GB815159A - Organotitanium compounds - Google Patents
Organotitanium compoundsInfo
- Publication number
- GB815159A GB815159A GB12579/56A GB1257956A GB815159A GB 815159 A GB815159 A GB 815159A GB 12579/56 A GB12579/56 A GB 12579/56A GB 1257956 A GB1257956 A GB 1257956A GB 815159 A GB815159 A GB 815159A
- Authority
- GB
- United Kingdom
- Prior art keywords
- titanate
- groupings
- titanium
- mols
- grouping
- 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
- 150000001875 compounds Chemical class 0.000 title abstract 2
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 abstract 24
- 239000010936 titanium Substances 0.000 abstract 20
- -1 aromatic monocarboxylic acid Chemical class 0.000 abstract 17
- 229910052719 titanium Inorganic materials 0.000 abstract 17
- 125000004429 atom Chemical group 0.000 abstract 11
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 abstract 8
- 125000004423 acyloxy group Chemical group 0.000 abstract 8
- 125000003545 alkoxy group Chemical group 0.000 abstract 8
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 abstract 7
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 abstract 6
- FPCJKVGGYOAWIZ-UHFFFAOYSA-N butan-1-ol;titanium Chemical compound [Ti].CCCCO.CCCCO.CCCCO.CCCCO FPCJKVGGYOAWIZ-UHFFFAOYSA-N 0.000 abstract 6
- 125000001931 aliphatic group Chemical group 0.000 abstract 5
- 229920006395 saturated elastomer Polymers 0.000 abstract 5
- ODIGIKRIUKFKHP-UHFFFAOYSA-N (n-propan-2-yloxycarbonylanilino) acetate Chemical compound CC(C)OC(=O)N(OC(C)=O)C1=CC=CC=C1 ODIGIKRIUKFKHP-UHFFFAOYSA-N 0.000 abstract 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 abstract 3
- 235000021355 Stearic acid Nutrition 0.000 abstract 3
- 229910003088 Ti−O−Ti Inorganic materials 0.000 abstract 3
- 239000002253 acid Substances 0.000 abstract 3
- 125000004103 aminoalkyl group Chemical group 0.000 abstract 3
- 125000005843 halogen group Chemical group 0.000 abstract 3
- 125000002768 hydroxyalkyl group Chemical group 0.000 abstract 3
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 abstract 3
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 abstract 3
- 239000008117 stearic acid Substances 0.000 abstract 3
- 125000003696 stearoyl group Chemical group O=C([*])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])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 abstract 3
- VXUYXOFXAQZZMF-UHFFFAOYSA-N titanium(IV) isopropoxide Chemical compound CC(C)O[Ti](OC(C)C)(OC(C)C)OC(C)C VXUYXOFXAQZZMF-UHFFFAOYSA-N 0.000 abstract 3
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 abstract 2
- AKNUHUCEWALCOI-UHFFFAOYSA-N N-ethyldiethanolamine Chemical compound OCCN(CC)CCO AKNUHUCEWALCOI-UHFFFAOYSA-N 0.000 abstract 2
- SLINHMUFWFWBMU-UHFFFAOYSA-N Triisopropanolamine Chemical compound CC(O)CN(CC(C)O)CC(C)O SLINHMUFWFWBMU-UHFFFAOYSA-N 0.000 abstract 2
- LVTYICIALWPMFW-UHFFFAOYSA-N diisopropanolamine Chemical compound CC(O)CNCC(C)O LVTYICIALWPMFW-UHFFFAOYSA-N 0.000 abstract 2
- 229940043276 diisopropanolamine Drugs 0.000 abstract 2
- POULHZVOKOAJMA-UHFFFAOYSA-N dodecanoic acid Chemical compound CCCCCCCCCCCC(O)=O POULHZVOKOAJMA-UHFFFAOYSA-N 0.000 abstract 2
- 239000000295 fuel oil Substances 0.000 abstract 2
- ORTFAQDWJHRMNX-UHFFFAOYSA-N hydroxidooxidocarbon(.) Chemical compound O[C]=O ORTFAQDWJHRMNX-UHFFFAOYSA-N 0.000 abstract 2
- FBUKVWPVBMHYJY-UHFFFAOYSA-N nonanoic acid Chemical compound CCCCCCCCC(O)=O FBUKVWPVBMHYJY-UHFFFAOYSA-N 0.000 abstract 2
- 125000001402 nonanoyl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 abstract 2
- 238000003756 stirring Methods 0.000 abstract 2
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 abstract 1
- 125000006176 2-ethylbutyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(C([H])([H])*)C([H])([H])C([H])([H])[H] 0.000 abstract 1
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 abstract 1
- XRHGYUZYPHTUJZ-UHFFFAOYSA-N 4-chlorobenzoic acid Chemical compound OC(=O)C1=CC=C(Cl)C=C1 XRHGYUZYPHTUJZ-UHFFFAOYSA-N 0.000 abstract 1
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 abstract 1
- 239000005639 Lauric acid Substances 0.000 abstract 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 abstract 1
- 239000005642 Oleic acid Substances 0.000 abstract 1
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 abstract 1
- 239000005643 Pelargonic acid Substances 0.000 abstract 1
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 abstract 1
- 230000010933 acylation Effects 0.000 abstract 1
- 238000005917 acylation reaction Methods 0.000 abstract 1
- 125000000217 alkyl group Chemical group 0.000 abstract 1
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 abstract 1
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 abstract 1
- 239000000919 ceramic Substances 0.000 abstract 1
- 239000008199 coating composition Substances 0.000 abstract 1
- 238000001246 colloidal dispersion Methods 0.000 abstract 1
- 239000006185 dispersion Substances 0.000 abstract 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 abstract 1
- 230000008020 evaporation Effects 0.000 abstract 1
- 238000001704 evaporation Methods 0.000 abstract 1
- 239000004744 fabric Substances 0.000 abstract 1
- 229910052500 inorganic mineral Inorganic materials 0.000 abstract 1
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 abstract 1
- 239000003350 kerosene Substances 0.000 abstract 1
- 239000011707 mineral Substances 0.000 abstract 1
- 239000000203 mixture Substances 0.000 abstract 1
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 abstract 1
- 239000000049 pigment Substances 0.000 abstract 1
- 239000005871 repellent Substances 0.000 abstract 1
- 150000004671 saturated fatty acids Chemical class 0.000 abstract 1
- 239000002904 solvent Substances 0.000 abstract 1
- 235000015096 spirit Nutrition 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
- C07F7/003—Compounds containing elements of Groups 4 or 14 of the Periodic Table without C-Metal linkages
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Cosmetics (AREA)
Abstract
Fuel oil compositions, coating compositions and pigment dispersions, comprise kerosene or mineral spirits containing monomeric or polymeric b -aminoalkyl acyl titanates in which the Ti is quadrivalent, the monomeric form contains Ti covalently bonded to 1 to 3 mols. of b -aminoalkoxy groupings, 0.2 to 2 mols. of acyloxy groupings and 0 to 2.8 mols. of C2-18 alkoxy groupings per gram atom of titanium and the polymeric form contains from 1 to 2.8 Ti-O-Ti bonds per titanium atom, 1 to 2.8 mols. of covalently bonded b -aminoalkoxy grouping per gram atom of titanium and 0.2 to 2 mols. of covalently bonded acyloxy groupings per gram atom of titanium, any remaining covalencies being satisfied by C2-18 alkoxy groupings, said acyloxy grouping being a C2-20 grouping derived from a saturated or unsaturated aliphatic or aromatic monocarboxylic acid which may bear unreactive halogen substituents and said b -aminoalkoxy grouping being derived from a b -aminoalcohol of the formula: HO-CHR11-CH2-NR111R1111 where R11 is H or a C1-5 aliphatic hydrocarbon grouping and R111 and R1111 are H, C1-20 aliphatic hydrocarbon groupings, C2-9 aminoalkyl groupings or C2-5 hydroxyalkyl groupings. A solution of a b -aminoethylethanolamine oleoyl titanate in xylene is brushed on to a ceramic body to give a thin water-repellent film thereon after evaporation of the solvent. Specification 755,728 is referred to.ALSO:Polymeric b -aminoalkyl acyl titanates in which the Ti is quadrivalent and which contain from 1 to 2.8 Ti-O-Ti bonds per titanium atom, 1 to 2.8 mols. of covalently bonded b -aminoalkoxy groupings per gram atom of titanium and 0.2 to 2 mols. of covalently bonded acyloxy groupings per gram atom of titanium, any remaining covalencies being satisfied by C2-18 alkoxy groupings, said acyloxy grouping being a C2-20 grouping derived from a saturated or unsaturated aliphatic or aromatic monocarboxylic acid which may bear unreactive halogen substituents and said b -aminoalkoxy grouping being derived from a b -aminoalcohol of the formula HO-CHR11-CH2-NR111R1111, where R11 is H or a C1-5 aliphatic hydrocarbon grouping and R111 and R1111 are H, C1-20 aliphatic hydrocarbon groupings, C2-9 aminoalkyl groupings or C2-5 hydroxyalkyl groupings, are prepared by acylating a condensed C2-18 alkyl titanate with from 0.2 to 2 mols. of an acid R1.COOH, where R1 is a C2-20 saturated or unsaturated aliphatic or aromatic radical, for each gram atom of titanium present and reacting the condensed alkoxy titanium acylate product with from 1 to 2.8 mols. of a b -aminoalcohol of the formula HO-CHR11-CH2-NR111R1111 per gram atom of titanium present. In an example, slightly aqueous butanol is added with stirring to a butanol solution of butyl titanate to produce a solution of condensed butyl titanate, which is acylated with stearic acid and the resulting condensed stearoyl butyl titanate is reacted with triethanolamine to give a condensed triethanolamine stearoyl titanate. Uses.-The above products may be added to fuel oils or to aqueous systems to give colloidal dispersions suitable for imparting water-repellancy to fabrics. Specification 755,728 is referred to.ALSO:The invention comprises monomeric and polymeric b -aminoalkyl acyl titanates in which the Ti is quadrivalent, the monomeric form contains Ti covalently bonded to 1 to 3 mols. of b -aminoalkoxy groups, 0.2 to 2 mols. of acyloxy groupings and 0 to 2.8 mols. of C2-18 alkoxy groupings per gram atom of titanium and the polymeric form contains from 1 to 2.8 Ti-O-Ti bonds per titanium atom, 1 to 2.8 mols. of covalently bonded b -aminoalkoxy groupings per gram atom of titanium and 0.2 to 2 mols. of covalently bonded acyloxy groupings per gram atom of titanium, any remaining covalencies being satisfied by C2-18 alkoxy groupings, said acyloxy grouping being a C2-20 grouping derived from a saturated or unsaturated aliphatic or aromatic monocarboxylic acid and said b -aminoalkoxy grouping being derived from a b -aminoalcohol of the formula HO-CHR11-CH2-NR111R1111 where R11 is H or a C1-5 aliphatic hydrocarbon grouping and R111 and R1111 are H,C1-20 aliphatic hydrocarbon groupings, C2-9 aminoalkyl groupings or C2-5 hydroxyalkyl groupings. The compounds are prepared by reacting an alkyl titanate of the formula Ti(OR)4, where R is a C2-18 alkyl group, or the corresponding condensed alkyl titanate, with an appropriate amount of an acid R1.COOH, where R1 is a C2-20 saturated or unsaturated aliphatic or aromatic radical, to form an alkoxy titanium acylate of the formula (RO)4-nTi(OCOR1)n, where n is from 0.2 to 2, or the corresponding condensed alkoxy titanium acylate, and reacting the products respectively with from 1 to 3 or from 1 to 2.8 mols. per gram atom of titanium of a b -aminoalcohol of the formula HO-CHR11-CH2-NR111R1111 The acid employed for acylation may contain non-reactive halogen atoms but is preferably a C12-18 saturated fatty acid. In the examples isopropyl titanate is acylated with stearic acid and the stearoyl isopropyl titanate is reacted with triethanolamine or triisopropanolamine to give a triethanolamine or triisopropanolamine stearoyl titanate; isopropyl titanate is acylated with lauric acid and the lauroyl isopropyl titanate is reacted with monoethanolamine to give a monoethanolamine lauryl titanate; butyl titanate is acylated with oleic acid and the oleoyl butyl titanate is reacted with b -aminoethylethanolamine to give a b -aminoethylethanolamine oleoyl titanate; 2-ethylbutyl titanate is acylated with pelargonic acid and the pelargonoyl 2-ethylbutyl titanate is reacted with diisopropanolamine to give a diisopropanolamine pelargonoyl titanate; butyl titanate is acylated with acetic acid and the acetyl butyl titanate is reacted with N-ethyldiethanolamine to give an N-ethyldiethanolamine acetyl titanate; isopropyl titanate is acylated with benzoic or para-chlorobenzoic acid and the benzoyl or para-chlorobenzoyl isopropyl titanate is reacted with triethanolamine to give a triethanolamine benzoyl or para-chlorobenzoyl titanate; slightly aqueous butanol is added with stirring to a butanol solution of butyl titanate to produce a solution of condensed butyl titanate, which is acylated with stearic acid and the condensed stearoyl butyl titanate is reacted with triethanolamine to give a condensed triethanolamine stearoyl titanate. Specification 755,728 is referred to.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US815159XA | 1955-05-16 | 1955-05-16 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB815159A true GB815159A (en) | 1959-06-17 |
Family
ID=22164693
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB12579/56A Expired GB815159A (en) | 1955-05-16 | 1956-04-24 | Organotitanium compounds |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB815159A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2039673A5 (en) * | 1969-03-18 | 1971-01-15 | British Titan Products |
-
1956
- 1956-04-24 GB GB12579/56A patent/GB815159A/en not_active Expired
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2039673A5 (en) * | 1969-03-18 | 1971-01-15 | British Titan Products |
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