NZ617527B2 - Functionalized polyorganosiloxanes or silanes for treating lignocellulosic materials - Google Patents
Functionalized polyorganosiloxanes or silanes for treating lignocellulosic materials Download PDFInfo
- Publication number
- NZ617527B2 NZ617527B2 NZ617527A NZ61752712A NZ617527B2 NZ 617527 B2 NZ617527 B2 NZ 617527B2 NZ 617527 A NZ617527 A NZ 617527A NZ 61752712 A NZ61752712 A NZ 61752712A NZ 617527 B2 NZ617527 B2 NZ 617527B2
- Authority
- NZ
- New Zealand
- Prior art keywords
- silanes
- group
- polyorganosiloxanes
- wood
- groups
- Prior art date
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- 150000004756 silanes Chemical class 0.000 title claims abstract description 123
- 239000000463 material Substances 0.000 title claims abstract description 58
- 125000004469 siloxy group Chemical group [SiH3]O* 0.000 claims abstract description 15
- 125000004122 cyclic group Chemical group 0.000 claims description 13
- 229910018557 Si O Inorganic materials 0.000 claims description 2
- 229910052760 oxygen Inorganic materials 0.000 claims description 2
- 241000233866 Fungi Species 0.000 abstract description 19
- 238000000034 method Methods 0.000 abstract description 11
- 241000238631 Hexapoda Species 0.000 abstract description 10
- 125000001424 substituent group Chemical group 0.000 abstract description 7
- 239000001913 cellulose Substances 0.000 abstract description 6
- 229920002678 cellulose Polymers 0.000 abstract description 6
- 229920005610 lignin Polymers 0.000 abstract description 4
- 244000005700 microbiome Species 0.000 abstract description 4
- 150000003254 radicals Chemical class 0.000 description 96
- 239000002023 wood Substances 0.000 description 90
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 81
- -1 Polysiloxane Polymers 0.000 description 80
- 229920001296 polysiloxane Polymers 0.000 description 60
- 239000000203 mixture Substances 0.000 description 52
- 238000010521 absorption reaction Methods 0.000 description 45
- 125000005373 siloxane group Chemical group [SiH2](O*)* 0.000 description 33
- 238000006243 chemical reaction Methods 0.000 description 30
- 125000000524 functional group Chemical group 0.000 description 28
- 238000005470 impregnation Methods 0.000 description 24
- QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 21
- BLRPTPMANUNPDV-UHFFFAOYSA-N silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 description 21
- 229910000077 silane Inorganic materials 0.000 description 21
- 125000004432 carbon atoms Chemical group C* 0.000 description 19
- WFDIJRYMOXRFFG-UHFFFAOYSA-N acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 18
- 239000000839 emulsion Substances 0.000 description 18
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 17
- 125000003277 amino group Chemical group 0.000 description 16
- 229910052710 silicon Inorganic materials 0.000 description 16
- 125000004185 ester group Chemical group 0.000 description 15
- 230000002522 swelling Effects 0.000 description 15
- 125000002091 cationic group Chemical group 0.000 description 14
- 150000001875 compounds Chemical class 0.000 description 14
- RYGMFSIKBFXOCR-UHFFFAOYSA-N copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 14
- 235000010099 Fagus sylvatica Nutrition 0.000 description 12
- 235000008331 Pinus X rigitaeda Nutrition 0.000 description 12
- 241000018646 Pinus brutia Species 0.000 description 12
- 235000011613 Pinus brutia Nutrition 0.000 description 12
- 125000000129 anionic group Chemical group 0.000 description 12
- 229910052799 carbon Inorganic materials 0.000 description 12
- 239000003995 emulsifying agent Substances 0.000 description 12
- 239000010949 copper Substances 0.000 description 11
- QGZKDVFQNNGYKY-UHFFFAOYSA-O ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 10
- 229910052802 copper Inorganic materials 0.000 description 10
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 10
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 10
- 210000002421 Cell Wall Anatomy 0.000 description 9
- 241001070947 Fagus Species 0.000 description 9
- AQSJGOWTSHOLKH-UHFFFAOYSA-N Phosphite Chemical group [O-]P([O-])[O-] AQSJGOWTSHOLKH-UHFFFAOYSA-N 0.000 description 9
- 150000001299 aldehydes Chemical class 0.000 description 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 9
- 239000001257 hydrogen Substances 0.000 description 9
- 229910052739 hydrogen Inorganic materials 0.000 description 9
- 125000004435 hydrogen atoms Chemical group [H]* 0.000 description 9
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 9
- 150000002500 ions Chemical class 0.000 description 9
- 230000002335 preservative Effects 0.000 description 9
- 239000003755 preservative agent Substances 0.000 description 9
- 239000002904 solvent Substances 0.000 description 9
- ABLZXFCXXLZCGV-UHFFFAOYSA-L CHEBI:8154 Chemical group [O-]P([O-])=O ABLZXFCXXLZCGV-UHFFFAOYSA-L 0.000 description 8
- 150000007942 carboxylates Chemical group 0.000 description 8
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 description 8
- 125000005496 phosphonium group Chemical group 0.000 description 8
- 239000000047 product Substances 0.000 description 8
- QAOWNCQODCNURD-UHFFFAOYSA-L sulfate group Chemical group S(=O)(=O)([O-])[O-] QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 8
- 239000002253 acid Substances 0.000 description 7
- 150000001639 boron compounds Chemical class 0.000 description 7
- OKTJSMMVPCPJKN-UHFFFAOYSA-N carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 7
- 238000001035 drying Methods 0.000 description 7
- 150000002148 esters Chemical class 0.000 description 7
- 229910052757 nitrogen Inorganic materials 0.000 description 7
- 150000003839 salts Chemical class 0.000 description 7
- 239000011780 sodium chloride Substances 0.000 description 7
- 239000000126 substance Substances 0.000 description 7
- 125000001273 sulfonato group Chemical group [O-]S(*)(=O)=O 0.000 description 7
- 125000004423 acyloxy group Chemical group 0.000 description 6
- 125000003545 alkoxy group Chemical group 0.000 description 6
- 230000003115 biocidal Effects 0.000 description 6
- 230000015556 catabolic process Effects 0.000 description 6
- 239000003795 chemical substances by application Substances 0.000 description 6
- 239000011248 coating agent Substances 0.000 description 6
- 238000000576 coating method Methods 0.000 description 6
- 230000004059 degradation Effects 0.000 description 6
- 238000006731 degradation reaction Methods 0.000 description 6
- 235000013870 dimethyl polysiloxane Nutrition 0.000 description 6
- 239000003063 flame retardant Substances 0.000 description 6
- 125000002467 phosphate group Chemical group [H]OP(=O)(O[H])O[*] 0.000 description 6
- 229920000435 poly(dimethylsiloxane) Polymers 0.000 description 6
- 230000002829 reduced Effects 0.000 description 6
- 239000000758 substrate Substances 0.000 description 6
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 6
- KGBXLFKZBHKPEV-UHFFFAOYSA-N Boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 description 5
- 239000004721 Polyphenylene oxide Substances 0.000 description 5
- 125000004036 acetal group Chemical group 0.000 description 5
- 125000001931 aliphatic group Chemical group 0.000 description 5
- 230000015572 biosynthetic process Effects 0.000 description 5
- 239000004327 boric acid Substances 0.000 description 5
- CURLTUGMZLYLDI-UHFFFAOYSA-N carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 5
- 239000001569 carbon dioxide Substances 0.000 description 5
- 229910002092 carbon dioxide Inorganic materials 0.000 description 5
- 230000000875 corresponding Effects 0.000 description 5
- 239000004205 dimethyl polysiloxane Substances 0.000 description 5
- 238000005516 engineering process Methods 0.000 description 5
- LYCAIKOWRPUZTN-UHFFFAOYSA-N glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 5
- 230000000749 insecticidal Effects 0.000 description 5
- 239000002917 insecticide Substances 0.000 description 5
- 238000002386 leaching Methods 0.000 description 5
- XYFCBTPGUUZFHI-UHFFFAOYSA-N phosphine group Chemical group P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 5
- 229920000570 polyether Polymers 0.000 description 5
- 241000256602 Isoptera Species 0.000 description 4
- 102000014961 Protein Precursors Human genes 0.000 description 4
- 108010078762 Protein Precursors Proteins 0.000 description 4
- DKGZKEKMWBGTIB-UHFFFAOYSA-N [diacetyloxy(propyl)silyl] acetate Chemical compound CCC[Si](OC(C)=O)(OC(C)=O)OC(C)=O DKGZKEKMWBGTIB-UHFFFAOYSA-N 0.000 description 4
- 238000006640 acetylation reaction Methods 0.000 description 4
- 230000002378 acidificating Effects 0.000 description 4
- 125000003172 aldehyde group Chemical group 0.000 description 4
- 125000003118 aryl group Chemical group 0.000 description 4
- 239000003139 biocide Substances 0.000 description 4
- BTBUEUYNUDRHOZ-UHFFFAOYSA-N borate Chemical compound [O-]B([O-])[O-] BTBUEUYNUDRHOZ-UHFFFAOYSA-N 0.000 description 4
- 230000001680 brushing Effects 0.000 description 4
- 150000001768 cations Chemical class 0.000 description 4
- 150000001880 copper compounds Chemical class 0.000 description 4
- 125000004663 dialkyl amino group Chemical group 0.000 description 4
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
- 238000007598 dipping method Methods 0.000 description 4
- 238000002474 experimental method Methods 0.000 description 4
- 229910052736 halogen Inorganic materials 0.000 description 4
- 125000005842 heteroatoms Chemical group 0.000 description 4
- 238000007654 immersion Methods 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
- 230000001264 neutralization Effects 0.000 description 4
- 230000035515 penetration Effects 0.000 description 4
- OZAIFHULBGXAKX-UHFFFAOYSA-N precursor Substances N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 description 4
- 239000003223 protective agent Substances 0.000 description 4
- 239000010703 silicon Substances 0.000 description 4
- 239000004328 sodium tetraborate Substances 0.000 description 4
- 235000010339 sodium tetraborate Nutrition 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- 238000003786 synthesis reaction Methods 0.000 description 4
- 230000002194 synthesizing Effects 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 239000010876 untreated wood Substances 0.000 description 4
- 241000411449 Anobium punctatum Species 0.000 description 3
- 241001600095 Coniophora puteana Species 0.000 description 3
- 239000005749 Copper compound Substances 0.000 description 3
- 239000004593 Epoxy Substances 0.000 description 3
- 240000000731 Fagus sylvatica Species 0.000 description 3
- 241000832180 Hylotrupes bajulus Species 0.000 description 3
- 206010061217 Infestation Diseases 0.000 description 3
- WYVVKGNFXHOCQV-UHFFFAOYSA-N Iodopropynyl butylcarbamate Chemical compound CCCCNC(=O)OCC#CI WYVVKGNFXHOCQV-UHFFFAOYSA-N 0.000 description 3
- 241001182492 Nes Species 0.000 description 3
- 241000233647 Phytophthora nicotianae var. parasitica Species 0.000 description 3
- 238000007792 addition Methods 0.000 description 3
- 125000000217 alkyl group Chemical group 0.000 description 3
- 238000005804 alkylation reaction Methods 0.000 description 3
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 3
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 3
- 229910052796 boron Inorganic materials 0.000 description 3
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 3
- 150000001244 carboxylic acid anhydrides Chemical class 0.000 description 3
- 239000000969 carrier Substances 0.000 description 3
- 210000004027 cells Anatomy 0.000 description 3
- 150000001879 copper Chemical class 0.000 description 3
- 239000000975 dye Substances 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 125000001240 enamine group Chemical group 0.000 description 3
- 238000005227 gel permeation chromatography Methods 0.000 description 3
- 150000004820 halides Chemical class 0.000 description 3
- 150000002430 hydrocarbons Chemical class 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxyl anion Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 3
- 150000002576 ketones Chemical class 0.000 description 3
- 239000004530 micro-emulsion Substances 0.000 description 3
- 230000000813 microbial Effects 0.000 description 3
- 239000003973 paint Substances 0.000 description 3
- 235000021317 phosphate Nutrition 0.000 description 3
- 238000004381 surface treatment Methods 0.000 description 3
- 230000004584 weight gain Effects 0.000 description 3
- 235000019786 weight gain Nutrition 0.000 description 3
- 230000004580 weight loss Effects 0.000 description 3
- PSBDWGZCVUAZQS-UHFFFAOYSA-N (dimethylsulfonio)acetate Chemical group C[S+](C)CC([O-])=O PSBDWGZCVUAZQS-UHFFFAOYSA-N 0.000 description 2
- ZVAYUUUQOCPZCZ-UHFFFAOYSA-N 4-(diethoxyphosphorylmethyl)aniline Chemical class CCOP(=O)(OCC)CC1=CC=C(N)C=C1 ZVAYUUUQOCPZCZ-UHFFFAOYSA-N 0.000 description 2
- ZRSNZINYAWTAHE-UHFFFAOYSA-N 4-Anisaldehyde Chemical compound COC1=CC=C(C=O)C=C1 ZRSNZINYAWTAHE-UHFFFAOYSA-N 0.000 description 2
- XAYDWGMOPRHLEP-UHFFFAOYSA-N 6-ethenyl-7-oxabicyclo[4.1.0]heptane Chemical compound C1CCCC2OC21C=C XAYDWGMOPRHLEP-UHFFFAOYSA-N 0.000 description 2
- 241000894006 Bacteria Species 0.000 description 2
- HUMNYLRZRPPJDN-UHFFFAOYSA-N Benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 2
- 241000318995 Bostrichidae Species 0.000 description 2
- 241000195493 Cryptophyta Species 0.000 description 2
- XPFVYQJUAUNWIW-UHFFFAOYSA-N Furfuryl alcohol Chemical compound OCC1=CC=CO1 XPFVYQJUAUNWIW-UHFFFAOYSA-N 0.000 description 2
- HHLFWLYXYJOTON-UHFFFAOYSA-N Glyoxylic acid Natural products OC(=O)C=O HHLFWLYXYJOTON-UHFFFAOYSA-N 0.000 description 2
- MWUXSHHQAYIFBG-UHFFFAOYSA-N Nitrogen oxide Substances O=[N] MWUXSHHQAYIFBG-UHFFFAOYSA-N 0.000 description 2
- 235000008582 Pinus sylvestris Nutrition 0.000 description 2
- 241000218626 Pinus sylvestris Species 0.000 description 2
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 2
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- 239000005822 Propiconazole Substances 0.000 description 2
- STJLVHWMYQXCPB-UHFFFAOYSA-N Propiconazole Chemical compound O1C(CCC)COC1(C=1C(=CC(Cl)=CC=1)Cl)CN1N=CN=C1 STJLVHWMYQXCPB-UHFFFAOYSA-N 0.000 description 2
- 239000002262 Schiff base Substances 0.000 description 2
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- PXMNMQRDXWABCY-UHFFFAOYSA-N Tebuconazole Chemical compound C1=NC=NN1CC(O)(C(C)(C)C)CCC1=CC=C(Cl)C=C1 PXMNMQRDXWABCY-UHFFFAOYSA-N 0.000 description 2
- OGIDPMRJRNCKJF-UHFFFAOYSA-N TiO Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 2
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Classifications
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- B27K—PROCESSES, APPARATUS OR SELECTION OF SUBSTANCES FOR IMPREGNATING, STAINING, DYEING, BLEACHING OF WOOD OR SIMILAR MATERIALS, OR TREATING OF WOOD OR SIMILAR MATERIALS WITH PERMEANT LIQUIDS, NOT OTHERWISE PROVIDED FOR; CHEMICAL OR PHYSICAL TREATMENT OF CORK, CANE, REED, STRAW OR SIMILAR MATERIALS
- B27K2240/00—Purpose of the treatment
- B27K2240/20—Removing fungi, molds or insects
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B27—WORKING OR PRESERVING WOOD OR SIMILAR MATERIAL; NAILING OR STAPLING MACHINES IN GENERAL
- B27K—PROCESSES, APPARATUS OR SELECTION OF SUBSTANCES FOR IMPREGNATING, STAINING, DYEING, BLEACHING OF WOOD OR SIMILAR MATERIALS, OR TREATING OF WOOD OR SIMILAR MATERIALS WITH PERMEANT LIQUIDS, NOT OTHERWISE PROVIDED FOR; CHEMICAL OR PHYSICAL TREATMENT OF CORK, CANE, REED, STRAW OR SIMILAR MATERIALS
- B27K2240/00—Purpose of the treatment
- B27K2240/70—Hydrophobation treatment
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B27—WORKING OR PRESERVING WOOD OR SIMILAR MATERIAL; NAILING OR STAPLING MACHINES IN GENERAL
- B27K—PROCESSES, APPARATUS OR SELECTION OF SUBSTANCES FOR IMPREGNATING, STAINING, DYEING, BLEACHING OF WOOD OR SIMILAR MATERIALS, OR TREATING OF WOOD OR SIMILAR MATERIALS WITH PERMEANT LIQUIDS, NOT OTHERWISE PROVIDED FOR; CHEMICAL OR PHYSICAL TREATMENT OF CORK, CANE, REED, STRAW OR SIMILAR MATERIALS
- B27K3/00—Impregnating wood, e.g. impregnation pretreatment, for example puncturing; Wood impregnation aids not directly involved in the impregnation process
- B27K3/02—Processes; Apparatus
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B27—WORKING OR PRESERVING WOOD OR SIMILAR MATERIAL; NAILING OR STAPLING MACHINES IN GENERAL
- B27K—PROCESSES, APPARATUS OR SELECTION OF SUBSTANCES FOR IMPREGNATING, STAINING, DYEING, BLEACHING OF WOOD OR SIMILAR MATERIALS, OR TREATING OF WOOD OR SIMILAR MATERIALS WITH PERMEANT LIQUIDS, NOT OTHERWISE PROVIDED FOR; CHEMICAL OR PHYSICAL TREATMENT OF CORK, CANE, REED, STRAW OR SIMILAR MATERIALS
- B27K3/00—Impregnating wood, e.g. impregnation pretreatment, for example puncturing; Wood impregnation aids not directly involved in the impregnation process
- B27K3/02—Processes; Apparatus
- B27K3/08—Impregnating by pressure, e.g. vacuum impregnation
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B27—WORKING OR PRESERVING WOOD OR SIMILAR MATERIAL; NAILING OR STAPLING MACHINES IN GENERAL
- B27K—PROCESSES, APPARATUS OR SELECTION OF SUBSTANCES FOR IMPREGNATING, STAINING, DYEING, BLEACHING OF WOOD OR SIMILAR MATERIALS, OR TREATING OF WOOD OR SIMILAR MATERIALS WITH PERMEANT LIQUIDS, NOT OTHERWISE PROVIDED FOR; CHEMICAL OR PHYSICAL TREATMENT OF CORK, CANE, REED, STRAW OR SIMILAR MATERIALS
- B27K3/00—Impregnating wood, e.g. impregnation pretreatment, for example puncturing; Wood impregnation aids not directly involved in the impregnation process
- B27K3/02—Processes; Apparatus
- B27K3/08—Impregnating by pressure, e.g. vacuum impregnation
- B27K3/083—Impregnating by pressure, e.g. vacuum impregnation along the fibers, i.e. longitudinal impregnation
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B27—WORKING OR PRESERVING WOOD OR SIMILAR MATERIAL; NAILING OR STAPLING MACHINES IN GENERAL
- B27K—PROCESSES, APPARATUS OR SELECTION OF SUBSTANCES FOR IMPREGNATING, STAINING, DYEING, BLEACHING OF WOOD OR SIMILAR MATERIALS, OR TREATING OF WOOD OR SIMILAR MATERIALS WITH PERMEANT LIQUIDS, NOT OTHERWISE PROVIDED FOR; CHEMICAL OR PHYSICAL TREATMENT OF CORK, CANE, REED, STRAW OR SIMILAR MATERIALS
- B27K3/00—Impregnating wood, e.g. impregnation pretreatment, for example puncturing; Wood impregnation aids not directly involved in the impregnation process
- B27K3/02—Processes; Apparatus
- B27K3/15—Impregnating involving polymerisation including use of polymer-containing impregnating agents
- B27K3/153—Without in-situ polymerisation, condensation, or cross-linking reactions
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B27—WORKING OR PRESERVING WOOD OR SIMILAR MATERIAL; NAILING OR STAPLING MACHINES IN GENERAL
- B27K—PROCESSES, APPARATUS OR SELECTION OF SUBSTANCES FOR IMPREGNATING, STAINING, DYEING, BLEACHING OF WOOD OR SIMILAR MATERIALS, OR TREATING OF WOOD OR SIMILAR MATERIALS WITH PERMEANT LIQUIDS, NOT OTHERWISE PROVIDED FOR; CHEMICAL OR PHYSICAL TREATMENT OF CORK, CANE, REED, STRAW OR SIMILAR MATERIALS
- B27K3/00—Impregnating wood, e.g. impregnation pretreatment, for example puncturing; Wood impregnation aids not directly involved in the impregnation process
- B27K3/34—Organic impregnating agents
- B27K3/36—Aliphatic compounds
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B27—WORKING OR PRESERVING WOOD OR SIMILAR MATERIAL; NAILING OR STAPLING MACHINES IN GENERAL
- B27K—PROCESSES, APPARATUS OR SELECTION OF SUBSTANCES FOR IMPREGNATING, STAINING, DYEING, BLEACHING OF WOOD OR SIMILAR MATERIALS, OR TREATING OF WOOD OR SIMILAR MATERIALS WITH PERMEANT LIQUIDS, NOT OTHERWISE PROVIDED FOR; CHEMICAL OR PHYSICAL TREATMENT OF CORK, CANE, REED, STRAW OR SIMILAR MATERIALS
- B27K3/00—Impregnating wood, e.g. impregnation pretreatment, for example puncturing; Wood impregnation aids not directly involved in the impregnation process
- B27K3/34—Organic impregnating agents
- B27K3/50—Mixtures of different organic impregnating agents
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B32—LAYERED PRODUCTS
- B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
- B32B21/00—Layered products comprising a layer of wood, e.g. wood board, veneer, wood particle board
- B32B21/04—Layered products comprising a layer of wood, e.g. wood board, veneer, wood particle board comprising wood as the main or only constituent of a layer, which is next to another layer of the same or of a different material
- B32B21/08—Layered products comprising a layer of wood, e.g. wood board, veneer, wood particle board comprising wood as the main or only constituent of a layer, which is next to another layer of the same or of a different material of synthetic resin
-
- 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
- C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
- C08G63/68—Polyesters containing atoms other than carbon, hydrogen and oxygen
- C08G63/695—Polyesters containing atoms other than carbon, hydrogen and oxygen containing silicon
-
- 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
- C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
- C08G77/04—Polysiloxanes
- C08G77/045—Polysiloxanes containing less than 25 silicon atoms
-
- 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
- C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
- C08G77/04—Polysiloxanes
- C08G77/14—Polysiloxanes containing silicon bound to oxygen-containing groups
-
- 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
- C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
- C08G77/04—Polysiloxanes
- C08G77/22—Polysiloxanes containing silicon bound to organic groups containing atoms other than carbon, hydrogen and oxygen
- C08G77/26—Polysiloxanes containing silicon bound to organic groups containing atoms other than carbon, hydrogen and oxygen nitrogen-containing groups
-
- 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
- C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
- C08G77/04—Polysiloxanes
- C08G77/22—Polysiloxanes containing silicon bound to organic groups containing atoms other than carbon, hydrogen and oxygen
- C08G77/28—Polysiloxanes containing silicon bound to organic groups containing atoms other than carbon, hydrogen and oxygen sulfur-containing groups
-
- 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
- C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
- C08G77/04—Polysiloxanes
- C08G77/22—Polysiloxanes containing silicon bound to organic groups containing atoms other than carbon, hydrogen and oxygen
- C08G77/30—Polysiloxanes containing silicon bound to organic groups containing atoms other than carbon, hydrogen and oxygen phosphorus-containing groups
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J3/00—Processes of treating or compounding macromolecular substances
- C08J3/24—Crosslinking, e.g. vulcanising, of macromolecules
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D183/00—Coating compositions based on macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon, with or without sulfur, nitrogen, oxygen, or carbon only; Coating compositions based on derivatives of such polymers
- C09D183/04—Polysiloxanes
- C09D183/06—Polysiloxanes containing silicon bound to oxygen-containing groups
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D183/00—Coating compositions based on macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon, with or without sulfur, nitrogen, oxygen, or carbon only; Coating compositions based on derivatives of such polymers
- C09D183/04—Polysiloxanes
- C09D183/08—Polysiloxanes containing silicon bound to organic groups containing atoms other than carbon, hydrogen, and oxygen
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D5/00—Coating compositions, e.g. paints, varnishes or lacquers, characterised by their physical nature or the effects produced; Filling pastes
- C09D5/14—Paints containing biocides, e.g. fungicides, insecticides or pesticides
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T428/00—Stock material or miscellaneous articles
- Y10T428/4935—Impregnated naturally solid product [e.g., leather, stone, etc.]
- Y10T428/662—Wood timber product [e.g., piling, post, veneer, etc.]
Abstract
Disclosed are functionalized polyorganosiloxanes or silanes containing 2-30 siloxy units of formula Q, T, D or M, wherein the substituents are as described in the specification. The polyorganosiloxanes or silanes are used in a single process step for the treatment of lignocellulosic materials (materials based on cellulose and/or lignin) to protect them against weather conditions, microorganisms, insects, and fungi. ials based on cellulose and/or lignin) to protect them against weather conditions, microorganisms, insects, and fungi.
Description
Functionalized polyorganosiloxanes or silanes for treating
lignocellulosic als
The present invention relates to functionalized polyorganosiloxanes or s
for the treatment of lignocellulosic materials that are suitable to preserve wood and
other materials based on cellulose and/or lignin, and particularly to protect them
against weather conditions, microorganisms, insects and fungi. Furthermore, the
water absorption of lignocellulosic materials, particularly wood, is increased, the
shrinkage or of lignocellulosic materials, particularly wood, is improved, by the
use of the ganosiloxanes or silanes according to the present invention.
Furthermore, by using the polyorganosiloxanes or silanes of the present invention an
icidal equipment can be achieved, which makes the use of conventional
insecticides unnecessary.
It is known to increase the resistance of wood against weather conditions by a
coating of lacquer and color paints. Dimensional changes of the wood, for e
caused by swelling and age due to water absorption or release, caused by
external humidity changes, nevertheless lead to peeling of such paints.
It is further known, to protect the optical appearance and the resistance of
wood against harmful rganisms, for example blueing fungi or white rot, brown
rot and soft rot, by an impregnation with a mixture of arsenic, ionic copper and
chromium VI.
Such wood preservatives are disadvantageous for the reason that at least
chromium and arsenic are l and toxic for the environment. Even copper
complexes and boron compounds are now seen as critical under the same aspects.
Furthermore, soluble wood preservatives are known which comprise a
quaternary ammonium compound such as for example benzalkonium chloride. Such
wood preservatives are disadvantageous as they are deposited only in the upper
layers of the wood due to their immediate bonding to wood.
r biocidal actives are 3-iodopropynyl butyl carbamate (IPBC) or
triazoles (propiconazole, tebuconazole).
The known c wood preservatives are used in the application categories
1, 2 and 3 according to DIN EN 351 and do not lead to hydrophobing
(10903736_1):MGH
the wood so that the tendency of the wood to absorb water and therewith the
dimensional stability remain unchanged.
To reduce the water absorption of wood, essentially compounds based on
oils, fats and waxes (paraffins and silicones) were used.
Known wood preservatives, which are used for hydrophobing and which
have a t of silicon nds, are known too. Thus, JP 48567 A
describes wood preservatives, which consist of a mixture of different
alkoxysilanes, including amino group containing alkoxysilanes and boric acid.
US 6294608 discloses aqueous emulsions for treating mineral construction
materials and wood with a mixture of silanes which have alkyl and alkoxy groups
or aminoalkyl groups. Polysiloxane compounds are not disclosed.
EP 0716127 discloses polyorganosiloxanes as well
as aqueous mixtures
thereof, which are particularly used for hydrophobing surfaces, e.g. in the
impregnation of leather and textiles made from natural and/or artificial materials
and in the field of organic and mineral construction als as well as building
tion.
EP 8 discloses aminoalkyl alkoxysilanes which can be used among
others for hobing cellulose products or as additives for paints and
lacquers. Polyorganosiloxanes are not disclosed therein.
2O US 2002/0026881 describes a composition for hydrophobing surfaces
which contains silicone among others.
US 4757106 discloses the combination of aminoorganosiloxanes with
basic nitrogen ts of >0.5 % with siloxanes with a molecular weight of > 620
g/mol in substantially solvent-free formulations as equipment for l
substrates.
DE 3447636 discloses the combination of aminoorganosiloxanes with
basic nitrogen contents of >0.5 % with a second amino ne with basic
nitrogen content of 0 to 0.5 % and ally a siloxane with molar masses <600
g/mol in the presence of solvents.
3O EP 0621115 and DE 4241727 disclose the combination of
aminoorganosiloxanes with basic nitrogen contents of >0.5 % with repellent
agents, e.g. siloxanes, optionally in the presence of a second compound with
basic nitrogen in contents of 0 to 0.5 % for
the treatment of wood.
DE10 2004 036918 proposes the use of aminoorganosiloxanes in wood
preservatives. The siloxanes shall have a molecular weight of 500 to 0 g/mol
and the degree of substitution of the siloxane units with amino groups shall be up to
50 %.
DE 4202320 describes the impregnation of wood with a non-functionalized
polydimethylsiloxane by using supercritical carbon dioxide as a carrier medium. The
disadvantage of this proposal is that the non-functionalized polydimethylsiloxane can
be d from the wood.
EP 680810 describes the modification of wood by acetylation with acetic
anhydride at elevated temperatures. The disadvantage of this procedure is an
insufficient reduction of the water uptake of the modified wood.
The disadvantage of all of the above tions is that a long-lasting
tion of wood in practice can only be achieved with a two-stage treatment of the
wood so far. In the so-called Royal s the wood is first impregnated in a first
step with an c copper salt (Cu-HDO) or an organic copper salt, and
subsequently in a second step an impregnation with oil is carried out to prevent the
leaching of the biocidal copper.
nes having hydrolysable groups tend to condensation after contact with
water and acids or bases, which s solubility, emulsifying capacity and
penetration capacity of the wood. Impregnation with nes as disclosed in DE 10
2004 036918 is not long-lasting, as these siloxanes can be ed again after
prolonged exposure to water.
The present invention therefore relates to impregnating wood long-lasting in a
practicable one-step method, and thereby further reduce the tendency of wood to
absorb water, to improve the dimensional stability in changing humidity conditions of
the environment and to reduce the degradation of the wood by fungi, bacteria and
insects, such as wood destroying insects, for example termites, house longhorn
beetle, common furniture beetle, powder post beetle, effectively. At the same time
yellowing and graying of the woods due to light and weather impact shall be
ssed.
In a first aspect, the present invention provides use of polyorganosiloxanes or
silanes for the treatment of ellulosic materials, characterized in that the
polyorganosiloxanes are straight-chained, branched or cyclic polyorganosiloxanes,
formed from a number average of 2 to 30 siloxy units, which are selected from the
group consisting of
AH26(11521684_1):EOR
O R1 R1 R1
O Si O O Si O O Si O O Si R1
1/2 1/2 1/2 1/2 1/2 1/2 1/2
O O R1 R1
1/2 1/2
(Q) (T) (D) (M)
- wherein the radicals R1 represent organic radicals as defined below, which
may be the same or different, with the proviso that at least one of the radicals
R1 is an organic radical RF, containing a functional group F, which is selected
from the group of functional groups consisting of
- an acyloxy group Si-bonded via O, and
- optionally ed from the group of functional groups consisting of:
- phosphonium group,
- ine group,
- epoxy group
- carbonate group,
- urethane group,
- isocyanate group including blocked isocyanate group,
- urea group,
- amido group,
- aldehyde group,
- hemiacetal and acetal group,
- enamine group,
- imine group,
- zwitterionic group,
- carboxylic acid / ylate group,
- sulfonic acid / sulfonate group,
- sulfuric acid half-ester / te group,
- phosphoric ester / phosphate group
- phosphonic ester / phosphonate group,
AH26(11521684_1):EOR
- phosphorous ester / phosphite group,
- xanthate / genate ester group,
- organo amino group Si-bonded via N,
- y group,
- alkoxy group Si-bonded via O, and
- lfato group
and characterized in that the silanes are represented by the formula (I)
Si (R1)
4 (I)
wherein the radicals R1 are as defined below, with the proviso that at least one of the
radicals R1 is a radical RF containing a functional group F, which is as defined above,
and at least one of the radicals R1 is bonded to the silicon atom via a hetero atom
and at least one of the radicals R1 is bonded to the n atom via a carbon atom,
or by the formula (II)
(R1)
3 Si R3 Si (R1)
3 (II)
wherein R1 is the same or different and has the meaning as defined for formula (I),
and R3 is a divalent, ht-chained, branched, cyclic, aliphatic, unsaturated, or
aromatic hydrocarbon l having up to 30 carbon atoms, which may contain one
or more groups selected from -O-, -NR4-, wherein R4 is hydrogen or C1alkyl, -
C(O)- and -C(S)-, and which may optionally be substituted by hydroxy and is bonded
to the silicon atom via carbon,
and salts thereof,
and wherein the substituents R1 are selected from the group consisting of:
straight-chain, cyclic or branched, saturated, unsaturated or aromatic hydrocarbon
radicals having up to 100 carbon atoms, which may optionally contain one or more
groups selected from
–O–,
(10903680_1):MGH
–S–,
–NR2–, wherein R2 represents hydrogen, a monovalent straight-
chained, cyclic or branched, saturated, unsaturated or aromatic hydrocarbon radical
having up to 60 carbon atoms, which may contain one or more groups selected from
-O-, -S-, -NH-, -C(O)- and -C(S)-, and which may optionally be substituted by one or
more substituents selected from the group consisting of a hydroxyl group, an
optionally tuted cyclic group, amino, alkylamino, dialkylamino,
ammonium, her radicals and polyether ester ls, wherein in case that
multiple groups -NR2 are present, these may be the same or different,
R2 , wherein R2 is as defined above,
P(R2)
2 , wherein R2 is as defined above,
–C(O)– and
–C(S)–,
(10903680_1):MGH
and may be substituted by one or more radicals selected from the group consisting
- hydroxyl,
- mercapto (-SH or-S-),
- isocyanato,
- halogen,
- a polyether l having up to 60 carbon atoms, which may optionally contain one
or more amino, mono- or dialkylamino, or arylamino groups,
- a saccharide-containing organic radical,
or two substituents R1 from different siloxy units together form a straight-chained,
ed or cyclic alkandiyl radical having 2 to 20 carbon atoms between two silicon
atoms, which is ally interrupted by -O-, -S-, -C(O)-, -NH- and is optionally
tuted by OH,
wherein the bonding to silicon may be via a carbon atom and/or a heteroatom and,
wherein said treatment comprises coating or impregnating said lignocellulosic
material with said polyorganosiloxanes or silanes .
In a second aspect, the present invention provides use of a composition sing
at least one polyorganosiloxane and/or silane, as defined in the first aspect, and at
least one solvent and/or at least one biocidal agent for the treatment of
lignocellulosic als.
In a third aspect, the present invention es a composition comprising
a) at least one polyorganosiloxane and/or silane as defined in the first aspect,
having a functional group F selected from the group of the acidic functional
groups:
- carboxylic acid/carboxylate group,
b) at least one polyorganosiloxane and/or silane having a basic functional group
selected from amino groups, ammonium groups, phosphonium groups and
phosphine groups.
11822965v2:gcc
In a fourth aspect, the present invention es a process for treating
lignocellulosic material, comprising the treatment of the lignocellulosic material with
at least one polyorganosiloxane or silane, as defined in the first aspect, or a
ition as defined in the second or third aspect, by surface treatment,
immersion treatment, or vacuum or pressure impregnation.
In a fifth aspect, the present invention provides use of a composition as defined in
the second or third aspect for the treatment of lignocellulosic material and, wherein
said treatment comprises coating or impregnating said lignocellulosic material with
said polyorganosiloxanes or silanes.
In a sixth aspect, the present invention provides use of at least one
polyorganosiloxane and/or silane, as defined in the first aspect, or a composition as
defined in the second or third aspect for repelling es with or without additional
insecticides for combating termites.
In a seventh aspect, the present invention provides lignocellulosic material,
comprising at least one ganosiloxane and/or silane, as defined in the first
aspect.
In an eighth aspect, the present invention provides lignocellulosic material,
comprising a composition as defined in the second or third aspect.
The t invention relates to polyorganosiloxanes and s for the
treatment of lignocellulosic materials, in particular wood and other lignocellulosic
materials, to se their ance, for example against microbial degradation or
degradation caused by fungi and/or weather ions such as sunlight (UV rays),
rain and other ional variations of humidity. The Polyorganosiloxanes
11822965v2:gcc
or silanes used in the present invention serve for use as a protective agent for
Iignocellulosic materials against weather impact, fungi, es and insects.
Furthermore, the use of the ganosiloxanes or silanes in ance with
the present ion leads to an improvement of the properties such as
shrinkage and swelling of wood or Iignocellulosic materials by treating the
Iignocellulosic materials therewith. in a further aspect, the t ion
relates to Iignocellulosic materials, in particular wood, which has been treated
with the polyorganosiloxanes and / or silanes used according to the present
invention.
The polyorganosiloxanes and / or silanes used in the present invention
may in particular be used for the treatment of Iignocellulosic materials such as
wood and wood products, particleboards, medium density fiberboards, oriented
beach boards (088), paper, cardboards, insulation boards based on
Iignocellulose, plywood, veneers and packaging material with a content of
biodegradable compounds (hereinafter tively referred to as "Iignocellulosic
materials"). The ganosiloxanes and / or silanes used in the present
invention further have a high resistance to leaching after nation.
As a further advantage the polyorganosiloxanes and / or silanes used in
accordance with the present invention permit application, such as e.g. by
impregnation, in a single process step. Surprisingly, the desired improvement is
possible with n organo-functional radicals in short-chain
ganosiloxanes or s. Amino-functionalized silicones are primarily not
required.
The present invention thus relates to polyorganosiloxanes or silanes for
the treatment of Iignocellulosic materials, characterized in that the
polyorganosiloxanes are straight-chained, branched or cyclic
polyorganosiloxanes, formed from a number average of 2 to 30 siloxy units,
which are selected from the group consisting of:
01/2
I. 1'21 Ill 1T1
. . —OU§SI—R1. —o—Sl—ol/7 —01—/381—01/—2— —ol—/Esl—ol—E
| | I l
(Bl/2 $1/2 R1 R1
(Q) (T) (D) (M)
wherein the radicals R1 represent organic radicals, which may be the same or
different, with the proviso that at least one of the radicals R1 is a radical RF
containing a functional group F, which is ed from the group of functional
groups consisting of:
- phosphonium group,
- epoxy group
- carbonate group,
- urethanegroup,
- nate group including blocked isocyanate group,
- urea group,
- amido group,
- aldehyde group,
- hemiacetal and acetal group,
- an enamine group, or
- imine group,
- a zwitterionic group,
- carboxylic acid / carboxylate group,
- sulfonic acid / sulfonate group,
- sulfuric acid half-ester/ sulphate group,
- phosphoric ester/ phosphate group
- onic esters / phosphonate group,
- phosphorous ester / phosphite group,
- xanthate / xanthogenate ester group,
- organo amino group Si-bonded via N,
- y group,
- acyloxy group Si-bonded via 0,
- alkoxy group Si-bonded via 0, and
- thiosulfato group
and terized in that the silanes are represented by the formula (I)
SI._(R )4
wherein the radicals R1 are as defined above, with the proviso that at least one of
the radicals R1 is a radical RF ning a functional group F, which is as defined
above, and at least one of the ls R1 is bonded to the silicon atom via a
hetero atom and at least one of the radicals R1 is bonded to the silicon atom via a
carbon atom,
or by the formula (II)
(R1)3—Si—R§-Si—(R1)3
(II)
wherein R1 is the same or different and has the meaning as defined for formula
(I), and R3 is a divalent, straight-chained, ed, cyclic, aliphatic, unsaturated,
or aromatic hydrocarbon radical having up to 30 carbon atoms, which may
n one or more groups selected from -O-, -NH-, -C(O)- and , and
which may optionally be substituted by hydroxy and is bonded to the silicon atom
via carbon,
and salts thereof.
Preferably, the group of functional groups consists of:
- phosphonium group,
— phosphine group,
- epoxy group
- carbonate group,
- urethane group,
- isocyanate group including blocked isocyanate group,
- urea group,
- amido group,
- aldehyde group,
- an enamine group,
- a zwitterionic group,
- ylic acid / carboxylate group,
- sulfonic acid / sulfonate group,
- sulfuric acid half-ester/ sulphate group,
- phosphoric ester / phosphate group
- phosphonic acd esters / phosphonate group,
- phosphorous ester/ phosphite group,
- xanthate / xanthogenat ester group,
— organo amino group Si-bonded via N,
- acyloxy group ded via 0,
- alkoxy group Si-bonded via 0, and
- thiosulfato group.
The polyorganosiloxanes and silanes of the present invention are in ular
characterized in that the radicals R1 are selected from the group consisting of RF
and RN, wherein the radicals RF are such radicals R1 which have the mentioned
functional groups F and wherein the radicals RN are such radicals R1 which do
not have the above functional groups F.
In a preferred embodiment of the ion, the polyorganosiloxanes used
in the present invention have a molar t of the radicals RF, which comprise
at least one functional group F, from 3.33 to 100 mol-%, based on the number of
siloxy units. More preferably this content is from 5 to 100%, even more preferred
to 50%, even more preferred 10 to 50% and most preferred 10 to 30 mol-%.
The polyorganosiloxanes used in the present invention suitably have a
molar content of branched radicals T and Q of 0 to 50%, preferably 0 to 20%,
more preferably 0 to 10%, especially 0 to 5%, very especially 0%, based on the
total number of siloxy units .
The polyorganosiloxanes used in the t invention suitably have an
average number of siloxy units (number of silicon atoms) of 2 to 30. The average
number of siloxy units in the polyorganosiloxanes used in the present ion is
for example determined by gel permeation chromatography (GPC) after
appropriate calibration, particularly with polystyrene as standard. ably, the
average number of siloxy units is 2 to 20, more ably 2 to 15, even more
preferred 2 to 12, even more red 2 to 7.
it is within the scope of the present invention to use mixtures of the
polyorganosiloxanes used in the present invention with one another, as well as
mixtures of polyorganosiloxanes used in the present invention with silanes. When
using mixtures of polyorganosiloxanes bi-, tri- and higher modal butions are
formed. In this case, binary mixtures with a bimodal distribution are preferred. A
preferred ment is then the use of mixtures of short chain
polyorganosiioxanes having an average of 2 to 15 siloxy units and long-chain
polyorganosiioxanes having 16 to 30 siloxy units. The use of such mixtures is
advantageous in that in the lignocelluiosic materials different sites of action are
operated. Thus, the long-chain polyorganosiioxanes are preferably located in the
ellular spaces (Iumens) while the short-chain polyorganosiioxanes are more
accumulated in the cells or cell walls. Overall this leads to a higher active
penetration and concentration, and thus an improved effect is achieved.
The functional groups F of the polyorganosiioxanes or silanes used in the
t invention serve both to improve the solubility of the polyorganosiioxane or
silanes in the preferably aqueous formulation, on the other hand to the ing
of the polyorganosiioxanes or silanes in the lignocelluiose materials, in particular
in the cells and cell walls of the mentioned materials, particularly for increasing
the dimensional stability of the materials or of the shrinkage or in the
presence of swelling ts, in particular humidity. From these points, the
following functional groups F are ularly suitable:
- epoxy group,
- carbonate group,
- isocyanate group including blocked isocyanate group,
- xanthate / Xanthogenat ester group,
- organo amino group Si-bonded via N,
- y group Si-bonded via 0,
— alkoxy group Si-bonded via 0, and
- thiosulfato group.
The c substituents R1 of the polyorganosiioxanes or silanes used in the
present invention are suitably selected from the group consisting of:
straight-chain, cyclic or branched, saturated, unsaturated or aromatic
hydrocarbon radicals having up to 100 carbon atoms, which may optionally
contain one or more groups selected from
_O_’
_s_,
—NR2—, wherein R2 ents hydrogen, a lent straight-
chained, cyclic or branched, saturated, unsaturated or ic hydrocarbon
radical having up to 60 carbon atoms, which may contain one or more groups
selected from -O-, -S-, -NH-, -C(O)- and -C(S)-, and which may optionally be
substituted by one or more substituents selected from the group consisting of a
hydroxyl group, an optionally substituted heterocyclic group, ably containing
one or more nitrogen atoms, amino, alkylamino, dialkylamino, ammonium,
polyether radicals and polyether ester radicals, wherein in case that multiple
groups -N R2 are present, these may be the same or different, may comprise
, wherein R2 is as defined above,
_P<R )2
, wherein R2 is as defined above,
—C(O)— and
-C(S)-.
and may be substituted by one or more radicals selected from the group
consisting of:
- hydroxyl,
- mercapto (-SH or-S'),
- isocyanato,
- halogen (such as chlorine, fluorine),
- a polyether radical having up to 60 carbon atoms, which may optionally n
one or more amino, mono- or dialkylamino, or arylamino groups,
- a saccharide-containing organic radical,
or two tuents R1 from different siloxy units together form a straight-chained,
branched or cyclic alkandiyl radical having 2 to 20 carbon atoms between two
silicon atoms, which is ally interrupted by -O-, -S-, -C(O)—, -NH- and is
optionally substituted by OH,
wherein the bonding to n may be via a carbon atom and / or a heteroatom.
As mentioned above, these radicals R1 are selected from the group consisting of
the radicals RF and RN, wherein the radicals RF are radicals R1 having the
mentioned functional groups F and the radicals RN are radicals R1 not having the
ned functional groups F.
Preferably, the radicals R1, R2 and R3 in the polyorganosiloxanes or silanes used
in the present invention, including RF and RN, have no amino groups. Except for
such amino group-containing radicals having a zwitterionic group such as a
betaine or a sulfobetaine group, or such radicals wherein the amino group is
bonded to the silicon atom via the nitrogen atom.
Preferably, R2 is en, a saturated arbon radical having up to 24
carbon atoms, which may contain one or two groups selected from -O-, -S-, -NH-,
,-C(O)— and -C(S)—, and which may optionally be substituted by one or two
hydroxyl groups.
Preferably, R3 is a divalent saturated aliphatic arbon radical having up to
carbon atoms, which may contain one or two groups, and which may
ally be substituted by hydroxy, and which is bonded to the silicon atom via
carbon.
The radicals RN preferably include: n-, iso-, or tert.-C1-ng-alkyl, 02-sz-
alkoxyalkyl, -cycloalkyl, Ce-Cgo-aryl, Ce-Cgo-aryl(C1-Ce)alkyl, C6-C30-
alkylaryl, C2-C22-alkenyl, C2-sz-alkenyloxyalkyl, which may all be substituted by
one or more (such as one to five) substituents, such as hydroxyl, halogen
(particularly fluorine), and which may have one or more ether groups, such as
HsC-, CHsCH2-, CH3CH20H2-, (CH3)2CH-, C3H17- and C10H21-, HzC=CH-O-(CH2)1-
6, cycloaliphatic radicals such as cyclohexylethyl, limonyl, norbonenyl, ,
tolyl, xylyl, benzyl and 2-phenylethyl, halogen(C1-C1o)alkyl, such as
Cfan+1CH2CH2' n f = 1 to 8, such as CF3CH2CH2-, C4F9CH20H2-,
CeF13CHzCH2-, CzF5—O(CF2—CF2—O)1-1oCF2—, F3)—CF2—O]1-5—(CF2)0-2—,
F(CF3)— and C3F7—OCF(CF3)—CF2—OCF(CF3)—.
Particularly preferred are methyl, vinyl, phenyl, 3,3,3-trifluoropropyl, and most
preferred is RN = Methyl.
In the polyorganosiioxanes or silanes used in the present invention the radicals
RF are ably selected from the group consisting of:
- quaternary phosphonium groups containing radicals of the formula:
2O —R3—P+(R2)3
wherein R3 is as defined above and is bonded to the silicon atom via , the
radicals R2 may be the same or ent and are as defined above, and
preferably at least one of R2 is not hydrogen,
—R3—P(R2>2
wherein R3 is as defined above and is bonded to the silicon atom via carbon, the
radicals R2 may be the same or different and the radicals R2 are as defined
above,
- epoxy groups containing radicals selected from:
carbonate groups containing radicals ed from:
—\/\O/fi___‘
O 0
urethane groups containing radicals selected from:
—R3—OC(O)NH-R2
wherein R2 and R3 are as described above,
isocyanate groups containing radicals selected from:
—-R3—NCO
wherein R3 is as described above,
urea groups containing radicals ed from:
—R3—NHC(O)NHR2, wherein R2 and R3 are as defined above,
amid or amido groups containing radicals selected from:
—R3—NHC(O)—R2 or O)NH-R2,
wherein R2 and R3 are as defined above,
- enamine groups containing radicals selected from:
—-gi/ \N/ 2
I R (imine form) which may be present as a tautomer
when one of the radicals R2 is a hydrogen atom in B-position to the
nitrogen atom:
—Si/ \NHl
l R
, wherein the radical
R2* from the radical R2
formally
results from shifting of a hydrogen atom, and wherein R2 are the same or
different and R2 and R3 are each as defined above,
which are particularly obtainable by reaction of amino-functional
ganosiloxanes with ketones, such as tic or aromatic ketones having
up to 14 carbon atoms, such as C3-C14 aliphatic ketones, aromatic C8 to C12
ketones, further enamines of the formula
wherein R2 and R3 are as defined above,
which are particularly obtainable by reaction of amino-functional
polyorganosiloxanes with monoaldehydes, such as aliphatic or aromatic
aldehydes having up to 14 carbon atoms, for example, dehyde,
butyraldehyde, furfural, acrolein, crotanaldehyde, glycolaldehyde , dol,
aromatic C7 to C11 aldehydes, for example benzaldehyde, anisaldehyde, vanillin,
salizylaldehyde,
aldehyde groups containing radicals, such as selected from:
n R3 are the same or different and R2 and R3 are as defined above,
which are particularly obtainable by reaction of aminofunctional
polyorganosiloxanes with dialdehydes, such as glyoxal, malonaldehyde,
aldehyde, phthalaldehyde, isophthalaldehyde, terephthalaldehyde,
i0 — hemiacetal and acetal group containing radicals such as those resulting
from the reaction of aldehyde groups containing polysiloxanes or silanes
with monovalent or polyvalent alcohols, such as methanol, ethanol, glycol
zwitterionic group containing radicals such as carbobetaine groups
containing ls selected from:
—-—R§-lTl—R3—COO_ IIRZ
R2 —R3—N—R3-COOH or its neutral form:
and salts thereof,
wherein R2 and R3 are the same or different and are as defined above,
sulfobetaine groups containing radicals ed from:
if 2
—R§-lTl—R3—SO3+ _ Fl?
2 3_
R __ L _R N R
or its neutral form:
SO3H
and salts thereof,
n R2 and R3 are the same or different and are as defined above,
carboxylic acid/carboxylate groups containing radicals selected from:
-R3-COOR2, -R3-COO'
wherein R2 and R3 each are as defined above,
sulfonic acid / sulfonate groups containing radicals selected from:
-R3-SO3R2, -R3-sog'
wherein R2 and R3 each are as defined above,
- ic acid halfesters / sulfate groups containing radicals selected from:
2, -oso3'
wherein R2 is as defined above,
oric ester/ phosphate groups containing radicals selected from:
wherein R2 and R3 are as defined above, and
fluorophosphoric ester selected from:
F OR2 0'
--R3—O—ll3—OR2 —R3—o—I|=—F -—R§—O-F"—F
n n n
o o 0
, and
wherein R2 and R3 are as defined above,
phosphonic esters / phosphonate groups containing radicals selected from:
or the protonated forms thereof, wherein R2 and R3 are as defined above,
in R3 is bonded to the phosphorus atom via a carbon atom), and
wherein R3 is as defined above,
phosphorous ester/ phosphite groups containing radicals,
OR2 OR2 0'
I I i
3 2 3 - 3 —
—R—o—P——0R —O
lO , and —R—O—P—Ol
wherein R2 and R3 are as defined above (and are bonded to the oxygen
atom of the phosphorous ester/ phosphite groups via carbon),
l5 te/ xanthogenate ester groups containing radicals
S S
n n
—R3—O-C—S—R2 —R3—O—C—S'
wherein R2 and R3 each are as defined above,
amino groups Si-bonded via N, selected from:
-N(R2)2, wherein R2 is as d above, with the proviso that at least one
radical R2 is not hydrogen,
hydroxy group,
acyloxy groups Si-bonded via 0, selected from:
_O—C_R
wherein R2 is as defined above.
- alkoxy groups Si-bonded via 0, selected from:
-OR2, wherein R2 is as defined above,
and the cations, which neutralize the anionic functional groups, are selected from
the group consisting of:
ammonium groups (N+(R2)4, wherein R2 is as d ,
phosphonium groups (P+(R2)4, wherein R2 is as defined above) and mono- to
trivalent metal cations,
and the anions, which neutralize the cationic functional groups, are selected from
the group consisting of:
halide,
hydroxide,
borate,
sulphate,
phosphate,
nitrate and
carboxylate.
Particularly preferred groups RF include:
- quaternary phosphonium groups containing radicals of the formula:
-R3—P*(R2)3
n R3 is as defined above, bonded to the silicon atom via carbon, the
ls R2 may be the same or ent and the radicals R2 are as defined
above, and preferably at least one of the radicals R2 is not hydrogen,
phosphine groups containing radicals of the formula:
—R3—P (R2)2
wherein R3 is as defined above, bonded to the silicon atom via carbon, the
radicals R2 may be the same or different and the ls R2 are as defined
above,
isocyanate groups ning radicals, selected from:
—R3—NCO
Wherein R3 is as bed above, and blocked derivatives thereof, such
as lactams, oximes, pyrazoles, sterically hindered amines or malonic acid
ester (C. Githler, M. Homann M. Mager, M. Schelhaas, T. Stingl, Farbe & ,
Lack, 110. Volume, 12/2004, 34-37),
epoxy groups containing radicals, ed from:
Mo/%
carbonate groups containing radicals selected from:
LR‘LCOO' R2
3 3
or its neutral form: _R_N—R_COOH
wherein R2 and R3 are the same or different and are as defined above,
sulfobetain groups containing radicals selected from:
* 2
—R3—lTl—R3—SO3+ _ if
or its neutral form
—R3—N-R3—803H
wherein R2 and R3 are the same or different and are as defined above,
ylic acid / carboxylate groups ning radicals selected from:
-R3-COOR2, -R3-COO'
wherein R2 and R3 each are as defined above,
sulfonic acid / sulfonate groups ning radicals selected from:
423-303 R2,, -R3-sog'
wherein R2 and R3 each are as defined above,
- phosphonic acid esters / phosphonate groups containing ls selected
from:
9H 9H 9
—R3—l[=|’—OH l’—O' —R3—IIDI—0'
O O o
, and
wherein R3 are as defined above,
- phosphorous ester/ phosphite groups ning radicals
9H 9H
—R§—o—P—0H 9'
—R3—o-P—0’ and —-R3—O—P-O'l
wherein R3 is as defined above,
- xanthate / xanthogenate ester groups containing radicals
S S
n n
—R3—O—C—S—R2 —R3—o—c—S'
wherein R2 and R3 each are as defined above,
amino groups Si-bonded via N, selected from:
-N(R2)2, wherein R2 is as d above, with the proviso that at least one
radical R2 is not hydrogen
acyloxy groups Si-bonded via 0, selected from:
—-O—C—R
, wherein R2 is as defined above,
- alkoxy groups Si-bonded via 0, selected from:
-OR2, wherein R2 is as defined above, except hydrogen.
Preferred cations which neutralize the anionic functional groups are selected from
the group consisting of:
Ammonium groups )4, wherein R2 is as d above),
phosphonium groups (P+(R2)4, n R2 is as defined above), and mono- to
trivalent metal cations, such as for example Na+, K”, Fe”, Fe 3+, Al“, Cu”, Zn2+
und Cr3+.
Preferred anions which neutralize the cationic functional groups are selected from
the group consisting of:
halide,
hydroxide,
borate,
sulfate,
phosphate,
nitrate and
carboxylate.
Polyorganosiloxanes according to the present invention preferably contain
at least one radical of the formula MF:
—o,—,2—Si—RF
, wherein R1 is as defined above, preferably RN as defined above,
and RF as d above.
In a further preferred embodiment polyorganosiloxanes are used having
the formula:
(lll)
wherein n1 + n2 = 1 to 28, preferably 1 to 20, more preferably 1 to 15, more
preferably 5 to 15, and n2 2 0, preferably 1 to 28, more preferably 1 to 10, more
preferably 1 to 5, and R1 and RF are as defined above.
ularly preferred are polyorganosiloxanes according to the present
invention having the formula
R1 R R
F l I
R—sl—o F
si—o si—R
R1 R1 R1
(VI)
n n is in number average 0 to 28, preferably 0 to 20, more preferably 0 to
, more preferably 5 to 15, and R1 is as defined above, preferably RN as defined
above, and RF is as defined above.
In a further preferred embodiment polyorganosiloxanes are used having the
formula:
R1l T1 R F|{1
RLsu-o si—o slsi—R1
1 1 sl—o
1 1
R R R
n1 n2R
(IV)
n n1 + n2 = 1 to 28, and n2 2 1, preferably 1 to 28, more preferably 1 to 10,
more preferably 1 to 5 and R1 and RF are as defined above.
In a further preferred embodiment cyclic polyorganosiloxanes are used
having the formula:
wherein n1 + n2 = 3 to 7 and n2 2 1, preferably 1 to 7, more preferably 1 to 5,
particularly preferably 1 to 3 and R1 and RF are as defined above.
It is r possible that the radical RF is located on a silicon atom, which forms a
In a further red embodiment of the invention, several types of the inventive
compounds are used simultaneously.
The polyorganosiloxanes or silanes of the present invention may be used in
combination with other polyorganosiloxanes or silanes different from those of the
present invention. Such polyorganosiloxanes or silanes, which are ent from
the polyorganosiloxanes or silanes according to the present invention, may for
example also comprise functional groups which are ent from RF, and which
for e comprise amino groups (NH2, NHR1, NR12, wherein R1 represents an
organic radical) or ammonium groups (NH4+, NR1H3+, NR12H2+, NR13H+ and
NR1 +, wherein R1 represents an organic radical).
Therein, a combination of polyorganosiloxanes or silanes with basic functional
polyorganosiloxanes or silanes with acidic functional groups and groups are
particularly preferred. Herein, the term "basic" includes both the basic functional
groups, such as amino groups, as well as their salts or protonated forms,
such as
ammonium groups. hangeably the term "cationic" polyorganosiloxanes or
silanes is used. The term c" includes both an acidic onal group, such
as carboxyl groups, as well as their salts, such as carboxylates. lnterchangeably
the term "anionic" polyorganosiloxanes or silanes is used.
Especially red are: combinations of led cationic polyorganosiloxanes
or silanes, which se for example, amino groups (such as mentioned
above), ammonium groups (such as mentioned above), quaternary ammonium
groups (such as mentioned above), quaternary phosphonium groups (such as
ned above), with so-called anionic polyorganosiloxanes or silanes, which
comprise for example carboxylic acid groups / carboxylate groups, sulfonic acid /
ate groups, sulfuric acid half ester groups / sulfate groups, phosphoric ester
/ phosphate groups, phosphonic ester / phosphonate groups, phosphorig
ester groups / phosphite groups, xanthate / xanthogenate ester groups.
The molar ratio of the cationic to the anionic groups in the polyorganosiloxane or
silanes is preferably selected as follows:
cationic : anionic = 90 : 10 to 10 : 90, preferably 70 : 30 to 30 : 70, particularly 60
: 40 to 40 : 60.
Accordingly the present invention further relates to a composition sing:
a) at least one polysiloxane and / or silane as defined in any of claims 1 to 10
having a functional group F selected from the group of the acidic
functional groups:
- a zwitterionic group,
— carboxylic acid / carboxylate group,
- sulfonic acid / sulfonate group,
- sulfuric acid half-ester/ sulphate group,
- phosphoric ester/ phosphate group
- phosphonic ester/ phosphonate group,
- phosphorous ester/ ite group,
(each as previously defined)
b) at least one polysiloxane and / or silane having a basic functional group
selected from amino groups, ammonium , phosphonium groups
and phosphine groups (each as defined above and below).
The molar ratio of cationic groups (corresponding to component b)) to the anionic
groups (corresponding to component a)) in the ganosiloxanes or s is
preferably selected as follows:
cationic : anionic = 90 : 10 to 10 : 90, preferably 70 : 30 to 30 : 70, particularly 60
: 40 to 40 : 60.
The content of the cationic component b) is for example 1-90 wt -%, ably 5-
80 wt -% based on the total amount of component a) and b).
It is also within the scope of the present invention, to substitute the cationic and /
or anionic polyorganosiloxanes or silanes partially by cationic and / or anionic
hydrocarbon compounds, wherein the the terms cationic and c must be
understood as described above. Examples are cationic or anionic tants,
such as long-chain alkyl or aryl sulphonates, long-chain alkyl ammonium
compounds.
According to the present invention it is also possible to combine the rionic,
ularly betainic polyorganosiloxanes or silanes with the cationic or anionic
polyorganosiloxanes or silanes.
In a preferred embodiment, the polyorganosiloxanes or silanes according to the
invention have a lar weight of <2000 g / mol, preferably of <1500 g / mol,
more preferably of <1000 g / mol.
For the said polyorganosiloxanes of formulas (III), (IV) and (VI), n1 + n2 is
preferably 0 to 18, more preferably 0 to 13, even more preferably 0 to 10, even
more preferably 0 to 5, wherein at least one siloxy group with RF must be present.
The synthesis of thiosulfate groups containing polysiloxane or silane
compounds is also known (Silicones, Chemistry and Technology, Vulkan Verlag
Essen 1989, p 121).
Phosphine groups containing polysiloxane or silane compounds are for
example obtainable by alkylation of dialkyl or diaryl phosphines with the haloalkyl-
substituted siloxanes or silanes. (Organikum VEB Deutscher Verlag der
Wissenschaften 1988, 17. edition, p. 203).
Phosphonium groups containing polysiloxane or silane compounds are for
example obtainable by alkylation of yl or triaryl phosphines with kyl-
substituted siloxanes or s or by alkylation of the aforementioned phosphine
groups containing polysiloxane or silane nds (Organikum VEB Deutscher
Verlag der Wissenschaften, 1988, 17. edition, p. 203).
Epoxy—polyorganosiloxanes or -silanes are advantageously prepared by
hydrosilylation of unsaturated epoxy-functional compounds, such as allyl yl
ether and vinyl cyclohexene oxide, with SiH functional precursors under Pt
catalysis (Silicones, Chemistry and Technology, Vulkan Verlag Essen 1989, p.
90).
ate-functional polyorganosiloxanes or -silanes are obtainable either
by hydrosilylation of unsaturated carbonate-functional compounds, such as allyl
carbonate, with SiH-functional sors under Pt catalysis (US 5672338, US
5686547). Alternatively, they may be prepared from the ponding es
by insertion of 002 (DE 19505892) or by reacting rganosiloxanes or
2O silanes with bifunctional carbonate coupling agents ().
Polyorganosiloxanes or silanes modified with isocyanate groups, including
blocked isocyanate groups, are obtainable by reacting polyorganosiloxanes which
are functionalized with CH-acidic groups, such as hydroxyl or amino functional
polyorganosiloxane or silanes, with an excess of di— or higher functional
isocyanates, or by reaction of amino-functional polyorganosiloxanes or silanes
with COCI2, or by pyrolysis of carbamato-functional polyorganosiloxanes or
Urea groups containing polyorganosiloxanes or silanes are obtainable, for
example, by reaction of the above mentioned isocyanate-functional
polyorganosiloxanes or silanes with .
Urethane and urea-units containing ganosiloxanes or silanes are on
the one hand obtainable by reaction of hydroxyl- or amino-functional precursors
with isocyanates (Organikum VEB Deutscher Verlag der Wissenschaften 1988,
17. edition, p. 429). Alternatively, urethanes can also be obtained by reaction of
aminoorganosiloxanes or silanes with for e cyclocarbonates or ate-
functional siloxanes or silanes with amines (US 8).
Amide-functional siloxanes or silanes are, for example, obtainable by
reaction of aminoorganosiloxanes or silanes with lactones (DE 6,
Example 22).
Schiff base, imine, and enamine groups containing siloxanes or silanes
are, for example, obtainable by reaction of aminosiloxanes or s with
aldehydes or ketones, as demonstrated, for example, in W02008113820,
Example 1, and DE 4318536, Example 20a.
Hemiacetal and acetal groups containing siloxanes and silanes are, for
example, able by reaction of hydroxyI-functional (COH functional) siloxanes
with aldehydes to form structures, which contain hemiacetal or acetal functions
(Organikum German VEB Deutscher Verlag der Wissenschaften 1988, 17.
edition, p. 398-400) or, as described above, by reaction of aldehyde groups
containing polyorganosiloxanes or silanes with mono- or lent (particularly
divalent) alcohols.
Aldehyde groups containing siloxanes or silanes are, for example,
obtainable by reaction of aminosiloxanes with dialdehydes, for e C2 to 05
dialdehydes, with the formation of structures which, for example, contain the
combination of Schiff bases with aldehyde functions or enamines and aldehyde
functions. Alternatively, hydroxy-functional (COH functional) siloxanes can react
with dialdehydes to form structures, which contain etal and aldehyde or
acetal and aldehyde functions. (Organikum German VEB Deutscher Verlag der
Wissenschaften 1988, 17. edition, p. 390-400). Further, hydroxyl-functional (COH
functional) siloxanes can react with epoxy aldehydes to these end products. It is
also possible, to convert hydroxy-functional (COH functional) siloxanes by
catalytic dehydrogenation on Cu and Ag catalysts into aldehydes. A further
preferred group of aldehyde-functional siloxanes are compounds which can be
obtained by reaction of functional siloxanes, for example on the basis of
the addition of allyl glycidyl ether or vinyl cyclohexene oxide and SiH sors,
with aldehyde carboxylic acids, for example glyoxylic acid HC(=O)C(= O)OH. The
preparation can, for e be carried out in accordance with US 8,
Example 3.
Siloxane or silane-based carbobetaines are, for example, obtainable by
on of tertiary amino structures with oroacetate (Silicones, Chemistry
and logy, Vulkan Verlag Essen 1989, p 121). On the other hand, they can
be obtained by reaction of epoxy siloxanes or silanes with the alkaline salts of
amino acids (DE 10036532, Example 1).
Siloxane or silane—based sulfobetaines are, for example, obtainable by
reaction of tertiary amino structures with sultones (DE 4140447, Example 1).
Alternatively, they may be obtained by reaction of epoxy nes or silanes with
the alkaline salts of amino sulfonic acids, such as taurine, in analogy to the
corresponding carbobetaines.
Siloxane or silane-based carboxylic acids are, for example, obtainable by
reaction of hydroxyl- or amino-functional precursors with a carboxylic acid
anhydrides, such as phthalic anhydride, succinic anhydride and maleic anhydride
(DE 9, Example 1).
Acetoxy—functional siloxanes or silanes, for example with acyloxy groups
Si-bonded via 0, are, for example, obtainable by reaction of silanoles with
acetoxy silanes (Silicones, Chemistry and Technology, Vulkan Verlag Essen
1989, p 58). Alternatively, for example, silanols and alkoxysilanes can react with
acid anhydrides to form these end products. For the synthesis of such
compounds it is also possible to cleave siloxane bonds in the presence of acid
anhydrides and catalysts (V. Bazant, Organosilicon Compounds, Volume 1,
Academic Press New York, 1965, pp. 61-64).
Siloxane or silane-based sulfonic acid derivatives are, for example,
obtainable by reaction of epoxy-functional precursors with sodium bisulfite
(Silicones, Chemistry and Technology, Vulkan Verlag Essen 1989, p 121).
Siloxane or silane-based e derivatives are, for e, obtainable
by reaction of hydroxyl-functional sors with amido ic acid (DE
9, Example 3).
The synthesis of silicone-based phosphate derivatives or derivatives of
phosphoric acid is, for example, bed in US 1 and US 6175028.
Alkoxy-functional siloxanes are, for example, obtainable by alkaline
equilibration of silanes with cyclosiloxanes (Silicones, Chemistry and
Technology, Vulkan Verlag Essen 1989, p 5).
Phosphonic esters / phosphonate group-containing polyorganosiloxanes or
silanes are, for example, obtainable by reaction of alkenyl- polyorganosiloxanes
or silanes with phosphorous esters.
Phosphorous ester/ phosphite groups containing polyorganosiloxanes and
silanes are, for example, able by reaction of hydroxyalkyl-
polyorganosiloxanes or silanes with phosphorous esters or phosphites.
Xanthate / xanthogenate ester groups containing polyorganosiloxanes or
s are, for example, obtainable by reaction of alcolates of the alkoxy
polyorganosiloxanes or silanes with carbon disulfide and optionally uent
reaction with alkyl halides to form xanthogenate ester.
Via N to Si bonded organoamino groups containing polyorganosiloxanes or
silanes are, for example, obtainable by reaction of halogen- polyorganosiloxanes
or silanes with .
The invention r relates to compositions comprising at least one
polyorganosiloxane and / or silane, as defined above, and at least one solvent
and / or at least one biocidal agent for the treatment of ellulosic als.
The compositions of the present invention comprising at least one onalized
polyorganosiloxane and / or silane, as defined above, may for example comprise
a solubilizer and / or an emulsifier which particularly leads to an increase in
stability of the compositions of this invention, such as for example an aqueous
composition, such as an emulsion or a solution or a dispersion in a solvent.
Suitable solubilizer or emulsifier are particularly amino-modified silicones,
quaternary fatty aminalkoholate, especially a quaternary fatty hanolat.
le ts, depending on the method of ation, are:
carbon dioxide, alcohol, water, ethane, ethylene, propane, butane, sulfur
hexafluoride, nitrogen oxides, ionic s, chlorotrifluoromethane,
monofluoromethane, methanol, ethanol, DMSO, isopropanol, acetone, THF,
acetic acid, ethylene glycol, polyethylene glycol, acetic anhydride, N,N-dimethyl
aniline, methane, e, hexane, cyclohexane, toluene, heptane, benzene,
ammonia, propanol etc. and mixtures thereof, more preferably water, organic
solvents, such as polyalcohols, such as in particular propylene glycol, ethylene
glycol or butyl diglycol, ethanol, propanol, isopropanol, n-butanol, furfuryl alcohol,
THF, DMSO, dioxane, aliphatic and / or nated hydrocarbons, etc., or
mixtures f.
A preferred emulsion of the functionalized polyorganosiloxane and / or silanes as
defined in the present invention contains:
a) at least one functionalized polyorganosiloxane and / or silane as defined
according to the invention (optionally in combination with one or more non-
inventive polyorganosiloxanes and / or silanes) in a concentration of 1-80 wt -%,
ably 5—60 wt-%, most preferred from 10-50 wt-% (wherein this amount
includes the total amount of the onalized polyorganosiloxanes and/or
silanes as defined according to the present invention and of the non-inventive
polyorganosiloxanes and / or silanes),
b) water in an amount of 99 to 20 wt-%, ably 95 to 40 wt -%, most
preferred 90 to 50 wt -%,
in each case based on the total amount of components a) and b),
and optionally:
0) one or more emulsifiers in an amount of 0-20 wt -%, preferably 0.5-20 wt -
2O %, more preferably 1-15 wt -%, most preferred from 2-10 -%, preferably selected
from ionic or non-ionic emulsifiers
d) one or more compounds for controlling the pH of the emulsion, such as a
base or an acid, preferably an acid such as acetic acid,
e) one or more solvents in a range of 0-50 —%, preferably 1 —50 wt -%,
preferably 1-20 wt -%,
wherein the amounts of the optionally present components 0) to e) refer to the
total amount of the emulsion.
The weight ratio of the components [a) + b)] to [c) + d) + e)] is from 100 : 0 to 100
: 70, preferably from 100 : 1 to 100 : 30.
The pH of such an emulsion is preferably in the range of 2-12, ably 2-7,
most preferred 3-5, which generally increases the stability of the emulsion.
Optionally, the amount of component d) is accordingly selected.
Examples of biocides, which may optionally be present in the compositions
of the t invention comprise for example:
Boron compounds, such as borax, borate, boric acid, boric acid ester,
Copper compounds, such as water-soluble copper compounds such as
copper (ll) salts (copper (ll) oxide, micronized copper, copper (ll) sulfate, copper
(ll) hydroxide ate, bis (N-cyclohexyldiazeniumdioxy) copper (ll),
mixtures of boron compounds and copper compounds
organic biocidal compounds, such as triazoles (as azaconazole,
cyproconazole, propiconazole, tebuconazole, TCMTB) sulfamide (such as
dichlorofluanid, tolylfluanid), carbamates (such as IPBC, carbendazim), aromatic
fungicides (such as ortho-phenylphenol, chlorothalonil) and other ides
(such as bethoxazin, isothiazolone), synthetic pyrethroids (such as permethrin,
ethrin, cyfluthrin, deltamethrin, silafluofen), insecticides (such as
imidacloprid, flufenoxuron, chlorpyrifos, fenoxycarb).
The boron compounds are usually used in an amount of 0.1 to 300 parts
by weight per 100 parts by weight of the total amount of polysiloxane and / or
silane.
The boron compounds stop microbial decomposition and allow for repelling
insects such as termites. Suitable boron compounds include boric acid, borax,
boric esters, such as trialkyl borate, such as hyl , triethyl ,
tripropyl borate and tributyl borate, borates as NangO13 x 4H20 or Timbor (R)
available from U.S. Borax |nc., borax and borates such as Timbor (R) are
preferred. An amount of boron of more than 300 parts by weight deteriorates the
ity of the emulsions. When boron nds are used, they are preferably
used in a concentration of at least 10 wt% based on the total amount of the
polyorganosiloxanes and silanes.
Further auxiliaries which can be used in the compositions of the invention
include for example: emulsifiers, as mentioned above, thickener, pigments, dyes,
antistatic agents, defoaming agents, flame retardants, etc.
Preferred compositions of the invention contain 2 5 weight -%, preferably
210 wt -%, more preferably 215 wt -°/o, most preferred 230 wt -% functionalized
polysiloxane and / or onalized , as defined above.
Preferred compositions of the invention contain:
to 50, preferably 15 to 50 parts by weight of onalized
polyorganosiloxane and / or functionalized silane, as defined above,
to 95, preferably 40 to 80 parts by weight solvent, such as the above-
mentioned, as defined above,
0 to 100, preferably 0 to 80 parts by weight of r es, such as the
above-mentioned
O to 100, preferably 1 to 80 parts by weight of other aries, such as the
above-mentioned, such as in particular emulsifiers.
The present application further relates to a process for treating
Iignocellulosic material, comprising the treatment of the ellulosic material
with at least one polysiloxane or silane, as defined above, or a composition as
defined above, by surface treatment, immersion treatment, or vacuum or
pressure nation.
In the method according to the present inventive the Iignocellulosic
materials may be coated or impregnated with the itions of the invention by
all methods for introducing aqueous solutions, common in wood treatment and
known from the literature, such as coating or impregnation, for example by
brushing, spraying, dipping, flow coating, hutch soaking, vessel pressure
impregnation, vacuum impregnation, vacuum pressure impregnation, borehole
impregnation or by the sap displacement method, see also "Encyclopedia of
Wood AZ" (Volumes | and II), Ulf Lohmann, DRW Verlag, ld-Echterdingen,
2003, see, inter alia "Einbringungsverfahren" Volume l, pages 289 to 292.
Preferably a vessel pressure impregnation or a surface treatment method
is carried out, such as brushing, spraying, dipping or flow coating. It is ularly
red to carry out a vacuum-pressure impregnation in the method of the
present invention. The substrate to be impregnated can be placed in a pressure-
resistant impregnation reactor and subjected to a first absolute pressure of 10 to
500 mbar, preferably 50 to 200 mbar abs., particularly about 100 mbar abs. for 5
minutes to 8 hours, preferably 15 minutes to 2 hours, particularly about one half
to one hour, maintaining this pressure, and then immersing the substrate in the
impregnating agent or covering the substrate with the impregnating agent and
increasing the pressure to 1.5 to 20 bar abs. for 0.5 to 4 hours, preferably to 5 to
bar abs. for 1 to 3 hours, particularly preferred to 10 to 12 bar abs. for about 2
to 3 hours. Subsequently, the re can be lowered to atmospheric pressure.
The substrate is taken from the impregnating solution, ally affects
subsequent vacuum or drains and then conveys the vacuum pressure
IO impregnated substrate to drying. Advantageously, a ic drying process is
carried out after the impregnation step. A specific air drying and/or a ic
technical drying method should follow the nation step, for example a
microwave , infrared drying, fresh / exhaust air drying, hot air drying,
vacuum drying, freeze drying, or a combination of these methods, such as
described, for example, in "Holzlexikon von A-Z" (Volume | and II), Ulf Lohmann,
DRW Verlag, lden-Echterdingen, 2003, see, "Holztrocknung", Volume I,
page 605).
The combination of the polyorganosiloxanes or silanes used in the present
invention with copper and / or boron and / or biocidal organic preservatives can
be used both in a preferred one-step process or in a less preferred two-step
process. One-step processes are for e brushing, dipping or impregnating
with formulations of polyorganosiloxanes or silanes used in the present invention
in organic solvents or as aqueous emulsions. In two-step processes, preferably
the copper and / or boron compounds and / or c biocidal preservatives are
applied first, for example by brushing, dipping or impregnating, and then the
polyorganosiloxanes or s used in the t invention.
In a preferred embodiment, the polyorganosiloxanes or silanes used in the
present invention are present as an aqueous emulsion. For the preparation and /
or stabilization of such an aqueous on, an emulsifier may be added,
wherein the emulsifier may also be an amino-modified silicone.
It is believed that the mechanism by which the polyorganosiloxanes
or s used in the present ion achieve an increased resistance of wood
and other lignocellulosic materials against weather and / or humidity deviations is
at least partially effected from hydrophobing the surface, preferably the layers
adjoining the surface up to the entire volume, of the wood or lignocellulosic
material. Regarding wood, it is assumed that the polyorganosiloxanes or silanes
used in the present invention lead to a d absorption of liquid water and a
reduced moisture on (gaseous water), which in turn leads to less variation in
the dimensions in the rain or with changing environmental humidity. Thus,
polyorganosiloxanes or silanes used in the present ion therefore achieve a
better dimensional stability of wood, because they penetrate into the cell wall of
the wood and remain there permanently, apparently by reason of their
functionalization. Therefore, the wooden cell wall is also in the dry state in a form
of a pre-swollen state and therefore absorbs less water than untreated wood. The
penetration of the polyorganosiloxanes or silanes used in the present invention is
particularly achieved with so-called microemulsions, for example with an e
particle size of 10 to 100 nm. Such microemulsions may penetrate into the pores
of wood cell walls and even between the cellulose s, thus permanently
reducing the further uptake of water. In this way, the dimensional change, such
2O as age during the drying of the wood, is reduced when the moisture content
of the environment ses. In case of macroemulsions, for example having a
le size of greater than 50 to 100 nm, it is assumed that the
polyorganosiloxanes or s used in the present invention at least partially
coat the inner surfaces of the wood cells and penetrate into the pores of the wood
cell wall. The polyorganosiloxanes or s used in the present invention on the
one hand allow a greater association with the lignocellulosic material and on the
other hand provide a growth-inhibiting effect on microorganisms. The treatment
especially effects resistance against fungi, so that lignocellulosic materials such
as wood, treated with the polyorganosiloxanes or silanes used in the present
invention, are less affected by staining, for example ””6“" fungi, or molds, or
destructive fungi (white rot, brown rot) , and therefore have a greater resistance
against microbial degradation. It is ed that impregnation with the
polyorganosiloxanes or silanes used in the present invention presses the
moisture t in the wood below the level required for growth of the fungi. By
means of the polyorganosiloxanes or silanes of the invention it is surprisingly
possible to permanently impregnate wood in a practical one—step process, and
thus to further reduce the tendency of the wood to absorb water, to improve the
dimensional stability in changing moisture contents of the environment and to
reduce the degradation of wood by fungi, bacteria and insects, such as wood-
destroying insects, such as termites, house longhorn , common furniture
beetle, powder post beetles effectively. At the same time yellowing and graying of
the wood by light and weather impact is suppressed.
In a further particularly preferred embodiment of the present invention, the
functionalized ganosiloxanes or silanes are incorporated into the
lignocellulosic material in a method using supercritical carbon dioxide, or other
preferably gaseous ts (such as the above-mentioned) as a carrier medium.
In case of the particularly preferred use of carbon dioxide this method
comprises a pressure impact of, for example, about 10 to 400 bar at about 0 to
180°C, especially from 50 to 300 bar at 32 to 100°C, very specifically 70 to 300
bar at 32 to 70°C. This s often requires special decompression methods
for not damaging the lignocellulosic al during ression. During
decompression the lly gaseous carrier medium, such as particularly
carbon dioxide, excapes and the polysiloxanes or silanes used in the present
invention remain in the lignocellulosic material, wherein generally cell walls and
intercellular spaces are filled with the polysiloxanes or silanes used in the present
ion. For more details on supercritical fluid treatments of wood materials
reference can be made to DE 4202320, , EP 1128939, EP
1146969, EP 1501664 and Morrell & Levien: "Entwicklung Neuer
Behandlungsverfahren zum Holzschutz" Conference report from "Konferenz fiir
Holzschutz in den 90er Jahren und er hinaus", Savannah, a, USA,
September 26-28,1994.
3O in a further particularly red embodiment of the present invention
alkoxy and / or acyloxy, preferably acetoxy-functionalized polysiloxanes and / or
silanes are introduced into the lignocellulosic material by means of a method
using carboxylic acid anhydrides, especially acetic anhydride, as a solvent and
reactant. Preferably, for this purpose the wood is placed in a vacuum and
pressure-resistant reactor and first set under , then a mixture comprising
acetic anhydride and aikoxy and / or acetoxy-functionalized poiysiloxanes and / or
silanes are . Preferably, at elevated pressure and temperature the wood
impregnation is ed over several hours. Thereafter, excess impregnating
liquid is discharged. By applying a vacuum and optionally vapor tion
volatile compounds are removed from the wood. It is preferred to use alkoxy and /
or acetoxy-functionalized poiysiloxanes and / or silanes in an amount of 0.01 to
wt -%, preferably 0.1 to 10%, more preferably 0.1 to 5 wt -% based on the
weight of the wood. More technical details about impregnation in the presence of
acetic anhydride can be found in EP 680 810. In this procedure, the weight ratio
of aikoxy and / or acetoxy-functionalized poiysiloxanes and / or silanes to
carboxylic acid anhydrides, especially acetic anhydride, is preferably from 0.1 :
100 to 20: 100, ably 1 : 100 to 10 : 100.
The aikoxy and / or acetoxy-functionalized poiysiloxanes and / or silanes,
especially acetoxypolysiloxane may also be prepared in-situ by using
polyorganosiloxanols, in particular erminated polyorganosiloxane, in
particular hydroxy-terminated polydimethylsiloxane in the presence of di, tri or
tetraalkoxysilanes, so that they can react with the polyorganosiloxanols to form
2O among others alkoxy and / or acetoxypolysiloxanes. Generally, poiysiloxanes with
acyloxy groups Si-bonded via 0, such as the acetoxy group, may be ed in-
situ from the corresponding polyorganosiloxanols, in particular SiOH terminated
polyorganosiloxanes, in particular hydroxy—terminated polydimethylsiloxanes and
the corresponding anhydrides.
According to the invention, it is preferred to achieve contents of the
polyorganosiloxanes or s used in the present invention by the method of
application or introduction of said ganosiloxanes or silanes of up to 20 wt-
%, preferably up to 10 wt.-%, more preferably up to 7 wt -%, ally 1 to 7 wt-
%, especially about 2 to 5 wt-%, based on the total mass of the dried treated
lignocellulosic material.
Using the ganosiloxanes or silanes used in the t invention it is
possible to achieve a m protection of the lignocellulosic material with a
very low content of the same.
According to the invention, the content of the polyorganosiloxanes or
silanes used in the present invention in the lignocellulosic materials can be
increased by using a very concentrated aqueous emulsion of the
polyorganosiloxanes or silanes. Therefore, preferred concentrations of said
s emulsions are at least about 5, preferably at least about 10, more
preferably at least about 15 wt -%, based on the total amount of the emulsion.
Alternatively, polyorganosiloxanes or s can be used, wherein the preferred
concentrations correspond to those of the emulsion.
The use of the microemulsions (average droplet diameter of the
polyorganosiloxanes or silanes less than 200 nm) is particularly red, since
T5 the uptake into the lignocellulosic material occurs very easily. According to the
invention it has been found that the penetration depth and therefore the
effectiveness of the functionalized polyorganosiloxanes or silanes of the present
invention also depends from the molecular weight and the wettability of the
lignocellulosic material with said functionalized polyorganosiloxanes or silanes. It
is shown that ally the chained or low molecular weight
ganosiloxanes or silanes of the present invention, which are used
according to the invention are preferred herein. The polyorganosiloxanes used in
the present invention, for example, have number average molecular weights Mn
of less than 3000 g/mol, preferably less than 2000 g/mol, more preferably less
than 1000 g/mol (in each case determined by gel permeation chromatography on
polystyrene as the standard). The silanes of the present invention are low
molecular weight compounds per se and in general have a molecular weight of
less than 500 g/mol, more preferably less than 400 g/mol, more preferably less
than 300 g/mol.
Examples
Example 1:
Test items of size 25 * 25 * 10 mm3 l * tangential * longitudinal) of the wood
types pine splint (Pinus sylvestris L.) and beech (Fagus sylvatica L.) were kiln
dried at 103 °C to constant mass. Subsequently, a vacuum impregnation was
carried out with an aqueous on containing 10 wt -% of a sarcosin-
functionalized silicon having a chain length D10 (10 D units), prepared ing
to Example 1 of DE 10036532, having the structure
KO+>/\N K+
OMS?CH3
H3 CH3S|i\/\/OVi/Nw:
Kiln drying was d out for 4 days at temperatures rising up to 103 °C.
Subsequently, a washout has been carried out according to EN 84 to remove
extractable siloxanes and other materials.
This was a 14-days e in water with multiple water exchanges. A percentage
weight increase of about 9% in e, relating to the initial weight of each dried
on-treated wood resulted.
To determine the water absorption the samples were loaded with bars and
poured with about 300 ml of water. From the weight gain after 2, 4 6 and 24 ,
hours, the water absorption in % was calculated. In each case, the water content
was related to the initial weight of the (still) untreated test items, in order to
exclude an influence of the weight gain due to the treatment.
wnass_ Wtrbeh
Water absorption = wtrunbeh *100 [0/0]
wnass: weight of wet test items
wtrbeh: weight of dry test items after treatment
wirunbeh: weight of dry test items before treatment
It was found that the wood samples treated with the zwitterionic functional
siloxanes showed a reduced water absorption of about 36 wt-% after 24 hours
compared to the respective untreated reference.
Example 2:
Test items of size 25 * 25 * 10 mm3 (radial * tangential * longitudinal) of the wood
types pine splint (Pinus tris L.) and beech (Fagus sylvatica L.) were kiln
dried at 103 °C to constant mass. Subsequently, a vacuum impregnation was
carried out with an aqueous emulsion containing 30 wt -% of
propyltriacetoxysilane in acetic acid, additionally containing 0.07 wt-% H2804.
The test items were subjected to a vacuum of 7 mbar for about 15 min in a
vacuum vessel. Then the impregnation solution was sprayed and normal
pressure ed (impregnation according to EN 113).
The test items were heated in the on for 5 hours at 120 °C under reflux and
in the absence of moisture (CaClz tube). The test items were then ted with
acetic acid in a Soxhlet extractor to soluble silane or siloxane and extracted with
ethanol, to remove the acetic acid. The test items were then dried at 103 °C to
constant mass. Then immersion in water was d out as described in
Example 1. The test items showed a strongly retarded absorption of water,
compared to the untreated wood samples (control). After 24 hours, this was
approximately 25 % lower ed to the control. In addition, a permanent
swelling of the cell wall was ed. The cross-sectional area was increased by
7% (bulking).
The g could not be undone by leaching with water. The average weight
increase in the kiln dry state was about 14 wt - % based on the initial weights of
the 10 samples. The swelling - shrinkage efficiency (ASE = anti shrink efficiency)
was calculated using the following formula:
ASE = au- at locu *100 [%]
ocu = swelling coefficient of the controls
at = swelling coefficient of the untreated samples
ASE = “u x100 [%]
[9|u = swelling coefficient of the controls
t = swelling coefficient of the treated samples.
Wherein the swelling coefficients were calculated using the ing formula:
swelling coefficient ct = Adry- Awet /Adry *100 [%]
n nass
n X1 00 [0/0]
Ad -A
swelling coefficientoc= ry—wet x100[%]
Adry = cross-sectional area dry
Awet= cross-sectional area wet
The achieved swelling - age efficiency (ASE) was in average about 50 %
compared to the untreated reference.
Example 3:
Test items of size 25 * 25 * 10 mm3 l * tangential * longitudinal) of the wood
types pine splint (Pinus sylvestris L.) and beech (Fagus sylvatica L.) were kiln
dried at 103 °C to constant mass. Subsequently, a vacuum impregnation (as
described in Example 2) was carried out with an 100 % of propyltriacetoxysilane.
The test items impregnated in such manner were heated in propyltriacetoxysilane
at 90 °C for 5 hours, the removed from the propyltriacetoxysilane solution and
stored at ambient condition 25 °C and 50 % relative humidity for 24 hours. Then a
kiln drying at 103 °C to constant mass followed and subsequently te
immersion in water at 25 °C. This was carried out as described in Example 1. The
weight increase after anew kiln drying was in average imately 68 %
compared to the initial weight of the 10 test items. Compared to the untreated
wood s a strongly retarded absorption of water was shown; after 24 hours,
this was reduced by about 70 wt-% in average.
e 4: Reference Example without siloxane (,, acetylated wood“ )
8 samples of pine splint (20 * 20 * 10 mm 3; radial * tangential * longitudinal) were
kiln dried at 103 °C and subsequently impregnated with acetic anhydride
according to EN 113. The samples were then heated to 120 °C when lying in the
chemical product and this temperature was maintained for 5 hours. After the
reaction time, the samples were placed in deionized water to stop the reaction
and to remove the excess acetic ide. The s were left in the water
for 2 days, after a day the water was exchanged. Subsequently, the samples
were dried, first at room temperature then at 103 °C.
The water absorption was tested in the kiln dried samples, by loading the
samples in a vessel and pouring with about 300 ml of water. After 2, 4, 6 and 24
hours, the weight was determined after a brief dabbing of the samples, which
were then rapidly put back into the vessel. The relative water absorption was
calculated based on the dry weight of the s prior to acetylation. Then, a
reduction of water absorption after 24 hours was calculated by relating the
reduction of the water absorption after 24 hours, compared to the control, to the
value of the control. In the first water absorption his reduction was -12,8 % and
increased to -34.9 % in the 4th water absorption.
Example 5: Synthesis of an acetoxy—functionalized polydimethylsiloxane
234 g (1 mol) ethyltriacetoxysilane were introduced into a round bottom flask and
231 g (0.5 mol) of a SiOH-stopped polydimethylsiloxane of the average structure
l l |
HO/TiO/TiO/TKOH
with a chain length distribution of 2 to 10 and remaining cyclodimethylsiloxanes
were added dropwise. During the dropwise addition, the ature rose from
°C to about 38 °C. After 5 hours reaction the product was igated by 1H
NMR and it was found that no free ethyltriacetoxysilane exists any longer.
The product has the following average structure:
e I Et
[Acoi' a a s
o’ I 0’ {‘OAc]
2 2
Example 6: lmpregnation with acetic anhydride acetoxy—functional
loxane-mixture according to Example 5
Each of 16 pine splint samples (20 * 20 * 10 mm3; radial * tangential *
udinal) were kiln dried at 103 °C and then impregnated with acetic
anhydride mixed with various amounts of acetoxy-functional polysiloxane (0%,
1%, 3%, 6 %, 10%, 20 wt -%) according to EN 113. The samples were then
heated to 120 °C when lying in the chemical product and this temperature was
ined for 5 hours. After the reaction time, the samples were placed in
deionized water to stop the reaction and to remove the excess chemical product.
The samples were left in the water for 2 days, after a day the water was
exchanged. Subsequently, the samples were dried, first at room temperature then
at 103 °C.
As can be seen from Figure 1, the Weight Percent Gain (WPG), i.e. the percentage
weight gain, sharply increases by treatment with increasing content of acetoxyfunctional
siloxane. The WPG was calculated based on the dry weight using the
ing formula:
weightafter treatment
WPG [%] = -1 • 100
weightbefore treatment
But even the g, the permanent ng in dry state due to the treatment, rises.
With pure acetylation (0% siloxane) it is 7.9% and significantly increases with 20%
admixture of siloxane to 8.7%. The Bulking was calculated based on the dry
dimensions using the following formula:
radafter treatment • tanafter treatment
bulking [%] = -1 • 100
radbefore treatment • tanbefore treatment
The water tion (Figure 2) was determined in the samples by placing in each
case 8 test items per treatment in a vessel, loading and pouring with about 300 ml of
water. After 2, 4, 6 and 24 hours, the weight of the samples was determined and the
relative water absorption based on the dry weight of the s prior to
(10903027_1):MGH
acetylation calculated. Based on the 24-hour values a water absorption reduction
(Reduct. WA) ed to the controls and the acetylated samples was calculated.
For this purpose the reduction of the relative water absorption in percentage points
was related to the relative water absorption of the controls and the acetylated
samples. In the first contact with water, the water absorption of the combinations with
polysiloxane was significantly reduced compared to the purely acetylated samples.
However, the maximum reduction of water absorption was ed with an
admixture of 6% polysiloxane. In the 4th water absorption hardly any differences
between the different combinations with polysiloxanes were recognizable. This
means that even an addition of 1% acetoxy-functional polysiloxane may effect a
maximum reduction of water tion. Compared to the pure ation the
combination with loxane shows much better hydrophobing.
Figure 2 shows reduction of Water absorption compared to non-acetylated wood
(black bars) and acetylated wood (shaded bars (top: 1th water absorption, bottom:
2nd water tion).
Example 7 (Reference):
(10903027_1):MGH
Pine splint samples 20*20*1Omm3 (radial*tangential*longitudinal) were
impregnated with an aqueous emulsion consisting of 10 wt -% (m/m) of amino-
onal polysiloxane having an average chain length of 12 siloxy units of the
formula:
O H l I H
H2N/\/N\j\/O\/\/Si[o//Ii 00’’ISi\/\/O\)\/N\/\NH2
3 wt-% acetic acid, 5 wt-% of a e of three emulsifiers, (isotridecyl alcohol
C13-polyethylene oxide with different polyethylene oxide chain s such as
in ®) and 82 % of water. The amino-functional polysiloxane was prepared
according to Example 22a in DE 4318536 by reaction of epoxy-functional
siloxane with nediamine.
Subsequently, the ination of the water absorption was carried out as
described in Example 6. In the first water absorption, the reduction of water
absorption after 24 hours was only -8.2%, this is probably due to the high
emulsifier content, which supported a water absorption. In the second water
absorption, the reduction was -18.6 %.
In the fungi test, as described below, the samples treated with this material
showed a weight loss upon incubation with Coniophora puteana of 9.7% (pine)
and 26.9 % (beech), and upon incubation with Trametes olor of 6.3%
(beech). The values of the controls are listed in the table below.
Example 8:
Pine splint samples 20*20*10 mm3 (radial*tangential*longitudinal) were
impregnated with an aqueous emulsion consisting of 10 wt -% (m/m) of carboxy-
functional polysiloxane having an average chain length of 12 of the formula:
wt-% emulsifiers (as in Example 7) and 80% water.
Subsequently, the water absorption was carried out as described in Example 6.
In the first water absorption, the reduction of water absorption after 24 hours was
-11.2%, in the second water absorption an increase of water absorption by +4.7%
occurred, compared to the control.
In the fungi test, as described below, the samples treated with this material
showed a weight loss upon incubation with hora puteana of 2.7% (pine)
and 14.1 % ), and upon incubation with Trametes versicolor of 2.7%
(beech). The values of the ls are listed in the table below.
e 9:
Pine splint samples 20*20*10 mm3 l*tangential*longitudinal) were
impregnated with an aqueous emulsion consisting of 10 wt -% (m/m) of a mixture
of the amino-functional polysiloxane as described in Example 7 (80 wt.-%) with
the carboxy-functional polysiloxane as described in e 8 (20 wt.-%), 3 %
acetic acid, 5 % emulsifier and 82 % water.
Subsequently, the water absorption was carried out as described in Example 6.
In the first water absorption, the reduction of water absorption after 24 hours was
-16.5% and was increased in the second water absorption to .
Accordingly, by combining the two functional polysiloxanes an improvement of
the water repellency of the treated wood can be achieved compared to the two
pure products. This is particularly interesting under the aspect, that the carboxy-
functional polysiloxane has a very good efficiency against wood-destroying fungi,
whereas the absorption of water is increased and t to heavy ng. By a
combination with the amino-functional polysiloxane the leaching can be the
hydrophobicity can be improved. Mixtures of amino-functional polysiloxane to
carboxy—functional polysiloxane of 50:50 and 20:80 showed better results in some
cases in the first water absorption, but in the second water absorption the
combination of 80:20 was superior.
fungi test
A fungi test was carried out in ance with EN 113, wherein, deviating from
the standard, in each case 2 treated and 2 untreated samples were incubated in
a Kolle flask. The table below shows the results.
Control 1
(Ref. )
amino/ carbo-
_—_-8 2 -36
absorption __—
Coniophora
puteana on 2,7 52,4
orne
fungi-. Coniophora
reSIstance
pubteana on
(weight-loss
eech
[%])
Trametes
on beech
)5: will be provided later
The examples show that functionalized polysiloxanes or silanes of the present
invention lower the water absorption in wood bodies. The sed water
absorption allows to use the functionalized polysiloxanes or silanes of the
invention as a protective agent for wood and other ellulosic materials,
wherein wood etc. may be made more resistant to weather influences such as
changes in the moisture content of the nment.
It has further been shown that wood, treated with functionalized polysiloxanes or
silanes according to the invention as a tive agent, is subjected to a
significantly lower surface infestation by mold and blue stain fungi.
As a further advantage, the functionalized polysiloxanes or s of the present
invention used as a protective agent for lignocellulosic materials, such as wood,
offer an increased resistance to infestation with harmful algae and marine
organisms, such as piddock. As a further advantage, the functionalized
polysiloxanes or silanes of the invention used as a protective agent for wood,
offer an increased ance to infestation with algae.
Further, the onalized polysiloxanes or silanes of the present invention can
increase the resistance of wood against wood-destroying insects, such as
es, house longhorn beetles, common furniture beetles, powder post beetles.
Furthermore, ation experiments, i.e. measurement of mass loss of beech
and pine in contact with the white rot fungus Trametes versicolor and the brown
rot fungus Coniophora puteana, that functionalized polysiloxanes or silanes
according to the invention se resistance of wood and other ellulosic
materials against these wood destroying fungi.
Experiments on the swelling and shrinkage behaviour of beech and spruce wood
samples show that the functionalized polysiloxanes or silanes of the present
invention provide wood with an increased dimensional stability when d to
water or humidity of the environment. This is a d property, as swelling and
shrinkage is a major disadvantage when using wood. For example, the increase
in the dimensional stability leads to a significantly reduced cracking, as has been
demonstrated in weathering tests.
Experiments in outdoor exposure ed that wood samples treated with the
functionalized loxanes or silanes according to the invention, exhibit an
increased color stability. This protection can be ascribed to the fact that in
particular the lignin degradation in the upper layers of the cell walls of the wood
takes place less rapidly than in untreated wood.
The leaching experiments with boric acid as a co-biocidal agent for determining
the fixation of hydrophilic substances by the functionalized loxanes or
silanes of the present invention in lignocellulosic als show that the
functionalized polysiloxanes or silanes of the present invention achieve a fixation
or retention of hydrophilic substances in wood or lignocellulose materials. The
fixation or retention even of lipophilic substances in lignocellulosic materials by
the functionalized polysiloxanes or silanes according to the invention derive from
the general lipophilic properties of these silicone derivatives. Therefore, the
functionalized polysiloxanes or silanes of the t invention are also le
for fixation of conventional wood treatment agents, such as flame retardants,
fungicides, insecticides or dyes. This particularly s to such conventional
compounds which are poorly retained in the matrix of the lignocellulosic material
and are easily washed out by water.
To detect a reduction of flammability, pine wood impregnated with the
onalized polysiloxanes or silanes according to the invention are examined
using a thermo-balance (TGA). Therefore, pine wood samples of the size 5 x 10 x
mm3 are treated with the functionalized polysiloxanes or silanes of the t
invention as well as with a commercial flame retardant for wood (lmpralit F3/66 ,
Ruetgers cs). The wood samples are then ground. By means of a thermo-
balance (STA 409 PC, Netzsch), the wood flour is continuously heated from 0 °C
to 800 °C under oxygen as a shielding gas with a heating rate of 20 °C / min, and
the weight changes are measured. The thermogravimetric analysis shows that
the functionalized polysiloxanes or s of the present invention, lead to a
higher flame resistance or fire ance of the so treated lignocellulosic
materials, as demonstrated on the example of wood. This is particularly the case
if in addition to the functionalized polysiloxanes or silanes of the present
invention, conventional flame retardants are applied to the lignocellulosic
material, such as those of or nds (phosphates, polyphosphates),
magnesium compounds (magnesium hydroxide), aluminum nds
(aluminum hydroxide), bromine / chlorine compounds (hydrogen halides) and
flame retardant systems with expanding materials.
The functionalized polysiloxanes or silanes of the present invention may also be
used for the physical and / or chemical bonding of conventional treatment agents
for wood and other cellulose-based materials, thus increasing its ance. This
ularly related to the combination of functionalized polysiloxanes or silanes
according to the invention with flame retardants, insecticides or dyes, especially
those compounds, which are particularly stable in a hydrophobic environment or
retained n.
Furthermore, wood treated with functionalized polysiloxanes or silanes according
to the ion may comprise more resilient surfaces, i.e. for example harder and
/ or abrasion resistant surfaces.
I
Claims (1)
1. Use of polyorganosiloxanes or silanes for the treatment of lignocellulosic materials, characterized in that the ganosiloxanes are straight-chained, branched or cyclic polyorganosiloxanes, formed from a number average of 2 to 30 siloxy units, which are selected from the group consisting of O R1 R1 R1 O Si O O Si O O Si O O Si R1
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
NZ716105A NZ716105B2 (en) | 2011-04-18 | 2012-04-18 | Functionalized polyorganosiloxanes or silanes for treating lignocellulose materials |
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
EP11162827 | 2011-04-18 | ||
EP11162827.7 | 2011-04-18 | ||
PCT/EP2012/057042 WO2012143371A1 (en) | 2011-04-18 | 2012-04-18 | Functionalized polyorganosiloxanes or silanes for treating lignocellulose materials |
Publications (2)
Publication Number | Publication Date |
---|---|
NZ617527A NZ617527A (en) | 2016-10-28 |
NZ617527B2 true NZ617527B2 (en) | 2017-01-31 |
Family
ID=
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