US3524751A - Parting compositions - Google Patents
Parting compositions Download PDFInfo
- Publication number
- US3524751A US3524751A US644082A US3524751DA US3524751A US 3524751 A US3524751 A US 3524751A US 644082 A US644082 A US 644082A US 3524751D A US3524751D A US 3524751DA US 3524751 A US3524751 A US 3524751A
- Authority
- US
- United States
- Prior art keywords
- weight
- castor oil
- lower alkyl
- parting
- composition
- 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
Links
- 239000000203 mixture Substances 0.000 title description 22
- 239000004359 castor oil Substances 0.000 description 16
- 235000019438 castor oil Nutrition 0.000 description 16
- ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 description 16
- -1 hydroxy fatty acid Chemical class 0.000 description 14
- 125000005907 alkyl ester group Chemical group 0.000 description 11
- 235000014113 dietary fatty acids Nutrition 0.000 description 11
- 229930195729 fatty acid Natural products 0.000 description 11
- 239000000194 fatty acid Substances 0.000 description 11
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 9
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 7
- 229910052782 aluminium Inorganic materials 0.000 description 7
- 238000000034 method Methods 0.000 description 7
- BEWFIPLBFJGWSR-UHFFFAOYSA-N butyl 12-acetyloxyoctadec-9-enoate Chemical compound CCCCCCC(OC(C)=O)CC=CCCCCCCCC(=O)OCCCC BEWFIPLBFJGWSR-UHFFFAOYSA-N 0.000 description 6
- 239000000463 material Substances 0.000 description 6
- 239000000956 alloy Substances 0.000 description 5
- 229910045601 alloy Inorganic materials 0.000 description 5
- 238000005266 casting Methods 0.000 description 5
- 239000000498 cooling water Substances 0.000 description 5
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- 238000009749 continuous casting Methods 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- 125000004432 carbon atom Chemical group C* 0.000 description 3
- 238000002156 mixing Methods 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
- HGWAKQDTQVDVRP-OKULMJQMSA-N butyl (z,12r)-12-hydroxyoctadec-9-enoate Chemical compound CCCCCC[C@@H](O)C\C=C/CCCCCCCC(=O)OCCCC HGWAKQDTQVDVRP-OKULMJQMSA-N 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- 239000011248 coating agent Substances 0.000 description 2
- 238000000576 coating method Methods 0.000 description 2
- 239000000306 component Substances 0.000 description 2
- 238000011109 contamination Methods 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 239000008240 homogeneous mixture Substances 0.000 description 2
- 239000000314 lubricant Substances 0.000 description 2
- JGHSBPIZNUXPLA-UHFFFAOYSA-N 2-hydroxyhexadecanoic acid Chemical compound CCCCCCCCCCCCCCC(O)C(O)=O JGHSBPIZNUXPLA-UHFFFAOYSA-N 0.000 description 1
- JYZJYKOZGGEXSX-UHFFFAOYSA-N 2-hydroxymyristic acid Chemical compound CCCCCCCCCCCCC(O)C(O)=O JYZJYKOZGGEXSX-UHFFFAOYSA-N 0.000 description 1
- NKASEPJANRVKDD-UHFFFAOYSA-N 2-hydroxypentadecanoic acid Chemical compound CCCCCCCCCCCCCC(O)C(O)=O NKASEPJANRVKDD-UHFFFAOYSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 230000021736 acetylation Effects 0.000 description 1
- 238000006640 acetylation reaction Methods 0.000 description 1
- 125000005233 alkylalcohol group Chemical group 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 235000011187 glycerol Nutrition 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 230000001050 lubricating effect Effects 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- XMHIUKTWLZUKEX-UHFFFAOYSA-N n-hexacosanoic acid Natural products CCCCCCCCCCCCCCCCCCCCCCCCCC(O)=O XMHIUKTWLZUKEX-UHFFFAOYSA-N 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- WBHHMMIMDMUBKC-XLNAKTSKSA-N ricinelaidic acid Chemical compound CCCCCC[C@@H](O)C\C=C\CCCCCCCC(O)=O WBHHMMIMDMUBKC-XLNAKTSKSA-N 0.000 description 1
- 229940066675 ricinoleate Drugs 0.000 description 1
- WBHHMMIMDMUBKC-QJWNTBNXSA-M ricinoleate Chemical compound CCCCCC[C@@H](O)C\C=C/CCCCCCCC([O-])=O WBHHMMIMDMUBKC-QJWNTBNXSA-M 0.000 description 1
- 229960003656 ricinoleic acid Drugs 0.000 description 1
- FEUQNCSVHBHROZ-UHFFFAOYSA-N ricinoleic acid Natural products CCCCCCC(O[Si](C)(C)C)CC=CCCCCCCCC(=O)OC FEUQNCSVHBHROZ-UHFFFAOYSA-N 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 238000005809 transesterification reaction Methods 0.000 description 1
- 239000002966 varnish Substances 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 238000003466 welding Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M1/00—Liquid compositions essentially based on mineral lubricating oils or fatty oils; Their use as lubricants
- C10M1/08—Liquid compositions essentially based on mineral lubricating oils or fatty oils; Their use as lubricants with additives
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
- C10M2207/28—Esters
- C10M2207/281—Esters of (cyclo)aliphatic monocarboxylic acids
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
- C10M2207/28—Esters
- C10M2207/282—Esters of (cyclo)aliphatic oolycarboxylic acids
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
- C10M2207/28—Esters
- C10M2207/283—Esters of polyhydroxy compounds
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
- C10M2207/28—Esters
- C10M2207/286—Esters of polymerised unsaturated acids
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
- C10M2207/40—Fatty vegetable or animal oils
- C10M2207/402—Castor oils
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
- C10N2040/00—Specified use or application for which the lubricating composition is intended
- C10N2040/20—Metal working
Definitions
- castor oil possesses certain properties which has rendered it useful as a mold lubricant and parting agent in the casting of aluminum and its alloys.
- castor oil has been generally satisfactory in its ability to carry relative high loads without rupture of the lubricant film, polymerization has been found to occur leading to the deposit of a varnish-like film on aluminum ingots which results in welding, seizing and galling. This condition is undesirable and has become more pronounced as the aluminum industry shifts over to continuous casting of long billets versus the earlier practice of casting individual ingots.
- parting material is also used to describe a composition which has lubricating properties.
- compositions of this invention has been found highly effective as a parting material in either the batch or continuous casting of aluminum and its alloys.
- the success of the composition is based on the combination of about .20 to 40% by weight of a lower alkyl ester of an acetylated hydroxy fatty acid having eight to twentytwo carbon atoms with about 80 to 60% by weight of a castor oil.
- the preferred composition is one comprising a mixture of about 75% by weight castor oil and about by weight butyl acetyl ricinoleate.
- the lower alkyl ester of an acetylated hydroxy fatty acid used in the composition may be prepared by transesterification of a hydroxy fatty acid having eight to twenty-two carbon atoms with a lower alkyl alcohol, e.g.
- hydroxy fatty acids are ricinoleic acid, l2-hydroxy stearic acid, hydroxy palmitic acid, hydroxy pentadecanoic acid, hydroxy myristic acid, hydroxy cerotic acid, etc.
- the ester interchange is complete, the unreacted alcohol is distilled off, the lower alkyl hydroxy fatty acid is converted to a lower alkyl ester of an acetylated hydroxy fatty acid by reacting it with acetic anhydride.
- the lower alkyl ester of an acetylated hydroxy fatty acid is then combined with a castor oil in the proportions heretofor described by simply blending the two compo nents together at ambient temperature until a homogeneous mixture is obtained.
- EXAMPLE 100 pounds of castor oil is reacted with 46 pounds of n-butanol in the presence 0.4% by weight sulfuric acid. A gentle reflux of these components accomplishes the ester interchange.
- the butyl ricinoleate is converted to butyl acetyl ricinoleate by reacting it with 31 pounds of acetic anhydride per 100 pounds of butyl ricinoleate.
- the unreacted acetic anhydride plus by-product acetic acid are then distilled off to yield butyl acetyl ricinoleate.
- T Wenty-five parts by weight of the butyl acetyl ricinoleate is blended at ambient temperature with seventyfive parts by weight of a castor oil, mixing being continued until a homogeneous mixture is obtained.
- compositions falling within the scope of this invention are prepared in the same manner as described in the above example.
- compositions herein described are outstanding parting materials for molds used in the casting of aluminum and its alloys in that they have a reduced viscosity in comparison to castor oil alone so that application to the mold by conventional techniques is more uniform and formation of a varnish deposit or film is minimixed or eliminated.
- the compositions described herein also possess outstanding heat stability and the acetylation of some of the hydroxyl groups in the composition reduces Water sensitivity so that any material carried into the cooling water during the casting operation is more readily separated from the cooling water than when castor oil is used as the parting material.
- a process of improving the parting properties of a mold for continuous casting of aluminum and its alloys which comprises coating said mold with a composition comprising a mixture of about 60 to 80% by weight of a castor oil and about 40 to 20% by weight of a lower alkyl ester of an acetylated hydroxy fatty acid having eight to twenty-two carbon atoms.
- composition comprises a mixture of about by Weight of a castor oil and about 25% by weight of said lower alkyl ester of an acetylated hydroxy fatty acid.
- a method of improving casting of aluminum and its alloys which comprises coating a mold with a composition comprising a mixture of about 60 to by weight of a castor oil and about 40 to 20% by weight of a lower alkyl ester of an acetylated ricinoleate.
Landscapes
- Chemical & Material Sciences (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Lubricants (AREA)
- Mold Materials And Core Materials (AREA)
Description
United States Patent 3,524,751 PARTING COMPOSITIONS Malcolm Kent Smith, 1083 Sunny View Road, Mountainside, NJ. 07092, and Robert L. Vignolo, 842 Kimball Ave., Westfield, NJ. 07090 No Drawing. Filed June 7, 1967, Ser. No. 644,082 Int. Cl. B29c 1/04; B28b 7/ 36' US. Cl. 117-51 6 Claims ABSTRACT OF THE DISCLOSURE BACKGROUND OF THE INVENTION This invention relates to a composition comprising a mixture of a castor oil and an alkyl ester of an acetylated hydroxy fatty acid.
Brief description of the prior art It is well known that castor oil possesses certain properties which has rendered it useful as a mold lubricant and parting agent in the casting of aluminum and its alloys. Although castor oil has been generally satisfactory in its ability to carry relative high loads without rupture of the lubricant film, polymerization has been found to occur leading to the deposit of a varnish-like film on aluminum ingots which results in welding, seizing and galling. This condition is undesirable and has become more pronounced as the aluminum industry shifts over to continuous casting of long billets versus the earlier practice of casting individual ingots.
Another problem encountered during the continuous casting process is that considerable amount of cooling water is used. Therefore, it is most desirable that if the parting material mixes with the cooling water, it be of a type which separates readily to avoid contamination of discharged water. In this regard castor oil is not completely satisfactory because its separation from the cooling water is not sufficiently rapid to avoid some contamination of discharged water.
It has now been discovered that an outstanding parting composition can be obtained by mixing about 60% to 80% by weight of a castor oil with about 40% to about by weight of a lower alkyl ester of an acetylated hydroxy fatty acid.
In the context of the present invention the expression parting material is also used to describe a composition which has lubricating properties.
DETAILED DESCRIPTION OF THE INVENTION The compositions of this invention has been found highly effective as a parting material in either the batch or continuous casting of aluminum and its alloys. The success of the composition is based on the combination of about .20 to 40% by weight of a lower alkyl ester of an acetylated hydroxy fatty acid having eight to twentytwo carbon atoms with about 80 to 60% by weight of a castor oil. The preferred composition is one comprising a mixture of about 75% by weight castor oil and about by weight butyl acetyl ricinoleate.
The lower alkyl ester of an acetylated hydroxy fatty acid used in the composition may be prepared by transesterification of a hydroxy fatty acid having eight to twenty-two carbon atoms with a lower alkyl alcohol, e.g.
ice
methyl, ethyl, n-butyl, isobutyl and 2-ethyl n-hexyl alcohols, in the presence of sulfuric acid as a catalyst. Illustrative of hydroxy fatty acids are ricinoleic acid, l2-hydroxy stearic acid, hydroxy palmitic acid, hydroxy pentadecanoic acid, hydroxy myristic acid, hydroxy cerotic acid, etc. After the ester interchange is complete, the unreacted alcohol is distilled off, the lower alkyl hydroxy fatty acid is converted to a lower alkyl ester of an acetylated hydroxy fatty acid by reacting it with acetic anhydride.
The lower alkyl ester of an acetylated hydroxy fatty acid is then combined with a castor oil in the proportions heretofor described by simply blending the two compo nents together at ambient temperature until a homogeneous mixture is obtained.
The following example is illustrative of the preparation of the parting composition of this invention.
EXAMPLE 100 pounds of castor oil is reacted with 46 pounds of n-butanol in the presence 0.4% by weight sulfuric acid. A gentle reflux of these components accomplishes the ester interchange. After distilling off unreacted n-butanol and washing out the by-product glycerine, the butyl ricinoleate is converted to butyl acetyl ricinoleate by reacting it with 31 pounds of acetic anhydride per 100 pounds of butyl ricinoleate. The unreacted acetic anhydride plus by-product acetic acid are then distilled off to yield butyl acetyl ricinoleate.
T Wenty-five parts by weight of the butyl acetyl ricinoleate is blended at ambient temperature with seventyfive parts by weight of a castor oil, mixing being continued until a homogeneous mixture is obtained.
Other compositions falling within the scope of this invention are prepared in the same manner as described in the above example.
The compositions herein described are outstanding parting materials for molds used in the casting of aluminum and its alloys in that they have a reduced viscosity in comparison to castor oil alone so that application to the mold by conventional techniques is more uniform and formation of a varnish deposit or film is minimixed or eliminated. In addition, the compositions described herein also possess outstanding heat stability and the acetylation of some of the hydroxyl groups in the composition reduces Water sensitivity so that any material carried into the cooling water during the casting operation is more readily separated from the cooling water than when castor oil is used as the parting material.
It is to be understood that changes and variations may be made without departing from the spirit and scope of the invention as defined in the appended claims.
What is claimed is:
1. A process of improving the parting properties of a mold for continuous casting of aluminum and its alloys which comprises coating said mold with a composition comprising a mixture of about 60 to 80% by weight of a castor oil and about 40 to 20% by weight of a lower alkyl ester of an acetylated hydroxy fatty acid having eight to twenty-two carbon atoms.
2. A process according to claim 1, wherein said lower alkyl ester is a lower alkyl acetyl ricinoleate.
3. A process according to claim *1, wherein said composition comprises a mixture of about by Weight of a castor oil and about 25% by weight of said lower alkyl ester of an acetylated hydroxy fatty acid.
4. A process according to claim 3 wherein said lower alkyl ester is butyl acetyl ricinoleate.
5. A method of improving casting of aluminum and its alloys which comprises coating a mold with a composition comprising a mixture of about 60 to by weight of a castor oil and about 40 to 20% by weight of a lower alkyl ester of an acetylated ricinoleate.
6. A method according to claim 5 wherein the com- DONALD J. ARNOLD, Primary Examiner position comprises about 75% by weight of a castor oil and about 25% by weight of butyl acetyl ricinoleate. HAYES Assistant Examiner References Cited 6 US. C1.X.R. UNITED STATES PATENTS 5 33 24 244; 154 73 2,045,913 6/1936 Hoy et a1 10638-24 XR 2,585,053 2/1952 Smith 106244
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US64408267A | 1967-06-07 | 1967-06-07 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US3524751A true US3524751A (en) | 1970-08-18 |
Family
ID=24583377
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US644082A Expired - Lifetime US3524751A (en) | 1967-06-07 | 1967-06-07 | Parting compositions |
Country Status (1)
| Country | Link |
|---|---|
| US (1) | US3524751A (en) |
Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4522250A (en) * | 1982-12-29 | 1985-06-11 | Aluminum Company Of America | Continuous casting with glycerol trioleate parting composition |
| US4602670A (en) * | 1984-12-06 | 1986-07-29 | Aluminum Company Of America | Lubricating process |
| US4607679A (en) * | 1984-12-06 | 1986-08-26 | Aluminum Company Of America | Providing oligomer moisture barrier in direct chill casting of aluminum-lithium alloy |
| US4628985A (en) * | 1984-12-06 | 1986-12-16 | Aluminum Company Of America | Lithium alloy casting |
| US5100697A (en) * | 1984-05-01 | 1992-03-31 | Castrol A/S | Method for improving the release of a moulded concrete body from the mould |
| US5494502A (en) * | 1994-10-03 | 1996-02-27 | The Chemmark Corporation | Asphalt release agent |
| US20020017629A1 (en) * | 2000-08-02 | 2002-02-14 | Benjamin Mosier | Transesterification composition of fatty acid esters, and uses thereof |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2045913A (en) * | 1933-08-28 | 1936-06-30 | Dow Chemical Co | Casting light metal |
| US2585053A (en) * | 1952-02-12 | Solid esteks and method of making |
-
1967
- 1967-06-07 US US644082A patent/US3524751A/en not_active Expired - Lifetime
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2585053A (en) * | 1952-02-12 | Solid esteks and method of making | ||
| US2045913A (en) * | 1933-08-28 | 1936-06-30 | Dow Chemical Co | Casting light metal |
Cited By (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4522250A (en) * | 1982-12-29 | 1985-06-11 | Aluminum Company Of America | Continuous casting with glycerol trioleate parting composition |
| US5100697A (en) * | 1984-05-01 | 1992-03-31 | Castrol A/S | Method for improving the release of a moulded concrete body from the mould |
| US4602670A (en) * | 1984-12-06 | 1986-07-29 | Aluminum Company Of America | Lubricating process |
| US4607679A (en) * | 1984-12-06 | 1986-08-26 | Aluminum Company Of America | Providing oligomer moisture barrier in direct chill casting of aluminum-lithium alloy |
| US4628985A (en) * | 1984-12-06 | 1986-12-16 | Aluminum Company Of America | Lithium alloy casting |
| US5494502A (en) * | 1994-10-03 | 1996-02-27 | The Chemmark Corporation | Asphalt release agent |
| US20020017629A1 (en) * | 2000-08-02 | 2002-02-14 | Benjamin Mosier | Transesterification composition of fatty acid esters, and uses thereof |
| WO2002010114A3 (en) * | 2000-08-02 | 2002-08-15 | Mj Res & Dev L P Of Which Mjrd | Transesterified fatty esters for lubricant and refrigerant oil system |
| US7252779B2 (en) | 2000-08-02 | 2007-08-07 | Mj Research Limited Partnership | Transesterification composition of fatty acid esters, and uses thereof |
| US20080020956A1 (en) * | 2000-08-02 | 2008-01-24 | M/J Research And Development, Lp. | Transesterification composition of fatty acid esters, and uses thereof |
| US7968504B2 (en) | 2000-08-02 | 2011-06-28 | MJ Research and Development, LP | Transesterification composition of fatty acid esters, and uses thereof |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| AS | Assignment |
Owner name: NL CHEMICALS, INC., A CORP. OF DE., NEW YORK Free format text: ASSIGNMENT OF ASSIGNORS INTEREST;ASSIGNOR:NL INDUSTRIES, INC.;REEL/FRAME:004661/0323 Effective date: 19861118 Owner name: NL CHEMICALS, INC., 1230 AVENUE OF THE AMERICAS, N Free format text: ASSIGNMENT OF ASSIGNORS INTEREST.;ASSIGNOR:NL INDUSTRIES, INC.;REEL/FRAME:004661/0323 Effective date: 19861118 |