GB833867A - Neopentyl glycol alkyl phthalates - Google Patents
Neopentyl glycol alkyl phthalatesInfo
- Publication number
- GB833867A GB833867A GB26175/58A GB2617558A GB833867A GB 833867 A GB833867 A GB 833867A GB 26175/58 A GB26175/58 A GB 26175/58A GB 2617558 A GB2617558 A GB 2617558A GB 833867 A GB833867 A GB 833867A
- Authority
- GB
- United Kingdom
- Prior art keywords
- esters
- carbon atoms
- plasticized
- polyvinyl chloride
- formula
- 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 Neopentyl glycol alkyl phthalates Chemical class 0.000 title abstract 2
- 150000002148 esters Chemical class 0.000 abstract 7
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 abstract 4
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 abstract 3
- 125000004432 carbon atom Chemical group C* 0.000 abstract 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 abstract 3
- 229920000915 polyvinyl chloride Polymers 0.000 abstract 3
- 239000004800 polyvinyl chloride Substances 0.000 abstract 3
- 239000011347 resin Substances 0.000 abstract 3
- 229920005989 resin Polymers 0.000 abstract 3
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 abstract 2
- RTOSJSSWYMWLIG-UHFFFAOYSA-J C(CCCCCCCCCCC)(=O)[O-].[Ba+2].[Cd+2].C(CCCCCCCCCCC)(=O)[O-].C(CCCCCCCCCCC)(=O)[O-].C(CCCCCCCCCCC)(=O)[O-] Chemical compound C(CCCCCCCCCCC)(=O)[O-].[Ba+2].[Cd+2].C(CCCCCCCCCCC)(=O)[O-].C(CCCCCCCCCCC)(=O)[O-].C(CCCCCCCCCCC)(=O)[O-] RTOSJSSWYMWLIG-UHFFFAOYSA-J 0.000 abstract 2
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 abstract 2
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 abstract 2
- BZHJMEDXRYGGRV-UHFFFAOYSA-N Vinyl chloride Chemical compound ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 abstract 2
- 125000000217 alkyl group Chemical group 0.000 abstract 2
- 229920001577 copolymer Polymers 0.000 abstract 2
- 239000007788 liquid Substances 0.000 abstract 2
- 239000000203 mixture Substances 0.000 abstract 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 abstract 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 abstract 1
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 abstract 1
- 125000005907 alkyl ester group Chemical group 0.000 abstract 1
- 239000003054 catalyst Substances 0.000 abstract 1
- 125000002704 decyl 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])* 0.000 abstract 1
- 230000032050 esterification Effects 0.000 abstract 1
- 238000005886 esterification reaction Methods 0.000 abstract 1
- 235000011087 fumaric acid Nutrition 0.000 abstract 1
- 150000002238 fumaric acids Chemical class 0.000 abstract 1
- 229920001519 homopolymer Polymers 0.000 abstract 1
- 150000002689 maleic acids Chemical class 0.000 abstract 1
- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 abstract 1
- 239000004014 plasticizer Substances 0.000 abstract 1
- 238000010992 reflux Methods 0.000 abstract 1
- 239000002904 solvent Substances 0.000 abstract 1
- 239000004408 titanium dioxide Substances 0.000 abstract 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 abstract 1
- 239000008096 xylene Substances 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/04—Oxygen-containing compounds
- C08K5/10—Esters; Ether-esters
- C08K5/12—Esters; Ether-esters of cyclic polycarboxylic acids
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/76—Esters of carboxylic acids having a carboxyl group bound to a carbon atom of a six-membered aromatic ring
- C07C69/80—Phthalic acid esters
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Manufacture Of Macromolecular Shaped Articles (AREA)
Abstract
The invention comprises esters of formula <FORM:0833867/IV (b)/1> wherein R is an alkyl residue of a monohydric aliphatic alcohol which contains at least 6 carbon atoms and is such that the ester is liquid at room temperatures and n is 0 or 1. They are used as plasticizers in polyvinyl chloride resins (see Group IV(a)). They are prepared by mixing appropriate amounts of a phthalic acid, an alkanol preferably having 6-10 carbon atoms and neopentyl glycol with an esterification catalyst such as sulphuric, phosphoric or p-toluenesulphonic acid and refluxing in the presence of a water-entraining solvent such as hexane, toluene or xylene. In examples, the esters wherein R is iso-octyl and n is O and R is decyl and n=1, the -C6H4- residue being derived from o-phthalic acid, are prepared.ALSO:Polyvinyl chloride resins are plasticized by the addition of esters of formula <FORM:0833867/IV (a)/1> wherein R is an alkyl residue of a monohydric aliphatic alcohol which contains at least 6 carbon atoms and is such that the ester is liquid at room temperatures and n is 0 or 1 (see Group IV (b)). Homopolymers of vinyl chloride or its copolymers with, for example, vinyl acetate or the alkyl esters of maleic or fumaric acids, may be used. In examples compositions of polyvinyl chloride and barium cadmium laurate, or of a copolymer of vinyl chloride and vinyl acetate with barium cadmium laurate and titanium dioxide are plasticized with esters of the above formula and the properties of the plasticized resin compared with similar compositions using other plasticizing esters.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US67953857A | 1957-08-21 | 1957-08-21 | |
| US40180A US3028352A (en) | 1960-07-01 | 1960-07-01 | Neopentyl glycol alkyl phthalates and polyvinyl chloride compositions plasticized therewith |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB833867A true GB833867A (en) | 1960-05-04 |
Family
ID=26716803
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB26175/58A Expired GB833867A (en) | 1957-08-21 | 1958-08-14 | Neopentyl glycol alkyl phthalates |
| GB4556/61A Expired GB924526A (en) | 1957-08-21 | 1961-02-07 | Neopentyl glycol alkyl phthalates |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB4556/61A Expired GB924526A (en) | 1957-08-21 | 1961-02-07 | Neopentyl glycol alkyl phthalates |
Country Status (5)
| Country | Link |
|---|---|
| BE (1) | BE570394A (en) |
| DE (2) | DE1182809B (en) |
| FR (2) | FR1242842A (en) |
| GB (2) | GB833867A (en) |
| NL (3) | NL105368C (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN111621255A (en) * | 2020-06-05 | 2020-09-04 | 美邦（黄山）胶业有限公司 | Medium-resistant bi-component solvent-free polyurethane adhesive |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5164122A (en) * | 1988-04-18 | 1992-11-17 | The Lubrizol Corporation | Thermal oxidatively stable synthetic fluid composition |
| DE68920723T3 (en) * | 1988-04-18 | 1999-07-22 | The Lubrizol Corp., Wickliffe, Ohio | THERMAL AND OXYDATIVE STABLE SYNTHETIC FLUID COMPOSITION. |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2617779A (en) * | 1949-05-28 | 1952-11-11 | Gen Electric | Plasticized vinyl halide resins and electrical conductors insulated therewith |
| GB734115A (en) * | 1952-04-01 | 1955-07-27 | Distillers Co Yeast Ltd | Plasticised composition |
-
0
- NL NL230545D patent/NL230545A/xx unknown
-
1958
- 1958-08-14 GB GB26175/58A patent/GB833867A/en not_active Expired
- 1958-08-15 NL NL230545A patent/NL105368C/xx active
- 1958-08-16 BE BE570394D patent/BE570394A/xx unknown
- 1958-08-19 FR FR772756A patent/FR1242842A/en not_active Expired
- 1958-08-20 DE DEA30126A patent/DE1182809B/en active Pending
-
1960
- 1960-10-19 NL NL257018A patent/NL106657C/xx active
- 1960-10-24 DE DEA35872A patent/DE1186621B/en active Pending
- 1960-10-25 FR FR842127A patent/FR78599E/en not_active Expired
-
1961
- 1961-02-07 GB GB4556/61A patent/GB924526A/en not_active Expired
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN111621255A (en) * | 2020-06-05 | 2020-09-04 | 美邦（黄山）胶业有限公司 | Medium-resistant bi-component solvent-free polyurethane adhesive |
| CN111621255B (en) * | 2020-06-05 | 2021-01-29 | 美邦（黄山）胶业有限公司 | Medium-resistant bi-component solvent-free polyurethane adhesive |
Also Published As
| Publication number | Publication date |
|---|---|
| FR1242842A (en) | 1961-01-09 |
| NL106657C (en) | 1963-11-15 |
| DE1182809B (en) | 1964-12-03 |
| FR78599E (en) | 1962-08-10 |
| BE570394A (en) | 1958-09-15 |
| NL230545A (en) | |
| GB924526A (en) | 1963-04-24 |
| DE1186621B (en) | 1965-02-04 |
| NL105368C (en) | 1963-07-15 |
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