US3809535A - Dry cleaning of textiles - Google Patents

Dry cleaning of textiles Download PDF

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Publication number
US3809535A
US3809535A US00208436A US20843671A US3809535A US 3809535 A US3809535 A US 3809535A US 00208436 A US00208436 A US 00208436A US 20843671 A US20843671 A US 20843671A US 3809535 A US3809535 A US 3809535A
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US
United States
Prior art keywords
cleaning
solvent
acid
sim
examples
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
US00208436A
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English (en)
Inventor
Jean Neel
Bernard Papillon
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.)
Rhone Progil SA
Original Assignee
Rhone Progil SA
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 DK130650D priority Critical patent/DK130650A/da
Priority to FR7045517A priority patent/FR2117779B1/fr
Priority to GB5580171A priority patent/GB1379739A/en
Priority to NL7116615A priority patent/NL7116615A/xx
Priority to CA129,464A priority patent/CA964806A/en
Application filed by Rhone Progil SA filed Critical Rhone Progil SA
Priority to US00208436A priority patent/US3809535A/en
Priority to DE2162416A priority patent/DE2162416C3/de
Priority to AT1080071A priority patent/AT314466B/de
Application granted granted Critical
Publication of US3809535A publication Critical patent/US3809535A/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
    • C11D7/00—Compositions of detergents based essentially on non-surface-active compounds
    • C11D7/50—Solvents
    • C11D7/5004—Organic solvents
    • C11D7/5013—Organic solvents containing nitrogen
    • 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
    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06L—DRY-CLEANING, WASHING OR BLEACHING FIBRES, FILAMENTS, THREADS, YARNS, FABRICS, FEATHERS OR MADE-UP FIBROUS GOODS; BLEACHING LEATHER OR FURS
    • D06L1/00—Dry-cleaning or washing fibres, filaments, threads, yarns, fabrics, feathers or made-up fibrous goods
    • D06L1/02—Dry-cleaning or washing fibres, filaments, threads, yarns, fabrics, feathers or made-up fibrous goods using organic solvents
    • D06L1/04—Dry-cleaning or washing fibres, filaments, threads, yarns, fabrics, feathers or made-up fibrous goods using organic solvents combined with specific additives
    • 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
    • C11D7/00—Compositions of detergents based essentially on non-surface-active compounds
    • C11D7/22—Organic compounds
    • C11D7/24—Hydrocarbons
    • 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
    • C11D7/00—Compositions of detergents based essentially on non-surface-active compounds
    • C11D7/22—Organic compounds
    • C11D7/28—Organic compounds containing halogen
    • 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
    • C11D7/00—Compositions of detergents based essentially on non-surface-active compounds
    • C11D7/22—Organic compounds
    • C11D7/32—Organic compounds containing nitrogen
    • C11D7/3209—Amines or imines with one to four nitrogen atoms; Quaternized amines
    • 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
    • C11D7/00—Compositions of detergents based essentially on non-surface-active compounds
    • C11D7/22—Organic compounds
    • C11D7/32—Organic compounds containing nitrogen
    • C11D7/3263—Amides or imides

Definitions

  • the intensifier is a primary or secondary amide of a dicarboxylic aliphatic acid or anhydride wherein one carbon atom in the chain connecting the two acid groups bears an alkyl or alkenyl radical containing at least six carbon atoms.
  • the method gives better whiteness and more particularly prevents the re-deposition of dirt.
  • the invention relates to an improvement to dry cleaning of textiles, i.e., the washing of textile fibres or articles with non-aqueous solvents.
  • the invention relates more particularly to the use of a novel kind of adjuvants which improve cleaning and give more thorough bleaching or cleaning.
  • the invention relates to the novel kind of drycleaning intensifiers and to baths containing the aforementioned adjuvants.
  • Dry cleaning is an activity which has recently become widely extended and which uses large tonnages of solvents.
  • the solvents are mainly chlorinated hydrocarbons, more particularly perchloroethylene and trichloroethylene which, owing to their nonflammability and other advantageous properties, have become the main solvents used in this branch of industry. Whatever solvent is used, however, i.e.
  • the solvent does not usually produce adequate cleaning by itself; it is well known to add surface-active agents soluble in the given solvent to the cleaning bath, For example it has become conventional to add agents such as the following to the solvents: amine alkyl-aryl sulphonates, ethoxylated derivatives of aliphatic amines or alcohols, or alkyl-polyethoxy-phenols.
  • the invention provides a novel kind of adjuvants for dry-cleaning baths which substantially improve the degree of cleaning compared with that obtained with conventional surface-active agents.
  • the novel adjuvants are particularly effective when used together with conventional surfactants in the presence of a small proportion of water in the solvent; the resulting cleaning is much more thorough than could be obtained with either of the additivesi.e., the adjuvant according to the invention and the conventional agent-if used alone.
  • the intensifier according to the invention comprises one or more primary or secondary amides derived from an aliphatic diacid or anhydride, bearing an alkyl or alkenyl substituent, and an aliphatic polyamine, the number of carbon atoms in the substituent being greater than in the polyamine.
  • the length of the chain of the hydrocarbon substituent is such that the intensifier is soluble in the given solvent; this means that the chain must usually contain at least 6 carbon atoms, preferably more than 12 C.
  • the best intensifiers are those in which the hydrocarbon substituent forms a chain of 18 to 200 carbon atoms, preferably 24 to C.
  • the carboxylic acid entering into the composition of the primary amides or secondary amides (imides) according to the invention may have their two carboxylic groups in all positions from 11-13 to ot-w. Since, for economic reasons, the products used are mainly derived from C to C diacids (or anhydrides), i.e. from malonic to adipic acid, the carboxylic groups are at the two ends of a chain formed by l to 4 CH and the alkyl or alkenyl substituents is attached to one of the carbon atoms in the chain.
  • acids i.e. malonic, succinic, glutaric and adipic acid-a number of others can be used as the base of the primary amides or imides according to the invention.
  • the base can also comprise derivatives corresponding e.g. to pimelic, suberic, azelaic, sebacic acid, etc., i.e. heptane-, octane-, nonaneor decane-dioic acid respectively, bearing a long alkyl or alkenyl group on one of the carbon atoms connecting the two COOH or --CO--OCO groups.
  • derivatives corresponding e.g. to pimelic, suberic, azelaic, sebacic acid, etc., i.e. heptane-, octane-, nonaneor decane-dioic acid respectively, bearing a long alkyl or alkenyl group on one of the carbon atoms connecting the two COOH or --CO--OCO groups.
  • the amide derivatives according to the invention can come from acids whose carboxyl groups are in positions other than the oc-w positions in their aliphatic chains.
  • Suitable acids correspond e.g. to: 2,5-dicarboxylhexane; 1,4-dicarboxyhexane; 1,6 dicarboxyoctane; 5,7 dicarboxyundecane; 1,4-dicarboxydodecane; 1,8-dicarboxyoctadecane (a derivative of oleic acid), etc.
  • the polyamines from which the amide group of the intensifiers according to the invention is derived are preferably alkylene-polyamines but can if required comprise alcohol-amines, phenol-amines or aromatic amines, provided that they contain at least two atoms of aminated nitrogen per molecule.
  • the following substances are preferred examples of the first group: ethylene-diamine; diethylene-triamine, triethylene-tetramine, tetraethylenepentamine, pentaethylene-hexamine, pentamethylene-diamine, hexamethylene-diamine, tripropylene-tetramine, tetrapropylene-pentamine, etc., or polyalkylene-polyamines or mixtures of heavy polyalkylene polyamines obtained as residues in the manufacture of the aforementioned substances.
  • Cyclic polyamines are also suitable, more particularly piperazine and derivative thereof substituted on the nitrogen atom by one or more alkyl groups, e.g. N- ethyl, N-methyl, N-isopropyl, N-methyl-(fi-amino-ethyD- piperazine etc.
  • the alkyl groups of the aforementioned polyamines may also be branched.
  • the amides according to the invention may also be derived from other amines such as: alkylor dialkylamino-alkyl amines such as methyl-amino-, propylamine, dimethylamino-ethylamine, diethylamino-butylamine; aryl polyamines such as phenylene dior tri-amine, triamino toluene, triamino-triphenyl-methane, diamino-diphenolamine, triamine-phenol, etc.; or alcohol-amines such as di-l,3-amino-2-propanol, 1,2-diamino-3-propanol, triaminohexanol etc.
  • alkylor dialkylamino-alkyl amines such as methyl-amino-, propylamine, dimethylamino-ethylamine, diethylamino-butylamine
  • aryl polyamines such as phenylene dior
  • the primary or secondary amide in the intensifier contains nitrogen atoms bearing hydrocarbyl radicals, inter alia aryl, more particularly alkyl radicals, acyl groups, aryl-soulphonic radicals, or alkoxy or polyoxyalkylene groups.
  • the amine groups can be blocked by adding a molecule of an organic, mineral or mixed acid.
  • the amine groups can be blocked before or during the preparation of the amide.
  • Appropriate reagents inter alia alkyl halides such as methyl, ethyl, propyl, butyl or amyl chloride or bromide, are described in American Pat. No. 2,638,450, which also cites some examples of polyalkylene-polyamines, e.g. N-alkylated polyamines.
  • alkyl halides such as methyl, ethyl, propyl, butyl or amyl chloride or bromide
  • polyalkylene-polyamines e.g. N-alkylated polyamines.
  • the aforementioned examples in no way limit the present invention.
  • the reagents can also be acids or acid anhydrides and halides such as acetic, propionic and butyric acid and anhydrides and chlorides thereof; other reagents are nonlimitatively cited in American Pat. No. 2,568,876.
  • aryl-sulphonic groups are fixed with sulphonic acids whose alkali metal salts are known surfactants and whose amine salts are used in conventional dry cleaning.
  • alkoxy or poly-oxyalkylene groups can be fixed on all or some of the nitrogen atoms in the starting amine or the final amide by a conventional condensation reaction with an oxide of an olefin or a poly-oxyalkylene.
  • Ethylene oxide and propylene oxide are the most common reagents but others can of course be used, e.g. the oxides of butenes, amylenes or hexenes.
  • the primary or secondary amides according to the invention can be on one or more of the amine groups of the starting polyamine.
  • the number of mols of polyamine may vary with respect to the number of mols of diacid or anhydride; the ratio may vary for instance from 0.5 to 2 but is preferably between 0.5 and 1.
  • the aforementioned imides come from the condensation of an anhydride wilth a polyethylene-polyamine in which R is an alkyl or alkenyl group preferably having between 18 and 120 carbon atoms in the chain, n is usually between 0 and 6; Z is a hydrogen atom or one of the aforementioned groups blocking the amine group, e.g. an alkyl, an acyl, a moiety of an alkylor arylsulphonic acid, or a polyoxyalkylene group; Q is a hydrogen atom or a blocking group similar to but not necessarily identical with Z, and the sum (m+p) is usually between 2 and 7, since the amino chain need not be very long.
  • R is a straight polypropylene chain containing 13 propylene links
  • the product is a polypropenyl-glutaric 4 monoimide of tetraethylene pentamine in which the terminal, non-amido nitrogen atom is blocked in the form of dodecylbenzene sulphonates:
  • the aforementioned illustration relates to a monoimide, i.e. a secondary mono-amide, but a di-imide could of course also be used according to the invention; in the latter case the Z group is a second glutaric acid or anhydride radical (2 mole of diacid per mol of polyamine).
  • the last-mentioned formula has the same configuration at the right and at the left end.
  • the bath besides containing one or more intensfiers according to the invention, can contain normal adjuvants such as optical blueing agents, chemical bleaching agents l(peroxides), finishing agents, antistatic agents and the baths may also advantageously contain a small proportion of water, which facilitates the elimination of hydrophilic dirt; the products according to the invention are most efiicient in such cases.
  • water is present in the dry-cleaning organic solvent, it is advisable to add a small proportion of surfactant to the intensifiers according to the invention, in order to emulsify the water in the solvent.
  • ionic or non-ionic surfactants can be used; amine alkyl-aryl-sulphonates are particularly suitable and are widely used in the dry or wet washing of textiles. In such cases it is found that the intensifiers according to the invention cooperate with the surfactants, resulting in considerably improved cleaning.
  • amide to be incorporated according to the invention in the organic solvent used for dry cleaning, a content of 50 g. per litre is usually plenty, and the preferred quantity is usually between approx. 0.1 and 15 g. of intensifier dissolved in each litre of solvent used. More particularly, the proportions of intensifier are lowest in baths containing water.
  • the proportions of surfacants, when used, may be of the same order.
  • the proportion of water the advantage of using which has already been mentioned, preferably does not exceed 100 g./l., the best proportions being between 0 and 20 g./l.
  • the amides according to the invention can be used for dry-cleaning textiles of whatever nature and form; for example, the amides can be used to improve baths for cleaning wool, cotton, synthetic textiles, linen, jute, etc., mixed if required, in the form of yarn, fibres, cloth, knit-
  • the results of tests with two known adjuvants are given: isopropylamine dodecyl-benzene-sulphonate or DBSI and another commercial'amine alkylbenzene-sulphonate known as ABSA and manufactured by ERGOL-TD.
  • SIM imides and ting, finished clothing, etc., either white or colored. 5 DBSI surfactant were used simultaneously.
  • each adjuvant is given in grams per portant application of the intensifiers according to the inlitre of solvent, shown in brackets beside the correspondvention, the adjuvants can also be used to improve varing symbol. ious methods of washing or degreasing all kinds of articles with solvents, as performed every day in industry. For whiteness ofexample, improvements can be made in the action of or- EL Dirty Clean ganic baths for various metal articles before electroplating, No. fabrl fabric Total enamelling, varnishing or painting, y adding about 1 Unwashedcommuabm 25 856 1m to 5% of a primary or secondary amide according to the 2 Washing with solvent. alone--. 29.5 60.5 90.0 invention to the baths 3-- Solvent plus ABSA (1.45 g.) 36.3 57. 8 94. 0
  • SIM ad uvants according to the invention Scnbmg the total efiiect of the adluvant tested considerably improve cleaning, when the organic solvent Examples 1 to 8 contains water.
  • the perchloroethylene used did not Examples 12 to 15 contain water
  • the intensifiers accordin to the in- T tested q l to the Invention was the vention were th: SIM-l mono-succinimides if the prelmlde of spcclmc acld i whlc ⁇ ? a group replaqed vious examples in which the terminal amine had been by lmlylwiutme l havmg lwbutene blocked by dodecyl-benzene-sulphonic (-DBS) acid radi tetraethylene pentamine.
  • the reaction product Wlll have caL
  • the resulting general Structure would be:
  • the quantities of adjuvants and relative proportions of amine per l anhydride, SIM and DBSI are the same as in the preceding example.
  • Examples 12 to 15 all show a marked improvement compared with the results of Examples 3, 4 in accordance with the prior art.
  • Example 18 A mono-adipamide of triethylene-tetramine substituted by a C hydrocarbon radical in its adipic group was used as the intensifier instead of succinimide in tests similar to those in Examples 1 to 8. The results were similar to those given by SIM-0.8.
  • adjuvant F i.e. the succinimide having 8 butene links (32 carbon atoms) on the succinic group.
  • a method for washing solid articles consisting of immersing the articles in a bath consisting of (a) an oragnic solvent belonging to the group consisting of hydrocarbon and halo-hydrocarbon dry cleaning liquids, and (b) a monoimide, added to the solvent to a concentration of 0.1 to 50 g. per litre solvent, the monoamide being defined by the formula:
  • R is a radical selected from the group consisting of alkyls and alkenyls having 18 to carbon atoms; n is an integer of 0 to 6; (m -i-p) is 2 to 7; Z and Q are hydrogen.

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  • Chemical & Material Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Wood Science & Technology (AREA)
  • Organic Chemistry (AREA)
  • Textile Engineering (AREA)
  • Detergent Compositions (AREA)
  • Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
US00208436A 1970-12-17 1971-12-15 Dry cleaning of textiles Expired - Lifetime US3809535A (en)

Priority Applications (8)

Application Number Priority Date Filing Date Title
DK130650D DK130650A (enrdf_load_stackoverflow) 1970-12-17
FR7045517A FR2117779B1 (enrdf_load_stackoverflow) 1970-12-17 1970-12-17
GB5580171A GB1379739A (en) 1970-12-17 1971-12-01 Dry cleaning of textiles
NL7116615A NL7116615A (enrdf_load_stackoverflow) 1970-12-17 1971-12-02
CA129,464A CA964806A (en) 1970-12-17 1971-12-06 Nettoyage a sec de textiles
US00208436A US3809535A (en) 1970-12-17 1971-12-15 Dry cleaning of textiles
DE2162416A DE2162416C3 (de) 1970-12-17 1971-12-16 Mittel zur Reinigung von festen Gegenständen
AT1080071A AT314466B (de) 1970-12-17 1971-12-16 Reinigungsmittel

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
FR7045517A FR2117779B1 (enrdf_load_stackoverflow) 1970-12-17 1970-12-17
US00208436A US3809535A (en) 1970-12-17 1971-12-15 Dry cleaning of textiles

Publications (1)

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US3809535A true US3809535A (en) 1974-05-07

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US00208436A Expired - Lifetime US3809535A (en) 1970-12-17 1971-12-15 Dry cleaning of textiles

Country Status (8)

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US (1) US3809535A (enrdf_load_stackoverflow)
AT (1) AT314466B (enrdf_load_stackoverflow)
CA (1) CA964806A (enrdf_load_stackoverflow)
DE (1) DE2162416C3 (enrdf_load_stackoverflow)
DK (1) DK130650A (enrdf_load_stackoverflow)
FR (1) FR2117779B1 (enrdf_load_stackoverflow)
GB (1) GB1379739A (enrdf_load_stackoverflow)
NL (1) NL7116615A (enrdf_load_stackoverflow)

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3969073A (en) * 1975-01-20 1976-07-13 E. I. Du Pont De Nemours And Company Dry cleaning additive for decreasing soil redeposition
US4597898A (en) * 1982-12-23 1986-07-01 The Proctor & Gamble Company Detergent compositions containing ethoxylated amines having clay soil removal/anti-redeposition properties
US4759865A (en) * 1986-11-06 1988-07-26 Colgate-Palmolive Company Pasty acid detergent composition
US4891160A (en) * 1982-12-23 1990-01-02 The Proctor & Gamble Company Detergent compositions containing ethoxylated amines having clay soil removal/anti-redeposition properties
US4935158A (en) * 1986-10-30 1990-06-19 Aszman Harry W Solid detergent cleaning composition, reusable cleaning pad containing same and method of manufacture

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4317805A (en) * 1979-01-25 1982-03-02 Hooker Chemicals & Plastics Corp. Removal of hydrogen fluoride from gaseous mixtures of hydrogen fluoride and hydrogen chloride
JP2002537444A (ja) * 1999-02-19 2002-11-05 ザ、プロクター、エンド、ギャンブル、カンパニー 布地改良ポリアミンを含んでなる洗濯洗剤組成物

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3969073A (en) * 1975-01-20 1976-07-13 E. I. Du Pont De Nemours And Company Dry cleaning additive for decreasing soil redeposition
US4597898A (en) * 1982-12-23 1986-07-01 The Proctor & Gamble Company Detergent compositions containing ethoxylated amines having clay soil removal/anti-redeposition properties
US4891160A (en) * 1982-12-23 1990-01-02 The Proctor & Gamble Company Detergent compositions containing ethoxylated amines having clay soil removal/anti-redeposition properties
US4935158A (en) * 1986-10-30 1990-06-19 Aszman Harry W Solid detergent cleaning composition, reusable cleaning pad containing same and method of manufacture
US4759865A (en) * 1986-11-06 1988-07-26 Colgate-Palmolive Company Pasty acid detergent composition

Also Published As

Publication number Publication date
DK130650A (enrdf_load_stackoverflow)
FR2117779A1 (enrdf_load_stackoverflow) 1972-07-28
GB1379739A (en) 1975-01-08
CA964806A (en) 1975-03-25
AT314466B (de) 1974-04-10
NL7116615A (enrdf_load_stackoverflow) 1972-06-20
DE2162416C3 (de) 1975-01-16
FR2117779B1 (enrdf_load_stackoverflow) 1973-12-07
DE2162416B2 (de) 1974-06-06
DE2162416A1 (de) 1972-07-13

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