TW202307077A - 苯醚寡聚物及含該苯醚寡聚物之可固化熱固性組成物 - Google Patents
苯醚寡聚物及含該苯醚寡聚物之可固化熱固性組成物 Download PDFInfo
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- TW202307077A TW202307077A TW111114826A TW111114826A TW202307077A TW 202307077 A TW202307077 A TW 202307077A TW 111114826 A TW111114826 A TW 111114826A TW 111114826 A TW111114826 A TW 111114826A TW 202307077 A TW202307077 A TW 202307077A
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- Prior art keywords
- bis
- phenylene ether
- methyl
- meth
- ether oligomer
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- 239000000203 mixture Substances 0.000 title claims abstract description 161
- 229920001187 thermosetting polymer Polymers 0.000 title claims abstract description 130
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- YCUALLYXPZGZFN-UHFFFAOYSA-N 2-cyclohexyl-6-methylphenol Chemical compound CC1=CC=CC(C2CCCCC2)=C1O YCUALLYXPZGZFN-UHFFFAOYSA-N 0.000 claims abstract description 5
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- 238000000034 method Methods 0.000 claims description 39
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- QKJGTZOWMVHEHS-UHFFFAOYSA-N triethoxy-[3-(phenyltetrasulfanyl)propyl]silane Chemical compound CCO[Si](OCC)(OCC)CCCSSSSC1=CC=CC=C1 QKJGTZOWMVHEHS-UHFFFAOYSA-N 0.000 description 1
- BDZBKCUKTQZUTL-UHFFFAOYSA-N triethyl phosphite Chemical compound CCOP(OCC)OCC BDZBKCUKTQZUTL-UHFFFAOYSA-N 0.000 description 1
- YFNKIDBQEZZDLK-UHFFFAOYSA-N triglyme Chemical compound COCCOCCOCCOC YFNKIDBQEZZDLK-UHFFFAOYSA-N 0.000 description 1
- BPSIOYPQMFLKFR-UHFFFAOYSA-N trimethoxy-[3-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CO[Si](OC)(OC)CCCOCC1CO1 BPSIOYPQMFLKFR-UHFFFAOYSA-N 0.000 description 1
- CYTQBVOFDCPGCX-UHFFFAOYSA-N trimethyl phosphite Chemical compound COP(OC)OC CYTQBVOFDCPGCX-UHFFFAOYSA-N 0.000 description 1
- XPEMYYBBHOILIJ-UHFFFAOYSA-N trimethyl(trimethylsilylperoxy)silane Chemical compound C[Si](C)(C)OO[Si](C)(C)C XPEMYYBBHOILIJ-UHFFFAOYSA-N 0.000 description 1
- 125000003258 trimethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])[*:1] 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
- YFTHZRPMJXBUME-UHFFFAOYSA-N tripropylamine Chemical compound CCCN(CCC)CCC YFTHZRPMJXBUME-UHFFFAOYSA-N 0.000 description 1
- OOZBTDPWFHJVEK-UHFFFAOYSA-N tris(2-nonylphenyl) phosphate Chemical compound CCCCCCCCCC1=CC=CC=C1OP(=O)(OC=1C(=CC=CC=1)CCCCCCCCC)OC1=CC=CC=C1CCCCCCCCC OOZBTDPWFHJVEK-UHFFFAOYSA-N 0.000 description 1
- DSROZUMNVRXZNO-UHFFFAOYSA-K tris[(1-naphthalen-1-yl-3-phenylnaphthalen-2-yl)oxy]alumane Chemical compound C=1C=CC=CC=1C=1C=C2C=CC=CC2=C(C=2C3=CC=CC=C3C=CC=2)C=1O[Al](OC=1C(=C2C=CC=CC2=CC=1C=1C=CC=CC=1)C=1C2=CC=CC=C2C=CC=1)OC(C(=C1C=CC=CC1=C1)C=2C3=CC=CC=C3C=CC=2)=C1C1=CC=CC=C1 DSROZUMNVRXZNO-UHFFFAOYSA-K 0.000 description 1
- BIKXLKXABVUSMH-UHFFFAOYSA-N trizinc;diborate Chemical compound [Zn+2].[Zn+2].[Zn+2].[O-]B([O-])[O-].[O-]B([O-])[O-] BIKXLKXABVUSMH-UHFFFAOYSA-N 0.000 description 1
- QVWDCTQRORVHHT-UHFFFAOYSA-N tropone Chemical compound O=C1C=CC=CC=C1 QVWDCTQRORVHHT-UHFFFAOYSA-N 0.000 description 1
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- 238000005406 washing Methods 0.000 description 1
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- 239000008096 xylene Substances 0.000 description 1
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- PJEUXMXPJGWZOZ-UHFFFAOYSA-L zinc;diphenylphosphinate Chemical compound [Zn+2].C=1C=CC=CC=1P(=O)([O-])C1=CC=CC=C1.C=1C=CC=CC=1P(=O)([O-])C1=CC=CC=C1 PJEUXMXPJGWZOZ-UHFFFAOYSA-L 0.000 description 1
Classifications
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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
- C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B32—LAYERED PRODUCTS
- B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
- B32B5/00—Layered products characterised by the non- homogeneity or physical structure, i.e. comprising a fibrous, filamentary, particulate or foam layer; Layered products characterised by having a layer differing constitutionally or physically in different parts
- B32B5/02—Layered products characterised by the non- homogeneity or physical structure, i.e. comprising a fibrous, filamentary, particulate or foam layer; Layered products characterised by having a layer differing constitutionally or physically in different parts characterised by structural features of a fibrous or filamentary layer
- B32B5/022—Non-woven fabric
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B32—LAYERED PRODUCTS
- B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
- B32B5/00—Layered products characterised by the non- homogeneity or physical structure, i.e. comprising a fibrous, filamentary, particulate or foam layer; Layered products characterised by having a layer differing constitutionally or physically in different parts
- B32B5/02—Layered products characterised by the non- homogeneity or physical structure, i.e. comprising a fibrous, filamentary, particulate or foam layer; Layered products characterised by having a layer differing constitutionally or physically in different parts characterised by structural features of a fibrous or filamentary layer
- B32B5/024—Woven fabric
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B32—LAYERED PRODUCTS
- B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
- B32B5/00—Layered products characterised by the non- homogeneity or physical structure, i.e. comprising a fibrous, filamentary, particulate or foam layer; Layered products characterised by having a layer differing constitutionally or physically in different parts
- B32B5/22—Layered products characterised by the non- homogeneity or physical structure, i.e. comprising a fibrous, filamentary, particulate or foam layer; Layered products characterised by having a layer differing constitutionally or physically in different parts characterised by the presence of two or more layers which are next to each other and are fibrous, filamentary, formed of particles or foamed
- B32B5/24—Layered products characterised by the non- homogeneity or physical structure, i.e. comprising a fibrous, filamentary, particulate or foam layer; Layered products characterised by having a layer differing constitutionally or physically in different parts characterised by the presence of two or more layers which are next to each other and are fibrous, filamentary, formed of particles or foamed one layer being a fibrous or filamentary layer
- B32B5/26—Layered products characterised by the non- homogeneity or physical structure, i.e. comprising a fibrous, filamentary, particulate or foam layer; Layered products characterised by having a layer differing constitutionally or physically in different parts characterised by the presence of two or more layers which are next to each other and are fibrous, filamentary, formed of particles or foamed one layer being a fibrous or filamentary layer another layer next to it also being fibrous or filamentary
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
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Abstract
線型雙官能苯醚寡聚物包含衍生自2-甲基-6-環己酚之重複單元且具有(甲基)丙烯酸酯端基。線型雙官能苯醚寡聚物特別可用於可固化組成物、熱固性組成物、以及由彼形成之物件。
Description
本揭露內容係關於封端苯醚寡聚物(end-capped phenylene ether oligomer)、形成彼之方法、包含彼之可固化熱固性組成物、以及由彼衍生之物件。
熱固性樹脂為固化以形成極硬塑膠之材料。該等材料可用於各式各樣消費性產品及工業產品。例如,熱固物(thermosets)係用於保護性塗層、黏著劑、電子層合物(諸如用於電腦電路板之製造者)、地板(flooring)、及鋪面(paving)應用、玻璃纖維強化管(glass fiber-reinforced pipe)、及汽車零件(automotive part)(包含片彈簧(leaf spring)、泵(pump)、及電氣組件(electrical component))。聚(芳醚)共聚物(poly(arylene ether) copolymer)通常具有良好介電性質(dielectric property)。因其廣泛用途,特別是用於電子應用(諸如印刷電路板之層合物(laminate)),希望提供具有較低黏度且同時維持或改善介電常數(dielectric constant)、耗散因子(dissipation factor)、耐熱性(heat resistance)、及吸水性(water absorption)之包含聚(芳醚)共聚物的可固化熱固性組成物。
因此,本領域中仍需要具有用於可固化熱固性組成物之一組理想性質的封端(end-capped)芳醚(arylene ether)聚合物(polymer)及寡聚物(oligomer)。若封端芳醚材料可提供具有改善之介電常數、耗散因子、耐熱性、及吸水性的可固化熱固性組成物,會是進一步的優點。
提供包含衍生自2-甲基-6-環己酚(2-methyl-6-cyclohexylphenol)之重複單元且具有(甲基)丙烯酸酯端基((meth)acrylate end group)的線型雙官能苯醚寡聚物(linear bifunctional phenylene ether oligomer)。
還提供形成線型雙官能苯醚寡聚物之方法,其包含於觸媒之存在下氧化聚合(oxidatively polymerizing) 2-甲基-6-環己酚以提供苯醚寡聚物;以及,使苯醚寡聚物與含(甲基)丙烯酸酯之化合物((meth)acrylate-containing compound)反應以提供線型雙官能苯醚寡聚物。
另外提供包含線型雙官能苯醚寡聚物之可固化熱固性組成物(curable thermosetting composition)以及由可固化熱固性組成物所衍生之物件(article)。
上述及其他特徵係以下文詳細說明為例。
本案發明人有利地發現衍生自2-甲基-6-環己酚且以(甲基)丙烯酸酯基團((meth)acrylate group)封端之苯醚寡聚物可包含於可固化熱固性組成物中以,與包含無衍生自2-甲基-6-環己酚之重複單元的苯醚寡聚物之熱固性組成物相比,獲致改善的性質。例如,衍生自2-甲基-6-環己酚之苯醚寡聚物可提供諸如溶液黏度(solution viscosity)、耗散因子(dissipation factor)、樹脂流動(resin flow)、及介電常數(dielectric constant)之性質組合的改善。
寡聚物可由上述衍生自2-甲基-6-環己酚之重複單元所組成或可包含衍生自不同於2-甲基-6-環己酚的一元酚(monohydric phenol)之重複單元。當寡聚物包含另外的重複單元時,苯醚寡聚物包含少於30重量百分比(以苯醚寡聚物之總重為基準計)之衍生自在2-位(2-position)及6-位(6- position)具有相同取代基的一元酚(例如,2,6-二甲苯酚(2,6-dimethylphenol)、2,3,6-二甲苯酚(2,3,6-dimethylphenol)等或其組合)之重複單元。較佳的,苯醚寡聚物包含少於20、或少於15、或少於10、或少於5、或少於2、或少於1、或少於0.5或少於0.1重量百分比之衍生自在2-位及6-位具有相同取代基的一元酚之重複單元。寡聚物可不含衍生自在2-位及6-位具有相同取代基的一元酚之重複單元。於一態樣中,本揭露內容之苯醚寡聚物不包括衍生自2-環己酚(2-cyclohexylphenol)之重複單元。
苯醚寡聚物進一步包含(甲基)丙烯酸酯端基((meth)acrylate end group)。因此,苯醚寡聚物具有以下結構之端基
其中,R為氫或甲基。於一態樣中,R為甲基,且苯醚寡聚物包含甲基丙烯酸酯端基。於一態樣中,R為氫,且苯醚寡聚物包含丙烯酸酯端基。
苯醚寡聚物具有線型架構(linear architecture)且為雙官能。此處所使用之「雙官能(bifunctional)」意指苯醚寡聚物於寡聚物鏈(oligomer chain)兩端具有官能基(functional group)。於寡聚物鏈兩端具有官能基之雙官能寡聚物(bifunctional oligomer)亦稱為「遙螯(telechelic)」寡聚物。因此,苯醚寡聚物之每一寡聚物鏈平均具有2個官能端基(functional end group)(即,(甲基)丙烯酸酯基)。例如,雙官能寡聚物之每一分子具有至少1.5至2、或至少1.70至2、或至少1.8至2、或至少1.9至2、或至少1.95至2個(甲基)丙烯酸酯基,或每一分子高達1.99個(甲基)丙烯酸酯基。
於一態樣中,苯醚寡聚物具有結構
其中,R
1及R
2各自獨立地為鹵素、未經取代或經取代之C
1-
12一級(primary)或二級(secondary)烴基(hydrocarbyl)、C
1-
12烴硫基(hydrocarbylthio)、C
1-
12烴氧基(hydrocarbyloxy)、或C
2-
12鹵烴氧基(halohydrocarbyloxy),其中至少兩個碳原子使鹵素原子及氫原子分開;R
3及R
4於各次出現時各自獨立地為氫、鹵素、未經取代或經取代之C
1-
12一級或二級烴基、C
1-
12烴硫基、C
1-
12烴氧基、或C
2-
12鹵烴氧基,其中至少兩個碳原子使鹵素原子及氫原子分開;x及y獨立地為0至30、較佳為0至20、更佳為0至15、又更佳為0至10、甚至更佳為0至8,其條件係x與y之總和至少為2、較佳至少為3、更佳至少為4;以及Y具有包含下列之結構
其中,R
7於各次出現時獨立地為氫或C
1-
12烴基,而R
8及R
9於各次出現時獨立地為氫、C
1-
12烴基、或C
1-
6伸烴基(hydrocarbylene),其中R
8及R
9共同形成C
4-
12伸烷基(alkylene group);以及z為0或1。
本揭露內容之苯醚寡聚物的製造可藉由於觸媒之存在下氧化聚合2-甲基-6-環己酚以提供苯醚寡聚物。苯醚寡聚物可透過在包含單體(monomer)、溶劑、及聚合觸媒(polymerization catalyst)之反應混合物中連續添加氧而藉由使包含2-甲基-6-苯基酚(2-methyl-6-phenylphenol)及二元酚(dihydric phenol)之單體(monomer)聚合(polymerization)而形成。
例如,二元酚可為1,1-雙(3,5-二甲基-4-羥基苯基)乙烷(1,1-bis(3,5-dimethyl-4-hydroxyphenyl) ethane)、1,1-雙(3-氯-4-羥基苯基)乙烷(1,1-bis(3-chloro-4-hydroxyphenyl)ethane)、1,1-雙(3-甲基-4-羥基苯基)-乙烷(1,1-bis(3-methyl-4-hydroxyphenyl)-ethane)、1,2-雙(4-羥基-3,5-二甲基苯基)-1,2-二苯乙烷(1,2-bis(4-hydroxy-3,5-dimethylphenyl)-1,2-diphenylethane)、1,2-雙(3-甲基-4-羥基苯基)-1,2-二苯乙烷(1,2-bis(3-methyl-4-hydroxyphenyl)-1,2-diphenylethane)、1,2-雙(3-甲基-4-羥基苯基)乙烷(1,2-bis(3-methyl-4-hydroxyphenyl)ethane)、2,2'-聯萘酚(2,2'-binaphthol)、2,2'-聯苯酚(2,2'-biphenol)、2,2'-二羥基-4,4'-二甲氧基二苯基酮(2,2'-dihydroxy-4,4'-
dimethoxybenzophenone)、2,2'-二羥基-4-甲氧基二苯基酮(2,2'-dihydroxy-4-methoxybenzo-phenone)、2,2'-二羥基二苯基酮(2,2'-dihydroxybenzophenone)、2,2-雙(3,5-二氯-4-羥基苯基)丙烷(2,2-bis(3,5-dichloro-4-
hydroxyphenyl)propane)、2,2-雙(3-溴-4-羥基苯基)丙烷(2,2-bis(3-bromo-4-hydroxyphenyl)propane)、2,2-雙(3-苯基-4-羥基苯基)丙烷(2,2-bis(3-phenyl-4-
hydroxyphenyl)propane)、2,2-雙(3-甲基-4-羥基苯基)丙烷(2,2-bis(3-methyl-4-hydroxyphenyl)propane)、2,2-雙(3,5-二甲基-4-羥基苯基)丙烷(2,2-bis(3,5-dimethyl-4-
hydroxyphenyl)propane)、1,1-雙(3,5-二甲基-4-羥基苯基)-1-苯乙烷(1,1-bis(3,5-dimethyl-4-hydroxyphenyl)-1-
phenylethane)、1,1-雙(3-氯-4-羥基苯基)-1-苯乙烷(1,1-bis(3-chloro-4-hydroxyphenyl)-1-phenylethane)、1,1-雙(3-甲基-4-羥基苯基)-1-苯乙烷(1,1-bis(3-methyl-4-hydroxyphenyl)-1-phenylethane)、2,2-雙(4-羥基-3,5-二甲基苯基)-1-苯丙烷(2,2-bis(4-hydroxy-3,5-dimethyl phenyl)-1-phenylpropane)、2,2-雙(4-羥基-3,5-二甲基苯基)己烷(2,2-bis(4-hydroxy-3,5-dimethyl phenyl)hexane)、2,2-雙(4-羥基-3,5-二甲基苯基)戊烷(2,2-bis(4-hydroxy-3,5-dimethylphenyl)pentane)、2,2-雙(3-甲基-4-羥基萘基)丙烷(2,2-bis(3-methyl-4-hydroxynaphthyl)propane)、2,2-雙(3-甲基-4-羥基苯基)-1-苯丙烷(2,2-bis(3-methyl-4-hydroxyphenyl)-1-phenylpropane)、2,2-雙(3-甲基-4-羥基苯基)己烷(2,2-bis(3-methyl-4-hydroxyphenyl)hexane)、2,2-雙(3-甲基-4-羥基苯基)戊烷(2,2-bis(3-methyl-4-hydroxyphenyl)pentane)、2,2'-亞甲基雙(4-甲苯酚)(2,2'-methylenebis(4-methylphenol))、2,2'-亞甲基雙[4-甲基-6-(1-甲基環己基)酚](2,2'-methylenebis[4-methyl-6-(1-methylcyclohexyl)phenol])、3,3',5,5'-四甲基-4,4'-聯苯酚(3,3',5,5'-tetramethyl-4,4'-biphenol)、3,3'-二甲基-4,4'-聯苯酚(3,3'-dimethyl-4,4'-biphenol)、雙(2-羥基苯基)-甲烷(bis(2-hydroxyphenyl)-methane)、雙(4-羥基-2,6-二甲基-3-甲氧基苯基)甲烷(bis(4-hydroxy-2,6-dimethyl-3-
methoxyphenyl)methane)、雙(3,5-二甲基-4-羥基苯基)甲烷(bis(3,5-dimethyl-4-hydroxyphenyl)methane)、雙(3-甲基-4-羥基苯基)甲烷(bis(3-methyl-4-
hydroxyphenyl)methane)、雙-(4-羥基-3,5-二甲基苯基)-環己基甲烷(bis-(4-hydroxy-3,5-dimethyl phenyl)-
cyclohexylmethane)、雙(4-羥基-3,5-二甲基苯基)苯基甲烷(bis(4-hydroxy-3,5-dimethyl phenyl)phenylmethane)、雙(3-甲基-4-羥基苯基)環己基甲烷(bis(3-methyl-4-
hydroxyphenyl)cyclohexylmethane)、雙(3-甲基-4-羥基苯基)甲烷(bis(3-methyl-4-hydroxyphenyl)methane)、雙(3,5-二甲基-4-羥基苯基)甲烷(bis(3,5-dimethyl-4-
hydroxyphenyl)methane)、雙(3-甲基-4-羥基苯基)苯基甲烷(bis(3-methyl-4-hydroxyphenyl)phenylmethane)、2,2',3,3',5,5'-六甲基-4,4'-聯苯酚(2,2',3,3',5,5'-hexamethyl-4,4'-biphenol)、八氟-4,4'-聯苯酚(octafluoro-4,4'-biphenol)、2,3,3',5,5'-五甲基-4,4'-聯苯酚(2,3,3',5,5'-pentamethyl-4,4'-biphenol)、1,1-雙(3,5-二溴-4-羥基苯基)環己烷(1,1-bis(3,5-dibromo-4-hydroxyphenyl)cyclohexane)、1,1-雙(3,5-二甲基-4-羥基苯基)環己烷(1,1-bis(3,5-dimethyl-4-hydroxyphenyl)cyclohexane)、雙(3-甲基-4-羥基苯基)環己烷(bis(3-methyl-4-hydroxyphenyl)cyclohexane)、四溴雙酚(tetrabromobisphenol)、四溴雙酚A(tetrabromobisphenol A)、四溴雙酚S(tetrabromobisphenol S)、2,2'-二烯丙基-4,4'-雙酚A(2,2'-diallyl-4,4'-bisphenol A)、2,2'-二烯丙基-4,4'-雙酚S(2,2'-diallyl-4,4'-bisphenol S)、硫化3,3',5,5'-四甲基-4,4'-雙酚(3,3',5,5'-tetramethyl-4,4'-bisphenol sulfide)、硫化3,3'-二甲基雙酚(3,3'-dimethyl bisphenol sulfide)、3,3',5,5'-四甲基-4,4'-雙酚碸(3,3',5,5'-tetramethyl-4,4'-bisphenol sulfone)、或其組合。
可以空氣或純氧提供分子氧(molecular oxygen)(O
2)。聚合觸媒(polymerization catalyst)為包含過渡金屬陽離子(transition metal cation)之金屬錯合物(metal complex)。金屬陽離子可包含來自周期表之VIB、VIIB、VIIIB、或IB族的離子、或其組合。其中,可使用鉻、錳、鈷、銅、及包含前述離子中至少一者之組合。於一態樣中,金屬離子為銅離子(Cu
+及Cu
2+)。可用作金屬陽離子之來源的金屬鹽包含氯化銅(I)(cuprous chloride)、氯化銅(II)(cupric chloride)、溴化銅(I)(cuprous bromide)、溴化銅(II)(cupric bromide)、碘化銅(I)(cuprous iodide)、碘化銅(II)(cupric iodide)、硫酸銅(I)(cuprous sulfate)、硫酸銅(II)(cupric sulfate)、硫酸四胺亞銅(cuprous tetraamine sulfate)、硫酸四胺銅(cupric tetraamine sulfate)、乙酸銅(I)(cuprous acetate)、乙酸銅(II)(cupric acetate)、丙酸銅(I)(cuprous propionate)、丁酸銅(II)(cupric butyrate)、月桂酸銅(II)(cupric laurate)、棕櫚酸銅(I)(cuprous palmitate)、苯甲酸銅(I)(cuprous benzoate)、及對應之錳鹽(manganese salt)及鈷鹽(cobalt salt)。代替使用上述舉例說明之金屬鹽的任一者,亦可添加金屬或金屬氧化物及無機酸(inorganic acid)、有機酸(organic acid)或此種酸之水溶液,以及原位(
in situ)形成對應之金屬鹽或水合物(hydrate)。例如,可添加氧化銅(I)及氫溴酸(hydrobromic acid)以原位產生溴化銅(I)。
聚合觸媒(polymerization catalyst)進一步包含至少一個胺配位基(amine ligand)。胺配位基可為例如單胺(monoamine)、烷二胺(alkylene diamine)、或包含前述至少一者之組合。單胺包含二烷基單胺(dialkylmonoamine) (諸如二正丁胺(di-
n-butylamine),或DBA)以及三烷基單胺(trialkylmonoamine)(諸如N,N-二甲基丁胺(N,N-dimethylbutylamine),或DMBA)。二胺包含烷二胺(alkylenediamine),諸如N,N'-二-三級丁基乙二胺(N,N'-di-
tert-butylethylenediamine),或DBEDA。適合的二烷基單胺包含二甲胺(dimethylamine)、二正丙胺(di-
n-propylamine)、二正丁胺(di-
n-butylamine)、二-二級丁胺(di-
sec-butyl amine)、二-三級丁胺(di-
tert-butylamine)、二戊胺(dipentylamine)、二己胺(dihexylamine)、二辛胺(dioctylamine)、二癸胺(didecylamine)、二苄胺(dibenzylamine)、甲基乙胺(methylethylamine)、甲基丁胺(methylbutylamine)、二環己胺(dicyclohexylamine)、N-苯基乙醇胺(N-phenylethanolamine)、N-(對甲基)苯基乙醇胺(N-(
p-methyl)phenylethanolamine)、N-(2,6-二甲基)苯基乙醇胺(N-(2,6-dimethyl)phenylethanolamine)、N-(對氯)苯基乙醇胺(N-(
p-chloro)phenylethanolamine)、N-乙基苯胺(N-ethylaniline)、N-丁基苯胺(N-butyl aniline)、N-甲基-2-甲基苯胺(N-methyl-2-methylaniline)、N-甲基-2,6-二甲基苯胺(N-methyl-2,6-dimethylaniline)、二苯胺(diphenylamine)等、或其組合。適合的三烷基單胺(trialkylmonoamine)包含三甲胺(trimethylamine)、三乙胺(triethylamine)、三丙胺(tripropylamine)、三丁胺(tributylamine)、丁基二甲胺(butyldimethylamine)、苯基二乙胺(phenyldiethylamine)等、或其組合。
適合的烷二胺(alkylenediamine)包含具有下式者:
(R
d)
2N–R
c–N(R
d)
2其中,R
c為經取代或未經取代之二價殘基(divalent residue);以及各R
d獨立地為氫或C
1-
8烷基。於上式之一些實例中,二或三個脂族碳原子在兩個二胺氮原子(diamine nitrogen atom)之間形成最緊密鍵聯(closest link)。具體烷二胺配位基(alkylenediamine ligand)包含其中R
c為二亞甲基(–CH
2CH
2–)或三亞甲基(–CH
2CH
2CH
2–)者。R
d可獨立地為氫、甲基、丙基、異丙基、丁基、或C
4-
8α-三級烷基(C
4-
8alpha‑tertiary alkyl group)。烷二胺配位基之實例包含N,N,N',N'-四甲基乙二胺(N,N,N',N' tetramethylethylene diamine)(TMED)、N,N'-二-三級丁基乙二胺(N,N'-di-tert-butylethylenediamine)(DBEDA)、N,N,N',N'-四甲基-1,3-二胺基丙烷(N,N,N',N'-tetramethyl-l,3-diaminopropane) (TMPD)、N-甲基-1,3-二胺基丙烷(N‑methyl-1,3-diaminopropane)、N,N'-二甲基-1,3-二胺基丙烷(N,N'-dimethyl-1,3-diaminopropane)、N,N,N'-二甲基-1,3-二胺基丙烷(N,N,N'‑dimethyl‑1,3‑diaminopropane)、N-乙基-1,3-二胺基丙烷(N-ethyl-1,3-diaminopropane)、N-甲基-1,4-二胺基丁烷(N‑methyl‑l,4‑diaminobutane)、N,N'-三甲基-1,4-二胺基丁烷(N,N'-trimethyl-l,4-diaminobutane)、N,N,N'-三甲基-1,4-二胺基丁烷(N,N,N'‑trimethyl‑l,4‑diaminobutane)、N,N,N',N'-四甲基-1,4-二胺基丁烷(N,N,N',N'-tetramethyl-l,4-diaminobutane)、N,N,N',N'-四甲基-1,5-二胺基戊烷(N,N,N',N'‑tetramethyl-l,5-diaminopentane)、或其組合。於一態樣中,胺配位基為二正丁胺(DBA)、N,N-二甲基丁胺(DMBA)、N,N'-二-三級丁基乙二胺(DBEDA)、或其組合。觸媒可藉由混合金屬離子源(例如氧化銅(I)及氫溴酸)與胺配位基而原位製備(prepared
in situ)。於一態樣中,聚合觸媒包含銅離子、溴離子、及
N,N'-二-三級丁基乙二胺(
N,N'-di-
tert-butylethylenediamine)。
製造官能化苯醚寡聚物(functionalized phenylene ether oligomer)之方法進一步包含使苯醚寡聚物(例如「未封端」的羥基為末端("uncapped" hydroxyl-terminated)之苯醚寡聚物)與包含(甲基)丙烯酸酯基團之化合物反應以提供官能化苯醚寡聚物。例如,該方法可包含使羥基為末端(hydroxyl-terminated)之苯醚寡聚物與(甲基)丙烯醯氯((meth)acryloyl chloride)反應。苯醚寡聚物與包含(甲基)丙烯酸酯基團之化合物之間的反應可於溶劑中進行。於一些態樣中,苯醚寡聚物可呈粉末(powder)形式獲得,該粉末隨後與包含(甲基)丙烯酸酯基團之化合物及溶劑組合。於另外的態樣中,未封端之苯醚寡聚物(uncapped phenylene ether oligomer)可呈來自氧化聚合反應(oxidative polymerization reaction)而未移除溶劑之溶液形式獲得,且未封端之苯醚寡聚物並非從溶劑溶液分離為粉末。例如,包含(甲基)丙烯酸酯基團之化合物可直接添加至由在溶劑中氧化聚合(oxidatively polymerizing)2-甲基-6-環己酚與二元酚(dihydric phenol)直接獲得的未封端之苯醚寡聚物之溶液,其中在與包含(甲基)丙烯酸酯基團之化合物反應之前溶劑未從反應產物移除。例示性合成係於以下操作實例中進一步說明。熟習本領域之人士可易於判定包含(甲基)丙烯酸酯基團及對羥基為末端之苯醚寡聚物(hydroxyl-terminated phenylene ether oligomer)有反應性之基團的適宜化合物。
苯醚寡聚物可具有每莫耳600至5,000克之數量平均分子量(number average molecular weight)(Mn),例如每莫耳600至3,500克、或每莫耳1,000至5,000克、或每莫耳1,000至3,500克。數量平均分子量可藉由例如凝膠滲透層析術(gel permeation chromatography)相對於聚苯乙烯標準品(polystyrene standard)測定。
本揭露內容之苯醚寡聚物可具有低於每克0.15分升(deciliter)、或每克0.02至0.15分升、或每克0.03至0.10分升、或每克0.035至0.075分升之固有黏度(intrinsic viscosity)。固有黏度可藉由烏氏黏度計(Ubbelohde viscometer)於25℃於氯仿中測量。
還提供包含具有(甲基)丙烯酸酯端基之線型雙官能苯醚寡聚物的可固化熱固性組成物。例如,雙官能苯醚寡聚物可以1至95重量百分比(wt%)、或5至95 wt%、或10至85 wt%、或20至80 wt%、30至70 wt%、或5至30 wt%、或5至15 wt%之量(以可固化熱固性組成物之總重為基準計)存在於可固化熱固性組成物中。
可固化熱固性組成物可進一步包含交聯劑(crosslinking agent)、固化劑(curing agent)、固化觸媒(curing catalyst)、固化引發劑(curing initiator)、或其組合中之一或多者。於一些態樣中,可固化熱固性組成物可進一步包含阻燃劑(flame retardant)、填料(filler)、偶合劑(coupling agent)、或其組合中之一或多者。例如,可固化熱固性組成物可包含交聯劑、固化劑、固化觸媒、固化引發劑、或其組合中之一或多者;以及可進一步包含阻燃劑、填料、偶合劑、或其組合中之一或多者。
熱固性樹脂、交聯劑、及偶合劑間有相當大的重疊。如本文所使用,術語「交聯劑(crosslinking agent)」包含可用作熱固性樹脂、交聯劑、偶合劑、或其組合之化合物。例如,在一些實例中,為熱固性樹脂之化合物亦可用作交聯劑、偶合劑、或二者。
熱固性樹脂無特別限制,以及熱固性樹脂可單獨使用或組合使用二或更多熱固性樹脂(例如,包含一或多種輔助熱固性樹脂(auxiliary thermosetting resin))。例示性熱固性樹脂包含環氧樹脂(epoxy resin)、氰酸酯樹脂(cyanate ester resin)、(雙)順丁烯二醯亞胺樹脂((bis) maleimide resin)、(聚)苯并㗁𠯤樹脂((poly)benzoxazine resin)、乙烯系樹脂(vinyl resin)(例如,乙烯基苄基醚樹脂(vinyl benzyl ether resin))、酚樹脂(phenolic resin)、醇酸樹脂(alkyd resin)、不飽和聚酯樹脂(unsaturated polyester resin)、芳基環丁烯樹脂(arylcyclobutene resin)、全氟乙烯醚樹脂(perfluorovinyl ether resin)、具有可固化不飽和(curable unsaturation)(例如乙烯基官能性(vinyl functionality))之單體、寡聚物或聚合物等、或其組合。
環氧樹脂(epoxy resin)通常可為適用於熱固性樹脂之任何環氧樹脂。上下文中之術語「環氧樹脂」係指如C. A. May, Epoxy Resins (2.sup.nd Edition, (New York & Basle: Marcel Dekker Inc.), 1988中所述的含氧環之化合物(oxirane ring-containing compound)的可固化組成物。環氧樹脂可包含雙酚A型環氧樹脂(bisphenol A type epoxy resin),諸如由雙酚A與藉由以鹵素原子、具有6或更少碳原子之烷基或苯基取代雙酚A之2-位、3-位及5-位之至少一個位置所獲得的樹脂所獲得者;雙酚F型環氧樹脂(bisphenol F type epoxy resin),諸如由雙酚F與藉由以鹵素原子、具有6或更少碳原子之烷基或苯基取代雙酚F之2-位、3-位及5-位中至少一個位置所獲得的樹脂所獲得者;環氧丙基醚化合物(glycidyl ether compound),衍生自二價(bivalent)或三或更高價酚類(phenols),諸如氫醌(hydroquinone)、間苯二酚(resorcinol)、參-4-(羥基苯基)甲烷(tris-4-(hydroxyphenyl)methane)及1,1,2,2-肆(4-羥基苯基)乙烷(1,1,2,2-tetrakis(4-hydroxyphenyl)ethane);酚醛型環氧樹脂(novolak type epoxy resin),衍生自酚醛樹脂(novolak resin),其為酚類(諸如酚(phenol)及鄰甲酚(o-cresol))與甲醛(formaldehyde)之間的反應產物,包含雙酚A酚醛型環氧樹脂(bisphenol A novolak type epoxy resin)以及甲酚酚醛型環氧樹脂(cresol novolak type epoxy resin);環脂族環氧化合物(cyclic aliphatic epoxy compound),諸如2,2-雙(3,4-環氧基環己基)丙烷(2,2-bis(3,4-epoxycyclohexyl)propane)、2,2-雙[4-(2,3-環氧基丙基)環己基]丙烷(2,2-bis[4-(2,3-epoxypropyl)cyclohexyl]propane)、二氧化乙烯基環己烯(vinylcyclohexene dioxide)、3,4-環氧基環己基甲基-3,4-環氧基環己烷羧酸酯(3,4-epoxycyclohexylmethyl-3,4-epoxycyclohexane carboxylate);含雙環戊二烯之聚環氧化物(dicyclopentadiene-containing polyepoxide);胺型環氧樹脂(amine type epoxy resin),衍生自苯胺(aniline)、對胺基苯酚(p-aminophenol)、間胺基苯酚(m-aminophenol)、4-胺基-間甲酚(4-amino-m-cresol)、6-胺基-間甲酚(6-amino-m-cresol)、4,4'-二胺基二苯基-乙烷(4,4′-diaminodiphenyl-ethane)、3,3'-二胺基二苯基甲烷(3,3′-diaminodiphenylmethane)、4,4'-二胺基二苯基醚(4,4′-diaminodiphenyl ether)、3,4'-二胺基二苯基醚(3,4′-diaminodiphenylether)、1,4-雙(4-胺基苯氧基)苯(1,4-bis(4-aminophenoxy)benzene)、1,4-雙(3-胺基苯氧基)-苯(1,4-bis(3-aminophenoxy)-benzene)、1,3-雙(4-胺基苯氧基)-苯(1,3-bis(4-aminophenoxy)-benzene)、1,3-雙(3-胺基苯氧基)苯(1,3-bis(3-aminophenoxy)benzene)、2,2-雙(4-胺基-苯氧基苯基)丙烷(2,2-bis(4-amino-phenoxyphenyl)propane)、對苯二胺(p-phenylenediamine)、間苯二胺(m-
phenylenediamine)、2,4-甲苯二胺(2,4-toluenediamine)、2,6-甲苯二胺(2,6-toluenediamine)、對二甲苯-二胺(p-xylylene-diamine)、間二甲苯二胺(m-xylylenediamine)、1,4-環己烷-雙(甲胺)(1,4-cyclohexane-bis(methylamine))、5-胺基-1-(4'-胺基苯基)-1,3,3-三甲基二氫茚(5-amino-1-(4′-aminophenyl)-1,3,3-trimethylindane)、6-胺基-1-(4'-胺基苯基)-1,3,3-三甲基-二氫茚(6-amino-1-(4′-aminophenyl)-1,3,3-trimethyl-indane)等;雜環環氧化合物(hetero-cyclic epoxy compound)、以及環氧丙酯型環氧化合物(glycidyl ester type epoxy compound),例如,衍生自芳族羧酸(aromatic carboxylic acid)之環氧丙酯(glycidyl ester)者,該芳族羧酸係諸如對氧苯甲酸(p-oxybenzoic acid)、間氧苯甲酸(m-oxybenzoic acid)、對苯二甲酸(terephthalic acid)、及間苯二甲酸(isophthalic acid)。「環氧樹脂(epoxy resin)」亦可包含含有二或更多個環氧基(epoxy group)之化合物與芳族二羥基化合物(aromatic dihydroxy compound)的反應產物,其可視需要的(optionally)經鹵素取代(halogen-substituted)以及可單獨使用或二或更多者組合使用。
氰酸酯(cyanate ester)並無限制,以及可使用由氰酸酯單體(cyanate ester monomer)所構成之任何樹脂,該氰酸酯單體聚合而形成含有多個氰酸酯(-OCN)官能基之聚合物。氰酸酯單體、預聚合物(prepolymer)(即,部分聚合之氰酸酯單體或氰酸酯單體之摻合物(blend))、同元聚合物(homopolymer)、及共聚物係使用氰酸酯前驅物(cyanate ester precursor)以及此等化合物之組合製成。例如,氰酸酯可根據"Chemistry and Technology of Cyanate Ester Resins", by Ian Hamerton, Blackie Academic and Professional、美國專利3,553,244號及JP-A-7-53497中所揭露之方法製備。例示性氰酸酯樹脂包含2,2-雙(4-氰氧苯基)-丙烷(2,2-bis(4-cyanatophenyl)-propane)、雙(4-氰氧苯基)乙烷(bis(4-cyanatophenyl)ethane)、雙(3,5-二甲基-4-氰氧苯基)甲烷(bis(3,5-dimethyl-4-cyanatophenyl)methane)、2,2-雙(4-氰氧苯基)-1,1,1,3,3,3-六氟丙烷(2,2-bis(4-cyanatophenyl)-1,1,1,3,3,3-hexafluoropropane)、α,α'-雙(4-氰氧苯基)-間二異丙基-苯(α,α′-bis(4-cyanatophenyl)-m-diisopropyl-benzene)、由二環戊二烯-酚共聚物(dicyclopentadiene-phenol copolymer)所製備之氰酸酯樹脂(cyanate ester resin)、以及由此等單體所製備之預聚合物。預聚合物之實例為PRIMASET BA-230S (Lonza)。氰酸酯預聚合物可為同元聚合物或可為合併其他單體之共聚物。此等共聚物之實例包含得自Mitsubishi Gas Chemical之BT樹脂,諸如BT 2160及BT2170,其為以氰酸酯單體及雙順丁烯二醯亞胺單體(bismaleimide monomer)所製成的預聚合物。其他氰酸酯聚合物、單體、預聚合物、及氰酸酯單體與其他非氰酸酯單體之摻合物係揭露於US 7393904、US 7388057、US 7276563、及US 7192651。
雙順丁烯二醯亞胺(bismaleimide)樹脂可藉由單體雙順丁烯二醯亞胺(monomeric bismaleimide)與親核劑(nucleophile)(諸如二胺(diamine)、胺基苯酚(aminophenol)、或胺基苯甲醯肼(amino benzhydrazide))之反應、或藉由雙順丁烯二醯亞胺與二烯丙基雙酚A(diallyl bisphenol A)之反應而製造。例示性雙順丁烯二醯亞胺樹脂包含1,2-雙順丁烯二醯亞胺基乙烷(1,2-bismaleimidoethane)、1,6-雙順丁烯二醯亞胺基己烷(1,6-bismaleimidohexane)、1,3-雙順丁烯二醯亞胺基苯(1,3-bismaleimidobenzene)、1,4-雙順丁烯二醯亞胺基-苯(1,4‑bismaleimido-benzene)、2,4-雙順丁烯二醯亞胺基甲苯(2,4-bismaleimidotoluene)、4,4'-雙順丁烯二醯亞胺基二苯基甲烷(4,4'-bismaleimidodiphenylmethane)、4,4'-雙順丁烯二醯亞胺基-二苯基醚(4,4'-bismaleimido-diphenylether)、3,3'-雙順丁烯二醯亞胺基二苯碸(3,3'-bismaleimidodiphenylsulfone)、4,4'-雙順丁烯二醯亞胺基-二苯碸(4,4'‑bismaleimido-diphenylsulfone)、4,4'-雙順丁烯二醯亞胺基二環己基甲烷(4,4'-bismaleimidodicyclohexylmethane)、3,5-雙(4-順丁烯二醯亞胺基苯基)吡啶(3,5-bis(4-maleimidophenyl)pyridine)、2,6-雙順丁烯二醯亞胺基-吡啶(2,6-bismaleimido-pyridine)、1,3-雙(順丁烯二醯亞胺基甲基)環己烷(1,3-bis(maleimidomethyl)cyclohexane)、1,3-雙(順丁烯二醯亞胺基甲基)苯(1,3-bis(maleimidomethyl) benzene)、1,1-雙(4-順丁烯二醯亞胺基苯基)環己烷(1,1-bis(4-maleimidophenyl)cyclohexane)、1,3-雙(二氯順丁烯二醯亞胺基)苯(1,3-bis(dichloromaleimido)benzene)、4,4'-雙(檸康-醯亞胺基)二苯基甲烷(4,4'-bis(citracon-imido)diphenylmethane)、2,2-雙(4-順丁烯二醯亞胺基苯基)丙烷(2,2-bis(4-maleimidophenyl)propane)、1-苯基-1,1-雙(4-順丁烯二醯亞胺基-苯基)乙烷(1-phenyl-1,1-bis(4-maleimido-phenyl)ethane)、N,N-雙(4-順丁烯二醯亞胺基苯基)甲苯(N,N-bis(4-maleimidophenyl)toluene)、3,5-雙順丁烯二醯亞胺基-1,2,4-三唑(3,5-bismaleimido-1,2,4-triazole)、N,N'-伸乙基雙順丁烯二醯亞胺(N,N'-ethylenebismaleimide)、N,N'-六亞甲基雙順丁烯二醯亞胺(N,N'-hexamethylenebismaleimide)、N,N'-間伸苯基-雙順丁烯二醯亞胺(N,N'-m-phenylene-bismaleimide)、N,N'-對伸苯基雙順丁烯二醯亞胺(N,N'-p-phenylenebismaleimide)、N,N'-4,4'-二苯基甲烷雙順丁烯二醯亞胺(N,N'-4,4'-diphenylmethanebismaleimide)、N,N'-4,4'-二苯基-醚雙順丁烯二醯亞胺(N,N'-4,4'-diphenyl-etherbismaleimide)、N,N'-4,4'-二苯碸雙順丁烯二醯亞胺(N,N'-4,4'-diphenylsufonebismaleimide)、N,N'-4,4'-二環己基甲烷-雙順丁烯二醯亞胺(N,N'-4,4'-dicyclohexylmethane-bismaleimide)、N,N'-α,α'-4,4'-二亞甲基環己烷雙順丁烯二醯亞胺(N,N'-α,α'-4,4'-dimethylenecyclohexanebismaleimide)、N,N'-間亞甲基-雙順丁烯二醯亞胺(N,N'-m-methaxylene-bismaleimide)、N,N'-4,4'-二苯基環己烷雙順丁烯二醯亞胺(N,N'-4,4'-diphenylcyclohexanebismaleimide)、及N,N'-亞甲基-雙(3-氯-對伸苯基)雙順丁烯二醯亞胺(N,N'-methylene-bis(3-chloro-p-phenylene)bismaleimide),以及US 3,562,223、US 4,211,860、及US 4,211,861中所揭露者,或藉由例如US 3,018,290中所述之方法製備。
苯并㗁𠯤化合物(benzoxazine compound)的分子中具有苯并㗁𠯤環(benzoxazine ring)。例示性苯并㗁𠯤單體可由醛類(aldehydes)、酚類(phenols)與一級胺類(primary amines)在有或無溶劑之情況下反應而製備。用於形成苯并㗁𠯤之酚化合物(phenolic compound)包含酚類(phenols)及多酚(polyphenols)。使用具有二或更多個在形成苯并㗁𠯤時具有反應性之羥基的多酚可形成分枝產物(branched product)、交聯產物(crosslinked product)、或分枝且交聯產物之組合。將酚基(phenolic group)連接至酚(phenol)之基團可為聚苯并㗁𠯤(polybenzoxazine)中之分枝點(branch point)或連接基團(connecting group)。
用於製備苯并㗁𠯤單體之例示性酚類(phenols)包含酚(phenol)、甲酚(cresol)、間苯二酚(resorcinol)、兒茶酚(catechol)、氫醌(hydroquinone)、2-烯丙苯酚(2-allylphenol)、3-烯丙苯酚、4-烯丙苯酚、2,6-二羥萘(2,6-dihydroxynaphthalene)、2,7-二羥萘、2-(二苯基-磷醯基)氫醌(2-(diphenyl-phosphoryl)hydroquinone)、2,2'-聯苯酚(2,2'-biphenol)、4,4-聯苯酚、4,4'-亞異丙基二酚(4,4'-isopropylidenediphenol)、4,4'-亞異丙基雙(2-甲基-苯酚)(4,4'-isopropylidenebis(2-methyl-phenol))、4,4'-亞異丙基雙(2-烯丙苯酚)(4,4'-isopropylidenebis(2-allylphenol))、4,4'(1,3-伸苯基二亞異丙基)雙酚(4,4'(1,3-phenylenediisopropylidene)bisphenol)(雙酚M(bisphenol M))、4,4'-亞異丙基雙(3-苯基苯酚)(4,4'-isopropylidenebis (3-phenylphenol))、4,4'-(1,4-伸苯基二亞異丙基)-雙酚(4,4'-(1,4-phenylenediisoproylidene)-bisphenol)、4,4'-亞乙基二酚(4,4'-ethylidenediphenol)、4,4'-氧二酚(4,4'-oxydiphenol)、4,4'-硫二酚(4,4'-thiodiphenol)、4,4'-磺醯基二酚(4,4'-sufonyldiphenol)、4,4'-亞磺醯基二酚(4,4'-sulfinyldiphenol)、4,4'-六氟亞異丙基)雙酚(4,4'-hexafluoroisopropylidene)bisphenol)、4,4'(1-苯基亞乙基)-雙酚(4,4'(1-phenylethylidene)-bisphenol)、雙(4-羥基苯基)-2,2-二氯乙烯(bis(4-hydroxyphenyl)-2,2-dichloroethylene)、雙(4-羥基苯基)甲烷(bis(4-hydroxyphenyl)methane)、4,4'-(亞環戊基)二酚(4,4'-(cyclopentylidene)diphenol)、4,4'-(亞環己基)二酚(4,4'-(cyclohexylidene)diphenol)、4,4'-(亞環十二基)二酚(4,4'-(cyclododecylidene)diphenol)、4,4'-(雙環[2.2.1]亞庚基)二酚(4,4'-(bicyclo[2.2.1]heptylidene) diphenol)、4,4'-(9H-茀-9,9-二基)二酚(4,4'-(9H-fluorene-9,9-diyl)diphenol)、亞異丙基-雙(2-烯丙苯酚) (isopropylidene-bis(2-allylphenol))、3,3-雙(4-羥基苯基)異苯并呋喃-1(3H)-酮(3,3-bis(4-hydroxyphenyl)isobenzofuran-1 (3H)-one)、1-(4-羥基苯基)-3,3-二甲基-2,3-二氫-1H-茚-5-醇(1-(4-hydroxyphenyl)-3,3-dimethyl-2,3-dihydro-1H-inden -5-ol)、3,3,3',3'-四甲基-2,2',3,3'-四氫-1,1'-螺二-[茚]5,6'-二醇(3,3,3',3'-tetramethyl-2,2',3,3'-tetrahydro-1,1'-spirobi-[indene]5,6'-diol)、二羥基二苯基酮(dihydroxybenzophenone)、參(4-羥基苯基)甲烷(tris(4-hydroxyphenyl)methane)、參(4-羥基-苯基)乙烷(tris(4-hydroxy-phenyl)ethane)、參(4-羥基苯基)丙烷(tris(4-hydroxyphenyl)propane)、參(4-羥基苯基)丁烷(tris(4-hydroxyphenyl)butane)、參(3-甲基-4-羥基苯基)甲烷(tris(3-methyl-4-hydroxyphenyl)methane)、肆(4-羥基苯基)乙烷(tetrakis(4-hydroxyphenyl)ethane)、二環戊二烯基雙(2,6-二甲苯酚)(dicyclopentadienylbis(2,6-dimethyl phenol))、二環戊二烯基雙(鄰甲酚)(dicyclopentadienyl bis(ortho-cresol))、二環戊二烯基雙酚(dicyclopentadienyl bisphenol)等。
用以形成苯并㗁𠯤之醛類(aldehydes)可為任何醛,諸如具有1至10個碳原子之醛。例如,醛可為甲醛(formaldehyde)。用以形成苯并㗁𠯤之胺可為芳族胺(aromatic amine)、脂族胺(aliphatic amine)、烷基取代之芳族胺、或芳族取代之烷基胺。胺可為多胺(polyamine),例如,用以製備用於交聯之多官能苯并㗁𠯤單體。
用於形成苯并㗁𠯤之胺具有1至40個碳原子,除非其包含芳族環,則可具有6至40個碳原子。二官能或多官能之胺可為用以使聚苯并㗁𠯤彼此連接之分枝點(branch point)。
於一些實例中,於150至300℃之熱聚合(thermal polymerization)可用於聚合(polymerizing)苯并㗁𠯤單體。聚合可整體(in bulk)進行、從溶液(from solution)進行、或者其他。觸媒(諸如羧酸)可用以降低聚合溫度或加速在相同溫度之聚合速率(polymerization rate)。
乙烯基苄基醚樹脂(vinyl benzyl ether resins)可由酚(phenol)與乙烯基苄基鹵化物(vinyl benzyl halide)(諸如乙烯基苄基氯化物(vinyl benzyl chloride))之縮合(condensation)而製備。雙酚-A以及參酚(trisphenols)和多酚(polyphenols)通常用以製造可用於製造經交聯熱固性樹脂(crosslinked thermosetting resin)之聚(乙烯基苄基醚)(poly(vinylbenzyl ethers))。例示性乙烯基苄基醚(vinyl benzyl ethers)可包含由乙烯基苄基鹵化物與下列之反應所製造的乙烯基苄基醚:間苯二酚、兒茶酚、氫醌、2,6-二羥萘、2,7-二羥萘、2-(二苯基-磷醯基)氫醌、雙(2,6-二甲苯酚)(bis(2,6-dimethylphenol))、2,2'-聯苯酚、4,4-聯苯酚、2,2',6,6'-四甲基聯苯酚(2,2',6,6'-tetramethylbiphenol)、2,2',3,3',6,6'-六甲基聯苯酚(2,2',3,3',6,6'-
hexamethylbiphenol)、3,3',5,5'-四溴-2,2'6,6'-四甲基聯苯酚(3,3',5,5'-tetrabromo-2,2'6,6'-tetramethylbiphenol)、3,3'-二溴-2,2',6,6'-四甲基聯苯酚(3,3'-dibromo-2,2',6,6'-tetramethylbiphenol)、2,2',6,6'-四甲基-3,3'5-二溴聯苯酚(2,2',6,6'-tetramethyl-3,3'5-dibromobiphenol)、4,4'-亞異丙基二酚、4,4'-亞異丙基雙(2,6-二溴酚)(4,4'-isopropylidenebis (2,6-dibromophenol))、4,4'-亞異丙基雙(2,6-二甲苯酚)(4,4'-isopropylidenebis(2,6-dimethylphenol))(四甲基雙酚A(teramethylbisphenol A))、4,4'-亞異丙基雙(2-甲苯酚)(4,4'-isopropylidenebis(2-methylphenol))、4,4'-亞異丙基雙(2-烯丙苯酚)、4,4'(1,3-伸苯基二亞異丙基)雙酚(4,4'(1,3-phenylenediisopropylidene)bisphenol)、4,4'-亞異丙基雙(3-苯基苯酚)、4,4'-(1,4-伸苯基二亞異丙基)雙酚、4,4'-亞乙基二酚、4,4'-氧二酚、4,4'-硫二酚、4,4'-硫雙(2,6-二甲苯酚)(4,4'-thiobis(2,6-dimethylphenol))、4,4'-磺醯基二酚、4,4'-磺醯基雙(2,6-二甲苯酚)(4,4'-sulfonylbis(2,6-dimethylphenol))、4,4'-亞磺醯基-二酚、4,4'-六氟亞異丙基)雙酚、4,4'(1-苯基亞乙基)雙酚、雙(4-羥基苯基)-2,2-二氯乙烯、雙(4-羥基-苯基)甲烷(bis(4-hydroxy-phenyl)methane)、雙(2,6-二甲基-4-羥基苯基)甲烷(bis(2,6-dimethyl-4-hydroxyphenyl)methane)、4,4'-(亞環戊基)二酚、4,4'-(亞環己基)二酚、4,4'-(亞環十二基)二酚、4,4'-(雙環[2.2.1]亞庚基)二酚、4,4'-(9H-茀-9,9-二基)二酚、3,3-雙(4-羥基苯基)-異苯并呋喃-1(3H)-酮、1-(4-羥基苯基)-3,3-二甲基-2,3-二氫-1H-茚-5-醇、1-(4-羥基-3,5-二甲基苯基)-1,3,3,4,6-五甲基-2,3-二氫-1H-茚-5-醇(1-(4-hydroxy-3,5-dimethylphenyl)-1,3,3,4,6-pentamethyl-2,3-dihydro-1H-inden-5-ol)、3,3,3',3'-四甲基-2,2',3,3'-四氫-1,1'-螺二[茚]-5,6'-二醇(3,3,3',3'-tetramethyl-2,2',3,3'-tetrahydro-1,1'-spirobi[indene]-5,6'-diol)、二羥基二苯基酮、參(4-羥基苯基)甲烷、參(4-羥基苯基)乙烷、參(4-羥基苯基)-丙烷、參(4-羥基苯基)丁烷、參(3-甲基-4-羥基苯基)甲烷、參(3,5-二甲基-4-羥基-苯基)甲烷(tris(3,5-dimethyl-4-hydroxy-phenyl)methane)、肆(4-羥基苯基)乙烷(tetrakis(4-hydroxyphenyl)ethane)、肆(3,5-二甲基-4-羥基苯基)-乙烷(tetrakis(3,5-dimethyl-4-hydroxyphenyl)-ethane)、雙(4-羥基苯基)苯膦氧化物(bis(4-hydroxyphenyl) phenylphosphine oxide)、二環戊二烯基-雙(2,6-二甲苯酚)、二環戊二烯基雙酚(dicyclopentadienyl bisphenol)等。
芳基環丁烯(Arylcyclobutenes)包含衍生自具有以下結構之化合物者:
其中,B為n價之有機或無機基(包含羰基、磺醯基(sulfonyl)、亞磺醯基、硫化物(sulfide)、氧基(oxy)、烷基膦醯基(alkylphosphonyl)、芳基膦醯基(arylphosphonyl)、亞異烷基(isoalkylidene)、亞環烷基(cycloalkylidene)、芳基亞烷基(arylalkylidene)、二芳基亞甲基(diarylmethylidene)、亞甲基(methylidene)二烷基矽烷基(dialkylsilanyl)、芳基烷基矽烷基(arylalkylsilanyl)、二芳基矽烷基(diarylsilanyl)及C
6-20酚化合物(C
6-20phenolic compounds));X於各次出現時獨立地為羥基或C
1-24烴基(包含直鏈(linear)及分枝(branched)烷基及環烷基);以及,Z於各次出現時獨立地為氫、鹵素、或C
1-12烴基;以及n為1至1000、或1至8,或者n為2、3、或4。其他例示性芳基環丁烯(arylcyclobutenes)及芳基環丁烯合成之方法可見US 4,743,399、US 4,540,763、US 4,642,329、US 4,661,193、US 4,724,260、及5391,650。
全氟乙烯醚(Perfluorovinyl ethers)通常係由酚類(phenols)及溴四氟乙烷(bromotetrafluoroethane)合成,然後藉由鋅催化之還原消去(zinc catalyzed reductive elimination)製造ZnFBr及所希望的全氟乙烯醚(perfluorovinylether)。藉由此途徑,雙酚、參酚及其他多酚可製造雙(全氟乙烯醚)、參(全氟乙烯醚)及聚(全氟乙烯醚)(poly(perfluorovinylether))。可用於彼等之合成的酚類包含間苯二酚、兒茶酚、氫醌、2,6-二羥萘(2,6-dihydroxy naphthalene)、2,7-二羥萘、2-(二苯基-磷醯基)氫醌、雙(2,6-二甲苯酚)、2,2'-聯苯酚、4,4-聯苯酚、2,2',6,6'-四甲基聯苯酚、2,2',3,3',6,6'-六甲基聯苯酚、3,3',5,5'-四溴-2,2'6,6'-四甲基聯苯酚、3,3'-二溴-2,2',6,6'-四甲基聯苯酚、2,2',6,6'-四甲基-3,3'5-二溴聯苯酚、4,4'-亞異丙基二酚(雙酚A(bisphenol A))、4,4'-亞異丙基雙(2,6-二溴酚)、4,4'-亞異丙基雙(2,6-二甲苯酚)、4,4'-亞異丙基雙(2-甲苯酚)、4,4'-亞異丙基雙(2-烯丙苯酚)(4,4'-isopropylidenebis (2-allylphenol))、4,4'(1,3-伸苯基二亞異丙基)-雙酚、4,4'-亞異丙基雙(3-苯基苯酚)、4,4'-(1,4-伸苯基二亞異丙基)-雙酚、4,4'-亞乙基二酚、4,4'氧二酚、4,4'硫二酚、4,4'硫雙(2,6-二甲苯酚)、4,4'-磺醯基二酚、4,4'-磺醯基雙(2,6-二甲苯酚)、4,4'-亞磺醯基二酚、4,4'-六氟亞異丙基)雙酚、4,4'(1-苯基亞乙基)-雙酚、雙(4-羥基苯基)-2,2-二氯乙烯、雙(4-羥基苯基)-甲烷、雙(2,6-二甲基-4-羥基苯基)甲烷、4,4'-(亞環戊基)二酚、4,4'-(亞環己基)二酚、4,4'-(亞環十二基)二酚、4,4'-(雙環[2.2.1]亞庚基)-二酚、4,4'-(9H-茀-9,9-二基)二酚、3,3-雙(4-羥基苯基)異苯并呋喃-1(3H)-酮、1-(4-羥基苯基)-3,3-二甲基-2,3-二氫-1H-茚-5-醇、1-(4-羥基-3,5-二甲基苯基)-1,3,3,4,6-五甲基-2,3-二氫-1H-茚-5-醇、3,3,3',3'-四甲基-2,2',3,3'-四氫-1,1'-螺二[茚]-5,6'-二醇(螺二二氫茚(Spirobiindane))、二羥基二苯基酮、參(4-羥基苯基)甲烷、參(4-羥基苯基)乙烷、參(4-羥基苯基)丙烷、參(4-羥基苯基)丁烷、參(3-甲基-4-羥基苯基)甲烷、參(3,5-二甲基-4-羥基苯基)甲烷、肆(4-羥基苯基)乙烷、肆(3,5-二甲基-4-羥基苯基)乙烷、雙(4-羥基苯基)-苯膦氧化物、二環戊二烯基雙(2,6-二甲苯酚)(dicyclopentadienylbis(2,6-dimethyl phenol))、二環戊二烯基雙(2-甲苯酚)(dicyclopentadienyl bis(2-methylphenol))、二環戊二烯基雙酚(dicyclopentadienyl bisphenol)等。
交聯劑(crosslinking agent),其亦包含輔助交聯劑(auxiliary crosslinking agent),並無特別限制。交聯劑可單獨使用或以二或更多不同交聯劑組合使用。例示性交聯劑及輔助交聯劑包含具有可固化乙烯系官能基(curable vinyl functionality)之寡聚物或聚合物。此等材料包含具有可交聯不飽和(crosslinkable unsaturation)之寡聚物及聚合物。實例包含苯乙烯丁二烯橡膠(styrene butadiene rubber)(SBR)、丁二烯橡膠(butadiene rubber) (BR)、及具有基於丁二烯之不飽和鍵結(unsaturated bonding)的腈丁二烯橡膠(nitrile butadiene rubber)(NBR);天然橡膠(natural rubber)(NR)、異戊二烯橡膠(isoprene rubber)(IR)、氯丁二烯橡膠(chloroprene rubber)(CR)、丁基橡膠(butyl rubber)(IIR)、及具有基於異戊二烯之不飽和鍵結(unsaturated bonding based on isoprene)的鹵化丁基橡膠(halogenated butyl rubber);具有基於二環戊二烯(dicyclopentadiene)(DCPD)、亞乙基降莰烯(ethylidene norbornene)(ENB)、或1,4-二己二烯(1,4-dihexadiene)(1,4-HD)之不飽和鍵結的乙烯-α-烯烴共聚物彈性體(ethylene-α-olefin copolymer elastomers)(例如,藉由共聚(copolymerizing)乙烯(ethylene)、α-烯烴(α-olefin)、及二烯(diene)所獲得之乙烯-α-烯烴共聚物(ethylene-α-olefin copolymers),諸如乙烯-丙烯-二烯三聚物(ethylene-propylene-diene terpolymer)(EPDM)及乙烯-丁烯-二烯三聚物(ethylene-butene-diene terpolymer)(EBDM))。實例亦包含氫化腈橡膠(hydrogenated nitrile rubber)、氟碳橡膠(fluorocarbon rubbers)(諸如偏二氟乙烯-六氟丙烯共聚物(vinylidenefluoride-hexafluoropropene copolymer)及偏二氟乙烯-五氟丙烯共聚物(vinylidenefluoride-pentafluoropropene copolymer))、表氯醇同元聚合物(epichlorohydrin homopolymer)(CO)、由表氯醇(epichlorohydrin)與環氧乙烷(ethylene oxide)所製備之共聚物橡膠(copolymer rubber) (ECO)、表氯醇烯丙基環氧丙基共聚物(epichlorohydrin allyl glycidyl copolymer)、環氧丙烷烯丙基環氧丙基醚共聚物(propylene oxide allyl glycidyl ether copolymer)、環氧丙烷表氯醇烯丙基環氧丙基醚三聚物(propylene oxide epichlorohydrin allyl glycidyl ether terpolymer)、丙烯酸系橡膠(acrylic rubber)(ACM)、胺甲酸乙酯橡膠(urethane rubber)(U)、聚矽氧橡膠(silicone rubber)(Q)、氯磺化聚乙烯橡膠(chlorosulfonated polyethylene rubber)(CSM)、多硫橡膠(polysulfide rubber)(T)及乙烯丙烯酸系橡膠(ethylene acrylic rubber)。其他實例包含各種液態橡膠(liquid rubbers),例如數種液態丁二烯橡膠(liquid butadiene rubbers),以及係藉由陰離子活性聚合(anionic living polymerization)所製備之具有1,2-乙烯基連接(1,2-vinyl connection)的丁二烯聚合物(butadiene polymer)之液態雜排丁二烯橡膠(liquid atactic butadiene rubber)。亦可使用液態苯乙烯丁二烯橡膠(liquid styrene butadiene rubber)、液態腈丁二烯橡膠(liquid nitrile butadiene rubber)(CTBN、VTBN、ATBN等,Ube Industries, Ltd.)、液態氯丁二烯橡膠(liquid chloroprene rubber)、液態聚異戊二烯(liquid polyisoprene)、二環戊二烯型烴聚合物(dicyclopentadiene type hydrocarbon polymer)、以及聚降莰烯(polynorbornene) (例如,由Elf Atochem所售)。
含有增量1,2加成(1,2 addition)之聚丁二烯樹脂(polybutadiene resins)為熱固性基材(thermosetting matrices)所希望的。實例包含官能化聚丁二烯(functionalized polybutadienes)及聚(丁二烯-苯乙烯)隨機共聚物(poly(butadiene-styrene) random copolymers),由Ricon Resins, Inc.所售,商品名為RICON樹脂、RICACRYL樹脂、及RICOBOND樹脂。此等包括含有低乙烯基含量(vinyl content)之丁二烯(butadienes),諸如RICON 130、131、134、142;含有高乙烯基含量之聚丁二烯(polybutadienes),諸如RICON 150、152、153、154、156、157、及P30D;苯乙烯與丁二烯之隨機共聚物(random copolymers),包含RICON 100、181、184;以及順丁烯二酸酐接枝之聚丁二烯(maleic anhydride grafted polybutadienes)及由彼衍生之醇縮合物(alcohol condensates),諸如RICON 130MA8、RICON MA13、RICON 130MA20、RICON 131MAS、RICON 131MA10、RICON MA17、RICON MA20、RICON 184MA6及RICON 156MA17。亦包含可用以改善黏著(adhesion)之聚丁二烯,包含RICOBOND 1031、RICOBOND 1731、RICOBOND 2031、RICACRYL 3500、RICOBOND 1756、RICACRYL 3500;聚丁二烯RICON 104 (於庚烷中,25%聚丁二烯)、RICON 257 (於苯乙烯中,35%聚丁二烯)、及RICON 257 (於苯乙烯中,35%聚丁二烯);(甲基)丙烯酸官能化聚丁二烯((meth)acrylic functionalized polybutadienes),諸如聚丁二烯二丙烯酸酯(polybutadiene diacrylates)及聚丁二烯二甲基丙烯酸酯(polybutadiene dimethacrylates)。此等材料係以商品名RICACRYL 3100、RICACRYL 3500、及RICACRYL 3801銷售。亦包含官能聚丁二烯衍生物(functional polybutadiene derivatives)之粉末分散液(powder dispersions),例如RICON 150D、152D、153D、154D、P30D、RICOBOND 0 1731 HS、及RICOBOND 1756HS。另外的丁二烯樹脂包含聚(丁二烯-異戊二烯)(poly(butadiene-isoprene))嵌段共聚物及隨機共聚物,諸如分子量為3,000至50,000 g/mol者,以及分子量為3,000至50,000 g/mol之聚丁二烯同元聚合物。亦包含以順丁烯二酸酐官能(maleic anhydride functions)、2-羥乙基順丁烯二酸官能(2-hydroxyethylmaleic functions)、或羥化官能基(hydroxylated functionality)官能化(functionalize)之聚丁二烯、聚異戊二烯、及聚丁二烯-異戊二烯共聚物。
具有可固化乙烯系官能基(curable vinyl functionality)之寡聚物及聚合物的其他實例包含以順丁烯二酸酐(maleic anhydride)、反丁烯二酸(fumaric acid)、伊康酸(itaconic acid)及檸康酸(citraconic acid)為主之不飽和聚酯樹脂(unsaturated polyester resins);含有丙烯醯基(acryloyl groups)、或甲基丙烯醯基(methacryloyl group)之不飽和環氧基(甲基)丙烯酸酯樹脂(unsaturated epoxy (meth)acrylate resins);含有乙烯基或烯丙基之不飽和環氧樹脂(unsaturated epoxy resins)、胺甲酸乙酯(甲基)丙烯酸酯樹脂(urethane (meth)acrylate resin)、聚醚(甲基)丙烯酸酯樹脂(polyether (meth)acrylate resin)、多元醇(甲基)丙烯酸酯樹脂(polyalcohol (meth)acrylate resins)、醇酸丙烯酸酯樹脂(alkyd acrylate resin)、聚酯丙烯酸酯樹脂(polyester acrylate resin)、螺縮醛丙烯酸酯樹脂(spiroacetal acrylate resin)、酞酸二烯丙酯樹脂(diallyl phthalate resin)、四溴酞酸二烯丙酯樹脂(diallyl tetrabromophthalate resin)、二乙二醇二烯丙基碳酸酯樹脂(diethyleneglycol bisallylcarbonate resin)、及聚乙烯聚硫醇樹脂(polyethylene polythiol resins)。例如,交聯劑。其他例示性交聯劑進一步包含多官能交聯單體(polyfunctional crosslinking monomer),諸如每個單體分子具有二或更多個(甲基)丙烯酸酯部分((meth)acrylate moieties)的(甲基)丙烯酸酯單體。例示性多官能單體(polyfunctional monomer)包含二(甲基)丙烯酸酯,諸如1,6-己二醇二(甲基)丙烯酸酯(1,6-hexanediol di(meth)acrylate)、1,4-環己二醇二(甲基)丙烯酸酯(1,4-cyclohexanediol di(meth)acrylate)、三丙二醇二(甲基)丙烯酸酯(tripropylene glycol di(meth)acrylate)、新戊二醇二(甲基)丙烯酸酯(neopentyl glycol di(meth)acrylate)、新戊二醇丙氧基化二(甲基)丙烯酸酯(neopentyl glycol propoxylate di(meth)acrylate)、新戊二醇乙氧基化二(甲基)丙烯酸酯(neopentyl glycol ethoxylate di(meth)acrylate)、新戊二醇丙氧基化二(甲基)丙烯酸酯(neopentyl glycol propoxylate di(meth)acrylate)、新戊二醇乙氧基化二(甲基)丙烯酸酯(neopentyl glycol ethoxylate di(meth)acrylate)、聚乙二醇二(甲基)丙烯酸酯(polyethylene glycol di(meth) acrylate)、甘油二(甲基)丙烯酸酯(glycerol di(meth) acrylate)等;三(甲基)丙烯酸酯,諸如三羥甲基丙烷三(甲基)丙烯酸酯(trimethylolpropane tri(meth)acrylate)、1,2,4-丁三醇三(甲基)丙烯酸酯(1,2,4-butanetriol tri(meth) acrylate)、三羥甲基丙烷乙氧基化三(甲基)丙烯酸酯(trimethylolpropane ethoxylate tri(meth)acrylate)等;三(甲基)烯丙基(tri(meth)allyls),諸如三聚氰酸三(甲基)烯丙酯(tri(meth)allyl cyanurate)、三聚異氰酸三(甲基)烯丙酯(tri(meth)allyl isocyanurate)、檸檬酸之三(甲基)烯丙酯(tri(meth)allyl esters)、磷酸之三(甲基)烯丙酯、新戊四醇三(甲基)丙烯酸酯(pentaerythritol tri(meth)acrylate)、參(羥乙基)三聚異氰酸酯三(甲基)丙烯酸酯(tris(hydroxyethyl)isocyanurate tri(meth)acrylate)等;四(甲基)丙烯酸酯,諸如新戊四醇四(甲基)丙烯酸酯(pentaerythritol tetra(meth)acrylate)等;五(甲基)丙烯酸酯,諸如二新戊四醇五(甲基)丙烯酸酯(dipentaerythritol penta(meth)acrylate)等;六(甲基)丙烯酸酯,諸如二新戊四醇六(甲基)丙烯酸酯(dipentaerythritol hexa(meth) acrylate)、山梨醇六(甲基)丙烯酸酯(sorbitol hexa(meth) acrylate)等;環氧丙基化合物(glycidyl compound),諸如(甲基)丙烯酸環氧丙酯(glycidyl (meth)acrylate)、(甲基)烯丙基環氧丙基醚((meth)allyl glycidyl ether)、1-氯-2,3-環氧基丙基(甲基)丙烯酸酯(1-chloro-2,3-epoxypropyl (meth)acrylate)、2-溴-3,4-環氧基丁基(甲基)丙烯酸酯(2-bromo-3,4-epoxybutyl (meth)acrylate)、2-(環氧基乙基氧基)-乙基(甲基)丙烯酸酯(2-(epoxyethyloxy)-ethyl (meth)acrylate)、2-(3,4-環氧基丁基氧基)-乙基(甲基)丙烯酸酯(2-(3,4-epoxybutyloxy)-ethyl (meth)acrylate)等;聚硫醇化合物(polythiol compound),諸如三羥甲基丙烷參(巰基丙酸酯) (trimethylolpropane tris(mercaptopropionate))、新戊四醇肆(3-巰基丙酸酯)(pentaerythritol tetrakis(3-mercaptopropionate))等;矽烷(silanes),諸如四甲氧基矽烷(tetramethoxysilane)、四乙氧基矽烷(tetraethoxysilane)、四丙氧基矽烷(tetrapropoxysilane)、四正丁氧基矽烷(tetra-n-butoxysilane)、乙烯基參(甲基乙基羥亞胺基)矽烷(vinyltris(methylethyloximino)silane)、乙烯基參-(丙酮肟)矽烷(vinyltris-(acetoxime)silane)、甲基參(甲基乙基羥亞胺基)矽烷(methyltris(methylethyloximino)silane)、甲基參(丙酮肟)矽烷(methyltris(acetoxime)silane)、乙烯基三甲氧基矽烷(vinyltrimethoxysilane)、甲基三甲氧基矽烷(methyltrimethoxysilane)、乙烯基參(異丙烯氧基)矽烷(vinyltris(isopropenoxy)silane)、四乙醯氧基-矽烷(tetraacetoxy- silane)、甲基三乙醯氧基矽烷(methyltriacetoxysilane)、乙基三乙醯氧基矽烷(ethyltriacetoxysilane)、乙烯基三乙醯氧基矽烷(vinyltriacetoxysilane)、二-三級丁氧基二乙醯氧基矽烷(di-t-butoxy-diacetoxysilane)、甲基參(乙基乳酸)矽烷(methyltris(ethyl lactate)silane)、乙烯基參(乙基乳酸)矽烷(vinyltris(ethyl lactate)silane)等;碳二亞胺(carbodiimides),諸如N-(3-二甲基胺基丙基)-N'-乙基碳二亞胺鹽酸鹽(N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride)、二環己基碳二亞胺(dicyclohexylcarbodiimide)等;或其組合。可固化熱固性組成物可視需要地(optionally)包含交聯觸媒(crosslinking catalyst),諸如羧酸鹽。
當可固化熱固性組成物包含交聯劑(crosslinking agent)時,以可固化熱固性組成物之總重為基準計,交聯劑之含量可為1至60 wt%、或5至45 wt%、或10至30 wt%。
可固化熱固性組成物可包含一或多種固化劑(curing agent)。如本文所使用,術語「固化劑」包含不同地描述為固化劑、硬化劑(hardener)等或二者之化合物。
例示性固化劑及硬化劑包含胺(amines)、醇(alcohols)、酚(phenols)、羧酸(carboxylic acids)、酸酐(anhydrides)等。例如,酚系硬化劑(phenolic hardener)包含酚醛型酚樹脂(novolac type phenol resins)、可溶酚醛樹脂型酚樹脂(resole type phenol resins)、甲酚酚醛樹脂(cresol novolac resins)、芳烷基型酚樹脂(aralkyl type phenol resins)、酚芳烷基樹脂(phenol aralkyl resins)、甲酚芳烷基樹脂(cresol aralkyl resins)、萘酚芳烷基樹脂(naphthol aralkyl resins)、二環戊二烯型酚樹脂(dicyclopentadiene type phenol resins)、萜改質之酚樹脂(terpene modified phenol resins)、聯苯型酚樹脂(biphenyl type phenol resins)、聯苯改質之酚芳烷基樹脂(biphenyl-modified phenol aralkyl resins)、雙酚(bisphenols)、三苯甲烷型酚樹脂(triphenylmethane type phenol resins)、四苯氧基乙烷樹脂(tetraphenylol ethane resins)、萘酚酚醛樹脂(naphthol novolac resins)、萘酚-苯酚共縮合酚醛樹脂(naphthol-phenol co-condensed novolac resins)、萘酚-甲酚共縮合酚醛樹脂(naphthol-cresol co-condensed novolac resins)、胺基三𠯤改質之酚樹脂(amino triazine modified phenol resins)、或其組合。酐硬化劑(anhydride hardener)之實例包含甲基六氫酞酸酐(methylhexahydrophthalic anhydride) (MHHPA)、甲基四氫酞酸酐(methyltetrahydrophthalic anhydride)、苯乙烯-順丁烯二酸酐共聚物(styrene-maleic anhydride copolymers)(SMA)、以及烯烴-順丁烯二酸酐共聚物(olefin-maleic anhydride copolymers)諸如順丁烯二酸酐接枝之聚乙烯(maleic anhydride grafted polyethylene)、順丁烯二酸酐接枝之聚丙烯(maleic anhydride grafted polypropylene)、或其組合。其他固化劑及硬化劑包含諸如二氰二胺(dicyandiamides)、聚醯胺(polyamides)、醯胺基胺(amidoamines)、酚胺基胺(phenalkamines)、曼尼希鹼(Mannich bases)、酐(anhydrides)、酚-甲醛樹脂(phenol-formaldehyde resins)、胺-甲醛樹脂(amine-formaldehyde resins)、酚-甲醛樹脂(phenol-formaldehyde resins)、羧酸官能基聚酯(carboxylic acid functional polyesters)、多硫化物(polysulfides)、聚硫醇(polymercaptans)、異氰酸酯(isocyanates)、氰酸酯化合物(cyanate ester compounds)、或其任何組合之化合物。其他例示性固化劑包含三級胺(tertiary amines)、路易斯酸(Lewis acids)、及具有不飽和(unsaturation)之寡聚物或聚合物。
當可固化熱固性組成物包含固化劑時,以可固化熱固性組成物之總重為基準計,固化劑之含量可為0.01至50 wt%、或0.1至30 wt%、或0.1至20 wt%。
可固化熱固性組成物可包含固化觸媒。如本文所使用,術語「固化觸媒(curing catalyst)」包含不同地描述為固化加速劑(curing accelerator)、固化促進劑(curing promoter)、固化觸媒、及固化輔觸媒(curing co-catalyst)之化合物。
例示性固化加速劑包含雜環加速劑(heterocyclic accelerator),諸如包含1至4個環雜原子之經取代或未經取代之C
3-6雜環,其中各雜原子獨立地相同或不同,且為氮、氧、磷、矽、或硫。雜環加速劑包含苯并三唑(benzotriazoles);三𠯤(triazines);哌𠯤(piperazines),諸如胺基乙基哌𠯤(aminoethylpiperazine)、N-(3-胺基丙基)哌𠯤(N-(3-aminopropyl)piperazine)等;咪唑,諸如1-甲基咪唑(1-methylimidazole)、2-甲基咪唑、3-甲基咪唑、4-甲基咪唑、5-甲基咪唑、1-乙基咪唑、2-乙基咪唑、3-乙基咪唑、4-乙基咪唑、5-乙基咪唑、1-正丙基咪唑、2-正丙基咪唑、1-異丙基咪唑、2-異丙基咪唑、1-正丁基咪唑、2-正丁基咪唑、1-異丁基咪唑、2-異丁基咪唑、2-十一基-1H-咪唑(2-undecyl-1H-imidazole)、2-十七基-1H-咪唑(2-heptadecyl-1H-imidazole)、1,2-二甲基咪唑(1,2-dimethylimidazole)、1,3-二甲基咪唑、2,4-二甲基咪唑、2-乙基-4-甲基咪唑、1-苯基咪唑、2-苯基-1H-咪唑、4-甲基-2-苯基-1H-咪唑、2-苯基-4-甲基咪唑、1-苄基-2-甲基咪唑(1-benzyl-2-methylimidazole)、1-苄基-2-苯基咪唑、1-氰基乙基-2-甲基咪唑(1-cyanoethyl-2-methylimidazole)、1-氰基乙基-2-乙基-4-甲基咪唑、1-氰基乙基-2-十一基咪唑(1-cyanoethyl-2-undecylimidazole)、1-氰基乙基-2-苯基咪唑、2-苯基-4,5-二羥基甲基咪唑(2-phenyl-4,5-dihydroxymethylimidazole)、2-苯基-4-甲基-5-羥基甲基咪唑(2-phenyl-4-methyl-5-hydroxymethylimidazole)、1-氰基乙基-2-苯基-4,5-二(2-氰基乙氧基)甲基咪唑(1-cyanoethyl-2-phenyl-4,5-di(2-cyanoethoxy)methylimidazole);環脒(cyclic amidine),諸如4-二氮雜雙環(2,2,2)辛烷(4-diazabicyclo (2,2,2)octane)、二氮雜雙環十一烯(diazabicycloundecene)、2-苯基咪唑啉(2-phenyl imidazoline)等;N,N-二甲基胺基吡啶(N,N-dimethylaminopyridine);磺胺內酯(sulfamidate);或其組合。
胺固化加速劑(amine curing accelerator)包含異佛酮二胺(isophoronediamine)、三伸乙四胺(triethylenetetraamine)、二伸乙三胺(diethylenetriamine)、1,2-二胺基丙烷及1,3-二胺基丙烷(1,3‑diaminopropane)、2,2-二甲基丙二胺(2,2-dimethylpropylenediamine)、1,4-二胺基丁烷、1,6-二胺基己烷、1,7-二胺基庚烷、1,8-二胺基辛烷、1,9-二胺基壬烷、1,12-二胺基十二烷(1,12‑diaminododecane)、4-氮雜七亞甲基二胺(4-azaheptamethylenediamine)、N,N'-雙(3-胺基丙基)丁烷-1,4-二胺(N,N'‑bis(3‑aminopropyl)butane‑1,4-diamine)、二氰胺(dicyanamide)、二醯胺二苯基甲烷(diamide diphenylmethane)、二醯胺二苯基磺酸(diamide diphenylsulfonic acid)(胺加成物(amine adduct))、4,4'-亞甲基二苯胺(4,4'‑methylenedianiline)、二乙基甲苯二胺(diethyltoluenediamine)、間苯二胺(m-phenylenediamine)、對苯二胺(p-phenylenediamine)、三聚氰胺甲醛樹脂(melamine formaldehyde resins)、脲甲醛樹脂(urea formaldehyde resins)、四伸乙五胺(tetraethylenepentamine)、3-二乙基胺基丙胺(3-diethylaminopropylamine)、3,3'-亞胺基雙丙胺(3,3'-iminobispropylamine)、2,4-雙(對胺基苄基)苯胺(2,4-bis(p-aminobenzyl)aniline)、四伸乙五胺(tetraethylenepentamine)、3-二乙基胺基丙胺(3-diethylaminopropylamine)、2,2,4-三甲基六亞甲基二胺及2,4,4-三甲基六亞甲基二胺(2,4,4-trimethylhexamethylenediamine)、1,2-二胺基環己烷及1,3-二胺基環己烷、1,4-二胺基-3,6-二乙基環己烷、1,2-二胺基-4-乙基環己烷、1,4-二胺基-3,6-二乙基環己烷、1-環己基-3,4-二亞胺基環己烷(1-cyclohexyl-3,4-diminocyclohexane)、4,4'-二胺基二環己基甲烷、4,4'-二胺基二環己基丙烷、2,2-雙(4-胺基環己基)丙烷、3,3'-二甲基-4,4'-二胺基二環己基甲烷、3-胺基-1-環己烷胺基丙烷(3-amino-1-cyclohexaneaminopropane)、1,3-雙(胺基甲基)環己烷及1,4-雙(胺基甲基)環己烷(1,4-bis(aminomethyl) cyclohexane)、間二甲苯二胺(m-xylylenediamine)及對二甲苯二胺(p-xylylenediamine)、或二乙基甲苯二胺(diethyl toluene diamines);或三級胺硬化加速劑(tertiary amine hardening accelerator),諸如三乙胺(triethylamine)、三丁胺(tributylamine)、二甲基苯胺(dimethylaniline)、二乙基苯胺(diethylaniline)、苄基二甲胺(benzyldimethylamine) (BDMA)、α-甲基苄基二甲胺(α-methylbenzyldimethylamine)、N,N-二甲基胺基吡啶(N,N-dimethyl amino pyridine)、N,N-二甲基胺基乙醇(
N,N-dimethylaminoethanol)、N,N-二甲基胺基甲酚(
N,N‑dimethylaminocresol)、或三(N,N-二甲基胺基甲基)酚(tri(
N,N-dimethylaminomethyl)phenol);或其組合。
固化加速劑可為潛在陽離子固化觸媒(latent cationic cure catalyst),包含例如,二芳基錪鹽(diaryliodonium salts)、膦酸酯、磺酸酯、羧酸酯、膦酸偶極體(phosphonic ylides)、三芳基鋶鹽(triarylsulfonium salts)、苄基鋶鹽(benzylsulfonium salts)、芳基重氮鹽(aryldiazonium salts)、苄基吡啶鎓鹽(benzylpyridinium salts)、苄基銨鹽(benzylammonium salts)、異㗁唑鎓鹽(isoxazolium salts)等、或其組合。二芳基錪鹽可具有結構[(R
10)(R
11)I]
+X
-,其中R
10及R
11各自獨立地為C
6-14一價芳族烴基(C
6-14monovalent aromatic hydrocarbon radical),視需要地(optionally)經1至4個選自C
1-20烷基、C
1-20烷氧基、硝基、及氯基之一價基(monovalent radical)取代;以及其中X-為陰離子。另外的固化加速劑可具有結構[(R
10)(R
11)I]
+SbF
6 -,其中R
10及R
11各自獨立地為C
6-14一價芳族烴,視需要地經1至4個C
1-20烷基、C
1-20烷氧基、硝基、或氯基取代;例如,4-辛基氧基苯基苯基錪六氟銻酸鹽(4-octyloxyphenyl phenyl iodonium hexafluoroantimonate)。
固化加速劑可為金屬鹽錯合物(metal salt complex),諸如脂族或芳族羧酸之銅(II)、鋁(III)、鋅、鈷、錫鹽,選自乙酸、硬脂酸、葡萄糖酸、檸檬酸、苯甲酸之銅(II)、錫(II)、及鋁(III)鹽,及其混合物。例如,固化加速劑可為銅(II)或鋁(III)之β-二酮鹽(β-diketonates);銅(II)、鐵(II)、鐵(III)、鈷(II)、鈷(III)、或鋁(III)的乙醯丙酮鹽(acetylacetonates);鋅(II)、鉻(II)、或錳(II)之辛酸鹽(octoates);或其組合。
當可固化熱固性組成物包含固化觸媒時,以可固化熱固性組成物之總重為基準計,固化觸媒之含量可為0.01至5 wt%、或0.05至5 wt%、或0.1至5 wt%。
可固化熱固性組成物可視需要地包含固化引發劑(curing initiator),諸如過氧化物化合物(peroxide compound)。例示性過氧化物固化引發劑可包含過氧化苯甲醯(benzoyl peroxide)、過氧化二異丙苯(dicumyl peroxide)、甲基乙基酮(methyl ethyl ketone peroxide)過氧化物、過氧化月桂基(lauryl peroxide)、過氧化環己酮(cyclohexanone peroxide)、氫過氧化三級丁基(t-butyl hydroperoxide)、氫過氧化三級丁基苯(t-butyl benzene hydroperoxide)、過氧辛酸三級丁酯(t-butyl peroctoate)、三級丁基過氧基苯甲酸酯(t-butylperoxybenzoate)、三級丁基過氧基2-乙基己基碳酸酯(t-butylperoxy 2-ethylhexyl carbonate)、過氧化2,4-二氯苯甲醯基(2,4-dichlorobenzoyl peroxide)、2,5-二甲基己烷-2,5-二氫過氧化物(2,5-dimethylhexane-2,5-dihydroperoxide)、丁基-4,4-雙(三級丁基二氧基)戊酸酯(butyl-4,4-bis(tert-butyldioxy)valerate)、2,5-二甲基-2,5-二(三級丁基過氧基)-己-3-炔(2,5-dimethyl-2,5-di(t-butylperoxy)-hex-3-yne)、過氧化二-三級丁基(di-t-butylperoxide)、過氧化三級丁基異丙苯(t-butylcumyl peroxide)、α,α'-雙(三級丁基過氧基-間異丙基)苯(α,α′-bis(t-butylperoxy-m-isopropyl)benzene)、2,5-二甲基-2,5-二(三級丁基過氧基)己烷(2,5-dimethyl-2,5-di(t-butylperoxy) hexane)、過氧化二異丙苯(dicumylperoxide)、過氧異酞酸二(三級丁基酯(di(t-butylperoxy isophthalate)、過氧苯甲酸三級丁基酯(t-butylperoxybenzoate)、2,2-雙(三級丁基過氧基)丁烷(2,2-bis(t-butylperoxy)butane)、2,2-雙(三級丁基過氧基)辛烷(2,2-bis(t-butylperoxy)octane)、2,5-二甲基-2,5-二(苯甲醯基過氧基)己烷(2,5-dimethyl-2,5-di(benzoylperoxy)hexane)、1,1-二-(三級丁基過氧基)-3,3,5-三甲基環己烷(1,1-di-(tert-butylperoxy)-3,3,5-trimethylcyclohexane)、過氧化二(三甲基矽基)(di (trimethylsilyl)peroxide)、過氧化三甲基矽基苯基三苯基矽基(trimethylsilylphenyltriphenylsilyl peroxide)等、或其組合。
當可固化熱固性組成物包含固化引發劑時,以可固化熱固性組成物之總重為基準計,固化引發劑之含量可為0.1至5 wt%、或0.5至5 wt%、或1至5 wt%。
阻燃劑(flame retardant)包含例如包含磷、溴、或氯之有機化合物。基於監管因素,非溴化(non-brominated)及非氯化(non-chlorinated)含磷阻燃劑在某些應用中會較佳,例如有機磷酸酯(organic phosphates)及含磷-氮鍵之有機化合物。
磷阻燃劑(phosphorous flame retardant)之實例包含磷酸酯(phosphates)、磷腈(phosphazenes)、亞磷酸酯(phosphite esters)、膦(phosphines)、膦酸鹽(phosphinates)、多磷酸鹽(polyphosphates)及鏻鹽(phosphonium salts)。磷酸酯包含磷酸三苯酯(triphenyl phosphate)、磷酸三甲苯酯(tricresyl phosphate)、異丙基化磷酸三苯酯(isopropylated triphenyl phosphate)、磷酸苯基雙(十二基)酯(phenyl bis(dodecyl) phosphate)、磷酸苯基雙(新戊基)酯(phenyl bis(neopentyl) phosphate)、磷酸苯基雙(3,5,5'-三甲基己基)酯(phenyl bis(3,5,5'-trimethylhexyl) phosphate)、磷酸乙基二苯酯(ethyl diphenyl phosphate)、磷酸2-乙基己基二(對甲苯基)酯(2-ethylhexyl di(p-tolyl) phosphate)、磷酸雙(2-乙基己基)對甲苯酯(bis(2-ethylhexyl) p-tolyl phosphate)、磷酸三甲苯酯(tritolyl phosphate)、磷酸雙(2-乙基己基)苯酯(bis(2-ethylhexyl) phenyl phosphate)、磷酸三(壬基苯基)酯(tri(nonylphenyl) phosphate)、磷酸雙(十二基)對甲苯酯(bis(dodecyl) p-tolyl phosphate)、磷酸二丁基苯酯(dibutyl phenyl phosphate)、磷酸2-氯乙基二苯酯(2-chloroethyl diphenyl phosphate)、磷酸對甲苯基雙(2,5,5'-三甲基己基)酯(p-tolyl bis(2,5,5'-trimethylhexyl) phosphate)、磷酸2-乙基己基二苯酯(2-ethylhexyl diphenyl phosphate)、磷酸二甲苯基-二苯酯(xylenyl-diphenyl phosphate);磷酸甲苯基-二苯酯(cresyl-diphenyl phosphate);1,3-伸苯基雙(二-2,6-二甲苯磷酸酯)(1,3-phenylenebis(di-2,6-xylenyl phosphate));9,10-二氫-9-氧雜-10-磷雜菲-10-氧化物(9,10-dihydro-9-oxa-10-phosphaphenanthrene-10-oxide)(DOPO)、二磷酸四苯酯(tetraphenyl diphosphate)(RDP)、縮合磷酸酯化合物(condensed phosphate compounds),諸如芳族縮合磷酸酯化合物(aromatic condensed phosphate compounds);以及環磷酸酯化合物(cyclic phosphate compounds)、氫醌之磷酸雙(二苯基)酯(bis(diphenyl) phosphate of hydroquinone)、雙酚A之磷酸雙(二苯基)酯(bis(diphenyl) phosphate of bisphenol A)等、或其寡聚或聚合之對應體(counterpart)、或其組合。
磷腈化合物(phosphazene compounds)之實例包含環狀磷腈化合物(cyclic phosphazene compounds)及鏈磷腈化合物(chain phosphazene compounds)。環狀磷腈化合物(環磷腈(cyclophosphazenes))具有其中磷-氮雙鍵存在於分子中之環狀結構。膦酸鹽化合物(phosphinate compounds)之實例包含二烷基膦酸鋁(aluminum dialkylphosphinate)、參-(二乙基膦酸)鋁(aluminum tris-(diethylphosphinate))、參-(甲基乙基膦酸)鋁(aluminum tris-(methylethylphosphinate))、參-(二苯基膦酸)鋁(aluminum tris-(diphenylphosphinate))、雙-(二乙基膦酸)鋅(zinc bis-(diethylphosphinate))、雙-(甲基膦酸)鋅(zinc bis-(methylphosphinate))、雙-(二苯基膦酸)鋅(zinc bis-(diphenylphosphinate))、雙-(二乙基膦酸)氧鈦酯(titanyl bis-(diethylphosphinate))、雙-(甲基乙基膦酸)氧鈦酯(titanyl bis-(methylethylphosphinate))、及雙-(二苯基膦酸)氧鈦酯(titanyl bis-(diphenylphosphinate))。多磷酸鹽化合物(polyphosphate compounds)之實例包含多磷酸三聚氰胺(melamine polyphosphate)、多磷酸蜜白胺(melam polyphosphate)、及多磷酸蜜勒胺(melem polyphosphate)。鏻鹽化合物之實例包含四苯基硼四苯基鏻(tetraphenylphosphonium tetraphenylborate)。亞磷酸酯化合物之實例包含亞磷酸三甲酯(trimethylphosphite)及亞磷酸三乙酯(triethylphosphite)。含磷-氮鍵之阻燃劑化合物包含氯化磷腈(phosphonitrilic chloride)、磷酯醯胺(phosphorus ester amides)、磷酸醯胺(phosphoric acid amides)、膦酸醯胺(phosphonic acid amides)、膦酸醯胺(phosphinic acid amides)、及氧化參(氮基)膦(tris (aziridinyl) phosphine oxide)。
亦可使用鹵化材料(halogenated material)作為阻燃劑,例如雙酚(bisphenols),諸如2,2-雙-(3,5-二氯苯基)-丙烷(2,2-bis-(3,5-dichlorophenyl)-propane);雙-(2-氯苯基)-甲烷(bis-(2-chlorophenyl)-methane);雙(2,6-二溴苯基)-甲烷(bis(2,6-dibromophenyl)-methane);1,1-雙-(4-碘苯基)-乙烷(1,1-bis-(4-iodophenyl)-ethane);1,2-雙-(2,6-二氯苯基)-乙烷(1,2-bis-(2,6-dichlorophenyl)-ethane);1,1-雙-(2-氯-4-碘苯基)乙烷(1,1-bis-(2-chloro-4-iodophenyl) ethane);1,1-雙-(2-氯-4-甲基苯基)-乙烷(1,1-bis-(2-chloro-4-methylphenyl)-ethane);1,1-雙-(3,5-二氯苯基)-乙烷(1,1-bis-(3,5-dichlorophenyl)-ethane);2,2-雙-(3-苯基-4-溴苯基)-乙烷(2,2-bis-(3-phenyl-4-bromophenyl)-ethane);2,6-雙-(4,6-二氯萘基)-丙烷(2,6-bis-(4,6-dichloronaphthyl)-propane);以及2,2-雙-(3,5-二氯-4-羥基苯基)-丙烷(2,2-bis-(3,5-dichloro-4-hydroxyphenyl)-propane) 2,2 雙-(3-溴-4-羥基苯基)-丙烷(2,2 bis-(3-bromo-4-hydroxyphenyl)-propane)。其他鹵化材料包含1,3-二氯苯(1,3-dichlorobenzene)、1,4-二溴苯(1,4-dibromobenzene)、1,3-二氯-4-羥苯(1,3-dichloro-4-hydroxybenzene)、及聯苯(biphenyls)諸如2,2'-二氯聯苯(2,2'-dichlorobiphenyl)、多溴1,4-二苯氧基苯(polybrominated 1,4-diphenoxybenzene)、2,4'-二溴聯苯(2,4'-dibromobiphenyl)、及2,4'-二氯聯苯(2,4'-dichlorobiphenyl),以及十溴二苯基醚(decabromobiphenyl ether)、十溴二苯乙烷(decabromodiphenylethane),以及寡聚(oligomeric)及聚合(polymeric)鹵化芳族化合物(halogenated aromatic compounds),諸如溴化苯乙烯(brominated styrene)、4,4-二溴聯苯(4,4-dibromobiphenyl)、乙烯-雙(四溴酞醯亞胺)(ethylene-bis(tetrabromophthalimide))、或雙酚A(bisphenol A)及四溴雙酚A(tetrabromobisphenol A)之共聚碳酸酯(copolycarbonate)及碳酸酯前驅物(carbonate precursor)例如光氣(phosgene)。金屬增效劑(metal synergist)(例如氧化銻)亦可與阻燃劑一同使用。
亦可使用無機阻燃劑,例如C
1-16烷基磺酸鹽之鹽,諸如全氟丁磺酸鉀(potassium perfluorobutane sulfonate)(Rimar鹽(Rimar salt))、全氟辛磺酸鉀(potassium perfluoroctane sulfonate)、全氟己磺酸四乙銨(tetraethylammonium perfluorohexane sulfonate)、及二苯碸磺酸鉀(potassium diphenylsulfone sulfonate);諸如Na
2CO
3、K
2CO
3、MgCO
3、CaCO
3、及BaCO
3之鹽,或諸如Li
3AlF
6、BaSiF
6、KBF
4、K
3AlF
6、KAlF
4、K
2SiF
6、或Na
3AlF
6之氟陰離子錯合物(fluoro-anion complex)。
當可固化熱固性組成物包含阻燃劑時,以可固化熱固性組成物之總重為基準計,阻燃劑之含量可大於1 wt%、或1至20 wt%、或5至20 wt%。
可固化熱固性組成物可進一步包含無機或有機填料,諸如微粒填料(particulate filler)、纖維填料(fibrous filler)等、或其組合。可使用任何無機及有機填料(包含本領域中已知者)而無限制。
例示性填料包含例如黏土、滑石、高嶺土(kaolin)、矽灰石(wollastonite)、雲母(mica)、碳酸鈣、碳酸鎂;氧化鋁(alumina)、硫脲(thiourea)、玻璃粉末、以B或Sn為主之填料諸如硼酸鋅、錫酸鋅(zinc stannate)及羥基錫酸鋅(zinc hydroxystannate);金屬氧化物,諸如氧化鋅及氧化錫、氧化鋁、矽石(silica)(包含熔融矽石(fused silica)、燻製矽石(fumed silica)、球狀矽石(spherical silica)、及晶矽石(crystalline silica))、氮化硼(包含球狀氮化硼(spherical boron nitride))、氮化鋁、氮化矽、氧化鎂(magnesia)、矽酸鎂、三氧化二銻、玻璃纖維(glass fibers)(經切短(chopped)、經碾磨(milled)、或布狀(cloth))、玻璃氈(glass mat)、玻璃泡(glass bubbles)、中空玻璃微球體(hollow glass microspheres)、醯胺纖維(aramid fibers)、石英等、或其組合。其他例示性無機填料包含粉末狀鈦陶瓷(powdered titanium ceramics),諸如鋇、鉛、鍶、鈣、鉍、鎂等之鈦酸鹽中任一者。無機填料亦包含水合物(hydrate),諸如氫氧化鋁、氫氧化鎂、沸石、及水滑石(hydrotalcite)。於一些態樣中,填料可以本文所揭露之偶合劑(coupling agent)處理。
玻璃纖維(glass fiber)包含以E、A、C、ECR、R、S、D、及NE玻璃為主者,以及石英。玻璃纖維可具有任何適合的直徑,諸如2至30微米(μm)、或5至25 μm、或5至15 μm。配料混合(compounding)之前的玻璃纖維之長度無限制,以及可為2至7毫米(mm)、或1.5至5 mm。或者,可使用較長玻璃纖維或連續玻璃纖維。適合的玻璃纖維可由諸如Owens Corning、Nippon Electric Glass、PPG、及Johns Manville等供應商購得。
有機填料可為例如聚四氟乙烯(polytetrafluoroethylene)粉末、聚苯硫醚(polyphenylene sulfide)粉末、及聚(醚碸)( poly(ether sulfone))粉末、聚(苯醚)(poly(phenylene ether))粉末、聚苯乙烯、二乙烯苯樹脂(divinylbenzene resin)等、或其組合。
填料可根據熱膨脹係數(thermal expansion coefficient)(CTE)及熱傳導率(thermal conductivity)要求來選擇。例如,Al
2O
3、BN、AlN、或其組合可用於具有高熱傳導率之電子設備模組(electronics module)。例如,MgO可用於提高之熱傳導率及提高之CTE。例如,SiO
2(例如,非晶形(amorphous)SiO
2)可用於具有低CTE及小介電常數(dielectric constant)之輕量模組(lightweight module)。
當可固化熱固性組成物包含填料時,以可固化熱固性組成物之總重為基準計,填料之含量可大於1 wt%、或1至50 wt%、或1至30 wt%、或10至30 wt%。
偶合劑(coupling agent)(亦稱為黏著促進劑(adhesion promoter))包含鉻錯合物(chromium complex)、矽烷、鈦酸鹽(titanates)、鋯鋁酸鹽(zircon-aluminates)、烯烴-順丁烯二酸酐共聚物(olefin-maleic anhydride copolymers)、反應性纖維素酯(reactive cellulose esters)等。例示性烯烴-順丁烯二酸酐共聚物可包含順丁烯二酸酐接枝之聚乙烯(maleic anhydride grafted polyethylene)、順丁烯二酸酐接枝之聚丙烯(maleic anhydride grafted polypropylene)、或其組合。例示性矽烷可包含環氧基矽烷化合物(epoxysilane compound)、胺基矽烷化合物(aminosilane compounds)、甲基丙烯醯氧基矽烷化合物(methacryloxysilane compounds)、乙烯基矽烷化合物(vinylsilane compounds)、或其組合。
胺基矽烷偶合劑(aminosilane coupling agent)之實例為γ-胺基丙基三甲氧基矽烷(γ-aminopropyltrimethoxy-silane)、γ-胺基丙基三乙氧基矽烷(γ-
aminopropyltriethoxysilane)、N-β(胺基乙基) γ-胺基丙基甲基-二甲氧基矽烷(N-beta(aminoethyl) γ-
aminopropylmethyl-dimethoxysilane)、N-β(胺基乙基) γ-胺基丙基三甲氧基矽烷(N-beta(aminoethyl) γ-
aminopropyltrimethoxysilane)、及N-β(胺基乙基)γ-胺基丙基三乙氧基矽烷(N-beta(aminoethyl) γ-
aminopropyltriethoxysilane)。例示性環氧基矽烷偶合劑(epoxysilane coupling agent)包含γ-環氧丙氧基丙基甲基二乙氧基矽烷(γ -glycidoxypropylmethyldiethoxysilane)、γ-環氧丙氧基丙基三甲氧基矽烷(gamma-
glycidoxypropyltrimethoxysilane)、及γ-環氧丙氧基丙基三乙氧基矽烷(γ-glycidoxypropyltriethoxysilane)。甲基丙烯醯氧基矽烷偶合劑(methacryloxysilane coupling agent)之實例包含γ-甲基丙烯醯氧基丙基甲基二甲氧基矽烷(γ-methacryloxypropylmethyldimethoxysilane)、γ-甲基丙烯醯氧基丙基三甲氧基矽烷(γ-methacryloxypropyl-trimethoxysilane)、γ-甲基丙烯醯氧基丙基二乙氧基矽烷(γ-methacryloxypropyldiethoxysilane)、及γ-甲基丙烯醯氧基丙基三乙氧基矽烷(γ-
methacryloxypropyltriethoxysilane)。
其他例示性矽烷偶合劑包含雙(3-三乙氧基矽基丙基)四硫化物(bis(3-triethoxysilylpropyl) tetrasulfide)、雙(3-三乙氧基矽基丙基)三硫化物(bis(3-triethoxysilylpropyl) trisulfide)、雙(3-三乙氧基矽基丙基)二硫化物(bis(3-triethoxysilylpropyl) disulfide)、雙(2-三乙氧基矽基乙基)四硫化物(bis(2-triethoxysilylethyl) tetrasulfide)、雙(3-三甲氧基矽基丙基)四硫化物(bis(3-trimethoxysilylpropyl) tetrasulfide)、雙(2-三甲氧基矽基乙基)四硫化物(bis(2-trimethoxysilylethyl) tetrasulfide)、3-巰基丙基三甲氧基矽烷(3-mercaptopropyltrimethoxysilane)、3-巰基丙基三乙氧基矽烷(3-mercaptopropyltriethoxysilane)、2-巰基乙基三甲氧基矽烷(2-
mercaptoethyltrimethoxysilane)、2-巰基乙基三乙氧基矽烷(2-mercaptoethyltri-ethoxysilane)、3-三甲氧基矽基丙基-N,N-二甲基胺硫甲醯基四硫化物(3-trimethoxysilylpropyl-N,N-dimethylthiocarbamoyl tetrasulfide)、3-三乙氧基矽基丙基-N,N-二甲基胺硫甲醯基四硫化物(3-
triethoxysilylpropyl-N,N-dimethylthiocarbamoyl tetrasulfide)、2-三乙氧基矽基乙基-N,N-二甲基胺硫甲醯基四硫化物(2-triethoxysilylethyl-N,N-
dimethylthiocarbamoyl tetrasulfide)、3-三甲氧基矽基丙基苯并噻唑基四硫化物(3-
trimethoxysilylpropylbenzothiazolyl tetrasulfide)、3-三乙氧基矽基丙基苯甲醯基四硫化物(3-
triethoxysilylpropylbenzolyl tetrasulfide)、3-三乙氧基矽基丙基甲基丙烯酸酯一硫化物(3-triethoxysilylpropyl methacrylate monosulfide)、3-三甲氧基矽基丙基甲基丙烯酸酯一硫化物(3-trimethoxysilylpropyl methacrylate monosulfide)、雙(3-二乙氧基甲基矽基丙基)四硫化物(bis(3-diethoxymethylsilylpropyl) tetrasulfide)、3-巰基丙基二甲氧基甲基矽烷(3-
mercaptopropyldimethoxymethylsilane)、二甲氧基甲基矽基丙基-N,N-二甲基胺硫甲醯基四硫化物(dimethoxymethylsilylpropyl-N,N-dimethylthio-carbamoyl tetrasulfide)、二甲氧基甲基矽基丙基苯并噻唑基四硫化物(dimethoxymethylsilylpropylbenzothiazolyl tetrasulfide)等、或其組合。矽烷偶合劑可為具有2至4個形成多硫化物橋(polysulfide bridge)之硫原子的多硫矽烷偶合劑(polysulfide silane coupling agent)。例如,偶合劑可為雙(3-三乙氧基矽基丙基)二硫化物、雙(3-三乙氧基矽基丙基)三硫化物、或雙(3-三乙氧基矽基丙基)四硫化物(bis(3-triethoxysilylpropyl) tetrasulfide)。
當可固化熱固性組成物包含偶合劑時,以可固化熱固性組成物之總重為基準計,偶合劑之含量可為0.01至5 wt%、或0.05至5 wt%、或0.1至5 wt%。
可固化熱固性組成物可視需要地包含溶劑。溶劑可為例如C
3-8酮、C
3-8N,N-二烷基醯胺(C
3-8 N,N‑dialkylamide)、C
4-16二烷基醚、C
6-12芳族烴、C
1-3氯化烴(C
1-3chlorinated hydrocarbon)、烷酸C
3-6烷酯(C
3-6alkyl alkanoate)、C
2-6烷基氰化物(C
2-6alkyl cyanide)、或其組合。具體酮溶劑包含例如,丙酮、甲基乙基酮、甲基異丁基酮、或其組合。具體C
4-8N,N-二烷基醯胺溶劑包含例如,二甲基甲醯胺(dimethylformamide)、二甲基乙醯胺(dimethylacetamide)、N-甲基-2-吡咯啶酮(
N-methyl-2-pyrrolidone)、或其組合。具體二烷基醚溶劑包含例如,四氫呋喃、乙二醇一甲醚(ethylene glycol monomethylether)、二㗁烷(dioxane)、或其組合。具體芳族烴溶劑包含例如,苯、甲苯、二甲苯、苯乙烯、二乙烯苯(divinylbenzenes)、或其組合。芳族烴溶劑可未經鹵化。具體烷酸C
3-6烷酯包含例如,乙酸甲酯、乙酸乙酯、丙酸甲酯、丙酸乙酯、或其組合。具體C
2-6烷基氰化物包含例如,乙腈、丙腈、丁腈、或其組合。具體C
2-6烷基氰化物包含例如,乙腈、丙腈、丁腈、或其組合。例如,溶劑可為N,N-二甲基甲醯胺(N,N-dimethylformamide)、N,N-二甲基乙醯胺(N,N-dimethylacetamide)、N,N-二乙基乙醯胺(N,N-diethylacetamide)、N,N-二甲基甲氧基乙醯胺(N,N-dimethylmethoxyacetamide)、N-甲基-2-吡咯啶酮(N-methyl-2-pyrrolidone)、N-環己基吡咯啶酮(N-cyclohexylpyrrolidinone)、N-甲基己內醯胺(N-methylcaprolactam)、1,3-二甲基-2-四氫咪唑酮(1,3-dimethyl-2-imidazolidone)、1,2-二甲氧基乙烷、1,3-二㗁烷(1,3-dioxane)、1,4-二㗁烷(1,4-dioxane)、四氫呋喃、γ-丁內酯(γ-butyrolactone)、γ-己內酯(γ-caprolactone)、二甲亞碸(dimethylsulfoxide)、二苯基酮(benzophenone)、甲基乙基酮、甲基異丁基酮、環己酮(cyclohexanone)、二甘二甲醚(diglyme)、三甘二甲醚(triglyme)、四甘二甲醚(tetraglyme)、N,N-二甲基伸乙脲(N,N-dimethylethyleneurea)、N,N-二甲基伸丙脲(N,N-dimethylpropyleneurea)、四甲脲(tetramethylurea)、丙二醇苯基醚(propylene glycol phenyl ether)、甲基苯基醚(anisole)、藜蘆醚(veratrole)、鄰二氯苯(o-dichlorobenzene)、氯苯(chlorobenzene)、三氯乙烷(trichloroethane)、二氯甲烷(methylene chloride)、氯仿、吡啶、甲吡啶(picoline)、乳酸乙酯、乙酸正丁酯、丁賽路蘇乙酸酯(butyl cellosolve acetate)、丁基卡必醇乙酸酯(butyl carbitol acetate)、乙賽路蘇乙酸酯(ethyl cellosolve acetate)、乙基卡必醇乙酸酯(ethyl carbitol acetate)、碳酸丙二酯(propylene carbonate)、環丁碸(sulfolane)、離子液體(ionic liquid)、或其組合。
使用溶劑時,以可固化熱固性組成物之總重為基準計,可固化熱固性組成物可包含2至99 wt%之溶劑。例如,以可固化熱固性組成物之總重為基準計,溶劑量可為5至80 wt%、或10至60 wt%、或20至50 wt%。溶劑可部分經選擇以調整可固化熱固性組成物之黏度。因此,溶劑量可視包含下列之變數而定:封端聚(芳醚)共聚物(capped poly(arylene ether) copolymer)之類型及量、其他組分(諸如固化添加劑)之類型及量、任何輔助熱固性樹脂(auxiliary thermosetting resin)之類型及量、以及用於可固化熱固性組成物之任何後續處理(例如以可固化熱固性組成物浸漬(impregnation)強化結構(reinforcing structure)以製備複材)之處理溫度。溶劑可為無水的(anhydrous)。例如,以溶劑之總重為基準計,溶劑可包含少於每百萬分之100份(ppm)、或少於50 ppm、或少於10 ppm之水。
可固化熱固性組成物可進一步包含可固化不飽和單體組成物(curable unsaturated monomer composition),其可包含例如單官能苯乙烯系化合物(monofunctional styrenic compound)(例如,苯乙烯)、單官能(甲基)丙烯酸系化合物(monofunctional (meth)acrylic compound)等、或其組合。例如,可固化不飽和單體組成物可為含烯單體或含炔單體。例示性含烯(alkene)單體及含炔(alkyne)單體包含描述於頒予Yeager等人之美國專利6,627,704號中所述者,以及包含如Heilman等人之美國專利4,304,705號中所揭露之(甲基)丙烯酸酯、(甲基)丙烯醯胺((meth)acrylamides)、N-乙烯基吡咯啶酮(N-
vinylpyrrolidone)、及乙烯基氮代內酯(vinylazalactones)。例示性單官能單體包含一(甲基)丙烯酸酯,諸如(甲基)丙烯酸甲酯、(甲基)丙烯酸乙酯、(甲基)丙烯酸異丙酯、(甲基)丙烯酸異辛酯、(甲基)丙烯酸異莰酯(isobornyl (meth)acrylate)、(甲基)丙烯酸、(甲基)丙烯酸正己酯、(甲基)丙烯酸四氫呋喃甲酯(tetrahydrofurfuryl (meth)acrylate)、N-乙烯基己內醯胺(N-
vinylcaprolactam)、N-乙烯基吡咯啶酮、(甲基)丙烯腈((meth)acrylonitrile)等、或其組合。
可固化熱固性組成物可視需要地進一步包含一或多種額外的添加劑。額外的添加劑包含例如染料(dye)、顏料(pigment)、著色劑(colorant)、抗氧化劑(antioxidant)、熱安定劑(heat stabilizer)、光安定劑(light stabilizer)、塑化劑(plasticizer)、消泡劑(defoaming agent)、潤滑劑(lubricant)、分散劑(dispersant)、調流劑(flow modifier)、阻滴劑(drip retardant)、抗結塊劑(antiblocking agent)、抗靜電劑(antistatic agent)、流動促進劑(flow‑promoting agent)、加工助劑(processing aid)、基板黏著劑(substrate adhesion agent)、脫模劑(mold release agent)、韌化劑(toughening agent)、低外形添加劑(low-profile additive)、應力釋放添加劑(stress-relief additive)等、或其組合。存在額外的添加劑時,可包含任何有效量之額外的添加劑,例如,以可固化熱固性組成物之總重為基準計為0.01至20 wt%、或0.01至10 wt%、或0.01至5 wt%、或0.01至1 wt%之量。
可固化熱固性組成物可使用任何適合的方法,藉由結合雙官能苯醚寡聚物(bifunctional phenylene ether oligomer)與本文所揭露之其他視需要的組分(optional component)而製備。
還提供包含可固化熱固性組成物的固化產物的固化之熱固性組成物。對於可藉以固化可固化熱固性組成物之方法無特別限制。可固化組成物可例如熱固化(cured thermally)或藉由使用輻射技術(irradiation technique)(包括UV照射或電子束照射(electron beam irradiation))固化。例如,固化產物可藉由加熱本文所定義之可固化熱固性組成物達足以蒸發溶劑及有效固化之時間及溫度而獲得。使用熱固化時,溫度可為30至400℃、或50至250℃、或100至250℃。加熱可為1分鐘至24小時、或1分鐘至6小時、或3小時至5小時。固化可分階段以製造部分固化且經常無黏性(tack-free)之樹脂,然後藉由加熱較長期間或在上述範圍內之溫度使其完全固化。如本文所使用,術語「固化(cured)」包含部分固化或完全固化。
固化之熱固性組成物可具有一或多種希望的性質。例如,熱固性組成物可具有大於或等於165℃、較佳係大於或等於170℃、更佳係165至180℃之玻璃轉移溫度(glass transition temperature)。熱固性組成物亦可有利地展現低介電常數(dielectric constant)(Dk)、低耗散因子(dissipation factor)(Df)、及降低之吸濕性(moisture absorption)。例如,熱固性組成物於10 GHz之頻率可具有低於3.0、較佳係低於2.75、更佳係低於2.6之介電常數。熱固性組成物於10 GHz之頻率可具有低於0.01、或低於0.005之耗散因子。因此,包含本揭露內容之苯醚寡聚物的熱固性組成物可特別適用於電子設備應用。
可固化熱固性組成物及固化之熱固性組成物可用於各種應用及用途,包含使用慣用熱固性組成物之任何應用。例如,包含可固化熱固性組成物或固化之熱固性組成物的可用物件可呈複材(composite)、發泡體(foam)、纖維、層、塗層(coating)、封裝劑(encapsulant)、黏著劑(adhesive)、密封劑(sealant)、模製組件(molded component)、預浸材(prepreg)、護罩(casing)、層合物(laminate)、覆金屬層合物(metal clad laminate)、電子複材(electronic composite)、結構複材(structural composite)、或其組合之形式。例示性用途及應用包含塗層,諸如保護性塗層(protective coating)、密封劑、耐候性塗層(weather resistant coating)、抗刮塗層(scratch resistant coating)、及電絕緣塗層(electrical insulative coating);黏著劑;黏合劑(binder);膠(glue);複材料(composite material),諸如使用碳纖維及玻璃纖維(fiberglass)強化體(reinforcement)者。使用作為塗層時,所揭露之化合物及組成物可沉積於各種下層基板之表面上。例如,組成物可沉積於金屬、塑膠、玻璃、纖維上漿(fiber sizings)、陶瓷(ceramics)、石材(stone)、木材、或其任何組合之表面上。所揭露之組成物可用作金屬容器(例如鋁或鋼)之表面上的塗層,諸如常用於塗料及表面覆蓋產業之封裝(packaging)及圍阻(containment)者。可固化熱固性組成物及由彼衍生的固化之熱固性組成物亦可特別適用於形成電氣組件及電腦組件。
形成複材之方法可包含以可固化熱固性組成物浸漬(impregnating)強化結構(reinforcing structure);部分固化(partially curing)可固化熱固性組成物以形成預浸材(prepreg);以及層合(laminating)多個預浸材。強化結構可為多孔基底材料(porous base material),諸如纖維預製件(fibrous preform)或基板,或包含陶瓷、聚合物、玻璃、碳或其組合之其他多孔材料。例如,多孔基底材料可為編織(woven)或不織(non-woven)玻璃織物(glass fabric)、玻璃纖維織物(fiberglass fabric)、或碳纖維。當物件包含纖維預製件時,製造物件之方法可包含藉由以可固化組成物塗布(coating)或浸漬(impregnating)預製件(preform)而由可固化熱固性組成物形成物件(article)。浸漬之纖維預製件(impregnated fibrous preform)可視需要地在去除溶劑之前或之後成形(shaped)。於一些態樣中,可固化熱固性組成物層可進一步包含編織或不織的玻璃織物。例如,可固化層可藉由以可固化組成物浸漬玻璃織物且從經浸漬之玻璃織物去除溶劑而製備。例示性強化結構係描述於例如匿名(Anonymous)(Hexcel Corporation),"Prepreg Technology", March 2005, Publication No. FGU 017b;匿名(Hexcel Corporation),"Advanced Fibre Reinforced Matrix Products for Direct Processes", June 2005, Publication No. ITA 272;以及Bob Griffiths, "Farnborough Airshow Report 2006", CompositesWorld.com, September 2006。強化結構之重量及厚度係使用熟習纖維強化之樹脂複材之製造的人士熟知之標準,根據複材之預期用途選擇。強化結構可含有適合可固化熱固性組成物之熱固性組分的各種最後加工(finishes)。
由可固化熱固性組成物製造物件之方法可包含部分固化可固化熱固性組成物以形成預浸材,或完全固化可固化熱固性組成物以形成複材物件。此處提及之「固化之組成物」的性質係指實質上完全固化之組成物。例如,由預浸材所形成之層合物中的樹脂通常實質上完全固化。熟習熱固物領域之人士不需要過度實驗即可決定樣本係部分固化或實質上完全固化。固化可在從可固化組成物去除溶劑之前或之後進行。此外,物件可在去除溶劑之前或去除溶劑之後、固化之前、部分固化之後、或完全固化之後,例如藉由熱成形(thermoforming)而進一步成形(shaped)。於一態樣中,形成物件,且去除溶劑;物件係經部分固化(B階段化(B-staged));視需要地成形(optionally shaped);然後進一步固化。
形成複材之商業規模方法(commercial-scale method)於本領域中已知,以及本文中描述之可固化熱固性組成物易適應現有製程及設備。例如,預浸材經常於處理器(treater)上製造。處理器之主要組件包含進料器滾筒(feeder roller)、樹脂浸漬槽(resin impregnation tank)、處理器烘箱(treater oven)、及接收器滾筒(receiver roller)。強化結構(例如E玻璃)經常滾軋(roll)成大型捲軸(spool)。然後,將捲軸置於進料器滾筒上,進料器滾筒轉動且緩慢展開(roll out)強化結構。然後,強化結構移動通過含有可固化熱固性組成物之樹脂浸漬槽。可固化組成物浸漬強化結構。於從槽(tank)浮現(emerging)之後,經塗布之強化結構向上移動通過通常為175至200℃之溫度的垂直處理器烘箱(vertical treater oven),以及使溶劑蒸發。此時樹脂開始聚合。當複材(composite)從塔(tower)出來時,其充分固化因此幅材(web)不潮濕(wet)或膠黏(tacky)。然而,固化程序在未達完成就停止,因此於製造層合物時會發生額外固化。然後幅材將預浸材滾軋(roll)於接收器滾筒上。
還提供包含或衍生自可固化熱固性組成物之電氣及電子物件。物件包括包含醫療或航太產業中所使用之印刷電路的物件。又另外的物件包括天線(antennae)及類似物件。諸如印刷電路板之物件係用於例如照明、太陽能、顯示器、照相機、影音設備(audio and video equipment)、個人電腦、行動電話、電子記事本(electronic notepad)、以及類似裝置,或辦公室自動化設備(office automation equipment)。例如,電氣部件可安裝於包含層合物之印刷電路板。由可固化組成物所製備之用於各種不同應用的其他例示性物件可包含覆銅層合物(copper clad laminate)(CCL),例如金屬核心之覆銅層合物(metal core copper clad laminate)(MCCCL)、複材物件(composite article)、及經塗布物件(coated article),例如多層物件。
介電層可由可固化熱固性組成物製備,其可用於電路裝配件(circuit assembly),例如用於覆金屬層合物(metal-clad laminate),諸如覆銅層合物。例如,層合物可包含介電層(dielectric layer)、配置於介電層上之傳導性金屬電路層(conductive metal circuit layer),以及視需要的,配置於介電層上(傳導性金屬層之相對側)之散熱金屬基質層(heat dissipating metal matrix layer)。介電層可視需要的包含纖維預製件(例如,織物層(fabric layer))。例如,介電層可進一步包含玻璃織物層(glass fabric layer)。
傳導性金屬層(conductive metal layer)可呈電路(circuit)形式,以及可為銅、鋅、錫、黃銅、鉻、鉬、鎳、鈷、鋁、不鏽鋼、鐵、金、銀、鉑、鈦等、或其組合。其他金屬包含銅鉬合金、鎳-鈷鐵合金(諸如KOVAR,得自Carpenter Technology Corporation)、鎳-鐵合金(諸如INVAR,得自National Electronic Alloys, Inc.)、雙金屬(bimetal)、三金屬(trimetal)、衍生自兩層銅及一層INVAR之三金屬、以及衍生自兩層銅及一層鉬之三金屬。例示性金屬層包含銅或銅合金。或者,可使用鍛軋銅箔(wrought copper foil)。傳導性金屬層可具有2至200微米(μm)、或5至50 μm、或5至40 μm之厚度。
散熱金屬基質層(heat dissipating metal matrix layer)可為熱傳導性金屬,諸如鋁、氮化硼、氮化鋁、銅、鐵、鋼等、或其組合。可使用熱傳導性、導電金屬,其條件係該金屬與金屬電路層電隔離(electrically isolated)。較佳之支撐金屬基質層(supporting metal matrix layer)可具有0.1至20毫米(mm)、或0.5至10 mm、或0.8至2 mm之厚度。
傳導性金屬層及支撐金屬基質層(supporting metal matrix layer)可經預處理以具有高表面粗糙度(surface roughness)以增強對介電層之黏著。處理方法包含洗滌(washing)、火焰處理(flame treatment)、電漿放電(plasma discharge)、電暈放電(corona discharge)等,例如以增強金屬層之黏著。介電層在不使用黏著劑的情況下可牢固地黏附至傳導性金屬層或散熱層,或可使用黏著劑以改善介電層對傳導性金屬層或散熱層之黏著。用以黏合複材薄片與金屬之例示性黏著劑包含聚醯亞胺黏著劑(polyimide adhesives)、丙烯酸系黏著劑(acrylic adhesives)、環氧樹脂(epoxies)等、或其組合。
覆銅層合物(copper clad laminate)可在不使用熱固性黏著劑的情況下藉由在壓力下熱層合一或多個介電層、一或多個傳導性金屬層、及支撐金屬基質層而製造。介電層可由可固化熱固性組成物製備,以及可在熱層合(thermal lamination)步驟之前藉由溶劑鑄造製程(solvent casting process)製備以形成層。例如,介電層、傳導性金屬層、及散熱層可藉由無黏著劑製程(adhesive-free process)在壓力下熱層合(thermally laminate)在一起以形成層合物。導電金屬層在層合之前可視需要地呈電路形式,或傳導性金屬層在層合之後可視需要地經蝕刻(etch)以形成電路。層合(laminating)可藉由熱壓(hot press)或輥軋(roll calendaring)法,例如捲至捲法(roll-to-roll method)進行。覆銅層合物(copper clad laminate)中之傳導性金屬層可進一步圖案化(pattern)以提供印刷電路板(printed circuit board)。此外,覆銅層合物可成形(shaped)以提供具有薄片(sheet)、管(tube)、或棒(rod)形之電路板。
或者,用於電路裝配件(circuit assembly)之層合物可藉由將可固化熱固性組成物直接鑄(cast)於導電金屬層上之溶液鑄造法(solution casting method)、然後藉由層合至散熱金屬基質層而製造。例如,可固化熱固性組成物可直接鑄於散熱金屬基質層上,然後層合至導電金屬層。
包含額外層之多層層合物(multilayer laminate)亦可藉由如熱壓或輥軋法之製程以一步驟或以二或更多連續步驟藉熱層合(thermal lamination)製造。例如,層合物中可存在七層或更少層、或六層或更少層。於一態樣中,層合物可以一步驟或以二或更多連續步驟以織物(fabric)-熱固物(thermoset)-金屬-熱固物-織物-熱固物-金屬箔(metal foil)之連續層或具有較少層之其子組合(sub-combination)形成,以使層合物包含在任一層金屬箔及任一層織物之間的熱固物膜(thermoset film)層。於另一態樣中,第一層合物可以一步驟或以二或更多連續步驟以在兩層熱固物之間有一層織物而形成,諸如在兩層熱固物之間有一層編織玻璃織物(woven glass fabric)。第二層合物然後可藉由將金屬箔(metal foil)層合至第一層合物之熱固物側(thermoset side)而製備。
由可固化熱固性組成物所製備之印刷電路板可具有0.1至20 mm、具體而言為0.5至10 mm之整體厚度,其中,整體厚度(overall thickness)係指包含介電層、導電金屬層、及支撐金屬基質層各者之層的裝配件。電路裝配件可具有0.5至2 mm、具體而言為0.5至1.5之整體厚度。介電層之厚度無特別限制,以及可為5至1500 μm、或5至750μm、或10至150μm、或10至100μm。例如,印刷電路板可為用於發光二極體(LED)應用之金屬核心印刷電路板(metal core printed circuit board)(MCPCB)。
可固化熱固性組成物可呈塗層(coating)使用,例如用於製備多層物件。製造塗層之方法可包含結合可固化熱固性組成物及視需要的氟聚合物(fluoropolymer)以及於基板上形成塗層。例如,多層物件可藉由下述方法製造:形成包含可固化熱固性組成物之層、由該層去除溶劑以及視需要地固化以提供底層(primer layer)、在底層上形成包含陶瓷(例如,Al
2O
3、TiO
2、ZrO
2、Cr
2O
3、SiO
2、MgO、BeO、Y
2O
3、Al
2O
3-SiO
2、MgO-ZrO
2、SiC、WC、B
4C、TiC、Si
3N
4、TiN、BN、AlN、TiB、ZrB
2等)、熱塑性聚合物、氟聚合物(例如,聚四氟乙烯、四氟乙烯-全氟烷基乙烯醚共聚物(tetrafluoroethylene-perfluoroalkylvinylether copolymers)、四氟乙烯-六氟丙烯共聚物、聚氯三氟乙烯(polychlorotrifluoroethylene)、四氟乙烯-乙烯共聚物(tetrafluoroethylene-ethylene copolymers)、聚偏二氟乙烯(polyvinylidene fluoride)等)、或其組合之第二層以提供多層物件,以及視需要地熱處理多層物件以固化可固化熱固性組成物。於一些態樣中,第二層可進一步包含可固化熱固性組成物。
可固化熱固性組成物之另外的應用包含例如,酸浴容器(acid bath container);中和槽(neutralization tank);航空器組件(aircraft component);橋樑(bridge beam);橋面(bridge decking);電解槽(electrolytic cell);排氣管(exhaust stack);洗滌器(scrubber);運動設備;樓梯(stair case);走道(walkway);汽車外板(automobile exterior panel),諸如引擎蓋(hood)及行李箱蓋(trunk lid);車身底板(floor pan);進氣口(air scoop);管(pipe)及導管(duct),包含加熱器導管(heater duct);工業扇(industrial fan)、風罩(fan housing)、及鼓風機(blower);工業混合機(industrial mixer);船體(boat hull)及甲板(deck);船舶護舷材(marine terminal fender);瓷磚(tile)及塗層(coating);建築板(building panel);商用機殼(business machine housing);托盤(tray),包含電纜托盤(cable tray);混凝土改質劑(concrete modifier);洗碗機及冷凍機(refrigerator)零件;電氣封裝(electrical encapsulant);電氣面板(electrical panel);槽,包含電解精煉槽(electrorefining tank)、水軟化劑槽(water softener tank)、燃料槽(fuel tank)、及各種纏絲槽(filament-wound tank)及槽襯料(tank lining);家具;車庫門;格柵(grating);防護裝備(protective body gear);行李箱(luggage);戶外機動車輛(outdoor motor vehicle);壓力槽(pressure tank);光學波導(optical waveguide);天線罩(radome);欄杆(railing);鐵道部件(railroad part),諸如槽車(tank car);斗車蓋(hopper car cover);車門;卡車襯料(truck bed liner);衛星接收碟(satellite dish);招牌(sign);太陽能板(solar energy panel);電話開關設備外罩(telephone switchgear housing);曳引機部件(tractor part);變壓器外罩(transformer cover);卡車部件,諸如檔板(fender)、引擎蓋(hood)、車身(body)、駕駛室(cab)、及車斗(bed);旋轉機器(rotating machine)之絕緣(insulation),包含接地絕緣(ground insulation)、匝間絕緣(turn insulation)、及相分離絕緣(phase separation insulation);換向器(commutator);鐵心絕緣(core insulation)以及繩(cord)和編織帶(lacing tape);驅動軸聯結器(drive shaft coupling);槳葉(propeller blade);飛彈組件(missile component);火箭引擎外殼(rocket motor case);翼剖面(wing section);抽油桿(sucker rod);機身剖面(fuselage section);機翼(wing)蒙皮(skin)及擴口(flaring);引擎機艙(engine narcelles);貨艙門(cargo door);網球拍;高爾夫球桿桿身(golf club shaft);釣竿(fishing rod);滑雪板(skis)和滑雪杖(ski pole);腳踏車部件;橫向片彈簧(transverse leaf spring);泵,諸如汽車煙霧泵(automotive smog pump);電氣組件(electrical component)、嵌埋(embedding)、及工具(tooling),諸如電氣電纜接頭(electrical cable joint);繞線(wire winding)及密集封裝多組件裝配件(densely packed multi-element assemblies);電化學裝置(electromechanical device)之密封(sealing);電池外殼(battery case);電阻器(resistor);保險絲(fuse)及熱斷路裝置(thermal cut-off device);印刷線路板(printed wiring board)之塗層(coating);鑄件(casting item),諸如電容器(capacitor)、變壓器(transformer)、曲軸箱加熱器(crankcase heater);小型模製電子部件(small molded electronic part),包含線圈(coil)、電容器、電阻器(resistor)、及半導體;作為化學處理(chemical processing)中之鋼、紙漿(pulp)及紙、發電(power generation)、及廢水處理(wastewater treatment)的替代品(replacement);洗滌塔(scrubbing tower);用於結構應用(structural application)之拉擠成型部件(pultruded part),包含結構構件(structural member)、格柵(grating)、及安全欄杆(safety rail);游泳池、游泳池滑道(swimming pool slide)、熱水池(hot-tub)、及三溫暖(sauna);用於引擎蓋應用(hood application)下方之驅動軸(drive shaft);影印機之乾碳粉樹脂(dry toner resin);船用工具(tooling)及複材(composite);遮熱板(heat shield);潛艇殼體(submarine hull);原型生成(prototype generation);實驗模型(experimental model)之開發(development);層合修整(laminated trim);鑽探設備(drilling fixture);黏合夾具(bonding jig);檢驗設備(inspection fixture);工業金屬成型模(industrial metal forming die);航空器(aircraft)拉伸模(stretch block)及錘模型(hammer form);真空模製工具(vacuum molding tool);地板(flooring),包含製造及裝配區、無塵室(clean room)、機工間(machine shop)、控制室(control room)、實驗室(laboratories)、停車庫(parking garage)、冷凍庫(freezer)、冷卻器(cooler)、及戶外卸貨平台(outdoor loading dock)之地板;抗靜電應用(antistatic application)之導電組成物(electrically conductive composition);用於裝飾性地板(decorative flooring);橋樑之伸縮接頭(expansion joint);用於結構混凝土(structural concrete)中之裂縫(crack)的補綴(patch)及修補(repair)之可注射砂漿(injectable mortar);用於磚瓦之灌漿(grouting for tile);機械軌道(machinery rail);金屬合釘(metal dowel);螺栓(bolt)及支柱(post);油及燃料儲槽之修補,以及眾多其他應用。
可用於製備物件及材料之方法包含熱固性樹脂之加工領域中通常已知者。此等方法已描述於文獻,例如Engineered Materials Handbook, Volume 1, Composites, ASM International Metals Park, Ohio, copyright 1987 Cyril A. Dostal Senior Ed, pp. 105-168 and 497-533,以及"Polyesters and Their Applications" by Bjorksten Research Laboratories, Johan Bjorksten (pres.) Henry Tovey (Ch. Lit. Ass.), Betty Harker (Ad. Ass.), James Henning (Ad. Ass.), Reinhold Publishing Corporation, New York, 1956。加工技術(processing techniques)包含樹脂轉注成形(resin transfer molding);片狀成形(sheet molding);塊狀成形(bulk molding);拉擠成形(pultrusion);射出成形(injection molding),包含反應射出成形(reaction injection molding)(RIM);大氣壓力成形(atmospheric pressure molding)(APM);鑄造(casting),包含離心(centrifugal)及靜壓(static)鑄造、敞模鑄造(open mold casting);層合(lamination),包含濕式(wet)或乾式(dry)積層(lay up)及噴霧積層(spray lay up);亦包含接觸模製(contact molding),包含圓筒接觸模製(cylindrical contact molding);壓縮模製(compression molding);包含真空輔助樹脂轉注成形(vacuum assisted resin transfer molding)及化學輔助樹脂轉注成形(chemically assisted resin transfer molding);配套工具模製(matched tool molding);熱壓器固化(autoclave curing);於空氣中熱固化;真空裝袋(vacuum bagging);拉擠成形(pultrusion);Seeman複合樹脂灌注製造加工(Seeman's Composite Resin Infusion Manufacturing Processing (SCRIMP));敞開式模製(open molding)、樹脂及玻璃之連續結合(continuous combination);以及纏繞成形(filament winding),包含圓筒纏繞成形(cylindrical filament winding)。例如,物件可藉由樹脂轉注成形法(resin transfer molding process)製備。
還提供衍生自可固化熱固性組成物之物件,其中該物件為複材、發泡體、纖維、層、塗層、封裝劑、黏著劑、密封劑、模製組件、預浸材、護罩、鑄造物件(cast article)、層合物、或其組合;或其中物件為覆金屬層合物(metal clad laminate)、電子複材、結構複材、或其組合。物件可如本文所揭露製造,例如藉由鑄造(casting)、模製(molding)、擠出(extruding)等,以及由所形成之物件去除溶劑。於一些態樣中,物件可為層,以及可藉由將可固化組成物鑄(casting)於基板上以形成鑄造層(cast layer)。溶劑可藉由任何數量之手法去除,包含藉由加熱鑄造層、在熱及壓力之下加熱鑄造層、例如藉由將鑄造層層合至另一基板。於一些態樣中,藉由上述方法所製備之物件可包含黏著劑(adhesive)、封裝材料(packaging material)、電容器膜(capacitor film)、或電路板層(circuit board layer)。於一些態樣中,由可固化組成物所製備之物件可為介電層(dielectric layer),或配置於基板上之塗層,例如電線(wire)或電纜(cable)塗層(coating)。例如,物件可為用於例如照明(lighting)或通訊(communications)應用之電路材料(circuit material)中(例如印刷電路板中)之介電層。由可固化組成物所製備之其他例示性物件可為一或多個印刷層(painted layer)。可固化組成物可用以製備如本文所揭露之其他可固化熱固性組成物的物件。
本揭露內容係以下列非限制性實例進一步闡明。
實施例
用於下列實例之材料描述於表1。
表1
組分 | 說明 | CAS# | 供應商 |
CMP | 2-甲基-6-環己酚 | 4855-68-9 | SI Group |
CP | 2-環己酚 | 119-42-6 | Sigma-Aldrich |
TMBPA | 四甲基雙酚A | 5613-46-7 | Deepak Novachem |
Cu 2O | 氧化銅(I) | 1317-39-1 | American Chemet Corporation |
HBr | 氫溴酸 | 10035-10-6 | Chemtura Corporation |
DBEDA | 二-三級丁基乙二胺 | 4062-60-6 | Achiewell LLC |
DBA | 二正丁胺 | 111-92-2 | Oxea Corporation |
DMBA | N,N-二甲基丁胺 | 927-62-8 | Oxea Corporation |
PTC-1 | 於50 %甲苯中之50 %氯化二癸基二甲基銨(didecyl dimethyl ammonium chloride),為MAQUAT | 7173-51-5 | Mason Chemical Company |
NTA | 氮基三乙酸三鈉鹽(Nitrilotriacetic acid trisodium salt) | 5064-31-3 | Akzo Nobel Functional Chemicals LLC |
DMAP | N,N-二甲基胺基吡啶 | 1122-58-3 | Sigma Aldrich |
MAA | 甲基丙烯酸酐 | 760-93-0 | Alfa Aesar |
MEK | 甲基乙基酮 | 78-93-3 | Fisher Scientific |
甲苯 | - | 108-88-3 | Fisher Scientific |
氯仿 | - | 67-66-3 | Fisher Scientific |
TAIC | 三聚異氰酸三烯丙酯 | 1025-15-6 | Acros Organics |
DTBPIB | 二(三級丁基過氧基異丙基)苯,為Perkodax 14S-FL | 25155-25-3 | Akzo Nobel |
BPBPE | 1,2-雙(2,3,4,5,6-五溴苯基)乙烷,為Saytex 8010 | 84852-53-9 | Albemarle |
矽石 | 球形矽石(Spherical silica) | 631-86-9 | Denka |
TMSPMA | 3-三甲氧基矽基-丙基-甲基丙烯酸酯 | 2530-85-0 | Fisher Scientific |
PPE-2MA | 包含2,6-二甲基-1,4-苯醚(2,6-dimethyl-1,4-phenylene ether)重複單元且具有甲基丙烯酸酯端基之雙官能苯醚寡聚物 | SABIC |
氧化偶合聚合反應(oxidative coupling polymerization reaction)係在鼓泡反應器(bubbling reactor)中進行,為具備頂置式攪拌器(overhead agitator)、熱電偶(thermocouple)、氮墊(nitrogen pad)及用於氧鼓泡(oxygen bubbling)之傾斜管(dip tube)的500 ml夾套玻璃反應器(jacketed glass reactor)。衍生(derivatization)或封端(end capping)反應係於配備有加熱包(heating mantle)、迪安斯達克冷凝器(dean stark condenser)、熱電偶、及額外的漏斗(funnel)之500 ml玻璃反應器中進行。
用於隨後固化之可固化組成物的鑄造(casting)係使用得自Specac之手動液壓機(manual hydraulic press)進行。
PPE-CMP寡聚物係根據下列製程合成。將甲苯(42.45克)、CMP (42.3克)、TMBPA (5.76克)、DMBA (4.32克)、DBA (0.28克)、以及DBEDA (0.075克)、PTC-1 (0.04克)、和甲苯(0.13克)之混合物裝入500 ml鼓泡聚合容器(bubbling polymerization vessel)且在氮之下攪拌。將觸媒溶液(0.02克Cu
2O及0.33克之48% HBr)添加至上述反應混合物。於添加觸媒溶液之後,開始氧流動(oxygen flow)。溫度在15分鐘內從25℃升至32℃,以及於115分鐘時提高至49℃。氧流動維持1500分鐘,於此時停止該流動,以及將0.46克 NTA及5.68克水添加至反應混合物。所得混合物係於60℃攪拌2小時。藉由離心(centrifugation)分離(separate)層,以及藉由去除甲苯而分離(isolate)輕相(light phase)。寡聚物係在氮之下於真空烘箱(vacuum oven)中以110℃乾燥一夜之後獲得。
PPE-CMP-2MA寡聚物係根據下列製程合成。PPE-CMP寡聚物(36克)係於配備有加熱包、迪安斯達克冷凝器、攪拌器及熱電偶之500 ml 3頸圓底燒瓶(3-neck round bottom flas)中溶於甲苯(75克)。將溶液加熱至120℃以藉由共沸蒸餾(azeotropic distillation)去除水。於去除水之後,將反應混合物冷卻至85℃且添加DMAP (0.36克)。於DMAP完全溶解之後,使用加料漏斗(addition funnel)在20分鐘內添加MAA (6.63克)。使反應溫度升高至110℃,以及該反應攪拌4小時。藉由沉澱至甲醇來分離PPE-CMP-2MA。粉末係在真空及氮之下於110℃進一步乾燥一夜。
可固化組成物係藉由將PPE-CMP-2MA溶於氯仿中所製備。在真空及氮之下去除氯仿直到獲得乾燥粉末為止。乾燥粉末用於化學流變學(chemorheology)以及進一步固化以評估性能。固化鑄件(cured casting)係藉由部分固化組成物(例如至膠凝時間(gel time))所製備。將部分固化組成物(partially cured composition)移至40毫米直徑模且將該模置於熱模壓機(hot die press)中。樣本係藉由在壓力(1噸(ton))下將溫度提高至150℃來固化。一旦溫度達到150℃之後,使樣本冷卻至70℃且將模移至烘箱,樣本係在真空下以200℃固化120分鐘。
使用下列測試程序進行組成物之定性(characterize)。
核磁共振(NMR)譜法分析(Nuclear Magnetic Resonance (NMR) Spectroscopy Analysis):藉由NMR分析測定寡聚物之化學結構及組成。所有
1H NMR譜係於Varian Mercury Plus 400儀上以400.14 MHz之觀察頻率(observe frequency)操作獲得。
凝膠滲透層析術(Gel Permeation Chromatography)係相對於聚苯乙烯標準品(polystyrene standard)進行,且用以測定數量平均分子量(number average molecular weight)(Mn)及重量平均分子量(weight average molecular weight)(Mw)。
溶液黏度測量(Solution Viscosity Measurement):使用備配用於低黏度材料之UL轉接器(UL adaptor)的DV2+ pro Brookfield黏度計(DV2+ pro Brookfield viscometer)。使用藉由水套(water jacket)控制之於25℃的轉軸(spindle)00進行測量以測定於MEK中之50 wt.%寡聚物的溶液黏度。
微差掃描熱量法(Differential scanning calorimetry)(DSC):寡聚物之玻璃轉移溫度(Tg)係使用TA Instruments之微差掃描熱量計(differential scanning calorimeter)以20℃/min之溫變(temperature ramp)自25℃至300℃測量。分析係在氮之下進行。所有樣本重量係在8至11毫克之範圍。使用T-zero盤(T-zero pan)。
放熱之熱(heat of exotherm)及固化程度(extent of cure)亦使用DSC,以10℃/min溫變(temperature ramp)從25℃升溫至300℃來測定。所有樣本重量係在8至11毫克之範圍。固化程度係藉由未固化組成物及部分固化(B階段(B-stage))組成物的放熱之熱(heat of exotherm)的比率(ratio)來測定。
膠凝時間(Gel time)係使用得自TA Instruments之Ares G2流變計(Ares G2 Rheometer)在氮氣氛(nitrogen atmosphere)下使用目標間隙(target gap)為1 mm之25 mm平行板(parallel plate)測量。利用振盪溫變(oscillation temperature ramp),起始溫度(starting temperature)為80℃且溫變速率(ramp rate)為5℃/分鐘,以及等應變(constant strain)為30%且角頻率(angular frequency)為10 Rad/s。
黏度測量(Viscosity measurement)(於下列表中稱為「樹脂流動(resin flow)」)係使用得自TA Instruments之Ares G2流變計在氮氣氛下使用目標間隙為1 mm之25 mm平行板進行。利用振盪溫變,起始溫度為80℃且溫變速率為3℃/分鐘,以及等應變為1%且角頻率為10 Rad/s。
進行熱重分析(Thermal gravimetric analysis) (TGA)以定性(characterize)固化樣本(cured sample)之分解。使用10℃/min之溫變速率(temperature ramp rate)從25℃開始且升至800℃。
介電測量(Dielectric measurement)之進行係使用Agilent Technologies E5071C網路分析儀(network analyzer),配備有分離式介質共振器(split post dielectric resonator)(SPDR)設備,用於介電常數(dielectric constant) (Dk)及耗散因子(Df)之測量,於10 GHz。
吸濕性(Moisture absorption)之定性係藉由將鑄件置於50℃之水浴中。從該浴移出樣本、半乾(damp dried)、以及每24小時測量重量。
實施例1
PPE-CMP-2MA係根據上述合成製備。PPE-CMP-2MA之結構係藉由溶液NMR譜法(solution NMR spectroscopy)確認。
1H NMR譜法(
1H NMR spectroscopy)亦確認寡聚物之端基(end group)為甲基丙烯酸酯單元,形成平均官能(average functionality)為2之雙官能寡聚物(bi-functional oligomer)。
表2顯示實施例1之PPE-CMP-2MA寡聚物的一些性質。
表2
性質 | 單位 | 實施例1 |
物理形式 | -- | 粉末 |
平均官能度(Average degree of functionality) | -- | 2 |
Tg | ℃ | 147 |
Mn | g/mol | 2978 |
Mw | g/mol | 4752 |
溶解度,甲苯(環境條件(ambient)) | Wt% | >50 |
溶解度,MEK (環境條件) | Wt% | >50 |
溶液黏度(MEK,25℃,50 rpm) | cP | 60 |
可固化組成物係根據表3製備。調配物之流變(rheological)及固化(curing)表現(behavior)係在溶劑去除之後測量。固化材料(cured material)之性能亦顯示於表3。將包含實施例1之寡聚物的組成物之性能與包含衍生自2,6-二甲苯酚的重複單元之雙官能PPE-甲基丙烯酸酯寡聚物(顯示為比較例1)比較。
表3
表4
組分 | 單位 | 實施例2 | 比較例1 |
PPE-CMP-2MA (得自實施例1) | Wt% | 68 | |
PPE-2MA | Wt% | 68 | |
TAIC | Wt% | 29 | 29 |
DTBPIB | Wt% | 3 | 3 |
性質 | |||
放熱之熱 | J/g | 177 | 204 |
膠凝時間 | 秒 | 800 | 485 |
樹脂流動(於B階段前) | Pa-s | 22.20 ± 0.19 | 273 |
樹脂流動(於B階段後) | Pa-s | 6569 ± 233 | 1566 4 |
固化程度 | % | ||
Tg | ℃ | 197 | 225 |
開始分解溫度(Onset Decomposition Temperature) | ℃ | 455 | 469 |
介電常數 | -- | 2.57±0.0072 | 2.83±0.03 |
耗散因子 x10 3 | -- | 3.58±0.023 | 5.75±0.083 |
平衡吸水性(Equilibrium Water Absorption) | Wt% | 0.54 | 0.79 |
組分 | 單位 | 實施例3 | 比較例1 |
PPE-CMP-2MA (得自實施例1) | Wt% | 49 | |
PPE-2MA | Wt% | 49 | |
TAIC | Wt% | 21 | 21 |
DTBPIB | Wt% | 2 | 2 |
BPBPE | Wt% | 8 | 8 |
矽石 | Wt% | 20 | 20 |
TMSPMA | Wt% | 0.3 | 0.3 |
性質 | |||
放熱之熱 | J/g | 177 | 204 |
膠凝時間 | 秒 | 786 | 446 813 |
樹脂流動(於B階段前) | Pa-s | 17 | 273 |
樹脂流動(於B階段後) | Pa-s | 8185.7 | 1566 4 |
固化程度 | % | 10 | 9.1 |
Tg | ℃ | 198 | 228 |
介電常數 | -- | 2.70±0.021 | 2.83±0.03 |
耗散因子 x10 3 | -- | 3.34±0.0 3 | 5.75±0.083 |
開始分解溫度 | ℃ | 390 | 400 |
平衡吸水性 | Wt% | 0.54 | 0.79 |
如表3所示,PPE-CMP-2MA寡聚物展現介電性能之改善。因此,本文所述之材料視為極適用於電子材料,尤其是用於印刷電路板之預浸材層合物及覆金屬層合物。
比較例2
根據下列製程合成CP-PPE寡聚物以與上述CMP-PPE寡聚物比較。將甲苯(168克)、CP (49克)、TMBPA (6.40克)、DMBA (1.68克)、DBA (0.56克)、以及0.088克DBEDA、0.047克PTC-1、和0.15克甲苯之混合物裝入500毫升鼓泡聚合容器且在氮之下攪拌。將觸媒溶液(0.42克;0.03克 Cu
2O及0.39克 (48%) HBr)添加於上述反應混合物。於添加觸媒溶液之後,開始氧流動。溫度在15分鐘內從25℃升至39.4℃,以及於70分鐘時提高至48.9℃。氧流動維持130分鐘,於此時停止該流動,以及將1.0克 NTA及6.0克水添加至反應混合物。所得混合物係於60℃攪拌2小時。藉由離心分離層,以及藉由沉澱至甲醇而分離輕相。在氮之下於真空烘箱中以110℃乾燥一夜之後過濾及分析沉澱之粒子(precipitated particle)。
CP-PPE寡聚物係藉由
1H及
31P NMR譜法來定性。所有
1H NMR譜係於 Agilent DD2 600儀上以599.90 MHz之觀察頻率(observe frequency)操作獲得。在定量條件(quantitative conditions)下收集所有樣本之譜(spectra)。將大約30 mg 2-環己酚最終ppt樣本(final ppt sample)添加至1毫升1,1,2,2-四氯乙烷-d
2(1,1,2,2-tetrachloroethane-d
2)。譜參數(spectral parameter)包含9615 Hz譜寬(spectral width)、1.7 s獲得時間(acquisition time)(16 K資料點(data point))、4.20 µs脈衝寬度(pulse width)(45°翻轉角度(flip angle))、及15 s脈衝延遲(pulse delay)。使用s2pul脈衝序列(pulse sequence)。通常,32獲得(acquisitions)足以獲致良好訊噪比(signal-to-noise)。資料處理(data processing)係使用NetNMR軟體以0.25 Hz譜線增寬(line broadening)及多項式基線校正常式(polynomial baseline correction routine)來進行。
31P-NMR譜法用來鑑定(identification)及量化(quantification)各種聚合物樣本中之酚官能性(phenolic functionality)。此技術涉及以2-氯-1,3,2-二㗁磷雜環戊烷(2-chloro-1,3,2-dioxaphospholane)衍生(derivatization)聚合物酚殘基(polymer phenolic residue)。此反應產生僅芳族環取代(aromatic ring substitution)不同之各種結構相似的2-芳氧基-1,3,2-二㗁磷雜環戊烷(2-aryloxy-1,3,2-dioxaphospholane)。由於
31P-核(
31P-nucleus)對其電子環境(electronic environment)之敏感度緣故,可由其對應磷酸酯衍生物(corresponding phosphate derivative)之
31P-化學位移(
31P-chemical shift)來識別(identify)各種酚端基(phenolic endgroup)。除了酚端基以外,此方法亦量化許多樹脂中之醇(alcohol)及酸性官能基(acidic functionalities)。透過使用內標準品(internal standard)2,4-二溴酚(2,4-dibromophenol),可測定聚合樹脂(polymeric resin)之羥基端基官能性(hydroxyl end-group functionality)的量化。
所有譜(spectra)係於Agilent DD2 600光譜儀(Agilent DD2 600 spectrometer)上以242.84 MHz針對
31P操作而獲得。該儀器配備有5mm OneNMR™ PFG探針(probe)。將大約80mg之樣本溶於4.0 ml之含有0.95mg/ml 2,4-二溴酚(內標準品)及15mg/ml Cr(acac)
3(用以減少資料獲取時間(data acquisition times)之T1鬆弛增強試劑(T1 relaxation enhancement reagent))的氯仿-d(chloroform-d)。此外,以每100ml CDCl
3內標準品原液(internal standard stock solution)1ml吡啶之量添加吡啶作為酸清除劑(acid scavenger)。記錄樣本及內標準品重量至小數點第4位。於脈衝延遲(pulse delay)期間斷開(gated off)解偶器(decoupler)以消除(eliminate)NOE以及確保掃描(scan)之間的磷核(phosphorus nuclei)完全鬆弛(complete relaxation)。獲得參數(acquisition parameter)包含3s之脈衝延遲及45°翻轉角度。並且,23.6 kHz譜寬(100至200 ppm區)及32 K資料點(data points)形成1.39s獲得時間(acquisition time)。通常,需要1024次掃描以供適當的訊噪比。寬頻質子去偶(broadband proton decoupling)係使用Waltz-16脈衝序列進行。使用內標準品2,4-二溴酚訊號作為化學位移參考(chemical shift reference)(δ =130.24ppm)。使用1 Hz指數變跡法(exponential apodization)來處理所得之譜以及使用多項式擬合常式(polynomial fit routine)來校正基線(baseline correct)。所有資料處理(data processing)均使用NetNMR軟體完成。
環己酚(cyclohexyl phenol)及四甲基雙酚A(tetramethyl bisphenol A)共聚物(CP-PPE)係藉由氧化偶合聚合(oxidative coupling polymerization)來合成,如前文所述。使材料沉澱以去除未反應之單體以供較佳的結構分析。使用NMR譜法來測定化學結構。單體之殘留量(residual amount)係藉由
31P NMR來測定。於未經取代之6-位(unsubstituted 6-position)的分枝(branching)係經由
1H NMR譜法基於芳族環中之質子數(number of protons)來確認。若獲得線型聚合物(linear polymer),則質子數應為3,然而,確認其為2.5。因此,CP-PPE寡聚物展現分枝結構(branched structure)。
本揭露內容進一步包含下列態樣。
態樣1:線型雙官能苯醚寡聚物(linear bifunctional phenylene ether oligomer),其包含衍生自2-甲基-6-環己酚(2-methyl-6-cyclohexylphenol)之重複單元且具有(甲基)丙烯酸酯((meth)acrylate)端基(end group)。
態樣2:如態樣1之雙官能苯醚寡聚物,其中,苯醚寡聚物包含少於30重量百分比之衍生自在2-及6-位具有相同取代基的一元酚(monohydric phenol)之重複單元。
態樣4:如態樣1至3中任一項之苯醚寡聚物,其中,苯醚寡聚物具有結構
其中,R為甲基或氫;x及y獨立地為0至30,先決條件係x與y之總和至少為2;R
1、R
2 、R
3、及R
4於各次出現時立獨地包含氫、鹵素、未經取代或經取代之C
1-
12一級或二級烴基、C
1-
12烴硫基、C
1-
12烴氧基、或C
2-
12鹵烴氧基,其中至少兩個碳原子使鹵素原子及氫原子分開;z為0或1;Y具有包含以下之結構
其中,R
7於各次出現時獨立地包含氫及C
1-
12烴基,而R
8及R
9於各次出現時各自獨立地為氫、C
1-
12烴基、或C
1-
6伸烴基,其中R
8及R
9共同形成C
4-
12伸烷基;較佳係其中R
1及R
2於各次出現時為甲基,R
3及R
4於各次出現時為氫,z為1,以及Y為亞異丙基。
態樣5:一種製造如態樣1至4中任一項之線型雙官能苯醚寡聚物之方法,該方法包含於觸媒之存在下氧化聚合2-甲基-6-環己酚以提供苯醚寡聚物;以及使苯醚寡聚物與含(甲基)丙烯酸酯之化合物反應以提供線型雙官能苯醚寡聚物。
態樣6:如態樣5之方法,其中,氧化聚合係進一步於雙酚、較佳為四甲基雙酚A之存在下進行。
態樣7:一種可固化熱固性組成物,其包含如態樣1至4中任一項之線型雙官能苯醚寡聚物。
態樣8:如態樣7之可固化熱固性組成物,其進一步包含交聯劑、固化劑、固化觸媒、固化引發劑、或其組合中之一或多者。
態樣9:如態樣7或8之可固化熱固性組成物,其進一步包含阻燃劑、填料、偶合劑、或其組合中之一或多者。
態樣10:一種固化之熱固性組成物,其包含如態樣7至9中任一或多項之可固化熱固性組成物的固化產物,較佳係其中,熱固性組成物具有使用微差掃描熱量法(differential scanning calorimetry)測定之大於或等於165℃、較佳係大於或等於170℃、更佳係165至180℃之玻璃轉移溫度(glass transition temperature);其中,熱固性組成物於10 GHz之頻率具有低3.0、較佳係低於2.75、更佳係低於2.6之介電常數(dielectric constant);以及其中,熱固性組成物於10 GHz之頻率具有低於0.01、或低於0.005之耗散因子(dissipation factor)。
態樣11:一種製造態樣10之固化之熱固性組成物之方法,該方法包含固化可固化熱固性組成物,較佳於50至250℃之溫度。
態樣12:一種物件,其包含如態樣10之固化之熱固性組成物,較佳係其中,物件為複材、發泡體、纖維、層、塗層、封裝劑、黏著劑、密封劑、模製組件、預浸材、護罩、鑄造物件、層合物、或其組合;或其中,物件為覆金屬層合物、電子複材、結構複材、或其組合。
態樣13:清漆組成物,其包含如態樣7至9中任一項之可固化熱固性組成物;以及溶劑。
態樣14:一種物件,其係由如態樣13之清漆組成物所製造,較佳係其中物件為纖維、層、塗層、鑄造物件、預浸材、複材、層合物、或覆金屬層合物。
態樣15:一種製造如態樣14之物件之方法,其包含將清漆組成物浸入基材以形成預浸材;以及,固化清漆組成物。
該等組成物、方法、及物件可或包含下列者、由下列者組成、或基本上由下列者組成:本文所揭露之任何適當材料、步驟或組分。該等組成物、方法、及物件可額外、或者經調配以使其沒有、或實質上不含對獲致該等組成物、方法、及物件之功能或目標非必要的任何材料(或物種(species))、步驟或組分。
本文所揭示之所有範圍係包括端點(endpoint),且該等端點可獨立地彼此組合。「組合(combination)」包括摻合物(blend)、混合物(mixture)、合金(alloy)、反應產物(reaction product)等。術語「第一」、「第二」等不表示任何順序、數量或重要性,而是用以區分一要素與另一要素。除非本文另指明或上下文顯有抵觸,否則本文中之術語「一」及「該」不表示數量限制,應視為涵括單數(singular)及複數(plural)。除非另有明確陳述,否則所使用之「或」意指「及/或」。整篇說明書中所指之「態樣(aspect)」意指關於該態樣所述之特定要素係包含在本文所述之至少一態樣中,以及可或可能不存在於其他態樣中。本文所使用之術語「其組合(combination thereof)」包含所列要素之一或多者且為開放式,容許一或更多未提及之類似要素存在。此外,應瞭解所述要素在各種態樣中可以任何適用方式結合。
除非本文中有相反指明,否則所有測試標準為至本申請案之申請日、或者若主張優先權則為測試標準出現之最早優先權案之申請日有效(in effect)之最近標準。
除非另有界定,否則本文所使用之技術及科學術語具有如同本案所屬領域之通常知識者一般所瞭解的意義。所引用之所有專利、專利申請案及其他參考資料係以其整體以引用的方式併入本文中。然而,若本案中之術語與所併入參考資料中之術語矛盾或衝突,則來自本案之術語有高於來自所併入參考資料之衝突術語的優先性。
使用標準命名法(standard nomenclature)描述化合物。例如,未被任何所指基團取代的任何位置應理解為其價(valency)係被所指之鍵(bond)或氫原子所填。非在兩個字母或符號之間的破折號("-")係用以表示取代基的附接點(point of attachment)。例如,-CHO係經由羰基之碳附接。
如本文所使用,術語「烴基(hydrocarbyl)」,不論是單獨使用或者作為另一術語之前綴(prefix)、後綴(suffix)、或片段(fragment),係指僅含碳及氫之殘基(residue)。該殘基可為脂族或芳族、直鏈、環狀、雙環、分枝(branched)、飽和(saturated)或不飽和(unsaturated)。亦可含有脂族、芳族、直鏈、環狀、雙環、分枝、飽和及不飽和烴部分(hydrocarbon moiety)之組合。然而,當烴基殘基描述為經取代(substituted)時,其可視需要地含有在取代基殘基之碳及氫成員之上的雜原子。因此,具體描述為經取代時,烴基殘基亦可含有一或多個羰基、胺基、羥基等,或者其可含有在烴基殘基之主鏈(backbone)內的雜原子。術語「烷基(alkyl)」意指分枝或直鏈的飽和脂族烴基,例如甲基、乙基、正丙基、異丙基、正丁基、二級丁基、三級丁基、正戊基、二級戊基、及正己基和二級己基。「烯基(alkenyl)」意指具有至少一個碳-碳雙鍵之直鏈(straight chain)或支鏈(branched chain)的一價烴基(monovalent hydrocarbon group)(例如,乙烯基(-HC=CH
2))。「烷氧基(alkoxy)」意指經由氧鍵聯(link)之烷基(即,烷基-O-),例如甲氧基、乙氧基、及二級丁氧基。「伸烷基(alkylene)」意指直鏈或支鏈的飽和二價脂族烴基(divalent aliphatic hydrocarbon group)(例如,亞甲基(methylene)(-CH
2-)或伸丙基(propylene)(-(CH
2)
3-))。「伸環烷基(cycloalkylene)」意指二價環狀伸烷基(divalent cyclic alkylene group)-C
nH
2n-x,其中x為藉由環化(cyclization)置換的氫之數目。「環烯基(cycloalkenyl)」意指具有一或多個環以及在環中一或多個碳-碳雙鍵之一價基團,其中所有環成員均為碳(例如,環戊基及環己基)。「芳基(aryl)」意指含有所指碳原子數之芳族烴基,諸如苯基、䓬酮(tropone)、二氫茚基(indanyl)、或萘基(naphthyl)。「伸芳基(arylene)」意指二價芳基。「烷基伸芳基(Alkylarylene)」意指經烷基取代之伸芳基。「芳基伸烷基(Arylalkylene)」意指經芳基(例如,苄基(benzyl))取代之伸烷基。前綴「鹵(halo)」意指包含氟、氯、溴或碘取代基中之一或多者的基團或化合物。可存在不同鹵原子(例如溴及氟)之組合、或僅存在氯原子。前綴「雜(hetero)」意指包含至少一個為雜原子之環成員(例如,1、2、或3個雜原子)的化合物或基團,其中雜原子各自獨立地為N、O、S、Si、或P。「經取代(substituted)」意指化合物或基團係經至少一(例如,1、2、3、或4)個取代基取代,該等取代基可各自獨立地為C
1-9烷氧基、C
1-9鹵烷氧基(haloalkoxy)、硝基(-NO
2)、氰基(-CN)、C
1-6烷基磺醯基(alkyl sulfonyl)(-S(=O)
2-烷基)、C
6-12芳基磺醯基(aryl sulfonyl)(-S(=O)
2-芳基)、氫硫基(thiol)(-SH)、硫氰基(thiocyano)(-SCN)、甲苯磺醯基(tosyl)(CH
3C
6H
4SO
2-)、C
3-12環烷基、C
2-12烯基、C
5-12環烯基、C
6-12芳基、C
7-13芳基伸烷基、C
4-12雜環烷基(heterocycloalkyl)、及C
3-12雜芳基(heteroaryl)代替氫,先決條件係不超過經取代之原子的正常價(normal valence)。基團中所表示之碳原子數不包括任何取代基。例如,-CH
2CH
2CN為經腈(nitrile)取代之C
2烷基(C
2alkyl groupa)。
雖然已描述特定態樣,但申請人或其他熟習本領域之人士可發現目前未預見或可能未預見的替代、修改、變化、改良及實質上相當者。因此,申請時所附申請專利範圍以及可能經修正者係意欲包括所有此等替代、修改、變化、改良及實質上相當者。
Claims (15)
- 一種線型雙官能苯醚寡聚物(linear bifunctional phenylene ether oligomer),其包含衍生自2-甲基-6-環己酚(2-methyl-6-cyclohexylphenol)之重複單元且具有(甲基)丙烯酸酯端基(end group)。
- 如請求項1之雙官能苯醚寡聚物,其中,該苯醚寡聚物包含少於30重量百分比之衍生自在2-及6-位具有相同取代基的一元酚(monohydric phenol)之重複單元。
- 如請求項1至3中任一項之苯醚寡聚物,其中,該苯醚寡聚物具有結構 其中 R為甲基或氫; x及y獨立地為0至30,先決條件係x與y之總和至少為2; R 1、R 2、R 3、及R 4於各次出現時獨立地包含氫、鹵素、未經取代或經取代之C 1- 12一級(primary)或二級(secondary)烴基、C 1- 12烴硫基(hydrocarbylthio)、C 1- 12烴氧基(hydrocarbyloxy)、或C 2- 12鹵烴氧基(halohydrocarbyloxy),其中至少兩個碳原子使鹵素原子及氧原子分開; z為0或1; Y具有包含以下之結構 其中,R 7於各次出現時獨立地包含氫及C 1- 12烴基,而R 8及R 9於各次出現時各自獨立地為氫、C 1- 12烴基、或C 1- 6伸烴基(hydrocarbylene),其中R 8及R 9共同形成C 4- 12伸烷基; 較佳地,其中,R 1及R 2於各次出現時為甲基,R 3及R 4於各次出現時為氫,z為1,以及Y為亞異丙基(isopropylidene group)。
- 一種製造如請求項1至4中任一項之線型雙官能苯醚寡聚物之方法,該方法包含 於觸媒之存在下氧化聚合(oxidatively polymerizing)2-甲基-6-環己酚以提供苯醚寡聚物;以及 使苯醚寡聚物與含(甲基)丙烯酸酯之化合物反應以提供該線型雙官能苯醚寡聚物。
- 如請求項5之方法,其中,該氧化聚合係進一步於雙酚(bisphenol)、較佳為四甲基雙酚A(tetramethyl bisphenol A)之存在下進行。
- 一種可固化熱固性組成物,其包含 如請求項1至4中任一項之線型雙官能苯醚寡聚物。
- 如請求項7之可固化熱固性組成物,其進一步包含交聯劑、固化劑、固化觸媒、固化引發劑、或其組合中之一或多者。
- 如請求項7或8之可固化熱固性組成物,其進一步包含阻燃劑、填料、偶合劑、或其組合中之一或多者。
- 一種固化之熱固性組成物,其包含如請求項7至9中任一或多項之可固化熱固性組成物的固化產物。
- 一種製造如請求項10之固化之熱固性組成物之方法,該方法包含固化該可固化熱固性組成物,較佳於50至250℃之溫度。
- 一種物件,其包含如請求項10之固化之熱固性組成物, 較佳的 其中,該物件為複材(composite)、發泡體(foam)、纖維、層、塗層、封裝劑(encapsulant)、黏著劑、密封劑(sealant)、模製組件(molded component)、預浸材(prepreg)、護罩(casing)、鑄造物件(cast article)、層合物(laminate)、或其組合;或 其中,該物件為覆金屬層合物(metal clad laminate)、電子複材(electronic composite)、結構複材(structural composite)、或其組合。
- 一種清漆組成物(varnish composition),其包含 如請求項7至9中任一項之可固化熱固性組成物;以及 溶劑。
- 一種物件,其係由如請求項13之清漆組成物所製造,較佳係其中該物件為纖維、層、塗層、鑄造物件、預浸材、複材、層合物、或覆金屬層合物。
- 一種製造如請求項14之物件之方法,其包含將該清漆組成物浸入基材以形成預浸材;以及,固化該清漆組成物。
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EP21169518.4A EP4079784A1 (en) | 2021-04-20 | 2021-04-20 | Phenylene ether oligomer and curable thermosetting composition comprising the phenylene ether oligomer |
EP21169518.4 | 2021-04-20 |
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TW202307077A true TW202307077A (zh) | 2023-02-16 |
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TW111114826A TW202307077A (zh) | 2021-04-20 | 2022-04-19 | 苯醚寡聚物及含該苯醚寡聚物之可固化熱固性組成物 |
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EP (1) | EP4079784A1 (zh) |
JP (1) | JP2024516137A (zh) |
KR (1) | KR20230170675A (zh) |
CN (1) | CN117178007A (zh) |
TW (1) | TW202307077A (zh) |
WO (1) | WO2022224144A1 (zh) |
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FR1555564A (zh) | 1967-07-13 | 1969-01-31 | ||
DE2754631C2 (de) | 1977-12-08 | 1986-05-07 | Technochemie Gmbh, Verfahrenstechnik, 6901 Dossenheim | Heißhärtbare Imidharze |
DE2754632C2 (de) | 1977-12-08 | 1984-04-19 | Technochemie Gmbh, Verfahrenstechnik, 6901 Dossenheim | Heißhärtbare Imidharze |
US4304705A (en) | 1980-01-02 | 1981-12-08 | Minnesota Mining And Manufacturing Company | Radiation-curable polymers containing pendant unsaturated peptide groups derived from azlactone polymers |
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US4540763A (en) | 1984-09-14 | 1985-09-10 | The Dow Chemical Company | Polymers derived from poly(arylcyclobutenes) |
US5391650A (en) | 1992-12-30 | 1995-02-21 | The Dow Chemical Company | Bisbenzocyclobutene thermosetting compounds and process for preparing the same |
JP3319061B2 (ja) | 1993-08-20 | 2002-08-26 | 住友化学工業株式会社 | シアネート化合物の製造方法 |
US6627704B2 (en) * | 1999-12-01 | 2003-09-30 | General Electric Company | Poly(arylene ether)-containing thermoset composition, method for the preparation thereof, and articles derived therefrom |
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US6835785B2 (en) | 2002-01-28 | 2004-12-28 | Mitsubishi Gas Chemical Company, Inc. | Polyphenylene ether oligomer compound, derivatives thereof and use thereof |
US7192651B2 (en) | 2003-08-20 | 2007-03-20 | Mitsubishi Gas Chemical Company, Inc. | Resin composition and prepreg for laminate and metal-clad laminate |
JP2006316092A (ja) * | 2005-05-10 | 2006-11-24 | Showa Denko Kk | ポリフェニレンエーテル、その製造方法および用途 |
WO2008103599A2 (en) * | 2007-02-22 | 2008-08-28 | Sabic Innovative Plastics Ip B.V. | Composition, its use in the preparation of membranes, and systems comprising the membranes |
JP5649773B2 (ja) * | 2007-05-31 | 2015-01-07 | 三菱瓦斯化学株式会社 | 硬化性樹脂組成物および硬化性フィルムならびにそれらの硬化物 |
KR101558446B1 (ko) * | 2012-04-25 | 2015-10-07 | 사빅 글로벌 테크놀러지스 비.브이. | 폴리(페닐렌 에테르) 코폴리머 및 이의 제조 방법 |
US10995182B2 (en) * | 2018-04-30 | 2021-05-04 | Shpp Global Technologies B.V. | Phenylene ether oligomer, curable composition comprising the phenylene ether oligomer, and thermoset composition derived therefrom |
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- 2022-04-19 CN CN202280029723.7A patent/CN117178007A/zh active Pending
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KR20230170675A (ko) | 2023-12-19 |
JP2024516137A (ja) | 2024-04-12 |
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