EP1747254A1 - Antifreezes and/or coolants - Google Patents
Antifreezes and/or coolantsInfo
- Publication number
- EP1747254A1 EP1747254A1 EP05739037A EP05739037A EP1747254A1 EP 1747254 A1 EP1747254 A1 EP 1747254A1 EP 05739037 A EP05739037 A EP 05739037A EP 05739037 A EP05739037 A EP 05739037A EP 1747254 A1 EP1747254 A1 EP 1747254A1
- Authority
- EP
- European Patent Office
- Prior art keywords
- hydroxypropionic acid
- antifreeze
- coolant
- weight percent
- glycol
- 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.)
- Withdrawn
Links
- 239000002826 coolant Substances 0.000 title claims abstract description 65
- 230000002528 anti-freeze Effects 0.000 title claims abstract description 64
- ALRHLSYJTWAHJZ-UHFFFAOYSA-N 3-hydroxypropionic acid Chemical compound OCCC(O)=O ALRHLSYJTWAHJZ-UHFFFAOYSA-N 0.000 claims abstract description 196
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims abstract description 63
- -1 alkali metal salt Chemical class 0.000 claims abstract description 29
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 claims abstract description 24
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 claims abstract description 23
- 239000000203 mixture Substances 0.000 claims abstract description 22
- 125000005907 alkyl ester group Chemical group 0.000 claims abstract description 16
- 150000003863 ammonium salts Chemical class 0.000 claims abstract description 13
- 229910052783 alkali metal Inorganic materials 0.000 claims abstract description 12
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims abstract description 12
- 125000005210 alkyl ammonium group Chemical group 0.000 claims abstract description 12
- 238000000034 method Methods 0.000 claims description 16
- 239000012736 aqueous medium Substances 0.000 claims description 15
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 9
- 150000004702 methyl esters Chemical class 0.000 claims description 3
- 125000004494 ethyl ester group Chemical group 0.000 claims description 2
- 159000000000 sodium salts Chemical class 0.000 claims description 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 1
- 239000007864 aqueous solution Substances 0.000 abstract description 6
- 239000012457 nonaqueous media Substances 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 description 8
- 239000000463 material Substances 0.000 description 7
- 239000000243 solution Substances 0.000 description 7
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 6
- 238000005260 corrosion Methods 0.000 description 5
- 230000007797 corrosion Effects 0.000 description 5
- 239000012895 dilution Substances 0.000 description 5
- 238000010790 dilution Methods 0.000 description 5
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 5
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 4
- SVTBMSDMJJWYQN-UHFFFAOYSA-N 2-methylpentane-2,4-diol Chemical compound CC(O)CC(C)(C)O SVTBMSDMJJWYQN-UHFFFAOYSA-N 0.000 description 4
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 4
- 239000002253 acid Substances 0.000 description 3
- 239000000654 additive Substances 0.000 description 3
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- 230000008014 freezing Effects 0.000 description 3
- 238000007710 freezing Methods 0.000 description 3
- 150000002334 glycols Chemical class 0.000 description 3
- 239000003112 inhibitor Substances 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 229940058015 1,3-butylene glycol Drugs 0.000 description 2
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 2
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 235000019437 butane-1,3-diol Nutrition 0.000 description 2
- 229910052791 calcium Inorganic materials 0.000 description 2
- 239000011575 calcium Substances 0.000 description 2
- 238000002485 combustion reaction Methods 0.000 description 2
- 229940051250 hexylene glycol Drugs 0.000 description 2
- 229910052700 potassium Inorganic materials 0.000 description 2
- 239000011591 potassium Substances 0.000 description 2
- 229960004063 propylene glycol Drugs 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- DURPTKYDGMDSBL-UHFFFAOYSA-N 1-butoxybutane Chemical class CCCCOCCCC DURPTKYDGMDSBL-UHFFFAOYSA-N 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
- 229910001369 Brass Inorganic materials 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 150000005215 alkyl ethers Chemical class 0.000 description 1
- 150000003851 azoles Chemical class 0.000 description 1
- 239000003139 biocide Substances 0.000 description 1
- 239000010951 brass Substances 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 230000000994 depressogenic effect Effects 0.000 description 1
- SZXQTJUDPRGNJN-UHFFFAOYSA-N dipropylene glycol Chemical compound OCCCOCCCO SZXQTJUDPRGNJN-UHFFFAOYSA-N 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 229910003002 lithium salt Inorganic materials 0.000 description 1
- 159000000002 lithium salts Chemical class 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 159000000003 magnesium salts Chemical class 0.000 description 1
- 239000002609 medium Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 238000005555 metalworking Methods 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 150000002823 nitrates Chemical class 0.000 description 1
- 150000002826 nitrites Chemical class 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- QYHFIVBSNOWOCQ-UHFFFAOYSA-N selenic acid Chemical class O[Se](O)(=O)=O QYHFIVBSNOWOCQ-UHFFFAOYSA-N 0.000 description 1
- 150000004760 silicates Chemical class 0.000 description 1
- 238000002076 thermal analysis method Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K5/00—Heat-transfer, heat-exchange or heat-storage materials, e.g. refrigerants; Materials for the production of heat or cold by chemical reactions other than by combustion
- C09K5/20—Antifreeze additives therefor, e.g. for radiator liquids
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K5/00—Heat-transfer, heat-exchange or heat-storage materials, e.g. refrigerants; Materials for the production of heat or cold by chemical reactions other than by combustion
- C09K5/08—Materials not undergoing a change of physical state when used
- C09K5/10—Liquid materials
Definitions
- the present invention relates to antifreezes and/or coolants.
- BACKGROUND It is well known to use as antifreezes and/or coolants, mixtures of water and a freezing point depressant such as an alkylene glycol and a glycol monoether.
- glycols examples include ethylene glycol, diethylene glycol, propylene glycol, hexylene glycol, and 1,3-butylene glycol.
- Exemplary glycol monoethers that are used include the alkyl ethers of the glycols. Accordingly, it would be desirable to provide other materials for use as antifreezes and/or coolants that would be suitable for use particularly for internal combustion engines.
- the present invention provides a process for using, as an antifreeze and/or coolant, a component selected from 3-hydroxypropionic acid; to C 4 alkyl esters of 3-hydroxypropionic acid; or mixtures thereof.
- the present invention provides a process for using, as an antifreeze and/or coolant, an aqueous or non-aqueous solution comprising a component selected from 3-hydroxypropionic acid; - C alkyl esters of 3-hydroxypropionic acid; certain salts of 3-hydroxypropionic acid; or mixtures thereof.
- the present invention provides antifreezes and/or coolants comprising a glycol and a component selected from 3-hydroxypropionic acid; Ci - C alkyl esters of 3-hydroxypropionic acid; ammonium salts of 3-hydroxypropionic acid; C ⁇ - C 4 alkyl ammonium salts of 3-hydroxypropionic acid; alkali metal salts of 3- hydroxypropionic acid; alkaline earth metal salts of 3-hydroxypropionic acid; or mixtures thereof.
- the glycol-containing antifreezes and/or coolants may be used without dilution (i.e., neat) or they may be diluted with an aqueous or non-aqueous medium, for example, water.
- Antifreezes and/or coolants of the invention are particularly useful for use in internal combustion engines.
- the antifreezes and/or coolants may be useful in reducing the pour points of oils, lubricants, metal working fluids, and the like.
- DETAILED DESCRIPTION in one aspect, provides a process for using, as an antifreeze and/or coolant, a component selected from 3-hydroxypropionic acid; to C alkyl esters of 3-hydroxypro ⁇ ionic acid; or mixtures thereof.
- the present invention provides a process for using, as an antifreeze and/or coolant, an aqueous or non-aqueous solution comprising a component selected from 3-hydroxypropionic acid; - C alkyl esters of 3-hydroxypropionic acid; certain salts of 3-hydroxypropionic acid; or mixtures thereof.
- the present invention provides antifreezes and/or coolants comprising a glycol and a component selected from 3-hydroxypropionic acid; - C 4 alkyl esters of 3-hydroxypropionic acid; ammonium salts of 3-hydroxypropionic acid; - C 4 alkyl ammonium salts of 3-hydroxypropionic acid; alkali metal salts of 3- hydroxypropionic acid; alkaline earth metal salts of 3-hydroxypropionic acid; or mixtures thereof.
- the glycol-containing antifreezes and/or coolants may be used without dilution
- aqueous or non-aqueous medium for example, water.
- materials useful as antifreezes and/or coolants without dilution include 3-hydroxypropionic acid; and C]-C 4 alkyl esters of 3-hydroxypropionic acid (e.g., methyl, ethyl, propyl and butyl esters of 3-hydroxypropionic acid).
- materials useful as antifreezes and/or coolants, when utilized in the form of an aqueous or non- aqueous solution, for example, water-based solutions.
- Solutions useful as antifreezes and/or coolants typically comprise from about 0.1 weight percent to about 99.9 weight percent of a component selected from 3-hydroxypropionic acid; C ⁇ -C 4 alkyl esters of 3- hydroxypropionic acid (e.g., methyl, ethyl, propyl or butyl esters of 3-hydroxypropionic acid); or mixtures thereof.
- the component is present in the solution in an amount ranging from about 25 to about 75 weight percent, or in an amount ranging from about 40 to about 60 weight percent.
- the solutions useful as antifreezes and/or coolants comprise salts of 3-hydroxypropionic acid.
- salts of 3-hydroxypropionic acid that are suitable in preparing the solutions include ammonium salt of 3- hydroxypropionic acid; C ⁇ -C 4 alkyl ammonium salts of 3-hydroxypropionic acid; alkali metal salts of 3-hydroxypropionic acid (e.g., sodium, potassium, lithium, and the like); alkaline earth metal salts of 3-hydroxypropionic acid (e.g., calcium, magnesium, and the like); and mixtures thereof.
- the solutions typically comprise from about 0.1% by weight to about 90% by weight of a salt of 3-hydroxypropionic acid. In other embodiments, the solutions comprise from about 25 to about 75% by weight of a salt of 3-hydroxypropionic acid.
- blends comprising: (i) a glycol; and (ii) a component selected from 3-hydroxypropionic acid; C ⁇ -C alkyl esters of 3-hydroxypropionic acid; ammonium salts of 3-hydroxypropionic acid; Q- C alkyl ammonium salts of 3-hydroxypropionic acid; alkali metal salts of 3-hydroxypropionic acid; alkaline earth metal salts of 3-hydroxypropionic acid; and mixtures thereof.
- the glycol-containing antifreezes and/or .coolants may be utilized without dilution (i.e., neat) or they may be diluted with an aqueous or non-aqueous medium, for example, water.
- glycols that may be used include alkylene glycols (e.g., ethylene glycol, diethylene glycol, propylene glycol, hexylene glycol, 1,3-butylene glycol, and the like); and glycol monoethers (e.g., methyl, ethyl, propyl and butyl ethers of ethylene glycol, dipropylene glycol, and the like). Mixtures of the foregoing may also be used.
- alkylene glycols e.g., ethylene glycol, diethylene glycol, propylene glycol, hexylene glycol, 1,3-butylene glycol, and the like
- glycol monoethers e.g., methyl, ethyl, propyl and butyl ethers of ethylene glycol, dipropylene glycol, and the like.
- the component that is blended with the glycol in producing the antifreezes and/or coolants of invention is selected from 3-hydroxypropionic acid; C ⁇ -C 4 alkyl esters of 3- hydroxypropionic acid (e.g., methyl, ethyl, propyl and butyl esters of 3-hydroxypropionic acid); ammonium salts of 3-hydroxypropionic acid; C ⁇ -C alkyl ammonium salts of 3- hydroxypropionic acid; alkali metal salts of 3-hydroxypropionic acid (e.g., a sodium, potassium, or lithium salt of 3-hydroxypropionic acid); alkaline earth metal salt of 3- hydroxypropionic acid (e.g., a calcium or magnesium salt of 3-hydroxypropionic acid); and mixtures thereof.
- 3-hydroxypropionic acid e.g., methyl, ethyl, propyl and butyl esters of 3-hydroxypropionic acid
- ammonium salts of 3-hydroxypropionic acid e.g., methyl,
- the glycol is typically present in an amount ranging from about 0.1% by weight to about 99.9% by weight, based on the total weight of the antifreeze and/or coolant. In some embodiments, the glycol is present in an amount ranging from about 25% to about 75% by weight.
- the component is typically present in the antifreeze and/or coolant in an amount ranging from about 0.1% to about 99.9% by weight, based on the total weight of the antifreeze and/or coolant. In some embodiments, the component is present in an amount ranging from about 25 to about 75% by weight.
- the glycol-containing antifreezes and/or coolants may further comprise an aqueous or non-aqueous medium, for example, an aqueous medium such as water.
- the aqueous or non-aqueous medium of the glycol-containing antifreezes and/or coolants of the invention is typically present in an amount ranging from about 0.1% by weight to about 99.8% by weight, based on the total weight of the antifreeze and/or coolant. In some embodiments, the medium is present in an amount ranging from about 25% to about 75% by weight.
- the glycol is typically present in an amount ranging from about 0.1 to about 99.8% by weight, based on the total weight of the antifreeze and/or coolant.
- the glycol is present in an amount ranging from about 25 to about 75% by weight.
- the component is typically present in the antifreeze and/or coolant in an amount ranging from about 0.1% by weight to about 99.8% by weight, based on the total weight of the antifreeze and/or coolant. In some embodiments, the component is present in an amount ranging from about 25 to about 75% by weight.
- any additives conventionally known and used with other antifreezes and/or coolants may be used.
- additives known to be generally useful in antifreezes and/or coolants are expected to be useful in the antifreezes and/or coolants herein.
- Various monobasic acids, and the salts of such acids are known corrosion inhibitors.
- 3-hydroxypropionic acid, the -C 4 alkyl esters, the ammonium and C ⁇ -C alkyl ammonium, alkali metal and alkaline earth metal salts of 3-hydroxypropionic acid could also be corrosion inhibitors.
- Silicates are known corrosion inhibitors for antifreezes and/or coolants, as are also molybdates, tungstates and selenates.
- antifreezes and/or coolants For inhibiting salt corrosion, there have been utilized in antifreezes and/or coolants, nitrates and nitrites, as well as carbonates. Azoles have been used in antifreezes and/or coolants to inhibit corrosion of yellow metal such as copper and brass. There may also be incorporated in the antifreezes and/or coolants, other additives such as pH controlling compounds, defoamers, dyes, biocides and the like. The invention will be more readily understood by reference to the following examples.
- EXAMPLE 1 In evaluating the performance as an antifreeze and/or coolant in the following Table I, the following procedure was utilized. The melting points of the samples of the material were measured by using a Perkin Elmer Differential Scanning Calorimeter (DSC) mode 7 with robotic system model DSC 7Rse and Thermal Analysis Controller (TAC) mode 7/DX. The melting points of the samples were determined in accordance with the instructions provided by the manufacturer of the instrument. The melting points that were determined are reported for the samples that were measured, as Freezing Point, in Table 1, for convenience. In the following Table 1, each of the materials shown was evaluated in the form of an aqueous solution comprising water and the specified weight percent of the material.
- DSC Perkin Elmer Differential Scanning Calorimeter
- TAC Thermal Analysis Controller
- the antifreezes and/or coolants of the present invention are generally as effective as the propylene glycol antifreeze and/or coolant control.
- the data reveal that the antifreezes and/or coolants of the present invention are more effective than the propylene glycol antifreeze and/or coolant control.
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- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Physics & Mathematics (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Combustion & Propulsion (AREA)
- Thermal Sciences (AREA)
- Materials Engineering (AREA)
- Organic Chemistry (AREA)
- Preventing Corrosion Or Incrustation Of Metals (AREA)
Abstract
There is disclosed the use as an antifreeze and/or coolant of 3-hydroxypropionic acid, a C1 - C4 alkyl ester of 3-hydroxypropionic acid, an ammonium salt of 3-hydroxypropionic acid, a C1 - C4 alkyl ammonium salt of 3-hydroxypropionic acid, an alkali metal salt of 3-hydroxypropionic acid, an alkaline earth metal salt of 3-hydroxypropionic acid, or mixture thereof. Also disclosed are aqueous and non-aqueous solutions thereof, and blends of the antifreezes and/or coolants that additionally comprise a glycol, such as ethylene glycol or propylene glycol.
Description
ANTIFREEZES AND/OR COOLANTS FIELD The present invention relates to antifreezes and/or coolants. BACKGROUND It is well known to use as antifreezes and/or coolants, mixtures of water and a freezing point depressant such as an alkylene glycol and a glycol monoether. Examples of glycols that are used include ethylene glycol, diethylene glycol, propylene glycol, hexylene glycol, and 1,3-butylene glycol. Exemplary glycol monoethers that are used include the alkyl ethers of the glycols. Accordingly, it would be desirable to provide other materials for use as antifreezes and/or coolants that would be suitable for use particularly for internal combustion engines.
SUMMARY In one aspect, the present invention provides a process for using, as an antifreeze and/or coolant, a component selected from 3-hydroxypropionic acid; to C4 alkyl esters of 3-hydroxypropionic acid; or mixtures thereof. In another aspect, the present invention provides a process for using, as an antifreeze and/or coolant, an aqueous or non-aqueous solution comprising a component selected from 3-hydroxypropionic acid; - C alkyl esters of 3-hydroxypropionic acid; certain salts of 3-hydroxypropionic acid; or mixtures thereof. In yet another aspect, the present invention provides antifreezes and/or coolants comprising a glycol and a component selected from 3-hydroxypropionic acid; Ci - C alkyl esters of 3-hydroxypropionic acid; ammonium salts of 3-hydroxypropionic acid; Cι- C4 alkyl ammonium salts of 3-hydroxypropionic acid; alkali metal salts of 3- hydroxypropionic acid; alkaline earth metal salts of 3-hydroxypropionic acid; or mixtures thereof. The glycol-containing antifreezes and/or coolants may be used without dilution (i.e., neat) or they may be diluted with an aqueous or non-aqueous medium, for example, water. Antifreezes and/or coolants of the invention are particularly useful for use in internal combustion engines. In addition, the antifreezes and/or coolants may be useful in reducing the pour points of oils, lubricants, metal working fluids, and the like.
DETAILED DESCRIPTION In one aspect, the present invention provides a process for using, as an antifreeze and/or coolant, a component selected from 3-hydroxypropionic acid; to C alkyl esters of 3-hydroxyproρionic acid; or mixtures thereof. In another aspect, the present invention provides a process for using, as an antifreeze and/or coolant, an aqueous or non-aqueous solution comprising a component selected from 3-hydroxypropionic acid; - C alkyl esters of 3-hydroxypropionic acid; certain salts of 3-hydroxypropionic acid; or mixtures thereof. In yet another aspect, the present invention provides antifreezes and/or coolants comprising a glycol and a component selected from 3-hydroxypropionic acid; - C4 alkyl esters of 3-hydroxypropionic acid; ammonium salts of 3-hydroxypropionic acid; - C4 alkyl ammonium salts of 3-hydroxypropionic acid; alkali metal salts of 3- hydroxypropionic acid; alkaline earth metal salts of 3-hydroxypropionic acid; or mixtures thereof. The glycol-containing antifreezes and/or coolants may be used without dilution
(i.e., neat) or they may be diluted with an aqueous or non-aqueous medium, for example, water. Representative examples of materials useful as antifreezes and/or coolants without dilution include 3-hydroxypropionic acid; and C]-C4 alkyl esters of 3-hydroxypropionic acid (e.g., methyl, ethyl, propyl and butyl esters of 3-hydroxypropionic acid). In another embodiment of the invention, it has been found that certain materials are useful as antifreezes and/or coolants, when utilized in the form of an aqueous or non- aqueous solution, for example, water-based solutions. Solutions useful as antifreezes and/or coolants typically comprise from about 0.1 weight percent to about 99.9 weight percent of a component selected from 3-hydroxypropionic acid; Cι-C4 alkyl esters of 3- hydroxypropionic acid (e.g., methyl, ethyl, propyl or butyl esters of 3-hydroxypropionic acid); or mixtures thereof. In other embodiments, the component is present in the solution in an amount ranging from about 25 to about 75 weight percent, or in an amount ranging from about 40 to about 60 weight percent. In other embodiments, the solutions useful as antifreezes and/or coolants comprise salts of 3-hydroxypropionic acid. Representative examples of salts of 3-hydroxypropionic acid that are suitable in preparing the solutions include ammonium salt of 3-
hydroxypropionic acid; Cι-C4 alkyl ammonium salts of 3-hydroxypropionic acid; alkali metal salts of 3-hydroxypropionic acid (e.g., sodium, potassium, lithium, and the like); alkaline earth metal salts of 3-hydroxypropionic acid (e.g., calcium, magnesium, and the like); and mixtures thereof. The solutions typically comprise from about 0.1% by weight to about 90% by weight of a salt of 3-hydroxypropionic acid. In other embodiments, the solutions comprise from about 25 to about 75% by weight of a salt of 3-hydroxypropionic acid. Also found to be useful as antifreezes and/or coolants are blends comprising: (i) a glycol; and (ii) a component selected from 3-hydroxypropionic acid; Cι-C alkyl esters of 3-hydroxypropionic acid; ammonium salts of 3-hydroxypropionic acid; Q- C alkyl ammonium salts of 3-hydroxypropionic acid; alkali metal salts of 3-hydroxypropionic acid; alkaline earth metal salts of 3-hydroxypropionic acid; and mixtures thereof. The glycol-containing antifreezes and/or .coolants may be utilized without dilution (i.e., neat) or they may be diluted with an aqueous or non-aqueous medium, for example, water. Representative examples of the glycols that may be used include alkylene glycols (e.g., ethylene glycol, diethylene glycol, propylene glycol, hexylene glycol, 1,3-butylene glycol, and the like); and glycol monoethers (e.g., methyl, ethyl, propyl and butyl ethers of ethylene glycol, dipropylene glycol, and the like). Mixtures of the foregoing may also be used. The component that is blended with the glycol in producing the antifreezes and/or coolants of invention is selected from 3-hydroxypropionic acid; Cι-C4 alkyl esters of 3- hydroxypropionic acid (e.g., methyl, ethyl, propyl and butyl esters of 3-hydroxypropionic acid); ammonium salts of 3-hydroxypropionic acid; Cι-C alkyl ammonium salts of 3- hydroxypropionic acid; alkali metal salts of 3-hydroxypropionic acid (e.g., a sodium, potassium, or lithium salt of 3-hydroxypropionic acid); alkaline earth metal salt of 3- hydroxypropionic acid (e.g., a calcium or magnesium salt of 3-hydroxypropionic acid); and mixtures thereof. When the glycol-containing antifreezes and/or coolants of the invention are used without dilution, the glycol is typically present in an amount ranging from about 0.1% by weight to about 99.9% by weight, based on the total weight of the antifreeze and/or
coolant. In some embodiments, the glycol is present in an amount ranging from about 25% to about 75% by weight. The component is typically present in the antifreeze and/or coolant in an amount ranging from about 0.1% to about 99.9% by weight, based on the total weight of the antifreeze and/or coolant. In some embodiments, the component is present in an amount ranging from about 25 to about 75% by weight. The glycol-containing antifreezes and/or coolants may further comprise an aqueous or non-aqueous medium, for example, an aqueous medium such as water. The aqueous or non-aqueous medium of the glycol-containing antifreezes and/or coolants of the invention is typically present in an amount ranging from about 0.1% by weight to about 99.8% by weight, based on the total weight of the antifreeze and/or coolant. In some embodiments, the medium is present in an amount ranging from about 25% to about 75% by weight. When an aqueous or non-aqueous medium is present, the glycol is typically present in an amount ranging from about 0.1 to about 99.8% by weight, based on the total weight of the antifreeze and/or coolant. In some embodiments, the glycol is present in an amount ranging from about 25 to about 75% by weight. When an aqueous or non-aqueous medium is present, the component is typically present in the antifreeze and/or coolant in an amount ranging from about 0.1% by weight to about 99.8% by weight, based on the total weight of the antifreeze and/or coolant. In some embodiments, the component is present in an amount ranging from about 25 to about 75% by weight. In producing antifreezes and/or coolants of the invention, including those comprising an aqueous or non-aqueous medium, any additives conventionally known and used with other antifreezes and/or coolants may be used. For example, and without intending to be so limited thereby, the following are representative of additives known to be generally useful in antifreezes and/or coolants, and as such, are expected to be useful in the antifreezes and/or coolants herein. Various monobasic acids, and the salts of such acids, are known corrosion inhibitors. In this respect, 3-hydroxypropionic acid, the -C4 alkyl esters, the ammonium and Cι-C alkyl ammonium, alkali metal and alkaline earth metal salts of 3-hydroxypropionic acid, could also be corrosion inhibitors. Silicates are known corrosion inhibitors for antifreezes and/or coolants, as are also molybdates, tungstates and selenates. For inhibiting salt corrosion, there have been utilized in antifreezes and/or coolants, nitrates and nitrites, as well as carbonates. Azoles have been
used in antifreezes and/or coolants to inhibit corrosion of yellow metal such as copper and brass. There may also be incorporated in the antifreezes and/or coolants, other additives such as pH controlling compounds, defoamers, dyes, biocides and the like. The invention will be more readily understood by reference to the following examples. There are, of course, many other forms of this invention which will become obvious to one skilled in the art, once the invention has been fully disclosed, and it will accordingly be recognized that these examples are given for the purpose of illustration only, and are not to be construed as limiting the scope of this invention in any way. EXAMPLE 1 In evaluating the performance as an antifreeze and/or coolant in the following Table I, the following procedure was utilized. The melting points of the samples of the material were measured by using a Perkin Elmer Differential Scanning Calorimeter (DSC) mode 7 with robotic system model DSC 7Rse and Thermal Analysis Controller (TAC) mode 7/DX. The melting points of the samples were determined in accordance with the instructions provided by the manufacturer of the instrument. The melting points that were determined are reported for the samples that were measured, as Freezing Point, in Table 1, for convenience. In the following Table 1, each of the materials shown was evaluated in the form of an aqueous solution comprising water and the specified weight percent of the material.
This is listed in the Table as Concentration, Weight %. For reference, the normality of each of the aqueous solutions has been calculated and is shown in the Table as
Concentration, Normal. Furthermore, for convenience, the materials that are reported in Table 1, are identified as follows: Propylene glycol NH4-3HP: ammonium salt of 3-hydroxypropionic acid Na-3HP: sodium salt of 3-hydroxypropionic acid 3HP: 3-hydroxypropionic acid Methyl 3HP: methyl ester of 3-hydroxypropionic acid Ethyl 3HP: ethyl ester of 3-hydroxypropionic acid
TABLE 1 - FREEZING POINTS
From the above data, it is observed that the antifreezes and/or coolants of the present invention are generally as effective as the propylene glycol antifreeze and/or coolant control. In many instances, moreover, the data reveal that the antifreezes and/or coolants of the present invention are more effective than the propylene glycol antifreeze and/or coolant control. The invention has been described with reference to various specific and illustrative embodiments and techniques. However, one skilled in the art will recognize that many variations and modifications may be made while remaining within the spirit and scope of the invention.
Claims
1. A process that comprises using as an antifreeze and/or coolant a component selected from the group consisting of 3-hydroxypropionic acid, C1-C4 alkyl esters of 3- hydroxypropionic acid, and mixtures thereof.
2. The process according to claim 1, wherein the -C alkyl ester of 3- hydroxypropionic acid is selected from the group consisting of a methyl ester of 3- hydroxypropionic acid and an ethyl ester of 3-hydroxypropionic acid.
3. A process that comprises using as an antifreeze and/or coolant a solution comprising an amount of from about 0.1 weight percent to about 99.9 weight percent of a component selected from the group consisting of 3-hydroxypropionic acid, -C4 alkyl esters of 3-hydroxypropionic acid, and mixtures thereof, based on a total weight of the antifreeze and/or coolant.
4. The process according to claim 3, wherein the component is present in an amount ranging from about 25 weight percent to about 75 weight percent.
5. The process according to claim 3, wherein the component is 3- hydroxypropionic acid.
6. The process according to claim 3, wherein the component is the methyl ester of 3-hydroxypropionic acid.
7. A process that comprises using as an antifreeze and/or coolant a solution comprising an amount of from about 0.1 weight percent to about 90 weight percent, based on a total weight of the antifreeze and/or coolant, of a component selected from the group consisting of: ammonium salts of 3-hydroxypropionic acid; Ci - C4 alkyl ammonium salts of 3-hydroxypropionic acid; alkali metal salts of 3-hydroxypropionic acid; alkaline earth metal salts of 3-hydroxypropionic acid; and mixtures thereof.
8. The process according to claim 7, wherein the component is selected from the group consisting of: an ammonium salt of 3-hydroxypropionic acid and a sodium salt of 3-hydroxypropionic acid.
9. The process according to claim 7, wherein the solution comprises an aqueous medium.
10. The process according to claim 9, wherein the aqueous medium comprises water.
11. An antifreeze and/or coolant comprising: (i) an amount of from about 0.1 weight percent to about 99.9 weight percent of a glycol based on a total weight of the antifreeze and/or coolant; and (ii) an amount of from about 0.1 weight percent to about 99.9 weight percent, based on the total weight of the antifreeze and/or coolant, of a component selected from the group consisting of: 3-hydroxypropionic acid; - C4 alkyl esters of 3-hydroxypropionic acid; ammonium salts of 3- hydroxypropionic acid; Ci - C4 alkyl ammonium salts of 3-hydroxypropionic acid; alkali metal salts of 3-hydroxypropionic acid; alkaline earth metal salts of 3- hydroxypropionic acid; and mixtures thereof.
12. The antifreeze and/or coolant according to claim 11, wherein the glycol is selected from the group consisting of ethylene glycol and propylene glycol.
13. The antifreeze and/or coolant according to claim 12, wherein the component is selected from the group consisting of: ammonium salts of 3- hydroxypropionic acid; Ci - C alkyl ammonium salts of 3-hydroxypropionic acid; alkali metal salts of 3-hydroxypropionic acid; alkaline earth metal salts of 3-hydroxypropionic acid; and mixtures thereof.
14. An antifreeze and/or coolant comprising: (i) an amount of from about 0.1 weight percent to about 99.8 weight percent of a glycol based on a total weight of the antifreeze and/or coolant; (ii) an amount of from about 0.1 weight percent to about 99.8 weight percent, based on the total weight of the antifreeze and/or coolant, of a first component selected from the group consisting of: 3-hydroxypropionic acid; - C4 alkyl esters of 3-hydroxypropionic acid; ammonium salts of 3- hydroxypropionic acid; Ci - C4 alkyl ammonium salts of 3-hydroxypropionic acid; alkali metal salts of 3-hydroxypropionic acid; alkaline earth metal salt of 3- hydroxypropionic acid; and mixtures thereof; and (iii) an amount of from about 0.1 weight percent to about 99.8 weight percent, based on the total weight of the antifreeze and/or coolant, of a second component selected from the group consisting of an aqueous medium and a non-aqueous medium.
15. The antifreeze and/or coolant according to claim 14, wherein the glycol is selected from the group consisting of ethylene glycol and propylene glycol.
16. The antifreeze and/or coolant according to claim 15, wherein the first component is selected from the group consisting of: ammonium salts of 3- hydroxypropionic acid; - C4 alkyl ammonium salts of 3-hydroxypropionic acid; alkali metal salts of 3-hydroxypropionic acid; alkaline earth metal salts of 3-hydroxypropionic acid; and mixtures thereof.
17. The antifreeze and/or coolant according to claim 14, wherein the second component is an aqueous medium.
18. The antifreeze and/or coolant according to claim 17, wherein the aqueous medium is water.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US56399004P | 2004-04-21 | 2004-04-21 | |
| PCT/US2005/013621 WO2005105946A1 (en) | 2004-04-21 | 2005-04-21 | Antifreezes and/or coolants |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| EP1747254A1 true EP1747254A1 (en) | 2007-01-31 |
Family
ID=35241663
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| EP05739037A Withdrawn EP1747254A1 (en) | 2004-04-21 | 2005-04-21 | Antifreezes and/or coolants |
Country Status (3)
| Country | Link |
|---|---|
| EP (1) | EP1747254A1 (en) |
| CA (1) | CA2563989A1 (en) |
| WO (1) | WO2005105946A1 (en) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7790054B2 (en) | 2007-06-28 | 2010-09-07 | Chevron U.S.A. Inc. | Antifreeze concentrate and coolant compositions and preparation thereof |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5876621A (en) * | 1997-09-30 | 1999-03-02 | Sapienza; Richard | Environmentally benign anti-icing or deicing fluids |
-
2005
- 2005-04-21 CA CA002563989A patent/CA2563989A1/en not_active Abandoned
- 2005-04-21 EP EP05739037A patent/EP1747254A1/en not_active Withdrawn
- 2005-04-21 WO PCT/US2005/013621 patent/WO2005105946A1/en not_active Ceased
Non-Patent Citations (1)
| Title |
|---|
| See references of WO2005105946A1 * |
Also Published As
| Publication number | Publication date |
|---|---|
| CA2563989A1 (en) | 2005-11-10 |
| WO2005105946A1 (en) | 2005-11-10 |
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