadecyl dimethyl-4-hydroxyphenylammonium chloride or iodide, 2-benzimidazolo methyl hexadecyldimethylammonium chloride and 2-benzimidazolo methyl octadecyldimethyl ammonium chloride. The agent may be formulated as a rinse additive composition containing pH buffering agents (e.g. water soluble phosphates, borates, carbonates; citrates or tartrates and their corresponding acids) in such an amount as to generate an aqueous solution having the pH required by step (a) on dilution with tap water or by addition to a rinse solution. Alternatively the agent may be formulated as an alkaline detergent composition containing the usual building salts (e.g. alkali metal phosphates, polyphosphates, carbonates or silicates), chelating agents (e.g. nitriloacetates polycarboxylates, citrates or gluconates), neutral salts (e.g. alkali metal chlorides or sulphates), bleaching agents (e.g. sodium perborate, percarbonates or perphosphates) and non-cationic surface active agents. Suitable non-cationics include anionics when compatible, e.g. alkylaryl sulphonates, alkyl sulphates, and alkyl ether sulphates; nonionics e.g. polyoxyethylene alcohols, alkylphenols, fatty acids and amines, polyethylene oxide-polypropylene oxide condensates and polyoxyethylene sorbitan esters; zwitterionics e.g. quaternary ammonium carboxylates, and sulphonates; and semi-polar nonionic surfactants e.g. tertiary amine oxides and phosphine oxides. The agent, when in cationic form, improves the substantivity of the nonionics and zwitterionics. The agent may be present in an amount of 0.01-5% on the dry weight of the textile. The solution in step (b) for washing the agent off the surface preferably has a pH at least 3 units above the pKa value of the agent, and may be tap water (pH 6.5).
GB1488371*[A 1970-12-08 1971-12-08 Surface treating method Expired GB1374989A (en)

Priority Applications (24)

Application Number Priority Date Filing Date Title
GB669971A GB1370111A (en) 1970-12-08 1971-03-12 Quaternary ammonium benzimidazole derivatives as their use as textile treatment agents
US00203415A US3809646A (en) 1970-12-08 1971-11-30 Novel ammoniophenolate compounds
DE19712160411 DE2160411A1 (en) 1970-12-08 1971-12-06 Surface-active compounds
FR7143907A FR2117493A5 (en) 1970-12-08 1971-12-07
BE776343A BE776343A (en) 1970-12-08 1971-12-07 TENSIO-ACTIVE COMPOUNDS
AT1053271A AT324514B (en) 1970-12-08 1971-12-07 TEXTILE SOFTENING MIX
NL7116806A NL7116806A (en) 1970-12-08 1971-12-07
CA129,534A CA999596A (en) 1970-12-08 1971-12-07 Surface active and textile softening compounds
GB1488371*[A GB1374989A (en) 1970-12-08 1971-12-08 Surface treating method
GB5822570A GB1344634A (en) 1970-12-08 1971-12-08 Surface active and textile softening compounds
NLAANVRAGE7203245,A NL168281C (en) 1970-12-08 1972-03-10 METHOD FOR PREPARING A TEXTILE SOFTENING PREPARATION BASED ON AN IMIDA SOLE DERIVATIVE
FR7208507A FR2128852B1 (en) 1970-12-08 1972-03-10
NL7203246A NL7203246A (en) 1970-12-08 1972-03-10
SE7203106A SE378817B (en) 1970-12-08 1972-03-10
CA136,804A CA970781A (en) 1970-12-08 1972-03-10 Surface active compounds and compositions
AT204272A AT323302B (en) 1970-12-08 1972-03-10 TEXTILE TREATMENT PRODUCTS
DE2211576A DE2211576C3 (en) 1970-12-08 1972-03-10 Use of quaternary benzimidazoles as fabric softeners with a simultaneous dirt-releasing effect
CH357472A CH549685A (en) 1970-12-08 1972-03-10 COMMERCIAL TEXTILE TREATMENT AGENT.
DE19722211577 DE2211577A1 (en) 1970-12-08 1972-03-10 New surface-active compounds
FR7208508A FR2129614A5 (en) 1970-12-08 1972-03-10
BE780516A BE780516A (en) 1970-12-08 1972-03-10 NEW SURFACTANTS
AT204372A AT321906B (en) 1970-12-08 1972-03-10 PROCESS FOR PRODUCING NEW IMIDAZOLE DERIVATIVES
BE780512A BE780512A (en) 1970-12-08 1972-03-10 TEXTILE TREATMENT AGENTS
US00361740A US3856684A (en) 1970-12-08 1973-05-18 Composition containing benzimidazole derivatives for softening rinse

Applications Claiming Priority (7)

Application Number Priority Date Filing Date Title
GB5822570 1970-12-08
GB669971A GB1370111A (en) 1970-12-08 1971-03-12 Quaternary ammonium benzimidazole derivatives as their use as textile treatment agents
GB5701971 1971-12-08
GB5702071 1971-12-08
GB1488371*[A GB1374989A (en) 1970-12-08 1971-12-08 Surface treating method
US23003272A 1972-02-28 1972-02-28
US00361740A US3856684A (en) 1970-12-08 1973-05-18 Composition containing benzimidazole derivatives for softening rinse

Publications (1)

Publication Number Publication Date
GB1374989A true GB1374989A (en) 1974-11-20

Family

ID=27562556

Family Applications (3)

Application Number Title Priority Date Filing Date
GB669971A Expired GB1370111A (en) 1970-12-08 1971-03-12 Quaternary ammonium benzimidazole derivatives as their use as textile treatment agents
GB1488371*[A Expired GB1374989A (en) 1970-12-08 1971-12-08 Surface treating method
GB5822570A Expired GB1344634A (en) 1970-12-08 1971-12-08 Surface active and textile softening compounds

Family Applications Before (1)

Application Number Title Priority Date Filing Date
GB669971A Expired GB1370111A (en) 1970-12-08 1971-03-12 Quaternary ammonium benzimidazole derivatives as their use as textile treatment agents

Family Applications After (1)

Application Number Title Priority Date Filing Date
GB5822570A Expired GB1344634A (en) 1970-12-08 1971-12-08 Surface active and textile softening compounds

Country Status (10)

Country Link
US (2) US3809646A (en)
AT (3) AT324514B (en)
BE (3) BE776343A (en)
CA (2) CA999596A (en)
CH (1) CH549685A (en)
DE (3) DE2160411A1 (en)
FR (3) FR2117493A5 (en)
GB (3) GB1370111A (en)
NL (3) NL7116806A (en)
SE (1) SE378817B (en)

Families Citing this family (14)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3951879A (en) * 1973-12-14 1976-04-20 Colgate-Palmolive Company Detergent that reduces electrostatic cling of synthetic fabrics
US3997453A (en) * 1974-02-11 1976-12-14 Colgate-Palmolive Company Softener dispersion
US3984335A (en) * 1975-01-16 1976-10-05 Basf Wyandotte Corporation Compositions for souring and softening laundered textile materials and stock solutions prepared therefrom
US4306081A (en) * 1980-01-18 1981-12-15 Albee Laboratories, Inc. Symmetrical quaternary ammonium compounds and their use in heavy metals recovery
US4335219A (en) * 1981-04-06 1982-06-15 The Dow Chemical Company Process for reacting isocyanates in the presence of quaternary ammonium zwitterions
US4485048A (en) * 1982-08-09 1984-11-27 Akzona Incorporated Ethoxylated quaternary benzyl compounds
US4687509A (en) * 1986-05-19 1987-08-18 The Dow Chemical Company N,N,N-tributyl-(3-hydroxybenzyl)ammonium salts and a method for increasing yield of soybeans
US5234817A (en) * 1988-10-07 1993-08-10 Eastman Kodak Company Wash solution containing a cationic surfactant and its use in chlamydial and gonococcal determinations
EP0736594A1 (en) * 1995-04-03 1996-10-09 The Procter & Gamble Company Soaker compositions
US6087313A (en) * 1997-02-27 2000-07-11 The Procter & Gamble Company Soaker compositions
CA2547749A1 (en) * 2003-12-03 2005-07-07 The Procter & Gamble Company Automatic machine laundering of fabrics
US7371718B2 (en) * 2005-04-22 2008-05-13 The Dial Corporation Liquid fabric softener
US9826876B2 (en) 2013-09-30 2017-11-28 Kimberly-Clark Worldwide, Inc. Low-moisture cloud-making cleaning article
CN103951702B (en) * 2014-05-09 2016-05-18 齐齐哈尔大学 1,1 '-dialkyl group-3, the preparation method of salt compound in 3 '-(2-phosphate-1,3-propylidene) imidazoles

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE1287585B (en) * 1963-12-13 1969-01-23 Hoechst Ag Process for the preparation of benzimidazolium compounds
CH443777A (en) * 1965-08-06 1968-02-15 Agripat Sa Process for protecting textile keratin fibers from insect caused damage and means for carrying out this process
US3673209A (en) * 1965-08-06 1972-06-27 Geigy Chem Corp Biocidally active benzimidazole compounds

Also Published As

Publication number Publication date
BE780516A (en) 1972-09-11
NL168281C (en) 1981-10-16
US3809646A (en) 1974-05-07
DE2160411A1 (en) 1972-06-22
NL7203245A (en) 1972-09-14
FR2128852A1 (en) 1972-10-20
NL7203246A (en) 1972-09-14
BE776343A (en) 1972-06-07
SE378817B (en) 1975-09-15
DE2211576C3 (en) 1982-01-28
GB1370111A (en) 1974-10-09
US3856684A (en) 1974-12-24
AT323302B (en) 1975-07-10
DE2211576B2 (en) 1981-04-30
FR2117493A5 (en) 1972-07-21
CA970781A (en) 1975-07-08
CA999596A (en) 1976-11-09
FR2128852B1 (en) 1976-08-06
GB1344634A (en) 1974-01-23
DE2211577A1 (en) 1972-09-21
BE780512A (en) 1972-09-11
NL7116806A (en) 1972-06-12
CH549685A (en) 1974-05-31
AT324514B (en) 1975-09-10
NL168281B (en) 1981-10-16
FR2129614A5 (en) 1972-10-27
DE2211576A1 (en) 1972-09-21
AT321906B (en) 1975-04-25

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Legal Events

Date Code Title Description
PS Patent sealed [section 19, patents act 1949]
PCNP Patent ceased through non-payment of renewal fee

Free format text: IN PAT.BUL.5032,PAGE 1916 FOR 1374948 READ 1374989