US3451844A - Cationic active agent and a method for softening a washable textile fabric therewith - Google Patents
Cationic active agent and a method for softening a washable textile fabric therewith Download PDFInfo
- Publication number
- US3451844A US3451844A US519002A US3451844DA US3451844A US 3451844 A US3451844 A US 3451844A US 519002 A US519002 A US 519002A US 3451844D A US3451844D A US 3451844DA US 3451844 A US3451844 A US 3451844A
- Authority
- US
- United States
- Prior art keywords
- softening
- mole
- active agent
- textile fabric
- cation
- 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
- 239000004753 textile Substances 0.000 title description 11
- 238000000034 method Methods 0.000 title description 10
- 239000004744 fabric Substances 0.000 title description 6
- 239000013543 active substance Substances 0.000 title description 2
- 125000002091 cationic group Chemical group 0.000 title 1
- 150000001875 compounds Chemical class 0.000 description 22
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 12
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 9
- 238000005406 washing Methods 0.000 description 8
- 125000004432 carbon atom Chemical group C* 0.000 description 7
- 239000000203 mixture Substances 0.000 description 7
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- 238000001035 drying Methods 0.000 description 5
- 239000000839 emulsion Substances 0.000 description 5
- ALSTYHKOOCGGFT-KTKRTIGZSA-N (9Z)-octadecen-1-ol Chemical compound CCCCCCCC\C=C/CCCCCCCCO ALSTYHKOOCGGFT-KTKRTIGZSA-N 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- 235000014113 dietary fatty acids Nutrition 0.000 description 4
- 229930195729 fatty acid Natural products 0.000 description 4
- 239000000194 fatty acid Substances 0.000 description 4
- IPCSVZSSVZVIGE-UHFFFAOYSA-N hexadecanoic acid Chemical compound CCCCCCCCCCCCCCCC(O)=O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 description 4
- 239000001257 hydrogen Substances 0.000 description 4
- 229910052739 hydrogen Inorganic materials 0.000 description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 4
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 4
- 229940055577 oleyl alcohol Drugs 0.000 description 4
- XMLQWXUVTXCDDL-UHFFFAOYSA-N oleyl alcohol Natural products CCCCCCC=CCCCCCCCCCCO XMLQWXUVTXCDDL-UHFFFAOYSA-N 0.000 description 4
- 235000021355 Stearic acid Nutrition 0.000 description 3
- 239000007795 chemical reaction product Substances 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 239000003599 detergent Substances 0.000 description 3
- -1 fatty acid esters Chemical class 0.000 description 3
- 150000004665 fatty acids Chemical class 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 3
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 3
- 239000008117 stearic acid Substances 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 2
- 229920000742 Cotton Polymers 0.000 description 2
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 235000021314 Palmitic acid Nutrition 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- 229920000297 Rayon Polymers 0.000 description 2
- YRIUSKIDOIARQF-UHFFFAOYSA-N dodecyl benzenesulfonate Chemical compound CCCCCCCCCCCCOS(=O)(=O)C1=CC=CC=C1 YRIUSKIDOIARQF-UHFFFAOYSA-N 0.000 description 2
- 235000019253 formic acid Nutrition 0.000 description 2
- WQEPLUUGTLDZJY-UHFFFAOYSA-N n-Pentadecanoic acid Natural products CCCCCCCCCCCCCCC(O)=O WQEPLUUGTLDZJY-UHFFFAOYSA-N 0.000 description 2
- 229920002239 polyacrylonitrile Polymers 0.000 description 2
- 229920000728 polyester Polymers 0.000 description 2
- 229920000151 polyglycol Polymers 0.000 description 2
- 239000010695 polyglycol Substances 0.000 description 2
- 239000002964 rayon Substances 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- VILCJCGEZXAXTO-UHFFFAOYSA-N 2,2,2-tetramine Chemical compound NCCNCCNCCN VILCJCGEZXAXTO-UHFFFAOYSA-N 0.000 description 1
- IHCCLXNEEPMSIO-UHFFFAOYSA-N 2-[4-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]piperidin-1-yl]-1-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)ethanone Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C1CCN(CC1)CC(=O)N1CC2=C(CC1)NN=N2 IHCCLXNEEPMSIO-UHFFFAOYSA-N 0.000 description 1
- NIPNSKYNPDTRPC-UHFFFAOYSA-N N-[2-oxo-2-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)ethyl]-2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidine-5-carboxamide Chemical compound O=C(CNC(=O)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F)N1CC2=C(CC1)NN=N2 NIPNSKYNPDTRPC-UHFFFAOYSA-N 0.000 description 1
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- 150000001470 diamides Chemical class 0.000 description 1
- 150000005690 diesters Chemical class 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 125000000896 monocarboxylic acid group Chemical group 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 229920001522 polyglycol ester Polymers 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 229960001124 trientine Drugs 0.000 description 1
- 238000009827 uniform distribution Methods 0.000 description 1
- 210000002268 wool Anatomy 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
- D06M13/322—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 nitrogen
- D06M13/402—Amides imides, sulfamic acids
- D06M13/405—Acylated polyalkylene polyamines
-
- 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
- C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
- C11D1/38—Cationic compounds
- C11D1/52—Carboxylic amides, alkylolamides or imides or their condensation products with alkylene oxides
- C11D1/528—Carboxylic amides (R1-CO-NR2R3), where at least one of the chains R1, R2 or R3 is interrupted by a functional group, e.g. a -NH-, -NR-, -CO-, or -CON- group
-
- 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
- C11D3/0005—Other compounding ingredients characterised by their effect
- C11D3/001—Softening compositions
Definitions
- the required amounts of the cation-active compounds can readily be established during preliminary experiments; amounts of 0.1%, referred to the dry weight of the textiles to be treated, are in general already found to be suflicient.
- the compounds to be employed according to the invention are distinguished by an unexpectedly more intensive activity compared with the fatty acid esters and fatty acid amides mentioned above, particularly with regard to an improvement in the feel of the textiles.
- EXAMPLE 1 3 kg. of a textile fabric (towelling) consisting of cotton which had been washed and rinsed about 20 times in an automatic drum washing machine with a commercial detergent based on dodecyl-benzene sulphonate, and which had become stiff and hard after drying, are treated with the cation-active compound of the formula R is an alkyl radical of 1-4 carbon atoms; and n is an by adding 3 g. of this compound, in the form of its 7.5%
- the cation-active compounds which can be suitably employed according to the invention may for instance be obtained by heating 1 mole of the compound of the formula with 1 mole of the compound of the formula R -COOH and 1 mole of the formula R COOH at 180 to 190 C. for several hours; in these formulae the symbols R R R and R, as well as X and n have the significance mentioned above.
- the cation-active compounds are conveniently employed in the form of their salts with lower organic acids or with inorganic acids, such as formic acid and acetic acid or hydrochloric acid and phosphoric acid.
- inorganic acids such as formic acid and acetic acid or hydrochloric acid and phosphoric acid.
- aqueous emulsion which also contains 3.8% acetic acid as well as 1% oleyl alcohol polyglycol ether, to the last rinsing liquor during a further washing operation.
- the fabric which has thus been treated then no longer exhibits hardness or stiffness after drying, but has a pleasant soft feel.
- EXAMPLE 2 (1 mole) were reacted with a mixture of 256 g. (1 mole) palmitic acid and 284 g. stearic acid (1 mole) as well as with 10.2 g. acetic anhydride (0.1 mole) by the method described in Example 1. Thereafter, 75 g. of the resultant cation-active compound of the formula 4 with 10.2 g. acetic anhydride (0.1 mole) by the method described in Example 1. 75 g. of the cation-active com- CHzCHa EXAMPLE 3 3 kg.
- EXAMPLE 4 3 kg. of a mixed fabric consisting of polyester fibres and rayon which had been washed and rinsed 20 times in an automatic washing machine with a commercial detergent based on dodecyl-benzene sulphonate and which had become stiff and hard after drying, are treated with the cation-active compound of the formula pound thus obtained were then stirred with 905 g. water, with 10 g. of the reaction product of 25 moles ethylene oxide with 1 mole oleyl alcohol and with 10 g. 100% formic acid by the method described in Example 1 to form an aqueous emulsion.
- R and R are individually defined as alkyl radicals of 11-21 carbon atoms; R is hydrogen or methyl; R is an alkyl radical of 14 carbon atoms; and n is an integer of 0-2.
- R and R are respectively alkyl of 15-17 carbon atoms; R is hydrogen; R is ethyl and n is 1.
- a method for softening washable textiles comprising contacting the textiles with an active amount of a compound of claim 1.
- Washable textiles are cotton, polyacrylonitrile, lWOOl, polyester or rayon, and about 1% by weight of active compound is utilized by weight of dry textile.
Landscapes
- 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)
- Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
United States Patent M F 45, Int. Cl. C21h 1/00; C08j 1/38; D06m 3/02 US. Cl. 117-1395 4 Claims ABSTRACT OF THE DISCLOSURE Cation active compounds of the type exemplified by the formula wherein R and R are individually defined as alkyl radicals of 11-21 carbon atoms; R is hydrogen or methyl;
AGENT AND A METHOD FOR 3,451,844- Patented June 24, 1969 and in fact in the form of dilute, about 510% aqueous solutions or emulsions, in order to ensure their rapid and uniform distribution in this rinsing liquor.
The required amounts of the cation-active compounds can readily be established during preliminary experiments; amounts of 0.1%, referred to the dry weight of the textiles to be treated, are in general already found to be suflicient.
The compounds to be employed according to the invention are distinguished by an unexpectedly more intensive activity compared with the fatty acid esters and fatty acid amides mentioned above, particularly with regard to an improvement in the feel of the textiles.
The following examples serve to illustrate the invention without, however, limiting its scope.
EXAMPLE 1 3 kg. of a textile fabric (towelling) consisting of cotton which had been washed and rinsed about 20 times in an automatic drum washing machine with a commercial detergent based on dodecyl-benzene sulphonate, and which had become stiff and hard after drying, are treated with the cation-active compound of the formula R is an alkyl radical of 1-4 carbon atoms; and n is an by adding 3 g. of this compound, in the form of its 7.5%
integer of 0-2; and a method for softening washable textiles by utilizing said compounds.
It is known that textiles which are repeatedly washed can, after washing and rinsing, be after-treated with cation-active agents in order to improve their properties during their use. The monoor di-esters of fatty acids with triethanolamine and the diamides of fatty acids with triethylene tetramine have been employed as the cationactive agents for this purpose.
According to the present invention, compounds of the formula wherein R and R each individually represent an alkyl radical containing 11 to 21 and preferably 15 to 17 carbon atoms, R is hydrogen or methyl, and R is an alkyl radical containing 1 to 4 carbon atoms, whilst X denotes oxygen, the group -NH or the group NCH and n is a number of 0-2, are particularly suitable as cationactive agents for use in a process of this kind.
The cation-active compounds which can be suitably employed according to the invention may for instance be obtained by heating 1 mole of the compound of the formula with 1 mole of the compound of the formula R -COOH and 1 mole of the formula R COOH at 180 to 190 C. for several hours; in these formulae the symbols R R R and R, as well as X and n have the significance mentioned above.
The cation-active compounds are conveniently employed in the form of their salts with lower organic acids or with inorganic acids, such as formic acid and acetic acid or hydrochloric acid and phosphoric acid. When washing and rinsing of the textiles is carried out in automatic washing machines, it is recommended to add the cation-active compounds or their salts, optionally as a mixture with nonionic surface-active compounds such as polyglycol esters of fat alcohols, to the last rinsing liquor,
aqueous emulsion which also contains 3.8% acetic acid as well as 1% oleyl alcohol polyglycol ether, to the last rinsing liquor during a further washing operation. The fabric which has thus been treated then no longer exhibits hardness or stiffness after drying, but has a pleasant soft feel.
The above mentioned cation-active compound and its emulsion as applied had been prepared by the following method:
143 g. bis-N-(B-aminopropyl)-met'hylamine (1 mole) were treated dropwise at 120 in an atmosphere of nitrogen with 568 g. stearic acid (2 moles), and the mixture was thereafter heated at 180-185 C. for 4 hours, again in an atmosphere of nitrogen, in order to distill off the resultant water, the mixture being maintained under a reduced pressure of 100 mm. Hg during the last two hours, The reaction product was then cooled to 100 C., treated with 10.2 g. acetic anhydride (0.1 mole) in order to combine with any remaining unreacted amine, and kept at 100 C. for another 30 minutes.
75 g. of the resultant cation-active compound were heated to 8 090 C. in a sealed vessel in an atmosphere 'of nitrogen whilst stirring, then treated with 877 g. water and 10 g. of the reaction product of 25 moles ethylene oxide with -1 mole oleyl alcohol and finally stirred at C. for another 10 minutes. The solution was thereafter treated with 38 g. of acetic acid, stirred at 90-95 C. for another 15 minutes, and then cooled as quickly as possible.
EXAMPLE 2 (1 mole) were reacted with a mixture of 256 g. (1 mole) palmitic acid and 284 g. stearic acid (1 mole) as well as with 10.2 g. acetic anhydride (0.1 mole) by the method described in Example 1. Thereafter, 75 g. of the resultant cation-active compound of the formula 4 with 10.2 g. acetic anhydride (0.1 mole) by the method described in Example 1. 75 g. of the cation-active com- CHzCHa EXAMPLE 3 3 kg. of a mixed fabric consisting of polyacrylonitrile fibres and of wool with a shrink-proofing finish, which had been washed and rinsed 20 times in an automatic drum washing machine with a commercial fine detergent based on alkyl sulphates and which had become stiff and hard after drying, are treated with a mixture of equal parts by weight of the cation-active compounds specified in Example 1 and Example 2, by adding 3 g. of this mixture, in the form of its 7.5% aqueous emulsion which had been prepared in accordance with the statements in Example 1 and which also contains 3.8% acetic acid as well as 1% oleyl alcohol polyglycol ether, to the last rinsing liquor during a further washing operation. The fabric which has thus been treated then no longer exhibits hardness or stifiness after drying, but has a full soft feel.
EXAMPLE 4 3 kg. of a mixed fabric consisting of polyester fibres and rayon which had been washed and rinsed 20 times in an automatic washing machine with a commercial detergent based on dodecyl-benzene sulphonate and which had become stiff and hard after drying, are treated with the cation-active compound of the formula pound thus obtained were then stirred with 905 g. water, with 10 g. of the reaction product of 25 moles ethylene oxide with 1 mole oleyl alcohol and with 10 g. 100% formic acid by the method described in Example 1 to form an aqueous emulsion.
We claim:
1. A compound of the formula wherein R and R are individually defined as alkyl radicals of 11-21 carbon atoms; R is hydrogen or methyl; R is an alkyl radical of 14 carbon atoms; and n is an integer of 0-2.
2. A compound of claim 1 wherein R and R are respectively alkyl of 15-17 carbon atoms; R is hydrogen; R is ethyl and n is 1.
3. A method for softening washable textiles comprising contacting the textiles with an active amount of a compound of claim 1.
4. The method of claim 3 wherein the Washable textiles are cotton, polyacrylonitrile, lWOOl, polyester or rayon, and about 1% by weight of active compound is utilized by weight of dry textile.
(1 mole) were reacted with a mixture of 256 g. palmitic acid (1 mole) and 2 84 g. stearic acid (1 mole) as well as References Cited UNITED STATES PATENTS 2,205,042 6/1940 Lenher et al. 11 7-1395 2,243,980 6/1941 Rheiner et al. 260-4045 X 2,496,776 2/1950 Caldwell 117-1395 2,734,830 2/1956 Hagge et a1. 117-47 3,038,820 6/ 1962 Albrecht 260-4045 X 3,095,373 6/1963 Blomfield 117-47 X 3,168,416 2/ 1965 Zech 1l7-l39.5
WILLIAM D. MARTIN, Primary Examiner.
T. G. DAVIS, Assistant Examiner.
US. Cl. X.R.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEF0045004 | 1965-01-20 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US3451844A true US3451844A (en) | 1969-06-24 |
Family
ID=7100301
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US519002A Expired - Lifetime US3451844A (en) | 1965-01-20 | 1966-01-06 | Cationic active agent and a method for softening a washable textile fabric therewith |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US3451844A (en) |
| BE (1) | BE675375A (en) |
| CH (1) | CH419042A (en) |
| DE (1) | DE1469359A1 (en) |
| FR (1) | FR1465039A (en) |
| GB (1) | GB1111396A (en) |
| NL (1) | NL6600468A (en) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2156772A1 (en) * | 1971-10-18 | 1973-06-01 | Procter & Gamble | |
| US3844959A (en) * | 1972-10-16 | 1974-10-29 | Procter & Gamble | Detergent composition with an amido-amine fabric softening agent |
| US4044034A (en) * | 1975-07-22 | 1977-08-23 | The Miranol Chemical Company, Inc. | Nitrogenous condensation products |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2539349C2 (en) * | 1975-09-04 | 1985-04-11 | Hoechst Ag, 6230 Frankfurt | Laundry treatment agents |
| NL7609628A (en) * | 1975-09-04 | 1977-03-08 | Hoechst Ag | TEXTILE TREATMENT AGENT. |
| US4762645A (en) * | 1987-11-16 | 1988-08-09 | The Procter & Gamble Company | Detergent plus softener with amide ingredient |
| NZ235490A (en) * | 1989-10-16 | 1993-08-26 | Colgate Palmolive Co | Fabric-softening compositions |
Citations (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2205042A (en) * | 1937-10-26 | 1940-06-18 | Du Pont | Softening of textile materials and compositions therefor |
| US2243980A (en) * | 1936-10-30 | 1941-06-03 | Sandoz Ltd | Softening textiles |
| US2496776A (en) * | 1946-06-21 | 1950-02-07 | Eastman Kodak Co | Textile yarns impregnated with lubricating compositions |
| US2734830A (en) * | 1950-01-13 | 1956-02-14 | ||
| US3038820A (en) * | 1955-07-15 | 1962-06-12 | Ciba Ltd | Process for imparting a soft feel to textile fibers |
| US3095373A (en) * | 1959-01-30 | 1963-06-25 | Wyandotte Chemicals Corp | Fabric softeners |
| US3168416A (en) * | 1957-04-23 | 1965-02-02 | Atlas Chem Ind | Textile yarn coated with cationic surfactant |
-
1965
- 1965-01-20 DE DE19651469359 patent/DE1469359A1/en active Pending
-
1966
- 1966-01-05 CH CH11166A patent/CH419042A/en unknown
- 1966-01-06 US US519002A patent/US3451844A/en not_active Expired - Lifetime
- 1966-01-13 NL NL6600468A patent/NL6600468A/xx unknown
- 1966-01-20 GB GB2665/66A patent/GB1111396A/en not_active Expired
- 1966-01-20 BE BE675375D patent/BE675375A/xx unknown
- 1966-01-20 FR FR46574A patent/FR1465039A/en not_active Expired
Patent Citations (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2243980A (en) * | 1936-10-30 | 1941-06-03 | Sandoz Ltd | Softening textiles |
| US2205042A (en) * | 1937-10-26 | 1940-06-18 | Du Pont | Softening of textile materials and compositions therefor |
| US2496776A (en) * | 1946-06-21 | 1950-02-07 | Eastman Kodak Co | Textile yarns impregnated with lubricating compositions |
| US2734830A (en) * | 1950-01-13 | 1956-02-14 | ||
| US3038820A (en) * | 1955-07-15 | 1962-06-12 | Ciba Ltd | Process for imparting a soft feel to textile fibers |
| US3168416A (en) * | 1957-04-23 | 1965-02-02 | Atlas Chem Ind | Textile yarn coated with cationic surfactant |
| US3095373A (en) * | 1959-01-30 | 1963-06-25 | Wyandotte Chemicals Corp | Fabric softeners |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2156772A1 (en) * | 1971-10-18 | 1973-06-01 | Procter & Gamble | |
| US3844959A (en) * | 1972-10-16 | 1974-10-29 | Procter & Gamble | Detergent composition with an amido-amine fabric softening agent |
| US4044034A (en) * | 1975-07-22 | 1977-08-23 | The Miranol Chemical Company, Inc. | Nitrogenous condensation products |
Also Published As
| Publication number | Publication date |
|---|---|
| BE675375A (en) | 1966-05-16 |
| CH419042A (en) | 1966-08-31 |
| NL6600468A (en) | 1966-07-21 |
| DE1469359A1 (en) | 1968-12-19 |
| FR1465039A (en) | 1967-01-06 |
| GB1111396A (en) | 1968-04-24 |
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