IL43714A - Quaternary phosphonium salts their preparation and their use in dyeing - Google Patents
Quaternary phosphonium salts their preparation and their use in dyeingInfo
- Publication number
- IL43714A IL43714A IL43714A IL4371473A IL43714A IL 43714 A IL43714 A IL 43714A IL 43714 A IL43714 A IL 43714A IL 4371473 A IL4371473 A IL 4371473A IL 43714 A IL43714 A IL 43714A
- Authority
- IL
- Israel
- Prior art keywords
- quaternary phosphonium
- moles
- phosphonium salts
- formula
- dyeing
- Prior art date
Links
- 150000004714 phosphonium salts Chemical group 0.000 title claims description 14
- 238000004043 dyeing Methods 0.000 title claims description 7
- 238000002360 preparation method Methods 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims description 10
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 8
- 238000006243 chemical reaction Methods 0.000 claims description 8
- 238000000034 method Methods 0.000 claims description 7
- 239000002202 Polyethylene glycol Substances 0.000 claims description 5
- 229920001223 polyethylene glycol Polymers 0.000 claims description 5
- 229910052757 nitrogen Inorganic materials 0.000 claims description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 3
- 229910052799 carbon Inorganic materials 0.000 claims description 3
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- 238000002844 melting Methods 0.000 claims description 2
- 230000008018 melting Effects 0.000 claims description 2
- 150000003839 salts Chemical group 0.000 claims description 2
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims 4
- 239000005977 Ethylene Substances 0.000 claims 4
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 claims 2
- NFAOATPOYUWEHM-UHFFFAOYSA-N 2-(6-methylheptyl)phenol Chemical compound CC(C)CCCCCC1=CC=CC=C1O NFAOATPOYUWEHM-UHFFFAOYSA-N 0.000 claims 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 1
- 125000004429 atom Chemical group 0.000 claims 1
- LQZZUXJYWNFBMV-UHFFFAOYSA-N dodecan-1-ol Chemical compound CCCCCCCCCCCCO LQZZUXJYWNFBMV-UHFFFAOYSA-N 0.000 claims 1
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 6
- 239000000203 mixture Substances 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 4
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 125000005496 phosphonium group Chemical group 0.000 description 3
- 238000001556 precipitation Methods 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- PRBXPAHXMGDVNQ-UHFFFAOYSA-N 2-[2-(2-hydroxyethoxy)ethoxy]acetic acid Chemical compound OCCOCCOCC(O)=O PRBXPAHXMGDVNQ-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 239000012299 nitrogen atmosphere Substances 0.000 description 2
- 229910000073 phosphorus hydride Inorganic materials 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- FSVRFCBLVIJHQY-UHFFFAOYSA-N 2-[2-(2-hexadecoxyethoxy)ethoxy]ethanol Chemical compound CCCCCCCCCCCCCCCCOCCOCCOCCO FSVRFCBLVIJHQY-UHFFFAOYSA-N 0.000 description 1
- OWTQQPNDSWCHOV-UHFFFAOYSA-N 2-[2-[2-[2-[2-[2-[2-[2-[2-[2-[2-[2-[2-[2-(2-hydroxyethoxy)ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethanol Chemical compound OCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCO OWTQQPNDSWCHOV-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 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
- 150000001450 anions Chemical class 0.000 description 1
- 230000001174 ascending effect Effects 0.000 description 1
- 125000002091 cationic group Chemical group 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 239000003599 detergent Substances 0.000 description 1
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 1
- 238000007865 diluting Methods 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 229920002239 polyacrylonitrile Polymers 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000007711 solidification Methods 0.000 description 1
- 230000008023 solidification Effects 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- -1 triethylene glycol butyl triethylene glycol Chemical compound 0.000 description 1
Classifications
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
- D06P3/00—Special processes of dyeing or printing textiles, or dyeing leather, furs, or solid macromolecular substances in any form, classified according to the material treated
- D06P3/70—Material containing nitrile groups
- D06P3/76—Material containing nitrile groups using basic dyes
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/54—Quaternary phosphonium compounds
- C07F9/5407—Acyclic saturated phosphonium compounds
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
- D06P1/00—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed
- D06P1/44—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed using insoluble pigments or auxiliary substances, e.g. binders
- D06P1/655—Compounds containing ammonium groups
- D06P1/6556—Compounds containing phosphonium groups
Landscapes
- Chemical & Material Sciences (AREA)
- Textile Engineering (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- General Health & Medical Sciences (AREA)
- Biochemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Molecular Biology (AREA)
- Health & Medical Sciences (AREA)
- Coloring (AREA)
- Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
quaternary p their preparation and their use in dyeing The present invention relates to a new method of preparing quaternary phosphonium their use in and to certain such new quaternary phosphonium In particular the invention relates to a method of preparing quaternary phosphonium salts of the formula X wherein B represents an alkyl radical with 4 to 18 carbon atoms alkyl radical with 8 12 carbon is 1 or X is a chlorine or bromine atom and n is an integer between 3 and which comprises treating 1 mole triphenylphosphine with moles of polyethylene glycol monoether of formula wherein and n are as defined in the presence of moles HC1 or the reaction taking place at the melting of the components or in an excess of polyethoxylate compound of the formula II as at a temperature from and preferably from and at atmospheric pressure and under nitrogen The polyethylene glycol mono ethers are easily obtainable intermediates and final products of the detergent Some examples of compounds of formula II are triethylene glycol butyl triethylene glycol or pentadeca ethylene glycol monolauryl or entadecaethlene lcol monocet l In these procedures it is possible to use chemically homogeneous compounds of formula or mixtures of such compounds where the components of the mixture differ by Unetherized polyethylene glycol often present in such does not disturb the quaternary salts obtained in the reaction may be prepared in pure state either by precipitation from the mixture with an organic in which the phosphonium salts are insoluble or by precipitation with an anion with large followed by the decomposition o the complex or by preparatory but when used as the product may not be in a pure There may also be used the solution of the quaternary phosphonium salts in the excess of polyethoxylate compound as they result from the These solutions are much stabler than the pure phosphonium salts and they may be kept The pure quaternary phosphonium salts of the formula I are very colourless crystalline solids or viscous The obtained quaternary phosphonium salts I possess excellent properties as retarder in dyein polyacrylonitrile fibres or fibres from polyaerylonltrile copolymers with basic In comparison with the ordinary cationic retarders they display a satisfying at already very small concentrations as by weight to the Their action is not by surfactants and it becomes as the dyeing so that a better usage of the dye The fibres are dyed according to the known procedure of dyeing with basic but instead of the retarder in use the above described quaternary phosphonium salts are So quaternary phosphonium salt have not been used as retarder in the of The compounds of formula I wherein S is an to 18 carbon atoms or from 8 to 12 n is an integer from 3 to are new In the following examples the for n in the general formula is to b understood as a mean that stands for a homogenous chemical compound which is actually equivalent to a mixture of either polyethylene glycol monoethers or quaternary phosphonium Example 1 Into a flask with four with ascending thermometer and nitrogen g phosphine and g triethylene glycol ether are Nitrogen is blown inside and a nitrogen atmosphere is maintained by continuous There are duced g hydrochloric acid in concentrated lution and while stirring the mixture of is heated up to This temperature is maintained till no more water is this markin the end of the The conversion is The obtained precipitates a lower temperature than its solidification point from the ture of by diluting the latter with a 40 fold amount of anhydrous After the precipitate saturated with ethyl acetate is dried in a vacuum dryer in the presence of phosphorus The precipitation of the product in order to obtain it in pure state can be made with carbon tetrachloride or The same as in the above can be reached if one works with a bigger excess of polyetoxylate the adding of an amount larger than 3 moles to 1 mole of tertiary phosphine being If we use g instead of c Q with Example 2 Into a flask like the one in example g triphenylphosphine and g triethylene glycol reaction is continued art This operation is repeated once The total amount of hydrochloric g When no water the reaction is The separation be as in example with quantitative I use g instead of in centrated we get the corresponding in tive 4 Into a flask like the one in example g triphenylphosphine and g triethylene glycol monocetyl ether are At nitrogen atmosphere g in concentrated solution are added and the flask is heated at During the reactio iore are added in three The reaction is completed when more water The of separation may be as If instead of glycol ether there are used or glycol get the also wit quantitative A redaction of the reaction rate with the increase of the etoxylation degree If nse triethylene glycol ether the equivalent of triethylene glycol we get in quantitative dye bath prepared adding a litre of g acid of 3 g anhydrous g B and g heated at 30 g of are In 30 minutes the temperature is to and it is maintained for 90 The dyeing process s interrupted and dyed material is and is uniformly in contraittstinction another dyed in the the absence of the obvious inequalities in The same result is reached if or g of phosphor from this example to the dye bath in a ution of of triethylene glycol inonolauryl ether or i instead of same amsnnt of is 6 dye bath is prepared adding to a litre of water aeetic acid of 3 g anhydrous sodium g nonionic agent ethoxilate fatty Maxxlonblau and g 8 A dye bath is to litre of water g acetic acid of 3 g anhydrous g onblaa and g in of in triethylene glycol and 30 g insufficientOCRQuality
Claims (1)
1. 8 A of preparing quaternary phosphonium salts of the general formula I wherein R represents an containing from 4 to 18 carbon atoms or an alkyl radical containing from 8 to 12 carbon is 0 or X is or and n is an integer from 3 to which comprises treating 1 mole with moles polyethylene glycol monoether of the formula II R OH wherein R and n are as defined in the presence of moles or the reaction taking place at the melting of the components or in an excess of ethoxylated compound of the formula at tures from to preferably from at atmospheric pressure and under nitrogen A method according to claim wherein said compounds of the formula II are adducts of butyl alcohol and 3 moles of ethylene of lauryl alcohol and 9 or moles of ethylene of alcohol and 12 or 15 moles ethylene or of isooctylphenol and 3 moles of ethylene A method of applying quaternary phosphonium salts of the general formula I in claim 1 as retarders in the dyeing of polyacryloaitrlle fibres with basic consisting in adding of of the said quaternary phosphonium salts to the the bath and dyeing in the usual prescribed for basic 9 A of applying quaternary salts according to claim wherein quaternary phosphonium salts of the general are added to the dye hath in pure or as solutions in the excess of the polyethoxylated compound XX used as Quaternary phosphonium salts of the general X wherein is an containing 7 to 18 carbo atoms or radical containing 8 to 12 carbon is or or and a integer 3 to insufficientOCRQuality
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
RO7347973A RO57360A2 (en) | 1973-01-13 | 1973-01-13 | |
RO7518573A RO57361A2 (en) | 1973-01-13 | 1973-01-13 |
Publications (2)
Publication Number | Publication Date |
---|---|
IL43714A0 IL43714A0 (en) | 1974-03-14 |
IL43714A true IL43714A (en) | 1977-10-31 |
Family
ID=26653516
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
IL43714A IL43714A (en) | 1973-01-13 | 1973-11-28 | Quaternary phosphonium salts their preparation and their use in dyeing |
Country Status (4)
Country | Link |
---|---|
CH (2) | CH1707473A4 (en) |
DE (1) | DE2360145C3 (en) |
FR (1) | FR2213944A1 (en) |
IL (1) | IL43714A (en) |
Families Citing this family (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4260826A (en) * | 1973-11-15 | 1981-04-07 | The Dow Chemical Company | Novel onium surfactants |
-
1973
- 1973-11-28 IL IL43714A patent/IL43714A/en unknown
- 1973-12-03 DE DE2360145A patent/DE2360145C3/en not_active Expired
- 1973-12-03 FR FR7343032A patent/FR2213944A1/en active Granted
- 1973-12-05 CH CH1707473D patent/CH1707473A4/xx unknown
- 1973-12-05 CH CH1707473A patent/CH575043B5/xx not_active IP Right Cessation
Also Published As
Publication number | Publication date |
---|---|
DE2360145A1 (en) | 1974-08-01 |
CH1707473A4 (en) | 1975-08-15 |
CH575043B5 (en) | 1976-04-30 |
DE2360145B2 (en) | 1977-10-06 |
DE2360145C3 (en) | 1978-05-24 |
IL43714A0 (en) | 1974-03-14 |
FR2213944B1 (en) | 1977-08-05 |
FR2213944A1 (en) | 1974-08-09 |
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