US2945840A - Process for manufacture of a polyethylene terephthalate in finely divided form - Google Patents
Process for manufacture of a polyethylene terephthalate in finely divided form Download PDFInfo
- Publication number
- US2945840A US2945840A US769594A US76959458A US2945840A US 2945840 A US2945840 A US 2945840A US 769594 A US769594 A US 769594A US 76959458 A US76959458 A US 76959458A US 2945840 A US2945840 A US 2945840A
- Authority
- US
- United States
- Prior art keywords
- polyethylene terephthalate
- finely divided
- halogenated
- acid
- weight
- 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 - Lifetime
Links
- -1 polyethylene terephthalate Polymers 0.000 title claims description 20
- 229920000139 polyethylene terephthalate Polymers 0.000 title claims description 20
- 239000005020 polyethylene terephthalate Substances 0.000 title claims description 20
- 238000000034 method Methods 0.000 title claims description 15
- 238000004519 manufacturing process Methods 0.000 title claims description 8
- 239000007864 aqueous solution Substances 0.000 claims description 20
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical class CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 16
- 239000000203 mixture Substances 0.000 claims description 14
- 150000001243 acetic acids Chemical class 0.000 claims description 13
- 239000000243 solution Substances 0.000 claims description 12
- 239000002904 solvent Substances 0.000 claims description 7
- 235000014113 dietary fatty acids Nutrition 0.000 description 25
- 239000000194 fatty acid Substances 0.000 description 25
- 229930195729 fatty acid Natural products 0.000 description 25
- 150000004665 fatty acids Chemical class 0.000 description 25
- 229920000728 polyester Polymers 0.000 description 20
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 7
- 239000000049 pigment Substances 0.000 description 6
- JXTHNDFMNIQAHM-UHFFFAOYSA-N dichloroacetic acid Chemical compound OC(=O)C(Cl)Cl JXTHNDFMNIQAHM-UHFFFAOYSA-N 0.000 description 5
- 235000011054 acetic acid Nutrition 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- 238000012505 colouration Methods 0.000 description 4
- YNJBWRMUSHSURL-UHFFFAOYSA-N trichloroacetic acid Chemical compound OC(=O)C(Cl)(Cl)Cl YNJBWRMUSHSURL-UHFFFAOYSA-N 0.000 description 4
- 229960004319 trichloroacetic acid Drugs 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- 229960005215 dichloroacetic acid Drugs 0.000 description 3
- 238000003801 milling Methods 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 150000007513 acids Chemical class 0.000 description 2
- 239000010419 fine particle Substances 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 238000000465 moulding Methods 0.000 description 2
- 239000002245 particle Substances 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 230000001376 precipitating effect Effects 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- NDUPDOJHUQKPAG-UHFFFAOYSA-N Dalapon Chemical compound CC(Cl)(Cl)C(O)=O NDUPDOJHUQKPAG-UHFFFAOYSA-N 0.000 description 1
- 239000004952 Polyamide Substances 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- FOCAUTSVDIKZOP-UHFFFAOYSA-N chloroacetic acid Chemical group OC(=O)CCl FOCAUTSVDIKZOP-UHFFFAOYSA-N 0.000 description 1
- 239000008199 coating composition Substances 0.000 description 1
- 235000009508 confectionery Nutrition 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- 230000006866 deterioration Effects 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000001125 extrusion Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 238000010348 incorporation Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000011259 mixed solution Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 239000004753 textile Substances 0.000 description 1
- 238000010792 warming Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J3/00—Processes of treating or compounding macromolecular substances
- C08J3/12—Powdering or granulating
- C08J3/14—Powdering or granulating by precipitation from solutions
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J2367/00—Characterised by the use of polyesters obtained by reactions forming a carboxylic ester link in the main chain; Derivatives of such polymers
- C08J2367/02—Polyesters derived from dicarboxylic acids and dihydroxy compounds
Definitions
- This invention relates to synthetic polyesters and more particularly it relates to a process for the manufacture of synthetic polyesters in Arde'ly divided form.
- a process for the manufacture of synthetic polyesters in a finely divided form which comprises adding a dilute aqueous solution of a halogenated lower fatty acid to a solution of the synthetic polyester in a halogenated lower fatty :acid or in a concentrated aqueous solution of a halogenated lower fatty acid and isolating the finely divided synthetic polyester which is precipitated.
- polyethylene terephthalate As an example of a synthetic polyester which may be used in the process of the invention there may be mentioned polyethylene terephthalate.
- a concentrated aqueous solution of a halogenated lower fatty acid when used for dissolving the synthetic polyester this should contain not less than 80% by weight of the halogenated lower fatty acid and preferably not less than 90% of the halogenated lower fatty acid.
- the dilute aqueous solution of the halogenated lower fatty acid used for precipitating the polyester should contain not more than 50% by weight of the halogenated lower fatty acid and preferably between 20% and 40% by weight of the halogenated lower fatty acid.
- the amount of the dilute aqueous solution of the halogenated lower fatty acid required for precipitating the synthetic polyester from the solution in the halogenated lower fatty acid is such as to give a mixed aqueous solution of the halogenated lower fatty acid in which the synthetic polyester is not appreciably soluble.
- the most satisfactory results are obtained when the mixed aqueous solution of the halogenated lower fatty acid contains between 50% and 65% by weight of the halogenated lower .fatty acid.
- the process of the invention is conveniently carried out at about 30 C. (although temperatures up to 50 C. may be used if desired) by dissolving a synthetic polyester in a halogen-ated lower fatty acid or in a concentrated aqueous solution of a halogenated lower fatty acid containing not less than 80% by weight of a halogenated lower fatty acid, adding such an amount of a dilute aqueous solution of a halogenated lower fatty acid, containing between 20% and 40% by weight of a halogenated lower fatty acid, that the resulting mixed solution contains between 50% and 65% by weight of the lower mean Patented July- 19, 1,950
- fatty acid, filtering ed the finely divided synthetic poly may be mentioned dichloracetic acid, trichloracetic acid,
- halogenated lower fatty acid used need not be pure and may, for example contain a small amount of the corresponding lower fatty acid. If desired mixtures of the halogenated lower fatty acids may be used, for example dichloracetic acid containing monochloro and trichloracetic acid, the said mixture being obtained by chlorinating acetic acid. Such mixtures may also contain minor amounts of the parent lower fatty acid.
- halogenated lower fatty acids or mixtures thereof which are liquid at ordinary temperatures
- halogenated lower fatty acids or mixtures thereof which are solid at ordinary temperatures may be used by warming the said acids until they are in a liquid state.
- the finely divided synthetic polyester obtained by .the process of the invention consists of small particles of uniform size, and when dry the product may be used as a moulding powder. It may also be used, preferably before drying, for incorporation with pigments. Pigment mixtures so obtained are of value for the mass colouration of synthetic polyesters and polyamides and may also be used for the preparation of coating compositions for application to paper or textiles or for the colouration of polymeric materials suitable for moulding or extrusion.
- the process of the invention does not produce any appreciable deterioration in the colour of the synthetic polyester nor result in any marked degradation of the synthetic polyester.
- Example 1 The aqueous paste, which contains 15% of solids, is i then dried at between 50 and 100 C. Polyethylene terephthalate is obtained in the form of a white powder of small particle size.
- Example 2 To a solution of 60 parts of polyethylene terephthalate in a mixture containing 78 parts of acetic acid, 102 parts of trichloroacetic acid and 600 parts dichloroacet-ic acid at 30 C. there are added with stirring 1025 parts of a dilute aqueous solution of acid containing 3.1% of acetic acid, 4% trichloroacetic acid and 23.9% dichloroacetic acid. The mixture is stirred for 2 /2 hours, then allowed to stand for 16 hours and the polyethylene terephthalate which is precipitated in the form of fine particles is filtered off and washed with 10,000 parts of water.
- the aqueous paste which contains approximately 15 of solids is suitable for milling with pigments to produce pigment compositions which may be used in the mass colouration of polyethylene terephthalate.
- Example 3 To a solution of 60 parts of polyethylene terephthalate in 780 parts of 80% trifluoroacetic acid at 20 C. there are added with stirring 1200 parts of a dilute aqueous solution of trifiuoroacetic acid containing 20% of trifluoroacetic acid. The mixture is stirred for 2 /2 hours, then allowed to stand for 16 hours and the polyethylene terephthalate which is precipitated in the form of fine particles is filtered oif and washed with 10,000 parts of water.
- the aqueous paste is suitable for milling with pigments to produce pigment compositions which may be used in the mass colouration of polyethylene terephthalate.
- a process for the manufacture of polyethylene terephthalate in a finely divided particulate form which comprises adding a dilute aqueous solution of a halogenated acetic acid containing between 20% and 40% by weight of the halogenated acetic acid to a solution of polyethylene terephthalate in a solvent selected from the group of solvents consisting of halogenated acetic acids and concentrated aqueous solutions of halogenated acetic acids containing not less than 80% by weight of halogenated acetic acid, said dilute aqueous solution being added to said polyethylene terephthalate solution in v 2.
- a process for the manufacture of polyethylene terephthalate in a finely divided particulate form which comprises adding a dilute aqueous solution of a halogenated acetic acid containing between 20% and by weight of the halogenated acetic acid to a solution of polyethylene terephthalate in a solvent selected from the group of solvents'consisting of halogenated acetic acids and concentrated aqueous solutions of halogenated acetic acids containing not less than 90% by weight of halogenated acettic acids, said dilute aqueous solution being added to said polyethylene terephthalate solution in an amount so that the resulting mixture contains between and by weight of halogenated acetic acid, and thereafter isolating the finely divided polyethylene terephthalate which is precipitated.
- halogenated acetic acid is a mixture obtained by chlorinating acetic acid.
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Processes Of Treating Macromolecular Substances (AREA)
- Paints Or Removers (AREA)
- Paper (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB33842/57A GB838669A (en) | 1957-10-30 | 1957-10-30 | Synthetic polyesters |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US2945840A true US2945840A (en) | 1960-07-19 |
Family
ID=10358149
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US769594A Expired - Lifetime US2945840A (en) | 1957-10-30 | 1958-10-27 | Process for manufacture of a polyethylene terephthalate in finely divided form |
Country Status (4)
| Country | Link |
|---|---|
| US (1) | US2945840A (is") |
| BE (1) | BE572494A (is") |
| FR (1) | FR1214308A (is") |
| GB (1) | GB838669A (is") |
Cited By (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3627733A (en) * | 1964-06-10 | 1971-12-14 | Asahi Chemical Ind | Method for particularizing thermoplastic polyesters |
| US3865899A (en) * | 1973-06-01 | 1975-02-11 | Unifilm Corp | Flatting compositions |
| US3931082A (en) * | 1971-07-27 | 1976-01-06 | Fmc Corporation | Microcrystalline polyesters and dispersions thereof |
| US3935169A (en) * | 1972-10-02 | 1976-01-27 | Ici United States Inc. | Method of preparing polyester powder |
| US4064079A (en) * | 1975-04-25 | 1977-12-20 | Monsanto Company | Polyester polymer recovery |
| US4137393A (en) * | 1977-04-07 | 1979-01-30 | Monsanto Company | Polyester polymer recovery from dyed polyester fibers |
| US4148989A (en) * | 1976-03-17 | 1979-04-10 | Dynamit Nobel Aktiengesellschaft | Crosslinking powder lacquers of polyesters |
| CN116284991A (zh) * | 2023-05-19 | 2023-06-23 | 广东绿王新材料有限公司 | 一种废旧聚酯材料制备聚酯粉的方法 |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AU2002366482A1 (en) | 2001-12-15 | 2003-06-30 | Hyo-Sung Kim | A toner for electrostatic development and its fabrication method by treatment of suspension with reverse-neutralization |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2597643A (en) * | 1947-10-31 | 1952-05-20 | Du Pont | Manufacture of highly polymeric linear polymethylene terephthalates in solution and precipitation thereof |
| US2710848A (en) * | 1953-06-25 | 1955-06-14 | Eastman Kodak Co | Polymeric linear terephthalates dissolved in a solvent comprising trifluoroacetic acid |
| US2762788A (en) * | 1951-06-21 | 1956-09-11 | Johannes Kleine | Dissolution and purification of polyethylene terephthalate |
-
0
- BE BE572494D patent/BE572494A/xx unknown
-
1957
- 1957-10-30 GB GB33842/57A patent/GB838669A/en not_active Expired
-
1958
- 1958-10-27 US US769594A patent/US2945840A/en not_active Expired - Lifetime
- 1958-10-30 FR FR1214308D patent/FR1214308A/fr not_active Expired
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2597643A (en) * | 1947-10-31 | 1952-05-20 | Du Pont | Manufacture of highly polymeric linear polymethylene terephthalates in solution and precipitation thereof |
| US2762788A (en) * | 1951-06-21 | 1956-09-11 | Johannes Kleine | Dissolution and purification of polyethylene terephthalate |
| US2710848A (en) * | 1953-06-25 | 1955-06-14 | Eastman Kodak Co | Polymeric linear terephthalates dissolved in a solvent comprising trifluoroacetic acid |
Cited By (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3627733A (en) * | 1964-06-10 | 1971-12-14 | Asahi Chemical Ind | Method for particularizing thermoplastic polyesters |
| US3931082A (en) * | 1971-07-27 | 1976-01-06 | Fmc Corporation | Microcrystalline polyesters and dispersions thereof |
| US3935169A (en) * | 1972-10-02 | 1976-01-27 | Ici United States Inc. | Method of preparing polyester powder |
| US3865899A (en) * | 1973-06-01 | 1975-02-11 | Unifilm Corp | Flatting compositions |
| US4064079A (en) * | 1975-04-25 | 1977-12-20 | Monsanto Company | Polyester polymer recovery |
| US4148989A (en) * | 1976-03-17 | 1979-04-10 | Dynamit Nobel Aktiengesellschaft | Crosslinking powder lacquers of polyesters |
| US4137393A (en) * | 1977-04-07 | 1979-01-30 | Monsanto Company | Polyester polymer recovery from dyed polyester fibers |
| CN116284991A (zh) * | 2023-05-19 | 2023-06-23 | 广东绿王新材料有限公司 | 一种废旧聚酯材料制备聚酯粉的方法 |
Also Published As
| Publication number | Publication date |
|---|---|
| GB838669A (en) | 1960-06-22 |
| BE572494A (is") | |
| FR1214308A (fr) | 1960-04-07 |
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