CA2289881A1 - Improved polyester polymers - Google Patents
Improved polyester polymers Download PDFInfo
- Publication number
- CA2289881A1 CA2289881A1 CA002289881A CA2289881A CA2289881A1 CA 2289881 A1 CA2289881 A1 CA 2289881A1 CA 002289881 A CA002289881 A CA 002289881A CA 2289881 A CA2289881 A CA 2289881A CA 2289881 A1 CA2289881 A1 CA 2289881A1
- Authority
- CA
- Canada
- Prior art keywords
- polyester
- group
- compound
- weight
- carbonyl
- 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.)
- Abandoned
Links
- 229920000728 polyester Polymers 0.000 title claims abstract description 80
- 229920000642 polymer Polymers 0.000 title claims description 16
- 150000001875 compounds Chemical class 0.000 claims abstract description 20
- 125000003277 amino group Chemical group 0.000 claims abstract description 14
- 239000000203 mixture Substances 0.000 claims abstract description 11
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims abstract description 7
- 239000000835 fiber Substances 0.000 claims description 14
- 239000000975 dye Substances 0.000 claims description 13
- 238000000034 method Methods 0.000 claims description 12
- 239000000049 pigment Substances 0.000 claims description 11
- 229910052739 hydrogen Inorganic materials 0.000 claims description 6
- 230000008569 process Effects 0.000 claims description 6
- 239000001257 hydrogen Substances 0.000 claims description 5
- 150000002440 hydroxy compounds Chemical class 0.000 claims description 4
- 238000002156 mixing Methods 0.000 claims description 4
- 150000004027 organic amino compounds Chemical group 0.000 claims description 4
- 239000004594 Masterbatch (MB) Substances 0.000 claims description 3
- 239000011872 intimate mixture Substances 0.000 claims description 3
- 238000006068 polycondensation reaction Methods 0.000 claims description 3
- 238000004040 coloring Methods 0.000 claims description 2
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims 1
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 1
- -1 polyethylene terephthalate Polymers 0.000 description 19
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 17
- 125000003118 aryl group Chemical group 0.000 description 10
- 230000000704 physical effect Effects 0.000 description 9
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 8
- 238000009987 spinning Methods 0.000 description 8
- 150000002148 esters Chemical class 0.000 description 7
- 229920001707 polybutylene terephthalate Polymers 0.000 description 7
- 229920000139 polyethylene terephthalate Polymers 0.000 description 7
- 239000005020 polyethylene terephthalate Substances 0.000 description 7
- 125000000217 alkyl group Chemical group 0.000 description 6
- 230000007774 longterm Effects 0.000 description 6
- 230000014759 maintenance of location Effects 0.000 description 6
- QUAMTGJKVDWJEQ-UHFFFAOYSA-N octabenzone Chemical compound OC1=CC(OCCCCCCCC)=CC=C1C(=O)C1=CC=CC=C1 QUAMTGJKVDWJEQ-UHFFFAOYSA-N 0.000 description 6
- 229920001634 Copolyester Polymers 0.000 description 5
- 150000001412 amines Chemical class 0.000 description 5
- XITRBUPOXXBIJN-UHFFFAOYSA-N bis(2,2,6,6-tetramethylpiperidin-4-yl) decanedioate Chemical compound C1C(C)(C)NC(C)(C)CC1OC(=O)CCCCCCCCC(=O)OC1CC(C)(C)NC(C)(C)C1 XITRBUPOXXBIJN-UHFFFAOYSA-N 0.000 description 5
- XNGIFLGASWRNHJ-UHFFFAOYSA-L phthalate(2-) Chemical compound [O-]C(=O)C1=CC=CC=C1C([O-])=O XNGIFLGASWRNHJ-UHFFFAOYSA-L 0.000 description 5
- 239000000654 additive Substances 0.000 description 4
- 230000000996 additive effect Effects 0.000 description 4
- 150000001408 amides Chemical class 0.000 description 4
- 229920001400 block copolymer Polymers 0.000 description 4
- 239000003086 colorant Substances 0.000 description 4
- 229910052736 halogen Inorganic materials 0.000 description 4
- 150000002367 halogens Chemical class 0.000 description 4
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 4
- 230000006872 improvement Effects 0.000 description 4
- QQVIHTHCMHWDBS-UHFFFAOYSA-N isophthalic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- 239000000155 melt Substances 0.000 description 4
- 238000012545 processing Methods 0.000 description 4
- KKEYFWRCBNTPAC-UHFFFAOYSA-L terephthalate(2-) Chemical compound [O-]C(=O)C1=CC=C(C([O-])=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-L 0.000 description 4
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 4
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 230000032683 aging Effects 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 150000002009 diols Chemical class 0.000 description 3
- 230000032050 esterification Effects 0.000 description 3
- 238000005886 esterification reaction Methods 0.000 description 3
- 238000009998 heat setting Methods 0.000 description 3
- 150000002431 hydrogen Chemical group 0.000 description 3
- 238000010348 incorporation Methods 0.000 description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 3
- 238000006116 polymerization reaction Methods 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 239000000985 reactive dye Substances 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 238000009281 ultraviolet germicidal irradiation Methods 0.000 description 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 2
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 2
- 125000003545 alkoxy group Chemical group 0.000 description 2
- 125000003282 alkyl amino group Chemical group 0.000 description 2
- QMKYBPDZANOJGF-UHFFFAOYSA-N benzene-1,3,5-tricarboxylic acid Chemical compound OC(=O)C1=CC(C(O)=O)=CC(C(O)=O)=C1 QMKYBPDZANOJGF-UHFFFAOYSA-N 0.000 description 2
- 125000001231 benzoyloxy group Chemical group C(C1=CC=CC=C1)(=O)O* 0.000 description 2
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 description 2
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 229920001577 copolymer Polymers 0.000 description 2
- 238000004043 dyeing Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 239000004744 fabric Substances 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 239000000178 monomer Substances 0.000 description 2
- 238000000465 moulding Methods 0.000 description 2
- 239000002530 phenolic antioxidant Substances 0.000 description 2
- 125000003884 phenylalkyl group Chemical group 0.000 description 2
- 229920002215 polytrimethylene terephthalate Polymers 0.000 description 2
- 239000011347 resin Substances 0.000 description 2
- 229920005989 resin Polymers 0.000 description 2
- 239000003381 stabilizer Substances 0.000 description 2
- 238000010998 test method Methods 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- NIDFGXDXQKPZMA-UHFFFAOYSA-N 14h-benz[4,5]isoquino[2,1-a]perimidin-14-one Chemical compound C1=CC(N2C(=O)C=3C4=C(C2=N2)C=CC=C4C=CC=3)=C3C2=CC=CC3=C1 NIDFGXDXQKPZMA-UHFFFAOYSA-N 0.000 description 1
- ADVWVIQNAOXLCV-UHFFFAOYSA-N 2,2,6,6-tetramethylpiperazine Chemical compound CC1(C)CNCC(C)(C)N1 ADVWVIQNAOXLCV-UHFFFAOYSA-N 0.000 description 1
- KTNPVRSKFWZJEZ-UHFFFAOYSA-N 2,2,6,6-tetramethylpiperidin-1-amine Chemical group CC1(C)CCCC(C)(C)N1N KTNPVRSKFWZJEZ-UHFFFAOYSA-N 0.000 description 1
- FTVFPPFZRRKJIH-UHFFFAOYSA-N 2,2,6,6-tetramethylpiperidin-4-amine Chemical compound CC1(C)CC(N)CC(C)(C)N1 FTVFPPFZRRKJIH-UHFFFAOYSA-N 0.000 description 1
- NEQFBGHQPUXOFH-UHFFFAOYSA-N 4-(4-carboxyphenyl)benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1C1=CC=C(C(O)=O)C=C1 NEQFBGHQPUXOFH-UHFFFAOYSA-N 0.000 description 1
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 208000028257 Joubert syndrome with oculorenal defect Diseases 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- SJEYSFABYSGQBG-UHFFFAOYSA-M Patent blue Chemical compound [Na+].C1=CC(N(CC)CC)=CC=C1C(C=1C(=CC(=CC=1)S([O-])(=O)=O)S([O-])(=O)=O)=C1C=CC(=[N+](CC)CC)C=C1 SJEYSFABYSGQBG-UHFFFAOYSA-M 0.000 description 1
- 229920001283 Polyalkylene terephthalate Polymers 0.000 description 1
- 239000004952 Polyamide Substances 0.000 description 1
- 239000002202 Polyethylene glycol Substances 0.000 description 1
- 229920004935 Trevira® Polymers 0.000 description 1
- 230000006750 UV protection Effects 0.000 description 1
- 239000006096 absorbing agent Substances 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000000980 acid dye Substances 0.000 description 1
- 125000002252 acyl group Chemical group 0.000 description 1
- 235000011037 adipic acid Nutrition 0.000 description 1
- 239000001361 adipic acid Substances 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 125000003302 alkenyloxy group Chemical group 0.000 description 1
- 125000004453 alkoxycarbonyl group Chemical group 0.000 description 1
- 230000004075 alteration Effects 0.000 description 1
- 125000003368 amide group Chemical group 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- 150000008430 aromatic amides Chemical class 0.000 description 1
- UWCPYKQBIPYOLX-UHFFFAOYSA-N benzene-1,3,5-tricarbonyl chloride Chemical compound ClC(=O)C1=CC(C(Cl)=O)=CC(C(Cl)=O)=C1 UWCPYKQBIPYOLX-UHFFFAOYSA-N 0.000 description 1
- 239000012965 benzophenone Substances 0.000 description 1
- 150000008366 benzophenones Chemical class 0.000 description 1
- 150000001565 benzotriazoles Chemical class 0.000 description 1
- 230000036760 body temperature Effects 0.000 description 1
- CDQSJQSWAWPGKG-UHFFFAOYSA-N butane-1,1-diol Chemical compound CCCC(O)O CDQSJQSWAWPGKG-UHFFFAOYSA-N 0.000 description 1
- QXJJQWWVWRCVQT-UHFFFAOYSA-K calcium;sodium;phosphate Chemical compound [Na+].[Ca+2].[O-]P([O-])([O-])=O QXJJQWWVWRCVQT-UHFFFAOYSA-K 0.000 description 1
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 125000002091 cationic group Chemical group 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- 150000001844 chromium Chemical class 0.000 description 1
- 229910052804 chromium Inorganic materials 0.000 description 1
- 239000011651 chromium Substances 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 230000001143 conditioned effect Effects 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 230000009849 deactivation Effects 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- 150000001991 dicarboxylic acids Chemical class 0.000 description 1
- 150000001993 dienes Chemical class 0.000 description 1
- GKHRLTCUMXVTAV-UHFFFAOYSA-N dimoracin Chemical compound C1=C(O)C=C2OC(C3=CC(O)=C(C(=C3)O)C3C4C(C5=C(O)C=C(C=C5O3)C=3OC5=CC(O)=CC=C5C=3)C=C(CC4(C)C)C)=CC2=C1 GKHRLTCUMXVTAV-UHFFFAOYSA-N 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 238000010016 exhaust dyeing Methods 0.000 description 1
- 238000005562 fading Methods 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 239000003365 glass fiber Substances 0.000 description 1
- 150000002334 glycols Chemical class 0.000 description 1
- 125000004356 hydroxy functional group Chemical group O* 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- QQVIHTHCMHWDBS-UHFFFAOYSA-L isophthalate(2-) Chemical compound [O-]C(=O)C1=CC=CC(C([O-])=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-L 0.000 description 1
- 238000010128 melt processing Methods 0.000 description 1
- NYGZLYXAPMMJTE-UHFFFAOYSA-M metanil yellow Chemical group [Na+].[O-]S(=O)(=O)C1=CC=CC(N=NC=2C=CC(NC=3C=CC=CC=3)=CC=2)=C1 NYGZLYXAPMMJTE-UHFFFAOYSA-M 0.000 description 1
- KYTZHLUVELPASH-UHFFFAOYSA-N naphthalene-1,2-dicarboxylic acid Chemical compound C1=CC=CC2=C(C(O)=O)C(C(=O)O)=CC=C21 KYTZHLUVELPASH-UHFFFAOYSA-N 0.000 description 1
- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- XRBCRPZXSCBRTK-UHFFFAOYSA-N phosphonous acid Chemical compound OPO XRBCRPZXSCBRTK-UHFFFAOYSA-N 0.000 description 1
- 230000000176 photostabilization Effects 0.000 description 1
- 238000013031 physical testing Methods 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 229920001748 polybutylene Polymers 0.000 description 1
- 238000012643 polycondensation polymerization Methods 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 229920005644 polyethylene terephthalate glycol copolymer Polymers 0.000 description 1
- 230000000379 polymerizing effect Effects 0.000 description 1
- 229920001451 polypropylene glycol Polymers 0.000 description 1
- 229920000909 polytetrahydrofuran Polymers 0.000 description 1
- 229920002635 polyurethane Polymers 0.000 description 1
- 239000004814 polyurethane Substances 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- ULWHHBHJGPPBCO-UHFFFAOYSA-N propane-1,1-diol Chemical compound CCC(O)O ULWHHBHJGPPBCO-UHFFFAOYSA-N 0.000 description 1
- 229920005604 random copolymer Polymers 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- UIIMBOGNXHQVGW-UHFFFAOYSA-N sodium;hydron;carbonate Chemical compound [Na+].OC(O)=O UIIMBOGNXHQVGW-UHFFFAOYSA-N 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 230000006641 stabilisation Effects 0.000 description 1
- 238000011105 stabilization Methods 0.000 description 1
- 230000000087 stabilizing effect Effects 0.000 description 1
- 238000007655 standard test method Methods 0.000 description 1
- 230000003068 static effect Effects 0.000 description 1
- 238000003878 thermal aging Methods 0.000 description 1
- 229920001169 thermoplastic Polymers 0.000 description 1
- 239000004416 thermosoftening plastic Substances 0.000 description 1
- 239000004408 titanium dioxide Substances 0.000 description 1
- 230000000699 topical effect Effects 0.000 description 1
- 238000011282 treatment Methods 0.000 description 1
- 150000003918 triazines Chemical class 0.000 description 1
- 125000004306 triazinyl group Chemical group 0.000 description 1
- 150000003628 tricarboxylic acids Chemical class 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 238000004804 winding Methods 0.000 description 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
- C08K5/13—Phenols; Phenolates
- C08K5/132—Phenols containing keto groups, e.g. benzophenones
-
- 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
- C08K5/07—Aldehydes; Ketones
-
- 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
- C08K5/3412—Heterocyclic compounds having nitrogen in the ring having one nitrogen atom in the ring
- C08K5/3432—Six-membered rings
- C08K5/3435—Piperidines
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T428/00—Stock material or miscellaneous articles
- Y10T428/29—Coated or structually defined flake, particle, cell, strand, strand portion, rod, filament, macroscopic fiber or mass thereof
- Y10T428/2913—Rod, strand, filament or fiber
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Artificial Filaments (AREA)
- Polyesters Or Polycarbonates (AREA)
- Processes Of Treating Macromolecular Substances (AREA)
- Polyamides (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US09/192,608 US5965261A (en) | 1998-11-16 | 1998-11-16 | Polyester |
| US09/192,608 | 1998-11-16 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2289881A1 true CA2289881A1 (en) | 2000-05-16 |
Family
ID=22710373
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002289881A Abandoned CA2289881A1 (en) | 1998-11-16 | 1999-11-15 | Improved polyester polymers |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US5965261A (https=) |
| EP (1) | EP1000967B1 (https=) |
| JP (1) | JP2000143955A (https=) |
| KR (1) | KR100629381B1 (https=) |
| AT (1) | ATE264883T1 (https=) |
| CA (1) | CA2289881A1 (https=) |
| DE (1) | DE69916554T2 (https=) |
| ES (1) | ES2217722T3 (https=) |
| TW (1) | TW494122B (https=) |
Families Citing this family (31)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB9800935D0 (en) | 1998-01-17 | 1998-03-11 | Clariant Int Ltd | Improvements in or relating to organic compounds |
| US6538056B1 (en) * | 2000-10-10 | 2003-03-25 | Clariant International Ltd. | Polyolefin articles with long-term elevated temperature stability |
| MXPA03007914A (es) * | 2001-03-28 | 2003-12-11 | Ciba Sc Holding Ag | Proceso para preparar un poliester estabilizado. |
| US6683124B2 (en) | 2001-09-27 | 2004-01-27 | Clariant Finance (Bvi) Limited | Fluorescent pigment compositions |
| US7081213B2 (en) | 2002-05-14 | 2006-07-25 | Clariant Finance (Bvi) Limited | Stabilizer mixtures for the protection of polymer substrates |
| GB0219260D0 (en) | 2002-08-19 | 2002-09-25 | Clariant Gmbh | Improvements in or relating to organic compounds |
| US20040143041A1 (en) * | 2003-01-13 | 2004-07-22 | Pearson Jason Clay | Polyester compositions |
| US7297735B2 (en) * | 2003-03-05 | 2007-11-20 | Eastman Chemical Company | Polycarbonate compositions |
| US7482397B2 (en) * | 2003-01-13 | 2009-01-27 | Eastman Chemical Company | Polycarbonate compositions |
| EP1449872A1 (de) * | 2003-02-21 | 2004-08-25 | Clariant International Ltd. | Stabilisierung polymerer Materialien |
| US20050277713A1 (en) * | 2003-03-05 | 2005-12-15 | Pearson Jason C | Polymer blends |
| US20040180994A1 (en) * | 2003-03-05 | 2004-09-16 | Pearson Jason Clay | Polyolefin compositions |
| KR101158123B1 (ko) * | 2003-03-05 | 2012-06-19 | 이스트만 케미칼 컴파니 | 자외선 흡수 화합물을 함유하는 중합체 조성물 |
| US7338992B2 (en) * | 2003-03-05 | 2008-03-04 | Eastman Chemical Company | Polyolefin compositions |
| CN100594220C (zh) * | 2003-03-05 | 2010-03-17 | 伊士曼化工公司 | 聚合物共混物 |
| US20040192813A1 (en) * | 2003-03-20 | 2004-09-30 | Pearson Jason Clay | Polymer compositions containing an ultraviolet light absorbing compound |
| US20040183053A1 (en) * | 2003-03-20 | 2004-09-23 | Pearson Jason Clay | Process for the preparation of a hindered amine light stabilizer salt |
| JP4677726B2 (ja) * | 2004-03-01 | 2011-04-27 | 東レ株式会社 | ポリエステル組成物及びそれからなる繊維 |
| DE102004045639A1 (de) * | 2004-09-21 | 2006-04-06 | Clariant Masterbatch Gmbh & Co. Ohg | Polyester-Farbmittelkonzentrat |
| JP2006282933A (ja) * | 2005-04-04 | 2006-10-19 | Asahi Kasei Chemicals Corp | 熱可塑性強化樹脂組成物 |
| US8007885B2 (en) * | 2005-09-14 | 2011-08-30 | Georgios Topoulos | Light-emitting diode assembly housing comprising poly(cyclohexanedimethanol terephthalate) compositions |
| MX2010011288A (es) | 2008-04-23 | 2010-11-09 | Rigel Pharmaceuticals Inc | Compuestos de carboxamida para el tratamiento de trastornos metabolicos. |
| US8480254B2 (en) | 2011-04-14 | 2013-07-09 | Ticona, Llc | Molded reflective structures for light-emitting diodes |
| US9062198B2 (en) | 2011-04-14 | 2015-06-23 | Ticona Llc | Reflectors for light-emitting diode assemblies containing a white pigment |
| US9453119B2 (en) | 2011-04-14 | 2016-09-27 | Ticona Llc | Polymer composition for producing articles with light reflective properties |
| US9284448B2 (en) | 2011-04-14 | 2016-03-15 | Ticona Llc | Molded reflectors for light-emitting diode assemblies |
| US9187621B2 (en) | 2011-12-30 | 2015-11-17 | Ticona Llc | Reflector for light-emitting devices |
| WO2014099745A1 (en) | 2012-12-18 | 2014-06-26 | Ticona Llc | Molded reflectors for light-emitting diode assemblies |
| CN103508938B (zh) * | 2013-03-30 | 2015-07-08 | 烟台瑞龙化学技术有限公司 | N,n’-二(2,2,6,6-四甲基-4-哌啶基)-1,3-苯二甲酰胺的制备方法 |
| DE102013012622A1 (de) * | 2013-07-30 | 2015-02-05 | Clariant lnternational Ltd | Neue sterisch gehinderte cyclische Amine |
| CN104974075A (zh) * | 2015-08-07 | 2015-10-14 | 新秀化学（烟台）有限公司 | 一种n, n-二(2,2,6,6-四甲基-4-哌啶基) -1,3-苯二甲酰胺的制备方法 |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3907926A (en) * | 1973-12-19 | 1975-09-23 | Du Pont | Blends of thermoplastic copolyetherester with poly-butylene terephthalate |
| US4185003A (en) * | 1978-02-16 | 1980-01-22 | E. I. Du Pont De Nemours And Company | Stabilized copolyetheresters |
| US4136090A (en) * | 1978-03-02 | 1979-01-23 | E. I. Du Pont De Nemours And Company | Stabilized copolyetherester compositions |
| US4340718A (en) * | 1980-06-02 | 1982-07-20 | Eastman Kodak Company | Stabilized copolyester material |
| US4355155A (en) * | 1980-10-14 | 1982-10-19 | Gaf Corporation | Thermoplastic copolyester elastomer |
| US4405749A (en) * | 1980-10-14 | 1983-09-20 | Gaf Corporation | Thermoplastic elastomer compositions |
| US4469851A (en) * | 1983-06-06 | 1984-09-04 | Gaf Corporation | Molding composition |
| US4525504A (en) * | 1983-10-24 | 1985-06-25 | Eastman Kodak Company | Stabilized polyester compositions suitable for outdoor applications |
| US4524165A (en) * | 1983-10-24 | 1985-06-18 | Eastman Kodak Company | Stabilized copolyesterether compositions suitable for outdoor applications |
| GB9609742D0 (en) * | 1996-05-10 | 1996-07-17 | Clariant Int Ltd | Improvements in or relating to organic compounds |
-
1998
- 1998-11-16 US US09/192,608 patent/US5965261A/en not_active Expired - Fee Related
-
1999
- 1999-11-11 TW TW088119681A patent/TW494122B/zh not_active IP Right Cessation
- 1999-11-11 JP JP11321559A patent/JP2000143955A/ja not_active Withdrawn
- 1999-11-12 DE DE69916554T patent/DE69916554T2/de not_active Expired - Fee Related
- 1999-11-12 ES ES99811042T patent/ES2217722T3/es not_active Expired - Lifetime
- 1999-11-12 EP EP99811042A patent/EP1000967B1/en not_active Expired - Lifetime
- 1999-11-12 AT AT99811042T patent/ATE264883T1/de not_active IP Right Cessation
- 1999-11-15 CA CA002289881A patent/CA2289881A1/en not_active Abandoned
- 1999-11-16 KR KR1019990050810A patent/KR100629381B1/ko not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| EP1000967B1 (en) | 2004-04-21 |
| ATE264883T1 (de) | 2004-05-15 |
| JP2000143955A (ja) | 2000-05-26 |
| ES2217722T3 (es) | 2004-11-01 |
| KR100629381B1 (ko) | 2006-09-29 |
| TW494122B (en) | 2002-07-11 |
| DE69916554D1 (de) | 2004-05-27 |
| EP1000967A1 (en) | 2000-05-17 |
| US5965261A (en) | 1999-10-12 |
| KR20000035501A (ko) | 2000-06-26 |
| DE69916554T2 (de) | 2005-04-14 |
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| EEER | Examination request | ||
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