GB2194947A - Nitrogen-containing additives and their production - Google Patents
Nitrogen-containing additives and their production Download PDFInfo
- Publication number
- GB2194947A GB2194947A GB08724821A GB8724821A GB2194947A GB 2194947 A GB2194947 A GB 2194947A GB 08724821 A GB08724821 A GB 08724821A GB 8724821 A GB8724821 A GB 8724821A GB 2194947 A GB2194947 A GB 2194947A
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- alkyl
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
- C07C323/23—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton
- C07C323/24—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton
- C07C323/25—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton the carbon skeleton being acyclic and saturated
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- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10L—FUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G, C10K; LIQUEFIED PETROLEUM GAS; ADDING MATERIALS TO FUELS OR FIRES TO REDUCE SMOKE OR UNDESIRABLE DEPOSITS OR TO FACILITATE SOOT REMOVAL; FIRELIGHTERS
- C10L1/00—Liquid carbonaceous fuels
- C10L1/10—Liquid carbonaceous fuels containing additives
- C10L1/14—Organic compounds
- C10L1/22—Organic compounds containing nitrogen
- C10L1/222—Organic compounds containing nitrogen containing at least one carbon-to-nitrogen single bond
- C10L1/2222—(cyclo)aliphatic amines; polyamines (no macromolecular substituent 30C); quaternair ammonium compounds; carbamates
- C10L1/2225—(cyclo)aliphatic amines; polyamines (no macromolecular substituent 30C); quaternair ammonium compounds; carbamates hydroxy containing
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10L—FUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G, C10K; LIQUEFIED PETROLEUM GAS; ADDING MATERIALS TO FUELS OR FIRES TO REDUCE SMOKE OR UNDESIRABLE DEPOSITS OR TO FACILITATE SOOT REMOVAL; FIRELIGHTERS
- C10L1/00—Liquid carbonaceous fuels
- C10L1/10—Liquid carbonaceous fuels containing additives
- C10L1/14—Organic compounds
- C10L1/24—Organic compounds containing sulfur, selenium and/or tellurium
- C10L1/2406—Organic compounds containing sulfur, selenium and/or tellurium mercaptans; hydrocarbon sulfides
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10L—FUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G, C10K; LIQUEFIED PETROLEUM GAS; ADDING MATERIALS TO FUELS OR FIRES TO REDUCE SMOKE OR UNDESIRABLE DEPOSITS OR TO FACILITATE SOOT REMOVAL; FIRELIGHTERS
- C10L1/00—Liquid carbonaceous fuels
- C10L1/10—Liquid carbonaceous fuels containing additives
- C10L1/14—Organic compounds
- C10L1/24—Organic compounds containing sulfur, selenium and/or tellurium
- C10L1/2431—Organic compounds containing sulfur, selenium and/or tellurium sulfur bond to oxygen, e.g. sulfones, sulfoxides
-
- 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
- C10M135/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing sulfur, selenium or tellurium
- C10M135/08—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing sulfur, selenium or tellurium containing a sulfur-to-oxygen bond
-
- 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
- C10M135/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing sulfur, selenium or tellurium
- C10M135/20—Thiols; Sulfides; Polysulfides
- C10M135/22—Thiols; Sulfides; Polysulfides containing sulfur atoms bound to acyclic or cycloaliphatic carbon atoms
- C10M135/24—Thiols; Sulfides; Polysulfides containing sulfur atoms bound to acyclic or cycloaliphatic carbon atoms containing hydroxy groups; Derivatives thereof
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- Chemical & Material Sciences (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention relates to compounds of formula I <IMAGE> wherein X is -O-, -S-, -SO-, -SO2-, -C(O)-O- or -N(R<3>)-, in which R<3> is hydrogen or C1-C12 alkyl, R<1> is unsubstituted C1-C4 alkyl or C2-C5 alkyl substituted by one to three hydroxyl groups, R<2> is hydrogen, unsubstituted C1-C4 alkyl or C2-C5 alkyl substituted by one to three hydroxyl groups, with the proviso that at least one of the residues R<1> and R<2> is hydroxy-substituted, and wherein R is C4-C20 alkyl, a residue -CH2-CH(OH)-CH2-NR<1>R<2>, in which R<1> and R<2> have their previous significance, or R is C2-C18 alkenyl, C2-C3 alkynyl or C5-C12 cycloalkyl, with the proviso that, when X is -O-, -S- or -N(R<3>)-, R is branched C8-C20 alkyl and, when X is C(O)-O-, R is as defined above but is different from C4-C20 alkyl. The compounds of formula I are very suitable as corrosion inhibitors for non-aqueous functional fluids.
Description
SPECIFICATION
Nitrogen-containing additives for non-aqueous functional fluids
The present invention relates to novel nitrogen-containing compounds and to a process for the preparation of said nitrogen-containing compounds.
In US Patent Specification 2856363 there are described compounds of the formula RCH(OH)
CH(R')N(Y)R"OH, in which R is C2-C,2 alkyl, R' is hydrogen or C2-C,2 alkyl, R" is a C2-C5 hydrocarbon chain and Y is hydrogen or R"-OH. Specifically disclosed compounds are those of formulae C10H23-CH(0H)-CH2-NH-CH2-CH2-0H and C10H23-CH(0H)-CH2-N(CH2-CH2-0H)2. The compounds are described as corrosion inhibitors in lubricating oils.
Further, in GB Patent Specification 1152947 there are described N-(2-hydroxy-3-alkoxypropy
I)ethanolamines and N(2-hydroxy-3-alkoxypropyl)diethanolamines and quaternary ammonium salts thereof as antistatic agents for polymers. In GB Patent Specification 979667 there are described adducts of mono or dialkanolamines with glycidyi alkyl esters as starting materials in the preparation of polyurethanes.
Furthermore, in GB Specification 980003 there are described 1-N-alkyl- and 1-N-hydroxyalkyl-3- alkylcarboxy-2-propanols and the quaternary ammonium salts thereof for use in cosmetic preparations.
The present invention relates to compounds of formula I
wherein X is -O-, -S-, -SO-, -SO2-, -C(O)-O- or -N(R3)-, in which R3 is hydrogen or C,-C,2 alkyl, R' is unsubstituted C,-C4 alkyl or C2-C5 alkyl substituted by one to three hydroxyl groups,
R2 is hydrogen, unsubstituted C,-C4 alkyl or C2-C5 alkyl substituted by one to three hydroxyl groups, with the proviso that at least one of the residues R' and R2 is hydroxy-substituted, and wherein R is C4-C20 alkyl, a residue -CH2-CH(0H)-CH2-NR1R2, in which R' and R2 have their previous significance, or R is C2-C,8 alkenyl, C2-C3 alkynyl or C5-C,2 cycloalkyl, with the proviso that, when X is -O-, -S- or -N(R3)-, R is branched C8-C20 alkyl and, when X is C(O)-O-, R is as defined above but is different from C4-C20 alkyl.
R as C4-C20 alkyl may be straight chain or branched alkyl, e.g. n-butyl, isobutyl, sec-butyl, tertbutyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, undecyl, dodecyl, tridecyl, tetradecyl, pentadecyl, hexadecyl, heptadecyl, octadecyl or eicosyl with C8-C20 alkyl being preferred and Cg-C,2 alkyl being most preferred. R is preferably branched, especially tertiary alkyl.
R as C2-C18 alkenyl may be straight chain or branched alkenyl, e.g. vinyl, n-propenyl, isopropenyl, n-butenyl, isobutenyl, n-pentenyl, n-hexenyl, n-heptenyl, n-octenyl, n-nonenyl, n-decenyl, ndodecenyl, n-tetradecenyl, n-hexadecenyl or n-octadecenyl, with C2-C4 alkenyl being preferred.
C2-C3 Alkynyl groups are ethynyl or propargyl groups.
C5-C12 Cycloalkyl groups are exemplified by cyclopentyl, cycohexyl, cyclooctyl, cyclodecyl and cyclododecyl groups.
Unsubstituted C1-C,2 alkyl groups R3 may be straight chain or branched, e.g. methyl, ethyl, npropyl, n-butyl, n-hexyl, n-octyl, n-decyl, n-dodecyl, isopropyl, t-butyl or t-octyl.
Hydroxy-substituted C2-C5 alkyl groups R1 and R2 are e.g. -CH2-CH2-0H, -CH2-CH2-CH2-OH, -CH2-CH(0H)-CH3, -CH(CH20H)2C2H5 or -C(CH20H)3, with -CH2-CH2-0H being preferred.
Examples of compounds of formula I are listed in the following Table 1.
Table 1
R # I x | R I I I I Ii-C9H19 I -O- ICH2CH20H IH I I I I Ii-C9H19 I -O- ICH2CH2OH ICH2CH2OH I I i-C9H19 I -O- ICH2CH(oH)CH2oH ICH2CH(OH)CH2OH I I I I i-C12H25 I -O- ICH2CH2CH2OH ICH2CH2OH I I I Ii-C12B25 I -O- ICH2CH2OH ICH2CH(OH)CH3 I I I t-C9H19 -S- CH2CH2OH CH2CH2OH I I It-C9H19 I -S- ICH2CH(OH)CH2oH ICH2CH(OH)CH2oH I I I I I t-C12H25 -S- CH2CH2OH CH2CH2OH I I t-C12H25 -S- CH2CH2OH CH2CH(OH)CH3 t-C16H33 -S- CH2CH2OH CH2CH2OH I I I I t-C16H23 I -S- IC(CH20H)3 IH I I I I I IC4H9CH(C2H5)CH2 I -SO- ICH2CH2OH ICH2CH2OH I IC4H9CH(C2H5)CH2 I -SO2- ICH2CH2OH ICH2CH2OH i-C8H17 -N(CH3)- CH2CH2OH H I I I I t-C9H19 -N(CH3)- CH2CH(OH)CH2OH CH2CH(OH)CH2OH Preferred compounds of formula I are those wherein X is -O-, -S- or -C(O)-O-, and/or R1 and R3 are C2-C5 alkyl monosubstituted by hydroxy.
Especially preferred compounds of formula I are those wherein X is -S- and/or R is preferably tertiary C9-C18 alkyl.
Further preferred compounds of formula I are those wherein X is -S-, R1 is hydroxy-substituted C4-C5 alkyl, especially C4-C5 alkyl polysubstituted by hydroxy, and R2 is hydrogen and R is C4-C20 alkyl, preferably C8-C20 alkyl, in particular branched C8-C20 alkyl, most preferably tertiary C9-C18 alkyl.
The present invention also provides a process for the preparation of compounds of formula I by reacting a compound of formula II
R-XH (II) wherein X is -O-, -S-, SO2, -C(O)-O- or -N(R3)-, in which R3 is hydrogen or C,-C12 alkyl, and wherein R is C4-C20 alkyl, a residue -CH2-CH(OH)-CH2-NR1R2, in which R' is unsubstituted C1-C4 alkyl or C2-C5 alkyl substituted by one to three hydroxyl groups, and R2 is hydrogen, unsubstituted C1-C4 alkyl or C2-C5 alkyl substituted by one to three hydroxyl groups, with the proviso that at least one of the residues R' or R2 is hydroxy-substituted, or R is C2-C18 alkenyl, C2-C3 alkynyl or C5-C12 cycloalkyl, with the proviso that, when X is -O-, -S- or -N(R3)-, R is branched C8-CaO alkyl and, when X is -C(O)-O-, R is different from C4-C20 alkyl, or a metal salt thereof, e.g. the sodium or potassium salt, in the absence or presence of a catalyst, with a compound of Formula Ill
to produce a compound of formula iV
which is then reacted with an amine of formula V
wherein R1 and R2 have their previous significance.
The catalyst may be for example an acid, a base or a phase transfer catalyst.
The compounds of formula I are very suitable for improving the properties, especially the corrosion-inhibiting properties in non-aqueous functional fluids.
Copending British Patent Application No. 8605820 (Serial No. 2172284) describes and claims the use of the compounds of formula I as corrosion inhibitors in non-aqueous functional fluids in amounts of 0.001 to 5% by weight, especially 0.05 to 3% by weight, based on the nonaqueous functional fluid.
Example 1
10.5 parts of diethanolamine are heated to 6000 and 27.1 parts of tert-dodecylglycidyl thioether are added dropwise. After completion of the addition, the mixture is stirred for 1 hour at 70 C. 3-tert-Dodecylthio-1- [ di(2-hydroxyethyl)amino ] -propan-2-ol is obtained as a yellow viscous liquid having refractive index nD20=1.4972 in a yield of 100% of theory.
Example 2
By following a procedure analogous to that of Example 1, 21 parts of diethanolamine are reacted with 45.4 parts of tertnonylglycidyl thioether to produce 3-tert-nonylthio-1- [ di(2-hydroxy- ethyl)amino]propan-2-ol as a yellow viscous liquid having refractive index nD =1.5008 in a yield of 100% of theory.
Examples 3 to 20
Further compounds of formula I
are prepared by following a procedure analogous to those of Example 1. These compounds are listed in Table 2.
Table 2
EX. R X R1 R2 b.p.( C)/mb 3 i-C8H17 -O- CH2CH2OH CH2CH2OH 190/2.34 4 i-C8H17 -O- (CH2)3OH (CH2)3OH viscous oil 5 i-C8H17 -O- CH3 CH2CH2OH 180/0.065 6 i-C8H17 -O- CH2CHOHCH3 CH2CHOHCH3 210/0.05 7 CH2=CHCH2 -O- CH2CH2OH CH2CH2OH viscous oil 8 C4H9CH(C2H5)CH2 -N(CH2CH(C4H9)C2H5)- CH2CH2OH CH2CH2OH viscous oil 9 C4H9CH(C2H5)CH2 -N(CH2CH(C4H9)C2H5)- CH2CH2OH (CH2)3OH OH CH2CH2OH 10 CH2CHCH2N -N(C12H25)- CH2CH2OH CH2CH2OH 170/0.35 CH2CH2OH 11 t-C9H19 -S- CH2CH2OH H 12 t-C9H19 -S- CH3 CH2CH2OH 155/0.16 13 t-C12H25 -S- CH2CH2OH CH2CH2OH 14 t-C9H19 -S- CH2CH2OH CH2CH2OH 15 t-C16H33 -S- CH2CH2OH CH2CH2OH viscous oil 16 t-C9H19 -S- C(CH2OH)3 H m.p. 61-63 C 17 t-C12H25 -S- C(CH2OH)2C2H5 H viscous oil 18 t-C16H33 -S- C(CH2OH)3 H viscous oil 19 t-C4H9 -S- C(CH2OH)3 H 20 C2H5 -S- C(CH2OH)3 H
Claims (6)
1. A compound of formula I
wherein X is -O-, -S-, -SO-, -SO2-, -C(O)-O- or -N(R3)-, in which R3 is hydrogen or C,-C12 alkyl, R' is unsubstituted C,-C4 alkyl or C2-C5 alkyl substituted by one to three hydroxyl groups,
R2 is hydrogen, unsubstituted C1-C4 alkyl or C2-C5 alkyl substituted by one to three hydroxyl groups, with the proviso that at least one of the residues R' and R2 is hydroxy-substituted, and wherein R is C4-C20 alkyl, a residue -CH2-CH(OH)-CH2-NR1R2, in which R1 and R2 have their previous significance, or R is C2-C,8 alkenyl, C2-C3 alkynyl or C5-C12 cycloalkyl, with the proviso that, when X is -O-, -S- or -N(R3)-, R is branched C8-C20 alkyl and, when X is C(O)-O-, R is as defined above but is different from C4-C20 alkyl.
2. A compound according to claim 1, wherein in formula I X is -O-, -S- or -C(O)-O-.
3. A compound according to claim 1, wherein in formula I R1 and R2 are C2-C5 alkyl monosubstituted by hydroxy.
4. A compound according to claim 2, wherein in formula I X is -S-.
5. A compound according to claim 1, wherein in formula I R is tertiary Cg-Cl8 alkyl.
6. A compound according to claim 1, wherein in formula I X is -S-, R1 is C4-C5 alkyl polysubstituted by hydroxy, R2 is hydrogen and R is branched C8-C20 alkyl.
6. A compound according to claim 1, wherein in formula I X is -S-, R' is C4-C5 alkyl polysubstituted by hydroxy, R2 is hydrogen and R is C4-C20 alkyl.
7. A process for the preparation of a compound of formula I, which process comprises reacting a compound of formula II
R-XH (II) wherein X is -O-, -S-, -SO-, SO2, -C(O)-O- or -N(R3)-, in which R3 is hydrogen or C,-C,2 alkyl, and wherein R is C4-C20 alkyl, a residue -CH2-CH(OH)-CH2-N1R2, in which R' is unsubstituted C1-C4 alkyl or C2-C5 alkyl substituted by one to three hydroxyl groups, and R2 is hydrogen, unsubstituted C1-C4 alkyl or C2-C5 alkyl substituted by one to three hydroxyl groups, with the proviso that at least one of the residues R1 or R2 is hydroxy-substituted, or R is C2-C18 alkenyl, C2-C3 alkynyl or C5-C12 cycloalkyl, with the proviso that, when X is -O-, -S- or -N(R3)-, R is branched C8-C20 alkyl and, when X is -C(O)-O-, R is different from C4-C20 alkyl, or of a metal salt thereof, in the absence or presence of a catalyst, with a compound of formula lll
to produce a compound of formula IV
which is then reacted with an amine of formula V
wherein R' and R2 have their previous signficance.
CLAIMS
Amendments to the claims have been filed, and have the following effect:
Claims 6 above have been deleted or textually amended.
New or textually amended claims have been filed as follows:
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB08724821A GB2194947B (en) | 1985-03-12 | 1987-10-23 | Nitrogen-containing additives for non-aqueous functional fluids |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB858506352A GB8506352D0 (en) | 1985-03-12 | 1985-03-12 | Corrosion inhibition |
| GB08724821A GB2194947B (en) | 1985-03-12 | 1987-10-23 | Nitrogen-containing additives for non-aqueous functional fluids |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| GB8724821D0 GB8724821D0 (en) | 1987-11-25 |
| GB2194947A true GB2194947A (en) | 1988-03-23 |
| GB2194947B GB2194947B (en) | 1988-07-27 |
Family
ID=26288969
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB08724821A Expired GB2194947B (en) | 1985-03-12 | 1987-10-23 | Nitrogen-containing additives for non-aqueous functional fluids |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB2194947B (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0435219A2 (en) * | 1989-12-28 | 1991-07-03 | Hoechst Aktiengesellschaft | Surfactant compounds containing a perfluoroalkyl group and an aliphatic moiety containing nitrogen, process for their preparation and their use |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB980003A (en) * | 1961-11-02 | 1965-01-13 | Oreal | New amine and quaternary ammonium compounds,their preparation and their use |
-
1987
- 1987-10-23 GB GB08724821A patent/GB2194947B/en not_active Expired
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB980003A (en) * | 1961-11-02 | 1965-01-13 | Oreal | New amine and quaternary ammonium compounds,their preparation and their use |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0435219A2 (en) * | 1989-12-28 | 1991-07-03 | Hoechst Aktiengesellschaft | Surfactant compounds containing a perfluoroalkyl group and an aliphatic moiety containing nitrogen, process for their preparation and their use |
| EP0435219A3 (en) * | 1989-12-28 | 1991-11-21 | Hoechst Aktiengesellschaft | Surfactant compounds containing a perfluoroalkyl group and an aliphatic moiety containing nitrogen, process for their preparation and their use |
Also Published As
| Publication number | Publication date |
|---|---|
| GB8724821D0 (en) | 1987-11-25 |
| GB2194947B (en) | 1988-07-27 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PCNP | Patent ceased through non-payment of renewal fee |
Effective date: 19930310 |