JP5457471B2 - ポリエステルとポリアミドの安定化ブレンド - Google Patents
ポリエステルとポリアミドの安定化ブレンド Download PDFInfo
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- JP5457471B2 JP5457471B2 JP2011553436A JP2011553436A JP5457471B2 JP 5457471 B2 JP5457471 B2 JP 5457471B2 JP 2011553436 A JP2011553436 A JP 2011553436A JP 2011553436 A JP2011553436 A JP 2011553436A JP 5457471 B2 JP5457471 B2 JP 5457471B2
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- Japan
- Prior art keywords
- acid
- composition
- stabilizers
- polyester
- polyamide
- 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.)
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- 239000000203 mixture Substances 0.000 title claims description 76
- 229920002647 polyamide Polymers 0.000 title claims description 45
- 239000004952 Polyamide Substances 0.000 title claims description 44
- 229920006149 polyester-amide block copolymer Polymers 0.000 title description 7
- -1 poly-m-xylene adipamide Chemical compound 0.000 claims description 74
- 150000001875 compounds Chemical class 0.000 claims description 73
- 239000003381 stabilizer Substances 0.000 claims description 73
- 229920000728 polyester Polymers 0.000 claims description 49
- 150000001299 aldehydes Chemical class 0.000 claims description 35
- 150000002596 lactones Chemical class 0.000 claims description 34
- 239000002530 phenolic antioxidant Substances 0.000 claims description 29
- 239000000654 additive Substances 0.000 claims description 23
- 239000002516 radical scavenger Substances 0.000 claims description 22
- 229920002959 polymer blend Polymers 0.000 claims description 20
- 238000010438 heat treatment Methods 0.000 claims description 15
- PXBFMLJZNCDSMP-UHFFFAOYSA-N 2-Aminobenzamide Chemical class NC(=O)C1=CC=CC=C1N PXBFMLJZNCDSMP-UHFFFAOYSA-N 0.000 claims description 13
- 230000000996 additive effect Effects 0.000 claims description 12
- 238000000034 method Methods 0.000 claims description 12
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims description 10
- 229910052698 phosphorus Inorganic materials 0.000 claims description 10
- 239000011574 phosphorus Substances 0.000 claims description 10
- 239000000155 melt Substances 0.000 claims description 9
- 229910052757 nitrogen Inorganic materials 0.000 claims description 9
- 230000015572 biosynthetic process Effects 0.000 claims description 7
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- 239000000314 lubricant Substances 0.000 claims description 6
- 239000003795 chemical substances by application Substances 0.000 claims description 5
- RQKYHDHLEMEVDR-UHFFFAOYSA-N oxo-bis(phenylmethoxy)phosphanium Chemical compound C=1C=CC=CC=1CO[P+](=O)OCC1=CC=CC=C1 RQKYHDHLEMEVDR-UHFFFAOYSA-N 0.000 claims description 5
- YJEULLIOUKINGM-UHFFFAOYSA-N 2-amino-n-[6-[(2-aminobenzoyl)amino]hexyl]benzamide Chemical compound NC1=CC=CC=C1C(=O)NCCCCCCNC(=O)C1=CC=CC=C1N YJEULLIOUKINGM-UHFFFAOYSA-N 0.000 claims description 4
- 229940123973 Oxygen scavenger Drugs 0.000 claims description 4
- ZLMKQJQJURXYLC-UHFFFAOYSA-N bis(2-ethylhexoxy)-oxophosphanium Chemical compound CCCCC(CC)CO[P+](=O)OCC(CC)CCCC ZLMKQJQJURXYLC-UHFFFAOYSA-N 0.000 claims description 4
- 239000003054 catalyst Substances 0.000 claims description 4
- 238000002425 crystallisation Methods 0.000 claims description 4
- 230000008025 crystallization Effects 0.000 claims description 4
- LXCYSACZTOKNNS-UHFFFAOYSA-N diethoxy(oxo)phosphanium Chemical compound CCO[P+](=O)OCC LXCYSACZTOKNNS-UHFFFAOYSA-N 0.000 claims description 4
- LUJKYTUFQMQIBA-UHFFFAOYSA-N 1-octadecoxyphosphonoyloxyoctadecane Chemical compound CCCCCCCCCCCCCCCCCCOP(=O)OCCCCCCCCCCCCCCCCCC LUJKYTUFQMQIBA-UHFFFAOYSA-N 0.000 claims description 3
- CYXGBTZYTXLVDN-UHFFFAOYSA-N 1-octoxyphosphonoyloxyoctane Chemical compound CCCCCCCCOP(=O)OCCCCCCCC CYXGBTZYTXLVDN-UHFFFAOYSA-N 0.000 claims description 3
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- 239000002904 solvent Substances 0.000 claims description 3
- 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 claims description 2
- 239000007800 oxidant agent Substances 0.000 claims 2
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 24
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- QQVIHTHCMHWDBS-UHFFFAOYSA-N isophthalic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 description 19
- 239000004645 polyester resin Substances 0.000 description 19
- 229920000139 polyethylene terephthalate Polymers 0.000 description 18
- 239000005020 polyethylene terephthalate Substances 0.000 description 18
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- 230000001588 bifunctional effect Effects 0.000 description 14
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 13
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 12
- 125000004432 carbon atom Chemical group C* 0.000 description 12
- GLDOVTGHNKAZLK-UHFFFAOYSA-N octadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCO GLDOVTGHNKAZLK-UHFFFAOYSA-N 0.000 description 12
- 150000002148 esters Chemical class 0.000 description 11
- 238000004519 manufacturing process Methods 0.000 description 11
- 150000005846 sugar alcohols Polymers 0.000 description 11
- 125000000217 alkyl group Chemical group 0.000 description 10
- 229920005989 resin Polymers 0.000 description 10
- 239000011347 resin Substances 0.000 description 10
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 9
- 230000004888 barrier function Effects 0.000 description 9
- 238000001125 extrusion Methods 0.000 description 9
- KKEYFWRCBNTPAC-UHFFFAOYSA-N terephthalic acid group Chemical group C(C1=CC=C(C(=O)O)C=C1)(=O)O KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 9
- 239000002253 acid Substances 0.000 description 8
- 239000008188 pellet Substances 0.000 description 8
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 8
- 238000006116 polymerization reaction Methods 0.000 description 8
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 7
- 229920006121 Polyxylylene adipamide Polymers 0.000 description 7
- KBPLFHHGFOOTCA-UHFFFAOYSA-N caprylic alcohol Natural products CCCCCCCCO KBPLFHHGFOOTCA-UHFFFAOYSA-N 0.000 description 7
- 239000000463 material Substances 0.000 description 7
- KYTZHLUVELPASH-UHFFFAOYSA-N naphthalene-1,2-dicarboxylic acid Chemical group C1=CC=CC2=C(C(O)=O)C(C(=O)O)=CC=C21 KYTZHLUVELPASH-UHFFFAOYSA-N 0.000 description 7
- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 description 7
- 239000012071 phase Substances 0.000 description 7
- 229920000642 polymer Polymers 0.000 description 7
- 229920001169 thermoplastic Polymers 0.000 description 7
- 239000004416 thermosoftening plastic Substances 0.000 description 7
- KGRVJHAUYBGFFP-UHFFFAOYSA-N 2,2'-Methylenebis(4-methyl-6-tert-butylphenol) Chemical compound CC(C)(C)C1=CC(C)=CC(CC=2C(=C(C=C(C)C=2)C(C)(C)C)O)=C1O KGRVJHAUYBGFFP-UHFFFAOYSA-N 0.000 description 6
- XUQNLOIVFHUMTR-UHFFFAOYSA-N 2-[[2-hydroxy-5-nonyl-3-(1-phenylethyl)phenyl]methyl]-4-nonyl-6-(1-phenylethyl)phenol Chemical compound OC=1C(C(C)C=2C=CC=CC=2)=CC(CCCCCCCCC)=CC=1CC(C=1O)=CC(CCCCCCCCC)=CC=1C(C)C1=CC=CC=C1 XUQNLOIVFHUMTR-UHFFFAOYSA-N 0.000 description 6
- IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 description 6
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 6
- 125000001931 aliphatic group Chemical group 0.000 description 6
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 6
- 235000013305 food Nutrition 0.000 description 6
- 239000007789 gas Substances 0.000 description 6
- 238000001746 injection moulding Methods 0.000 description 6
- 239000001301 oxygen Substances 0.000 description 6
- 229910052760 oxygen Inorganic materials 0.000 description 6
- ABLZXFCXXLZCGV-UHFFFAOYSA-N Phosphorous acid Chemical compound OP(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 description 5
- 239000007983 Tris buffer Substances 0.000 description 5
- 125000002723 alicyclic group Chemical group 0.000 description 5
- QYQADNCHXSEGJT-UHFFFAOYSA-N cyclohexane-1,1-dicarboxylate;hydron Chemical compound OC(=O)C1(C(O)=O)CCCCC1 QYQADNCHXSEGJT-UHFFFAOYSA-N 0.000 description 5
- 150000002009 diols Chemical class 0.000 description 5
- XXMIOPMDWAUFGU-UHFFFAOYSA-N hexane-1,6-diol Chemical compound OCCCCCCO XXMIOPMDWAUFGU-UHFFFAOYSA-N 0.000 description 5
- 125000001183 hydrocarbyl group Chemical group 0.000 description 5
- 239000000178 monomer Substances 0.000 description 5
- 238000000465 moulding Methods 0.000 description 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 5
- 229920006012 semi-aromatic polyamide Polymers 0.000 description 5
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 description 4
- BPXVHIRIPLPOPT-UHFFFAOYSA-N 1,3,5-tris(2-hydroxyethyl)-1,3,5-triazinane-2,4,6-trione Chemical compound OCCN1C(=O)N(CCO)C(=O)N(CCO)C1=O BPXVHIRIPLPOPT-UHFFFAOYSA-N 0.000 description 4
- ALVZNPYWJMLXKV-UHFFFAOYSA-N 1,9-Nonanediol Chemical compound OCCCCCCCCCO ALVZNPYWJMLXKV-UHFFFAOYSA-N 0.000 description 4
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- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 4
- FBPFZTCFMRRESA-KVTDHHQDSA-N D-Mannitol Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KVTDHHQDSA-N 0.000 description 4
- FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- 101000576320 Homo sapiens Max-binding protein MNT Proteins 0.000 description 4
- ORLQHILJRHBSAY-UHFFFAOYSA-N [1-(hydroxymethyl)cyclohexyl]methanol Chemical compound OCC1(CO)CCCCC1 ORLQHILJRHBSAY-UHFFFAOYSA-N 0.000 description 4
- 150000007513 acids Chemical class 0.000 description 4
- 229920003231 aliphatic polyamide Polymers 0.000 description 4
- 125000003118 aryl group Chemical group 0.000 description 4
- 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 4
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 4
- 239000004305 biphenyl Substances 0.000 description 4
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- 125000006267 biphenyl group Chemical group 0.000 description 4
- 150000004985 diamines Chemical class 0.000 description 4
- DNIAPMSPPWPWGF-UHFFFAOYSA-N monopropylene glycol Natural products CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 4
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- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 4
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- AKEUNCKRJATALU-UHFFFAOYSA-N 2,6-dihydroxybenzoic acid Chemical compound OC(=O)C1=C(O)C=CC=C1O AKEUNCKRJATALU-UHFFFAOYSA-N 0.000 description 2
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Classifications
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- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
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- C08L67/02—Polyesters derived from dicarboxylic acids and dihydroxy compounds
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- 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
- C08G63/02—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds
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- C08G63/181—Acids containing aromatic rings
- C08G63/183—Terephthalic acids
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- 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
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- 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
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- C08K5/005—Stabilisers against oxidation, heat, light, ozone
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- 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
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- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
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- 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
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- C08K5/49—Phosphorus-containing compounds
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
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- 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
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- C08K5/151—Heterocyclic compounds having oxygen in the ring having one oxygen atom in the ring
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- 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
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- 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
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- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
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- 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
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- Y10T428/1397—Single layer [continuous layer]
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Description
バリア・ブレンドを教示する。
本明細書において議論される米国特許及び公開された出願は、参照することにより組み込まれる。
A)a)アルデヒドスカベンジャー(捕捉剤)から選択される一種以上の化合物及び
b)フェノール系抗酸化剤、有機リン系安定剤及びラクトン系安定剤から選択される一種以上の化合物
の組み合わせ又は
B)c)一種以上のラクトン系安定剤及び
d)フェノール系抗酸化剤及び有機リン系安定剤から選択される一種以上の化合物
の組み合わせを含む、加熱工程において着色及びヘイズ形成しやすいポリマーブレンド組成物が開示される。
A)a)アルデヒドスカベンジャー(捕捉剤)から選択される一種以上の化合物及び
b)フェノール系抗酸化剤、有機リン系安定剤及びラクトン系安定剤から選択される一種以上の化合物
の組み合わせ又は
B)c)一種以上のラクトン系安定剤及び
d)フェノール系抗酸化剤及び有機リン系安定剤から選択される一種以上の化合物
の組み合わせの混合物を溶融ブレンドする工程を含む、方法が開示される。
ポリエステル及びポリアミドは既知のものであって、例えば、米国特許出願公開第2004/0013833号明細書、米国特許出願公開第2008/0009574号明細書、及び米国特許出願公開第2007/0093616号明細書に開示されるものであり、本開示の内容は参照することによって組み込まれる。
を含むコポリエステルは製造が容易であることから、好ましい脂環式二官能性化合物単位である。さらにこれらの単位は、コンテナの落下衝撃強度を改善し、透明性を著しく改善する。
(2−ヒドロキシエトキシ)エトキシ)フェニル)−2−(4−(2−ヒドロキシエトキシ)フェニル)プロパン、2,2−ビス(4−(2−(2−ヒドロキシエトキシ)エトキシ)フェニル)プロパン、ビス(4−(2−ヒドロキシエトキシ)フェニル)スルホン、(4−((2−ヒドロキシエトキシ)エトキシ)フェニル)−(4−(2−ヒドロキシエトキシ)フェニル)スルホン、1,1−ビス(4−(2−ヒドロキシエトキシ)フェニル)シクロヘキサン、1−(4−(2−(2−ヒドロキシエトキシ)エトキシ)エトキシ)フェニル)−1−(4−(2−ヒドロキシエトキシ)フェニル)シクロヘキサン、1,1−ビス(4−(2−(2−ヒドロキシエトキシ)エトキシ)フェニル)シクロヘキサン、2,2−ビス(4−(2−ヒドロキシエトキシ)−2,3,5,6−テトラブロモフェニル)プロパン、1,4−ビス(2−ヒドロキシエトキシ)ベンゼン、1−(2−ヒドロキシエトキシ)−4−(2−(2−ヒドロキシエトキシ)エトキシ)ベンゼン又は1,4−ビス(2−(2−ヒドロキシエトキシ)エトキシ)ベンゼンから誘導されるジオール単位が挙げられる。上述したこれらのジオール単位のうち、好ましいものは、これらジオール単位の何れかを含むポリエステル樹脂が、優れた溶融安定性を有するとともに、製造容易であることから、2,2−ビス(4−(2−ヒドロキシエトキシ)フェニル)プロパン単位、ビス(4−(2−ヒドロキシエトキシ)フェニル)スルホン単位及び1,4−ビス(2−ヒドロキシエトキシ)ベンゼン単位である。更に、前記樹脂からの成形品は、優れた色調と優れた耐衝撃性を有する。
酒石酸及びリンゴ酸などの脂肪族ヒドロキシカルボン酸;及びそれらのエステル形成誘導体から誘導されるものが挙げられる。
本質的にそれから構成されことが望ましい。好ましい実施態様に従い使用されるPETは、適切な量の一種以上のコモノマー成分と共重合し得る。従って、共重合化されたポリエステル樹脂は、ポリエステルの全構成単位の総モルに対して、1乃至6モル%の量で、例えば約1.5、2、2.5、3、3.5、4、4.5、5及び5.5モル%の量で、コモノマー成分を含むことが望ましい。樹脂の製造工程において副生成物として製造され得るジエチレングリコールとの共重合物の程度を考慮して、上述の範囲内でいくつかの他の成分がそれらとの共重合樹脂を作成するために樹脂に添加され得る。そのような他の成分は特に定義されないが、上述した任意のモノマーが使用できる。幾つかの好ましいモノマーとしては、ただし限定されないが、ネオペンチルグリコール、シクロヘキサンジメタノール(CHDM)、シクロヘキサンジカルボン酸、イソフタル酸(IPA)、及びナフタレンジカルボン酸(NDC)が挙げられる。
ジアミン複合体が使用される場合、混合物は平衡に達するまで加熱溶融及び撹拌される。分子量は二酸−ジアミン割合によってコントロールされる。二酸の過剰は、アセトアルデヒドと反応し得る高濃度の末端アミノ基を製造する。二酸−ジアミン複合体が分離ステップで製造される場合、過剰のジアミンが重合の前に加えられる。重合は大気圧で又は高圧で実施され得る。
アセトアルデヒド(アルデヒド)スカベンジャーは既知であり、例えば米国特許第6,762,275号明細書、米国特許第6,936,204号明細書及び米国特許第6,274,212号明細書に開示されるものであり、参照することによってそれぞれ本書に組み込まれる。適当なアルデヒドスカベンジャーはまた、米国特許第6,191,209号明細書及び米国特許第7,138,457号明細書において教示され、それぞれ参照することによって本書に組み込まれる。適当なアルデヒドスカベンジャーはまた、米国特許出願公開第2005/0176859号明細書において教示され、参照することによって組み込まれる。アルデヒドスカベンジャーはポリエステルにおける使用に関して既知の添加剤である。
T1は直鎖又は分岐鎖の炭素原子数1乃至36のアルキル基、炭素原子数5乃至12のシ
クロアルキル基、炭素原子数7乃至9のアラルキル基、又は、1つ又は2つの炭素原子数1乃至12のアルキル基もしくは1つ又は2つのハロゲン原子で置換された前記アラルキル基を表し;そしてT2は水素原子、又は独立して、T1と同じ意味を有する。)
で表されるジアルキルヒドロキシルアミンである。
フェノール系抗酸化剤は既知であり、例えば:
クチルチオメチル−6−エチルフェノール、2,6−ジドデシルチオメチル−4−ノニルフェノール。
アセテート。
、i−オクタノール、オクタデカノール、1,6−ヘキサンジオール、1,9−ノナンジオール、エチレングリコール、1,2−プロパンジオール、ネオペンチルグリコール、チオジエチレングリコール、ジエチレングリコール、トリエチレングリコール、ペンタエリスリトール、トリス(ヒドロキシエチル)イソシアヌレート、N,N’−ビス(ヒドロキシエチル)オキサミド、3−チアウンデカノール、3−チアペンタデカノール、トリメチルヘキサンジオール、トリメチロールプロパン、4−ヒドロキシメチル−1−ホスファ−2,6,7−トリオキサビシクロ[2.2.2]オクタンとのエステル。
4,6−ジ−第三ブチルフェノール)、2,2’−エチリデンビス(4,6−ジ−第三ブチルフェノール)、2,2’−エチリデンビス(6−第三ブチル−4−イソブチルフェノール)、2,2’−メチレンビス[6−(α−メチルベンジル)−4−ノニルフェノール]、2,2’−メチレンビス[6−(α,α−ジメチルベンジル)−4−ノニルフェノール]、2,6−ビス(3−第三ブチル−5−メチル−2−ヒドロキシベンジル)−4−メチルフェノール、及び1,1−ビス(3,5−ジメチル−2−ヒドロキシフェニル)ブタンからなる群から選択される化合物のモノアクリレートエステルである。
有機リン系化合物は、既知のポリマー加工安定剤である。例えば、プラスチック添加剤ハンドブック(Plastics Additives Handbook),R.ガハター(R.Gaechter)及びH.ミューラー(H.Mueller)編集,第4版,1993年,40−71ページには、ポリプロピレン(PP)とポリエチレン(PE)の安定化が議論されている。
、テトラキス(2,4−ジ−第三ブチルフェニル)4,4’−ビフェニレンジホスホニット(H)、6−イソオクチルオキシ−2,4,8,10−テトラ−第三ブチル−ジベンゾ[d,f][1,3,2]−ジオキサホスフェピン(C)、6−フルオロ−2,4,8,10−テトラ−第三ブチル−12−メチル−ジベンゾ[d,g]−1,3,2−ジオキサホスホシン(A)、ビス(2,4−ジ−第三ブチル−6−メチルフェニル)メチルホスフィット、ビス(2,4−ジ−第三ブチル−6−メチルフェニル)エチルホスフィット(G)、2,2’,2”−ニトリロ[トリエチルトリス(3,3’,5,5’−テトラ−第三ブチル−1,1’−ビフェニル−2,2’―ジイル)ホスフィット](B)、ビス(2,4−ジ−第三ブチルフェニル)オクチルホスフィット、ポリ(4,4’−{2,2’−ジメチル−5,5’−ジ−第三ブチルフェニルスルフィド−}オクチルホスフィット)、ポリ(4,4’{−イソプロピリデンジフェノール}−オクチルホスフィット)、ポリ(4,4’−{イソプロピリデンビス[2,6−ジブロモフェノール]}−オクチルホスフィット)、ポリ(4,4’−{2,2−ジメチル−5,5’−ジ−第三ブチルフェニルスルフィド}−ペンタエリスリチルジホスフィット)、
ヒドロカルビル(di−hydrocarbyl hydrogen phosphonates)である。各基Rは独立してヒドロカルビル基として定義される。例えば、ホスホン酸ジヒドロカルビルは、ホスホン酸ジエチル〔ジエチルホスホナート〕、ホスホン酸ジステアリル〔ジステアリルホスホナート〕、ホスホン酸ジベンジル〔ジベンジルホスホナート〕、ホスホン酸ジ−(2エチルヘキシル)〔ジ(2−エチルヘキシル)ホスホナート〕、ホスホン酸ジ−n−オクチル〔ジ−n−オクチルホスホナート〕、
Phosphonites)は、一般式RO−(R)−P(=O)Hで表される化合物である。各基Rは独立してヒドロカルビル基として定義される。ホスホニット(亜ホスホン酸)化合物は、例えば、上述のホスホナート(phosphonates)の類似化合物である。そのようなホスホニットは、例えば、米国特許第4,940,772号明細書、米国特許第5,717,127号明細書及び米国特許第5,734,072号明細書に開示され、それぞれ参照することによって本明細書に組み込まれる。9,10−ジヒドロ−9−オキサ−10−ホスファフェンアントラセン 10−オキシド化合物は例示化合物である。
ラクトン(ベンゾフラノン)系安定剤は、既知であり、例えば米国特許第6,521,681号明細書に記載されるものであって、参照することによって本明細書に組み込まれる。
、溶融押出又は熱成形が含まれる。
A)a)アルデヒドスカベンジャー(捕捉剤)から選択される一種以上の化合物及び
b)フェノール系抗酸化剤、有機リン系安定剤及びラクトン系安定剤から選択される一種以上の化合物
の組み合わせを含む、加熱工程において着色及びヘイズ形成しやすいポリマーブレンド組成物が好ましい。
B)c)一種以上のラクトン系安定剤及び
d)フェノール系抗酸化剤及び有機リン系安定剤から選択される一種以上の化合物
の組み合わせを含む、加熱工程において着色及びヘイズ形成しやすいポリマーブレンド組成物が好ましい。
A)a)アルデヒドスカベンジャー(捕捉剤)から選択される一種以上の化合物及び
b)フェノール系抗酸化剤、有機リン系安定剤及びラクトン系安定剤から選択される一種以上の化合物
の組み合わせ又は
B)c)一種以上のラクトン系安定剤及び
d)フェノール系抗酸化剤及び有機リン系安定剤から選択される一種以上の化合物
の組み合わせの溶融ブレンドを含む成形品が好ましい。
A)a)アルデヒドスカベンジャー(捕捉剤)から選択される一種以上の化合物及び
b)フェノール系抗酸化剤、有機リン系安定剤及びラクトン系安定剤から選択される一種以上の化合物
の組み合わせ又は
B)c)一種以上のラクトン系安定剤及び
d)フェノール系抗酸化剤及び有機リン系安定剤から選択される一種以上の化合物
の組み合わせを含み、ポリエステル対ポリアミドの質量比が99:1乃至85:15である、加熱工程において着色及びヘイズ形成しやすいポリマーブレンド組成物が好ましい。
A)a)アルデヒドスカベンジャー(捕捉剤)から選択される一種以上の化合物及び
b)フェノール系抗酸化剤、有機リン系安定剤及びラクトン系安定剤から選択される一種以上の化合物
の組み合わせ又は
B)c)一種以上のラクトン系安定剤及び
d)フェノール系抗酸化剤及び有機リン系安定剤から選択される一種以上の化合物
の組み合わせを含み、プレフォーム加熱速度エンハンサー、減摩剤、UV吸収剤、不活性粒子添加剤、着色剤、分岐剤、難燃剤、結晶化制御剤、衝撃改質剤、触媒不活性化剤、溶融強度エンハンサー、帯電防止剤、滑剤、鎖延長剤、核剤、溶剤、充填剤及び可塑剤からなる群から選択されるさらなる添加剤が存在してなる、加熱工程において着色及びヘイズ形成しやすいポリマーブレンド組成物が好ましい。
PET:M&G クリアタフ(CLEARTUF)8006、ボトルグレード PET、コポリマー IV 0.80
ナイロンMXD−6:三菱ガス化学アドバンスドポリマーズ社、グレード S6007、CAS登録番号25718−70−1
50 射出成形機に2”×2”×0.0060”型(=50.8mm×50.8mm×1.52mm型)を備え付け、プラークを射出圧(900psi[=6205kPa=62bar])、ノズル温度(288℃)、型温(70°F[=21℃])、スクリュー速度(150rpm)条件で、成形した。
一般手順に従い、有機リン系安定剤A及び有機リン系安定剤B、ビス(2,4−ジ−第三ブチルフェノール)ペンタエリスリトールジホスフィット、CAS登録番号26741−53−7をアルデヒドスカベンジャー1、アントラニルアミドと一緒に使用した。プラークの黄色度及び白色度を1通過後に評価した。コントロールは安定剤を含まない。結果は以下のとおりである。
一般手順に従い、有機リン系安定剤A及びアルデヒドスカベンジャー2、N,N’−1,6−ヘキサンジイルビス(2−アミノベンズアミド)、CAS登録番号103956−07−6を添加剤として一緒に使用した。コントロールは安定剤を含まない。黄色度を1通過後のプラークで評価した。結果は以下のとおりである。
一般手順に従い、ラクトン4をアルデヒドスカベンジャー1と一緒に、並びに、リン系安定剤Aと一緒に試験した。プラークの黄色度(b*)及び白色度(L*)を1通過後に評価した。コントロールは安定剤を含まない。結果は以下のとおりである。
実施例1及び実施例2を、リン系安定剤の代わりに、アルデヒドスカベンジャー1及び2と、フェノール系抗酸化剤Aを用いて繰り返した。卓越した結果が得られた。
実施例1を、リン系安定剤の代わりに、アルデヒドスカベンジャー1とラクトン系安定剤1−3を用いて繰り返した。実施例1を、リン系安定剤の代わりに、アルデヒドスカベンジャー2とラクトンスカベンジャー1−4を用いて繰り返した。卓越した結果が得られた。
実施例3をラクトン系安定剤1−3を用いて繰り返した。卓越した結果が得られた。
実施例3を、アルデヒドスカベンジャーとリン系安定剤の代わりに、ラクトン系安定剤1−4とフェノール系抗酸化剤を用いて、繰り返した。卓越した結果が得られた。
Claims (18)
- 少なくとも一種のポリエステル及び少なくとも一種のポリアミド、並びに、
A)a)アントラニルアミド又はN,N’−1,6−ヘキサンジイルビス(2−アミノ−ベンズアミド)であるアルデヒドスカベンジャー(捕捉剤)から選択される一種以上の化合物及び
b)フェノール系抗酸化剤、有機リン系安定剤及びラクトン系安定剤から選択される一種以上の化合物
の組み合わせ又は
B)c)一種以上のラクトン系安定剤及び
d)フェノール系抗酸化剤及び有機リン系安定剤から選択される一種以上の化合物
の組み合わせを含む、ポリマーブレンド組成物。 - 前記ポリエステルがPETである、請求項1記載の組成物。
- 前記ポリアミドがポリ−m−キシレンアジポアミドである、請求項1記載の組成物。
- 成分A)を含む、請求項1記載の組成物。
- 成分B)を含む、請求項1記載の組成物。
- 前記ポリエステルとポリアミドの質量比が99:1乃至85:15である、請求項1記載の組成物。
- 成分A)又はB)の添加剤が、組成物の質量に基づいて、それぞれ0.01乃至0.3質量%で存在する、請求項1記載の組成物。
- プレフォームの加熱速度エンハンサー、減摩剤、UV吸収剤、不活性粒子添加剤、着色剤、分岐剤、難燃剤、結晶化制御剤、衝撃改質剤、触媒不活性化剤、溶融強度エンハンサー、帯電防止剤、滑剤、鎖延長剤、核剤、溶媒、充填剤又は可塑剤をさらに含む、請求項1記載の組成物。
- 相溶化剤又は酸素スカベンジャー(捕捉剤)をさらに含む、請求項1記載の組成物。
- 熱処理の際のポリマーブレンドの着色及びヘイズ形成を減少する方法であって、
少なくとも一種のポリエステル及び少なくとも一種のポリアミド、並びに
A)a)アントラニルアミド又はN,N’−1,6−ヘキサンジイルビス(2−アミノ−ベンズアミド)であるアルデヒドスカベンジャー(捕捉剤)から選択される一種以上の化合物及び
b)フェノール系抗酸化剤、有機リン系安定剤及びラクトン系安定剤から選択される
一種以上の化合物
の組み合わせ又は
B)c)一種以上のラクトン系安定剤及び
d)フェノール系抗酸化剤及び有機リン系安定剤から選択される一種以上の化合物
の組み合わせの混合物を溶融ブレンドする工程を含む、方法。 - 少なくとも一種のポリエステル及び少なくとも一種のポリアミド、並びに
A)a)アントラニルアミド又はN,N’−1,6−ヘキサンジイルビス(2−アミノ−ベンズアミド)であるアルデヒドスカベンジャー(捕捉剤)から選択される一種以上の化合物及び
b)フェノール系抗酸化剤、有機リン系安定剤及びラクトン系安定剤から選択される一種以上の化合物
の組み合わせ又は
B)c)一種以上のラクトン系安定剤及び
d)フェノール系抗酸化剤及び有機リン系安定剤から選択される一種以上の化合物
の組み合わせの溶融ブレンドを含む、成形品。 - ボトル、コンテナ又はフィルムである、請求項17記載の成形品。
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US21001109P | 2009-03-13 | 2009-03-13 | |
US61/210,011 | 2009-03-13 | ||
PCT/EP2010/053005 WO2010103023A1 (en) | 2009-03-13 | 2010-03-10 | Stabilized blends of polyester and polyamide |
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JP2012520364A JP2012520364A (ja) | 2012-09-06 |
JP5457471B2 true JP5457471B2 (ja) | 2014-04-02 |
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JP2011553436A Expired - Fee Related JP5457471B2 (ja) | 2009-03-13 | 2010-03-10 | ポリエステルとポリアミドの安定化ブレンド |
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US (1) | US8440281B2 (ja) |
EP (1) | EP2406320A1 (ja) |
JP (1) | JP5457471B2 (ja) |
KR (1) | KR20120014889A (ja) |
CN (1) | CN102348762A (ja) |
TW (1) | TW201038664A (ja) |
WO (1) | WO2010103023A1 (ja) |
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US8344172B2 (en) | 2011-03-25 | 2013-01-01 | Stepan Company | Preparation of antiplasticizers for thermoplastic polyesters |
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CN103275470A (zh) * | 2013-06-21 | 2013-09-04 | 苏州新区特氟龙塑料制品厂 | 一种用于种植作物的塑料薄膜 |
CA2934776A1 (en) | 2013-12-25 | 2015-07-02 | Mitsubishi Gas Chemical Company, Inc. | Polyester-based resin composition, and molded body using the resin composition |
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-
2010
- 2010-03-10 WO PCT/EP2010/053005 patent/WO2010103023A1/en active Application Filing
- 2010-03-10 KR KR1020117020168A patent/KR20120014889A/ko not_active Application Discontinuation
- 2010-03-10 JP JP2011553436A patent/JP5457471B2/ja not_active Expired - Fee Related
- 2010-03-10 EP EP10708759A patent/EP2406320A1/en not_active Withdrawn
- 2010-03-10 CN CN2010800113828A patent/CN102348762A/zh active Pending
- 2010-03-11 US US12/721,777 patent/US8440281B2/en not_active Expired - Fee Related
- 2010-03-12 TW TW099107343A patent/TW201038664A/zh unknown
Also Published As
Publication number | Publication date |
---|---|
KR20120014889A (ko) | 2012-02-20 |
JP2012520364A (ja) | 2012-09-06 |
US20100233405A1 (en) | 2010-09-16 |
US8440281B2 (en) | 2013-05-14 |
TW201038664A (en) | 2010-11-01 |
EP2406320A1 (en) | 2012-01-18 |
CN102348762A (zh) | 2012-02-08 |
WO2010103023A1 (en) | 2010-09-16 |
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