GB772454A - A process for producing dispersing agents from polyalkylene oxide waxes - Google Patents
A process for producing dispersing agents from polyalkylene oxide waxesInfo
- Publication number
- GB772454A GB772454A GB18362/54A GB1836254A GB772454A GB 772454 A GB772454 A GB 772454A GB 18362/54 A GB18362/54 A GB 18362/54A GB 1836254 A GB1836254 A GB 1836254A GB 772454 A GB772454 A GB 772454A
- Authority
- GB
- United Kingdom
- Prior art keywords
- acid
- alcohols
- oxide wax
- hydroxyl
- dispersing agents
- 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
- 239000001993 wax Substances 0.000 title abstract 8
- 239000002270 dispersing agent Substances 0.000 title abstract 4
- 229920000233 poly(alkylene oxides) Polymers 0.000 title abstract 3
- 238000000034 method Methods 0.000 title abstract 2
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 abstract 9
- -1 hydroxyl compound Chemical class 0.000 abstract 6
- GLDOVTGHNKAZLK-UHFFFAOYSA-N octadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCO GLDOVTGHNKAZLK-UHFFFAOYSA-N 0.000 abstract 6
- 239000002253 acid Substances 0.000 abstract 5
- 150000001298 alcohols Chemical class 0.000 abstract 4
- 125000004432 carbon atom Chemical group C* 0.000 abstract 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 4
- YDSWCNNOKPMOTP-UHFFFAOYSA-N mellitic acid Chemical compound OC(=O)C1=C(C(O)=O)C(C(O)=O)=C(C(O)=O)C(C(O)=O)=C1C(O)=O YDSWCNNOKPMOTP-UHFFFAOYSA-N 0.000 abstract 4
- 239000003921 oil Substances 0.000 abstract 4
- 235000019198 oils Nutrition 0.000 abstract 4
- 239000000126 substance Substances 0.000 abstract 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 abstract 3
- 229920003171 Poly (ethylene oxide) Polymers 0.000 abstract 3
- 125000000217 alkyl group Chemical group 0.000 abstract 3
- JXLHNMVSKXFWAO-UHFFFAOYSA-N azane;7-fluoro-2,1,3-benzoxadiazole-4-sulfonic acid Chemical compound N.OS(=O)(=O)C1=CC=C(F)C2=NON=C12 JXLHNMVSKXFWAO-UHFFFAOYSA-N 0.000 abstract 3
- HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical compound OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 abstract 3
- 239000011347 resin Substances 0.000 abstract 3
- 229920005989 resin Polymers 0.000 abstract 3
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 abstract 2
- RLHGFJMGWQXPBW-UHFFFAOYSA-N 2-hydroxy-3-(1h-imidazol-5-ylmethyl)benzamide Chemical compound NC(=O)C1=CC=CC(CC=2NC=NC=2)=C1O RLHGFJMGWQXPBW-UHFFFAOYSA-N 0.000 abstract 2
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 abstract 2
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 abstract 2
- KCXVZYZYPLLWCC-UHFFFAOYSA-N EDTA Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(O)=O)CC(O)=O KCXVZYZYPLLWCC-UHFFFAOYSA-N 0.000 abstract 2
- 239000005642 Oleic acid Substances 0.000 abstract 2
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 abstract 2
- 229910006074 SO2NH2 Chemical group 0.000 abstract 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 abstract 2
- 229920002472 Starch Polymers 0.000 abstract 2
- 150000008064 anhydrides Chemical class 0.000 abstract 2
- QMKYBPDZANOJGF-UHFFFAOYSA-N benzene-1,3,5-tricarboxylic acid Chemical compound OC(=O)C1=CC(C(O)=O)=CC(C(O)=O)=C1 QMKYBPDZANOJGF-UHFFFAOYSA-N 0.000 abstract 2
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 abstract 2
- 150000001732 carboxylic acid derivatives Chemical class 0.000 abstract 2
- 150000001735 carboxylic acids Chemical class 0.000 abstract 2
- 229920002678 cellulose Polymers 0.000 abstract 2
- 239000001913 cellulose Substances 0.000 abstract 2
- 150000001875 compounds Chemical class 0.000 abstract 2
- 239000006185 dispersion Substances 0.000 abstract 2
- 229960001484 edetic acid Drugs 0.000 abstract 2
- 150000002148 esters Chemical class 0.000 abstract 2
- 239000003925 fat Substances 0.000 abstract 2
- 150000004820 halides Chemical class 0.000 abstract 2
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 abstract 2
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 abstract 2
- MGFYIUFZLHCRTH-UHFFFAOYSA-N nitrilotriacetic acid Chemical compound OC(=O)CN(CC(O)=O)CC(O)=O MGFYIUFZLHCRTH-UHFFFAOYSA-N 0.000 abstract 2
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 abstract 2
- 150000003839 salts Chemical class 0.000 abstract 2
- 239000008107 starch Substances 0.000 abstract 2
- 235000019698 starch Nutrition 0.000 abstract 2
- 125000000565 sulfonamide group Chemical group 0.000 abstract 2
- 229920003002 synthetic resin Polymers 0.000 abstract 2
- 239000000057 synthetic resin Substances 0.000 abstract 2
- PHYFQTYBJUILEZ-IUPFWZBJSA-N triolein Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OCC(OC(=O)CCCCCCC\C=C/CCCCCCCC)COC(=O)CCCCCCC\C=C/CCCCCCCC PHYFQTYBJUILEZ-IUPFWZBJSA-N 0.000 abstract 2
- 239000001124 (E)-prop-1-ene-1,2,3-tricarboxylic acid Substances 0.000 abstract 1
- GHCOFNPBUBWTPW-DEXHTJMYSA-N (z)-4-[(z)-octadec-9-enoyl]oxy-4-oxobut-2-enoic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OC(=O)\C=C/C(O)=O GHCOFNPBUBWTPW-DEXHTJMYSA-N 0.000 abstract 1
- LBLYYCQCTBFVLH-UHFFFAOYSA-N 2-Methylbenzenesulfonic acid Chemical compound CC1=CC=CC=C1S(O)(=O)=O LBLYYCQCTBFVLH-UHFFFAOYSA-N 0.000 abstract 1
- 241000173529 Aconitum napellus Species 0.000 abstract 1
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 abstract 1
- 241001465754 Metazoa Species 0.000 abstract 1
- 239000004952 Polyamide Substances 0.000 abstract 1
- 229940023019 aconite Drugs 0.000 abstract 1
- 229940091181 aconitic acid Drugs 0.000 abstract 1
- 239000003054 catalyst Substances 0.000 abstract 1
- GTZCVFVGUGFEME-IWQZZHSRSA-N cis-aconitic acid Chemical compound OC(=O)C\C(C(O)=O)=C\C(O)=O GTZCVFVGUGFEME-IWQZZHSRSA-N 0.000 abstract 1
- 239000000839 emulsion Substances 0.000 abstract 1
- 230000032050 esterification Effects 0.000 abstract 1
- 238000005886 esterification reaction Methods 0.000 abstract 1
- 235000021323 fish oil Nutrition 0.000 abstract 1
- 238000010438 heat treatment Methods 0.000 abstract 1
- 229920006158 high molecular weight polymer Polymers 0.000 abstract 1
- 239000012442 inert solvent Substances 0.000 abstract 1
- 229910052500 inorganic mineral Inorganic materials 0.000 abstract 1
- 239000001023 inorganic pigment Substances 0.000 abstract 1
- 239000000463 material Substances 0.000 abstract 1
- 239000011707 mineral Substances 0.000 abstract 1
- 229920003052 natural elastomer Polymers 0.000 abstract 1
- 239000000025 natural resin Substances 0.000 abstract 1
- 229920001194 natural rubber Polymers 0.000 abstract 1
- 239000012860 organic pigment Substances 0.000 abstract 1
- 229920002647 polyamide Polymers 0.000 abstract 1
- 229920000728 polyester Polymers 0.000 abstract 1
- 239000011780 sodium chloride Substances 0.000 abstract 1
- 229920003051 synthetic elastomer Polymers 0.000 abstract 1
- 239000005061 synthetic rubber Substances 0.000 abstract 1
- 239000004753 textile Substances 0.000 abstract 1
- GTZCVFVGUGFEME-UHFFFAOYSA-N trans-aconitic acid Natural products OC(=O)CC(C(O)=O)=CC(O)=O GTZCVFVGUGFEME-UHFFFAOYSA-N 0.000 abstract 1
- 235000013311 vegetables Nutrition 0.000 abstract 1
- 229920002554 vinyl polymer Polymers 0.000 abstract 1
- 239000002023 wood Substances 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K23/00—Use of substances as emulsifying, wetting, dispersing, or foam-producing agents
-
- 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
- D06M13/322—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 nitrogen
- D06M13/372—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 nitrogen containing etherified or esterified hydroxy groups ; Polyethers of low molecular weight
-
- 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
- C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
- C08G63/66—Polyesters containing oxygen in the form of ether groups
- C08G63/668—Polyesters containing oxygen in the form of ether groups derived from polycarboxylic acids and polyhydroxy compounds
-
- 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
- D06M13/184—Carboxylic acids; Anhydrides, halides or salts thereof
- D06M13/207—Substituted carboxylic acids, e.g. by hydroxy or keto groups; Anhydrides, halides or salts thereof
- D06M13/217—Polyoxyalkyleneglycol ethers with a terminal carboxyl group; Anhydrides, halides or salts thereof
-
- 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
- C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
- C08G63/78—Preparation processes
- C08G63/82—Preparation processes characterised by the catalyst used
- C08G63/87—Non-metals or inter-compounds thereof
Landscapes
- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Organic Chemistry (AREA)
- Textile Engineering (AREA)
- Materials Engineering (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Paints Or Removers (AREA)
- Emulsifying, Dispersing, Foam-Producing Or Wetting Agents (AREA)
Abstract
Dispersing agents are produced by condensing a carboxylic acid with a basicity of 3 or more or a functional derivative thereof with a polyalkylene oxide wax and simultaneously or subsequently with an hydroxyl compound containing at least 6 carbon atoms or a corresponding body containing an NH2, SH, CONH2 or SO2NH2 group in place of hydroxyl. Suitable carboxylic acids are citric acid, aconitic acid, diadipic acid, 1,2,3,4 - butanetetracarboxylic acid, trimeric acid, mellitic acid, nitrilo-triacetic acid, an oleic acid-maleic anhydride adduct and ethylenedinitrilo-tetra-acetic acid. Derivatives mentioned are halides, esters or anhydrides. Suitable hydroxyl compounds are alcohols with at least 6 carbon atoms, naphthene alcohols, resin alcohols, cyclohexyl alcohol, alkylated cyclohexyl alcohol, alkylphenols or alkylnaphthols (alkyl residues C3-C18). The process may consist of heating in vacuo up to 180 DEG C. Esterification catalysts, e.g. toluene sulphonic acid and inert solvents, e.g. benzene, may be present. The products may be used for dispersing a great variety of materials, especially for making saliferous dispersions of synthetic resins, starch, cellulose derivatives or fatty substances, e.g. for impregnating textiles or wood or for tanning. In the examples dispersing agents are prepared from (1) polyethylene oxide wax, citric acid and octadecyl alcohol; (2) oxide wax, nitrilo-triacetic acid and octadecyl alcohol; (4) polyethylene oxide wax, diadipic acid and an alkylsulphamide with alkyl residues C12-C16. This product is used to prepare a paste from spindle oil and olein sulphonate; (5) polyethylene oxide wax, an adduct from oleic acid and maleic anhydride and octadecyl alcohol. In Example (3) the product of Example (1) is used to prepare a paste from spindle oil and olein sulphonate. This paste forms a dispersion of tanning salts. In Example (6), the product of Example (5) is dissolved in neutralized sulphonated fish oil and the product used to produce stable tanning emulsions, e.g. with sodium chloride, basic chrome tanning salt and fat.ALSO:Dispersing agents are produced by condensing a carboxylic acid with a basicity of 3 or more or a functional derivative thereof with a polyalkylene oxide wax and simultaneously or subsequently with a hydroxyl compound containing at least 6 carbon atoms or a corresponding body containing a NH2, SH, CONH2 or SO2NH2 group in place of the hydroxyl. Carboxylic acids exemplified are citric acid, aconite acid, diadipic acid an adduct from oleic acid and maleic anhydride, 1, 2, 3, 4 - butane tetra-carboxylic acid, trimesic acid, mellitic acid, nitrillo-triacetic acid, ethylenedinitrilo - tetra - acetic acid. Derivatives mentioned are halides, esters and anhydrides. Hydroxyl compounds exemplified are alcohols with at least 6 carbon atoms, naphthene alcohols, resin alcohols, cyclohexyl alcohols, alkylated cyclohexyl alcohol, alkylphenols or alkylnaphthols (alkyl residues C3 - C18). Substances exemplified are mineral, or resins, natural or synthetic rubber, albumenous substances, synthetic high molecular weight polymer compounds such as polyvinyl compounds, polyesters, polyamides, inorganic or organic pigments, animal, vegetable or synthetic oils, fats and waxes, natural or synthetic resin oils starch, cellulose derivatives and fatty substances.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE772454X | 1953-06-25 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB772454A true GB772454A (en) | 1957-04-10 |
Family
ID=6681464
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB18362/54A Expired GB772454A (en) | 1953-06-25 | 1954-06-23 | A process for producing dispersing agents from polyalkylene oxide waxes |
Country Status (2)
| Country | Link |
|---|---|
| GB (1) | GB772454A (en) |
| NL (1) | NL100609C (en) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1115027B (en) * | 1958-03-26 | 1961-10-12 | Bayer Ag | Process for the preparation of diesters from polyethers having a free hydroxyl group |
| FR2427382A1 (en) * | 1978-05-30 | 1979-12-28 | Cincinnati Milacron Inc | AQUEOUS COMPOSITIONS BASED ON A DIESTER WITH CARBOXYLIC ACID TERMINAL GROUPS OF A POLYOXYALKYLENEDIOL, INTENDED FOR METAL MACHINING |
| FR2623422A1 (en) * | 1987-11-23 | 1989-05-26 | Stepan Europe | Mild and biodegradable mono- or polycarboxylic surface-active agents |
-
0
- NL NL100609D patent/NL100609C/xx active
-
1954
- 1954-06-23 GB GB18362/54A patent/GB772454A/en not_active Expired
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1115027B (en) * | 1958-03-26 | 1961-10-12 | Bayer Ag | Process for the preparation of diesters from polyethers having a free hydroxyl group |
| FR2427382A1 (en) * | 1978-05-30 | 1979-12-28 | Cincinnati Milacron Inc | AQUEOUS COMPOSITIONS BASED ON A DIESTER WITH CARBOXYLIC ACID TERMINAL GROUPS OF A POLYOXYALKYLENEDIOL, INTENDED FOR METAL MACHINING |
| FR2623422A1 (en) * | 1987-11-23 | 1989-05-26 | Stepan Europe | Mild and biodegradable mono- or polycarboxylic surface-active agents |
Also Published As
| Publication number | Publication date |
|---|---|
| NL100609C (en) |
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