CN106008866A - 摩擦材料用甲阶型酚醛树脂、其制造方法、摩擦材料用粘接剂和湿式摩擦板 - Google Patents
摩擦材料用甲阶型酚醛树脂、其制造方法、摩擦材料用粘接剂和湿式摩擦板 Download PDFInfo
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- CN106008866A CN106008866A CN201610200994.0A CN201610200994A CN106008866A CN 106008866 A CN106008866 A CN 106008866A CN 201610200994 A CN201610200994 A CN 201610200994A CN 106008866 A CN106008866 A CN 106008866A
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- friction material
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- phenol resin
- type phenol
- phenols
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- 229920003987 resole Polymers 0.000 title claims abstract description 88
- 239000005011 phenolic resin Substances 0.000 title claims abstract description 82
- 239000002783 friction material Substances 0.000 title claims abstract description 79
- 239000000853 adhesive Substances 0.000 title claims abstract description 22
- 230000001070 adhesive effect Effects 0.000 title claims abstract description 22
- 238000004519 manufacturing process Methods 0.000 title claims description 25
- KXGFMDJXCMQABM-UHFFFAOYSA-N 2-methoxy-6-methylphenol Chemical compound [CH]OC1=CC=CC([CH])=C1O KXGFMDJXCMQABM-UHFFFAOYSA-N 0.000 title abstract description 8
- 229920001568 phenolic resin Polymers 0.000 title abstract description 8
- 239000000463 material Substances 0.000 claims abstract description 22
- 229910052751 metal Inorganic materials 0.000 claims abstract description 14
- 239000002184 metal Substances 0.000 claims abstract description 14
- 150000003739 xylenols Chemical class 0.000 claims abstract description 10
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 9
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical group OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 57
- 239000007767 bonding agent Substances 0.000 claims description 48
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 41
- 238000010276 construction Methods 0.000 claims description 31
- 150000002989 phenols Chemical class 0.000 claims description 26
- 238000000034 method Methods 0.000 claims description 24
- MOZWGCRWGKSWAJ-UHFFFAOYSA-N phenol;1,2-xylene Chemical class OC1=CC=CC=C1.CC1=CC=CC=C1C MOZWGCRWGKSWAJ-UHFFFAOYSA-N 0.000 claims description 22
- 229920005989 resin Polymers 0.000 claims description 13
- 239000011347 resin Substances 0.000 claims description 13
- TUAMRELNJMMDMT-UHFFFAOYSA-N 3,5-xylenol Chemical compound CC1=CC(C)=CC(O)=C1 TUAMRELNJMMDMT-UHFFFAOYSA-N 0.000 claims description 12
- 150000001299 aldehydes Chemical class 0.000 claims description 11
- 239000003054 catalyst Substances 0.000 claims description 9
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- 238000012986 modification Methods 0.000 claims description 9
- 239000007795 chemical reaction product Substances 0.000 claims description 6
- 229920001971 elastomer Polymers 0.000 claims description 6
- 239000000806 elastomer Substances 0.000 claims description 5
- 229920002037 poly(vinyl butyral) polymer Polymers 0.000 claims description 5
- 150000005207 1,3-dihydroxybenzenes Chemical class 0.000 claims description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 4
- 229920000459 Nitrile rubber Polymers 0.000 claims description 3
- 239000003822 epoxy resin Substances 0.000 claims description 3
- 229920000647 polyepoxide Polymers 0.000 claims description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
- QTWJRLJHJPIABL-UHFFFAOYSA-N 2-methylphenol;3-methylphenol;4-methylphenol Chemical compound CC1=CC=C(O)C=C1.CC1=CC=CC(O)=C1.CC1=CC=CC=C1O QTWJRLJHJPIABL-UHFFFAOYSA-N 0.000 claims 1
- 239000005062 Polybutadiene Substances 0.000 claims 1
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 claims 1
- 239000010931 gold Substances 0.000 claims 1
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- 229920002857 polybutadiene Polymers 0.000 claims 1
- -1 methylol group Chemical group 0.000 abstract description 17
- 239000002585 base Substances 0.000 description 24
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 15
- 239000004567 concrete Substances 0.000 description 14
- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 description 12
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 10
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- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- 229910000831 Steel Inorganic materials 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 3
- YCIMNLLNPGFGHC-UHFFFAOYSA-N catechol Chemical compound OC1=CC=CC=C1O YCIMNLLNPGFGHC-UHFFFAOYSA-N 0.000 description 3
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- NXXYKOUNUYWIHA-UHFFFAOYSA-N 2,6-Dimethylphenol Chemical compound CC1=CC=CC(C)=C1O NXXYKOUNUYWIHA-UHFFFAOYSA-N 0.000 description 2
- IQUPABOKLQSFBK-UHFFFAOYSA-N 2-nitrophenol Chemical compound OC1=CC=CC=C1[N+]([O-])=O IQUPABOKLQSFBK-UHFFFAOYSA-N 0.000 description 2
- HMNKTRSOROOSPP-UHFFFAOYSA-N 3-Ethylphenol Chemical compound CCC1=CC=CC(O)=C1 HMNKTRSOROOSPP-UHFFFAOYSA-N 0.000 description 2
- VGMJYYDKPUPTID-UHFFFAOYSA-N 4-ethylbenzene-1,3-diol Chemical compound CCC1=CC=C(O)C=C1O VGMJYYDKPUPTID-UHFFFAOYSA-N 0.000 description 2
- HXDOZKJGKXYMEW-UHFFFAOYSA-N 4-ethylphenol Chemical compound CCC1=CC=C(O)C=C1 HXDOZKJGKXYMEW-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- YNQLUTRBYVCPMQ-UHFFFAOYSA-N Ethylbenzene Chemical compound CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 description 2
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 2
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- IOVCWXUNBOPUCH-UHFFFAOYSA-N Nitrous acid Chemical compound ON=O IOVCWXUNBOPUCH-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- NBBJYMSMWIIQGU-UHFFFAOYSA-N Propionic aldehyde Chemical compound CCC=O NBBJYMSMWIIQGU-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
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- PXKLMJQFEQBVLD-UHFFFAOYSA-N bisphenol F Chemical compound C1=CC(O)=CC=C1CC1=CC=C(O)C=C1 PXKLMJQFEQBVLD-UHFFFAOYSA-N 0.000 description 2
- 229910000019 calcium carbonate Inorganic materials 0.000 description 2
- AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 description 2
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- GEHJYWRUCIMESM-UHFFFAOYSA-L sodium sulfite Chemical compound [Na+].[Na+].[O-]S([O-])=O GEHJYWRUCIMESM-UHFFFAOYSA-L 0.000 description 2
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- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 2
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- UFBJCMHMOXMLKC-UHFFFAOYSA-N 2,4-dinitrophenol Chemical compound OC1=CC=C([N+]([O-])=O)C=C1[N+]([O-])=O UFBJCMHMOXMLKC-UHFFFAOYSA-N 0.000 description 1
- 125000001917 2,4-dinitrophenyl group Chemical group [H]C1=C([H])C(=C([H])C(=C1*)[N+]([O-])=O)[N+]([O-])=O 0.000 description 1
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- 229910052802 copper Inorganic materials 0.000 description 1
- 238000004132 cross linking Methods 0.000 description 1
- MLUCVPSAIODCQM-NSCUHMNNSA-N crotonaldehyde Chemical compound C\C=C\C=O MLUCVPSAIODCQM-NSCUHMNNSA-N 0.000 description 1
- MLUCVPSAIODCQM-UHFFFAOYSA-N crotonaldehyde Natural products CC=CC=O MLUCVPSAIODCQM-UHFFFAOYSA-N 0.000 description 1
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 1
- OQRWAMBQGTYSRD-UHFFFAOYSA-N dipotassium;oxygen(2-);titanium(4+) Chemical compound [O-2].[O-2].[O-2].[O-2].[O-2].[O-2].[O-2].[O-2].[O-2].[K+].[K+].[Ti+4].[Ti+4].[Ti+4].[Ti+4] OQRWAMBQGTYSRD-UHFFFAOYSA-N 0.000 description 1
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- NRZWYNLTFLDQQX-UHFFFAOYSA-N p-tert-Amylphenol Chemical compound CCC(C)(C)C1=CC=C(O)C=C1 NRZWYNLTFLDQQX-UHFFFAOYSA-N 0.000 description 1
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 1
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- QCDYQQDYXPDABM-UHFFFAOYSA-N phloroglucinol Chemical compound OC1=CC(O)=CC(O)=C1 QCDYQQDYXPDABM-UHFFFAOYSA-N 0.000 description 1
- 229960001553 phloroglucinol Drugs 0.000 description 1
- 238000005554 pickling Methods 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 229940079877 pyrogallol Drugs 0.000 description 1
- 239000011134 resol-type phenolic resin Substances 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 239000005060 rubber Substances 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- KKCBUQHMOMHUOY-UHFFFAOYSA-N sodium oxide Chemical compound [O-2].[Na+].[Na+] KKCBUQHMOMHUOY-UHFFFAOYSA-N 0.000 description 1
- 229910001948 sodium oxide Inorganic materials 0.000 description 1
- 235000010265 sodium sulphite Nutrition 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-L sulfite Chemical compound [O-]S([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-L 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- AGGKEGLBGGJEBZ-UHFFFAOYSA-N tetramethylenedisulfotetramine Chemical compound C1N(S2(=O)=O)CN3S(=O)(=O)N1CN2C3 AGGKEGLBGGJEBZ-UHFFFAOYSA-N 0.000 description 1
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- RYFMWSXOAZQYPI-UHFFFAOYSA-K trisodium phosphate Chemical compound [Na+].[Na+].[Na+].[O-]P([O-])([O-])=O RYFMWSXOAZQYPI-UHFFFAOYSA-K 0.000 description 1
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Abstract
根据本发明，提供一种摩擦材料用甲阶型酚醛树脂，是在用于粘接摩擦材料与金属基材的粘接剂中使用的摩擦材料用甲阶型酚醛树脂，该摩擦材料用甲阶型酚醛树脂具有被二甲基苯酚类改性的下述式(1)表示的结构单元A和下述通式(2)表示的结构单元B。(式(1)中，m为1以上的整数。m为1时，R为羟甲基。m为2以上时，R独立地为氢原子或羟甲基，且至少1个R为羟甲基。)
Description
技术领域
本发明涉及摩擦材料用甲阶型酚醛树脂、其制造方法、摩擦材料用粘接剂和湿式摩擦板。
背景技术
甲阶型酚醛树脂是机械特性、电特性和粘接性优异的树脂材料。因此，甲阶型酚醛树脂被广泛用作在制作离合器、制动器等摩擦材料时使用的粘结剂树脂。其中，对于制作在自动挡车等的自动变速器中使用的摩擦材料，即，湿式摩擦板时作为粘结剂树脂使用的甲阶型酚醛树脂，为了改善其粘接强度等固化特性，提高湿式摩擦板的摩擦特性，一直以来进行了各种研究。
作为着眼于提高甲阶型酚醛树脂的固化特性的技术，例如有以下技术。
专利文献1中公开了一种粘接剂组合物，含有固化时间短、具有优异的粘接强度的甲阶型酚醛树脂(A)、聚乙烯醇缩丁醛树脂(B)、多价金属盐(C)和亚硝酸的金属盐或亚硝酸的酯(D)。
专利文献2中公开了显示优异的粘接强度的含有甲阶型酚醛树脂和硝酸盐或硝酸的湿式摩擦板用粘接剂。
现有技术文献
专利文献
专利文献1：日本特开2014―24881号公报
专利文献2：日本特开2006―83892号公报
发明内容
如上述背景技术一项中所述，为了提高以往的甲阶型酚醛树脂的固化特性进行了各种研究。然而，近年来，从提高摩擦材料的制造效率的观点考虑，需要能够以短的固化时间实现优异的粘接强度的甲阶型酚醛树脂。
因此，本发明提供能够以短的粘接时间实现高的粘接强度的摩擦材料用甲阶型酚醛树脂及其制造方法、含有该摩擦材料用甲阶型酚醛树脂的摩擦材料用粘接剂和湿式摩擦板。
根据本发明，提供一种摩擦材料用甲阶型酚醛树脂，是在用于粘接摩擦材料与金属基材的粘接剂中使用的摩擦材料用甲阶型酚醛树脂，
该摩擦材料用甲阶型酚醛树脂在分子结构中具有被二甲基苯酚类改性的下述式(1)表示的结构单元A和下述式(2)表示的结构单元B。
(式(1)中，m为1以上的整数。m为1时，R为羟甲基。m为2以上时，R独立地为氢原子或羟甲基，且至少1个R为羟甲基。)
(式(2)中，n为1以上的整数。n为1时，R为羟甲基。n为2以上时，R独立地为氢原子或羟甲基，且至少1个R为羟甲基。)
此外，根据本发明，提供一种摩擦材料用甲阶型酚醛树脂的制造方法，是在用于粘接摩擦材料与金属基材的粘接剂中使用的摩擦材料用甲阶型酚醛树脂的制造方法，包含：
第1工序，在碱性催化剂的存在下，使不包括二甲基苯酚类的酚类与醛类得到第1反应生成物；
第2工序，在碱性催化剂的存在下，使上述第1反应生成物与二甲基苯酚类反应得到甲阶型酚醛树脂。
此外，根据本发明，提供一种摩擦材料用粘接剂，含有上述摩擦材料用甲阶型酚醛树脂，和
选自聚乙烯醇缩丁醛树脂、丁腈橡胶、苯乙烯-丁二烯橡胶和环氧树脂中的1种以上的弹性体。
此外，根据本发明，提供一种湿式摩擦板，包含摩擦材料、金属基材、和介于上述摩擦材料与上述金属基材之间的上述摩擦材料用粘接剂。
根据本发明，能够提供能够以短的粘接时间实现高的粘接强度的摩擦材料用甲阶型酚醛树脂及其制造方法，含有该摩擦材料用甲阶型酚醛树脂的摩擦材料用粘接剂和湿式摩擦板。
具体实施方式
＜摩擦材料用甲阶型酚醛树脂＞
本实施方式的摩擦材料用甲阶型酚醛树脂(以下，也称为甲阶型酚醛树脂)在用于粘接摩擦材料与金属基材的粘接剂中使用。上述甲阶型酚醛树脂在分子结构中具有被二甲基苯酚类改性的下述式(1)表示的结构单元A和下述式(2)表示的结构单元B。换言之，本发明的甲阶型酚醛树脂在由结构单元B构成的一般的甲阶型酚醛树脂的结构中含有具有二甲基苯酚骨架的结构单元A。这样，该甲阶型酚醛树脂含有在结构单元中具有2个作为供电子基团的甲基的结构单元A，因此与用于粘接摩擦材料与金属基材的以往的粘接剂相比反应性优异。另外，采用该甲阶型酚醛树脂，如上所述具有在结构单元中具有2个作为供电子基团的甲基的结构单元A，因此也能够提高使该树脂热固化时的交联密度。因此，采用该甲阶型酚醛树脂，与以往的粘接剂相比能够以短的粘接时间实现高的粘接强度。
(式(1)中，m为1以上的整数。m为1时，R为羟甲基。m为2以上时，R独立地为氢原子或羟甲基，且至少1个R为羟甲基。)
(式(2)中，n为1以上的整数。n为1时，R为羟甲基。n为2以上时，R独立地为氢原子或羟甲基，且至少1个R为羟甲基。)
上述甲阶型酚醛树脂通过包括二甲基苯酚类的酚类与醛类反应而得到。
本发明的甲阶型酚醛树脂除了作为一般的甲阶型酚醛树脂所具有的结构的结构单元B，还含有具有二甲基苯酚骨架的结构单元A。作为成为结构单元A的来源的二甲基苯酚类的具体例，可举出2,3-二甲基苯酚、2,4-二甲基苯酚、2,5-二甲基苯酚、2,6-二甲基苯酚、3,4-二甲基苯酚和3,5-二甲基苯酚等。其中，从与作为取代基的甲基的大体积相伴的、得到的树脂的反应性、加热时的结构稳定性等观点考虑，优选3,5-二甲基苯酚。这时，得到的甲阶型酚醛树脂具有被3,5-二甲基苯酚改性的下述式(3)表示的结构单元C。
(式(3)中，m为1以上的整数。m为1时，R为羟甲基。m为2以上时，R独立地为氢原子或羟甲基，且至少1个R为羟甲基。)
在优选的实施方式中，本发明的甲阶型酚醛树脂由结构单元A和结构单元B构成。
作为成为结构单元B的来源的酚类的具体例，可举出苯酚、邻甲酚、间甲酚、对甲酚等甲酚类。
另外，上述甲阶型改性酚醛树脂除了上述式(1)表示的来自二甲基苯酚类的结构单元A和式(2)表示的来自酚类的结构单元B，还可以具有来自其他酚类的结构单元。作为上述其他酚类的具体例，可举出邻乙基苯酚、间乙基苯酚、对乙基苯酚等乙基苯酚类；异丙基苯酚、丁基苯酚、对叔丁基苯酚等丁基苯酚类；对叔戊基苯酚、对辛基苯酚、对壬基苯酚、对枯基苯酚等烷基苯酚类；氟苯酚、氯苯酚、溴苯酚、碘苯酚等卤代苯酚类；对苯基苯酚、氨基苯酚、硝基苯酚、二硝基苯酚、三硝基苯酚等一元苯酚取代物：和1-萘酚、2-萘酚等一元酚类；间苯二酚、烷基间苯二酚、邻苯三酚、邻苯二酚、烷基邻苯二酚、对苯二酚、烷基对苯二酚、间苯三酚、双酚A、双酚F、双酚S、二羟基萘等多元酚类等。它们可以单独使用或混合2种以上使用。其中，从提高固化物的机械强度的观点考虑，优选为选自苯酚、甲酚类和双酚A中的任一种以上。另外，从制造树脂的工序的操作性的观点考虑，优选酚类可溶于后述的有机溶剂。
对于该甲阶型酚醛树脂，从加热时的反应性、固化物的机械强度和固化物的制造成本等的平衡的观点考虑，将该甲阶型酚醛树脂中含有的具有酚性羟基的全部结构单元中的上述式(1)表示的结构单元A的比例作为二甲基苯酚改性率时，上述二甲基苯酚改性率优选为3％～50％，进一步优选为3％～40％，最优选为3％～35％。通过为上述下限值以上，从而得到甲阶型酚醛树脂的充分的固化性提高效果。另外，从成本的观点考虑，通过为上述上限值以下，能够在甲阶型酚醛树脂的制造中减少昂贵的二甲基苯酚类的使用量，能够得到实用性优异的甲阶型酚醛树脂。
这里，从操作性的观点考虑，该甲阶型酚醛树脂优选为液态的形式。以下，举出该甲阶型酚醛树脂为液态的形式的情况为例进行说明。
该甲阶型酚醛树脂在碱性催化剂下使包括二甲基苯酚类的酚类与醛类反应而得到。作为用于制造该甲阶型酚醛树脂的原料的酚类的具体例如上所述。
接下来，对该甲阶型酚醛树脂的制造方法进行说明。
如上所述，该甲阶型酚醛树脂的制造方法包含在碱性催化剂下使包括二甲基苯酚类的酚类与醛类反应的工序。具体而言，该甲阶型酚醛树脂的制造方法包含：第1工序，在碱性催化剂的存在下，使不包括二甲基苯酚类的酚类与醛类反应而得到第1反应生成物；第2工序，在碱性催化剂的存在下，使上述第1反应生成物与二甲基苯酚类反应而得到甲阶型酚醛树脂。
在上述第1工序中使用的酚类作为成为结构单元B的来源的酚类和其他酚类如上所述。
在上述第2工序中使用的二甲基苯酚类作为成为结构单元A的来源的二甲基苯酚类如上所述。
作为属于用于制造该甲阶型酚醛树脂的原料的醛类的具体例，可举出甲醛、多聚甲醛、三烷、乙醛、丙醛、聚甲醛、三氯乙醛、六亚甲基四胺、糠醛、乙二醛、正丁醛、己醛、烯丙醛、苯甲醛、巴豆醛、丙烯醛、四聚甲醛、苯乙醛、邻甲基苯甲醛、水杨醛等。它们可以单独使用，也可组合2种以上使用。另外，也可以使用这些醛类的前体或这些醛类的溶液。其中，从制造成本的观点考虑，优选使用甲醛水溶液。
作为用于制造该甲阶型酚醛树脂的碱性催化剂的具体例，可举出氢氧化钠、氢氧化钾、氢氧化钙等碱金属或碱土金属的氢氧化物；碳酸钠、碳酸钙等碳酸盐；石灰等氧化物；亚硫酸钠等亚硫酸盐；磷酸钠等磷酸盐；氨、三甲胺、三乙胺、单乙醇胺、二乙醇胺、三乙醇胺、六亚甲基四胺、吡啶等胺类。
从提高得到的甲阶型酚醛树脂的反应性和固化性的观点考虑，在上述第2工序中使用的二甲基苯酚类的量相对于该不包括二甲基苯酚类的酚类100重量份，优选为5重量份～100重量份，进一步优选为5重量份～50重量份。通过为上述下限值以上，从而得到所得的甲阶型酚醛树脂的充分的固化性提高效果。另外，从成本的观点考虑，通过为上述上限值以下，能够减少昂贵的二甲基苯酚类的使用量，能够成为实用性优异的甲阶型酚醛树脂。
另外，从提高得到的甲阶型酚醛树脂的粘接强度的观点考虑，在上述制造方法中使用的包括二甲基苯酚类的各种酚类的合计量(P)与醛类的量(F)的摩尔比换算的(F/P)值优选为0.8～3，进一步优选为1～2.5。通过为上述下限值以上，能够在甲阶型酚醛树脂热固化时实现充分的交联密度，因此能够进一步提高粘接强度。另外，通过为上述上限值以下，能够防止交联密度提高到损害其粘接性的程度，因此作为结果得到粘接强度优异的甲阶型酚醛树脂。
另外，从减少未反应的酚类和醛类的量的观点考虑，在本制造方法中使用的碱性催化剂量相对于包括二甲基苯酚类的各种酚类1摩尔，优选为0.01摩尔～1摩尔，进一步优选为0.05摩尔～0.5摩尔。通过为上述下限值以上，能够缩短甲阶型酚醛树脂的合成反应时间，因此能够实现生产率优异的甲阶型酚醛树脂。另外，通过为上述上限值以下，能够防止甲阶型酚醛树脂的合成反应的反应速度急剧上升，因此能够以稳定的品质得到甲阶型酚醛树脂。
另外，甲阶型酚醛树脂中含有的未反应酚类(游离酚)的含量相对于甲阶型酚醛树脂总量，优选小于5质量％，进一步优选小于3质量％。通过使未反应酚类为上述范围内，能够抑制酚成分的挥发，提供良好的作业环境。另外，使未反应酚类(游离酚)的含量为上述上限值以下时，从而在制造该甲阶型酚醛树脂时无需进行需要繁琐步骤的脱单体处理。
作为在上述第1工序和第2应工序中使用的反应溶剂，一般为水，但也可以使用有机溶剂。作为上述有机溶剂的具体例，可举出醇类、酮类、芳香族类等。而且，作为上述醇类的具体例，可举出甲醇、乙醇、丙醇、乙二醇、二乙二醇、三乙二醇、甘油等。另外，作为酮类的具体例，可举出丙酮、甲乙酮等。作为芳香族类的具体例，可举出甲苯、二甲苯等。
＜摩擦材料用粘接剂＞
本实施方式的摩擦材料用粘接剂含有上述摩擦材料用甲阶型酚醛树脂和选自聚乙烯醇缩丁醛树脂、丁腈橡胶、苯乙烯-丁二烯橡胶和环氧树脂中的1种以上的弹性体。由此能够实现能够得到挠性和韧性等机械特性优异的固化物的摩擦材料用粘接剂。
从改善得到的固化物的机械特性的观点考虑，上述弹性体的含量相对于摩擦材料用粘接剂总量，优选为1重量％～20重量％，进一步优选为2重量％～10重量％。通过为上述下限值以上，粘接剂的柔软性能够提高，结果能够得到粘接强度优异的粘接剂。另外，通过为上述上限值以下，能够降低耐热性差的弹性体的含量，因此作为结果能够实现耐热性优异的粘接剂。
另外，本摩擦材料用粘接剂可以进一步含有间苯二酚类。由此能够进一步提高该摩擦材料用粘接剂的固化速度。作为上述间苯二酚类的具体例，可举出间苯二酚、2-甲基间苯二酚、5-甲基间苯二酚、2,5-二甲基间苯二酚等甲基间苯二酚类、4-乙基间苯二酚、4-氯间苯二酚、2-硝基间苯二酚、4-溴间苯二酚、4-正己基间苯二酚等。它们可以单独使用，也可以混合2种以上使用。其中，从粘接剂的制造成本和成型性的观点考虑，优选使用选自间苯二酚、甲基间苯二酚类中的1种以上。
从提高固化物的固化特性的观点考虑，上述间苯二酚类的含量相对于摩擦材料用粘接剂总量，优选为0.01重量％～10重量％，进一步优选为0.02重量％～5重量％。通过为上述下限值以上，粘接剂的固化性能够提高，结果能够得到固化特性优异的粘接剂。另外，通过为上述上限值以下，能够抑制交联密度降低，因此能够实现固化特性和粘接强度优异的粘接剂。
另外，摩擦材料用粘接剂从提高其操作性的观点考虑可以以有机溶剂中的溶液的方式提供。作为上述有机溶剂的具体例，可举出甲醇、乙醇、异丙醇、丁醇等醇系有机溶剂、丙酮、甲乙酮、甲基异丁基酮等酮系有机溶剂、甲苯、乙苯等芳香族烃溶剂和它们的混合物。
＜湿式摩擦板＞
本实施方式的湿式摩擦板由摩擦材料、金属基材、和介于摩擦材料与金属基材之间的上述摩擦材料用粘接剂构成。换言之，湿式摩擦板通过用上述粘接剂粘接摩擦材料与金属基材而得到。通过使用耐热性、固化性优异的上述粘接剂，能够实现摩擦材料与金属基材(钢板等)的粘接性优异的湿式摩擦板。
本实施方式的摩擦材料例如可以通过以下方法制作。但是，本实施方式的摩擦材料的制造方法不限定于以下例子。
首先，以成为规定的组成比例的方式对含有纤维基材和填充剂的粉末原料与粘合材料进行计量，使用混合机将它们混合。应予说明，作为混合机的具体例，可举出爱立许混合机等一般的混合机。接下来，将混合得到的原料组合物按规定量分出，进行预成型而制成块体。其后，将得到的预成型体投入到例如加热至150℃的模具，加压3～7分钟左右，由此制作成型体。接下来，将制成的成型体在例如200℃以上的温度下进行1小时左右热处理而使其固化，由此能够得到本实施方式的摩擦材料。
作为上述纤维基材的具体例，可举出钢纤维、铜纤维、玻璃纤维、陶瓷纤维、钛酸钾纤维等无机纤维、芳纶纤维、纤维素纤维等有机纤维。它们可以单独使用，也可以组合2种以上使用。其中，优选含有芳纶纤维等有机纤维。
作为上述填充剂的具体例，可举出硅藻土、碳酸钙、氢氧化钙、硫酸钡、云母、磨料、高岭土和滑石等无机填充剂、腰果粉和橡胶粉等有机填充剂、石墨、三硫化锑、二硫化钼和二硫化锌等润滑材料。它们可以单独使用，也可以组合2种以上使用。其中，优选使用无机填充剂。
这里，本实施方式的湿式摩擦板用于形成离合器、制动器等摩擦部件。
以上对本发明的实施方式进行了描述，但这些是本发明的例示，也可以采用上述以外的各种构成。
[实施例]
以下，通过实施例和比较例说明本发明，但本发明不限定于此。
＜实施例1＞
在具备搅拌装置、回流冷却器和温度计的反应装置中添加苯酚100重量份、37％福尔马林水溶液117重量份(F/P摩尔比＝1.2)、30％氨水溶液4重量份，在回流条件下反应40分钟。其后，一边在91kPa的减压条件下进行脱水，一边使体系内的温度达到70℃，此时加入20重量份的甲醇、15重量份的3,5-二甲基苯酚，在80℃下反应3小时。接下来，加入7重量份的甲醇、15重量份的甲苯，由此得到甲阶型酚醛树脂。得到的甲阶型酚醛树脂在分子结构中具有来自3,5-二甲基苯酚的结构单元和来自苯酚的结构单元。
将得到的甲阶型酚醛树脂混合在使聚乙烯醇缩丁醛树脂29重量份溶解在甲醇78重量份和甲苯6重量份中而成的溶液中，得到摩擦材料用粘接剂391重量份。
＜实施例2＞
相对于实施例1的摩擦材料用粘接剂添加间苯二酚3重量份，得到摩擦材料用粘接剂，除此以外，采用与实施例1相同的方法。
＜实施例3＞
使用5重量份的3,5-二甲基苯酚，除此以外，用与实施例1相同的方法制作甲阶型酚醛树脂和摩擦材料用粘接剂。得到的甲阶型酚醛树脂在分子结构中具有来自3,5-二甲基苯酚的结构单元和来自苯酚的结构单元。
＜实施例4＞
使用50重量份的3,5-二甲基苯酚，除此以外，用与实施例1相同的方法制作甲阶型酚醛树脂和摩擦材料用粘接剂。得到的甲阶型酚醛树脂在分子结构中具有来自3,5-二甲基苯酚的结构单元和来自苯酚的结构单元。
＜比较例1＞
未使用3,5-二甲基苯酚，除此以外，用与实施例1相同的方法制作甲阶型酚醛树脂和摩擦材料用粘接剂。应予说明，得到的甲阶型酚醛树脂虽然在分子结构中具有来自苯酚的结构单元，但不具有来自3,5-二甲基苯酚的结构单元。
使用实施例和比较例的摩擦材料用粘接剂进行以下评价。应予说明，确认用于制作实施例的甲阶型酚醛树脂的3,5-二甲基苯酚几乎全部反应。因此，二甲基苯酚改性率用后述方法进行计算。
·粘接强度：在2张酸洗处理钢板上涂布实施例或比较例的摩擦材料用粘接剂后，在80℃下实施15分钟干燥处理。接下来，以5MPa的压力条件在160℃下进行30分钟热压接处理，由此制作试验片。使用得到的试验片，按照JISK6850进行拉伸剪切试验，测定粘接强度。应予说明，单位为MPa。
·固化性：将实施例或比较例的摩擦材料用粘接剂2.5mL滴加到加热至165℃的模具，在通过目视确认的情况下，使该摩擦材料用粘接剂凝胶化，由此测定硫化曲线扭矩。其后，将达到90％扭矩的时间作为固化结束时间来评价摩擦材料用粘接剂的固化性。应予说明，单位为分钟。
·二甲基苯酚改性率：算出将甲阶型酚醛树脂的的制造中使用的3,5-二甲基苯酚的重量份数除以3,5-二甲基苯酚和苯酚的重量份数的合计值而得的值再乘以100而得到的值，作为二甲基苯酚改性率。应予说明，单位为％。
将与上述评价项目有关的评价结果与甲阶型酚醛树脂和摩擦材料用粘接剂的配合组成一起示于以下的表1。
[表1]
与比较例1的摩擦材料用粘接剂相比，使用实施例的摩擦材料用粘接剂时能够以短的粘接时间实现高的粘接强度。
该申请基于2015年3月31日申请的日本申请特愿2015-72169号主张优先权，将其公开的全部内容援引于此。
Claims (8)
1.一种摩擦材料用甲阶型酚醛树脂，是在用于粘接摩擦材料与金属基材的粘接剂中使用的摩擦材料用甲阶型酚醛树脂，
该摩擦材料用甲阶型酚醛树脂具有被二甲基苯酚类改性的下述式(1)表示的结构单元A和下述式(2)表示的结构单元B，
式(1)中，m为1以上的整数，m为1时，R为羟甲基，m为2以上时，R独立地为氢原子或羟甲基，且至少1个R为羟甲基，
式(2)中，n为1以上的整数，n为1时，R为羟甲基，n为2以上时，R独立地为氢原子或羟甲基，且至少1个R为羟甲基。
2.根据权利要求1所述的摩擦材料用甲阶型酚醛树脂，其中，所述二甲基苯酚类为3,5-二甲基苯酚。
3.根据权利要求1或2所述的摩擦材料用甲阶型酚醛树脂，其中，将相对于该摩擦材料用甲阶型酚醛树脂中含有的具有酚性羟基的全部的结构单元的所述结构单元A的比例作为二甲基苯酚改性率时，所述二甲基苯酚改性率为3％～50％。
4.一种摩擦材料用甲阶型酚醛树脂的制造方法，是在用于粘接摩擦材料与金属基材的粘接剂中使用的摩擦材料用甲阶型酚醛树脂的制造方法，包含：
第1工序，在碱性催化剂的存在下，使不包括二甲基苯酚类的酚类与醛类反应而得到第1反应生成物；
第2工序，在碱性催化剂的存在下，使所述第1反应生成物与二甲基苯酚类反应而得到甲阶型酚醛树脂。
5.根据权利要求4所述的摩擦材料用甲阶型酚醛树脂的制造方法，其中，在所述第2工序中反应的所述二甲基苯酚类的量相对于不包括所述二甲基苯酚类的酚类100重量份为5重量份～100重量份。
6.一种摩擦材料用粘接剂，含有权利要求1～3中任一项所述的摩擦材料用甲阶型酚醛树脂，和选自聚乙烯醇缩丁醛树脂、丁腈橡胶、苯乙烯-丁二烯橡胶和环氧树脂中的1种以上的弹性体。
7.根据权利要求6所述的摩擦材料用粘接剂，其中，进一步含有间苯二酚类。
8.一种湿式摩擦板，包含摩擦材料、金属基材、和介于所述摩擦材料与所述金属基材之间的权利要求6或7所述的摩擦材料用粘接剂。
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN111620989A (zh) * | 2019-02-27 | 2020-09-04 | Nsk沃纳株式会社 | 湿式摩擦材料用酚醛树脂、酚醛树脂组合物和湿式摩擦材料 |
| CN114599757A (zh) * | 2019-11-01 | 2022-06-07 | 住友电木株式会社 | 湿式摩擦材料用粘接剂组合物 |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP7172422B2 (ja) * | 2018-10-17 | 2022-11-16 | 住友ベークライト株式会社 | 湿式摩擦材用接着剤組成物 |
| US20240076533A1 (en) * | 2021-03-09 | 2024-03-07 | Ddp Specialty Electronic Materials Us, Llc | Advanced bonding agent |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2441860A (en) * | 1943-11-16 | 1948-05-18 | Shell Dev | Accelerated curing of phenol-form-aldehyde resins to the infusible state with 3, 5-xyenol |
| JPH09118730A (ja) * | 1995-10-26 | 1997-05-06 | Hitachi Chem Co Ltd | 積層板用フェノール樹脂組成物及び該フェノール樹脂組成物を用いたフェノール樹脂積層板 |
| CN104072942A (zh) * | 2013-03-27 | 2014-10-01 | 住友电木株式会社 | 湿式摩擦材料用树脂组合物、湿式摩擦材料用酚醛树脂及湿式摩擦材料 |
Family Cites Families (38)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2114121A (en) * | 1935-07-27 | 1938-04-12 | Bakelite Corp | Friction material |
| US3398107A (en) * | 1965-10-28 | 1968-08-20 | Exxon Research Engineering Co | Modified xylene-formaldehyde resins |
| DE1770816C3 (de) * | 1968-07-06 | 1973-10-18 | Reichhold-Albert-Chemie Ag, 2000 Hamburg | Verfahren zur Herstellung von flexiblen Phenolharzen |
| JPS4816352B1 (zh) * | 1970-12-28 | 1973-05-21 | ||
| US3761441A (en) * | 1972-02-02 | 1973-09-25 | Union Carbide Corp | Thermosetting friction compositions and friction elements thereof containing an acrylimide resin |
| US4197352A (en) * | 1977-12-22 | 1980-04-08 | Hooker Chemicals & Plastics Corp. | Composite friction assemblies and methods of making such assemblies |
| JPS5655732A (en) * | 1979-10-11 | 1981-05-16 | Sumitomo Electric Ind Ltd | Shoe for disc brake |
| US4268657A (en) * | 1979-12-10 | 1981-05-19 | Minnesota Mining And Manufacturing Company | Friction element containing phenol-formaldehyde-alkylphenol binder |
| US4316827A (en) * | 1980-04-17 | 1982-02-23 | Union Carbide Corporation | Rubber modified phenolic friction particles |
| US4420571A (en) * | 1980-04-17 | 1983-12-13 | Union Carbide Corporation | Phenolic friction particles |
| US4514462A (en) * | 1983-04-14 | 1985-04-30 | Westinghouse Electric Corp. | Warp resistant laminates having a core impregnated with a mixture of phenolix resin and alkyl substituted phenol |
| US4743634A (en) * | 1986-01-22 | 1988-05-10 | Raymark Industries, Inc. | Molded non-asbestos friction member containing diatomaceous earth |
| US5346799A (en) * | 1991-12-23 | 1994-09-13 | Ocg Microelectronic Materials, Inc. | Novolak resins and their use in radiation-sensitive compositions wherein the novolak resins are made by condensing 2,6-dimethylphenol, 2,3-dimethylphenol, a para-substituted phenol and an aldehyde |
| DE4206697A1 (de) * | 1992-03-04 | 1993-09-09 | Hoechst Ag | Verfahren zur herstellung von modifizierten phenolharzen |
| EP0606149B1 (en) * | 1993-01-05 | 2001-09-12 | Kao Corporation | Binder composition for mold and method for producing mold |
| US5516816A (en) * | 1993-02-12 | 1996-05-14 | Alliedsignal Inc. | Friction composition and friction element fabricated therefrom |
| JP3010963B2 (ja) * | 1993-02-17 | 2000-02-21 | 信越化学工業株式会社 | レジスト組成物 |
| US5721332A (en) * | 1994-05-16 | 1998-02-24 | Sumikin Chemical Co., Ltd. | Phenolic resin |
| US5750632A (en) * | 1994-12-30 | 1998-05-12 | Clariant Finance (Bvi) Limited | Isolation of novolak resin by low temperature sub surface forced steam distillation |
| US5645970A (en) * | 1995-10-25 | 1997-07-08 | Industrial Technology Research Institute | Weak base developable positive photoresist composition containing quinonediazide compound |
| FR2760503B1 (fr) * | 1997-03-06 | 1999-04-23 | Valeo | Garniture de frottement destinee a equiper un dispositif mettant en oeuvre un frottement a sec, procede de fabrication d'une telle garniture de frottement et disque de friction d'embrayage equipe d'une telle garniture |
| JPH10259368A (ja) * | 1997-03-18 | 1998-09-29 | Sumitomo Bakelite Co Ltd | 木材用接着剤 |
| US6022502A (en) * | 1997-09-30 | 2000-02-08 | Lockhart; Wayne | Composite friction assembly |
| WO2001096472A1 (fr) * | 2000-06-12 | 2001-12-20 | Mitsui Chemicals, Inc. | Composition de resine phenolique |
| JP2002226834A (ja) * | 2001-01-30 | 2002-08-14 | Nisshinbo Ind Inc | 非石綿系摩擦材 |
| DE10112620A1 (de) * | 2001-03-14 | 2002-09-19 | Bakelite Ag | Bindemittelmischungen und ihre Verwendung |
| JP4005350B2 (ja) * | 2001-12-14 | 2007-11-07 | 住友ベークライト株式会社 | 湿式摩擦材 |
| JP4053330B2 (ja) * | 2002-03-29 | 2008-02-27 | 住友ベークライト株式会社 | 湿式摩擦材用樹脂組成物および湿式摩擦材 |
| JP2004138121A (ja) * | 2002-10-16 | 2004-05-13 | Nsk Warner Kk | 湿式摩擦材 |
| JP4901085B2 (ja) * | 2004-09-14 | 2012-03-21 | 株式会社ダイナックス | 湿式摩擦板用接着剤 |
| US20060094853A1 (en) * | 2004-11-02 | 2006-05-04 | Hexion Specialty Chemicals, Inc. | Modified phenol-formaldehyde resole resins, methods of manufacture, methods of use, and articles formed therefrom |
| JP2006282972A (ja) * | 2005-04-05 | 2006-10-19 | Nsk Warner Kk | 湿式摩擦材 |
| JP5526891B2 (ja) * | 2010-03-15 | 2014-06-18 | セメダイン株式会社 | フェノール樹脂・ポリビニルアセタール樹脂系接着剤 |
| US9328188B2 (en) * | 2011-12-29 | 2016-05-03 | Industrial Technology Research Institute | Method for preparing phenol-formaldehyde resins, resin materials and method for preparing resin molding materials |
| JP5753518B2 (ja) * | 2012-07-04 | 2015-07-22 | 日清紡ブレーキ株式会社 | 摩擦材 |
| US8822123B2 (en) * | 2012-07-13 | 2014-09-02 | Momentive Specialty Chemicals Inc. | Polymeric materials and methods for making the polymeric materials |
| JP6044820B2 (ja) * | 2012-07-24 | 2016-12-14 | Dic株式会社 | 接着剤組成物及び湿式摩擦板 |
| WO2016159218A1 (ja) * | 2015-03-31 | 2016-10-06 | 住友ベークライト株式会社 | レゾール型変性フェノール樹脂組成物、その製造方法および接着剤 |
-
2015
- 2015-03-31 JP JP2015072169A patent/JP2016190968A/ja active Pending
-
2016
- 2016-03-31 US US15/087,232 patent/US10259902B2/en active Active
- 2016-03-31 CN CN201610200994.0A patent/CN106008866A/zh active Pending
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2441860A (en) * | 1943-11-16 | 1948-05-18 | Shell Dev | Accelerated curing of phenol-form-aldehyde resins to the infusible state with 3, 5-xyenol |
| JPH09118730A (ja) * | 1995-10-26 | 1997-05-06 | Hitachi Chem Co Ltd | 積層板用フェノール樹脂組成物及び該フェノール樹脂組成物を用いたフェノール樹脂積層板 |
| CN104072942A (zh) * | 2013-03-27 | 2014-10-01 | 住友电木株式会社 | 湿式摩擦材料用树脂组合物、湿式摩擦材料用酚醛树脂及湿式摩擦材料 |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN111620989A (zh) * | 2019-02-27 | 2020-09-04 | Nsk沃纳株式会社 | 湿式摩擦材料用酚醛树脂、酚醛树脂组合物和湿式摩擦材料 |
| CN114599757A (zh) * | 2019-11-01 | 2022-06-07 | 住友电木株式会社 | 湿式摩擦材料用粘接剂组合物 |
| CN114599757B (zh) * | 2019-11-01 | 2022-09-13 | 住友电木株式会社 | 湿式摩擦材料用粘接剂组合物 |
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