US3309312A - Stabilization of silicone fluids - Google Patents
Stabilization of silicone fluids Download PDFInfo
- Publication number
- US3309312A US3309312A US472010A US47201065A US3309312A US 3309312 A US3309312 A US 3309312A US 472010 A US472010 A US 472010A US 47201065 A US47201065 A US 47201065A US 3309312 A US3309312 A US 3309312A
- Authority
- US
- United States
- Prior art keywords
- iron
- alkyl
- fluids
- silicone
- aryl
- 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 - Lifetime
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- 239000012530 fluid Substances 0.000 title claims description 54
- 229920001296 polysiloxane Polymers 0.000 title claims description 38
- 230000006641 stabilisation Effects 0.000 title description 4
- 238000011105 stabilization Methods 0.000 title description 4
- 239000000203 mixture Substances 0.000 claims description 30
- -1 POLYSILOXANE Polymers 0.000 claims description 28
- 125000000217 alkyl group Chemical group 0.000 description 20
- 125000003118 aryl group Chemical group 0.000 description 16
- XEEYBQQBJWHFJM-UHFFFAOYSA-N iron Substances [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 13
- 229910052742 iron Inorganic materials 0.000 description 11
- 150000002506 iron compounds Chemical class 0.000 description 10
- KXDHJXZQYSOELW-UHFFFAOYSA-N Carbamic acid Chemical class NC(O)=O KXDHJXZQYSOELW-UHFFFAOYSA-N 0.000 description 8
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 8
- UQSXHKLRYXJYBZ-UHFFFAOYSA-N Iron oxide Chemical compound [Fe]=O UQSXHKLRYXJYBZ-UHFFFAOYSA-N 0.000 description 8
- RWZYAGGXGHYGMB-UHFFFAOYSA-N anthranilic acid Chemical compound NC1=CC=CC=C1C(O)=O RWZYAGGXGHYGMB-UHFFFAOYSA-N 0.000 description 8
- 125000004432 carbon atom Chemical group C* 0.000 description 8
- 239000002253 acid Substances 0.000 description 7
- 235000008206 alpha-amino acids Nutrition 0.000 description 7
- 239000000499 gel Substances 0.000 description 7
- 239000000654 additive Substances 0.000 description 6
- 150000001370 alpha-amino acid derivatives Chemical class 0.000 description 6
- 150000005840 aryl radicals Chemical group 0.000 description 6
- 125000000753 cycloalkyl group Chemical group 0.000 description 6
- 239000000314 lubricant Substances 0.000 description 6
- 150000007513 acids Chemical class 0.000 description 5
- 125000002877 alkyl aryl group Chemical group 0.000 description 5
- 239000004471 Glycine Substances 0.000 description 4
- 125000003710 aryl alkyl group Chemical group 0.000 description 4
- 229910052736 halogen Inorganic materials 0.000 description 4
- 150000002367 halogens Chemical group 0.000 description 4
- 230000000996 additive effect Effects 0.000 description 3
- 125000001931 aliphatic group Chemical group 0.000 description 3
- 150000002505 iron Chemical class 0.000 description 3
- 159000000014 iron salts Chemical class 0.000 description 3
- 239000003921 oil Substances 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- 239000003381 stabilizer Substances 0.000 description 3
- 238000012360 testing method Methods 0.000 description 3
- 239000002562 thickening agent Substances 0.000 description 3
- 235000001014 amino acid Nutrition 0.000 description 2
- 150000001413 amino acids Chemical class 0.000 description 2
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 2
- 150000001735 carboxylic acids Chemical class 0.000 description 2
- 125000005843 halogen group Chemical group 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 150000007524 organic acids Chemical class 0.000 description 2
- 235000005985 organic acids Nutrition 0.000 description 2
- 125000003944 tolyl group Chemical group 0.000 description 2
- MTCFGRXMJLQNBG-REOHCLBHSA-N (2S)-2-Amino-3-hydroxypropansäure Chemical compound OC[C@H](N)C(O)=O MTCFGRXMJLQNBG-REOHCLBHSA-N 0.000 description 1
- 125000002030 1,2-phenylene group Chemical group [H]C1=C([H])C([*:1])=C([*:2])C([H])=C1[H] 0.000 description 1
- RZVAJINKPMORJF-UHFFFAOYSA-N Acetaminophen Chemical compound CC(=O)NC1=CC=C(O)C=C1 RZVAJINKPMORJF-UHFFFAOYSA-N 0.000 description 1
- 229910014033 C-OH Inorganic materials 0.000 description 1
- 229910014570 C—OH Inorganic materials 0.000 description 1
- 239000004129 EU approved improving agent Substances 0.000 description 1
- XUJNEKJLAYXESH-REOHCLBHSA-N L-Cysteine Chemical compound SC[C@H](N)C(O)=O XUJNEKJLAYXESH-REOHCLBHSA-N 0.000 description 1
- QNAYBMKLOCPYGJ-REOHCLBHSA-N L-alanine Chemical compound C[C@H](N)C(O)=O QNAYBMKLOCPYGJ-REOHCLBHSA-N 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- MTCFGRXMJLQNBG-UHFFFAOYSA-N Serine Natural products OCC(N)C(O)=O MTCFGRXMJLQNBG-UHFFFAOYSA-N 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 235000004279 alanine Nutrition 0.000 description 1
- 125000003545 alkoxy group Chemical class 0.000 description 1
- 150000001371 alpha-amino acids Chemical class 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- MASBWURJQFFLOO-UHFFFAOYSA-N ammeline Chemical compound NC1=NC(N)=NC(O)=N1 MASBWURJQFFLOO-UHFFFAOYSA-N 0.000 description 1
- 159000000032 aromatic acids Chemical class 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 150000003851 azoles Chemical class 0.000 description 1
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid group Chemical group C(C1=CC=CC=C1)(=O)O WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000001055 blue pigment Substances 0.000 description 1
- 235000013877 carbamide Nutrition 0.000 description 1
- 150000007942 carboxylates Chemical group 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 125000004966 cyanoalkyl group Chemical group 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 235000018417 cysteine Nutrition 0.000 description 1
- XUJNEKJLAYXESH-UHFFFAOYSA-N cysteine Natural products SCC(N)C(O)=O XUJNEKJLAYXESH-UHFFFAOYSA-N 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 125000002704 decyl group Chemical group [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])* 0.000 description 1
- 239000003599 detergent Substances 0.000 description 1
- 125000004185 ester group Chemical group 0.000 description 1
- 125000001033 ether group Chemical group 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 230000005484 gravity Effects 0.000 description 1
- 239000004519 grease Substances 0.000 description 1
- 125000003106 haloaryl group Chemical group 0.000 description 1
- 150000008282 halocarbons Chemical group 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 1
- 230000002209 hydrophobic effect Effects 0.000 description 1
- 125000002349 hydroxyamino group Chemical group [H]ON([H])[*] 0.000 description 1
- 150000002460 imidazoles Chemical class 0.000 description 1
- UHOKSCJSTAHBSO-UHFFFAOYSA-N indanthrone blue Chemical compound C1=CC=C2C(=O)C3=CC=C4NC5=C6C(=O)C7=CC=CC=C7C(=O)C6=CC=C5NC4=C3C(=O)C2=C1 UHOKSCJSTAHBSO-UHFFFAOYSA-N 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 description 1
- 230000001050 lubricating effect Effects 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 1
- 239000002480 mineral oil Substances 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Chemical group 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 239000006069 physical mixture Substances 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000005297 pyrex Substances 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 235000004400 serine Nutrition 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000013112 stability test Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 125000000446 sulfanediyl group Chemical group *S* 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- 150000003672 ureas Chemical class 0.000 description 1
- 239000000984 vat dye Substances 0.000 description 1
- 125000005023 xylyl group Chemical group 0.000 description 1
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- C10M2229/04—Siloxanes with specific structure
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Definitions
- Silicone fluids have achieved wide acceptance as lubricants and hydraulic fluids which function effectively under conditions requiring high-temperature stability. At elevated temperatures, for example in the range of about 350 to about 450 F., mineral oils or synthetic lubricants become unduly viscous or even deteriorate during extended use. Silicone fluids have been found to be a satisfactory substitute. More recently, however, with the advent of engines and other machinery operating at relatively higher temperatures than before even these silicones have shown evidence of failure. At temperatures of about 600 F. and above, silicone fluids tend to gel or solidify in so short a time that the useful life of lubricants prepared from these fluids has been undesirably decreased.
- the major object of the present invention is to provide silicone fluids having extended service life at high temperatures.
- a further object is to provide silicone fluids containing iron compounds, having improved high temperature stability.
- silicone fluids may be unexpectedly increased by adding thereto a minor amount of an iron compound and an amino acid which has the formula Ht-NR'C-0ii wherein R may be alkyl, cycloalkyl, aralkyl, aryl, and aikaryl having from 1 to about 20 carbon atoms. R may also have other substituents, namely hydroxy, sulfhydryl, thio and additional amino groups.
- the silicone fluids which are used in the practice of this invention are polysiloxanes having as its repeating unit the formula n L-n/Z wherein n is in the range of from about 1.1 to about 2.9 and R is an alkyl or aryl radical, which terms cover cycloalkyl, alkaryl, and aralkyl radicals. R also includes substituted radicals containing halogen, oxygen and nitrogen atoms attached thereto, such as halogenated hydrocarbon groups, ether groups, carboxylate groups, ester groups, and cyanoalkyl groups. In general, R contains from 1 to about 20 carbon atoms.
- R may be both alkyl and aryl in the same molecule.
- polysiloxane fluids wherein the R group contains (1) alkyl radicals; (2) mixed alkyl and aryl radicals wherein the mol ratio of alkyl to aryl is in the range of from 1 to about 15 to 1; or (3) mixed alkyl, aryl, and haloaryl radicals wherein the mol ratio of alkyl to the total aryl and haloaryl is from 1 to about 15 to 1, and the said haloaryl radicals contain from 1 to 5 halogen atoms each.
- polysiloxanes containing one or more of the R groups of (1), (2) and (3) above in physical mixture are also within the scope of this invention.
- these silicone fluids vary depending upon the method of preparation and the reactants used in their preparation. Broadly, these fluids may possess molecular weights fro-m about 200, and more frequently from about 500, to about 10,000.
- Polysiloxanes of the type used in the present invention are well known to the art. Their preparation and purpose are disclosed in Introduction to the Chemistry of the Siiico-nes, E. G. Rochow, Second Edition (1951) lohn Wiley & Sons, New York, and Organo Silicon as Compounds, C. Eaborne (1960), Academic Trust, New York.
- These polysiloxane fluids contain, as a first additive stabilizer, an iron compound, such as iron oxide, and preferably the iron salts of organic acids.
- the organic acids used to prepare the iron compound stabilizers are carboxylic acids which may be saturated or unsaturated; aliphatic, cycloaliphatic or aromatic acids. Included in this category are acetic, propionic, butyric, 2- ethylhexanoic (octoic), benzoic, toluic, cyclohexanoic, and other iron salts disclosed in US. Patent No. 2,445,- 5 67. Of primary interest in this invention is iron octoate.
- the second additive which provides the increased stabilization of the polysiloxane fluids, as described above, are amino mono-carboxylic acids having the formula wherein R may be an aliphatic or aromatic radical having u to about 20 carbon atoms.
- the most preferred acids are the alpha-amino acids, including the two simplest acids of each R-type: glycine, wherein R is methylene, and anthranilic, wherein R is an o-phenylene.
- Other-suitable acids include those of the hydroxyamino acid class and the sulfur-substituted amino acid class. Acids such as alanine, cysteine, serine and paminobenzoic acid are included in the defined group of acids in this invention.
- the amount of iron compound to be added to the silicone fluids of this invention is in the range of about 0.001% to about 10% by weight. These iron compounds are so effective that as little as about 0.001% to about 0.75% furnish significant results in extending the service life of these fluids.
- amounts ranging from about 0.1% to about 10%, and preferably about 0.5% to about 5%, by weight of the total composition are employed.
- the high temperature stability of the silicone compositions of this invention is measured by subjecting the fluid composition to 600 F. temperature in the presence of air and by determining the time at which the composition gels or commences to turn solid.
- the test procedure is as follows:
- a sample of the silicone fluid composition is added to a Pyrex beaker and is placed in an oven held at 600 F. under forced air circulation. The fluidity of the compositions is checked visually at regular intervals until the sample shows no gravity flow. The time elapsed from the beginning of the test to this point is denoted as the gel time of the sample.
- compositions in these examples may be prepared by any simple mixing means using any desired sequence of addition.
- Example I The silicone fluid used in this example is a methyl phenyl polysiloxane having a methyl to phenol mol ratio of 8:1, a molecular weight of about 3000 and a kinematic viscosity at 210 F. of 20 centistokes.
- To two portions of the silicone fluid were added varying quantities of iron octoate and both iron octoate and glycine in a combined composition.
- the high temperature gel test was applied to the uninhibited silicone fluid and to the two inhibited compositions. The results are tabulated below
- the silicone fluid of Example I was combined with 0.2% by Weight of iron octoate and 1.0% by weight of anthranilic acid.
- the high temperature stability test was applied to these compositions with the following results tabulated in Table II.
- the stabilized silicone compositions of this invention may be employed as lubricants, whether alone or in admixture with petroleum oils or synthetic oils, and as hydraulic fluids in many industrial applications.
- the silicone fluid compositions of this invention may also contain other known additives including detergents, rust inhibitors, viscosity improving agents, and extreme pressure agents.
- These fluids may also be thickened into lubricating greases by the addition of known pigment thickeners.
- perylimids which have the structure wherein R and R may he hydrogen, alkyl, aryl, alkaryl, and halogen derivatives thereof, and may be alike or different.
- Other suitable thickeners are the anthanthrones:
- R and R are the same or different, being halogen, alkyl, aryl, alkoxy, and halogen derivatives thereof.
- azoles naphthalic imidazoles, Milori blues (terrocyanides), indanthrene blue pigment or vat dye, polyaryl ureas, ammeline and hydrophobic clays.
- thickeners may be used together and they may represent about 5% to 75% by weight, and preferably about 15% to 30%, of the total composition.
- the remainder of the grease composition is the silicone and sulfur-containing substance of this invention.
- a high temperature stabilized composition comprising a major proportion of a polysiloxane fluid having the unit formula:
- n has a value from about 1.1 to about 2.9 and R represents an organyl radical selected from the group consisting of alkyl and aromatic radicals and halogenated derivatives thereof R containing from 1 to about 20 carbon atoms and a minor proportion suflicient to stabilize said fluid of (1) an iron compound selected from the group consisting of iron oxide and iron carboxylate salts soluble in said polysiloxane fluid and (2) an amino mono-carboxylic acid.
- a high temperature stabilized fluid composition comprising a major proportion of a polysiloxane fluid having the unit formula:
- n has a value from about 1.1 to about 2.9 and R represents an organyl radical selected from the group consisting of alkyl, cycloalkyl, aralkyl R containing from 1 to about 20 carbon atoms, aryl, and alkaryl, and halogenated derivatives thereof and a minor proportion sumcient to stabilize said fluid of (1) an iron compound selected from the group consisting of iron oxide and an iron 0 salt of a carboxylic acid soluble in said polysiloxane fluid wherein R is selected from the group consisting of alkyl, cycloalkyl, aralkyl, aryl and alkaryl having from 1 to about 20 carbon atoms.
- the high temperature stabilized fluid composition comprising a major proportion of a polysiloxanc fluid having the unit formula:
- n has a value from 1.1 to 2.9 and R is selected from the group consisting of (a) alkyl radicals, (b) mixed alkyl and aryl radicals in a mol ratio of alkyl to aryl of from 1 to about 15, (c) mixed alkyl and halogenated aryl radicals in a mol ratio of alkyl to halogenated aryl of from 1 to about 15 and (d) mixed alkyl, aryl and halog-enated aryl radicals in a mol ratio of alkyl to total aryl and halogenated aryl of from 1 to about 15 said halogenated aryl radicals in all instances containing from 1 to 5 halogen atoms each R containing from 1 to about 20 carbon atoms, and a minor proportion sufficient to stabilize said fluid of (1) from about 0.001% to about 10% by weight of a soluble iron salt of a carboxylic acid selected from the group consisting of aliphatic, cyclo-aliphatic, and
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Description
. 3,309,312 .Qfi
Patented Mar. 14, 1967 3,309,312 STABILIZATION OF SlLlCONE FLUIDS Fritz A. Bnehler, Erlton, N.J., assignor to Mobil Oil Corporation, a corporation of New York No Drawing. Filed Italy 14, 1965, Ser. No. 472,010 12 Claims. (Cl. 252-18) This invention relates to stable fluid compositions and more particularly to silicone fluid compositions capable of withstanding high temperatures.
Silicone fluids have achieved wide acceptance as lubricants and hydraulic fluids which function effectively under conditions requiring high-temperature stability. At elevated temperatures, for example in the range of about 350 to about 450 F., mineral oils or synthetic lubricants become unduly viscous or even deteriorate during extended use. Silicone fluids have been found to be a satisfactory substitute. More recently, however, with the advent of engines and other machinery operating at relatively higher temperatures than before even these silicones have shown evidence of failure. At temperatures of about 600 F. and above, silicone fluids tend to gel or solidify in so short a time that the useful life of lubricants prepared from these fluids has been undesirably decreased.
Hitherto, it has been attempted to improve the service life of silicone-based lubricants and hydraulic fluids by admixing therewith certain additives which prevent or at least delay gel formation. Of these additives, iron compounds, such as iron oxide, iron octoate, and iron salts of other carboxylic acids, as described in US. Patent No. 2,445,567, have been used with some success. Unfortunately, with the ever-increasing demand for functional lubricants and fluids to operate for long periods of time at such extreme temperatures, it has been found that the stabilization obtained from the use of these iron compounds alone is not always sutficient and further improvement in the stability of silicone fluids would be highly desirable.
The major object of the present invention is to provide silicone fluids having extended service life at high temperatures. A further object is to provide silicone fluids containing iron compounds, having improved high temperature stability. These and other objects will become apparent from the following description.
It has now been discovered that the high temperature stability of silicone fluids may be unexpectedly increased by adding thereto a minor amount of an iron compound and an amino acid which has the formula Ht-NR'C-0ii wherein R may be alkyl, cycloalkyl, aralkyl, aryl, and aikaryl having from 1 to about 20 carbon atoms. R may also have other substituents, namely hydroxy, sulfhydryl, thio and additional amino groups.
The silicone fluids which are used in the practice of this invention are polysiloxanes having as its repeating unit the formula n L-n/Z wherein n is in the range of from about 1.1 to about 2.9 and R is an alkyl or aryl radical, which terms cover cycloalkyl, alkaryl, and aralkyl radicals. R also includes substituted radicals containing halogen, oxygen and nitrogen atoms attached thereto, such as halogenated hydrocarbon groups, ether groups, carboxylate groups, ester groups, and cyanoalkyl groups. In general, R contains from 1 to about 20 carbon atoms. Included in the above definition are methyl, propyl, pentyl, hexyl, decyl, and the like as examples of alkyl groups; cyclo-hexyl, cyciopentyl and the like as examples of cycloalkyl groups; and phenyl, naphthyl, benzyl, tolyl, xylyl and the like as examples of the various aromatic groups. Also included are mixed groups in which R may be both alkyl and aryl in the same molecule. Of special interest in this invention are polysiloxane fluids wherein the R group contains (1) alkyl radicals; (2) mixed alkyl and aryl radicals wherein the mol ratio of alkyl to aryl is in the range of from 1 to about 15 to 1; or (3) mixed alkyl, aryl, and haloaryl radicals wherein the mol ratio of alkyl to the total aryl and haloaryl is from 1 to about 15 to 1, and the said haloaryl radicals contain from 1 to 5 halogen atoms each. Instead of the above groups being mixed in the same molecule, polysiloxanes containing one or more of the R groups of (1), (2) and (3) above in physical mixture are also within the scope of this invention.
The molecular weights of these silicone fluids vary depending upon the method of preparation and the reactants used in their preparation. Broadly, these fluids may possess molecular weights fro-m about 200, and more frequently from about 500, to about 10,000.
Polysiloxanes of the type used in the present invention are well known to the art. Their preparation and purpose are disclosed in Introduction to the Chemistry of the Siiico-nes, E. G. Rochow, Second Edition (1951) lohn Wiley & Sons, New York, and Organo Silicon as Compounds, C. Eaborne (1960), Academic Trust, New York.
These polysiloxane fluids (also termed silicone fluids for the purpose of this invention), contain, as a first additive stabilizer, an iron compound, such as iron oxide, and preferably the iron salts of organic acids. The organic acids used to prepare the iron compound stabilizers are carboxylic acids which may be saturated or unsaturated; aliphatic, cycloaliphatic or aromatic acids. Included in this category are acetic, propionic, butyric, 2- ethylhexanoic (octoic), benzoic, toluic, cyclohexanoic, and other iron salts disclosed in US. Patent No. 2,445,- 5 67. Of primary interest in this invention is iron octoate.
The second additive which provides the increased stabilization of the polysiloxane fluids, as described above, are amino mono-carboxylic acids having the formula wherein R may be an aliphatic or aromatic radical having u to about 20 carbon atoms. The most preferred acids are the alpha-amino acids, including the two simplest acids of each R-type: glycine, wherein R is methylene, and anthranilic, wherein R is an o-phenylene. Other-suitable acids include those of the hydroxyamino acid class and the sulfur-substituted amino acid class. Acids such as alanine, cysteine, serine and paminobenzoic acid are included in the defined group of acids in this invention.
The amount of iron compound to be added to the silicone fluids of this invention is in the range of about 0.001% to about 10% by weight. These iron compounds are so effective that as little as about 0.001% to about 0.75% furnish significant results in extending the service life of these fluids. With regard to the amino mono-carboxylic acid, amounts ranging from about 0.1% to about 10%, and preferably about 0.5% to about 5%, by weight of the total composition are employed.
The following examples are intended to illustrate the instant invention without introducing limitations theretO.
EVALUATION OF SILICONE COMPOSITIONS The high temperature stability of the silicone compositions of this invention is measured by subjecting the fluid composition to 600 F. temperature in the presence of air and by determining the time at which the composition gels or commences to turn solid. The test procedure is as follows:
A sample of the silicone fluid composition is added to a Pyrex beaker and is placed in an oven held at 600 F. under forced air circulation. The fluidity of the compositions is checked visually at regular intervals until the sample shows no gravity flow. The time elapsed from the beginning of the test to this point is denoted as the gel time of the sample.
The compositions in these examples may be prepared by any simple mixing means using any desired sequence of addition.
Example I The silicone fluid used in this example is a methyl phenyl polysiloxane having a methyl to phenol mol ratio of 8:1, a molecular weight of about 3000 and a kinematic viscosity at 210 F. of 20 centistokes. To two portions of the silicone fluid were added varying quantities of iron octoate and both iron octoate and glycine in a combined composition. The high temperature gel test was applied to the uninhibited silicone fluid and to the two inhibited compositions. The results are tabulated below The silicone fluid of Example I was combined with 0.2% by Weight of iron octoate and 1.0% by weight of anthranilic acid. The high temperature stability test was applied to these compositions with the following results tabulated in Table II.
TABLE II Wt. Gel Additive Percent Time,
Hrs.
1. None. 2. Iron Octoate 0.2 550 3. Anthranilic acid/iron octoate 1. 0/0 2 1, 100
It will be noted from the results of the gel test in the above examples that the amino mono-carboxylic acids, when used in combination with iron containing stabilizers are effective in improving the high temperature stability of silicone fluids.
The stabilized silicone compositions of this invention may be employed as lubricants, whether alone or in admixture with petroleum oils or synthetic oils, and as hydraulic fluids in many industrial applications. The silicone fluid compositions of this invention may also contain other known additives including detergents, rust inhibitors, viscosity improving agents, and extreme pressure agents.
These fluids may also be thickened into lubricating greases by the addition of known pigment thickeners. Chief among these are the perylimids which have the structure wherein R and R may he hydrogen, alkyl, aryl, alkaryl, and halogen derivatives thereof, and may be alike or different. Other suitable thickeners are the anthanthrones:
wherein R and R are the same or different, being halogen, alkyl, aryl, alkoxy, and halogen derivatives thereof. Also suitable are azoles, naphthalic imidazoles, Milori blues (terrocyanides), indanthrene blue pigment or vat dye, polyaryl ureas, ammeline and hydrophobic clays. One or several of these thickeners may be used together and they may represent about 5% to 75% by weight, and preferably about 15% to 30%, of the total composition. The remainder of the grease composition is the silicone and sulfur-containing substance of this invention.
The present invention has been described and illustrated by reference to certain specific examples without intending to limit the invention in any way thereto; and modifications may be employed without departing from the scope of this invention thereby, except as indicated in the following-claims.
I claim:
1. A high temperature stabilized composition comprising a major proportion of a polysiloxane fluid having the unit formula:
wherein n has a value from about 1.1 to about 2.9 and R represents an organyl radical selected from the group consisting of alkyl and aromatic radicals and halogenated derivatives thereof R containing from 1 to about 20 carbon atoms and a minor proportion suflicient to stabilize said fluid of (1) an iron compound selected from the group consisting of iron oxide and iron carboxylate salts soluble in said polysiloxane fluid and (2) an amino mono-carboxylic acid.
2. A high temperature stabilized fluid composition comprising a major proportion of a polysiloxane fluid having the unit formula:
wherein n has a value from about 1.1 to about 2.9 and R represents an organyl radical selected from the group consisting of alkyl, cycloalkyl, aralkyl R containing from 1 to about 20 carbon atoms, aryl, and alkaryl, and halogenated derivatives thereof and a minor proportion sumcient to stabilize said fluid of (1) an iron compound selected from the group consisting of iron oxide and an iron 0 salt of a carboxylic acid soluble in said polysiloxane fluid wherein R is selected from the group consisting of alkyl, cycloalkyl, aralkyl, aryl and alkaryl having from 1 to about 20 carbon atoms.
3. The fluid composition of claim 2 wherein the aminomonocarboxylic acid is an alpha-amino acid.
4. The fluid composition of claim 3 wherein the alphaamino acid is glycine.
5. The fluid composition of claim 3 wherein the alphaamino acid is anthranilic acid.
6. The high temperature stabilized fluid composition comprising a major proportion of a polysiloxanc fluid having the unit formula:
wherein n has a value from 1.1 to 2.9 and R is selected from the group consisting of (a) alkyl radicals, (b) mixed alkyl and aryl radicals in a mol ratio of alkyl to aryl of from 1 to about 15, (c) mixed alkyl and halogenated aryl radicals in a mol ratio of alkyl to halogenated aryl of from 1 to about 15 and (d) mixed alkyl, aryl and halog-enated aryl radicals in a mol ratio of alkyl to total aryl and halogenated aryl of from 1 to about 15 said halogenated aryl radicals in all instances containing from 1 to 5 halogen atoms each R containing from 1 to about 20 carbon atoms, and a minor proportion sufficient to stabilize said fluid of (1) from about 0.001% to about 10% by weight of a soluble iron salt of a carboxylic acid selected from the group consisting of aliphatic, cyclo-aliphatic, and aromatic carboxylic acids and (2) from about 0.1% to about 10% by weight of an amino mono-carboxylic acid having a formula II HrN-IV-C-OH wherein R is selected from the group consisting of alkyl, cycloalkyl, aralkyl, aryl and alkaryl having from 1 to about 20 carbon atoms.
7. The fluid composition of claim 6 wherein from about 0.001% to about 0.75% by weight of said iron salt is present.
8. The fluid composition of claim 6 wherein from about 0.5 to about 5% by weight of the said amino mono-carboxylic acid is present.
9. The fluid composition of claim 6 wherein the iron salt is iron octoate.
10. The fluid composition of claim 6 wherein the amino mono-carboxylic acid is an alpha-amino acid.
11. The fluid composition of claim 10 wherein the alpha-amino acid is glycine.
12. The fluid composition of claim 10 wherein the alpha-amino acid is anthranilic acid.
References Cited by the Examiner UNITED STATES PATENTS DANIEL E. WY MAN, Primary Examiner.
C. F. DEES, Assistant Examiner.
Claims (1)
1. A HIGH TEMPERATURE STABILIZED COMPOSITION COMPRISING A MAJOR PORTION OF A POLYSILOXANE FLUID HAVING THE UNIT FORMULA:
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US472010A US3309312A (en) | 1965-07-14 | 1965-07-14 | Stabilization of silicone fluids |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US472010A US3309312A (en) | 1965-07-14 | 1965-07-14 | Stabilization of silicone fluids |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US3309312A true US3309312A (en) | 1967-03-14 |
Family
ID=23873852
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US472010A Expired - Lifetime US3309312A (en) | 1965-07-14 | 1965-07-14 | Stabilization of silicone fluids |
Country Status (1)
| Country | Link |
|---|---|
| US (1) | US3309312A (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3518189A (en) * | 1968-01-03 | 1970-06-30 | Us Air Force | Grease composition for use at high temperatures and high speeds |
| US5932650A (en) * | 1996-01-26 | 1999-08-03 | General Electric Company | One component room temperature vulcanizable (RTV) silicone sealant with improved high temperature adhesion |
Citations (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2340438A (en) * | 1942-02-06 | 1944-02-01 | Texas Co | Oxidation-stable grease composition |
| US2369090A (en) * | 1941-12-17 | 1945-02-06 | Gulf Research Development Co | Insulating oil compositions |
| US2445567A (en) * | 1948-07-20 | Stabilizing organo-substituted | ||
| US2945838A (en) * | 1960-07-19 | Amide stabilized organopolysiloxane | ||
| US3009877A (en) * | 1959-12-17 | 1961-11-21 | Gen Electric | Stabilized lubricant composition |
| US3108962A (en) * | 1961-04-20 | 1963-10-29 | Socony Mobil Oil Co Inc | Grease |
| US3146201A (en) * | 1960-07-22 | 1964-08-25 | Lubrizol Corp | Lubricant composition |
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1965
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Patent Citations (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2445567A (en) * | 1948-07-20 | Stabilizing organo-substituted | ||
| US2945838A (en) * | 1960-07-19 | Amide stabilized organopolysiloxane | ||
| US2369090A (en) * | 1941-12-17 | 1945-02-06 | Gulf Research Development Co | Insulating oil compositions |
| US2340438A (en) * | 1942-02-06 | 1944-02-01 | Texas Co | Oxidation-stable grease composition |
| US3009877A (en) * | 1959-12-17 | 1961-11-21 | Gen Electric | Stabilized lubricant composition |
| US3146201A (en) * | 1960-07-22 | 1964-08-25 | Lubrizol Corp | Lubricant composition |
| US3108962A (en) * | 1961-04-20 | 1963-10-29 | Socony Mobil Oil Co Inc | Grease |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3518189A (en) * | 1968-01-03 | 1970-06-30 | Us Air Force | Grease composition for use at high temperatures and high speeds |
| US5932650A (en) * | 1996-01-26 | 1999-08-03 | General Electric Company | One component room temperature vulcanizable (RTV) silicone sealant with improved high temperature adhesion |
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