US2350688A - Metallic soap composition - Google Patents
Metallic soap composition Download PDFInfo
- Publication number
- US2350688A US2350688A US351110A US35111040A US2350688A US 2350688 A US2350688 A US 2350688A US 351110 A US351110 A US 351110A US 35111040 A US35111040 A US 35111040A US 2350688 A US2350688 A US 2350688A
- Authority
- US
- United States
- Prior art keywords
- soap
- aluminum
- soaps
- polyvalent metal
- solution
- 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
Links
- 239000000344 soap Substances 0.000 title description 73
- 239000000203 mixture Substances 0.000 title description 13
- 239000000243 solution Substances 0.000 description 33
- 229910052782 aluminium Inorganic materials 0.000 description 29
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 29
- 239000002904 solvent Substances 0.000 description 24
- ULQISTXYYBZJSJ-UHFFFAOYSA-N 12-hydroxyoctadecanoic acid Chemical compound CCCCCCC(O)CCCCCCCCCCC(O)=O ULQISTXYYBZJSJ-UHFFFAOYSA-N 0.000 description 21
- 229910052751 metal Inorganic materials 0.000 description 20
- 239000002184 metal Substances 0.000 description 20
- 238000004078 waterproofing Methods 0.000 description 19
- 229940114072 12-hydroxystearic acid Drugs 0.000 description 11
- 239000004359 castor oil Substances 0.000 description 11
- 229960001777 castor oil Drugs 0.000 description 11
- 235000019438 castor oil Nutrition 0.000 description 11
- ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 description 11
- 239000004922 lacquer Substances 0.000 description 9
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 8
- 238000009835 boiling Methods 0.000 description 8
- 239000002657 fibrous material Substances 0.000 description 8
- 238000004519 manufacturing process Methods 0.000 description 7
- CEGOLXSVJUTHNZ-UHFFFAOYSA-K aluminium tristearate Chemical compound [Al+3].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O CEGOLXSVJUTHNZ-UHFFFAOYSA-K 0.000 description 6
- 229940063655 aluminum stearate Drugs 0.000 description 6
- 239000011133 lead Substances 0.000 description 5
- 239000000463 material Substances 0.000 description 5
- 238000002844 melting Methods 0.000 description 5
- 230000008018 melting Effects 0.000 description 5
- 239000000843 powder Substances 0.000 description 5
- 239000008149 soap solution Substances 0.000 description 5
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 4
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 4
- 229940072049 amyl acetate Drugs 0.000 description 4
- PGMYKACGEOXYJE-UHFFFAOYSA-N anhydrous amyl acetate Natural products CCCCCOC(C)=O PGMYKACGEOXYJE-UHFFFAOYSA-N 0.000 description 4
- 235000014113 dietary fatty acids Nutrition 0.000 description 4
- 239000000194 fatty acid Substances 0.000 description 4
- 229930195729 fatty acid Natural products 0.000 description 4
- 150000004665 fatty acids Chemical class 0.000 description 4
- MNWFXJYAOYHMED-UHFFFAOYSA-M heptanoate Chemical compound CCCCCCC([O-])=O MNWFXJYAOYHMED-UHFFFAOYSA-M 0.000 description 4
- 238000000034 method Methods 0.000 description 4
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- DIZPMCHEQGEION-UHFFFAOYSA-H aluminium sulfate (anhydrous) Chemical compound [Al+3].[Al+3].[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O DIZPMCHEQGEION-UHFFFAOYSA-H 0.000 description 3
- 229910052791 calcium Inorganic materials 0.000 description 3
- 239000011575 calcium Substances 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 239000003209 petroleum derivative Substances 0.000 description 3
- 239000004753 textile Substances 0.000 description 3
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 2
- 238000000576 coating method Methods 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 239000012530 fluid Substances 0.000 description 2
- 229930195733 hydrocarbon Natural products 0.000 description 2
- 150000002430 hydrocarbons Chemical class 0.000 description 2
- 239000003208 petroleum Substances 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- 229910052725 zinc Inorganic materials 0.000 description 2
- 239000011701 zinc Substances 0.000 description 2
- KIHBGTRZFAVZRV-UHFFFAOYSA-N 2-Hydroxyoctadecanoic acid Natural products CCCCCCCCCCCCCCCCC(O)C(O)=O KIHBGTRZFAVZRV-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- JJCSYJVFIRBCRI-UHFFFAOYSA-K aluminum;hexadecanoate Chemical compound [Al].CCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCC([O-])=O JJCSYJVFIRBCRI-UHFFFAOYSA-K 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000011449 brick Substances 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- XXJWXESWEXIICW-UHFFFAOYSA-N diethylene glycol monoethyl ether Chemical compound CCOCCOCCO XXJWXESWEXIICW-UHFFFAOYSA-N 0.000 description 1
- 229940075557 diethylene glycol monoethyl ether Drugs 0.000 description 1
- 238000005108 dry cleaning Methods 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000004744 fabric Substances 0.000 description 1
- 238000007429 general method Methods 0.000 description 1
- 229910001385 heavy metal Inorganic materials 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 239000012454 non-polar solvent Substances 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 239000000123 paper Substances 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 235000011121 sodium hydroxide Nutrition 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- XOOUIPVCVHRTMJ-UHFFFAOYSA-L zinc stearate Chemical class [Zn+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O XOOUIPVCVHRTMJ-UHFFFAOYSA-L 0.000 description 1
Classifications
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
- D06M13/00—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment
- D06M13/10—Treating 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 oxygen
- D06M13/184—Carboxylic acids; Anhydrides, halides or salts thereof
- D06M13/188—Monocarboxylic acids; Anhydrides, halides or salts thereof
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
- D06M13/00—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment
- D06M13/10—Treating 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 oxygen
- D06M13/184—Carboxylic acids; Anhydrides, halides or salts thereof
- D06M13/192—Polycarboxylic acids; Anhydrides, halides or salts thereof
Definitions
- aluminum soaps such as aluminum stearate, aluminum palmitate and the like may be dissolved-insolvents such as toluol, etc. in order to form solutions which are useful for waterproofing materials such as bricks, cloth, paper, etc. While these solutions have many valuable properties and have been widely used, the aluminum soaps contained therein are ordinarily not very soluble in easily available solvents, as is evidenced by the fact that the solutions now on the market usually contain only about 2% to 3% of the soap. Hence storage or transportation of such solvents necessitates storing or transporting large quantities of solvent,
- these soaps In the first place these soaps have considerably higher melting points than the corresponding soaps derived from other fatty acids; hence they may be blended with parafiin wax in order to give mixtures having softening points much higher than those heretofore attainable.
- the polyvalent metal soaps of our invention are soluble in many relatively high boiling lacquer solvents of the polar type but tend to be relatively insoluble in non-polar solvents such as the petroleum hydrocarbons.
- polyvalent metal soaps of our invention are capable of producing waterproof coatings upon fibrous materials which are resistant to petro-l leum hydrocarbon solvents; hence these fibrous materials may be subjected to drycleaning or other similar operations without losing their waterproof characteristics.
- Our novel soaps may be easily and economically prepared and because of their many important properties will find great use in the trade.
- the aluminum soaps of our invention may be prepared by reacting an alkali metal soap prepared from hydrogenated castor oil or the corresponding fatty acids with a suitable aluminum I r of this invention to provide novel outlined above.
- the hydrogenated castor oil may be formed by hydrogenating dium soap in water and then adding suillcient aluminum sulfate to the solution, which is preferably heated, e. g. to about 80 0., so as to cause substantially complete precipitation of the aluminum soap.
- the aluminum soap thus obtained may then be washed free of soluble salts.-dried-.
- Lead, calcium and zinc soaps of hydrogenated castor oil may also be prepared by following the general method However other methods for the if desired.
- the polyvalent metal soaps of our invention are generally white powders. These soaps usually have higher melting points than those of the corresponding soaps derived from other fatty acids. Thus the aluminum soap of our invention melts at 160 C. and the lead soap between 130 and 136 (3.; the corresponding stearates melt at about 140 C. and 105 C. respectively. Analysis indicates that our novel compounds are constituted chiefly of soaps of 12-hydroxy stearic acid.
- the aluminum soap of our invention is somewhat soluble in toluol but has a higher gel point in this solvent than aluminum stearate. Because of their relatively high melting points, the soaps of our inventionare of particular value for blending with paramn wax in order to substantially increase the softening point of the paraflin wax without detrimentally affecting the waterproofing characteristics thereof. Other uses for these soaps of our invention will be evident to those skilled in the art from the above description of their properties.
- the aluminum soap of our invention forms stable, clear solutions in sol-' vents such as butanol, amyl acetate, ethylene glycol monoethylether, diethylene glycol monoethylether and the like.
- the aluminum soap of our invention also possesses the unique property of being soluble in castor oil.
- Our experiments have also demonstrated that our novel soaps are relatively insoluble in petroleum hydrocarbon sol- I vents such as solvent naphtha and the like.
- the solutions of our invention are particularly adaptable for waterproofing fibrous materials of all kinds; thus, for. example, textile materials .waterproofed with the solutions of our invention
- Example I 1,000 parts ofhydrogenated castoroil having an iodine value of about 4.2 were saponified by reaction with an aqueous solution containing 167 parts of caustic soda. The sodium soap t'hus obtained wasthen dissolved in water in amounts sufiicient to give a soap concentration of about 10%. The temperature of the solution was then raised to about 80 C. and sufficient aluminum sulfate solution was added to completely react with the soap. After the aluminum soap had The resulting product was a white pow'defhiwing a melting point of about 160-C.; it'iblended easily with any desirable amounts of paraflin wax.
- Example III 95 parts of amyl acetate were heated to a temperature of about 70 C., and 5 parts of the aluminum soap of hydrogenated castor oil prepared in accordance with Example I were dissolved therein. Upon cooling, a stable, completely fluid solution was obtained, which was found to be highly suitable for waterproofing purposes.
- Example IV parts of ethylene glycol monoethyl ether were heated to about 70 C. and 5 parts of the aluminum soap of hydrogenated castor oil prepared as described inExample I were dissolved'
- Example V 95 parts of castor oil were heated to a temperature of about 130 C. and parts of the aluminum soap of hydrogenated castor oil prepared as described in Example I were dissolved therein, whereby a slightly thickened solution was obtained. Upon cooling, the solution remained per fectly clear.
- Example VI solution was added to completely react with the soap. After the lead soap had settled from the solution-it was withdrawn, washed, dried and ground to a powder. The resulting product was a white powder having a melting point between v 130 and 136 C. r
- Example VII 1000 parts of hydrogenated castor oil having' from the solution, it was withdrawn, washed
- polyvalent metal soap is used throughout the specification and claims in the usual manner to include higher fatty acid soaps of heavy metals such as aluminum, calcium, zinc and lead.
- composition of matter comprising chiefly the lead soap of 12-hydroxy stearic acid.
- composition of matter comprising chiefly a solution of a polyvalent metal soap of 12-hydroxy stearic acid in a relatively high boiling lacquer solvent of the polar type.
- composition of matter comprising chiefly a solution of an aluminum soap ofi2-hydroxy stearic acid in a relatively high boiling lacquer 7.
- a composition of matter comprising chiefly a solution of an aluminum soap of 12-hydroxy stearic acid in butanol.
- composition of matter comprising chiefly a solution of an aluminum soap of 12-hydroxy stearlc acid in amyl acetate.
- composition of matter comprising chiefly a solution of an aluminum soap of 12-hydroxy stearic acid in ethylene glycol monoethylether.
- a process for preparing solutions suitable for waterproofing purposes which comprises dissolving a' polyvalent metal soap of 12 -hydroxy stearic acid in a relatively high boiling lacquer solvent of the polar type.
- a process for preparing solutions suitable for waterproofing purposes which comprises dis solving the aluminum soap of -12-hydroxy stearic acid in a relatively high boiling lacquer solvent of the polar type.
- a process for preparing solutions suitable for waterproofing purposes which comprises dissolving the aluminum soap'of lz hydroxy stearic acid in butanol.
- a process for preparing solutions suitable for waterproofing purposes which comprises dissolving the aluminum soap of 12-hydroxystearic acid in amyl acetate.
- a process for preparing solutions suitable for waterproofing purposes which comprises dissolving the aluminum soap of 12-hydroxy stearic acid'in ethylene glycol monoethylether.
- a process for waterproofing fibrous materials which comprises impregnating the fibrous material with a solution of a polyvalent metal soap of 12-hydroxy stearic acid in a relatively high boiling lacquer solvent of the polar type and evaporating the solvent from the impregnated material.
- a process for waterproofing fibrous materials which comprises impregnating the fibrous material with a solution 0! the aluminum soap of l2-hydroxy stearic acid in a relatively high boiling lacquer solvent of the polar type and 1 evaporating the solvent from the impreimated material.
Landscapes
- Engineering & Computer Science (AREA)
- Textile Engineering (AREA)
- Detergent Compositions (AREA)
- Materials Applied To Surfaces To Minimize Adherence Of Mist Or Water (AREA)
Priority Applications (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
FR962151D FR962151A (enrdf_load_stackoverflow) | 1940-08-03 | ||
US351110A US2350688A (en) | 1940-08-03 | 1940-08-03 | Metallic soap composition |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US351110A US2350688A (en) | 1940-08-03 | 1940-08-03 | Metallic soap composition |
Publications (1)
Publication Number | Publication Date |
---|---|
US2350688A true US2350688A (en) | 1944-06-06 |
Family
ID=23379610
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US351110A Expired - Lifetime US2350688A (en) | 1940-08-03 | 1940-08-03 | Metallic soap composition |
Country Status (2)
Country | Link |
---|---|
US (1) | US2350688A (enrdf_load_stackoverflow) |
FR (1) | FR962151A (enrdf_load_stackoverflow) |
Cited By (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2445936A (en) * | 1945-04-27 | 1948-07-27 | Shell Dev | Waterproofing of lubricating greases |
US2628202A (en) * | 1949-09-23 | 1953-02-10 | Leffingwell Chemical Company | Soap useful for making lubricating greases |
US2785989A (en) * | 1954-03-29 | 1957-03-19 | American Cyanamid Co | Metallic soaps of fatty acids and polyhydroxy monocarboxylic acids |
US2793132A (en) * | 1954-03-29 | 1957-05-21 | American Cyanamid Co | Metallic soaps of fatty acids and alphahydroxy alkanoic acids |
US2827384A (en) * | 1954-07-01 | 1958-03-18 | Philadelphia Quartz Co | Waterproof coatings and adhesives |
US2922800A (en) * | 1956-10-22 | 1960-01-26 | Exxon Research Engineering Co | Two-stage preparation of soap thickener for hydrocarbon |
-
0
- FR FR962151D patent/FR962151A/fr not_active Expired
-
1940
- 1940-08-03 US US351110A patent/US2350688A/en not_active Expired - Lifetime
Cited By (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2445936A (en) * | 1945-04-27 | 1948-07-27 | Shell Dev | Waterproofing of lubricating greases |
US2628202A (en) * | 1949-09-23 | 1953-02-10 | Leffingwell Chemical Company | Soap useful for making lubricating greases |
US2785989A (en) * | 1954-03-29 | 1957-03-19 | American Cyanamid Co | Metallic soaps of fatty acids and polyhydroxy monocarboxylic acids |
US2793132A (en) * | 1954-03-29 | 1957-05-21 | American Cyanamid Co | Metallic soaps of fatty acids and alphahydroxy alkanoic acids |
US2827384A (en) * | 1954-07-01 | 1958-03-18 | Philadelphia Quartz Co | Waterproof coatings and adhesives |
US2922800A (en) * | 1956-10-22 | 1960-01-26 | Exxon Research Engineering Co | Two-stage preparation of soap thickener for hydrocarbon |
Also Published As
Publication number | Publication date |
---|---|
FR962151A (enrdf_load_stackoverflow) | 1950-06-02 |
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