CN1809621A - 用于固体表面的部分氟化的润滑剂 - Google Patents
用于固体表面的部分氟化的润滑剂 Download PDFInfo
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- CN1809621A CN1809621A CN200480009967.0A CN200480009967A CN1809621A CN 1809621 A CN1809621 A CN 1809621A CN 200480009967 A CN200480009967 A CN 200480009967A CN 1809621 A CN1809621 A CN 1809621A
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- 239000000314 lubricant Substances 0.000 title claims abstract description 16
- 239000007787 solid Substances 0.000 title claims abstract description 8
- 150000001875 compounds Chemical class 0.000 claims abstract description 32
- -1 polycyclic hydrocarbon Chemical class 0.000 claims abstract description 12
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 6
- 229930195733 hydrocarbon Natural products 0.000 claims abstract description 5
- 239000004215 Carbon black (E152) Substances 0.000 claims abstract description 4
- 125000002947 alkylene group Chemical group 0.000 claims abstract description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 4
- 239000001257 hydrogen Substances 0.000 claims abstract description 4
- 125000002950 monocyclic group Chemical group 0.000 claims abstract description 4
- 229920006395 saturated elastomer Polymers 0.000 claims abstract description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 3
- 239000006185 dispersion Substances 0.000 claims description 2
- 125000006702 (C1-C18) alkyl group Chemical group 0.000 abstract 1
- 125000000923 (C1-C30) alkyl group Chemical group 0.000 abstract 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 1
- 125000000732 arylene group Chemical group 0.000 abstract 1
- 239000001993 wax Substances 0.000 description 12
- 239000000047 product Substances 0.000 description 6
- 150000003254 radicals Chemical class 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 5
- 239000013543 active substance Substances 0.000 description 5
- 238000000576 coating method Methods 0.000 description 5
- 238000000034 method Methods 0.000 description 5
- 125000003118 aryl group Chemical group 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 239000011248 coating agent Substances 0.000 description 4
- UZILCZKGXMQEQR-UHFFFAOYSA-N decyl-Benzene Chemical compound CCCCCCCCCCC1=CC=CC=C1 UZILCZKGXMQEQR-UHFFFAOYSA-N 0.000 description 4
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 4
- 229910052731 fluorine Inorganic materials 0.000 description 4
- 239000011737 fluorine Substances 0.000 description 4
- 238000003786 synthesis reaction Methods 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- 150000001336 alkenes Chemical class 0.000 description 3
- 230000008878 coupling Effects 0.000 description 3
- 238000010168 coupling process Methods 0.000 description 3
- 238000005859 coupling reaction Methods 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- 230000001050 lubricating effect Effects 0.000 description 3
- 125000005010 perfluoroalkyl group Chemical group 0.000 description 3
- BDERNNFJNOPAEC-UHFFFAOYSA-N 1-propanol Substances CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 2
- CYEJMVLDXAUOPN-UHFFFAOYSA-N 2-dodecylphenol Chemical compound CCCCCCCCCCCCC1=CC=CC=C1O CYEJMVLDXAUOPN-UHFFFAOYSA-N 0.000 description 2
- YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 2
- 239000004305 biphenyl Substances 0.000 description 2
- 235000010290 biphenyl Nutrition 0.000 description 2
- 239000004913 cyclooctene Substances 0.000 description 2
- 235000014113 dietary fatty acids Nutrition 0.000 description 2
- 229930195729 fatty acid Natural products 0.000 description 2
- 239000000194 fatty acid Substances 0.000 description 2
- 150000002430 hydrocarbons Chemical class 0.000 description 2
- 239000003999 initiator Substances 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 2
- 239000004810 polytetrafluoroethylene Substances 0.000 description 2
- 229920001343 polytetrafluoroethylene Polymers 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
- WTARULDDTDQWMU-RKDXNWHRSA-N (+)-β-pinene Chemical compound C1[C@H]2C(C)(C)[C@@H]1CCC2=C WTARULDDTDQWMU-RKDXNWHRSA-N 0.000 description 1
- WTARULDDTDQWMU-IUCAKERBSA-N (-)-Nopinene Natural products C1[C@@H]2C(C)(C)[C@H]1CCC2=C WTARULDDTDQWMU-IUCAKERBSA-N 0.000 description 1
- XJSRKJAHJGCPGC-UHFFFAOYSA-N 1,1,1,2,2,3,3,4,4,5,5,6,6-tridecafluorohexane Chemical compound FC(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F XJSRKJAHJGCPGC-UHFFFAOYSA-N 0.000 description 1
- WYOUGCMQGOWHCQ-UHFFFAOYSA-N 1-but-1-enyl-3-(3-but-1-enyl-2-dodecylphenoxy)-2-dodecylbenzene Chemical compound C1=CC=C(C=CCC)C(CCCCCCCCCCCC)=C1OC1=CC=CC(C=CCC)=C1CCCCCCCCCCCC WYOUGCMQGOWHCQ-UHFFFAOYSA-N 0.000 description 1
- LGJCFVYMIJLQJO-UHFFFAOYSA-N 1-dodecylperoxydodecane Chemical compound CCCCCCCCCCCCOOCCCCCCCCCCCC LGJCFVYMIJLQJO-UHFFFAOYSA-N 0.000 description 1
- GMBSMYPBNXMSFR-UHFFFAOYSA-N 5-[2-(3-but-1-enyldodecoxy)ethyl]tetradec-3-ene Chemical compound C(=CCC)C(CCOCCC(CCCCCCCCC)C=CCC)CCCCCCCCC GMBSMYPBNXMSFR-UHFFFAOYSA-N 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 1
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- 238000003547 Friedel-Crafts alkylation reaction Methods 0.000 description 1
- NUGPIZCTELGDOS-QHCPKHFHSA-N N-[(1S)-3-[4-(3-methyl-5-propan-2-yl-1,2,4-triazol-4-yl)piperidin-1-yl]-1-pyridin-3-ylpropyl]cyclopentanecarboxamide Chemical compound C(C)(C)C1=NN=C(N1C1CCN(CC1)CC[C@@H](C=1C=NC=CC=1)NC(=O)C1CCCC1)C NUGPIZCTELGDOS-QHCPKHFHSA-N 0.000 description 1
- 239000004698 Polyethylene Substances 0.000 description 1
- WTARULDDTDQWMU-UHFFFAOYSA-N Pseudopinene Natural products C1C2C(C)(C)C1CCC2=C WTARULDDTDQWMU-UHFFFAOYSA-N 0.000 description 1
- OUUQCZGPVNCOIJ-UHFFFAOYSA-M Superoxide Chemical compound [O-][O] OUUQCZGPVNCOIJ-UHFFFAOYSA-M 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 1
- 238000007259 addition reaction Methods 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 150000001335 aliphatic alkanes Chemical class 0.000 description 1
- XCPQUQHBVVXMRQ-UHFFFAOYSA-N alpha-Fenchene Natural products C1CC2C(=C)CC1C2(C)C XCPQUQHBVVXMRQ-UHFFFAOYSA-N 0.000 description 1
- 230000000386 athletic effect Effects 0.000 description 1
- 229930006722 beta-pinene Natural products 0.000 description 1
- 230000001680 brushing effect Effects 0.000 description 1
- PBGVMIDTGGTBFS-UHFFFAOYSA-N but-3-enylbenzene Chemical compound C=CCCC1=CC=CC=C1 PBGVMIDTGGTBFS-UHFFFAOYSA-N 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 229940125904 compound 1 Drugs 0.000 description 1
- 229940125782 compound 2 Drugs 0.000 description 1
- 229940126214 compound 3 Drugs 0.000 description 1
- 229940125898 compound 5 Drugs 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000007334 copolymerization reaction Methods 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- URYYVOIYTNXXBN-UPHRSURJSA-N cyclooctene Chemical compound C1CCC\C=C/CC1 URYYVOIYTNXXBN-UPHRSURJSA-N 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000007786 electrostatic charging Methods 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 150000002191 fatty alcohols Chemical class 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- LCWMKIHBLJLORW-UHFFFAOYSA-N gamma-carene Natural products C1CC(=C)CC2C(C)(C)C21 LCWMKIHBLJLORW-UHFFFAOYSA-N 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 1
- 239000010931 gold Substances 0.000 description 1
- 229910052737 gold Inorganic materials 0.000 description 1
- 229910002804 graphite Inorganic materials 0.000 description 1
- 239000010439 graphite Substances 0.000 description 1
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 1
- 230000002209 hydrophobic effect Effects 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 239000012948 isocyanate Substances 0.000 description 1
- 150000002513 isocyanates Chemical class 0.000 description 1
- 239000010687 lubricating oil Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- 238000006384 oligomerization reaction Methods 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- 239000012188 paraffin wax Substances 0.000 description 1
- 235000019809 paraffin wax Nutrition 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 229960004624 perflexane Drugs 0.000 description 1
- ZJIJAJXFLBMLCK-UHFFFAOYSA-N perfluorohexane Chemical compound FC(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F ZJIJAJXFLBMLCK-UHFFFAOYSA-N 0.000 description 1
- 235000019271 petrolatum Nutrition 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 229920000058 polyacrylate Polymers 0.000 description 1
- 125000003367 polycyclic group Chemical group 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- GMVPRGQOIOIIMI-DWKJAMRDSA-N prostaglandin E1 Chemical compound CCCCC[C@H](O)\C=C\[C@H]1[C@H](O)CC(=O)[C@@H]1CCCCCCC(O)=O GMVPRGQOIOIIMI-DWKJAMRDSA-N 0.000 description 1
- 238000007342 radical addition reaction Methods 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- MWNQXXOSWHCCOZ-UHFFFAOYSA-L sodium;oxido carbonate Chemical compound [Na+].[O-]OC([O-])=O MWNQXXOSWHCCOZ-UHFFFAOYSA-L 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 150000003673 urethanes Chemical class 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M105/00—Lubricating compositions characterised by the base-material being a non-macromolecular organic compound
- C10M105/50—Lubricating compositions characterised by the base-material being a non-macromolecular organic compound containing halogen
- C10M105/54—Lubricating compositions characterised by the base-material being a non-macromolecular organic compound containing halogen containing carbon, hydrogen, halogen and oxygen
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09G—POLISHING COMPOSITIONS; SKI WAXES
- C09G3/00—Ski waxes
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M105/00—Lubricating compositions characterised by the base-material being a non-macromolecular organic compound
- C10M105/50—Lubricating compositions characterised by the base-material being a non-macromolecular organic compound containing halogen
- C10M105/52—Lubricating compositions characterised by the base-material being a non-macromolecular organic compound containing halogen containing carbon, hydrogen and halogen only
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2211/00—Organic non-macromolecular compounds containing halogen as ingredients in lubricant compositions
- C10M2211/02—Organic non-macromolecular compounds containing halogen as ingredients in lubricant compositions containing carbon, hydrogen and halogen only
- C10M2211/022—Organic non-macromolecular compounds containing halogen as ingredients in lubricant compositions containing carbon, hydrogen and halogen only aliphatic
- C10M2211/0225—Organic non-macromolecular compounds containing halogen as ingredients in lubricant compositions containing carbon, hydrogen and halogen only aliphatic used as base material
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2211/00—Organic non-macromolecular compounds containing halogen as ingredients in lubricant compositions
- C10M2211/02—Organic non-macromolecular compounds containing halogen as ingredients in lubricant compositions containing carbon, hydrogen and halogen only
- C10M2211/024—Organic non-macromolecular compounds containing halogen as ingredients in lubricant compositions containing carbon, hydrogen and halogen only aromatic
- C10M2211/0245—Organic non-macromolecular compounds containing halogen as ingredients in lubricant compositions containing carbon, hydrogen and halogen only aromatic used as base material
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2211/00—Organic non-macromolecular compounds containing halogen as ingredients in lubricant compositions
- C10M2211/04—Organic non-macromolecular compounds containing halogen as ingredients in lubricant compositions containing carbon, hydrogen, halogen, and oxygen
- C10M2211/042—Alcohols; Ethers; Aldehydes; Ketones
- C10M2211/0425—Alcohols; Ethers; Aldehydes; Ketones used as base material
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Health & Medical Sciences (AREA)
- Emergency Medicine (AREA)
- Lubricants (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Moulds For Moulding Plastics Or The Like (AREA)
Abstract
用于固体表面，特别是用于滑雪板的润滑剂，其包含式(1)：RF－(A) a－(O) b－(B) c－(D) d－(RF) e的部分氟化化合物，其中RF是式F(CF2) n－的全氟化基团，n是1－20的数，A是C1－C30－亚烷基，优选C1－C18－亚烷基，B是具有6－14个碳原子的亚芳基或者是具有3－30个，优选3－18个碳原子的饱和或不饱和的单或多环烃，D是氢或C1－C30－烷基，优选C1－C18－烷基，a是0或1，b、c和d是0、1或2，e是0或1，条件是，b和c不同时为0。
Description
本发明涉及部分氟化的化合物作为滑雪板用润滑剂的用途。
使用滑雪板蜡是为了改善滑雪板的润滑性能。传统的滑雪板蜡一般包含高分子量的烃，如石蜡、脂肪酸、脂肪酸酯和脂肪醇，或其混合物和类似化合物。某些氟化的化合物已被证明是十分有效的滑雪板蜡，其特别用于高效体育运动中。氟化蜡的高有效性的原因是，滑雪板上涂有具有十分低的表面张力的氟化表面，由此大大减少了摩擦。通过涂覆含氟化学品使得例如聚乙烯的表面张力(31dyn/cm)可降低至6-18dyn/cm的值。对于由完美取向的CF3-基团构成的表面，达到6dyn/cm的值。
已经知道一些能够用作滑雪板用润滑剂的氟化化合物。WO 89/10950描述了例如向未氟化的滑雪板蜡中加入PTFE-微细粉末。PTFE的分子量优选为50000-400000g/mol且其粒子尺寸小于15μm。在EP 0132879中描述了式F(CF2)nF的长链金氟化烷烃的合成方法，以及其作为表面用润滑剂的用途。在EP 0444752中描述了通式F(CF2)n-(CH2)mH(其中n＝3-15，m＝5-23)的氟化二嵌段化合物作为滑雪板蜡的用途。这些化合物显示出的优点是，它们通过烃嵌段而与未氟化的石蜡-蜡相容。DE 4139765描述了式F(CF2)n-CH＝CH2的氟化烯烃的低聚物。该产物可通过已知烯烃的自由基低聚反应来制备，并且适用作各种表面用的润滑油和润滑剂。在US 5502225和DE 10029623中描述了含氟低聚物氨基甲酸酯，其通过作为主要成分的无氟异氰酸酯和氟化醇的加成反应而获得。EP 0421303描述了部分氟化的聚丙烯酸酯的应用。其是通过氟化的丙烯酸酯例如丙烯酸-2-全氟烷基乙基酯与未氟化的单体例如长链脂肪醇丙烯酸酯进行自由基共聚反应而制备。另外，滑雪板蜡可被提供有各种添加剂，以防止由摩擦产生的静电带电，该带电可能导致水膜附着。例如，CH 660018描述了例如石墨用于提高电导率的用途。
现已发现，某些部分氟化的化合物令人意外地同样能够用作滑雪板蜡。这些化合物是指一个或多个全氟烷基与一个无氟的烷基或芳基的偶联产物。该偶联产物可以除了由以醚键形式的氧原子以外，仅仅由元素氟、碳和氢构成。如果不含醚键，则所述无氟的烷基或芳基必须具有至少一个单环或多环结构单元，其可以是饱和的、不饱和的、芳族的，可能为支链的和单或双官能的。
本发明的目的是提供一种用于固体表面的润滑剂，其含有式1的部分氟化的化合物：
RF-(A)a-(O)b-(B)c-(D)d-(RF)e (1)
其中，
RF是式F(CF2)n-的全氟化基团，
n是1-20的数，
A是C1-C30-亚烷基，优选C1-C18-亚烷基，
B是具有6-14个碳原子的亚芳基，或者具有3-30个，优选3-18个碳原子的饱和或不饱和的单环或多环烃，
D是氢，或C1-C30-烷基，优选C1-C18-烷基，
a是0或1，
b、c和d是0、1或2，e是0或1，条件是，b和c不同时为0。
优选，上述式的化合物是这样的化合物：其中a＝1，b＝0，c＝1，d＝1，D＝H和e＝0，其中其余的符号具有上述含义。
原则上，可采用多种方式合成上式的化合物。最常见的是，全氟烷基碘化物在烯烃双键上加成，例如以自由基或金属催化方式；以及全氟烷基碘化物在芳族体系上的取代反应，其例如以金属催化方式来实施。当然，这里没提到但本领域技术人员充分已知的其他方式，也可能将全氟烷基与无氟的化合物连接。
令人意外的是，现已发现，上述化合物优异地适合于涂覆滑雪板以改善润滑性能。该效果可能归因于：氟基向空气中取向，并且由于这样构成的CF3-表面涂层，形成了具有表面张力很低且同时润滑性能很好的低能量表面。
根据雪以及天气条件而定，对于滑雪板蜡的物理和化学性能的要求显著不相同。通过适当选择氟化和无氟的活性物质部分，可以容易地在宽范围内改变所述物理-化学性能，并且适应各种需要。也可以使用两种或更多种所述活性物质的组合。≥C8F17的长链全氟烷基提高了例如活性物质的硬度。此外，由于存在的无氟部分，可获得与无氟滑雪板蜡的可溶混性或相容性。
可按本身已知的方式将所述化合物施涂到滑雪板的滑移面上，例如通过将这些化合物用热铁熔融，因此它们是以固体形式存在，并将其涂刷到滑雪板上来进行。对此另选地，可将在一种或多种有机溶剂中的溶液形式的所述化合物，优选以浓度为0.5-5％，或以固体形式施涂到滑雪板上。如果将蜡以溶液形式使用，则必须根据氟含量而定来选择适当的溶剂。对于高氟含量，可能要求使用氟化的溶剂，例如全氟己烷、1H-全氟己烷或氟利根型。对于低氟含量，未氟化的溶剂也适合，例如乙酸乙酯、乙酸丁酯或THF。也可使用两种或更多种溶剂的混合物。另外，可能使用悬浮液或分散体形式的活性物质。所述氟化的化合物可单独结合，或者以与其他氟化的或未氟化的滑雪板蜡的混合形式结合。
所述氟化的活性物质不仅适合作为滑雪板蜡，而且适合用于涂覆各种类型例如金属、塑料和玻璃的表面。通过涂覆，向相应的表面上施涂疏水和疏油的膜，其大大降低了摩擦。
实施例
合成
通过将全氟烷基碘化物在C-C双键上进行自由基加成反应，随后进行加氢脱卤化反应来合成化合物1-6，其按照反应流程图I以及以下的通用规程来进行。
反应流程图I：
用于合成化合物1-6的通用规程：
将全氟烷基碘化物和烯烃组分以摩尔比例为1∶1与5摩尔％的过碳酸盐或过氧化物自由基引发剂(例如二月桂基过氧化物)在100-110℃下反应2小时。然后再加入5摩尔％的自由基引发剂，并再在100-110℃下反应2小时。在冷却至室温后，加入1.5倍质量的异丙醇、0.5倍质量的乙酸以及150摩尔％锌粉，并搅拌1小时。然后在回流条件下再反应3小时。在过滤出不溶解的部分后抽出溶剂，并在高真空下将残留物中未转化的反应物和副产物去除。产物的纯度为85-95％。
化合物7的合成
根据“J.Org.Chem.6，(2002)，第7185-7192页”中的操作规程，通过将2摩尔RFI和1摩尔联苯用铜在作为溶剂的DMSO中进行偶合而制备化合物7。
化合物8的合成
根据“Organikum，Wiley-VCH，第21版，2001，第375页”中的操作规程，通过将全氟烷基丙基氯(通过3-全氟烷基-1-丙醇和亚硫酰氯的反应制备)和癸基苯用氯化铝催化的Friedel-Crafts烷基化反应而制备化合物8。
化合物9的合成
按照依据“Organikum，Wiley-VCH，第21版，2001，第239页”的操作规程，通过甲苯磺酸全氟烷基丙基酯(通过3-全氟烷基-1-丙醇与对甲苯磺酰氯反应制备)和十二烷基苯酚在丙酮中用碳酸钾进行反应而制备化合物9。
实施例
化合物1：
由RFI(RF＝F(CF2)n，n＝63％10，30％12，7％≥14)和苯乙烯制得的产物
1 RF-CH2-CH2-C6H5
化合物2：
由RFI(RF＝F(CF2)n，n＝63％10，30％12，7％≥14)和4-苯基-1-丁烯制得的产物
2 RF-(CH2)4-C6H5
化合物3：
由RFI(RF＝F(CF2)n，n＝8)和3-丁烯基-十二烷基醚制得的产物
3 RF-(CH2)4-O-C12H25
化合物4：
由RFI(RF＝F(CF2)n，n＝63％10，30％12，7％≥14)和β-蒎烯制得的产物
4 RF-β-蒎烯
化合物5：
由RFI(RF＝F(CF2)n，n＝63％10，30％12，7％≥14)和环辛烯制得的产物
5 RF-环辛烯
化合物6：
由RFI(RF＝F(CF2)n，n＝8)和3-丁烯基-(十二烷基苯基)醚制得的产物
6 RF-(CH2)4-O-C6H4-C12H25
化合物7：
由2摩尔RFI(RF＝F(CF2)n，n＝8)和1摩尔联苯制得的产物
7 RF-C6H4-C6H4-RF
化合物8：
由全氟烷基丙基氯和癸基苯(RF＝F(CF2)n，n＝7％6，63％8，28％10，2％≥12)制得的产物
8 RF-(CH2)3-C6H4-C10H21 
化合物9：
由甲苯磺酸全氟烷基丙基酯和十二烷基苯酚(RF＝F(CF2)n，n＝7％6，63％8，28％10，2％≥12)制得的产物
9 RF-(CH2)3-O-C6H4-C12H25 
Claims (5)
1.用于固体表面的润滑剂，其包含式1的部分氟化的化合物：
RF-(A)a-(O)b-(B)c-(D)d-(RF)e (1)
其中
RF是式F(CF2)n-的全氟化基团，
n是1-20的数，
A是C1-C30-亚烷基，优选C1-C18-亚烷基，
B是具有6-14个碳原子的亚芳基，或者是具有3-30个，优选3-18个碳原子的饱和或不饱和的单或多环烃，
D是氢，或C1-C30-烷基，优选C1-C18-烷基，
a是0或1，
b、c和d是0、1或2，e是0或1，条件是，b和c不同时为0。
2.权利要求1的润滑剂，其特征在于，其包含式1的化合物，其中a＝1，b＝0，c＝1，d＝1，D＝H和e＝0，且其余的符号具有权利要求1中所述的含义。
3.权利要求1的润滑剂，其特征在于，其是滑雪板蜡。
4.权利要求1的润滑剂，其特征在于，该润滑剂以固体、溶液或分散体的形式存在。
5.权利要求1的润滑剂，其特征在于，该润滑剂含有其他氟化或未氟化的润滑剂。
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
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| DE10317198.3 | 2003-04-15 | ||
| DE10317198A DE10317198A1 (de) | 2003-04-15 | 2003-04-15 | Gleitmittel für feste Oberflächen |
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| Country | Link |
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| US (1) | US20060270570A1 (zh) |
| EP (1) | EP1615976B1 (zh) |
| JP (1) | JP2006523738A (zh) |
| CN (1) | CN1809621A (zh) |
| AT (1) | ATE377637T1 (zh) |
| DE (2) | DE10317198A1 (zh) |
| ES (1) | ES2294491T3 (zh) |
| NO (1) | NO20055169L (zh) |
| WO (1) | WO2004092291A1 (zh) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102154052A (zh) * | 2011-01-29 | 2011-08-17 | 锦州惠发天合化学有限公司 | 一种氟脂的制备方法 |
| CN107653041A (zh) * | 2017-09-29 | 2018-02-02 | 上海永玺环境科技有限公司 | 一种陆地冰上运动赛道润滑剂及其应用 |
| CN108350112A (zh) * | 2015-11-20 | 2018-07-31 | 旭硝子株式会社 | 制造碘原子含量得以减少的含氟化合物的方法 |
| CN112029419A (zh) * | 2020-09-15 | 2020-12-04 | 河北体育学院 | 一种通用型滑雪板助滑蜡 |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE102004039381A1 (de) * | 2004-08-13 | 2006-02-23 | Holmenkol Sport-Technologies Gmbh & Co. Kg | Gleitmittel für Sportgeräte |
| DE102009054802B4 (de) | 2009-12-16 | 2017-08-17 | Holmenkol Gmbh | Verwendung von Fettalkoholethern als Gleitmittel für Sportgeräte, Gleitmittelzusammensetzung und Verfahren zur Beschichtung eines Sportgeräts |
| DE102010001861A1 (de) | 2010-02-11 | 2011-08-11 | Holmenkol Ag, 71254 | Pulverförmige Gleitmittel für Sportgeräte |
| US20200255684A1 (en) * | 2017-08-21 | 2020-08-13 | Drake Powderworks, Llc | Lubricious coatings for skis and snowboards and related methods of use |
| EP3927546A4 (en) * | 2019-02-20 | 2022-11-16 | Drake Powderworks, LLC. | LUBRICATING COATINGS FOR SKIS AND SNOWBOARDS AND SYSTEMS AND METHODS OF USE THEREFOR |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
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| DD246788A1 (de) * | 1986-03-18 | 1987-06-17 | Adw Ddr Inst Kosmosforschung | Verfahren zur schmierung bei tiefen temperaturen |
| US5118879A (en) * | 1989-02-27 | 1992-06-02 | Nippon Oil And Fats Co., Ltd. | Fluoroalkyl derivative and process for preparing the same |
| US5131674A (en) * | 1989-09-29 | 1992-07-21 | Asahi Glass Company Ltd. | Lubricant for skis |
| US5914298A (en) * | 1996-08-13 | 1999-06-22 | Karydas; Athanasios | Fluorinated lubricants for polyethylene snow sliders |
| US5839311A (en) * | 1996-09-17 | 1998-11-24 | Minnesota Mining And Manufacturing Company | Composition to aid in the forming of metal |
-
2003
- 2003-04-15 DE DE10317198A patent/DE10317198A1/de not_active Withdrawn
-
2004
- 2004-04-08 ES ES04726455T patent/ES2294491T3/es not_active Expired - Lifetime
- 2004-04-08 CN CN200480009967.0A patent/CN1809621A/zh active Pending
- 2004-04-08 US US10/553,217 patent/US20060270570A1/en not_active Abandoned
- 2004-04-08 JP JP2006505061A patent/JP2006523738A/ja not_active Withdrawn
- 2004-04-08 DE DE502004005433T patent/DE502004005433D1/de not_active Expired - Fee Related
- 2004-04-08 AT AT04726455T patent/ATE377637T1/de not_active IP Right Cessation
- 2004-04-08 WO PCT/EP2004/003755 patent/WO2004092291A1/de active IP Right Grant
- 2004-04-08 EP EP04726455A patent/EP1615976B1/de not_active Expired - Lifetime
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Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102154052A (zh) * | 2011-01-29 | 2011-08-17 | 锦州惠发天合化学有限公司 | 一种氟脂的制备方法 |
| CN102154052B (zh) * | 2011-01-29 | 2013-07-17 | 锦州惠发天合化学有限公司 | 一种氟脂的制备方法 |
| CN108350112A (zh) * | 2015-11-20 | 2018-07-31 | 旭硝子株式会社 | 制造碘原子含量得以减少的含氟化合物的方法 |
| CN107653041A (zh) * | 2017-09-29 | 2018-02-02 | 上海永玺环境科技有限公司 | 一种陆地冰上运动赛道润滑剂及其应用 |
| CN107653041B (zh) * | 2017-09-29 | 2020-07-10 | 上海永玺环境科技有限公司 | 一种陆地冰上运动赛道润滑剂及其应用 |
| CN112029419A (zh) * | 2020-09-15 | 2020-12-04 | 河北体育学院 | 一种通用型滑雪板助滑蜡 |
Also Published As
| Publication number | Publication date |
|---|---|
| NO20055169L (no) | 2005-11-03 |
| US20060270570A1 (en) | 2006-11-30 |
| ES2294491T3 (es) | 2008-04-01 |
| DE502004005433D1 (de) | 2007-12-20 |
| DE10317198A1 (de) | 2004-11-04 |
| JP2006523738A (ja) | 2006-10-19 |
| EP1615976B1 (de) | 2007-11-07 |
| WO2004092291A1 (de) | 2004-10-28 |
| ATE377637T1 (de) | 2007-11-15 |
| EP1615976A1 (de) | 2006-01-18 |
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