WO1993007241A1 - Use of a triethanolamine product mixture - Google Patents

Use of a triethanolamine product mixture Download PDF

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Publication number
WO1993007241A1
WO1993007241A1 PCT/SE1992/000701 SE9200701W WO9307241A1 WO 1993007241 A1 WO1993007241 A1 WO 1993007241A1 SE 9200701 W SE9200701 W SE 9200701W WO 9307241 A1 WO9307241 A1 WO 9307241A1
Authority
WO
WIPO (PCT)
Prior art keywords
triethanolamine
product mixture
weight
diethanolamine
alkanolamine
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.)
Ceased
Application number
PCT/SE1992/000701
Other languages
French (fr)
Inventor
Rolf Sköld
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Nouryon Surface Chemistry AB
Original Assignee
Berol Nobel AB
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Berol Nobel AB filed Critical Berol Nobel AB
Priority to EP92921659A priority Critical patent/EP0607289B1/en
Priority to FI941626A priority patent/FI941626A0/en
Priority to US08/211,217 priority patent/US5431834A/en
Priority to DE69218448T priority patent/DE69218448T2/en
Publication of WO1993007241A1 publication Critical patent/WO1993007241A1/en
Priority to NO941260A priority patent/NO306412B1/en
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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Classifications

    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/40—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing nitrogen
    • A61K8/41—Amines
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q19/00—Preparations for care of the skin
    • 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
    • C10M133/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing nitrogen
    • C10M133/02—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing nitrogen having a carbon chain of less than 30 atoms
    • 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
    • C10M133/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing nitrogen
    • C10M133/02—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing nitrogen having a carbon chain of less than 30 atoms
    • C10M133/04—Amines, e.g. polyalkylene polyamines; Quaternary amines
    • C10M133/06—Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to acyclic or cycloaliphatic carbon atoms
    • C10M133/08—Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to acyclic or cycloaliphatic carbon atoms containing hydroxy groups
    • 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
    • C10M173/00—Lubricating compositions containing more than 10% water
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
    • C11D1/38—Cationic compounds
    • C11D1/42—Amino alcohols or amino ethers
    • C11D1/44—Ethers of polyoxyalkylenes with amino alcohols; Condensation products of epoxyalkanes with amines
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
    • C11D3/16—Organic compounds
    • C11D3/26—Organic compounds containing nitrogen
    • C11D3/30—Amines; Substituted amines ; Quaternized amines
    • 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
    • C10M2201/00—Inorganic compounds or elements as ingredients in lubricant compositions
    • C10M2201/02—Water
    • 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
    • C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant Compositions
    • 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
    • C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant Compositions
    • C10M2215/02—Amines, e.g. polyalkylene polyamines; Quaternary amines
    • C10M2215/04—Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to acyclic or cycloaliphatic carbon atoms
    • C10M2215/042—Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to acyclic or cycloaliphatic carbon atoms containing hydroxy groups; Alkoxylated derivatives thereof
    • 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
    • C10N2040/06—Instruments or other precision apparatus, e.g. damping fluids
    • 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
    • C10N2040/08—Hydraulic fluids, e.g. brake-fluids
    • 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
    • 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
    • C10N2050/00—Form in which the lubricant is applied to the material being lubricated
    • C10N2050/01—Emulsions, colloids, or micelles

Definitions

  • a triethanol ⁇ amine mixture containing a major part of triethanolamine, a minor part of diethanolmono-C 3 . 4 -alkanolamine and monoethanoldi- Cg ⁇ -alkanolamine, and less than 1% by weight of diethanolamine and monoethanolamine.
  • major part of tri- ethanolamine is here understood that said triethanolamine constitutes at least 50% by weight of the product mixture.
  • the triethanol amine product mixture used in accordance with the invention can easily be obtained by reacting a conventional triethanolamine reaction mixture, obtained when reacting ammonia in one or more steps, with a C 3 -C 4 -alkylene oxide.
  • Example l 100 grams of the same triethanolamine products mixture as specified in Example A were reacted with 10.9 grams of propy ⁇ lene oxide at 150°C. The ratio between the molecules of propy ⁇ lene oxide and the number of hydrogen atoms bound to a nitrogen atom were 1.3. After reaction the content of secondary and primary alkanolamines was found to be less than 0.1% by weight.
  • Example l 100 grams of the same triethanolamine products mixture as specified in Example A were reacted with 10.9 grams of propy ⁇ lene oxide at 150°C. The ratio between the molecules of propy ⁇ lene oxide and the number of hydrogen atoms bound to a nitrogen atom were 1.3. After reaction the content of secondary and primary alkanolamines was found to be less than 0.1% by weight. Example l.
  • the trietanolamine product mixtures TEA85-PO and TEA85-BO from Examples A and B were diluted with water having a water hardness of 0,2°dH to solutions containing 1, 2 and 3% by weight. The solutions were then neutralized with acetic acid to a pH-value of 9. As comparisons corresponding solution was also formulated from the triethanolamine product mixture used as starting product in Example A (hereinafter referred to as TEA85) and a distillation product of TEA85 containing 99% by weight of triethanolamine. The latter product are hereinafter referred to as TEA99.

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  • Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • General Chemical & Material Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • Veterinary Medicine (AREA)
  • Wood Science & Technology (AREA)
  • Engineering & Computer Science (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Birds (AREA)
  • Dermatology (AREA)
  • Epidemiology (AREA)
  • Detergent Compositions (AREA)
  • Cosmetics (AREA)
  • Lubricants (AREA)
  • Preventing Corrosion Or Incrustation Of Metals (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

Use of a triethanolamine product mixture in cosmetic products, cleaning compositions and functional fluids, the triethanolamine product mixture containing a major part of triethanolamine, a minor part of diethanolmono-C3-C4-alkanolamine and monoethanoldi-C3-C4-alkanolamine and less than 1 % by weight diethanolamine and monoethanolamine.

Description

USE OF A TRIETHANOLAMINE PRODUCT MIXTURE
The present application relates to the use of a triethanol- amine product mixture having a low content of diethanolamine and monoethanolamine in functional fluids, such as lubricants, metal working fluids and hydraulic fluids.
The use of triethanolamine in a variety of industrial fluids is well known. Triethanolamines are normally produced in one or more steps by ethoxylating ammonia with ethylene oxide. In order to avoid the formation of polyalkyleneglycol chains, HOC2H4(OC2H4)n, where n > 0, and the nitrogen atom to be quater- nized the ethoxylation is normally stopped, when the reaction mixture contains 60-90% by weight of triethanolamine and 10-40% by weight of diethanolamine and monethanolamine. Such a reac¬ tion mixture may be subjected to distillation to obtain purer triethanolamine. The fact that the triethanolamine reaction product contains a large amount of diethanolamine has not previously been considered a real drawback, as diethanolamine contributes to anticorrosion properties low foaming and desired alkalinity when used in functional fluids.
Recently, more attention has been paid to the fact the diethanolamine is toxic and forms nitrosamines, which are carcinogenic in animal tests. Therefore, a reduction of the content of diethanolamine is desirable. The content should according to recommentations be less than 1% by weight.
Thus, one object of the invention is to produce a trietha¬ nolamine product mixture which contains diethanolamine in an amount less than 1% by weight. This triethanolamine product mixture shall at least have about the same corrosion inhibiting ability and/or defoaming properties in functional fluids. Another object of the invention is that the method of producing a triethanolamine product mixture shall be simple to perform and that the mixture shall be usable without any additional cleaning and/or working-up processes, such as destination. Still another object of the invention is to keep the forma¬ tion of quartemized triethanolamine and polyalkylene glycol chain containing ethanola ine products to a low level.
According to the invention it has now been found that these objects can be met by using in functional fluids, a triethanol¬ amine mixture containing a major part of triethanolamine, a minor part of diethanolmono-C3.4-alkanolamine and monoethanoldi- Cg^-alkanolamine, and less than 1% by weight of diethanolamine and monoethanolamine. By the expression "major part of tri- ethanolamine" is here understood that said triethanolamine constitutes at least 50% by weight of the product mixture. The triethanol amine product mixture used in accordance with the invention can easily be obtained by reacting a conventional triethanolamine reaction mixture, obtained when reacting ammonia in one or more steps, with a C3-C4-alkylene oxide.
Such a process is described in British Patent No 1 140 867. Diethanolamine and monoethanolamine which are both reactants in the process have a catalytic effect and catalyze rather selec¬ tively their own alkoxylation. The presence of an effective amount of alkoxylation catalyst other than the diethanolamine and monoethanolamine shall preferably be avoided in order not to favour undesired side reactions. By the process the contents of diethanolamine and monoethanolamine are reduced to less than 1% by weight, while the undesired side reactions, such as alkoxylation of hydroxyl groups or quarternization of the nitrogen atom is kept on a low level. In order to further suppress side reactions, it has been found suitable to perform the reaction below 160°C, preferably between 120-150°C. The amount of alkylene oxide added has to be adjusted in relation to the amount of diethanolamine and monoethanolamine, so that the latter ones can be alkoxylated to the corresponding ter¬ tiary amine. Normally, the molar ratio of the alkylene oxide to the reactive hydrogen atoms bound to the nitrogen in diethanol¬ amine and monoethanolamine is 1.0-1.4 and suitably 1.0-1.10. The choice of alkylene oxide affects the HLB-value of the triethanolamine mixture formed during the reaction and the butylene oxide may be preferred if a product mixture with the more hydrophobic and surface active character is desired. Normally, the alkylene oxide used is propylene oxide. Both propylene oxide and butylene oxides react with a high selec- tivity with respect to the hydrogen atoms bound to the nitrogen atom in the primary and secondary amine resulting in a lower degree of side reactions like propoxylation of hydroxyl groups in monoethanolamine, diethanolamine or triethanolamine.
The triethanol amine product mixture used in accordance with the invention has many advantageous properties. Thus, application tests have clearly indicated that the triethanol¬ amine product mixture is very suitable to replace triethanol¬ amine as a component in aqueous functional fluids, such as lubricants, metal working fluids and hydraulic fluids. The diethanolmono-C3-C-alkanolamine in the triethanolamine product mixture contributes to improved corrosion inhibiting and low foaming properties.
The present invention is further illustrated by the follow¬ ing examples. Example A.
100 grams of a triethanolamine product mixture containing 85% by weight of triethanolamine and 15% by weight of dietha¬ nolamine and monoethanolamine (hereinafter referred to as TEA85) were reached with 8,4 grams of propylene oxide at 60°C. The ratio between the molecules of propylene oxide and the number of hydrogen atoms bound to a nitrogen atom was 1,01. After all propylene oxide had reacted the product obtained (hereinafter referred to as TEA85+PO) was analyzed with respect to the presence of secondary and primary ethanolamines. The total content of these alkanolamines was found to be less than 0,5% by weight. Example B.
100 grams of the same triethanolamine product mixture as specified in Example A were reacted with 10,4 grams of butylene oxide at 70°C. The ratio between the molecules of butylene oxide and the number of hydrogen atoms bound to a nitrogen atom was 1,00. After reaction with product mixture obtained (here¬ inafter referred to as TEA85-B0) was analyzed and the content of secondary and primary alkanolamines was found to be 0,7% by weigh . Example C.
100 grams of the same triethanolamine products mixture as specified in Example A were reacted with 10.9 grams of propy¬ lene oxide at 150°C. The ratio between the molecules of propy¬ lene oxide and the number of hydrogen atoms bound to a nitrogen atom were 1.3. After reaction the content of secondary and primary alkanolamines was found to be less than 0.1% by weight. Example l.
The trietanolamine product mixtures TEA85-PO and TEA85-BO from Examples A and B were diluted with water having a water hardness of 0,2°dH to solutions containing 1, 2 and 3% by weight. The solutions were then neutralized with acetic acid to a pH-value of 9. As comparisons corresponding solution was also formulated from the triethanolamine product mixture used as starting product in Example A (hereinafter referred to as TEA85) and a distillation product of TEA85 containing 99% by weight of triethanolamine. The latter product are hereinafter referred to as TEA99.
The twelve solutions were then tested with regard to their Fe corrosion according to cast iron chip-on-filter paper test (IP 287) and copper corrosion. In the measuring of copper corrosion 0,2 grams of copper powder was mixed with 10 grams of glass beads in 200 ml of the solution containing the alkanol¬ amines. The solutions were shaked for 24, 48 and 72 hours and the content of copper in the solutions was determined. The following results were obtained.
Figure imgf000007_0001
Figure imgf000007_0002
It is obvious that the alkanolamine product mixtures in accordance with the invention have favourable corrosion proper¬ ties in comparison with prior used alkanolamine products. Example 2.
The solutions of Example 1 containing 3% by weight of the alkanolamines were also tested with regard to foaming. 200 ml of each solution was vigorously stirred during 5 minutes and the volume of the fluid and the foam was measured. The follow¬ ing results were obtained.
Figure imgf000008_0001
^ Volume of the solutions before stirring is 200 ml.
From the results it is evident that the product mixtures of the invention has a low foaming like the prior art products. Example 3.
Synthetic metal working fluid concentrates were prepared from 20 parts by weight of TEA85-P0 or TEA99, 25 parts by weight of dodecandioic acid, 55 parts by weight of distilled water and potassium hydroxide in an amount sufficient to give a pH of 9,8. The concentrates were then diluted with water having a water hardness of 200 ppm in accordance with the table below and tested with regard of foaming ability in accordance with Institute of Petroleum, IP 312 and with regard to iron corro¬ sion in the same manner as in Example 1. The following results were obtained.
Figure imgf000009_0001
From the results it is evident that the triethanolamine product mixture of the invention with advantage can replace TEA99.

Claims

1. Use of a triethanolamine product mixture in functional fluids, the triethanolamine product mixture containing a major part of triethanolamine, a minor part of diethanolmono-C3-C4- alkanolamine and monoethanoldi-C3-C4-alkanolamine and less than 1% by weight diethanolamine and monoethanolamine.
2. Use in accordance with claim 1, characterised in that the major part is 60-90% by weight, and the minor part is 10-
40% by weight.
3. Use of the triethanolamine product mixture of claim 1 or 2 in an aqueous metal working fluid.
PCT/SE1992/000701 1991-10-10 1992-10-07 Use of a triethanolamine product mixture Ceased WO1993007241A1 (en)

Priority Applications (5)

Application Number Priority Date Filing Date Title
EP92921659A EP0607289B1 (en) 1991-10-10 1992-10-07 Use of a triethanolamine product mixture
FI941626A FI941626A0 (en) 1991-10-10 1992-10-07 Use of a triethanolamine product mixture
US08/211,217 US5431834A (en) 1991-10-10 1992-10-07 Use of a triethanolamine product mixture
DE69218448T DE69218448T2 (en) 1991-10-10 1992-10-07 USE OF A TRIETHANOLAMINE PRODUCT MIXTURE
NO941260A NO306412B1 (en) 1991-10-10 1994-04-07 Use of a triethanolamine product mixture

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
SE9102931A SE469058B (en) 1991-10-10 1991-10-10 APPLICATION OF A TRIETANOLAMINE-CONTAINING PRODUCT MIXTURE IN COSMETIC PRODUCTS AND CLEANING COMPOSITIONS
SE9102931-4 1991-10-10

Publications (1)

Publication Number Publication Date
WO1993007241A1 true WO1993007241A1 (en) 1993-04-15

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Family Applications (2)

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PCT/SE1992/000700 Ceased WO1993006814A1 (en) 1991-10-10 1992-10-07 Use of a triethanolamine product mixture
PCT/SE1992/000701 Ceased WO1993007241A1 (en) 1991-10-10 1992-10-07 Use of a triethanolamine product mixture

Family Applications Before (1)

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PCT/SE1992/000700 Ceased WO1993006814A1 (en) 1991-10-10 1992-10-07 Use of a triethanolamine product mixture

Country Status (9)

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US (2) US5447723A (en)
EP (2) EP0607289B1 (en)
JP (2) JP3162385B2 (en)
DE (2) DE69210411T2 (en)
DK (2) DK0607289T3 (en)
FI (2) FI941626A0 (en)
NO (2) NO303764B1 (en)
SE (1) SE469058B (en)
WO (2) WO1993006814A1 (en)

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CN1077465C (en) * 1994-09-30 2002-01-09 J·迪芬巴赫机器制造有限公司 Hydraulic deep dawing equipment of a pressing machine for mfg. streched thin plate former
US6132739A (en) * 1998-09-01 2000-10-17 Amway Corporation Makeup compositions and methods of making same
SE514315C2 (en) * 1998-09-07 2001-02-12 Rolf Skoeld A process for mechanical machining of a metal containing copper or aluminum
US20050107270A1 (en) * 2003-11-19 2005-05-19 Gernon Michael D. Alkyl ethanolamines for the control of mycobacteria in functional fluid
US20060160710A1 (en) * 2005-01-19 2006-07-20 Steven E. Rayfield Synthetic metal working fluids for ferrous metals
US7632458B2 (en) * 2006-01-31 2009-12-15 General Electric Company Corrosion inhibitor treatment for closed loop systems
CN103204779A (en) * 2013-04-27 2013-07-17 弗克科技(苏州)有限公司 Alkylol amine and preparation method

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US4420414A (en) * 1983-04-11 1983-12-13 Texaco Inc. Corrosion inhibition system
US4726914A (en) * 1986-10-10 1988-02-23 International Minerals & Chemical Corp. Corrosion inhibitors

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US4273937A (en) * 1979-12-19 1981-06-16 Union Carbide Corporation Organic amine compositions
US4420414A (en) * 1983-04-11 1983-12-13 Texaco Inc. Corrosion inhibition system
US4726914A (en) * 1986-10-10 1988-02-23 International Minerals & Chemical Corp. Corrosion inhibitors

Also Published As

Publication number Publication date
DE69210411T2 (en) 1996-09-12
EP0607289A1 (en) 1994-07-27
WO1993006814A1 (en) 1993-04-15
NO941260D0 (en) 1994-04-07
FI941626L (en) 1994-04-08
EP0607319B1 (en) 1996-05-01
DK0607319T3 (en) 1996-09-16
EP0607289B1 (en) 1997-03-19
FI941626A7 (en) 1994-04-08
US5447723A (en) 1995-09-05
FI103474B (en) 1999-07-15
FI941625A0 (en) 1994-04-08
EP0607319A1 (en) 1994-07-27
US5431834A (en) 1995-07-11
DE69218448D1 (en) 1997-04-24
SE469058B (en) 1993-05-10
FI103474B1 (en) 1999-07-15
NO303764B1 (en) 1998-08-31
SE9102931D0 (en) 1991-10-10
NO941259L (en) 1994-04-07
JPH07500103A (en) 1995-01-05
NO941259D0 (en) 1994-04-07
FI941626A0 (en) 1994-04-08
JP3162385B2 (en) 2001-04-25
DK0607289T3 (en) 1997-10-13
FI941625L (en) 1994-04-08
NO306412B1 (en) 1999-11-01
NO941260L (en) 1994-04-07
DE69218448T2 (en) 1997-06-26
JPH07502056A (en) 1995-03-02
DE69210411D1 (en) 1996-06-05

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