US3692884A - Phosphate esters - Google Patents

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US3692884A
US3692884A US797691A US3692884DA US3692884A US 3692884 A US3692884 A US 3692884A US 797691 A US797691 A US 797691A US 3692884D A US3692884D A US 3692884DA US 3692884 A US3692884 A US 3692884A
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    • G—PHYSICS
    • G11—INFORMATION STORAGE
    • G11B—INFORMATION STORAGE BASED ON RELATIVE MOVEMENT BETWEEN RECORD CARRIER AND TRANSDUCER
    • G11B5/00—Recording by magnetisation or demagnetisation of a record carrier; Reproducing by magnetic means; Record carriers therefor
    • G11B5/62—Record carriers characterised by the selection of the material
    • G11B5/68—Record carriers characterised by the selection of the material comprising one or more layers of magnetisable material homogeneously mixed with a bonding agent
    • G11B5/70—Record carriers characterised by the selection of the material comprising one or more layers of magnetisable material homogeneously mixed with a bonding agent on a base layer
    • G11B5/7013—Record carriers characterised by the selection of the material comprising one or more layers of magnetisable material homogeneously mixed with a bonding agent on a base layer characterised by the dispersing agent
    • 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
    • C07F9/08—Esters of oxyacids of phosphorus
    • C07F9/09—Esters of phosphoric acids
    • C07F9/091—Esters of phosphoric acids with hydroxyalkyl compounds with further substituents on alkyl
    • 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
    • C07F9/24—Esteramides

Definitions

  • Such oxide coated tapes are generally employed in widths such as one-quarter or one-half inch and utilized in rolls of up to about 2,500 feet. Information is recorded on a series of parallel tracks extending the length of the tape. As this type of equipment has become more sophisticated, the characteristics of the oxide coating have become more critical. Thus, an accurate dispersion of the metal oxide in the coating is now essential to uniformity of reproduction.
  • Various dispersing agents have heretofore been employed to assist in providing such a uniform iron oxide coating over the base tape; see for example US. Pat. No. 3,144,352 where surfactants such as lecithin have been utilized for this purpose.
  • the present invention is directed to a novel group of amine salts of complex phosphate esters that have been found to be particularly advantageous when employed for dispersing finely divided ferromagnetic oxide particles, such as acicular gamma ferric oxide, in tape-coating systems.
  • novel compounds are broadly described by the following formula:
  • x and z are integers from 1 to 2, y is an integer of 0 to l and the sum of x, y and z is always 3;
  • R is a hydrocarbon radical of up to 30 carbons that is selected from aliphatic, cyclic, aromatic and combinations thereof; n is an integer from 3 to 25;
  • A is an alkylene radical of from two to three carbon atoms;
  • R is a monovalent radical of from 0-20 carbons (preferably 0-12 carbons) selected from aliphatic amines of the formula -NH(A'NH),,,H and monocyclic heterocyclic compounds containing from one to three nitrogen atoms and from zero to one oxygen atoms as the only annular hetero atoms.
  • aliphatic amines is intended to include alkylene polyamines such as triethylene tetraamine, diethylene triamine as well as ammonia.
  • heterocyclic compounds is intended to include morpholine, piperazine, pyridine, triazine, pyrrole, pyrrolidine, and the like with and without substituents.
  • R is an alkylaromatic radical of from to 20 carbons such as octylor nonylphenyl; A and A are ethylene radicals; m is an integer of from 2 to 3; n is an integer of from 6 to 15, more preferably an average of 8 to 10; and y is O and x and 2 total 3.
  • any combination of up to a total of three alkoxy and/or amino groups may be attached to the pentavalent phosphorous atom, it being understood of course that at least one alkoxy and at least one amino radical are always present in the resulting composition.
  • novel products of this invention are produced by a carefully controlled two-step process wherein a long chain organic alcohol such as alkylphenoxypoly(alkyleneoxy)alkanol is first reacted (esterified) with, preferably, phosphorous pentoxide to form at least a partial phosphate ester. Thereafter, the resulting monoor diphosphate ester is reacted with the abovedescribed amine either through partial neutralization, or displacement of the ester by the amine.
  • a long chain organic alcohol such as alkylphenoxypoly(alkyleneoxy)alkanol
  • estersified preferably, phosphorous pentoxide to form at least a partial phosphate ester.
  • the resulting monoor diphosphate ester is reacted with the abovedescribed amine either through partial neutralization, or displacement of the ester by the amine.
  • a pentavalent phosphorous such as phosphorous pentoxide P 0 the acid anhydride of phosphoric acid, or phosphorous oxychloride, in an amount in excess of that theoretically required, is combined with a high molecular weight nonionic surface active agent having the general formula:
  • R OH 2 wherein R, A, and n have the definitions set forth for formula (1), above.
  • the excess of pentavalent phosphorous is necessary to ensure that no free surface active agent remains.
  • the phosphate ester of formula (3) is reacted with an amine having at least one nitrogen and including from O to 20 carbon atoms.
  • the amine can be either aliphatic or heterocyclic. Sufficient of the amine is introduced to adjust the pH of the resulting amine salt to about 5 to 7.
  • the amine is aliphatic and an alkylene polyamine defined by the following formula:
  • nonionic surface-active alcohols useful for reaction with the acid anhydride of phosphoric acid include the ethylene oxide adducts of the alkanols and alkylphenols. Such substances are commercially available under trademarks such as Neodol, from Shell Oil Company and Igepal, from General Analine and Film Corporation. For purposes of convenience, reference will frequently be made in the remainder of this specification to the use of Igepal CO-630, a nonylphenoxypoly(ethyleneoxy)ethanol, as the surface active alcohol.
  • alkylpoly(alkyleneoxy)alkanols such as Igepal CO-430, Igepal CA- 630 and the like, as well as alkylpoly(alkyleneoxy)-alkanols containing up to about 25 alkyleneoxy units, are suitable.
  • reaction conditions during formation of the phosphate esters in the initial step are not particularly critical, it has been found to be critical for the amount of amine employed to be sufficient to adjust the pH of the resulting complex salt to the range of about 5-7, and preferably 5-6.
  • the pH of the resulting amine salt is substantially in excess of about 6, the reactants become solid and hard to handle when introduced into the ferromagnetic oxide coating composition.
  • a pH lower than about 5 inhibits subsequent dispersion of the metal oxide in the coating system.
  • the temperature conditions may vary over a wide range, but it is desirable that the reaction temperature at no time greatly exceed the boiling point of water at atmospheric pressure.
  • the reaction pressure employed can be either sub-atmospheric or superatmospheric, in addition to ambient.
  • novel dispersing agents of this invention can be incorporated with any of the iron oxide-containing systems presently employed in the magnetic tape production industry. Such systems have heretofore been prepared with iron oxide as well as various other components normally incorporated in the binder system, including resin materials, lubricants, and solvents, such as set forth in U.S. Pat. No. 3,144,352, supra. For this reason, the present invention is not intended to be limited to any particular metal oxide system, but is useful whenever uniform dispersion of the metal oxide is desirable.
  • the .amount of dispersing agent employed can vary widely, as little as about 1 percent by weight being suitable, while amounts up to percent can be advantageous. It is preferable to use from about 2-5 percent based on the total weight of the coating composition.
  • the resulting coating incorporating the novel dispersing agent of this invention can be employed with a wide variety of known tape bases.
  • tapes formed of polyesters such as polyethylene terephthalate, and available under the trade name Mylar, are particularly suitable as they have an extremely long life.
  • organophosphorous compounds resulting from the reaction of the long chain alcohol with the pentavalent phosphorous oxides, depend upon both the extent to which the esterification reaction is allowed to continue and the relative concentration of the reactants. Subsequently, the amount of amine displacement (or neutralization) will again depend upon the amount of reactants present as well as upon the actual reaction conditions. As previously set forth it is only critical that at least one alkoxy and one amino radical remain complexed with each pentavalent phosphorous. Suitable solvents include toluene and tetrahydrofuran among the many others that could be utilized.
  • EXAMPLE l lgepal C0-630 a nonylphenoxypoly(ethyleneoxy)ethanol, in an amount of about 1,000 grams was heated with agitation to about F.
  • Phosphorous pentoxide in an amount of about 96 grams was slowly added while the reaction temperature was allowed to rise to about 180 F.
  • the phosphorous pentoxide was added at a rate sufficient to maintain the temperature in the range of to 190 F during the addition which took about 1 hour. The rate of addition was decreased as the reaction neared completion.
  • the reaction temperature was retained at about F for about 1 hour after the addition of the phosphorous pentoxide. Some phosphorous pentoxide remained unreacted in the clear liquid portion.
  • the resulting ester was filtered through diatomaceous earth. Other filters having a 50-75 micron porosity are also suitable for this filtering operation. Care was taken to dispose of the filtering medium as the free phosphorous pentoxide presented a fire hazard.
  • EXAMPLE ll Utilizing 30 parts of the complex ester formed in example l, above, in lieu of 30 parts of lecithin, the coating composition set forth in example I of US. Pat. No. 3,144,352 is prepared. The coating is applied to a Mylar tape, and the dispersion characteristics of the iron oxide in the coating are found to be excellent.
  • composition of matter having the following for mula:
  • R is a hydrocarbon radical of up to 30 carbon atoms
  • n is an integer of from 3 to 35;
  • A is an alkylene radical of from two to three carbon atoms
  • R is a monovalent radical of the formula:
  • A is an alkylene radical of from two to three A commsmon according to clam where"! m ls carbon atoms; and 3, isA about IOand R is no ylphenall 5 h m is a whole number integer of from to 5. composltlon accor mg to c aim w erem m 2.
  • a composition according to claim 1 wherein A iiabout lo.a.ndRis z i g 5 h and are ethylene m is n is 645 and R is an composition accor mg to c aim w erem m IS alkyl radical of from to carbons. n about 1 R y p y 3.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
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  • General Health & Medical Sciences (AREA)
  • Molecular Biology (AREA)

Abstract

A novel group of compounds, the reaction product of an amine and a phosphate ester that are useful as dispersing agents for the finely divided metal oxides used in preparing magnetic tape coatings. The compound having the formula: WHERE R is a hydrocarbon radical; A is an alkylene radical; R'' is an amine; and the sum of x, y and z is 3.

Description

United States Patent [151 3,692,884 Gaskell [4 Sept. 19, 1972 [54] PHOSPHATE ESTERS OTHER PUBLICATIONS lnvemorl Edwin Gflske||, 956 Bfansten Houben-Weyl, Methoden Der Organischen Chemie,
San Carlos, Callf- 94070 Band XII/2 (1964) p, 401 and 402. [22] Filed: Feb. 7, 1969 Primary Examiner-Joseph Rebold PP No.1 797,691 Assistant ExaminerRichard L. Raymond Attomey-Townsend and Townsend [52] US. Cl ..260/944, 117/235, 260/290 R,
260/247, 260/268 R, 260/925, 260/950, ABSTRACT 260/951, 260/980, 260/984, 260/987 A novel group of compounds, the reaction product of 51 11 C1,. ..c07r 9/08, C07f 9/22 an amine and a phosphate ester that are useful as [58] 0 Search 260,925 dispersing agents for the finely divided metal oxides I used in preparing magnetic tape coatings. The com- References Cited pound having the formula:
' UNITED STATES PATENTS mm) 0] K m 2,853,471 9/1958 Beadell ..260/925 X 2,904,416 9/1959 Clarke et a1. ..260/925 X where R is a hydrocarbon di l; A is an alkylene 3,326,919 6/1967 walfeman et x radical; R is an amine; and the sum ofx, y and z is 3. 3,422,166 1/1969 Davis ..260/924 3,346,670 10/ 1965 Papalos ..260/944 X 11 Claims, N0 Drawings PHOSPHATE ESTERS The use of a moving magnetic wire as a means for reproducing audio signals was first demonstrated in 1898. However, it is only since the late 1940's that theories, techniques, and materials have been developed which make possible the reproduction of audio signals with a satisfactory performance from the standpoint of frequency range, signal-tomoise ratio, and distortion. Although satisfactory performances have heretofore been obtained with magnetic wire, magnetic tape consisting of a paper or plastic-base tape coated with a thin layer of magnetized ferromagnetic powder such as iron oxide, is now almost universally used in magnetic sound-reproduction.
Such oxide coated tapes are generally employed in widths such as one-quarter or one-half inch and utilized in rolls of up to about 2,500 feet. Information is recorded on a series of parallel tracks extending the length of the tape. As this type of equipment has become more sophisticated, the characteristics of the oxide coating have become more critical. Thus, an accurate dispersion of the metal oxide in the coating is now essential to uniformity of reproduction. Various dispersing agents have heretofore been employed to assist in providing such a uniform iron oxide coating over the base tape; see for example US. Pat. No. 3,144,352 where surfactants such as lecithin have been utilized for this purpose.
The present invention is directed to a novel group of amine salts of complex phosphate esters that have been found to be particularly advantageous when employed for dispersing finely divided ferromagnetic oxide particles, such as acicular gamma ferric oxide, in tape-coating systems. These novel compounds are broadly described by the following formula:
lR( )n0]Xi [0H]y[R']. (1
wherein x and z are integers from 1 to 2, y is an integer of 0 to l and the sum of x, y and z is always 3; R is a hydrocarbon radical of up to 30 carbons that is selected from aliphatic, cyclic, aromatic and combinations thereof; n is an integer from 3 to 25; A is an alkylene radical of from two to three carbon atoms; R is a monovalent radical of from 0-20 carbons (preferably 0-12 carbons) selected from aliphatic amines of the formula -NH(A'NH),,,H and monocyclic heterocyclic compounds containing from one to three nitrogen atoms and from zero to one oxygen atoms as the only annular hetero atoms. The term aliphatic amines is intended to include alkylene polyamines such as triethylene tetraamine, diethylene triamine as well as ammonia. The term heterocyclic compounds is intended to include morpholine, piperazine, pyridine, triazine, pyrrole, pyrrolidine, and the like with and without substituents.
IN the preferred embodiment the phosphate esters are of the formula:
0 [R 0A ..0],i [om mmA mnmn (la) wherein R is an alkylaromatic radical of from to 20 carbons such as octylor nonylphenyl; A and A are ethylene radicals; m is an integer of from 2 to 3; n is an integer of from 6 to 15, more preferably an average of 8 to 10; and y is O and x and 2 total 3. Depending upon the extent of the reaction, any combination of up to a total of three alkoxy and/or amino groups may be attached to the pentavalent phosphorous atom, it being understood of course that at least one alkoxy and at least one amino radical are always present in the resulting composition.
The novel products of this invention are produced by a carefully controlled two-step process wherein a long chain organic alcohol such as alkylphenoxypoly(alkyleneoxy)alkanol is first reacted (esterified) with, preferably, phosphorous pentoxide to form at least a partial phosphate ester. Thereafter, the resulting monoor diphosphate ester is reacted with the abovedescribed amine either through partial neutralization, or displacement of the ester by the amine.
Briefly, in the 2-step reaction of this invention, a pentavalent phosphorous such as phosphorous pentoxide (P 0 the acid anhydride of phosphoric acid, or phosphorous oxychloride, in an amount in excess of that theoretically required, is combined with a high molecular weight nonionic surface active agent having the general formula:
R OH 2) wherein R, A, and n have the definitions set forth for formula (1), above. The excess of pentavalent phosphorous is necessary to ensure that no free surface active agent remains.
The product obtained from this esterification reaction is thought to be primarily a mixture of the monoand di-ester. The excess of pentavalent phosphorous ensures that little, if any, tri-ester will be formed. Thus the resulting compounds appear to be defined by the formula:
wherein R, A, x and n have the definitions set forth with respect to formula l supra.
Thereafter, and following the removal of the excess pentavalent phosphorous, such as by filtering, the phosphate ester of formula (3) is reacted with an amine having at least one nitrogen and including from O to 20 carbon atoms. As previously discussed with respect to formula l) and la), the amine can be either aliphatic or heterocyclic. Sufficient of the amine is introduced to adjust the pH of the resulting amine salt to about 5 to 7. In the preferred embodiment, the amine is aliphatic and an alkylene polyamine defined by the following formula:
HNH(A' NH),,,H 4 wherein A and m have the definitions set forth for formulas l) and (la), above.
The nonionic surface-active alcohols useful for reaction with the acid anhydride of phosphoric acid include the ethylene oxide adducts of the alkanols and alkylphenols. Such substances are commercially available under trademarks such as Neodol, from Shell Oil Company and Igepal, from General Analine and Film Corporation. For purposes of convenience, reference will frequently be made in the remainder of this specification to the use of Igepal CO-630, a nonylphenoxypoly(ethyleneoxy)ethanol, as the surface active alcohol. However other long chain alkylphenoxylpoly(alkyleneoxy)alkanols such as Igepal CO-430, Igepal CA- 630 and the like, as well as alkylpoly(alkyleneoxy)-alkanols containing up to about 25 alkyleneoxy units, are suitable.
Although the reaction conditions during formation of the phosphate esters in the initial step are not particularly critical, it has been found to be critical for the amount of amine employed to be sufficient to adjust the pH of the resulting complex salt to the range of about 5-7, and preferably 5-6. When the pH of the resulting amine salt is substantially in excess of about 6, the reactants become solid and hard to handle when introduced into the ferromagnetic oxide coating composition. Furthermore, a pH lower than about 5 inhibits subsequent dispersion of the metal oxide in the coating system. During formation of the novel compounds of this invention, the temperature conditions may vary over a wide range, but it is desirable that the reaction temperature at no time greatly exceed the boiling point of water at atmospheric pressure. The reaction pressure employed can be either sub-atmospheric or superatmospheric, in addition to ambient.
The novel dispersing agents of this invention can be incorporated with any of the iron oxide-containing systems presently employed in the magnetic tape production industry. Such systems have heretofore been prepared with iron oxide as well as various other components normally incorporated in the binder system, including resin materials, lubricants, and solvents, such as set forth in U.S. Pat. No. 3,144,352, supra. For this reason, the present invention is not intended to be limited to any particular metal oxide system, but is useful whenever uniform dispersion of the metal oxide is desirable. The .amount of dispersing agent employed can vary widely, as little as about 1 percent by weight being suitable, while amounts up to percent can be advantageous. It is preferable to use from about 2-5 percent based on the total weight of the coating composition.
The resulting coating incorporating the novel dispersing agent of this invention can be employed with a wide variety of known tape bases. However, it will be appreciated by those skilled in the art that tapes formed of polyesters such as polyethylene terephthalate, and available under the trade name Mylar, are particularly suitable as they have an extremely long life.
The organophosphorous compounds, resulting from the reaction of the long chain alcohol with the pentavalent phosphorous oxides, depend upon both the extent to which the esterification reaction is allowed to continue and the relative concentration of the reactants. Subsequently, the amount of amine displacement (or neutralization) will again depend upon the amount of reactants present as well as upon the actual reaction conditions. As previously set forth it is only critical that at least one alkoxy and one amino radical remain complexed with each pentavalent phosphorous. Suitable solvents include toluene and tetrahydrofuran among the many others that could be utilized.
To further illustrate the invention, the following examples are provided. It should be understood that the particular details of the examples are not to be regarded as limitations as they may be varied, as will be understood by one skilled in this art.
EXAMPLE l lgepal C0-630, a nonylphenoxypoly(ethyleneoxy)ethanol, in an amount of about 1,000 grams was heated with agitation to about F. Phosphorous pentoxide in an amount of about 96 grams was slowly added while the reaction temperature was allowed to rise to about 180 F. The phosphorous pentoxide was added at a rate sufficient to maintain the temperature in the range of to 190 F during the addition which took about 1 hour. The rate of addition was decreased as the reaction neared completion. The reaction temperature was retained at about F for about 1 hour after the addition of the phosphorous pentoxide. Some phosphorous pentoxide remained unreacted in the clear liquid portion. The resulting ester was filtered through diatomaceous earth. Other filters having a 50-75 micron porosity are also suitable for this filtering operation. Care was taken to dispose of the filtering medium as the free phosphorous pentoxide presented a fire hazard.
500 grams of the resulting phosphate ester were combined with 550 grams of toluene and heated to approximately 200 F. Triethylene tetraamine, in an amount of 50 grams was added slowly to avoid raising the temperature of the reaction to above 225 F. The resulting amine salt of the complex phosphate ester was filtered and found to have the following characteristics: The viscosity was found to be about 100-200 centapoise and the composition had a weight of about 8.2 pounds per gallon. The acid number was found to be in the range of 50-60 and the pH of a 1 percent aqueous solution of the complex ester was found to be between about 5 and 7.
EXAMPLE ll Utilizing 30 parts of the complex ester formed in example l, above, in lieu of 30 parts of lecithin, the coating composition set forth in example I of US. Pat. No. 3,144,352 is prepared. The coating is applied to a Mylar tape, and the dispersion characteristics of the iron oxide in the coating are found to be excellent.
Although the foregoing invention has been described in some detail by way of illustration and example for purposes of clarity of understanding, it will be appreciated that certain changes and modifications may be practiced within the scope of the invention as limited only by the scope of the appended claims.
What is claimed is:
l. A composition of matter having the following for mula:
wherein at and z are whole number integers of from 1 to 2, y is a whole number integer of from 0 to l, with the proviso that the sum of x, y and z is 3;
R is a hydrocarbon radical of up to 30 carbon atoms,
which is aliphatic, alicyclic, aromatic or combinations thereof;
n is an integer of from 3 to 35;
A is an alkylene radical of from two to three carbon atoms;
R is a monovalent radical of the formula:
3 ,692,884 5 6 NH(A'NH),,,H, radicals.
wherein A is an alkylene radical of from two to three A commsmon according to clam where"! m ls carbon atoms; and 3, isA about IOand R is no ylphenall 5 h m is a whole number integer of from to 5. composltlon accor mg to c aim w erem m 2. A composition according to claim 1 wherein A iiabout lo.a.ndRis z i g 5 h and are ethylene m is n is 645 and R is an composition accor mg to c aim w erem m IS alkyl radical of from to carbons. n about 1 R y p y 3. A composition according to claim 1, wherein m is composmon aicordmg to claim 5, Where"! IS 2, n is about 4 and R is dodecyl. 0, 18 about 10 a R 18 y y 4. A composition according to claim 1, wherein m is l0 10. A composition according to claim 5, wherein m [S 3, n is about 8 and R is pentadecyl. an integer of l". 2 to 5. A composition according to claim 1, wherein R is A composltlon accordmg to clam where! m IS an alkylaromatic radical of from 10 to 20 carbons, n is an integer of from 6-15, and A and A are ethylene 5

Claims (10)

  1. 2. A composition according to claim 1 wherein A and A'' are ethylene, m is 0-3, n is 6-15 and R is an alkyl radical of from 10 to 20 carbons.
  2. 3. A composition according to claim 1, wherein m is 2, n is about 4 and R is dodecyl.
  3. 4. A composition according to claim 1, wherein m is 3, n is about 8 and R is pentadecyl.
  4. 5. A composition according to claim 1, wherein R is an alkylaromatic radical of from 10 to 20 carbons, n is an integer of from 6-15, and A and A'' are ethylene radicals.
  5. 6. A composition according to claim 5, wherein m is 3, n is about 10 and R is nonylphenyl.
  6. 7. A composition according to claim 5, wherein m is 2, n is about 10 and R is nonylphenyl.
  7. 8. A composition according to claim 5, wherein m is 3, n is about 11 and R is octylphenyl.
  8. 9. A composition according to claim 5, wherein m is 0, n is about 10 and R is nonylphenyl.
  9. 10. A composition according to claim 5, wherein m is an integer of from 2 to 3.
  10. 11. A composition according to claim 5, wherein m is 0.
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JPS5040103A (en) * 1973-08-16 1975-04-12
JPS5092103A (en) * 1973-12-14 1975-07-23
US4018968A (en) * 1973-10-05 1977-04-19 Basf Aktiengesellschaft Coated magnetic recording media
US4018967A (en) * 1973-10-05 1977-04-19 Basf Aktiengesellschaft Magnetic recording tape
FR2374945A1 (en) * 1976-12-21 1978-07-21 Philips Nv MAGNETIC RECORDING ELEMENT CONTAINING LIKE A DISPERSANT A SALT OF AN AMINE AND OF AN OLEFINIC ESTER OF PHOSPHORIC ACID
EP0197608A1 (en) * 1985-04-11 1986-10-15 PD Magnetics B.V. Magnetic recording element
US20080257553A1 (en) * 2005-12-09 2008-10-23 Clearwater International, Llc Aggregating reagents, modified particulate metal-oxides and proppants
US10434493B2 (en) 2015-12-18 2019-10-08 3M Innovative Properties Company Metal-containing sorbents for nitrogen-containing compounds
US10597564B2 (en) 2015-12-22 2020-03-24 3M Innovative Properties Company Internally incorporated phenolic resins in water-based (meth)acrylate adhesive compositions, pre-adhesive reaction mixtures, methods, and articles
US10759980B1 (en) 2015-12-22 2020-09-01 3M Innovative Properties Company Packaged pre-adhesive composition including a polylactic acid-containing packaging material, adhesives, and articles

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US2904416A (en) * 1957-10-30 1959-09-15 Exxon Research Engineering Co Petroleum distillate fuels
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US2904416A (en) * 1957-10-30 1959-09-15 Exxon Research Engineering Co Petroleum distillate fuels
US3346670A (en) * 1962-12-11 1967-10-10 Gen Aniline & Film Corp Method for the preparation of phosphate esters
US3326919A (en) * 1963-07-29 1967-06-20 Millmaster Onyx Corp Quaternary ammonium salts of phosphoric acid esters
US3422166A (en) * 1964-03-20 1969-01-14 Mobil Oil Corp Triethanolamine salts of mono- and dinonyl phenol (ethoxylate) phosphate acid esters

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Houben-Weyl, Methoden Der Organischen Chemie, Band XII/2 (1964) p. 401 and 402. *

Cited By (15)

* Cited by examiner, † Cited by third party
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JPS5040103A (en) * 1973-08-16 1975-04-12
US4018968A (en) * 1973-10-05 1977-04-19 Basf Aktiengesellschaft Coated magnetic recording media
US4018967A (en) * 1973-10-05 1977-04-19 Basf Aktiengesellschaft Magnetic recording tape
JPS5092103A (en) * 1973-12-14 1975-07-23
FR2374945A1 (en) * 1976-12-21 1978-07-21 Philips Nv MAGNETIC RECORDING ELEMENT CONTAINING LIKE A DISPERSANT A SALT OF AN AMINE AND OF AN OLEFINIC ESTER OF PHOSPHORIC ACID
US4197357A (en) * 1976-12-21 1980-04-08 U.S. Philips Corporation Magnetic recording element in which a salt of an amine and a phosphoric acid ester are used as a dispersion agent
EP0197608A1 (en) * 1985-04-11 1986-10-15 PD Magnetics B.V. Magnetic recording element
US20080257553A1 (en) * 2005-12-09 2008-10-23 Clearwater International, Llc Aggregating reagents, modified particulate metal-oxides and proppants
US7956017B2 (en) * 2005-12-09 2011-06-07 Clearwater International, Llc Aggregating reagents, modified particulate metal-oxides and proppants
GB2433067B (en) * 2005-12-09 2011-09-21 Clearwater Int Llc Aggregating reagants,modified particulate metal-oxides, and methods for making and using same
AU2006203050B2 (en) * 2005-12-09 2012-06-21 The Lubrizol Corporation Aggregating Reagents, Modified Particulate Metal-Oxides, and Methods for Making and Using Same
US10434493B2 (en) 2015-12-18 2019-10-08 3M Innovative Properties Company Metal-containing sorbents for nitrogen-containing compounds
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