TWI664213B - 聚氨酯燒焦抑制劑 - Google Patents
聚氨酯燒焦抑制劑 Download PDFInfo
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- TWI664213B TWI664213B TW104113352A TW104113352A TWI664213B TW I664213 B TWI664213 B TW I664213B TW 104113352 A TW104113352 A TW 104113352A TW 104113352 A TW104113352 A TW 104113352A TW I664213 B TWI664213 B TW I664213B
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- TW
- Taiwan
- Prior art keywords
- tert
- derived
- butyl
- weight
- hydroquinone
- Prior art date
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- 239000004814 polyurethane Substances 0.000 title claims description 18
- 239000003112 inhibitor Substances 0.000 title claims description 12
- 229920002635 polyurethane Polymers 0.000 title claims description 9
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- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 claims abstract description 28
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- CZNRFEXEPBITDS-UHFFFAOYSA-N 2,5-bis(2-methylbutan-2-yl)benzene-1,4-diol Chemical group CCC(C)(C)C1=CC(O)=C(C(C)(C)CC)C=C1O CZNRFEXEPBITDS-UHFFFAOYSA-N 0.000 claims description 6
- 229940033628 2,5-di-tert-pentylhydroquinone Drugs 0.000 claims description 6
- 229910052760 oxygen Inorganic materials 0.000 claims description 5
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- 239000001301 oxygen Substances 0.000 claims description 4
- 229910052794 bromium Inorganic materials 0.000 claims description 3
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- 229910052801 chlorine Inorganic materials 0.000 claims description 3
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 3
- 229910052731 fluorine Inorganic materials 0.000 claims description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims description 3
- 229910052740 iodine Inorganic materials 0.000 claims description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 3
- XCPFSALHURPPJE-UHFFFAOYSA-N (3,5-ditert-butyl-4-hydroxyphenyl) propanoate Chemical compound CCC(=O)OC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 XCPFSALHURPPJE-UHFFFAOYSA-N 0.000 claims 2
- 230000002401 inhibitory effect Effects 0.000 claims 2
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- FXNDIJDIPNCZQJ-UHFFFAOYSA-N 2,4,4-trimethylpent-1-ene Chemical compound CC(=C)CC(C)(C)C FXNDIJDIPNCZQJ-UHFFFAOYSA-N 0.000 description 6
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- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 5
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- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 4
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- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 description 3
- 125000003118 aryl group Chemical group 0.000 description 3
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- KGRVJHAUYBGFFP-UHFFFAOYSA-N 2,2'-Methylenebis(4-methyl-6-tert-butylphenol) Chemical compound CC(C)(C)C1=CC(C)=CC(CC=2C(=C(C=C(C)C=2)C(C)(C)C)O)=C1O KGRVJHAUYBGFFP-UHFFFAOYSA-N 0.000 description 2
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- JZODKRWQWUWGCD-UHFFFAOYSA-N 2,5-di-tert-butylbenzene-1,4-diol Chemical compound CC(C)(C)C1=CC(O)=C(C(C)(C)C)C=C1O JZODKRWQWUWGCD-UHFFFAOYSA-N 0.000 description 2
- BVUXDWXKPROUDO-UHFFFAOYSA-N 2,6-di-tert-butyl-4-ethylphenol Chemical compound CCC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 BVUXDWXKPROUDO-UHFFFAOYSA-N 0.000 description 2
- SLUKQUGVTITNSY-UHFFFAOYSA-N 2,6-di-tert-butyl-4-methoxyphenol Chemical compound COC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 SLUKQUGVTITNSY-UHFFFAOYSA-N 0.000 description 2
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- 238000009835 boiling Methods 0.000 description 1
- OCWYEMOEOGEQAN-UHFFFAOYSA-N bumetrizole Chemical compound CC(C)(C)C1=CC(C)=CC(N2N=C3C=C(Cl)C=CC3=N2)=C1O OCWYEMOEOGEQAN-UHFFFAOYSA-N 0.000 description 1
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- 229910052736 halogen Inorganic materials 0.000 description 1
- 230000036541 health Effects 0.000 description 1
- 125000005842 heteroatom Chemical group 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 239000011159 matrix material Substances 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
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- DUWWHGPELOTTOE-UHFFFAOYSA-N n-(5-chloro-2,4-dimethoxyphenyl)-3-oxobutanamide Chemical compound COC1=CC(OC)=C(NC(=O)CC(C)=O)C=C1Cl DUWWHGPELOTTOE-UHFFFAOYSA-N 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
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- 239000002245 particle Substances 0.000 description 1
- 150000002978 peroxides Chemical class 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-M phenolate Chemical compound [O-]C1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-M 0.000 description 1
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- 229910052698 phosphorus Inorganic materials 0.000 description 1
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- 238000001556 precipitation Methods 0.000 description 1
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- 230000005855 radiation Effects 0.000 description 1
- 238000007348 radical reaction Methods 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 239000005060 rubber Substances 0.000 description 1
- 238000012216 screening Methods 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 230000006641 stabilisation Effects 0.000 description 1
- 238000011105 stabilization Methods 0.000 description 1
- 238000007655 standard test method Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- KKEYFWRCBNTPAC-UHFFFAOYSA-L terephthalate(2-) Chemical compound [O-]C(=O)C1=CC=C(C([O-])=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-L 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- AOBORMOPSGHCAX-DGHZZKTQSA-N tocofersolan Chemical compound OCCOC(=O)CCC(=O)OC1=C(C)C(C)=C2O[C@](CCC[C@H](C)CCC[C@H](C)CCCC(C)C)(C)CCC2=C1C AOBORMOPSGHCAX-DGHZZKTQSA-N 0.000 description 1
- 229960000984 tocofersolan Drugs 0.000 description 1
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- 239000002446 δ-tocopherol Substances 0.000 description 1
Classifications
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- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J9/00—Working-up of macromolecular substances to porous or cellular articles or materials; After-treatment thereof
- C08J9/0014—Use of organic additives
- C08J9/0023—Use of organic additives containing oxygen
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- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
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- C08G65/02—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
- C08G65/26—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers and other compounds
- C08G65/2603—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers and other compounds the other compounds containing oxygen
- C08G65/2606—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers and other compounds the other compounds containing oxygen containing hydroxyl groups
- C08G65/2612—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers and other compounds the other compounds containing oxygen containing hydroxyl groups containing aromatic or arylaliphatic hydroxyl groups
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- C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
- C08G65/02—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
- C08G65/26—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers and other compounds
- C08G65/2603—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers and other compounds the other compounds containing oxygen
- C08G65/2615—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers and other compounds the other compounds containing oxygen the other compounds containing carboxylic acid, ester or anhydride groups
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- C08G65/02—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
- C08G65/32—Polymers modified by chemical after-treatment
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Abstract
一種抑制聚氨酯泡棉組成物燒焦的添加組成物。此添加組成物包括一衍生的對苯二酚；一衍生的內酯；及一衍生的酚醛化合物。一種含有此添加組成物的聚氨酯泡綿組成物。
Description
本發明係有關於抑制燒焦的聚氨酯泡綿(polyurethane foam)添加劑。
本發明係有關於一種抑制燒焦的聚氨酯泡綿添加劑。聚氨酯塊狀泡綿的製造包括一劇烈的發熱反應。延長的補充反應熱暴露會導致化學改變，造成生產泡綿塊的內部變黑，其為燒焦。為了防止燒焦，製造業會添加抗氧化混合物，其一般為燒焦抑制劑。燒焦抑制劑可透過複合犧牲反應以降低因熱誘導而變黑的傷害。因此，燒焦抑制劑可有效地減少產物損失。
在聚氨酯塊狀泡綿的製造中，劇烈的發熱反應被發現會導致內部變色1。一般已知多元醇及二-異氰酸酯縮合(膠體)反應及“下列反應”的結果如下2。
第1圖、式1(上方)異氰酸酯的水解，式2(下方)異氰酸酯進行胺縮合以生成尿素。
製造業已計算出對應於聚氨酯泡綿基質中形成之
成分的反應熱：氨基甲酸乙酯(urethane)為約24kcal/mol，尿素為約47kcal/mol。視覺上，泡綿表面上的暗黃色汙點(discoloration)已知為因未消散的熱造成生產泡綿塊內部燒焦。已有科學家顯示複合的自由基反應會導致燒焦程序3。間接測量到之降解效果顯示斷鍊及聚醚多元醇配方成分的氧化4。某些配方，如本發明配方可降低斷鍊及一般的PUR泡綿之化學改變。
環境因子與泡綿汙點
氮氧化物所導致的PUR泡綿汙點
聚氨酯泡綿的製備有關於PUR泡綿降解現象5。一般來說，熱、光、光氧化及NOx煙氣(fume)(主要為一氧化氮(NO)及二氧化氮(NO2))在泡綿表面產生黃或粉紅色(第2圖)6。
第2圖、丙烷燃燒
關於氮氧化物煙氣，汙點與倉庫中所增加的NOx量有極大的關係。已有文獻探討季節性的影響。在寒冷的月份裡，若倉庫的通風不佳，丙烷燃料堆高機及煤氣加熱爐會造成NOx煙氣濃度大量的累積7。此影響是可充分理解的。Tompkins與Smith說明倉庫中的多種逸散排放，如一氧化碳、二手煙、新產品的化學廢氣及廢氣收集8。在溫暖的月份裡，工廠運作
與汽車的廢氣導致大氣中NOx濃度增加而造成汙點9。溫暖月份具有一額外會影響NOx煙氣濃度與其化學特性的特點。依據一些大氣研究，NOx持續與氧及水汽反應會形成硝酸氣霧10。顯然地，可在高溼度環境的水合形式中發現硝酸。在一研究顯示，比起低濕度環境，玻璃纖維中的硝酸粒子量在高濕度環境會大量增加11。因此，含有豐富NOx煙氣的倉庫空氣會形成酸性氣霧。NOx煙氣的化學特性複雜，但其對泡綿成分及顏色之影響為廣泛被接受的12、13。相較於其它已知抗氧化燒焦抑制劑，本發明可降低儲存於倉庫之PUR泡綿中可普遍觀察到的汙點。
PUR泡綿的螢光及UV誘發之汙點
已有許多相關的實驗顯示PUR如何可能與從光-氧化效應所產生的顏色有關14。Chandra揭露短波長(<340nm)射線可促使Photo-Fries機制，其中氨基甲酸酯鍵可被破壞且再連結至芳香環，釋放自由的NH2。在較長波長上，顏色物質源自於過氧化氫反應。根據Noack與Schwetlick，所發現的黃化為芳香環上暴露之胺官能基氧化的結果(第3圖)。
第3圖、PUR中無胺TDI片段的光-氧化
以MDI為基礎的(MDI-based)聚氨酯同樣經由2步驟途徑透過去除氫原子，接著形成過氧化物獲得醌(quinone)類15。泡綿組成物中的其它成份可能有助於產生顏色。例如，
BHT與烷基二苯胺已被報導在暴露於氮氧化物中會形成染色的醌化合物(第19圖)1。相較於其他抗氧化燒焦抑制物，本發明延遲第3圖中的轉換，或其本身較不助於光-氧化誘導之色體。
源自聚氨酯泡綿的FOG及VOC逸散
全球對於室內(住家、車輛、工作場所)的空氣品質擔憂日益增加，進而對特定潛在有害的揮發氣體物質立法管制。對應的策略為，聚氨酯泡綿部門，包含所有添加物質的供應商，已朝減少或去除不符合規定的產品之策略方向前進。對於汽車內部，已開發一特定測試來計算塑膠、橡膠及聚氨酯物質的總揮發物含量。目前德國汽車協會可接受的方法為VDA278，其採用一種熱脫附(thermodesorption)GC分析法，來偵測有機揮發物含量(VOC)及汽車內飾材料的霧化可能性16。此方法可測量出高達n-C20的有機揮發物(樣品於90℃下30分鐘的脫附)，以及n-C16至n-C32的半揮發性與重化合物(FOG值)(樣品於120℃下60分鐘的脫附)。接著，偵測值依據產品規格書進行比較，來判定合格或不合格。重量法也可被使用作為篩選工具，其將用以分析此述之有機液體的揮發性特徵17。
本發明係有關於用於製備聚氨酯泡綿之液體添加混合組成物，此添加物包括A：衍生的對苯二酚(derivatized hydroquinones)；B：衍生的內酯(lactone)；以及
C：衍生的酚醛化合物(phenolic compound)。
衍生的對苯二酚(A)部分擇自於下列化合物：二-叔-丁基-對苯二酚(di-tert-butyl-hydroquinone,DTBHQ)、t-丁基對苯二酚(TBHQ)、2-甲基-5-異丙基對苯二酚以及較佳化合物2,5-二-叔-戊基-對苯二酚(DTAHQ)；美國專利第2758119號所揭露的烷基化對苯二酚單縮水甘油醚於此併入作為參考；美國專利第4209648號所揭露的單辛基化對苯二酚於此併入作為參考；藉由一含有對苯二酚與擇自於壬烯及2,2,4-三甲基-1-戊烯的烯烴的組合，於65℃至低於烯烴沸點的溫度，在Friedel-Crafts催化劑存在下，進行反應以製備對苯二酚產品；烯烴與對苯二酚的莫耳比為1：1至10：1，當烯烴為壬烯，以及為1.5：1至3：1，當烯烴為2,4,4-三甲基-1-戊烯，如美國專利第4209648號所示，相關內容於此併入作為參考；以及前述之任一組合。
衍生的內酯化合物(B)部分係擇自於內酯穩定劑或其混合物，如美國專利第7390912與7601853號，以及美國專利公開號20060135792所述，其於此內容併入作為參考，且較佳為市售產品，如Milliguard®AOX-1。內酯穩定劑通常為聚合或寡聚內酯抗氧化劑，例如，聚(氧化烯)(poly(oxyalkylene))鏈取代之3-芳基苯並呋喃酮，或聚(己內酯)鏈取代之3-芳基苯並呋喃酮。
較佳之內酯如美國專利第7390912號所述之聚內
酯化合物。
其中R1與R3獨立地擇自於下列所組成之族群：H、F、Cl、Br、I、C1-C20烷基、C1-C20環烷基、C1-C20烷氧基、C7-C20苯烷基及苯基；q為1至20之間的正整數，且t為0至20之間的正整數，且q+t等於或大於3。
衍生的酚醛化合物(C)通常包括一第4位置經脂肪族、芳香或脂肪族-芳香基結構取代的(2,6-二-叔-丁基)苯酚，選擇性地具有雜原子O、N、S與P之組合；及其混合物。此類化合物的代表例子包括，但不限於：2,6-二-叔-丁基-4-壬基酚、2,4-二辛基甲硫基-6-甲基苯酚，4,6-雙(辛基甲硫基)-o-甲酚、異十三烷基-3-(3,5-二-叔-丁基-4-羥苯基)丙酸酯、異-辛基-3-(3,5-二-叔-丁基-4-羥苯基)丙酸酯，其它許多固態或液態形式之酚醛也可能混合或單獨使用於組成物中，包括2,6-二-叔-丁基-4-甲基苯酚、2-叔-丁基-4,6-二甲基苯酚、2,6-二-叔-丁基-4-乙基-苯酚、2,6-二-叔-4-n-丁基苯酚、2,6-二-叔-丁基-4-異丁基苯酚、2,6-二環戊基-4-甲基苯酚、2-(α-甲基環己基)-4,6-二甲基苯酚、2,6-二十八基-4-甲基苯酚、2,4,6-三
環己基苯酚、2,6-二-叔-4-丁基-甲氧甲基苯酚、直鏈或分支狀側鏈壬基酚，例如2,6-二-壬基-4-甲基苯酚、2,4-二甲基-6-(1’-甲基十一-1’碳烯)苯酚、2,4-二甲基-6-(1’-甲基十七-1’碳烯)苯酚、2,4-二甲基-6-(1’-甲基十三-1’碳烯)苯酚、2,4-二辛基甲硫基-6-叔-丁基苯酚、2,4-二辛基甲硫基-6-叔-丙基苯酚、2,4-二辛基甲硫基-6-乙基苯酚、2,6-二-十二烷基甲硫基-4-壬基苯酚、2,6-二-叔-丁基-4-甲氧基苯酚、2,5-二-叔-丁基苯二酚、2,5-二-叔-戊基氫-醌、2,6-二苯基-4-十八烷氧基苯酚、2,6-二-叔-丁基氫醌、2,5-二-叔-丁基-4-羥苯甲醚、3,5-二-叔-丁基-4-羥苯甲醚、3,5-二-叔-丁基-4-羥苯基硬酯酸、二(3,5-二-叔-丁基-4-羥苯基)己二酸、α-生育酚、β-生育酚、γ-生育酚、δ-生育酚、2,2’-亞甲基二(6-叔-丁基-4-甲基苯酚)、2,2’-亞甲基二(6-叔-丁基-4-乙基苯酚)、2,2’-亞甲基二[4-甲基-6-(α-甲基環己基)苯酚]、2,2’-亞甲基二[4-甲基-6-環己基苯酚)]、2,2’-亞甲基二(6-壬基-4-甲基苯酚)、2,2’-亞甲基二(4,6-二-叔-丁基苯酚)、2,2’-亞乙基二(4,6-二-叔-丁基苯酚)、2,2’-亞乙基二(6-叔-丁基-4-異丁基苯酚)、2,2-亞甲基二[6-(α-甲基芐基)-4-壬基-苯酚]、2,2’-亞甲基二[6-(α,α-二甲基芐基)-4-壬基苯基]、4,4’-亞甲基二(2,6-二-叔-丁基苯酚)、4,4’-亞甲基二(6-叔-丁基-2-甲基苯酚)、1,1-二(5-叔-丁基-4-羥-2-甲基苯基)丁烷、2,6-二(叔-丁基-5-甲基-2-羥芐基)-4-甲基-苯酚、1,1,3-三(5-叔-丁基-4-羥-2-甲基苯基)丁烷、1,1-二(5-叔-丁基-4-羥-2-甲基-苯基)3-n-十二烷基巰基丁烷、乙烯乙二醇二[3,3-二(3’-叔-丁基-4-羥苯基)丁酸]、二(3-叔-丁基-4-羥-5-甲基
-苯基)二環戊二烯、二[2-(3’-叔-丁基-2’-羥-5’-甲基苄基)-6-叔-丁基-4-甲基苯基]對苯二甲酸酯、1,1-二(3,5-二甲基-2-羥苯基)丁烷、2,2-二(3,5-二-叔-丁基-4-羥苯基)丙烷、2,2-二(5-叔-丁基-4-羥2-甲基苯基)-4-n-十二烷基巰基丁烷、1,1,5,5-四-(5-叔-丁基-4-羥-2-甲基苯基)戊烷、β-(3,5-二-叔-丁基-4-羥苯基)-丙酸與單或多元醇的酯，如甲醇、乙醇、n-辛醇、i-辛醇、十八醇、1,6-己二醇、1,9-壬二醇、乙二醇、1,2-丙二醇、新戊二醇、硫代二乙二醇、二甘醇、三乙二醇、新戊四醇、三(羥基乙基)異氰脲酸酯、N,N’-二(羥基乙基)草醯胺、3-硫基十一醇(3-thiaundecanol)、3-硫基十五醇(3-thiapentadecanol)、三甲基己二醇、三羥甲基丙烷、4-羥甲基-1-磷-2,6,7-三氧雜二環[2,2,2]辛烷；β-(5-叔-丁基-4-羥-3-甲基苯基)丙酸與單元或多元醇的酯，如甲醇、乙醇、n-辛醇、i-辛醇、十八醇、1,6-己二醇、1,9-壬二醇、乙二醇、1,2-丙二醇、新戊二醇、硫代二乙二醇、二甘醇、三乙二醇、新戊四醇、三(羥基乙基)異氰脲酸酯、N,N’-二(羥基乙基)草醯胺、3-硫基十一醇(3-thiaundecanol)、3-硫基十五醇(3-thiapentadecanol)、三甲基己二醇、三羥甲基丙烷、4-羥甲基-1-磷-2,6,7-三氧雜二環[2,2,2]辛烷；3,9-二[2-{3-(3-叔-丁基-4羥-5-甲基苯基)丙醯氧基}-1,1-二甲基乙基]-2,4,8-10-四雜螺[5.5]十一烷、β-(3,5-二環己基-4-羥苯基)丙酸與單元或多元醇的酯，如甲醇、乙醇、辛醇、十八醇、1,6-己二醇、1,9-壬二醇、乙二醇、1,2-丙二醇、新戊二醇、硫代二乙二醇、二甘醇、三乙二醇、新戊四醇、三(羥基乙基)異氰脲酸酯、N,N’-
二(羥基乙基)草醯胺、3-硫基十一醇(3-thiaundecanol)、3-硫基十五醇(3-thiapentadecanol)、三甲基己二醇、三羥甲基丙烷、4-羥甲基-1-磷-2,6,7-三氧雜二環[2,2,2]辛烷；3,5-二-叔-丁基-4-羥-苯基-醋酸與單元或多元醇的酯，如甲醇、乙醇、辛醇、十八醇、1,6-己二醇、1,9-壬二醇、乙二醇、1,2-丙二醇、新戊二醇、硫代二乙二醇、二甘醇、三乙二醇、新戊四醇、三(羥基乙基)異氰脲酸酯、N,N’-二(羥基乙基)草醯胺、3-硫基十一醇(3-thiaundecanol)、3-硫基十五醇、三甲基己二醇、三羥甲基丙烷、4-羥甲基-1-磷-2,6,7-三氧雜二環[2,2,2]辛烷；β-(3,5-二-叔-丁基-4-羥苯基)丙酸的醯胺，如N,N’-二(3,5-二-叔-丁基-4-羥苯基丙醯基)環己烷二醯胺、N,N’-二(3,5-二-叔-丁基-4-羥苯基丙醯基)環丙烷二醯胺、N,N’-二(3,5-二-叔-丁基-4-羥苯基丙醯基)醯肼、N,N’-二[2-3-[3,5-二-叔-丁基-4-羥苯基]丙醯氧基]乙基)草醯胺(Naugard®XL-1，Uniroyal)與其混合物。較佳化合物為異-辛基-3-(3,5-二-叔-丁基-4-羥苯基)丙酸酯及C-13至C-15醇酯-3-(3,5-二-叔-丁基-4-羥苯基)丙酸酯的混合物。
燒焦抑制物配方的較佳比例包括以下重量比例配方：約1-25%A組的對苯二酚，較佳約5-15%；約5-25%B組的內酯，如Milliguard®AOX-1；較佳為5-15%；約70-90% C組的酚醛化合物，較佳約75-85%。
配方在聚氨酯泡綿中的比例較佳為約0.001至
5pbw；更佳為約0.2-3.5pbw；最佳為約0.2-0.5pbw。
燒焦抑制劑配方的一例子，實施例1，包括約10%的2,5-二-叔-戊基-對苯二酚(A組)；約10%的市售聚合或寡聚內酯產品Milliguard®AOX-1，其認定為內酯混合物(B組)；以及約80%的異-辛基-3-(3,5-二-叔-丁基-4-羥苯基)丙酸酯(C組)。本發明說明書中所述之所有比例為重量百分比。
以下顯示一代表性的泡綿配方(表1，泡綿A)。一些例子亦採用依照非燃性阻燃劑之配方，證明新的混合物相對於傳統配方(表1，泡綿B)的效力。
檢測程序如下所示。
利用不同的抗氧化劑組製備泡綿，以評估新混合相較於“基準”的效力。
利用微波加熱蛋糕盒大小的泡綿，以評估燒焦特性。此盒狀泡綿以微波加熱8分鐘，或依日常情況所需-根據
濕度有時延長或縮短。(微波爐：通用電子家用微波爐；Mod.Num.JE1860GB001；KW：1.55；VAC/HZ：120/60.8min；在30%功率的微波中)。在微波爐中經短固化週期(2分鐘)後，在進行檢測內部燒焦區域前，將生產的泡綿冷卻至室溫。由各樣本切割出泡綿樣品以評估汙點。將經微波的泡綿之燒焦區域中的黑化程度定量評估。利用Technidyne Corp.Brightimeter Micro S4Mc收集δE值。
在聚氨酯泡綿配方中，檢測本發明混合物(表1)。
檢測包括3個市售產品，以其作為新混合物效力的基準(表2)。
實施例C3對應於本發明燒焦抑制劑之化合物B，且其為一市售混合物，供應商表示可參照US7,390,912B2，其為聚合或寡聚內酯抗氧化劑，已知為Milliguard®AOX-1，可購自Milliken Chemical.。
實施例C4為VANOX®液體燒焦抑制劑，可購自Vanderbilt Chemical,LLC，可參照US5219892，含有烷基化聯苯胺與一烷基化酚醛化合物，特別是(a)四[亞甲基(3,5-二-叔-丁基-4-羥氫化肉桂酸鹽)]甲烷，以及(b)二苯基胺與二異丁烯的反應產物，其中胺與二異丁烯的莫耳比為1：1.1至1：2.5。穩定劑組合物可包括一第3協同成份、吩噻嗪或其它吩
噻嗪的特定烷基衍生物。
實施例C5為一市售Irgastab®PUR68產品，可購自Ciba Specialty Chemicals，其被認為是依照美國專利第5356966號之教示，且應包括內酯衍生物及其他抗氧化劑，但不知確切的組成份。
實施例C6係由衍生苯酚異三癸基-3-(3,5-二-叔-丁基-4-羥苯基)丙酸酯(80%)及Milliguard®AOX-1內酯(實施例3C)(20%)組成。比較混合物採用近似於美國專利7247658(實施例4)所教示之成分的比例。
實施例C7係為衍生苯酚異-辛基-3-(3,5-二-叔-丁基-4-羥苯基)丙酸酯(9%)；二苯基胺與二異丁烯的反應產物，其中胺與二異丁烯的莫耳比例為1：1.1至1：2.5(14%)；市售聚合或寡聚內酯產品Milliguard®AOX-1(34%)與Songsorb®3260 2-(2’-羥-3’-t-丁基-5’-甲基苯基)-5-氯苯並三唑(43%)(Songwon生產，可購於Vanderbilt Chemicals,LLC)。比較混合物採用如美國專利7601853B2(添加組BB)所教示之成分的比例。
實施例8
實施例8包括2,5-二-叔-戊基-對苯二酚(10%)與市售聚合或寡聚內酯產品Milliguard®AOX-1(10%)，及C-13至C-15醇酯-3-(3,5-二-叔-丁基-4-羥苯基)丙酸酯(ANOX®13-15(Addivant USA,LLC),CAS：171090-93-0)的混合物。
如表2及2A所示，在相同添加量(0.2pbw)之泡
綿組成物中，，本發明實施例1有極小的汙點，如減少的dE測量值所示。
其它輪的檢測比較新混合物與2種內酯組成物，參照最相近的前案(US7,390,912B2)，其顯示新混合物(實施例1)較顯著地減少燒焦(表3)。發明人於此注意到實施例C7為一酚醛、烷基化二苯基胺、聚合內酯及苯並三唑的組合，其不會因混合形成液體混合物，與實施例1不同，其確實形成一液體-在商業應用上具高度理想特性。
其它組別證明新配方在不含阻燃劑下可持續減少
燒焦。應注意的是，新混合物的總重量低於現存的配方，帶依然顯示較低的燒焦(表4)。
氣體褪色測試
環境因子及泡綿汙點
泡綿製造業者發覺氮氧化物煙氣的影響，已公開資訊公告提醒使用者汙點的問題，且指出新產品可緩和此問題18。為模擬PUR泡綿暴露於NOx煙氣，開發一種氣體褪色(Gas Fade)檢測，使用第一簡單實驗設備來捕捉產生之燃燒煙氣，材料被暴露於此煙氣19。對此，製造業者開始提供煙氣腔室，其設置本生燈圍繞樣品轉盤。將樣本暴露於被捕捉的燃燒氣體一設定的時間20。在我們的評估中，將樣本置於腔室內，且使用比色測量定期檢測。
在此試驗中，檢測2個濃度，包括本發明混合物與傳統配方(C7)。在更高的濃度(3.5pbw)中，本發明混合物的汙點(dE=4.81)明顯地少於傳統配方(dE=7.05)，且在較低濃度(0.5pbw)中，也明顯優於傳統配方。應注意的是，所選擇的濃度(3.5pbw)引用於取得C7之專利中，因此可作
為實施例1的對照組(表5)。
比較實施例1與C4(酚醛/ADPA混合)的氣體褪色分析以及光褪色分析。
在2個工業配方上常用的濃度，對實施例1(本發明混合物)與一常用酚醛/ADPA混合物進行比較。此外，將配方以使用於PUR泡綿的阻燃劑(根據表1，泡綿A)進行修飾。Fyrol®HF-5與HF-4阻燃劑分別為專賣的磷酯混合物及非-鹵素磷酯，可購自ICL Industrial Products。顯示的數據超過試驗長度，其具有另人感興趣之處。本發明配方在不受阻燃劑影響的試驗過程(2小時)中，顏色產生較(表6)。
比較實施例1與C4(酚醛/ADPA混合)的光褪色分析。
最後，泡綿樣本暴露於一般螢光，且觀察6天。與ADPA/酚醛混合物(C4)相比，整個試驗期間本發明混合物在2個選擇的濃度上具有較少的汙點(表7)。
成分vs混合物的評估
為了證明本發明混合物比起單獨成分具有協同作用，分析實施例1中各個成分的燒焦效力。另外，也對生產的泡綿進行氣體褪色分析(表8)。使用2種工具來分析混合物的效力，包括算數平均及加權平均，依據混合物中特定成分的濃度計算加權平均。各成分具有各種程度的效力，由最深至最淺內部，如下：衍生的酚醛PH-1(23.24)>衍生的內酯AOX-1(8.88)>對苯二酚HQ-1(4.14)。假設各成分對混合物最終燒焦效力的影響相同，預測dE值為x□=12.53。假設各成分的影響是根據其於混合物中之重量，預測值為x□=26.64。事實上，混合物低於算數平均與加權平均，因此顯示具有協同作用(dE=5.47)。氣煙腔室結果顯示一類似的趨勢，但另人驚訝的是，汙點不但在預測的平均值最低，且更低於所有的偵測值(表8)，再次證明混合物具有協同作用。
配方調整
對混合物中成份的相對濃度進行調整及分析(表9)。在此一系列的實驗中，發現不論是增加內酯、對苯二酚或兩者的濃度，比起實施例1，大致上會增進燒焦效力(A-C)。酚醛的增加及內酯與對苯二酚的減少，相較於實施例1，會降低燒焦效力(D)。然而，對苯二酚濃度的增加會造成液體不穩定性，而在混合物製成後數日產生沉澱。成功的市售產品條件之一為儘可能地長時間維持液體狀，其意指某些調整的混合物較不佳。
揮發性考慮
如上所述，期望可降低聚氨酯泡綿中成分的揮發性。Gossner et al.說明“由文獻已知聚氨酯泡綿會逸散揮發性有機組成(VOC)，此逸散通常不恰當。此逸散可被(偵測)...”21。本發明可調整為使用較高分子量的烷基化酚醛化合物，其可能可降低化合物的揮發性。為證明此事，製備實施例8，除了置換為分子量較高的酚醛(C-13至C-15醇酯-3-(3,5-二-叔-丁基-4-羥苯基)丙酸酯(ANOX®13-15)的混合物)之外，其餘與實施例1相同。首先，實施例8經修飾混合物的效力類似實施例1(表10)。
對燒焦抑制劑組使用者較佳為調整配方以降低逸散或VOC。相較於實施例1，經調整組成物之實施例8在檢測時間中有較低揮發性。利用熱重量分析法(ASTM E2008)計算隨時間而產生的重量損失，顯示2種混合物具有顯著的差異(表11)。如期地，在整個試驗期間，較高的分子量成分有助於降低重量損失(實施例1 vs實施例8)。
評估檢測結果，如下所述
相較於單一成分，實施例1混合物在一相同的重量基礎上，具有更大程度的減少燒焦，證明一真實的協同作用。相較於使用內酯混合物的本發明組成物(實施例1)，US7,390,912 B2的內酯抗氧化劑(實施例C3)在減少燒焦的效果不佳。本發明混合物之其它抗氧化劑成分在減少燒焦的效果上同樣比混合物差(實施例1)。此外，如上所述，實施例C3(0.5pbw)中所測得的內酯電荷程度(charge level)遠大於實施例1(0.05pbw)的混合物的內酯程度(level)。關於揭露於“內酯”專利家族的前案C3，如C6及C7的其它混合物比起本發明混合物亦產生更多的燒焦。
實施例C5為一市售內酯組成物-儘管製造廠未揭示確切的配方。同樣，本發明配方(實施例1)在相同使用量下有較少的燒焦。
實施例1也不具有烷基化二苯基胺(使用於實施例C4)及其母起始原料二苯基胺。在許多產品中及歐洲，不可使用DPA 23。如此實施例1在促使燒焦減少的同時，亦降低對健康的影響。因此，本發明也包括一合併添加物配方的聚氨酯泡綿，其不具有，或實質上不具有二苯基胺。相較於烷基化二苯基胺混合物，如C4，本發明在暴露於NOx煙氣及常見螢光下時，亦較少產生顏色。
雖然實施例1證明本發明混合物在減少汙點上，比許多前案或市售組成物好，但其亦可經調整以減少在各種市場部門所擔心之可能的揮發性。
【參考文獻】
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Claims (8)
- 一種抑制聚氨酯海綿組成物燒焦的添加組成物，該添加組成物包括：大於5至約15重量%之一衍生的對苯二酚；約10-20重量%之一衍生的內酯；以及約70-80重量%之一衍生的酚醛化合物，其中該添加組成物實質上不具有二苯基胺。
- 如申請專利範圍第1項所述之抑制聚氨酯海綿組成物燒焦的添加組成物，其中該衍生的對苯二酚以約10重量%存在。
- 如申請專利範圍第1項所述之抑制聚氨酯海綿組成物燒焦的添加組成物，其中該衍生的對苯二酚為2,5-二-叔-戊基-對苯二酚；該衍生的內酯為：其中R1與R3獨立地擇自於下列所組成之族群：H、F、Cl、Br、I、C1-C20烷基、C1-C20環烷基、C1-C20烷氧基、C7-C20苯烷基及苯基；q為1至20之間的正整數，且t為0至20之間的正整數，且其中q+t等於或大於3；且該衍生的酚醛化合物為(a)異辛基-3-(3,5-二-叔-丁基-4-羥苯基)丙酸酯或(b)C-13至C-15醇酯-3-(3,5-二-叔-丁基-4-羥苯基)丙酸酯的混合物。
- 一種聚氨酯泡綿組成物，包括約0.001-5pbw的一燒焦抑制劑添加組成物，該添加組成物包括，佔總添加組成物重量為：大於5至約15重量%之一衍生的對苯二酚；約10-20重量%之一衍生的內酯；以及約70-80重量%之一衍生的酚醛化合物，其中該泡綿組成物實質上不具有二苯基胺。
- 如申請專利範圍第4項所述之聚氨酯泡綿組成物，其中該添加組成物以約0.2-3.5pbw存在。
- 如申請專利範圍第4項所述之聚氨酯泡綿組成物，其中該添加組成物以約0.2-0.5pbw存在。
- 如申請專利範圍第5項所述之聚氨酯泡綿組成物，其中該添加組成物包括：約10重量%之衍生的對苯二酚。
- 如申請專利範圍第4項所述之聚氨酯泡綿組成物，其中該衍生的對苯二酚為2,5-二-叔-戊基-對苯二酚；該衍生的內酯為：其中R1與R3獨立地擇自於下列所組成之族群：H、F、Cl、Br、I、C1-C20烷基、C1-C20環烷基、C1-C20烷氧基、C7-C20苯烷基及苯基；q為1至20之間的正整數，且t為0至20之間的正整數，且其中q+t等於或大於3；且該衍生的酚醛化合物為(a)異辛基-3-(3,5-二-叔-丁基-4-羥苯基)丙酸酯或(b)C-13至C-15醇酯-3-(3,5-二-叔-丁基-4-羥苯基)丙酸酯的混合物。
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| US20110046250A1 (en) * | 2007-07-06 | 2011-02-24 | Stowell Jeffrey K | Flame retardant composition and flexible polyurethane foam prepared therewith |
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- 2015-05-05 JP JP2016564234A patent/JP6548669B2/ja not_active Expired - Fee Related
- 2015-05-05 KR KR1020167030988A patent/KR20170032219A/ko unknown
- 2015-05-05 CA CA2945385A patent/CA2945385A1/en not_active Abandoned
- 2015-05-05 MX MX2016013633A patent/MX2016013633A/es unknown
- 2015-05-05 WO PCT/US2015/026808 patent/WO2015167856A1/en active Application Filing
- 2015-05-05 AU AU2015253576A patent/AU2015253576C1/en not_active Ceased
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Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS61130320A (ja) * | 1984-11-29 | 1986-06-18 | Daihachi Kagaku Kogyosho:Kk | 難燃性ポリウレタンフオ−ム組成物 |
| TW399079B (en) * | 1995-05-12 | 2000-07-21 | Ciba Sc Holding Ag | Polyether polyol and polyurethane compositions protected against oxidation and core scorching |
| CN101080451A (zh) * | 2004-12-17 | 2007-11-28 | 美利肯公司 | 内酯稳定组合物 |
| TW201132698A (en) * | 2010-03-18 | 2011-10-01 | Vanderbilt Co R T | Polyurethane foam scorch inhibitor |
Also Published As
| Publication number | Publication date |
|---|---|
| RU2016146235A3 (zh) | 2018-12-10 |
| AR100764A1 (es) | 2016-11-02 |
| PH12016502135A1 (en) | 2017-01-09 |
| RU2686833C2 (ru) | 2019-04-30 |
| JP6548669B2 (ja) | 2019-07-24 |
| EP3137541A4 (en) | 2017-12-20 |
| JP2017516889A (ja) | 2017-06-22 |
| CN106332548B (zh) | 2019-06-14 |
| US20150307676A1 (en) | 2015-10-29 |
| BR112016024879A2 (pt) | 2017-08-15 |
| RU2016146235A (ru) | 2018-05-28 |
| KR20170032219A (ko) | 2017-03-22 |
| CA2945385A1 (en) | 2015-11-05 |
| TW201609904A (zh) | 2016-03-16 |
| MX2016013633A (es) | 2017-07-25 |
| AU2015253576B2 (en) | 2018-03-08 |
| CN106332548A (zh) | 2017-01-11 |
| MY172329A (en) | 2019-11-21 |
| AU2015253576A1 (en) | 2016-11-03 |
| AU2015253576C1 (en) | 2019-05-02 |
| WO2015167856A1 (en) | 2015-11-05 |
| EP3137541A1 (en) | 2017-03-08 |
| US9481775B2 (en) | 2016-11-01 |
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