ES268679A1 - Stable aqueous emulsions from water-insoluble epoxy resins and water-insoluble aminoplasts - Google Patents
Stable aqueous emulsions from water-insoluble epoxy resins and water-insoluble aminoplastsInfo
- Publication number
- ES268679A1 ES268679A1 ES0268679A ES268679A ES268679A1 ES 268679 A1 ES268679 A1 ES 268679A1 ES 0268679 A ES0268679 A ES 0268679A ES 268679 A ES268679 A ES 268679A ES 268679 A1 ES268679 A1 ES 268679A1
- Authority
- ES
- Spain
- Prior art keywords
- emulsions
- water
- epoxide
- ether
- stiffening
- 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
- 239000000839 emulsion Substances 0.000 title abstract 13
- 229920003180 amino resin Polymers 0.000 title abstract 6
- 239000003822 epoxy resin Substances 0.000 title abstract 4
- 229920000647 polyepoxide Polymers 0.000 title abstract 4
- 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 title 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 abstract 12
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 abstract 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract 6
- DURPTKYDGMDSBL-UHFFFAOYSA-N 1-butoxybutane Chemical group CCCCOCCCC DURPTKYDGMDSBL-UHFFFAOYSA-N 0.000 abstract 5
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 abstract 5
- 235000011128 aluminium sulphate Nutrition 0.000 abstract 5
- 239000001164 aluminium sulphate Substances 0.000 abstract 5
- 239000004202 carbamide Substances 0.000 abstract 5
- BUACSMWVFUNQET-UHFFFAOYSA-H dialuminum;trisulfate;hydrate Chemical compound O.[Al+3].[Al+3].[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O BUACSMWVFUNQET-UHFFFAOYSA-H 0.000 abstract 5
- 150000002118 epoxides Chemical class 0.000 abstract 5
- -1 methane Epoxide Chemical class 0.000 abstract 5
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 abstract 4
- SUPOBRXPULIDDX-UHFFFAOYSA-N [[4-amino-6-(hydroxymethylamino)-1,3,5-triazin-2-yl]amino]methanol Chemical compound NC1=NC(NCO)=NC(NCO)=N1 SUPOBRXPULIDDX-UHFFFAOYSA-N 0.000 abstract 4
- 239000003795 chemical substances by application Substances 0.000 abstract 4
- BXWNKGSJHAJOGX-UHFFFAOYSA-N hexadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCO BXWNKGSJHAJOGX-UHFFFAOYSA-N 0.000 abstract 4
- 239000000463 material Substances 0.000 abstract 4
- 229920001592 potato starch Polymers 0.000 abstract 4
- 150000001298 alcohols Chemical class 0.000 abstract 3
- 239000004411 aluminium Substances 0.000 abstract 3
- 229910052782 aluminium Inorganic materials 0.000 abstract 3
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 abstract 3
- BIOOACNPATUQFW-UHFFFAOYSA-N calcium;dioxido(dioxo)molybdenum Chemical compound [Ca+2].[O-][Mo]([O-])(=O)=O BIOOACNPATUQFW-UHFFFAOYSA-N 0.000 abstract 3
- 238000000576 coating method Methods 0.000 abstract 3
- 239000004753 textile Substances 0.000 abstract 3
- YIWUKEYIRIRTPP-UHFFFAOYSA-N 2-ethylhexan-1-ol Chemical compound CCCCC(CC)CO YIWUKEYIRIRTPP-UHFFFAOYSA-N 0.000 abstract 2
- 239000004593 Epoxy Substances 0.000 abstract 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract 2
- 239000005057 Hexamethylene diisocyanate Substances 0.000 abstract 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 abstract 2
- 239000004372 Polyvinyl alcohol Substances 0.000 abstract 2
- 229920002472 Starch Polymers 0.000 abstract 2
- 239000011230 binding agent Substances 0.000 abstract 2
- 239000004566 building material Substances 0.000 abstract 2
- 229960000541 cetyl alcohol Drugs 0.000 abstract 2
- 150000001875 compounds Chemical class 0.000 abstract 2
- 238000001035 drying Methods 0.000 abstract 2
- 239000004744 fabric Substances 0.000 abstract 2
- 239000000835 fiber Substances 0.000 abstract 2
- 239000011521 glass Substances 0.000 abstract 2
- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 abstract 2
- 238000005470 impregnation Methods 0.000 abstract 2
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 abstract 2
- 229910052751 metal Inorganic materials 0.000 abstract 2
- 239000002184 metal Substances 0.000 abstract 2
- ZWRUINPWMLAQRD-UHFFFAOYSA-N nonan-1-ol Chemical compound CCCCCCCCCO ZWRUINPWMLAQRD-UHFFFAOYSA-N 0.000 abstract 2
- 229920002451 polyvinyl alcohol Polymers 0.000 abstract 2
- 239000008107 starch Substances 0.000 abstract 2
- 235000019698 starch Nutrition 0.000 abstract 2
- SZNYYWIUQFZLLT-UHFFFAOYSA-N 2-methyl-1-(2-methylpropoxy)propane Chemical group CC(C)COCC(C)C SZNYYWIUQFZLLT-UHFFFAOYSA-N 0.000 abstract 1
- LCFVJGUPQDGYKZ-UHFFFAOYSA-N Bisphenol A diglycidyl ether Chemical compound C=1C=C(OCC2OC2)C=CC=1C(C)(C)C(C=C1)=CC=C1OCC1CO1 LCFVJGUPQDGYKZ-UHFFFAOYSA-N 0.000 abstract 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 abstract 1
- 229920000742 Cotton Polymers 0.000 abstract 1
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 abstract 1
- 239000004952 Polyamide Substances 0.000 abstract 1
- SMEGJBVQLJJKKX-HOTMZDKISA-N [(2R,3S,4S,5R,6R)-5-acetyloxy-3,4,6-trihydroxyoxan-2-yl]methyl acetate Chemical compound CC(=O)OC[C@@H]1[C@H]([C@@H]([C@H]([C@@H](O1)O)OC(=O)C)O)O SMEGJBVQLJJKKX-HOTMZDKISA-N 0.000 abstract 1
- QBRPPCVQOLMIJM-UHFFFAOYSA-N [1-(hydroxymethyl)cyclohex-2-en-1-yl]methanol Chemical compound OCC1(CO)CCCC=C1 QBRPPCVQOLMIJM-UHFFFAOYSA-N 0.000 abstract 1
- YGCOKJWKWLYHTG-UHFFFAOYSA-N [[4,6-bis[bis(hydroxymethyl)amino]-1,3,5-triazin-2-yl]-(hydroxymethyl)amino]methanol Chemical compound OCN(CO)C1=NC(N(CO)CO)=NC(N(CO)CO)=N1 YGCOKJWKWLYHTG-UHFFFAOYSA-N 0.000 abstract 1
- DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 abstract 1
- 125000002777 acetyl group Chemical class [H]C([H])([H])C(*)=O 0.000 abstract 1
- 229940081735 acetylcellulose Drugs 0.000 abstract 1
- 239000002253 acid Substances 0.000 abstract 1
- 230000002378 acidificating effect Effects 0.000 abstract 1
- 239000000654 additive Substances 0.000 abstract 1
- QQQCWVDPMPFUGF-ZDUSSCGKSA-N alpinetin Chemical group C1([C@H]2OC=3C=C(O)C=C(C=3C(=O)C2)OC)=CC=CC=C1 QQQCWVDPMPFUGF-ZDUSSCGKSA-N 0.000 abstract 1
- XETRDYSPPPDVAB-UHFFFAOYSA-N butan-1-ol;propan-1-ol Chemical compound CCCO.CCCCO XETRDYSPPPDVAB-UHFFFAOYSA-N 0.000 abstract 1
- 235000013877 carbamide Nutrition 0.000 abstract 1
- 125000004432 carbon atom Chemical group C* 0.000 abstract 1
- 239000003054 catalyst Substances 0.000 abstract 1
- 229920002301 cellulose acetate Polymers 0.000 abstract 1
- 239000000084 colloidal system Substances 0.000 abstract 1
- 238000009833 condensation Methods 0.000 abstract 1
- 230000005494 condensation Effects 0.000 abstract 1
- 229910052802 copper Inorganic materials 0.000 abstract 1
- 239000010949 copper Substances 0.000 abstract 1
- XPCJYQUUKUVAMI-UHFFFAOYSA-N cyclohex-2-ene-1-carbaldehyde Chemical compound O=CC1CCCC=C1 XPCJYQUUKUVAMI-UHFFFAOYSA-N 0.000 abstract 1
- HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical compound OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 abstract 1
- GYZLOYUZLJXAJU-UHFFFAOYSA-N diglycidyl ether Chemical compound C1OC1COCC1CO1 GYZLOYUZLJXAJU-UHFFFAOYSA-N 0.000 abstract 1
- 238000007598 dipping method Methods 0.000 abstract 1
- 230000000694 effects Effects 0.000 abstract 1
- 239000003995 emulsifying agent Substances 0.000 abstract 1
- 150000002148 esters Chemical class 0.000 abstract 1
- 239000002657 fibrous material Substances 0.000 abstract 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 abstract 1
- 229910052742 iron Inorganic materials 0.000 abstract 1
- 150000002739 metals Chemical class 0.000 abstract 1
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Natural products C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 abstract 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Natural products OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 abstract 1
- 239000000203 mixture Substances 0.000 abstract 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 abstract 1
- QUBQYFYWUJJAAK-UHFFFAOYSA-N oxymethurea Chemical compound OCNC(=O)NCO QUBQYFYWUJJAAK-UHFFFAOYSA-N 0.000 abstract 1
- 229950005308 oxymethurea Drugs 0.000 abstract 1
- 239000000049 pigment Substances 0.000 abstract 1
- 229920002239 polyacrylonitrile Polymers 0.000 abstract 1
- 229920002647 polyamide Polymers 0.000 abstract 1
- 229920002857 polybutadiene Polymers 0.000 abstract 1
- 229920000728 polyester Polymers 0.000 abstract 1
- 229920000098 polyolefin Polymers 0.000 abstract 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 abstract 1
- 230000001681 protective effect Effects 0.000 abstract 1
- 239000004627 regenerated cellulose Substances 0.000 abstract 1
- 229920005989 resin Polymers 0.000 abstract 1
- 239000011347 resin Substances 0.000 abstract 1
- 238000005507 spraying Methods 0.000 abstract 1
- 239000000758 substrate Substances 0.000 abstract 1
- 238000011282 treatment Methods 0.000 abstract 1
- QQOWHRYOXYEMTL-UHFFFAOYSA-N triazin-4-amine Chemical compound N=C1C=CN=NN1 QQOWHRYOXYEMTL-UHFFFAOYSA-N 0.000 abstract 1
- 210000002268 wool Anatomy 0.000 abstract 1
Classifications
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
- D06M15/00—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment
- D06M15/19—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment with synthetic macromolecular compounds
- D06M15/37—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
- D06M15/55—Epoxy resins
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L61/00—Compositions of condensation polymers of aldehydes or ketones; Compositions of derivatives of such polymers
- C08L61/20—Condensation polymers of aldehydes or ketones with only compounds containing hydrogen attached to nitrogen
-
- 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
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
- D06M15/00—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment
- D06M15/19—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment with synthetic macromolecular compounds
- D06M15/37—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
- D06M15/39—Aldehyde resins; Ketone resins; Polyacetals
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
- D06M15/00—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment
- D06M15/19—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment with synthetic macromolecular compounds
- D06M15/37—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
- D06M15/39—Aldehyde resins; Ketone resins; Polyacetals
- D06M15/423—Amino-aldehyde resins
Landscapes
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Textile Engineering (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
- Epoxy Resins (AREA)
- Paper (AREA)
Abstract
Oil-in-water emulsions contain a mixture of 3-85% by weight of a water-insoluble curable viz. epoxy compound having an epoxide equivalency greater than 1, and 97-15% of a water-insoluble curable aminoplast resin. They may also contain a protective colloid, and a non-ionic or ionic emulsifying agent, many of which are referred to. Many suitable epoxy compounds are referred to. Examples use: Epoxide A-a diglycidyl ether of 4,41-dihydroxydiphenyldimethyl methane Epoxide B-an epoxidized acetal from tetrahydrobenzaldehyde and 1,1 - dimethylolcyclohexene - 3 Epoxide C-Epoxidized ester obtained by condensation of 2 mols. of 2-methyl-tetrahydrobenzaldehyde Epoxide D-vinyl cyclohexene di-epoxide Epoxide E-glycidyl ether of 3,4-epoxy-dicyclopentan - 8 - ol Epoxides F, G and H-partially epoxidized polybutadienes Epoxide I-a condensate of 4,41-dihydroxydiphenyl-dimethylmethate and epichlohydrin. The aminoplasts used are water-insoluble methylol compound of urea or an aminotriazine, which have been etherified with mono-alcohols containing 3-10 carbon atoms. Some suitable alcohols are propanol butanol amyl alcohols hexyl alcohols cyclohexanol, 2-ethyl hexanol nonyl alcohol 2,6-dimethyl-4-heptanol tetrahydrofuran - 2 - methanol 2,2 - dimethyl - 1 - butanol 2,2,4 - trimethyl - I - pentanol 2-propyl-1-heptanol. The emulsions, with or without additives have a wide variety of applications e.g. stiffening textile materials, paper or pasteboard, for which purpose it preferably includes an acidic curing agent, many examples of which are listed, and may also include starch and/or urea. The emulsions may also, together with a curing catalyst, if desired, make coatings on substrates of glass, metals or building materials or be used as binders for pigments or fibre tufts. Aminoplasts used in the examples are: A. A butanol solution of dimethylolmelamine ether containing two n-butyl ether groups. B. butanol solution of hexamethylolmelamine ether containing 6 n-butyl ether groups. C. propanol solution of dimethylolmelamine ether with about two n-propyl ether groups. D. isobutanol solution of dimethylolmelamine ether with two iso-butyl ether groups. E. butanol solution of dimethylolbenzoguanamine ether during two n-butyl ether groups. F. butanol solution of dimethylolurea ether having 2 n-butyl ether groups. Example 1 is similar to the many others. Epoxide A is dispersed in aqueous polyvinyl alcohol with an ethylene oxide adduct of cetyl alcohol. Aminoplast A is emulsified in water containing an ethylene oxide adduct of hydroabityl alcohol, cross-linked with hexamethylene diisocyanate. The emulsions are mixed, and used together with zinc fluoborate, or with urea, potato starch and aluminium sulphate, or with potato starch and aluminium sulphate for stiffening collars by impregnation, followed by drying and curing.ALSO:Aqueous oil-in-water emulsions containing an epoxy resin and an aminoplast (see Division C3) are suitable for making coatings, e.g. by spreading or spraying on substrata, such as building materials, glass or metal, e.g. iron, aluminium or copper. The emulsions may include curing agents and application is followed by curing for 10-60 minutes at 120-240 DEG C., or for 1-2 minutes at 300 DEG C. In Example 15, emulsions containing zinc fluoborate are spread on aluminium sheets and cured for 10 minutes at 150 DEG C. In Example 18, emulsions are diluted with water and brushed on to sheets or bars of aluminium, or are diluted with less water and the sheets or bars are coated by dipping. The coatings are dried for 45 minutes at 180-200 DEG C.ALSO:Fibrous material is stiffened by aqueous oil-in-water emulsions of an epoxy resin and an amino-plant (see Division C3) containing an acid curing agent. The emulsions are especially useful for textile material, e.g. stiffening collars, but may also be used for stiffening paper or plasterboard, or as binders for fibre tufts. Starch and/or urea may be added to the textile stiffening emulsions and aluminium sulphate is an advantageous curing agent. Impregnation is followed by drying and curing. Stiffening effects may be imparted to native, mercerised or regenerated cellulose materials, acetylcellulose, wool, silk, polyamides, polyurthanes, polyolefines, polyacrylonitrile or polyesters, e.g. as yarns, fleeces, felts, woven or knitted fabrics. In Example 1, aqueous emulsions containing an epoxy resin from epichlorohydrin and 4, 41-dihydroxydiphenyl-dimethyl methane, as butanol solution of a dimethylolmelamine butyl ether, polyvinyl alcohol, an ethylene oxide adduct of cetyl alcohol, an ethylene oxide adduct of hydroabutyl alcohol cross-linked with hexamethylene diisocyanate, and trithanolamine to bring the pH to 7 are used for collar stiffening material, (d) with added zinc fluoborate, (e) with added potato starch, urea and aluminium sulphate, and (f) p with added potato starch and aluminium sulphate. Example 14 describes similar treatments of cotton fabric.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH743760A CH364482A (en) | 1960-06-30 | 1960-06-30 | Process for the permanent stiffening of textiles |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ES268679A1 true ES268679A1 (en) | 1961-12-16 |
Family
ID=4325107
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES0268679A Expired ES268679A1 (en) | 1960-06-30 | 1961-06-28 | Stable aqueous emulsions from water-insoluble epoxy resins and water-insoluble aminoplasts |
Country Status (5)
| Country | Link |
|---|---|
| BE (1) | BE605553A (en) |
| CH (1) | CH364482A (en) |
| ES (1) | ES268679A1 (en) |
| GB (1) | GB987432A (en) |
| NL (1) | NL266514A (en) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6255364B1 (en) | 1994-06-21 | 2001-07-03 | Shell Oil Company | Crosslinkable waterborne dispersions of epoxidized polydiene block copolymers and amino resins |
| EP0698638B1 (en) * | 1994-07-18 | 1998-01-28 | Shell Internationale Researchmaatschappij B.V. | Crosslinkable waterborne dispersions of hydroxy functional polydiene polymers and amino resins |
| NL1004711C1 (en) * | 1996-12-06 | 1998-06-09 | Lamers Beheer Bv | Method for reinforcing a plate, sheet or foil. |
-
0
- NL NL266514D patent/NL266514A/xx unknown
- BE BE605553D patent/BE605553A/xx unknown
-
1960
- 1960-06-30 CH CH743760A patent/CH364482A/en unknown
-
1961
- 1961-06-27 GB GB2321361A patent/GB987432A/en not_active Expired
- 1961-06-28 ES ES0268679A patent/ES268679A1/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| NL266514A (en) | |
| CH743760A4 (en) | 1962-05-30 |
| BE605553A (en) | |
| CH364482A (en) | 1962-11-15 |
| GB987432A (en) | 1965-03-31 |
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