JP2005504158A

JP2005504158A - ヒドロキシルアミンエステルの使用による不飽和ポリマーの架橋

ヒドロキシルアミンエステルの使用による不飽和ポリマーの架橋 Download PDF

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Publication number: JP2005504158A
Authority: JP; Japan
Prior art keywords: group; carbon atoms; alkyl; hydrogen atom; acid
Prior art date: 2001-09-25
Legal status : Pending

Application number

JP2003532570A

Other languages

English (en)

Japanese (ja)

Other versions

JP2005504158A5 (enExample

Inventor

ロス，ミハエル

シモン，ターク

Current Assignee

BASF Schweiz AG

Original Assignee

Ciba Spezialitaetenchemie Holding AG

Priority date

2001-09-25

Filing date

2002-09-17

Publication date

2005-02-10

2002-09-17 Application filed by Ciba Spezialitaetenchemie Holding AG filed Critical Ciba Spezialitaetenchemie Holding AG

2005-02-10 Publication of JP2005504158A publication Critical patent/JP2005504158A/ja

2006-01-05 Publication of JP2005504158A5 publication Critical patent/JP2005504158A5/ja

Status Pending legal-status Critical Current

Links

229920000642 polymer Polymers 0.000 title claims abstract description 32
238000004132 cross linking Methods 0.000 title claims abstract description 13
150000002443 hydroxylamines Chemical class 0.000 title abstract description 13
-1 hydroxylamine ester Chemical class 0.000 claims abstract description 138
238000000034 method Methods 0.000 claims abstract description 54
239000000203 mixture Substances 0.000 claims abstract description 38
229920006337 unsaturated polyester resin Polymers 0.000 claims abstract description 22
239000002952 polymeric resin Substances 0.000 claims abstract description 18
229920003002 synthetic resin Polymers 0.000 claims abstract description 18
125000004432 carbon atom Chemical group C* 0.000 claims description 310
125000000217 alkyl group Chemical group 0.000 claims description 91
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 49
125000003118 aryl group Chemical group 0.000 claims description 42
125000002947 alkylene group Chemical group 0.000 claims description 40
239000000178 monomer Substances 0.000 claims description 38
125000001931 aliphatic group Chemical group 0.000 claims description 26
238000000576 coating method Methods 0.000 claims description 25
239000002253 acid Substances 0.000 claims description 23
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 23
238000006243 chemical reaction Methods 0.000 claims description 22
150000001875 compounds Chemical class 0.000 claims description 21
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 21
OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims description 18
125000003342 alkenyl group Chemical group 0.000 claims description 18
125000000753 cycloalkyl group Chemical group 0.000 claims description 18
239000011248 coating agent Substances 0.000 claims description 16
125000002723 alicyclic group Chemical group 0.000 claims description 14
125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 14
238000010438 heat treatment Methods 0.000 claims description 13
229910052757 nitrogen Inorganic materials 0.000 claims description 13
125000003055 glycidyl group Chemical group C(C1CO1)* 0.000 claims description 12
150000002978 peroxides Chemical class 0.000 claims description 12
239000000843 powder Substances 0.000 claims description 12
125000002252 acyl group Chemical group 0.000 claims description 11
125000003710 aryl alkyl group Chemical group 0.000 claims description 11
239000003365 glass fiber Substances 0.000 claims description 11
125000000732 arylene group Chemical group 0.000 claims description 10
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 10
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 9
125000002993 cycloalkylene group Chemical group 0.000 claims description 9
125000004437 phosphorous atom Chemical group 0.000 claims description 9
229910052698 phosphorus Inorganic materials 0.000 claims description 9
125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 claims description 9
125000000304 alkynyl group Chemical group 0.000 claims description 8
239000002131 composite material Substances 0.000 claims description 8
239000000463 material Substances 0.000 claims description 8
125000001731 2-cyanoethyl group Chemical group [H]C([H])(*)C([H])([H])C#N 0.000 claims description 7
150000007933 aliphatic carboxylic acids Chemical class 0.000 claims description 7
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 7
238000004519 manufacturing process Methods 0.000 claims description 7
125000004430 oxygen atom Chemical group O* 0.000 claims description 7
125000004450 alkenylene group Chemical group 0.000 claims description 6
WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims description 6
150000001735 carboxylic acids Chemical class 0.000 claims description 6
125000001624 naphthyl group Chemical group 0.000 claims description 6
125000003884 phenylalkyl group Chemical group 0.000 claims description 6
238000011417 postcuring Methods 0.000 claims description 6
229920002554 vinyl polymer Polymers 0.000 claims description 6
150000007934 α,β-unsaturated carboxylic acids Chemical class 0.000 claims description 6
125000003545 alkoxy group Chemical group 0.000 claims description 5
229910052799 carbon Inorganic materials 0.000 claims description 5
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 5
150000001991 dicarboxylic acids Chemical class 0.000 claims description 5
230000003287 optical effect Effects 0.000 claims description 5
125000003161 (C1-C6) alkylene group Chemical group 0.000 claims description 4
125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 4
125000004183 alkoxy alkyl group Chemical group 0.000 claims description 4
125000004419 alkynylene group Chemical group 0.000 claims description 4
125000004429 atom Chemical group 0.000 claims description 4
KXDHJXZQYSOELW-UHFFFAOYSA-N carbonic acid monoamide Natural products NC(O)=O KXDHJXZQYSOELW-UHFFFAOYSA-N 0.000 claims description 4
125000004093 cyano group Chemical group *C#N 0.000 claims description 4
125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 claims description 4
125000002768 hydroxyalkyl group Chemical group 0.000 claims description 4
125000004817 pentamethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 claims description 4
KJAMZCVTJDTESW-UHFFFAOYSA-N tiracizine Chemical compound C1CC2=CC=CC=C2N(C(=O)CN(C)C)C2=CC(NC(=O)OCC)=CC=C21 KJAMZCVTJDTESW-UHFFFAOYSA-N 0.000 claims description 4
125000006839 xylylene group Chemical group 0.000 claims description 4
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 3
MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 claims description 3
XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 3
125000001309 chloro group Chemical group Cl* 0.000 claims description 3
150000001990 dicarboxylic acid derivatives Chemical class 0.000 claims description 3
239000000976 ink Substances 0.000 claims description 3
125000004433 nitrogen atom Chemical group N* 0.000 claims description 3
150000002976 peresters Chemical class 0.000 claims description 3
125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims description 3
238000007639 printing Methods 0.000 claims description 3
229920000089 Cyclic olefin copolymer Polymers 0.000 claims description 2
CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 claims description 2
125000004423 acyloxy group Chemical group 0.000 claims description 2
125000005078 alkoxycarbonylalkyl group Chemical group 0.000 claims description 2
125000005250 alkyl acrylate group Chemical group 0.000 claims description 2
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 2
229910052801 chlorine Inorganic materials 0.000 claims description 2
125000003073 divalent carboacyl group Chemical group 0.000 claims description 2
238000005538 encapsulation Methods 0.000 claims description 2
125000001424 substituent group Chemical group 0.000 claims description 2
239000004711 α-olefin Substances 0.000 claims description 2
125000006702 (C1-C18) alkyl group Chemical group 0.000 claims 4
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 2
125000000041 C6-C10 aryl group Chemical group 0.000 claims 2
XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical group NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims 2
125000001589 carboacyl group Chemical group 0.000 claims 1
150000001721 carbon Chemical group 0.000 claims 1
125000004122 cyclic group Chemical group 0.000 claims 1
125000005442 diisocyanate group Chemical group 0.000 claims 1
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238000001723 curing Methods 0.000 description 32
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239000011347 resin Substances 0.000 description 24
150000003254 radicals Chemical class 0.000 description 23
PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 22
239000003999 initiator Substances 0.000 description 16
229920000728 polyester Polymers 0.000 description 12
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 10
QQVIHTHCMHWDBS-UHFFFAOYSA-N isophthalic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 description 10
NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 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 9
229920005862 polyol Polymers 0.000 description 9
239000007787 solid Substances 0.000 description 9
TXBCBTDQIULDIA-UHFFFAOYSA-N 2-[[3-hydroxy-2,2-bis(hydroxymethyl)propoxy]methyl]-2-(hydroxymethyl)propane-1,3-diol Chemical compound OCC(CO)(CO)COCC(CO)(CO)CO TXBCBTDQIULDIA-UHFFFAOYSA-N 0.000 description 8
150000001732 carboxylic acid derivatives Chemical class 0.000 description 8
238000009472 formulation Methods 0.000 description 8
238000003860 storage Methods 0.000 description 8
QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 7
150000001252 acrylic acid derivatives Chemical class 0.000 description 7
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 7
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125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 4
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CXMXRPHRNRROMY-UHFFFAOYSA-N sebacic acid Chemical compound OC(=O)CCCCCCCCC(O)=O CXMXRPHRNRROMY-UHFFFAOYSA-N 0.000 description 4
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MYWOJODOMFBVCB-UHFFFAOYSA-N 1,2,6-trimethylphenanthrene Chemical compound CC1=CC=C2C3=CC(C)=CC=C3C=CC2=C1C MYWOJODOMFBVCB-UHFFFAOYSA-N 0.000 description 3
PXGZQGDTEZPERC-UHFFFAOYSA-N 1,4-cyclohexanedicarboxylic acid Chemical compound OC(=O)C1CCC(C(O)=O)CC1 PXGZQGDTEZPERC-UHFFFAOYSA-N 0.000 description 3
SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 3
XMNIXWIUMCBBBL-UHFFFAOYSA-N 2-(2-phenylpropan-2-ylperoxy)propan-2-ylbenzene Chemical compound C=1C=CC=CC=1C(C)(C)OOC(C)(C)C1=CC=CC=C1 XMNIXWIUMCBBBL-UHFFFAOYSA-N 0.000 description 3
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150000008064 anhydrides Chemical class 0.000 description 3
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238000000748 compression moulding Methods 0.000 description 3
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238000002156 mixing Methods 0.000 description 3
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GJBRNHKUVLOCEB-UHFFFAOYSA-N tert-butyl benzenecarboperoxoate Chemical compound CC(C)(C)OOC(=O)C1=CC=CC=C1 GJBRNHKUVLOCEB-UHFFFAOYSA-N 0.000 description 3
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PTJWCLYPVFJWMP-UHFFFAOYSA-N 2-[[3-hydroxy-2-[[3-hydroxy-2,2-bis(hydroxymethyl)propoxy]methyl]-2-(hydroxymethyl)propoxy]methyl]-2-(hydroxymethyl)propane-1,3-diol Chemical compound OCC(CO)(CO)COCC(CO)(CO)COCC(CO)(CO)CO PTJWCLYPVFJWMP-UHFFFAOYSA-N 0.000 description 2
WFUGQJXVXHBTEM-UHFFFAOYSA-N 2-hydroperoxy-2-(2-hydroperoxybutan-2-ylperoxy)butane Chemical compound CCC(C)(OO)OOC(C)(CC)OO WFUGQJXVXHBTEM-UHFFFAOYSA-N 0.000 description 2
XCZKKZXWDBOGPA-UHFFFAOYSA-N 2-phenylbenzene-1,4-diol Chemical compound OC1=CC=C(O)C(C=2C=CC=CC=2)=C1 XCZKKZXWDBOGPA-UHFFFAOYSA-N 0.000 description 2
LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 description 2
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FJKROLUGYXJWQN-UHFFFAOYSA-N 4-hydroxybenzoic acid Chemical compound OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 2
CYYZDBDROVLTJU-UHFFFAOYSA-N 4-n-Butylphenol Chemical compound CCCCC1=CC=C(O)C=C1 CYYZDBDROVLTJU-UHFFFAOYSA-N 0.000 description 2
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