GB2282383A - Process for the production of modified polyester moulding materials - Google Patents
Process for the production of modified polyester moulding materials Download PDFInfo
- Publication number
- GB2282383A GB2282383A GB9417416A GB9417416A GB2282383A GB 2282383 A GB2282383 A GB 2282383A GB 9417416 A GB9417416 A GB 9417416A GB 9417416 A GB9417416 A GB 9417416A GB 2282383 A GB2282383 A GB 2282383A
- Authority
- GB
- United Kingdom
- Prior art keywords
- polyester
- process according
- diisocyanate
- antioxidant
- modified
- 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.)
- Withdrawn
Links
- 229920000728 polyester Polymers 0.000 title claims description 50
- 238000000034 method Methods 0.000 title claims description 27
- 239000000463 material Substances 0.000 title claims description 23
- 238000000465 moulding Methods 0.000 title claims description 14
- 238000004519 manufacturing process Methods 0.000 title claims description 8
- 125000005442 diisocyanate group Chemical group 0.000 claims description 15
- 239000003963 antioxidant agent Substances 0.000 claims description 10
- 230000003078 antioxidant effect Effects 0.000 claims description 9
- 229920001169 thermoplastic Polymers 0.000 claims description 9
- 239000004416 thermosoftening plastic Substances 0.000 claims description 8
- 239000000155 melt Substances 0.000 claims description 7
- 238000004806 packaging method and process Methods 0.000 claims description 7
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 6
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 claims description 6
- 238000006243 chemical reaction Methods 0.000 claims description 6
- 229920000139 polyethylene terephthalate Polymers 0.000 claims description 6
- 239000005020 polyethylene terephthalate Substances 0.000 claims description 6
- 125000001931 aliphatic group Chemical group 0.000 claims description 5
- 229920006395 saturated elastomer Polymers 0.000 claims description 5
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 claims description 4
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 claims description 4
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 claims description 4
- 239000011888 foil Substances 0.000 claims description 4
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 claims description 4
- CXMXRPHRNRROMY-UHFFFAOYSA-N sebacic acid Chemical compound OC(=O)CCCCCCCCC(O)=O CXMXRPHRNRROMY-UHFFFAOYSA-N 0.000 claims description 4
- SBJCUZQNHOLYMD-UHFFFAOYSA-N 1,5-Naphthalene diisocyanate Chemical compound C1=CC=C2C(N=C=O)=CC=CC2=C1N=C=O SBJCUZQNHOLYMD-UHFFFAOYSA-N 0.000 claims description 2
- 229940008841 1,6-hexamethylene diisocyanate Drugs 0.000 claims description 2
- 239000005058 Isophorone diisocyanate Substances 0.000 claims description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 claims description 2
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 claims description 2
- 239000001361 adipic acid Substances 0.000 claims description 2
- 235000011037 adipic acid Nutrition 0.000 claims description 2
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 claims description 2
- 229940093476 ethylene glycol Drugs 0.000 claims description 2
- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 claims description 2
- XXMIOPMDWAUFGU-UHFFFAOYSA-N hexane-1,6-diol Chemical compound OCCCCCCO XXMIOPMDWAUFGU-UHFFFAOYSA-N 0.000 claims description 2
- NIMLQBUJDJZYEJ-UHFFFAOYSA-N isophorone diisocyanate Chemical compound CC1(C)CC(N=C=O)CC(C)(CN=C=O)C1 NIMLQBUJDJZYEJ-UHFFFAOYSA-N 0.000 claims description 2
- 229920001707 polybutylene terephthalate Polymers 0.000 claims description 2
- 238000006068 polycondensation reaction Methods 0.000 claims description 2
- 229960004063 propylene glycol Drugs 0.000 claims description 2
- 235000013772 propylene glycol Nutrition 0.000 claims description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims 1
- OJMIONKXNSYLSR-UHFFFAOYSA-N phosphorous acid Chemical compound OP(O)O OJMIONKXNSYLSR-UHFFFAOYSA-N 0.000 claims 1
- 239000000047 product Substances 0.000 description 6
- 238000007792 addition Methods 0.000 description 4
- 239000007858 starting material Substances 0.000 description 4
- UPMLOUAZCHDJJD-UHFFFAOYSA-N 4,4'-Diphenylmethane Diisocyanate Chemical compound C1=CC(N=C=O)=CC=C1CC1=CC=C(N=C=O)C=C1 UPMLOUAZCHDJJD-UHFFFAOYSA-N 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- -1 aromatic dicarboxylic acids Chemical class 0.000 description 2
- 150000001718 carbodiimides Chemical class 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 238000001125 extrusion Methods 0.000 description 2
- 239000004744 fabric Substances 0.000 description 2
- 239000004746 geotextile Substances 0.000 description 2
- 239000008187 granular material Substances 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- RNFJDJUURJAICM-UHFFFAOYSA-N 2,2,4,4,6,6-hexaphenoxy-1,3,5-triaza-2$l^{5},4$l^{5},6$l^{5}-triphosphacyclohexa-1,3,5-triene Chemical compound N=1P(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP=1(OC=1C=CC=CC=1)OC1=CC=CC=C1 RNFJDJUURJAICM-UHFFFAOYSA-N 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- 150000001991 dicarboxylic acids Chemical class 0.000 description 1
- 150000002009 diols Chemical class 0.000 description 1
- 229920001971 elastomer Polymers 0.000 description 1
- 239000000806 elastomer Substances 0.000 description 1
- 239000003063 flame retardant Substances 0.000 description 1
- 230000003301 hydrolyzing effect Effects 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000003607 modifier Substances 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- AQSJGOWTSHOLKH-UHFFFAOYSA-N phosphite(3-) Chemical class [O-]P([O-])[O-] AQSJGOWTSHOLKH-UHFFFAOYSA-N 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 238000004064 recycling Methods 0.000 description 1
- 238000007493 shaping process Methods 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 229920005992 thermoplastic resin Polymers 0.000 description 1
- 238000009849 vacuum degassing Methods 0.000 description 1
- 239000013585 weight reducing agent Substances 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
Classifications
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D39/00—Filtering material for liquid or gaseous fluids
- B01D39/08—Filter cloth, i.e. woven, knitted or interlaced material
- B01D39/083—Filter cloth, i.e. woven, knitted or interlaced material of organic material
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B65—CONVEYING; PACKING; STORING; HANDLING THIN OR FILAMENTARY MATERIAL
- B65D—CONTAINERS FOR STORAGE OR TRANSPORT OF ARTICLES OR MATERIALS, e.g. BAGS, BARRELS, BOTTLES, BOXES, CANS, CARTONS, CRATES, DRUMS, JARS, TANKS, HOPPERS, FORWARDING CONTAINERS; ACCESSORIES, CLOSURES, OR FITTINGS THEREFOR; PACKAGING ELEMENTS; PACKAGES
- B65D65/00—Wrappers or flexible covers; Packaging materials of special type or form
- B65D65/38—Packaging materials of special type or form
-
- 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
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/40—High-molecular-weight compounds
- C08G18/42—Polycondensates having carboxylic or carbonic ester groups in the main chain
-
- 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
- C08G63/91—Polymers modified by chemical after-treatment
- C08G63/914—Polymers modified by chemical after-treatment derived from polycarboxylic acids and polyhydroxy compounds
- C08G63/916—Dicarboxylic acids and dihydroxy compounds
-
- D—TEXTILES; PAPER
- D01—NATURAL OR MAN-MADE THREADS OR FIBRES; SPINNING
- D01F—CHEMICAL FEATURES IN THE MANUFACTURE OF ARTIFICIAL FILAMENTS, THREADS, FIBRES, BRISTLES OR RIBBONS; APPARATUS SPECIALLY ADAPTED FOR THE MANUFACTURE OF CARBON FILAMENTS
- D01F6/00—Monocomponent artificial filaments or the like of synthetic polymers; Manufacture thereof
- D01F6/78—Monocomponent artificial filaments or the like of synthetic polymers; Manufacture thereof from copolycondensation products
- D01F6/84—Monocomponent artificial filaments or the like of synthetic polymers; Manufacture thereof from copolycondensation products from copolyesters
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D2239/00—Aspects relating to filtering material for liquid or gaseous fluids
- B01D2239/04—Additives and treatments of the filtering material
Description
- 1 PROCESS FOR THE PRODUCTION OF MODIFIED POLYESTER MOULDING MATERIALS is
2282383 The present invention concernsa process for the production of modified polyester moulding materials, and the moulding materials obtained by using the process.
Polyester products are widely used as they have good physical properties and high thermal and chemical stability. Thus, polyester moulding materials are widely processed to make foil, fibres and strip, for example geotextiles, cooling-tower foil, filter fabrics and monofilaments.
A particularly important application is polyester packaging straps used in the packaging of goods for transport. Besides high tensile strength, such straps must also show well defined elongation properties and low tendency to split when kinked.
In the present state of the art it has been attempted to achieve this combination of properties by using a polyester, f or example polyethyleneterephthalate with an exceptionally high molecular weight. Apart from the fact that even with such polyesters the splitting tendency leaves something to be desired, polyesters of that kind are very expensive and so call into question the economics of using moulding materials of the type under discussion.
It has therefore been sought to realize the abovementioned combination of properties by making additions to the raw polyester material. For example, additives that have been tried are modifiers, elastomers and copolymers.
2 Material obtained by recycling has been considered as the raw polyester material. However, its processing results in a significant molecular weight reduction owing to the high thermal load, the shear forces and the hydrolytic breakdown entailed. Attempts have been made to counteract this by the use of wetting agents and/or stabilizers, and diisocyanate adducts, carbodiimides, diisocyanates and other reactive compounds have been proposed for this.
DE-A-26 10 531 describes thermoplastic polymers modified with a polycarbodiimide. These are obtained by reacting a thermoplastic saturated polyester with a polycarbodiimide derived from at least one aromatic diisocyanate that is unsubstituted or that has one methyl substituent on each aromatic ring, and comprises at least three carbodiimide units per molecule. The polyesters obtained are suitable for extrusion and have a melt strength ratio TI/T2 of less than 2.
DE-A-27 12 319 describes a process for the production of a flameretardant thermoplastic resin in which a reaction product of a thermoplastic polyester of low molecular weight and a diisocyanate is used.
with the methods proposed at the present state of the art it is not possible to achieve the above-mentioned properties in combination. Though the state-of-the-art methods result in an increase of the viscosity of the polyester materials, when they are stretched to the desired shape the crystallinity increases and the resistance to splitting therefore falls.
The aim of the present invention was thus to find a process for the production of polyester moulding materials, which can be carried out simply and economically and give products with a low tendency to 01 I- 3 split.
is Surprisingly, it was found that polyester materials can be modified by the addition of diisocyanates in such a way as considerably to increase the intrinsic viscosity, the impact strength and the splitting resistance of shaped articles made from them, while the tensile strength and elongation remain unchanged.
Thus, the object of the present invention is a process for the production of stretched, modified polyester moulding materials characterized in that thermoplastic, saturated polyesters are caused to react with aliphatic or aromatic diisocyanates in the melt, and that the product can be shaped, especially by extrusion, and stretched.
The use of a diisocyanate increases the intrinsic viscosity and hence also the impact strength of the polyesters or polyester moulding materials. Surprisingly, despite the increase in impact strength, there is no reduction of the tensile strength or the resistance to splitting. Rather, the resistance to splitting is observed to increase.
The process of the invention can therefore be used to produce polyesters and polyester moulding materials with improved properties. They are particularly suitable for the production of stretched products such as packaging straps, fibres including monofilaments, foils of all kinds, filter fabrics, geotextiles, etc.
Surprisingly, the process of the invention can even be carried out with recycled polyesters having intrinsic viscosities below 0.65 dl/g as starting material. There is hardly any other economically viable use for material of this type.
A In the process of the present invention any of the common thermoplastic, saturated polyesters can be used as the starting material. Homopo'ymers or mixed polymers can be used, in particular polyesters based on aliphatic or aromatic dicarboxylic acids and aliphatic diols. Suitable dicarboxylic acids are, for example, succinic acid, adipic acid, sebacic acid, phthalic acid or terephthalic acid.
Suitable diols are, for example, ethyleneglycol, propyleneglycol, 1,3- and 1,4-butanediol, or 1,6hexanediol.
Particularly preferable polyesters are polyethyleneterephthalate and polybutyleneterephthalate, and mixed polymers thereof.
Diisocyanates that can be used for the process conforming to the invention are, for preference, 1,4tetramethylenediisocyanate, 1, 6hexamethylenediisocyanate, isophoronediisocyanate, 2,4and 2,6toluylenediisocyanate, 4,41diphenylmethanediisocyanate or 1, 5naphthylenediisocyanate. Particularly to be preferred is 4,4'diphenylmethanediisocyanate (MDI).
The quantity of diisocyanate used depends on the quality of the initial polyester and on the properties desired in the product. It is generally in the range from 0.1 to 5 weight-percent, most commonly from 0.2 to 3 weight percent.
The reaction between the polyester starting material and the diisocyanate takes place in the melt, i.e. generally at a temperature in the range 200 to 3300C and most often 200 to 3000C. Depending on the case, the reaction may take place directly after the - 5 polycondensation or in an extruder. While it is in progress, provision must be made for the effective removal of gaseous reaction products, especially carbon dioxide.
is In accordance with a preferred-form, the polyester starting material is reacted together with a diisocyanate and an antioxidant. The polyester so obtained possesses particularly advantageous properties. Thus, a further object of the invention is a modified thermoplastic polyester material obtained by reaction between a thermoplastic, saturated polyester in the melt and at least one aliphatic or aromatic diisocyanate and at least one antioxidant.
The antioxidants used for preference are sterically hindered phenols or organic phosphites. Particularly to be preferred is pentaerythrityltetrakis-3-(3,5-ditert.-butyl-4-hydroxyphenyl) propionate, or bis(2,4ditert.- butylphenyl)-pentaerythrityldiphosphite.
The quantity of antioxidant used depends on the quality of the initial polyester and on the purpose for which the modified polyester is to be used. For preference, it is in the range from 0.05 to 1 weight-percent, based on the polyester.
The shaping and stretching of the moulding materials obtained in accordance with the invention takes place in the normal way, choosing the conditions in accordance with the product desired.
The invention is illustrated by the following examples:
Example 1
990 parts by weight of polyethyleneterephthalate with an intrinsic viscosity of 0.64 dl/g were modified in the 6 - melt at 2700C in an extruder with vacuum degassing, by the addition of 0. 75 weight percent of 4,41diphenylmethylene-diisocyanate and 0.25 weight percent of pentaerythrityl-tetrakis-3-(3,5-di-tert.butyl-4hydroxyphenyl)- propionate. The granulate obtained from this after cooling and cutting- had an intrinsic viscosity of 0.84 dl/g.
The granulate was remelted in a second extruder at 2700C and extruded to a strip. After cooling, this strip was reheated to restore plasticity and stretched to approximately 5.5 times its original length by means of takeup rollers running at different speeds. The strips so obtained showed the following properties:
intrinsic viscosity tensile strength (at break), DIN 53455 tensile elongation (at break), DIN 53455 splitting coefficient (at break), DIN 53374 0. 82 dl/g 3029 N 12. 9 % 81 Comparative Example 1 Preparation of packaging straps from unmodified polyethyleneterephthalate with an intrinsic viscosity of 0.64 dl/g:
To attain the requisite tensile strength a stretch ratio of the extruded strips of 1:5.5 would be needed. This cannot be done because the strips break at a considerably lower stretch ratio. It is also impossible to prepare packaging straps usable in practice and with the required properties by the method of Comparative Example 2.
Comnarative ExamDle 2 Starting with an unmodified polyethyleneterephthalate of intrinsic viscosity 0.84 dl/g, packaging straps were prepared as in Example 1, but without the addition of 7 any diisocyanate or antioxidant.
had the following properties:
The straps produced intrinsic viscosity tensile strength (at break), DIN 53455 tensile elongation (at break),-DIN 53455 splitting coefficient (at break), DIN 53374 0. 82 dl/g 2900 N 13. 0'-. 57 8
Claims (14)
1. A process for the production of stretched, modified polyester moulding material, characterized in that a thermoplastic polyester is reacted in the melt with at least one aliphatic or aromatic diisocyanate, the modified polyester so formed is shaped, and the material so obtained is stretched.
2. A process according to claim 1 in which an aliphatic diisocyanate is used.
3. A process according to claim 1 or claim 2 in which the diisocyanate used is selected from 1,4tetramethylenediisocyanate, 1, 6hexamethylenediisocyanate, isophoronediisocyanate, 2,4and 2,6toluylenediisocyanate, 4,41diphenylmethanediisocyanate, and 1, 5naphthylenediisocyanate.
4. A process according to any preceding claim in which the diisocyanate is used in an amount of 0.1 to
5 weight percent, based on the amount of polyester.
A process according to any preceding claim in which the polyester used is based on succinic acid, adipic acid, sebacic acid, phthalic acid and/or terephthalic acid and ethyleneglycol, propyleneglycol, 1,3- or 1, 4butanediol and/or 1,6-hexanediol.
6. A process according to any preceding claim in which the polyester used is polyethyleneterephthalate or polybutyleneterephthalate and the diisocyanate used is 4,41-diphenylmethanediisocyanate.
7. A process according to any preceding claim in which the polyester used is recycled material with an 9 - intrinsic viscosity lower than 0.80 dl/g.
8. A process according to any preceding claim in which the reaction of the polyester with the diisocyanate is caused to take place in the melt directly after the polycondensation or in an extruder in the temperature range 200 to 3300C.
9. A process according to any preceding claim in which the reaction of the polyester with the diisocyanate takes place in the presence of at least one antioxidant.
10. A process according to claim 9 in which the antioxidant is a sterically hindered phenol or an organic phosphite.
11. A process according to claim 9 or claim 10 in which the antioxidant is pentaerythrityl-tetrakis-3-(3,5-ditert.-butyl-4-hydroxyphenyl)propionate, or bis(2,4-ditert.-butylphenyl)-pentaerythrityldiphosphite.
12. A process according to any of claims 9 to 11 in which the antioxidant is used in an amount of 0.05 to 1 weight percent based on the amount of polyester.
13. Stretched, modified polyester moulding material obtained by a process according to any of claims 1 to 12.
14. The use of modified polyesters or polyester moulding materials obtained by reaction of a thermoplastic, saturated polyester in the melt with at least one aliphatic or aromatic diisocyanate and if necessary at least one antioxidant in accordance with any of claims 1 to 12, to produce packaging straps, fibres including monofilaments, or foils.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE4329310A DE4329310A1 (en) | 1993-08-31 | 1993-08-31 | Process for the preparation of modified polyester molding compositions |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| GB9417416D0 GB9417416D0 (en) | 1994-10-19 |
| GB2282383A true GB2282383A (en) | 1995-04-05 |
Family
ID=6496454
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB9417416A Withdrawn GB2282383A (en) | 1993-08-31 | 1994-08-30 | Process for the production of modified polyester moulding materials |
Country Status (4)
| Country | Link |
|---|---|
| JP (1) | JPH07188433A (en) |
| DE (1) | DE4329310A1 (en) |
| GB (1) | GB2282383A (en) |
| IT (1) | IT1274732B (en) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2814746B1 (en) * | 2000-09-29 | 2003-06-27 | Ct D Etudes Sur Le Recyclage D | PROCESS FOR THE SYNTHESIS OF ADDITIVES FOR IMPROVING THE CHARACTERISTICS OF POLYESTER WASTE FOR RECYCLING AND ADDITIVES OBTAINED |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1540545A (en) * | 1976-03-22 | 1979-02-14 | Dainippon Ink & Chemicals | Process for the preparation of flame retardant thermoplastic resin compositions |
| US4409167A (en) * | 1981-01-13 | 1983-10-11 | E. I. Du Pont De Nemours & Co, | Process for extruding a modified high molecular weight poly(ethylene terephthalate) resin |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1356068A (en) * | 1971-02-25 | 1974-06-12 | Fuji Photo Film Co Ltd | Regeneration of waste plastics materials |
| SU530047A1 (en) * | 1974-07-05 | 1976-09-30 | Казанский Филиал Всесоюзного Ордена Трудового Красного Знамени Научно-Исследовательского Института Синтетического Каучука Им. Академика С.В.Лебедева | Polyester composition |
| SU603650A1 (en) * | 1975-07-29 | 1978-04-25 | Предприятие П/Я Р-6768 | Method of reprocessing polyethyleneterephthalate waste |
| JPS6072915A (en) * | 1983-09-29 | 1985-04-25 | Unitika Ltd | Production of heat-resistant polyester |
| SU1184846A1 (en) * | 1984-01-04 | 1985-10-15 | Uk P Kt I Mestnoj Promy | Composition for moulding articles |
| US4540768A (en) * | 1984-10-09 | 1985-09-10 | Texaco Inc. | Rim elastomers made from terephthalate polyester polyol derived polymer polyols |
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| EP0458261A1 (en) * | 1990-05-23 | 1991-11-27 | The Dow Chemical Company | Compositions prepared using finely-divided isocyanate based thermoset polymers |
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-
1993
- 1993-08-31 DE DE4329310A patent/DE4329310A1/en not_active Withdrawn
-
1994
- 1994-08-25 IT ITMI941772A patent/IT1274732B/en active IP Right Grant
- 1994-08-26 JP JP6225855A patent/JPH07188433A/en not_active Withdrawn
- 1994-08-30 GB GB9417416A patent/GB2282383A/en not_active Withdrawn
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1540545A (en) * | 1976-03-22 | 1979-02-14 | Dainippon Ink & Chemicals | Process for the preparation of flame retardant thermoplastic resin compositions |
| US4409167A (en) * | 1981-01-13 | 1983-10-11 | E. I. Du Pont De Nemours & Co, | Process for extruding a modified high molecular weight poly(ethylene terephthalate) resin |
Also Published As
| Publication number | Publication date |
|---|---|
| JPH07188433A (en) | 1995-07-25 |
| ITMI941772A1 (en) | 1996-02-25 |
| GB9417416D0 (en) | 1994-10-19 |
| IT1274732B (en) | 1997-07-24 |
| DE4329310A1 (en) | 1995-03-02 |
| ITMI941772A0 (en) | 1994-08-25 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| WAP | Application withdrawn, taken to be withdrawn or refused ** after publication under section 16(1) |