GB1267259A - - Google Patents
Info
- Publication number
- GB1267259A GB1267259A GB1267259DA GB1267259A GB 1267259 A GB1267259 A GB 1267259A GB 1267259D A GB1267259D A GB 1267259DA GB 1267259 A GB1267259 A GB 1267259A
- Authority
- GB
- United Kingdom
- Prior art keywords
- ether
- radical
- ethers
- carbon atoms
- acid
- 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
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 abstract 5
- 125000004432 carbon atom Chemical group C* 0.000 abstract 3
- 239000003054 catalyst Substances 0.000 abstract 3
- 150000001875 compounds Chemical class 0.000 abstract 3
- 150000002170 ethers Chemical class 0.000 abstract 3
- YSUQLAYJZDEMOT-UHFFFAOYSA-N 2-(butoxymethyl)oxirane Chemical group CCCCOCC1CO1 YSUQLAYJZDEMOT-UHFFFAOYSA-N 0.000 abstract 2
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 abstract 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 abstract 2
- 239000002253 acid Substances 0.000 abstract 2
- 125000004106 butoxy group Chemical group [*]OC([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 abstract 2
- 235000011187 glycerol Nutrition 0.000 abstract 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 2
- 239000000203 mixture Substances 0.000 abstract 2
- GLDOVTGHNKAZLK-UHFFFAOYSA-N octadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCO GLDOVTGHNKAZLK-UHFFFAOYSA-N 0.000 abstract 2
- 229920000570 polyether Polymers 0.000 abstract 2
- 229920006395 saturated elastomer Polymers 0.000 abstract 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 abstract 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 abstract 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 abstract 1
- 230000003197 catalytic effect Effects 0.000 abstract 1
- LQZZUXJYWNFBMV-UHFFFAOYSA-N dodecan-1-ol Chemical compound CCCCCCCCCCCCO LQZZUXJYWNFBMV-UHFFFAOYSA-N 0.000 abstract 1
- 125000005843 halogen group Chemical group 0.000 abstract 1
- 229910052739 hydrogen Inorganic materials 0.000 abstract 1
- 239000001257 hydrogen Substances 0.000 abstract 1
- 239000000543 intermediate Substances 0.000 abstract 1
- 239000003456 ion exchange resin Substances 0.000 abstract 1
- 229920003303 ion-exchange polymer Polymers 0.000 abstract 1
- 238000000034 method Methods 0.000 abstract 1
- GOQYKNQRPGWPLP-UHFFFAOYSA-N n-heptadecyl alcohol Natural products CCCCCCCCCCCCCCCCCO GOQYKNQRPGWPLP-UHFFFAOYSA-N 0.000 abstract 1
- 229910052760 oxygen Inorganic materials 0.000 abstract 1
- 239000001301 oxygen Substances 0.000 abstract 1
- 125000004430 oxygen atom Chemical group O* 0.000 abstract 1
- 125000000913 palmityl group Chemical group [H]C([*])([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 1
- 150000003839 salts Chemical class 0.000 abstract 1
- -1 stearyl alcohols Chemical class 0.000 abstract 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-N sulfonic acid Chemical compound OS(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-N 0.000 abstract 1
- 239000004094 surface-active agent Substances 0.000 abstract 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract 1
Classifications
-
- 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
- C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
- C08G65/02—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
- C08G65/04—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers only
- C08G65/22—Cyclic ethers having at least one atom other than carbon and hydrogen outside the ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C43/00—Ethers; Compounds having groups, groups or groups
- C07C43/02—Ethers
- C07C43/03—Ethers having all ether-oxygen atoms bound to acyclic carbon atoms
- C07C43/04—Saturated ethers
- C07C43/10—Saturated ethers of polyhydroxy compounds
- C07C43/11—Polyethers containing —O—(C—C—O—)n units with ≤ 2 n≤ 10
-
- 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
- C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
- C08G65/02—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
- C08G65/32—Polymers modified by chemical after-treatment
- C08G65/321—Polymers modified by chemical after-treatment with inorganic compounds
- C08G65/324—Polymers modified by chemical after-treatment with inorganic compounds containing oxygen
-
- 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
- C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
- C08G65/02—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
- C08G65/32—Polymers modified by chemical after-treatment
- C08G65/329—Polymers modified by chemical after-treatment with organic compounds
- C08G65/334—Polymers modified by chemical after-treatment with organic compounds containing sulfur
- C08G65/3342—Polymers modified by chemical after-treatment with organic compounds containing sulfur having sulfur bound to carbon and hydrogen
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- General Chemical & Material Sciences (AREA)
- Inorganic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Abstract
1,267,259. Ethers. L'OREAL. 9 Dec., 1969 [9 Dec., 1968], No. 60134/69. Heading C2C. A process for the preparation of polyhydroxylated ethers and polyhydroxylated polyethers and compositions containing them, comprises (1) reacting tertiary butyl-glycidyl-ether, in the presence of an acid or basic catalyst, with a compound, or mixture of compounds, containing at least one reactive hydrogen atom, having the general formula: R(XH) a in which a is an integer from 1 to 6; R is a radical of valency " a " and represents a hydrogen atom, a saturated or unsaturated, linear or branched, aliphatic hydrocarbon radical containing 1 to 30 carbon atoms, optionally substituted by one or more halogen atoms, a divalent polyoxyalkylene radical, an alkyl-polyoxyalkylene radical or an alkenyl-polyoxyalkylene radical containing 3 to 60 carbon atoms and 1 to 10 oxygen atoms, a saturated or unsaturated substituted or unsubstituted, cycloaliphatic radical containing 6 to 30 carbon atoms, or a substituted or unsubstituted aromatic radical; the or each of the X radicals, which may be the same or different, represents an oxygen or sulphur atom; the ratio (n), expressed in moles of tertiary butylglycidyl-ether per gram-atom of active hydrogen in the compound of formula R(XH) a being from 0À1 : 1 to 10 : 1 so as to obtain mono- or polyethers containing units of formula and (2) heterolysing the tertiary butoxy group or groups in the presence of controlled amounts of water (as hereinbefore defined) and a catalytic amount of a sulphonic acid. Stage (1) may be effected in the presence of acid or basic catalysts. Simple ethers or telomers may be produced. The catalysts from stage (2) may be removed as their insoluble salts by basic ionexchange resins or merely be neutralized. If they contain carboxyl groups these may esterify the hydroxy-ether product; such derivatives may be saponified. The hydroxy-ether products are surfactants. Examples prepare: the α-nhexyl ether of glycerine; telomers from lauryl alcohol, mixed cetyl and stearyl alcohols, propoxylated stearyl alcohol and glycerol α- monodichlorohydrin; 3-phenoxypropanediol-1,2 and dodecylthipropanediol, the t - butylated derivatives being obtained as intermediates in each case.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| LU57504 | 1968-12-09 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1267259A true GB1267259A (en) | 1972-03-15 |
Family
ID=19725824
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB1267259D Expired GB1267259A (en) | 1968-12-09 | 1969-12-09 |
Country Status (6)
| Country | Link |
|---|---|
| BE (1) | BE742779A (en) |
| CH (1) | CH517136A (en) |
| DE (1) | DE1961731C3 (en) |
| FR (1) | FR2027585A1 (en) |
| GB (1) | GB1267259A (en) |
| LU (1) | LU57504A1 (en) |
Cited By (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4003961A (en) * | 1974-02-20 | 1977-01-18 | The Dow Chemical Company | Linear copolymers of glycidol |
| US4014854A (en) * | 1974-02-20 | 1977-03-29 | The Dow Chemical Company | Linear copolymers of glycidol |
| US4048237A (en) * | 1973-11-12 | 1977-09-13 | The Dow Chemical Company | Process for the dealkylation of t-butyl and t-amyl ethers on polymeric backbones |
| US4077991A (en) * | 1974-05-02 | 1978-03-07 | The Dow Chemical Company | Copolymers of glycidol and glycidyl esters |
| US4080161A (en) | 1976-04-20 | 1978-03-21 | The Dow Chemical Company | Permanent topical antistats |
| US4086151A (en) * | 1974-02-20 | 1978-04-25 | The Dow Chemical Company | Curable mixtures and cured resins made from linear polymers of glycidol |
| US4092339A (en) * | 1974-05-02 | 1978-05-30 | The Dow Chemical Company | Process for making polyglycidyl esters |
| US4125369A (en) | 1977-03-28 | 1978-11-14 | The Dow Chemical Company | Permanent topical textile antistats |
| US4496494A (en) * | 1981-04-02 | 1985-01-29 | The Dow Chemical Company | Process for preparation of (halo)(hydroxy)-substituted phosphites and phosphorates |
| GB2185746A (en) * | 1986-01-27 | 1987-07-29 | Oreal | New polyglycerol ethers and their use in cosmetics and in pharmacy |
| US4754048A (en) * | 1981-04-02 | 1988-06-28 | The Dow Chemical Company | (Halo)(hydroxy)-substituted phosphites and phosphorates |
| US4864049A (en) * | 1981-04-02 | 1989-09-05 | The Dow Chemical Company | (Halo)(hydroxy)-substituted phosphites and phosphorates |
| EP2524938A1 (en) | 2011-05-18 | 2012-11-21 | Evonik Goldschmidt GmbH | Alkoxylation products and method for producing same by means of DMC catalysts |
| WO2013017360A1 (en) | 2011-08-03 | 2013-02-07 | Evonik Goldschmidt Gmbh | Method for producing branched polyethercarbonates and use thereof |
| CN114716661A (en) * | 2021-09-03 | 2022-07-08 | 联泓(江苏)新材料研究院有限公司 | Short-chain alcohol intermediate for efficiently preparing high-molecular-weight polyether synthetic oil and preparation method and application thereof |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2430944A1 (en) * | 1978-07-13 | 1980-02-08 | Oreal | NOVEL SURFACTANT POLYPOD COMPOUNDS, PROCESS FOR PREPARING THE SAME AND COMPOSITIONS CONTAINING THE SAME |
| JPS5993022A (en) * | 1982-11-16 | 1984-05-29 | Kao Corp | Polyol ether compound, its preparation and cosmetic containing the same |
| FR2560880B1 (en) * | 1984-03-07 | 1989-03-31 | Oreal | NOVEL GLYCOSYL POLYETHERS, THEIR PREPARATION PROCESS AND THEIR USE |
| FR2574786B1 (en) * | 1984-12-17 | 1988-06-10 | Oreal | PROCESS FOR THE PREPARATION OF NON-IONIC SURFACES FROM GLYCEROL MONOCHLORHYDRIN, PRODUCTS OBTAINED AND COMPOSITION CONTAINING THEM |
| FR2641985B1 (en) * | 1989-01-26 | 1992-06-19 | Oreal | |
| FR2643828B1 (en) * | 1989-01-26 | 1994-01-07 | Oreal | PROCESS FOR THE PREPARATION OF NON-IONIC SURFACTANTS FROM ISOPROPYLIDENE-1,2 EPOXYPROPYL-3 GLYCEROL AND HYDROXYL COMPOUNDS, NEW NON-IONIC SURFACTANTS AND THEIR USE |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2089569A (en) * | 1932-03-02 | 1937-08-10 | Gen Aniline Works Inc | Addition products of glycide to organic compounds |
| US2260753A (en) * | 1939-10-23 | 1941-10-28 | Shell Dev | Process for the production of derivatives of epihalohydrins |
| GB802325A (en) * | 1954-06-16 | 1958-10-01 | Thomas Hedley & Company Ltd | Improvements in or relating to alkyl polyglyceryl ether compounds |
-
1968
- 1968-12-09 LU LU57504D patent/LU57504A1/xx unknown
-
1969
- 1969-12-08 FR FR6942388A patent/FR2027585A1/fr active Pending
- 1969-12-08 BE BE742779D patent/BE742779A/xx not_active IP Right Cessation
- 1969-12-08 CH CH1824369A patent/CH517136A/en not_active IP Right Cessation
- 1969-12-09 DE DE19691961731 patent/DE1961731C3/en not_active Expired
- 1969-12-09 GB GB1267259D patent/GB1267259A/en not_active Expired
Cited By (19)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4048237A (en) * | 1973-11-12 | 1977-09-13 | The Dow Chemical Company | Process for the dealkylation of t-butyl and t-amyl ethers on polymeric backbones |
| US4003961A (en) * | 1974-02-20 | 1977-01-18 | The Dow Chemical Company | Linear copolymers of glycidol |
| US4014854A (en) * | 1974-02-20 | 1977-03-29 | The Dow Chemical Company | Linear copolymers of glycidol |
| US4086151A (en) * | 1974-02-20 | 1978-04-25 | The Dow Chemical Company | Curable mixtures and cured resins made from linear polymers of glycidol |
| US4077991A (en) * | 1974-05-02 | 1978-03-07 | The Dow Chemical Company | Copolymers of glycidol and glycidyl esters |
| US4092339A (en) * | 1974-05-02 | 1978-05-30 | The Dow Chemical Company | Process for making polyglycidyl esters |
| US4080161A (en) | 1976-04-20 | 1978-03-21 | The Dow Chemical Company | Permanent topical antistats |
| US4125369A (en) | 1977-03-28 | 1978-11-14 | The Dow Chemical Company | Permanent topical textile antistats |
| US4496494A (en) * | 1981-04-02 | 1985-01-29 | The Dow Chemical Company | Process for preparation of (halo)(hydroxy)-substituted phosphites and phosphorates |
| US4754048A (en) * | 1981-04-02 | 1988-06-28 | The Dow Chemical Company | (Halo)(hydroxy)-substituted phosphites and phosphorates |
| US4864049A (en) * | 1981-04-02 | 1989-09-05 | The Dow Chemical Company | (Halo)(hydroxy)-substituted phosphites and phosphorates |
| GB2185746A (en) * | 1986-01-27 | 1987-07-29 | Oreal | New polyglycerol ethers and their use in cosmetics and in pharmacy |
| GB2185746B (en) * | 1986-01-27 | 1989-11-01 | Oreal | New polyglycerol ethers and their use in cosmetics and in pharmacy |
| EP2524938A1 (en) | 2011-05-18 | 2012-11-21 | Evonik Goldschmidt GmbH | Alkoxylation products and method for producing same by means of DMC catalysts |
| DE102011076019A1 (en) | 2011-05-18 | 2012-11-22 | Evonik Goldschmidt Gmbh | Alkoxylation products and processes for their preparation by means of DMC catalysts |
| US9068044B2 (en) | 2011-05-18 | 2015-06-30 | Evonik Degussa Gmbh | Alkoxylation products and process for preparing them by means of DMC catalysts |
| WO2013017360A1 (en) | 2011-08-03 | 2013-02-07 | Evonik Goldschmidt Gmbh | Method for producing branched polyethercarbonates and use thereof |
| DE102011109614A1 (en) | 2011-08-03 | 2013-02-07 | Evonik Goldschmidt Gmbh | Process for the preparation of branched polyethercarbonates and their use |
| CN114716661A (en) * | 2021-09-03 | 2022-07-08 | 联泓(江苏)新材料研究院有限公司 | Short-chain alcohol intermediate for efficiently preparing high-molecular-weight polyether synthetic oil and preparation method and application thereof |
Also Published As
| Publication number | Publication date |
|---|---|
| DE1961731B2 (en) | 1980-10-09 |
| FR2027585A1 (en) | 1970-10-02 |
| CH517136A (en) | 1971-12-31 |
| LU57504A1 (en) | 1970-06-09 |
| DE1961731C3 (en) | 1981-10-29 |
| DE1961731A1 (en) | 1970-06-18 |
| BE742779A (en) | 1970-06-08 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| GB1267259A (en) | ||
| US7189408B2 (en) | Cosmetic compositions | |
| US4650865A (en) | Process for preparing tertiary ether amines | |
| ES450081A1 (en) | Detergent compositions containing ether sulfates | |
| GB2129004A (en) | Poloxyalkylene ethers of glycerol or 1,2-propane diol which are esterified with a fatty acid and/or isostearic acid their preparation and their use as thickeners or solubilisers | |
| CN102395550A (en) | Processes and compositions for low foaming, non-gelling surfactants | |
| US3852314A (en) | Surface-active organoboron compounds | |
| US3772357A (en) | Organoboron compound | |
| US3184490A (en) | Organic aluminium compounds | |
| JPH03506027A (en) | hair dye preparations | |
| IT1116819B (en) | PROCEDURE AND CATALYST FOR THE PREPARATION OF POLES (CHLOROALKYLENE ETHERS) AND PRODUCT OBTAINED | |
| JPS5738736A (en) | Improvement for ethoxylating wide range of primary alcohols | |
| FR2268070B1 (en) | ||
| EP0295578B1 (en) | Use of alkaline earth salts of ethercarboxylic acids as alkoxylation catalysts | |
| GB1461994A (en) | Liquid composition of fatty acid/alkanolamine condensates | |
| GB1526825A (en) | Hydroxy unsaturated diesters | |
| US3959460A (en) | Cosmetic compositions containing anionic surface active agent containing mono- or polyhydroxylated mono- or poly ether chains and a terminal acid group | |
| US4117237A (en) | Unsymmetrical sulfosuccinate diesters | |
| JPS55145634A (en) | Manufacture of monocarboxylic acid | |
| US3870749A (en) | Preparation of salts and complexes of substituted oxyacetate | |
| GB903204A (en) | Surface active agents | |
| DE3032216A1 (en) | Hair shampoo and cosmetic compsn. - contg. polyester prepd. by condensing di:carboxylic acid and alkoxylated tert. amine and opt. neutralising with acid | |
| JPS54106415A (en) | Partially esterified product and cosmetics containing the same | |
| US5250202A (en) | Phenyalkyl glycidyl ether addition products | |
| EP0337239A2 (en) | Use of alkaline earth salts of polycarboxylic acid monoesters as alkoxylation catalysts |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PS | Patent sealed | ||
| PE20 | Patent expired after termination of 20 years |