US3057676A - Dry-cleaning composition and process - Google Patents
Dry-cleaning composition and process Download PDFInfo
- Publication number
- US3057676A US3057676A US730049A US73004958A US3057676A US 3057676 A US3057676 A US 3057676A US 730049 A US730049 A US 730049A US 73004958 A US73004958 A US 73004958A US 3057676 A US3057676 A US 3057676A
- Authority
- US
- United States
- Prior art keywords
- alkyl
- dry
- cleaning
- amine
- liter
- 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
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- 238000005108 dry cleaning Methods 0.000 title claims description 41
- 238000000034 method Methods 0.000 title claims description 12
- 239000000203 mixture Substances 0.000 title description 26
- 150000001412 amines Chemical class 0.000 claims description 36
- -1 AMINO, IMINO Chemical group 0.000 claims description 22
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 17
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 16
- 235000014113 dietary fatty acids Nutrition 0.000 claims description 15
- 229930195729 fatty acid Natural products 0.000 claims description 15
- 239000000194 fatty acid Substances 0.000 claims description 15
- 150000004665 fatty acids Chemical class 0.000 claims description 15
- 150000002191 fatty alcohols Chemical class 0.000 claims description 13
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 claims description 12
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 9
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 8
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 8
- 238000004140 cleaning Methods 0.000 claims description 8
- 239000002657 fibrous material Substances 0.000 claims description 8
- 229910052757 nitrogen Inorganic materials 0.000 claims description 8
- 229910052760 oxygen Inorganic materials 0.000 claims description 8
- 239000001301 oxygen Substances 0.000 claims description 8
- 239000002904 solvent Substances 0.000 claims description 8
- 229910052717 sulfur Inorganic materials 0.000 claims description 8
- 239000011593 sulfur Substances 0.000 claims description 8
- 150000001408 amides Chemical class 0.000 claims description 6
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical compound S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 claims description 5
- 150000004996 alkyl benzenes Chemical class 0.000 claims description 5
- 150000008051 alkyl sulfates Chemical class 0.000 claims description 5
- 229940045714 alkyl sulfonate alkylating agent Drugs 0.000 claims description 5
- 150000008052 alkyl sulfonates Chemical class 0.000 claims description 5
- 239000011538 cleaning material Substances 0.000 claims 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-L sulfite Chemical compound [O-]S([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-L 0.000 claims 1
- 125000004432 carbon atom Chemical group C* 0.000 description 18
- 125000000217 alkyl group Chemical group 0.000 description 11
- 239000002270 dispersing agent Substances 0.000 description 10
- 239000003760 tallow Substances 0.000 description 9
- 125000005842 heteroatom Chemical group 0.000 description 8
- 239000006185 dispersion Substances 0.000 description 7
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 6
- 239000012459 cleaning agent Substances 0.000 description 6
- IPCSVZSSVZVIGE-UHFFFAOYSA-N hexadecanoic acid Chemical compound CCCCCCCCCCCCCCCC(O)=O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 description 6
- 239000002689 soil Substances 0.000 description 6
- 239000000654 additive Substances 0.000 description 4
- 150000003973 alkyl amines Chemical class 0.000 description 4
- POULHZVOKOAJMA-UHFFFAOYSA-N dodecanoic acid Chemical compound CCCCCCCCCCCC(O)=O POULHZVOKOAJMA-UHFFFAOYSA-N 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 235000021314 Palmitic acid Nutrition 0.000 description 3
- CYTYCFOTNPOANT-UHFFFAOYSA-N Perchloroethylene Chemical class ClC(Cl)=C(Cl)Cl CYTYCFOTNPOANT-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000013543 active substance Substances 0.000 description 3
- WQEPLUUGTLDZJY-UHFFFAOYSA-N n-Pentadecanoic acid Natural products CCCCCCCCCCCCCCC(O)=O WQEPLUUGTLDZJY-UHFFFAOYSA-N 0.000 description 3
- 229950011008 tetrachloroethylene Drugs 0.000 description 3
- FJLUATLTXUNBOT-UHFFFAOYSA-N 1-Hexadecylamine Chemical compound CCCCCCCCCCCCCCCCN FJLUATLTXUNBOT-UHFFFAOYSA-N 0.000 description 2
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- 239000005639 Lauric acid Substances 0.000 description 2
- 125000000129 anionic group Chemical group 0.000 description 2
- 150000001735 carboxylic acids Chemical class 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- PAFZNILMFXTMIY-UHFFFAOYSA-N cyclohexylamine Chemical compound NC1CCCCC1 PAFZNILMFXTMIY-UHFFFAOYSA-N 0.000 description 2
- 210000003746 feather Anatomy 0.000 description 2
- 239000000945 filler Substances 0.000 description 2
- IOKYPACLTOWHCM-UHFFFAOYSA-N n,n-diethyldodecan-1-amine Chemical compound CCCCCCCCCCCCN(CC)CC IOKYPACLTOWHCM-UHFFFAOYSA-N 0.000 description 2
- NQYKSVOHDVVDOR-UHFFFAOYSA-N n-hexadecylhexadecan-1-amine Chemical compound CCCCCCCCCCCCCCCCNCCCCCCCCCCCCCCCC NQYKSVOHDVVDOR-UHFFFAOYSA-N 0.000 description 2
- LYRFLYHAGKPMFH-UHFFFAOYSA-N octadecanamide Chemical compound CCCCCCCCCCCCCCCCCC(N)=O LYRFLYHAGKPMFH-UHFFFAOYSA-N 0.000 description 2
- 238000005191 phase separation Methods 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- 239000004753 textile Substances 0.000 description 2
- BMYAJQCQJQBMQL-UHFFFAOYSA-N 2-dodecylsulfanylethanamine Chemical compound CCCCCCCCCCCCSCCN BMYAJQCQJQBMQL-UHFFFAOYSA-N 0.000 description 1
- 235000013162 Cocos nucifera Nutrition 0.000 description 1
- 244000060011 Cocos nucifera Species 0.000 description 1
- MHZGKXUYDGKKIU-UHFFFAOYSA-N Decylamine Chemical compound CCCCCCCCCCN MHZGKXUYDGKKIU-UHFFFAOYSA-N 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- 241000272168 Laridae Species 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- WREBNDYJJMUWAO-LWYYNNOASA-N [(1r,4ar,4br,10ar)-1,4a-dimethyl-7-propan-2-yl-2,3,4,4b,5,6,10,10a-octahydrophenanthren-1-yl]methanamine Chemical compound NC[C@]1(C)CCC[C@]2(C)[C@@H](CCC(C(C)C)=C3)C3=CC[C@H]21 WREBNDYJJMUWAO-LWYYNNOASA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 238000005576 amination reaction Methods 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 150000003863 ammonium salts Chemical class 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 125000002091 cationic group Chemical group 0.000 description 1
- 150000008280 chlorinated hydrocarbons Chemical class 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- JRBPAEWTRLWTQC-UHFFFAOYSA-N dodecylamine Chemical compound CCCCCCCCCCCCN JRBPAEWTRLWTQC-UHFFFAOYSA-N 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- QUSNBJAOOMFDIB-UHFFFAOYSA-N monoethyl amine Natural products CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- IOQPZZOEVPZRBK-UHFFFAOYSA-N octan-1-amine Chemical compound CCCCCCCCN IOQPZZOEVPZRBK-UHFFFAOYSA-N 0.000 description 1
- 150000003141 primary amines Chemical class 0.000 description 1
- 150000003335 secondary amines Chemical class 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- JHJUUEHSAZXEEO-UHFFFAOYSA-M sodium;4-dodecylbenzenesulfonate Chemical compound [Na+].CCCCCCCCCCCCC1=CC=C(S([O-])(=O)=O)C=C1 JHJUUEHSAZXEEO-UHFFFAOYSA-M 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- 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
Definitions
- This invention relates to a method and a bath composition for dry-cleaning of textiles, feathers, fillers or like materials. It more particularly relates to a drycleaning method and bath modified with high molecular weight amine compounds as dispersing agents.
- a further object is to provide a dry-cleaning bath comprising a stable dispersion of an organic dry-cleaning agent and water.
- Another object is to provide a dispersing agent for use in preparing dry-cleaning baths containing an organic cleaning agent and water.
- Another object is to provide a dry-cleaning bath containing a dry-cleaning agent and water which has improved dispersion stability without decrease in filterability.
- alkyl radicals of the high molecular weight amines used in accordance with my invention may be interrupted by heteroatoms, such as nitrogen, oxygen or sulfur, and/ or may be substituted by amino-, iminoor hydroxylgroups.
- Compounds of this type are, for example, octyl amine, decyl amine, dodecyl amine, hexadecyl amine, primary amine mixtures, such as those which are obtained by reduction of naturally-occurring fatty acid mixtures and subsequent amination thereof, for example, amine mixtures which are derived from coconut fatty acids or tallow fatty acids.
- secondary amines such as dodecyl-oxyethyl amine, hexadecyl-methyl amine,
- dihexadecyl amine tertiary amines, such as dodecyl-di ethyl amine, octadecyl-diethyl amine, as well as amines the aliphatic hydrocarbon radicals of which are interrupted by heteroatoms, such as B-aminoethyl-decyl ether, ⁇ 3 aminoethyl dodecyl thioether, dodecylamino-ethyl amine and the like.
- non-aliphatic amines as naphthenyl amine, abietyl amine, cyclohexyl amine or alkyl-cyclohexyl amine may be used.
- an essential characteristic of my invention is that the high molecular weight alkyl amines are primarily used in the form of free bases. If technical amines or amine mixtures which in some cases contain ammonia from the manufacturing process are used, the undesirable, strong alkalinity may be buffered by adding less than stoichiometric amounts (based on the amine) of carboxylic acids. However, too high a degree of neutralization may decrease the dispersing capability to a substantial extent.
- the addition of the high molecular weight amines is accomplished in the customary fashion by adding to the cleaning bath amounts of 0.1 to 10.0 gm., preferably 0.1 to 2.0 gm., per liter of cleaning bath, the amounts within certain limits being dependent upon the amount of water to be dispersed. In general, the amount of water in the dry-cleaning bath should not exceed 1% of the total amount of liquid.
- the alkyl amines may be added to all customary drycleaning baths.
- Suitable dry-cleaning agents include, for example, gasoline, ligroin and other low-boiling-point parafiin hydrocarbons and mixtures thereof; benzene, toluene, xylene and other low-boiling-point aromatic hydrocarbons or mixtures thereof; as well as chlorinated hydrocarbons, such as carbon tetrachloride, trichloroethylene, perchloro-ethylene and mixtures thereof.
- the drycleaning baths may be used for all customary purposes, i.e., for cleaning textiles, feathers, pillow material, filler material and the like.
- the water-dispersing capability of cleansing intensifiers can be increased by the addition of high molecular weight fatty alcohols, ethyoxylated products of high molecular weight fatty alcohols, carboxylic acids or acid amides, or similar products.
- high molecular weight amines especially the alkyl amines, exhibit a far better waterdispersing capability in dry-cleaning baths in comparison to the known additives, and that dry-cleaning baths modified with the amine additives are also marked by a substantially better filterability.
- TEST ARRANGEMENT The dispersion stability of mixtures which consisted of perchloroethylene modified with 5 gm./ liter of a cleansing intensifier and 10 00. per liter of water, and to which varying amounts of different dispersing agents had been added, was tested in a shaking cylinder. The mixtures were vigorously shaken for three minutes with a shaking machine, and thereafter the time which elapsed until the first indication of a phase separation was measured. In this manner the varying effectiveness of the respective dispersing agents was visualized.
- a process for drycleaning fibrous materials which comprises cleaning said fibrous materials in a dry-cleaning bath comprising a dry-cleaning solvent, a quantity of water not greater than 1%, and 0.1 to 10 gn1./liter of high molecular weight alkyl monoamines having from 8 to 32 carbon atoms in the molecule, said alkyl monoamines being selected from the group consisting of those with at least one alkyl radical having at least 8 carbon atoms, derivatives thereof wherein the alkyl radicals are interrupted by hetero-atoms selected from the group consisting of oxygen, nitrogen and sulfur, and derivatives thereof wherein the alkyl radicals are substituted by groups selected from the group consisting of amino, imino and hydroxyl groups, in the form of their free bases.
- a process for dry-cleaning fibrous materials which comprises cleaning said fibrous materials in a dry-cleaning bath comprising a dry-cleaning solvent, a quantity of water not greater than 1%, cleansing intensifiers selected from the group consisting of alkyl sulfates, alkyl sulfonates, alkyl benzene sulfonates, ethylene oxide addition products of high molecular weight fatty alcohols and fatty acids, and high molecular weight acid amides, amines and mercaptans, and 0.1 to 10 gm./liter of high molecular weight alkyl monoamines having from 8 to 32 carbon atoms in the molecule, said alkyl monoamines being selected from the group consisting of those with at least one alkyl radical having at least 8 carbon atoms, derivatives thereof wherein the alkyl radicals are interrupted by hetero-atoms selected from the group consisting of oxygen, nitrogen and sulfur, and derivatives thereof wherein the alkyl radicals are substituted by groups selected from the group consist
- a method for forming a dry-cleaning bath effective against both water-soluble and water-insoluble soil which comprises adding to a dry-cleaning solvent not greater than about 1% water, and 0.1 to 10 gm./liter of high molecular weight alkyl monoamines having from 8 to 32 carbon atoms in the molecule, said alkyl monoamines being selected from the group consisting of those with at least one alkyl radical having at least 8 carbon atoms, derivatives thereof wherein the alkyl radicals are interrupted by hetero-atoms selected from the group consisting of oxygen, nitrogen and sulfur, and derivatives thereof wherein the alkyl radicals are substituted by groups selected from the group consisting of amino, imino and hydroxyl groups, in the form of their free bases.
- a method for forming a dry-cleaning bath effective against both water-soluble and water-insoluble soil which comprises adding to a dry-cleaning solvent not greater than about 1% water, cleansing intensifiers selected from the group consisting of alkyl sulfates, alkyl sulfonates, alkyl benzene sulfonates, ethylene oxide addition products of high molecular Weight fatty alcohols and fatty acids and high molecular weight acid amides, amines and mercaptans, and 0.1 to 10 gm./liter of high molecular weight alkyl monoamines having from 8 to 32 carbon atoms in the molecule, with at least one alkyl radical having at least 8 carbon atoms, wherein the alkyl radicals of said high molecular weight amines may be interrupted by hetero-atoms selected from the group consisting of oxygen, nitrogen and sulfur and substituted by groups selected from the group consisting of amino, imino and hydroxyl groups, in the form of their free bases.
- a dry-cleaning bath for cleaning fibrous materials containing some water-soluble soil which comprises a dry-cleaning solvent, not greater than about 1% water, and 0.1 to g m./liter of high molecular weight alkyl monoamines having from 8 to 32 carbon atoms in the molecule, said alkyl monoamines being selected from the group consisting of those with at least one alkyl radical having at least 8 carbon atoms, derivatives thereof wherein the alkyl radicals are interrupted by hetero-atoms selected from the group consisting of oxygen, nitrogen and sulfur, and derivatives thereof wherein the alkyl radicals are substituted by groups selected from the group consisting of amino, imino and hydroxyl groups, in the form of their free bases.
- a dry-cleaning bath for cleaning fibrous materials containing some water-soluble soil which comprises a dry-cleaning solvent, not greater than about 1% of water, cleansing intensifiers selected from the group consisting of alkyl sulfates, alkyl sulfonates, alkyl benzene sulfonates, ethylene oxide addition products of high molecular weight fatty alcohols and fatty acids, and high molecular Weight acid amides, amines and mercaptans, and 0.1 to 10 gm./ liter of high molecular weight alkyl monoamines having from 8 to 32 carbon atoms in the molecule, said alkyl monoamines being selected from the group consisting of those with at least one alkyl radical having at least.
Landscapes
- Engineering & Computer Science (AREA)
- Textile Engineering (AREA)
- Detergent Compositions (AREA)
- Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEB44444A DE1057275B (de) | 1957-04-27 | 1957-04-27 | Verfahren zur chemischen Reinigung von Textilmaterial |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US3057676A true US3057676A (en) | 1962-10-09 |
Family
ID=6967331
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US730049A Expired - Lifetime US3057676A (en) | 1957-04-27 | 1958-04-22 | Dry-cleaning composition and process |
Country Status (7)
Cited By (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3272754A (en) * | 1961-08-08 | 1966-09-13 | Sandoz Ltd | Dry cleaning agents for textile materials |
| US3335091A (en) * | 1965-02-08 | 1967-08-08 | Dow Chemical Co | Dry cleaning method and composition |
| US3357922A (en) * | 1964-08-18 | 1967-12-12 | Bohme Fettchemie Gmbh | Novel disinfectant and dry cleaning compositions |
| US3395086A (en) * | 1963-09-11 | 1968-07-30 | Res Dev Co | Removal of moisture from organic liquid solvent |
| US3505005A (en) * | 1965-02-08 | 1970-04-07 | Dow Chemical Co | Dry cleaning method |
| US3628911A (en) * | 1967-12-08 | 1971-12-21 | Henkel & Cie Gmbh | Textile chemical cleaning processes |
| US3630661A (en) * | 1968-12-19 | 1971-12-28 | Soltex Soc Civ | Process for degreasing and desizing fabrics having synthetic fibers |
| US3951596A (en) * | 1972-10-13 | 1976-04-20 | Colgate-Palmolive Company | Soap curd dispersant |
| US3962151A (en) * | 1972-08-11 | 1976-06-08 | Lever Brothers Company | Solvent type cleaners |
| US4097397A (en) * | 1976-10-27 | 1978-06-27 | Kao Soap Co., Ltd. | Dry cleaning detergent composition |
| US4405511A (en) * | 1981-03-21 | 1983-09-20 | Chemische Fabrik Kreussler & Co. Gmbh | Cleaning intensifier for use in dry-cleaning machines equipped with adsorption filters |
| US4406809A (en) * | 1981-03-21 | 1983-09-27 | Chemische Fabrik Kreussler & Co. Gmbh | Disinfecting cleaning intensifier for dry cleaning |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB8418320D0 (en) * | 1984-07-18 | 1984-08-22 | Procter & Gamble | Dispersible fabric softeners |
Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US1911289A (en) * | 1932-02-04 | 1933-05-30 | Emery Industries Inc | Method of cleaning fabrics |
| US2052891A (en) * | 1932-04-22 | 1936-09-01 | Union Oil Co | Method for cleaning fabrics |
| US2267205A (en) * | 1938-08-04 | 1941-12-23 | Monsanto Chemicals | Detergent |
| US2271635A (en) * | 1935-09-25 | 1942-02-03 | Allied Chem & Dye Corp | Dry cleaning composition and method |
| US2334517A (en) * | 1941-03-28 | 1943-11-16 | Procter & Gamble | High molecular weight surface active amines |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB555421A (en) * | 1942-02-18 | 1943-08-23 | Bertram Pusey Ridge | Improvements in or relating to dry cleaning |
| GB759143A (en) * | 1953-02-19 | 1956-10-17 | Monsanto Chemicals | Improvements relating to detergent compositions |
-
0
- NL NL227206D patent/NL227206A/xx unknown
- BE BE566231D patent/BE566231A/xx unknown
- NL NL96437D patent/NL96437C/xx active
- FR FR1194382D patent/FR1194382A/fr not_active Expired
-
1957
- 1957-04-27 DE DEB44444A patent/DE1057275B/de active Pending
-
1958
- 1958-03-22 CH CH358062D patent/CH358062A/de unknown
- 1958-04-22 US US730049A patent/US3057676A/en not_active Expired - Lifetime
- 1958-04-25 GB GB13128/58A patent/GB847017A/en not_active Expired
Patent Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US1911289A (en) * | 1932-02-04 | 1933-05-30 | Emery Industries Inc | Method of cleaning fabrics |
| US2052891A (en) * | 1932-04-22 | 1936-09-01 | Union Oil Co | Method for cleaning fabrics |
| US2271635A (en) * | 1935-09-25 | 1942-02-03 | Allied Chem & Dye Corp | Dry cleaning composition and method |
| US2267205A (en) * | 1938-08-04 | 1941-12-23 | Monsanto Chemicals | Detergent |
| US2334517A (en) * | 1941-03-28 | 1943-11-16 | Procter & Gamble | High molecular weight surface active amines |
Cited By (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3272754A (en) * | 1961-08-08 | 1966-09-13 | Sandoz Ltd | Dry cleaning agents for textile materials |
| US3395086A (en) * | 1963-09-11 | 1968-07-30 | Res Dev Co | Removal of moisture from organic liquid solvent |
| US3357922A (en) * | 1964-08-18 | 1967-12-12 | Bohme Fettchemie Gmbh | Novel disinfectant and dry cleaning compositions |
| US3335091A (en) * | 1965-02-08 | 1967-08-08 | Dow Chemical Co | Dry cleaning method and composition |
| US3505005A (en) * | 1965-02-08 | 1970-04-07 | Dow Chemical Co | Dry cleaning method |
| US3628911A (en) * | 1967-12-08 | 1971-12-21 | Henkel & Cie Gmbh | Textile chemical cleaning processes |
| US3630661A (en) * | 1968-12-19 | 1971-12-28 | Soltex Soc Civ | Process for degreasing and desizing fabrics having synthetic fibers |
| US3962151A (en) * | 1972-08-11 | 1976-06-08 | Lever Brothers Company | Solvent type cleaners |
| US3951596A (en) * | 1972-10-13 | 1976-04-20 | Colgate-Palmolive Company | Soap curd dispersant |
| US4097397A (en) * | 1976-10-27 | 1978-06-27 | Kao Soap Co., Ltd. | Dry cleaning detergent composition |
| US4405511A (en) * | 1981-03-21 | 1983-09-20 | Chemische Fabrik Kreussler & Co. Gmbh | Cleaning intensifier for use in dry-cleaning machines equipped with adsorption filters |
| US4406809A (en) * | 1981-03-21 | 1983-09-27 | Chemische Fabrik Kreussler & Co. Gmbh | Disinfecting cleaning intensifier for dry cleaning |
Also Published As
| Publication number | Publication date |
|---|---|
| BE566231A (US07166745-20070123-C00016.png) | |
| GB847017A (en) | 1960-09-07 |
| DE1057275B (de) | 1959-05-14 |
| FR1194382A (US07166745-20070123-C00016.png) | 1959-11-09 |
| NL96437C (US07166745-20070123-C00016.png) | |
| NL227206A (US07166745-20070123-C00016.png) | |
| CH358062A (de) | 1961-11-15 |
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