GB882061A - Organosilicon acylamino compounds and process for producing the same - Google Patents
Organosilicon acylamino compounds and process for producing the sameInfo
- Publication number
- GB882061A GB882061A GB30944/57A GB3094457A GB882061A GB 882061 A GB882061 A GB 882061A GB 30944/57 A GB30944/57 A GB 30944/57A GB 3094457 A GB3094457 A GB 3094457A GB 882061 A GB882061 A GB 882061A
- Authority
- GB
- United Kingdom
- Prior art keywords
- dimethylsiloxane
- radical
- dimethylsiloxane copolymer
- formula
- siloxane
- 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
Links
- 238000000034 method Methods 0.000 title abstract 2
- 125000004442 acylamino group Chemical group 0.000 title 1
- -1 aryloxy silanes Chemical class 0.000 abstract 6
- 229920001577 copolymer Polymers 0.000 abstract 5
- KJFMBFZCATUALV-UHFFFAOYSA-N phenolphthalein Chemical compound C1=CC(O)=CC=C1C1(C=2C=CC(O)=CC=2)C2=CC=CC=C2C(=O)O1 KJFMBFZCATUALV-UHFFFAOYSA-N 0.000 abstract 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 abstract 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 abstract 3
- KPUWHANPEXNPJT-UHFFFAOYSA-N disiloxane Chemical class [SiH3]O[SiH3] KPUWHANPEXNPJT-UHFFFAOYSA-N 0.000 abstract 3
- 239000000376 reactant Substances 0.000 abstract 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 abstract 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 abstract 2
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 abstract 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 abstract 2
- 239000002253 acid Substances 0.000 abstract 2
- 150000004820 halides Chemical class 0.000 abstract 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract 2
- IJVLVRYLIMQVDD-UHFFFAOYSA-N 1,3-thiazole-2-carboxylic acid Chemical compound OC(=O)C1=NC=CS1 IJVLVRYLIMQVDD-UHFFFAOYSA-N 0.000 abstract 1
- KOPFEFZSAMLEHK-UHFFFAOYSA-N 1h-pyrazole-5-carboxylic acid Chemical compound OC(=O)C=1C=CNN=1 KOPFEFZSAMLEHK-UHFFFAOYSA-N 0.000 abstract 1
- SMNDYUVBFMFKNZ-UHFFFAOYSA-N 2-furoic acid Chemical compound OC(=O)C1=CC=CO1 SMNDYUVBFMFKNZ-UHFFFAOYSA-N 0.000 abstract 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 abstract 1
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 abstract 1
- 239000002250 absorbent Substances 0.000 abstract 1
- 230000002745 absorbent Effects 0.000 abstract 1
- 150000001253 acrylic acids Chemical class 0.000 abstract 1
- 125000003342 alkenyl group Chemical group 0.000 abstract 1
- 125000003545 alkoxy group Chemical group 0.000 abstract 1
- 125000000217 alkyl group Chemical group 0.000 abstract 1
- 150000008064 anhydrides Chemical class 0.000 abstract 1
- 150000005840 aryl radicals Chemical group 0.000 abstract 1
- 238000010533 azeotropic distillation Methods 0.000 abstract 1
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid group Chemical group C(C1=CC=CC=C1)(=O)O WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 abstract 1
- 230000015572 biosynthetic process Effects 0.000 abstract 1
- 239000006227 byproduct Substances 0.000 abstract 1
- 150000001728 carbonyl compounds Chemical class 0.000 abstract 1
- 239000007795 chemical reaction product Substances 0.000 abstract 1
- 239000011248 coating agent Substances 0.000 abstract 1
- 238000000576 coating method Methods 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 abstract 1
- 125000004122 cyclic group Chemical group 0.000 abstract 1
- 150000002148 esters Chemical class 0.000 abstract 1
- 125000005843 halogen group Chemical group 0.000 abstract 1
- 125000000623 heterocyclic group Chemical group 0.000 abstract 1
- 239000000463 material Substances 0.000 abstract 1
- 150000002814 niacins Chemical class 0.000 abstract 1
- 235000001968 nicotinic acid Nutrition 0.000 abstract 1
- 239000003921 oil Substances 0.000 abstract 1
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid group Chemical group C(CCCCCCC\C=C/CCCCCCCC)(=O)O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 abstract 1
- 125000005375 organosiloxane group Chemical group 0.000 abstract 1
- 239000003208 petroleum Substances 0.000 abstract 1
- 229920000642 polymer Polymers 0.000 abstract 1
- 238000002360 preparation method Methods 0.000 abstract 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 abstract 1
- WRHZVMBBRYBTKZ-UHFFFAOYSA-N pyrrole-2-carboxylic acid Chemical compound OC(=O)C1=CC=CN1 WRHZVMBBRYBTKZ-UHFFFAOYSA-N 0.000 abstract 1
- 150000003254 radicals Chemical class 0.000 abstract 1
- 239000011541 reaction mixture Substances 0.000 abstract 1
- 229920005989 resin Polymers 0.000 abstract 1
- 239000011347 resin Substances 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
- 229910000077 silane Inorganic materials 0.000 abstract 1
- 239000002904 solvent Substances 0.000 abstract 1
- 239000007858 starting material Substances 0.000 abstract 1
- 150000003512 tertiary amines Chemical class 0.000 abstract 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 abstract 1
- QERYCTSHXKAMIS-UHFFFAOYSA-N thiophene-2-carboxylic acid Chemical compound OC(=O)C1=CC=CS1 QERYCTSHXKAMIS-UHFFFAOYSA-N 0.000 abstract 1
- 239000008096 xylene Substances 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/0834—Compounds having one or more O-Si linkage
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Silicon Polymers (AREA)
Abstract
The invention comprises organosiloxane and alkoxy or aryloxy silanes containing a siliconbond acylaminoalkyl radical of the formula <FORM:0882061/IV (a)/1> wherein R is an alkyl, alkenyl or aryl radical or a monovalent heterocyclic ring and a is an integer of at least 3. The compounds are made by reacting a siloxane or silane containing an aminoalkyl radical of the formula H2N(CH2)a-with an organic carbonyl compound of the formula <FORM:0882061/IV (a)/2> wherein M is a halogen atom or an -OH, -OR or <FORM:0882061/IV (a)/3> radical, at a temperature within the range of 0 DEG to 300 DEG C. Aminoalkyl silanes and siloxanes used as starting materials are described in Specifications 882,096 and 882,097. Organic reactants specified are formic, acetic, oleic, stearic, benzoic, p-aminobenzoic, p-nitrobenzoic, acrylic and nicotinic acids, 2-carboxypyrrole, 2-carboxyfuran, 2-carboxythiophene, 2-carboxythiazole, 3-carboxypyrazole and 2-carboxyglyoxaline; and esters, acid halides and anhydrides thereof, many examples of which are given. The reaction is preferably effected in a solvent for the reactants, e.g. water, tetrahydrofuran, petroleum ether, benzene, toluene or xylene. By-products are removed from the reaction mixture, e.g. water is removed by azeotropic distillation or by hydrophilic absorbents; HCl is removed together with unreacted organic reactant under reduced pressure; acid halides are removed by salt formation by adding tertiary amines, e.g. pyridine and quinoline. The examples describe the preparation of (1) d -dichloroacetylaminobutylmethyldiethoxysilane; (2) d -benzoylaminobutylmethylsiloxane-dimethylsiloxane copolymer; (3) d -oleylaminobutylmethylsiloxane-dimethylsiloxane copolymer; (4) d -p-nitrobenzoylaminobutylmethylsiloxane-dimethylsiloxane copolymer, (5) g -benzoylaminopropylethoxydihydroxysilane; (6) reaction product of d -aminobutylmethylsiloxane and phenolphthalein; (7)g -p - aminobenzoylaminopropylmethylsiloxane - dimethylsiloxane and g -o-hydroxybenzoylaminopropylmethylsiloxane-dimethylsiloxane copolymers; (8) cyclic g -acetylaminopropylmethylsiloxanes; and (9) g -acryloylaminopropylmethylsiloxane-dimethylsiloxane copolymer. Uses: the polymers obtained from phenolphthalein are useful as indicators in siloxane equilibrating procedures; for modifying siloxane oils, gums and resins for coating materials; as skin protectants. Reference has been directed by the Comptroller to Specifications 684,296, 769,498 and 795,894.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US882061XA | 1956-10-12 | 1956-10-12 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB882061A true GB882061A (en) | 1961-11-08 |
Family
ID=22210001
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB30944/57A Expired GB882061A (en) | 1956-10-12 | 1957-10-03 | Organosilicon acylamino compounds and process for producing the same |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB882061A (en) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3447246A1 (en) * | 1984-01-04 | 1985-07-11 | General Electric Co., Schenectady, N.Y. | METHOD FOR PRODUCING ZWITTERIONIC SILOXANE POLYMERS |
| US7956150B2 (en) | 2004-12-16 | 2011-06-07 | Dow Corning Corporation | Amide-substituted silicones and methods for their preparation and use |
| US8618039B2 (en) | 2006-12-15 | 2013-12-31 | Dow Corning India | Granular materials for finishing denim |
| WO2023173368A1 (en) * | 2022-03-17 | 2023-09-21 | Dow Global Technologies Llc | Polymeric brominated flame retardant, composition, and cable with same |
-
1957
- 1957-10-03 GB GB30944/57A patent/GB882061A/en not_active Expired
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3447246A1 (en) * | 1984-01-04 | 1985-07-11 | General Electric Co., Schenectady, N.Y. | METHOD FOR PRODUCING ZWITTERIONIC SILOXANE POLYMERS |
| US7956150B2 (en) | 2004-12-16 | 2011-06-07 | Dow Corning Corporation | Amide-substituted silicones and methods for their preparation and use |
| US8618039B2 (en) | 2006-12-15 | 2013-12-31 | Dow Corning India | Granular materials for finishing denim |
| WO2023173368A1 (en) * | 2022-03-17 | 2023-09-21 | Dow Global Technologies Llc | Polymeric brominated flame retardant, composition, and cable with same |
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