TWI653260B - 具有提升之衝擊強度、抗變色能力以及反射率的聚對苯二甲酸環己烷二甲醇酯共聚物以及以此製成之樹脂模製品 - Google Patents

具有提升之衝擊強度、抗變色能力以及反射率的聚對苯二甲酸環己烷二甲醇酯共聚物以及以此製成之樹脂模製品 Download PDF

Info

Publication number: TWI653260B
Authority: TW; Taiwan
Prior art keywords: resin molded; copolymer; group; terephthalate; weight
Prior art date: 2013-12-30

Application number

TW103145826A

Other languages

English (en)

Chinese (zh)

Other versions

TW201527357A (zh

Inventor

李秀珉

金鍾亮

金泰榮

白智元

李富淵

Original Assignee

Sk化學公司

Priority date (The priority date 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 date listed.)

2013-12-30

Filing date

2014-12-26

Publication date

2019-03-11

2014-12-26 Application filed by Sk化學公司 filed Critical Sk化學公司

2015-07-16 Publication of TW201527357A publication Critical patent/TW201527357A/zh

2019-03-11 Application granted granted Critical

2019-03-11 Publication of TWI653260B publication Critical patent/TWI653260B/zh

Links

229920001577 copolymer Polymers 0.000 title claims abstract description 62
229920005989 resin Polymers 0.000 title claims abstract description 53
239000011347 resin Substances 0.000 title claims abstract description 53
-1 Polybutylene terephthalate dimethanol Polymers 0.000 title claims description 76
238000002310 reflectometry Methods 0.000 title abstract description 10
KKEYFWRCBNTPAC-UHFFFAOYSA-L terephthalate(2-) Chemical compound [O-]C(=O)C1=CC=C(C([O-])=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-L 0.000 claims abstract description 26
238000005886 esterification reaction Methods 0.000 claims description 57
KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 claims description 56
239000003054 catalyst Substances 0.000 claims description 42
239000000126 substance Substances 0.000 claims description 35
150000001875 compounds Chemical class 0.000 claims description 34
238000006068 polycondensation reaction Methods 0.000 claims description 33
229920001296 polysiloxane Polymers 0.000 claims description 27
125000004432 carbon atom Chemical group C* 0.000 claims description 26
RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 claims description 24
WOZVHXUHUFLZGK-UHFFFAOYSA-N dimethyl terephthalate Chemical compound COC(=O)C1=CC=C(C(=O)OC)C=C1 WOZVHXUHUFLZGK-UHFFFAOYSA-N 0.000 claims description 23
239000010936 titanium Substances 0.000 claims description 23
229910052719 titanium Inorganic materials 0.000 claims description 23
DQWPFSLDHJDLRL-UHFFFAOYSA-N triethyl phosphate Chemical compound CCOP(=O)(OCC)OCC DQWPFSLDHJDLRL-UHFFFAOYSA-N 0.000 claims description 20
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 19
239000000203 mixture Substances 0.000 claims description 18
GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 claims description 17
OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 claims description 17
238000000034 method Methods 0.000 claims description 14
125000003118 aryl group Chemical group 0.000 claims description 12
LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 12
239000003381 stabilizer Substances 0.000 claims description 12
OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims description 11
229910052698 phosphorus Inorganic materials 0.000 claims description 11
239000011574 phosphorus Substances 0.000 claims description 11
125000001183 hydrocarbyl group Chemical group 0.000 claims description 10
125000000217 alkyl group Chemical group 0.000 claims description 9
125000002723 alicyclic group Chemical group 0.000 claims description 7
WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 claims description 7
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims description 6
125000004464 hydroxyphenyl group Chemical group 0.000 claims description 6
VXUYXOFXAQZZMF-UHFFFAOYSA-N titanium(IV) isopropoxide Chemical compound CC(C)O[Ti](OC(C)C)(OC(C)C)OC(C)C VXUYXOFXAQZZMF-UHFFFAOYSA-N 0.000 claims description 6
125000001931 aliphatic group Chemical group 0.000 claims description 5
238000006243 chemical reaction Methods 0.000 claims description 5
HKJYVRJHDIPMQB-UHFFFAOYSA-N propan-1-olate;titanium(4+) Chemical compound CCCO[Ti](OCCC)(OCCC)OCCC HKJYVRJHDIPMQB-UHFFFAOYSA-N 0.000 claims description 5
GGUBFICZYGKNTD-UHFFFAOYSA-N triethyl phosphonoacetate Chemical compound CCOC(=O)CP(=O)(OCC)OCC GGUBFICZYGKNTD-UHFFFAOYSA-N 0.000 claims description 5
WVLBCYQITXONBZ-UHFFFAOYSA-N trimethyl phosphate Chemical group COP(=O)(OC)OC WVLBCYQITXONBZ-UHFFFAOYSA-N 0.000 claims description 5
XZZNDPSIHUTMOC-UHFFFAOYSA-N triphenyl phosphate Chemical compound C=1C=CC=CC=1OP(OC=1C=CC=CC=1)(=O)OC1=CC=CC=C1 XZZNDPSIHUTMOC-UHFFFAOYSA-N 0.000 claims description 5
QUVMSYUGOKEMPX-UHFFFAOYSA-N 2-methylpropan-1-olate;titanium(4+) Chemical compound [Ti+4].CC(C)C[O-].CC(C)C[O-].CC(C)C[O-].CC(C)C[O-] QUVMSYUGOKEMPX-UHFFFAOYSA-N 0.000 claims description 3
229910000147 aluminium phosphate Inorganic materials 0.000 claims description 3
239000013522 chelant Substances 0.000 claims description 3
238000002156 mixing Methods 0.000 claims description 3
ISIJQEHRDSCQIU-UHFFFAOYSA-N tert-butyl 2,7-diazaspiro[4.5]decane-7-carboxylate Chemical compound C1N(C(=O)OC(C)(C)C)CCCC11CNCC1 ISIJQEHRDSCQIU-UHFFFAOYSA-N 0.000 claims description 3
YFESLUXJCTZZFA-UHFFFAOYSA-N [4-(hydroxymethyl)cyclohexyl]methanol Chemical compound OCC1CCC(CO)CC1.OCC1CCC(CO)CC1 YFESLUXJCTZZFA-UHFFFAOYSA-N 0.000 claims 1
FPCJKVGGYOAWIZ-UHFFFAOYSA-N butan-1-ol;titanium Chemical compound [Ti].CCCCO.CCCCO.CCCCO.CCCCO FPCJKVGGYOAWIZ-UHFFFAOYSA-N 0.000 claims 1
230000006641 stabilisation Effects 0.000 claims 1
238000011105 stabilization Methods 0.000 claims 1
230000000704 physical effect Effects 0.000 abstract description 16
239000000654 additive Substances 0.000 abstract description 7
238000002845 discoloration Methods 0.000 abstract description 7
YIMQCDZDWXUDCA-UHFFFAOYSA-N [4-(hydroxymethyl)cyclohexyl]methanol Chemical compound OCC1CCC(CO)CC1 YIMQCDZDWXUDCA-UHFFFAOYSA-N 0.000 description 22
230000000052 comparative effect Effects 0.000 description 14
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 12
239000004205 dimethyl polysiloxane Substances 0.000 description 11
229920000435 poly(dimethylsiloxane) Polymers 0.000 description 11
125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 11
MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 9
239000000463 material Substances 0.000 description 6
230000000694 effects Effects 0.000 description 5
229920001707 polybutylene terephthalate Polymers 0.000 description 5
229920000728 polyester Polymers 0.000 description 5
229920000139 polyethylene terephthalate Polymers 0.000 description 5
239000005020 polyethylene terephthalate Substances 0.000 description 5
238000005259 measurement Methods 0.000 description 4
229920001123 polycyclohexylenedimethylene terephthalate Polymers 0.000 description 4
238000002360 preparation method Methods 0.000 description 3
DNIAPMSPPWPWGF-VKHMYHEASA-N (+)-propylene glycol Chemical compound C[C@H](O)CO DNIAPMSPPWPWGF-VKHMYHEASA-N 0.000 description 2
YPFDHNVEDLHUCE-UHFFFAOYSA-N 1,3-propanediol Substances OCCCO YPFDHNVEDLHUCE-UHFFFAOYSA-N 0.000 description 2
OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 2
229920001283 Polyalkylene terephthalate Polymers 0.000 description 2
239000004952 Polyamide Substances 0.000 description 2
230000009286 beneficial effect Effects 0.000 description 2
229910052799 carbon Inorganic materials 0.000 description 2
238000002425 crystallisation Methods 0.000 description 2
230000008025 crystallization Effects 0.000 description 2
125000000753 cycloalkyl group Chemical group 0.000 description 2
230000032050 esterification Effects 0.000 description 2
SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 description 2
229920002647 polyamide Polymers 0.000 description 2
238000006116 polymerization reaction Methods 0.000 description 2
229920000166 polytrimethylene carbonate Polymers 0.000 description 2
238000012360 testing method Methods 0.000 description 2
ISPYQTSUDJAMAB-UHFFFAOYSA-N 2-chlorophenol Chemical compound OC1=CC=CC=C1Cl ISPYQTSUDJAMAB-UHFFFAOYSA-N 0.000 description 1
SXOZLNQCRCKKHK-UHFFFAOYSA-N CCOC(C)=O.OP(O)(=O)OP(O)(=O)OP(O)(O)=O Chemical compound CCOC(C)=O.OP(O)(=O)OP(O)(=O)OP(O)(O)=O SXOZLNQCRCKKHK-UHFFFAOYSA-N 0.000 description 1
229920000106 Liquid crystal polymer Polymers 0.000 description 1
WJJGAKCAAJOICV-UHFFFAOYSA-N N-dimethyltyrosine Natural products CN(C)C(C(O)=O)CC1=CC=C(O)C=C1 WJJGAKCAAJOICV-UHFFFAOYSA-N 0.000 description 1
ZVOOGERIHVAODX-UHFFFAOYSA-N O-demycinosyltylosin Natural products O=CCC1CC(C)C(=O)C=CC(C)=CC(CO)C(CC)OC(=O)CC(O)C(C)C1OC1C(O)C(N(C)C)C(OC2OC(C)C(O)C(C)(O)C2)C(C)O1 ZVOOGERIHVAODX-UHFFFAOYSA-N 0.000 description 1
239000004734 Polyphenylene sulfide Substances 0.000 description 1
230000000692 anti-sense effect Effects 0.000 description 1
JRFMZTLWVBLNLM-UHFFFAOYSA-N benzene-1,3-dicarboxylic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1.OC(=O)C1=CC=CC(C(O)=O)=C1 JRFMZTLWVBLNLM-UHFFFAOYSA-N 0.000 description 1
INDXRDWMTVLQID-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO.OCCCCO INDXRDWMTVLQID-UHFFFAOYSA-N 0.000 description 1
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
230000015556 catabolic process Effects 0.000 description 1
230000003197 catalytic effect Effects 0.000 description 1
238000006731 degradation reaction Methods 0.000 description 1
230000006866 deterioration Effects 0.000 description 1
150000001990 dicarboxylic acid derivatives Chemical class 0.000 description 1
KYSOBKNOVNLMJS-UHFFFAOYSA-N dimethyl benzene-1,3-dicarboxylate 4,6-dimethylbenzene-1,3-dicarboxylic acid Chemical compound CC1=CC(=C(C=C1C(=O)O)C(=O)O)C.C(C1=CC(C(=O)OC)=CC=C1)(=O)OC KYSOBKNOVNLMJS-UHFFFAOYSA-N 0.000 description 1
KPUWHANPEXNPJT-UHFFFAOYSA-N disiloxane Chemical class [SiH3]O[SiH3] KPUWHANPEXNPJT-UHFFFAOYSA-N 0.000 description 1
239000006185 dispersion Substances 0.000 description 1
229920006351 engineering plastic Polymers 0.000 description 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
230000007717 exclusion Effects 0.000 description 1
239000000835 fiber Substances 0.000 description 1
239000003365 glass fiber Substances 0.000 description 1
150000002334 glycols Chemical class 0.000 description 1
125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
238000002347 injection Methods 0.000 description 1
239000007924 injection Substances 0.000 description 1
239000007788 liquid Substances 0.000 description 1
238000004519 manufacturing process Methods 0.000 description 1
238000002844 melting Methods 0.000 description 1
230000008018 melting Effects 0.000 description 1
229910052751 metal Inorganic materials 0.000 description 1
239000002184 metal Substances 0.000 description 1
150000002739 metals Chemical class 0.000 description 1
230000004048 modification Effects 0.000 description 1
238000012986 modification Methods 0.000 description 1
KBWUXUSGYHVTSX-UHFFFAOYSA-N naphthalene-2,6-dicarboxylic acid Chemical compound C1=C(C(O)=O)C=CC2=CC(C(=O)O)=CC=C21.C1=C(C(O)=O)C=CC2=CC(C(=O)O)=CC=C21 KBWUXUSGYHVTSX-UHFFFAOYSA-N 0.000 description 1
125000001624 naphthyl group Chemical group 0.000 description 1
HMMGMWAXVFQUOA-UHFFFAOYSA-N octamethylcyclotetrasiloxane Chemical compound C[Si]1(C)O[Si](C)(C)O[Si](C)(C)O[Si](C)(C)O1 HMMGMWAXVFQUOA-UHFFFAOYSA-N 0.000 description 1
230000003647 oxidation Effects 0.000 description 1
238000007254 oxidation reaction Methods 0.000 description 1
239000013618 particulate matter Substances 0.000 description 1
239000008188 pellet Substances 0.000 description 1
230000008447 perception Effects 0.000 description 1
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
125000004437 phosphorous atom Chemical group 0.000 description 1
229920000069 polyphenylene sulfide Polymers 0.000 description 1
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
230000035484 reaction time Effects 0.000 description 1
238000011160 research Methods 0.000 description 1
230000000630 rising effect Effects 0.000 description 1
238000007086 side reaction Methods 0.000 description 1
239000007790 solid phase Substances 0.000 description 1
239000000243 solution Substances 0.000 description 1
239000002904 solvent Substances 0.000 description 1
238000005494 tarnishing Methods 0.000 description 1
238000005979 thermal decomposition reaction Methods 0.000 description 1
238000005809 transesterification reaction Methods 0.000 description 1
239000013585 weight reducing agent Substances 0.000 description 1
238000004383 yellowing Methods 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L83/00—Compositions of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon only; Compositions of derivatives of such polymers
- C08L83/10—Block- or graft-copolymers containing polysiloxane sequences
- 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
- C08G63/68—Polyesters containing atoms other than carbon, hydrogen and oxygen
- C08G63/695—Polyesters containing atoms other than carbon, hydrogen and oxygen containing silicon
- C08G63/6954—Polyesters containing atoms other than carbon, hydrogen and oxygen containing silicon derived from polxycarboxylic acids and polyhydroxy compounds
- C08G63/6956—Dicarboxylic acids and dihydroxy compounds
- 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
- C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
- C08G77/42—Block-or graft-polymers containing polysiloxane sequences
- C08G77/445—Block-or graft-polymers containing polysiloxane sequences containing polyester sequences

Landscapes

Chemical & Material Sciences (AREA)
Health & Medical Sciences (AREA)
Chemical Kinetics & Catalysis (AREA)
Medicinal Chemistry (AREA)
Polymers & Plastics (AREA)
Organic Chemistry (AREA)
Polyesters Or Polycarbonates (AREA)

TW103145826A 2013-12-30 2014-12-26 具有提升之衝擊強度、抗變色能力以及反射率的聚對苯二甲酸環己烷二甲醇酯共聚物以及以此製成之樹脂模製品 TWI653260B (zh)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
??10-2013-0167676		2013-12-30
KR20130167676		2013-12-30

Publications (2)

Publication Number	Publication Date
TW201527357A TW201527357A (zh)	2015-07-16
TWI653260B true TWI653260B (zh)	2019-03-11

Family

ID=53493598

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
TW103145826A TWI653260B (zh)	2013-12-30	2014-12-26	具有提升之衝擊強度、抗變色能力以及反射率的聚對苯二甲酸環己烷二甲醇酯共聚物以及以此製成之樹脂模製品

Country Status (3)

Country	Link
KR (1)	KR102252792B1 (fr)
TW (1)	TWI653260B (fr)
WO (1)	WO2015102302A1 (fr)

Family Cites Families (11)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JP2583412B2 (ja) *	1986-02-24	1997-02-19	チッソ株式会社	ヒドロキシル基含有シロキサン化合物
US5102941A (en) *	1989-04-19	1992-04-07	Mitsubishi Rayon Co., Ltd.	Thermoplastic polyester resin composition
US5334656A (en) *	1990-08-27	1994-08-02	Matsubishi Rayon Co., Ltd.	Polyester resin compositions
DE69123210T2 (de) *	1990-08-27	1997-05-28	Mitsubishi Rayon Co	Polyesterharzmasse
KR100361961B1 (ko) *	2000-05-17	2002-11-23	에스케이케미칼주식회사	1,4-사이클로헥산디메탄올이 공중합된 폴리에스테르수지의 제조방법
US6569958B1 (en) *	2001-10-19	2003-05-27	Dow Corning Corporation	Thermoplastic silicone elastomers from compatibilized polyester resins
US8007885B2 (en) *	2005-09-14	2011-08-30	Georgios Topoulos	Light-emitting diode assembly housing comprising poly(cyclohexanedimethanol terephthalate) compositions
KR101297912B1 (ko) *	2006-12-08	2013-08-22	에스케이케미칼주식회사	1,4-사이클로헥산디메탄올이 공중합된 난연성 폴리에스테르수지 조성물 및 이의 제조방법
KR101430264B1 (ko) *	2007-10-25	2014-08-18	에스케이케미칼주식회사	색상이 우수한 고투명성 1,4-사이클로헥산디메탄올 공중합폴리에스테르 수지 및 그 제조방법
KR101360892B1 (ko) *	2011-06-21	2014-02-11	제일모직주식회사	반사성, 내열성, 내황변성 및 내습성이 우수한 폴리에스테르　수지 조성물.
KR101549492B1 (ko) *	2011-12-28	2015-09-03	제일모직주식회사	내황변성과 내충격성이 우수한 폴리에스테르 수지 조성물

2014
- 2014-12-24 WO PCT/KR2014/012830 patent/WO2015102302A1/fr not_active Ceased
- 2014-12-24 KR KR1020140188718A patent/KR102252792B1/ko active Active
- 2014-12-26 TW TW103145826A patent/TWI653260B/zh not_active IP Right Cessation

Also Published As

Publication number	Publication date
TW201527357A (zh)	2015-07-16
KR102252792B1 (ko)	2021-05-17
KR20150079432A (ko)	2015-07-08
WO2015102302A1 (fr)	2015-07-09

Legal Events

Date	Code	Title	Description
2021-12-11	MM4A	Annulment or lapse of patent due to non-payment of fees

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