GB1581953A - Method for clear-colouring of linear aromatic polyester - Google Patents
Method for clear-colouring of linear aromatic polyester Download PDFInfo
- Publication number
- GB1581953A GB1581953A GB343779A GB343779A GB1581953A GB 1581953 A GB1581953 A GB 1581953A GB 343779 A GB343779 A GB 343779A GB 343779 A GB343779 A GB 343779A GB 1581953 A GB1581953 A GB 1581953A
- Authority
- GB
- United Kingdom
- Prior art keywords
- pigment
- parts
- mixture
- linear aromatic
- polyester
- 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
Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B57/00—Other synthetic dyes of known constitution
- C09B57/12—Perinones, i.e. naphthoylene-aryl-imidazoles
-
- 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
- C08K5/16—Nitrogen-containing compounds
- C08K5/34—Heterocyclic compounds having nitrogen in the ring
- C08K5/3442—Heterocyclic compounds having nitrogen in the ring having two nitrogen atoms in the ring
- C08K5/3445—Five-membered rings
- C08K5/3447—Five-membered rings condensed with carbocyclic rings
-
- 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
- C08K5/36—Sulfur-, selenium-, or tellurium-containing compounds
- C08K5/45—Heterocyclic compounds having sulfur in the ring
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B7/00—Indigoid dyes
- C09B7/10—Bis-thionapthene indigos
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)
- Artificial Filaments (AREA)
Description
(45) METHOD FOR CLEAR-COLOURING OF LINEAR
AROMATIC POLYESTER (71) We, DAINIPPON INK AND CHEMICALS, INC., a Japanese Body Corporate, of 35-58, 3-chome, Sakashita, Itabashi-ku, Tokyo, Japan, do hereby declare the invention, for which we pray that a patent may be granted to us, and the method by which it is to be performed, to be particularly described in and by the following statement:- This invention relates to a colouring method, and more soecifically, to a method for clearcolouring linear aromatic polyesters.
Linear aromatic polyesters are used to produce textile products, film products and other molded products. For example, polyethylene terephthalate is commercially utilised in the production of fibres and films, and polyethylene terephthalate, polypropylene terephthalate and polybutylene terephthalate, in the production of other shape articles.
The basic requirements for colouration of linear aromatic polyesters using pigments are that (1) the pigments should have good fastness characteristics, for example, they must withstand high melting temperatures (up to 3000C) and have superior fastness to light and sublimation, and (2) the pigment particles should be finely and uniformly dispersed in the polyesters without being agglomerated.
In recent years, the consumers have not been content merely with pigment-coloured nontransparent pastel-like colours, but tended to demand products having brilliant and clear colours. To obtain clear-coloured linear aromatic polyesters, a method of "dope dyeing" was suggested which involves mixing a dye with a polyester, and melting the mixture.
Japanese Patent Publication No. 26095/68 and U.S. Patent Specification No. 3,401,142 disclose some anthraquinonic dyes as suitable for use in dope dyeing.
The present inventors have found that instead of such dyes, certain pigments give brilliant and clear colours when used to colour linear aromatic polyesters.
Thus, the present invention provides a method for clear-colouring linear aromatic polyesters, which comprises mixing the pigment of formula (I) below,
with a linear aromatic polyester; and then heating the mixture to the melting temperature of the polyester to dissolve or substantially dissolve the pigment in the polyester.
This pigment (1) is described in "Colour
Index, 3rd Edition, Volume 3" (published by The Society of Dyers and Colourists with acknowledgement to The American Association of Textile Chemists and Colourists) as (1) C.I. Pigment Red 194. This pigment has a melting point of at least 3000C, and is widely used as a colouring agent for printing inks, paints and lacquers. It is known that this pigment may be used for dyeing cotton as a vat dye, or for colouring polyolefins, rubber, vinyl plastics, etc.
Investigations of the pigment of the present invention show that when the pigment of the
Formula (I) is used for colouring polypropylene, the pigment particles disperse in polvDropylene to afford a dull red colour or a dull reddish violet colour, and when used for colouring 6-nylon, they discolour at the time of melting 6-nylon. It was found, surprisingly, that when this pigment is used to colour linear aromatic polyesters whose melting temperatures are as high as 250 to 3000C, the pigment dissolves in the polyesters during melting, and no pigment particle is seen to disperse; and that the colour imDarted is a clear brilliant red colour or reddish violet colour, and the coloured polyesters have superior fastness to heat, light and to sublimation.
The linear aromatic polyesters that can be coloured by the method of this invention are linear polyalkylene terephthalates obtained by the reaction of terephthalic acid or dialkyl terephthalates with glycols of the formula HOCH2OH, n being an integer of 2 to 10, or 1 ,4-di ( hydroxymethyl ) cyclohexane.
These polyesters have long been known as materials for fibres and films, and methods for their production are described, for example, in U.S. Patent Specification No.
2,475,319 (Whinfield) and U.S. Patent Speci fiction No. 3,047,539 (Pengilly).
The linear aromatic polyesters, namely linear polyalkylene terephthalates containing 2 to 10 alkylene groups, as used in this application are also meant to include copolyesters based on these polyesters. These copolyesters can be obtained by replacing the starting terephthalic acid component partly by another dicarboxylic acid or hydroxycarboxylic acid, and/or the starting glycol partly by another glycol. Examples of the other dicarboxylic acid or hydroxycarboxylic acid are isophthalic acid, naphthalenedicarboxylic acid, diphenyldicarboxylic acid, hydroxyethoxybenzoic acid, hydroxypropoxybenzoic acid, p-hydroxybenzoic acid, adipic acid, and sebacic acid.
Typical examples of the linear aromatic polyesters are polyethylene terephthalate, polypropylene terephthalate, polybutylene terephthalate, and copolyesters resulting from the replacement of a part of the constituent monomers by other monomers.
The linear aromatic polyesters used in this invention have an intrinsic viscosity, measured at 250C in a mixture of equal amounts of tetrachloroethane and phenol, of 0.4 to 1.2.
The method of this invention is achieved by mixing the pigment with a linear aromatic polyester, advantageously mixing the finely divided pigment with a chip-like or granular linear aromatic polyester, and heating the mix
ture to the melting temperature of the poly
ester, preferably to 250 to 300 C, to dissolve
or substantially dissolve the pigment in the
polyester.
The amount of the pigment to be mixed with the linear aromatic polyester is usually up to 1% by weight based on the total weight of the polyester and the pigment. When the operability of the coloured polyester in spinning and other fabrication processes is considered, the amount of the pigment should desirably be 0.01 to 0.5% by weight.
The coloured linear aromatic polyester produced by the method of this invention contains no detectable pigment particle, and has a brilliant and dear colour. It also has superior fastness to heat, light and sublimation.
If desired, other pigments such as C.I.
Pigment Red 87 and/or C.I. Pigment Violet 36 (as described in "Colour Index", 3rd
Edition, Volume 3), fillers, reinforcing agents or stabilisers, may also be incorporated.
In this connection it is to be noted that our co-pending Application No. 30659/77 (Serial
No. 1,581,952) describes and claims a method
similar to the method of the present invention wherein the pigment is selected from certain thioindigo pigments including C.I. Pigment
Red 87 and C.I. Pigment Violet 36.
The following Examples illustrate the present invention without any intention of limiting it.
All parts in these Examples are by weight.
Example 1.
0.5 parts of C.I. Pigment Red 194 and 99.5 parts of polyethylene terephthalate having an intrinsic viscosity of 0.70, were mixed and dried at 1800 C and 0.01 mmHg for 5 hours.
The mixture was melt-spun in a customary manner at 3000 C with a residence time of 3 minutes to afford 3-denier coloured filaments.
The characteristics of the coloured filaments are shown in the following table.
Example 1 Pigment C.l. Pigment Red 194 Color of the colored filaments Red Orange State of the pigment in the No pigment polyester (*1) particle observed light (*2) 7 8 heat (*3) 4 - 5 washing (*4) change 4 - 5 staining 4-5 a organic change 4-5 solvent (perchloro ethylene) staining 4 - 5 (*5) (nylon) Sublimation (*6) ) 3 4 Rubbing (*7) wet 5 dry 5
Note (*1): Ten milligrams of a coloured filament sample was melted. It was placed at 2900 C between two thin-layer glass plates and observed with a 400X microscope.
(*2): Measured on a blue scale in accordance with JIS L 0483-71 (Xenon arc).
(*3): A coloured filament obtained by spinning in the same way as described above except that the residence time was changed to 15 minutes was compared with a gray scale for assessing change in colour.
(*4): Measured on a gray scale in accordance with JIS L-0844-73 (700 C + 2" C, 45 min.).
(*5): Measured on a gray scale in accordance with JIS L 0860-74 (400 C + 20 C, 30 min.).
(*6): A sample coloured filament was wrapped by a polyester cloth, and allowed to
stand for 90 minutes in a hot air dryer at 1800 C, and then the stained state of the poly
ester cloth was measured by using a gray scale
for assessing stain in colour.
(*7): Measured in accordance with JIS
L 0849-71 using a gray scale for assessing stain
in colour.
Example 2.
C.I. Pigment Violet 36 (0.2 part), 0.3 part
of C.I. Pigment Red 194 and 99.5 parts of
polyethylene terephthalate (intrinsic viscosity
0.68) were uniformly mixed, and dried at 120"C and 0.01 mmHg for 16 hours. The
mixture was spun at 2900 C in a customary
manner to afford 6-denier filaments having a
brilliant red colour. No particle of the pig
ments was detected by observation with 400X
microscope.
The filaments had substantially the same
fastness characteristics as the filaments obtained in Example 1.
Example 3.
C.I. Pigment Red 87 (2 parts), 6 parts of
C.I. Pigment Red 194, 2 parts of carbon black and 90 parts of polyethylene terephthalate (in tlinsic viscosity 0.70) were mixed, and dried at 180"C and 0.01 mmHg for 5 hours. The mixture was extruded at 2900 C to afford a master batch of 10% pigment concentration.
Five parts of the master batch was mixed with 95 parts of polyethylene terephthalate, and the.
mixture was dried at 1300 C and 0.01 mmHg for 10 hours. The dry mixture was spun at 290 C and drawn in a customary manner to obtain 10-denier filaments, having a brown colour. Ten milligrams of a coloured filament was melted and placed at 2900 C between two thin layer glass plates and observed with a 400X microscope. Only carbon black particles were seen. The resulting filaments had substantially the same fastness characteristics as the filaments obtained in Example 1.
Example 4.
C.I. Pigment Red 194 (0.3 part) and 99.7 parts of reinforced polybutylene terephthalate (intrinsic viscosity 0.7, containing 30% by weight of glass fibres) were mixed, and dried at 120"C under atmospheric pressure for 4 hours. The dried mixture was molded at 2500 C to afford plates uniformly coloured red violet.
WHAT WE CLAIM IS:
1. A method for clear-colouring of linear aromatic polyesters, which comprise mixing a pigment of the formula
with a linear aromatic polyester, and heating the mixture to the melting temperature of the polyester to dissolve or substantially dissolve the pigment in the polyester.
2. The method of claim 1 substantially as herein described in Example 1.
3. The method of claim 1 substantially as herein described in Example 4.
4. Linear aromatic polyesters coloured by the method of claim 1.
**WARNING** end of DESC field may overlap start of CLMS **.
Claims (4)
1. A method for clear-colouring of linear aromatic polyesters, which comprise mixing a pigment of the formula
with a linear aromatic polyester, and heating the mixture to the melting temperature of the polyester to dissolve or substantially dissolve the pigment in the polyester.
2. The method of claim 1 substantially as herein described in Example 1.
3. The method of claim 1 substantially as herein described in Example 4.
4. Linear aromatic polyesters coloured by the method of claim 1.
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP8662776A JPS5910389B2 (en) | 1976-07-22 | 1976-07-22 | How to color polyester |
Publications (1)
Publication Number | Publication Date |
---|---|
GB1581953A true GB1581953A (en) | 1980-12-31 |
Family
ID=13892254
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB343779A Expired GB1581953A (en) | 1976-07-22 | 1977-07-21 | Method for clear-colouring of linear aromatic polyester |
Country Status (2)
Country | Link |
---|---|
JP (1) | JPS5910389B2 (en) |
GB (1) | GB1581953A (en) |
Families Citing this family (21)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4452720A (en) * | 1980-06-04 | 1984-06-05 | Teijin Limited | Fluorescent composition having the ability to change wavelengths of light, shaped article of said composition as a light wavelength converting element and device for converting optical energy to electrical energy using said element |
JPS59204545A (en) * | 1983-05-10 | 1984-11-19 | 住友ベークライト株式会社 | Laminated conductive film |
JPS60120093U (en) * | 1984-01-23 | 1985-08-13 | 遠藤 隆昭 | Katado retaining assembly gutter |
JPS6122327A (en) * | 1984-07-11 | 1986-01-30 | Toray Ind Inc | Photochromic molding |
JPS6179644A (en) * | 1984-09-28 | 1986-04-23 | 住友ベークライト株式会社 | Transparent laminated conductive film |
JPH0622970B2 (en) * | 1987-05-26 | 1994-03-30 | 昭和電工株式会社 | Flavor-barrier multi-layer wrapping material |
JPH0234328A (en) * | 1988-07-25 | 1990-02-05 | Mitsubishi Monsanto Chem Co | Gas barrier laminated film |
JP2536578B2 (en) * | 1988-03-02 | 1996-09-18 | 東洋紡績株式会社 | Method for producing vapor-deposited polyester film |
JPH0712649B2 (en) * | 1988-04-19 | 1995-02-15 | 三菱化学株式会社 | Transparent plastic film with excellent gas barrier properties |
JPH0655471B2 (en) * | 1988-04-19 | 1994-07-27 | 三菱化成株式会社 | Transparent plastic film with excellent gas barrier properties |
JPH0825244B2 (en) * | 1988-05-10 | 1996-03-13 | 三菱化学株式会社 | Transparent plastic film with excellent gas barrier properties |
JPH0774872B2 (en) * | 1988-08-24 | 1995-08-09 | 三菱化学株式会社 | Package film for backlight of liquid crystal display |
JPH0622976B2 (en) * | 1989-08-30 | 1994-03-30 | 株式会社麗光 | Plastic film for packaging |
JPH0454842U (en) * | 1990-09-14 | 1992-05-11 | ||
MY113596A (en) * | 1995-04-11 | 2002-04-30 | Daicel Chem | Barrier composite films and method of producing the same |
US7297414B2 (en) | 2003-09-30 | 2007-11-20 | Fujifilm Corporation | Gas barrier film and method for producing the same |
US7635525B2 (en) | 2003-09-30 | 2009-12-22 | Fujifilm Corporation | Gas barrier laminate film and method for producing the same |
WO2007123006A1 (en) | 2006-04-21 | 2007-11-01 | Konica Minolta Holdings, Inc. | Gas barrier film, resin base for organic electroluminescent device, organic electroluminescent device using the same, and method for producing gas barrier film |
US8846187B2 (en) | 2007-02-06 | 2014-09-30 | Konica Minolta Holdings, Inc. | Transparent gas barrier film and method for producing transparent gas barrier film |
JP2009028949A (en) | 2007-07-25 | 2009-02-12 | Fujifilm Corp | Barrier-film substrate, its manufacturing method, and organic device |
JP6040140B2 (en) | 2013-12-06 | 2016-12-07 | 双葉電子工業株式会社 | Organic electroluminescence device |
-
1976
- 1976-07-22 JP JP8662776A patent/JPS5910389B2/en not_active Expired
-
1977
- 1977-07-21 GB GB343779A patent/GB1581953A/en not_active Expired
Also Published As
Publication number | Publication date |
---|---|
JPS5312953A (en) | 1978-02-06 |
JPS5910389B2 (en) | 1984-03-08 |
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Legal Events
Date | Code | Title | Description |
---|---|---|---|
PS | Patent sealed | ||
PCNP | Patent ceased through non-payment of renewal fee |
Effective date: 19950721 |