EP0368119B1 - Verwendung von Methylpolysiloxanen mit quartären Ammoniumgruppen als Korrosionsinhibitoren für überwiegend aus Wasser bestehende Zubereitungen - Google Patents
Verwendung von Methylpolysiloxanen mit quartären Ammoniumgruppen als Korrosionsinhibitoren für überwiegend aus Wasser bestehende Zubereitungen Download PDFInfo
- Publication number
- EP0368119B1 EP0368119B1 EP89120152A EP89120152A EP0368119B1 EP 0368119 B1 EP0368119 B1 EP 0368119B1 EP 89120152 A EP89120152 A EP 89120152A EP 89120152 A EP89120152 A EP 89120152A EP 0368119 B1 EP0368119 B1 EP 0368119B1
- Authority
- EP
- European Patent Office
- Prior art keywords
- quaternary ammonium
- ammonium groups
- radical
- value
- carbon atoms
- 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
- -1 polysiloxanes Polymers 0.000 title claims description 26
- 238000005260 corrosion Methods 0.000 title claims description 21
- 125000001453 quaternary ammonium group Chemical group 0.000 title claims description 21
- 230000007797 corrosion Effects 0.000 title claims description 20
- 238000002360 preparation method Methods 0.000 title claims description 11
- 239000003112 inhibitor Substances 0.000 title claims description 7
- 229920001296 polysiloxane Polymers 0.000 title claims 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 title description 3
- 150000001875 compounds Chemical class 0.000 claims description 18
- 150000003254 radicals Chemical class 0.000 claims description 17
- 125000004432 carbon atom Chemical group C* 0.000 claims description 16
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 10
- 239000005068 cooling lubricant Substances 0.000 claims description 6
- 150000001449 anionic compounds Chemical class 0.000 claims description 4
- 150000002891 organic anions Chemical class 0.000 claims description 4
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical group [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 claims description 3
- 239000002826 coolant Substances 0.000 claims description 3
- WCYWZMWISLQXQU-UHFFFAOYSA-N methyl Chemical compound [CH3] WCYWZMWISLQXQU-UHFFFAOYSA-N 0.000 claims description 3
- 239000000839 emulsion Substances 0.000 description 6
- 235000014113 dietary fatty acids Nutrition 0.000 description 5
- 229930195729 fatty acid Natural products 0.000 description 5
- 239000000194 fatty acid Substances 0.000 description 5
- 150000004665 fatty acids Chemical class 0.000 description 5
- 230000002401 inhibitory effect Effects 0.000 description 5
- 238000005555 metalworking Methods 0.000 description 4
- 239000004215 Carbon black (E152) Substances 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- 229930195733 hydrocarbon Natural products 0.000 description 3
- 238000012360 testing method Methods 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 150000001450 anions Chemical class 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 229910052710 silicon Inorganic materials 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- KTOQRRDVVIDEAA-UHFFFAOYSA-N 2-methylpropane Chemical compound [CH2]C(C)C KTOQRRDVVIDEAA-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 1
- 229910001060 Gray iron Inorganic materials 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O ammonium group Chemical group [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
- 239000010775 animal oil Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 230000033228 biological regulation Effects 0.000 description 1
- 125000002843 carboxylic acid group Chemical group 0.000 description 1
- 229940125904 compound 1 Drugs 0.000 description 1
- 229940125782 compound 2 Drugs 0.000 description 1
- 229940126214 compound 3 Drugs 0.000 description 1
- 229940125898 compound 5 Drugs 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000010730 cutting oil Substances 0.000 description 1
- 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 238000007865 diluting Methods 0.000 description 1
- KPUWHANPEXNPJT-UHFFFAOYSA-N disiloxane Chemical class [SiH3]O[SiH3] KPUWHANPEXNPJT-UHFFFAOYSA-N 0.000 description 1
- 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 238000005553 drilling Methods 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 230000003301 hydrolyzing effect Effects 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 229910001412 inorganic anion Inorganic materials 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 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
- 239000007788 liquid Substances 0.000 description 1
- 230000001050 lubricating effect Effects 0.000 description 1
- 238000003754 machining Methods 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- MDLWEBWGXACWGE-UHFFFAOYSA-N octadecane Chemical compound [CH2]CCCCCCCCCCCCCCCCC MDLWEBWGXACWGE-UHFFFAOYSA-N 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 235000019198 oils Nutrition 0.000 description 1
- 150000003961 organosilicon compounds Chemical class 0.000 description 1
- 125000004437 phosphorous atom Chemical group 0.000 description 1
- 238000005096 rolling process Methods 0.000 description 1
- 238000007493 shaping process Methods 0.000 description 1
- 239000000344 soap Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000011550 stock solution Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- UFTFJSFQGQCHQW-UHFFFAOYSA-N triformin Chemical compound O=COCC(OC=O)COC=O UFTFJSFQGQCHQW-UHFFFAOYSA-N 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
- 238000011179 visual inspection Methods 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C23—COATING METALLIC MATERIAL; COATING MATERIAL WITH METALLIC MATERIAL; CHEMICAL SURFACE TREATMENT; DIFFUSION TREATMENT OF METALLIC MATERIAL; COATING BY VACUUM EVAPORATION, BY SPUTTERING, BY ION IMPLANTATION OR BY CHEMICAL VAPOUR DEPOSITION, IN GENERAL; INHIBITING CORROSION OF METALLIC MATERIAL OR INCRUSTATION IN GENERAL
- C23F—NON-MECHANICAL REMOVAL OF METALLIC MATERIAL FROM SURFACE; INHIBITING CORROSION OF METALLIC MATERIAL OR INCRUSTATION IN GENERAL; MULTI-STEP PROCESSES FOR SURFACE TREATMENT OF METALLIC MATERIAL INVOLVING AT LEAST ONE PROCESS PROVIDED FOR IN CLASS C23 AND AT LEAST ONE PROCESS COVERED BY SUBCLASS C21D OR C22F OR CLASS C25
- C23F11/00—Inhibiting corrosion of metallic material by applying inhibitors to the surface in danger of corrosion or adding them to the corrosive agent
- C23F11/08—Inhibiting corrosion of metallic material by applying inhibitors to the surface in danger of corrosion or adding them to the corrosive agent in other liquids
- C23F11/10—Inhibiting corrosion of metallic material by applying inhibitors to the surface in danger of corrosion or adding them to the corrosive agent in other liquids using organic inhibitors
- C23F11/14—Nitrogen-containing compounds
- C23F11/141—Amines; Quaternary ammonium compounds
-
- C—CHEMISTRY; METALLURGY
- C23—COATING METALLIC MATERIAL; COATING MATERIAL WITH METALLIC MATERIAL; CHEMICAL SURFACE TREATMENT; DIFFUSION TREATMENT OF METALLIC MATERIAL; COATING BY VACUUM EVAPORATION, BY SPUTTERING, BY ION IMPLANTATION OR BY CHEMICAL VAPOUR DEPOSITION, IN GENERAL; INHIBITING CORROSION OF METALLIC MATERIAL OR INCRUSTATION IN GENERAL
- C23F—NON-MECHANICAL REMOVAL OF METALLIC MATERIAL FROM SURFACE; INHIBITING CORROSION OF METALLIC MATERIAL OR INCRUSTATION IN GENERAL; MULTI-STEP PROCESSES FOR SURFACE TREATMENT OF METALLIC MATERIAL INVOLVING AT LEAST ONE PROCESS PROVIDED FOR IN CLASS C23 AND AT LEAST ONE PROCESS COVERED BY SUBCLASS C21D OR C22F OR CLASS C25
- C23F11/00—Inhibiting corrosion of metallic material by applying inhibitors to the surface in danger of corrosion or adding them to the corrosive agent
- C23F11/08—Inhibiting corrosion of metallic material by applying inhibitors to the surface in danger of corrosion or adding them to the corrosive agent in other liquids
- C23F11/10—Inhibiting corrosion of metallic material by applying inhibitors to the surface in danger of corrosion or adding them to the corrosive agent in other liquids using organic inhibitors
- C23F11/14—Nitrogen-containing compounds
- C23F11/141—Amines; Quaternary ammonium compounds
- C23F11/142—Hydroxy amines
-
- C—CHEMISTRY; METALLURGY
- C23—COATING METALLIC MATERIAL; COATING MATERIAL WITH METALLIC MATERIAL; CHEMICAL SURFACE TREATMENT; DIFFUSION TREATMENT OF METALLIC MATERIAL; COATING BY VACUUM EVAPORATION, BY SPUTTERING, BY ION IMPLANTATION OR BY CHEMICAL VAPOUR DEPOSITION, IN GENERAL; INHIBITING CORROSION OF METALLIC MATERIAL OR INCRUSTATION IN GENERAL
- C23F—NON-MECHANICAL REMOVAL OF METALLIC MATERIAL FROM SURFACE; INHIBITING CORROSION OF METALLIC MATERIAL OR INCRUSTATION IN GENERAL; MULTI-STEP PROCESSES FOR SURFACE TREATMENT OF METALLIC MATERIAL INVOLVING AT LEAST ONE PROCESS PROVIDED FOR IN CLASS C23 AND AT LEAST ONE PROCESS COVERED BY SUBCLASS C21D OR C22F OR CLASS C25
- C23F11/00—Inhibiting corrosion of metallic material by applying inhibitors to the surface in danger of corrosion or adding them to the corrosive agent
- C23F11/08—Inhibiting corrosion of metallic material by applying inhibitors to the surface in danger of corrosion or adding them to the corrosive agent in other liquids
- C23F11/10—Inhibiting corrosion of metallic material by applying inhibitors to the surface in danger of corrosion or adding them to the corrosive agent in other liquids using organic inhibitors
- C23F11/173—Macromolecular compounds
Definitions
- DE-PS 30 15 864 recommends polyoxyalkylenediamides with terminal carboxylic acid groups and their salts as corrosion-preventing additives for metalworking agent emulsions. These products are also said to improve the lubricating properties of the preparation.
- R is a monovalent hydrocarbon radical with up to 18 carbon atoms
- R ′ is a divalent hydrocarbon radical having up to 18 carbon atoms or a divalent hydrocarbonoxy radical having up to 18 carbon atoms
- the oxygen in the hydrocarbonoxy radical being in the form of an ether bond and the hydrocarbon portion of the hydrocarbonoxy radical being in the form of a divalent alkylene radical
- X is the anion of an acid
- x has an average value from 1 to about 100
- y has an average value from 0 to about 1000, where the ratio of y: x is no greater than about 50: 1.
- the object of the invention is to find further organosilicon compounds which have improved corrosion-inhibiting properties and give the person skilled in the art the possibility of formulating aqueous systems which are particularly suitable for dissipating heat with improved corrosion protection.
- this object is achieved by using methylpolysiloxanes with quaternary ammonium groups bonded to silicon atoms via carbon atoms, the quotient of the number of dimethylsiloxy groups and the number of quaternary ammonium groups being from 0.5 to 15, as corrosion inhibitors for predominantly water existing preparations, in particular coolants, such as water-mixed cooling lubricants, in quantities of 0.01 to 0.1% by weight, based on the total preparation in a form suitable for the application.
- coolants such as water-mixed cooling lubricants
- these dimethylsiloxy groups and quaternary ammonium groups which are in the specified ratio to one another, have excellent corrosion-inhibiting properties.
- the connections are soluble or well dispersible in water. They have a high chemical resistance in aqueous solution and are effective in a very small amount. Quantities of 0.01 to 0.1% by weight, based on the total preparation, which is diluted in a form suitable for the application, are generally sufficient to achieve good corrosion protection.
- a preferred embodiment of the subject of the present invention is that compounds of the general formula are used as methylpolysiloxanes with quaternary ammonium groups used in which R1 is the same or different in the molecule and is a methyl radical or the radical means R2 is the same or different in the molecule and denotes an alkyl radical with 1 to 18 carbon atoms or the radical R5-CONH- (CH2) 3-, in which R5 is an alkyl radical with 7 to 17 carbon atoms, R3, R4 are the same or different in the molecule and represent an alkyl radical with 1 to 4 carbon atoms, Z the rest or is X (-) is an inorganic or organic anion, n has a value from 5 to 20, m has a value from 1 to 10, wherein the quotient of the number of dimethylsiloxy groups and the number of quaternary ammonium groups has a value from 0.5 to 15.
- R2 can have different meanings within the polymeric molecule.
- R2 denotes an alkyl radical having 1 to 18 carbon atoms, such as e.g. the methyl, ethyl, propyl, isopropyl, butyl, isobutyl, hexyl, decyl, dodecyl or octadecyl radical.
- R2 can also mean the radical R5-CONH- (CH2) 3-.
- R5 is an alkyl radical with 7 to 17 carbon atoms, which is usually derived from a fatty acid R5COOH.
- R3 and R4 can also be the same or different within the polymeric molecule and mean an alkyl radical with 1 to 4 carbon atoms, such as e.g. the methyl, ethyl, propyl, isopropyl, butyl or isobutyl radical.
- the quaternary ammonium groups are each bonded to a silicon atom via the radical Z.
- the remainder Z corresponds to the formula
- X (-) is the counter ion of the ammonium group, so that the number of anions X (-) corresponds to the number of quaternary nitrogen atoms.
- X can be an inorganic or organic anion.
- X is usually an inorganic anion, such as a chlorine ion.
- An example of an organic anion is the acetate anion.
- n indicates the number of difunctional units.
- n has a value of 5 to 20.
- m denotes the methylsiloxy groups to which quaternary ammonium groups are bound laterally in the polymeric molecule.
- m has a value from 1 to 10. However, the condition must be fulfilled that the quotient of the number of dimethylsiloxy groups and the number of quaternary ammonium groups has a value of 0.5 to 15.
- a further preferred embodiment of the subject of the present invention is characterized in that compounds of the general formula are used as methylpolysiloxanes with quaternary ammonium groups used where R2, R3, R4, X (-) and Z have the meaning already given and p has a value from 1 to 29.
- these are linear methylpolysiloxanes which have quaternary ammonium groups only in the ⁇ , ⁇ position.
- the radicals R2, R3, R4, X (-) and Z have the meaning already given.
- the index p has a value from 1 to 29.
- the methylpolysiloxanes containing quaternary ammonium groups to be used according to the invention are preferably added to commercially available concentrates of the preparations.
- the compounds to be used according to the invention can e.g. dissolve in ethylene glycol, the user then diluting the stock solution to the appropriate concentration.
- the siloxanes can be added to the concentrated, commercially available emulsion, the essential components of which are vegetable, synthetic or animal oils, water and emulsifier. This stock emulsion is then diluted with water to the application concentration at the point of use.
- the siloxanes to be used according to the invention can be prepared, for example, according to DE-PS 37 19 086.
- This production process uses siloxanes of the general formula as starting compounds.
- R6 has the meaning of a methyl radical or the radical Q.
- Q is the rest The remaining radicals and indices have the meaning already given.
- the corrosion protection properties are determined in accordance with DIN 51 360, Part 2, for the testing of cooling lubricants in accordance with the specification of the determination of the corrosion protection properties of water-mixed cooling lubricants using the swarf / filter paper method. Reference is made to the DIN regulation for the details of the determination.
- the water-mixed cooling lubricant is provided with the anti-corrosion agent.
- Gray cast iron test chips which were checked visually for freedom from corrosion prior to the determination, are sieved and the fraction is used to carry out the tests used, where 30 ⁇ 5 chips have a total weight of 2 g.
- a round filter is placed in a Petri dish measuring 80 x 20 mm. 2 g of the chips are evenly applied to the surface of the round filter. The chips are evenly wetted with 2 ml of the aqueous preparation to be tested. Then the lid of the petri dish is put on. The Petri dishes prepared in this way are then exposed to a temperature of about 8 to 22 ° C. for two hours.
- the chips are then removed, the round filter rinsed under running water, swirled in acetone for about 5 seconds and dried at room temperature.
- the degree of corrosion of the corrosion markings on the round filter is then determined by visual inspection. The evaluation is based on the following classification:
- the compounds to be investigated for their corrosion-inhibiting properties are each dissolved in 0.1% by weight in the water-mixed cooling lubricant.
- the following connections were examined and evaluated:
Landscapes
- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Mechanical Engineering (AREA)
- Metallurgy (AREA)
- Organic Chemistry (AREA)
- Lubricants (AREA)
- Preventing Corrosion Or Incrustation Of Metals (AREA)
- Silicon Polymers (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE3837811 | 1988-11-08 | ||
| DE3837811A DE3837811C1 (it) | 1988-11-08 | 1988-11-08 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| EP0368119A1 EP0368119A1 (de) | 1990-05-16 |
| EP0368119B1 true EP0368119B1 (de) | 1992-12-30 |
Family
ID=6366687
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| EP89120152A Expired - Lifetime EP0368119B1 (de) | 1988-11-08 | 1989-10-31 | Verwendung von Methylpolysiloxanen mit quartären Ammoniumgruppen als Korrosionsinhibitoren für überwiegend aus Wasser bestehende Zubereitungen |
Country Status (3)
| Country | Link |
|---|---|
| US (1) | US5246607A (it) |
| EP (1) | EP0368119B1 (it) |
| DE (2) | DE3837811C1 (it) |
Families Citing this family (21)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE4309070A1 (de) * | 1993-03-20 | 1994-09-22 | Licentia Gmbh | Hochtemperaturbatterie |
| US5399737A (en) * | 1994-04-04 | 1995-03-21 | Alcon Laboratories, Inc. | Quaternary ammonium siloxane compounds and methods for their use |
| GB9503596D0 (en) * | 1995-02-23 | 1995-04-12 | Unilever Plc | Cleaning composition comprising quaternised poly-dimethylsiloxane and nonionic surfactant |
| DE19610234C2 (de) * | 1996-03-15 | 1999-08-05 | Goldschmidt Ag Th | Verwendung von Siloxanen mit betainischen und quaternären Gruppen zur Herstellung von Dämmstoffplatten auf Mineral- und Papierfaserbasis |
| DE19651287A1 (de) * | 1996-12-10 | 1998-06-18 | Wacker Chemie Gmbh | Ionische Organosiliciumverbindungen, deren Herstellung und Verwendung |
| ES2124195B1 (es) * | 1997-05-29 | 1999-09-16 | Krafft S A | Composicion anticongelante/refrigerante. |
| US6072735A (en) * | 1998-06-22 | 2000-06-06 | Lucent Technologies, Inc. | Built-in redundancy architecture for computer memories |
| US6384254B1 (en) * | 1999-11-04 | 2002-05-07 | Shin-Etsu Chemical Co., Ltd. | Quaternary ammonium salt-containing polysiloxane, making method, and fiber or fabric treating agent composition |
| GB2359500B (en) * | 2000-02-23 | 2004-08-18 | Illinois Tool Works | Corrosion inhibitors |
| US6866797B1 (en) | 2000-08-03 | 2005-03-15 | Bj Services Company | Corrosion inhibitors and methods of use |
| US6482969B1 (en) * | 2001-10-24 | 2002-11-19 | Dow Corning Corporation | Silicon based quaternary ammonium functional compositions and methods for making them |
| WO2003101947A2 (en) * | 2002-05-31 | 2003-12-11 | Ciba Specialty Chemicals Holding Inc. | Alkylaminosiloxanes as corrosion inhibitors |
| US7622512B2 (en) * | 2005-12-21 | 2009-11-24 | Bausch & Lomb Incorporated | Cationic hydrophilic siloxanyl monomers |
| US7759408B2 (en) * | 2005-12-21 | 2010-07-20 | Bausch & Lomb Incorporated | Silicon-containing monomers end-capped with polymerizable cationic hydrophilic groups |
| US20070161769A1 (en) * | 2006-01-06 | 2007-07-12 | Schorzman Derek A | Polymerizable silicon-containing monomer bearing pendant cationic hydrophilic groups |
| US7960447B2 (en) * | 2006-04-13 | 2011-06-14 | Bausch & Lomb Incorporated | Cationic end-capped siloxane prepolymer for reduced cross-link density |
| US20080152540A1 (en) * | 2006-12-22 | 2008-06-26 | Bausch & Lomb Incorporated | Packaging solutions |
| US7691917B2 (en) | 2007-06-14 | 2010-04-06 | Bausch & Lomb Incorporated | Silcone-containing prepolymers |
| ATE509136T1 (de) * | 2008-10-21 | 2011-05-15 | Atotech Deutschland Gmbh | Nachbehandlungszusammensetzung zur steigerung des rostschutzes von metall oder metalllegierungsflächen |
| CN102317354B (zh) * | 2009-01-22 | 2015-06-03 | 高露洁-棕榄公司 | 烷基季铵硅酮化合物 |
| DE102013219046A1 (de) | 2013-09-23 | 2015-03-26 | Rudolf Gmbh | Polysiloxane mit quaternierten heterocyclischen Gruppen |
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| US3121692A (en) * | 1958-12-02 | 1964-02-18 | Union Carbide Corp | Antifreeze compositions |
| US3085908A (en) * | 1959-05-26 | 1963-04-16 | Union Carbide Corp | Aminosilicon treated metals and methods of treatment and production |
| US3248329A (en) * | 1961-04-06 | 1966-04-26 | Union Carbide Corp | Aminosilicone-silicate polymers as corrosion inhibitors |
| US3203969A (en) * | 1961-04-06 | 1965-08-31 | Union Carbide Corp | Amino silicone-silicate polymers |
| US3471541A (en) * | 1963-08-27 | 1969-10-07 | Union Carbide Corp | N,n-disubstituted aminoalkoxyalkylsilicon compounds and derivatives thereof |
| US3402191A (en) * | 1963-08-27 | 1968-09-17 | Union Carbide Corp | N, n-disubstituted aminoalkylsiloxane copolymers and amine oxide, quaternary ammonium salt, and coordination compounds of transition metal derivatives thereof |
| BE666745A (it) * | 1964-07-14 | 1966-01-12 | ||
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| USRE30885E (en) * | 1981-03-13 | 1982-03-23 | Cincinnati Milacron Inc. | Novel diamide and lubricants containing same |
| GR77641B (it) * | 1981-09-25 | 1984-09-25 | Procter & Gamble | |
| JPS60106891A (ja) * | 1983-11-14 | 1985-06-12 | Shin Etsu Chem Co Ltd | 作動流体 |
| GB8400899D0 (en) * | 1984-01-13 | 1984-02-15 | Procter & Gamble | Granular detergent compositions |
| US4564456A (en) * | 1984-06-01 | 1986-01-14 | Dow Corning Corporation | Method of treating water to inhibit corrosion and diminish mineral deposition |
| DE3427499A1 (de) * | 1984-07-26 | 1986-02-13 | Bayer Ag, 5090 Leverkusen | Elektroviskose fluessigkeiten |
| US4639321A (en) * | 1985-01-22 | 1987-01-27 | The Procter And Gamble Company | Liquid detergent compositions containing organo-functional polysiloxanes |
| DE3614412A1 (de) * | 1986-04-29 | 1987-11-05 | Goldschmidt Ag Th | Erdoel mit erniedrigtem stockpunkt |
| DE3719086C1 (de) * | 1987-06-06 | 1988-10-27 | Goldschmidt Ag Th | Diquartaere Polysiloxane,deren Herstellung und Verwendung in kosmetischen Zubereitungen |
| US4844888A (en) * | 1987-11-13 | 1989-07-04 | The Gillette Company | Polysiloxane cosmetic composition |
-
1988
- 1988-11-08 DE DE3837811A patent/DE3837811C1/de not_active Expired - Lifetime
-
1989
- 1989-10-12 US US07/420,348 patent/US5246607A/en not_active Expired - Fee Related
- 1989-10-31 EP EP89120152A patent/EP0368119B1/de not_active Expired - Lifetime
- 1989-10-31 DE DE8989120152T patent/DE58903171D1/de not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| DE3837811C1 (it) | 1990-04-26 |
| US5246607A (en) | 1993-09-21 |
| DE58903171D1 (de) | 1993-02-11 |
| EP0368119A1 (de) | 1990-05-16 |
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