JPH0122849B2 - - Google Patents

Info

Publication number: JPH0122849B2
Authority: JP; Japan
Prior art keywords: amines; phenols; curing agent; unreacted; mol
Prior art date: 1981-05-25
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

JP7910181A

Other languages

English (en)

Japanese (ja)

Other versions

JPS57195118A (en

Inventor

Akira Myamoto

Katsuo Sato

Shigeo Mine

Takeshige Kasuya

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.)

Mitsubishi Gas Chemical Co Inc

Original Assignee

Mitsubishi Gas Chemical Co Inc

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.)

1981-05-25

Filing date

1981-05-25

Publication date

1989-04-28

1981-05-25 Application filed by Mitsubishi Gas Chemical Co Inc filed Critical Mitsubishi Gas Chemical Co Inc

1981-05-25 Priority to JP7910181A priority Critical patent/JPS57195118A/ja

1982-05-25 Priority to EP82302683A priority patent/EP0066447A1/fr

1982-11-30 Publication of JPS57195118A publication Critical patent/JPS57195118A/ja

1989-04-28 Publication of JPH0122849B2 publication Critical patent/JPH0122849B2/ja

Status Granted legal-status Critical Current

Links

WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims description 46
150000001412 amines Chemical class 0.000 claims description 37
150000002989 phenols Chemical class 0.000 claims description 36
239000003795 chemical substances by application Substances 0.000 claims description 30
239000003822 epoxy resin Substances 0.000 claims description 23
229920000647 polyepoxide Polymers 0.000 claims description 23
239000007795 chemical reaction product Substances 0.000 claims description 22
NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 claims description 12
238000006243 chemical reaction Methods 0.000 claims description 12
239000000203 mixture Substances 0.000 claims description 9
238000003756 stirring Methods 0.000 claims description 8
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 8
239000011541 reaction mixture Substances 0.000 claims description 5
238000004519 manufacturing process Methods 0.000 claims description 4
238000000034 method Methods 0.000 description 19
239000000047 product Substances 0.000 description 18
150000001299 aldehydes Chemical class 0.000 description 15
IVSZLXZYQVIEFR-UHFFFAOYSA-N 1,3-Dimethylbenzene Natural products CC1=CC=CC(C)=C1 IVSZLXZYQVIEFR-UHFFFAOYSA-N 0.000 description 9
QWVGKYWNOKOFNN-UHFFFAOYSA-N o-cresol Chemical compound CC1=CC=CC=C1O QWVGKYWNOKOFNN-UHFFFAOYSA-N 0.000 description 9
-1 octylphenol Chemical compound 0.000 description 6
229920000768 polyamine Polymers 0.000 description 5
239000000126 substance Substances 0.000 description 5
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 4
230000000052 comparative effect Effects 0.000 description 4
229910001873 dinitrogen Inorganic materials 0.000 description 4
230000000704 physical effect Effects 0.000 description 4
WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 3
239000003085 diluting agent Substances 0.000 description 3
WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 description 3
NFIDBGJMFKNGGQ-UHFFFAOYSA-N 2-(2-methylpropyl)phenol Chemical compound CC(C)CC1=CC=CC=C1O NFIDBGJMFKNGGQ-UHFFFAOYSA-N 0.000 description 2
CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
206010040880 Skin irritation Diseases 0.000 description 2
125000001931 aliphatic group Chemical group 0.000 description 2
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 2
239000003054 catalyst Substances 0.000 description 2
150000001875 compounds Chemical class 0.000 description 2
230000032798 delamination Effects 0.000 description 2
239000007789 gas Substances 0.000 description 2
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 2
NAQMVNRVTILPCV-UHFFFAOYSA-N hexane-1,6-diamine Chemical compound NCCCCCCN NAQMVNRVTILPCV-UHFFFAOYSA-N 0.000 description 2
238000002156 mixing Methods 0.000 description 2
KIDHWZJUCRJVML-UHFFFAOYSA-N putrescine Chemical compound NCCCCN KIDHWZJUCRJVML-UHFFFAOYSA-N 0.000 description 2
230000036556 skin irritation Effects 0.000 description 2
231100000475 skin irritation Toxicity 0.000 description 2
238000001308 synthesis method Methods 0.000 description 2
BGJSXRVXTHVRSN-UHFFFAOYSA-N 1,3,5-trioxane Chemical compound C1OCOCO1 BGJSXRVXTHVRSN-UHFFFAOYSA-N 0.000 description 1
VILCJCGEZXAXTO-UHFFFAOYSA-N 2,2,2-tetramine Chemical compound NCCNCCNCCN VILCJCGEZXAXTO-UHFFFAOYSA-N 0.000 description 1
YSUQLAYJZDEMOT-UHFFFAOYSA-N 2-(butoxymethyl)oxirane Chemical compound CCCCOCC1CO1 YSUQLAYJZDEMOT-UHFFFAOYSA-N 0.000 description 1
CDMGNVWZXRKJNS-UHFFFAOYSA-N 2-benzylphenol Chemical compound OC1=CC=CC=C1CC1=CC=CC=C1 CDMGNVWZXRKJNS-UHFFFAOYSA-N 0.000 description 1
229930185605 Bisphenol Natural products 0.000 description 1
RPNUMPOLZDHAAY-UHFFFAOYSA-N Diethylenetriamine Chemical compound NCCNCCN RPNUMPOLZDHAAY-UHFFFAOYSA-N 0.000 description 1
239000004593 Epoxy Substances 0.000 description 1
PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 1
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
IGFHQQFPSIBGKE-UHFFFAOYSA-N Nonylphenol Natural products CCCCCCCCCC1=CC=C(O)C=C1 IGFHQQFPSIBGKE-UHFFFAOYSA-N 0.000 description 1
229930040373 Paraformaldehyde Natural products 0.000 description 1
FQYUMYWMJTYZTK-UHFFFAOYSA-N Phenyl glycidyl ether Chemical compound C1OC1COC1=CC=CC=C1 FQYUMYWMJTYZTK-UHFFFAOYSA-N 0.000 description 1
QLBRROYTTDFLDX-UHFFFAOYSA-N [3-(aminomethyl)cyclohexyl]methanamine Chemical compound NCC1CCCC(CN)C1 QLBRROYTTDFLDX-UHFFFAOYSA-N 0.000 description 1
239000000654 additive Substances 0.000 description 1
230000001070 adhesive effect Effects 0.000 description 1
230000002411 adverse Effects 0.000 description 1
IMUDHTPIFIBORV-UHFFFAOYSA-N aminoethylpiperazine Chemical compound NCCN1CCNCC1 IMUDHTPIFIBORV-UHFFFAOYSA-N 0.000 description 1
125000003118 aryl group Chemical group 0.000 description 1
235000019445 benzyl alcohol Nutrition 0.000 description 1
LLEMOWNGBBNAJR-UHFFFAOYSA-N biphenyl-2-ol Chemical compound OC1=CC=CC=C1C1=CC=CC=C1 LLEMOWNGBBNAJR-UHFFFAOYSA-N 0.000 description 1
239000001569 carbon dioxide Substances 0.000 description 1
229910002092 carbon dioxide Inorganic materials 0.000 description 1
238000000576 coating method Methods 0.000 description 1
230000007797 corrosion Effects 0.000 description 1
238000005260 corrosion Methods 0.000 description 1
ZWAJLVLEBYIOTI-UHFFFAOYSA-N cyclohexene oxide Chemical compound C1CCCC2OC21 ZWAJLVLEBYIOTI-UHFFFAOYSA-N 0.000 description 1
FWFSEYBSWVRWGL-UHFFFAOYSA-N cyclohexene oxide Natural products O=C1CCCC=C1 FWFSEYBSWVRWGL-UHFFFAOYSA-N 0.000 description 1
230000007547 defect Effects 0.000 description 1
230000002939 deleterious effect Effects 0.000 description 1
PVAONLSZTBKFKM-UHFFFAOYSA-N diphenylmethanediol Chemical compound C=1C=CC=CC=1C(O)(O)C1=CC=CC=C1 PVAONLSZTBKFKM-UHFFFAOYSA-N 0.000 description 1
230000000694 effects Effects 0.000 description 1
239000000945 filler Substances 0.000 description 1
239000008098 formaldehyde solution Substances 0.000 description 1
OIAUFEASXQPCFE-UHFFFAOYSA-N formaldehyde;1,3-xylene Chemical compound O=C.CC1=CC=CC(C)=C1 OIAUFEASXQPCFE-UHFFFAOYSA-N 0.000 description 1
239000000383 hazardous chemical Substances 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
239000001257 hydrogen Substances 0.000 description 1
229910052739 hydrogen Inorganic materials 0.000 description 1
125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
239000007788 liquid Substances 0.000 description 1
RLSSMJSEOOYNOY-UHFFFAOYSA-N m-cresol Chemical compound CC1=CC=CC(O)=C1 RLSSMJSEOOYNOY-UHFFFAOYSA-N 0.000 description 1
LSHROXHEILXKHM-UHFFFAOYSA-N n'-[2-[2-[2-(2-aminoethylamino)ethylamino]ethylamino]ethyl]ethane-1,2-diamine Chemical compound NCCNCCNCCNCCNCCN LSHROXHEILXKHM-UHFFFAOYSA-N 0.000 description 1
SNQQPOLDUKLAAF-UHFFFAOYSA-N nonylphenol Chemical compound CCCCCCCCCC1=CC=CC=C1O SNQQPOLDUKLAAF-UHFFFAOYSA-N 0.000 description 1
229920003986 novolac Polymers 0.000 description 1
GJYCVCVHRSWLNY-UHFFFAOYSA-N ortho-butylphenol Natural products CCCCC1=CC=CC=C1O GJYCVCVHRSWLNY-UHFFFAOYSA-N 0.000 description 1
IWDCLRJOBJJRNH-UHFFFAOYSA-N p-cresol Chemical compound CC1=CC=C(O)C=C1 IWDCLRJOBJJRNH-UHFFFAOYSA-N 0.000 description 1
229920002866 paraformaldehyde Polymers 0.000 description 1
WVDDGKGOMKODPV-ZQBYOMGUSA-N phenyl(114C)methanol Chemical compound O[14CH2]C1=CC=CC=C1 WVDDGKGOMKODPV-ZQBYOMGUSA-N 0.000 description 1
239000000049 pigment Substances 0.000 description 1
231100000614 poison Toxicity 0.000 description 1
230000007096 poisonous effect Effects 0.000 description 1
239000002994 raw material Substances 0.000 description 1
239000007787 solid Substances 0.000 description 1
239000002904 solvent Substances 0.000 description 1
150000003512 tertiary amines Chemical class 0.000 description 1
FAGUFWYHJQFNRV-UHFFFAOYSA-N tetraethylenepentamine Chemical compound NCCNCCNCCNCCN FAGUFWYHJQFNRV-UHFFFAOYSA-N 0.000 description 1
150000003739 xylenols Chemical class 0.000 description 1

Landscapes

Compositions Of Macromolecular Compounds (AREA)
Phenolic Resins Or Amino Resins (AREA)
Epoxy Resins (AREA)

JP7910181A 1981-05-25 1981-05-25 Preparation of curing agent for epoxy resin Granted JPS57195118A (en)

Priority Applications (2)

Application Number	Priority Date	Filing Date	Title
JP7910181A JPS57195118A (en)	1981-05-25	1981-05-25	Preparation of curing agent for epoxy resin
EP82302683A EP0066447A1 (fr)	1981-05-25	1982-05-25	Réaction d'un phénol, d'une aldéhyde et d'une amine pour produire un agent de durcissement pour le résines epoxy

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
JP7910181A JPS57195118A (en)	1981-05-25	1981-05-25	Preparation of curing agent for epoxy resin

Publications (2)

Publication Number	Publication Date
JPS57195118A JPS57195118A (en)	1982-11-30
JPH0122849B2 true JPH0122849B2 (fr)	1989-04-28

Family

ID=13680484

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
JP7910181A Granted JPS57195118A (en)	1981-05-25	1981-05-25	Preparation of curing agent for epoxy resin

Country Status (1)

Country	Link
JP (1)	JPS57195118A (fr)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JPS58219220A (ja) *	1982-06-14	1983-12-20	Daito Sangyo Kk	エポキシ樹脂硬化剤
CN1048741C (zh) *	1996-05-03	2000-01-26	左新民	酚醛改性固化剂及其制备方法

1981
- 1981-05-25 JP JP7910181A patent/JPS57195118A/ja active Granted

Also Published As

Publication number	Publication date
JPS57195118A (en)	1982-11-30

Publication	Publication Date	Title
JP2661678B2 (ja)	1997-10-08	水分散性ポリアミン−エポキシアダクト及びエポキシ塗布組成物
US5204385A (en)	1993-04-20	Water reducible epoxy resin curing agent
WO2016049832A1 (fr)	2016-04-07	Composition époxyde
EP0066447A1 (fr)	1982-12-08	Réaction d'un phénol, d'une aldéhyde et d'une amine pour produire un agent de durcissement pour le résines epoxy
JPH09124773A (ja)	1997-05-13	水に担持された二成分コーティング系に使用するための伸長されたポリアミン付加物エポキシ樹脂硬化剤
EP0114875B1 (fr)	1989-11-02	Procede de production d'agents de polymerisation de phenol-formaldehyde-polyamine pour des resines epoxydes
US4368299A (en)	1983-01-11	Epoxy resin compositions
JPS59223716A (ja)	1984-12-15	改質アスフアルト−エポキシ樹脂組成物
JPS6253530B2 (fr)	1987-11-11
CN108794984B (zh)	2021-07-09	一种耐冲击高热残重的改性环氧树脂及其制备方法和用途
JP2003528952A (ja)	2003-09-30	アルキルジプロピレントリアミンをベースとするマンニッヒ塩基及びさらなる化合物
JPS5817776B2 (ja)	1983-04-09	被覆の製造法
US3036975A (en)	1962-05-29	Rapid-curing epoxy resin compositions and method of making
JPH0122849B2 (fr)	1989-04-28
JP4265023B2 (ja)	2009-05-20	フェノール系樹脂の製造方法
JP2015519293A (ja)	2015-07-09	ガラス質炭素組成物
JPS62127140A (ja)	1987-06-09	シエルモ−ルド用樹脂被覆砂
JPH1081733A (ja)	1998-03-31	エポキシ樹脂系用硬化剤
JPWO2023084913A5 (fr)	2024-07-25
JP4562241B2 (ja)	2010-10-13	エポキシ樹脂組成物
JPH0363968B2 (fr)	1991-10-03
JPS6222812A (ja)	1987-01-31	熱硬化性樹脂組成物
JPS6056168B2 (ja)	1985-12-09	アミン変性物の製造法
JPH11130840A (ja)	1999-05-18	エポキシ樹脂用硬化剤及びエポキシ樹脂組成物
US3950309A (en)	1976-04-13	Novel thermosetting resins and process for preparing the same comprising reacting a novolak with a titanic acid ester