GB1061768A - Hydroxyalkylated alkenyl phosphonic acids and esters thereof and process for preparing them - Google Patents
Hydroxyalkylated alkenyl phosphonic acids and esters thereof and process for preparing themInfo
- Publication number
- GB1061768A GB1061768A GB3773263A GB3773263A GB1061768A GB 1061768 A GB1061768 A GB 1061768A GB 3773263 A GB3773263 A GB 3773263A GB 3773263 A GB3773263 A GB 3773263A GB 1061768 A GB1061768 A GB 1061768A
- Authority
- GB
- United Kingdom
- Prior art keywords
- alkyl
- oxide
- reaction
- ethylene oxide
- alkylene
- 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
Links
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
- D06M15/00—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment
- D06M15/19—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment with synthetic macromolecular compounds
- D06M15/21—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
- D06M15/356—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds of other unsaturated compounds containing nitrogen, sulfur, silicon or phosphorus atoms
- D06M15/3564—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds of other unsaturated compounds containing nitrogen, sulfur, silicon or phosphorus atoms containing phosphorus
-
- 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 System
- C07F9/02—Phosphorus compounds
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/38—Phosphonic acids RP(=O)(OH)2; Thiophosphonic acids, i.e. RP(=X)(XH)2 (X = S, Se)
- C07F9/40—Esters thereof
- C07F9/4003—Esters thereof the acid moiety containing a substituent or a structure which is considered as characteristic
- C07F9/4015—Esters of acyclic unsaturated acids
-
- 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 System
- C07F9/02—Phosphorus compounds
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/38—Phosphonic acids RP(=O)(OH)2; Thiophosphonic acids, i.e. RP(=X)(XH)2 (X = S, Se)
- C07F9/40—Esters thereof
- C07F9/4071—Esters thereof the ester moiety containing a substituent or a structure which is considered as characteristic
- C07F9/4075—Esters with hydroxyalkyl compounds
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F30/00—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and containing phosphorus, selenium, tellurium or a metal
- C08F30/02—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and containing phosphorus, selenium, tellurium or a metal containing phosphorus
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/49—Phosphorus-containing compounds
- C08K5/51—Phosphorus bound to oxygen
- C08K5/53—Phosphorus bound to oxygen bound to oxygen and to carbon only
- C08K5/5317—Phosphonic compounds, e.g. R—P(:O)(OR')2
- C08K5/5333—Esters of phosphonic acids
-
- 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
- D06M13/244—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 sulfur or phosphorus
- D06M13/282—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 sulfur or phosphorus with compounds containing phosphorus
- D06M13/288—Phosphonic or phosphonous acids or derivatives thereof
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
- D06M13/00—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment
- D06M13/244—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 sulfur or phosphorus
- D06M13/282—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 sulfur or phosphorus with compounds containing phosphorus
- D06M13/313—Unsaturated compounds containing phosphorus atoms, e.g. vinylphosphonium compounds
Abstract
The invention comprises hydroxyalkyl esters of a ,b -unsaturated alkenyl phosphonic acids of formula <FORM:1061768/C2/1> wherein R1 and R2 are each hydrogen or C1 to C6 alkyl; R3 is H, Cl, Br, or C1 to C6 alkyl; R4 and R5 are each H, C1 to C6 alkyl, hydroxymethyl, chloromethyl, or phenyl which may be substituted by e.g. C1 to C4 alkyl, or Cl, at least one of R4 and R5 being H; and optionally R4 and R5 in some groups of formula <FORM:1061768/C2/2> being different from R4 and R5 in other such groups in the chain; n is a number from 1 to 40; and X is H, alkyl, alkenyl, cycloalkyl, or the group <FORM:1061768/C2/3> wherein R4, R5, and n are as above, and where the said group may be different from the corresponding group attached to the other oxygen atom. The compounds are prepared by reacting an a ,b -unsaturated alkenyl phosphonic acid, or an alkyl, cyclo-alkyl or alkenyl semi-ester thereof, or an alkali metal or ammonium salt of such an acid or ester, with a 1,2-alkylene oxide, or a haloalkyl or hydroxyalkyl substituted 1,2-alkylene oxide at a temperature of from 10 DEG to 180 DEG C. Suitable a ,b -unsaturated alkenyl phosphonic acids are vinyl- or propenyl-phosphonic acids and higher homologues having up to 8 C in the alkenyl group, and the corresponding halogenated acids. Semi-esters thereof may be those of saturated or unsaturated C1 to C21 aliphatic alcohols, e.g. methanol, ethanol, butanol, iso-butanol, 2-ethyl hexanol, dodecanol, octadecanol, and allyl or oleyl alcohol, or their salts such as the ammonium, potassium, lithium or sodium salts, or mixtures of free acids, semi-esters, and salts. Suitable alkylene oxides are ethylene oxide and derivatives thereof; propylene-; 1,2-butylene-; and 1,2-pentylene oxides; halo-alkyl-alkylene oxides and hydroxy-alkyl-alkylene oxides, e.g. epichlorohydrin, epibromohydrin, and hydroxymethyl ethylene oxide. Also styrene oxide and its derivatives-e.g. substituted in the phenyl group by C1 to C4 alkyl or chlorine-may be used. The reaction may be carried out by reacting the starting materials at 10-180 DEG C., preferably in the absence of air under an inert atmosphere, and, if necessary, in an inert or reacting solvent -e.g. benzene, toluene, xylene, chlorobenzene, ethyl acetate, acetone, acetophenone, diethyl ether, dioxan, methanol, ethanol, or water. If reacting solvents such as water, are used, they must react to only a minor degree with the alkylene oxide compared with the reaction of the latter with the phosphonic acid. For example, when reacting sodium vinyl phosphonate and ethylene oxide in water the reaction is: <FORM:1061768/C2/4> When low boiling point alkylene oxides are employed, the reaction may be conducted under superatmospheric pressure in a closed vessel. The reaction usually occurs in the absence of hydroxyalkylation catalysts, but these may be used, especially to prepare products having a high degree of hydroxyalkylation, e.g. having more than 4 hydroxy alkyl groups bound to each other. Such catalysts may be alkali metal or earth metal hydroxides, oxides, carbonates or bicarbonates; free alkali metals; Lewis acids such as boron fluoride and complexes thereof with ethers or alcohols. Also, to achieve such higher hydroxylation, the reaction may be performed in two stages, the first without a catalyst, and the product being further hydroxylated with the aid of a catalyst. Mixtures of alkylene oxides may be employed in the process; alternatively an unsaturated alkenyl phosphonic acid may be first reacted with an alkylene oxide more hydrophobic than ethylene oxide-e.g. propylene or 1,2-butylene oxide-and the resulting product then polyhydroxyethylated. The reaction is complete when no more alkylene oxide is taken up, but may be interrupted prematurely to yield a product of lower degree of hydroxylation. Examples are given for the preparation of the reaction products of the following reactants: (a) vinyl phosphonic acid and (i) ethylene oxide, under several different conditions; (ii) propylene oxide; (iii) propylene oxide followed by ethylene oxide; or (iv) epichlorohydrin; and (b) vinyl phosphonic acid-2-ethylhexyl ester and ethylene oxide.
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE1962F0037919 DE1300296B (en) | 1962-09-29 | 1962-09-29 | Process for the production of esters of alpha, beta-unsaturated alkene phosphonic acids |
Publications (1)
Publication Number | Publication Date |
---|---|
GB1061768A true GB1061768A (en) | 1967-03-15 |
Family
ID=7097121
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB3773263A Expired GB1061768A (en) | 1962-09-29 | 1963-09-25 | Hydroxyalkylated alkenyl phosphonic acids and esters thereof and process for preparing them |
Country Status (4)
Country | Link |
---|---|
AT (1) | AT250990B (en) |
BE (1) | BE638017A (en) |
DE (1) | DE1300296B (en) |
GB (1) | GB1061768A (en) |
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
FR2083625A1 (en) * | 1970-03-27 | 1971-12-17 | Stauffer Chemical Co | |
WO1999029957A1 (en) * | 1997-12-06 | 1999-06-17 | Albright & Wilson Uk Limited | Fibrous substrate treatment |
Families Citing this family (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE2945945A1 (en) * | 1979-11-14 | 1981-05-27 | Hoechst Ag, 6000 Frankfurt | ALKANPHOSPHONIC ACID SEMI-SALTS, THEIR PRODUCTION AND THEIR APPLICATION AS A PREPARATION AGENT FOR TEXTILE FIBERS |
-
0
- BE BE638017D patent/BE638017A/xx unknown
-
1962
- 1962-09-29 DE DE1962F0037919 patent/DE1300296B/en active Pending
-
1963
- 1963-09-25 GB GB3773263A patent/GB1061768A/en not_active Expired
- 1963-09-27 AT AT778863A patent/AT250990B/en active
Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
FR2083625A1 (en) * | 1970-03-27 | 1971-12-17 | Stauffer Chemical Co | |
WO1999029957A1 (en) * | 1997-12-06 | 1999-06-17 | Albright & Wilson Uk Limited | Fibrous substrate treatment |
US6485525B1 (en) | 1997-12-06 | 2002-11-26 | Rhodia Consumer Specialties Limited | Fibrous substrate treatment |
Also Published As
Publication number | Publication date |
---|---|
DE1300296B (en) | 1969-07-31 |
AT250990B (en) | 1966-12-12 |
BE638017A (en) |
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