GB697315A - Solid surface active agents - Google Patents
Solid surface active agentsInfo
- Publication number
- GB697315A GB697315A GB157250A GB157250A GB697315A GB 697315 A GB697315 A GB 697315A GB 157250 A GB157250 A GB 157250A GB 157250 A GB157250 A GB 157250A GB 697315 A GB697315 A GB 697315A
- Authority
- GB
- United Kingdom
- Prior art keywords
- urea
- reaction
- c2h4o
- active agents
- alkyl group
- 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
- 239000004094 surface-active agent Substances 0.000 title abstract 23
- 239000007787 solid Substances 0.000 title abstract 10
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 abstract 47
- 235000013877 carbamide Nutrition 0.000 abstract 25
- 239000004202 carbamide Substances 0.000 abstract 22
- 239000007788 liquid Substances 0.000 abstract 17
- 239000000047 product Substances 0.000 abstract 17
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 abstract 12
- 239000012190 activator Substances 0.000 abstract 12
- 125000000217 alkyl group Chemical group 0.000 abstract 12
- 238000006243 chemical reaction Methods 0.000 abstract 12
- 239000003085 diluting agent Substances 0.000 abstract 8
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 abstract 6
- 150000001298 alcohols Chemical class 0.000 abstract 6
- 239000007795 chemical reaction product Substances 0.000 abstract 6
- QWTDNUCVQCZILF-UHFFFAOYSA-N isopentane Chemical group CCC(C)C QWTDNUCVQCZILF-UHFFFAOYSA-N 0.000 abstract 6
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 abstract 6
- 239000002904 solvent Substances 0.000 abstract 4
- RSWGJHLUYNHPMX-UHFFFAOYSA-N Abietic-Saeure Natural products C12CCC(C(C)C)=CC2=CCC2C1(C)CCCC2(C)C(O)=O RSWGJHLUYNHPMX-UHFFFAOYSA-N 0.000 abstract 3
- 239000004215 Carbon black (E152) Substances 0.000 abstract 3
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical class S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 abstract 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract 3
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical group C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 abstract 3
- KHPCPRHQVVSZAH-HUOMCSJISA-N Rosin Natural products O(C/C=C/c1ccccc1)[C@H]1[C@H](O)[C@@H](O)[C@@H](O)[C@@H](CO)O1 KHPCPRHQVVSZAH-HUOMCSJISA-N 0.000 abstract 3
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 abstract 3
- 239000005864 Sulphur Chemical group 0.000 abstract 3
- 239000002253 acid Substances 0.000 abstract 3
- 150000007513 acids Chemical class 0.000 abstract 3
- 125000003118 aryl group Chemical group 0.000 abstract 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 abstract 3
- 235000014113 dietary fatty acids Nutrition 0.000 abstract 3
- AFABGHUZZDYHJO-UHFFFAOYSA-N dimethyl butane Natural products CCCC(C)C AFABGHUZZDYHJO-UHFFFAOYSA-N 0.000 abstract 3
- LQZZUXJYWNFBMV-UHFFFAOYSA-N dodecan-1-ol Chemical compound CCCCCCCCCCCCO LQZZUXJYWNFBMV-UHFFFAOYSA-N 0.000 abstract 3
- 229930195729 fatty acid Natural products 0.000 abstract 3
- 239000000194 fatty acid Substances 0.000 abstract 3
- 150000004665 fatty acids Chemical class 0.000 abstract 3
- 229930195733 hydrocarbon Natural products 0.000 abstract 3
- 150000002430 hydrocarbons Chemical class 0.000 abstract 3
- 150000002894 organic compounds Chemical class 0.000 abstract 3
- 230000003647 oxidation Effects 0.000 abstract 3
- 238000007254 oxidation reaction Methods 0.000 abstract 3
- 239000001301 oxygen Substances 0.000 abstract 3
- 229910052760 oxygen Inorganic materials 0.000 abstract 3
- 239000008188 pellet Substances 0.000 abstract 3
- 239000012071 phase Substances 0.000 abstract 3
- 150000002989 phenols Chemical class 0.000 abstract 3
- 229920000151 polyglycol Polymers 0.000 abstract 3
- 239000010695 polyglycol Substances 0.000 abstract 3
- 239000000843 powder Substances 0.000 abstract 3
- 239000011541 reaction mixture Substances 0.000 abstract 3
- 239000011347 resin Substances 0.000 abstract 3
- 229920005989 resin Polymers 0.000 abstract 3
- 239000010802 sludge Substances 0.000 abstract 3
- 239000002002 slurry Substances 0.000 abstract 3
- 239000007790 solid phase Substances 0.000 abstract 3
- 125000004079 stearyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 abstract 3
- 238000003756 stirring Methods 0.000 abstract 3
- 239000003784 tall oil Substances 0.000 abstract 3
- 150000003585 thioureas Chemical class 0.000 abstract 3
- KHPCPRHQVVSZAH-UHFFFAOYSA-N trans-cinnamyl beta-D-glucopyranoside Natural products OC1C(O)C(O)C(CO)OC1OCC=CC1=CC=CC=C1 KHPCPRHQVVSZAH-UHFFFAOYSA-N 0.000 abstract 3
- 150000003672 ureas Chemical class 0.000 abstract 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract 3
- 150000001735 carboxylic acids Chemical class 0.000 abstract 2
- 238000010438 heat treatment Methods 0.000 abstract 2
- 239000000080 wetting agent Substances 0.000 abstract 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 abstract 1
- 238000004821 distillation Methods 0.000 abstract 1
Classifications
-
- 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
- C11D3/16—Organic compounds
- C11D3/26—Organic compounds containing nitrogen
- C11D3/32—Amides; Substituted amides
- C11D3/323—Amides; Substituted amides urea or derivatives thereof
-
- 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
- C11D1/66—Non-ionic compounds
- C11D1/72—Ethers of polyoxyalkylene glycols
-
- 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
- C11D11/00—Special methods for preparing compositions containing mixtures of detergents
- C11D11/0082—Special methods for preparing compositions containing mixtures of detergents one or more of the detergent ingredients being in a liquefied state, e.g. slurry, paste or melt, and the process resulting in solid detergent particles such as granules, powders or beads
Landscapes
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Wood Science & Technology (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Solid-Sorbent Or Filter-Aiding Compositions (AREA)
- Lubricants (AREA)
Abstract
Liquid non-ionic surface-active agents having in the molecule a chain of condensed ethylene oxide units are converted into solid form by stirring therewith an excess by weight of urea in the presence of a hydrocarbon reaction diluent in which urea and the reaction product of urea with the liquid surface-active agent are insoluble whereby the reaction mixture takes the form of a slurry and thereafter separating and recovering the solid phase of the reaction product which phase comprises solid non-ionic surface-active addition product. The urea may be present in amounts up to 5 parts by weight per part surface-active agent. p The reaction is preferably effected in the presence of an activator comprising a solvent for urea which does not react with urea at the temperature of reaction, said activator constituting not more than 25 per cent of the weight of the liquid surface-active agent, e.g. water and the C1-3 alcohols. The reaction may be effected at room temperature or higher up to about 100 DEG C. The diluent and activator may be partially removed by distillation and the residual sludge centrifuged and/or filtered and then dried. The resulting powder may be converted into pellets or bars and used as a wetting-agent in photography. Specified liquid surface-active agents are the products derived from fatty and resin acids and having the formula R.COO(C2H4O)n.C2H4OH where R is a C5-50 alkyl group and n is 5-50, e.g. "Ethofats 242/20 and 25" from rosin fatty acids, "Soromin S.G." (Registered Trade Mark) which is a stearyl polyglycol ether, "Renex" from tall oil and those from carboxylic acids obtained by oxidation of paraffins; products obtained from alcohols and having the formula R-O-(C2H4O)n-C2H4OH, where R is a C5-50 alkyl group and n is 5-50, e.g. "Aeto PC 6 or 12" derived from a C15 alcohol and "Brig 30" derived from lauryl alcohol; products derived from alkylated phenols and having the formula R-A-O-(C2H4O)n-C2H4OH where R is a C8-12 alkyl group, A is an aromatic group and n is 5-50, e.g. "Lissapol N," "Igepal C" and "Antarox A200" (Registered Trade Marks); and products derived from mercaptans and having the formula R-S-(C2H4O)n-C2H4OH where R is a C10-14 alkyl group and n is 5-50, e.g. "Nonic 218" described in Specification 643,456. The urea-addition products obtained from those surface-active agents having the first and fourth general formul are believed to be novel. Examples are given wherein the diluent is isopentane and the activator methanol. The Provisional Specification states that liquid surface-active agents in general may be converted into a solid by mixing with an organic compound containing the group >N-C.X-N<, wherein X is oxygen or sulphur, e.g. urea, thiourea and alkylated ureas and thioureas.ALSO:Liquid non-ionic surface-active agents having in the molecule a chain of condensed ethylene oxide groups are converted into solid form by stirring therewith an excess by weight of urea in the presence of a hydrocarbon reaction diluent in which urea and the reaction product of urea and said liquid surface-active agent are insoluble, whereby the reaction mixture takes the form of a slurry, and thereafter separating and recovering the solid phase of the reaction product which phase comprises solid non-ionic surface-active addition product. The urea may be present in a proportion up to 5 parts by weight per part liquid surface-active agent. The reaction is preferably effected in the presence of an activator comprising a solvent for urea which does not react with urea at the temperature of the reaction, the activator constituting not more than 25 per cent based on the weight of the liquid surface-active agent employed; specified solvents are water and C1-3 alcohols. The reaction may be effected at room temperature or higher to about 100 DEG C. The diluent and activator may be partially removed by heating and the residual sludge filtered or centrifuged and then dried. The resulting powder may be converted into pellets or bars and may be used for photographic purposes. Specified liquid surface-active agents are those derived from fatty and resin acids and having the formula R.COO(C2H4O)nC2H4OH, where R is a C5-50 alkyl group and n is an integer preferably 5-50, e.g. "Ethofat 242/20 or 25" from rosin fatty acids, "Soromin SG" (Registered Trade Mark) which is a stearyl polyglycol ether "Renex" from tall oil and carboxy acids obtained by oxidation of paraffins; products derived from alcohols and having the formula R-O-(C2H4O)n-C2H4OH, where R is a C5-50 alkyl group and n preferably 5-50, e.g. "Aeto PC 6 or 12" derived from a C15 alcohol and "Brig 30" derived from lauryl alcohol; products derived from alkylated phenols and having the formula R-A-O(C2H4O)n-C2H4OH, where R is a C8-12 alkyl group, A is an aromatic group and n is preferably 5-50, e.g. "Lissapol N," Igepal C" and "Antarox A200" (Registered Trade Marks); products derived from mercaptans and having the formula R-S-(C2H4O)n-C2H4OH where R is a C10-14 alkyl group and n is preferably 5-50, e.g. "Nonic 218". The urea-addition products obtained from those surfaceactive agents having the first and fourth formul are believed to be new. Examples are given wherein various of these surface-active agents are mixed with urea in presence of isopentane and methanol or aqueous methanol. Specification 643,456 is referred to. The Provisional Specification states that liquid surface-active agents in general may be converted to solid form by mixing with an organic compound containing the group >N-C.X-N<, wherein X is oxygen or sulphur, e.g. urea, thiourea and alkylated ureas and thioureas.ALSO:Liquid non-ionic surface-active agents having in the molecule a chain of condensed ethylene oxide groups are converted into solid form by stirring therewith an excess by weight of urea in the presence of a hydrocarbon reaction diluent in which urea and the reaction product of urea and the liquid surface-active agent are insoluble whereby the reaction mixture takes the form of a slurry, and thereafter separating and recovering the solid phase of the reaction product, which phase comprises solid non-ionic surface-active addition product. The urea may be present in amount up to 5 parts per part by weight of liquid surface-active agent. The reaction is preferably effected in the presence of an activator comprising a solvent for urea which does not react with urea at the temperature of reaction, said activator constituting not more than 25 per cent of the weight of the liquid surface-active agents; specified activators are water and the C1-3 alcohols. The reaction may be effected at room temperature or higher up to about 100 DEG C. The diluent and activator may be partially removed by heating and the residual sludge centrifuged and/or filtered and then dried. The resulting powder may be converted into pellets or bars and used as wetting agent for photography. Specified liquid surface-active agents are the products derived from fatty and resin acids and having the formula R.COO(C2H4O)n.C2H4OH where R is a C5-50 alkyl group and n is 5-50, e.g. "Ethofats 242/20 and 25" from rosin fatty acids, "Soromin SG" (Registered Trade Mark) which is a stearyl polyglycol ether, "Renex" from tall oil and those from carboxylic acids obtained by oxidation of paraffins; products derived from alcohols and having the formula R-O-(C2H4O)n-C2H4OH where R is a C5-50 alkyl group and n is 5-50, e.g. "Aeto PC 6 or 12" derived from a C15 alcohol and "Brig 30" derived from lauryl alcohol; products derived from alkylated phenols and having the formula R-A-O(C2H4O)n-C2H4OH where R is a C8-12 alkyl group, A is an aromatic group and n is preferably 5-50, e.g. "Lissapol N," "Igepal C" and "Antarox A 200" (Registered Trade Marks); products derived from mercaptans and having the formula R-S-(C2H4O)n-C2H4OH where R is a C10-24 alkyl group and n is preferably 5-50, e.g. "Nonic 218" described in Specification 643,456. The urea-addition products obtained from those surface-active agents having the first and fourth formul are believed to be new. Examples are given wherein the diluent is isopentane and the activator methanol. The Provisional Specification states that liquid surface-active agents in general may be converted to solid form by mixing with an organic compound containing the group >N-C.X-N< wherein X is oxygen or sulphur, e.g. urea, thiourea and alkylated ureas and thioureas.
Priority Applications (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| NL78463D NL78463C (en) | 1950-01-20 | ||
| BE500734D BE500734A (en) | 1950-01-20 | ||
| GB157250A GB697315A (en) | 1950-01-20 | 1950-01-20 | Solid surface active agents |
| FR1031097D FR1031097A (en) | 1950-01-20 | 1951-01-17 | Nonionic solid agents active on surfaces |
| DEA12772A DE977288C (en) | 1950-01-20 | 1951-01-20 | Process for the production of solid, non-ionized surfactants |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB157250A GB697315A (en) | 1950-01-20 | 1950-01-20 | Solid surface active agents |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB697315A true GB697315A (en) | 1953-09-23 |
Family
ID=9724294
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB157250A Expired GB697315A (en) | 1950-01-20 | 1950-01-20 | Solid surface active agents |
Country Status (5)
| Country | Link |
|---|---|
| BE (1) | BE500734A (en) |
| DE (1) | DE977288C (en) |
| FR (1) | FR1031097A (en) |
| GB (1) | GB697315A (en) |
| NL (1) | NL78463C (en) |
Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2958665A (en) * | 1957-07-24 | 1960-11-01 | Gen Aniline & Film Corp | Non-ionic surface-active gel compositions and preparation thereof |
| US3062749A (en) * | 1958-09-02 | 1962-11-06 | Robert F Herrling | Composition and method for removing postage stamps |
| US4624713A (en) * | 1984-11-15 | 1986-11-25 | Economics Laboratory, Inc. | Solid rinse aids and methods of warewashing utilizing solid rinse aids |
| EP1020512A2 (en) * | 1994-09-02 | 2000-07-19 | ExxonMobil Research and Engineering Company (Delaware Corp) | Urea-surfactant clathrates |
| US11214763B2 (en) | 2018-01-26 | 2022-01-04 | Ecolab Usa Inc. | Solidifying liquid amine oxide, betaine, and/or sultaine surfactants with a carrier |
| US11377628B2 (en) | 2018-01-26 | 2022-07-05 | Ecolab Usa Inc. | Solidifying liquid anionic surfactants |
| US11655436B2 (en) | 2018-01-26 | 2023-05-23 | Ecolab Usa Inc. | Solidifying liquid amine oxide, betaine, and/or sultaine surfactants with a binder and optional carrier |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB482367A (en) * | 1936-07-08 | 1938-03-29 | Ig Farbenindustrie Ag | Improvements in the manufacture and production of pulverulent synthetic textile assisting agents |
-
0
- NL NL78463D patent/NL78463C/xx active
- BE BE500734D patent/BE500734A/xx unknown
-
1950
- 1950-01-20 GB GB157250A patent/GB697315A/en not_active Expired
-
1951
- 1951-01-17 FR FR1031097D patent/FR1031097A/en not_active Expired
- 1951-01-20 DE DEA12772A patent/DE977288C/en not_active Expired
Cited By (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2958665A (en) * | 1957-07-24 | 1960-11-01 | Gen Aniline & Film Corp | Non-ionic surface-active gel compositions and preparation thereof |
| US3062749A (en) * | 1958-09-02 | 1962-11-06 | Robert F Herrling | Composition and method for removing postage stamps |
| US4624713A (en) * | 1984-11-15 | 1986-11-25 | Economics Laboratory, Inc. | Solid rinse aids and methods of warewashing utilizing solid rinse aids |
| EP1020512A2 (en) * | 1994-09-02 | 2000-07-19 | ExxonMobil Research and Engineering Company (Delaware Corp) | Urea-surfactant clathrates |
| EP1020512A3 (en) * | 1994-09-02 | 2000-12-20 | ExxonMobil Research and Engineering Company (Delaware Corp) | Urea-surfactant clathrates |
| US11214763B2 (en) | 2018-01-26 | 2022-01-04 | Ecolab Usa Inc. | Solidifying liquid amine oxide, betaine, and/or sultaine surfactants with a carrier |
| US11377628B2 (en) | 2018-01-26 | 2022-07-05 | Ecolab Usa Inc. | Solidifying liquid anionic surfactants |
| US11655436B2 (en) | 2018-01-26 | 2023-05-23 | Ecolab Usa Inc. | Solidifying liquid amine oxide, betaine, and/or sultaine surfactants with a binder and optional carrier |
| US11834628B2 (en) | 2018-01-26 | 2023-12-05 | Ecolab Usa Inc. | Solidifying liquid anionic surfactants |
| US11976255B2 (en) | 2018-01-26 | 2024-05-07 | Ecolab Usa Inc. | Solidifying liquid amine oxide, betaine, and/or sultaine surfactants with a binder and optional carrier |
| US12006488B2 (en) | 2018-01-26 | 2024-06-11 | Ecolab Usa Inc. | Solidifying liquid amine oxide, betaine, and/or sultaine surfactants with a carrier |
Also Published As
| Publication number | Publication date |
|---|---|
| NL78463C (en) | |
| DE977288C (en) | 1965-09-23 |
| FR1031097A (en) | 1953-06-19 |
| BE500734A (en) |
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