GB951549A - Improvements in or relating to vapourpermeable films and coatings - Google Patents
Improvements in or relating to vapourpermeable films and coatingsInfo
- Publication number
- GB951549A GB951549A GB1768161A GB1768161A GB951549A GB 951549 A GB951549 A GB 951549A GB 1768161 A GB1768161 A GB 1768161A GB 1768161 A GB1768161 A GB 1768161A GB 951549 A GB951549 A GB 951549A
- Authority
- GB
- United Kingdom
- Prior art keywords
- diisocyanate
- copolymer
- solution
- water
- glycol
- 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
- 238000000576 coating method Methods 0.000 title abstract 13
- 229920001577 copolymer Polymers 0.000 abstract 28
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 abstract 26
- 229920000642 polymer Polymers 0.000 abstract 14
- 239000007788 liquid Substances 0.000 abstract 12
- 239000011248 coating agent Substances 0.000 abstract 10
- 125000005442 diisocyanate group Chemical group 0.000 abstract 10
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 abstract 10
- 239000002904 solvent Substances 0.000 abstract 10
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical group NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 abstract 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract 8
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 abstract 6
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 abstract 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical group CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 abstract 6
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 abstract 4
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 abstract 4
- 239000005864 Sulphur Substances 0.000 abstract 4
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 abstract 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 abstract 4
- BZHJMEDXRYGGRV-UHFFFAOYSA-N Vinyl chloride Chemical compound ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 abstract 4
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical group [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 abstract 4
- 238000003287 bathing Methods 0.000 abstract 4
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 abstract 4
- 150000001875 compounds Chemical class 0.000 abstract 4
- 229920001971 elastomer Polymers 0.000 abstract 4
- 238000010438 heat treatment Methods 0.000 abstract 4
- 229920003225 polyurethane elastomer Polymers 0.000 abstract 4
- 239000000047 product Substances 0.000 abstract 4
- AVQQQNCBBIEMEU-UHFFFAOYSA-N 1,1,3,3-tetramethylurea Chemical compound CN(C)C(=O)N(C)C AVQQQNCBBIEMEU-UHFFFAOYSA-N 0.000 abstract 2
- VGHSXKTVMPXHNG-UHFFFAOYSA-N 1,3-diisocyanatobenzene Chemical compound O=C=NC1=CC=CC(N=C=O)=C1 VGHSXKTVMPXHNG-UHFFFAOYSA-N 0.000 abstract 2
- WZCQRUWWHSTZEM-UHFFFAOYSA-N 1,3-phenylenediamine Chemical compound NC1=CC=CC(N)=C1 WZCQRUWWHSTZEM-UHFFFAOYSA-N 0.000 abstract 2
- RXYPXQSKLGGKOL-UHFFFAOYSA-N 1,4-dimethylpiperazine Chemical compound CN1CCN(C)CC1 RXYPXQSKLGGKOL-UHFFFAOYSA-N 0.000 abstract 2
- SBJCUZQNHOLYMD-UHFFFAOYSA-N 1,5-Naphthalene diisocyanate Chemical compound C1=CC=C2C(N=C=O)=CC=CC2=C1N=C=O SBJCUZQNHOLYMD-UHFFFAOYSA-N 0.000 abstract 2
- KGRVJHAUYBGFFP-UHFFFAOYSA-N 2,2'-Methylenebis(4-methyl-6-tert-butylphenol) Chemical compound CC(C)(C)C1=CC(C)=CC(CC=2C(=C(C=C(C)C=2)C(C)(C)C)O)=C1O KGRVJHAUYBGFFP-UHFFFAOYSA-N 0.000 abstract 2
- VOZKAJLKRJDJLL-UHFFFAOYSA-N 2,4-diaminotoluene Chemical compound CC1=CC=C(N)C=C1N VOZKAJLKRJDJLL-UHFFFAOYSA-N 0.000 abstract 2
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical class COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 abstract 2
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Chemical class OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 abstract 2
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 abstract 2
- HXDLWJWIAHWIKI-UHFFFAOYSA-N 2-hydroxyethyl acetate Chemical compound CC(=O)OCCO HXDLWJWIAHWIKI-UHFFFAOYSA-N 0.000 abstract 2
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 abstract 2
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 abstract 2
- 239000004215 Carbon black (E152) Substances 0.000 abstract 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 abstract 2
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 abstract 2
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 abstract 2
- LPEYYDRITDFCBO-UHFFFAOYSA-N N=C=O.N=C=O.C1=CC=C2CCCCC2=C1 Chemical compound N=C=O.N=C=O.C1=CC=C2CCCCC2=C1 LPEYYDRITDFCBO-UHFFFAOYSA-N 0.000 abstract 2
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 abstract 2
- -1 acrylic nitrile Chemical class 0.000 abstract 2
- 150000001298 alcohols Chemical class 0.000 abstract 2
- 229910052788 barium Inorganic materials 0.000 abstract 2
- DSAJWYNOEDNPEQ-UHFFFAOYSA-N barium atom Chemical compound [Ba] DSAJWYNOEDNPEQ-UHFFFAOYSA-N 0.000 abstract 2
- 229910052791 calcium Inorganic materials 0.000 abstract 2
- 239000011575 calcium Substances 0.000 abstract 2
- 125000004432 carbon atom Chemical group C* 0.000 abstract 2
- 150000001732 carboxylic acid derivatives Chemical class 0.000 abstract 2
- 239000007795 chemical reaction product Substances 0.000 abstract 2
- 229910017052 cobalt Inorganic materials 0.000 abstract 2
- 239000010941 cobalt Substances 0.000 abstract 2
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 abstract 2
- 239000000470 constituent Substances 0.000 abstract 2
- 238000004132 cross linking Methods 0.000 abstract 2
- 150000004985 diamines Chemical group 0.000 abstract 2
- AYOHIQLKSOJJQH-UHFFFAOYSA-N dibutyltin Chemical compound CCCC[Sn]CCCC AYOHIQLKSOJJQH-UHFFFAOYSA-N 0.000 abstract 2
- 150000001993 dienes Chemical class 0.000 abstract 2
- 239000000539 dimer Substances 0.000 abstract 2
- 229960001760 dimethyl sulfoxide Drugs 0.000 abstract 2
- 239000012971 dimethylpiperazine Substances 0.000 abstract 2
- 238000001035 drying Methods 0.000 abstract 2
- 239000000806 elastomer Substances 0.000 abstract 2
- 239000002657 fibrous material Substances 0.000 abstract 2
- 150000002334 glycols Chemical class 0.000 abstract 2
- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 abstract 2
- 150000002429 hydrazines Chemical class 0.000 abstract 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 2
- 239000012948 isocyanate Substances 0.000 abstract 2
- 150000002576 ketones Chemical class 0.000 abstract 2
- 229940018564 m-phenylenediamine Drugs 0.000 abstract 2
- 229910052749 magnesium Inorganic materials 0.000 abstract 2
- 239000011777 magnesium Substances 0.000 abstract 2
- 239000000463 material Substances 0.000 abstract 2
- 229910052751 metal Inorganic materials 0.000 abstract 2
- 239000002184 metal Substances 0.000 abstract 2
- 229910044991 metal oxide Inorganic materials 0.000 abstract 2
- 150000004706 metal oxides Chemical class 0.000 abstract 2
- 239000000178 monomer Substances 0.000 abstract 2
- 239000003960 organic solvent Substances 0.000 abstract 2
- 238000006116 polymerization reaction Methods 0.000 abstract 2
- 229910052712 strontium Inorganic materials 0.000 abstract 2
- CIOAGBVUUVVLOB-UHFFFAOYSA-N strontium atom Chemical compound [Sr] CIOAGBVUUVVLOB-UHFFFAOYSA-N 0.000 abstract 2
- 238000006467 substitution reaction Methods 0.000 abstract 2
- 239000000758 substrate Substances 0.000 abstract 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 abstract 2
- 229910052718 tin Inorganic materials 0.000 abstract 2
- 239000011135 tin Substances 0.000 abstract 2
- DVKJHBMWWAPEIU-UHFFFAOYSA-N toluene 2,4-diisocyanate Chemical compound CC1=CC=C(N=C=O)C=C1N=C=O DVKJHBMWWAPEIU-UHFFFAOYSA-N 0.000 abstract 2
- RUELTTOHQODFPA-UHFFFAOYSA-N toluene 2,6-diisocyanate Chemical compound CC1=C(N=C=O)C=CC=C1N=C=O RUELTTOHQODFPA-UHFFFAOYSA-N 0.000 abstract 2
- 239000011787 zinc oxide Substances 0.000 abstract 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 abstract 1
- 229930195733 hydrocarbon Natural products 0.000 abstract 1
- 150000002430 hydrocarbons Chemical class 0.000 abstract 1
- 150000002513 isocyanates Chemical class 0.000 abstract 1
Classifications
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06N—WALL, FLOOR, OR LIKE COVERING MATERIALS, e.g. LINOLEUM, OILCLOTH, ARTIFICIAL LEATHER, ROOFING FELT, CONSISTING OF A FIBROUS WEB COATED WITH A LAYER OF MACROMOLECULAR MATERIAL; FLEXIBLE SHEET MATERIAL NOT OTHERWISE PROVIDED FOR
- D06N3/00—Artificial leather, oilcloth or other material obtained by covering fibrous webs with macromolecular material, e.g. resins, rubber or derivatives thereof
- D06N3/04—Artificial leather, oilcloth or other material obtained by covering fibrous webs with macromolecular material, e.g. resins, rubber or derivatives thereof with macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
- D06N3/10—Artificial leather, oilcloth or other material obtained by covering fibrous webs with macromolecular material, e.g. resins, rubber or derivatives thereof with macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds with styrene-butadiene copolymerisation products or other synthetic rubbers or elastomers except polyurethanes
Landscapes
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Textile Engineering (AREA)
- Synthetic Leather, Interior Materials Or Flexible Sheet Materials (AREA)
- Polyurethanes Or Polyureas (AREA)
- Paints Or Removers (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Manufacture Of Porous Articles, And Recovery And Treatment Of Waste Products (AREA)
Abstract
Vapour-permeable microporous films and coatings are produced by forming a film or coating of a water-insoluble copolymer containing carboxyl groups on the polymer chain, with or without a proportion of a vinyl chloride polymer or a polyurethane elastomer which may exceed the proportion of the co-polymer, from a solution of the copolymer (and other polymer if employed) in a water-miscible solvent therefor, the solution containing also an oxide of a polyvalent metal, bathing the film or coating with water or an equivalent inert liquid to coagulate the copolymer and remove the solvent, and curing and drying the film or coating produced. The solution of the copolymer may also contain sulphur. The copolymer may be derived from two or more monomers, at least one of which is a conjugated diene having 4-9 carbon atoms in the molecule, and at least one of which is a carboxylic acid containing ethylenic unsaturation at which polymerization can take place. The copolymer may be a rubber ter-polymer of a butadiene-1,2-hydrocarbon, acrylonitrile or a substituted acrylic nitrile, or acrylic acid or a homologue or a -substitution product thereof. The solution may contain a vinyl chloride polymer in a weight ratio to the copolymer of up to 50:50. The solution may be brought to the verge of gelling before mixing it with water or an equivalent inert liquid. The solution may be applied as a coating to a substrate of a flexible porous fibrous material or of a smooth surfaced impervious material. In the latter case to form a film which is subsequently stripped from the film support. The copolymer in the film or layer may be partially cured by heating with water or an equivalent inert liquid to a temperature above normal room temperature. The copolymer may contain residual unsaturation and the solution may contain sulphur and after partial curing the film or coating may be heated until the copolymer is fully cured. An "equivalent" inert liquid is defined as one which is (a) a non-solvent for the copolymer and any other polymer which may be present in the solution; (b) miscible with water and the organic solvent in which the copolymer is dissolved; (c) chemically inert to all the constituents of the film-forming solution at the bathing temperature. Examples of suitable liquids are ethylene glycol, glycerol, glycol monoethyl ether, hydroxyethyl acetate, and water-miscible alcohols such as t-butyl alcohol. The preferred polyvalent metal oxide is zinc oxide, but oxides of calcium, magnesium, tin, dibutyl tin, lead, barium, cobalt or strontium known to be suitable for cross-linking polymers having carboxyl groups can also be used. The preferred solvent is N,N-dimethylformamide. Others which may be used include dimethyl sulphoxide, tetrahydrofuran, tetramethyl urea, N,N-dimethylacetamide, N-methyl-2-pyrrolidone and g -butyrolacetone. These solvents may be blended with water-miscible organic liquids such as ketones, e.g. methyl ethyl ketone. Polyurethane elastomers which may be used as components of the copolymer solution are prepared by chain-extending the reaction product of a polyalkylene-ether glycol and an organic diisocyanate with a compound having two active hydrogen atoms attached to amino nitrogen atoms. These elastomers can be made from a prepolymer (or "capped dimer") obtained by heating the glycol mixed with the diisocyanate until a prepolymer is formed having terminal -NCO group, or by reacting the diisocyanate with a molar excess of the glycol, and capping the product by reacting it with more diisocyanate. Polyalkyleneether glycols which may be used in making the prepolymers include polyethyleneether glycol to polydecamethyleneether glycol. Diisocyanates which may be used in forming the prepolymers include tolylene-2, 4-diisocyanate, tolylene-2, 6-diisocyanate, m-phenylene diisocyanate, bisphenylene-4, 41-diisocyanate, naphthalene-1, 5-diisocyanate, tetramethylene-1, 4-diisocyanate, hexamethylene-1, 6-diisocyanate, decamethylene-1, 10-diisocyanate, cyclohexylene-1, 4-diisocyanate, methylene bis(4-cyclohexylene) isocyanate and tetrahydronaphthalene diisocyanate. The chain extending compound may be hydrazine (which is preferred), a substituted hydrazine or a primary or secondary diamine. Examples are dimethyl piperazine, 4-methyl-m-phenylene diamine, m-phenylene diamine, and 4,41-diaminodiphenyl-methane. Specification 849,155, U.S.A. Specifications 2,395,017, 2,724,707, and 3,067,483 are referred to.ALSO:Vapour-permeable microporous coatings are produced by forming a coating of a water-insoluble copolymer containing carboxyl groups on the polymer chain, with or without a proportion of a vinyl chloride polymer or a polyurethane elastomer which may exceed the proportion of the copolymer, from a solution of the copolymer (and other polymer if employed) in a water-miscible solvent therefor, the solution containing also an oxide of a polyvalent metal, bathing the coating with water or an equivalent inert liquid to coagulate the copolymer and remove the solvent, and curing and drying the coating produced. The solution of the copolymer may also contain sulphur. The copolymer may be derived from two or more monomers, at least one of which is a conjugated diene having 4-9 carbon atoms in the molecule, and at least one of which is a carboxylic acid containing ethylenic unsaturation at which polymerization can take place. The copolymer may be a rubber ter-polymer of a butadiene-1,2 hydrocarbon, acrylonitrile or a substituted acrylic nitrile, or acrylic acid or a homologue or a -substitution product thereof. The solution may contain a vinyl chloride polymer in a weight ratio to the copolymer of up to 50 : 50. The solution may be brought to the verge of gelling before mixing it with water or an equivalent inert liquid. The solution may be applied as a coating to a substrate of a flexible porous fibrous material or of a smooth surfaced impervious material from which it may be subsequently stripped. The copolymer may be partially cured by heating with water or an equivalent inert liquid to a temperature above normal room temperature. The copolymer may contain residual unsaturation and the solution may contain sulphur and after partial curing the coating may be heated until the copolymer is fully cured. An "equivalent" inert liquid is defined as one which is (a) a non-solvent for the copolymer and any other polymer which may be present in the solution; (b) miscible with water and the organic solvent in which the copolymer is dissolved; (c) chemically inert to all the constituents of the film-forming solution at the bathing temperature. Examples of suitable liquids are ethylene glycol, glycerol, glycol monoethyl ether, hydroxyethyl acetate, and water-miscible alcohols such as t-butyl alcohol. The preferred polyvalent metal oxide is zinc oxide, but oxides of calcium, magnesium, tin, dibutyl tin, lead, barium, cobalt or strontium known to be suitable for cross-linking polymers having carboxyl groups can also be used. The preferred solvent is N,N-dimethylformamide. Others which may be used include dimethyl sulphoxide, tetrahydrofuran, tetramethyl urea, N,N-dimethylacetamide, N-methyl - 2 - pyrrolidone and g - butyrolacetone. These solvents may be blended with water-miscible organic liquids such as ketones, e.g. methyl ethyl ketone. Polyurethane elastomers which may be used as components of the copolymer solution are prepared by chain-extending the reaction product of a polyalkyleneether glycol and an organic diisocyanate with a compound having two active hydrogen atoms attached to amino nitrogen atoms. These elastomers can be made from a prepolymer (or "capped dimer") obtained by heating the glycol mixed with the diisocyanate until a prepolymer is formed having terminal -NCO group, or by reacting the diisocyanate with a molar excess of the glycol, and capping the product by reacting it with more diisocyanate. Polyalkyleneether glycols which may be used in making the prepolymers include polyethyleneether glycol to polydecamethyleneether glycol. Diisocyanates which may be used in forming the prepolymers include tolylene-2,4-diisocyanate, tolylene-2,6-diisocyanate, m-phenylene diisocyanate, bisphenylene - 4,41 - diisocyanate, naphthalene-1,5-diisocyanate, tetramethylene-1, 4-diisocyanate, hexamethylene-1,6-diisocyanate, decamethylene-1,10-diisocyanate, cyclohexylene-1,4-diisocyanate, methylene bis(4-cyclohexylene isocyanate and tetrahydronaphthalene diisocyanate. The chain extending compound may be hydrazine (which is preferred), a substituted hydrazine or a primary or secondary diamine. Examples are dimethyl piperazine, 4-methyl-m-phenylene diamine, m-phenylene diamine, and 4,41-diamino-diphenyl-methane. Specification 849,155 and U.S.A. Specifications 2,395,017, 2,724,707 and 3,067,483 are referred to.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US2912560A | 1960-05-16 | 1960-05-16 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB951549A true GB951549A (en) | 1964-03-04 |
Family
ID=21847369
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB1768161A Expired GB951549A (en) | 1960-05-16 | 1961-05-15 | Improvements in or relating to vapourpermeable films and coatings |
Country Status (3)
| Country | Link |
|---|---|
| BE (1) | BE603821A (en) |
| DE (1) | DE1470918A1 (en) |
| GB (1) | GB951549A (en) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB2174641A (en) * | 1985-04-29 | 1986-11-12 | Grace W R & Co | Non-adsorptive, semipermeable filtration membrane |
| WO2003095419A1 (en) * | 2002-05-09 | 2003-11-20 | Bayer Materialscience Llc | Tetralin isocyanates |
| US9701824B2 (en) | 2014-12-23 | 2017-07-11 | Dow Global Technologies Llc | Polyolefin dispersion compositions for making high vapor transport hydrophobic coatings |
-
1961
- 1961-05-15 GB GB1768161A patent/GB951549A/en not_active Expired
- 1961-05-15 BE BE603821A patent/BE603821A/fr unknown
- 1961-05-16 DE DE19611470918 patent/DE1470918A1/en active Pending
Cited By (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB2174641A (en) * | 1985-04-29 | 1986-11-12 | Grace W R & Co | Non-adsorptive, semipermeable filtration membrane |
| US4787976A (en) * | 1985-04-29 | 1988-11-29 | W. R. Grace & Co. | Non-adsorptive, semipermeable filtration membrane |
| GB2174641B (en) * | 1985-04-29 | 1989-07-12 | Grace W R & Co | Non-adsorptive, semipermeable filtration membrane |
| WO2003095419A1 (en) * | 2002-05-09 | 2003-11-20 | Bayer Materialscience Llc | Tetralin isocyanates |
| US6750367B2 (en) | 2002-05-09 | 2004-06-15 | Bayer Polymers Llc | Tetralin isocyanates |
| US6841585B2 (en) | 2002-05-09 | 2005-01-11 | Bayer Materialscience Llc | Tetralin isocyanates |
| JP2005524716A (en) * | 2002-05-09 | 2005-08-18 | バイエル マテリアルサイエンス エルエルシー | Tetralin isocyanate |
| US9701824B2 (en) | 2014-12-23 | 2017-07-11 | Dow Global Technologies Llc | Polyolefin dispersion compositions for making high vapor transport hydrophobic coatings |
Also Published As
| Publication number | Publication date |
|---|---|
| DE1470918A1 (en) | 1969-08-07 |
| BE603821A (en) | 1961-11-16 |
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