US2903485A - Alkylphenoxypblyethoxyalkandlil - Google Patents

Alkylphenoxypblyethoxyalkandlil Download PDF

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US2903485A
US2903485A US2903485DA US2903485A US 2903485 A US2903485 A US 2903485A US 2903485D A US2903485D A US 2903485DA US 2903485 A US2903485 A US 2903485A
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    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
    • C08G65/02—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
    • C08G65/26—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers and other compounds
    • C08G65/2603—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers and other compounds the other compounds containing oxygen
    • C08G65/2606—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers and other compounds the other compounds containing oxygen containing hydroxyl groups
    • C08G65/2612—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers and other compounds the other compounds containing oxygen containing hydroxyl groups containing aromatic or arylaliphatic hydroxyl groups
    • 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
    • Y10S516/02—Organic and inorganic agents containing, except water

Definitions

  • the compounds of this invention may be represented by the formula ocznnnonn in which R is an alkyl group of six to twelve carbon atoms,jD'is one of the groups -C H O--,
  • the groups represented by the symbolD may be represented by the formulas C H O and are derived from octylene oxide, styrene oxide, isopropyl glycidyl ether, and phenyl glycidyl ether, respectively.
  • the spatial representations of the D groups are thosethatr-are. most likely, based on the best analytical and theoretical considerations. sible that the D group derived from styrene oxide, for instance, may be represented as either It may be pos-" geous uses of the present compounds are apparently based latented Sept. 8, 1959 or either respectively, with the former representations more probable.
  • the group C H 5O- as a representation of D may have the oxygen atom positioned at any possible chain location although the terminal location is more readily dbtained.
  • the foregoing and following formulas containing the defined D groups must be construed in the light of the above discussion in that the more likely formula is given. Nevertheless the other spatial possibilities are encompassed within this invention.
  • the number of ethylene oxide groups in the above compound varies from ten to thirty-five. It is important in the present compounds that, While the number of ethylene oxide units varies within the defined range, only a single unit of D is employed. While it is possible to have a second unit of D in the present compound, such is not desirable or advantageous because, it is difiicult to attach the second unit of D and, even with the second unit of the. structure just defined can the desirable results of this invention be obtained.
  • the products of this invention are generally pale yellow liquids, although some approach colorlessness. These products exhibit excellent detergency, particularly 7 on They also possess the valuable properties of low solidification temperature and stability in built formulations. Surprisingly, the compounds of this invention possess all of the above properties to a highly advantageous degree which makes them available for many important applications,
  • Dishwashing detersive characteristics were determined by the Fineman dynamic hard surface detergency test in which the compound under test was evaluated against glass, steel, and plastic substrates.
  • the present compounds gave excellent results on all three substrates both as to cleansing efficiency and prevention of redeposition of soil.
  • These compounds are also effective textile detergents, particularly for removal of oily carbon from cotton and wool.
  • a detergent have a cloud point appreciably above the normal temperature at which it is to be stored. This is even more significant where automatic, dispensing units are contemplated. If the cloud point of a detergent is too low, undesired Stratification occurs from its aqueous solutions so that, especially on prolonged storage, the concentration of any given portion of the stratified aqueous detergent system is unpredictable and, therefore, highly undesirable. Under such circumstances it is highly problematical what detersive effects will be realized. Asv a general rule it is advantageous for a detergent to have a cloud point at least above normal room temperatures.
  • the instant compounds have cloud points that are, entirely acceptable, usually ranging from about 50 C., and up as determined in 1% distilled aqueous systems by a standard method.
  • the compounds of this invention have very low solidification temperatures. This is significant inthat the present compounds may be stored in containers in cooled temperatures and still be pourable and, therefore, readily transferable and usable. Many alkylphenoxypolyethoxyalkanols lacking the exact formula of the present compounds are at least semi-solidsat room temperatures and, therefore, must be stored with care or reheated in order to restore pourability.
  • the compounds of this invention may be built into desirable formulations by employing borates, carbonates, silicates, phosphates, and the like, in known ways. These formulations are efiective and stable.
  • the compounds of this invention are prepared by reacting an alkylphenol with ethylene oxide in the temperature range of 130 to 200 C., preferably, 170 to 195 C., in the presence of a strong basic catalyst such as sodium, potassium, sodium hydroxide, potassium hydroxide, sodium methoxide, potassium ethoxide, and the like. Pressures from atmospheric to about thirty pounds per square inch gauge may be advantageously employed. Following the ethylene oxide addition there is added, in a similar way and under similar reaction conditions, either phenyl glycidyl ether, styrene oxide, octylene oxide, or isopropyl glycidyl ether.
  • the product is isolated in yields consistently above 85% by neutralizing the catalyst, steam stripping if necessary until residual oxide odors disappear, and then by stripping off water, preferably under reduced pressure. If desired, the product may be filtered to remove minor amounts of colored bodies but such is not usually necessary.
  • Example 1 There are added to a reaction vessel 153 parts of octylphenol and one part of powdered potassium hydroxide. The system is flushed out with nitrogen and the temperature raised to 185 C. Ethylene oxide is slowly introduced over a period of three hours, while the reaction temperature is heated at 195 to 200 C. A total of 495 parts of ethylene oxide is added.
  • Example 2 There are added to a reaction vessel 356 parts of hexylphenol and five parts of sodium. The reaction mixture is heated to C. and then over a period of two and one-half hours, 1,936 parts of ethylene oxide is introduced while the temperature is heated at to 188 C. The system is flushed out with nitrogen and there is then added over a 50-minute period 256 parts of octylene oxide during which time the temperature is maintained at 176 to 187 C. The temperature is maintained at this level for two hours after the octylene oxide addition. The product is neutralized with sulfuric acid, then washed with water and toluene. The water layer is discarded and the toluene then stripped off under water vacuum at 120 C. The product is filtered and is identified as the compound having the formula Ca ia In a similar way there are prepared the following compounds:
  • GaHfl mmmo omonomoQ 02110180 omgrromo sausage We claim: W p I I 1.
  • R is an alkyl group of six to twelve carbon atoms
  • n is an integer of ten to thirty-five
  • D is a member from the class consisting of C H O'
  • composition of matter the compound having the formula @(WmnmomgnQ in which R is an alkyl group of six to twelve carbon atoms and n is an integer of ten to thirty-five.
  • composition of matter the compound having the formula @wmmmcomgnomoo H CH3 in which R is an alkyl group of six to twelve carbon atoms and n is an integer of ten to thirty-five.
  • composition of matter the compound having the formula QwmHmOQmc JHoHmQ in which R is an alkyl group of six to twelve carbon atoms and n is an integer of ten to thirty-five.
  • composition of matter the compound having the formula CsHu @(ommmoomgnQ 7.
  • composition of matter the compound having the formula Ca rI @(ommmoomgnQ 7 -8.
  • Ce ia OCBHDHOCBHMOH 5 9.
  • a composition of matter the compound having the formula @(0 2 0100 ompncmoQ References Cited in the file of this patent UNITED STATES PATENTS Steindorlf etal. Sept. 3, 1940 Benneville May 13, 1952 Benneville May 13, 1952 Johnson Sept. 2, 1952 FOREIGN PATENTS France Apr. 23, 1956 Great Britain Mar. 13, 1957 OTHER REFERENCES Schwartz et 211.: Surface Active Agents (1949), pp.

Description

ALKYLiHENOXYPbLYETiidXYALKANdLb 7 Earl W. Lane,- Philadelphia, Pa., and George L. Brown,
Moores'town, N.J., assignors to Ro'hm&..Haas Comp'any, Philadelphia, Pa., a corporation of Delaware No Drawing. ApplicationNovmher 29, 1956 p Serial Ne. 624,981 '10 Claims. to]. 260-613) This invention deals with specific alkylphenoxypolyethoxyalkanols as new compositions of matter. It further concerns a method for the preparation of these compositions. 7
The compounds of this invention may be represented by the formula ocznnnonn in which R is an alkyl group of six to twelve carbon atoms,jD'is one of the groups -C H O--,
(I) (I) V ,'CH5
"glass, plastic, metal, wool, and cotton. They also have satisfactory cloud points and exhibit very slight or no foam especially at'normal temperatures of use.
The groups represented by the symbolD may be represented by the formulas C H O and are derived from octylene oxide, styrene oxide, isopropyl glycidyl ether, and phenyl glycidyl ether, respectively. Actually, the spatial representations of the D groups are thosethatr-are. most likely, based on the best analytical and theoretical considerations. sible that the D group derived from styrene oxide, for instance, may be represented as either It may be pos-" geous uses of the present compounds are apparently based latented Sept. 8, 1959 or either respectively, with the former representations more probable. The group C H 5O- as a representation of D may have the oxygen atom positioned at any possible chain location although the terminal location is more readily dbtained. The foregoing and following formulas containing the defined D groups must be construed in the light of the above discussion in that the more likely formula is given. Nevertheless the other spatial possibilities are encompassed within this invention.
The number of ethylene oxide groups in the above compound varies from ten to thirty-five. It is important in the present compounds that, While the number of ethylene oxide units varies within the defined range, only a single unit of D is employed. While it is possible to have a second unit of D in the present compound, such is not desirable or advantageous because, it is difiicult to attach the second unit of D and, even with the second unit of the. structure just defined can the desirable results of this invention be obtained.
The products of this invention are generally pale yellow liquids, although some approach colorlessness. These products exhibit excellent detergency, particularly 7 on They also possess the valuable properties of low solidification temperature and stability in built formulations. Surprisingly, the compounds of this invention possess all of the above properties to a highly advantageous degree which makes them available for many important applications,
particularly commercial and residential automatic dishthat otherwise have some structural similarities.
It is known in the art that various alkylene oxides can be added to compounds having reactive hydrogen atoms to form compounds that are surface active. The known 45' compounds generally suffer from one or more deficienabsence of any one of which can act as a bar to many cies with regard to the above-enumerated properties, the
practical applications. For instance, many otherwise ac- :ceptable detergents exhibit high foam which bars their use m many applications. others are unstable in built formulations and become discolored in an unsightly way frequently 'with concurrent diminution of detersive proper- 'ties; others tend to become very viscous even to the point of solidification even in the range of normal room temperatur'es which bars their use in automatic dispensing ;umts; others have unsatisfactory cloud points under normal storage conditions. The unique compounds of this "invention suffer no such limitations and,hence, have a wide range of valuable applications not available to the know compounds. i
The unusual characteristics and concurrent advantaon the critical hydrophobic-hydrophilic balance caused by the relationship between the R group, the group,
Same volume of same temperature of water was used as a blank. The speed of the rotor spray arm in revolutions per minute for water alone was 100. For a detergent to be commercially acceptable it must give a value of about 75 and preferably 80 or above. The present compounds consistently give values ranging between 90 and 100. On the other hand, similar alkylphenoxypolyethoxyalkanols not having the single unit of the defined D groups gave values below 30 down to the point of stalling the motor, with concurrent serious diminution of cleansing powers reduced to the range of unacceptability.
Dishwashing detersive characteristics were determined by the Fineman dynamic hard surface detergency test in which the compound under test was evaluated against glass, steel, and plastic substrates. The present compounds gave excellent results on all three substrates both as to cleansing efficiency and prevention of redeposition of soil. These compounds are also effective textile detergents, particularly for removal of oily carbon from cotton and wool.
It is important in most practical applications that a detergent have a cloud point appreciably above the normal temperature at which it is to be stored. This is even more significant where automatic, dispensing units are contemplated. If the cloud point of a detergent is too low, undesired Stratification occurs from its aqueous solutions so that, especially on prolonged storage, the concentration of any given portion of the stratified aqueous detergent system is unpredictable and, therefore, highly undesirable. Under such circumstances it is highly problematical what detersive effects will be realized. Asv a general rule it is advantageous for a detergent to have a cloud point at least above normal room temperatures. The instant compounds have cloud points that are, entirely acceptable, usually ranging from about 50 C., and up as determined in 1% distilled aqueous systems by a standard method.
The compounds of this invention have very low solidification temperatures. This is significant inthat the present compounds may be stored in containers in cooled temperatures and still be pourable and, therefore, readily transferable and usable. Many alkylphenoxypolyethoxyalkanols lacking the exact formula of the present compounds are at least semi-solidsat room temperatures and, therefore, must be stored with care or reheated in order to restore pourability.
If desired, the compounds of this invention may be built into desirable formulations by employing borates, carbonates, silicates, phosphates, and the like, in known ways. These formulations are efiective and stable.
The compounds of this invention are prepared by reacting an alkylphenol with ethylene oxide in the temperature range of 130 to 200 C., preferably, 170 to 195 C., in the presence of a strong basic catalyst such as sodium, potassium, sodium hydroxide, potassium hydroxide, sodium methoxide, potassium ethoxide, and the like. Pressures from atmospheric to about thirty pounds per square inch gauge may be advantageously employed. Following the ethylene oxide addition there is added, in a similar way and under similar reaction conditions, either phenyl glycidyl ether, styrene oxide, octylene oxide, or isopropyl glycidyl ether. The product is isolated in yields consistently above 85% by neutralizing the catalyst, steam stripping if necessary until residual oxide odors disappear, and then by stripping off water, preferably under reduced pressure. If desired, the product may be filtered to remove minor amounts of colored bodies but such is not usually necessary.
The compounds of this invention and the method of their preparation may be more fully understood from the following illustrative examples in which parts byweight are used throughout.
Example 1 There are added to a reaction vessel 153 parts of octylphenol and one part of powdered potassium hydroxide. The system is flushed out with nitrogen and the temperature raised to 185 C. Ethylene oxide is slowly introduced over a period of three hours, while the reaction temperature is heated at 195 to 200 C. A total of 495 parts of ethylene oxide is added.
Into another reaction flask there is charged 200 parts of the above octylphenoxypolyethoxyalkanol. The system is swept out with nitrogen and then 33.4- parts of styrene oxide is added over a 60-minute period, while the temperature of the reaction mixture is heated at 178 to 183 C. The temperature is maintained at that level for six hours after the styrene oxide addition. The product is neutralized with aqueous 96% sulfuric acid, then washed with water in toluene. The water layer is discarded and the mixture of toluene and product is stripped to C. under water vacuum to remove the toluene. The product is filtered and identified as the compound apparently having the formula Cs n In a similar way, there are prepared the corresponding products having 10, 24, 32, and 35 ethylene oxide units.
Example 2 There are added to a reaction vessel 356 parts of hexylphenol and five parts of sodium. The reaction mixture is heated to C. and then over a period of two and one-half hours, 1,936 parts of ethylene oxide is introduced while the temperature is heated at to 188 C. The system is flushed out with nitrogen and there is then added over a 50-minute period 256 parts of octylene oxide during which time the temperature is maintained at 176 to 187 C. The temperature is maintained at this level for two hours after the octylene oxide addition. The product is neutralized with sulfuric acid, then washed with water and toluene. The water layer is discarded and the toluene then stripped off under water vacuum at 120 C. The product is filtered and is identified as the compound having the formula Ca ia In a similar way there are prepared the following compounds:
( CZHOQZO OBHMOH C iz zs Example 3 added and the temperature raisedto 185 to 192 C. A total of 115 parts of iso'propyl glycidyl ether is added over a period of one and one-half hours. The reaction mixture is neutralized with sulfuric acid and steam stripped. Water is removed by heating the mixture up to 148 (3; under watervacuum. The mixtureis filtered and the product is collected as the filtrate. The product corresponds to the compound having the formula There are added to a reaction vessel 187.2 parts of decylphenol and two parts of sodium hydroxide. The temperature of the reaction mixture is raised to 170 C. and then ethylene oxide is introduced. A total of 704 parts of ethylene oxide is added over a period of four hours while the temperature is maintained at 172 to 190 C. The system is swept out with nitrogen and there is then added over a period of four hours 120 parts of phenyl glycidyl ether while the temperature is heated at 190 to 198 C. The product is neutralized with aqueous sulfuric acid and washed with water and toluene. The water layer is discarded and the toluene is removed by steam stripping under Water vacuum at 100 C. The mixture is filtered and the product is collected as the filtrate. The product corresponds to the compound having the formula D) 0 0 00 CHgZHCHgOQ In an analogous way there are prepared compounds having the following formulas:
GaHfl mmmo omonomoQ 02110180 omgrromo sausage We claim: W p I I 1. As a composition of matter the compound having the formula 0 onamnonrr .in which R is an alkyl group of six to twelve carbon atoms, n is an integer of ten to thirty-five, and D is a member from the class consisting of C H O',
V r I ,/oH, -QEQHQ, -0H2CHCH10CE A H A on, s I l and -omgrromo 2 (OCIHOBOCEHHOH in which R is an alkyl group of six to twelve carbon atoms and n is an integer of ten to thirty-five.
3. As a composition of matter the compound having the formula @(WmnmomgnQ in which R is an alkyl group of six to twelve carbon atoms and n is an integer of ten to thirty-five.
4. As a composition of matter the compound having the formula @wmmmcomgnomoo H CH3 in which R is an alkyl group of six to twelve carbon atoms and n is an integer of ten to thirty-five.
5. As a composition of matter the compound having the formula QwmHmOQmc JHoHmQ in which R is an alkyl group of six to twelve carbon atoms and n is an integer of ten to thirty-five.
6. As a composition of matter the compound having the formula CsHu @(ommmoomgnQ 7. As a composition of matter the compound having the formula Ca rI @(ommmoomgnQ 7 -8. As a composition of matter the compound having the formula Ce ia (OCBHDHOCBHMOH 5 9. As a composition of matter the compound having the formula @(0 2 0100 ompncmoQ References Cited in the file of this patent UNITED STATES PATENTS Steindorlf etal. Sept. 3, 1940 Benneville May 13, 1952 Benneville May 13, 1952 Johnson Sept. 2, 1952 FOREIGN PATENTS France Apr. 23, 1956 Great Britain Mar. 13, 1957 OTHER REFERENCES Schwartz et 211.: Surface Active Agents (1949), pp.

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1. AS A COMPOSITION OF MATTER THE COMPOUND HAVING THE FORMULA
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Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3123561A (en) * 1961-01-04 1964-03-03 Hydroxyphenyl
US3154514A (en) * 1960-12-05 1964-10-27 Union Carbide Corp Ethylene oxide polymers having improved stress endurance
US3334147A (en) * 1962-02-28 1967-08-01 Economics Lab Defoaming and surface active compositions
US4237320A (en) * 1978-09-11 1980-12-02 Basf Aktiengesellschaft 1,3-Bis-aryl-2-oxyalkylated-glycerol ethers
US4302349A (en) * 1979-06-26 1981-11-24 Chemische Werke Huls, A.G. Adducts of alcohols and olefin oxides, suitable for reducing the interfacial surface tension of oily phases with respect to water
US6552091B1 (en) * 1999-08-27 2003-04-22 Goldschmidt Ag Block-copolymeric polyalkylene oxides containing styrene oxide, obtained by alkoxylation, and their use

Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2213477A (en) * 1935-12-12 1940-09-03 Gen Aniline & Film Corp Glycol and polyglycol ethers of isocyclic hydroxyl compounds
US2596092A (en) * 1950-03-28 1952-05-13 Rohm & Haas Bis alkylbenzyl ethers of polyethylene glycols
US2596091A (en) * 1950-03-28 1952-05-13 Rohm & Haas Nonionic surface-active agents
US2609344A (en) * 1948-08-14 1952-09-02 Nat Aluminate Corp Prevention of foaming in steam generation
FR1120963A (en) * 1954-03-22 1956-07-18 Rohm & Haas ethers and their preparation
GB770073A (en) * 1954-03-22 1957-03-13 Rohm & Haas Improvements in or relating to ethers of alkylphenoxy-polyethoxyethanols and the preparation thereof

Patent Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2213477A (en) * 1935-12-12 1940-09-03 Gen Aniline & Film Corp Glycol and polyglycol ethers of isocyclic hydroxyl compounds
US2609344A (en) * 1948-08-14 1952-09-02 Nat Aluminate Corp Prevention of foaming in steam generation
US2596092A (en) * 1950-03-28 1952-05-13 Rohm & Haas Bis alkylbenzyl ethers of polyethylene glycols
US2596091A (en) * 1950-03-28 1952-05-13 Rohm & Haas Nonionic surface-active agents
FR1120963A (en) * 1954-03-22 1956-07-18 Rohm & Haas ethers and their preparation
GB770073A (en) * 1954-03-22 1957-03-13 Rohm & Haas Improvements in or relating to ethers of alkylphenoxy-polyethoxyethanols and the preparation thereof

Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3154514A (en) * 1960-12-05 1964-10-27 Union Carbide Corp Ethylene oxide polymers having improved stress endurance
US3123561A (en) * 1961-01-04 1964-03-03 Hydroxyphenyl
US3334147A (en) * 1962-02-28 1967-08-01 Economics Lab Defoaming and surface active compositions
US4237320A (en) * 1978-09-11 1980-12-02 Basf Aktiengesellschaft 1,3-Bis-aryl-2-oxyalkylated-glycerol ethers
US4302349A (en) * 1979-06-26 1981-11-24 Chemische Werke Huls, A.G. Adducts of alcohols and olefin oxides, suitable for reducing the interfacial surface tension of oily phases with respect to water
US6552091B1 (en) * 1999-08-27 2003-04-22 Goldschmidt Ag Block-copolymeric polyalkylene oxides containing styrene oxide, obtained by alkoxylation, and their use

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