GB1012418A - A process for the preparation of water-soluble surface-active phosphorus-containing products - Google Patents
A process for the preparation of water-soluble surface-active phosphorus-containing productsInfo
- Publication number
- GB1012418A GB1012418A GB4911163A GB4911163A GB1012418A GB 1012418 A GB1012418 A GB 1012418A GB 4911163 A GB4911163 A GB 4911163A GB 4911163 A GB4911163 A GB 4911163A GB 1012418 A GB1012418 A GB 1012418A
- Authority
- GB
- United Kingdom
- Prior art keywords
- mixture
- phosphating
- alcohols
- mol
- products
- 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
- 229910052698 phosphorus Inorganic materials 0.000 title abstract 5
- 239000011574 phosphorus Substances 0.000 title abstract 3
- 238000002360 preparation method Methods 0.000 title abstract 3
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 title abstract 2
- 239000000203 mixture Substances 0.000 abstract 15
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 abstract 9
- 150000001875 compounds Chemical class 0.000 abstract 9
- 150000001298 alcohols Chemical class 0.000 abstract 8
- 239000000047 product Substances 0.000 abstract 8
- DLYUQMMRRRQYAE-UHFFFAOYSA-N tetraphosphorus decaoxide Chemical compound O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 abstract 8
- KBPLFHHGFOOTCA-UHFFFAOYSA-N 1-Octanol Chemical compound CCCCCCCCO KBPLFHHGFOOTCA-UHFFFAOYSA-N 0.000 abstract 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 6
- 125000002947 alkylene group Chemical group 0.000 abstract 6
- 229910052739 hydrogen Inorganic materials 0.000 abstract 6
- 239000001257 hydrogen Substances 0.000 abstract 6
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 abstract 6
- -1 C12 organic compound Chemical class 0.000 abstract 5
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 abstract 5
- 239000003795 chemical substances by application Substances 0.000 abstract 5
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 abstract 4
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 abstract 4
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 abstract 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract 4
- 239000002253 acid Substances 0.000 abstract 3
- 150000007513 acids Chemical class 0.000 abstract 3
- 125000001931 aliphatic group Chemical group 0.000 abstract 3
- 125000005529 alkyleneoxy group Chemical group 0.000 abstract 3
- 125000003368 amide group Chemical group 0.000 abstract 3
- 150000001408 amides Chemical class 0.000 abstract 3
- 239000003599 detergent Substances 0.000 abstract 3
- 150000002989 phenols Chemical class 0.000 abstract 3
- 125000000467 secondary amino group Chemical class [H]N([*:1])[*:2] 0.000 abstract 3
- XFRVVPUIAFSTFO-UHFFFAOYSA-N 1-Tridecanol Chemical compound CCCCCCCCCCCCCO XFRVVPUIAFSTFO-UHFFFAOYSA-N 0.000 abstract 2
- MQWCXKGKQLNYQG-UHFFFAOYSA-N 4-methylcyclohexan-1-ol Chemical compound CC1CCC(O)CC1 MQWCXKGKQLNYQG-UHFFFAOYSA-N 0.000 abstract 2
- 229910019213 POCl3 Inorganic materials 0.000 abstract 2
- 239000004115 Sodium Silicate Substances 0.000 abstract 2
- 229910000147 aluminium phosphate Inorganic materials 0.000 abstract 2
- 238000001816 cooling Methods 0.000 abstract 2
- HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical compound OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 abstract 2
- LQZZUXJYWNFBMV-UHFFFAOYSA-N dodecan-1-ol Chemical compound CCCCCCCCCCCCO LQZZUXJYWNFBMV-UHFFFAOYSA-N 0.000 abstract 2
- SNQQPOLDUKLAAF-UHFFFAOYSA-N nonylphenol Chemical class CCCCCCCCCC1=CC=CC=C1O SNQQPOLDUKLAAF-UHFFFAOYSA-N 0.000 abstract 2
- 125000004437 phosphorous atom Chemical group 0.000 abstract 2
- UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 abstract 2
- FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 abstract 2
- 235000019795 sodium metasilicate Nutrition 0.000 abstract 2
- NTHWMYGWWRZVTN-UHFFFAOYSA-N sodium silicate Chemical compound [Na+].[Na+].[O-][Si]([O-])=O NTHWMYGWWRZVTN-UHFFFAOYSA-N 0.000 abstract 2
- 229910052911 sodium silicate Inorganic materials 0.000 abstract 2
- 239000004094 surface-active agent Substances 0.000 abstract 2
- 229940087291 tridecyl alcohol Drugs 0.000 abstract 2
- 229920002134 Carboxymethyl cellulose Polymers 0.000 abstract 1
- DPXJVFZANSGRMM-UHFFFAOYSA-N acetic acid;2,3,4,5,6-pentahydroxyhexanal;sodium Chemical compound [Na].CC(O)=O.OCC(O)C(O)C(O)C(O)C=O DPXJVFZANSGRMM-UHFFFAOYSA-N 0.000 abstract 1
- 239000007864 aqueous solution Substances 0.000 abstract 1
- 239000001768 carboxy methyl cellulose Substances 0.000 abstract 1
- 235000010948 carboxy methyl cellulose Nutrition 0.000 abstract 1
- 239000008112 carboxymethyl-cellulose Substances 0.000 abstract 1
- 239000007859 condensation product Substances 0.000 abstract 1
- 239000000463 material Substances 0.000 abstract 1
- 235000019832 sodium triphosphate Nutrition 0.000 abstract 1
- 230000007928 solubilization Effects 0.000 abstract 1
- 238000005063 solubilization Methods 0.000 abstract 1
- RYCLIXPGLDDLTM-UHFFFAOYSA-J tetrapotassium;phosphonato phosphate Chemical compound [K+].[K+].[K+].[K+].[O-]P([O-])(=O)OP([O-])([O-])=O RYCLIXPGLDDLTM-UHFFFAOYSA-J 0.000 abstract 1
- UEUXEKPTXMALOB-UHFFFAOYSA-J tetrasodium;2-[2-[bis(carboxylatomethyl)amino]ethyl-(carboxylatomethyl)amino]acetate Chemical compound [Na+].[Na+].[Na+].[Na+].[O-]C(=O)CN(CC([O-])=O)CCN(CC([O-])=O)CC([O-])=O UEUXEKPTXMALOB-UHFFFAOYSA-J 0.000 abstract 1
Classifications
-
- 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
- C07F9/06—Phosphorus compounds without P—C bonds
- C07F9/22—Amides of acids of 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 Table
- C07F9/02—Phosphorus compounds
-
- 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
- C07F9/06—Phosphorus compounds without P—C bonds
-
- 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
- C11D1/02—Anionic compounds
- C11D1/34—Derivatives of acids of phosphorus
- C11D1/345—Phosphates or phosphites
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Health & Medical Sciences (AREA)
- Biochemistry (AREA)
- Molecular Biology (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Wood Science & Technology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Detergent Compositions (AREA)
- Emulsifying, Dispersing, Foam-Producing Or Wetting Agents (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Detergent compositions comprise the product obtained by phosphating a mixture of (a) a water soluble or dispersible condensate of at least 1 mol. of C2 to C4 alkylene oxide with 1 mol. of a reactive hydrogen containing compound of at least C6; and (b) a C1 to C12 organic compound having one or more -OH, amino, or amide groups, but no alkyleneoxy groups, dissolved in water together with various builders. Suitable reactive hydrogen containing compounds are phenols, alcohols, primary and secondary amines, carboxylic and sulphonic acids, and amides thereof; preferred compounds of group (b) are aliphatic and cycloaliphatic alcohols. The phosphated products may be neutralized, e.g. by NaOH. The builders specified are: sodium tripolyphosphate, potassium pyrophosphate, sodium metasilicate, sodium EDTA, and carboxymethyl cellulose, and they may be added to the phosphorus containing products in large amounts, e.g. three parts by weight of builder : 1 part phosphorus compound. Additional alkylene oxide adducts (e.g. ethylene oxide/alkyl phenols) may be dissolved in the composition. Examples include a composition containing, in aqueous solution 60% by weight of sodium metasilicate, 5% by weight of 15-etho-nonyl phenol, with 20% by weight of the phosphated product of a mixture of 6-etho-nonyl phenol (1 mol.), and octanol (1 mol.). U.S.A. Specification 2,674,619 is referred to.ALSO:Phosphated surface-active agents are prepared by phosphating a mixture comprising: (a) a water-soluble or dispersible condensate of at least 1 mol. of C2 to C4 alkylene oxide with 1 mol. of a reactive hydrogen containing compound of at least C6; and (b) a C1 to C12 organic compound having one or more -OH, amino, or amide groups, but no alkyleneoxy groups. Specific phosphating agents are P2O5, PCl3, PCl5, POCl3, or phosphoric acid, or a mixture thereof. Mole ratios of (a) to (b) may vary from 0.5 to 2.0 : 0.5 to 4.0, and a mixture of (a) and (b) within the upper limits of this ratio is suitably reacted with up to 1 mole of P2O5 or up to 2 moles of the other phosphating agents having only 1 phosphorus atom/molecule. Suitable active hydrogen containing compounds are phenols, alcohols, primary and secondary amines, carboxylic and sulphonic acids, and their amides. Preferred compounds of group (b) are aliphatic or cycloaliphatic alcohols (e.g. butanol, octanol, cyclohexanol, methylcyclohexanol). The reaction is suitably performed by gradual addition of the phosphating agent to the mixture of (a) and (b), an appropriate temperature of 95-110 DEG C. being maintained, with cooling if needed. The products may be neutralized with NaOH, and admixed with large proportions of builders to enhance detergent properties (see Division C5), and effect water softening and solubilization of other materials such as alkylene oxide adducts. Examples are given for the preparation of phosphated products from nonyl phenols condensed with six, eight, ten, and twelve molecules of ethylene oxide, and the adducts of six and five molecules of ethylene oxide respectively with tridecyl alcohol and lauryl alcohol, using various alcohols as component (b). An example for a composition with a builder and an alkylene oxide adduct is also given.ALSO:Phosphated surface active agents are prepared by phosphating a mixture comprising: (a) a water soluble or dispersible condensation product of at least 1 mole of C2 to C4 alkylene oxide and 1 mole of a reactive hydrogen containing compound of at least C6, and (b) a C1 to C12 organic compound containing one or more -OH, amino or amide groups, but having no alkyleneoxy groups, with P2O5, PCl3, POCl3 PCl5, or phosphoric acid, or a mixture thereof. Mole ratios of (a) to (b) may vary from 0.5 to 2.0: 0.5 to 4, and a mixture of (a) and (b) within the upper limits of this ratio is suitably reacted with up to 1 mole of P2O5 or up to 2 moles of the other phosphating agents, having only 1 phosphorus atom/molecule. Suitable active hydrogen containing compounds are phenols, alcohols, primary or secondary amines, carboxylic or sulphonic acids, and their amides. Preferred compounds of group (b) are aliphatic cycloaliphatic alcohols (e.g. butanol, octanol, cyclohexanol, and methyl cyclohexanol). The reaction may be performed by gradual addition of the phosphating agent to the mixture of (a) and (b) an appropriate temperature of 95-110 DEG C. being maintained, if necessary with cooling. The products may be neutralized, e.g. with NaOH, and may be admixed with large amounts (e.g. up to 3 parts by weight) of builders to form detergent compositions (see Division C5). Examples are given for preparation of phosphated products from nonyl phenols condensed with six, eight, ten and twelve molecules of ethylene oxide, and the adducts of six and five molecules of ethylene oxide with respectively tridecyl alcohol and lauryl alcohol, using various alcohols as component (b). Specification U.S.A. 2,674,619 is referred to.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| SE1378662A SE303167B (en) | 1962-12-20 | 1962-12-20 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1012418A true GB1012418A (en) | 1965-12-08 |
Family
ID=20297985
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB4911163A Expired GB1012418A (en) | 1962-12-20 | 1963-12-12 | A process for the preparation of water-soluble surface-active phosphorus-containing products |
Country Status (4)
| Country | Link |
|---|---|
| DE (1) | DE1520353B2 (en) |
| GB (1) | GB1012418A (en) |
| NL (1) | NL302219A (en) |
| SE (1) | SE303167B (en) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5047930A (en) * | 1973-08-25 | 1975-04-28 | ||
| US4389259A (en) | 1980-04-30 | 1983-06-21 | Sandoz Ltd. | Asymmetrical diesters of orthophosphoric acid useful as corrosion inhibitors |
| US4465516A (en) * | 1981-04-24 | 1984-08-14 | Sandoz Ltd. | Asymmetrical diesters of ortho-phosphoric acid useful as corrosion inhibitors |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3633940A1 (en) * | 1986-10-04 | 1988-04-07 | Pfersee Chem Fab | METHOD FOR PRODUCING AQUEOUS, CONCENTRATED POLYMERISATE DISPERSIONS BASED ON VINYL AND / OR ACRYLIC ACID ESTERS |
| DE3819374A1 (en) * | 1988-06-07 | 1989-12-14 | Hoechst Ag | PHOSPHORIC ACID PARTIAL SUBSTANCES, METHOD FOR THE PRODUCTION THEREOF, THE USE THEREOF, AND WASHING AND CLEANING AGENTS CONTAINING SUCH MIXTURES |
-
0
- NL NL302219D patent/NL302219A/xx unknown
-
1962
- 1962-12-20 SE SE1378662A patent/SE303167B/xx unknown
-
1963
- 1963-12-12 GB GB4911163A patent/GB1012418A/en not_active Expired
- 1963-12-14 DE DE19631520353 patent/DE1520353B2/en active Pending
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5047930A (en) * | 1973-08-25 | 1975-04-28 | ||
| US4389259A (en) | 1980-04-30 | 1983-06-21 | Sandoz Ltd. | Asymmetrical diesters of orthophosphoric acid useful as corrosion inhibitors |
| US4465516A (en) * | 1981-04-24 | 1984-08-14 | Sandoz Ltd. | Asymmetrical diesters of ortho-phosphoric acid useful as corrosion inhibitors |
Also Published As
| Publication number | Publication date |
|---|---|
| SE303167B (en) | 1968-08-19 |
| NL302219A (en) | |
| DE1520353B2 (en) | 1972-11-16 |
| DE1520353A1 (en) | 1969-04-10 |
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