CA1047306A - Synthetic meat flavors for texturised vegetable protein - Google Patents
Synthetic meat flavors for texturised vegetable proteinInfo
- Publication number
- CA1047306A CA1047306A CA219,083A CA219083A CA1047306A CA 1047306 A CA1047306 A CA 1047306A CA 219083 A CA219083 A CA 219083A CA 1047306 A CA1047306 A CA 1047306A
- Authority
- CA
- Canada
- Prior art keywords
- protein
- plastein
- weight
- process according
- product
- 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
- 239000000796 flavoring agent Substances 0.000 title claims abstract description 91
- 235000019634 flavors Nutrition 0.000 title claims description 65
- 108010082495 Dietary Plant Proteins Proteins 0.000 title claims description 10
- 235000013372 meat Nutrition 0.000 title description 10
- 108090000623 proteins and genes Proteins 0.000 claims abstract description 68
- 102000004169 proteins and genes Human genes 0.000 claims abstract description 68
- 108010024951 plastein Proteins 0.000 claims abstract description 47
- 239000000203 mixture Substances 0.000 claims abstract description 40
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 33
- 235000013355 food flavoring agent Nutrition 0.000 claims abstract description 24
- 150000001413 amino acids Chemical class 0.000 claims abstract description 14
- 238000006243 chemical reaction Methods 0.000 claims abstract description 13
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims abstract description 11
- 229910052717 sulfur Inorganic materials 0.000 claims abstract description 9
- 239000011593 sulfur Substances 0.000 claims abstract description 9
- 150000002772 monosaccharides Chemical class 0.000 claims abstract description 6
- 238000004519 manufacturing process Methods 0.000 claims abstract description 4
- 235000018102 proteins Nutrition 0.000 claims description 66
- 238000000034 method Methods 0.000 claims description 42
- 230000008569 process Effects 0.000 claims description 23
- 238000010438 heat treatment Methods 0.000 claims description 15
- 244000068988 Glycine max Species 0.000 claims description 13
- 235000010469 Glycine max Nutrition 0.000 claims description 13
- 235000001014 amino acid Nutrition 0.000 claims description 13
- 150000002402 hexoses Chemical class 0.000 claims description 11
- 229930182817 methionine Natural products 0.000 claims description 10
- HMFHBZSHGGEWLO-SOOFDHNKSA-N D-ribofuranose Chemical compound OC[C@H]1OC(O)[C@H](O)[C@@H]1O HMFHBZSHGGEWLO-SOOFDHNKSA-N 0.000 claims description 9
- PYMYPHUHKUWMLA-LMVFSUKVSA-N Ribose Natural products OC[C@@H](O)[C@@H](O)[C@@H](O)C=O PYMYPHUHKUWMLA-LMVFSUKVSA-N 0.000 claims description 9
- HMFHBZSHGGEWLO-UHFFFAOYSA-N alpha-D-Furanose-Ribose Natural products OCC1OC(O)C(O)C1O HMFHBZSHGGEWLO-UHFFFAOYSA-N 0.000 claims description 9
- FFEARJCKVFRZRR-BYPYZUCNSA-N L-methionine Chemical compound CSCC[C@H](N)C(O)=O FFEARJCKVFRZRR-BYPYZUCNSA-N 0.000 claims description 8
- XUJNEKJLAYXESH-UHFFFAOYSA-N cysteine Natural products SCC(N)C(O)=O XUJNEKJLAYXESH-UHFFFAOYSA-N 0.000 claims description 8
- LPUQAYUQRXPFSQ-DFWYDOINSA-M monosodium L-glutamate Chemical group [Na+].[O-]C(=O)[C@@H](N)CCC(O)=O LPUQAYUQRXPFSQ-DFWYDOINSA-M 0.000 claims description 8
- 235000013923 monosodium glutamate Nutrition 0.000 claims description 8
- 239000004223 monosodium glutamate Substances 0.000 claims description 8
- -1 pentose monosaccharide Chemical class 0.000 claims description 7
- 150000002972 pentoses Chemical class 0.000 claims description 5
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 claims description 4
- 235000018417 cysteine Nutrition 0.000 claims description 4
- 229960003067 cystine Drugs 0.000 claims description 4
- 239000008103 glucose Substances 0.000 claims description 4
- DWPCPZJAHOETAG-UHFFFAOYSA-N meso-lanthionine Natural products OC(=O)C(N)CSCC(N)C(O)=O DWPCPZJAHOETAG-UHFFFAOYSA-N 0.000 claims description 4
- XUJNEKJLAYXESH-REOHCLBHSA-N L-Cysteine Chemical compound SC[C@H](N)C(O)=O XUJNEKJLAYXESH-REOHCLBHSA-N 0.000 claims description 3
- DWPCPZJAHOETAG-IMJSIDKUSA-N L-lanthionine Chemical compound OC(=O)[C@@H](N)CSC[C@H](N)C(O)=O DWPCPZJAHOETAG-IMJSIDKUSA-N 0.000 claims description 3
- 125000000217 alkyl group Chemical group 0.000 claims description 3
- PYMYPHUHKUWMLA-WDCZJNDASA-N arabinose Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)C=O PYMYPHUHKUWMLA-WDCZJNDASA-N 0.000 claims description 3
- PYMYPHUHKUWMLA-UHFFFAOYSA-N arabinose Natural products OCC(O)C(O)C(O)C=O PYMYPHUHKUWMLA-UHFFFAOYSA-N 0.000 claims description 3
- SRBFZHDQGSBBOR-UHFFFAOYSA-N beta-D-Pyranose-Lyxose Natural products OC1COC(O)C(O)C1O SRBFZHDQGSBBOR-UHFFFAOYSA-N 0.000 claims description 3
- 239000003607 modifier Substances 0.000 claims description 3
- 125000005907 alkyl ester group Chemical group 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- 239000013589 supplement Substances 0.000 claims description 2
- LEVWYRKDKASIDU-QWWZWVQMSA-N D-cystine Chemical compound OC(=O)[C@H](N)CSSC[C@@H](N)C(O)=O LEVWYRKDKASIDU-QWWZWVQMSA-N 0.000 claims 1
- WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 claims 1
- 239000000047 product Substances 0.000 description 99
- 235000015278 beef Nutrition 0.000 description 26
- 230000002085 persistent effect Effects 0.000 description 16
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- 239000003795 chemical substances by application Substances 0.000 description 10
- 230000002688 persistence Effects 0.000 description 10
- 229940024606 amino acid Drugs 0.000 description 9
- 235000006109 methionine Nutrition 0.000 description 9
- 239000000243 solution Substances 0.000 description 9
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
- 230000001055 chewing effect Effects 0.000 description 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 7
- 229960004452 methionine Drugs 0.000 description 7
- YNJBWRMUSHSURL-UHFFFAOYSA-N trichloroacetic acid Chemical compound OC(=O)C(Cl)(Cl)Cl YNJBWRMUSHSURL-UHFFFAOYSA-N 0.000 description 7
- 229960004319 trichloroacetic acid Drugs 0.000 description 7
- 239000000463 material Substances 0.000 description 6
- 102000057297 Pepsin A Human genes 0.000 description 5
- 108090000284 Pepsin A Proteins 0.000 description 5
- 238000001125 extrusion Methods 0.000 description 5
- 235000013305 food Nutrition 0.000 description 5
- 235000012054 meals Nutrition 0.000 description 5
- 229940111202 pepsin Drugs 0.000 description 5
- WHUUTDBJXJRKMK-VKHMYHEASA-N L-glutamic acid Chemical compound OC(=O)[C@@H](N)CCC(O)=O WHUUTDBJXJRKMK-VKHMYHEASA-N 0.000 description 4
- 239000007864 aqueous solution Substances 0.000 description 4
- 235000012343 cottonseed oil Nutrition 0.000 description 4
- 229930195712 glutamate Natural products 0.000 description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- 239000000843 powder Substances 0.000 description 4
- 235000011121 sodium hydroxide Nutrition 0.000 description 4
- 235000017060 Arachis glabrata Nutrition 0.000 description 3
- 244000105624 Arachis hypogaea Species 0.000 description 3
- 235000010777 Arachis hypogaea Nutrition 0.000 description 3
- 235000018262 Arachis monticola Nutrition 0.000 description 3
- 235000003255 Carthamus tinctorius Nutrition 0.000 description 3
- 244000020518 Carthamus tinctorius Species 0.000 description 3
- 239000004470 DL Methionine Substances 0.000 description 3
- 241000287828 Gallus gallus Species 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 239000005018 casein Substances 0.000 description 3
- BECPQYXYKAMYBN-UHFFFAOYSA-N casein, tech. Chemical compound NCCCCC(C(O)=O)N=C(O)C(CC(O)=O)N=C(O)C(CCC(O)=N)N=C(O)C(CC(C)C)N=C(O)C(CCC(O)=O)N=C(O)C(CC(O)=O)N=C(O)C(CCC(O)=O)N=C(O)C(C(C)O)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=O)N=C(O)C(CCC(O)=O)N=C(O)C(COP(O)(O)=O)N=C(O)C(CCC(O)=N)N=C(O)C(N)CC1=CC=CC=C1 BECPQYXYKAMYBN-UHFFFAOYSA-N 0.000 description 3
- 235000021240 caseins Nutrition 0.000 description 3
- 229960002433 cysteine Drugs 0.000 description 3
- 150000002148 esters Chemical class 0.000 description 3
- 235000013312 flour Nutrition 0.000 description 3
- 238000006703 hydration reaction Methods 0.000 description 3
- FFEARJCKVFRZRR-UHFFFAOYSA-N methionine Chemical compound CSCCC(N)C(O)=O FFEARJCKVFRZRR-UHFFFAOYSA-N 0.000 description 3
- 235000020232 peanut Nutrition 0.000 description 3
- 238000001556 precipitation Methods 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- 241000894007 species Species 0.000 description 3
- 108010028690 Fish Proteins Proteins 0.000 description 2
- LEVWYRKDKASIDU-IMJSIDKUSA-N L-cystine Chemical compound [O-]C(=O)[C@@H]([NH3+])CSSC[C@H]([NH3+])C([O-])=O LEVWYRKDKASIDU-IMJSIDKUSA-N 0.000 description 2
- 102000035195 Peptidases Human genes 0.000 description 2
- 108091005804 Peptidases Proteins 0.000 description 2
- 239000005864 Sulphur Substances 0.000 description 2
- 241000209140 Triticum Species 0.000 description 2
- 235000021307 Triticum Nutrition 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 235000019658 bitter taste Nutrition 0.000 description 2
- 235000015223 cooked beef Nutrition 0.000 description 2
- 229940078469 dl- cysteine Drugs 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- ARJXIGOIOGJAKR-LURJTMIESA-N ethyl L-methioninate Chemical group CCOC(=O)[C@@H](N)CCSC ARJXIGOIOGJAKR-LURJTMIESA-N 0.000 description 2
- 125000004494 ethyl ester group Chemical group 0.000 description 2
- 235000012438 extruded product Nutrition 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- DWPCPZJAHOETAG-ZXZARUISSA-N meso-lanthionine Chemical compound OC(=O)[C@@H](N)CSC[C@@H](N)C(O)=O DWPCPZJAHOETAG-ZXZARUISSA-N 0.000 description 2
- NXPNPYNCKSWEHA-WDSKDSINSA-N methyl (2r)-2-amino-3-[[(2r)-2-amino-3-methoxy-3-oxopropyl]disulfanyl]propanoate Chemical compound COC(=O)[C@@H](N)CSSC[C@H](N)C(=O)OC NXPNPYNCKSWEHA-WDSKDSINSA-N 0.000 description 2
- 230000000813 microbial effect Effects 0.000 description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 2
- 108090000765 processed proteins & peptides Proteins 0.000 description 2
- 230000017854 proteolysis Effects 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- PNROREDTZJCOHF-UHFFFAOYSA-N 2-(3,5-dichlorophenoxy)acetonitrile Chemical compound ClC1=CC(Cl)=CC(OCC#N)=C1 PNROREDTZJCOHF-UHFFFAOYSA-N 0.000 description 1
- MCYHPZGUONZRGO-UHFFFAOYSA-N 2-azaniumyl-3-methoxy-3-oxopropane-1-thiolate Chemical compound COC(=O)C(N)CS MCYHPZGUONZRGO-UHFFFAOYSA-N 0.000 description 1
- WROIATXTPLVOLU-UHFFFAOYSA-N 2-methylpropyl 2-amino-3-sulfanylpropanoate;hydrochloride Chemical compound Cl.CC(C)COC(=O)C(N)CS WROIATXTPLVOLU-UHFFFAOYSA-N 0.000 description 1
- 241000003910 Baronia <angiosperm> Species 0.000 description 1
- GVAZBGDSSYDLEQ-UHFFFAOYSA-N Br.Br.CCCCOC(=O)C(N)CSSCC(N)C(=O)OCCCC Chemical compound Br.Br.CCCCOC(=O)C(N)CSSCC(N)C(=O)OCCCC GVAZBGDSSYDLEQ-UHFFFAOYSA-N 0.000 description 1
- 241000518994 Conta Species 0.000 description 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 1
- 108090000790 Enzymes Proteins 0.000 description 1
- 102000004190 Enzymes Human genes 0.000 description 1
- 239000005905 Hydrolysed protein Substances 0.000 description 1
- 239000004158 L-cystine Substances 0.000 description 1
- 235000019393 L-cystine Nutrition 0.000 description 1
- 229930195722 L-methionine Natural products 0.000 description 1
- 241001163743 Perlodes Species 0.000 description 1
- 244000000231 Sesamum indicum Species 0.000 description 1
- 235000003434 Sesamum indicum Nutrition 0.000 description 1
- 241000364027 Sinoe Species 0.000 description 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- 240000008042 Zea mays Species 0.000 description 1
- 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 1
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 1
- VLSOAXRVHARBEQ-UHFFFAOYSA-N [4-fluoro-2-(hydroxymethyl)phenyl]methanol Chemical compound OCC1=CC=C(F)C=C1CO VLSOAXRVHARBEQ-UHFFFAOYSA-N 0.000 description 1
- 239000001058 brown pigment Substances 0.000 description 1
- DQZMWKCUEHXYCE-UHFFFAOYSA-N butyl 2-amino-3-[(2-amino-3-butoxy-3-oxopropyl)disulfanyl]propanoate Chemical compound CCCCOC(=O)C(N)CSSCC(N)C(=O)OCCCC DQZMWKCUEHXYCE-UHFFFAOYSA-N 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- XTEGARKTQYYJKE-UHFFFAOYSA-N chloric acid Chemical compound OCl(=O)=O XTEGARKTQYYJKE-UHFFFAOYSA-N 0.000 description 1
- 229940005991 chloric acid Drugs 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 235000008504 concentrate Nutrition 0.000 description 1
- 238000010411 cooking Methods 0.000 description 1
- 235000005822 corn Nutrition 0.000 description 1
- 230000002939 deleterious effect Effects 0.000 description 1
- 239000011928 denatured alcohol Substances 0.000 description 1
- 238000000502 dialysis Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000002255 enzymatic effect Effects 0.000 description 1
- 229940088598 enzyme Drugs 0.000 description 1
- 239000012634 fragment 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
- 230000036571 hydration Effects 0.000 description 1
- 229960000443 hydrochloric acid Drugs 0.000 description 1
- 235000011167 hydrochloric acid Nutrition 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 238000010348 incorporation Methods 0.000 description 1
- 150000002605 large molecules Chemical class 0.000 description 1
- 230000005923 long-lasting effect Effects 0.000 description 1
- UJTVUMVERRXLBT-UHFFFAOYSA-N methyl 2-amino-3-(2-amino-3-methoxy-3-oxopropyl)sulfanylpropanoate dihydrochloride Chemical compound Cl.Cl.COC(=O)C(N)CSCC(N)C(=O)OC UJTVUMVERRXLBT-UHFFFAOYSA-N 0.000 description 1
- 150000004702 methyl esters Chemical class 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 238000006068 polycondensation reaction Methods 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 102000004196 processed proteins & peptides Human genes 0.000 description 1
- WLUAUPQSKOQURS-ZETCQYMHSA-N propan-2-yl (2s)-2-amino-4-methylsulfanylbutanoate Chemical compound CSCC[C@H](N)C(=O)OC(C)C WLUAUPQSKOQURS-ZETCQYMHSA-N 0.000 description 1
- QAAOQCWMSDMQMI-UHFFFAOYSA-N propyl 2-amino-4-methylsulfanylbutanoate Chemical compound CCCOC(=O)C(N)CCSC QAAOQCWMSDMQMI-UHFFFAOYSA-N 0.000 description 1
- 235000019833 protease Nutrition 0.000 description 1
- 229940070376 protein Drugs 0.000 description 1
- 239000003531 protein hydrolysate Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 108010027322 single cell proteins Proteins 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 230000009469 supplementation Effects 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 235000019640 taste Nutrition 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
- KMIOJWCYOHBUJS-HAKPAVFJSA-N vorolanib Chemical compound C1N(C(=O)N(C)C)CC[C@@H]1NC(=O)C1=C(C)NC(\C=C/2C3=CC(F)=CC=C3NC\2=O)=C1C KMIOJWCYOHBUJS-HAKPAVFJSA-N 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23L—FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES, NOT OTHERWISE PROVIDED FOR; PREPARATION OR TREATMENT THEREOF
- A23L27/00—Spices; Flavouring agents or condiments; Artificial sweetening agents; Table salts; Dietetic salt substitutes; Preparation or treatment thereof
- A23L27/20—Synthetic spices, flavouring agents or condiments
- A23L27/21—Synthetic spices, flavouring agents or condiments containing amino acids
- A23L27/215—Synthetic spices, flavouring agents or condiments containing amino acids heated in the presence of reducing sugars, e.g. Maillard's non-enzymatic browning
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Health & Medical Sciences (AREA)
- Nutrition Science (AREA)
- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Food Science & Technology (AREA)
- Polymers & Plastics (AREA)
- Seasonings (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Meat, Egg Or Seafood Products (AREA)
- Confectionery (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB735074A GB1469331A (en) | 1974-02-18 | 1974-02-18 | Flavouring agent |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1047306A true CA1047306A (en) | 1979-01-30 |
Family
ID=9831444
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA219,083A Expired CA1047306A (en) | 1974-02-18 | 1975-01-30 | Synthetic meat flavors for texturised vegetable protein |
Country Status (10)
Families Citing this family (27)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3300402A (en) * | 1964-01-09 | 1967-01-24 | Purifax Inc | Purification of putrescible unstable wastes |
| CH670743A5 (enrdf_load_stackoverflow) * | 1987-04-06 | 1989-07-14 | Nestle Sa | |
| CH682878A5 (fr) * | 1991-11-01 | 1993-12-15 | Nestle Sa | Procédé permettant d'éviter le brunissement d'un produit alimentaire. |
| GB0319463D0 (en) * | 2003-08-20 | 2003-09-17 | Givaudan Sa | Compounds |
| KR101963076B1 (ko) | 2005-07-26 | 2019-03-27 | 크나우프 인설레이션, 인크. | 접착제 및 이들로 만들어진 물질 |
| GB0520872D0 (en) * | 2005-10-14 | 2005-11-23 | Hofmann Thomas F | Onion flavour compounds and use |
| BRPI0721232B1 (pt) | 2007-01-25 | 2023-01-24 | Knauf Insulation Limited | Placa de madeira compósita |
| EP2125650B1 (en) | 2007-01-25 | 2024-05-15 | Knauf Insulation | Mineral fibre board |
| PL2108006T3 (pl) | 2007-01-25 | 2021-04-19 | Knauf Insulation Gmbh | Spoiwa i wytworzone z nich materiały |
| CA2683706A1 (en) | 2007-04-13 | 2008-10-23 | Knauf Insulation Gmbh | Composite maillard-resole binders |
| GB0715100D0 (en) | 2007-08-03 | 2007-09-12 | Knauf Insulation Ltd | Binders |
| CA2770396A1 (en) | 2009-08-07 | 2011-02-10 | Knauf Insulation | Molasses binder |
| US9493603B2 (en) | 2010-05-07 | 2016-11-15 | Knauf Insulation Sprl | Carbohydrate binders and materials made therewith |
| MX339814B (es) | 2010-05-07 | 2016-06-02 | Knauf Insulation * | Aglutinantes de poliamina carbohidrato y materiales hechos con los mismos. |
| WO2011154368A1 (en) | 2010-06-07 | 2011-12-15 | Knauf Insulation | Fiber products having temperature control additives |
| CA2834816C (en) | 2011-05-07 | 2020-05-12 | Knauf Insulation | Liquid high solids binder composition |
| GB201206193D0 (en) | 2012-04-05 | 2012-05-23 | Knauf Insulation Ltd | Binders and associated products |
| GB201214734D0 (en) | 2012-08-17 | 2012-10-03 | Knauf Insulation Ltd | Wood board and process for its production |
| PL2928936T3 (pl) | 2012-12-05 | 2022-12-27 | Knauf Insulation Sprl | Spoiwo |
| EP3102587B1 (en) | 2014-02-07 | 2018-07-04 | Knauf Insulation, LLC | Uncured articles with improved shelf-life |
| GB201408909D0 (en) | 2014-05-20 | 2014-07-02 | Knauf Insulation Ltd | Binders |
| GB201412709D0 (en) | 2014-07-17 | 2014-09-03 | Knauf Insulation And Knauf Insulation Ltd | Improved binder compositions and uses thereof |
| GB201517867D0 (en) | 2015-10-09 | 2015-11-25 | Knauf Insulation Ltd | Wood particle boards |
| GB201610063D0 (en) | 2016-06-09 | 2016-07-27 | Knauf Insulation Ltd | Binders |
| GB201701569D0 (en) | 2017-01-31 | 2017-03-15 | Knauf Insulation Ltd | Improved binder compositions and uses thereof |
| GB201804907D0 (en) | 2018-03-27 | 2018-05-09 | Knauf Insulation Ltd | Composite products |
| GB201804908D0 (en) | 2018-03-27 | 2018-05-09 | Knauf Insulation Ltd | Binder compositions and uses thereof |
-
1974
- 1974-02-18 GB GB735074A patent/GB1469331A/en not_active Expired
-
1975
- 1975-01-30 CA CA219,083A patent/CA1047306A/en not_active Expired
- 1975-02-05 JP JP50015235A patent/JPS50111265A/ja active Pending
- 1975-02-11 BE BE153262A patent/BE825417A/xx not_active IP Right Cessation
- 1975-02-14 NL NL7501741A patent/NL7501741A/xx unknown
- 1975-02-17 DK DK57175*#A patent/DK57175A/da unknown
- 1975-02-17 FR FR7504833A patent/FR2260957B3/fr not_active Expired
- 1975-02-17 IE IE306/75A patent/IE40609B1/xx unknown
- 1975-02-17 LU LU71861A patent/LU71861A1/xx unknown
- 1975-02-18 DE DE2506715A patent/DE2506715C3/de not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| IE40609B1 (en) | 1979-07-04 |
| DK57175A (enrdf_load_stackoverflow) | 1975-10-27 |
| JPS50111265A (enrdf_load_stackoverflow) | 1975-09-01 |
| BE825417A (fr) | 1975-08-11 |
| DE2506715B2 (de) | 1977-11-17 |
| GB1469331A (en) | 1977-04-06 |
| IE40609L (en) | 1975-08-18 |
| LU71861A1 (enrdf_load_stackoverflow) | 1977-01-05 |
| FR2260957A1 (enrdf_load_stackoverflow) | 1975-09-12 |
| FR2260957B3 (enrdf_load_stackoverflow) | 1977-10-28 |
| DE2506715A1 (de) | 1975-08-21 |
| NL7501741A (nl) | 1975-08-20 |
| DE2506715C3 (de) | 1978-06-29 |
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