US2060568A - Assisting agents for the textile industry - Google Patents
Assisting agents for the textile industry Download PDFInfo
- Publication number
- US2060568A US2060568A US27609A US2760935A US2060568A US 2060568 A US2060568 A US 2060568A US 27609 A US27609 A US 27609A US 2760935 A US2760935 A US 2760935A US 2060568 A US2060568 A US 2060568A
- Authority
- US
- United States
- Prior art keywords
- oxide
- matter
- composition
- carbon atoms
- parts
- 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 3
- 239000000203 mixture Substances 0.000 description 24
- 125000004432 carbon atom Chemical group C* 0.000 description 14
- QTWJRLJHJPIABL-UHFFFAOYSA-N 2-methylphenol;3-methylphenol;4-methylphenol Chemical group CC1=CC=C(O)C=C1.CC1=CC=CC(O)=C1.CC1=CC=CC=C1O QTWJRLJHJPIABL-UHFFFAOYSA-N 0.000 description 12
- 229930003836 cresol Natural products 0.000 description 12
- 239000003795 chemical substances by application Substances 0.000 description 10
- 150000003512 tertiary amines Chemical class 0.000 description 8
- -1 ether alcohols Chemical class 0.000 description 7
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 6
- WOSXILICBSSMRZ-UHFFFAOYSA-N n,n-dimethylbutan-1-amine oxide Chemical compound CCCC[N+](C)(C)[O-] WOSXILICBSSMRZ-UHFFFAOYSA-N 0.000 description 6
- 150000002989 phenols Chemical class 0.000 description 6
- 239000003921 oil Substances 0.000 description 5
- MMAXOAIHEPNELR-UHFFFAOYSA-N n,n-dimethylcyclohexanamine oxide Chemical compound C[N+](C)([O-])C1CCCCC1 MMAXOAIHEPNELR-UHFFFAOYSA-N 0.000 description 4
- LKQUDAOAMBKKQW-UHFFFAOYSA-N N,N-dimethylaniline N-oxide Chemical compound CN(C)(=O)C1=CC=CC=C1 LKQUDAOAMBKKQW-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 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
- 125000004433 nitrogen atom Chemical group N* 0.000 description 3
- 239000000080 wetting agent Substances 0.000 description 3
- AEFTZVMBNWKTMT-UHFFFAOYSA-N 1-benzyl-1-oxidopiperidin-1-ium Chemical compound C=1C=CC=CC=1C[N+]1([O-])CCCCC1 AEFTZVMBNWKTMT-UHFFFAOYSA-N 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- GRMDYZRESXOHID-UHFFFAOYSA-N 1-butyl-1-oxidopiperidin-1-ium Chemical class CCCC[N+]1([O-])CCCCC1 GRMDYZRESXOHID-UHFFFAOYSA-N 0.000 description 1
- POAOYUHQDCAZBD-UHFFFAOYSA-N 2-butoxyethanol Chemical compound CCCCOCCO POAOYUHQDCAZBD-UHFFFAOYSA-N 0.000 description 1
- LCHYEKKJCUJAKN-UHFFFAOYSA-N 2-propylphenol Chemical class CCCC1=CC=CC=C1O LCHYEKKJCUJAKN-UHFFFAOYSA-N 0.000 description 1
- ZYCQUXBZBHFZER-UHFFFAOYSA-N C(CCC)[N+](CC)(CC)[O-] Chemical compound C(CCC)[N+](CC)(CC)[O-] ZYCQUXBZBHFZER-UHFFFAOYSA-N 0.000 description 1
- NEEIPDKIQZSXHW-UHFFFAOYSA-N COCCN(C1CCCCC1)O Chemical compound COCCN(C1CCCCC1)O NEEIPDKIQZSXHW-UHFFFAOYSA-N 0.000 description 1
- JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 description 1
- 229960000583 acetic acid Drugs 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000004359 castor oil Substances 0.000 description 1
- 235000019438 castor oil Nutrition 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 150000001896 cresols Chemical class 0.000 description 1
- SYELZBGXAIXKHU-UHFFFAOYSA-N dodecyldimethylamine N-oxide Chemical compound CCCCCCCCCCCC[N+](C)(C)[O-] SYELZBGXAIXKHU-UHFFFAOYSA-N 0.000 description 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 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 1
- 238000004519 manufacturing process Methods 0.000 description 1
- ZIPXQSWJIRXBEM-UHFFFAOYSA-N n,n-diethylcyclohexanamine oxide Chemical compound CC[N+]([O-])(CC)C1CCCCC1 ZIPXQSWJIRXBEM-UHFFFAOYSA-N 0.000 description 1
- LFMTUFVYMCDPGY-UHFFFAOYSA-N n,n-diethylethanamine oxide Chemical compound CC[N+]([O-])(CC)CC LFMTUFVYMCDPGY-UHFFFAOYSA-N 0.000 description 1
- SZPMPIRRJBQQCU-UHFFFAOYSA-N n,n-diethylpropan-1-amine oxide Chemical compound CCC[N+]([O-])(CC)CC SZPMPIRRJBQQCU-UHFFFAOYSA-N 0.000 description 1
- HTBSGBIWKJSAGD-UHFFFAOYSA-N n,n-dimethylpropan-1-amine oxide Chemical compound CCC[N+](C)(C)[O-] HTBSGBIWKJSAGD-UHFFFAOYSA-N 0.000 description 1
- KTTGGOPAXFFNDT-UHFFFAOYSA-N n-methyl-n-propylpropan-1-amine oxide Chemical compound CCC[N+](C)([O-])CCC KTTGGOPAXFFNDT-UHFFFAOYSA-N 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 239000007800 oxidant agent Substances 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- UYPYRKYUKCHHIB-UHFFFAOYSA-N trimethylamine N-oxide Chemical compound C[N+](C)(C)[O-] UYPYRKYUKCHHIB-UHFFFAOYSA-N 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
- D06M13/152—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 having a hydroxy group bound to a carbon atom of a six-membered aromatic ring
-
- 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
- D06M11/00—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with inorganic substances or complexes thereof; Such treatment combined with mechanical treatment, e.g. mercerising
- D06M11/32—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with inorganic substances or complexes thereof; Such treatment combined with mechanical treatment, e.g. mercerising with oxygen, ozone, ozonides, oxides, hydroxides or percompounds; Salts derived from anions with an amphoteric element-oxygen bond
- D06M11/36—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with inorganic substances or complexes thereof; Such treatment combined with mechanical treatment, e.g. mercerising with oxygen, ozone, ozonides, oxides, hydroxides or percompounds; Salts derived from anions with an amphoteric element-oxygen bond with oxides, hydroxides or mixed oxides; with salts derived from anions with an amphoteric element-oxygen bond
- D06M11/38—Oxides or hydroxides of elements of Groups 1 or 11 of the Periodic Table
-
- 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
- D06M13/388—Amine oxides
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S516/00—Colloid systems and wetting agents; subcombinations thereof; processes of
- Y10S516/01—Wetting, emulsifying, dispersing, or stabilizing agents
- Y10S516/07—Organic amine, amide, or n-base containing
Definitions
- compositions of matter thus obtained there may be added further substances, such as, for example ether alcohols, for instance, glycolmonobutylether, glycerine-monoalkylether and glycerine-dialkylether.
- ether alcohols for instance, glycolmonobutylether, glycerine-monoalkylether and glycerine-dialkylether.
- All these compounds are oxides derived from such tertiary amines which contain not more than 12 carbon atoms and which contain at least one radical which comprises at least 3 carbon atoms.
- these amine-oxides those are particu- 35 larly valuable which are derived from non-aromatic tertiary amines; further those non-aromatic tertiary amines which contain at least one radical comprising 4 to 6 carbon atoms, But if use is made of amine-oxides which are derived 40 from tertiary amines'containing higher aliphatic radicals, such as, for example, the dodecyldimethylamine oxide, no compositions of matter are obtained which are useful as wetting agents, for mercerizing baths, since the solubility-promot- 45 ing agent is no longer capable of keeping such highly molecular amine-oxides in solution in mercerizing baths.
- the low molecular amineoxides such as trimethylamine-oxide or tri
- Solubility-promoting agents 1. e. products which have been selected from a group of com-'- pounds consisting of phenols, or highly suli'onated 55 oils. and which have the property of increasing the solubility of organic compounds in mercerizing baths, are for example, phenol itself, the various cresols, crude cresol, phenols substituted in the aromatic nucleus by alkyl radicals commercerization.
- Example 1 25 parts of butyldimethylamine-oxide are mixed with 75 parts of crude cresol. The mixture may be used forthwith as an assistant in tained, if instead of '75 parts of crude cresol a mixture of 65 parts of crude cresol, and 10 parts of glacial acetic acid is used.
- Example 3 To the mercerizing liquor there is added, per litre, 5 grams of a mixture consisting of 38.5 parts of dimethylaniline-oxide and 61.5 parts of crude cresol. solved in the mercerizing liquor. The tests made in the same manner as described in Example 2 'gave the following shrinkage values:-
- amine-oxides there may be substituted n-butyl-piperidine-oxide, benzylpiperidine oxide, dimethyl-cyclo-hexylamine-oxide, diethylcyclohexyiamine oxide, methyloxyethylcyclohexylamine-oxide or these, or the like.
- a stable, clear solution is oh This addition remains fully disaooasoa 1.
- a composition of matter comprising a solubility-promoting agent and a tertiary amine oxide which is sparingly soluble in mercerizing baths, but which is soluble in mercerizing baths with the aid of a solubility-promoting agent selected from the group consisting of phenols and highly sulfonated oils.
- a composition of matter comprising crude cresol and an amine-oxide which is sparingly soluble in mercerizing baths, but which is soluble in mercerizing baths with the aid of crude cresol.
- A'composition of matter comprising a solubility-promoting agent selected from the group consistingof phenols and highly sulfonated oils and a tertiary amine-oxide derived from a nonaromatic tertiary amine containing not more than 12 carbon atoms and at least one radical containing at least 4 and at the most 6 carbon atoms.
- a composition of matter comprising a phenol and a tertiary amine-oxide derived from a nonaromatic tertiary amine containing not more than 12 carbon atoms and at least one radical containing at least 4 and at the most 6 carbon atoms.
- a composition of matter comprising crude cresol and a tertiary amine-oxide derived from a non-aromatic tertiary amine containing not more than 12 carbon atoms and at least one radical containing at least 4 and at the most 6 carbon atoms.
- composition of matter comprising a solubility-promoting agent selected from the group consisting of phenols and highly sulfonated oils and a tertiary amine-oxide derived from a nonarornatic tertiary amine containing at least 6 and at the most 8 carbon atoms, and in which two methyl groups are linked to the nitrogen atom.
- composition 01 matter comprising a phenol and a tertiary amine-oxide derived from a non-aromatic tertiary amine containing at least 6 and at the most 8 carbon atoms, and in which two methyl groups are linked to the nitrogen atom.
- a composition of matter comprising crude cresol and a tertiary amine-oxide derived from a non-aromatic tertiary amine containing at least 6 and at the most 8 carbon atoms, and in which two methyl groups are linked to the nitrogen atom.
- composition of matter comprising a phenol and butyldimethylamine-oxide.
- a composition of matter comprising crude cresol and butyldimethylamine-oxide.
- a composition of matter consisting of a mixture of 70 to 95 parts of a phenol and 5 to 30 parts of butyldimethylamine-oxide.
- a composition of matter consisting of a mixture of 70 to 95 parts of crude cresol and 5 to 30 parts of butyldimethylamine-oxide.
- a composition oi matter comprising a solubility-promoting agent selected from the group consisting of phenols. and highly sulfonated oils and dimethylcyclohexylamine-oxide.
- composition oi matter comprising a phenol and dimethylcyclohexylamine-oxide.
- a composition of matter consisting of a mixture of about 85 to 95 parts of crude cresol 41.21% 5' to 15 parts of dimethylcyclohewlamineo e.
Landscapes
- Engineering & Computer Science (AREA)
- Textile Engineering (AREA)
- Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
- Fats And Perfumes (AREA)
- Emulsifying, Dispersing, Foam-Producing Or Wetting Agents (AREA)
- Paper (AREA)
- Detergent Compositions (AREA)
Description
Patented Nov. 10, 1936 iED STATES ASSISTING AGENTS FOR THE TEXTILE INDUSTRY Charles Graenacher and Richard Sallmann, Basel, Switzerland, assignors to firm Society of Chemical Industry in Basic, Basel, Switzerland No Drawing.
Application June 20, 1935, Serial No. 27,609. In Switzerland June 23, 1934 15 Claims. (Ci. 8-20) 'It is known that when tertiary amines are treated with suitable oxidizing agents they may be converted into so-cal1ed tertiary amine-oxides.
Hitherto these products have only been described in scientific literature and there has been no 5 reason to suppose that they could be applied as assistants in the textile industry.
It has now been found that certain of these tertiary amine-oxides, i. e. those which, due to their molar magnitude, are not soluble in mercerizing baths, or only sparingly soluble, but which can be dissolved in mercerizing baths with aid of so-called solubility-promoting agents, may be used for the production of excellent wetting agents for mercerizing liquors. In order to produce such wetting agents for mercerizing baths,
it is only necessary to mix these amine oxides with, the so-called solubility-promoting agents.
To the compositions of matter thus obtained there may be added further substances, such as, for example ether alcohols, for instance, glycolmonobutylether, glycerine-monoalkylether and glycerine-dialkylether.
As amine-oxides which come into consideration for carrying out the present invention there may i be named amine-oxides derived from tertiary amines which contain at least one radical comprising 3 carbon atoms, such as, for example, the propyldimethylamine-oxide oi the formula- CHPGHPCHPI1I=O the propyldiethylamine-oxide of the formula- CHI YOHr-CHz-OHr-N=O I 13' 40 the butyldimethylamine-oxide oi the formula- CH: CH:-'CHr-CHr-CHr-I T=O I (3B4 the dipropylmethylamine-oxide of the formula-- CHr-CHr-CH:
, OHr-CHr-CHg-N=O 1 HI the butyldiethylamine-oxide of the formula- CHrCHr-CH:CH:N- O
the li-butylpiperidine -oxide oi the formula- CHr-C cnroar-cnrcnrn OKs-CH,
the dimethylcyclohexylamine-oxide of the formu- 1a W V CH:
CIiCH: CH1
the diethylcyclohexylamine-oxide of the formu- 1a- CHr-OHi CHz I 10 the methylhydroxyethylcyclohexylamine-oxide of CHP-CHI III Hr-CHr-OH 20 the phenyldimethylamine-oxide of the formulathe benzylpiperidine-oxide of the formula QHr-CH:
CHz-CH: 30
etc. All these compounds are oxides derived from such tertiary amines which contain not more than 12 carbon atoms and which contain at least one radical which comprises at least 3 carbon atoms. Of these amine-oxides, those are particu- 35 larly valuable which are derived from non-aromatic tertiary amines; further those non-aromatic tertiary amines which contain at least one radical comprising 4 to 6 carbon atoms, But if use is made of amine-oxides which are derived 40 from tertiary amines'containing higher aliphatic radicals, such as, for example, the dodecyldimethylamine oxide, no compositions of matter are obtained which are useful as wetting agents, for mercerizing baths, since the solubility-promot- 45 ing agent is no longer capable of keeping such highly molecular amine-oxides in solution in mercerizing baths. The low molecular amineoxides, such as trimethylamine-oxide or triethylamine-oxide are useless, since as such they are too easily soluble in the mercerizing baths.
Solubility-promoting agents. 1. e. products which have been selected from a group of com-'- pounds consisting of phenols, or highly suli'onated 55 oils. and which have the property of increasing the solubility of organic compounds in mercerizing baths, are for example, phenol itself, the various cresols, crude cresol, phenols substituted in the aromatic nucleus by alkyl radicals commercerization.
prising more than one carbon atom such as the alkylor propyl-phenols, highly sulionated castor oil and the like. The following examples illustrate the invention, the parts being by weight:-
Example 1 25 parts of butyldimethylamine-oxide are mixed with 75 parts of crude cresol. The mixture may be used forthwith as an assistant in tained, if instead of '75 parts of crude cresol a mixture of 65 parts of crude cresol, and 10 parts of glacial acetic acid is used.
Example 2 To a memorization liquor '"(sodium hydroxide solution of 30 B.) there is added, per litre,
Li uor Liquor Seconds wit out with I addition addition The liquor to which the addition has been made remains quite clear even on long standing and after 72 hours has the same shrinkage values as those recorded with the liquor immediately after addition has been made.
Example 3 To the mercerizing liquor there is added, per litre, 5 grams of a mixture consisting of 38.5 parts of dimethylaniline-oxide and 61.5 parts of crude cresol. solved in the mercerizing liquor. The tests made in the same manner as described in Example 2 'gave the following shrinkage values:-
- Li 1101' Liquor Seconds wit out wit addition addition A like mixture, which contains dimethylaniline instead of dimethylaniline-oxide is completely useless on account of the immediate separation of the base.
For the foregoing amine-oxides there may be substituted n-butyl-piperidine-oxide, benzylpiperidine oxide, dimethyl-cyclo-hexylamine-oxide, diethylcyclohexyiamine oxide, methyloxyethylcyclohexylamine-oxide or these, or the like.-
What we claim is:-
A stable, clear solution is oh This addition remains fully disaooasoa 1. A composition of matter comprising a solubility-promoting agent and a tertiary amine oxide which is sparingly soluble in mercerizing baths, but which is soluble in mercerizing baths with the aid of a solubility-promoting agent selected from the group consisting of phenols and highly sulfonated oils.
2. A composition of matter comprising crude cresol and an amine-oxide which is sparingly soluble in mercerizing baths, but which is soluble in mercerizing baths with the aid of crude cresol.
3. A'composition of matter comprising a solubility-promoting agent selected from the group consistingof phenols and highly sulfonated oils and a tertiary amine-oxide derived from a nonaromatic tertiary amine containing not more than 12 carbon atoms and at least one radical containing at least 4 and at the most 6 carbon atoms.
4. A composition of matter comprising a phenol and a tertiary amine-oxide derived from a nonaromatic tertiary amine containing not more than 12 carbon atoms and at least one radical containing at least 4 and at the most 6 carbon atoms.
5. A composition of matter comprising crude cresol and a tertiary amine-oxide derived from a non-aromatic tertiary amine containing not more than 12 carbon atoms and at least one radical containing at least 4 and at the most 6 carbon atoms.
6. A composition of matter comprising a solubility-promoting agent selected from the group consisting of phenols and highly sulfonated oils and a tertiary amine-oxide derived from a nonarornatic tertiary amine containing at least 6 and at the most 8 carbon atoms, and in which two methyl groups are linked to the nitrogen atom.
'7. A composition 01 matter comprising a phenol and a tertiary amine-oxide derived from a non-aromatic tertiary amine containing at least 6 and at the most 8 carbon atoms, and in which two methyl groups are linked to the nitrogen atom.
8. A composition of matter comprising crude cresol and a tertiary amine-oxide derived from a non-aromatic tertiary amine containing at least 6 and at the most 8 carbon atoms, and in which two methyl groups are linked to the nitrogen atom.
9. A composition of matter comprising a phenol and butyldimethylamine-oxide.
10. A composition of matter comprising crude cresol and butyldimethylamine-oxide.
11. A composition of matter consisting of a mixture of 70 to 95 parts of a phenol and 5 to 30 parts of butyldimethylamine-oxide.
12. A composition of matter consisting of a mixture of 70 to 95 parts of crude cresol and 5 to 30 parts of butyldimethylamine-oxide.
13. A composition oi matter comprising a solubility-promoting agent selected from the group consisting of phenols. and highly sulfonated oils and dimethylcyclohexylamine-oxide.
14. A composition oi matter comprising a phenol and dimethylcyclohexylamine-oxide.
15. A composition of matter consisting of a mixture of about 85 to 95 parts of crude cresol 41.21% 5' to 15 parts of dimethylcyclohewlamineo e.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH449209X | 1934-06-23 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US2060568A true US2060568A (en) | 1936-11-10 |
Family
ID=4515425
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US27609A Expired - Lifetime US2060568A (en) | 1934-06-23 | 1935-06-20 | Assisting agents for the textile industry |
Country Status (5)
| Country | Link |
|---|---|
| US (1) | US2060568A (en) |
| CH (1) | CH177545A (en) |
| DE (1) | DE670813C (en) |
| FR (1) | FR792239A (en) |
| GB (1) | GB449209A (en) |
Cited By (19)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2999068A (en) * | 1959-04-27 | 1961-09-05 | Procter & Gamble | Personal use detergent lotion |
| US3001945A (en) * | 1959-04-29 | 1961-09-26 | Procter & Gamble | Liquid detergent composition |
| US3085982A (en) * | 1959-04-22 | 1963-04-16 | Procter & Gamble | Liquid detergent composition |
| US3086943A (en) * | 1959-06-10 | 1963-04-23 | Procter & Gamble | Shampoo containing amine oxide |
| US3179599A (en) * | 1961-07-03 | 1965-04-20 | Procter & Gamble | Detergent composition |
| US3179598A (en) * | 1961-07-03 | 1965-04-20 | Procter & Gamble | Detergent composition |
| US3194840A (en) * | 1961-12-18 | 1965-07-13 | Procter & Gamble | N, n-diloweralkyl, 1, 1-dihydrogen perfluoroalkyl amine oxides |
| US3197509A (en) * | 1961-12-21 | 1965-07-27 | Procter & Gamble | Diamine dioxide compounds |
| US3202714A (en) * | 1961-12-04 | 1965-08-24 | Procter & Gamble | Oxy containing tertiary amine oxides |
| US3223647A (en) * | 1959-04-20 | 1965-12-14 | Procter & Gamble | Mild detergent compositions |
| US3249587A (en) * | 1961-09-29 | 1966-05-03 | Gen Electric | Mixture of epoxy resin and a tertiary amine oxide |
| US3317430A (en) * | 1960-05-05 | 1967-05-02 | Lever Brothers Ltd | Detergent compositions |
| US3441611A (en) * | 1961-12-04 | 1969-04-29 | Procter & Gamble | Hydroxyalkylamine oxide detergent compounds |
| US3447956A (en) * | 1966-09-02 | 1969-06-03 | Eastman Kodak Co | Process for strengthening swellable fibrous material with an amine oxide and the resulting material |
| US3449430A (en) * | 1960-07-14 | 1969-06-10 | Henkel & Cie Gmbh | Amino oxides |
| US3508941A (en) * | 1966-09-02 | 1970-04-28 | Eastman Kodak Co | Method of preparing polymers from a mixture of cyclic amine oxides and polymers |
| WO1981000527A1 (en) * | 1979-08-15 | 1981-03-05 | Sherex Chem | Amine oxide promoters for froth flotation of mineral ores |
| US5824115A (en) * | 1995-04-06 | 1998-10-20 | Kao Corporation | Method for improving cellulose fiber |
| US6500215B1 (en) | 2000-07-11 | 2002-12-31 | Sybron Chemicals, Inc. | Utility of selected amine oxides in textile technology |
-
1934
- 1934-06-23 CH CH177545D patent/CH177545A/en unknown
- 1934-10-19 DE DEG89001D patent/DE670813C/en not_active Expired
-
1935
- 1935-06-20 US US27609A patent/US2060568A/en not_active Expired - Lifetime
- 1935-06-20 FR FR792239D patent/FR792239A/en not_active Expired
- 1935-06-24 GB GB18070/35A patent/GB449209A/en not_active Expired
Cited By (20)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3223647A (en) * | 1959-04-20 | 1965-12-14 | Procter & Gamble | Mild detergent compositions |
| US3085982A (en) * | 1959-04-22 | 1963-04-16 | Procter & Gamble | Liquid detergent composition |
| US2999068A (en) * | 1959-04-27 | 1961-09-05 | Procter & Gamble | Personal use detergent lotion |
| US3001945A (en) * | 1959-04-29 | 1961-09-26 | Procter & Gamble | Liquid detergent composition |
| US3086943A (en) * | 1959-06-10 | 1963-04-23 | Procter & Gamble | Shampoo containing amine oxide |
| US3317430A (en) * | 1960-05-05 | 1967-05-02 | Lever Brothers Ltd | Detergent compositions |
| US3449430A (en) * | 1960-07-14 | 1969-06-10 | Henkel & Cie Gmbh | Amino oxides |
| US3179599A (en) * | 1961-07-03 | 1965-04-20 | Procter & Gamble | Detergent composition |
| US3179598A (en) * | 1961-07-03 | 1965-04-20 | Procter & Gamble | Detergent composition |
| US3249587A (en) * | 1961-09-29 | 1966-05-03 | Gen Electric | Mixture of epoxy resin and a tertiary amine oxide |
| US3202714A (en) * | 1961-12-04 | 1965-08-24 | Procter & Gamble | Oxy containing tertiary amine oxides |
| US3441611A (en) * | 1961-12-04 | 1969-04-29 | Procter & Gamble | Hydroxyalkylamine oxide detergent compounds |
| US3194840A (en) * | 1961-12-18 | 1965-07-13 | Procter & Gamble | N, n-diloweralkyl, 1, 1-dihydrogen perfluoroalkyl amine oxides |
| US3197509A (en) * | 1961-12-21 | 1965-07-27 | Procter & Gamble | Diamine dioxide compounds |
| US3447956A (en) * | 1966-09-02 | 1969-06-03 | Eastman Kodak Co | Process for strengthening swellable fibrous material with an amine oxide and the resulting material |
| US3508941A (en) * | 1966-09-02 | 1970-04-28 | Eastman Kodak Co | Method of preparing polymers from a mixture of cyclic amine oxides and polymers |
| WO1981000527A1 (en) * | 1979-08-15 | 1981-03-05 | Sherex Chem | Amine oxide promoters for froth flotation of mineral ores |
| US4325821A (en) * | 1979-08-15 | 1982-04-20 | Sherex Chemical Company, Inc. | Amine oxide promoters for froth flotation of mineral ores |
| US5824115A (en) * | 1995-04-06 | 1998-10-20 | Kao Corporation | Method for improving cellulose fiber |
| US6500215B1 (en) | 2000-07-11 | 2002-12-31 | Sybron Chemicals, Inc. | Utility of selected amine oxides in textile technology |
Also Published As
| Publication number | Publication date |
|---|---|
| FR792239A (en) | 1935-12-26 |
| DE670813C (en) | 1939-01-25 |
| GB449209A (en) | 1936-06-23 |
| CH177545A (en) | 1935-06-15 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US2060568A (en) | Assisting agents for the textile industry | |
| US2169976A (en) | Process of producing assistants in the textile and related industries | |
| US3133916A (en) | -ch chj | |
| US2143388A (en) | Manufacture of hydroxyalkylated nitrogen bases | |
| GB881332A (en) | Arylsulphonyl acrylonitriles and compositions containing the same | |
| US2271707A (en) | Wetting agent | |
| US2438092A (en) | Nu-sulfodicarboxylic acid aspartates | |
| US1924698A (en) | Alkylated acidyl polyalkylene polyamines | |
| US2083482A (en) | Carbocyclic compounds containing acid salt-forming groups | |
| US2004864A (en) | Imidazole derivatives, useful especially as textile assistants and process of makingsame | |
| US2056449A (en) | Alkylated imidazoles of high molec | |
| DE634037C (en) | Process for the production of organic compounds with acidic, salt-forming groups | |
| US2083181A (en) | Composition of matter for dyeing animal fibers | |
| US2302749A (en) | Dithiocarbamates | |
| IT999647B (en) | PROCEDURE FOR THE PREPARATION OF HYDRAZONES | |
| US1923179A (en) | Treatment of textiles and agents therefor | |
| GB382942A (en) | Manufacture of sulphuric acid esters of alcohols | |
| US2642430A (en) | Hydroxy substituted aliphatic ether derivatives of nitrogen heterocyclics | |
| US2257183A (en) | Wetting agent useful for alkaline mercerizing solutions | |
| DE1617209A1 (en) | Process for the production of a dry, finely divided cleaning agent | |
| GB484906A (en) | Manufacture of carbocyclic basic products | |
| US2242211A (en) | Quaternary compounds of the pyridine series and process for the production of the same | |
| GB721917A (en) | Improved methods of and preparations for cleaning textiles | |
| US1932176A (en) | Sulphuric acid derivatives of amides | |
| DE881946C (en) | Process for the preparation of monoacyl derivatives of 1,2-alkylenediamines |