JPS6121268B2 - - Google Patents

Info

Publication number: JPS6121268B2
Authority: JP; Japan
Prior art keywords: rubber; parts; adhesive composition; potassium; adhesive
Prior art date: 1978-12-27
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.): Expired

Application number

JP16261678A

Other languages

English (en)

Japanese (ja)

Other versions

JPS5589370A (en

Inventor

Fumio Tashiro

Toyoji Toda

Takeshi Sando

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Resonac Corp

Original Assignee

Hitachi Chemical Co Ltd

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1978-12-27

Filing date

1978-12-27

Publication date

1986-05-26

1978-12-27 Application filed by Hitachi Chemical Co Ltd filed Critical Hitachi Chemical Co Ltd

1978-12-27 Priority to JP16261678A priority Critical patent/JPS5589370A/ja

1980-07-05 Publication of JPS5589370A publication Critical patent/JPS5589370A/ja

1986-05-26 Publication of JPS6121268B2 publication Critical patent/JPS6121268B2/ja

Status Granted legal-status Critical Current

Links

239000000853 adhesive Substances 0.000 claims description 48
230000001070 adhesive effect Effects 0.000 claims description 48
239000000203 mixture Substances 0.000 claims description 30
229920001971 elastomer Polymers 0.000 claims description 26
239000005060 rubber Substances 0.000 claims description 26
239000005011 phenolic resin Substances 0.000 claims description 19
KXGFMDJXCMQABM-UHFFFAOYSA-N 2-methoxy-6-methylphenol Chemical compound [CH]OC1=CC=CC([CH])=C1O KXGFMDJXCMQABM-UHFFFAOYSA-N 0.000 claims description 9
229920001568 phenolic resin Polymers 0.000 claims description 9
150000003112 potassium compounds Chemical class 0.000 claims description 7
229910044991 metal oxide Inorganic materials 0.000 claims description 6
150000004706 metal oxides Chemical class 0.000 claims description 6
230000001747 exhibiting effect Effects 0.000 claims description 5
238000006243 chemical reaction Methods 0.000 claims description 4
238000006482 condensation reaction Methods 0.000 claims description 3
125000002485 formyl group Chemical class [H]C(*)=O 0.000 claims 1
238000010438 heat treatment Methods 0.000 claims 1
230000020477 pH reduction Effects 0.000 claims 1
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 12
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 12
229920005989 resin Polymers 0.000 description 10
239000011347 resin Substances 0.000 description 10
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 7
ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 6
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
125000000217 alkyl group Chemical group 0.000 description 5
230000014759 maintenance of location Effects 0.000 description 5
238000005191 phase separation Methods 0.000 description 5
WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 4
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 4
XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 4
230000000052 comparative effect Effects 0.000 description 4
239000007788 liquid Substances 0.000 description 4
-1 methylol groups Chemical group 0.000 description 4
230000000704 physical effect Effects 0.000 description 4
229920001084 poly(chloroprene) Polymers 0.000 description 4
XXQBEVHPUKOQEO-UHFFFAOYSA-N potassium superoxide Chemical compound [K+].[K+].[O-][O-] XXQBEVHPUKOQEO-UHFFFAOYSA-N 0.000 description 4
LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 4
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
229920000459 Nitrile rubber Polymers 0.000 description 3
MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
238000007259 addition reaction Methods 0.000 description 3
150000001299 aldehydes Chemical class 0.000 description 3
125000003118 aryl group Chemical group 0.000 description 3
239000003795 chemical substances by application Substances 0.000 description 3
238000000034 method Methods 0.000 description 3
GJYCVCVHRSWLNY-UHFFFAOYSA-N 2-butylphenol Chemical compound CCCCC1=CC=CC=C1O GJYCVCVHRSWLNY-UHFFFAOYSA-N 0.000 description 2
QHPQWRBYOIRBIT-UHFFFAOYSA-N 4-tert-butylphenol Chemical compound CC(C)(C)C1=CC=C(O)C=C1 QHPQWRBYOIRBIT-UHFFFAOYSA-N 0.000 description 2
229930040373 Paraformaldehyde Natural products 0.000 description 2
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
230000002378 acidificating effect Effects 0.000 description 2
239000000654 additive Substances 0.000 description 2
RQPZNWPYLFFXCP-UHFFFAOYSA-L barium dihydroxide Chemical compound [OH-].[OH-].[Ba+2] RQPZNWPYLFFXCP-UHFFFAOYSA-L 0.000 description 2
229910001863 barium hydroxide Inorganic materials 0.000 description 2
LLEMOWNGBBNAJR-UHFFFAOYSA-N biphenyl-2-ol Chemical compound OC1=CC=CC=C1C1=CC=CC=C1 LLEMOWNGBBNAJR-UHFFFAOYSA-N 0.000 description 2
HYBBIBNJHNGZAN-UHFFFAOYSA-N furfural Chemical compound O=CC1=CC=CO1 HYBBIBNJHNGZAN-UHFFFAOYSA-N 0.000 description 2
VKYKSIONXSXAKP-UHFFFAOYSA-N hexamethylenetetramine Chemical compound C1N(C2)CN3CN1CN2C3 VKYKSIONXSXAKP-UHFFFAOYSA-N 0.000 description 2
229910052742 iron Inorganic materials 0.000 description 2
239000000395 magnesium oxide Substances 0.000 description 2
CPLXHLVBOLITMK-UHFFFAOYSA-N magnesium oxide Inorganic materials [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 2
AXZKOIWUVFPNLO-UHFFFAOYSA-N magnesium;oxygen(2-) Chemical compound [O-2].[Mg+2] AXZKOIWUVFPNLO-UHFFFAOYSA-N 0.000 description 2
238000004519 manufacturing process Methods 0.000 description 2
BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
150000007522 mineralic acids Chemical class 0.000 description 2
239000012046 mixed solvent Substances 0.000 description 2
150000007524 organic acids Chemical class 0.000 description 2
229920002866 paraformaldehyde Polymers 0.000 description 2
IOLCXVTUBQKXJR-UHFFFAOYSA-M potassium bromide Chemical compound [K+].[Br-] IOLCXVTUBQKXJR-UHFFFAOYSA-M 0.000 description 2
CHWRSCGUEQEHOH-UHFFFAOYSA-N potassium oxide Chemical compound [O-2].[K+].[K+] CHWRSCGUEQEHOH-UHFFFAOYSA-N 0.000 description 2
229910001950 potassium oxide Inorganic materials 0.000 description 2
238000004904 shortening Methods 0.000 description 2
150000003505 terpenes Chemical class 0.000 description 2
235000007586 terpenes Nutrition 0.000 description 2
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
239000011787 zinc oxide Substances 0.000 description 2
CJWNFAKWHDOUKL-UHFFFAOYSA-N 2-(2-phenylpropan-2-yl)phenol Chemical class C=1C=CC=C(O)C=1C(C)(C)C1=CC=CC=C1 CJWNFAKWHDOUKL-UHFFFAOYSA-N 0.000 description 1
CYEJMVLDXAUOPN-UHFFFAOYSA-N 2-dodecylphenol Chemical compound CCCCCCCCCCCCC1=CC=CC=C1O CYEJMVLDXAUOPN-UHFFFAOYSA-N 0.000 description 1
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 description 1
MEEKGULDSDXFCN-UHFFFAOYSA-N 2-pentylphenol Chemical compound CCCCCC1=CC=CC=C1O MEEKGULDSDXFCN-UHFFFAOYSA-N 0.000 description 1
WJQOZHYUIDYNHM-UHFFFAOYSA-N 2-tert-Butylphenol Chemical compound CC(C)(C)C1=CC=CC=C1O WJQOZHYUIDYNHM-UHFFFAOYSA-N 0.000 description 1
OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
244000043261 Hevea brasiliensis Species 0.000 description 1
229920000877 Melamine resin Polymers 0.000 description 1
IGFHQQFPSIBGKE-UHFFFAOYSA-N Nonylphenol Natural products CCCCCCCCCC1=CC=C(O)C=C1 IGFHQQFPSIBGKE-UHFFFAOYSA-N 0.000 description 1
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
235000021355 Stearic acid Nutrition 0.000 description 1
GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 1
229920006311 Urethane elastomer Polymers 0.000 description 1
235000011054 acetic acid Nutrition 0.000 description 1
229910000272 alkali metal oxide Inorganic materials 0.000 description 1
150000001340 alkali metals Chemical class 0.000 description 1
229910001860 alkaline earth metal hydroxide Inorganic materials 0.000 description 1
229910000147 aluminium phosphate Inorganic materials 0.000 description 1
150000001412 amines Chemical class 0.000 description 1
230000003712 anti-aging effect Effects 0.000 description 1
YXVFYQXJAXKLAK-UHFFFAOYSA-N biphenyl-4-ol Chemical compound C1=CC(O)=CC=C1C1=CC=CC=C1 YXVFYQXJAXKLAK-UHFFFAOYSA-N 0.000 description 1
239000004566 building material Substances 0.000 description 1
AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 description 1
239000000920 calcium hydroxide Substances 0.000 description 1
229910001861 calcium hydroxide Inorganic materials 0.000 description 1
239000000378 calcium silicate Substances 0.000 description 1
229910052918 calcium silicate Inorganic materials 0.000 description 1
OYACROKNLOSFPA-UHFFFAOYSA-N calcium;dioxido(oxo)silane Chemical compound [Ca+2].[O-][Si]([O-])=O OYACROKNLOSFPA-UHFFFAOYSA-N 0.000 description 1
239000006229 carbon black Substances 0.000 description 1
239000007809 chemical reaction catalyst Substances 0.000 description 1
YACLQRRMGMJLJV-UHFFFAOYSA-N chloroprene Chemical compound ClC(=C)C=C YACLQRRMGMJLJV-UHFFFAOYSA-N 0.000 description 1
238000013329 compounding Methods 0.000 description 1
238000007796 conventional method Methods 0.000 description 1
229930003836 cresol Natural products 0.000 description 1
230000000694 effects Effects 0.000 description 1
229920005558 epichlorohydrin rubber Polymers 0.000 description 1
239000003822 epoxy resin Substances 0.000 description 1
238000001914 filtration Methods 0.000 description 1
235000019253 formic acid Nutrition 0.000 description 1
238000009472 formulation Methods 0.000 description 1
LNEPOXFFQSENCJ-UHFFFAOYSA-N haloperidol Chemical compound C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 LNEPOXFFQSENCJ-UHFFFAOYSA-N 0.000 description 1
239000004312 hexamethylene tetramine Substances 0.000 description 1
235000010299 hexamethylene tetramine Nutrition 0.000 description 1
150000002576 ketones Chemical class 0.000 description 1
238000004898 kneading Methods 0.000 description 1
VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
239000011976 maleic acid Substances 0.000 description 1
238000005259 measurement Methods 0.000 description 1
JDSHMPZPIAZGSV-UHFFFAOYSA-N melamine Chemical compound NC1=NC(N)=NC(N)=N1 JDSHMPZPIAZGSV-UHFFFAOYSA-N 0.000 description 1
229920003052 natural elastomer Polymers 0.000 description 1
229920001194 natural rubber Polymers 0.000 description 1
SNQQPOLDUKLAAF-UHFFFAOYSA-N nonylphenol Chemical compound CCCCCCCCCC1=CC=CC=C1O SNQQPOLDUKLAAF-UHFFFAOYSA-N 0.000 description 1
QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
235000005985 organic acids Nutrition 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
235000006408 oxalic acid Nutrition 0.000 description 1
239000003208 petroleum Substances 0.000 description 1
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
229920000647 polyepoxide Polymers 0.000 description 1
229910052700 potassium Inorganic materials 0.000 description 1
239000011591 potassium Substances 0.000 description 1
229910000028 potassium bicarbonate Inorganic materials 0.000 description 1
235000015497 potassium bicarbonate Nutrition 0.000 description 1
239000011736 potassium bicarbonate Substances 0.000 description 1
TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
238000001556 precipitation Methods 0.000 description 1
230000035484 reaction time Effects 0.000 description 1
230000009257 reactivity Effects 0.000 description 1
150000003839 salts Chemical class 0.000 description 1
229910001220 stainless steel Inorganic materials 0.000 description 1
239000010935 stainless steel Substances 0.000 description 1
239000008117 stearic acid Substances 0.000 description 1
238000003756 stirring Methods 0.000 description 1
238000003860 storage Methods 0.000 description 1
229920003048 styrene butadiene rubber Polymers 0.000 description 1
OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
238000004073 vulcanization Methods 0.000 description 1
238000005406 washing Methods 0.000 description 1
239000008096 xylene Substances 0.000 description 1

Landscapes

Compositions Of Macromolecular Compounds (AREA)
Adhesives Or Adhesive Processes (AREA)

JP16261678A 1978-12-27 1978-12-27 Rubber adhesive composition Granted JPS5589370A (en)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
JP16261678A JPS5589370A (en)	1978-12-27	1978-12-27	Rubber adhesive composition

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
JP16261678A JPS5589370A (en)	1978-12-27	1978-12-27	Rubber adhesive composition

Publications (2)

Publication Number	Publication Date
JPS5589370A JPS5589370A (en)	1980-07-05
JPS6121268B2 true JPS6121268B2 (de)	1986-05-26

Family

ID=15757979

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
JP16261678A Granted JPS5589370A (en)	1978-12-27	1978-12-27	Rubber adhesive composition

Country Status (1)

Country	Link
JP (1)	JPS5589370A (de)

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4456727A (en) *	1982-04-30	1984-06-26	Phillips Petroleum Company	Phenol-formaldehyde resins as additives for solution-polymerized copolymers of conjugated alkadienes and vinyl arenes
JPH01132672A (ja) *	1987-11-17	1989-05-25	Saiden Kagaku Kk	感熱性接着剤組成物
JP5830938B2 (ja) *	2011-05-30	2015-12-09	横浜ゴム株式会社	タイヤ用ゴム組成物およびそれを用いた空気入りタイヤの製造方法
JP5772227B2 (ja) *	2011-05-30	2015-09-02	横浜ゴム株式会社	重荷重用タイヤトレッド用ゴム組成物およびそれを用いた空気入りタイヤ

1978
- 1978-12-27 JP JP16261678A patent/JPS5589370A/ja active Granted

Also Published As

Publication number	Publication date
JPS5589370A (en)	1980-07-05

Publication	Publication Date	Title
US4257926A (en)	1981-03-24	Adhesion of rubber to reinforcing materials
JP2784610B2 (ja)	1998-08-06	高温接着剤組成物
SU1579920A1 (ru)	1990-07-23	Клеева композици
JP3461040B2 (ja)	2003-10-27	ゴム系接着剤組成物
JPS6121268B2 (de)	1986-05-26
US4260704A (en)	1981-04-07	Resins based on novolaks, their production and their use as tackifiers
US4032511A (en)	1977-06-28	Process for the production of phenol silicate compounds and their condensation products
US3471443A (en)	1969-10-07	Curing phenol-aldehyde novolak resins employing aniline or aniline hcl
USRE29157E (en)	1977-03-22	High temperature resistant polychloroprene adhesive resin
JP2850360B2 (ja)	1999-01-27	合板用接着剤
JP3594105B2 (ja)	2004-11-24	加硫接着剤組成物
JP2006160909A (ja)	2006-06-22	クロロプレンゴム接着剤組成物
JPH08109233A (ja)	1996-04-30	接着用プライマーの成分のためのフェノール・レゾルシン樹脂の製造方法、接着用プライマー及びゴムと補強材との接着方法
JPS61138614A (ja)	1986-06-26	フエノ−ルノボラツクの製造方法
JPS62212411A (ja)	1987-09-18	変性フエノ−ル樹脂の製造法
EP0126625B1 (de)	1991-09-04	Verfahren zur Herstellung von Phenol-Verbindungen und -Harzen
JP4865303B2 (ja)	2012-02-01	クロロプレンゴム接着剤組成物
JPH11131039A (ja)	1999-05-18	木材用接着剤
JPH04175323A (ja)	1992-06-23	粘着性付与樹脂の製造法
US2576735A (en)	1951-11-27	Nitrogenous resins from ketonealdehyde-nitrogenous base and phenol-aldehyde
KR0161802B1 (ko)	1999-01-15	가구용 고강도 속경화형 접착제
US2510837A (en)	1950-06-06	Method of preparing resinous reaction products from a phenol-formaldehyde condensate and a monohydric alcohol ester of rosin
JPH09124531A (ja)	1997-05-13	メチル置換ポリアルキリデンポリフェノール類の製造方法
TW202219094A (zh)	2022-05-16	水溶性甲階型酚醛樹脂
JP4126898B2 (ja)	2008-07-30	加硫接着剤組成物