JP2017531701A - 安定化剤としての3−フェニル−ベンゾフラン−2−オンジホスファイト誘導体 - Google Patents
安定化剤としての3−フェニル−ベンゾフラン−2−オンジホスファイト誘導体 Download PDFInfo
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- JP2017531701A JP2017531701A JP2017506341A JP2017506341A JP2017531701A JP 2017531701 A JP2017531701 A JP 2017531701A JP 2017506341 A JP2017506341 A JP 2017506341A JP 2017506341 A JP2017506341 A JP 2017506341A JP 2017531701 A JP2017531701 A JP 2017531701A
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- YMFIUXNOXADSQY-UHFFFAOYSA-N OP(O)OP(O)O.C1(=CC=CC=C1)C1C(OC2=C1C=CC=C2)=O Chemical class OP(O)OP(O)O.C1(=CC=CC=C1)C1C(OC2=C1C=CC=C2)=O YMFIUXNOXADSQY-UHFFFAOYSA-N 0.000 title description 3
- 150000001875 compounds Chemical class 0.000 claims abstract description 185
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- 229910052739 hydrogen Inorganic materials 0.000 claims description 114
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- 229920000642 polymer Polymers 0.000 claims description 71
- 239000002530 phenolic antioxidant Substances 0.000 claims description 46
- XRBCRPZXSCBRTK-UHFFFAOYSA-N phosphonous acid Chemical class OPO XRBCRPZXSCBRTK-UHFFFAOYSA-N 0.000 claims description 25
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- 239000002253 acid Substances 0.000 claims description 18
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- WPMYUUITDBHVQZ-UHFFFAOYSA-N 3-(3,5-ditert-butyl-4-hydroxyphenyl)propanoic acid Chemical compound CC(C)(C)C1=CC(CCC(O)=O)=CC(C(C)(C)C)=C1O WPMYUUITDBHVQZ-UHFFFAOYSA-N 0.000 claims description 5
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- BGYHLZZASRKEJE-UHFFFAOYSA-N [3-[3-(3,5-ditert-butyl-4-hydroxyphenyl)propanoyloxy]-2,2-bis[3-(3,5-ditert-butyl-4-hydroxyphenyl)propanoyloxymethyl]propyl] 3-(3,5-ditert-butyl-4-hydroxyphenyl)propanoate Chemical compound CC(C)(C)C1=C(O)C(C(C)(C)C)=CC(CCC(=O)OCC(COC(=O)CCC=2C=C(C(O)=C(C=2)C(C)(C)C)C(C)(C)C)(COC(=O)CCC=2C=C(C(O)=C(C=2)C(C)(C)C)C(C)(C)C)COC(=O)CCC=2C=C(C(O)=C(C=2)C(C)(C)C)C(C)(C)C)=C1 BGYHLZZASRKEJE-UHFFFAOYSA-N 0.000 description 9
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- 239000000155 melt Substances 0.000 description 9
- 239000000047 product Substances 0.000 description 9
- JKIJEFPNVSHHEI-UHFFFAOYSA-N Phenol, 2,4-bis(1,1-dimethylethyl)-, phosphite (3:1) Chemical compound CC(C)(C)C1=CC(C(C)(C)C)=CC=C1OP(OC=1C(=CC(=CC=1)C(C)(C)C)C(C)(C)C)OC1=CC=C(C(C)(C)C)C=C1C(C)(C)C JKIJEFPNVSHHEI-UHFFFAOYSA-N 0.000 description 8
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- 239000000010 aprotic solvent Substances 0.000 description 8
- 239000002585 base Substances 0.000 description 8
- 230000015572 biosynthetic process Effects 0.000 description 8
- KBPLFHHGFOOTCA-UHFFFAOYSA-N caprylic alcohol Natural products CCCCCCCCO KBPLFHHGFOOTCA-UHFFFAOYSA-N 0.000 description 8
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- 230000014759 maintenance of location Effects 0.000 description 8
- 239000010813 municipal solid waste Substances 0.000 description 8
- GLDOVTGHNKAZLK-UHFFFAOYSA-N octadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCO GLDOVTGHNKAZLK-UHFFFAOYSA-N 0.000 description 8
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 8
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- 239000000463 material Substances 0.000 description 7
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- 239000002184 metal Substances 0.000 description 7
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 7
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- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 6
- 239000004594 Masterbatch (MB) Substances 0.000 description 6
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 6
- 150000001252 acrylic acid derivatives Chemical class 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
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- ACZGCWSMSTYWDQ-UHFFFAOYSA-N 3h-1-benzofuran-2-one Chemical compound C1=CC=C2OC(=O)CC2=C1 ACZGCWSMSTYWDQ-UHFFFAOYSA-N 0.000 description 5
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- 235000019149 tocopherols Nutrition 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- KHPCPRHQVVSZAH-UHFFFAOYSA-N trans-cinnamyl beta-D-glucopyranoside Natural products OC1C(O)C(O)C(CO)OC1OCC=CC1=CC=CC=C1 KHPCPRHQVVSZAH-UHFFFAOYSA-N 0.000 description 1
- 238000005809 transesterification reaction Methods 0.000 description 1
- 150000003918 triazines Chemical class 0.000 description 1
- INNSFNJTGFCSRN-UHFFFAOYSA-N tridecyl 2-[(3,5-ditert-butyl-4-hydroxyphenyl)methylsulfanyl]acetate Chemical compound CCCCCCCCCCCCCOC(=O)CSCC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 INNSFNJTGFCSRN-UHFFFAOYSA-N 0.000 description 1
- IVIIAEVMQHEPAY-UHFFFAOYSA-N tridodecyl phosphite Chemical compound CCCCCCCCCCCCOP(OCCCCCCCCCCCC)OCCCCCCCCCCCC IVIIAEVMQHEPAY-UHFFFAOYSA-N 0.000 description 1
- CNUJLMSKURPSHE-UHFFFAOYSA-N trioctadecyl phosphite Chemical compound CCCCCCCCCCCCCCCCCCOP(OCCCCCCCCCCCCCCCCCC)OCCCCCCCCCCCCCCCCCC CNUJLMSKURPSHE-UHFFFAOYSA-N 0.000 description 1
- AAAQKTZKLRYKHR-UHFFFAOYSA-N triphenylmethane Chemical compound C1=CC=CC=C1C(C=1C=CC=CC=1)C1=CC=CC=C1 AAAQKTZKLRYKHR-UHFFFAOYSA-N 0.000 description 1
- DCXXMTOCNZCJGO-UHFFFAOYSA-N tristearoylglycerol Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCC(OC(=O)CCCCCCCCCCCCCCCCC)COC(=O)CCCCCCCCCCCCCCCCC DCXXMTOCNZCJGO-UHFFFAOYSA-N 0.000 description 1
- 229920001862 ultra low molecular weight polyethylene Polymers 0.000 description 1
- KJIOQYGWTQBHNH-UHFFFAOYSA-N undecanol Chemical compound CCCCCCCCCCCO KJIOQYGWTQBHNH-UHFFFAOYSA-N 0.000 description 1
- 229920006337 unsaturated polyester resin Polymers 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
- 229920001866 very low density polyethylene Polymers 0.000 description 1
- 235000019154 vitamin C Nutrition 0.000 description 1
- 239000011718 vitamin C Substances 0.000 description 1
- 235000019165 vitamin E Nutrition 0.000 description 1
- 239000011709 vitamin E Substances 0.000 description 1
- 229940046009 vitamin E Drugs 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
- 239000002351 wastewater Substances 0.000 description 1
- 239000010456 wollastonite Substances 0.000 description 1
- 229910052882 wollastonite Inorganic materials 0.000 description 1
- 239000002983 wood substitute Substances 0.000 description 1
- 239000002759 woven fabric Substances 0.000 description 1
- 150000003751 zinc Chemical class 0.000 description 1
- XOOUIPVCVHRTMJ-UHFFFAOYSA-L zinc stearate Chemical compound [Zn+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O XOOUIPVCVHRTMJ-UHFFFAOYSA-L 0.000 description 1
- 239000004711 α-olefin Substances 0.000 description 1
- 239000002076 α-tocopherol Substances 0.000 description 1
- 235000004835 α-tocopherol Nutrition 0.000 description 1
- 239000011590 β-tocopherol Substances 0.000 description 1
- 235000007680 β-tocopherol Nutrition 0.000 description 1
- 239000002478 γ-tocopherol Substances 0.000 description 1
- QUEDXNHFTDJVIY-UHFFFAOYSA-N γ-tocopherol Chemical class OC1=C(C)C(C)=C2OC(CCCC(C)CCCC(C)CCCC(C)C)(C)CCC2=C1 QUEDXNHFTDJVIY-UHFFFAOYSA-N 0.000 description 1
- QUEDXNHFTDJVIY-DQCZWYHMSA-N γ-tocopherol Chemical compound OC1=C(C)C(C)=C2O[C@@](CCC[C@H](C)CCC[C@H](C)CCCC(C)C)(C)CCC2=C1 QUEDXNHFTDJVIY-DQCZWYHMSA-N 0.000 description 1
- 239000002446 δ-tocopherol Substances 0.000 description 1
Classifications
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- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/6564—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms
- C07F9/6571—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms having phosphorus and oxygen atoms as the only ring hetero atoms
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- C08L23/00—Compositions of homopolymers or copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond; Compositions of derivatives of such polymers
- C08L23/02—Compositions of homopolymers or copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond; Compositions of derivatives of such polymers not modified by chemical after-treatment
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- C09K15/00—Anti-oxidant compositions; Compositions inhibiting chemical change
- C09K15/04—Anti-oxidant compositions; Compositions inhibiting chemical change containing organic compounds
- C09K15/32—Anti-oxidant compositions; Compositions inhibiting chemical change containing organic compounds containing two or more of boron, silicon, phosphorus, selenium, tellurium or a metal
- C09K15/322—Anti-oxidant compositions; Compositions inhibiting chemical change containing organic compounds containing two or more of boron, silicon, phosphorus, selenium, tellurium or a metal containing only phosphorus
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- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/655—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having oxygen atoms, with or without sulfur, selenium, or tellurium atoms, as the only ring hetero atoms
- C07F9/65515—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having oxygen atoms, with or without sulfur, selenium, or tellurium atoms, as the only ring hetero atoms the oxygen atom being part of a five-membered ring
- C07F9/65517—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having oxygen atoms, with or without sulfur, selenium, or tellurium atoms, as the only ring hetero atoms the oxygen atom being part of a five-membered ring condensed with carbocyclic rings or carbocyclic ring systems
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Abstract
Description
a)酸化的分解、熱的分解または光誘発性分解を受けやすい有機材料と、
b)式I−P、I−OまたはI−M
R1Pは、部分式II−P、II−OもしくはII−M
R1Oは、部分式II−OもしくはII−Mの1つを表すか、または
R1Mは、部分式II−Mを表し、
R4、R5、R6およびR7は、互いに独立して、水素もしくはC1〜C8−アルキルであり、
RP2、RP3、RP5およびRP6は、互いに独立して、水素もしくはC1〜C8−アルキルであり、
RO1、RO2、RO5およびRO6は、互いに独立して、水素もしくはC1〜C8−アルキルであり、かつ
RM1、RM3、RM5およびRM6は、互いに独立して、水素もしくはC1〜C8−アルキルである]の化合物と、
を含む組成物に関する。
a) ラジカル重合(通常は、高圧および高められた温度下で)
b) 周期律表の第IVb族、第Vb族、第VIb族(例えばクロム)もしくは第VIII族の1種のもしくは1種より多くの金属を通常含む触媒を使用した触媒重合。これらの金属は、通常は、1種もしくは1種より多くの配位子、一般に酸化物、ハロゲン化物、アルコラート、エステル、エーテル、アミン、アルキル、アルケニルおよび/またはアリールを有し、それらはπ配位またはσ配位されていてよい。これらの金属錯体は、遊離形または基材上に、一般に活性化塩化マグネシウム、塩化チタン(III)、アルミナもしくは酸化ケイ素上に固定化されていてよい。これらの触媒は、重合媒体中に可溶性または不溶性であってよい。前記触媒は、それ自体で重合において使用できるか、または更に活性化剤を、一般的に金属アルキル、金属水素化物、金属アルキルハロゲン化物、金属アルキル酸化物もしくは金属アルキルオキサンを使用でき、前記金属は、周期律表の第Ia族、第IIa族および/または第IIIa族の元素である。前記活性化剤は、適宜、更なるエステル基、エーテル基、アミン基もしくはシリルエーテル基で変性されてよい。これらの触媒系は、通常は、フィリップス(Phillips)触媒、スタンダード・オイル・インディアナ(Standard Oil Indiana)触媒、ツィーグラー(ナッタ)触媒、TNZ(デュポン)触媒、メタロセン触媒またはシングルサイト触媒(SSC)と呼ばれる。
R4およびR6は、水素であり、かつ
R5およびR7は、互いに独立して、水素またはC1〜C8−アルキル、特に水素またはC1〜C4−アルキルである、化合物が好ましい。
R4、R6およびR7は、水素であり、かつR5は、水素またはC1〜C8−アルキル、特に水素またはC1〜C4−アルキルである、化合物が好ましい。
RP2およびRP6は、互いに独立して、水素もしくはC1−アルキルであり、RP3およびRP5は、互いに独立して、水素もしくはC1〜C4−アルキルであり、
RO1およびRO6は、互いに独立して、水素もしくはC1〜C8−アルキルであり、RO2は、水素もしくはC1−アルキルであり、RO5は、水素もしくはC1〜C4−アルキルであり、
RM1は、水素もしくはC1−アルキルであり、RM3およびRM5は、互いに独立して、水素もしくはC1〜C4−アルキルであり、かつRM6は、水素もしくはC1〜C8−アルキルである、化合物が好ましい。
RP2およびRP6は、水素であり、かつRP3およびRP5は、互いに独立して、水素もしくはC1〜C4−アルキルであり、
RO1は、水素もしくはC1〜C8−アルキルであり、RO2は、水素であり、RO5およびRO6は、互いに独立して、水素もしくはC1〜C4−アルキルであり、
RM1およびRM3は、水素もしくはC1−アルキルであり、RM5は、水素もしくはC1〜C4−アルキルであり、かつRM6は、水素もしくはC1〜C8−アルキルである、化合物が好ましい。
RP2およびRP6は、水素であり、かつRP3およびRP5は、互いに独立して、水素もしくはC1〜C4−アルキルであり、ここで、RP3およびRP5の一方はC4−アルキルではなく、
RO1は、水素もしくはC1〜C8−アルキルであり、RO2は、水素であり、RO5は、水素もしくはC1〜C3−アルキルであり、かつRO6は、水素もしくはC1〜C4−アルキルであり、かつ
RM1およびRM3は、水素もしくはC1−アルキルであり、RM5は、水素もしくはC1〜C3−アルキルであり、かつRM6は、水素もしくはC1〜C8−アルキルである、化合物が好ましい。
RP2およびRP6は、水素であり、かつRP3およびRP5の一方は、水素であるが、もう一方は、水素もしくはC1〜C4−アルキルであり、
RO1は、水素もしくはC1〜C8−アルキルであり、RO2は、水素であり、RO5は、水素もしくはC1−アルキルであり、かつRO6は、水素もしくはC1〜C4−アルキルであり、かつ
RM1、RM3およびRM5は、水素であり、かつRM6は、水素もしくはC1〜C8−アルキルである、化合物が好ましい。
R1Pは、部分式II−Pを表し、
R1Oは、式II−Oを表し、かつ
R1Mは、部分式II−Mを表す、化合物が好ましい。
R1Pは、部分式II−PもしくはII−Oの1つを表し、
R1Oは、部分式II−Oを表す、化合物が好ましい。
R1Pは、部分式II−Pを表す、化合物が好ましい。
R1Oは、部分式II−Oを表す、化合物が好ましい。
R1Pは、部分式II−P、II−OもしくはII−Mの1つを表し、
R1Oは、部分式II−OもしくはII−Mの1つを表し、
R1Mは、部分式II−Mを表し、
R4およびR6は、水素であり、
R5およびR7は、互いに独立して、水素もしくはC1〜C8−アルキルであり、
RP2およびRP6は、互いに独立して、水素もしくはC1−アルキルであり、
RP3およびRP5は、互いに独立して、水素もしくはC1〜C4−アルキルであり、
RO1およびRO6は、互いに独立して、水素もしくはC1〜C8−アルキルであり、
RO2は、水素またはC1−アルキルであり、
RO5は、水素またはC1〜C4−アルキルであり、
RM1は、水素またはC1−アルキルであり、
RM3およびRM5は、互いに独立して、水素もしくはC1〜C4−アルキルであり、かつ
RM6は、水素またはC1〜C8−アルキルである、化合物が好ましい。
R1Pは、部分式II−Pを表し、
R1Oは、部分式II−Oを表し、
R1Mは、部分式II−Mを表し、または
R4、R5、R6およびR7は、互いに独立して、水素もしくはC1〜C8−アルキルであり、
RP2、RP3、RP5およびRP6は、互いに独立して、水素もしくはC1〜C8−アルキルであり、
RO1、RO2、RO5およびRO6は、互いに独立して、水素もしくはC1〜C8−アルキルであり、かつ
RM1、RM3、RM5およびRM6は、互いに独立して、水素もしくはC1〜C8−アルキルである、化合物が好ましい。
R1Pは、部分式II−PもしくはII−Oの1つを表し、
R1Oは、部分式II−Oを表し、
R4、R5、R6およびR7は、互いに独立して、水素もしくはC1〜C8−アルキルであり、
RP2、RP3、RP5およびRP6は、互いに独立して、水素もしくはC1〜C8−アルキルであり、かつ
RO1、RO2、RO5およびRO6は、互いに独立して、水素もしくはC1〜C8−アルキルである、化合物が好ましい。
R1Pは、部分式II−PもしくはII−Oの1つを表し、
R1Oは、部分式II−Oを表し、
R4およびR6は、水素であり、
R5およびR7は、互いに独立して、水素もしくはC1〜C8−アルキルであり、
RP2およびRP6は、水素であり、
RP3およびRP5は、互いに独立して、水素もしくはC1〜C4−アルキルであり、ここで、RP3およびRP5の一方はC4−アルキルではなく、
RO1は、水素またはC1〜C8−アルキルであり、
RO2は、水素であり、
RO5は、水素またはC1〜C3−アルキルであり、かつ
RO6は、水素またはC1〜C4−アルキルである、化合物が好ましい。
1.1. アルキル化モノフェノール類、例えば2,6−ジ−t−ブチル−4−メチルフェノール、2−t−ブチル−4,6−ジメチルフェノール、2,6−ジ−t−ブチル−4−エチルフェノール、2,6−ジ−t−ブチル−4−n−ブチルフェノール、2,6−ジ−t−ブチル−4−イソブチルフェノール、2,6−ジシクロペンチル−4−メチルフェノール、2−(α−メチルシクロヘキシル)−4,6−ジメチルフェノール、2,6−ジオクタデシル−4−メチルフェノール、2,4,6−トリシクロヘキシルフェノール、2,6−ジ−t−ブチル−4−メトキシメチルフェノール、直鎖状または側鎖で分岐したノニルフェノール、例えば2,6−ジ−ノニル−4−メチルフェノール、2,4−ジメチル−6−(1’−メチルウンデカ−1’−イル)フェノール、2,4−ジメチル−6−(1’−メチルヘプタデカ−1’−イル)フェノール、2,4−ジメチル−6−(1’−メチルトリデカ−1’−イル)フェノール、2,4−ジメチル−6−(1’−メチル−1’−テトラデシル−メチル)フェノールおよびそれらの混合物。
− 該有機材料、すなわち成分a)を準備するステップと、
− 前記準備された有機材料中に式I−P、I−OもしくはI−Mの化合物、すなわち成分b)を導入するか、または前記有機材料上に前記化合物を適用するステップと、
を含む方法に関する。
− 該酸化的分解、熱的分解もしくは光誘発性分解を受けやすい有機材料を準備するステップと、
− 式I−P、I−OもしくはI−Mの化合物を前記準備された有機材料中に導入するステップであって、部分的もしくは完全な導入が135〜350℃、好ましくは150℃〜140℃、特に180℃〜330℃、殊に190℃〜320℃の範囲の温度で行われるステップと
を含む方法が好ましい。
a)酸化的分解、熱的分解または光誘発性分解を受けやすい有機材料と、
b)式I−P、I−OまたはI−Mの化合物と、
を含む組成物から製造される物品に関する。
R1Pは、部分式II−P、II−OもしくはII−M
R1Oは、部分式II−OもしくはII−Mの1つを表し、または
R1Mは、部分式II−Mを表し、
R4、R5、R6およびR7は、互いに独立して、水素もしくはC1〜C8−アルキルであり、
RP2、RP3、RP5およびRP6は、互いに独立して、水素もしくはC1〜C8−アルキルであり、
RO1、RO2、RO5およびRO6は、互いに独立して、水素もしくはC1〜C8−アルキルであり、かつ
RM1、RM3、RM5およびRM6は、互いに独立して、水素もしくはC1〜C8−アルキルである]の化合物に関する。
b)式I−P、I−OまたはI−Mの化合物と、
c)式I−P、I−OまたはI−Mの化合物とは異なるホスファイトもしくはホスホナイト、酸捕捉剤、フェノール系酸化防止剤およびアミン系酸化防止剤からなる群から選択される更なる添加剤と、
を含む前記組成物に関する。
b)式I−P、I−OまたはI−Mの化合物と、
c)フェノール系酸化防止剤または式I−P、I−OもしくはI−Mの化合物とは異なるホスファイトもしくはホスホナイトである更なる添加剤と、
を含む添加剤組成物が好ましい。
b)式I−P、I−OまたはI−Mの化合物と、
c)フェノール系酸化防止剤である更なる添加剤と、
を含む添加剤組成物が好ましい。
b)式I−P、I−OまたはI−Mの化合物と、
c)式I−P、I−OもしくはI−Mの化合物とは異なるホスファイトもしくはホスホナイトである更なる添加剤と、
を含む添加剤組成物が好ましい。
b)式I−P、I−OまたはI−Mの化合物と、
c)テトラキス−[β−(3,5−ジ−t−ブチル−4−ヒドロキシフェニル)−プロピオニルオキシメチル]メタン、ステアリルβ−(3,5−ジ−t−ブチル−4−ヒドロキシフェニル)−プロピオネートまたはトリス−(2,4−ジ−t−ブチル)ホスファイトである更なる添加剤と、
を含む添加剤組成物が好ましい。
b)式I−P、I−OまたはI−Mの化合物と、
c)式I−P、I−OまたはI−Mの化合物とは異なるホスファイトもしくはホスホナイト、酸捕捉剤、フェノール系酸化防止剤およびアミン系酸化防止剤からなる群から選択される更なる添加剤と、
d)式I−P、I−OまたはI−Mの化合物とは異なるホスファイトもしくはホスホナイト、酸捕捉剤、フェノール系酸化防止剤およびアミン系酸化防止剤からなる群から選択される第二の更なる添加剤と、
を含むが、但し、成分c)が成分d)とは異なる化合物である添加剤組成物が好ましい。
b)式I−P、I−OまたはI−Mの化合物と、
c)フェノール系酸化防止剤である更なる添加剤と、
d)式I−P、I−OもしくはI−Mの化合物とは異なるホスファイトもしくはホスホナイトである第二の更なる添加剤と、
を含む添加剤組成物が好ましい。
b)式Iの化合物と、
c)テトラキス−[β−(3,5−ジ−t−ブチル−4−ヒドロキシフェニル)−プロピオニルオキシメチル]メタンまたはステアリルβ−(3,5−ジ−t−ブチル−4−ヒドロキシフェニル)−プロピオネートである更なる添加剤と、
d)式I−P、I−OもしくはI−Mの化合物とは異なるホスファイトもしくはホスホナイトである第二の更なる添加剤と、
を含む添加剤組成物が好ましい。
b)式I−P、I−OまたはI−Mの化合物と、
c)フェノール系酸化防止剤である更なる添加剤と、
d)トリス−(2,4−ジ−t−ブチル)ホスファイトである第二の更なる添加剤と、
を含む添加剤組成物が好ましい。
b)式I−P、I−OまたはI−Mの化合物と、
c)テトラキス−[β−(3,5−ジ−t−ブチル−4−ヒドロキシフェニル)−プロピオニルオキシメチル]メタンまたはステアリルβ−(3,5−ジ−t−ブチル−4−ヒドロキシフェニル)−プロピオネートである更なる添加剤と、
d)トリス−(2,4−ジ−t−ブチル)ホスファイトである第二の更なる添加剤と、
を含む添加剤組成物が好ましい。
− 式S−IN−P
塩基および場合により非プロトン性溶剤の存在下で反応させて、式IN−P
− 式IN−Pの化合物と、式S1−IN−P
HO−R1P (S1−IN−P)
の化合物とを、塩基および場合により非プロトン性溶剤の存在下で反応させて、式I−Pの化合物を得るステップと、
を含み、前記式中、
R1Pは、部分式II−P、II−OもしくはII−M
R4、R5、R6およびR7は、互いに独立して、水素もしくはC1〜C8−アルキルであり、
RP2、RP3、RP5およびRP6は、互いに独立して、水素もしくはC1〜C8−アルキルであり、
RO1、RO2、RO5およびRO6は、互いに独立して、水素もしくはC1〜C8−アルキルであり、
RM1、RM3、RM5およびRM6は、互いに独立して、水素もしくはC1〜C8−アルキルであり、かつ
Z1P-INおよびZ2P-INは、互いに独立して、ハロゲンである、製造方法が好ましい。
− 式S−IN−O
塩基および場合により非プロトン性溶剤の存在下で反応させて、式IN−O
− 式IN−Oの化合物と、式S1−IN−O
HO−R1O (S1−IN−O)
の化合物とを、塩基および場合により非プロトン性溶剤の存在下で反応させて、式I−Oの化合物を得るステップと、
を含み、前記式中、
R1Oは、部分式II−OもしくはII−M
R4、R5、R6およびR7は、互いに独立して、水素もしくはC1〜C8−アルキルであり、
RO1、RO2、RO5およびRO6は、互いに独立して、水素もしくはC1〜C8−アルキルであり、
RM1、RM3、RM5およびRM6は、互いに独立して、水素もしくはC1〜C8−アルキルであり、かつ
Z1O-INおよびZ2O-INは、互いに独立して、ハロゲンである、製造方法が好ましい。
− 式S−IN−M
塩基および場合により非プロトン性溶剤の存在下で反応させて、式IN−M
− 式IN−Mの化合物と、式S1−IN−M
HO−R1M (S1−IN−M)
の化合物とを、塩基および場合により非プロトン性溶剤の存在下で反応させて、式I−Mの化合物を得るステップと、
を含み、前記式中、
R1Mは、部分式II−M
R4、R5、R6およびR7は、互いに独立して、水素もしくはC1〜C8−アルキルであり、
RM1、RM3、RM5およびRM6は、互いに独立して、水素もしくはC1〜C8−アルキルであり、かつ
Z1M-INおよびZ2M-INは、互いに独立して、ハロゲンである、製造方法が好ましい。
Z1P-IN、Z1O-INおよびZ1M-INは、互いに独立して、ハロゲンであり、
R4、R5、R6およびR7は、互いに独立して、水素もしくはC1〜C8−アルキルであり、
RP2、RP3、RP5およびRP6は、互いに独立して、水素もしくはC1〜C8−アルキルであり、
RO1、RO2、RO5およびRO6は、互いに独立して、水素もしくはC1〜C8−アルキルであり、かつ
RM1、RM3、RM5およびRM6は、互いに独立して、水素もしくはC1〜C8−アルキルである]の中間体化合物に関する。
該合成手順は、窒素雰囲気下で行われる。
1H−NMR(トルエン−d8):4.4ppm(s,2H,ラクトン環のCH)
MS(LC/MS,ACPIポジティブモード):[M+1]+=870。
1H−NMR(トルエン−d8):4.3ppm(s,2H,ラクトン環のCH)
MS(LC/MS,ACPIポジティブモード):[M+1]+=1094。
1H−NMR(トルエン−d8):4.3ppm(s,2H,ラクトン環のCH)
MS(LC/MS,ACPIポジティブモード):[M+1]+=926。
1H−NMR(トルエン−d8):4.3ppm(s,2H,ラクトン環のCH)
MS(LC/MS,ACPIポジティブモード):[M+1]+=1010。
以下の既知の安定化剤を、本発明による化合物に加えて部分的に使用する。
様々な添加剤を、本質的に全く添加剤を含まないMoplen HF 501 N(LyondellBasell社の登録商標、ポリプロピレンホモポリマー、粉末、メルトフローレート10g/10分(230℃/2.16kg))と表A−1による組成でブレンドする。そのブレンドは、ターブラ・ミキサーを使用して実施される。
ポリマー加工実験
様々な添加剤を、それぞれの表A−2−1〜表A−2−4による組成において、安定化添加剤を本質的に一切含まない指定され利用される粒状ポリマーと一緒に配合する。その配合は、ヘンシェルミキサー、ターブラーミキサーまたはキッチンエイドミキサーを使用して実施される。
塊状/スラリー相重合法からの4dg/分のメルトフローレートを有する成形グレードのチーグラー・ナッタ系のポリプロピレンホモポリマー(zn−PP−ホモポリマー)を評価する。
塊状/スラリー相重合法からの3dg/分のメルトフローレートを有する成形グレードのチーグラー・ナッタ系のポリプロピレンコポリマー(zn−PP−コポリマー;コモノマーとして約2質量%のエチレン)を評価する。
気相重合法からの190℃および2.16kgで2dg/分のメルトフローレートを有するフィルムグレードのチーグラー・ナッタ系のポリエチレンコポリマー(zn−LLDPE−コポリマー;コモノマーとしてブテン、密度0.92g/cm3)を評価する。
気相重合法からの190℃および2.16kgで0.3dg/分のメルトフローレートを有する成形グレードのクロム触媒型ポリエチレン(Cr−HDPE;密度0.955g/cm3)を評価する。
Claims (19)
- a)酸化的分解、熱的分解または光誘発性分解を受けやすい有機材料と、
b)式I−P、I−OまたはI−M
R1Pは、部分式II−P、II−OまたはII−M
R1Oは、部分式II−OまたはII−Mの1つを表し、または
R1Mは、部分式II−Mを表し、
R4、R5、R6およびR7は、互いに独立して、水素またはC1〜C8−アルキルであり、
RP2、RP3、RP5およびRP6は、互いに独立して、水素またはC1〜C8−アルキルであり、
RO1、RO2、RO5およびRO6は、互いに独立して、水素またはC1〜C8−アルキルであり、かつ
RM1、RM3、RM5およびRM6は、互いに独立して、水素またはC1〜C8−アルキルである]の化合物と、
を含む組成物。 - 前記有機材料は、ポリマー、オリゴヒドロキシ化合物、ワックス、脂肪または鉱油である、請求項1に記載の組成物。
- 前記有機材料は、ポリマーであり、該ポリマーは、ポリオレフィンまたはそのコポリマー、ポリスチレンまたはそのコポリマー、ポリウレタンまたはそのコポリマー、エポキシド、オキセタンもしくはテトラヒドロフランの重合によって得られるポリエーテルまたはそのコポリマー、ポリエステルまたはそのコポリマー、ポリカーボネートまたはそのコポリマー、ポリ(塩化ビニル)またはそのコポリマー、ポリ(塩化ビニリデン)またはそのコポリマー、ポリスルホンまたはそのコポリマー、ポリ(ビニルアセテート)またはそのコポリマー、ポリ(ビニルアルコール)またはそのコポリマー、ポリ(ビニルアセタール)またはそのコポリマー、あるいはポリアミドまたはそのコポリマーである、請求項2に記載の組成物。
- 請求項1から3までのいずれか1項に記載の組成物であって、式中、
R4およびR6は、水素であり、
R5およびR7は、互いに独立して、水素またはC1〜C8−アルキルであり、
RP2およびRP6は、互いに独立して、水素またはC1−アルキルであり、
RP3およびRP5は、互いに独立して、水素またはC1〜C4−アルキルであり、
RO1およびRO6は、互いに独立して、水素またはC1〜C8−アルキルであり、
RO2は、水素またはC1−アルキルであり、
RO5は、水素またはC1〜C4−アルキルであり、
RM1は、水素またはC1−アルキルであり、
RM3およびRM5は、互いに独立して、水素またはC1〜C4−アルキルであり、かつ
RM6は、水素またはC1〜C8−アルキルである、組成物。 - 請求項1から4までのいずれか1項に記載の組成物であって、
前記化合物は、式I−PまたはI−Oの化合物であり、
R1Pは、部分式II−PまたはII−Oの1つを表し、かつ
R1Oは、部分式II−Oを表す、組成物。 - 請求項1から5までのいずれか1項に記載の組成物であって、
a)ポリオレフィンもしくはそのコポリマー、またはポリスチレンもしくはそのコポリマーであるポリマーと、
b)式I−PまたはI−Oの化合物と、
を含み、その式中、
R1Pは、部分式II−Pを表し、
R1Oは、部分式II−Oを表し、
R4およびR6は、水素であり、
R5およびR7は、互いに独立して、水素またはC1〜C8−アルキルであり、
RO1は、水素またはC1〜C8−アルキルであり、
RO2、RO5およびRO6は、水素であり、
RP2およびRP6は、水素であり、かつ
RP3およびRP5は、互いに独立して、水素またはC1〜C4−アルキルである、組成物。 - 成分b)は、成分a)の質量に対して0.0005%〜10%の量で含まれている、請求項1から6までのいずれか1項に記載の組成物。
- 成分c)として更なる添加剤を含む、請求項1から7までのいずれか1項に記載の組成物。
- 成分c)として、成分b)とは異なるホスファイトもしくはホスホナイト、酸捕捉剤、フェノール系酸化防止剤またはアミン系酸化防止剤である更なる添加剤を含む、請求項8に記載の組成物。
- 成分c)として、β−(3,5−ジ−t−ブチル−4−ヒドロキシフェニル)プロピオン酸のエステルであるフェノール系酸化防止剤を含む、請求項9に記載の組成物。
- 成分d)として、成分b)とは異なるホスファイトもしくはホスホナイト、酸捕捉剤、フェノール系酸化防止剤またはアミン系酸化防止剤である第二の更なる添加剤を含むが、但し、成分d)が成分c)とは異なる化合物である、請求項8から10までのいずれか1項に記載の組成物。
- 酸化的分解、熱的分解または光誘発性分解を受けやすい有機材料の保護方法であって、
− 有機材料を準備するステップと、
− 前記準備された有機材料中に請求項1に定義される式I−P、I−OもしくはI−Mの化合物を導入するか、または前記有機材料上に前記化合物を適用するステップと、
を含む、保護方法。 - 前記有機材料は、ポリマーであり、該ポリマー中への導入が行われ、かつ部分的または完全な導入は、135℃から350℃の間の温度で行われる、請求項12に記載の方法。
- 請求項1に定義される式I−P、I−OまたはI−Mの化合物の、酸化的分解、熱的分解または光誘発性分解を受けやすい有機材料を酸化、熱または光による分解に対して安定化するための使用。
- 添加剤組成物であって、
b)請求項1に定義される式I−P、I−OまたはI−Mの化合物と、
c)成分b)とは異なるホスファイトもしくはホスホナイト、酸捕捉剤、フェノール系酸化防止剤またはアミン系酸化防止剤である更なる添加剤と、
を含む、添加剤組成物。 - 成分c)として、β−(3,5−ジ−t−ブチル−4−ヒドロキシフェニル)プロピオン酸のエステルであるフェノール系酸化防止剤を含む、請求項16に記載の添加剤組成物。
- 成分d)として、成分b)とは異なるホスファイトもしくはホスホナイト、酸捕捉剤、フェノール系酸化防止剤またはアミン系酸化防止剤である第二の更なる添加剤を含むが、但し、成分d)が成分c)とは異なる化合物である、請求項16または17に記載の添加剤組成物。
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CN106574090A (zh) | 2017-04-19 |
AU2015299175A1 (en) | 2017-02-16 |
AU2015299175B2 (en) | 2018-12-20 |
KR102377818B1 (ko) | 2022-03-24 |
SA517380827B1 (ar) | 2020-06-04 |
JP6559224B2 (ja) | 2019-08-14 |
CA2955260C (en) | 2022-06-28 |
EP3177681A1 (en) | 2017-06-14 |
PL3177681T3 (pl) | 2019-02-28 |
BR112017002203A2 (pt) | 2018-01-16 |
RU2017107097A (ru) | 2018-09-06 |
KR20170039165A (ko) | 2017-04-10 |
EP3177681B1 (en) | 2018-09-12 |
US20170226323A1 (en) | 2017-08-10 |
BR112017002203B1 (pt) | 2021-10-26 |
RU2700027C2 (ru) | 2019-09-12 |
ES2701529T3 (es) | 2019-02-22 |
WO2016020322A1 (en) | 2016-02-11 |
RU2017107097A3 (ja) | 2019-02-19 |
US10072136B2 (en) | 2018-09-11 |
CN106574090B (zh) | 2019-11-19 |
MX2017001645A (es) | 2017-05-09 |
TWI659992B (zh) | 2019-05-21 |
CA2955260A1 (en) | 2016-02-11 |
TW201612223A (en) | 2016-04-01 |
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