WO1999028365A1 - Adducts of aromatic monoepoxy compounds and norbornanediamine - Google Patents
Adducts of aromatic monoepoxy compounds and norbornanediamine Download PDFInfo
- Publication number
- WO1999028365A1 WO1999028365A1 PCT/EP1998/007463 EP9807463W WO9928365A1 WO 1999028365 A1 WO1999028365 A1 WO 1999028365A1 EP 9807463 W EP9807463 W EP 9807463W WO 9928365 A1 WO9928365 A1 WO 9928365A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- general formula
- adduct
- compound
- adducts
- diglycidyl ether
- Prior art date
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 24
- 125000003118 aryl group Chemical group 0.000 title claims abstract description 10
- XMSVKICKONKVNM-UHFFFAOYSA-N bicyclo[2.2.1]heptane-3,4-diamine Chemical compound C1CC2(N)C(N)CC1C2 XMSVKICKONKVNM-UHFFFAOYSA-N 0.000 title abstract description 3
- 239000004593 Epoxy Substances 0.000 claims abstract description 22
- 239000000203 mixture Substances 0.000 claims abstract description 14
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 claims abstract description 6
- CREXVNNSNOKDHW-UHFFFAOYSA-N azaniumylideneazanide Chemical group N[N] CREXVNNSNOKDHW-UHFFFAOYSA-N 0.000 claims abstract description 5
- 238000000034 method Methods 0.000 claims abstract description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 4
- 239000001257 hydrogen Substances 0.000 claims abstract description 4
- 238000002360 preparation method Methods 0.000 claims abstract description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 3
- 150000001412 amines Chemical class 0.000 claims description 15
- GYZLOYUZLJXAJU-UHFFFAOYSA-N diglycidyl ether Chemical compound C1OC1COCC1CO1 GYZLOYUZLJXAJU-UHFFFAOYSA-N 0.000 claims description 12
- RNLHGQLZWXBQNY-UHFFFAOYSA-N 3-(aminomethyl)-3,5,5-trimethylcyclohexan-1-amine Chemical compound CC1(C)CC(N)CC(C)(CN)C1 RNLHGQLZWXBQNY-UHFFFAOYSA-N 0.000 claims description 9
- 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 8
- 238000003756 stirring Methods 0.000 claims description 7
- 125000001931 aliphatic group Chemical group 0.000 claims description 6
- PXKLMJQFEQBVLD-UHFFFAOYSA-N bisphenol F Chemical compound C1=CC(O)=CC=C1CC1=CC=C(O)C=C1 PXKLMJQFEQBVLD-UHFFFAOYSA-N 0.000 claims description 6
- 239000003085 diluting agent Substances 0.000 claims description 6
- 125000003700 epoxy group Chemical group 0.000 claims description 6
- 238000010438 heat treatment Methods 0.000 claims description 4
- YCUKMYFJDGKQFC-UHFFFAOYSA-N 2-(octan-3-yloxymethyl)oxirane Chemical compound CCCCCC(CC)OCC1CO1 YCUKMYFJDGKQFC-UHFFFAOYSA-N 0.000 claims description 3
- HSDVRWZKEDRBAG-UHFFFAOYSA-N 2-[1-(oxiran-2-ylmethoxy)hexoxymethyl]oxirane Chemical compound C1OC1COC(CCCCC)OCC1CO1 HSDVRWZKEDRBAG-UHFFFAOYSA-N 0.000 claims description 3
- 229920003986 novolac Polymers 0.000 claims description 3
- HPILSDOMLLYBQF-UHFFFAOYSA-N 2-[1-(oxiran-2-ylmethoxy)butoxymethyl]oxirane Chemical compound C1OC1COC(CCC)OCC1CO1 HPILSDOMLLYBQF-UHFFFAOYSA-N 0.000 claims description 2
- SEFYJVFBMNOLBK-UHFFFAOYSA-N 2-[2-[2-(oxiran-2-ylmethoxy)ethoxy]ethoxymethyl]oxirane Chemical compound C1OC1COCCOCCOCC1CO1 SEFYJVFBMNOLBK-UHFFFAOYSA-N 0.000 claims description 2
- 239000011541 reaction mixture Substances 0.000 claims description 2
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 57
- 235000019445 benzyl alcohol Nutrition 0.000 description 19
- CUFXMPWHOWYNSO-UHFFFAOYSA-N 2-[(4-methylphenoxy)methyl]oxirane Chemical compound C1=CC(C)=CC=C1OCC1OC1 CUFXMPWHOWYNSO-UHFFFAOYSA-N 0.000 description 11
- 239000004848 polyfunctional curative Substances 0.000 description 8
- 230000006750 UV protection Effects 0.000 description 5
- 239000011230 binding agent Substances 0.000 description 5
- 239000003822 epoxy resin Substances 0.000 description 5
- 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 5
- 229920000647 polyepoxide Polymers 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- 239000011347 resin Substances 0.000 description 4
- 229920005989 resin Polymers 0.000 description 4
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 238000000576 coating method Methods 0.000 description 3
- 239000011521 glass Substances 0.000 description 3
- 238000005259 measurement Methods 0.000 description 3
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 238000012360 testing method Methods 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- 101000623895 Bos taurus Mucin-15 Proteins 0.000 description 2
- FQYUMYWMJTYZTK-UHFFFAOYSA-N Phenyl glycidyl ether Chemical compound C1OC1COC1=CC=CC=C1 FQYUMYWMJTYZTK-UHFFFAOYSA-N 0.000 description 2
- 239000011248 coating agent Substances 0.000 description 2
- 150000004985 diamines Chemical class 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 150000002170 ethers Chemical class 0.000 description 2
- -1 poly- oxypropylene diglycidyl ether Chemical compound 0.000 description 2
- YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 2
- 239000000758 substrate Substances 0.000 description 2
- BBBUAWSVILPJLL-UHFFFAOYSA-N 2-(2-ethylhexoxymethyl)oxirane Chemical compound CCCCC(CC)COCC1CO1 BBBUAWSVILPJLL-UHFFFAOYSA-N 0.000 description 1
- YSUQLAYJZDEMOT-UHFFFAOYSA-N 2-(butoxymethyl)oxirane Chemical compound CCCCOCC1CO1 YSUQLAYJZDEMOT-UHFFFAOYSA-N 0.000 description 1
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 1
- HHRACYLRBOUBKM-UHFFFAOYSA-N 2-[(4-tert-butylphenoxy)methyl]oxirane Chemical compound C1=CC(C(C)(C)C)=CC=C1OCC1OC1 HHRACYLRBOUBKM-UHFFFAOYSA-N 0.000 description 1
- VPWNQTHUCYMVMZ-UHFFFAOYSA-N 4,4'-sulfonyldiphenol Chemical class C1=CC(O)=CC=C1S(=O)(=O)C1=CC=C(O)C=C1 VPWNQTHUCYMVMZ-UHFFFAOYSA-N 0.000 description 1
- RREANTFLPGEWEN-MBLPBCRHSA-N 7-[4-[[(3z)-3-[4-amino-5-[(3,4,5-trimethoxyphenyl)methyl]pyrimidin-2-yl]imino-5-fluoro-2-oxoindol-1-yl]methyl]piperazin-1-yl]-1-cyclopropyl-6-fluoro-4-oxoquinoline-3-carboxylic acid Chemical compound COC1=C(OC)C(OC)=CC(CC=2C(=NC(\N=C/3C4=CC(F)=CC=C4N(CN4CCN(CC4)C=4C(=CC=5C(=O)C(C(O)=O)=CN(C=5C=4)C4CC4)F)C\3=O)=NC=2)N)=C1 RREANTFLPGEWEN-MBLPBCRHSA-N 0.000 description 1
- 229930185605 Bisphenol Natural products 0.000 description 1
- 239000004606 Fillers/Extenders Substances 0.000 description 1
- AWMVMTVKBNGEAK-UHFFFAOYSA-N Styrene oxide Chemical compound C1OC1C1=CC=CC=C1 AWMVMTVKBNGEAK-UHFFFAOYSA-N 0.000 description 1
- GKXVJHDEWHKBFH-UHFFFAOYSA-N [2-(aminomethyl)phenyl]methanamine Chemical compound NCC1=CC=CC=C1CN GKXVJHDEWHKBFH-UHFFFAOYSA-N 0.000 description 1
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 150000004982 aromatic amines Chemical class 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- SSJXIUAHEKJCMH-UHFFFAOYSA-N cyclohexane-1,2-diamine Chemical compound NC1CCCCC1N SSJXIUAHEKJCMH-UHFFFAOYSA-N 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 230000004069 differentiation Effects 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 150000002191 fatty alcohols Chemical class 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 238000009408 flooring Methods 0.000 description 1
- 238000001879 gelation Methods 0.000 description 1
- 125000002636 imidazolinyl group Chemical group 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 239000004922 lacquer Substances 0.000 description 1
- 150000002734 metacrylic acid derivatives Chemical class 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 239000004570 mortar (masonry) Substances 0.000 description 1
- FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 229960004889 salicylic acid Drugs 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 239000000057 synthetic resin Substances 0.000 description 1
- 229920003002 synthetic resin Polymers 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 238000004383 yellowing Methods 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
- C08G59/182—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 using pre-adducts of epoxy compounds with curing agents
- C08G59/184—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 using pre-adducts of epoxy compounds with curing agents with amines
Definitions
- Curable mixtures based on amine hardeners and epoxy resins are widely used in the industry for coating and improving metallic and mineral substrates.
- the amine hardeners used are, in particular, aliphatic, cycloaliphatic or aromatic amines as well as, optionally, imidazo- line group-containing polyaminoamides and adducts thereof.
- binder systems are rapidly cured after being applied to the substrates to make them e.g. quickly passable or recoatable.
- Essential criteria are high early water resistance of the still unhardened film (e.g. by drop formation at high relative atmospheric humidity) as well as low viscosity of the binder system to ensure its processability even at low temperatures.
- Mannich bases i.e reaction products of amines and formaldehyde with a phenolic component
- hardeners for epoxy resins which develop a hardness that is to some extent satisfactory at low temperatures.
- JP Hei 7-507900 JP Hei 7-5117899 or USP 4,269,742.
- the disadvantage of the systems proposed therein is on the one hand their high viscosity and, on the other hand, the bad UV resistance of the cured coatings owing to the phenolic components present in these systems.
- EP 0 288 975 describes adducts of monoepoxy compounds and specific diamines which can be used at very low temperatures. However, these compounds also need to be accelerated with salicylic acid, phenol, alkylphenol or with a Mannich base. These accelerators in turn also produce bad UV resistance.
- WO 96/34032 describes adducts of cycloaliphatic di- or polyglycidyl ethers with norbomanediamine, if required using in addition acrylates or methacrylates. Although these products have to some extent good UV resistance, the development of the hardness of these systems (measured in accordance with Shore D) is far too low even at room temperature; the surface properties of the cured films are insufficient for many applications and the viscosities of the amine adducts are very high in spite of a high diluent proportion of about 45 %.
- the object of this invention is therefore to overcome these disadvantages and to provide hardeners for binder systems which, at high UV resistance and low viscosity, provide the cured systems with a rapid complete cure and with uniformly good surface properties both at room temperature and under unfavourable curing conditions, such as at low temperatures and/or high relative atmospheric humidity.
- this invention relates to adducts containing free active hydrogen bound to amino nitrogen atoms, which are obtainable by reacting
- Ri , R3, R5 are each independently of one another H or an unbranched or branched alkyl radical containing 1 to 10 carbon atoms,
- R2, R4 are H
- RQ is a radical of formula 2 y7 .
- V7 using at most 2 mol of the compound of the general formula (2) per mol of the compound of the general formula (1). It is preferred, however, to use a molar ratio of 1 :1.
- novel adducts are prepared by known processes by placing the diamines in a vessel and adding the aromatic monoepoxy compounds dropwise, with stirring, at 60 to 80 °C and then stirring this mixture for about 1 hour (h) at that temperature until the adduct formation is complete.
- isolated adducts are also used, which are prepared with an excess of norbor- nanediamine (NBDA).
- NBDA norbor- nanediamine
- the 1.5- to 10-fold, preferably the 4- to 6-fold, molar amount of amine is placed in a vessel and the aromatic monoepoxy compound is added dropwise, with stirring, conveniently at 60 to 80 °C. Excess amine is then removed by distillation under vacuum.
- this invention thus relates to a process for the preparation of the adducts according to claim 1 , which process comprises
- the reaction temperature is not critical and may thus be varied but is conveniently from 60 to
- This invention also relates to curable mixtures consisting of
- the novel adducts are preferably adjusted with the components (C) to (E) to a user-friendly mixture ratio of 50 parts of hardener (adducts I) per 100 parts of resin (component II).
- the mixture ratios can also vary from 30 to 100 parts of hardener/100 g of resin.
- the diluent proportion should not exceed 40 %, based on the hardener, since this would result in too great a drop in the mechanical data.
- the ratio between reactive groups of the adducts according to (I) and, optionally, the amines according to (D) and the epoxy groups (II) and, optionally, the higher- or monofunctional glycidyl ethers according to (E) is preferably adjusted about equivalently.
- the preferred aliphatic or cycloaliphatic amines of (D) are isopho- ronediamine, bisaminomethylcyclohexane and/or 2,4,4(2,2,4)-trimethylhexamethylenedi-1 ,6- amine.
- the mono- or higher-functional glycidyl ethers (E) according to claim 4 are preferably ethylhexyl glycidyl ether, hexanediol diglycidyl ether, butanediol digly- cidyl ether, cyclohexanedimethylol diglycidyl ether, diethylene glycol diglycidyl ether, poly- oxypropylene diglycidyl ether and glycidyl ether based on bisphenol A, bisphenol F and novolaks.
- the epoxy compounds (component II) additionally used in accordance with this invention are commercially available products containing at least one epoxy group per molecule and are derived from mono- and/or polyvalent and/or polynuclear phenols, in particular bisphenols, and from novolaks, such as diglycidyl ethers of bisphenol A and bisphenol F.
- binders for synthetic resin mortar standard pebbles and sands are additionally used in the grain size distributions and amounts customarily used in this field.
- NBDA norbomanediamine
- 320 g of benzyl alcohol 450 g of norbomanediamine (NBDA) and 320 g of benzyl alcohol are placed in a reaction vessel. After heating this mixture to 60 to 80 °C, 230 g of cresyl glycidyl ether (epoxy value: about 0.55) are added dropwise, with stirring, over 30 min, keeping the temperature within this range by cooling. To ensure complete adduct formation, stirring is continued for 60 min at 60 °C to 80 °C.
- NBDA norbomanediamine
- Viscosity 210 mPa.s /25 °C; H equivalent: about 95
- Viscosity 230 mPa.s /25 °C; H equivalent: about 95
- Viscosity 455 mPa.s /25 °C; H equivalent: about -95
- Viscosiy 160 mPa.s /25 °C; H equivalent: about -95
- Example 1 450 g of NBDA, 150 g of phenyl glycidyl ether (epoxy value: about 0.58), 80 g of hexanediol diglycidyl ether and 320 g of benzyl alcohol are reacted according to Example 1.
- Viscosity 320 mPa.s /25 °C; H equivalent: about -95
- Viscosity 270 mPa-s /25 °C; H equivalent: about -95
- Viscosity 400 mPa.s /25 °C; NH equivalent: about 95
- Viscosity 360 mPa.s /25 °C; NH equivalent: about 95
- Viscosity 310 mPa-s /25 °C; H equivalent: about 95
- Viscosity 290 mPa-s /25 °C; H equivalent: about 95
- 530 g of the adduct of Example 13 are homogenised with 200 g of IPD and 270 g of benzyl alcohol at about 60 °C.
- Viscosity 280 mPa-s /25 °C; NH equivalent: about 95
- 320 g of the adduct of Example 13 are homogenised with 300 g of IPD and 380 g of benzyl alcohol at about 60 °C.
- Viscosity 160 mPa-s /25 °C; NH equivalent: about 95
- 530 g of the adduct of Example 13 are homogenised with 181 g of NBDA and 289 g of benzyl alcohol at about 60 °C.
- Viscosity 185 mPa-s /25 °C; NH equivalent: about 95
- Viscosity 60 mPa-s /25 °C; NH equivalent: 95
- Viscosity 385 mPa.s /25 °C; NH equivalent: 95
- Measurement is carried out using a Haake rotary viscometer RV20 in accordance with the instructions of the producer.
- the calculated amounts of epoxy resins and amine hardener are weighed into a mixing vessel and are vigorously mixed with a spatula for about 2 min without working in any excess air. Local inhomogeneities show as streaks and are to be avoided.
- a 500 ⁇ m film transfer frame, of Erichsen, is placed on a glass plate which has been cleaned first with acetone and then dried, and this frame is then filled with about 15 g of the reactive mixture and drawn evenly over the free area.
- the freshly coated glass plates are immediately laid out into the corresponding climatic chambers, typically at relative atmospheric humidity (r.h.) at 23 °C/r. h. about 95 %. at 10 °C/r. h. about 80 % at 5 °C/r. h. > 70 %.
- the glass plates After curing for 24 hours, the glass plates are taken back to the test laboratory for assessment of their surface.
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)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19752954 | 1997-11-28 | ||
| DE19752954.2 | 1997-11-28 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| WO1999028365A1 true WO1999028365A1 (en) | 1999-06-10 |
Family
ID=7850201
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PCT/EP1998/007463 WO1999028365A1 (en) | 1997-11-28 | 1998-11-20 | Adducts of aromatic monoepoxy compounds and norbornanediamine |
Country Status (1)
| Country | Link |
|---|---|
| WO (1) | WO1999028365A1 (fi) |
Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2007060091A1 (en) * | 2005-11-25 | 2007-05-31 | Huntsman Advanced Materials (Switzerland) Gmbh | Curing agent for epoxy resins |
| EP2752437A1 (de) | 2013-01-08 | 2014-07-09 | Sika Technology AG | Härter für emissionsarme Epoxidharz-Produkte |
| WO2014108304A3 (de) * | 2013-01-08 | 2014-12-18 | Sika Technology Ag | Härter für emissionsarme epoxidharz-produkte |
| WO2016137791A1 (en) * | 2015-02-27 | 2016-09-01 | 3M Innovative Properties Company | Two-part structural adhesive |
| US9580622B2 (en) | 2013-12-16 | 2017-02-28 | Dow Global Technologies Llc | Crosslinkable composition, a method of making the same and a crosslinked composition produced therefrom |
| US9718990B2 (en) | 2013-12-11 | 2017-08-01 | Dow Global Technologies Llc | Coating system, a method of applying the coating system and an article comprising the coating system |
| CN115926114A (zh) * | 2021-08-05 | 2023-04-07 | 中国石油化工股份有限公司 | 一种室温固化低色泽改性脂环胺固化剂及其制备方法 |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS544992A (en) * | 1977-06-14 | 1979-01-16 | Nippon Zeon Co Ltd | Novel epoxy hardener |
| JPH0480228A (ja) * | 1990-07-20 | 1992-03-13 | Mitsui Toatsu Chem Inc | エポキシ樹脂用硬化剤 |
-
1998
- 1998-11-20 WO PCT/EP1998/007463 patent/WO1999028365A1/en active Application Filing
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS544992A (en) * | 1977-06-14 | 1979-01-16 | Nippon Zeon Co Ltd | Novel epoxy hardener |
| JPH0480228A (ja) * | 1990-07-20 | 1992-03-13 | Mitsui Toatsu Chem Inc | エポキシ樹脂用硬化剤 |
Non-Patent Citations (2)
| Title |
|---|
| DATABASE WPI Section Ch Week 7908, Derwent World Patents Index; Class A21, AN 79-14693B, XP002100663 * |
| DATABASE WPI Section Ch Week 9217, Derwent World Patents Index; Class A21, AN 92-138016, XP002100662 * |
Cited By (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2007060091A1 (en) * | 2005-11-25 | 2007-05-31 | Huntsman Advanced Materials (Switzerland) Gmbh | Curing agent for epoxy resins |
| US7683154B2 (en) | 2005-11-25 | 2010-03-23 | Huntsman International Llc | Epoxy resin curing agent of polyethylene polyamine-monoglycidyl ether adduct and amine compound |
| US9790319B2 (en) | 2013-01-08 | 2017-10-17 | Sika Technology Ag | Curing agents for low-emission epoxy resin products |
| WO2014108304A3 (de) * | 2013-01-08 | 2014-12-18 | Sika Technology Ag | Härter für emissionsarme epoxidharz-produkte |
| CN104870509A (zh) * | 2013-01-08 | 2015-08-26 | Sika技术股份公司 | 用于低排放环氧树脂产品的固化剂 |
| US9631047B2 (en) | 2013-01-08 | 2017-04-25 | Sika Technology Ag | Curing agents for low-emission epoxy resin products |
| EP2752437A1 (de) | 2013-01-08 | 2014-07-09 | Sika Technology AG | Härter für emissionsarme Epoxidharz-Produkte |
| US9718990B2 (en) | 2013-12-11 | 2017-08-01 | Dow Global Technologies Llc | Coating system, a method of applying the coating system and an article comprising the coating system |
| US9580622B2 (en) | 2013-12-16 | 2017-02-28 | Dow Global Technologies Llc | Crosslinkable composition, a method of making the same and a crosslinked composition produced therefrom |
| WO2016137791A1 (en) * | 2015-02-27 | 2016-09-01 | 3M Innovative Properties Company | Two-part structural adhesive |
| US10280345B2 (en) | 2015-02-27 | 2019-05-07 | 3M Innovative Properties Company | Two-part structural adhesive |
| CN115926114A (zh) * | 2021-08-05 | 2023-04-07 | 中国石油化工股份有限公司 | 一种室温固化低色泽改性脂环胺固化剂及其制备方法 |
| CN115926114B (zh) * | 2021-08-05 | 2024-12-03 | 中国石油化工股份有限公司 | 一种室温固化低色泽改性脂环胺固化剂及其制备方法 |
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