US2978415A - Guanidine soaps as dry cleaning detergents - Google Patents

Guanidine soaps as dry cleaning detergents Download PDF

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US2978415A
US2978415A US653277A US65327757A US2978415A US 2978415 A US2978415 A US 2978415A US 653277 A US653277 A US 653277A US 65327757 A US65327757 A US 65327757A US 2978415 A US2978415 A US 2978415A
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dry cleaning
guanidine
soaps
acid
solvent
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Ralph J Chamberlain
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Wyeth Holdings LLC
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American Cyanamid Co
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    • 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

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  • This invention relates to a class of guanidine soapsof unsaturated higher fatty acid mixtures which are particularly well suited for use as detergents in dry cleaning solvents.
  • the invention includes the washing or dry cleaning of soiled fabrics in organic solvents containing these guanidine soaps as Well as the soaps themselves, which are believed to be new compositions, and methods for their preparation. 7
  • Dry cleaning consists essentially in agitating soiled gar-- ments, cloth or other textiles in a dry cleaning solvent having solvent power for the grease or other soil to be removed.
  • Typical solvents that have been used cmmercially for this purpose include chlorinated aliphatic hydrocarbons such as perchlorethylene, trichlorethylene, carbon tetrachloride and mixtures of carbon tetrachloride (70 mole percent) with ethylene dichloride (30 mole percent).
  • the most widely used solvents are petroleum hydrocarbon fractions including particularly Stoddard solvent which is a petroleum distillate having a minimum flash point of 100 F.
  • 140-F solvent Another petroleum solvent'in com mon use is 140-F solvent, which is a petroleum distillate similar, to Stoddard solvent but with a minimum flash point of 140 F.
  • v y Soap detergents are commonly used in the above and similar dry cleaning solvents ,to facilitate the removal of soil from'the fabrics being washed. Alkali metal soaps and amine soaps of oleic, acid are most commonly used for this purpose.
  • the concentration of soap in the dry cleaning solvent may vary widely with thetype of soap used and with the nature of the textiles to be cleaned, but is usuallywithin the range of about 1 lb; for eachf 6-35 gallons of solvent.
  • the detergent is usually added to;, the washer after the clothhasbeen wet out in, the dry cleaning solyent;;in some'cases a'small amount of. Water; is also added.
  • the washer is then, turnedgwithoutr filiercirculation is begun to rinse the soil.an d. thede fuged to remove excess solvent and are driedin'a current; I
  • these new soaps possess goodrantistatic properties and small amounts retained by the cloth therefore assist in preventing the ac- 'cumulation of dust and lint on the dry cleaned fabrics or garments- Guanidine soaps falling within the scope, of my invention may ,be prepared from a number offatty acid mixtures that are available, cornmercially, or that can be prepared from, commercialfatty acid mixtures by simple refining processes
  • the fatty acid mixture should have a relatively high content, preferably within therange of about 30-60% by weight, of both oleic and linoleic acids and a comparatively low content of saturated fatty acids, which are undesirable in dry cleaning soaps.
  • the preferred raw materials are the tall oil fatty acids, which are obtainable commercially in large quantities. These acids are produced by the, vacuum steam distillation and fractionation of tall oil, a mixture of uns
  • My new guanidine soaps are preferably prepared by reacting one or more of these fatty acid mixtures with guanidine carbonate or'with a guanidine. salt of a stronger acid, such as guanidine hydrochloridefln the presence of, an acid acceptor such as sodium carbonate or sodium hydroxide.
  • a stronger acid such as guanidine hydrochloridefln the presence of, an acid acceptor such as sodium carbonate or sodium hydroxide.
  • the resulting soaps usually contain less than 5% of freefatty acid and are soluble in allproportions in polar organic solvents such asethan- 01 and isopropanol. Theyare also soluble 'in xylenq perchlorethylene and other chlorinated dry. meaning sole.
  • guanidine oleate-linoleate soaps of my invention are compatible in dry cleaning solvents with these soaps and with anionic wetting agents such as sodium dioctyl sulfosuccinate, sodium dihexyl sulfosuccinate, sodium lauryl sulfate, salts of alkylated aromatic sulfonic acids such as keryl benzene sulfonate and alkali metal salts of the sulfonic acids of condensation products of butylene and propylene polymers of about 12 carbon atoms with benzene or toluene.
  • anionic wetting agents such as sodium dioctyl sulfosuccinate, sodium dihexyl sulfosuccinate, sodium lauryl sulfate, salts of alkylated aromatic sulfonic acids such as keryl benzene sulfonate and alkali metal salts of the sulfonic acids of condensation products of
  • nonionic surface active agents such as ethylene oxide or propylene oxide condensation products of alkylated phenols; a typical compound of this class is the condensation product of 8-9 moles of ethylene oxide with one mole of nonyl phenol that is sold commercially as Aerosol NI.
  • these and other wetting agents of the same class may therefore be present during the dry cleaning method of my invention, preferably in quantities of about 0.05% to 1% on the weight of the solvent.
  • Other customary or preferred ingredients may also be present such as finely divided diatomaceous earth or other filter aids, which are usually employed in quantities of about 13%.
  • oleate-linoleate soap a commercial fatty acid mixture sold as Acintol FA-2 was used. This mixture has an acid number of 194, a saponification number of 196 and contains 96.8% of fatty acids of 18 carbon atoms, 1% rosin acids and 2.2% unsaponifiables.
  • the fatty acids consist of 50% oleic acid, 48% linoleic acid and 2% saturated acid.
  • the same product can be prepared from otherguanidine salts such as the nitrate, sulfate, hydrochloride and the like by the use of an acid acceptor such as sodium hydroxide or carbonate.
  • an acid acceptor such as sodium hydroxide or carbonate.
  • the following preparation from guanidine hydrochloride is typical.
  • the guanidine soaps of saturated fatty acids of 16 to 18 carbon atoms are not good dry cleaning detergents and therefore fatty acid mixtures having a relatively low content of these acids, preferably not more than about 10-15%, should be selected.
  • Commercial fatty acids which are otherwise suitable, such as cottonseed oil fatty acids may be pretreated by low temperature crystallization or solvent extraction to remove part or all of their saturated fatty acid content and may then be'converted into guanidine soaps by the above-described procedures.
  • the fatty acid mixtures used in making satisfactory guanidine soap dry cleaning detergents should contain from about 30% to 60% by weight of oleic acid and about 30-60% of linoleic acid.
  • Guanidine coconutate was prepared by dissolving 636 grams of coconut oil fatty acids in 1 liter of methyl isobutyl ketone, heating the solution to -90 C. and adding 283 grams of guanidine carbonate slowly followed by agitation at the same temperature for one hour and drying at 50 C.
  • EXAMPLE 2 Dry cleaning solutions having the following compositions and properties were prepared. In each case the solvent was 2 liters of perchlorethylene (tetrachlorethylene).
  • the potassium oleate was a standard 'dry cleaning soap (Textile Test Method CC C-T-1916, May 1951, Method 5580) prepared by pouring a solution of 35 grams of KOH in 89ml. of distilled water into a mixture of 250 ml. of oleic acid, 724 ml. of Stoddard solvent and ml. of cyclohexanol.
  • the guanidine oleaterlinoleate and guanidine coconutate were those prepared as described in Example 1.
  • a dry cleaning method which comprises washing soiledfabrics in a dry cleaning solvent containing detergent quantities of the guanidine' soap of a fatty acid mixture containing about 30-60% of oleic acid, about 30- of linoleic acid and not more than about 15% of saturated fatty acids.
  • a dry cleaning method which comprises washing soiled fabrics in a dry cleaning solvent containing detergent quantities of the guanidine soap of tall -oil fatty acids produced by the vacuum steam distillation and fracdonation of tall oil.
  • guanidine soap of a tall oil fatty acid mixture suited for use as a detergent in dry cleaning solvents of about 50% of oleic acid and 46-48% of linoleic acid, the balance being saturated fatty acids.

Description

' circulationof. thesolvent through the filter for some 15-40: minutes or until, thgfabrics-are cleaned, after which the:
'te rgent from ,thetextiles. tThe textiles are th'en centri- 'f h as es United States Patent GUANIDINE SOAPS AS DRY CLEANING DETERGENTS Ralph Chamberlain, Stamford, Conn., assignor to American Cyanamid Company, New York, N.Y., a
corporation of Maine No Drawing. Filed Apr. 17, 1957, Ser. No. 653,277 4 Claims. (Cl. 252-118) This invention relates to a class of guanidine soapsof unsaturated higher fatty acid mixtures which are particularly well suited for use as detergents in dry cleaning solvents. The invention includes the washing or dry cleaning of soiled fabrics in organic solvents containing these guanidine soaps as Well as the soaps themselves, which are believed to be new compositions, and methods for their preparation. 7
Dry cleaning consists essentially in agitating soiled gar-- ments, cloth or other textiles in a dry cleaning solvent having solvent power for the grease or other soil to be removed. Typical solvents that have been used cmmercially for this purpose include chlorinated aliphatic hydrocarbons such as perchlorethylene, trichlorethylene, carbon tetrachloride and mixtures of carbon tetrachloride (70 mole percent) with ethylene dichloride (30 mole percent). The most widely used solvents are petroleum hydrocarbon fractions including particularly Stoddard solvent which is a petroleum distillate having a minimum flash point of 100 F. and a volatility such that not' less than 50% is recovered by 350 F., not less than 90% by;375 F., and an end point of about 410 F; whena sample is distilled. Another petroleum solvent'in com mon use is 140-F solvent, which is a petroleum distillate similar, to Stoddard solvent but with a minimum flash point of 140 F. v y Soap detergents are commonly used in the above and similar dry cleaning solvents ,to facilitate the removal of soil from'the fabrics being washed. Alkali metal soaps and amine soaps of oleic, acid are most commonly used for this purpose. The concentration of soap in the dry cleaning solvent may vary widely with thetype of soap used and with the nature of the textiles to be cleaned, but is usuallywithin the range of about 1 lb; for eachf 6-35 gallons of solvent.
" Commercial'dry cleaningprocesse'siare frequently car:
ried out in; a perforate d horizontal cylinder rotating'in side a metal shell and; known, as a washer. Sufiicient solvent is run into-the washerso that the cylinder is filled'" to a depthof approximately A to %,of..its diameter and the textiles tobe dry'cleaned arethen placedin'the cylinder. In cleaning wool thequant'ity of solvent is usually about 1 gallon for each pound of fabric;,with cotton and rayon fabrics. the proportionisfslightly less. The washer is connected to a filter so that the solventcan be continuously freed from-suspended impurities during therinsing operation. The detergentis usually added to;, the washer after the clothhasbeen wet out in, the dry cleaning solyent;;in some'cases a'small amount of. Water; is also added. The washer is then, turnedgwithoutr filiercirculation is begun to rinse the soil.an d. thede fuged to remove excess solvent and are driedin'a current; I
i-My ress invention'is based 'OII'flIeI'dISCOVeIY. that. theguanidine soaps-ofhigher fatty acids containing both oleic acid-*anddinoleic acid: areexcellentdry cleaning dete'rg'ent'si -:In particular; "I have found that"-the1-'soapsf.-
. prepared by neutralizing "higher fatty acid mixtures "con .70
taining approximately, equal; percentages :of :;oleic "acid" sential feature of my dry cleaning method is the washing numerically, these quantities are usually within range 'ofabout 1 1b.;foreach 6 to 35 gallons .ofdry cleaning solvent, and preferably about ,1 lb. for each l0le25 fgal fcluding The guanidine soaps of my invention ma be.
v they1rnayrbe. replaced in. partfb'yt othe'r det e'rgents uchand :linoleiczaacidi withilguanidinei oraguanidine'isalts a Patented Apr. 4, 1961 hibit a number of advantageous properties when used in dry cleaning processes. They posses excellent detergency in dry cleaning solvents and also exhibita low degree of soil redeposition; that is, they maintain the grease and dirt suspended in the organic solvent so that it is not redeposited on the fabrics. In addition, these new soaps possess goodrantistatic properties and small amounts retained by the cloth therefore assist in preventing the ac- 'cumulation of dust and lint on the dry cleaned fabrics or garments- Guanidine soaps falling within the scope, of my invention may ,be prepared from a number offatty acid mixtures that are available, cornmercially, or that can be prepared from, commercialfatty acid mixtures by simple refining processes In general the fatty acid mixture should have a relatively high content, preferably within therange of about 30-60% by weight, of both oleic and linoleic acids and a comparatively low content of saturated fatty acids, which are undesirable in dry cleaning soaps.- -While a number of naturally occurring fatty acid mixtures such as 'soya bean oil fatty acids, sesame seed oil fatty acids and the like maybe used, the preferred raw materials are the tall oil fatty acids, which are obtainable commercially in large quantities. These acids are produced by the, vacuum steam distillation and fractionation of tall oil, a mixture of unsaturatedfatty'acids acid-and 46-48% is linoleic acid.
My new guanidine soaps are preferably prepared by reacting one or more of these fatty acid mixtures with guanidine carbonate or'with a guanidine. salt of a stronger acid, such as guanidine hydrochloridefln the presence of, an acid acceptor such as sodium carbonate or sodium hydroxide. Typical manufacturing processes are described in the following examples. The resulting soaps usually contain less than 5% of freefatty acid and are soluble in allproportions in polar organic solvents such asethan- 01 and isopropanol. Theyare also soluble 'in xylenq perchlorethylene and other chlorinated dry. meaning sole. vents By the' use of cosolvents such as-isopropyl a lcohol, isopropyhacetate or ethylene glycol monobut-yl ethen-theyacan readily'be dissolved in Stoddards'olvei t-f f or other similar petroleum hydrocarbon solvents'tof the' concentrations ordinarily used in dry cleaning which, as.
noted above, are usually on the order of about l'lb. of; the guanidine soap for-each 6- 35 gallons of solventx i 1 It will be .understood, froin-the foregoing that 'the;es-; x
of fabrics in a. drycleaning solvent containing detergent quantities of a guanidinesoap of a fatty acid rnixture having a substantial, content '.of both oleic acid and linoleic acid and a relatively low' content, preferably n more than about 15%, of saturated fatty acids: The term, detergent quantities, as used in the present spe ficationand claims, designatesquantities of the guanidine soap'suflicient to impart detergency and facilitate ith'e removal of soil from the fabrics beingwashed; Stated ions. 7 Theprocess'is njot restricted toth e useof any p ticular-organic dry "cleaning solvent or: solvent mixture and any known-or approved dry cleaning solvent, in-\ particularly those enumeratedabove maybe used.
the quantities indicatedabove'.-as the"'only' detergent or as potassium-or sodium oleatefsoapaaaminelo or otheraccepted dry cleaning detergents. It is an advantage of the guanidine oleate-linoleate soaps of my invention that they are compatible in dry cleaning solvents with these soaps and with anionic wetting agents such as sodium dioctyl sulfosuccinate, sodium dihexyl sulfosuccinate, sodium lauryl sulfate, salts of alkylated aromatic sulfonic acids such as keryl benzene sulfonate and alkali metal salts of the sulfonic acids of condensation products of butylene and propylene polymers of about 12 carbon atoms with benzene or toluene. They are also compatible in dry cleaning solvents with nonionic surface active agents such as ethylene oxide or propylene oxide condensation products of alkylated phenols; a typical compound of this class is the condensation product of 8-9 moles of ethylene oxide with one mole of nonyl phenol that is sold commercially as Aerosol NI. ,These and other wetting agents of the same class may therefore be present during the dry cleaning method of my invention, preferably in quantities of about 0.05% to 1% on the weight of the solvent. Other customary or preferred ingredients may also be present such as finely divided diatomaceous earth or other filter aids, which are usually employed in quantities of about 13%.
The invention will be further described and illustrated by the following specific examples. It will be understood, however, that although these examples may describe in detail certain preferred embodiments of the invention, including particularly the preferred guanidine soaps of tall oil fatty acid mixtures and their methods of manufacture, the examples are given primarily for purposes of illustration and the invention in its broader aspects is not limited thereto.
EXAMPLE 1 The guanidine soaps used in the tests of Example 2 were prepared by the following procedures.
In making the oleate-linoleate soap a commercial fatty acid mixture sold as Acintol FA-2 was used. This mixture has an acid number of 194, a saponification number of 196 and contains 96.8% of fatty acids of 18 carbon atoms, 1% rosin acids and 2.2% unsaponifiables. The fatty acids consist of 50% oleic acid, 48% linoleic acid and 2% saturated acid.
A portion of this mixture weighing 768 grams was dissolved in 1050 cc. of methyl isobutyl ketone in a reaction vessel equipped with a condenser and stirrer and 259 grams of guanidine carbonate was added slowly during 30 minutes. The solution was stirred for an additional hour and was then tray-dried to constant weight in a forced-draft oven. The yield was 911 grams, which is 98% of theory. The dried product was a browncolored stiff paste.
The same product can be prepared from otherguanidine salts such as the nitrate, sulfate, hydrochloride and the like by the use of an acid acceptor such as sodium hydroxide or carbonate. The following preparation from guanidine hydrochloride is typical.
Lbs. Acintol FA-Z 3,105 Guanidine hydrochloride 1,024 Toluene n 385 Isopropyl alcohol 128 Sodium hydroxide, 50% aq. ,soln. 856
: complete the batch is filtered hot (above 85 C.) to remove sodium chloride and the filtrate is stripped of solfinal temperature of about 100 C.
Oleic Linolelc Palmttic Stearlc Soya Bean Oil 33. 7 52. 6. 8 4. 4 Sesame Seed Oil... 49.4 37. 7 7. 8 4. 7 Pine Seed Oil 35.1 54. 5 2.0 Tall Oil Fatty Acids 50-51 4648 2-3 1 Contains 1-4% rosin acids and 24% unsaponifiablcs.
The guanidine soaps of saturated fatty acids of 16 to 18 carbon atoms are not good dry cleaning detergents and therefore fatty acid mixtures having a relatively low content of these acids, preferably not more than about 10-15%, should be selected. Commercial fatty acids which are otherwise suitable, such as cottonseed oil fatty acids, may be pretreated by low temperature crystallization or solvent extraction to remove part or all of their saturated fatty acid content and may then be'converted into guanidine soaps by the above-described procedures. In general the fatty acid mixtures used in making satisfactory guanidine soap dry cleaning detergents should contain from about 30% to 60% by weight of oleic acid and about 30-60% of linoleic acid.
Guanidine coconutate was prepared by dissolving 636 grams of coconut oil fatty acids in 1 liter of methyl isobutyl ketone, heating the solution to -90 C. and adding 283 grams of guanidine carbonate slowly followed by agitation at the same temperature for one hour and drying at 50 C.
EXAMPLE 2 Dry cleaning solutions having the following compositions and properties were prepared. In each case the solvent was 2 liters of perchlorethylene (tetrachlorethylene).
t The potassium oleate was a standard 'dry cleaning soap (Textile Test Method CC C-T-1916, May 1951, Method 5580) prepared by pouring a solution of 35 grams of KOH in 89ml. of distilled water into a mixture of 250 ml. of oleic acid, 724 ml. of Stoddard solvent and ml. of cyclohexanol. The guanidine oleaterlinoleate and guanidine coconutate were those prepared as described in Example 1. i
Wool flannel cloth was padded-to a pickup in a 1 mixture of the following:
vents by distillation under a vacuum such as. to attain a" It was then'cut into 6 x 6-inch pieces and 200 gram samples of these were dry cleaned in the test solutions.
In order to measure the soil redeposition-inhibiting properties of the detergents additional 6 X 6-inch pieces of unsoiled wool and of viscose rayon were washed in admixture with samples of the soiled wool. Test pieces of these were removed 7.5, 15 and 25 minutes after starting the washer (a rotating jar) and also at the end of the wash (35 minutes). Each piece was rinsed in 40 cc. of fresh perchlorethylene and dried by centrifuging and its reflectance was measured. The test results are shown in Table II; in this table the heading Soln. No. refers to the solutions described in Table I, and the percent of soil removed is calculated by the formula:
Reflectance: Washed fabric-soiled fabric 100 Reflectance: unsolled fabr1cso1led fabric Table II Reflectance at Soil Reflect- Wash 600 mu. Reancc $0111. No. Fabric Time, moved, Loss,
Minutes Per- Per- Meas- Avercent cent ured age Control Soiled None 52. 8
Wool. Do -1 Unsoiled None 70. 4
Wool. Do Unsoiled None 82.5
Rayon. 1 sovilled1 35 68. 9
oo 1.. ...do 35 69.5 69 2 93 1 d 85 60.3 1 Un oiled 7 68. 1. 9
W001 1 d 15 69. 2 1. 2 1 d0 25 69. 4 1. 0 1 do 35 69.4 1.0 1 Rayon 7 71. 1 l1. 4 1 do 15 68. 8 13.7 1 .--d0 25 66. 9 15.6 1 do 35 64. 9 17. 6 2 Soiled 35 69. 7 W001 2 an as 69.9 2 do 35 69. 7 2 Unsoiled 7 69. 9 0.5
Wool 2 do 15 69. 9 0. 5 2 do 25 70.4 0 2--- 35 70. 3 0.1 2 Rayon..- 7 82. 1 0. 4 2 do 15 81. 4 1. 1 2 ..--d0 25 81. 7 0. 7 3 sovil ed 35 43. 9
0o a an as 44. 5 0 do 35 43 6 3 Unsofled 7 53.9 16.5
Wool. -1 do 15 49. 7 20.0 n 25 47. 2 23. 2 do 35 45. 8 24. 6 Re yon- 7 81. 6 0. 9 r o 15 80. 5 2. 0 3 r o 25 80. 8 1. 7 l r o 35 79. 2, 3. 3
These results show that the guanidine oleate-linoleate soap is superior to potassium oleate both in its dry cleaning detergency and in its soil redeposition properties for W001 and that the latter properties are much better with respect to rayon. The guanidine salt of coconut fatty acids has very poor detergency in dry cleaning solvents.
What I claim is:
1. A dry cleaning method which comprises washing soiledfabrics in a dry cleaning solvent containing detergent quantities of the guanidine' soap of a fatty acid mixture containing about 30-60% of oleic acid, about 30- of linoleic acid and not more than about 15% of saturated fatty acids.
2. A dry cleaning method which comprises washing soiled fabrics in a dry cleaning solvent containing detergent quantities of the guanidine soap of tall -oil fatty acids produced by the vacuum steam distillation and fracdonation of tall oil.
3. The guanidine soap of a fatty acid mixture suited for use as a detergent in dry cleaning solvents containing about 30-60% of oleic acid, about 30-60% of linoleic acid and not more than about 15% of saturated fatty acids.
4. The guanidine soap of a tall oil fatty acid mixture suited for use as a detergent in dry cleaning solvents of about 50% of oleic acid and 46-48% of linoleic acid, the balance being saturated fatty acids.
References Cited in the file of this patent UNITED STATES PATENTS 1,830,970 Sullivan Nov. 10, 1931 2,240,365 Dreger Apr. 29, 1941 2,374,113 Lowe Apr. 17, 1945 2,551,634 Price May 8, 1951 2,695,250 Shields et a1 Nov. 23, 1954 OTHER REFERENCES Ind. and Eng. Chem, February 1948, vol. 40, No. 2, pages 335-337.
Soap and San. Chem., June 1951, pages 43, 45, 47, 57.
Dugan: Fatty Acid Composition of Food Fats and Oils, Am. Meat Institute Foundation, C36, August 1957, page 6.

Claims (1)

1. A DRY CLEANING METHOD WHICH COMPRISES WASHING SOILED FABRICS IN A DRY CLEANING SOLVENT CONTAINING DETERGENT QUANTITIES OF THE GUANIDINE SOAP OF A FATTY ACID MIXTURE CONTAINING ABOUT 30-60% OF OLEIC ACID ABOUT 3060% OF LINOLEIC ACID AND NOT MORE THAN ABOUT 15% OF SATURATED FATTY ACIDS.
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Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3322573A (en) * 1965-01-19 1967-05-30 Oakite Prod Inc Metal cleaning compositions and method and baths therefor
US3367798A (en) * 1965-01-19 1968-02-06 Oakite Prod Inc Metal cleaning compositions, baths and method
WO1996012054A1 (en) * 1994-10-14 1996-04-25 Henkel Kommanditgesellschaft Auf Aktien Use of guanidine salts of unsaturated fatty acids as anticorrosive active substances

Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US1830970A (en) * 1926-11-01 1931-11-10 Standard Oil Co Lubricant
US2240365A (en) * 1939-07-11 1941-04-29 Colgate Palmolive Peet Co Method of treating tall oil
US2374113A (en) * 1943-11-19 1945-04-17 Pennsylvania Salt Mfg Co Solvent emulsion cleaner
US2551634A (en) * 1945-12-17 1951-05-08 Price Robert Hamilton Liquid soap composition
US2695250A (en) * 1951-07-28 1954-11-23 Emery Industries Inc Method of dry cleaning and weatherproofing fabrics

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US1830970A (en) * 1926-11-01 1931-11-10 Standard Oil Co Lubricant
US2240365A (en) * 1939-07-11 1941-04-29 Colgate Palmolive Peet Co Method of treating tall oil
US2374113A (en) * 1943-11-19 1945-04-17 Pennsylvania Salt Mfg Co Solvent emulsion cleaner
US2551634A (en) * 1945-12-17 1951-05-08 Price Robert Hamilton Liquid soap composition
US2695250A (en) * 1951-07-28 1954-11-23 Emery Industries Inc Method of dry cleaning and weatherproofing fabrics

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3322573A (en) * 1965-01-19 1967-05-30 Oakite Prod Inc Metal cleaning compositions and method and baths therefor
US3367798A (en) * 1965-01-19 1968-02-06 Oakite Prod Inc Metal cleaning compositions, baths and method
WO1996012054A1 (en) * 1994-10-14 1996-04-25 Henkel Kommanditgesellschaft Auf Aktien Use of guanidine salts of unsaturated fatty acids as anticorrosive active substances
US5749947A (en) * 1994-10-14 1998-05-12 Henkel Kommanditgesellschaft Auf Aktien Use of guanidinium salts of unsaturated fatty acids as corrosion inhibitors

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