CA1181194A - Epoxy curing stystem - Google Patents

Epoxy curing stystem

Info

Publication number: CA1181194A
Authority: CA; Canada
Prior art keywords: salicylic acid; epoxy resin; combination; methyliminobispropylamine; amount
Prior art date: 1979-11-02
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

CA000362405A

Other languages

English (en)

French (fr)

Inventor

Harold G. Waddill

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.)

Texaco Development Corp

Original Assignee

Texaco Development Corp

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.)

1979-11-02

Filing date

1980-10-15

Publication date

1985-01-15

1980-10-15 Application filed by Texaco Development Corp filed Critical Texaco Development Corp

1985-01-15 Application granted granted Critical

1985-01-15 Publication of CA1181194A publication Critical patent/CA1181194A/en

Status Expired legal-status Critical Current

Links

239000004593 Epoxy Substances 0.000 title description 10
229920000647 polyepoxide Polymers 0.000 claims abstract description 53
YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 claims abstract description 50
239000003822 epoxy resin Substances 0.000 claims abstract description 26
FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 claims abstract description 25
229960004889 salicylic acid Drugs 0.000 claims abstract description 25
KMBPCQSCMCEPMU-UHFFFAOYSA-N n'-(3-aminopropyl)-n'-methylpropane-1,3-diamine Chemical compound NCCCN(C)CCCN KMBPCQSCMCEPMU-UHFFFAOYSA-N 0.000 claims abstract description 12
239000000203 mixture Substances 0.000 claims description 20
150000002118 epoxides Chemical class 0.000 claims description 5
238000000034 method Methods 0.000 claims description 5
238000002347 injection Methods 0.000 claims description 4
239000007924 injection Substances 0.000 claims description 4
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 claims description 2
GYZLOYUZLJXAJU-UHFFFAOYSA-N diglycidyl ether Chemical compound C1OC1COCC1CO1 GYZLOYUZLJXAJU-UHFFFAOYSA-N 0.000 claims description 2
239000011872 intimate mixture Substances 0.000 claims description 2
239000011342 resin composition Substances 0.000 claims 2
229920005989 resin Polymers 0.000 abstract description 9
239000011347 resin Substances 0.000 abstract description 9
YXVIXWDTSCFZHY-UHFFFAOYSA-N 3-imino-N-methyl-N-propylpropan-1-amine Chemical compound CN(CCC=N)CCC YXVIXWDTSCFZHY-UHFFFAOYSA-N 0.000 description 12
239000003795 chemical substances by application Substances 0.000 description 12
-1 amine salts Chemical class 0.000 description 8
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 7
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 6
239000000463 material Substances 0.000 description 4
GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 description 4
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 3
ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 3
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
150000001875 compounds Chemical class 0.000 description 3
125000003700 epoxy group Chemical group 0.000 description 3
229920003986 novolac Polymers 0.000 description 3
238000010107 reaction injection moulding Methods 0.000 description 3
150000005846 sugar alcohols Polymers 0.000 description 3
MQXNNWDXHFBFEB-UHFFFAOYSA-N 2,2-bis(2-hydroxyphenyl)propane Chemical compound C=1C=CC=C(O)C=1C(C)(C)C1=CC=CC=C1O MQXNNWDXHFBFEB-UHFFFAOYSA-N 0.000 description 2
FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 2
FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 description 2
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 2
ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 2
150000001412 amines Chemical class 0.000 description 2
239000003054 catalyst Substances 0.000 description 2
239000000470 constituent Substances 0.000 description 2
235000011187 glycerol Nutrition 0.000 description 2
229960005150 glycerol Drugs 0.000 description 2
229940090044 injection Drugs 0.000 description 2
239000003973 paint Substances 0.000 description 2
WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 2
150000002989 phenols Chemical class 0.000 description 2
229920000570 polyether Polymers 0.000 description 2
HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 2
239000000600 sorbitol Substances 0.000 description 2
235000010356 sorbitol Nutrition 0.000 description 2
CNHDIAIOKMXOLK-UHFFFAOYSA-N toluquinol Chemical compound CC1=CC(O)=CC=C1O CNHDIAIOKMXOLK-UHFFFAOYSA-N 0.000 description 2
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
VBICKXHEKHSIBG-UHFFFAOYSA-N 1-monostearoylglycerol Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCC(O)CO VBICKXHEKHSIBG-UHFFFAOYSA-N 0.000 description 1
XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 1
TXBCBTDQIULDIA-UHFFFAOYSA-N 2-[[3-hydroxy-2,2-bis(hydroxymethyl)propoxy]methyl]-2-(hydroxymethyl)propane-1,3-diol Chemical compound OCC(CO)(CO)COCC(CO)(CO)CO TXBCBTDQIULDIA-UHFFFAOYSA-N 0.000 description 1
AGNTUZCMJBTHOG-UHFFFAOYSA-N 3-[3-(2,3-dihydroxypropoxy)-2-hydroxypropoxy]propane-1,2-diol Chemical compound OCC(O)COCC(O)COCC(O)CO AGNTUZCMJBTHOG-UHFFFAOYSA-N 0.000 description 1
FBPFZTCFMRRESA-KVTDHHQDSA-N D-Mannitol Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KVTDHHQDSA-N 0.000 description 1
239000004386 Erythritol Substances 0.000 description 1
UNXHWFMMPAWVPI-UHFFFAOYSA-N Erythritol Natural products OCC(O)C(O)CO UNXHWFMMPAWVPI-UHFFFAOYSA-N 0.000 description 1
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
229930195725 Mannitol Natural products 0.000 description 1
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
239000004743 Polypropylene Substances 0.000 description 1
DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical class CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 1
ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 1
OORDEDRRTSWSRC-UHFFFAOYSA-N [3-hydroxy-2,2-bis(hydroxymethyl)propyl] acetate Chemical compound CC(=O)OCC(CO)(CO)CO OORDEDRRTSWSRC-UHFFFAOYSA-N 0.000 description 1
BWVAOONFBYYRHY-UHFFFAOYSA-N [4-(hydroxymethyl)phenyl]methanol Chemical compound OCC1=CC=C(CO)C=C1 BWVAOONFBYYRHY-UHFFFAOYSA-N 0.000 description 1
239000002253 acid Substances 0.000 description 1
239000000654 additive Substances 0.000 description 1
150000001298 alcohols Chemical class 0.000 description 1
125000001931 aliphatic group Chemical group 0.000 description 1
150000008064 anhydrides Chemical class 0.000 description 1
125000003118 aryl group Chemical group 0.000 description 1
WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical class OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 1
238000005266 casting Methods 0.000 description 1
238000000576 coating method Methods 0.000 description 1
229940000425 combination drug Drugs 0.000 description 1
238000007796 conventional method Methods 0.000 description 1
MIHINWMALJZIBX-UHFFFAOYSA-N cyclohexa-2,4-dien-1-ol Chemical compound OC1CC=CC=C1 MIHINWMALJZIBX-UHFFFAOYSA-N 0.000 description 1
239000000539 dimer Substances 0.000 description 1
WQABCVAJNWAXTE-UHFFFAOYSA-N dimercaprol Chemical compound OCC(S)CS WQABCVAJNWAXTE-UHFFFAOYSA-N 0.000 description 1
239000000975 dye Substances 0.000 description 1
UNXHWFMMPAWVPI-ZXZARUISSA-N erythritol Chemical compound OC[C@H](O)[C@H](O)CO UNXHWFMMPAWVPI-ZXZARUISSA-N 0.000 description 1
235000019414 erythritol Nutrition 0.000 description 1
229940009714 erythritol Drugs 0.000 description 1
150000002148 esters Chemical class 0.000 description 1
RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 1
239000000945 filler Substances 0.000 description 1
ZZUFCTLCJUWOSV-UHFFFAOYSA-N furosemide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC(C(O)=O)=C1NCC1=CC=CO1 ZZUFCTLCJUWOSV-UHFFFAOYSA-N 0.000 description 1
239000011521 glass Substances 0.000 description 1
230000009477 glass transition Effects 0.000 description 1
125000003055 glycidyl group Chemical group C(C1CO1)* 0.000 description 1
150000002334 glycols Chemical class 0.000 description 1
125000000623 heterocyclic group Chemical group 0.000 description 1
UFAPLAOEQMMKJA-UHFFFAOYSA-N hexane-1,2,5-triol Chemical compound CC(O)CCC(O)CO UFAPLAOEQMMKJA-UHFFFAOYSA-N 0.000 description 1
NWVVVBRKAWDGAB-UHFFFAOYSA-N hydroquinone methyl ether Natural products COC1=CC=C(O)C=C1 NWVVVBRKAWDGAB-UHFFFAOYSA-N 0.000 description 1
125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
239000000594 mannitol Substances 0.000 description 1
235000010355 mannitol Nutrition 0.000 description 1
WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 description 1
125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 1
PJUIMOJAAPLTRJ-UHFFFAOYSA-N monothioglycerol Chemical compound OCC(O)CS PJUIMOJAAPLTRJ-UHFFFAOYSA-N 0.000 description 1
239000000025 natural resin Substances 0.000 description 1
239000011368 organic material Substances 0.000 description 1
UWJJYHHHVWZFEP-UHFFFAOYSA-N pentane-1,1-diol Chemical class CCCCC(O)O UWJJYHHHVWZFEP-UHFFFAOYSA-N 0.000 description 1
239000000049 pigment Substances 0.000 description 1
229920001223 polyethylene glycol Polymers 0.000 description 1
229920000642 polymer Polymers 0.000 description 1
238000002360 preparation method Methods 0.000 description 1
235000013772 propylene glycol Nutrition 0.000 description 1
239000000376 reactant Substances 0.000 description 1
239000003340 retarding agent Substances 0.000 description 1
229920006395 saturated elastomer Polymers 0.000 description 1
239000000565 sealant Substances 0.000 description 1
239000002904 solvent Substances 0.000 description 1
125000001424 substituent group Chemical group 0.000 description 1
229920003002 synthetic resin Polymers 0.000 description 1
239000000057 synthetic resin Substances 0.000 description 1
150000003568 thioethers Chemical class 0.000 description 1
239000013638 trimer Substances 0.000 description 1
239000008096 xylene Substances 0.000 description 1

Classifications

- 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
- C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
- C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
- C08G59/40—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the curing agents used
- C08G59/62—Alcohols or phenols
- C08G59/625—Hydroxyacids
- 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
- C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
- C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
- C08G59/40—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the curing agents used
- C08G59/50—Amines
- C08G59/56—Amines together with other curing agents

Landscapes

Chemical & Material Sciences (AREA)
Health & Medical Sciences (AREA)
Chemical Kinetics & Catalysis (AREA)
Medicinal Chemistry (AREA)
Polymers & Plastics (AREA)
Organic Chemistry (AREA)
Epoxy Resins (AREA)
Injection Moulding Of Plastics Or The Like (AREA)

CA000362405A 1979-11-02 1980-10-15 Epoxy curing stystem Expired CA1181194A (en)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US090,765		1979-11-02
US06/090,765 US4264758A (en)	1979-11-02	1979-11-02	Novel epoxy curing system

Publications (1)

Publication Number	Publication Date
CA1181194A true CA1181194A (en)	1985-01-15

Family

ID=22224207

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA000362405A Expired CA1181194A (en)	1979-11-02	1980-10-15	Epoxy curing stystem

Country Status (9)

Country	Link
US (1)	US4264758A (2)
JP (1)	JPS5667334A (2)
BR (1)	BR8005841A (2)
CA (1)	CA1181194A (2)
DE (1)	DE3039546A1 (2)
FR (1)	FR2468623A1 (2)
GB (1)	GB2061951B (2)
IT (1)	IT1133741B (2)
SE (1)	SE8007605L (2)

Families Citing this family (12)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4341819A (en) *	1980-12-29	1982-07-27	The Polymer Corporation	Epoxy coating powders with wrinkle finishes
JPH093156A (ja) *	1995-06-15	1997-01-07	Yuka Shell Epoxy Kk	変性エポキシ樹脂、その製造法及び塗料用組成物
US5795927A (en) *	1996-05-17	1998-08-18	Morton International, Inc.	Color stable wrinkle finish epoxy powder coating
US5688878A (en) *	1996-05-17	1997-11-18	Morton International, Inc.	Epoxy powder coating with wrinkle finish
WO1998029468A1 (en) *	1996-12-31	1998-07-09	Shell Internationale Research Maatschappij B.V.	Storage stable compatible curing agent compositions for epoxy resins self curable at sub-ambient temperatures
US5932288A (en) *	1997-12-18	1999-08-03	Morton International, Inc.	Wrinkle epoxy powder coating with acid and its homolog methylenedisalicylic
EP2785762A2 (en) *	2011-12-01	2014-10-08	Dow Global Technologies LLC	Liquid accelerator composition for hardeners
JP2015524875A (ja) *	2012-08-16	2015-08-27	ダウグローバルテクノロジーズエルエルシー	エポキシ樹脂のための高速硬化剤
JP6043602B2 (ja) *	2012-11-22	2016-12-14	旭化成株式会社	樹脂組成物
WO2017106596A1 (en) *	2015-12-18	2017-06-22	3M Innovative Properties Company	Curable epoxy compositions and methods for accelerating the curing of epoxy compositions
WO2018000125A1 (en) *	2016-06-27	2018-01-04	Evonik Degussa Gmbh	Room temperature ionic liquid curing agent
WO2021029170A1 (ja) *	2019-08-14	2021-02-18	三菱瓦斯化学株式会社	エポキシ樹脂組成物、ガスバリア性フィルム及び積層体

Family Cites Families (5)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
BE606055A (2)	1960-07-14
FR1295086A (fr) *	1960-07-14	1962-06-01	Shell Int Research	Procédé de mûrissage des résines époxy
GB1061699A (en) *	1966-02-02	1967-03-15	Shell Int Research	Improvements in or relating to the curing of epoxy resins
US3639928A (en) *	1970-11-27	1972-02-08	Jefferson Chem Co Inc	Accelerator combination for epoxy curing
US3740373A (en) *	1971-07-28	1973-06-19	Jefferson Chem Co Inc	Epoxy resin composition containing a polyoxyalkylenepolyamine,substituted piperazine,salicylic acid and a phenol

1979
- 1979-11-02 US US06/090,765 patent/US4264758A/en not_active Expired - Lifetime
1980
- 1980-07-02 JP JP8930680A patent/JPS5667334A/ja active Granted
- 1980-09-12 BR BR8005841A patent/BR8005841A/pt unknown
- 1980-10-06 GB GB8032170A patent/GB2061951B/en not_active Expired
- 1980-10-15 CA CA000362405A patent/CA1181194A/en not_active Expired
- 1980-10-20 DE DE19803039546 patent/DE3039546A1/de not_active Withdrawn
- 1980-10-29 SE SE8007605A patent/SE8007605L/ not_active Application Discontinuation
- 1980-10-31 FR FR8023350A patent/FR2468623A1/fr active Granted
- 1980-10-31 IT IT25715/80A patent/IT1133741B/it active

Also Published As

Publication number	Publication date
DE3039546A1 (de)	1981-05-14
US4264758A (en)	1981-04-28
JPS5713573B2 (2)	1982-03-18
BR8005841A (pt)	1981-05-19
FR2468623B1 (2)	1983-04-29
JPS5667334A (en)	1981-06-06
GB2061951B (en)	1983-06-02
SE8007605L (sv)	1981-05-03
GB2061951A (en)	1981-05-20
FR2468623A1 (fr)	1981-05-08
IT1133741B (it)	1986-07-09
IT8025715A0 (it)	1980-10-31

Legal Events

Date	Code	Title	Description
2002-01-15	MKEX	Expiry

Publication	Publication Date	Title
US4331582A (en)	1982-05-25	Epoxy latent catalyst
CA1181194A (en)	1985-01-15	Epoxy curing stystem
EP2961785B1 (en)	2017-03-22	Anhydride accelerators for epoxy resin systems
JP3277256B2 (ja)	2002-04-22	エポキシド付加物の製造方法
CA1323120C (en)	1993-10-12	Epoxy adhesive
CA1161588A (en)	1984-01-31	Solvent resistant epoxy coatings
JP2005008884A (ja)	2005-01-13	硬化性エポキシ樹脂組成物、これを使用する二次元加工法とそれで得られる造形品
KR100571136B1 (ko)	2006-04-17	물에 영향을 받지 않는 에폭시 수지 경화촉진제인 노볼락
CA3124624A1 (en)	2020-07-27	Use of special thiol compounds to improve the storage stability of compositions based on epoxy resins containing amine compounds
US3732309A (en)	1973-05-08	Polyepoxide-polymercaptan-amine adducts
US3914288A (en)	1975-10-21	Reaction products of polyepoxides, mercaptoalkanoic acid esters and amines
EP0074798A1 (en)	1983-03-23	Polyoxyalkylenepolyamine curing agents for epoxy resins, method of making the curing agents, and curing method
US4195153A (en)	1980-03-25	Non-crystallizing epoxy resin accelerator
US4189564A (en)	1980-02-19	Non-crystallizing epoxy resin accelerator
US4147857A (en)	1979-04-03	Epoxy cure with polyamine-polyether succinimide systems
GB2031431A (en)	1980-04-23	Novel epoxy curing agent
US4122068A (en)	1978-10-24	Polyether dihydroxyalkyl carbamate epoxy additive for epoxy resins
US3352810A (en)	1967-11-14	Epoxy resin compositions
KR920007659B1 (ko)	1992-09-14	경화성 에폭시 수지 조성물 및 에폭시 수지 조성물 강화방법
EP0669949B1 (en)	2002-03-13	Tertiary amine derivatives as components of polymer forming systems
JPS5984916A (ja)	1984-05-16	硬化剤としてポリオキシアルキレンジアミンビグアナイド塩を有するエポキシ樹脂組成物
US4146701A (en)	1979-03-27	Polyether diureide epoxy additives
US4188474A (en)	1980-02-12	Epoxy curing accelerator
JPS63186726A (ja)	1988-08-02	常温速硬化型エポキシ樹脂組成物
US3394098A (en)	1968-07-23	Epoxy resin compositions