GB812505A - Titanate ester compositions and processes for imparting water-repellency - Google Patents
Titanate ester compositions and processes for imparting water-repellencyInfo
- Publication number
- GB812505A GB812505A GB8926/57A GB892657A GB812505A GB 812505 A GB812505 A GB 812505A GB 8926/57 A GB8926/57 A GB 8926/57A GB 892657 A GB892657 A GB 892657A GB 812505 A GB812505 A GB 812505A
- Authority
- GB
- United Kingdom
- Prior art keywords
- triethanolamine
- titanate
- silicone
- ester
- treated
- 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
- -1 Titanate ester Chemical class 0.000 title abstract 10
- 239000000203 mixture Substances 0.000 title abstract 7
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 abstract 19
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 abstract 12
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 abstract 12
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 abstract 8
- 239000000839 emulsion Substances 0.000 abstract 8
- 229960004418 trolamine Drugs 0.000 abstract 8
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 abstract 7
- 229920001296 polysiloxane Polymers 0.000 abstract 6
- 239000003054 catalyst Substances 0.000 abstract 5
- 229920002050 silicone resin Polymers 0.000 abstract 5
- XJDNKRIXUMDJCW-UHFFFAOYSA-J titanium tetrachloride Chemical compound Cl[Ti](Cl)(Cl)Cl XJDNKRIXUMDJCW-UHFFFAOYSA-J 0.000 abstract 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract 4
- 239000000047 product Substances 0.000 abstract 4
- 239000000126 substance Substances 0.000 abstract 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract 4
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 abstract 3
- 150000002148 esters Chemical class 0.000 abstract 3
- 229920001223 polyethylene glycol Polymers 0.000 abstract 3
- LLZRNZOLAXHGLL-UHFFFAOYSA-J titanic acid Chemical compound O[Ti](O)(O)O LLZRNZOLAXHGLL-UHFFFAOYSA-J 0.000 abstract 3
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 abstract 2
- 229920002134 Carboxymethyl cellulose Polymers 0.000 abstract 2
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 abstract 2
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 abstract 2
- 150000001298 alcohols Chemical class 0.000 abstract 2
- 125000000217 alkyl group Chemical group 0.000 abstract 2
- 150000001412 amines Chemical class 0.000 abstract 2
- 239000001768 carboxy methyl cellulose Substances 0.000 abstract 2
- 235000010948 carboxy methyl cellulose Nutrition 0.000 abstract 2
- 239000008112 carboxymethyl-cellulose Substances 0.000 abstract 2
- PAFZNILMFXTMIY-UHFFFAOYSA-N cyclohexylamine Chemical compound NC1CCCCC1 PAFZNILMFXTMIY-UHFFFAOYSA-N 0.000 abstract 2
- 239000002657 fibrous material Substances 0.000 abstract 2
- 239000007788 liquid Substances 0.000 abstract 2
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 abstract 2
- 239000011148 porous material Substances 0.000 abstract 2
- 239000003784 tall oil Substances 0.000 abstract 2
- 229910052719 titanium Inorganic materials 0.000 abstract 2
- 239000010936 titanium Substances 0.000 abstract 2
- ICLYJLBTOGPLMC-KVVVOXFISA-N (z)-octadec-9-enoate;tris(2-hydroxyethyl)azanium Chemical compound OCCN(CCO)CCO.CCCCCCCC\C=C/CCCCCCCC(O)=O ICLYJLBTOGPLMC-KVVVOXFISA-N 0.000 abstract 1
- QHQZEEGNGSZBOL-UHFFFAOYSA-N 2-(aminomethyl)-2-(hydroxymethyl)propane-1,3-diol Chemical compound NCC(CO)(CO)CO QHQZEEGNGSZBOL-UHFFFAOYSA-N 0.000 abstract 1
- IOAOAKDONABGPZ-UHFFFAOYSA-N 2-amino-2-ethylpropane-1,3-diol Chemical compound CCC(N)(CO)CO IOAOAKDONABGPZ-UHFFFAOYSA-N 0.000 abstract 1
- JCBPETKZIGVZRE-UHFFFAOYSA-N 2-aminobutan-1-ol Chemical compound CCC(N)CO JCBPETKZIGVZRE-UHFFFAOYSA-N 0.000 abstract 1
- KDSNLYIMUZNERS-UHFFFAOYSA-N 2-methylpropanamine Chemical compound CC(C)CN KDSNLYIMUZNERS-UHFFFAOYSA-N 0.000 abstract 1
- RPNUMPOLZDHAAY-UHFFFAOYSA-N Diethylenetriamine Chemical compound NCCNCCN RPNUMPOLZDHAAY-UHFFFAOYSA-N 0.000 abstract 1
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 abstract 1
- 229920000877 Melamine resin Polymers 0.000 abstract 1
- 239000002202 Polyethylene glycol Substances 0.000 abstract 1
- 235000021355 Stearic acid Nutrition 0.000 abstract 1
- 229910003074 TiCl4 Inorganic materials 0.000 abstract 1
- XSTXAVWGXDQKEL-UHFFFAOYSA-N Trichloroethylene Chemical group ClC=C(Cl)Cl XSTXAVWGXDQKEL-UHFFFAOYSA-N 0.000 abstract 1
- 229920001807 Urea-formaldehyde Polymers 0.000 abstract 1
- 125000004429 atom Chemical group 0.000 abstract 1
- 125000004432 carbon atom Chemical group C* 0.000 abstract 1
- 239000011111 cardboard Substances 0.000 abstract 1
- 239000007859 condensation product Substances 0.000 abstract 1
- 235000014113 dietary fatty acids Nutrition 0.000 abstract 1
- 238000010790 dilution Methods 0.000 abstract 1
- 239000012895 dilution Substances 0.000 abstract 1
- 239000003995 emulsifying agent Substances 0.000 abstract 1
- 230000032050 esterification Effects 0.000 abstract 1
- 238000005886 esterification reaction Methods 0.000 abstract 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 abstract 1
- 239000000194 fatty acid Substances 0.000 abstract 1
- 229930195729 fatty acid Natural products 0.000 abstract 1
- 150000004665 fatty acids Chemical class 0.000 abstract 1
- 239000000417 fungicide Substances 0.000 abstract 1
- 238000010438 heat treatment Methods 0.000 abstract 1
- 239000002917 insecticide Substances 0.000 abstract 1
- 239000010985 leather Substances 0.000 abstract 1
- 229940057995 liquid paraffin Drugs 0.000 abstract 1
- 239000000463 material Substances 0.000 abstract 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 1
- LAQFLZHBVPULPL-UHFFFAOYSA-N methyl(phenyl)silicon Chemical compound C[Si]C1=CC=CC=C1 LAQFLZHBVPULPL-UHFFFAOYSA-N 0.000 abstract 1
- GLPXGXQOVMEKIJ-UHFFFAOYSA-N octadecan-1-amine;octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC[NH3+].CCCCCCCCCCCCCCCCCC([O-])=O GLPXGXQOVMEKIJ-UHFFFAOYSA-N 0.000 abstract 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 abstract 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 abstract 1
- UPHWVVKYDQHTCF-UHFFFAOYSA-N octadecylazanium;acetate Chemical compound CC(O)=O.CCCCCCCCCCCCCCCCCCN UPHWVVKYDQHTCF-UHFFFAOYSA-N 0.000 abstract 1
- IOQPZZOEVPZRBK-UHFFFAOYSA-N octan-1-amine Chemical compound CCCCCCCCN IOQPZZOEVPZRBK-UHFFFAOYSA-N 0.000 abstract 1
- 125000000962 organic group Chemical group 0.000 abstract 1
- 239000000123 paper Substances 0.000 abstract 1
- 238000006116 polymerization reaction Methods 0.000 abstract 1
- 239000002244 precipitate Substances 0.000 abstract 1
- 238000002360 preparation method Methods 0.000 abstract 1
- 229920002545 silicone oil Polymers 0.000 abstract 1
- 239000003381 stabilizer Substances 0.000 abstract 1
- 239000008117 stearic acid Substances 0.000 abstract 1
- 239000004753 textile Substances 0.000 abstract 1
- 125000003944 tolyl group Chemical group 0.000 abstract 1
- UBOXGVDOUJQMTN-UHFFFAOYSA-N trichloroethylene Natural products ClCC(Cl)Cl UBOXGVDOUJQMTN-UHFFFAOYSA-N 0.000 abstract 1
- 229940117013 triethanolamine oleate Drugs 0.000 abstract 1
- 239000002023 wood Substances 0.000 abstract 1
Classifications
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
- D06M15/00—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment
- D06M15/19—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment with synthetic macromolecular compounds
- D06M15/37—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
- D06M15/643—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds containing silicon in the main chain
-
- 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
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
- D06M13/00—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment
- D06M13/10—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with compounds containing oxygen
- D06M13/144—Alcohols; Metal alcoholates
- D06M13/148—Polyalcohols, e.g. glycerol or glucose
Landscapes
- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Textile Engineering (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Emergency Medicine (AREA)
- Chemical Kinetics & Catalysis (AREA)
Abstract
A composition for imparting water-repellency to porous or fibrous materials comprises an aqueous emulsion of a silicone resin incorporating an ester of titanic acid with a dihydric alcohol. Suitable silicone resins are methyl, methylphenyl, amyl and methylamyl silicones having an R : Si ratio of between 1.2 and 1.9. Mixtures of silicone resins may be used. Suitable esters of titanic acid are those of ethylene glycol, diethylene glycol, polyethylene glycols, propylene glycol, 1 : 3 and 2 : 3-butanediol. A preferred titanate ester is obtained by esterifying titanium tetrachloride with a dihydric alcohol and treating the product with an alkaline-reacting organic substance such as an amine or amino-alcohol (see Group IV (b)). The emulsion may also contain silicone oils, for example liquid silicones in which the organic groups are lower alkyl groups and the R : Si ratio is about 2.0. To obtain stable emulsions it is preferable to add emulsifying agents such as the double titanate of triethanolamine and stearic acid, a condensation product of tall oil with ten mols. of ethylene oxide per acid group, a polyethylene glycol alkylphenyl ether in which the alkyl group has from 8 to 15 carbon atoms, triethanolamine oleate and octadecylamine stearate. Stabilizers such as carboxymethylcellulose can also be added. Liquid paraffin, fatty acids or alcohols, urea-formaldehyde resins and melamine resins, insecticides or fungicides may also be added. The titanate catalyst lowers the temperature required for final polymerization and curing of the silicones on the material being treated, but a certain amount of heating is still desirable and should take place at a temperature not exceeding 160 DEG C. Preferably the silicone resin content of the emulsion is from 0.5 to 6 per cent by weight and the titanate ester content corresponds to 0.01 to 0.5 per cent by weight of titanium. The composition is suitable for the treatment of textiles, leather, paper, cardboard, masonry, wood and concrete (see Group VIII). Examples describe the preparation of silicone emulsions comprising (5) an amyl silicone resin (R : Si = 1.6), stearylamine acetate, a titanate ester of 1 : 3-butanediol treated with triethanolamine, and water; (6) a methylphenyl silicone (R : Si = 1.6, Me : Ph = 2) in toluene, tall oil condensed with 10 mols. of ethylene oxide, trichloroethylene, carboxymethylcellulose, a titanate ester of propylene glycol treated with triethanolamine, and water; (7) an emulsion as described in (5) except that the catalyst is a titanate ester of diethylene glycol treated with triethanolamine; (8) a silicone emulsion as described in (6) except that the catalyst is a titanate ester of ethylene glycol treated with triethanolamine. Specification 723,989 is referred to.ALSO:An ester of titanic acid with a dihydric alcohol is obtained by esterifying titanium tetrachloride with a dihydric alcohol and treating the product with an alkaline-reacting organic substance. The esterification may be effected at about 115 DEG C. and the crude titanate mixed with 1 to 6 mols. of an amine or aminoalcohol per atom of titanium and heated carefully until a liquid is formed which gives no precipitate on dilution with water (170 DEG C.). Suitable dihydric alcohols for the ester-formation are ethylene glycol, diethylene glycol, polyethylene glycols, propylene glycol, 1 : 3 or 2 : 3-butanediol. Suitable alkaline-reacting substances are diethylenetriamine, monoisobutylamine, octylamine, cyclohexylamine, morpholine, di- and tri-ethanolamines, di- and tri-isopropanolamines, aminobutanol, aminoethylpropanediol and tri-(hydroxymethyl) aminoethane. Mixtures of such substances may be used. In examples: (1) titanium tetrachloride and 1,3-butanediol are heated together at 116 DEG C to form a water-soluble product, triethanolamine is added and the mixture is heated up to 170 DEG C.; (2) titanium tetrachloride and propylene glycol are heated at 110 DEG for 1 hour, triethanolamine is added and the mixture heated to 170 DEG C; (3) TiCl4 and diethylene glycol are similarly reacted and the product treated with triethanolamine; (4) a titanate catalyst is produced as in (3) using ethylene glycol. The titanate esters may be used as catalysts in silicone emulsions (Group IV (a)) for imparting water repellancy to porous and fibrous materials (see Group VIII). Specification 723,989, [Group VIII], is referred to.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| BE812505X | 1956-04-26 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB812505A true GB812505A (en) | 1959-04-29 |
Family
ID=3881212
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB8926/57A Expired GB812505A (en) | 1956-04-26 | 1957-03-19 | Titanate ester compositions and processes for imparting water-repellency |
Country Status (4)
| Country | Link |
|---|---|
| BE (1) | BE547326A (en) |
| FR (1) | FR1183022A (en) |
| GB (1) | GB812505A (en) |
| LU (1) | LU35081A1 (en) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1290518B (en) * | 1962-04-02 | 1969-03-13 | Dow Corning | Aqueous catalyst dispersion for hardening organopolysiloxanes in fiber finishing agents |
| FR2039672A5 (en) * | 1969-03-18 | 1971-01-15 | British Titan Products | |
| EP0169707A2 (en) * | 1984-07-27 | 1986-01-29 | Polyol International B.V. | Process for the production of polymers containing isocyanurate and/or oxazolidone linkages |
| WO1998018998A1 (en) * | 1996-10-29 | 1998-05-07 | Senecal Rene E | Water-repellant insecticide for tent fabric |
-
1956
- 1956-04-26 BE BE547326A patent/BE547326A/en unknown
-
1957
- 1957-03-19 GB GB8926/57A patent/GB812505A/en not_active Expired
- 1957-04-10 LU LU35081A patent/LU35081A1/en unknown
- 1957-04-24 FR FR1183022D patent/FR1183022A/en not_active Expired
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1290518B (en) * | 1962-04-02 | 1969-03-13 | Dow Corning | Aqueous catalyst dispersion for hardening organopolysiloxanes in fiber finishing agents |
| FR2039672A5 (en) * | 1969-03-18 | 1971-01-15 | British Titan Products | |
| EP0169707A2 (en) * | 1984-07-27 | 1986-01-29 | Polyol International B.V. | Process for the production of polymers containing isocyanurate and/or oxazolidone linkages |
| EP0169707A3 (en) * | 1984-07-27 | 1986-06-18 | Bp Chemicals Limited | Process for the production of polymers containing isocyanurate and/or oxazolidone linkages |
| WO1998018998A1 (en) * | 1996-10-29 | 1998-05-07 | Senecal Rene E | Water-repellant insecticide for tent fabric |
Also Published As
| Publication number | Publication date |
|---|---|
| FR1183022A (en) | 1959-07-02 |
| LU35081A1 (en) | 1957-06-11 |
| BE547326A (en) | 1956-05-15 |
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