GB880961A - Di-(3-cyclohexylbutyl) adipate and plasticised compositions thereof - Google Patents
Di-(3-cyclohexylbutyl) adipate and plasticised compositions thereofInfo
- Publication number
- GB880961A GB880961A GB3036658A GB3036658A GB880961A GB 880961 A GB880961 A GB 880961A GB 3036658 A GB3036658 A GB 3036658A GB 3036658 A GB3036658 A GB 3036658A GB 880961 A GB880961 A GB 880961A
- Authority
- GB
- United Kingdom
- Prior art keywords
- cyclohexylbutyl
- adipate
- acetate
- reducing
- ester
- 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
- UVJLQYHVLAJNDY-UHFFFAOYSA-N bis(3-cyclohexylbutyl) hexanedioate Chemical compound C(CCCCC(=O)OCCC(C)C1CCCCC1)(=O)OCCC(C)C1CCCCC1 UVJLQYHVLAJNDY-UHFFFAOYSA-N 0.000 title abstract 3
- 239000000203 mixture Substances 0.000 title abstract 3
- WFDIJRYMOXRFFG-UHFFFAOYSA-N acetic acid anhydride Natural products CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 abstract 4
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 abstract 4
- XHKHXJPTSALKON-UHFFFAOYSA-N 3-cyclohexylbutan-1-ol Chemical compound OCCC(C)C1CCCCC1 XHKHXJPTSALKON-UHFFFAOYSA-N 0.000 abstract 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 abstract 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 abstract 2
- 239000001361 adipic acid Substances 0.000 abstract 2
- 235000011037 adipic acid Nutrition 0.000 abstract 2
- 125000005907 alkyl ester group Chemical group 0.000 abstract 2
- BJQHLKABXJIVAM-UHFFFAOYSA-N bis(2-ethylhexyl) phthalate Chemical compound CCCCC(CC)COC(=O)C1=CC=CC=C1C(=O)OCC(CC)CCCC BJQHLKABXJIVAM-UHFFFAOYSA-N 0.000 abstract 2
- 150000002148 esters Chemical class 0.000 abstract 2
- 239000000463 material Substances 0.000 abstract 2
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 abstract 2
- OEPOKWHJYJXUGD-UHFFFAOYSA-N 2-(3-phenylmethoxyphenyl)-1,3-thiazole-4-carbaldehyde Chemical compound O=CC1=CSC(C=2C=C(OCC=3C=CC=CC=3)C=CC=2)=N1 OEPOKWHJYJXUGD-UHFFFAOYSA-N 0.000 abstract 1
- FUNWKJSCDPWPNV-UHFFFAOYSA-N 3-cyclohexylbutyl acetate Chemical compound CC(=O)OCCC(C)C1CCCCC1 FUNWKJSCDPWPNV-UHFFFAOYSA-N 0.000 abstract 1
- ZNALWYMGHPMOSK-UHFFFAOYSA-N 3-phenylbut-1-en-1-ol Chemical compound OC=CC(C)C1=CC=CC=C1 ZNALWYMGHPMOSK-UHFFFAOYSA-N 0.000 abstract 1
- OOXTUZYASRPMLY-UHFFFAOYSA-N 3-phenylbut-1-enyl acetate Chemical class C(C)(=O)OC=CC(C)C1=CC=CC=C1 OOXTUZYASRPMLY-UHFFFAOYSA-N 0.000 abstract 1
- JLBJTVDPSNHSKJ-UHFFFAOYSA-N 4-Methylstyrene Chemical compound CC1=CC=C(C=C)C=C1 JLBJTVDPSNHSKJ-UHFFFAOYSA-N 0.000 abstract 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract 1
- 229930040373 Paraformaldehyde Natural products 0.000 abstract 1
- BZHJMEDXRYGGRV-UHFFFAOYSA-N Vinyl chloride Chemical compound ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 abstract 1
- 229910000004 White lead Inorganic materials 0.000 abstract 1
- 125000005396 acrylic acid ester group Chemical group 0.000 abstract 1
- 239000003054 catalyst Substances 0.000 abstract 1
- 229920001577 copolymer Polymers 0.000 abstract 1
- 230000032050 esterification Effects 0.000 abstract 1
- 238000005886 esterification reaction Methods 0.000 abstract 1
- 125000002573 ethenylidene group Chemical group [*]=C=C([H])[H] 0.000 abstract 1
- 238000010438 heat treatment Methods 0.000 abstract 1
- 229920001519 homopolymer Polymers 0.000 abstract 1
- 230000007062 hydrolysis Effects 0.000 abstract 1
- 238000006460 hydrolysis reaction Methods 0.000 abstract 1
- 238000010348 incorporation Methods 0.000 abstract 1
- 150000002688 maleic acid derivatives Chemical class 0.000 abstract 1
- 238000000034 method Methods 0.000 abstract 1
- 239000000178 monomer Substances 0.000 abstract 1
- 229920002866 paraformaldehyde Polymers 0.000 abstract 1
- 239000004014 plasticizer Substances 0.000 abstract 1
- 229920000915 polyvinyl chloride Polymers 0.000 abstract 1
- 239000004800 polyvinyl chloride Substances 0.000 abstract 1
- 238000002360 preparation method Methods 0.000 abstract 1
- 229920001567 vinyl ester resin Polymers 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
- C08K5/11—Esters; Ether-esters of acyclic polycarboxylic acids
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Compositions Of Macromolecular Compounds (AREA)
Abstract
A composition comprises a polymeric material formed from monomers containing a vinylidene or a vinyl group and di-(3-cyclohexylbutyl) adipate as plasticizer. Polymeric materials specified are vinyl chloride homopolymers or copolymers with vinylidene chloride, vinyl esters, acrylic acid esters or maleate esters. An example describes the incorporation of the ester into polyvinyl chloride stabilized with white lead and the results of tests on the product given and compared with results obtained on a similar composition containing di(2-ethylhexyl) phthalate.ALSO:The invention comprises di-(3-cyclohexylbutyl) adipate and a process for its preparation by reducing 4-methyl-4-phenyl-dioxan to form 3-cyclohexylbutanol and heating the alcohol with adipic acid or a lower alkyl ester thereof in the presence of an esterification catalyst or by reacting a methyl-styrene, paraformaldehyde, acetic acid and acetic anhydride, reducing the 3-phenylbutenyl acetates formed to 3-cyclohexylbutyl acetate and subjecting the acetate to ester interchange with a lower alkyl ester of adipic acid. 3-cyclohexylbutanol may also be prepared by reducing the 3-phenylbutenol obtained by hydrolysis of the acetate.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB3036658A GB880961A (en) | 1958-09-23 | 1958-09-23 | Di-(3-cyclohexylbutyl) adipate and plasticised compositions thereof |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB3036658A GB880961A (en) | 1958-09-23 | 1958-09-23 | Di-(3-cyclohexylbutyl) adipate and plasticised compositions thereof |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB880961A true GB880961A (en) | 1961-10-25 |
Family
ID=10306528
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB3036658A Expired GB880961A (en) | 1958-09-23 | 1958-09-23 | Di-(3-cyclohexylbutyl) adipate and plasticised compositions thereof |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB880961A (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5013779A (en) * | 1989-12-08 | 1991-05-07 | Monsanto Company | Plasticized polyvinyl butyral and interlayer thereof |
| EP1516865A1 (en) * | 2003-09-20 | 2005-03-23 | Celanese Chemicals Europe GmbH | 3-(4'-methylcyclohexyl) butanol based carboxylic acid esters having low pour point |
-
1958
- 1958-09-23 GB GB3036658A patent/GB880961A/en not_active Expired
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5013779A (en) * | 1989-12-08 | 1991-05-07 | Monsanto Company | Plasticized polyvinyl butyral and interlayer thereof |
| EP1516865A1 (en) * | 2003-09-20 | 2005-03-23 | Celanese Chemicals Europe GmbH | 3-(4'-methylcyclohexyl) butanol based carboxylic acid esters having low pour point |
| US7196128B2 (en) | 2003-09-20 | 2007-03-27 | Celanese Chemicals Europe Gmbh | Carboxylic esters based on limonene alcohol [3-(4′-methylcyclohexyl)butanol] and having a low melting point |
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