JP2011517716A

JP2011517716A - エポキシ樹脂用の硬化剤としての、末端アミノ基を有する高分岐のポリマー及びオリゴマー

エポキシ樹脂用の硬化剤としての、末端アミノ基を有する高分岐のポリマー及びオリゴマー Download PDF

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Publication number: JP2011517716A
Authority: JP; Japan
Prior art keywords: group; amine; primary; alkyl; alkylene
Prior art date: 2008-04-11
Legal status : Ceased

Application number

JP2011503451A

Other languages

English (en)

Japanese (ja)

Other versions

JP2011517716A5 (enExample

Inventor

ペレトルヒンマキシム

リューバエヴァ

シェーンフェルダーダニエル

Current Assignee

BASF SE

Original Assignee

BASF SE

Priority date

2008-04-11

Filing date

2009-04-09

Publication date

2011-06-16

2009-04-09 Application filed by BASF SE filed Critical BASF SE

2011-06-16 Publication of JP2011517716A publication Critical patent/JP2011517716A/ja

2012-06-07 Publication of JP2011517716A5 publication Critical patent/JP2011517716A5/ja

Status Ceased legal-status Critical Current

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239000003822 epoxy resin Substances 0.000 title claims abstract description 118
229920000647 polyepoxide Polymers 0.000 title claims abstract description 118
239000003795 chemical substances by application Substances 0.000 title claims abstract description 88
LNEPOXFFQSENCJ-UHFFFAOYSA-N haloperidol Chemical compound C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 LNEPOXFFQSENCJ-UHFFFAOYSA-N 0.000 title claims abstract description 41
229920000587 hyperbranched polymer Polymers 0.000 title claims abstract description 35
125000003277 amino group Chemical group 0.000 title claims description 23
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims abstract description 144
125000000467 secondary amino group Chemical group [H]N([*:1])[*:2] 0.000 claims abstract description 105
239000000203 mixture Substances 0.000 claims abstract description 77
229920000642 polymer Polymers 0.000 claims abstract description 70
238000000034 method Methods 0.000 claims abstract description 19
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150000001412 amines Chemical class 0.000 claims description 291
XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 100
229910052757 nitrogen Inorganic materials 0.000 claims description 93
229920000877 Melamine resin Polymers 0.000 claims description 83
JDSHMPZPIAZGSV-UHFFFAOYSA-N melamine Chemical compound NC1=NC(N)=NC(N)=N1 JDSHMPZPIAZGSV-UHFFFAOYSA-N 0.000 claims description 80
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 74
125000003118 aryl group Chemical group 0.000 claims description 66
238000006243 chemical reaction Methods 0.000 claims description 63
150000004985 diamines Chemical class 0.000 claims description 55
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235000013877 carbamide Nutrition 0.000 claims description 54
150000001875 compounds Chemical class 0.000 claims description 48
239000004202 carbamide Substances 0.000 claims description 47
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 46
125000001931 aliphatic group Chemical group 0.000 claims description 38
150000003672 ureas Chemical class 0.000 claims description 36
229910052799 carbon Inorganic materials 0.000 claims description 35
238000009833 condensation Methods 0.000 claims description 34
125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims description 33
230000005494 condensation Effects 0.000 claims description 32
XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 29
239000007859 condensation product Substances 0.000 claims description 28
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 28
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239000000835 fiber Substances 0.000 claims description 27
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125000002947 alkylene group Chemical group 0.000 claims description 25
239000001257 hydrogen Substances 0.000 claims description 25
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UMGDCJDMYOKAJW-UHFFFAOYSA-N aminothiocarboxamide Natural products NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 claims description 20
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239000011347 resin Substances 0.000 claims description 17
CHJJGSNFBQVOTG-UHFFFAOYSA-N N-methyl-guanidine Natural products CNC(N)=N CHJJGSNFBQVOTG-UHFFFAOYSA-N 0.000 claims description 16
SWSQBOPZIKWTGO-UHFFFAOYSA-N dimethylaminoamidine Natural products CN(C)C(N)=N SWSQBOPZIKWTGO-UHFFFAOYSA-N 0.000 claims description 16
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239000000463 material Substances 0.000 claims description 13
150000007974 melamines Chemical class 0.000 claims description 13
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 12
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 11
150000002357 guanidines Chemical class 0.000 claims description 11
125000004430 oxygen atom Chemical group O* 0.000 claims description 11
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 10
150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 10
125000006574 non-aromatic ring group Chemical group 0.000 claims description 10
229910052760 oxygen Inorganic materials 0.000 claims description 10
239000001301 oxygen Substances 0.000 claims description 10
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125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 9
239000011593 sulfur Substances 0.000 claims description 9
150000003585 thioureas Chemical class 0.000 claims description 9
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239000012779 reinforcing material Substances 0.000 claims description 7
125000006832 (C1-C10) alkylene group Chemical group 0.000 claims description 6
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229920003235 aromatic polyamide Polymers 0.000 claims description 6
150000002431 hydrogen Chemical class 0.000 claims description 6
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125000004434 sulfur atom Chemical group 0.000 claims description 6
239000002023 wood Substances 0.000 claims description 6
125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 5
GZVHEAJQGPRDLQ-UHFFFAOYSA-N 6-phenyl-1,3,5-triazine-2,4-diamine Chemical compound NC1=NC(N)=NC(C=2C=CC=CC=2)=N1 GZVHEAJQGPRDLQ-UHFFFAOYSA-N 0.000 claims description 4
239000010439 graphite Substances 0.000 claims description 4
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229920006395 saturated elastomer Polymers 0.000 claims description 4
125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 3
125000004957 naphthylene group Chemical group 0.000 claims description 3
125000001174 sulfone group Chemical group 0.000 claims description 3
BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 claims description 2
125000006615 aromatic heterocyclic group Chemical group 0.000 claims description 2
125000002529 biphenylenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C12)* 0.000 claims description 2
125000002993 cycloalkylene group Chemical group 0.000 claims description 2
125000005842 heteroatom Chemical group 0.000 claims description 2
229910010272 inorganic material Inorganic materials 0.000 claims description 2
239000011147 inorganic material Substances 0.000 claims description 2
QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 2
125000005263 alkylenediamine group Chemical group 0.000 claims 1
238000001723 curing Methods 0.000 description 86
NAQMVNRVTILPCV-UHFFFAOYSA-N hexane-1,6-diamine Chemical compound NCCCCCCN NAQMVNRVTILPCV-UHFFFAOYSA-N 0.000 description 58
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239000000049 pigment Substances 0.000 description 34
XFNJVJPLKCPIBV-UHFFFAOYSA-N trimethylenediamine Chemical compound NCCCN XFNJVJPLKCPIBV-UHFFFAOYSA-N 0.000 description 27
RNLHGQLZWXBQNY-UHFFFAOYSA-N 3-(aminomethyl)-3,5,5-trimethylcyclohexan-1-amine Chemical compound CC1(C)CC(N)CC(C)(CN)C1 RNLHGQLZWXBQNY-UHFFFAOYSA-N 0.000 description 26
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LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 24
125000004432 carbon atom Chemical group C* 0.000 description 21
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 21
239000007983 Tris buffer Substances 0.000 description 20
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239000004848 polyfunctional curative Substances 0.000 description 19
PWGJDPKCLMLPJW-UHFFFAOYSA-N 1,8-diaminooctane Chemical compound NCCCCCCCCN PWGJDPKCLMLPJW-UHFFFAOYSA-N 0.000 description 18
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 18
PWSKHLMYTZNYKO-UHFFFAOYSA-N heptane-1,7-diamine Chemical compound NCCCCCCCN PWSKHLMYTZNYKO-UHFFFAOYSA-N 0.000 description 18
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125000006068 2,3-dimethyl-1-butenyl group Chemical group 0.000 description 1
125000006069 2,3-dimethyl-2-butenyl group Chemical group 0.000 description 1
125000006070 2,3-dimethyl-3-butenyl group Chemical group 0.000 description 1
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