GB1598750A - High-molecular weight amine compositions - Google Patents
High-molecular weight amine compositions Download PDFInfo
- Publication number
- GB1598750A GB1598750A GB23139/78A GB2313978A GB1598750A GB 1598750 A GB1598750 A GB 1598750A GB 23139/78 A GB23139/78 A GB 23139/78A GB 2313978 A GB2313978 A GB 2313978A GB 1598750 A GB1598750 A GB 1598750A
- Authority
- GB
- United Kingdom
- Prior art keywords
- composition
- amine
- molecular weight
- weight
- epoxide
- Prior art date
- 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
Links
- 150000001412 amines Chemical class 0.000 title claims description 45
- 239000000203 mixture Substances 0.000 title claims description 38
- -1 cyclic acetal Chemical class 0.000 claims description 15
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 claims description 14
- 238000000034 method Methods 0.000 claims description 11
- DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 claims description 9
- 229920000647 polyepoxide Polymers 0.000 claims description 9
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 claims description 7
- 125000000217 alkyl group Chemical group 0.000 claims description 6
- 229920001577 copolymer Polymers 0.000 claims description 6
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 claims description 4
- 239000003822 epoxy resin Substances 0.000 claims description 4
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
- 238000002156 mixing Methods 0.000 claims description 3
- DEWLEGDTCGBNGU-UHFFFAOYSA-N 1,3-dichloropropan-2-ol Chemical compound ClCC(O)CCl DEWLEGDTCGBNGU-UHFFFAOYSA-N 0.000 claims description 2
- JEYSGRBJLFJRLO-UHFFFAOYSA-N 4-(2-phenylpropan-2-yl)cyclohexa-2,4-diene-1,1-diol Chemical compound C=1C=CC=CC=1C(C)(C)C1=CCC(O)(O)C=C1 JEYSGRBJLFJRLO-UHFFFAOYSA-N 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- 239000007859 condensation product Substances 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims 1
- 239000002904 solvent Substances 0.000 description 14
- 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 8
- 150000002924 oxiranes Chemical class 0.000 description 7
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 6
- 150000004985 diamines Chemical class 0.000 description 6
- BGJSXRVXTHVRSN-UHFFFAOYSA-N 1,3,5-trioxane Chemical compound C1OCOCO1 BGJSXRVXTHVRSN-UHFFFAOYSA-N 0.000 description 5
- QWVGKYWNOKOFNN-UHFFFAOYSA-N o-cresol Chemical compound CC1=CC=CC=C1O QWVGKYWNOKOFNN-UHFFFAOYSA-N 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 125000003277 amino group Chemical group 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 239000000945 filler Substances 0.000 description 3
- XPFVYQJUAUNWIW-UHFFFAOYSA-N furfuryl alcohol Chemical compound OCC1=CC=CO1 XPFVYQJUAUNWIW-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- 229920013646 Hycar Polymers 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- 125000001931 aliphatic group Chemical group 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 239000003085 diluting agent Substances 0.000 description 2
- 125000005843 halogen group Chemical group 0.000 description 2
- 229920000768 polyamine Polymers 0.000 description 2
- 239000008096 xylene Substances 0.000 description 2
- 239000004953 Aliphatic polyamide Substances 0.000 description 1
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 1
- 229920000459 Nitrile rubber Polymers 0.000 description 1
- 150000001241 acetals Chemical class 0.000 description 1
- 229920003231 aliphatic polyamide Polymers 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- IMUDHTPIFIBORV-UHFFFAOYSA-N aminoethylpiperazine Chemical compound NCCN1CCNCC1 IMUDHTPIFIBORV-UHFFFAOYSA-N 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- NTXGQCSETZTARF-UHFFFAOYSA-N buta-1,3-diene;prop-2-enenitrile Chemical compound C=CC=C.C=CC#N NTXGQCSETZTARF-UHFFFAOYSA-N 0.000 description 1
- 239000004568 cement Substances 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 238000007334 copolymerization reaction Methods 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 238000009408 flooring Methods 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 229920003986 novolac Polymers 0.000 description 1
- 229920001568 phenolic resin Polymers 0.000 description 1
- 239000005011 phenolic resin Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 230000000717 retained effect Effects 0.000 description 1
- 150000004760 silicates Chemical class 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000011343 solid material Substances 0.000 description 1
- 239000012265 solid product Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 231100000563 toxic property Toxicity 0.000 description 1
- DSROZUMNVRXZNO-UHFFFAOYSA-K tris[(1-naphthalen-1-yl-3-phenylnaphthalen-2-yl)oxy]alumane Chemical compound C=1C=CC=CC=1C=1C=C2C=CC=CC2=C(C=2C3=CC=CC=C3C=CC=2)C=1O[Al](OC=1C(=C2C=CC=CC2=CC=1C=1C=CC=CC=1)C=1C2=CC=CC=C2C=CC=1)OC(C(=C1C=CC=CC1=C1)C=2C3=CC=CC=C3C=CC=2)=C1C1=CC=CC=C1 DSROZUMNVRXZNO-UHFFFAOYSA-K 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L15/00—Compositions of rubber derivatives
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/04—Oxygen-containing compounds
- C08K5/15—Heterocyclic compounds having oxygen in the ring
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L63/00—Compositions of epoxy resins; Compositions of derivatives of epoxy resins
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L9/00—Compositions of homopolymers or copolymers of conjugated diene hydrocarbons
- C08L9/02—Copolymers with acrylonitrile
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)
- Compositions Of Macromolecular Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Adhesives Or Adhesive Processes (AREA)
Description
(54) HIGH-MOLECULAR WEIGHT AMINE
COMPOSITIONS
(71) We, HOECHST AKTIENGESELLSCHAFT, a body corporate organised according to the laws of the Federal Republic of Germany, of 6230
Frankfurt (Main) 80, Postfach 80 03 20, Federal Republic of Germany, do hereby declare the invention for which we pray that a patent may be granted to us, and the method by which it is to be performed, to be particularly described in and by the following statement:- The present invention relates to high-molecular weight amine compositions and a process for reducing the viscosity of high-molecular weight amines.
It is known that numerous high-molecular weight amines can react with epoxides to give technically interesting products of substantially higher molecular weight. The products obtained, may, for example, be used as binding agents for foundation materials, for cements or gap-filling compositions. In some cases, for example, when amines which are derived from butadiene-acrylonitrile copolymers are used, elastomeric gap-filling compositions. are obtained.
The amines used may be aliphatic, aromatic or heterocyclic. They may be reacted with equivalent amounts of the reaction product of "Bisphenol A" and epichlorohydrin to give high-molecular weight solid products.
The consistency of high-molecular weight amines of this kind depends on the molecular weight and on the number of amino groups, and may vary from viscous to solid. In order to render these amines capable of being mixed with epoxide and fillers, it is necessary to "melt" the amines prior to mixing. Such a step requires a considerable technological expenditure. Accordingly attempts have been made to reduce the viscosity of the amine by dilution with a solvent, for example xylene, furfuryl alcohol or acetone.
Especially when the high-molecular weight amines are used together with fillers, generally silicates, and with epoxides for the preparation of jointless floorings, solvents, for example xylene, must be added as diluent for reasons of better processability. The addition of a solvent furthermore makes it possible to add a greater quantity of filler to the composition. A large portion of the diluent remains in the composition even after hardening. However, the main portion of these retained solvents gradually evaporates, which process may take months or even more than one year. It can easily be understood that the period of volatilization of the solvent from the composition is largely dependent on the vapour pressure of the solvent. It is quite evident that the evaporation of solvents from hardened compositions results in shrinkage, which in the course of time may cause the formation of cracks in the epoxide polyadducts. Further disadvantages of epoxide polyadducts which had to be hardened in the presence of solvents are that they have a lower resistance to chemicals and solvents, an increased thermal expansion, and a reduced heat stability.
The use of solvents in the processing of epoxide compounds involves further serious disadvantages, namely annoyance by the strong odours of the solvents and the toxic properties of those solvents which are volatile.
The present invention provides epoxide-free compositions comprising a high
molecular weight amine (as hereinafter defined) and a cyclic acetal of the formula
in which R represents a hydrogen atom or an alkyl group. A composition of the invention has a reduced viscosity compared to the high-molecular weight amine alone.
An alkyl group represented by R preferably contains from 1 to 4 carbon atoms, and is most preferably a methyl group. Using these acetals, the viscosity of the high-molecular weight amine is reduced to an extremely large extent, and the compositions do not give the above-mentioned undesired properties when used for producing epoxide polyadducts.
The present invention also provides a process for reducing the viscosity of a high-molecular weight amine (as hereinafter defined), which comprises mixing the amine with a cyclic acetal of the above formula. The present invention further provides epoxide resins prepared with the compositions of the invention.
The high-molecular weight amines used in the compositions and process according to the invention are defined as having a molecular weight of from 200 to 10,000, preferably from 1,000 to 5,000, especially from 1,500, to 3,500. Amines which have from 1 to 3, preferably approximately 2, primary amino groups in the molecule on average, and especially those which are derived from copolymers of butadiene and acrylonitrile, are particularly preferred.
High-molecular weight amines which are derived from copolymers consisting of from 10 to 30% by weight of acrylonitrile and from 90 to 70% by weight of butadiene are particularly preferred. These amines may be obtained, for example, by copolymerization of butadiene, acrylonitrile and a small amount of a vinyl compound which contains a reactive halogen atom, according to German
Offenlegungsschrift No. 25 57 559, and subsequently reacting the halogen atom with ammonia, or with a low-molecular bivalent amine containing at least one primary amino group, for example ethylene diamine or aminoethylpiperazine.
High-molecular weight amines derived from copolymers of butadiene and acrylonitrile are commercially available under the trade name Hycar ATNB (manufactured by Messrs. B. F. Goodrich Co., Ohio, USA).
It is generally advantageous to mix from 1 to 40, preferably from 5 to 25, parts by weight of the cyclic acetal with 100 parts by weight of the high-molecular weight amine. The most favorable composition may easily be determined by a preliminary test.
The pronounced viscosity reduction achieved by adding a cyclic acetal of the above formula to a high-molecular weight amine is shown in the following Table
I:
TABLE I:
Reduction of the viscosity of a high-molecular weight amine:
Composition Viscosity (mPa.s)
100 parts by weight of diamine, molar weight 1600 262000 at 30"C 190 parts by weight of diamine 105 000 at 30"C 10 parts by weight of trioxan
85 parts by weight of diamine 52000 at 30"C 15 parts by weight of trioxan
80 parts by weight of diamine 28000 at 30"C 20 parts by weight of trioxan
The diamine used for this test (Hycar ATBN) was derived from a copolymer consisting of 17% by weight of acrylonitrile and 83% by weight of butadiene.
Suitable compounds for hardening the high-molecular weight amines are epoxide compounds commonly used for this purpose, for example the reaction products of epichlorohydrin and
1) 4,4 - dihydroxy - 2,2 - diphenylpropane ("Bisphenol A"), 2) a condensation product of o-cresol and formaldehyde consisting of from 90 to
95 percent of a product which is formed by reaction of 2 mols of o-cresol
and 1 mole of formaldehyde
3) phenolic resins, especially novolaks, or
4) aliphatic polyhydroxy compounds.
The compounds which have been obtained by condensation of Bisphenol A with epichlorohydrin or 1,3-dichlorohydrin in the presence of an alkali, and which correspond to the formula
are preferably used.
Liquid bis- or polyepoxides, especially those having a viscosity of from 100 to 15,000 mPa. sec at 250C, react especially easily.
Epoxide resins which have been prepared using compositions according to the invention of amine and cyclic acetal do not become brittle, even after storage for a period of several months at 1100C, in contradistinction to those epoxide resins which have been prepared using amines mixed with solvents. With regard to the usual technological properties, for example the bond strength on solid materials, the products prepared with the compositions of the invention are equal to those prepared with the use of solvents.
Table 2 shows the good mechanical properties of epoxide resins prepared from compositions according to the invention:
TABLE 2:
1st mixture 2nd mixture
polyamine 85 parts by weight 85 parts by weight
trioxymethylene 15 parts by weight 15 parts by weight
epoxide resin 20 parts by weight 30 parts by weight
processing time about 2 h about 2 h Shore hardness A after 35 50
3 days at 20"C elongation at break 300% 70%
ultimate tensile strength 200N/cm2 600 N/cm2
The polyamine employed was the diamine of molar weight 1600 (Table 1). The epoxide resin used was Bisphenol A containing 0.45 mol of epoxide groups per 100 g and having a viscosity of 1 Pa. sec. at 200C.
The degree of reduction of the viscosity according to the process of invention depends to only a small extent on the constitution of the high-molecular weight amines. Table 3 shows the reduction of the viscosity of various amines:
TABLE 3:
Molar - Viscosity''' Viscosity Amine weight amine mixture
aliphatic diamine 242 3800 360 phenoUformaldehyde 302 18200 370
condensate containing
amino groups
aliphatic polyamide not determined 24000 1500
having terminal amino
groups
1) [mPa. sec.] measured at 200C.
2) mixture of 15% by weight of trioxan and 85 ó by weight of amine: [mPa.sl measured to 200 C.
Claims (19)
1. An epoxide-free composition comprising a high-molecular weight amine (as hereinbefore defined) and a cyclic acetal of the formula
in which each R, which may be the same or different represents a hydrogen atom or an alkyl group.
2. A composition as claimed in claim 1, wherein an alkyl group represented by
R has from 1 to 4 carbon atoms.
3. A composition as claimed in claim 2, wherein an alkyl group represented by
R is a methyl group.
4. A composition as claimed in any one of claims I to 3, wherein each R is the same.
5. A composition as claimed in any one of claims 1 to 4, wherein the amine has a molecular weight of from 1000 to 5000.
6. A composition as claimed in claim 5, wherein the molecular weight of the amine is from 1500 to 3500.
7. A composition as claimed in any one of claims 1 to 6, wherein the amine contains from 1 to 3 primary amino groups in the molecule on average.
8. A composition as claimed in claim 7, wherein the amine contains approximately 2 primary amino groups in the molecule on average.
9. A composition as claimed in any one of claims 1 to 8, wherein the amine is derived from a copolymer of butadiene and acrylonitrile.
10. A composition as claimed in claim 9, wherein the amine is derived from a copolymer comprising from 10 to 30% by weight of structural units derived from acrylonitrile and from 90 to 70% by weight of structural units derived from butadiene.
11. A composition as claimed in any one of claims 1 to 10 wherein the weight ratio of cyclic acetal to -high-molecular weight amine is from 1:100 to 40:100.
12. A composition as claimed in claim 11, wherein the weight ratio of cyclic acetal to high-molecular weight amine is from 5:100 to 25:100.
13. A composition as claimed in claim 1 and described herein.
14. A process for reducing the viscosity of a high-molecular weight amine (as hereinbefore defined), which comprises mixing the amine with a cyclic acetal of the formula
in which each R, which may be the same or different, represents a hydrogen atom or an alkyl group.
15. A process as claimed in claim 14, wherein a composition as claimed in any one of claims 2 to 13 is prepared.
16. A process for preparing an epoxide resin which comprises reacting an epoxide compound with a composition as claimed in any one of claims 1 to 13.
17. A process as claimed in claim 16, wherein the epoxide compound is a condensation product of 4,4- dihydroxy- 2,2- diphenylpropane with epichlorohydrin or 1,3-dichlorohydrin.
18. A process as claimed in claim 18, substantially as described herein.
19. An epoxide resin prepared by a process as claimed in any one of claims 16 to 18.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2724063A DE2724063C2 (en) | 1977-05-27 | 1977-05-27 | Diluent for high molecular weight amines |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1598750A true GB1598750A (en) | 1981-09-23 |
Family
ID=6010081
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB23139/78A Expired GB1598750A (en) | 1977-05-27 | 1978-05-26 | High-molecular weight amine compositions |
Country Status (10)
| Country | Link |
|---|---|
| BE (1) | BE867589A (en) |
| BR (1) | BR7803354A (en) |
| CA (1) | CA1097665A (en) |
| DE (1) | DE2724063C2 (en) |
| FR (1) | FR2392066A1 (en) |
| GB (1) | GB1598750A (en) |
| IT (1) | IT1096234B (en) |
| LU (1) | LU79708A1 (en) |
| NL (1) | NL7805777A (en) |
| SE (1) | SE7806089L (en) |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1034855B (en) * | 1956-09-05 | 1958-07-24 | Gen Aniline & Film Corp | Process for the multi-stage curing of epoxy resins by m-phenylenediamine |
| US3026285A (en) * | 1959-09-18 | 1962-03-20 | Frank N Hirosawa | Curing agent comprising the reaction product of an aliphatic polyamine and an aldehyde, and epoxy resin cured therewith |
| DE1110407B (en) * | 1959-10-23 | 1961-07-06 | Hoechst Ag | Process for curing epoxy resins |
| BE606055A (en) * | 1960-07-14 | |||
| CH487835A (en) * | 1967-06-22 | 1970-03-31 | Ciba Geigy | Process for the preparation of new adducts from polyepoxides and cycloaliphatic diprimary diamines |
-
1977
- 1977-05-27 DE DE2724063A patent/DE2724063C2/en not_active Expired
-
1978
- 1978-05-25 IT IT23808/78A patent/IT1096234B/en active
- 1978-05-25 LU LU79708A patent/LU79708A1/en unknown
- 1978-05-26 SE SE7806089A patent/SE7806089L/en unknown
- 1978-05-26 GB GB23139/78A patent/GB1598750A/en not_active Expired
- 1978-05-26 CA CA304,171A patent/CA1097665A/en not_active Expired
- 1978-05-26 NL NL7805777A patent/NL7805777A/en not_active Application Discontinuation
- 1978-05-26 BR BR7803354A patent/BR7803354A/en unknown
- 1978-05-29 FR FR7815908A patent/FR2392066A1/en active Granted
- 1978-05-29 BE BE188132A patent/BE867589A/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| DE2724063A1 (en) | 1978-12-07 |
| BR7803354A (en) | 1979-01-02 |
| SE7806089L (en) | 1978-11-28 |
| IT1096234B (en) | 1985-08-26 |
| FR2392066B1 (en) | 1982-12-03 |
| CA1097665A (en) | 1981-03-17 |
| IT7823808A0 (en) | 1978-05-25 |
| BE867589A (en) | 1978-11-29 |
| NL7805777A (en) | 1978-11-29 |
| DE2724063C2 (en) | 1986-10-30 |
| FR2392066A1 (en) | 1978-12-22 |
| LU79708A1 (en) | 1979-02-02 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PS | Patent sealed [section 19, patents act 1949] | ||
| PCNP | Patent ceased through non-payment of renewal fee |